TWI658117B - 有機電致發光裝置之發光材料 - Google Patents
有機電致發光裝置之發光材料 Download PDFInfo
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- TWI658117B TWI658117B TW106132388A TW106132388A TWI658117B TW I658117 B TWI658117 B TW I658117B TW 106132388 A TW106132388 A TW 106132388A TW 106132388 A TW106132388 A TW 106132388A TW I658117 B TWI658117 B TW I658117B
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- 239000000463 material Substances 0.000 title claims abstract description 62
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
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Abstract
一種由下式(1)表示的發光材料,使用該材料作為延遲螢光發光摻雜劑或螢光發光摻雜劑的有機電致發光裝置具有良好的性能表現,如低驅動電壓及低功耗,尤其是摻雜於主體(H1至H4)及第二主體(SH1至SH4)可提高效率及增長半衰期。
Description
本發明涉及一種發光材料及使用具有式(1)的該發光材料的有機電致發光(Organic Electroluminescence,本文中簡稱為有機EL)裝置,使用該發光材料作為發光層的延遲螢光發光摻雜劑或螢光發光摻雜劑的有機EL裝置具有良好的性能表現。
有機電致發光(有機EL)裝置是一種發光二極體(Light-emitting diode,LED),其中發射層為由響應於電流而發光的有機化合物製成的薄膜。有機化合物的發射層被夾置在兩個電極之間。有機EL裝置因其高照度、低重量、超薄外型、無背光的自照明、低能耗、廣視角、高對比度、製造簡單及反應時間快速而應用在平板顯示器中。
有機材料的電致發光係於1950年代早期由法國南錫大學的安德烈貝諾斯(Andre Bernanose)及其同事首先發現。馬丁伯普(Martin Pope)及其紐約大學的同事於1963年在真空下、在蔥的單一純晶體和摻有稠四苯的蔥晶體上首次觀察到直流(DC)電致發光。
伊士曼柯達(Eastman Kodak)公司的鄧青雲(Ching W.Tang)及史蒂芬范斯萊克(Steven Van Slyke)在1987年公佈了第一個二 極體裝置。該裝置採用具有個別的電洞傳輸層和電子傳輸層的雙層結構,使得操作電壓降低及效率提高,從而促成當今主流的有機EL研究及裝置生產。
有機EL裝置通常是由位於兩個電極之間的有機材料層所組成,有機材料層包括電洞傳輸層(hole transport layer,HTL)、發光層(emitting layer,EML)、電子傳輸層(electron transport layer,ETL)。有機EL的基本機制涉及載子的注入、傳輸、復合、以及形成而發光的激子。當施加外部電壓到有機EL裝置時,電子和電洞將分別自陰極和陽極注入,電子將從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital,LUMO),且電洞將從陽極注入最高佔用分子軌域(highest occupied molecular orbital,HOMO)。當電子與電洞在發光層中復合時將會形成激子並隨後發光。當發光分子吸收能量以達到激發態時,根據電子和電洞自旋組合的方式,激子可處於單重態或三重態。透過電子與電洞復合所形成的75%激子達到三重激發態。從三重態的衰減是自旋禁止的,因此,螢光電致發光裝置僅具有25%的內部量子效率。與螢光電致發光裝置相反,磷光有機EL裝置利用自旋-軌域交互作用來促進單重態與三重態之間的系統間跨越,從而獲得單重態和三重態的發射、以及25%至100%的電致發光裝置內部量子效率。
近來,安達(Adachi)及同事(2012年)已開發出整合熱活化型延遲螢光(thermally activated delayed fluorescence,TADF)機制的新型螢光有機EL裝置,其透過在單重態及三重態間使用具有較小能量間隙的材料得到的逆向系統間跨越(reverse intersystem crossing,RISC) 機制,將自旋禁止的三重態激子轉化為單重態而獲得高效率的激子形成。
對於主動矩陣有機發光二極體(active-matrix organic light-emitting diode,AMOLED)為發光面板的全彩平板顯示器來說,使用於藍色螢光發光層中該材料之半衰期、效率及驅動電壓方面仍無法令人滿意。在本發明中,為了延長有機EL裝置中發光層之螢光摻雜劑的半衰期及降低驅動電壓,我們使用吖啶基雜環(acridine-based hererocyclic)化合物骨架與氰基(cyano group)取代的萘基(naphthyl group)、菲基(phenanthrenyl group)、蒽基(anthracenyl group)、芘基(pyrenyl group)、屈基(chrysenyl group)、聯三伸苯基(triphenylenyl group)及苝基(perylenyl group)連接,以得到由式(1)表示的發光材料。該發光材料對於有機EL裝置來說,具有良好的熱穩定性及電荷載子遷移率。專利WO 2006033563A1、US20120168730A1、US20120248968A1、US9000171B2揭露的吖啶基雜環化合物骨架基衍生物已被說明用於有機EL裝置。尚未有先前技術表明吖啶基雜環化合物骨架與氰基取代的萘基、菲基、蒽基、芘基、屈基、聯三伸苯基及苝基連接用作有機EL裝置的延遲螢光發光摻雜劑或螢光發光摻雜劑。
根據上述原因,本發明之目的為解決現有技術的這些問題,並提供一種發光裝置,其在熱穩定性、高發光效率、高亮度及長半衰期上表現極佳。本發明揭露一種具有式(1)的發光材料,其用作發光層的延遲螢光發光摻雜劑或螢光發光摻雜劑,該層具有良好的電荷載子遷移率和極佳的操作耐用性,可降低有機EL裝置的驅動電壓和能耗、提高有機EL裝置的效率並延長其半衰期。
根據本發明,提供一種發光材料及該發光材料用於有機EL裝置發光層的延遲螢光摻雜劑或螢光摻雜劑的用途。該發光材料可克服習知材料的缺點,如半衰期較短、效率較低及高驅動電壓。
本發明的目的是將該發光材料用作有機EL裝置的螢光發光摻雜劑,並可降低驅動電壓、能耗及提高效率。
本發明的目的是將該發光材料用作有機EL裝置的延遲螢光發光摻雜劑或與主體及第二螢光主體材料共沉積,可提高效率及延長半衰期。
本發明具有產業應用的經濟優點。因此,本發明揭露了可用於有機EL裝置的發光材料。所述發光材料由下式(1)表示:
其中G表示下式(2):
A表示具有二至五個環的稠環烴(fused ring hydrocarbon)單元,其中A 表示萘基(naphthyl group)、菲基(phenanthrenyl group)、蒽基(anthracenyl group)、芘基(pyrenyl group)、屈基(chrysenyl group)、聯三伸苯基(triphenylenyl group)及苝基(perylenyl group);L表示單鍵、經取代或未經取代的伸苯基(phenylene group)或經取代或未經取代的雜伸苯基(heterophenylene group),X表示選自包含O、S、C(R5)(R6)、Si(R7)(R8)及N(R9)的原子或基團的二價橋,Ar表示稠合碳環(fused carbocyclic ring)或R1,m表示0至10的整數,n表示0至4的整數,p表示0至4的整數,R1至R9係獨立選自由氫原子、具有1至20個碳原子的經取代或未經取代的烷基(alkyl group)、具有6至30個碳原子的經取代或未經取代的芳基(aryl group)、及具有3至30個碳原子的經取代或未經取代的雜芳基(heteroaryl group)所組成之群組。
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧電子阻擋層
10‧‧‧發光層
11‧‧‧電洞阻擋層
12‧‧‧電子傳輸層
13‧‧‧電子注入層
14‧‧‧金屬電極
圖1為本發明之有機電致發光裝置的一個實施例之示意圖。
本發明探究發光材料及使用該材料的有機EL裝置。下面將詳細說明生產、結構及組成部分,以使對本發明的理解更充分。本發明的應用明顯不受限於所屬技術領域中具有通常知識者熟知的具體細節。另一方面,不對眾所周知的一般組成部分和程序作詳細描述,以避免對本發明造成不必要的限制。現在將在下面更詳細地介紹本發明的一些優選實施例。然而,應當瞭解的是,除了本文明確描述的實施例之外,本發明還可實施於各種其他實施例中,也就是說,本發明還可廣泛應用於其他 實施例,且本發明的範圍不會因此受到明確的限制,只受隨附申請專利範圍的內容限制。
在本發明的第一實施例中,揭露了可用作有機EL裝置的延遲螢光發光摻雜劑或螢光發光摻雜劑的發光材料。所述發光材料由下式(1)表示:
其中G表示下式(2):
A表示具有二至五個環的稠環烴單元,其中A表示萘基、菲基、蒽基、芘基、屈基、聯三伸苯基及苝基;L表示單鍵、經取代或未經取代的伸苯基或經取代或未經取代的雜伸苯基,X表示選自包含O、S、C(R5)(R6)、Si(R7)(R8)及N(R9)的原子或基團的二價橋,Ar表示稠合碳環或R1,m表示0至10的整數,n表示0至4的整數,p表示0至4的整數,R1至R9係獨立選自由氫原子、具有1至20個碳原子的經取代或未經取代的烷基、具有6至30個碳原子的經取代或未經取代的芳基、及具有3至30個碳原子的經取代或 未經取代的雜芳基所組成之群組。
根據上述發光材料式(1),其中A由下等式表示:
在此實施例中,一些發光材料如下所示:
本發明中發光材料的詳細製備可以以例示性實施例清 楚闡明,但本發明並不限於例示性實施例。實施例1至實施例4展示本發明有機材料實施例的製備。實施例5展示有機EL裝置的製造及有機EL裝置的I-V-B、半衰期測試報告。
實施例1
C16之合成
2-溴-6-(萘-2-基)苯酚(2-bromo-6-(naphthalen-2-yl)phenol)之合成
將39.5g(157mmol)2,6-二溴苯酚(2,6-dibromophenol)、27.0g(157mmol)萘-2-基硼酸(naphthalen-2-ylboronic acid)、3.5g(3mmol)四(三苯基膦)鈀(Pd(PPh3)4)、157ml 2M的Na2CO3、200ml乙醇(EtOH)及400ml甲苯(toluene)的混合物除氣並放在氮氣中,隨後在100℃下加熱12小時。反應完成後,讓混合物冷卻至室溫。將有機層用乙酸乙酯和水(ethyl acetate)萃取、用無水硫酸鎂(anhydrous magnesium sulfate)乾燥,移除溶劑並藉由矽膠管柱層析法純化殘餘物,得到白色固體產物(27.2g,91mmol,產率:58%)。
10-溴苯并[d]萘并[1,2-b]呋喃(10-bromobenzo[d]naphtho[1,2-b]furan)之合成
將27.2g(91mmol)2-二溴-6-(萘-2-基)苯酚(2-bromo-6-(naphthalen-2-yl)phenol)、2.2g(9.7mmol)乙酸鈀(Pd(OAc)2)、1.2g(9.7mmol)3-硝基吡啶(3-nitropyridine)、37.5g(193mmol)過氧苯甲酸叔丁酯(tert-butyl peroxybenzoate)、150ml六氟苯(C6F6)及100ml二甲基甲醯胺(Dimethylformamide,DMF)的混合物除氣並放在氮氣中,隨後在150℃下加熱24小時。反應完成後,讓混合物冷卻至室溫。將有機層用乙酸乙酯和水萃取、用無水硫酸鎂乾燥,移除溶劑並藉由矽膠管柱層析法純化殘餘物,得到白色固體產物(11g,37.3mmol,產率:41%)。
2-(苯并[d]萘并[1,2-b]呋喃-10-基胺基)苯甲酸甲酯(methyl 2-(benzo[d]naphtho[1,2-b]furan-10-ylamino)benzoate)之合成
將14.9g(50mmol)10-溴苯并[d]萘并[1,2-b]呋喃(10-bromobenzo[d]naphtho[1,2-b]furan)、8.3g(55mmol)2-胺基苯甲酸甲酯(methyl 2-aminobenzoate)、0.25g(1mmol)乙酸鈀(II)、0.75g(2.0mmol)2-(二環己基膦基)聯苯(2-(dicyclohexylphosphino)biphenyl)、9. 6g(100mmol)叔丁醇鈉(sodium tert-butoxide)及100ml鄰二甲苯(o-xylene)的混合物在氮氣下迴流過夜。反應完成後,在100℃過濾溶液,得到過濾物,將過濾物加入1L的甲醇(MeOH)中,同時攪拌並抽氣過濾出沉澱物。得到用己烷再結晶的黃色產物(9.4g,25.5mmol,產率:51%)。
2-(2-(苯并[d]萘并[1,2-b]呋喃-10-基胺基)苯基)丙-2-醇(2-(2-(benzo[d]naphtho[1,2-b]furan-10-ylamino)phenyl)propan-2-ol)之合成
將33.4g(91mmol)的2-(苯并[d]萘并[1,2-b]呋喃-10-基胺基)苯甲酸甲酯(methyl 2-(benzo[d]naphtho[1,2-b]furan-10-ylamino)benzoate)放入燒瓶中,並將燒瓶抽成真空,填入N2。加入700ml四氫呋喃(tetrahydrofuran),在-78℃下進行攪拌10分鐘。隨後,再加入284ml(455mol)甲基鋰(MeLi)(1.6M於己烷(hexane)中),在-78℃下攪拌10分鐘並在室溫下攪拌6小時。反應結束後,使用蒸餾水及乙酸乙酯萃取反應產物。所得有機層使用MgSO4乾燥、使用旋轉減壓濃縮機(rotary evaporator)進行蒸發移除溶劑,再使用己烷及乙酸乙酯作為展開溶劑(developing solvent)進行管柱層析,從而得到26g(71mmol,產率:78%)2-(2-(苯并[d]萘并[1,2-b]呋喃-10-基胺基)苯基)丙-2-醇(2-(2-(benzo[d]naphtha[1,2-b]furan-10-ylamino)phenyl)propan-2-ol)。
中間體I的合成
將26g(71mmol)2-(2-(苯并[d]萘并[1,2-b]呋喃-10-基胺基)苯基)丙-2-醇(2-(2-(benzo[d]naphtho[1,2-b]furan-10-ylamino)phenyl)propan-2-ol)放入燒瓶中,並將燒瓶抽成真空,填入N2。加入200ml乙酸(AcOH),在0℃下進行攪拌10分鐘。將400ml磷酸(H3PO4)加入反應混合物中並在室溫下攪拌3小時。反應結束後,將反應產物使用氫氧化鈉(NaOH)中和、並使用蒸餾水和乙酸乙酯萃取。將所得有機層使用MgSO4乾燥、使用旋轉減壓濃縮機(rotary evaporator)進行蒸發以移除溶劑、再使用己烷和乙酸乙酯作為展開溶劑(developing solvent)進行管柱層析,從而得到18.4g(產率:74%)的中間體I。
芘-1,6-二甲腈(pyrene-1,6-dicarbonitrile)之合成
將30g的1,6-二溴芘(1,6-dibromopyrene)稀釋於600ml二甲基甲醯胺(dimethylformamide,DMF)中,隨後滴入20g的氰化亞銅(CuCN),在170℃的溫度下迴流該混合物,同時進行攪拌。反應結 束後,將溫度冷卻至室溫,使用水來停止反應,並使用水和乙酸乙酯萃取。將所得有機層使用MgSO4乾燥、使用旋轉減壓濃縮機進行蒸發以移除溶劑、再使用己烷和乙酸乙酯作為展開溶劑進行管柱層析,從而得到芘-1,6-二甲腈(pyrene-1,6-dicarbonitrile)(19.6g,77.5mmol,產率:93%)。
3,8-二溴芘-1,6-二甲腈(3,8-dibromopyrene-1,6-dicarbonitrile)之合成
將所得芘-1,6-二甲腈(pyrene-1,6-dicarbonitrile)(19.6g,77.7mmol)及DMF(300ml)加入反應容器中。在冰冷卻條件下加入N-溴代琥珀醯亞胺(N-bromosuccinimide,NBS)(33g,186mmol),將混合物攪拌9小時。過濾分離沉澱的晶體,使用水和甲醇清洗,得到黃色固體產物(13.1g,31.8mmol,產率:41%)。
C16之合成
將4.1g(10mmol)3,8-二溴芘-1,6-二甲腈(3,8-dibromopyrene-1,6-dicarbonitrile)、7.1g(20.4mmol)中間體I、0.05g(0.2mmol)乙酸鈀(II)(palladium(II)acetate)、0.15g(0.4mmol)2-(二環己基膦)聯苯(2-(dicyclohexylphosphino)biphenyl)、3.8g(40mmol)叔丁醇鈉(sodium tert-butoxide)及50ml鄰二甲苯的混合物在氮氣中迴流過夜。反應完成後,在120℃過濾溶液,得到過濾物,將過濾物加入1L的甲醇中,同時攪拌並抽氣過濾出沉澱的產物。得到6.4g(產率61%)用甲苯再結晶並透過真空昇華純化的黃色產物。MS(m/z,FAB+):946.3。
實施例2
C17之合成
1,6-二異丙基芘(1,6-diisopropylpyrene)之合成
在1L的圓底三頸燒瓶中,將20g(55.6mmol)1,6- 二溴芘、120ml的1M異丙基溴化鎂(isopropylmagnesiumbromide)、2.3g(二苯基膦基二茂鐵)二氯化鈀(II)((diphenylphosphinoferrocene)palladium(II)dichloride)及200ml去水二噁烷(dioxane)放入燒瓶中,所得溶液在100℃的溫度下加熱攪拌24小時。反應完成後,加入100ml稀鹽酸,將有機層分離並在減壓下濃縮。隨後,使有機層通過矽膠短柱,並在減壓下再次濃縮之後過濾分離沉澱的晶體,得到6.2g的1,6-二異丙基芘(1,6-diisopropylpyrene)(產率:39%)。
1,6-二溴-3,8-二異丙基芘(1,6-dibromo-3,8-diisopropylpyrene)之合成
將所得1,6-二異丙基芘(1,6-diisopropylpyrene)(22.3g,77.7mmol)及DMF(300ml)加入反應容器中。在冰冷卻條件下加入N-溴代琥珀醯亞胺(N-bromosuccinimide)(33g,186mmol),將混合物攪拌9小時。過濾分離沉澱的晶體,使用水及甲醇清洗,得到黃色固體產物(9.7g,21.8mmol,產率:28%)。
C17之合成
將4.4g 1,6-二溴-3,8-二異丙基芘(1,6-dibromo-3,8-diisopropylpyrene)(10mmol)、7.1g(20.4mmol)中間體I、0.05g(0.2mmol)乙酸鈀(II)(palladium(II)acetate)、0.15g(0.4mmol)2-(二環己基膦)聯苯(2-((dicyclohexylphosphino)biphenyl)、3.8g(40mmol)叔丁醇鈉(sodium tert-butoxide)及50ml鄰二甲苯的混合物在氮氣中迴流過夜。反應完成後,在120℃過濾溶液以得到過濾物,將過濾物加入1L MeOH中,同時攪拌並抽氣過濾出沉澱的產物。得到4.6g(產率:47%)用甲苯再結晶並透過真空昇華純化的黃色產物。MS(m/z,FAB+):980.5。
實施例3
C18之合成
2-(二苯并[b,d]呋喃-4-基胺基)苯甲酸甲酯(2-(dibenzo[b,d]furan-4-ylamino)benzoate)之合成
將12.4g(50mmol)4-溴二苯并[b,d]呋喃(4-bromodibenzo[b,d]furan)、8.3g(55mmol)2-胺基苯甲酸甲酯(methyl 2-aminobenzoate)、0.25g(1mmol)乙酸鈀(II)(palladium(II)acetate)、0.75g(2.0mmol)2-(二環己基膦)聯苯(2-((dicyclohexylphosphino)biphenyl)、9.6g(100mmol)叔丁醇鈉(sodium tert-butoxide)及100ml鄰二甲苯的混合物在氮氣中迴流過夜。反應完成後,在100℃過濾溶液以得到過濾物,將過濾物加入1L MeOH中,同時攪拌並抽氣過濾出沉澱的產物。得到用己烷再結晶的黃色產物(14g,31.5mmol,產率:63%)。
2-(2-(二苯并[b,d]呋喃-4-基胺基)苯基)丙-2-醇(2-(2-(dibenzo[b,d]furan-4-ylamino)phenyl)propan-2-ol)之合成
在燒瓶中放入14g(31.5mmol)2-(二苯并[b,d]呋喃-4-基胺基)苯甲酸甲酯(methyl 2-(dibenzo[b,d]furan-4-ylamino)benzoate),將燒瓶抽成真空並充入N2。加入230ml四氫呋喃,在-78℃下進行攪拌10分鐘。隨後加入95ml(152mol)MeLi(1.6M於己烷中),在-78℃下攪 拌10分鐘並在室溫下攪拌6小時。反應結束後,反應產物使用蒸餾水及乙酸乙酯來萃取。將所得有機層使用MgSO4乾燥、使用旋轉減壓濃縮機進行蒸發以移除溶劑、再使用己烷及乙酸乙酯作為展開溶劑進行管柱層析,從而得到8.5g(26.8mmol,產率:85%)2-(2-(二苯幷[b,d]呋喃-4-基胺基)苯基)丙-2-醇。
5,5-二甲基-5,13-二氫苯并呋并[3,2-c]吖啶(5,5-dimethyl-5,13-dihydrobenzofuro[3,2-c]acridine)之合成
在燒瓶中放入8.5g(26.8mmol)2-(2-二苯并[b,d]呋喃-4-基胺基)苯基)丙-2-醇(2-(2-(dibenzo[b,d]furan-4-ylamino)phenyl)propan-2-ol),將燒瓶抽成真空並充入N2。加入70ml AcOH,在0℃下進行攪拌10分鐘。將130ml H3PO4加入反應混合物中並在室溫下攪拌3小時。反應結束後,將反應產物使用NaOH中和,並使用蒸餾水及乙酸乙酯來萃取。將所得有機層使用MgSO4乾燥、使用旋轉減壓濃縮機進行蒸發以移除溶劑、再使用己烷及乙酸乙酯作為展開溶劑進行管柱層析,從而得到6.6g(產率:83%)5,5-二甲基-5,13-二氫苯并呋并[3,2-c]吖啶(5,5-dimethyl-5,13-dihydrobenzofuro[3,2-c]acridine)。
C18之合成
將4.1g(10mmol)3,8-二溴芘-1,6-二甲腈(3,8-dibromopyrene-1,6-dicarbonitrile)、6.1g(20.4mmol)5,5-二甲基-5,13-二氫苯并呋并[3,2-c]吖啶(5,5-dimethyl-5,13-dihydrobenzofuro[3,2-c]acridine)、0.05g(0.2mmol)乙酸鈀(II)、0.15g(0.4mmol)2-(二環己基膦)聯苯、3.8g(40mmol)叔丁醇鈉及50ml鄰二甲苯的混合物在氮氣下迴流過夜。反應完成後,在120℃過濾溶液以得到過濾物,將過濾物加入1L MeOH中,同時攪拌並抽氣過濾出沉澱的產物。得到4.8g(產率:57%)用甲苯再結晶並透過真空昇華純化的黃色產物。MS(m/z,FAB+):846.5。
實施例4
C19之合成
將4.4g(10mmol)1,6-二溴-3,8-二異丙基芘(1,6-dibromo-3,8-diisopropylpyrene)、6.1g(20.4mmol)5,5-二甲基-5,13-二氫苯并呋并[3,2-c]吖啶(5,5-dimethyl-5,13-dihydrobenzofuro[3,2-c]acridine)、0.05g(0.2mmol)乙酸鈀(II)、0.15g(0.4mmol)2-(二環己基膦)聯苯(2-(dicyclohexylphosphino)biphenyl)、3.8g(40mmol)叔丁醇鈉及50ml鄰二甲苯的混合物在氮氣下迴流過夜。反應完成後,在120℃過濾溶液以得到過濾物,將過濾物加入1L MeOH中,同時攪拌並抽氣過濾出沉澱的產物。得到5.4g(產率:62%)用甲苯再結晶並透過真空昇華純化的黃色產物。MS(m/z,FAB+):880.1。
生產有機EL裝置的一般方法
提供阻值為9~12歐姆/平方(ohm/square)及厚度為120~160nm的銦錫氧化物(Indium Tin Oxide,ITO)塗層玻璃,並在超音波浴(例如洗滌劑、去離子水)中進行多步驟清洗。在氣相沉積有機層之 前,藉由紫外光(UV)和臭氧進一步處理清洗過的ITO基板。ITO基板的所有預處理製程皆在潔淨室(100級)內進行。
在高真空設備(例如:電阻加熱的石英舟,10-7Torr)中藉由氣相沉積將這些有機層依序塗佈到ITO基板上。藉助石英晶體監視器來精確監控或設定各層的厚度和氣相沉積速率(0.1~0.3nm/sec)。如上所述,還可以使個別層包含多於一種化合物,即通常摻雜有摻雜材料的主體材料,此可藉由來自兩個或更多個來源的共氣相沉積來實現。
在此有機EL裝置中使用二吡嗪并[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)作為電洞注入層,並在本發明中使用N4,N4’-二(聯苯-4-基)-N4,N4’-二苯基聯苯基-4,4’-二胺(N4,N4’-di(biphenyl-4-yl)-N4,N4’-diphenylbiphenyl-4,4’-diamine)(HT1)作為電洞傳輸層、使用N-(聯苯-4-基)-9,9-二甲基-N-(4’-苯基聯苯-4-基)-9氫-茀-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4’-phenyl biphenyl-4-yl)-9H-fluoren-2-amine)(EB2)作為電子阻擋層、使用H1至H4作為螢光主體材料、使用H5作為延遲螢光主體材料、且使用SH1至SH4作為第二螢光主體材料。化學結構如下所示:
本發明製備的以下發光材料實施例1至實施例4可由有機EL裝置驗證並用作其延遲螢光摻雜劑或螢光摻雜劑,且使用N1,N1,N6,N6-四甲苯基芘-1,6-二胺(N1,N1,N6,N6-tetram-tolylpyrene-1,6-diamine)(D1)作為藍色螢光摻雜劑進行比較。
使用2,2’,2”-(1,3,5-苯三基)-三(1-苯基-1-氫-苯并咪唑)(2,2’,2”-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole))(TPBi)及HB3(參見下列化學結構)作為電洞阻擋材料(HBM),並使用2-(10,10-二甲基-10氫-茚并[2,1-b]三伸苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)(ET2)作為電子傳輸材料,以在有機EL裝置中與8-羥基喹啉-鋰(8-hydroxyquinolato-lithium,LiQ)共沉積。本發明中用於製作標準有機EL裝置對照與比較材料的其他先前技術OLED材料之化學結構如下所示:
有機EL裝置一般包含透過熱蒸發作為陰極的低功函數金屬,例如Al、Mg、Ca、Li及K,且該低功函數金屬可有助於電子從陰極注入電子傳輸層。另外,在陰極與電子傳輸層之間引入薄膜電子注入 層,用於減少電子注入障礙並提高有機EL裝置性能。習知的電洞注入層材料為具有低功函數的金屬鹵化物或金屬氧化物,例如:LiF、LiQ、MgO或Li2O。
另一方面,在製作有機EL裝置之後,透過使用PR650光譜掃描光譜儀量測EL光譜及CIE座標。此外,電流/電壓、發光/電壓及產率/電壓特性都使用吉時利(Keithley)2400可編程電壓電流源來檢測。在室溫(約25℃)及大氣壓下操作上述設備。
實施例5
使用與上述一般方法類似的程序製作具有下列裝置結構的有機螢光或延遲螢光EL裝置(參見圖1)。有機EL裝置包含透明電極6與金屬電極14,其間依序分別為沉積在透明電極6上的電洞注入層7、沉積在電洞注入層7上的電洞傳輸層8、沉積在電洞傳輸層8上的電子阻擋層9、沉積在電子阻擋層9上的發光層10、沉積在發光層10上的電洞阻擋層11、沉積在電洞阻擋層11上的電子傳輸層12、沉積在電子傳輸層12上的電子注入層13,並且金屬電極14沉積在電子注入層13上。裝置:ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/Host+3%~15%摻雜劑(30nm)HBM(10nm)/摻雜40% LiQ的ETM(35nm)/LiQ(1nm)/Al(160nm)。有機EL裝置的I-V-B(1000nits亮度時)測試報告如表1所示。T70定義為3000cd/m2的初始亮度降至2100cd/m2的時間(小時)。
表1
在上述有機EL裝置的優選實施例之測試報告(參見表1)中,我們展示了本發明中用作有機EL裝置之發光摻雜材料的式(1)發光材料具有比先前技術的有機EL材料更良好的性能表現。更具體言之,本發明的有機EL裝置使用具有式(1)的發光材料作為發光客體材料 來與發光主體材料(例如H1、H2、H3、及H4)搭配使用,展現出低功耗、高效率、及長半衰期的優勢。另外,我們使用SH1至SH4作為第二螢光主體材料與H1至H4共沉積,展現出比其他更好的最佳效率及半衰期。
總而言之,本發明揭露了一種用作有機EL裝置的發光摻雜材料之具有式(1)的發光材料。所述發光材料由下式(1)表示:
其中G表示下式(2):
A表示具有二至五個環的稠環烴單元,其中A表示萘基、菲基、蒽基、芘基、屈基、聯三伸苯基及苝基;L表示單鍵、經取代或未經取代的伸苯基或經取代或未經取代的雜伸苯基,X表示選自包含O、S、C(R5)(R6)、Si(R7)(R8)及N(R9)的原子或基團的二價橋,Ar表示稠合碳環或R1,m表示0至10的整數,n表示0至4的整數,p表示0至4的整數,R1至R9係獨立選自由氫原子、具有1至20個碳原子的經取代或未經取代的烷基、具有6至30個碳原子的經取代或未經取代的芳基、及具有3至30個碳原子的經取代或 未經取代的雜芳基所組成之群組。
鑒於上述教示顯然可以作出許多的修改及變化。因此,應該瞭解,在隨附申請專利範圍的範圍內,本發明可以除本文具體所述方式之外的其他方式來進行實踐。雖然,本文已示出並說明了具體實施例,但對於所屬技術領域中具有通常知識者來說,可在不偏離旨在單獨由隨附申請專利範圍限制的那些情況下,對本發明作出許多修改。
Claims (14)
- 一種發光材料,其由下式(1)表示:其中G表示下式(2):A表示具有二至五個環的稠環烴單元,其中A表示萘基(naphthyl group)、菲基(phenanthrenyl group)、蒽基(anthracenyl group)、芘基(pyrenyl group)、屈基(chrysenyl group)、聯三伸苯基(triphenylenyl group)及苝基(perylenyl group);L表示單鍵、經取代或未經取代的伸苯基(phenylene group)或經取代或未經取代的雜伸苯基(heterophenylene group),X表示選自包含O、S、C(R5)(R6)、Si(R7)(R8)及N(R9)的原子或基團的二價橋,Ar表示稠合碳環,m表示0至10的整數,n表示0至4的整數,p表示1至4的整數,R1至R9係獨立選自由氫原子、具有1至20個碳原子的經取代或未經取代的烷基、具有6至30個碳原子的經取代或未經取代的芳基、及具有3至30個碳原子的經取代或未經取代的雜芳基所組成之群組。
- 一種有機電致發光裝置,其包含由陰極及陽極組成的一電極對,且該電極對之間至少包含一發光層、及一或多層有機薄膜層,其中該發光層包含如申請專利範圍第1項所述具有式(1)之發光材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包含具有式(1)之該發光材料的該發光層為一螢光摻雜材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包含具有式(1)之該發光材料的該發光層為一延遲螢光摻雜材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層包含一第二螢光摻雜材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層包含一螢光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層包含一第二螢光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一有機發光裝置。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一發光面板。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一背光面板。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130069439A (ko) * | 2011-12-16 | 2013-06-26 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN106397398A (zh) * | 2016-08-31 | 2017-02-15 | 北京绿人科技有限责任公司 | 一种有机化合物及其在有机电致发光器件中的应用 |
KR20170040011A (ko) * | 2015-10-02 | 2017-04-12 | 성균관대학교산학협력단 | 지연형광 재료 및 이를 포함하는 유기 발광장치 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3287344B2 (ja) * | 1998-10-09 | 2002-06-04 | 株式会社デンソー | 有機el素子 |
JP2010195708A (ja) * | 2009-02-25 | 2010-09-09 | Toyo Ink Mfg Co Ltd | カルバゾリル基を有する化合物およびその用途 |
KR101120892B1 (ko) | 2009-06-19 | 2012-02-27 | 주식회사 두산 | 아크리딘 유도체 및 이를 포함하는 유기 전계 발광 소자 |
KR101793880B1 (ko) * | 2011-02-16 | 2017-11-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자 |
EP2690681B1 (en) | 2011-03-25 | 2019-09-11 | Idemitsu Kosan Co., Ltd | Organic electroluminescent element |
JP2014103212A (ja) | 2012-11-19 | 2014-06-05 | Samsung Display Co Ltd | アクリジン部位及びカルバゾール部位を有するアミン誘導体を含む有機el材料及びそれを用いた有機el素子 |
US20140175383A1 (en) * | 2012-12-20 | 2014-06-26 | Luminescence Technology Corporation | Indenotriphenylene derivatives and organic light emitting device using the same |
WO2014208698A1 (ja) * | 2013-06-26 | 2014-12-31 | 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、および電子機器 |
US11121327B2 (en) * | 2013-07-02 | 2021-09-14 | Merck Patent Gmbh | Spiro-condensed lactam compounds for organic electroluminescent devices |
KR102191990B1 (ko) * | 2013-09-10 | 2020-12-17 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US10103339B2 (en) * | 2015-02-11 | 2018-10-16 | Feng-wen Yen | Iridium complexes and organic electroluminescence device using the same |
US9893305B2 (en) * | 2015-06-01 | 2018-02-13 | Feng-wen Yen | Indenotriphenylene-based iridium complexes for organic electroluminescence device |
US10079347B2 (en) * | 2015-06-22 | 2018-09-18 | Feng-wen Yen | Compounds for organic electroluminescence device |
CN105131938B (zh) * | 2015-07-29 | 2017-11-24 | 中节能万润股份有限公司 | 一种有机电致发光材料及其应用 |
US9537103B1 (en) * | 2015-08-14 | 2017-01-03 | Luminescence Technology Corporation | Material for organic electroluminescence device and organic electroluminescence device using the same |
-
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130069439A (ko) * | 2011-12-16 | 2013-06-26 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
KR20170040011A (ko) * | 2015-10-02 | 2017-04-12 | 성균관대학교산학협력단 | 지연형광 재료 및 이를 포함하는 유기 발광장치 |
CN106397398A (zh) * | 2016-08-31 | 2017-02-15 | 北京绿人科技有限责任公司 | 一种有机化合物及其在有机电致发光器件中的应用 |
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