TW201326360A - 用於有機電致發光裝置之材料 - Google Patents
用於有機電致發光裝置之材料 Download PDFInfo
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- TW201326360A TW201326360A TW101134157A TW101134157A TW201326360A TW 201326360 A TW201326360 A TW 201326360A TW 101134157 A TW101134157 A TW 101134157A TW 101134157 A TW101134157 A TW 101134157A TW 201326360 A TW201326360 A TW 201326360A
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- 239000000463 material Substances 0.000 title claims description 25
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- 238000000034 method Methods 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 67
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- -1 NR 2 Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 6
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- 238000007740 vapor deposition Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- 229960005544 indolocarbazole Drugs 0.000 description 3
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
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- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 239000008346 aqueous phase Substances 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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Abstract
本發明描述咔唑衍生物,特別是在有機電致發光裝置中作為三重態基質材料者。本發明另關於製造本發明之化合物的方法及包含彼之電子裝置。
Description
本發明描述咔唑衍生物,特別是在有機電致發光裝置中作為三重態基質材料者。本發明另關於製造本發明之化合物的方法及包含這些化合物之電子裝置。
有機半導體作為官能性材料的有機電致發光裝置(OLED)構造述於,例如,US 4539507、US 5151629、EP 0676461和WO 98/27136。所用發光材料常為發射磷光而非螢光的有機金屬錯合物。因量子力學的因素,使用有機金屬化合物作為磷光發光體,能量和功率效率提高至四倍是可行的。通常,對於在例如效率、操作電壓和壽命方面之改良的OLED(特別是具有三重態發光(磷光)的OLED)。
磷光OLED的性質不僅由所用的三重態發光體決定。特別地,所用其他材料(例如基質材料)亦特別重要。改良這些材料亦可明顯改良OLED性質。
根據先前的技術,尤其使用吲哚並咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)或茚並咔唑衍生物(例如根據WO 2010/136109或WO 2011/000455),特別是經缺電子的雜芳族化合物(如三)取代者,作為磷光發光體的基質材料。此外,使用雙二苯并呋喃衍生物(例如根據EP 2301926)作為磷光發光體的基質材料。但
是,對於改良這些基質材料之使用,特別是關於效率、壽命和操作電壓方面,仍有需求。
本發明的目的係提供適合用於螢光或特別適用於磷光OLED,特別是作為基質材料的化合物。特別地,本發明之目的係提供亦適合用於綠色磷光OLED(若必要時亦適用於藍色磷光OLED)且導致良好效率、長壽命和低操作電壓的基質材料。特別地,此基質材料之性質對於有機電致發光裝置之壽命和效率的影響顯著。
令人訝異地,已發現相較於先前技術,包含下列式(1)化合物的電致發光裝置獲得改良,特別是在作為磷光摻雜物的基質材料方面。
因此,本發明係關於下列式(1)化合物,
其中下列定義適用於所用符號:Y 於每次出現時相同或不同地為CR或N;X 選自C(R1)2、O、S、PR1、P(=O)R1或BR1;R,R1於每次出現時相同或不相同地為H、D、F、Cl、Br、I、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)Ar2、
S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、OSO2R2、具1至40個C原子的直鏈烷基、烷氧基或烷硫基或具3至40個C原子的支鏈或環狀烷基、烷氧基或烷硫基(各者可經一或多個R2基團取代,其中一或多個不相鄰的CH2基團可被R2C=CR2、C≡C、Si(R2)2、C=O、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2所代替且一或多個H原子可被D、F、Cl、Br、I、CN或NO2所代替)、或具5至60個芳環原子的芳環或雜芳環系統(其各者可經一或多個R2基團取代)、或具5至40個芳環原子的芳氧基或雜芳氧基(其各者可經一或多個R2基團取代)、或具5至40個芳環原子的芳烷基或雜芳烷基(其各者可經一或多個R2基團取代)、或這些系統之組合;此處的二或更多個取代基R和與其鍵結的原子一起,或兩個取代基R1和與其鍵結的原子一起,可彼此形成單-或多環狀脂族或芳族環系統;Ar 於每次出現時相同或不同地為具5至40個芳環原子的芳環或雜芳環,其可經一或多個R3基團取代;R2 於每次出現時相同或不相同地為H、D、F、Cl、Br、I、N(R3)2、N(Ar)2、C(=O)Ar、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR3=CR3Ar、CN、NO2、
Si(R3)3、B(OR3)2、OSO2R3、具1至40個C原子的直鏈烷基、烷氧基或烷硫基或具3至40個C原子的支鏈或環狀烷基、烷氧基或烷硫基(各者可經一或多個R3基團取代,其中一或多個不相鄰的CH2基團可被R3C=CR3、C≡C、Si(R3)2、C=O、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S或CONR3所代替且一或多個H原子可被D、F、Cl、Br、I、CN或NO2所代替)、或具5至60個芳環原子的芳環或雜芳環系統(其各者可經一或多個R3基團取代)、或具5至40個芳環原子的芳氧基或雜芳氧基(其各者可經一或多個R3基團取代)、或具5至40個芳環原子的芳烷基或雜芳烷基(其各者可經一或多個R3基團取代),或這些系統之組合;R3 於每次出現時相同或不同地為H、D或具1至20個C原子的脂族烴基或具5至40個環原子的芳基或雜芳基或這些基團之組合;先決條件為,若基團R、R1、R2、R3、Ar或Ar1中之一或多者含有不同於式(2)、(3)或(4)的雜芳基,則這些不是缺電子的雜芳基;其特徵在於存在有至少一個在每次出現時相同或不同地以下式(2)的基團表示之R基團,
其中虛鍵代表式(2)基團的鏈結,R2具有上述定義,此外:Q 若式(2)經由此基團鏈結至Ar1或分子的餘者,則是C;或在其他的情況中,各者相同或不同地為CR2或N;Z 是NR2或S;Ar1 是具5至40個芳環原子的二價芳環或雜芳環,其可經一或多個R2基團取代;p 是0或1;和/或存在有至少一個以下式(3)或(4)的基團表示的R1基團,
其中虛鍵代表式(3)或(4)基團的鏈結,R2、Ar1、Q和p具有上述定義,此外:W 是NR2、O或S。
本發明中,該芳基含有6至60 C原子;該雜芳基含有2至60 C原子和至少一個雜原子,先決條件為C原子和雜原子的和係至少5。該雜原子較佳選自N、O和/或S。此處的芳基或雜芳基是指簡單的芳環(即,苯)、或簡單的雜芳環(例如噻吩等)、或縮合(稠合)的芳基或雜芳基(例如萘、蒽、菲、二苯并呋喃)等。彼此藉單鍵連接的芳環(如聯苯基)不同於被稱為芳基或雜芳基者,而是被稱為芳環系統。
本發明中,芳環系統的環系統中含有6至80C原子。本發明中的雜芳環系統的環系統含有2至60C原子和至少一個雜原子,先決條件為C原子和雜原子的和係至少5。該雜原子較佳地選自N、O和/或S。本發明中,芳環或雜芳環不一定是指僅含有芳基或雜芳基的系統,而是,此外,多個芳基或雜芳基可以被非芳族單元(較佳低於10%的原子不是H),例如C、N或O原子所中斷的系統。因此,例如,例如茀、9,9’-螺二茀、9,9-二芳基茀、三芳基胺、二芳基醚和二苯乙烯等系統亦可以在本發明中被視為芳環系統,且二或更多個芳基以,例如,短烷基連接的系統亦是。此外,藉單鍵彼此鏈接的芳環,例如聯苯基,於此申請案中亦被視為芳環系統。
本發明中,缺電子的雜環基定義為具有至少兩個雜原子的5員環雜芳基(如咪唑、唑、二唑等)或具有至
少一個雜原子的6員環雜芳基,例如吡啶、嘧啶、吡、三等)。此外,6員環芳基或6員環雜芳基亦可稠合於這些基團上,例如,苯并咪唑或喹啉。
本發明中,脂族烴基或烷基或烯基或炔基基本上含有1至40或1至20 C原子,且其中個別的H原子或CH2基團可被上述基團所取代,較佳地是指甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、2-甲基丁基、正戊基、二級戊基、環戊基、正己基、環己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。具有1至40 C原子的烷氧基較佳地指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、正戊氧基、二級戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基或2,2,2-三氟乙氧基。具1至40 C原子的烷硫基特別是指甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基、三級丁硫基、正戊硫基、二級戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊
烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。通常,根據本發明之烷基、烯基、炔基、烷氧基或烷硫基可為直鏈、支鏈或環狀,其中一或多個不相鄰的CH2基團可經上述基團代替;此外,一或多個H原子亦可以D、F、Cl、Br、I、CN或NO2,較佳地F、Cl或CN,更佳地F或CN,特別佳地CN,代替。
具有5-80個芳環原子的芳或雜芳環系統(其各者可經上述基團取代且可經由芳或雜芳基上的任何所欲位置鏈接)特別是指衍生自苯、萘、蒽、苯并蒽(benzanthracene)、菲、苯并菲、芘(pyrene)、(chrysnen)、苝(perylene)、丙烯合茀(fluoranthene)、稠四苯(naphthacene)、稠五苯(phntacene)、苯并苝(benzopyrene)、聯苯、伸聯苯、聯三苯(terphenyl)、伸聯三苯(triphenylene)、芴、螺二芴、二氫菲、二氫芘、四氫芘、順-或反-茚并芴(indenofluorene)、順式-或反式-茚并咔唑(indenocarbazole)、順式-或反式-茚并咔唑(indolocarbazole)、參茚并苯(truxene)、異參茚并苯(isotruxene)、螺參茚并苯(spirotruxene)、螺異參茚并苯(spiroisotruxene)、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶(phenanthridine)、苯并-5,6-喹啉、苯并-6,7-喹啉、
苯并-7,8-喹啉、吩噻、吩、吡唑、吲唑(indazole)、咪唑、苯并咪唑、萘咪唑、菲咪唑(phenanthrimidazole)、吡啶咪唑、哌咪唑、喹啉咪唑、唑、苯并唑、萘唑、蒽唑、菲唑、異唑、1,2-噻唑、1,3-噻唑、苯并噻唑、吡、六氮雜苯井菲(hexaazatriphenylene)、苯并吡、嘧啶、苯并嘧啶、喹啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜芘、哌、吩、吩、吩噻、氟茹(fluorubine)、萘啶(naphthyridine)、氮咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、喋啶(pteridine)、吲哚(indolizine)和苯并噻二唑的基團或自這些系統的組合衍生的基團。這些基團各者經上述基團取代。
本發明的較佳具體實施例中,鍵結至氮原子的基團R1代表具5至60個芳環原子(較佳具有6至24個芳環原子)且亦可被一或多個基團R2取代的芳環或雜芳環系統,或是代表上述式(3)或(4)的基團。
根據本發明之化合物之其他較佳的具體實施例中,X代表C(R1)2。此情況中,鍵結至此碳原子的基團R1於每次出現時相同或不同地代表具1至10 C原子的直鏈烷基
或具3至10 C原子的支鏈或環狀烷基,其中各者可經一或多個基團R2取代,其中一或多個不相鄰的CH2基團可以R2C=CR2、C≡C、Si(R2)2、C=O、O、S或CONR2代替且其中一或多個H原子可以D、F或CN代替,或代表具有5至60(較佳地具有5至24)個芳族環原子的芳族環或雜芳族環系統(其亦可經一或多個基團R2取代)。鍵結至相同碳原子的這兩個基團R1亦可彼此形成脂環或芳環系統。
本發明之另一較佳的具體實施例中,每個環最多有一個基團Y代表N而其餘的基團Y於每次出現時相同或不同地代表CR。Y特別佳地於每次出現時相同或不同地代表CR。
因此,式(1)化合物的較佳具體實施例係下列式(5)化合物,
其中所用符號具有上述定義,且如上述者,式(2)至(4)基團中之至少一者存在。
式(5)結構之特別佳的具體實施例係以下式(5a)的結構,
其中所用符號具有上述定義。
特別佳者係以下式(6)、(7)和(8)的結構,
極特別佳者係以下式(6b)、(7b)和(8b)的化合物,
鍵結至式(6)或(6a)或(6b)中之相同C原子的兩個基團R1亦可與彼等所鍵結的碳原子一起形成脂環、芳環或雜芳環系統,例如,茀,並因此而整體形成螺系統。
特別佳者係茚并咔唑衍生物,即,式(6)或(6a)或(6b)化合物。
如上述者,根據本發明之化合物含有至少一個式(2)的基團R和/或至少一個式(3)或(4)的基團R1。
本發明的另一較佳具體實施例中,式(1)化合物含有一、二或三個如式(2)至(4)中之一或多者所示的基團,特別佳地,含有一或兩個如式(2)至(4)中之一或
多者所示的基團,極特別佳地恰好含有一個如式(2)至(4)中之一所示的基團。
若根據本發明之化合物含有式(3)或(4)的基團,則此式(3)或(4)的基團較佳地鍵結至化合物的氮原子,即較佳地非鍵結至基團X。
以下描述式(2)至(4)的基團之較佳具體實施例。
本發明的較佳具體實施例中,若基團Ar1或分子的其餘者鏈接至基團Q,則每個式(2)至(4)的基團中之每個環最多一個的該基團Q代表N,而其餘的基團Q於每次出現時相同或不同地代表CR2或C。本發明之特別佳的具體實施例中,若式(2)或(3)的基團經由基團Q鏈結至Ar1或至分子的其餘者,則該Q代表C,而其餘的基團Q相同或不同地代表CR2,或式(4)中之所有的Q代表CR2。
式(2)至(4)的較佳具體實施例為以下式(2a)至(4a)的基團,
式(2a)至(4a)之特別佳的具體實施例係式(2b)、(2c)、(2d)、(3b)、(3c)、(3d)和(4b)的結構,
上述結構中,Z和W較佳地代表NR2,其中R2代表根據上述定義的芳環或雜芳環系統,其亦可經上述基團取
代。
此外,鍵結至上述結構中之碳原子的基團R2較佳地代表H。
本發明的其他較佳具體實施例中,標號p=0。
特別佳者係式(2b)、(3b)和(4b)的結構。
若基團Ar1存在,則其較佳地代表具有6至24個芳環原子的二價芳環或雜芳環系統,其較佳地不含有具有超過兩個六員環彼此直接稠合之稠合的芳基或雜芳基。較佳的基團Ar1選自鄰-、間-或對-苯基、鄰-、間-或對-聯苯基、聯三苯基,特別係鄰-、間-或對-聯三苯基、聯四苯基,特別是鄰-、間-或對-聯四苯基、茀、呋喃、苯并呋喃、二苯并呋喃、二苯并噻吩、吡咯、吲哚或咔唑。這些基團可經一或多個基團R2取代,但較佳地係未經取代。若Ar1代表茀,則其較佳地在9-位置經兩個各具1至10 C原子的烷基取代。
必要時,本發明的上述具體實施例可以彼此合併。特別地,必要時,上述通式(1)或較佳的具體實施例可以與式(2)至(4)或對應的較佳具體實施例及與其他符號和標號的上述較佳具體實施例合併。本發明的較佳具體實施例中,上述較佳者同時發生。因此,特別地,可以令式(5)、(5a)、(6)、(6a)、(6b)、(7)、(7a)、(7b)、(8)、(8a)和(8b)各者與(2a)、(2b)、(2c)、(2d)、(3a)、(3b)、(3c)、(3d)、(4a)和(4b)各者合併。
若不等於H或D且不代表式(2)或(3)的基團之一或多個基團R存在於通式(1)化合物中,則這些基團較佳地選自N(Ar)2,較佳地為二苯胺基、經取代或未經取代的芳基胺、具1至20 C原子(較佳為1至10 C原子)的直鏈烷基、具3至20 C原子(較佳為1至10 C原子)的支鏈烷基或具5至40個芳環原子的芳環或雜芳環系統(其可經一或多個基團R2取代)。此芳環或雜芳環系統較佳地選自經取代或未經取代的苯基、萘基、噻吩、二苯并噻吩、二苯并呋喃、三苯基胺或這些基團之組合,其各者可經一或多個基團R2取代。
本發明的另一較佳具體實施例中,式(1)中的X代表C(R1)2,其中基團R1彼此形成環系統,而形成以下式(9)或(10)的結構:
其中所用符號具有上述定義,而Y較佳地於每次出現時相同或不同地代表CR1。
本發明的又另一較佳具體實施例中,在式(1)之基本結構上的兩個相鄰的基團R形成芳環系統,以形成以下式(11)或(12)的結構:
其中所用符號具有上述定義,而Y較佳地於每次出現時相同或不同地代表CR1。
上述相同較佳者用於式(9)至(12)的化合物。
根據本發明之化合物的例子係如下列結構式所示。
根據本發明之化合物可以較佳地藉嫻於此技術者已知的合成步驟(例如,溴化反應、Suzuki偶合、Ullmann偶合、Hartwig-Buchwald偶合等)製造。式(2)至(4)中之一者所示的單元較佳地藉Suzuki偶合、Ullmann偶合或Hartwig-Buchwald偶合,以橋中的O或S引至茚并咔唑基礎結構或對應的衍生物上。
因此,本發明另關於根據本發明之化合物之製法,其特徵在於式(2)、(3)或(4)的基團藉Suzuki偶合、Ullmann偶合或藉Hartwig-Buchwald偶合引入。
本發明另關於包含至少一種根據本發明之化合物和至少一種其他化合物之混合物。若使用根據本發明之化合物作為基質材料,則此其他化合物可為,例如,螢光或磷光
摻合物,特別是磷光摻雜物。下文描述適當的摻雜物和有機電致發光裝置及亦為根據本發明之混合物之較佳者。
為了自溶液或液相加工,例如藉旋轉塗覆或藉印刷法,須要根據本發明之化合物或混合物的溶液或調合物。可以較佳地使用二或更多種溶劑之混合物。適當且較佳的溶劑為,例如,甲苯、茴香醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、二甲基茴香醚、三甲苯、萘滿、藜蘆素(veratrol)、THF、甲基-THF、THP、氯苯、二烷或這些溶劑的混合物。
因此,本發明另關於調合物,特別是溶液、懸浮液或微乳液,其包含至少一種根據本發明之化合物或混合物及一或多種溶劑,特別是有機溶劑。此類型的溶液可藉嫻於此技術之人士已知的方法製造並述於,例如,WO 2002/072714、WO 2003/019694和其中所列文獻。
根據本發明之化合物或混合物適用於電子裝置。此處的電子裝置是指包含至少一層包含至少一種有機化合物之裝置。但是,此處的組件亦可包含無機材料或完全由無機材料堆積的層。
因此,本發明另關於根據本發明之化合物或混合物於電子裝置(特別是有機電致發光裝置)之用途。
此外,本發明另關於包含至少一種上述根據本發明之化合物或混合物的電子裝置。上述關於化合物之較佳者亦施於電子裝置。
此電子裝置較佳地選自有機電致發光裝置(OLED、
PLED)、有機積體電路(O-IC)、有機場效電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、有機染料敏化的太陽能電池、有機光學偵測器、有機光受體、有機場淬冷裝置(O-FQD)、發光電化學電池(LEC)、有機雷射二極體(O-雷射)和“有機電漿發射裝置(organic plasmon emitting device)”(D.M.Koller等人,Nature Photonics 2008,1-4),較佳地為有機電致發光裝置(OLED,PLED),特別是磷光OLED。
有機電致發光裝置包含陰極、陽極和至少一個發光層。除了這些層以外,其亦可包含其他層,例如,在各情況中,一或多個電洞注入層、電洞傳遞層、電洞阻斷層、電子傳遞層、電子注入層、激子阻斷層、電子阻斷層和/或電荷產生層。亦可將具有,例如,激子阻斷作用,的中間層引至兩個發光層之間。但是,應指出這些層的各者不一定存在。此處的有機電致發光裝置可包含一個發光層或多個發光層。若有多個發光層存在,這些較佳地共具有多個發光峰介於380奈米和750奈米之間,造成整體為白光,即,各種能夠發出螢光或磷光的發光化合物用於發光層。特別佳者為具有三個發光層的系統,其中這三個層發出藍、綠和橘或紅光(其基本構造見於,例如,WO 2005/011013)。這些可為螢光或磷光發光層或螢光和磷光發光層彼此合併的混合系統。
根據本發明之具體實施例,上述根據本發明之化合物
可用於各層中,此取決於確切的結構。較佳者係有機電致發光裝置包含式(1)或根據較佳具體實施例之化合物作為螢光或磷光發光體(特別是用於磷光發光體)的基質材料和/或用於電子傳遞層和/或電子阻斷或激子阻斷層和/或電洞傳遞層,此取決於確實的取代作用。上述較佳具體實施例亦用於有機電子裝置中之材料之用途。
本發明之具體實施例中,式(1)或根據較佳具體實施例之化合物作為發光層中之螢光或磷光化合物(特別是磷光化合物)的基質材料。此處的有機電致發光裝置可包含一個發光層或多個發光層,其中至少一個發光層包含至少一種根據本發明之化合物作為基質材料。
若式(1)或根據較佳具體實施例之化合物作為發光層中之發光化合物的基質材料,則其較佳地與一或多種磷光材料併用(三重態發光體)。本發明中之磷光是指來自自旋多重性(spin multiplicity)>1的激發態,特別是激發的三重態,的光。就此申請案之目的,所有的發光過渡金屬錯合物和發光鑭系錯合物(特別是所有的銥、鉑和銅錯合物)被視為磷光化合物。
以包含發光體和基質材料之整體混合物計,包含式(1)或根據較佳具體實施例的化合物和發光化合物之混合物包含介於99和1體積%之間,較佳地介於98和10體積%之間,特別佳地介於97和60體積%之間,特別介於95和80體積%之間,的式(1)或根據較佳具體實施例之化合物。據此,以包含發光物和基質材料之整體混合物
計,混合物包含介於1和99體積%之間,較佳地介於2和90體積%之間,特別佳地介於3和40體積%之間,特別介於5和20體積%之間,的發光體。
本發明的其他較佳實施例係式(1)或根據較佳具體實施例之化合物作為磷光發光體的基質材料與其他基質材料合併之用途。能夠與式(1)或根據較佳具體實施例之化合物併用之特別適合的基質材料為芳族酮、芳族氧化膦或芳族亞碸或碸(例如根據WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680)、三芳基胺、咔唑衍生物(例如CBP(N,N-雙咔唑聯苯)或揭示於WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527或WO 2008/086851的咔唑衍生物)、吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚并咔唑衍生物(例如根據WO 2010/136109和WO 2011/000455)、氮咔唑衍生物(例如根據EP 1617710、EP 1617711、EP 1731584、JP 2005/347160)、偶極基質材料(例如根據WO 2007/137725)、矽烷(例如根據WO 2005/111172)、氮硼雜環戊烯(azaborole)或硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據WO 2010/015306、WO 2007/063754或WO 2008/056746)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮矽雜環戊烯(diazasilole)或四氮矽雜環戊烯(tetraazasilole)衍生物(例如根據WO 2010/054729)、二氮雜磷雜環戊二烯(diazaphosphole)衍生物(例如根據WO 2010/054730)、橋
連的咔唑衍生物(例如根據US 2009/0136779、WO 2010/050778、WO 2011/042107、WO 2011/088877或根據未發佈的申請案EP 11003232.3)、苯并菲(triphenylene)衍生物(例如根據WO 2012/048781)或內醯胺(例如根據WO 2011/116865或WO 2011/137951)。發光波長短於實際發光體的其他磷光發光體亦存在於混合物中作為共基質(co-host)。
適當的磷光化合物(=三重態發光體)係,特別地,於適當激發下發光(較佳在可見光範圍)且所含的至少一個原子之原子數大於20(較佳大於38且低於84,特別佳地大於56且低於80,特別是具有此原子數的金屬)的化合物。所用磷光發光體較佳地係含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪,特別是含有銥或鉑的化合物。用於本發明之目的,將所有含有上述金屬的發光化合物視為磷光化合物。
上述發光體的例子揭示於申請案WO 00/70655,WO 2001/41512,WO 2002/02714,WO 2002/15645,EP 1191613,EP 1191612,EP 1191614,WO 05/033244,WO 05/019373,US 2005/0258742,WO 2009/146770,WO 2010/015307,WO 2010/031485,WO 2010/054731,WO 2010/054728,WO 2010/086089,WO 2010/099852,WO 2010/102709,WO 2011/032626,WO 2011/066898,WO 2011/157339或WO 2012/007086。通常,熟悉此項技術的人士均能夠進一步將先前技術中用於磷光OLED及嫻於有機電致發光領域之人士已知的所有磷光錯合物用作磷光錯
合物而無須創新步驟。
本發明的其他具體實施例中,根據本發明之有機電致發光裝置不包含分離的電洞注入層和/或電洞傳遞層和/或電洞阻斷層和/或電子傳遞層,即,發光層直接與電洞注入層或陽極相鄰,和/或發光層直接與電子傳遞層或電子注入層或陰極相鄰,例如,如WO 2005/053051中所述者。因此可以使用金屬錯合物(其與發光層中的金屬錯合物相同或類似)作為直接與發光層相鄰的電洞傳遞或電洞注入材料,例如,如WO 2009/030981中所述者。
另可能將根據本發明之化合物用於電洞傳遞層或電洞注入層或激子-或電子-阻斷層。
根據本發明之有機電致發光裝置的其他層中,可以使用根據先前技術中一般使用之所有材料。嫻於此技術者將因此而能夠無須創新步驟地令已知用於有機電致發光裝置的所有材料與根據本發明或根據較佳具體實施例的式(1)化合物併用。
較佳者另為有機電致發光裝置,其特徵在於一或多層藉昇華法施用(其中材料在真空昇華單元中於初壓力低於10-5毫巴,較佳地低於10-6毫巴下蒸氣沉積)。但是,初壓力亦可較低或較高,例如低於10-7毫巴。
較佳者亦為有機電致發光裝置,其特徵在於一或多層藉OVPD(有機蒸汽相沈沉積)法或藉載氣昇華之助施用(其中材料於介於10-5毫巴和1巴之間的壓力施用)。此方法的特殊情況為OVJP(有機蒸氣噴注印刷)法,其中
材料經由噴嘴直接施用並因此而結構化(例如M.S.Arnold等人,Appl.Phys.Lett. 2008, 92,053301)。
較佳者另為有機電致發光裝置,其特徵在於一或多層自溶液製得,如藉旋轉塗覆、或藉任何所欲的印刷法(例如,噴墨印刷、LITI(光誘發的熱成像、熱轉移印刷)、網版印刷、快乾印刷、套版印刷、噴嘴印刷(nozzle printing))。為用於此目的,可溶化合物(其可藉適當取代反應得到)是必須的。
這些方法亦特別適合於低聚物、樹枝狀聚合物和聚合物。
亦可能為混合法,其中,一或多層自溶液施用且一或多層藉蒸氣沉積施用。因此,可以自溶液施用發光層及藉蒸氣沉積施用電子傳遞層。
這些方法為嫻於此技術者一般已知者且可由彼等無須創新的步驟地施用於包含根據本發明之化合物的有機電致發光裝置。
關於有機電致發光裝置之使用,根據本發明之化合物具有一或多個如下之令人訝異之優於先前技術的優點:
1.相較於根據先前技術的系統,相對應的裝置的功率效率較高。
2.相較於根據先前技術的系統,相對應的裝置的安定性效率較高,此特別由明顯較長的壽命證實。
3.根據本發明之有機電致發光裝置具有降低之操作電壓。
4.若根據本發明之化合物作為磷光發光體的基質材料,則其可僅以低於10體積%的範圍內之低發光體濃度達到極佳結果。
5.根據本發明之化合物具有極佳的熱安定性。
現將藉以下實例更詳細地說明本發明,但不欲為其所限。
除非特別聲明,否則在保護性氣氛中於無水溶劑中進行以下合成。溶劑和試劑可購自,例如,Sigma-ALDRICH或ABCR。各實例中,文獻已知的化合物亦標出其對應的CAS編號。
A部分:先質之合成
S1:3-溴-9-[1,1’,3’,1”]聯三苯-5’-基-9H-咔唑
10克(41毫莫耳)3-溴-9H-咔唑(CAS 86-74-8)和16克(45毫莫耳,1.1當量)5’-碘-[1,1’,3’,1”]聯三苯與51克(270毫莫耳,6.6當量)銅元素、115克(540毫莫耳,13當量)碳酸鉀和0.52克(4.5毫莫耳,0.11當量)
18-冠醚-6溶於500毫升對-二甲苯中並迴流加熱。反應完全之後,混合物以水萃取3次,有機相經硫酸鈉乾燥,在真空中移除溶劑,所得固體藉管柱層析法(乙酸乙酯/庚烷)純化,得到17克(36毫莫耳,53%)產物。
藉類似方式製得下列合成物:
S5:溴-9-[1,1’,3’,1”]-聯三苯-5’-基-3-(4,4,5,5-四甲基-1,3,2-二氧硼雜環戊烷-2-基)9H-咔唑
20克(42毫莫耳)3-溴-9-[1,1’,3’,1”]聯三苯-5’-基-9H-咔唑S1、13克(50毫莫耳,1.2當量)雙(頻哪醇基)二硼烷(CAS 73183-34-4)和12克(130毫莫耳,3當量)醋酸鉀先引至300毫升1,4-二烷中並以氮脫氣30分鐘。之後添加470毫克(0.84毫莫耳,0.02當量)1,1’-雙(二苯基膦基)二茂鐵和190毫克(0.84毫莫耳,0.02當量)醋酸鈀(II)並加熱至內部溫度為100℃。反應完全時,乙酸乙酯加至該批料中,混合物以水萃取三次。有機相經蒸發,硼酸酯自庚烷沉澱出來。以乙腈再結晶得到20克(38毫莫耳,91%)產物。
藉類似方式製得下列合成物:
B部分:根據本發明之化合物之合成
B1:12,12-二甲基-10-(9-[1,1’,3’,1”]聯三苯-5’-基-9H-咔唑-3-基)-10,12-二氫-10-氮雜茚并[2,1-b]茀
7.6克(33毫莫耳)12,12-二甲基-10,12-二氫-10-氮雜茚并[2,1-b]茀(WO 2010-136109)、17克(36毫莫耳,1.1當量)3-溴-9-[1,1’,3’,1”]聯三苯-5’-基-9H-咔唑S1和12.1克(12毫莫耳,0.36當量)碘化銅(I)與150克(706毫莫耳,4當量)磷酸鉀懸浮於1升1,4-二烷中。此反應混合物脫氣30分鐘,於保護性氣體下添加17.6毫升(147毫莫耳,0.83當量)反式-環己胺。此批料於迴流下加熱12小時,及,當反應完全時,添加二氯甲烷。沉澱的固體藉抽氣濾出,溶於甲苯中並濾經矽膠。在真空中移除溶劑之後,殘渣以甲苯/庚烷再結晶數次並於最後昇華,得到17.6克(33.5毫莫耳,57%)無色固體,其HPLC純度>99.9%。
以類似於B1的方式製造以下化合物:
B28:12,12-二甲基-10-苯基-7-(9-[1,1’,3’,1”]聯三苯-5’-基-9H-咔唑-3-基)-10,12-二氫-10-氮雜茚并[2,1-b]茀
20克(38毫莫耳)9-[1,1’,3’,1”]-聯三苯-5’-基-3-(4,4,5,5-四甲基-1,3,2-二氧硼雜環戊烷-2-基)-9H-咔唑S5和17克(38毫莫耳,1當量)7-溴-12,12-二甲基-10-苯基-10,12-二氫-10-氮雜茚并[2,1-b]茀(WO 2010/136109)先引至250毫升丙酮中,添加62毫升(84毫莫耳,2.2當量)氫氧化四乙銨(20%水溶液)。此反應混合物以氮脫氣30分鐘,之後添加0.88克(0.76毫莫耳,0.02當量)肆(三苯基膦)鈀(0),此混合物於50℃攪拌隔夜。沉澱的固體藉抽氣濾出並藉熱萃取而純化,以庚烷/甲苯重複再結晶並於最後昇華,得到14克(19毫莫耳,51%)產物,其HPLC純度>99.9%。
以類似方式製造以下化合物:
3,7-二溴-5-苯基二苯并磷雜環戊二烯(dibenzophosphole)5-氧化物:
66毫升(106毫莫耳,2.0當量)正丁基鋰(1.6M於
己烷中)加至30克(53毫莫耳)4,4’-二溴-2,2’-二碘聯苯於500毫升無水THF中之-78℃溶液中,此混合物於此溫度攪拌30分鐘。之後逐滴添加11克(56毫莫耳,1.06當量)二氯苯基膦氧化物,且當反應完全之後,反應混合物溫熱至室溫。使用水加以水解之後,有機相以乙醚萃取,合併的有機相以硫酸鈉乾燥。在旋轉式蒸發器中移除溶劑,所得的粗產物藉管柱層析法(庚烷/乙酸乙酯6:1)純化,得到20克(45毫莫耳,85%)產物。
3-溴-5-苯基二苯并磷雜環戊二烯5-氧化物:
20克(45毫莫耳)3,7-溴-5-苯基二苯并磷雜環戊二烯5-氧化物於400毫升無水THF中冷卻至-78℃,於此溫度緩慢添加28毫升(45毫莫耳,1.0當量)正丁基鋰(1.6M,於己烷中)。1小時之後,此混合物緩慢溫熱至室溫,添加50毫升1M HCl,此混合物再攪拌2小時。之後,此混合物以乙酸乙酯萃取,以水清洗,合併的有機相以硫酸鈉乾燥。在旋轉式蒸發器中移除溶劑,無須其他純化步驟地直接使用,得到16克(43毫莫耳,96%)單溴化物。
(2-氯苯基)-(5-酮基-5-苯基-5H-5λ*5*-二苯并磷雜環戊二烯-3-基)胺:
16克(43毫莫耳)3-溴-5-苯基二苯并磷雜環戊二烯5-氧化物先與6.6毫升(52毫莫耳,1.2當量)2-氯苯胺
和11克(112毫莫耳,2.6當量)三級丁醇一起引入400毫升甲苯中,並添加480毫克(0.86毫莫耳,0.2當量)DPPF和97毫克(0.43毫莫耳,0.01當量)醋酸鈀。此反應混合物於迴流下加熱隔夜,及,當反應完全時,添加200毫升的水。相分離,含水相以甲苯萃取。合併的有機相以硫酸鈉乾燥並濾經氧化鋁。在真空中移除溶劑,所得殘渣藉管柱層析法(庚烷/乙酸乙酯5:1)純化,得到16克(39毫莫耳,91%)產物。
12-苯基-10H-10-氮雜-12-磷雜茚并[2,1-b]茀12-氧化物:
16克(39毫莫耳)(2-氯苯基)-(5-氧-5-苯基-5H-5λ*5*-二苯并磷雜環戊二烯-3-基)胺和14克(100毫莫耳,2.6當量)碳酸鉀先引至250毫升NMP中,添加1.4克(13毫莫耳,0.34當量)三甲基乙酸。之後添加3.1毫升1 M三-三級丁基膦於甲苯(3.1毫莫耳,0.08當量)中之溶液和440毫克(2.0毫莫耳,0.05當量)醋酸鈀,此反應混合物於內部溫度為130℃加熱隔夜。此批料冷卻至室溫,添加300毫升甲苯和100毫升水。含水相以甲苯萃取三次,合併的有機相亦以水清洗三次且最後以硫酸鈉乾燥。移除溶劑之後,所得的粗產物藉管柱層析法純化,得到13克(35毫莫耳,89%)產物。
B31:12-苯基-10-(9-苯基-9H-咔唑-3-基)-10H-10-氮雜-12-磷雜茚并[2,1-b]茀12-氧化物:
以類似於B1的方式進行此實驗,得到14克(23毫莫耳,67%)標的產物B31。
C部分:熱安定性之比較
若100毫克化合物ICvCbz1在玻璃安瓶中在真空(壓力約10-2毫巴)中熔化且其於烤箱中於310℃儲存14天,根據HPLC,純度由99.7%變為89.2%。使用化合物B29,根據HPLC,在相同程序中,根據HPLC,純度由99.8%變為99.6%,即,在相同的熱載量下,形成的分解產物少得多。由於在有機電致發光裝置之工業產製中,材料長時間處於高溫,所以此具有明顯的工業優點。
D部分:有機電致發光裝置
藉根據WO 2004/058911的一般方法,其採用此處描述的環境(層厚度變化,材料),製造根據本發明的OLED及根據先前技術的OLED。
各種OLED的數據示於以下的實例V1至E17(請參考表1和2)。經結構化的ITO(氧化銦錫)以50奈米厚度塗覆的玻璃板以20奈米PEDOT:PSS(聚(3,4-伸乙二氧基噻吩)聚(苯乙烯磺酸酯),商品名CLEVIOSTM P VP AL 4083,購自德國Heraeus Precious Metals GmbH)塗覆(藉水溶液的旋轉塗覆法塗覆)以改良加工性。這些經塗覆的玻璃板形成用於OLED的基板。此OLED具有以下的層結構:基板/電洞傳遞層(HTL)/中間層(IL)/電
子阻斷層(EBL)/發光層(EML)/電洞阻斷層(HBL)/電子傳遞層(ETL),及最後厚度為100奈米的鋁陰極。OLED的確實結構示於表1。製造OLED所須材料示於表3。
所有材料在真空槽中藉熱蒸氣沉積法施用。發光層均係由至少一個基質材料(主體材料)和發光摻雜物(發光體,其藉共蒸發而與一或多種基質材料以某些體積比摻合)所構成。此處的表示,如IC1:IC2:TEG1(30%:60%:10%),是指IC1在層中的存在體積比為30%,IC2在層中的存在體積比為60%,而TEG1在層中的存在體積比為10%。類似的情況用於電子傳遞層。
藉標準方法定出此OLED的特徵。為此目的,假設Lambert發光特性,由電流/電壓/發光密度特徵線(IUL特徵線)計算電致發光光譜、電流效率(單位為cd/A)、功率效率(單位為1m/W)和外部量子效率(EQE,單位為%)與發光密度的關係,及定出壽命。電致發光光譜於發光密度為1000cd/平方米測定,並自彼計算CIE 1931 x和y色座標。表2中的U1000代表發光密度為1000cd/平方米所須的電壓。CE1000和PE1000代表於1000cd/平方米的電流效率和功率效率。最後,EQE1000代表於操作發光密度為1000cd/平方米時的外部量子效率。壽命LT代表於固定電流操作的發光密度自初發光密度L0下降某些比例L1之後的時間。表2中之L0=10000cd/平方米而L1=70%的規格是指LT欄中的壽命對應於初發光密度自10000cd/
平方米降至7000cd/平方米之後的時間。
各種OLED的數據節錄於表2。實例V1-V8係根據先前技術的比較例,實例E1-E17為包含根據本發明之材料的OLED的數據。
以下更詳細地解釋一些實例以說明根據本發明之化合物的優點。但是,應指出此僅代表表2所示數據之中之一部分。如由表2可看出者,使用根據本發明中之未更詳細說明之化合物亦可得到相較於先前技術之顯著改良。
根據本發明之化合物於作為混合基質系統之用途
以下實例中,出示混合比經選擇以達到最高壽命的OLED數據。
若比較實例V2和E1,可看出相較於根據先前技術的化合物IC2(其具有聯三苯取代基),根據本發明之化合物B2(其氮上帶有咔唑取代基)提供顯著較佳的結果。使用B2,功率效率改良至多15%,壽命改良約20%。
以咔唑取代基代替茚并咔唑(實例V1和E2)亦得到明顯改良。此情況中,壽命實質提高2倍,而功率效率亦極高地改良20%。相較於雙咔唑BCbz1,使用B29亦得到明顯改良的壽命和功率效率(實例V3和E2)。
以未橋連的咔唑代替橋連的咔唑(實例V5和E2),壽命提高60%。雖然相較於根據本發明的化合物B29,以根據先前技術的化合物ICvCbz1得到或多或少較佳的量子效率,但是由於較佳的電壓而導致有相同的功率效率。
若包含根據先前技術之材料的OLED中之發光體濃度降至明顯低於10%,其效率和壽命顯著降低。使用化合物IC2時,例如,當發光體濃度自10%降至4%時,外部量子效率降低至多10%。更顯著的是壽命受損超過1.5倍(實例V7和V8)。反之,使用根據本發明之材料,觀察到效能未降低(實例E1相較於E12)或甚至略為改良(實例E2相較於E13-E15)。
因此,相較於先前技術者時,作為磷光OLED中的基質材料時,在一些或所有的參數上,根據本發明之材料提供顯著改良。此外,使用根據本發明之材料,可得到發光體濃度低的OLED,且不會降低效能。
Claims (18)
- 一種式(1)化合物,
- 如申請專利範圍第1項之化合物,其中鍵結至氮原子的R1基團代表具有5至60個芳環原子的芳環或雜芳環系統,其亦可經一或多個R2基團取代,或代表式(3)或(4)的基團。
- 如申請專利範圍第1項之化合物,其中X代表C(R1)2,其中R1於每次出現時相同或不同地代表具1至10個C原子的直鏈烷基或具3至10個C原子的支鏈或環狀烷基(其各者經一或多個R2基團取代,其中一或多個不相鄰的CH2基團可被R2C=CR2、C≡C、Si(R2)2、C=O、O、S或CONR2所代替且一或多個H原子可被D、F或CN所代替)、或具5至60個芳環原子的芳環或雜芳環系統(其各者可經一或多個R2基團取代);R1基團亦可彼此形成芳環或脂環系統。
- 如申請專利範圍第1項之化合物,其中每一個環有至多一個Y基團代表N,而其餘的Y基團於每次出現時相同或不同地代表CR。
- 如申請專利範圍第1項之化合物,其係選自式(5)化合物,
- 如申請專利範圍第5項之化合物,其係選自式(6)、(7)和(8)的結構,
- 如申請專利範圍第6項之化合物,其係選自式(6b)、(7b)和(8b)化合物,
- 如申請專利範圍第1項之化合物,其中式(2)至(4)的基團係選自式(2a)至(4a)的基團,
- 如申請專利範圍第1項之化合物,其中式(2)至(4)的基團係選自式(2b)、(2c)、(2d)、(3b)、(3c)、(3d)和(4b)的結構,
- 如申請專利範圍第8或9項之化合物,其中鍵結至式(2a)至(4b)中之碳原子的R2基團代表H。
- 如申請專利範圍第1項之化合物,其中Z或W代表NR2,其中R2代表芳環或雜芳環系統。
- 如申請專利範圍第1項之化合物,其係選自式(9)、(10)、(11)或(12)的結構,
- 一種製造如申請專利範圍第1至12項中任一項之化合物之方法,其特徵在於式(2)、(3)或(4)的基團藉Suzuki偶合、Ullmann偶合或藉Hartwig-Buchwald偶合引入。
- 一種混合物,其包含至少一種如申請專利範圍第1至12項中任一項之化合物和至少一種螢光或磷光摻雜物。
- 一種調合物,特別是溶液、懸浮液或微乳液,其包含至少一種如申請專利範圍第1至12項中任一項之化合物或如申請專利範圍第14項之混合物及一或多種溶劑。
- 一種如申請專利範圍第1至12項中任一項之化合物或如申請專利範圍第14項之混合物於電子裝置中之用途。
- 一種電子裝置,其特別選自有機電致發光裝置、有機積體電路、有機場效電晶體、有機薄膜電晶體、有機發光電晶體、有機太陽能電池、有機染料敏化的太陽能電池、有機光學偵測器、有機光受體、有機場淬冷裝置(organic field-quench device)、發光電化學電池、有機雷射二極體和“有機電漿發射裝置(organic plasmon emitting device)”,其包含如申請專利範圍第1至12項中任一項之化合物或如申請專利範圍第14項之混合物。
- 如申請專利範圍第17項之電子裝置,其為有機電致發光裝置,且如申請專利範圍第1至12項中任一項之化合物係用作為發光層中之磷光化合物的基質材料。
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- 2012-08-23 CN CN201280046210.3A patent/CN103842339B/zh active Active
- 2012-08-23 US US14/346,187 patent/US9818948B2/en active Active
- 2012-08-23 CA CA2849087A patent/CA2849087A1/en not_active Abandoned
- 2012-08-23 SG SG11201400709VA patent/SG11201400709VA/en unknown
- 2012-08-23 WO PCT/EP2012/003563 patent/WO2013041176A1/de active Application Filing
- 2012-08-23 KR KR1020147010455A patent/KR102077994B1/ko active IP Right Grant
- 2012-09-18 TW TW101134157A patent/TWI570217B/zh active
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI766884B (zh) * | 2016-09-30 | 2022-06-11 | 德商麥克專利有限公司 | 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途 |
US11530224B2 (en) | 2016-09-30 | 2022-12-20 | Merck Patent Gmbh | Compounds with diazadibenzofurane or diazadibenzothiophene structures |
TWI814711B (zh) * | 2016-09-30 | 2023-09-11 | 德商麥克專利有限公司 | 具有二氮雜二苯並呋喃或二氮雜二苯並噻吩結構之咔唑、製備彼之方法及其用途 |
US12030890B2 (en) | 2016-09-30 | 2024-07-09 | Merck Patent Gmbh | Compounds with diazadibenzofurane or diazadibenzothiophene structures |
Also Published As
Publication number | Publication date |
---|---|
RU2014115454A (ru) | 2015-10-27 |
SG11201400709VA (en) | 2014-06-27 |
CN103842339B (zh) | 2017-08-08 |
EP2758372B1 (de) | 2017-05-17 |
BR112014006697A2 (pt) | 2017-03-28 |
AU2012313001A1 (en) | 2014-05-01 |
AU2012313001B2 (en) | 2017-03-09 |
CA2849087A1 (en) | 2013-03-28 |
KR102077994B1 (ko) | 2020-02-17 |
JP6174030B2 (ja) | 2017-08-02 |
JP2014528942A (ja) | 2014-10-30 |
US20140225046A1 (en) | 2014-08-14 |
TWI570217B (zh) | 2017-02-11 |
EP2758372A1 (de) | 2014-07-30 |
US9818948B2 (en) | 2017-11-14 |
RU2626977C2 (ru) | 2017-08-02 |
IN2014KN00846A (zh) | 2015-10-02 |
CN103842339A (zh) | 2014-06-04 |
WO2013041176A1 (de) | 2013-03-28 |
KR20140069199A (ko) | 2014-06-09 |
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