TWI626240B - 延遲螢光化合物及使用其的有機電致發光裝置 - Google Patents
延遲螢光化合物及使用其的有機電致發光裝置 Download PDFInfo
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- TWI626240B TWI626240B TW106123147A TW106123147A TWI626240B TW I626240 B TWI626240 B TW I626240B TW 106123147 A TW106123147 A TW 106123147A TW 106123147 A TW106123147 A TW 106123147A TW I626240 B TWI626240 B TW I626240B
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明提供一種延遲螢光化合物及使用該延遲螢光化合物作為發光層及/或電子傳輸層及/或電洞阻擋層的發光主體的有機電致發光(有機EL)裝置，本發明之電致發光(有機EL)裝置具有良好的性能表現。
Description
本發明涉及一種化合物及使用該化合物的有機電致發光(有機EL)裝置。具體而言，本發明涉及一種具有通式(1)的延遲螢光化合物，且使用該延遲螢光化合物的有機EL裝置可顯示出極佳的性能。
有機電致發光(有機EL)裝置因其高照度、低重量、超薄外型、無背光的自照明、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。
有機材料電致發光的首次發現於1950年代早期，由法國南錫大學的安德烈貝諾斯(Andre Bernanose)及其同事所發現。馬丁伯普(Martin Pope)及其紐約大學的同事，於1963年在真空下摻有稠四苯蔥的單一純晶體上，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)及史帝芬凡斯萊克(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(HTL)、發光層(EML)、電子傳輸層(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，根據電子和電洞自旋組合方式，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。從三重態衰減為自旋禁阻(self forbidden)，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，铱、铑、铂、钯，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利用三重態和單重態激子。磷光有機EL通常在發光層(emitting layer，EML)及電子傳輸層(electron transport layer，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(hole transport layer，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長半衰期、提高效率及顯示極佳性能，我們使用2,3-二苯基吡
啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架作為受體並使用5個及/或8個骨架連接的位置來提供咔唑基(carbazole group)、二咔唑基(bicarbazole group)、二氫吲哚咔唑基(dihydroindolocarbazole group)、二氫咔唑基(dihyddoindenocarbazole group)、吩噻嗪基(phenothiazine group)、吩基(phenoxazine group)、二氫吖基(dihydroacridine group)、二氫化基(dihydrophenazine group)取代，以完成延遲螢光化合物的通式(1)。先前專利US7601435、US20100239339A1、WO2015099486、WO2016013875揭示了喹喔啉(quinoxaline)相關化合物並在喹喔啉核的6及7的位置中引入取代基。P.布羅頓(P.Brogdon)等人公佈了用於最高效率染料敏化太陽能電池(dye-sensitized solar cell，DSC)裝置的基於喹喔啉的染料。(SYNMET 15280 No.of Pages 10)。在先前技術中並未有以2,3-二苯基吡啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架作為有機EL裝置中延遲螢光化合物的受體。
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。本發明揭露了一種具有式(1)的延遲螢光化合物，其用作發光層的延遲螢光材料及/或發光層的磷光發光主體及/或電子傳輸層及/或電洞阻擋層，該等層具有良好的電荷載體遷移率及極佳的操作耐久性，可降低驅動電壓及能耗，增加有機EL裝置的效率及半衰期。
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裝置的延遲螢光化合物。所述延遲螢光化合物由以下式(1)表示：
其中，D1及D2單獨選自由式(2)及式(6)組成的群組
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為化合物C4的延遲螢光特性的瞬時衰變固化。
圖3為化合物Q的延遲螢光特性的瞬時衰變固化。
圖4為化合物若C4的UV-Vis(nm)及PL(nm)圖。
圖5為對比化合物若Q的UV-Vis(nm)及PL(nm)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。所述延遲螢光化合物由以下式(1)表示。
根據上述延遲螢光化合物式(1)，其中，L1及L2由下式(7)表示：
其中，Z1及Z5分別表示氮原子或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及具有6到30個碳原子的取代或未取代芳基。該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。
在本實施例中，一些延遲螢光化合物，如下所示：
本發明中延遲螢光化合物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6顯示本發明中延遲螢光化合物的製備實施例。實施例10至11顯示有機EL裝置及IVB
的製作及有機EL裝置測試報告的半衰期。
實施例1
化合物C4的合成
5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)的合成
於100℃下將10g(37.5mmol)2,5-二溴吡啶-3,4-二胺(2,5-dibromopyridine-3,4-diamine)、8.66g(41.2mmol)苯偶酰(benzil)、200ml醋酸的混合物加熱2小時。使所得混合物冷卻至室溫，隨後過濾得到黃色固體，產率(11g，66.7%)。1H NMR(CDCl3，400MHz)：化學位移(ppm)8.50(s，1H)，7.41-7.51(m，10H)。
9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(9H-咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(9H-carbazole))(C4)的合成
將5g(11.3mmol)的5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)及5.69g(34mmol)的咔唑
(carbazole)、2.16g(11.3mmol)的CuI、7.39g(22.6mmol)的Cs2CO3、2.27g(8.6mmol)的18-冠-6(18-crown-6)以及80ml的1,2-二氯苯(1,2-dichlorobenzene)的混合物除氣並置於氮氣中，隨後加熱迴流12小時。在完成反應之後，將混合物冷卻至室溫。加入250ml的甲醇，隨後過濾並使用甲醇清洗，得到紅色固體，產率(4.5g，64.7%)。1H NMR(CDCl3，400MHz)：化學位移(ppm)8.62(s，1H),、8.58(d，2H),8.15(d，2H)、7.92(d，2H)、7.65(d,2H)、7.41-7.51(m，12H)、7.25-7.33(m，6H)。MS(m/z，EI+)：613.5
實施例2
化合物C8的合成
9,9'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(3,1-亞苯基))雙(9H-咔唑)(9,9'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(9H-carbazole)(C8)
將5g(11.3mmol)的5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)及7.16g(24.9mmol)的3-(9H-咔唑-9-基)苯基硼酸(3-(9H-carbazol-9-yl)phenylboronic acid)、0.13g(0.11mmol)的Pd(PPh3)4、14.1ml的2M Na2CO3(aq)、50ml的EtOH以
及150ml的甲苯的混合物除氣並置於氮氣中，隨後於100℃下加熱12小時。在完成反應之後，將混合物冷卻至室溫。加入250ml的甲醇，隨後過濾並使用甲醇清洗，得到紅色固體，產率(5.04g，59%)。MS(m/z，EI+)：765.5
實施例3
化合物C17的合成
9,9',9",9'''-(5,5'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(苯5,3,1-三基))四(9H-咔唑)(9,9',9",9'''-(5,5'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole))(C17)的合成
使用如實施例2中的合成方法，將9,9'-(5-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)-1,3-亞苯基)雙(9H-咔唑)(9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole))取代3-(9H-咔唑-9-基)苯基-硼酸(3-(9H-carbazol-9-yl)phenyl-boronic acid)，得到所需化合物9,9',9",9'''-(5,5'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(苯5,3,1-三基))四(9H-咔唑)(9,9',9",9'''-(5,5'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole))。MS(m/z，EI+)：1096.4
實施例4
化合物C25的合成
9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(6-(9H-咔唑-9-基)-9H-3,9'-二咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole))(C25)的合成
使用如實施例1中的合成方法，6-(9H-咔唑-9-基)-9H-3,9'-二咔唑(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole)取代咔唑(carbazole)，得到9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(6-(9H-咔唑-9-基)-9H-3,9'-二咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole))(C25)MS(m/z，EI+)：1274.8
實施例5
化合物C38的合成
12,12'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(3,1-亞苯基))二(11-苯基-11,12-二氫吲哚并[2,3-a]咔唑)(12,12'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(11-phenyl-11,12-dihydroindolo[2,3-a]carbazole))(C38)的合成
使用如實施例2中的合成方法，11-苯基-12-(3-(4,4,5,5-四甲基-1,3,2-二氧硼雜環戊烷-2-基)苯基-11,12-二氫吲哚并[2,3-a]咔唑(11-phenyl-12-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-11,12-dihydroindolo[2,3-a]carbazole)取代3-(9H-咔唑-9-基)苯基硼酸(3-(9H-carbazol-9-yl)phenylboronic acid)，得到所需化合物12,12'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(3,1-亞苯基))雙(11-苯基-11,12-二氫吲哚并[2,3-a]咔唑)(12,12'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(11-phenyl-11,12-dihydroindolo[2,3-a]carbazole))(C38)。MS(m/z，EI+)：1096.6
實施例6
化合物C67的合成
10,10'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(10H-吩噁嗪)(10,10'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(10H-phenoxazine))(C67)的合成。
使用如實施例1中的合成方法，10H-吩噁嗪
(10H-phenoxazine)取代咔唑(carbazole)，得到所需化合物10,10'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)雙(10H-吩噁嗪)(10,10'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(10H-phenoxazine))(C67)。MS(m/z，EI+)：645.3
延遲螢光化合物光物理學特性的量測方法
光物理學特徵：在用於之後的研究之前，將合成的化合物在高真空下透過溫度梯度昇華進行純化。在具有<10-6torr本底壓力的真空室內，於石英基底上以1-2A/sec的速度透過熱蒸發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脉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。在發射光譜的脉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的時間相關單光子計數技術(FluoroCube,Horiba Jobin Yvon Inc.)及來自UV發光二極管的納秒(nanosecond)脉衝光激發(300nm)來監控PL峰值處強度的衰減，以確定時間解析(time-resolved)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脉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。
圖2及圖3顯示C4及對比化合物的延遲螢光於甲苯溶液的瞬時衰減曲綫的測量值。圖4及圖5顯示C4及對比化合物的光激螢光發射光譜的測量值。
生產有機EL裝置的一般方法
提供抗性為9~12ohm/square及厚度為120~160nm的氧化銦錫(ITO)塗層玻璃(之後以ITO為基材)，並在超聲波浴(例如：洗滌劑、去離子水)中進行幾步驟的清洗。在對有機層進行氣相沉積之前，透過UV及臭氧進一步處理清潔的ITO基材。ITO基材的所有預處理過程都在潔淨室(class 100)內進行。
將這些有機層透過高真空單元(10-7Torr)中藉由氣相沉積按順序施加在ITO基材上，比如：電阻加熱的石英船。使用石英晶體監視器精確監控或設定每層的厚度及氣相沉積速率(0.1~0.3nm/sec)。如上所
述，各層包含不止一種化合物，意即，通常為摻雜有摻雜劑材料的主體材料。這透過兩個或更多來源的共蒸發來實現的。
在該有機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，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)作為電洞傳輸層，N-(聯苯-4-基)-9,9-二甲基-N-(4'-苯基聯苯-4-基)-9H-芴-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4'-phenylbiphenyl-4-yl)-9H-fluoren-2-amine)(EB2)作為電子阻擋層，H1用作本發明磷光主體及延遲螢光主體的對照組或標準品。化學結構如下：
本發明中製備的下列延遲螢光實施例可作為延遲螢光摻雜劑、電洞阻擋材料或電子傳輸材料，並透過有機EL裝置進行測試。本發明中以化合物Q(CCQ)該延遲螢光摻雜劑的對照組。
有機銥絡合物廣泛用作發光層的磷光摻雜劑，其中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"-(1,3,5-三苯基)-三(1-苯基-1-H-苯并咪唑)(2,2',2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole))(TPBi)及HB3用作電洞阻擋材料(HBM)，而2-(10,10-二甲基-10H-茚并[2,1-b]苯并菲-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，在有機EL裝置中與8-羥基喹啉-鋰(8-hydroxyquinolato-lithium)(LiQ)共沉積。先前技術中用於生產標準有機EL裝置的其他OLED材料與及本發明的材料結構如下：
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於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。電子注入層之習知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，使用Keithley 2400可編程電壓電流源來檢測電流/電壓、發光/電壓及產率/電壓。上述裝置在室溫(約25℃)及大氣壓下進行操作。
實施例10
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(參閱圖1)。裝置：ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/主體+10%~30%摻雜劑(30nm)/HBM(10nm)/ETM摻雜40%
LiQ(35nm)/LiQ(1nm)/Al(160nm).有機EL裝置的I-V-B(於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(參閱表1)，我們揭露了本發明中具有通式(1)的延遲螢光化合物作為發光層及/或電子傳輸層及/或電洞阻擋層的發光主體、及/或有機EL裝置的發光層的延遲螢光(TADF)材料時，呈現出比先前技術中有機EL材料更良好的性能。尤其是，2,3-二苯基吡啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架(比如C4)用作有機EL裝置的延遲螢光化合物時，呈現了比喹喔啉核(比如CCQ)更好的效率。
總而言之，本發明揭露了一種延遲螢光化合物，其可作為發光層及/或電子傳輸層及/或電洞阻擋層的磷光發光主體及/或作為有機EL裝置的發光層的延遲螢光材料。所述延遲螢光化合物由下式(1)表示
其中，D1及D2分別包含選自由式(2)到式(6)的基團
L1或L2表示單鍵、具有6到30個環碳原子的取代或未取代亞芳基或具有3到30個環碳原子的取代或未取代雜亞芳基，m表示0到5的整數，n表示0到2的整數，p表示0到4的整數，q表示0到7的整數，r表示0到8的一整數，X為包含選自O、S、C(R14)(R15)、NR16及Si(R17)(R18)組成的原子或基團的二價橋，Y1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；R1及R2分別選自氫原子、鹵化物、硝基、吡啶、吡嗪、嘧啶、三嗪、具有1到30個碳原子的取代或未取代烷基及具有6到30個碳原子的取代或未取代芳基，而R3到R18分別選自氫原子、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及具有3到30個碳原子的取代或未取代雜芳基。
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 (18)
- 一種延遲螢光化合物，其由下式(1)表示：其中D1及D2分別選自式(2)至式(5)：
其中L1或L2表示一單鍵、具有6到30個環碳原子的取代或未取代亞芳基或具有3到30個環碳原子的取代或未取代雜芳基，m表示0到5的整數，n表示0到2的整數，p表示0到4的整數，q表示0到7的整數，r表示0到8的整數，X為包含選自O、S、C(R14)(R15)、NR16及Si(R17)(R18)組成的原子或基團的二價橋，Y1表示氮原子或C(Rs)，且各個Rs表示氫原子、具有1到30個碳原子的取代或未取代烷基、具有6到30個碳原子的一取代或未取代芳基；R1及R2分別選自氫原子、氟原子、硝基、吡啶、吡嗪、嘧啶、三嗪、具有1到30個碳原子的取代或未取代烷基及具有6到30個碳原子的取代或未取代芳基，而R3到R18分別選自氫原子、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個碳原子的取代或未取代芳烷基及具有3到30個碳原子的取代或未取代雜芳基。
- 如申請專利範圍第1項所述之延遲螢光化合物，其中L1及L2由下式(7)表示：其中Z1及Z5分別表示氮原子或C(Rs)，且各個Rs表示氫原子、具有1到30個碳原子的取代或未取代烷基及具有6到30個碳原子的取代或未取代芳基。
- 如申請專利範圍第1項所述之延遲螢光化合物，其中該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。
- 如申請專利範圍第1項所述之延遲螢光化合物，具有式(1)結構的該化合物為一發光材料。
- 如申請專利範圍第4項所述之延遲螢光化合物，其中該發光材料發出延遲螢光。
- 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，其中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、該有機薄膜層其中之一或二者包含具有一如申請專利範圍第1項所述之式(1)的該延遲螢光化合物。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該延遲螢光化合物的單重態能量與該延遲螢光化合物的三重態能量之間的差異小於0.25eV。
- 如申請專利範圍第6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化合物。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有式(1)之該延遲螢光化合物的該發光層為一延遲螢光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有式(1)之該延遲螢光化合物的該發光層為一延遲螢光摻雜材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該發光層包括一第二螢光摻雜材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中該發光層包括一第二螢光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有式(1)之該延遲螢光化合物的該發光層為一磷光主體材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有式(1)之該延遲螢光化合物的該有機薄膜層為一電洞阻擋材料。
- 如申請專利範圍第6項所述之有機電致發光裝置，其中包括具有式(1)之該延遲螢光化合物的該有機薄膜層為一電子傳輸層(ETL)材料。
- 如申請專利範圍第6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6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6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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| CN106118124A (zh) * | 2016-07-01 | 2016-11-16 | 华东理工大学 | 基于茚并噻吩给体D‑A‑π‑A型染料及其用途 |
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| CN106118124A (zh) * | 2016-07-01 | 2016-11-16 | 华东理工大学 | 基于茚并噻吩给体D‑A‑π‑A型染料及其用途 |
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