TWI659959B - 有機電致發光裝置的延遲螢光材料 - Google Patents
有機電致發光裝置的延遲螢光材料 Download PDFInfo
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- TWI659959B TWI659959B TW106130388A TW106130388A TWI659959B TW I659959 B TWI659959 B TW I659959B TW 106130388 A TW106130388 A TW 106130388A TW 106130388 A TW106130388 A TW 106130388A TW I659959 B TWI659959 B TW I659959B
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- 239000000463 material Substances 0.000 title claims abstract description 62
- 230000003111 delayed effect Effects 0.000 title claims abstract description 47
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 238000004735 phosphorescence spectroscopy Methods 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 238000000628 photoluminescence spectroscopy Methods 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 238000001161 time-correlated single photon counting Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
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Abstract
本發明揭露一種延遲螢光材料,此延遲螢光材料具有通式(1),且使用該材料作為發光層的延遲螢光材料或發光層的磷光發光主體之有機電致發光裝置具有良好的性能表現。
Description
本發明係為一種材料及使用該材料的有機電致發光(Organic Electroluminescence,以下簡稱為有機EL)裝置。具體而言,本發明涉及一種具有通式(1)的延遲螢光材料及一種有機電致發光裝置,該有機EL裝置使用該材料作為發光層的延遲螢光材料或發光層的磷光發光主體,本發明之電致發光裝置可顯示極佳的性能。
有機電致發光裝置因其高照度、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。
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。該裝置採用具有單獨的電洞傳輸層和電子傳輸層的雙層結構,可導致操作電壓的降低及效率的提高,這促成當今主流的有機EL研究及其裝置生產方式。
一般而言,有機EL裝置由位於兩個電極之間的有機材 料層組成,其包括電洞傳輸層(hole transport layer,HTL)、發光層(emitting layer,EML)、電子傳輸層(electron transport layer,ETL)。有機EL的基本機制包括載子的注入、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,電子及電洞將分別自陰極及陽極注入,電子將從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital,LUMO)中,且電洞將從陽極注入最高佔用分子軌域(highest occupied molecular orbital,HOMO)中。當電子與電洞在發光層中複合時,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,根據電子及電洞自旋組合方式,而激子可處於單重態或三重態。透過重組電子及電洞形成75%的激子而達到三重激發態。從三重態的衰減為自旋禁阻,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及三重態之間的跨系統交叉,從而獲得單重態和三重態的發射,以及電致發光裝置的內部量子效率從25%到100%。自旋軌域交互作用由一些重原子完成,比如,銥、銠、鉑、鈀,且可從有機金屬複合物的激發金屬配位基電荷轉移(metal-to-ligand charge-transfer transition,MLCT)狀態來觀察磷光躍遷。
近來,安達(Adachi)及同事已開發熱活化型延遲螢光(thermally activated delayed fluorescence,TADF)機制,並將其整合至新型螢光有機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穿越(reverse intersystem crossing,RISC)機制,將自旋禁阻的三重態激子轉化為單重態而獲得高效率的激子。然而,於高電流密度中仍需要進一步提高有機EL裝置的發光效率。
有機EL利用三重態激子和單重態激子。磷光有機EL通常在發光層(EML)及電子傳輸層(ETL)之間需要附加電洞阻擋層(hole blocking layer,HBL),或在發光層(EML)及電洞傳輸層(HTL)之間附加電子阻擋層(electron blocking layer,EBL),因此,與單重態激子相比,三重態激子壽命更長、擴散長度更長。使用HBL或EBL的目的是限制注入的電洞及電子的複合以及使EML內所產生的激子弛豫,藉此可提高裝置的效率。為了滿足這些作用,電洞阻擋材料或電子阻擋材料必須具有適合於阻斷電洞或電子從EML傳輸至ETL或到HTL的HOMO和LUMO能階。
對於主動矩陣有機發光二極體(active-matrix organic light-emitting diode,AMOLED)或有機發光二極體(organic light-emitting diode,OLED)為發光面板的全彩平板顯示器來說,使用於發光層中磷光主體材料之,對於工業實務使用而言,在半衰期、效率及驅動電壓方面仍無法令人滿意。除此之外,為了呈現有機EL裝置的優異性能,磷光發光主體材料需與其他有機薄膜層(例如:電洞阻擋層及電子傳輸層)配位,以達到低能耗、長半衰期及高效率。因此,需要設計及開發用於有機EL裝置的新型材料。
在本發明中,為了使有機EL裝置中延遲螢光化合物的偶極材料延遲半衰期、提高效率及顯示極佳性能,我們使用骨架式(1)作為供體並使用骨架中的R1、R2及R3位置連接受體,來完成表現極佳性能的如通式(1)的延遲螢光材料,該受體包含三嗪基(triazinyl group)、二嗪基(diazinyl group)、吡啶基(pyridinyl group)、喹啉基(quinoline group)、異喹啉基(isoquinoline group)、磺醯基二苯基(sulfonyldibenzene group)、二苯酮基(benzophenone group)及其他電子受體基團。
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、高發光效率及長衰期上表現極佳。本發明揭露一種具有通式(1)的延遲螢光材料,其用作發光層的延遲螢光材料或發光層的磷光發光主體,該等層具有良好的電荷載子遷移率,且極佳的使用壽命可降低有機EL裝置的驅動電壓和能耗、增加有機EL裝置的效率並延長其半衰期。
本發明具有工業應用的經濟優點。相應地,本發明揭露了可用於有機EL裝置的延遲螢光材料。所述延遲螢光材料由下式(1)表示:
其中W分別表示氧原子、硫原子及硒原子;R1、R2及R3分別選自由氫原子、氘原子、鹵化物、式(2)或式(3)組成的基團:
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係為本發明之用於有機電致發光裝置之延遲螢光化合物之實施例的有機EL裝置之示意圖。
圖2係為化合物TD4的延遲螢光特性的瞬時衰變固化。
本發明研究用於使用該材料的有機EL裝置的延遲螢光材料。下面將詳細說明生產、結構及組成部份,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具有通常知識者熟知的具體 細節。另一方面,眾所周知的一般組成成份和程序不作詳細說明,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,應該瞭解本發明可實際操作於各種其他實施例中,而非本發明詳細所述的實施例中,也就是說,本發明還可廣泛地應用於其他實施例,且本發明的範圍沒有明確的限制,除隨附申請專利權利範圍限定的內容。
在本發明的第一個實施例中,揭露了可用作有機EL裝置的發光層的熱活化延遲螢光(thermally activated delayed fluorescence,TADF)材料。所述延遲螢光材料由下式(1)表示:
其中W分別表示氧原子、硫原子及硒原子;R1、R2及R3分別選自由氫原子、氘原子、鹵化物、式(2)或式(3)組成的基團:
根據上述有機延遲螢光材料式(1),其中該延遲螢光材料式(1)由下式(4)至式(12)表示:
在本實施例中,一些延遲螢光材料所示如下:
本發明中延遲螢光材料的詳細製備由示例性實施例闡明,但本發明不限於示例性實施例。實施例1至實施例4展示出了本發明中延遲螢光材料的製備範例。實施例5展示出有機EL裝置及I-V-B的製作、有機EL裝置的半衰期測試報告。
實施例1
TD1的合成
中間體A的合成
混合20g(99mmol)1-溴-2-硝基苯(1-Bromo-2-nitrobe nzene)、19g(148.4mmol)3-噻吩硼酸(3-thienylboronic acid)、5.7g(4.93mmol)四(三苯基膦)鈀(Pd(pph3)4)、27.4g(198.2mmol)碳酸鉀(K2CO3)、300ml的二甲基甲醯胺(Dimethylformamide,DMF)及80ml的水,放置在氮氣中,隨後在80℃加熱攪拌5h。反應完成後,使混合物冷卻至室溫。溶液使用100ml乙酸乙酯(ethyl acetate)(3次)及300ml水 萃取。有機層使用無水硫酸鎂(anhydrous magnesium sulfate)乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到黃色液體產物(19g,92.5mmol,產率:93.5%)。
中間體B的合成
在0℃的環境下,10分鐘內,將溴化苯鎂(PhMgBr)(1M於THF溶液中)(170ml,170.5mmol)緩慢加入(0.3ml/min)中間體A(10g,48.7mmol)及無水四氫呋喃(Tetrahydrofuran,THF)(300ml)的混合物中。在此期間,嚴密監控內部溫度並控制保持在3℃以下。隨後,在0℃下攪拌該混合物5分鐘,之後緩慢並小心加入飽和氯化銨(NH4Cl)水溶液(30ml)。控制內部溫度以便其保持低於5℃。隨後,加入50ml水,使用乙酸乙酯(3×100mL)萃取所得混合物。使用鹽水(brine)(200ml)清洗混合有機層,在無水硫酸鈉(Na2SO4)下乾燥並在真空中濃縮。初步的產物透過矽膠管柱層析法純化,得到白色固體產物(4g,5.77mmol,產率:47.6%)。
中間體C的合成
混合5g(28.8mmol)中間體B、5.6g(32mmol)1-溴-2-氟苯(1-Bromo-2-fluorobenzene)、14.1g(43.3mmol)碳酸銫(Caesium carbonate)及80ml DMF,並放置在氮氣中,隨後在150℃加熱攪拌12h。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到紫色固體產物(9g,27.4mmol,產率:94.7%)。
中間體D的合成
混合7.5g(22.8mmol)中間體C、15.8g(114.3mmol)K2CO3、2.4g(9.15mmol)PPh3、5.2g(22.8mmol)苄基三乙基氯化銨(Benzyltriethyl ammonium chloride)、0.78g(3.47mmol)乙酸鈀(Pd(OAc)2)及150ml二甲基乙醯胺(Dimethylacetamide,DMAc),並放置在氮氣中,隨後在160℃加熱攪拌5h。反應完成後,使混合物冷卻至室溫。溶液使用250ml二氯甲烷(Dichloromethane,DCM)及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到粉紅色固體產物(2.1g,8.49mmol,產率:37.5%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.08-8.07(d,1H)、7.91-7.89(d,1H)、7.85-7.84(d,1H)、7.69-7.67(d,1H)、7.54-7.46(m,3H)、7.34-7.31(m,1H)、7.06-7.05(d,1H)。
中間體E的合成
在氮氣淨化系統中,將2.1g(8.49mmol)中間體D及1.6g(8.98mmol)N-溴琥珀醯亞胺(N-bromosuccinimide)加入50ml DMF中,將其密閉,並攪拌混合物12h。反應完成後,混合物使用250ml DCM及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到白色固體產物(2.2g,6.74mmol,產率:79.1%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.10-8.08(d,1H)、7.93-7.92(d,1H)、7.82-7.81(d,1H)、7.64-7.63(d,1H)、7.56-7.50(m,3H)、7.37-7.34(m,1H)。
TD1的合成
將2g(6.13mmol)中間體E、2.9g(6.66mmol)2,4-二 苯基-6-(3-(4’4,5,5-四甲基-1,3,2-二氧雜硼烷-2-基)苯基)-1,3,5-三嗪(2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine)、0.14g(0.12mmol)Pd(pph3)4、0.1g(0.28mmol)2-(二環己基磷基)聯苯(2-(dicyclohexylphosphino)biphenyl)、12ml 2M Na2CO3、20ml乙醇(EtOH)及60ml甲苯(toluene)混合物除氣並放置在氮氣中,隨後在90℃加熱過夜。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到淺黃色固體產物(2.8g,5.04mmol,產率:82.3%)。1H NMR(500MHz,CDCl3):化學位移(ppm)9.05(t,1H),8.82-8.80(q,4H),8.69-8.67(d,1H),8.10-8.09(d,1H),7.93-7.88(m,4H),7.76-7.74(d,1H),7.64-7.52(m,9H),7.35(t,1H);MS m/z:C37H22N4S的理論值:554.157;測量值:554.153。
實施例2
TD2的合成
TD2的合成
將2.2g(6.74mmol)中間體E、10.7g(7.35mmol)2,4-二苯基-6-(4-(4.4,5,5-四甲基-1,3,2-二氧碰雜環戊烷-2-基)苯基)-1,3,5- 三嗪(2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine)、0.16g(0.13mmol)Pd(pph3)4、0.1g(0.28mmol)2-(二環己基磷)聯苯(2-(dicyclohexylphosphino)biphenyl)、15ml 2M Na2CO3、30ml EtOH及90ml甲苯混合物除氣並放置在氮氣中,隨後在90℃加熱過夜。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到淺黃色固體產物(3g,5.4mmol,產率:80.1%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.83-8.81(d,2H)、8.79-8.78(d,4H)、8.11-8.10(d,1H)、7.94-7.86(m,4H)、7.75-7.74(d,1H)、7.62-7.53(m,9H)、7.36(t,1H);MS m/z:C37H22N4S的理論值:554.157;測量值:554.155。
實施例3
TD3的合成
中間體F的合成
混合4g(23.1mmol)中間體B、6.4g(25.4mmol)2,4-溴-1-氟苯(2,4-Bromo-2-fluorobenzene)、11.3g(34.6mmol)碳酸銫及80ml DMF,並放置在氮氣中,隨後在150℃加熱攪拌12h。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用 無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到白色固體產物(7.8g,19.2mmol,產率:83.1%)。
中間體G的合成
混合7.5g(18.4mmol)中間體F、12.7g(92.1mmol)K2CO3、1.9g(7.37mmol)PPh3、4g(18.4mmol)苄基三乙基氯化銨、0.62g(2.76mmol)Pd(OAc)2及150ml DMAc,並放置在氮氣中,隨後在160℃加熱攪拌5h。反應完成後,使混合物冷卻至室溫。溶液使用250ml DCM及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到粉紅色固體產物(1.9g,5.82mmol,產率:32.3%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.11-8.10(d,1H)、8.04(s,1H)、7.65-7.63(d,1H)、7.53-7.51(d,1H)、7.46-7.44(d,1H)、7.31-7.27(m,2H)、6.98-6.97(d,1H)。
TD3的合成
將1.9g(5.82mmol)中間體G、10.7g(6.40mmol)2,4-二苯基-6-(4-(4,4,5,5-四甲基-1,3,2-二氧雜硼烷-2-基)苯基)-1,3,5-三嗪(2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine)、0.13g(0.12mmol)Pd(pph3)4、0.1g(0.12mmol)2-(二環己基磷)聯苯(2-(dicyclohexylphosphino)biphenyl)、15ml 2M Na2CO3、30ml EtOH及90ml甲苯混合物除氣並放置在氮氣中,隨後在90℃加熱過夜。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到黃色固體產物(2.3g,4.1mmol,產率:73.1%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.62-8.58(m,4H),8.54-8.52(d,1H),8.41-8.39(m,3H),8.31(s,1H),7.83-7.72(m,2H),7.69-7.60(m,9H),7.41-7.39(d,1H)7.13-7.11(d,1H);MS m/z C37H22N4S的理論值:554.157;測量值:554.159。
實施例4
TD4的合成
中間體H的合成
混合15g(45.7mmol)4-溴-2-碘-1-硝基苯(4-bromo-2-iodo-1-nitrobenzene)、8.8g(68.6mmol)3-噻吩硼酸(3-thienylboronic acid)、2.6g(2.3mmol)Pd(pph3)2、12.6g(91.4mmol)K2CO3、300ml DMF及80ml水,並放置在氮氣中,隨後在80℃加熱攪拌5h。反應完成後,使混合物冷卻至室溫。溶液使用100ml乙酸乙酯(3次)及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到黃色液體產物(11.7g,41.2mmol,產率:90.1%)。
中間體I的合成
在0℃環境下,10分鐘內,將PhMgBr(1M於THF溶液中)(123.2ml,123.2mmol)緩慢加入(0.3ml/min)中間體H(10g,35.2mmol)及無水THF(300ml)的混合物中。在此期間,嚴密監控內部溫度並控制保持在3℃以下。隨後,在0℃下攪拌該混合物5分鐘,之後緩慢並小心加入飽和NH4Cl水溶液(30ml)。控制內部溫度以便其保持低於5℃。隨後,加入50ml水,使用乙酸乙酯(3×100mL)萃取所得混合物。 使用鹽水(200ml)清洗混合有機層,在無水Na2SO4下乾燥並在真空中濃縮。初始產物透過矽膠管柱層析法純化,得到白色固體產物(4.1g,16.3mmol,產率:46.3%)。
中間體J的合成
混合4g(15.8mmol)中間體I、3g(17.1mmol)1-溴-2-氟苯(1-Bromo-2-fluorobenzene)、3.2g(23.8mmol)碳酸銫及80ml DMF,並放置在氮氣中,隨後在150℃加熱攪拌12h。反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到紫色固體產物(6g,14.8mmol,產率:93.2%)。
中間體K的合成
混合6g(14.7mmol)中間體J、10.2g(73.8mmol)K2CO3、 1.5g(5.89mmol)PPh3、3.3g(14.7mmol)苄基三乙基氯化銨、0.5g(2.21mmol)Pd(OAc)2及150ml DMAc,並放置在氮氣中,隨後在160℃加熱攪拌5h。反應完成後,使混合物冷卻至室溫。溶液使用250ml DCM及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到粉紅色固體產物(1.9g,5.9mmol,產率:40.1%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.10-8.09(d,1H),8.08(s,1H),7.66-7.60(m,1H),7.52(s,1H),7.48-7.45(m,1H),7.32-7.29(m,1H),7.21-7.20(d,1H),6.92-6.91(d,1H)。
TD4的合成
將2g(6.13mmol)中間體E、2.9g(6.66mmol)2,4-二苯基-6-(3-(4,4,5,5-四甲基-1,3,2-二氧雜硼烷-2-基)苯基)-1,3,5-三嗪(2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine)、0.14g(0.12mmol)Pd(pph3)4、0.1g(0.28mmol)2-(二環己基磷基)聯苯(2-(dicyclohexylphosphino)biphenyl)、12ml 2M Na2CO3、20ml EtOH及60ml甲苯混合物除氣並放置在氮氣中,隨後在90℃加熱過夜。 反應完成後,使混合物冷卻至室溫。溶液使用250ml乙酸乙酯及300ml水萃取。有機層使用無水硫酸鎂乾燥並在減壓下蒸發溶劑。殘留物透過矽膠管柱層析法純化,得到淺黃色固體產物(2.9g,5.22mmol,產率:85.1%)。1H NMR(500MHz,CDCl3):化學位移(ppm)8.30-8.26(m,5H),8.12-8.10(d,1H),7.74(s,1H),7.70(s,1H),7.68-7.36(m,10H),7.32-7.29(m,2H),7.23-7.22(d,1H),6.96-6.95(d,1H);MS m/z:C37H22N4S的理論值:554.157;測量值:554.159
延遲螢光化合物之光物理特性的測量方法
光物理特徵:合成的化合物在高真空下透過溫度梯度進行昇華,隨後用在之後的研究中。透過在基礎壓力<10-6torr的真空室中以1-2A/sec的速率於石英基材上熱蒸發來製備光物理特徵的薄膜。所得薄膜及吸收溶液的吸收光譜由UV-vis-NIR分光光度儀(UV-1650 PC,Shimadzu)檢測。光激螢光(Photoluminescence,PL)光譜、冷光量子吸收量(photoluminescence quantum yields,PLQYs)及磷光光譜由螢光分光光度儀(FluoroMax-P,Horiba Jobin Yvon Inc.)檢測薄膜或稀釋溶液的PLQYs使用配備校準積分球的該螢光分光光度儀來檢測。使用選定的單色激發光來激發位於校準積分球中的激發樣本。透過對比單色激發光及PL發射的光譜強度,測定PL量子吸收量。透過配有微秒閃光燈作為脈衝激發光源的螢光分光光度儀在77K(液氮溫度)下進行薄膜或稀釋溶液的磷光光譜。在發射光譜的脈衝激發及收集之間插入10-ms延遲時間。透過使用具有螢光壽命系統(FluoroCube,Horiba Jobin Yvon Inc.)的時間相關單光子計數技術監控PL峰值波段處的強度衰減及來自UV發光二極體的奈米級脈衝 激發光(300nm)來量測時間解析PL(PL衰減曲綫)。將樣本放置在具有溫度控制的真空低溫恆溫室中。使用具有發射光譜的脈衝激發及收集之間為200-ns延遲時間及10-ns延遲時間的相同螢光壽命系統來收集瞬時成份及延遲成份的PL光譜。電化學特徵:使用CHI619B恆電位儀的循環伏安法來量測氧化/還原電位。透過使用0.1M n-Bu4NPF6(TBAPF6)在CH2Cl2中作為支持電解質,掃描速率為100mV s-1,藉由循環伏安法測定氧化電位。透過使用0.1M n-Bu4NClO4(TBAP)在DMF中作為支持電解質,掃描速率為100mV s-1,記錄還原電位。使用包含銀/氯化銀(Ag/AgCl)、鉑金線及玻璃碳電極分別作為參考、計數及工作電極的標準3-電極電池。記錄所有電位以Ag/AgCl(飽和)作為參考電極時,CH2Cl2/TBAPF6中二茂鐵鐵/二茂鐵離子(Fc/Fc+)氧化還原發生於氧化出現在E’o=+0.47V,且二茂鐵/二茂鐵離子(Fc/Fc+)氧化還原發生於還原出現在E”o=+0.51V。
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)塗層玻璃並在超聲波浴(例如,洗滌劑、等離子水)中進行多步驟清洗。在氣相沉積有機層之前,透過紫外光(UV)和臭氧進一步處理清洗後的ITO基底。ITO基底的所有預處理過程在潔淨室(100級)內進行。
這些有幾次透過高真空單位(10-7Torr)的氣相沉積依次施加在ITO基底上,比如:電阻加熱石英船。每層的厚度和氣相沉積速率(0.1~0.3nm/sec)由石英晶體監視器來精確監控或設置。如上所述,還可能使單個層包含多於一種化合物,即一般主體材料摻雜有摻雜材料。這 透過來自兩個或多個來源的共氣相來實現。
在該有機EL裝置中,使用二吡嗪[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)用作電洞注入層,且N4,N4’-二二(聯苯-4-基)-N4,N4’-二二苯基聯苯基-4,4’-二胺(N4,N4’-di(biphenyl-4-yl)-N4,N4’-diphenylbiphenyl-4,4’-diamine)(HT1)用作電洞傳輸層,N-(聯苯-4-基)-9,9-二甲基-N-(4’-苯基聯苯-4-基)-9H-茀-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4’-phenyl biphenyl-4-yl)-9H-fluoren-2-amine)(EB2)用作電洞阻擋層,H1及H2分別用作與本發明相當或標準的磷光主體材料及延遲螢光主體材料或第二延遲螢光主體材料。所示化學結構如下:
下列本發明製備的延遲螢光範例可進行驗證,且可於有機EL裝置中,用作延遲螢光摻雜劑(延遲螢光摻雜材料)或第二延遲螢光摻雜材料、磷光主體材料。
有機銥絡合物廣泛用作發光層的磷光摻雜劑(磷光摻雜 材料),Ir(ppy)3廣泛用作有機EL裝置的發光層的磷光綠色摻雜劑。
2,2’,2”-(1,3,5-苯并三嗪)-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(參閱下列化學結構)用作電洞阻擋材料(HBM),且2-(10,10-二甲基-10氫-茚並[2,1-b]三亞苯-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)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)共沉積。本發明中用於生產標準有機EL裝置控制及可比材料的其他OLED材料的先前技術所示如下:
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,比如,Al、Mg、Ca、Li及K,且該低功函數金屬可有助于電子從陰極注入電子傳輸層。另外,在陰極及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,比如: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/電壓特徵都使用吉時利(Keithley)2400可編程電壓電流源來檢測。上述設備在室溫(約25℃)及大氣壓下操作。
實施例5
使用與上述一般方法類似的程序,生產具有下列裝置結構的有機EL裝置(參見圖1)。有機EL裝置包含,透明電極6~金屬電極14,其之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,以及沉積在電子注入層13上的金屬電極14。裝置:ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/LiQ(1nm)/Al(160nm)有機EL裝置的I-V-B(1000nits亮度時)的測試報告如表1所示。
在上述有機EL裝置測試報告的最佳實施例中(參見表1),我們揭露了本發明中具有通式(1)的延遲螢光化合物用作有機EL裝置發光層的發光主體或發光層的延遲螢光材料,其性能表現良好。
總而言之,本發明揭示了一種延遲螢光材料,其可用作 有機EL裝置發光層的磷光發光主體或發光層的延遲螢光材料。所述延遲螢光化合物式(1)由下式(1)表示:
其中W分別表示氧原子、硫原子及硒原子;R1、R2及R3分別選自由氫原子、氘原子、鹵化物、式(2)或式(3)組成的基團:
鑒於上述教導,可能作出多數明顯的修改及變化。因此,應該瞭解,在隨附權利要求的範圍內,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,但對於所屬領域具有通常知識者來說,可在不偏離旨在單獨由隨附權利要求所限制的那些的情況下,作出多數修改。
Claims (13)
- 本發明專利申請範圍為:一種延遲螢光材料,其具有下列通式(1): 其中W分別表示氧原子、硫原子及晒原子;R1、R2及R3分別選自由氫原子、氘原子、鹵化物、式(2)或式(3)組成的基團: D為電子供體,其由式(1)、取代或未取代咔唑基、取代或未取代雙咔唑基、取代或未取代二氫吖啶基、取代或未取代吩噁嗪基及取代或未取代二芳基胺基表示;A為電子受體,其選自由下式組成的基團: L表示單鍵或具有6到30個環碳原子的取代或未取代二價亞芳基,p表示0到4的整數,q表示0到5的整數,r表示1到4的整數,Y1至Y4為包含選自O、S、C(R22)(R23)、NR24及Si(R25)(R26)組成的原子或基團的二價橋;X1至X7表示氮原子或C(Rs),且各個Rs表示氫原子、苯基、具有1到30個碳原子的取代或未取代烷基、具有6到30個碳原子的取代或未取代芳基;Z表示氰基,R4至R26分別選自由氫原子、鹵化物、具有1到30個碳原子的取代或未取代烷基、具有6到30個碳原子的取代或未取代芳基、具有6到30個碳原子的一取代或未取代芳烷基組成的基團。
- 一種有機電致發光裝置,其包含由陰極及陽極組成的一對電極對,且該對電極對之間至少包含一層發光層、一層或多層有機薄膜層,其中該發光層包含具有一如申請專利範圍第1項所述之通式(1)的該有機材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層包括該延遲螢光材料及/或該螢光材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有通式(1)之該延遲螢光材料的該發光層為一延遲螢光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有通式(1)之該延遲螢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,其中該發光層包括一第二延遲螢光摻雜材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層包括一第二延遲螢光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有通式(1)之該有機化合物的該發光層為一磷光主體材料。
- 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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