TW201326359A - 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 - Google Patents
新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 Download PDFInfo
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- TW201326359A TW201326359A TW101131740A TW101131740A TW201326359A TW 201326359 A TW201326359 A TW 201326359A TW 101131740 A TW101131740 A TW 101131740A TW 101131740 A TW101131740 A TW 101131740A TW 201326359 A TW201326359 A TW 201326359A
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- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 38
- -1 cyano, carbazolyl Chemical group 0.000 claims description 26
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- 150000002367 halogens Chemical class 0.000 claims description 26
- 230000005684 electric field Effects 0.000 claims description 25
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
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- 239000001257 hydrogen Substances 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
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- 125000005842 heteroatom Chemical group 0.000 claims description 8
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- 125000004076 pyridyl group Chemical group 0.000 claims description 6
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
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- 125000001769 aryl amino group Chemical group 0.000 claims description 4
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- HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
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- 230000005525 hole transport Effects 0.000 description 4
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- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- KNVVMNKJHCIPRV-UHFFFAOYSA-M lithium;3-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=CC=C2N=C(C([O-])=O)C(O)=CC2=C1 KNVVMNKJHCIPRV-UHFFFAOYSA-M 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Abstract
本發明係關於新穎化合物及包含該化合物之有機電場發光裝置。因根據本發明之化合物具有高電子傳輸效率,當製造該裝置時能避免結晶,且因它們可適應層的形成,改善了該裝置之電流特性,且最後它們能製造相較於包含傳統材料之裝置具有降低之驅動電壓、促進之功率效率和改善之發光效率與壽命特性之有機電場發光裝置。
Description
本發明係關於新穎有機電場發光化合物及使用該化合物之有機電場發光裝置。
電場發光(EL)裝置為自發光裝置,相較其他類型的顯示器裝置,其具有優點在於提供較寬之視角、較高之對比度及具有較快之反應時間。伊斯門-柯達(Eastman Kodak)首先研發了有機EL裝置,藉由使用小分子例如芳香族二胺及鋁錯合物作為形成發光層之材料。[Appl.Phys.Lett.51,913,1987]
決定有機EL裝置的發光效率的最重要因素係發光材料。到目前為止,螢光材料已被廣泛用作為發光材料。然而,鑑於電場發光機制,磷光材料理論上比螢光材料呈現出高於四倍的發光效率,故開發磷光材料是最好的方法之一。銥(III)錯合物係廣為人知之磷光材料,包含分別作為紅光材料、綠光材料及藍光材料之雙(2-(2'-苯并噻吩基)-吡啶-N、C3')銥(乙醯基丙酮)((acac)Ir(btp)2)、参(2-苯基吡啶)銥(Ir(ppy)3)及雙(4,6-二氟苯基吡啶-N、C2)甲吡啶銥(Firpic)。尤其,最近日本、歐洲與美國致力於研發許多磷光材料。
目前,4,4'-N,N'-二咔唑-聯苯(CBP)是最廣泛用於磷光物質之
主體材料。再者,已知使用浴銅靈(bathocuproine,BCP)與雙(2-甲基-8-羥基喹啉)(4-苯基酚)鋁(III)(BAlq)作為電洞阻隔層的有機EL裝置,以及先鋒(Pioneer(日本))等公司已開發採用BAlq之衍生物作為主體材料之高性能有機EL裝置。
雖然這些材料提供良好的發光特性,但它們仍有下述缺點。由於它們的玻璃轉換溫度低與熱穩定性差,在真空高溫沉積過程中它們可能發生降解。有機EL裝置的功率效率係由[(π/電壓)×電流效率]而得,且功率效率與電壓成反比,因此,為了減少功率消耗,而需要提高功率效率。雖然包含磷光材料的有機EL裝置相較於包含螢光材料者提供較高的電流效率(燭光(cd)/安培(A)),然而使用常用的磷光材料(例如BAlq與CBP)之有機EL裝置相較於使用螢光材料者具有較高的驅動電壓。因此,使用常用的磷光材料之EL裝置就功率效率(流明(lm)/瓦(W))而言並無優勢。此外,有機EL裝置的操作壽命短。因此,需要研究具有較好性質的紅光主體材料。
日本專利公開第1999-149987號揭露包含其中N-咔唑基係鍵結至丙二烯合茀結構之化合物及盧伯林(lublene)作為發光層之材料之裝置,該發光層亦有作為電洞注入層和傳輸層之功能。然而,該裝置發射黃光。該文件亦揭露發射綠光之螢光電場發光裝置且包含其中N-咔唑基係鍵結至丙二烯合茀結構之化合物作為電洞注入層和傳輸層之材料。
然而,其並未揭露發射紅光之磷光電場發光裝置且包含其中N-咔唑基係鍵結至丙二烯合茀結構之化合物作為發光層之主體材料。
本發明之目的係提供賦予裝置高發光效率與長操作壽命、以及發射紅光之有機電場發光化合物;以及使用該化合物作為發光材料之具有高效率與長壽命的有機電場發光裝置。
本案發明者發現上述目的可由下述式(1)表示之有機電場發光化合物達成:
其中,Z表示或;L1表示單鍵、經取代或未經取代之3員至30員伸雜芳基、或經取代或未經取代之(C6-C30)伸芳基;X表示-O-、-S-、-CR11R12-或-NR13-;R11至R13各獨立表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之3員至30
員雜芳基;R1至R6各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之5員至7員雜環烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、與至少一個(C3-C30)環烷基稠合之經取代或未經取代之(C6-C30)芳基、與至少一個經取代或未經取代之芳香環稠合之5員至7員雜環烷基、與至少一個經取代或未經取代之芳香環稠合之(C3-C30)環烷基、-NR14R15、-SiR16R17R18、-SR19、-OR20、(C2-C30)烯基、(C2-C30)炔基、氰基、或硝基;R14至R20各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基;或R14至R20各獨立連結至一個或多個相鄰取代基而形成其中一個或多個碳原子可經至少一個選自氮、氧和硫之雜原子置換之單環或多環之(C5-C30)脂族環或芳族環;a、d和e各獨立表示1至4之整數;當a、d或e係2或更大之整數時,各R1、各R4、和R5係相同或不同;b和f各獨立表示1至3之整數;當b或f係2或更大之整數時,各R2和各R6係相同或不同;c表示1至5之整數;當c係2或更大之整數時,各R3係相同或不同;m表示1、2或3;以及該雜環烷基和該(伸)雜芳基含有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子。
因根據本發明之有機電場發光裝置具有高電子傳輸效率,當製造裝置時能避免結晶。再者,該化合物具有良好的層成形性及改善該裝置之電流特徵。因此,它們可製造具有降低驅動電壓及促進功率效率的有機電場發光裝置。
後文,將詳細描述本發明。然而,以下描述係意欲解釋本發明,且不意欲以任何方式限制本發明之範疇。
本發明係有關上式(1)表示之有機電場發光化合物、包含該化合物之有機電場發光材料、及包含該材料之有機電場發光裝置。
本文中,「烷基」包含甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等;「烯基」包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;「炔基」包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等;「環烷基」包含環丙基、環丁基、環戊基、環己基等;「5員至7員雜環烷基」係具有至少一個選自B、N、O、S、P(=O)、Si和P,較佳係O、S和N之雜原子,以及5環至7環主鏈原子之環烷基,並包含四氫呋喃、吡咯啶、硫雜環戊烷、四氫哌喃等;「(伸)芳基」係衍生自芳香族烴之單環或稠合環,並包含苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基、芘基、并四苯基(tetracenyl)、苝基、蒯基(chrysenyl)、稠四苯基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等;「3員至
30員(伸)雜芳基」係具有至少一個,較佳1至4個選自B、N、O、S、P(=O)、Si和P所組成群組之雜原子,以及2至30個環主鏈原子之芳基;係與至少一個苯環縮合的單環或稠合環;可為部分飽和;可藉由將至少一個雜芳基或芳基透過一個或多個單鍵鍵結至雜芳基而形成者;且包含單環類型雜芳基,包含呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基、唑基、二唑基、三基、四基、三唑基、四唑基、呋吖基(furazanyl)、吡啶基、吡基、嘧啶基、嗒基等;與稠合環類型雜芳基,包含苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異唑基、苯并唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹啉基、咔唑基、啡基、啡啶基、苯并二呃基(benzodioxolyl)等。此外,「鹵素」包含F、Cl、Br和I。
本文中,(C1-C30)烷基較佳為(C1-C20)烷基,更佳為(C1-C6)烷基;(C6-C30)芳基較佳為(C6-C21)芳基;3員至30員雜芳基較佳為3員至21員雜芳基;(C3-C30)環烷基較佳為(C3-C20)環烷基,更佳為(C3-C7)環烷基。
本文中,在表達方式「經取代或未經取代」中之「經取代」意指在特定官能基之氫原子經其他原子或基團(例如,取代基)置換。
在式(1)之L1、R1至R6和R11至R20中,經取代之烷基、經取代之烯基、經取代之炔基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)環烷基、經取代之雜環烷基和經取代之芳烷基
之取代基,各獨立為選自下列所組成群組之至少一者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3員至30員雜芳基、5員至7員雜環烷基、(C3-C30)環烷基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、苯并咔唑基、二苯并咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基,且較佳係選自下列所組成群組之至少一者:氘、鹵素、經取代或未經取代之(C1-C6)烷基、經取代或未經取代之(C6-C21)芳基和經取代或未經取代之3員至21員雜芳基、三(C6-C12)芳基矽烷基,更佳係選自下列所組成群組之至少一者:氘、鹵素、未經取代之(C1-C6)烷基、未經取代之(C6-C21)芳基、未經取代之3員至21員雜芳基和三(C6-C12)芳基矽烷基。
根據本發明之一具體實施例,在上述式(1)中,L1表示單鍵、3員至30員伸雜芳基或(C6-C30)伸芳基;X表示-O-、-S-、-CR11R12-或-NR13-;R11至R13各獨立表示(C1-C30)烷基、(C6-C30)芳基、或3員至30員雜芳基;R1至R6各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3員至30員雜芳基、或咔唑基;m表示1或2;在L1中之伸雜芳基和伸芳基、在R1至R6和R11至R13中之烷基、芳基、雜芳基及咔唑基,可經選自下列所組成群組之至少一者取代:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)
芳基、3員至30員雜芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、咔唑基、苯并咔唑基、及二苯并咔唑基。
較佳地,L1表示單鍵、伸苯基、伸萘基、伸聯苯基、伸聯三苯基、伸蒽基、伸茚基、伸茀基、伸菲基、伸聯伸三苯基、伸芘基、伸苝基、伸蒯基(chrysenylene)、伸稠四苯基、伸丙二烯合茀基、伸苯基-伸萘基、伸呋喃基、伸噻吩基、伸吡咯基、伸咪唑基、伸吡唑基、伸噻唑基、伸噻二唑基、伸異噻唑基、伸異唑基、伸唑基、伸二唑基、伸三基、伸四基、伸三唑基、伸呋吖基、伸吡啶基、伸吡基、伸嘧啶基、伸嗒基、伸苯并呋喃基、伸苯并噻吩基、伸異苯并呋喃基、伸苯并咪唑基、伸苯并噻唑基、伸苯并異噻唑基、伸苯并異唑基、伸苯并唑基、伸異吲哚基、伸吲哚基、伸吲唑基、伸苯并噻二唑基、伸喹啉基、伸異喹啉基、伸噌啉基、伸喹唑啉基、伸喹啉基、伸咔唑基、伸啡啶基、伸苯并二呃基(benzodioxolylene)、伸二苯并呋喃基或伸二苯并噻吩基。
在上述式(1)中,L1較佳為單鍵、或經取代或未經取代之(C6-C21)伸芳基,更佳為單鍵、或經(C1-C6)烷基取代或未經取代之(C6-C21)伸芳基。
R1至R6較佳各獨立為氫、鹵素、經取代或未經取代之(C6-C21)芳基、經取代或未經取代之3員至21員雜芳基,更佳為氫、鹵素、經鹵素、氘、(C1-C6)烷基、(C6-C21)芳基、3員至21員雜芳基或三(C6-C12)芳基矽烷基取代或未經取代之(C6-C21)芳基、或未經取代之3員至21員雜芳基。
R11至R13較佳各獨立為經取代或未經取代之(C1-C6)烷基、經取代或未經取代之(C6-C21)芳基、或經取代或未經取代之3員至21員雜芳基,更佳為未經取代之(C1-C6)烷基、經鹵素、氘、或(C1-C6)烷基取代或未經取代之(C6-C21)芳基、或經(C6-C21)芳基取代之3員至21員雜芳基。
本發明之代表性化合物包含以下化合物:
本發明之有機電場發光化合物可根據以下反應方案製備:
其中,L1、Z、R1至R4、m、a、b、c和d係如上式(1)定義,
以及Hal表示鹵素。
此外,本發明提供包括式(1)之有機電場發光化合物之有機電場發光材料,以及包括該材料之有機電場發光裝置。上述材料可包括根據本發明之有機電場發光化合物本身或可進一步包含常用於有機電場發光材料之傳統材料。該有機電場發光裝置包括第一電極、第二電極以及至少一層置於該第一電極與第二電極間之有機層。該有機層包括至少一種根據本發明式(1)之化合物。此外,該有機層包括發光層,其中係包括作為主體材料之式(1)之化合物。
當使用式(1)之有機電場發光化合物作為發光層之主體材料時,能一起使用一種或多種磷光摻雜劑。
不限制施用於根據本發明之電場發光裝置中的磷光摻雜劑,但較佳可選自下式(2)表示之化合物:M1L101L102L103 式(2)
其中,M1係選自Ir、Pt、Pd和Os所組成之群組;L101、L102和L103係各獨立選自以下結構:
R201至R203各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、經一個或多個(C1-C30)烷基取代或未經取代之(C6-C30)芳基、或鹵素;R204至R219各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基、SF5、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、氰基或鹵素;R220至R223各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、或經一個或多個(C1-C30)烷基取代或未經取代之(C6-C30)芳基;R224和R225各獨立表示氫、氘、經取代或未經取代之(C1-C30)
烷基、經取代或未經取代之(C6-C30)芳基、或鹵素,或R224和R225連結至一個或多個相鄰取代基以形成單環或多環之(C5-C30)脂族環或芳族環;R226係表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3員至30員雜芳基或鹵素;R227至R229各獨立表示氫、氘、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基或鹵素;Q係表示、或;R231至R242各獨立表示氫、氘、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、(C1-C30)烷氧基、鹵素、經取代或未經取代之(C6-C30)芳基、氰基、或經取代或未經取代之(C5-C30)環烷基,或R231至R242各可透過伸烷基或伸烯基連結至相鄰取代基以形成螺環或稠合環,或各可透過伸烷基或伸烯基連結至R207或R208以形成飽和或不飽和之稠合環。
式(2)之摻雜劑包含以下,但其不限於此:
根據本發明之有機電場發光裝置,除了包括式(1)表示之有機電場發光化合物外,可進一步包括至少一種選自芳基胺系化合物和苯乙烯基芳基胺系化合物所組成群組之化合物。
根據本發明之有機電場發光裝置,該有機層可進一步包括至少一種選自週期表之第1族之金屬、第2族之金屬、第4週期之過渡金屬、第5週期之過渡金屬、鑭系金屬及d-過渡元素金屬之
有機金屬所組成群組之金屬,或至少一種包括該金屬之錯合物。該有機層可包括發光層及電荷產生層。
此外,除了本發明之化合物外,該有機電場發光裝置可藉由進一步包括其中包括藍光電場發光化合物、紅光電場發光化合物或綠光電場發光化合物之至少一層發光層,以發射白光。
較佳地,在本發明之有機電場發光裝置中,可將選自硫屬化合物(chalcogenide)層、金屬鹵化物層及金屬氧化物層之至少一層之層體(後文中稱為「表面層」)設置於該電極對之一個或兩個電極的內表面上。具體而言,較佳可將矽或鋁之硫屬化合物(包括氧化物)層設置於電場發光介質層之陽極表面上,並可將金屬鹵化物層或金屬氧化物層設置於電場發光介質層之陰極表面上。該表面層提供有機電場發光裝置之操作安定性。較佳地,該硫屬化合物包含SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等;該金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等;以及該金屬氧化物包含Cs2O、Li2O、MgO、SrO、BaO、CaO等。
較佳地,在本發明之有機電場發光裝置中,可將電子傳輸化合物與還原性摻雜劑之混合區域或電洞傳輸化合物與氧化性摻雜劑之混合區域設置於電極對的至少一個表面上。於此例中,將該電子傳輸化合物還原成陰離子,而使該電子傳輸化合物變得易於自混合區域注入與傳輸電子至電場發光介質。再者,將該電洞傳輸化合物氧化成陽離子,而使該電洞傳輸化合物變得易於自混合區域注入與傳輸電洞至電場發光介質。較佳地,該氧化性摻雜劑係包括各種路易士酸及接受者化合物;以及該還原性摻雜劑係包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。可
使用還原性摻雜劑層作為電荷產生層來製備具有兩層或更多層電場發光層和發射白光之電場發光裝置。
後文,將參考下列實施例詳細描述本發明之有機電場發光化合物、該化合物之製備方法以及包括該化合物之裝置的發光性質:
化合物1-2之製備
將化合物1-1(50 g,247.2 mmol)溶解於MeCN(50mL)並添加N-溴琥珀醯亞胺(NBS)(44 g,247.2 mmol)後,於室溫下攪拌該反應混合物1天。反應終止後,該反應混合物以乙酸乙酯(EA)萃取,且濃縮該有機層並透過矽膠管柱純化以獲得化合物1-2(55.6 g,80%)。
化合物1-3之製備
將化合物1-2(7.7 g,27.5 mmol)溶解於四氫呋喃(THF)(250 mL)後,冷卻該反應混合物至-78℃。將溶於己烷之2.5M n-BuLi(17.6 mL,44 mmol)添加至反應混合物,並攪拌該反應混合物1小時。於相同溫度下緩慢添加B(Oi-Pr)3(12.6 mL,55 mmol),並攪拌該反應混合物2小時。攪拌後,添加2M HCl使該反應混合物淬火(quench),以蒸餾水和EA萃取,並濃縮該有機層。以二氯甲烷(MC)和已烷
再結晶該有機層以獲得化合物1-3(4.0 g,60%)。
化合物1-4之製備
將化合物1-3(4.5 g,18.3 mol)、4-溴碘苯(6.73 g,23.8 mol)、Pd(PPh3)4(634 mg,0.55 mmol)和Na2CO3(5.8 g,54.9 mol)置於甲苯(110 mL)和純水(27 mL)中後,於75℃攪拌該反應混合物3小時。反應終止後,移除該水層,且濃縮該有機層並透過矽膠管柱純化以獲得化合物1-4(3.9 g,60%)。
化合物1-7之製備
將化合物1-5(14g,48.76 mmol)、化合物1-6(10g,40.63 mmol)、K2CO3(13.5 g,97.52 mmol)和Pd(PPh3)4(2.35 g,2.03 mmol)置於甲苯(200 mL)、乙醇(50mL)和純水(50 mL)中後,於95℃攪拌該反應混合物3小時。反應終止後,冷卻該反應混合物至室溫。移除該水層,且濃縮該有機層,與MC研磨,並過濾以獲得化合物1-7(12 g,72%)。
化合物C-35之製備
將化合物1-4(3.3 g,9.2 mmol)、化合物1-7(3.4 g,8.4 mmol)、Cs2CO3(8.2 g,25.2 mmol)、CuI(880 mg,4.62 mmol)和乙二胺(EDA)(0.6 mL,8.4 mmol)置於甲苯(50 mL)中後,於回流下攪拌該反應混合物1天。以EA萃取該反應混合物,經減壓蒸餾,並經管柱(MC和已烷)過濾以獲得化合物C-35(1.7 g,29.8%)。
MS/FAB實測值684.82;計算值684.26
化合物2-1之製備
將化合物1-3(10 g,40.6 mol)、4,4'-二溴聯苯(38 g,121.9 mol)、Pd(PPh3)4(2.3 g,2.03 mmol)和Na2CO3(12.9 g,121.9 mol)置於甲苯(244 mL)和純水(60 mL)中後,於75℃攪拌該反應混合物3小時。反應終止後,移除該水層,且濃縮該有機層並透過矽膠管柱純化以獲得化合物2-1(9.5 g,54%)。
化合物C-42之製備
將化合物2-1(5.0 g,11.5 mmol)、化合物1-7(4.7 g,11.5 mmol)、Pd(OAc)2(129 mg,0.575 mmol)、50% P(t-Bu)3(0.54 mL,2.3 mmol)和Cs2CO3(11.2 g,34.5 mmol)置於甲苯(50 mL)中後,於回流下攪拌該反應混合物1天。以EA萃取該反應混合物,經減壓蒸餾,並經管柱(MC和已烷)過濾以獲得化合物C-42(3.5 g,40%)。
MS/FAB實測值760.92;計算值760.29
使用根據本發明之化合物製造OLED裝置。使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水清洗有機發光二極體(OLED)裝置(Samsung Corning,Republic of Korea)之玻璃基質透明電極銦錫氧化物(ITO)薄膜(15 Ω/sq),然後儲存於異丙醇中。然後,將ITO基板裝配於真空氣相沉積裝置之基板夾中。將N1,N1'-([1,1'-聯
苯]-4,4'-二基)雙(N1-(萘-1-基)-N4,N4-二苯基苯-1,4,-二胺)導入該真空氣相沉積裝置之小室中,隨後控制該腔室內之壓力為10-6托(torr)。隨後,對該小室施加電流以蒸發上述導入物質,從而於ITO基板上形成厚度為60nm之電洞注入層。然後,將N,N'-二(4-聯苯基)-N,N'-二(4-聯苯基)-4,4'-二胺基聯苯導入該真空氣相沉積裝置之另一小室中,隨後對該小室施加電流以蒸發上述物質,從而於該電洞注入層上形成厚度為20nm之電洞傳輸層。接著,將化合物C-42導入該真空氣相沉積裝置之一小室中作為主體材料,並將化合物D-7導入另一小室中作為摻雜劑。以不同速率蒸發該兩種材料,並以(基於主體與摻雜劑總量計)摻雜劑之摻雜量為4重量%沈積於該電洞傳輸層上以形成厚度為30nm之發光層。然後,將2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑導入一小室中,並將羥基喹啉鋰(lithium quinolate)導入另一小室中。以相同速率蒸發該兩種材料,並以摻雜量為50重量%分別沉積於該電場發光層上形成厚度為30nm之電子傳輸層。然後,在沉積具有厚度為2 nm之羥基喹啉鋰作為電子傳輸層上之電子注入層後,用另一個真空氣相沉積裝置在該電子注入層上形成厚度為150nm之鋁(Al)陰極。因而製造出OLED裝置。用於製造該OLED裝置之所有材料皆已藉由於10-6托真空昇華予以純化。
該製得的OLED裝置在驅動電壓3.9 V下顯示具有亮度為1,060燭光(cd)/平方公尺(m2)以及電流密度為7.7毫安培(mA)/平方公分(cm2)之紅光發光。再者,從亮度為5,000尼特(nit)減少至90%亮度的時間為至少130小時。
除了使用化合物C-35作為主體材料及使用化合物D-7作為摻雜劑之外,以裝置實施例1之相同方法製造OLED裝置。
該製得的OLED裝置在驅動電壓3.8V下顯示具有亮度為1,020cd/cm2以及電流密度為7.5mA/cm2之紅光發光。再者,從亮度為5,000尼特減少至90%亮度的時間為至少130小時。
除了使用4,4'-N,N'-二咔唑-聯苯作為主體材料及使用化合物D-11作為摻雜劑沈積發光層,以及藉由使用雙(2-甲基-8-羥基喹啉)-4-苯基酚鋁(III)在發光層和電子傳輸層間沈積具有厚度為10nm之電洞阻擋層之外,以裝置實施例1之相同方法製造OLED裝置。
該製得的OLED裝置在驅動電壓8.2 V下顯示具有亮度為1,000cd/cm2,以及電流密度為20.4mA/cm2之紅光發光。再者,從亮度為5,000尼特減少至90%亮度的時間為至少10小時。
與傳統材料相比,本發明之有機電場發光化合物具有優越的發光特性。此外,使用根據本發明之化合物作為發光主體材料之裝置,係藉由降低驅動電壓增加功率效率,且具有優異的發光效率和壽命特性。
Claims (6)
- 一種下式(1)表示之有機電場發光化合物,
- 如申請專利範圍第1項所述之化合物,其中,在L1、R1至R6和R11至R20中,該經取代之烷基、經取代之烯基、經取代之炔基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)環烷基、經取代之雜環烷基和經取代之芳烷基之取代基各獨立 選自下列所組成群組之至少一者:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3員至30員雜芳基、5員至7員雜環烷基、(C3-C30)環烷基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、苯并咔唑基、二苯并咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基和羥基。
- 如申請專利範圍第1項所述之化合物,其中,L1表示單鍵、3員至30員伸雜芳基或(C6-C30)伸芳基;X表示-O-、-S-、-CR11R12-或-NR13-;R11至R13各獨立表示(C1-C30)烷基、(C6-C30)芳基、或3員至30員雜芳基;R1至R6各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3員至30員雜芳基、或咔唑基;m表示1或2;以及L1之該伸雜芳基和伸芳基、R1至R6和R11至R13之該烷基、芳基、雜芳基及咔唑基可經選自下列所組成群組之至少一者取代:氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、3員至30員雜芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30) 烷基二(C6-C30)芳基矽烷基、咔唑基、苯并咔唑基、及二苯并咔唑基。
- 如申請專利範圍第3項所述之化合物,其中,L1表示單鍵、伸苯基、伸萘基、伸聯苯基、伸聯三苯基、伸蒽基、伸茚基、伸茀基、伸菲基、伸聯伸三苯基、伸芘基、伸苝基、伸蒯基、伸稠四苯基、伸丙二烯合茀基、伸苯基-伸萘基、伸呋喃基、伸噻吩基、伸吡咯基、伸咪唑基、伸吡唑基、伸噻唑基、伸噻二唑基、伸異噻唑基、伸異唑基、伸唑基、伸二唑基、伸三基、伸四基、伸三唑基、伸呋吖基、伸吡啶基、伸吡基、伸嘧啶基、伸嗒基、伸苯并呋喃基、伸苯并噻吩基、伸異苯并呋喃基、伸苯并咪唑基、伸苯并噻唑基、伸苯并異噻唑基、伸苯并異唑基、伸苯并唑基、伸異吲哚基、伸吲哚基、伸吲唑基、伸苯并噻二唑基、伸喹啉基、伸異喹啉基、伸噌啉基、伸喹唑啉基、伸喹啉基、伸咔唑基、伸啡啶基、伸苯并二呃基(benzodioxolylene)、伸二苯并呋喃基或伸二苯并噻吩基。
- 如申請專利範圍第1項所述之化合物,其中,該式(1)表示之化合物係選自下列所組成群組者:
- 一種包括如申請專利範圍第1項所述之化合物之有機電場發光裝置。
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WO2013146117A1 (ja) * | 2012-03-26 | 2013-10-03 | 東レ株式会社 | 発光素子材料および発光素子 |
CN104488105B (zh) * | 2012-07-25 | 2017-03-22 | 东丽株式会社 | 发光元件材料和发光元件 |
CN104703969B (zh) * | 2012-11-21 | 2017-09-05 | 株式会社Lg化学 | 荧蒽化合物及包含其的有机电子器件 |
US20150364692A1 (en) * | 2013-05-02 | 2015-12-17 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
US10205099B2 (en) | 2013-05-31 | 2019-02-12 | Idemitsu Kosan Co., Ltd. | Condensed fluoranthene compound, organic electroluminescence element material including same, organic electroluminescence element using same, and electronic device |
KR101576562B1 (ko) | 2013-07-19 | 2015-12-10 | 주식회사 두산 | 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
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JP6298608B2 (ja) * | 2013-10-03 | 2018-03-20 | 出光興産株式会社 | フルオランテン誘導体、有機エレクトロルミネッセンス素子及び電子機器 |
CN104650118B (zh) * | 2014-07-01 | 2017-01-11 | 吉林奥来德光电材料股份有限公司 | 一种以二苯并呋喃为骨架核心的衍生物制备及其应用 |
WO2016017514A1 (ja) * | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、発光性薄膜、表示装置及び照明装置 |
US10629821B2 (en) | 2015-04-08 | 2020-04-21 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements using same, and organic electroluminescent element and electronic device each using same |
US20170229661A1 (en) | 2015-06-16 | 2017-08-10 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device |
WO2016204150A1 (ja) * | 2015-06-16 | 2016-12-22 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
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US20170141330A1 (en) * | 2015-11-17 | 2017-05-18 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
CN109251176B (zh) * | 2017-07-12 | 2020-11-13 | 北京鼎材科技有限公司 | 一种有机电致发光器件 |
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CN109553620A (zh) * | 2017-09-25 | 2019-04-02 | 北京鼎材科技有限公司 | 通式化合物及有机电致发光器件 |
CN108358891A (zh) * | 2018-02-11 | 2018-08-03 | 上海升翕光电科技有限公司 | 一种有机发光化合物及其制备方法和应用 |
CN108373463A (zh) * | 2018-02-11 | 2018-08-07 | 上海升翕光电科技有限公司 | 有机发光化合物及其制备方法和有机电致发光器件 |
KR102206482B1 (ko) | 2018-04-24 | 2021-01-22 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
CN112080273B (zh) * | 2019-06-14 | 2024-04-09 | 南京高光半导体材料有限公司 | 有机电致发光化合物及包含该化合物的有机电致发光器件 |
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JP4585786B2 (ja) * | 2004-04-01 | 2010-11-24 | キヤノン株式会社 | 発光素子及び表示装置 |
JP2008137978A (ja) * | 2006-12-05 | 2008-06-19 | Canon Inc | カルバゾール誘導体及びこれを用いた有機発光素子 |
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EP2141214A3 (en) * | 2008-06-25 | 2010-02-24 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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