TW201404862A - 有機電子材料和有機電致發光器件 - Google Patents

有機電子材料和有機電致發光器件 Download PDF

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TW201404862A
TW201404862A TW102120047A TW102120047A TW201404862A TW 201404862 A TW201404862 A TW 201404862A TW 102120047 A TW102120047 A TW 102120047A TW 102120047 A TW102120047 A TW 102120047A TW 201404862 A TW201404862 A TW 201404862A
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organic
organic electroluminescent
electroluminescent device
electronic material
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TW102120047A
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TWI510597B (zh
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jin-hai Huang
Lei Dai
jin-xin Chen
Li-Fei Cai
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Guangdong Aglaia Optoectronic Materials Co Ltd
Beijing Aglaia Technology Dev Co Ltd
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Abstract

本發明涉及“有機電子材料和有機電致發光器件”，具有如下式(I)或(II)所述的結構，。本發明的有機電致發光器件採用了含有熒蒽基團的化合物作為電子傳輸材料，具有較高的電子傳輸和注入能力，也由于其具有很好的熱穩定性和良好的成膜性能，在提高有機電致發光器件效率的同時，也提高了器件的使用壽命；同時，本發明的有機電致命發光器件採用了含有熒蒽基團的化合物作為磷光的主體材料，由于其不但具有較高的三線態能級，而且具有很好的電子傳輸性能，能有效的提高發光層中電子的數量，提高器件的效率。

Description

有機電子材料和有機電致發光器件
本發明涉及新型的有機電子材料，通過真空蒸渡沈積成薄膜，作為電子傳輸材料和磷光主體材料應用在有機電致發光二極管上，屬于有機電致發光器件顯示技術領域。
有機電致發光器件作為一種新型的顯示技術，具有自發光、寬視角、低能耗、效率高、薄、色彩豐富、響應速度快、適用溫度範圍廣、低驅動電壓、可制作柔性可彎曲與透明的顯示面板以及環境友好等獨特優點，因此，有機電致發光器件技術可以應用在平板顯示器和新一代照明上，也可以作為LCD的背光源。自1987年柯達公司的Tang等利用真空薄膜蒸鍍技術，用8-羥基喹啉鋁(Alq3)作為發光層，三苯胺衍生物作為空穴傳輸層做出的夾心式雙層器件，在10V的驅動電壓下，發光亮度達1000 cd/m2(Tang C. W.,Vanslyke S. A. Appl.Phys.Lett.1987,51,913-916)。這一突破性進展，引起了科技界和產業界的廣泛關注，掀起了人們對有機電致發光研究和應用的熱潮。隨後，于1989年，主客體技術的發明，更是極大提高了有機電致發光器件的發光效率和工作壽命。1998年，Forrest等發現了電致磷光現象，突破了有機電致發光量子效率低于25%的理論限制，提升到100%(Baldo M. A.,Forrest S. R. Et al，Nature,1998,395,151-154)，使得有機電子發光的研究進入了一個新時期，拓寬了其研究領域。
一個經典的三層有機電致發光器件包含有空穴傳輸層，發光層和電子傳輸層。其中器件的電子傳輸層，傳統使用的是Alq3，具有良好的成膜性和熱穩定性，但是其發很強的綠光和較低的電子遷移率，影響了它的產業化應用。隨後，一些具有優越性能的電子傳輸材料如TPBI,BCP，Bphen等也廣泛應用在有機電致發光器件上。而現有發光層材料基本可以分為兩 類，分別為熒光發光材料和磷光發光材料，往往採用的是主客體摻雜技術。CBP(4,4'-bis(9-carbazolyl)-biphenyl)是一個具有高效和高三線態能級的磷光主體材料，當CBP作為主體材料時，三線態能量能夠順利地轉移到磷光發光材料，從而產生高效的紅光和綠光材料。但是這些具有代表性的主體材料，往往由于其的熱穩定性和制備得到的器件壽命短而限制它們的應用。
盡管經過20年的發展，有機電致發光器件已經取得了長足的進步和發展，有機材料也隨之不斷的發展進行中，但是，符合市場化需求的且具有良好的器件效率和壽命，以及很好性能和穩定性的材料還是很少。
熒蒽作為電致發光材料，應用廣泛，可以作為電子傳輸材料，空穴傳輸材料，發光材料，但是報道的文獻要麽沒有詳細描述器件性能，要麽器件的效率比較低以及較低的器件穩定性，本發明就是在熒蒽的基礎上發明一系列新型化合物，並且應用在有機電致發光器件上。
本發明的目的是一種高效的新型有機電子傳輸和磷光主體材料的合成，以及在器件上的應用，提供高性能的有機電致發光器件和制備方法。本發明所述的有機電子材料具有化學式(I)或者化學式(II)的化學結構式：
其中，R1-R5中任意四個為氫，另一個為C1-C6烷基、C7-C24的芳基、含有一個或多個選自N、O、S的取代或未取代的雜芳環基、三芳香甲矽烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；或者R1、R3、R5為氫，R2、R4分別獨立為C1-C6烷基、C6-C24的芳基、含有一個或多個選自N、O、S的雜芳環、三芳香甲矽烷基、二芳胺基、二芳香氧磷基、 芳香羰基、芳硫基；A獨立地表示為C(R6)2、N(R7)、S、O、P(R8)、S(O)2或者B(R9)，R6-R9獨立地表示為氫、氘、C1-C6烷基、苯基、C1-C6烷基苯基、含有一個或多個選自N、O、S的雜芳基，或兩個R6與C之間形成環狀結構。
優選，R1-R5優選為芴基、C1-C4烷基或苯基或萘基取代的五元或六元雜芳環基、二苯基胺基、苯萘胺基、三苯基甲矽烷基、二苯基氧磷、苯基羰基、苯基硫基。
其中所述五元或六元雜環芳烴基為哢唑基、嘧啶基、吡啶基、噻唑基，三氮唑基，三嗪基。
所述芴基為9，9-二甲基芴基、9，9-二苯基芴基、9，9-二甲苯基芴基或螺芴基。
所述R1、R2、R4、R5為氫。
A優選C(R6)2、N(R7)、S、O、S(O)2，R6-R7優選氫、甲基，苯基或甲基苯基，或兩個R6與C之間形成五元環狀結構。
本發明優選的化合物如下，但是並沒有限制在這些裏面
更優選：
本發明的有機電致發光器件包括基板，于基板上形成的陽極層，于陽極層上依次蒸鍍空穴注入層，空穴傳輸層，發光層，電子傳輸層以及電子注入層和陰極陽極。
發光層可分為熒光發光層或者為磷光發光層。
本發明中的有機電子發光器件一個實施方式，利用本發明的 化合物作為電子傳輸材料；本發明的有機電致發光器件的另外一個實施方式為，利用以上化合物作為磷光主體材料，客體材料優選為有機銥化合物和有機鉑化合物；本發明的有機電致發光器件中，利用以上化合物作為磷光主體材料，並利用以上化合作為電子傳輸層。
本發明的有機電致發光器件採用了含有熒蒽基團的化合物作為電子傳輸材料，具有較高的電子傳輸和注入能力，也由于其具有很好的熱穩定性和良好的成膜性能，在提高有機電致發光器件效率的同時，也提高了器件的使用壽命；同時，本發明的有機電致命發光器件採用了含有熒蒽基團的化合物作為磷光的主體材料，由于其不但具有較高的三線態能級，而且具有很好的電子傳輸性能，能有效的提高發光層中電子的數量，提高器件的效率。
10‧‧‧玻璃基板
20‧‧‧陽極
30‧‧‧空穴注入層
40‧‧‧空穴傳輸層
50‧‧‧發光層
60‧‧‧電子傳輸層
70‧‧‧電子注入層
80‧‧‧陰極
圖1為本發明的器件結構圖。
圖2為化合物46的1H NMR圖。
圖3為化合物36的1H NMR圖。
圖4為化合物46的DSC圖。
下面結合實施例對本發明作進一步的詳細說明。
實施例1：化合物43合成
中間體1-1的合成
向燒瓶中加入7.5 g 2-溴-9,9-二甲基-芴，0.15 g碘化亞銅，0.3 g四三苯基磷鈀，然後加入三乙胺通氮氣，開始攪拌，使充分溶解，然後加入10 ml三甲基矽乙炔，過夜回流反應12小時。減壓除去溶劑。加入水，用乙醚萃取三次，合並有機相，用飽和食鹽水洗三次，乾燥，抽濾，濃縮，得到6.8 g產品，產率85%。
中間體1-2的合成
向燒瓶中加入45 ml甲醇，50 ml二氯甲烷，5 g氫氧化鉀，6.8 g中間體1-1，通氮氣，攪拌反應1小時。過濾除去無機鹽，除去有機溶劑，濾餅用甲醇重結晶，得到4.2 g，產率為82%。
中間體1-3的合成
將84 g苊醌，72.8 g1,3-二苯基丙酮，600ml乙醇，56g氫氧化鉀，加入四口燒瓶，開始攪拌，通氮氣，回流2小時。冷卻室溫，過濾，濾餅用乙醇淋洗2次，得到130 g黑色固體，產率為91%。
化合物43的合成
將4.2 g中間體1-2和6.3g中間體1-3，還60 ml二苯醚加入到四口燒瓶中， 開始攪拌，通氮氣10分鍾，開始加熱回流12小時，冷卻，過濾，濾餅用乙酸乙酯加熱回流，冷卻，過濾得到6.5 g淡黃色固體，產率為66%。1H NMR(400 MHz,CD2Cl2,δ)：7.56-7.74(m,9 H),7.21-7.44(m,14 H),7.76-7.70(m,1 H),1.27(s,6 H).MALDI-TOF-MS m/s計算值C43H30：546.2，實測值[M+]：546.5。
實施例2：化合物46合成
中間體2-1的合成
向燒瓶中加入8.0 g中間體2-0，0.15 g碘化亞銅，0.3 g四三苯基磷鈀，然後加入三乙胺通氮氣，開始攪拌，使充分溶解，然後加入10 ml三甲基矽乙炔，過夜回流反應12小時。減壓除去溶劑。加入水，用乙醚萃取三次，合並有機相，用飽和食鹽水洗三次，乾燥，抽濾，濃縮，得到6.8g產品，產率83%。
中間體2-2的合成
向燒瓶中加入45 ml甲醇，50 ml二氯甲烷，5g氫氧化鉀，7 g中間體2-1，通氮氣，攪拌反應1小時。過濾除去無機鹽，除去有機溶劑，濾餅用甲醇重結晶，得到4.0 g，產率為70%。
化合物46的合成
將4.0 g中間體2-2和4.2 g中間體1-3，60 ml二苯醚加入到四口燒瓶中，開始攪拌，通氮氣10分鍾，開始加熱回流12小時，冷卻，過濾，濾餅用乙酸乙酯加熱回流，冷卻，過濾得到7.0 g淡黃色固體，產率為89%。1H NMR(400 MHz,CDCl3,δ)：7.61-7,79(m,8 H),7.47-7.52(m,3 H),7.32-7.36(m,5 H),7.20-7.24(m,3 H),7.02-7.14(m,8 H),6.56-6.65(m,4 H),6.49(s,1 H)。如圖2。 MALDI-TOF-MS m/s計算值C53H32：668.3，實測值[M+]：668.5。
實施例3：化合物35合成
中間體3-1的合成
向燒瓶中加入7.7 g中間體3-0，0.15 g碘化亞銅，0.3 g四三苯基磷鈀，然後加入三乙胺通氮氣，開始攪拌，使充分溶解，然後加入10 ml三甲基矽乙炔，過夜回流反應12小時。減壓除去溶劑。加入水，用乙醚萃取三次，合並有機相，用飽和食鹽水洗三次，乾燥，抽濾，濃縮，得到6.8g產品，產率67%。
中間體3-2的合成
向燒瓶中加入45 ml甲醇，50 ml二氯甲烷，5g氫氧化鉀，5.5 g中間體3-1，通氮氣，攪拌反應1小時。過濾除去無機鹽，除去有機溶劑，濾餅用甲醇重結晶，得到4.11 g，產率為95%。
化合物35的合成
將4.0 g中間體3-2和5.5 g中間體1-3，60 ml二苯醚加入到四口燒瓶中，開始攪拌，通氮氣10分鍾，開始加熱回流12小時，冷卻，過濾，濾餅用乙酸 乙酯加熱回流，冷卻，過濾得到4.5 g淡黃色固體，產率為49%。1H NMR(400 MHz,CD2Cl2,δ)：8.12-8.13(d,J=7.6 Hz,2 H),7.74-7.77(m,4 H),7.52-7.60(m,3 H),7.25-7.45(m,19 H),6.69-6.81(d,J=7.2 Hz,1 H).MALDI-TOF-MS m/s計算值C46H29N：595.2，實測值[M+]：595.4。
實施例4：化合物26合成
合成工藝跟實施例1一樣
實施例5：化合物36合成
中間體5-1的合成
向燒瓶中加入9.1 g化合物5-0，0.15 g碘化亞銅，0.24 g四三苯基磷鈀，然後加入100 ml三乙胺通氮氣，開始攪拌，使充分溶解，然後加入10 ml三甲基矽乙炔，過夜回流反應12小時。減壓除去溶劑。加入水，用乙醚萃取三次，合並有機相，用飽和食鹽水洗三次，乾燥，抽濾，濃縮，得到6.8 g產品，產率74%。
中間體5-2的合成
向燒瓶中加入45 ml甲醇，50 ml二氯甲烷，5 g氫氧化鉀，7 g中間體2-1，通氮氣，攪拌反應1小時。過濾除去無機鹽，除去有機溶劑，濾餅用甲醇重結晶，得到5.0 g，產率為83%。
化合物36的合成
將4.8 g中間體6-2和3.9 g中間體1-3，60 ml二苯醚加入到四口燒瓶中，開始攪拌，通氮氣10分鍾，開始加熱回流12小時，冷卻，過濾，1濾餅用乙酸乙酯加熱回流，冷卻，過濾得到5.5 g淡黃色固體，產率為65%。1H NMR (400 MHz,CD2Cl2,δ)：8.14-8.16(d,J=8.4 Hz,4 H),7.72-7.80(m,4 H),7.54-7.69(m,11 H),7.27-7.50(m,16 H),6.74-6.76(d,J=6.8 Hz,1H).如圖3。
MALDI-TOF-MS m/s計算值C59H36N2：760.3，實測值[M+]：760.5。
實施例6
在氮氣保護下，以20℃/min的加熱和冷卻速度用DSC方法測試化合物26的玻璃化溫度。測得的化合物26的玻璃化轉變溫度Tg為140℃。用相同的方法測試化合物35，化合物36，化合物43，和化合物46的玻璃化溫度，所得結果列于表1中。
比較例1
跟實施例1一樣的條件，測得化合物mCP和BCP的玻璃化轉變溫度，所得結果也列于表1中。
從表1中，可以看出本發明的化合物比常規的市場化的主體材料具有更高的玻璃化轉變溫度，本發明改善了電致發光材料的熱穩定性。
實施7
使用本發明的有機電致發光材料制備OLED，器件結構如圖1首先，將透明導電ITO玻璃(帶有陽極20的玻璃基板10)依次經：洗滌劑溶液和去離子水，乙醇，丙酮，去離子水洗淨。再用氧等離子處理30秒，接著用等離子處理的CFx處理。
然後，在ITO上蒸渡5 nm厚的MoO3空穴注入層30。
然後，蒸渡TAPC形成50 nm厚的空穴傳輸層40。
然後，在空穴傳輸層上蒸渡10 nm厚發光層50，其中，化合物35為主體發光材料，而以10%FIrpic作為作為藍色磷光材料。
然後，在發光層上蒸渡50 nm厚的TmPyPb作為電子傳輸層60。
最後，蒸渡1.2 nm LiF作為電子注入層70和150 nm Al陰極。
本發明所制備的有機電致發光器件在4V的驅動電壓下的電流密度為0.28 mA/cm2，發射藍光。
比較例2
器件結構跟實施例7一樣，除了用CBP代替化合物35。
此比較例制備的有機電致發光器件在4V的驅動電壓下的電流密度為0.17 mA/cm2，發射藍光。
因此，本發明相比較常規的材料，在相同的驅動電壓下具有跟高的電流密度，改善了電致發光性質。

Claims (14)

  1. 一種有機電子材料，具有如下式(I)或(II)所述的結構， 其中，R1-R5中任意四個為氫，另一個為C1-C6烷基、C7-C24的芳基、含有一個或多個選自N、O、S的取代或未取代的雜芳環、三芳香甲矽烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；或者R1、R3、R5為氫，R2、R4分別獨立為C1-C6烷基、C6-C24的芳基、含有一個或多個選自N、O、S的雜芳環、三芳香甲矽烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；A獨立地表示為C(R6)2、N(R7)、S、O、P(R8)、S(O)2或者B(R9)，R6-R9獨立地表示為氫、氘、烷基、苯基、烷基苯基、含有一個或多個選自N、O、S的雜芳基，或兩個R6與C之間形成環狀結構。
  2. 根據權利要求1所述的有機電子材料，其中R1-R5中任意四個為氫，另一個為芴基、烷基或苯基或萘基取代的五元或六元雜芳環基、二苯基胺基、苯萘胺基、三苯基甲矽烷基、二苯基氧磷、苯基羰基或苯基硫基。
  3. 根據權利要求2所述的有機電子材料，其中所述五元或六元雜芳環基為哢唑基、嘧啶基、吡啶基、噻唑基、三氮唑基或三嗪基。
  4. 根據權利要求2所述的有機電子材料，其中所述芴基為9，9-二甲基芴基、9，9-二苯基芴基、9，9-二甲苯基芴基或螺芴基。
  5. 根據權利要求2-4任一所述的有機電子材料，其中R1、R2、R4、R5為氫。
  6. 根據權利要求1所述的有機電致發光材料，其中A為C(R6)2、N(R7)、S、O、S(O)2，R6、R7獨立為氫、甲基、苯基或甲基苯基，或兩個R6與C之間形成五元環狀結構。
  7. 權利要求1所述的有機電子材料，其結構如下：
  8. 權利要求1所述的有機電子材料，其結構式為：
  9. 一種含有權利要求1-8任一所述的有機電子材料的有機電致發光器件。
  10. 根據權利要求9所述的有機電致發光器件，包括空穴注入層，空穴傳輸層，發光層，電子傳輸層或/和電子注入層，其中權利要求1-8任一所述的有機電子材料作為空穴注入層，空穴傳輸層，發光層，電子傳輸層或/和電子注入層中的任一層或多層中的材料。
  11. 根據權利要求10所述的有機電致發光器件，權利要求1-8任一所述的有機電子材料作為電子傳輸層的材料。
  12. 根據權利要求10所述的有機電致發光器件，所述發光層中包括主體材料和客體材料，其中權利要求1-8任一所述的有機電子材料為發光層中紅色磷光的主體材料。
  13. 根據權利要求12所述的有機電致發光器件，其中客體材料為有機銥化合物或有機鉑化合物。
  14. 根據權利要求12或13所述的有機電致發光器件，權利要求1-8任一所述的有機電子材料作為電子傳輸層的材料。
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