TW201808901A - 電場發光裝置的有機化合物 - Google Patents
電場發光裝置的有機化合物 Download PDFInfo
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Abstract
Description
本發明係關於使用有機材料之有機化合物和有機電場發光(有機EL)裝置。具體而言,本發明提供具有通式(1)的有機化合物,使用該有機化合物作為發光層的螢光發光客體之有機EL裝置。
有機電場發光(有機EL)為發光二極體(LED),其中發射層為因呼應電流而發光之有機化合物所製成的薄膜。有機化合物之發射層夾在兩個電極之間。有機EL因其高照度、低重量、超薄外形、無背光的自照明、低功耗、寬視角、高對比度、製造簡單、快速反應時間而應用於平板顯示器中。
有機材料電場發光的首次發現於1950年代早期,由安德列貝諾斯(Andre Bernanose)與其同事於法國南錫大學所發現。馬丁伯普(Martin Pope)與其紐約大學的同事,於1963年在真空下摻雜有稠四苯蒽的單一純晶體上,首次觀察到直流(DC)電場發光。
第一個二極體裝置,是由在伊士曼柯達(Eastman Kodak)的鄧青雲(Ching W.Tang)和史蒂芬凡斯萊克(Steven Van Slyke)於1987年所提出。該裝置採用具有單獨的電洞傳輸和電子傳輸層的雙層結構,可導致
降低操作電壓並提高效率,這促成當今主流的有機EL研究和裝置生產方式。
一般而言,有機EL裝置由位於兩個電極間的有機材料層組成,其包括電洞傳輸層(HTL)、發射層(EML)、電子傳輸層(ETL)。有機EL之基本機制包括載子注入、載子傳輸、複合以及形成發光的激子。當外部電壓施加到有機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)中,電洞將從陽極注入最高佔用分子軌域(highest occupied molecular orbital,HOMO)中。當電子與發光層中的電洞複合時,將會形成激子然後發光。當發光分子吸收能量來達到激發態時,根據電子和電洞自旋組合方式,激子可處於單重或三重態。75%的激子藉由電子和電洞的重組形成而達到三重激發態。從三重態衰減是自旋禁阻(self forbidden)的,因此,螢光電場發光裝置僅具有25%的內量子效率。與螢光電場發光裝置相反,磷光有機EL裝置利用自旋軌道相互作用,來促進單重態和三重態間的跨系統交叉,從而獲得單重態和三重態的發射,以及電場發光裝置的內部量子效率從25%至100%。
對於主動式有機發光二極體(AMOLED)的全色平板顯示器,使用於螢光發射層的材料在半衰期、效率、驅動電壓方面仍無法令人滿意。於本發明中,為了延長使用於有機EL裝置發光層中螢光客體的半衰期、並降低驅動電壓的目的,我們使用茚並三亞苯基-蒽基骨架連接到咔唑基、二苯並噻吩基、二苯並呋喃基、二芳基胺基、和其它供體基反應來完成通式(1)表示的有機化合物。有機化合物顯示出有機EL裝置的良
好熱穩定性和電荷載子遷移率。用於有機EL裝置的JP2013232520、KR20120072784、WO2008062636、WO2012091471、US8962160B2、US8993130B2、US9040174B2、US9048437B2、和20140175383A1中揭露之基於茚並三亞苯基骨架的衍生物。沒有現有技術證明茚並三亞苯-蒽骨架鏈,與用作有機EL裝置的螢光發光客體的咔唑基、二苯並噻吩基、二苯並呋喃基、二芳基胺基、和其它供體基相連。
根據上述原因,本發明之目的為解決現有技術的這些問題,並提供一種熱穩定性、高發光效率、高亮度、和長半衰期的發光裝置。本發明公開了具有通式(1)的有機材料,用作螢光發射客體材料,並具有良好電荷載子遷移率和優秀的操作耐久性,可降低驅動電壓和功率消耗、增加有機EL裝置效率和半衰期。
本發明提供一種有機化合物與其用於有機EL裝置發光層之螢光客體的用途。有機化合物可克服傳統材料的缺點,如:較短的半衰期、更低的效率、更高的驅動電壓。
本發明之目的為將有機化合物用作有機EL裝置的螢光發光客體,並且可降低驅動電壓、降低功耗並提高效率。
本發明具有工業實務之經濟優點。因此,本發明提供可用於有機EL裝置的有機化合物,其中有機化合物由下式(1)表示:
其中A代表式(2)至式(5):
上列詳細說明係針對本發明之一可行實施例之具體說
明,惟該實施例並非用以限制本發明之專利範圍,凡未脫離本發明技藝精神所為之等效實施或變更,均應包含於本案之專利範圍中。
綜上所述,本案不但在空間型態上確屬創新,並能較習用物品增進上述多項功效,應已充分符合新穎性及進步性之法定發明專利要件,爰依法提出申請,懇請 貴局核准本件發明專利申請案,以勵發明,至感德便。
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧電子阻擋層
10‧‧‧發射層
11‧‧‧電子傳輸層
12‧‧‧電子注入層
13‧‧‧金屬電極
圖1為本發明之電場發光裝置的有機化合物之實施例的有機EL裝置之示意圖。
為利 貴審查委員了解本發明之技術特徵、內容與優點及其所能達到之功效,茲將本發明配合附圖,並以實施例之表達形式詳細說明如下,而其中所使用之圖式,其主旨僅為示意及輔助說明書之用,未必為本發明實施後之真實比例與精準配置,故不應就所附之圖式的比例與配置關係解讀、侷限本發明於實際實施上的權利範圍,合先敘明。
在本發明的第一實施範例中,揭露了可用作有機EL裝置螢光發光客體的有機化合物。所提及的衍生物由下式(1)表示:
其中A代表式(2)至式(5):
其中m表示0至10的整數,n表示0或1的整數,X是選自原子或選自O、S和NR7的原子的二價橋,Y是選自原子或由O、S、C(R8)(R9)、Si(R10)(R11)和NR12、Ar1和Ar2表示具有6至30個碳原子的取代或未取代的芳基,R1至R12獨立地選自由以下組成的群組氫原子、鹵素、取代或未取代的碳原子數為1~30的烷基、取代或未取代的碳原子數為6~30的芳基、和取代或未取代的碳原子數為6~30的芳烷基。
於本實施範例中,部分有機化合物如下所示:
本發明中有機化合物的詳細製備可透過示例性實施方案來闡明,但是本發明不限於示例性實施方案。實施範例1~7顯示本發明中有機化合物的實施例的製備。實施範例8顯示有機EL裝置的製造和I-V-B、有機EL裝置測試報告的半衰期。
範例1
化合物1的合成
2-(聯苯-2-基)-7-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene)的合成
將35.2g(100mmol)的2,7-二溴-9,9-二甲基-9H-芴(2,7-dibromo-9,9-dimethyl-9H-fluorene)、21.8g(110mmol)的聯苯-2-基硼酸(biphenyl-2-ylboronic acid)、2.31g(2mmol)的Pd(PPh3)4、將75ml 2M Na2CO3、150ml EtOH的混合物和300ml甲苯脫氣,並置於氮氣下,然後在100℃加熱12小時。反應完成後,使混合物冷卻至室溫。有機層用乙酸乙酯(ethyl acetate)和水萃取,用硫酸鎂乾燥,除去溶劑,透過以矽膠柱色譜來純化殘餘物,得到黃色固體狀的產物(26.8g,63.0mmol,63%)。
12-溴-10,10-二甲基-10H-茚並[2,1-b]三亞苯
(12-bromo-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
在脫氣並充滿氮氣的3000ml三頸燒瓶中,將26.8g(60mmol)的2-(聯苯-2-基)-7-溴-9,9-二甲基-9H-芴(2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene)溶於無水二氯甲烷(1500ml)中,然後加入97.5g(600mmol)的氯化鐵(III)(Iron(III)chloride),將混合物攪拌1小時。於混合物中加入500ml的甲醇,並分離有機層,以真空方式除去溶劑。殘餘物通過矽膠柱色譜(己烷-二氯甲烷)得到白色固體(10.7g,25.3mmol,40%)。1H NMR(CDCl3,400MHz):化學位移(ppm)8.95(s,1H),8.79~8.74(m,2H),8.69~8.68(m,3H),7.84(d,J=8.0Hz,1H),7.72~7.65(m,5H),7.57(d,J=8.0Hz,1H),1.66(s,6H)。
2-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)-4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)的合成
將10.7g(25.3mmol)的12-溴-10,10-二甲基-10H-茚並[1,2-b]三亞苯(12-bromo-10,10-dimethyl-10H-indeno-[1,2-b]triphenylene),7.7g(30.3mmol)的雙(頻哪醇)二硼(bis(pinacolato)diboron),0.3g(0.26mmol)的Pd(PPh3)4,7.4g(75.4mmol)的乙酸鉀(potassium acetate)混合物,並將300ml的1,4-二噁烷(1,4-dioxane)脫氣並置於氮氣下,然後在90℃加熱16小時。反應完成後,使混合物冷卻至室溫。分離有機相並用乙酸乙酯(ethyl acetate)和水洗滌。以硫酸鎂(magnesium sulfate)乾燥後,真空除去溶劑。殘餘物通過矽膠柱色譜(己烷-二氯甲烷)純化,得到淺黃色固體產物(6.4g,13.7mmol,54%);1H NMR(CDCl3,400MHz):化學位移(ppm)9.03(s,1H),8.81(d,J=7.84Hz,1H),8.77(d,J=7.88Hz,1H),8.70~8.67(m,3H),8.02~7.93(m,3H),7.71~7.67(m,4H),1.69(s,6H),1.42(s,12H)。
12-(蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(anthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
將4.7g(10mmol)的2-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)-4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷(2-(10,10-dimethyl-10H
-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane),2.8g(11mmol)的9-溴蒽(9-bromoanthracene),0.22g(0.2mmol)的四(三苯基膦)鈀(tetrakis(triphenylphosphine)palladium),20ml 2M Na2CO3,20ml EtOH的混合物,和50ml的甲苯(toluene)的混合物脫氣,置於氮氣下,然後在90℃加熱過夜。反應完成後,使混合物冷卻至室溫。之後加入150ml的MeOH,同時進行攪拌,並抽吸濾出沉澱的產物。得到3.5g(產率67%)黃色產物,將其從甲苯中再結晶。
12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)的合成
將得到的12-(蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(anthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene)(3.5g)和DMF(35ml)加入反應容器中。在冰冷卻的條件下,加入N-溴代琥珀酰亞胺(N-bromosuccinimide)(1.5g),將混合物攪拌9小時。加入水(350ml),有機層用二氯甲烷和水萃取,以無水硫酸鎂(anhydrous magnesium sulfate)乾燥,除去溶劑,殘餘物通過矽膠柱色譜(己烷-二氯甲烷)純化,得到淺黃色固體產物(3.1g,5.2mmol,78%)。
3-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-基)-9-苯基-9H-咔唑(3-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-
yl)anthracen-9-yl)-9-phenyl-9H-carbazole)的合成
將3.1g(5.2mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),2.2g(6mmol)的9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),0.22g(0.2mmol)的四(三苯基膦)鈀(tetrakis(triphenylphosphine)palladium),20ml 2M Na2CO3,20ml EtOH的混合物和50ml的甲苯(toluene)脫氣並置於氮氣下,然後在110℃加熱過夜。反應完成後,使混合物冷卻至室溫。之後加入150ml的MeOH,同時進行攪拌,並抽吸濾出沉澱的產物。得到2.6g(產率67%)黃色產物,將其從甲苯中再結晶。MS(m/z,FAB+):761.4,1H NMR(CDCl3,400MHz):化學位移(ppm)9.11(s,1H),8.87(d,J=7.84Hz,1H),8.80~8.75(m,2H),8.71~8.69(m,2H),8.28(d,J=7.84Hz,1H),8.22~8.11(m,2H),7.88~7.82(m,4H),7.76~7.63(m,10H),7.61~7.44(m,5H),7.39~7.28(m,5H),1.74(s,6H)。
範例2
化合物6的合成
10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)-N-苯基-N-間甲苯基蒽-9-胺(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-N-phenyl-N-m-tolylanthracen-9-amine)的合成
將6.0g(10mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),3g(15.1mmol)的3-甲基-N-苯基苯胺(3-methyl-N-phenylaniline),0.05g(0.2mmol)的乙酸鈀(II)(palladium(II)acetate),0.15g(0.4mmol)的2-(二環己基膦基)聯苯(2-(dicyclohexylphosphino)biphenyl),2g(20mmol)的叔丁醇鈉(sodium tert-butoxide)的混合物和100ml的鄰二甲苯(O-xylene)的混合物回流過夜。反應完成後,將溶液在100℃下過濾,以得到濾液,將濾液加入1L的MeOH中,同時進行攪拌,並將沉澱的產物抽濾。得到3.1g(產率45%)黃色產物,將其從甲苯中再結晶。MS(m/z,FAB+):701.6。
範例3
化合物12的合成
N-(2-氯苯基)-9,9-二甲基-9H-芴-2-胺(N-(2-chlorophenyl)
-9,9-dimethyl-9H-fluoren-2-amine)的合成
將6.9g(25.3mmol)的2-溴-9,9-二甲基-9H-芴(2-bromo-9,9-dimethyl-9H-fluorene),3.2g(25.3mmol)的2-氯苯胺(2-chloroaniline),0.11g(0.5mmol)的乙酸鈀(II)(palladium(II)acetate),0.55g(1.0mmol)的1,1-雙(二苯基膦基)二茂鐵(1,1-bis(diphenyl-phosphino)ferrocene),4.85g(50.6mmol)的叔丁醇鈉(sodium tert-butoxide)混合物和100ml甲苯(toluene)脫氣,置於氮氣下,然後在110℃加熱過夜。反應完成後,使混合物冷卻至室溫。分離有機相並用乙酸乙酯和水洗滌。以硫酸鎂乾燥後,真空除去溶劑。殘餘物通過矽膠柱色譜(己烷-二氯甲烷)純化,得到淺黃色固體產物(4.9g,18.0mmol,71%)。
3,3-二甲基-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
將4.9g(18.0mmol)的N-(2-氯苯基)-9,9-二甲基-9H-芴-2-胺(N-(2-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine),0.4g(1.6mmol)的乙酸鈀(II)(palladium(II)acetate),75ml的新戊酸(pivalic acid),將0.8g的
碳酸鉀(6mmol)(potassium carbonate)和240ml的1-甲基-2-吡咯烷酮(1-methyl-2-pyrrolidone)的混合物脫氣並置於氮氣下,然後在130℃加熱24小時。反應完成後,使混合物冷卻至室溫。有機層用二氯甲烷(dichloromethane)和水萃取,以無水硫酸鎂(anhydrous magnesium sulfate)乾燥,除去溶劑,殘餘物從己烷(hexane)和二氯甲烷(dichloromethane)中再結晶,得到產物(2.1g,7.4mmol,產率41%)。
3,3-二甲基-1-苯基-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
將4.9g(18mmol)的3,3-二甲基-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1,3-dihydroindeno[2,1-b]carbazole),3.4g(21.6mmol)的溴苯(bromobenzene),0.1g(0.4mmol)的乙酸鈀(II)(palladium(II)acetate),將0.3g(0.8mmol)的2-(二環己基膦基)聯苯(2-(dicyclohexylphosphino)biphenyl),4g(40mmol)的叔丁醇鈉(sodium tert-butoxide)的混合物和50ml的鄰二甲苯(o-xylene)在氮氣下回流過夜。反應完成後,將溶液在100℃下過濾以接收濾液,將濾液加入1L的MeOH中,同時進行攪拌,並將沉澱的產物抽吸過濾。得到(4.1g,11.5mmol,64%)黃色產物,將其從甲苯中再結晶。
10-溴-3,3-二甲基-1-苯基-1,3-二氫茚並[2,1-b]咔唑(10-br
omo-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
將得到的3,3-二甲基-1-苯基-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)(4.1g)和DMF(40ml)加入到反應容器中。於冰冷卻的條件下加入N-溴代琥珀酰亞胺(N-bromosuccinimide)(2g),將混合物攪拌6小時,然後靜置一夜。加入400ml水,有機層用二氯甲烷(dichloromethane)和水萃取,用無水硫酸鎂(anhydrous magnesium sulfate)乾燥,除去溶劑,殘餘物通過矽膠柱色譜(己烷-二氯甲烷)純化,得到產物(2.9g,6.7mmol,72%)。
3,3-二甲基-1-苯基-10-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1-phenyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydroindeno[2,1-b]carbazole)的合成
將2.9g(6.7mmol)的10-溴-3,3-二甲基-1-苯基-1,3-二氫茚並[2,1-b]咔唑(10-bromo-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole),2.2g(8.67mmol)的雙(頻哪醇)二硼(bis(pinacolato)diboron),0.36g(0.32mmol)的四(三苯基膦)鈀(tetrakis(triphenylphosphine)palladium),2g(20.28mmol)的乙酸鉀(potassium acetate)的混合物和300ml的1,4-二噁烷(1,4-dioxane)脫氣,置於氮氣下,然後在120℃加熱16小時。反應完成後,使混合物冷卻至室溫。有機層用乙酸乙酯(ethyl acetate)和水萃取,以無水硫酸鎂(anhydrous magnesium sulfate)乾燥,除去溶劑,產物透過使用己烷(hexanes)和乙酸乙酯(ethyl acetate)的混合物,作為洗脫劑的柱純化,得到2.4g淺黃色產物(產率76%)。
10-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-基)-3,3-二甲基-1-苯基-1,3-二氫茚並[2,1-b]咔唑(10-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)-3,3-dimethyl-1-phenyl-1,3-dihydroindeno[2,1-b]carbazole)的合成
將5g(5mmol)的12-(10-溴蒽-9-基)-10,10-二甲基-10H-茚並[2,1-b]三亞苯(12-(10-bromoanthracen-9-yl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene),2.4g(5mmol)的3,3-二甲基-1-苯基-10-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-1,3-二氫茚並[2,1-b]咔唑(3,3-dimethyl-1-phenyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydroindeno[2,1-b]carbazole),0.22g(0.2mmol)的四(三苯基膦)鈀(tetrakis(triphenyl phosphine)palladium),20ml 2M Na2CO3,20ml EtOH的混合物和50ml的甲苯(toluene)的混合物脫氣,置於氮氣下,然後在110℃加熱過夜。反應完成後,使混合物冷卻至室溫。之後加入150ml的MeOH,同時進行攪拌,並抽吸濾出沉澱的產物。得到2.6g(產率67%)黃色產物,將其從甲苯中再結晶。MS(m/z,FAB+):877.6,1H NMR(CDCl3,400MHz):化學位移(ppm)9.13(s,1H),8.85(d,J=7.84Hz,1H),8.78~8.74(m,2H),8.73~8.68(m,2H),8.28~8.24(m,3H),8.22~8.11(m,2H),7.88~7.82(m,4H),7.76~7.63(m,10H),7.62~7.43(m,5H),7.38~7.28(m,5H),1.74(s,6H),1.57(s,6H)。
範例4
化合物17的合成
2-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-
基)二苯並[b,d]呋喃(2-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenzo[b,d]furan)的合成
二苯並[b,d]呋喃-2-基硼酸(Dibenzo[b,d]furan-2-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用與合成實施範例1相同的方法,獲得化合物17的所需化合物(1.4g,產率=57%)。MS(m/z,FAB+):686.3。
範例5
化合物18的合成
4-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-基)二苯並[b,d]噻吩(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenzo[b,d]thiophene)的合成
二苯並[b,d]噻吩-4-基硼酸(Dibenzo[b,d]thiophen-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用與合成實施範例1中相同的方法,獲得化合物18的所需化合物(1.8g,產率=68%)。MS(m/z,FAB+):720.8。
範例6
化合物19的合成
4-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-基)二苯並[b,d]噻吩(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenzo[b,d]thiophene)的合成
二苯並[b,d]噻吩-4-基硼酸(Dibenzo[b,d]thiophen-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用與合成實施例1中相同的方法,獲得化合物19的所需化合物(1.8g,產率=68%)。MS(m/z,FAB+):720.8。
範例7
化合物20的合成
4-(10-(10,10-二甲基-10H-茚並[2,1-b]三苯基-12-基)蒽-9-基)二苯並[b,d]呋喃(4-(10-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)anthracen-9-yl)dibenzo[b,d]furan)的合成
二苯並[b,d]呋喃-4-基硼酸(Dibenzo[b,d]furan-4-ylboronic acid)代替9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷-2-基)-9H-咔唑(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole),使用與合成實施範例1中相同的方法,獲得化合物20的所需化合物(2.6g,產率=53%)。MS(m/z,FAB+):686.4。
生產有機EL裝置的一般方法
提供具有9~12歐姆/平方的電阻、120~160nm厚度的ITO塗裝的玻璃(以下稱為ITO基材),並在超聲波浴(例如:清潔劑、去離子水)中進行清潔。在有機層的氣相沉積之前,透過UV和臭氧進一步處理經清潔後的ITO基材。ITO基材的所有預處理流程,都在淨化室(100級)下進行。
透過氣相沉積在高真空單元(10-7Torr),將這些有機層按順序施加至ITO基材上,例如:電阻加熱的石英舟。借助於石英晶體監測器來精確地監測、或設置各層的厚度和氣相沉積速率(0.1~0.3nm/sec)。如上所述,單個層也可以由一種以上的化合物所組成,例:通常是摻
雜有摻雜劑材料的主體材料。這可透過兩個或更多個來源的共蒸發來實現。
二吡嗪並[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)用作該有機EL裝置中的電洞注入層,N,N-雙(萘-1-基)-N,N-雙(苯基)-聯苯胺(N,N-Bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine,NPB)被最廣泛地用作電洞傳輸層;在有機EL裝置中使用10,10-二甲基-12-(10-(4-(萘-1-基)苯基)蒽-9-基)-10H-茚並[2,1-b]三亞苯(H3)(10,10-dimethyl-12-(10-(4-(naphthalene-1-yl)phenyl)anthracen-9-yl)-10H-indeno[2,1-b]triphenylene)和10,10-二甲基-13-(10-(3-(萘-2-基)苯基)蒽-9-基)-10H-茚並[2,1-b]三亞苯(H4)(10,10-dimethyl-13-(10-(3-(naphthalen-2-yl)phenyl)anthracen-9-yl)-10H-indeno[2,1-b]triphenylene)作為發射主體,N1,N1,N6,N6-四-甲苯基芘-1,6-二胺(D1)(N1,N1,N6,N6-tetram-tolylpyrene-1,6-diamine)作為藍色客體並使用於比較用途;HB3(參見下面的化學結構)用作電洞阻擋材料(HBM)和1-(4-(10-(萘-2-基)蒽-9-基)苯基)-2-苯基-1H-苯並[d]咪唑(ET2)(1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole)用作電子傳輸材料,以在有機EL裝置中與8-羥基喹啉鋰(8-hydroxyquinolato-lithium,LiQ)共沉澱。用於產生標準有機EL裝置控制組之現有技術的OLED材料,和本發明中比較性材料的化學結構如下:
典型的有機EL裝置由低功函數金屬所組成,如:Al,Mg,Ca,Li和K,藉由熱蒸發來作為陰極,低功函數金屬可幫助從陰極注入電子傳輸層的電子。此外,為了減少電子注入阻障,並且改善有機EL裝置的性能,在陰極與電子傳輸層之間導入薄膜電子注入層。電子注入層的傳統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,於有機EL裝置製造後,可使用PR650光譜掃描光譜儀來測量EL光譜和CIE座標。此外,使用Keithley 2400可編程設計電壓-電流源,來獲得電流/電壓、發光/電壓以及良率/電壓等特性。上述提及的設備可在室溫(約25℃)下,並且於大氣壓力下進行操作。
範例8
使用與上述一般方法類似的方法,製作具有以下器件結構的螢光發射有機EL裝置(參見圖1),其中具有透明電極6及金屬電極13,及金屬電極13之間具有機依序沉積至透明電極6上的電洞注入層7、電洞傳輸層8,沉積到電洞傳輸層8上之電子阻擋層9,沉積到電子阻擋層9上之螢光或磷光發射層10,沉積到發射層10上之電子傳輸層11,沉積到電子傳輸層11上之電子注入層12。裝置:ITO/HAT-CN(20nm)/NPB(110nm)/發射主體摻雜5%發光客體(30nm)/HB3/ET2摻雜50%LiQ(35nm)/LiQ(1nm)/Al(160nm)。發射螢光的有機EL裝置測試報告的I-V-B(1000尼特(nit)下)和半衰期時間如表1所報導。半衰期時間被定義為1000cd/m 2的初始亮度降到一半的時間。
表1
在上述有機EL裝置試驗報告(參見表1)的優選實施方案中,我們顯示於本發明中用作有機EL的發光客體材料通式(1)的有機化合物,能顯示出良好的性能。更具體而言,本發明中的有機EL裝置使用具有通式(1)的有機化合物,作為發光客體材料,以及例如:H3和H4的發光主體材料配位,來表現出更低的功耗、更高的效率和更長的半衰期。
總而言之,本發明揭露了一種用作有機EL裝置的發光客體材料通式(1)的有機化合物。所述有機化合物由下式(1)表示:本發明具有工業實務之經濟優點。因此,本發明提供可用於有機EL裝置的有機化合物,其中有機化合物由下式(1)表示:
其中A代表式(2)至式(5):
綜上所述,本案不僅於技術思想上確屬創新,並具備習
用之傳統方法所不及之上述多項功效,已充分符合新穎性及進步性之法定發明專利要件,爰依法提出申請,懇請 貴局核准本件發明專利申請案,以勵發明,至感德便。
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧電子阻擋層
10‧‧‧發射層
11‧‧‧電子傳輸層
12‧‧‧電子注入層
13‧‧‧金屬電極
Claims (9)
- 一種具有通式(1)的有機化合物如下:
- 如申請專利範圍第1項所述之有機化合物,其中該有機化合物進一步選自:
- 一種有機電激發光裝置,其包括由陰極和陽極組成的一對電極對,其中該對電極對之間至少包含一層發光層、複數個有機薄膜層,其中該發光層包含如申請專利範圍第1項所述之有機化合物。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該發光層係由如申請專利範圍第1項所述之有機化合物作為客體材料。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該發光層係由如申請專利範圍第1項所述之有機化合物作為螢光發射客體材料。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該發光層係發射藍色螢光。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該有機電激發光裝置係為有機發光裝置(organic light emitting device,OLED)。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該有機電激發光裝置係為照明面板。
- 如申請專利範圍第3項所述之有機電激發光裝置,其中該有機電激發光裝置係為背光面板。
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