TW201331339A - 新穎有機電致發光化合物及使用該化合物之有機電致發光裝置 - Google Patents
新穎有機電致發光化合物及使用該化合物之有機電致發光裝置 Download PDFInfo
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- TW201331339A TW201331339A TW101143044A TW101143044A TW201331339A TW 201331339 A TW201331339 A TW 201331339A TW 101143044 A TW101143044 A TW 101143044A TW 101143044 A TW101143044 A TW 101143044A TW 201331339 A TW201331339 A TW 201331339A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 53
- -1 2-oxazolyl Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
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- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims 2
- RZFOAVRHEGQZRV-UHFFFAOYSA-N 2,3-diphenylthiophene Chemical group S1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RZFOAVRHEGQZRV-UHFFFAOYSA-N 0.000 claims 1
- 125000005264 aryl amine group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
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- 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 7
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- 125000001294 (C1-C30) cycloalkyl group Chemical group 0.000 description 3
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- 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 3
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- 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
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
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- 229910052797 bismuth Inorganic materials 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000007517 lewis acids Chemical class 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
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 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
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明係關於新穎有機電致發光化合物及含有該化合物之有機電致發光裝置。根據本發明之有機電致發光化合物,由於其高於傳統材料之發光效率,具有製造具有長操作壽命之OLED裝置的優點,且該裝置具有藉由改善之功率效率而降低功率損耗。
Description
本發明係關於新穎有機電致發光化合物及包含該化合物之有機電致發光裝置。
電致發光(EL)裝置係自發光裝置,與其他類型之顯示器裝置相比,其具有優勢在於提供更寬之視角,更大之對比度以及更快之反應時間。有機EL裝置係由伊士曼柯達(Eastman Kodak)首先研發,藉由使用芳香族二胺小分子以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裝置之發光效率之最重要因素係發光材料。迄今為止,螢光材料業經廣泛用作發光材料。惟,以電致發光機制之觀點,發展磷光材料係理論上將發光效率提升四(4)倍之最佳方法之一。銥(III)錯合物已廣為人知作為磷光材料,包括雙(2-(2’-苯并噻吩基)-吡啶-N,C3’)銥(乙醯基丙酮)((acac)Ir(btp)2)、參(2-苯基吡啶)銥(Ir(ppy)3)及雙(4,6-二氟苯基吡啶-N,C2)吡啶甲酸銥(Firpic)分別作為紅色、綠色及藍色材料。尤其,近年來多種磷光材料於日本、歐洲及美國已被研發。
迄今為止,4,4’-N,N’-二咔唑-聯苯(CBP)係最廣為人知之用於磷光物質的主體材料。再者,亦知使用浴銅靈(bathocuproine,BCP)及雙(2-甲基-8-羥基喹啉)(4-苯基苯酚)鋁(III)(BAlq)用於電洞阻擋層的有機EL裝置,及日本先鋒公司(Pioneer)研發了採用BAlq之衍生物作為主體材料之高效能有機EL裝置。
儘管這些材料提供良好之發光特徵,但他們仍具有下述缺點。由於他們的低玻璃轉化溫度及不良之熱安定性,可能於真空高溫沉積製程過程中出現退化。有機EL裝置之功率效率係藉由[(Π/電壓)×電流效率]給出,且功率效率係與電壓成反比,因此,為了降低功率損耗而應提升功率效率。儘管包含磷光材料之有機EL裝置係比包含螢光材料者提供較高的電流效率(燭光(cd)/安培(A)),使用傳統磷光材料如BAlq或CBP之有機EL裝置相較於使用螢光材料者具有較高之驅動電壓。因此,使用傳統磷光材料之EL裝置於功率效率(流明(lm)/瓦(W))方面不具優勢。再者,該有機EL裝置之操作壽命短。
公開第2011-0014752號韓國專利申請案揭露一種咔唑系化合物以及使用該咔唑化合物之有機EL裝置。該等化合物具有三個芳基作為該咔唑結構之取代基,且該裝置顯示綠色發光。
為了克服上述缺點,本發明之目的係提供一種有機電致發光化合物,與傳統材料相比,該化合物具有高發光效率以及長操作壽命;以及使用該化合物作為發光材料之具有高效率及長壽命的有機電致發光裝置。
本發明之發明人發現上揭目的係藉由下式1表示之有機電致發光化合物達成:
其中,L1係表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之3至30員伸雜芳基;Ar1至Ar5係各自獨立表示CR10、C-L2-(L3)m-Ar1或N,且其限制條件為Ar1至Ar5之至少一者係C-L2-(L3)m-Ar1;L2與L3係各自獨立表示經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之3至30員伸雜芳基;R1、R2、R10及Ar1係各自獨立表示氫、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(C3-C30)環烷基、經取代或未經取代之5至7員雜環烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3至30員雜芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、或硝基;R11至R17係各自獨立表示氫、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、或經取代或未經取代之3至30員雜芳基;a係表示1至6之整數;若a係2或更大之整數,則每一R1
係相同或不同;b係表示1至4之整數;若b係2或更大之整數,則每一R2係相同或不同;m係表示整數1或2;若m係2或更大之整數,則每一L3係相同或不同;該伸雜芳基、雜環烷基及雜芳基係含有選自B、N、O、S、P(=O)、Si及P所組成群組之至少一個雜原子;且其限制條件為R2不為2-咔唑基或3-咔唑基。
與傳統材料相比,根據本發明之有機電致發光化合物具有高發光效率及長操作壽命。因此,他們可製造具有藉由增加功率效率而提升之功率損耗效率以及傑出之操作壽命的有機電致發光裝置。
後文中,將詳細描述本發明。惟,下述描述係意於解釋本發明,而非意欲以任何方式限制本發明之範疇。
本發明係關於上式1表示之有機電致發光化合物、包含該有機電致發光化合物之有機電致發光材料、以及包含該材料之有機電致發光裝置。
本文中,「(C1-C30)(伸)烷基」係意指具有1至30個碳原子之直鏈或分支鏈(伸)烷基,其中,碳原子之數目較佳係1至20個,更佳係1至10個,且包括甲基、乙基、正丙基、異丙基、正丁基、
異丁基、第三丁基等;「(C2-C30)烯基」係意指具有2至30個碳原子之直鏈或分支鏈烯基,其中,碳原子之數目較佳係2至20個,更佳係2至10個,且包括乙烯基、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;「(C2-C30)炔基」係意指具有2至30個碳原子之直鏈或分支鏈炔基,其中,碳原子之數目較佳係2至20個,更佳係2至10個,且包括乙炔基、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;「(C3-C30)環烷基」係意指具有3至30個碳原子之單環烴或多環烴,其中,碳原子之數目較佳係3至20個,更佳係3至7個,且包括環丙基、環丁基、環戊基、環己基等;「5至7員雜環烷基」係具有選自B、N、O、S、P(=O)、Si及P,較佳係O、S及N所組成群組之至少一個雜原子,以及5至7個環骨架原子的環烷基,且包括四氫呋喃、吡咯啶、四氫噻吩(thiolan)、四氫吡喃等;「(C6-C30)(伸)芳基」係具有6至30個碳原子之衍生自芳香族烴之單環或稠合環,其中,碳原子之數目較佳係6至20個,更佳係6至15個,且包括苯基、聯苯基、聯三苯基(terphenyl)、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基(triphenylenyl)、芘基、稠四苯基(tetracenyl)、苝基(perylenyl)、蒯基(chrysenyl)、稠四苯基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等;「3至30員(伸)雜芳基」係具有選自B、N、O、S、P(=O)、Si及P所組成群組之至少一個,較佳1至4個雜原子,以及3至30個環骨架原子的芳基;係單環或與至少一個苯環稠合之稠合環;較佳具有5至20個,更佳5至15個環骨架原子;可為部份飽和;可藉由將至少一個雜芳基或芳基透過一個或多個單鍵鏈結至雜芳基所形成者;其包括單
環型雜芳基,包括呋喃基、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、吡啶基、吡基、嘧啶基、嗒基等,以及稠合環型雜芳基,包括苯并呋喃基、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。再者,「鹵素」係包括F、Cl、Br及I。
本文中,於「經取代或未經取代」表述中之「經取代」係意指在特定官能基中之氫原子經其他原子或基團(亦即,取代基)置換。
式1之L1、L2、L3、R1、R2、R10、Ar1及R11至R17基中之該經取代之烷基、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、及經取代之雜環烷基的取代基,係各自獨立為選自下列所組成群組的至少一者:氘;鹵素;(C1-C30)烷基;鹵(C1-C30)烷基;(C1-C30)烷氧基;(C6-C30)芳氧基;(C6-C30)芳基;3至30員雜芳基;經(C6-C30)芳基取代之3至30員雜芳基;經(C1-C30)烷基及(C6-C30)芳基取代之3至30員雜芳基;(C3-C30)環烷基;5至7員雜環烷基;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;(C1-C30)烷硫基;(C6-C30)芳硫基;N-咔唑基;單或
二(C1-C30)烷基胺基;單或二(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;以及羥基。
根據本發明之有機電致發光化合物係藉由下式2至4表示:
其中,R1、R2、a、b、L1及A1至A5係如上式1中定義者。
具體而言,L1係單鍵或(C6-C30)伸芳基;以及,係選自下列基團:
其中,L2與L3係各自獨立表示(C6-C30)伸芳基或3至30員伸雜芳基;R1與R2係各自獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、或3至30員雜芳基;R10與Ar1係各自獨立表示氫、氘、鹵素、(C1-C30)烷基、(C3-C30)環烷基、(C6-C30)芳基、3至30員雜芳基、或-SiR13R14R15;R13至R15係各自獨立表示(C1-C30)烷基或(C6-C30)芳基;a係表示0至6之整數;b係表示0至4之整數;m係表示整數1或2;以及L1中之伸芳基,L2與L3中之伸芳基及伸雜芳基,R1與R2中之烷基、芳基及雜芳基,R10與Ar1中之烷基、環烷基、芳基及雜芳基,以及R13至R15中之烷基及芳基,可各自獨立進一步經選自下列所組成群組之至少一者取代:氘、鹵素、(C1-C30)烷基、鹵(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3至30員雜芳基、經(C6-C30)芳基取代之3至30員雜芳基、經(C6-C30)芳基及(C1-C30)烷基取代之3至30員雜芳基、(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、氰基、(C1-C30)烷硫基、(C6-C30)芳硫基、(C6-C30)芳基(C1-C30)烷基、及(C1-C30)烷基(C6-C30)芳基。
更具體而言,L2係表示伸苯基、伸吡啶基、伸茀基、伸咔唑基、伸二苯并呋喃基或伸二苯并噻吩基;L3係表示伸苯基、伸聯苯基、伸聯三苯基、伸萘基、伸吡啶基、伸嘧啶基、伸茀基、伸二苯并呋喃基、伸二苯并噻吩基、伸咔唑基、伸5H-吡啶并[3,2-b]吲哚基或伸5H-茚并[1,2-b]吡啶基;Ar1係表示氫、鹵素、(C1-C30)烷基、(C3-C30)環烷基、(C6-C30)芳基、3至30員雜芳基或-SiR13R14R15;R10係表示氫或(C6-C30)芳基;R1與R2係各自獨立表示氫、鹵素、(C1-C30)烷基、(C6-C30)芳基或3至30員雜芳基;L2中之伸苯基、伸吡啶基、伸茀基、伸咔唑基、伸二苯并呋喃基及伸二苯并噻吩基,L3中之伸苯基、伸聯苯基、伸聯三苯基、伸萘基、伸吡啶基、伸嘧啶基、伸茀基、伸二苯并呋喃基、伸二苯并噻吩基、伸咔唑基、伸5H-吡啶并[3,2-b]吲哚基及伸5H-茚并[1,2-b]吡啶基,Ar1中之烷基、環烷基、芳基及雜芳基,R10中之芳基,以及R1與R2中之烷基、芳基及雜芳基,可各自獨立進一步經選自下列所組成群組之至少一者取代:氘、鹵素、(C1-C30)烷基、鹵(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3至30員雜芳基、經(C6-C30)芳基取代之3至30員雜芳基、(C1-C30)烷硫基、(C6-C30)芳硫基、(C6-C30)芳基(C1-C30)烷基、及(C1-C30)烷基(C6-C30)芳基。
再者,L1係表示單鍵、伸苯基、伸萘基、伸聯苯基、伸聯三苯基、伸蒽基、伸茚基、伸9,9-二甲基茀基、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、伸啡啶基、伸苯并二呃基(benzodioxolylene)、伸二苯并呋喃基及伸二苯并環戊烯基(dibenzocyophenylene)。
再者,R1與R2係各自獨立表示氫、鹵素、(C1-C30)烷基、或選自下列之基團:
其中,R'、R"及R'''係各自獨立表示(C1-C30)烷基或(C6-C30)芳基。
再者,Ar1係表示氫、鹵素、(C1-C30)烷基、或選自下列之基團:
其中,R'係表示鹵素或(C1-C30)烷基;以及,R"與R'''係各自獨立表示(C1-C30)烷基或(C6-C30)芳基。
本發明之有機電致發光化合物係包括下列化合物:
本發明之有機電致發光化合物可根據下列反應式製備。
其中,R1、R2、a、b、L1及Ar1至Ar5係如上式1中定義者,且Hal係表示鹵素。
此外,本發明提供包含式1之有機電致發光化合物的有機電致發光材料,以及包含該材料之有機電致發光裝置。該材料可僅由根據本發明之有機電致發光化合物構成,或可復包括通常用於有機電致發光材料中的傳統材料。
該有機電致發光裝置係包含第一電極、第二電極、以及位於該第一電極與第二電極之間的至少一層有機層。該有機層可包含至少一種式1的有機電致發光化合物。再者,該有幾層係包含發光層,其中,式1之有機電致發光化合物可用作主體材料。
該第一電極與第二電極之一者係陽極,另一者係陰極。該有機層復包含發光層,以及選自下列所組成群組之至少一層:電洞注入層、電洞傳輸層、電子傳輸層、電子注入層、中間層及電洞阻擋層。
本發明之式1之有機電致發光化合物可包含於該發光層中。當用於發光層時,本發明之式1之有機電致發光化合物可包含於該層中作為主體材料。較佳地,該發光層可包含至少一種摻雜劑。若需要,除了本發明之式1之有機電致發光化合物之外,可復包含其他化合物作為第二主體材料。
該第二主體材料可為來自任何習知之磷光主體。於發光效率方面,選自下式2至6之化合物所組成群組之化合物的主體係特佳者:H-(Cz-L4)h-M (2)
H-(Cz)i-L4-M (3)
其中,Cz係表示下述結構:
X係表示O或S;R21至R24係各自獨立表示氫、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5至30員雜芳基、或R25R26R27Si-;R25至R27係各自獨立表示經取代或未經取代之(C1-C30)烷基、或經取代或未經取代之
(C6-C30)芳基;L4係表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之5至30員伸雜芳基;M係表示經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之5至30員雜芳基;Y1與Y2係表示-O-、-S-、-N(R31)-或-C(R32)(R33)-,且其限制條件為Y1與Y2不同時存在;R31至R33係各自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5至30員雜芳基,且R32與R33係相同或不同;h與i係各自獨立表示1至3之整數;j、k、l及m係各自獨立表示0至4之整數;以及,若h、i、j、k、l或m係2或更大之整數,每一(Cz-L4)、每一(Cz)、每一R21、每一R22、每一R23或每一R24係相同或不同。
具體而言,該第二主體材料係包括下列:
根據本發明,於該有機電致發光裝置之製造中使用的摻雜劑較佳係一種或多種磷光摻雜劑。施用至本發明之有機電致發光裝置的磷光摻雜劑材料並無具體限制,但較佳可選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之錯合物化合物;更佳係銥、鋨、銅及鉑之鄰位金屬化的錯合物化合物;且又更佳係鄰位金屬化的銥錯合物化合物。
根據本發明,包含於該有機電致發光裝置中之摻雜劑可選自下式7至9表示之化合物:
其中,L係選自下列結構:
R100係表示氫、經取代或未經取代之(C1-C30)烷基、或經取代或未經取代之(C1-C30)環烷基;R101至R109及R111至R123係各自獨立表示氫、氘、鹵素、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)環烷基、氰基、或經取代或未經取代之(C1-C30)烷氧基;R120至R123係鏈結至一個或多個相鄰取代基以形成稠合環,如喹啉環;R124至R127係各自獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、或經取代或未經取代之(C6-C30)芳基;若R124至R127為芳基,則他們可鏈結至一個或多個相鄰取代基以形成稠合環,如茀環;R201至R211係各自獨立
表示氫、氘、鹵素、經一個或多個鹵素取代或未經取代之(C1-C30)烷基、或經取代或未經取代之(C1-C30)環烷基;f與g係各自獨立表示1至3之整數;若f或g係2或更大之整數,每一R100係相同或不同;以及,n係1至3之整數。
該等摻雜劑材料係包括下列:
本發明復提供用於該有機電致發光裝置之材料。該材料包括第一主體材料以及第二主體材料;且該第一主體材料可包含本發明之有機電致發光化合物。該第一主體材料與該第二主體材料可為1:99至99:1之重量比範圍。
再者,於包含第一電極、第二電極以及介於該第一電極與第二電極之間之至少一層有機層的本發明之有機電致發光裝置中,該有機層包含發光層,且該發光層包含根據本發明之用於有機電致發光裝置的材料以及磷光摻雜劑材料。該用於有機電致發光裝置之材料係用作主體材料。
根據本發明之有機電致發光裝置係包含式1表示之有機電致
發光化合物,且可復包括選自芳基胺系化合物及苯乙烯基芳基胺系化合物所組成群組之至少一種化合物。
於根據本發明之有機電致發光裝置中,該有機層除了式1表示之有機電致發光化合物外,可復包含選自週期表第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、鑭系元素及d-過渡元素之有機金屬所組成群組之至少一種金屬,或至少一種包含該金屬之錯合物化合物。該有機層可包含發光層及電荷產生層。
此外,該有機電致發光裝置可藉由復包含至少一層發光層而發出白光,該發光層除了包含根據本發明之有機電致發光化合物外,亦包含藍色電致發光化合物、紅色電致發光化合物或綠色電致發光化合物。
根據本發明,可將該有機電致發光裝置之至少一層較佳選自硫屬化合物(chalcogenide)層、金屬鹵化物層及金屬氧化物層之層(後文中稱為「表面層」)置於一個或兩個電極之一層或多層內表面上。具體而言,較佳係將矽或鋁之硫屬化合物(包括氧化物)層置於電致發光介質層之陽極表面上,並將金屬鹵化物層或金屬氧化物層置於電致發光介質層之陰極表面上。此表面層係對該有機電致發光裝置提供操作安定性。較佳地,該硫屬化合物包括SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等;該金屬鹵化物包括LiF、MgF2、CaF2、稀土金屬氟化物等;以及,該金屬氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
較佳地,於根據本發明之有機電致發光裝置中,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
摻雜劑之混合區域置於成對電極之至少一表面上。於此情況,該電子傳輸化合物係還原成陰離子,而使其變得更容易自該混合區域注入並傳輸電子至電致發光介質。再者,該電洞傳輸化合物係氧化成陽離子,而使其變得更容易自該混合區域注入並傳輸電洞至該電致發光介質。較佳地,該氧化性摻雜劑包括各種路易士酸(Lewis acid)以及接受者(acceptor)化合物;以及,該還原性摻雜劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬、及其混合物。還原性摻雜劑層可用作電荷產生層以製備具有兩層或更多層電致發光層並發射白光之電致發光裝置。
對於根據本發明之有機電致發光裝置之該等層的形成,可使用乾膜形成方法,如真空蒸發、濺射、電漿及離子鍍覆方法,或濕膜形成方法,如旋塗、浸塗、流動塗覆方法。
當使用濕膜形成方法時,可藉由將形成每一層之材料溶解或擴散於任何適宜之溶劑如乙醇、氯仿、四氫呋喃、二烷等中而形成薄膜。
後文中,將參照本發明之代表性化合物詳細解釋本發明之有機電致發光化合物、該化合物之製備方法、以及包含該化合物之裝置的發光特性:
化合物1-1之製備
將1-溴-2-硝基苯(50.0公克(g),0.247莫耳(mol))、萘-2-基硼酸(64.0g,0.37mol)、肆(三苯基膦)鈀(O)[Pd(PPh3)4](14.0g,0.012mol)、Na2CO3(81.0 g,0.60 mol)、甲苯(1000毫升(mL))、EtOH(500 mL)及H2O(200 mL)加入2000 mL圓底燒瓶中之後,於60℃攪拌該混合物12小時。於該反應完成之後,該反應混合物以乙酸乙酯萃取。所得有機層以MgSO4乾燥並過濾,於減壓下自該層移除溶劑。該有機層透過管柱分離以獲得白色固體化合物1-1(37 g,60%)。
化合物1-2之製備
將化合物1-1(37g,0.14mol)及亞磷酸三乙酯[P(OEt)3](180 mL)加入乾燥之250 mL圓底燒瓶中之後,將該反應混合物攪拌19小時。於反應完成後,蒸餾該反應混合物以移除P(OEt)3,並透過管柱分離以獲得黃色固體化合物1-2(17 g,52%)。
化合物1-3之製備
將化合物1-2(17.4g,1mol)、1-溴-4-碘苯(45.3 g,2mol)、CuI(7.63 g,0.5 mol)、乙二胺(EDA)(5.4 mL,2 mol)、K2CO3(51g,3 mol)及甲苯(400mL)加入2000 mL圓底燒瓶中後,該反應混合物於110℃攪拌12小時。於反應完成之後,該反應混合物以二氯甲烷萃取。所得有機層以MgSO4乾燥並過濾,於減壓下自該層移除溶劑。透過管柱分離該有機層以獲得白色固體化合物1-3(17.3 g,58%)。
化合物1-4之製備
將四氫呋喃(THF)(350 mL)及化合物1-3(17.3 g,1 mol)加入乾燥之3000 mL圓底燒瓶中之後,於N2氣氛下攪拌將該反應混合物並將其冷卻至-78℃。將正丁基鋰(n-BuLi)(28mL,2.5 M己烷溶液)緩慢滴加至該反應混合物中。於-78℃攪拌該反應混合物1小時,於-78℃將硼酸異丙酯硼[B(O-iPr)3](21mL,2mol)緩慢加入該反應混合物中,並於室溫將該反應混合物攪拌12小時。於反應完成之後,該反應混合物以乙酸乙酯萃取。所得有機層以MgSO4乾燥並過濾,於減壓下自該層移除溶劑。以二氯甲烷及己烷將該有機層再結晶以獲得白色固體化合物1-4(10 g,64%)。
化合物1-5之製備
將(1,1’-聯苯)-4-基硼酸(1.3 kg,6.5 mol)、1,3-二溴苯(2L,16.4 mol)、二氯雙(三苯基膦)鈀(II)[PdCl2(PPh3)2](138g,0.20 mol)、Na2CO3(1.74 kg,16.41 mol)、甲苯(12L)、EtOH(2L)及H2O(8L)加入20L圓底燒瓶中後,於120℃攪拌該反應混合物12小時。於反應完成之後,以乙酸乙酯萃取該反應混合物。所得有機層以MgSO4乾燥並過濾,於減壓下自該層移除溶劑。該有機層以乙酸乙酯再結晶以獲得白色固體化合物1-5(820 g,40%)。
化合物1-6之製備
將THF(16L)及化合物1-5(820 g,2.66 mol)加入乾燥之20 L圓底燒瓶中之後,於N2氣氛下攪拌該反應混合物並將其冷卻至-78℃。將N-BuLi(1.28L,2.5M己烷溶液)緩慢加入該反應混合物中。將該反應混合物於-78℃攪拌1小時,於-78℃將硼酸三甲酯[B(OMe)3](444 mL,3.99 mol)緩慢加入該反應混合物中,將該反應混合物於室溫攪拌12小時。於反應完成之後,以乙酸乙酯萃取該反應混合物。所得有機層以MgSO4乾燥並過濾,於減壓下自該層移除溶劑。使用己烷將該有機層再結晶以獲得白色固體化合物1-6(587 g,81%)。
化合物1-7之製備
將2,4-二氯嘧啶(478g,3.2 mol)、化合物1-6(587 g,2.14 mol)、Pd(PPh3)4(99 g,0.08 mol)、Na2CO3(567 g,5.35 mol)、甲苯(8L)、EtOH(2.7L)及H2O(2.7L)加入20 L圓底燒瓶中之後,於120℃將該反應混合物攪拌12小時。於反應完成之後,萃取該反應混合物並使用二甲基甲醯胺(DMF)再結晶以獲得化合物1-7(535 g,73%)。
化合物C-31之製備
將化合物1-7(9.8g,0.028mol)、化合物1-4(8g,0.024mol)、Pd(PPh3)4(1.37g,0.001mol)、K2CO3(9.83g,0.07 mol)、甲苯(120 mL)、EtOH(30mL)及H2O(36 mL)加入500mL圓底燒瓶中之後,該反應混合物於120℃攪拌12小時。於反應完成之後,將該反應混合物以己烷再結晶以獲得化合物C-31(4.5 g,26%)。
MS/FAB實測值為599.72;計算值為599.24。
裝置實施例1:使用根據本發明之有機電致發光化合物之
OLED裝置所製造
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、乙醇及蒸餾水洗滌有機發光二極體(OLED)裝置用之於玻璃基板(Samsung Corning,Republic of Korea)上之透明電極氧化銦錫(ITO)薄膜(15 Ω/sq),隨後儲存於異丙醇中。隨後,將該ITO基板裝配於真空氣相沉積設備之基板夾持器上。將N4,N4-雙(4-萘-2-基(N-苯基)胺基)苯基)-N1-(萘-2-基)-N1-苯基苯-1,4-二胺導入該真空氣相沉積設備之小室中,隨後將該設備之腔室內的壓力控制為10-6托(torr)。之後,將電流施加至該小室以蒸發上述導入之材料,從而於該ITO基板上形成厚度為60nm之電洞注入層。隨後,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設備之另一小室中,藉由將電流施加至該小室而蒸發該材料,從而於該電洞注入層上形成厚度為20nm之電洞傳輸層。該電洞注入層與電洞傳輸層形成之後,於其上真空沉積發光層。之後,將化合物C-31導入該真空氣相沉積設備之一小室中作為主體材料,將化合物D-1導入另一小室中作為摻雜劑。兩種材料係以不同速率蒸發,以該主體與摻雜劑之總量為基準,以該摻雜劑為15 wt%的摻雜量沉積,而於該電洞傳輸層上形成厚度為30nm之發光層。隨後,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8-羥基喹啉鋰(Liq)導入另一小室中。兩種材料係以相同速率蒸發並分別以50 wt%之摻雜量沉積,而於該發光層上形成厚度為30nm之電子傳輸層。隨後,於該電子傳輸層上沉積厚度為2nm之8-羥基喹啉鋰作為電子注入層之後,藉由另一真空氣相沉積設備於該電子注入層
上沉積厚度為150nm之鋁(Al)陰極。從而製造OLED裝置。用於製造該OLED裝置之全部材料係於使用前藉由在10-6托真空昇華而予以純化。
所製造之OLED裝置於3.3 V之驅動電壓下顯示具有亮度為1000燭光(cd)/平方公尺(m2)及電流密度為2.38毫安培(mA)/平方公分(cm2)之綠色發光。
裝置實施例2:使用根據本發明之有機電致發光化合物之OLED裝置的製造
以與裝置實施例1中相同之方式製造OLED裝置,但使用化合物C-31作為主體材料並使用化合物D-28作為摻雜劑。
所製造之OLED裝置於3.5 V之驅動電壓下顯示具有亮度為1000 cd/m2及電流密度為2.44 mA/cm2之橘色發光。
比較例1:使用傳統之電致發光化合物製造OLED裝置
以與裝置實施例1中相同之方式製造OLED裝置,但使用4,4'-N,N'-二咔唑-聯苯(CBP)作為主體材料且使用化合物D-1作為摻雜劑於該電洞傳輸層上沉積厚度為30nm之發光層,且藉由使用雙(2-甲基-8-羥基喹啉)(4-苯基苯酚)鋁(III)(Balq)沉積厚度為10nm之電洞阻擋層。
所製造之OLED裝置於4.9V之驅動電壓下顯示具有亮度為1,000 cd/m2及電流密度為2.86 mA/cm2之綠色發光。
比較例2:使用傳統之電致發光化合物製造OLED裝置
以與裝置實施例1中相同之方式製造OLED裝置,但使用4,4’-雙(咔唑-9-基)聯苯(CBP)作為主體材料且使用化合物D-28作為摻雜劑於該電洞傳輸層上沉積厚度為30 nm之發光層,且藉由
使用雙(2-甲基-8-羥基喹啉)(4-苯基苯酚)鋁(III)(Balq)沉積厚度為10nm之電洞阻擋層。
所製造之OLED裝置於4.6 V之驅動電壓下顯示具有亮度為1,000cd/m2及電流密度為3.04mA/cm2之橘色發光。
本發明之有機電致發光化合物比傳統材料具有較高的發光效率。此外,使用本發明之有機電致發光化合物作為主體材料的有機電致發光裝置由於低驅動電壓及改善之功率損耗而具有高功率效率。
Claims (7)
- 一種有機電致發光化合物,係藉由下式1表示:
- 如申請專利範圍第1項所述之有機電致發光化合物,其係選自下式2至4所組成之群組:
- 如申請專利範圍第1項所述之有機電致發光化合物,其中,式1之L1、L2、L3、R1、R2、R10、Ar1及R11至R17基中之該經取代之烷基、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、及經取代之雜環烷基的取代基,係各自獨立為選自下列所組成群組的至少一者:氘;鹵素;(C1-C30)烷基;鹵(C1-C30)烷基;(C1-C30)烷氧基;(C6-C30)芳氧基;(C6-C30)芳基;3至30員雜芳基;經(C6-C30)芳基取代之3至30員雜芳基;經(C1-C30)烷基及(C6-C30)芳基取代之3至30員雜芳基;(C3-C30)環烷基;5至7員雜環烷基;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;(C1-C30)烷硫基;(C6-C30)芳硫基;N-咔唑基;單或二(C1-C30)烷基胺基;單或二(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;以及羥基。
- 如申請專利範圍第1項所述之有機電致發光化合物,其中,L1係單鍵或(C6-C30)伸芳基;以及,係選自下列基團:
- 如申請專利範圍第1項所述之有機電致發光化合物,其中,L2係表示伸苯基、伸吡啶基、伸茀基、伸咔唑基、伸二苯并呋喃基或伸二苯并噻吩基;L3係表示伸苯基、伸聯苯基、伸聯三苯基、伸萘基、伸吡啶基、伸嘧啶基、伸茀基、伸二苯并呋喃基、伸二苯并噻吩基、伸咔唑基、伸5H-吡啶并[3,2-b]吲哚基或伸5H-茚并[1,2-b]吡啶基;Ar1係表示氫、鹵素、(C1-C30)烷基、(C3-C30)環烷基、(C6-C30)芳基、3至30員雜芳基或-SiR13R14R15;R10係表示氫或(C6-C30)芳基;R1與R2係各自獨立表示氫、鹵素、(C1-C30)烷基、(C6-C30)芳基或3至30員雜芳基;L2中之該伸苯基、伸吡啶基、伸茀基、伸咔唑基、伸二苯并呋喃基及伸二苯并噻吩基,L3中之該伸苯基、伸聯苯基、伸聯三苯基、伸萘基、伸吡啶基、伸嘧啶基、伸茀基、伸二苯并呋喃基、伸二苯并噻吩基、伸咔唑基、伸5H-吡啶并[3,2-b]吲哚基及伸5H-茚并[1,2-b]吡啶基,Ar1中之該烷基、環烷基、芳基及雜芳基,R10中之該芳基,以及R1與R2中之該烷基、芳基及雜芳基,可各自獨立進一步經選自下列所組成群組之至少一者取代:氘、鹵素、(C1-C30)烷基、鹵(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3至30員雜芳基、 經(C6-C30)芳基取代之3至30員雜芳基、(C1-C30)烷硫基、(C6-C30)芳硫基、(C6-C30)芳基(C1-C30)烷基、及(C1-C30)烷基(C6-C30)芳基。
- 如申請專利範圍第1項所述之有機電致發光化合物,其中,式1表示之化合物係選自下列所組成之群組:
- 一種有機電致發光裝置,係包含如申請專利範圍第1項所述之有機電致發光化合物。
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JP6264877B2 (ja) * | 2012-12-28 | 2018-01-24 | 東ソー株式会社 | 1,2,4−トリス置換ベンゼン化合物、その製造方法、および有機電界発光素子 |
JP6542192B2 (ja) | 2013-03-14 | 2019-07-10 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドThe Brigham and Women’s Hospital, Inc. | Bmp阻害剤およびその使用方法 |
EP3122355A4 (en) * | 2014-03-26 | 2017-08-09 | The Brigham and Women's Hospital, Inc. | Compositions and methods for inhibiting bmp |
US10513521B2 (en) | 2014-07-15 | 2019-12-24 | The Brigham And Women's Hospital, Inc. | Compositions and methods for inhibiting BMP |
KR101864473B1 (ko) * | 2014-09-22 | 2018-06-04 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 발광 소자 |
EP3201187A4 (en) * | 2014-10-01 | 2018-04-11 | The Brigham and Women's Hospital, Inc. | Compositions and methods for inhibiting bmp |
KR101709379B1 (ko) * | 2014-10-01 | 2017-02-23 | 주식회사 엘지화학 | 유기 발광 소자 |
US11192884B2 (en) | 2017-03-27 | 2021-12-07 | Lg Chem, Ltd. | Heterocyclic compound and organic light-emitting device comprising same |
CN111051282B (zh) * | 2017-11-16 | 2023-05-09 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN109912564B (zh) * | 2017-12-13 | 2022-08-16 | 江苏三月科技股份有限公司 | 一种以氰基氮杂苯为核心的化合物及其在oled器件上的应用 |
CN109912565A (zh) * | 2017-12-13 | 2019-06-21 | 江苏三月光电科技有限公司 | 一种以氰基氮杂苯为核心的化合物及其在有机电致发光器件中的应用 |
CN113166126A (zh) * | 2019-02-01 | 2021-07-23 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
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WO2020159334A1 (ko) * | 2019-02-01 | 2020-08-06 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN113195478A (zh) * | 2019-02-01 | 2021-07-30 | 株式会社Lg化学 | 化合物及包含其的有机发光二极管 |
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US20140316136A1 (en) | 2014-10-23 |
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CN104066728A (zh) | 2014-09-24 |
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