CN106565433B - 一种有机化合物及其在电致发光器件中的应用 - Google Patents

一种有机化合物及其在电致发光器件中的应用 Download PDF

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CN106565433B
CN106565433B CN201610945886.6A CN201610945886A CN106565433B CN 106565433 B CN106565433 B CN 106565433B CN 201610945886 A CN201610945886 A CN 201610945886A CN 106565433 B CN106565433 B CN 106565433B
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hydrogen atom
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CN106565433A (zh
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吕瑶
贾学艺
贾莹莹
王帅
冯玉
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Green People's Science And Technology Ltd Co In Beijing
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Abstract

本发明提供了一种式I所示的有机化合物。本发明还提供了所述有机化合物在电致发光器件中的应用。所述有机化合物可以有效地改善电致发光器件的性能。

Description

一种有机化合物及其在电致发光器件中的应用
技术领域
本发明涉及一种有机化合物及其在电致发光器件中的应用。
背景技术
有机金属化合物作为磷光发光体可以实现最高达四倍的能量和功率效率增加。然而，磷光OLED仍然需要进行改进，例如在效率、工作电压和寿命方面的改进。不能仅由三线态发光体确定磷光OLED的性能。特别是，使用的其它材料，例如基质材料、空穴阻挡材料、电子传输材料、空穴传输材料和电子或激子阻挡材料，此处同样具有特别重要的意义。因此，这些材料的改进同样可以导致OLED性能的显著改进。
本领域仍需要开发新型的化合物，使用所述化合物能够在一个或多个相关点例如发光的性能效率、寿命或颜色坐标实现电子器件的性质的改进。
发明内容
针对现有技术的状况，本发明首先提供了一种有机化合物，使用本发明的有机化合物能够在发光的性能效率、寿命或颜色坐标实现电子器件的性质的改进。
本发明的有机化合物的结构如式I所示，
Figure BDA0001141156390000011
L1和L2各自独立地为单键、取代或未取代的C6-C60亚芳基、取代或未取代的C3-C60亚杂芳基；
R3为取代或未取代的C1-C10烷氧基、取代或未取代的C3-C60环烷氧基、C6-C60芳基取代的胺基、C3-C60芳基取代的或未取代的咔唑基、取代或未取代的磷氧基、取代或未取代的C6-C40芳基或取代或未取代的C3-C40杂芳基；
R1、R2、R4、R5、R6、R7和R8相同或不同，各自独立为氢原子、重氢原子、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C10烷氧基、取代或未取代的C3-C60环烷氧基、取代或未取代的C3-C60环烷基、取代或未取代的C2-C50烯基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳基取代的胺基、C3-C60芳基取代的或未取代的咔唑基、取代或未取代的硅烷基、取代或未取代的磷氧基、取代或未取代的C3-C60杂芳基或取代或未取代的C6-C60稠合多环基。
根据本发明的一些实施方式，R3和R4各自独立地为取代或未取代的C1-C10烷氧基或取代或未取代的C3-C60环烷氧基；优选所述C1-C10烷氧基为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、异丁氧基、正戊氧基、异戊氧基、正己氧基或正庚氧基。
根据本发明的一些实施方式，L1和L2独立地选自以下基团：单键、
Figure BDA0001141156390000021
Figure BDA0001141156390000031
根据本发明的一些实施方式，R1、R2和R4独立地选自以下基团：氢原子、重氢原子、氰基、取代或未取代的C1-C10烷基、取代或未取代的C1-C10烷氧基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的菲啰啉基、取代或未取代的荧蒽基、取代或未取代的三亚苯基、取代或未取代的芴基、取代或未取代的9,9’-螺二芴基、取代或未取代的9,9-二甲基芴基、取代或未取代的9,9-二苯基芴基、取代或未取代的
Figure BDA0001141156390000033
基、取代或未取代的苯并[9,10]菲基、取代或未取代的苯并呋喃基、取代或未取代的异苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的异苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的联咔唑基、取代或未取代的二苯基磷氧基，取代或未取代的三苯基硅烷基、取代或未取代的四苯基硅烷基、C5-C60芳香基取代的胺基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的三嗪基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的喹唑啉基、取代或未取代的吲嗪基、取代或未取代的氮杂苯并[9,10]菲基、取代或未取代的二氮杂苯并[9,10]菲基、取代或未取代的氮杂咔唑基、取代或未取代的氮杂二苯并呋喃基、取代或未取代的氮杂二苯并噻吩基、取代或未取代的苯并咪唑基、取代或未取代的甲氧基芘基、取代或未取代的二氮杂咔唑基、取代或未取代的二氮杂二苯并呋喃基、取代或未取代的二氮杂二苯并噻吩基、取代或未取代的甲氧基芘基、取代或未取代的吲哚咔唑基以及取代或未取代的茚并咔唑基。
根据本发明的一些实施方式所述有机化合物的结构如式II所示，
Figure BDA0001141156390000032
其中，R为C1-C10烷基，优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、仲丁基、戊基、己基、庚基或辛基；
X9和X12独立地为单键、亚苯基、亚萘基或亚蒽基；
X10、X11、X13和X14相同或不同，各自独立地为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的菲啰啉基、取代或未取代的芴基、取代或未取代的9,9’-螺二芴基、取代或未取代的9,9-二甲基芴基、取代或未取代的9,9’-二苯基芴基、取代或未取代的苯并呋喃基、取代或未取代的异苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的异苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的联咔唑基或取代或未取代的苯并[9,10]菲基。
根据本发明的一些实施方式，所述有机化合物的结构如式III、IV、V、VI或VII所示，
Figure BDA0001141156390000041
其中，R13和R14独立地选自取代或未取代的苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的连咔唑基、取代或未取代的吲哚咔唑基、取代或未取代的茚并咔唑基、取代或未取代的芴基、取代或未取代的9,9’-螺二芴基、取代或未取代的9,9-二甲基芴基、取代或未取代的9,9’-二苯基芴基、取代或未取代的三联苯基、取代或未取代的氰基苯基、取代或未取代的1,3,5-三苯基苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的菲啰啉基、取代或未取代的荧蒽基或取代或未取代的三亚苯基；
R9、R10、R11、R12、R16、X1、X2、X3、X4、X5、X6、X7和X8独立地选自氢原子、重氢原子、氰基、取代或未取代的C1-C10烷基、取代或未取代的C1-C10烷氧基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的菲啰啉基、取代或未取代的荧蒽基、取代或未取代的三亚苯基、取代或未取代的芴基、取代或未取代的9,9’-螺二芴基、取代或未取代的9,9-二甲基芴基、取代或未取代的9,9-二苯基芴基、取代或未取代的
Figure BDA0001141156390000042
基、取代或未取代的苯并[9,10]菲基、取代或未取代的苯并呋喃基、取代或未取代的异苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的异苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的联咔唑基、取代或未取代的二苯基磷氧基，取代或未取代的三苯基硅烷基、取代或未取代的四苯基硅烷基、C5-C60芳香基取代的胺基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的三嗪基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的喹唑啉基、取代或未取代的吲嗪基、取代或未取代的氮杂苯并[9,10]菲基、取代或未取代的二氮杂苯并[9,10]菲基、取代或未取代的氮杂咔唑基、取代或未取代的氮杂二苯并呋喃基、取代或未取代的氮杂二苯并噻吩基、取代或未取代的苯并咪唑基、取代或未取代的二氮杂咔唑基、取代或未取代的二氮杂二苯并呋喃基、取代或未取代的二氮杂二苯并噻吩基、取代或未取代的甲氧基芘基、取代或未取代的吲哚咔唑基、取代或未取代的茚并咔唑基。
根据本发明的另一些实施方式，所述有机化合物的结构如式VIII所示，
Figure BDA0001141156390000051
其中，Y为O、S或NR15，R15为C6-C40芳基，优选为苯基。
根据本发明的一些实施方式，L1和L2独立地选自以下连接基团：
本发明中，各基团上的星号*表示基团与其他部分的连接点。
本发明的有机化合物的具体例子包括但不限于以下化合物：
Figure BDA0001141156390000053
Figure BDA0001141156390000061
Figure BDA0001141156390000071
Figure BDA0001141156390000081
Figure BDA0001141156390000091
Figure BDA0001141156390000101
Figure BDA0001141156390000111
Figure BDA0001141156390000161
Figure BDA0001141156390000171
本发明还提供了所述在电子器件特别是有机电致发光器件中的应用。根据本发明的实施方式，所述有机化合物可以用做荧光发光体、延迟荧光发光体或磷光发光体。根据本发明的实施方式，所述有机化合物可以用于荧光或磷光发光体的基质材料。根据本发明的实施方式，可以用于电子传输层、空穴阻挡层、电子阻挡层、激子阻挡层和/或空穴传输层中。
具体实施方式
以下结合实施例对本发明作进一步阐述，但应理解，本发明的范围并不限于此。
合成实施例1
化合物1的合成
将30g(0.083mol)1,6-二溴苯溶于300ml DMF溶液中，8.96g(0.166mol)甲醇钠溶于30ml甲醇中，将甲醇钠溶液滴加进底物的DMF溶液中，0.16g(0.00166mol)氯化亚铜做催化剂，加热搅拌至回流，反应5小时。将反应液倒入水中，调PH至中性，乙酸乙酯萃取，有机相通过旋蒸使溶剂蒸发，得到11.28g化合物1(产率:52％)。
计算值C18H14O2:C,88.42；H,5.38；O,12.20；实测值：C,88.50；H,5.36；O,12.14。1H-NMR(400MHz，CDCl3)(ppm)δ＝3.83(6H，s)，7.31-7.34(2H，d)，7.71(4H，s)，7.87-7.90(2H，d)。
合成实施例2
Figure BDA0001141156390000181
中间体2-1的合成
将11.28(0.043mol)化合物1溶于60mlDMF,30.6g(0.172mol)NBS溶于53mlDMF溶剂中，再将NBS溶液以每秒3至5滴的速度滴加进底物溶液中，搅拌。常温下，滴加完后反应也随之停止。在反应液中滴加23ml水，析晶，抽滤，得到14.1g中间体2-1(产率:78％)。
化合物17的合成
将14.1g(0.0335mol)中间体2-1、12.6g(0.0737ml)1-萘硼酸和13.8g(0.1005mol)碳酸钾依次加入140ml甲苯、70ml乙醇和28ml水的混合溶液中，氮气保护下，加入0.38g(0.000335mol)四(三苯基磷钯)，加热搅拌至回流，反应3小时。将反应液过硅藻土漏斗，滤液用水萃取，有机相通过旋蒸使溶剂蒸发，得到12.9g化合物17(产率:75％)。
计算值C38H26O2:C,88.69；H,5.09；O,6.22；实测值：C,88.79；H,5.14；O,6.17；1H-NMR(400MHz，CDCl3)(ppm)δ＝3.84(6H，s)，7.53-7.62(8H，m)，7.71(4H，s)，8.04-8.09(4H，m)，8.54-8.57(2H，d)，8.42-8.44(2H，d)。
合成实施例3
Figure BDA0001141156390000182
中间体3-1的合成
将20g(0.076mol)化合物1加入200ml氢溴酸中，加热搅拌至回流，反应2小时。反应完毕后，将反应液通过旋蒸使溶剂蒸发，得到14.76g中间体3-1(产率：83％)。
化合物140的合成
将14.76g(0.063mol)中间体3-1加入到150mlDMF中后将反应降温至0℃左右后搅拌30min后，滴加溴乙烷后将反应升温至室温后反应过夜。反应完毕后将反应降温至0℃左右后先反应中滴加100ml冰水，滴加完毕后有大量固体析出过滤得到粗品用甲苯重结晶得到15.35g化合物140(产率：84％)。
计算值C20H18O2:C,82.73；H,6.25；O,11.02；实测值：C,82.80；H,6.23；O,10.98；1H-NMR(400MHz，CDCl3)(ppm)δ＝1.30-1.35(6H，m)，4.70-4.74(4H，m)，7.32-7.34(2H，d)，7.71(4H，s)，7.87-7.90(2H，d)。
合成实施例4
中间体4-1的合成
将15.35g(0.052mol)化合物140溶于80mlDMF，37.0g(0.208mol)NBS溶于73mlDMF溶剂中，再将NBS溶液以每秒3至5滴的速度滴加进底物溶液中，搅拌。常温下，滴加完后反应也随之停止。在反应液中滴加30ml水，析晶，抽滤，得到19.56g中间体4-1(产率:85％)。
化合物141的合成：与化合物17的合成方法相同，产率:83％。
计算值C38H26O2:C,86.57；H,5.71；N,3.61；O,4.12；实测值：C,86.61；H,5.67；O,4.15。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.30-1.35(6H，t)，4.69-4.74(4H，q)，6.62-6.72(12H，m)，6.78-4.84(4H，m)，7.17-7.22(8H，m)，7.52-7.57(6H，m)，7.71(4H，s)。
合成实施例5
Figure BDA0001141156390000192
化合物148的合成：与化合物17的合成方法相同。产率:78％。
计算值C38H26O2:C,80.70；H,4.62；O,4.89；S,9.79实测值：C,88.79；H,4.60；O,4.85。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.30-1.34(6H，t)，4.70-4.73(4H，q)，7.49-7.57(8H，m)，7.71(4H，s)，7.97-7.99(2H，d)，8.21-8.23(2H，d)，8.40-8.47(6H，m)。
合成实施例6
Figure BDA0001141156390000193
化合物150的合成与化合物140的合成方法相同，产率：89％。
计算值C22H22O2:C,82.99；H,6.96；O,10.05；实测值：C,83.01；H,6.95；O,10.04。1H-NMR(400MHz，CDCl3)(ppm)δ＝0.89-0.92(6H，t)，1.71-1.76(4H，m)，4.14-4.18(4H，q)，7.31-7.34(2H，d)，7.71(4H，s)，7.88-7.90(2H，d)。
合成实施例7
Figure BDA0001141156390000194
中间体7-1的合成
将36.3g(0.114mol)化合物150溶于190mlDMF，84.1g(0.456mol)NBS溶于173mlDMF溶剂中，再将NBS溶液以每秒3至5滴的速度滴加进底物溶液中，搅拌。常温下，滴加完后反应也随之停止。在反应液中滴加72ml水，析晶，抽滤，得到46.6g中间体7-1(产率:86％)。
化合物158的合成：与化合物17的合成方法相同，产率:83％。
计算值C38H26O2:C,84.90；H,5.27；O,9.83；实测值：C,84.95；H,5.23；O,9.82。1H-NMR(400MHz，CDCl3)(ppm)δ＝0.89-0.92(6H，t)，1.71-1.76(4H，m)，4.14-4.18(4H，q)，7.31-7.39(6H，m)，7.54-7.56(2H，d)，7.64-7.67(2H，d)，7.71(4H，s)，7.80-7.90(6H，m)。
合成实施例8
Figure BDA0001141156390000201
化合物161的合成：与化合物140的合成方法相同，产率：81％。
计算值C22H22O2:C,82.99；H,6.96；O,10.05；实测值：C,83.04；H,6.93；O,10.03。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.33-1.37(12H，dt)，4.66-4.73(2H，m)，7.31-7.34(2H,d)，7.71(4H,s)，7.88-7.91(2H,d)。
合成实施例9
Figure BDA0001141156390000202
中间体9-1的合成与中间体2-1的合成方法相同，产率:86％。
化合物169的合成与化合物17的合成方法相同，产率:75％。
计算值C38H26O2:C,86.97；H,5.54；N,3.50；O,3.099实测值：C,87.01；H,5.52；O,3.10。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.35(12H，d)，4.70(2H，m)，7.23-7.30(6H，m)，7.50(2H，m)，7.55(2H，s)，7.63(2H，d)，7.68(4H，d)，7.71(4H，s)，7.79(4H，d)，7.94(2H，d)，8.12(2H，d)，8.11-8.14(2H，d)，8.52-8.56(2H，d)。
合成实施例10
Figure BDA0001141156390000203
中间体10-1的合成
将40g(0.16mol)2-氨基联苯、40g(0.24mol)4-溴二苯并呋喃和18.4g(0.192mol)叔丁醇那依次溶解在400ml甲苯中，氮气保护下，加入3.2ml(0.0016mol)三叔丁基磷和1.46g(0.0016mol)Pd2(dba)3，搅拌升温至90℃，反应约2小时。将所得反应液过硅藻土漏斗，滤液通过旋转蒸发仪使溶剂蒸发，得到40g中间体10-1(产率：75％)。
化合物165的合成
将40g(0.12mol)中间体10-1、25.7(0.054mol)中间体10-1和11.5g(0.12mol)叔丁醇那依次溶解在400ml甲苯中，氮气保护下，加入1.09ml(0.00054mol)三叔丁基磷和0.49g(0.00054mol)Pd2(dba)3，在约110℃下加热搅拌约12小时。将所得反应液过硅藻土漏斗，液通过过旋转蒸发仪使溶剂蒸发。再加入甲苯溶解，到入乙醇以获得固体，将固体过滤获得69.7g化合物165(产率：59％)。
计算值C38H26O2:C,85.34；H,5.32；N,2.84；O,6.50；实测值：C,89.69；H,6.09；O,7.22。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.33-1.36(12H，d)，4.67-4.73(2H，m)，6.38-6.41(6H，m)，6.53(2H，s)，6.68-6.70(2H，d)，6.85-6.89(2H，m)，7.06-7.18(8H，m)，7.22-7.56(2H，m)，7.31-7.43(6H，m)，7.50-7.56(6H，m)，7.71(4H，s)，7.66-7.69(2H，d)，7.88-7.90(2H，d)。
合成实施例11
Figure BDA0001141156390000211
化合物178的合成：与化合物140的合成方法相同，产率：88％。
计算值C24H26O2:C,83.20；H,7.56；O,9.42实测值：C,83.27；H,7.52；O,9.39。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.41(18H，s)，7.31-7.34(2H，d)，7.71(4H，d)，7.88-7.90(2H，d)。
合成实施例12
Figure BDA0001141156390000212
化合物65的合成与化合物165的合成方法相同。
计算值C54H40N2O2:C,86.60；H,5.38；N,3.74；O,4.27；实测值：C,86.69；H,5.34；O,4.22。1H-NMR(400MHz，CDCl3)(ppm)δ＝3.83(6H，s)，6.53(2H，s)，6.62-6.65(4H，m)，6.68-6.70(4H，m)，6.78-6.84(2H，m)，7.17-7.22(4H，m)，7.37-7.44(2H，m)，7.48-7.45(4H，m)，7.71(4H，s)。
合成实施例13
Figure BDA0001141156390000221
化合物149的合成与化合物17的合成方法相同。
计算值C44H30O2S2:C,80.70；H,4.62；S,9.79；O,4.89；实测值：C,80.73；H,4.62；O,4.87。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.30-1.35(6H，d)，4.69-4.73(4H，m)，7.48-7.60(8H，m)，7.71(2H，s)，7.80-7.84(2H，m)，7.91-8.02(4H，m)，8.44-8.46(2H，d)。
合成实施例14
Figure BDA0001141156390000222
化合物159的合成与化合物17的合成方法相同。
计算值C54H42O2:C,89.72；H,5.86；O,4.43；实测值：C,89.79；H,5.82；O,4.40。1H-NMR(400MHz，CDCl3)(ppm)δ＝0.87-0.91(6H，m)，1.70-1.76(4H，m)，4.13-4.18(4H，m)，7.25(8H，s)，7.50-7.63(8H，m)，7.71(4H，s)，8.01-8.10(4H，m)，8.40-8.46(2H，m)，8.53-8.56(2H，m)。
合成实施例15
化合物160的合成与化合物17的合成方法相同。
计算值C58H44N2O2:C,86.79；H,5.54；N,3.50；O,3.99；实测值：C,86.85；H,5.52；O,3.94。1H-NMR(400MHz，CDCl3)(ppm)δ＝0.87-0.91(6H，m)，1.70-1.76(4H，m)，4.13-4.18(4H，m)，7.20-7.35(6H，m)，7.47-7.58(10H，m)，7.62-7.64(2H，d)，7.71(4H，s)，7.92-7.95(2H，d)，8.05-8.13(4H，m)，8.54-8.57(2H，d)。
合成实施例16
Figure BDA0001141156390000231
化合物170的合成与化合物17的合成方法相同。
计算值C70H58O2Si2:C,85.15；H,5.92；O,3.24；Si,5.69；实测值：C,85.25；H,5.89；O,3.20。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.33-1.36(12H，d)，4.67-4.73(2H，m)，7.35-7.38(12H，m)，7.44-7.50(12H，m)，7.52-7.57(6H，m)，7.71(4H，s)，7.88-7.90(2H，d)。
合成实施例17
化合物171的合成与化合物17的合成方法相同。
计算值C54H42O2:C,89.72；H,5.86；O,4.43；实测值：C,89.79；H,5.83；O,4.40。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.33-1.36(12H，d)，4.67-4.73(2H，m)，7.39-43(2H，m)，7.47-7.61(14H，m)，7.70-7.74(8H，m)，7.90-7.94(4H，d)。
合成实施例18
Figure BDA0001141156390000233
化合物181的合成与化合物17的合成方法相同。
计算值C60H46O4:C,86.72；H,5.58；O,7.70；实测值：C,86.78；H,5.55；O,7.65。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.41(18H，d)，7.25(8H，s)，7.30-7.40(6H，m)，7.55(2H，s)，7.65-7.67(2H，d)，7.71(4H，s)，7.78-7.93(6H，m)。
合成实施例19
Figure BDA0001141156390000234
化合物179的合成：与化合物165的合成方法相同。
计算值C72H60N2O2:C,87.77；H,6.14；N,2.84；O,3.25；实测值：C,89.85；H,6.10；O,3.21。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.41(18H，d)，6.53(2H，S)，6.67-6.71(8H，m)，7.38-7.44(4H，m)，7.49-7.56(24H，m)，7.71(4H，S)。
合成实施例20
Figure BDA0001141156390000241
化合物40的合成与化合物17的合成方法相同。
计算值C54H36N2O2:C,87.07；H,4.87；N,3.76；O,4.30；实测值：C,86.90；H,4.90；O,4.33。1H-NMR(400MHz，CDCl3)(ppm)δ＝3.83(6H，s)，7.27-7.30(2H，m)，7.44-7.51(8H，m)，7.55(2H，s)，7.56-7.64(6H，m)，7.70-7.72(4H，d)，7.77(2H，s)，7.79-7.82(2H，d)，8.10-7.20(4H，m)。
合成实施例21
Figure BDA0001141156390000242
中间体21-1的合成与化合物17的合成方法相同
化合物208的合成与化合物165的合成方法相同。
计算值C58H38N4:C,88.07；H,4.84；N,7.08；实测值：C,88.11；H,4.83；N,7.07。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.72(6H，s)，7.23-7.46(11H，m)，7.60-7.62(1H，d)，7.68-7.73(5H，m)，7.81-7.95(4H，m)，8.03-8.19(6H，m)，8.27-8.29(4H，d)，8.54-8.56(1H，d)。
合成实施例22
Figure BDA0001141156390000243
中间体233-1的合成与化合物165的合成方法相同。
中间体233-2的合成与化合物165的合成方法相同。
化合物233的合成与化合物17的合成方法相同。
计算值C76H48N6:C,87.33；H,4.63；N,8.04；实测值：C,87.35；H,4.65；N,8.00。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.72(6H，s)，7.23-7.35(8H，m)，7.42-7.60(9H，m)，7.67-7.94(16H，m)，8.03-8.19(5H，m)，8.27-8.29(1H，m)，8.54-8.56(3H，d)。
合成实施例23
Figure BDA0001141156390000251
中间体213-1的合成与化合物165的合成方法相同。
化合物213的合成与化合物17的合成方法相同。
计算值C55H36N2:C,91.13；H,5.01；N,3.86；实测值：C,91.02；H,5.07；N,3.91。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.72(6H，s)，7.23-7.35(4H，m)，7.42-7.61(7H，m)，7.67-7.78(8H，m)，7.81-8.03(6H，m)，8.08-8.19(4H，m)，8.54-8.56(1H，d)。
合成实施例24
Figure BDA0001141156390000252
化合物192的合成与化合物165的合成方法相同。
计算值C66H60N2O4:C,83.87；H,6.40；N,2.96；O,6.77；实测值：C,83.95；H,6.37；O,6.75。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.33-7.38(30H，m)，4.69-4.72(2H，m)，6.38-6.41(2H，m)，6.53(2H，s)，6.62-6.65(4H，m)，6.80-6.83(2H，m)，7.05-7.08(2H，m)，7.19-7.27(10H，m)，7.68-7.72(6H，m)。
合成实施例25
Figure BDA0001141156390000261
中间体20-1的合成与化合物17的合成方法相同。
将46g(0.236mol)2-溴苯并恶唑溶于460ml二氧六环溶液中，搅拌加入29.3g(0.24mol)苯硼酸，加入90ml水，加入81.4g(0.59mol)无水碳酸钾，在氮气氛围下加入2.7g(0.00236)四三苯基膦钯。加热升温至回流反应5小时。降温后将反应液过硅藻土漏斗，滤液用水萃取，有机相通过旋蒸使溶剂蒸发后甲苯重结晶得到34.5g中间体20-1(产率:75％)。
中间体20-2的合成与中间体2-1的合成方法相同。
将34.5g(0.177mol)中间体20-1溶于250mlDMF31.7g(0.177mol)NBS溶于100mlDMF溶剂中，再将NBS溶液以每秒3至5滴的速度滴加进底物溶液中，常温下，滴加完后反应也随之停止。在反应液中滴加300ml水，析晶，抽滤得到粗品，甲苯重结晶后得到35g中间体20-2(产率:73％)。
中间体20-3的合成：
首先35g(0.129mol)中间体20-2放入2升三口瓶中，瓶中为氮气氛围。添加了840毫升的四氢呋喃并冷却到-78℃。冷却后，开始滴加83.2ml(0.141mol)1.6M-n-丁基锂,在相同的温度下混合搅拌2小时。一定时间后,滴加28.16ml(0.256mol)硼酸三甲酯，滴加完毕后提高溶液的温度到室温,然后,反应16个小时。之后后,加入640毫升1mol/L盐酸和搅拌1小时。获得的水相与乙酸乙酯提取的混合物。获得的提取液与饱和盐水洗有机层，然后硫酸镁干燥。获得的混合物过滤后，所得滤液旋蒸成固体。得到21g(0.0877mol)中间体20-3(产率:68％)
中间体20-4的合成与化合物17的合成方法相同。
将21g(0.0877mol)中间体20-3溶于210ml二氧六环溶液中，搅拌加入13.1g(0.0366mol)1,6-二溴芘，加入30ml水，加入25.3g(0.183mol)无水碳酸钾，在氮气氛围下加入0.27g(0.000366)二茂铁二氯化钯。加热升温至回流反应5小时。降温后将反应液过硅藻土漏斗，滤液用水萃取，有机相通过旋蒸使溶剂蒸发后，将得到粗品过快速硅胶柱得到15.07g中间体20-4(产率70％)。
中间体20-5的合成与中间体2-1的合成方法相同。
将15.07(0.0256mol)中间体20-4溶于90mlDMF,9.34g(0.0525mol)NBS溶于60mlDMF溶剂中，再将NBS溶液以每秒3至5滴的速度滴加进底物溶液中，搅拌，温度为80℃下，滴加完后反应也随之停止。在反应液中滴加150ml水，析晶，抽滤，得粗品后甲苯重结晶得到11.4g中间体20-5(产率:60％)。
化合物189的合成与化合物17的合成方法相同。
将20g(0.0269mol)中间体20-5溶于200ml二氧六环溶液中，搅拌加入8.2g(0.0672mol)苯硼酸，加入25ml水，加入18.56g(0.1345mol)无水碳酸钾，在氮气氛围下加入0.2g(0.000269)二茂铁二氯化钯。加热升温至回流反应10小时后结束。降温并将反应液过硅藻土漏斗，滤液用水萃取，有机相通过旋蒸使溶剂蒸发后，将得到粗品过快速硅胶柱得到13.9g化合物189(产率70％)。
计算值：C,87.55；H,4.35；N,3.78；O,4.32；实测值：C,87.58；H,4.34；N,3.79；O,4.29。1H-NMR(400MHz，CDCl3)(ppm)δ＝7.24-7.25(4H，d)，7.38-7.40(4H，m)，7.40-7.42(2H，m)，7.50-7.52(4H，t)，7.70-7.75(8H，m)，7.78-7.80(4H，m)，7.84-7.86(4H，m)，8.26(2H，s)。
合成实施例26
Figure BDA0001141156390000271
中间体26-1的合成与化合物17的合成方法相同，收率38％。
化合物292与化合物17的合成方法相同，收率62％。
计算值：C,87.82；H,4.45；N,7.73；实测值：C,87.85；H,4.43；N,7.73。
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.22-7.28(6H，m)，7.34-7.35(1H，m)，7.45-7.46(1H，m)，7.50-7.51(2H，m)，7.58-7.60(4H，m)，7.71-7.72(4H，s)，7.81-7.85(3H，m)，7.94-7.95(1H，d)，8.04-8.10(4H，m)，8.18-8.19(1H，m)，8.38-8.39(1H，d)，8.56-8.57(1H，m)，8.81-8.83(3H，m)。
合成实施例27
Figure BDA0001141156390000272
中间体27-1的合成与化合物17的合成方法相同，收率34％。
化合物299与化合物17的合成方法相同，收率55％。
计算值：C,86.88；H,4.19；N,6.47；O,2.46；实测值：C,86.86；H,4.18；N,6.48；O,2.48。1H-NMR(400MHz，CDCl3)(ppm)δ＝7.24-7.25(2H，d)，7.35-7.39(3H，m)，7.54-7.60(3H，m)，7.71-7.74(6H，m)，7.81-7.85(3H，m)，7.94-7.95(1H，d)，8.04-8.06(3H，m)，8.10-8.11(1H，m)，8.18-8.21(2H，m)，8.26-8.27(1H，m)，8.38-8.39(1H，m)，8.81-8.82(1H，m)。
器件实施例
实施例1-1ETL
先用蒸馏水、然后用溶剂例如异丙醇、丙酮和甲醇超声洗涤具有约1500埃厚度的氧化铟锡(ITO)电极(第一电极，阳极)的玻璃衬底之后，将经洗涤的玻璃衬底干燥，移到等离子体清洁系统，然后使用氧等离子体清洁约5分钟。然后将所述玻璃衬底装载到真空沉积设备中。
将化合物2-TNATA真空沉积到所述玻璃衬底的ITO电极上以形成具有约1000埃厚度的HIL，将NPB真空沉积到空穴注入层上形成具有约200埃厚度的HTL。
将化合物ADN和DPAVBi(掺杂剂)以98:2的质量比共沉积在所述空穴传输区域上以形成具有约300埃厚度的EML。
随后，将化合物1真空沉积在所述EML上以形成具有约250埃厚度的ETL。然后，将LiF沉积在ETL上以形成具有约5埃厚度的EIL，并将Al沉积在所述EIL上至约1000的厚度以形成第二电极(阴极)，由此完成有机发光器件的制造。
Figure BDA0001141156390000281
实施例1-2至实施例1-8
以与实施例1-1中相同的方式制造有机发光器件，除了使用表1中的化合物代替化合物1作为电子传输层之外。
对比例1
以与实施例1-1中相同的方式制造有机发光器件，除了使用Alq3代替化合物1以形成电子传输层之外。
表1
Figure BDA0001141156390000282
Figure BDA0001141156390000291
通过表1中的数据可以看出，本发明的电子传输材料可以降低OLED器件的驱动电压，提高OLED器件的寿命、效率及亮度。
实施例2-1
先用蒸馏水、然后用溶剂例如异丙醇、丙酮和甲醇超声洗涤具有约1500埃厚度的氧化铟锡(ITO)电极(第一电极，阳极)的玻璃衬底之后，将经洗涤的玻璃衬底干燥，移到等离子体清洁系统，然后使用氧等离子体清洁约5分钟。然后将所述玻璃衬底装载到真空沉积设备中。
将化合物2-TNATA真空沉积到所述玻璃衬底的ITO电极上以形成具有约600埃厚度的HIL，将化合物NPB真空沉积到空穴注入层上形成具有约300埃厚度的HTL。
将化合物40(绿色磷光主体)和Ir(ppy)3(绿光掺杂剂，10重量百分数(重量％))共沉积在所述空穴传输区域上以形成具有约300埃厚度的EML。将BCP真空沉积在发光层上形成50埃厚的空穴阻挡层。
随后，将Alq3真空沉积在所述空穴阻挡层上以形成具有约250埃厚度的ETL。然后，将LiF沉积在ETL上以形成具有约5埃厚度的EIL，并将Al沉积在所述EIL上至约1000埃的厚度以形成第二电极(阴极)，由此完成有机发光器件的制造。
Figure BDA0001141156390000292
实施例2-2至实施例2-17
以与实施例2-1中相同的方式制造有机发光器件，除了使用表2中的化合物代替发光层之外。
对比例2-1至对比例2-3
以与实施例2-1中相同的方式制造有机发光器件，除了使用表2中的化合物代替发光层之外。
Figure BDA0001141156390000293
表2
Figure BDA0001141156390000301
通过表2中的数据可以看出，与现有材料CBP相比，本发明的绿光主体，蓝光主体及蓝光掺杂剂可以降低OLED器件的驱动电压，提高OLED器件的效率及亮度。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (5)

1.一种有机化合物，其结构如式I所示，
Figure FDA0002188347320000011
其中在式I中，
L1和L2各自独立地为单键、
Figure FDA0002188347320000012
Figure FDA0002188347320000021
R3为苯或联苯取代或未取代的咔唑基、未取代的苯基、未取代的联苯基、未取代的三联苯基、未取代的萘基、未取代的蒽基、未取代的菲基、未取代的苯并[9,10]菲基、未取代的菲啰啉基、未取代的荧蒽基、未取代的三亚苯基、未取代的二苯并呋喃基、未取代的二苯并噻吩基、苯基取代的苯并咪唑基、未取代的噻吩基、未取代的苯并呋喃基；
R1为未取代的C1-C4烷氧基；
R2为未取代的C1-C4烷氧基；
R4为氢原子、未取代的苯基、未取代的联苯基、未取代的三联苯基、未取代的萘基、未取代的蒽基、未取代的菲基、未取代的菲啰啉基、未取代的荧蒽基、未取代的三亚苯基、未取代的苯并[9,10]菲基、未取代的苯并呋喃基、未取代的异苯并呋喃基、未取代的苯并噻吩基、未取代的异苯并噻吩基、未取代的二苯并呋喃基、未取代的二苯并噻吩基、未取代的噻吩基、苯基或联苯基取代或未取代的咔唑基、苯基取代的苯并咪唑基；
R5为氢原子或重氢原子；
R6为氢原子或重氢原子；
R7为氢原子或重氢原子；
R8为氢原子或重氢原子。
2.根据权利要求1所述的化合物，其特征在于，所述C1-C4烷氧基为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基。
3.根据权利要求1所述的化合物，其特征在于，所述化合物选自以下结构所示的化合物：
Figure FDA0002188347320000022
Figure FDA0002188347320000041
4.根据权利要求1-3中任一项所述的有机化合物在电子器件特别是有机电致发光器件中的应用。
5.根据权利要求4所述的应用，其特征在于，所述有机化合物用做荧光发光体、延迟荧光发光体或磷光发光体，和/或用于荧光或磷光发光体的基质材料，和/或用于电子传输层、空穴阻挡层、电子阻挡层、激子阻挡层和/或空穴传输层中。
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