TWI653315B - Quinoxaline dimer-containing electron transport material as organic light-emitting element - Google Patents
Quinoxaline dimer-containing electron transport material as organic light-emitting element Download PDFInfo
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Abstract
一種作為有機發光元件之含喹喔啉二聚體電子傳輸材料，分子結構上具有富含電子特性，其應用於有機發光二極體元件之製造時，可作為電子傳輸層，並且能促使此元件具有降低操作電壓與增進發光效率之效果。A quinoxaline dimer-containing electron transport material as an organic light-emitting element, which has electron-rich characteristics in the molecular structure. When applied to the manufacture of an organic light-emitting diode element, it can be used as an electron transport layer and can promote the element It has the effect of reducing the operating voltage and improving the luminous efficiency.
Description
本發明與有機發光元件之電子傳輸材料有關，尤指一種含喹喔啉二聚體電子傳輸材料。 The present invention relates to an electron transporting material for an organic light-emitting element, and more particularly to a quinoxaline dimer-containing electron transporting material.
按，美商柯達公司在1980年代中期，利用真空蒸鍍法發表了多層式的有機發光二極體元件，將電洞與電子侷限在電子傳輸層與電洞傳輸層之間，進行再結合而發光，成功地發表了具有高效率與低驅動電壓的有機發光二極體元件。此後，各種理論與材料不斷推陳出新，造就了有機發光二極體元件的快速發展。 According to the American Kodak company, in the mid-1980s, the vacuum evaporation method was used to publish a multilayer organic light-emitting diode element, which confined holes and electrons between the electron transport layer and the hole transport layer, and combined them. Luminescence, successfully published organic light-emitting diode devices with high efficiency and low driving voltage. Since then, various theories and materials have been continuously innovated, resulting in the rapid development of organic light emitting diode elements.
有機發光二極體元件中，各層結構各司其職，具有不同的功能性，其中電子傳輸層的主要功能為幫助電子傳輸至發光層；相對地電洞傳輸層則是幫助電洞傳輸至發光層。藉由電洞傳輸層與電子傳輸層增進電洞與電子的流動性，並視其載子傳輸效率進行調整修正再結合的區域，可降低驅動電壓並提高元件的發光效率。 In the organic light-emitting diode element, each layer structure has its own function and has different functionalities. The main function of the electron transport layer is to help electrons to the light-emitting layer; the hole transport layer is to help the hole to transmit light. Floor. By using the hole transport layer and the electron transport layer to improve the mobility of holes and electrons, and adjusting and recombining the regions according to their carrier transmission efficiency, the driving voltage can be reduced and the luminous efficiency of the device can be improved.
良好的電子傳輸材料通常具有以下特性：(1)LUMO能階適合搭配發光層的LUMO能階，以利電子傳遞。(2)HOMO能階低於發光層的HOMO能階，兼具電洞阻擋能力。(3)足夠高的三重態能階，避免發光被淬熄。(4)可形成非晶相的薄膜，避免光散射。(5)良好的熱穩定性以及高玻璃轉化溫度。 Good electron transport materials usually have the following characteristics: (1) The LUMO energy level is suitable for matching the LUMO energy level of the light-emitting layer to facilitate electron transfer. (2) The HOMO energy level is lower than the HOMO energy level of the light emitting layer, and has both hole blocking ability. (3) The triplet energy level is high enough to prevent the light from being quenched. (4) A thin film with an amorphous phase can be formed to avoid light scattering. (5) Good thermal stability and high glass transition temperature.
目前電子傳輸材料大致可分為金屬錯合物類與含氮及含氧的雜環類，分子結構上通常是具有共軛平面的芳香族化合物，可以容易地接受電子並傳輸電子。富含電子的分子結構一般具有良好的電子傳輸功能。例如噁二唑(oxadiazole)、***(triazole)，苯並咪唑(benzimidazole)、吡啶(pyridine)、三嗪(triazine)、二苯基膦氧化物(diphenylphosphineoxide)、喹啉(quinoline)、喹喔啉(quinoxaline)與安他唑啉(antazoline)等衍生物。在喹喔啉的相關研究中，Kanbara等人(Macromolecules,Vol.26,p3464,1993)以各種取代基合成喹喔啉衍生物，提升分子量並改善熱穩定性，其中spiro-quinoxaline具有適當的能階，LUMO為-2.8eV，容易與發光材料搭配。接著，Jandke等人(Macromolecules,Vol.31,p6434,1998)將分子結構設計成含有兩個或三個喹喔啉官能基，例如二酚喹喔啉(BPQ，bis(phenylquinoxaline))與三酚喹喔啉(TPQ，tris(phenylquinoxaline))，其玻璃轉化溫度在130℃以上，且證實其薄膜屬於非晶相薄膜。Redecker等人(Appl.Phys.Lett.,Vol.17,p109,1999)則研究BPQ與TPQ的電子傳輸效率，是噁二唑的100倍(約10-4cm2/Vs @ 106V/cm)，並嘗試以TPQ製作高分子發光二極體，其EQE約0.1%。 At present, electron transport materials can be roughly divided into metal complexes and nitrogen and oxygen-containing heterocycles. The molecular structure is usually an aromatic compound with a conjugate plane, which can easily accept electrons and transport electrons. Electron-rich molecular structures generally have good electron transport functions. For example, oxadiazole, triazole, benzimidazole, pyridine, triazine, diphenylphosphineoxide, quinoline, quinoxa Derivatives such as quinoxaline and antazoline. In related studies of quinoxaline, Kanbara et al. (Macromolecules, Vol. 26, p3464, 1993) synthesized quinoxaline derivatives with various substituents to increase molecular weight and improve thermal stability. Among them, spiro-quinoxaline has appropriate energy Level, LUMO is -2.8eV, easy to match with light-emitting materials. Next, Jandke et al. (Macromolecules, Vol. 31, p6434, 1998) designed the molecular structure to contain two or three quinoxaline functional groups, such as diphenol quinoxaline (BPQ, bis (phenylquinoxaline)) and triphenol Quinoxaline (TPQ, tris (phenylquinoxaline)) has a glass transition temperature above 130 ° C, and it has been confirmed that its film is an amorphous phase film. Redecker et al. (Appl. Phys. Lett., Vol. 17, p109, 1999) studied the electron transmission efficiency of BPQ and TPQ, which is 100 times that of oxadiazole (approximately 10-4 cm2 / Vs @ 106 V / cm), and Attempt to make polymer light-emitting diode with TPQ, its EQE is about 0.1%.
連接數個喹喔啉可有效提升電子傳輸效率，不過也容易造成分子結構過大，蒸鍍溫度過高，合成步驟變得複雜困難等缺點，因此需要提出改良。 Connecting several quinoxalines can effectively improve the electron transport efficiency, but it is also easy to cause shortcomings such as too large molecular structure, too high evaporation temperature, and complex and difficult synthesis steps, so it needs to be improved.
本發明之主要目的在於提供一種作為有機發光元件之含喹喔啉二聚體電子傳輸材料，主要係將喹喔啉的衍生物對接形成二聚體，以縮合反應方式大幅簡化合成步驟，串連兩個以上的喹喔啉官能基，並適當調整取代基， 除了具有優異的電子傳輸效率外，亦與Liq(8-Quinolinolato lithium)有良好的相容性。以共鍍方式製作有機發光二極體元件，單一鍍層可同時包含電子注入層、電子傳輸層以及電洞阻檔層等功能。 The main purpose of the present invention is to provide a quinoxaline-containing dimer electron-transporting material as an organic light-emitting element. The quinoxaline-containing dimer is mainly formed by docking a quinoxaline derivative to form a dimer, and the synthesis steps are greatly simplified by a condensation reaction. More than two quinoxaline functional groups, and adjust the substituents appropriately, In addition to having excellent electron transport efficiency, it also has good compatibility with Liq (8-Quinolinolato lithium). Co-plating is used to produce organic light-emitting diode devices. A single plating layer can include functions such as an electron injection layer, an electron transport layer, and a hole barrier layer.
本發明作為有機發光元件之含喹喔啉二聚體電子傳輸材料，其含喹喔啉二聚體化學結構為：
A表示取代基，為具有一至四碳雙烷基或雙苯基或雙2-甲苯基或雙3-甲苯基或雙4-甲苯基或雙聯苯基或2,2’-伸聯苯基或苊并架構。 A represents a substituent and has one to four carbon dialkyl or bisphenyl or bis 2-tolyl or bis 3-tolyl or bis 4-tolyl or biphenyl or 2,2'-biphenyl Or merge architecture.
[L]n表示連結段，L為1,2-伸苯基或1,3-伸苯基或1,4-伸苯基，n表示連結段數目，為0或1。 [L] n represents a connecting segment, L is 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene, and n represents the number of connecting segments, which is 0 or 1.
上述含喹喔啉二聚體化學結構依照不同的分子架構片段與取代基位置，可能為下列化合物結構：
I-4 I-5 I-6
I-16 I-17 I-18
而本發明之上述目的與優點，不難從下述所選用實施例之詳細說明與附圖中獲得深入了解。 The above-mentioned objects and advantages of the present invention can be easily understood from the detailed description and accompanying drawings of selected embodiments below.
000‧‧‧基板 000‧‧‧ substrate
100‧‧‧銦錫氧化物陽極 100‧‧‧ Indium tin oxide anode
105‧‧‧電洞注入層 105‧‧‧ Hole injection layer
110‧‧‧電洞傳輸層 110‧‧‧ Hole Transmission Layer
115‧‧‧電子阻擋層 115‧‧‧ electron blocking layer
120‧‧‧發光層 120‧‧‧Light-emitting layer
125‧‧‧電洞阻擋層 125‧‧‧ Hole barrier
130‧‧‧電子傳輸層 130‧‧‧ electron transmission layer
135‧‧‧電子注入層 135‧‧‧ electron injection layer
140‧‧‧金屬陰極 140‧‧‧metal cathode
第1圖為本發明有機發光元件的結構圖；第2圖為本發明顯示實驗例與比較例中使用之有機發光二極體材料，包含具有電洞注入功能之材料HT-1、具有電洞傳輸功能之材料HT-2、具有發光功能之客體材料RD-1、具有發光功能主體材料RH-1、具有電子傳輸功能之材料ET-1與ET-2；第3圖為本發明顯示實驗例與比較例中有機發光元件之電壓-電流密度曲線圖，調整不同電壓並量測電壓變化之結果； 第4圖為本發明顯示實驗例與比較例中有機發光元件之電壓-亮度曲線圖，調整不同電壓並量測亮度變化之結果；第5圖為本發明顯示實驗例與比較例中有機發光元件之亮度-效率曲線圖，調整不同電壓並量測亮度與電流密度變化之結果，再經數據分析整理成亮度與效率之相關曲線；第6圖為本發明顯示實驗例與比較例中有機發光元件之電流密度-亮度曲線圖，調整不同電壓並量測電流密度及亮度變化之結果；第7圖為本發明顯示實驗例與比較例中有機發光元件之光譜圖，在亮度2000cd/m2時量測之光譜圖。 FIG. 1 is a structural diagram of an organic light-emitting element according to the present invention; and FIG. 2 is an organic light-emitting diode material used in experimental examples and comparative examples of the present invention, including a material having a hole injection function HT-1 and a hole Material HT-2 for transmission function, guest material RD-1 with light function, host material RH-1 with light function, materials ET-1 and ET-2 with electron transmission function; Figure 3 is a display experimental example of the present invention Compared with the voltage-current density curve of the organic light-emitting element in the comparative example, adjusting the different voltages and measuring the results of the voltage changes; Fig. 4 is a graph showing the voltage-brightness curves of the organic light-emitting elements in the experimental examples and comparative examples of the present invention, and the results of adjusting different voltages and measuring the brightness changes; Fig. 5 is a diagram showing the organic light-emitting elements in the experimental examples and comparative examples of the present invention Brightness-efficiency curve, adjust the different voltages and measure the results of brightness and current density changes, and then organize the data to analyze the correlation curve of brightness and efficiency; Figure 6 shows the organic light-emitting elements in the experimental and comparative examples of the present invention. The current density-brightness curve, the results of adjusting different voltages and measuring the changes in current density and brightness; Figure 7 shows the spectral diagrams of the organic light-emitting elements in the experimental examples and comparative examples of the present invention, measured at a brightness of 2000 cd / m2 Spectrum chart.
本發明的實驗方式大致分成三個部份，首先是電子傳輸材料的合成與純化，接著是有機發光元件製作，最後是數據分析與效能評估。 The experimental method of the present invention is roughly divided into three parts, firstly the synthesis and purification of the electron transport material, then the production of organic light-emitting elements, and finally the data analysis and performance evaluation.
一、電子傳輸層材料合成例： I. Synthesis example of electron transport layer material:
I-1合成例 I-1 Synthesis Example
將3,3-二氨基聯苯氨(15g，70mmol)和二苯基乙二酮(29.5g，140mmol)放入三頸反應瓶中，並加入100ml醋酸作為反應溶劑，於120℃迴流反應12小時。反應結束後冷卻至室溫，過濾獲得深褐色固體，以蒸餾水和乙醇清洗固體去除醋酸後，再將固體溶於甲苯中利用管柱層析法純化，最後獲得化合物I-1，外觀為淡黃色粉末，產重30g，產率76%。 Put 3,3-diaminobenzidine (15g, 70mmol) and diphenylethylenedione (29.5g, 140mmol) into a three-necked reaction flask, add 100ml of acetic acid as the reaction solvent, and reflux at 120 ° C for 12 hour. After the reaction, it was cooled to room temperature and filtered to obtain a dark brown solid. The solid was washed with distilled water and ethanol to remove acetic acid. The solid was dissolved in toluene and purified by column chromatography. Finally, compound I-1 was obtained. The appearance was pale yellow. Powder, yield 30 g, yield 76%.
1H-NMR(CDCl3，500MHZ)：7.33-7.39(m，12 H)，7.54-7.56(m，8 H)，8.20-8.22(m，2 H)，8.22-8.30(m，2 H)，8.57(s，2 H)。 1H-NMR (CDCl3, 500MHZ): 7.33-7.39 (m, 12 H), 7.54-7.56 (m, 8 H), 8.20-8.22 (m, 2 H), 8.22-8.30 (m, 2 H), 8.57 (s, 2 H).
I-2合成例 I-2 Synthesis Example
將3,3-二氨基聯苯氨(15g，70mmol)和苊醌(25.5g，140mmol)放入三頸反應瓶中，並加入300ml醋酸作為反應溶劑，於120℃迴流反應12小時。反應結束後冷卻至室溫，過濾獲得深褐色固體，以蒸餾水和乙醇清洗固體去除醋酸後，再將固體溶於甲苯中利用管柱層析法純化，最後獲得化合物I-2，外觀為亮黃色粉末，產重31.5g，產率89%。 3,3-diaminobenzidine (15 g, 70 mmol) and fluorenone (25.5 g, 140 mmol) were placed in a three-necked reaction flask, 300 ml of acetic acid was added as a reaction solvent, and the reaction was refluxed at 120 ° C for 12 hours. After the reaction, it was cooled to room temperature, filtered to obtain a dark brown solid, the solid was washed with distilled water and ethanol to remove acetic acid, and the solid was dissolved in toluene and purified by column chromatography. Finally, the compound I-2 was obtained, and the appearance was bright yellow. Powder, yield 31.5 g, yield 89%.
I-3合成例 I-3 Synthesis Example
將3,3-二氨基聯苯氨(15g，70mmol)和9,10-菲醌(29.3g，140mmol)放入三頸反應瓶中，並加入300ml醋酸作為反應溶劑，於120℃迴流反應12小時。反應結束後冷卻至室溫，過濾獲得深褐色固體，以蒸餾水和乙醇清洗固體去除醋酸後，再將固體溶於甲苯中利用管柱層析法純化，最後獲得化合物I-3，外觀為淡黃色粉末，產重33g，產率84%。 Put 3,3-diaminobenzidine (15 g, 70 mmol) and 9,10-phenanthrenequinone (29.3 g, 140 mmol) into a three-necked reaction flask, and add 300 ml of acetic acid as a reaction solvent, and reflux the reaction at 120 ° C for 12 hour. After the reaction, it was cooled to room temperature and filtered to obtain a dark brown solid. The solid was washed with distilled water and ethanol to remove acetic acid. The solid was dissolved in toluene and purified by column chromatography. Finally, the compound I-3 was obtained with a pale yellow appearance. Powder with a yield of 33 g and a yield of 84%.
二、電子傳輸材料應用於有機發光元件：有機發光元件的製作一般包括基材前處理、有機層蒸鍍、金屬陰極蒸鍍與封裝等。其中，該有機發光元件結構如圖一所示，包含基板000、銦錫氧化物陽極100、電洞注入層105、電洞傳輸層110、電子阻擋層115、發光層120、電洞阻擋層125、電子傳輸層130、電子注入層135及金屬陰極140等結構。以本發明的電子傳輸材料應用於有機發光元件時，可作為有機發光元件之電子傳輸層。實驗例與比較例中不同元件結構的製作條件，詳細整理如表二。元件結構中使用之各層材料其分子結構如圖二所示。製作完成的有機發光元件，經過適當封裝後進行量測。電壓與電流量測設備為Keithley 2230，光譜量測設備為 Konica Minolta CS-1000A，設定起始為3V，逐漸升高至7V，並同時量測電流與亮度變化。各實驗例與比較例的元件分析結果，詳細整理如表三。 2. Application of electron transmission materials to organic light-emitting elements: The production of organic light-emitting elements generally includes substrate pretreatment, organic layer evaporation, metal cathode evaporation, and packaging. The structure of the organic light emitting element is shown in FIG. 1 and includes a substrate 000, an indium tin oxide anode 100, a hole injection layer 105, a hole transmission layer 110, an electron blocking layer 115, a light emitting layer 120, and a hole blocking layer 125. , Electron transport layer 130, electron injection layer 135, and metal cathode 140. When the electron transporting material of the present invention is applied to an organic light emitting element, it can be used as an electron transporting layer of the organic light emitting element. The fabrication conditions for the different element structures in the experimental and comparative examples are detailed in Table 2. The molecular structure of each layer of material used in the device structure is shown in Figure 2. The completed organic light-emitting element is measured after being appropriately packaged. The voltage and current measuring equipment is Keithley 2230, and the spectral measuring equipment is Konica Minolta CS-1000A, set the initial value to 3V, gradually increase to 7V, and measure current and brightness changes at the same time. The component analysis results of each experimental example and comparative example are summarized in Table III.
實驗例1 Experimental example 1
以化合物I-1作為電子傳輸層，製作成有機發光元件進行測試。詳細製作方式為，首先在銦錫氧化物陽極上蒸鍍電洞注入層3nm，材料為HT-1；接著是電洞傳輸層65nm，材料為HT-2，然後是發光層30nm，材料為10%的RD-1摻雜於RH-1中；接著是電子傳輸層10nm，材料為50%的I-1與50%的Liq(8-Quinolinolato lithium)進行共蒸鍍；最後是金屬陰極100nm，材料是Aluminum。 Using compound I-1 as an electron transport layer, an organic light emitting device was fabricated and tested. The detailed production method is: firstly, a hole injection layer 3nm is deposited on the indium tin oxide anode, and the material is HT-1; then a hole transmission layer is 65nm, the material is HT-2, then the light emitting layer is 30nm, and the material is 10 % Of RD-1 is doped in RH-1; then the electron transport layer is 10nm, the material is 50% I-1 and 50% Liq (8-Quinolinolato lithium) are co-evaporated; finally, the metal cathode is 100nm, The material is Aluminum.
實驗例2 Experimental example 2
以化合物I-2作為電子傳輸層，製作成有機發光元件進行測試。詳細製作方式為，首先在銦錫氧化物陽極上蒸鍍電洞注入層3nm，材料為HT-1；接著是電洞傳輸層65nm，材料為HT-2，然後是發光層30nm，材料為10%的RD-1摻雜於RH-1中；接著是電子傳輸層10nm，材料為50%的I-2與50%的Liq(8-Quinolinolato lithium)進行共蒸鍍；最後是金屬陰極100nm，材料是Aluminum。 Using compound I-2 as an electron transport layer, an organic light emitting device was fabricated and tested. The detailed production method is: firstly, a hole injection layer 3nm is deposited on the indium tin oxide anode, and the material is HT-1; then a hole transmission layer is 65nm, the material is HT-2, then the light emitting layer is 30nm, and the material is 10 % Of RD-1 is doped in RH-1; then the electron transport layer is 10nm, the material is 50% I-2 and 50% Liq (8-Quinolinolato lithium) are co-evaporated; finally, the metal cathode is 100nm, The material is Aluminum.
實驗例3 Experimental example 3
以化合物I-3作為電子傳輸層，製作成有機發光元件進行測試。詳細製作方式為，首先在銦錫氧化物陽極上蒸鍍電洞注入層3nm，材料為HT-1；接著是電洞傳輸層65nm，材料為HT-2，然後是發光層30nm，材料為10%的RD-1摻雜於RH-1中；接著是電子傳輸層10nm，材料為50%的I-3與50%的Liq(8-Quinolinolato lithium)進行共蒸鍍；最後是金屬陰極100nm，材料是Aluminum。 Using compound I-3 as an electron transport layer, an organic light emitting device was fabricated and tested. The detailed production method is: firstly, a hole injection layer 3nm is deposited on the indium tin oxide anode, and the material is HT-1; then a hole transmission layer is 65nm, the material is HT-2, then the light emitting layer is 30nm, and the material is 10 % Of RD-1 is doped in RH-1; then the electron transport layer is 10nm, the material is 50% I-3 and 50% Liq (8-Quinolinolato lithium) are co-evaporated; finally, the metal cathode is 100nm, The material is Aluminum.
比較例1 Comparative Example 1
以典型的電子傳輸材料ET-1(專利號：TW I469967)作為電子傳輸層，製作成有機發光元件進行測試。詳細製作方式為，首先在銦錫氧化物陽極上蒸鍍電洞注入層3nm，材料為HT-1；接著是電洞傳輸層65nm，材料為HT-2，然後是發光層30nm，材料為10%的RD-1摻雜於RH-1中；接著是電子傳輸層10nm，材料為50%的ET-1與50%的Liq(8-Quinolinolato lithium)進行共蒸鍍；最後是金屬陰極100nm，材料是Aluminum。 A typical electron-transporting material ET-1 (patent number: TW I469967) was used as the electron-transporting layer to make an organic light-emitting element for testing. The detailed production method is: firstly, a hole injection layer 3nm is deposited on the indium tin oxide anode, and the material is HT-1; then a hole transmission layer is 65nm, the material is HT-2, then the light emitting layer is 30nm, and the material is 10 % Of RD-1 is doped in RH-1; then the electron transport layer is 10nm, the material is 50% ET-1 and 50% Liq (8-Quinolinolato lithium) are co-evaporated; finally, the metal cathode is 100nm, The material is Aluminum.
比較例2 Comparative Example 2
以典型的電子傳輸材料ET-2(專利號：TW I402259)作為電子傳輸層，製作成有機發光元件進行測試。詳細製作方式為，首先在銦錫氧化物陽極上蒸鍍電洞注入層3nm，材料為HT-1；接著是電洞傳輸層65nm，材料為HT-2，然後是發光層30nm，材料為10%的RD-1摻雜於RH-1中；接著是電子傳輸層10nm，材料為50%的ET-2與50%的Liq(8-Quinolinolato lithium)進行共蒸鍍；最後是金屬陰極100nm，材料是Aluminum。 A typical electron-transporting material ET-2 (patent number: TW I402259) was used as the electron-transporting layer to make an organic light-emitting element for testing. The detailed production method is: firstly, a hole injection layer 3nm is deposited on the indium tin oxide anode, and the material is HT-1; then a hole transmission layer is 65nm, the material is HT-2, then the light emitting layer is 30nm, and the material is 10 % Of RD-1 is doped in RH-1; then the electron transport layer is 10nm, the material is 50% ET-2 and 50% Liq (8-Quinolinolato lithium) is co-evaporated; finally, the metal cathode is 100nm, The material is Aluminum.
評估：製作完成的有機發光元件經分析後，將數據整理後詳細如表二。不同的電子傳輸材料不僅能階不同，電子傳輸速率亦不同，適當的材料是提高有機發光元件效率的關鍵。如圖三、圖四、圖五與圖六分別為電壓-電流密度曲線圖、電壓-亮度曲線圖、亮度-效率曲線圖與電流密度-亮度曲線圖的分析結果。 Evaluation: After the completed organic light-emitting element is analyzed, the data is arranged as shown in Table II. Different electron transport materials not only have different energy levels, but also different electron transport rates. Appropriate materials are the key to improving the efficiency of organic light emitting elements. Figure 3, Figure 4, Figure 5 and Figure 6 show the analysis results of voltage-current density curve, voltage-luminance curve, brightness-efficiency curve, and current density-luminance curve.
本發明的喹喔啉衍生物二聚體相較於典型的電子傳輸材料具有低操作電壓與高發光效率的優勢。如實驗例1、實驗例2與實驗例3，只需3.8V操作電壓即可達到2000nits的亮度，而典型的電子傳輸材料如比較例1；或是單喹 喔啉衍生物的比較例2，則需要4.2V以上。其中，採用化合物I-1製作的有機發光元件如實驗例1，不僅優於一般典型的電子傳輸材料，且展現了最佳的與發光效率，達到10.9/cd/A，而比較例1與比較例2則分別為10.2cd/A與10.0cd/A。 Compared with typical electron transport materials, the quinoxaline derivative dimer of the present invention has the advantages of low operating voltage and high luminous efficiency. For example, Experimental Example 1, Experimental Example 2 and Experimental Example 3, a brightness of 2000 nits can be achieved with an operating voltage of only 3.8 V, and a typical electron-transporting material such as Comparative Example 1 or monoquine Comparative Example 2 of the oxaline derivative requires 4.2V or more. Among them, the organic light-emitting element using Compound I-1, such as Experimental Example 1, is not only better than the typical typical electron-transporting materials, but also exhibits the best and luminous efficiency, reaching 10.9 / cd / A, while Comparative Example 1 is compared with Example 2 is 10.2cd / A and 10.0cd / A.
惟，以上實施例之揭示僅用以說明本發明，並非用以限制本發明，故舉凡等效元件之置換仍應隸屬本發明之範疇。 However, the disclosure of the above embodiments is only used to illustrate the present invention and is not intended to limit the present invention. Therefore, the replacement of equivalent components should still belong to the scope of the present invention.
綜上所述，可使熟知本項技藝者明瞭本發明確可達成前述目的，實已符合專利法之規定，爰依法提出申請。 In summary, those skilled in the art can understand that the present invention can indeed achieve the aforementioned purpose, and it has indeed complied with the provisions of the Patent Law, and filed an application in accordance with the law.
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