CN106565705B - 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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CN106565705B
CN106565705B CN201610945555.2A CN201610945555A CN106565705B CN 106565705 B CN106565705 B CN 106565705B CN 201610945555 A CN201610945555 A CN 201610945555A CN 106565705 B CN106565705 B CN 106565705B
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synthesis
unsubstituted
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yield
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CN106565705A (zh
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吕瑶
贾学艺
纪秦思
李鑫
王晓明
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。
本发明提供的有机化合物的结构如式I所示：
其中，L1和L2各自独立地为单键、取代或未取代的C6-C60亚芳基；
R3为取代或未取代的C3-C60杂芳基或取代或未取代的C6-C60稠合多环基；
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C3-C60环烷基、取代或未取代的C2-C50烯基、取代或未取代的C5-C60芳基、取代或未取代的C5-C60芳基取代的胺基、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，L1-R3不是以下基团：
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，
其中，X1、X2、X4、X5和X代表N或C；Y1、Y2、Y3、Y4和Y5中的两个或三个任选地成环。
根据本发明的一些实施方式，R1、R2、R3、R4、R5、R6、R7和R8独立地选自以下基团：取代或未取代的甲基、取代或未取代的乙基、取代或未取代的正丙基、取代或未取代的异丙基、取代或未取代的正丁基、取代或未取代的异丁基、取代或未取代的仲丁基、取代或未取代的叔丁基、取代或未取代的戊基、取代或未取代的己基、取代或未取代的庚基、取代或未取代的辛基、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、取代或未取代的菲基、取代或未取代的菲罗琳基、取代或未取代的芴基、取代或未取代的9,9’-螺二芴基、取代或未取代的基、取代或未取代的苯并[9,10]菲基、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、取代或未取代的吲嗪基、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、取代或未取代的咕吨基、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、取代或未取代的荧蒽基。
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或IV所示，
X为O、S、Ph-P＝O、N-Ph或C(CH3)2；
R1、R2和R4-R11相同或不同，各自独立地为氢原子、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、取代或未取代的茚并咔唑基；
R9、R10和R11可以连接在二苯并呋喃、二苯并噻吩、咔唑、9,9-二甲基芴、9,9’-螺二芴的任何位置上，芘与二苯并呋喃、二苯并噻吩、咔唑、9,9-二甲基芴、9,9’-螺二芴可以在任何位置相连，且R9、R10和R11中至多有一个为氢原子。
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：
根据本发明的一些实施方式，R1、R2、R3、R4、R5、R6、R7和R8各自独立选自以下基团：
本发明中，各基团上的星号*表示基团与其他部分的连接点。
根据本发明的一些实施方式，所述化合物的结构如式V、VI、VII或VIII所示，
其中，在式VI中，L1为除苯、萘、二联苯以外的C6-C30亚芳基或除苯、萘、二联苯以外的C5-C30亚杂芳基。
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：
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9-蒽硼酸(10mmol)，1-溴-4碘萘(10mmol)，碳酸钾(30mmol)，四三苯基膦钯(0.1mmol)依次加入到甲苯，乙醇，水的混合溶液中在氮气保护下将反应升温至回流反应过夜。将反应降温至室温有大量固体析出后过滤得到的产品用甲苯热煮全部溶解后过滤，滤液冷却析晶得到产品219-1(收率65％)。
将219-1(10mmol)加入到无水四氢呋喃中后将反应降温至-78度后滴加(15mmol)的正丁基锂将反应控制在-78度，滴加完毕反应30分钟后，滴加硼酸三甲酯(12mmol)滴加完毕后将反应升温至室温反应后，想反应滴加1mol/L的盐酸水溶液，后用乙酸乙酯萃取，有机相脱溶后得到粗品用乙酸乙酯热煮过滤后得到产品219-2(90％)。
将219-2(10mmol)，2-溴邻菲罗啉(9mmol)，碳酸钾(30mmol)，四三苯基膦钯(0.1mmol)依次加入到甲苯，乙醇，水的混合溶液中在氮气保护下将反应升温至回流后反应6小时后将反应降温。将反应过滤，滤液分液，水相用乙酸乙酯萃取合并有机相，用无水硫酸钠干燥30分钟以上后过滤将有机相脱溶后得到粗品，粗品用DMF重结晶得到产品219-3(收率71％)。
将219-3(10mmol)溶于10倍的DMF中后分批加入NBS(10.5mmol)后反应2小时后水析后过滤得到产品219-4(80％)。
将219-4(10mmol)，1-芘硼酸(10mmol)，碳酸钾(30mmol)，四三苯基膦钯(0.1mmol)依次加入到甲苯，乙醇，水的混合溶液中在氮气保护下将反应升温至回流反应过夜。将反应降温至室温有大量固体析出后过滤得到的产品用甲苯热煮全部溶解后过滤，滤液冷却析晶得到产品219(收率65％)。
M.W＝682.24 W.F＝C52H30N2。
NMR:8.83(1H,m),8.52-8.55(3H,m),8.38(1H,m),8.04-8.12(6H,m),7.81-7.97(7H,m),7.71(4H,d),7.55-7.58(3H,m),7.35-7.39(5H,m)。
合成实施例2：化合物179的合成
中间体2-1的合成
将25g(0.1236mol)芘溶解在500ml二氯甲烷中，然后将49.39g(0.309)溴素缓慢滴加至反应液中，然后室温搅拌30h左右，TLC检测反应完毕停止反应，向反应液中加水萃取，将有机相利用减压旋蒸出有机溶剂，将残余物利用柱层析得到28.5g中间体2-1(产率64％)。
中间体2-2的合成
将24g(0.0667mol)1,6-二溴芘(中间体2-1)溶解在240ml甲苯中，然后依次加入16.07g(0.0653mol)1-芘硼酸、180ml乙醇、27.6g(0.2mol)碳酸钾、60ml水，搅拌下通氮气15min，加入0.77g(0.0007mol)四(三苯基膦)钯，搅拌加热至90℃反应3h，停止反应，将反应液过硅藻土后分水减压旋出有机溶剂，然后将得到粗品利用甲苯/乙醇重结晶得到18.6g中间体2-2(产率58％)。
化合物179的合成
将11.07g(0.023mol)中间体2-2溶解在110ml1,4-二氧六环中，通氮气下搅拌依次加入11.01g(0.0253mol)3，5-二苯基-1,3,5-三嗪-1-苯基频哪醇酯、6.348g(0.046mol)碳酸钾、10ml水、0.17g(0.00023mol)二茂铁二氯化钯，升温至回流反应12h后停止，将反应液降至室温过滤，将过滤得固体用DMF重结晶得到10g化合物179(产率61％)。
计算值C53H31N3:C,89.68；H,4.40；N,5.92；实测值:C,89.81；H,4.28；N,5.91。1H-NMR(400MHz,CDCl3)(ppm)δ＝7.31～7.36(2H,d),7.46～7.49(2H,m),7.59～7.64(4H,t),7.82～7.86(8H,s),7.92～8.08(5H,m),8.11～8.14(3H,d),8.20～8.29(3H,m),8.31～8.34(4H,d)
合成实施例3：化合物204的合成
中间体3-1的合成：合成方法同中间体1-1的合成，得到52g中间体3-1(产率60％)。
化合物204的合成：将50g(0.0878mol)中间体3-1溶解在500ml甲苯中，通氮气下搅拌然后依次加入20.55g(mol)4-(4-溴苯基)吡啶、16.86g(0.1756mol)叔丁醇钠、0.73g(0.0008mol)(DBA)3Pd2、1.7ml三叔丁基膦，加热搅拌至回流，3h后停止反应，然后过硅藻土，减压旋干有机溶剂，将残余物利用对二甲苯重结晶得到30g化合物204(产率45％)。
计算值C55H34N2:C,91.38；H,4.74；N,3.88；实测值：C,91.46；H,4.70,N,3.84。
1H-NMR(400MHz,CDCl3)(ppm)δ＝6.71～6.74(6H,d),7.56～7.59(6H,d),7.76～7.79(8H,s),7.87～7.96(4H,m),8.02～8.05(4H,m),8.16～8.24(4H,m),8.82～8.85(2H,d)。
合成实施例4:化合物189的合成
合成方法同化合物204的合成，得到30g化合物189(产率27％)。
计算值C56H32N2:C,91.78；H,4.40；N,3.82；实测值:C,91.88；H,4.35；N,3.77。
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.29～7.42(4H,m),7.51～7.63(6H,m),7.74～7.77(8H,s),7.89～8.02(6H,m),8.05～8.08(2H,d),8.15～8.21(4H,m),8.56～8.59(2H,d)。
合成实施例5：化合物196的合成
合成方法同中间体1-1的合成，得到35g化合物196(产率40.5％)。
计算值C46H26:C,95.47；H,4.53；实际值:C,95.58；H,4.42。
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.41～7.44(4H,d),7.74～7.77(8H,s),7.89～7.98(8H,m),8.08～8.11(2H,d),8.16～8.22(4H,m)。
合成实施例6：化合物191的合成
中间体6-1的合成：合成方法同中间体1-1的合成，得到52g中间体6-1(产率60％)。
化合物191的合成：合成方法同化合物化合物204的合成，得到30g化合物191(产率52％)。计算值C50H29N：C,93.28；H,4.54；N,2.18；实际值:C,93.18；H,4.31；N,2.51
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.65～7.68(7H,m),7.74～7.92(14H,m),8.21～8.30(8H,m)。
合成实施例7:化合物174的合成
合成方法同化合物204的合成，得到34g化合物174(产率51.5％)。
计算值C56H32N2:C,91.78；H,4.40；N,3.82；实际值:C,91.85；H,4.32；N,3.83。
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.28～7.40(6H,m),7.53～7.56(3H,m),7.68～7.77(10H,m),7.82～7.85(2H,d),8.14～8.20(10H,m),8.61～8.64(2H,d)。
合成实施例8：化合物177的合成
合成方法同化合物179的合成，得到44g化合物177(产率51％)。
计算值C64H38N4:C,89.07；H,4.44；N,6.49；实际值:C,89.16；H,4.38；N,6.46。
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.48～7.57(12H，m)，7.82～7.88(12H，m)，8.09～8.12(8H，t)，8.35～8.41(6H，m)。
合成实施例9：化合物192的合成
合成方法同中间体1-1的合成，得到49g化合物192(产率53％)。
计算值C42H24:C,95.42；H,4.58；实际值：C,95.51；,H,4.49。
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.56～7.59(2H,d),7.76～7.79(8H,s),7.86～7.92
(4H,m),8.09～8.15(4H,m),8.18～8.26(4H,m),8.71～8.74(2H,d)。
合成实施例10：化合物209的合成
合成方法同化合物204的合成，得到31g化合物209(产率52％)。
计算值C42H25N:C,92.79；H,4.64；N,2.58；实际值：C,93.85；H,4.58。1H-NMR(400MHz,CDCl3)(ppm)δ＝6.91～7.06(3H,m)，7.41～7.44(1H,m)，7.58～7.66(3H，m),7.75～7.78(8H,m),7.91～7.97(6H,m),8.05～8.17(4H,m)。
合成实施例11：化合物210的合成
中间体11-1合成：合成方法同中间体1-1的合成，得到25g中间体11-1(产率42％)。
化合物210的合成：合成方法同化合物204的合成，得到11.8g化合物210(产率47％)。
计算值C50H29N:C,93.28；H,4.54；N,2.18；计算值：C,93.12；H,4.38；
1H-NMR(400MHz,CDCl3)(ppm)δ＝7.48～7.56(5H,m)7.72～7.96(18H,m),8.07～8.10(2H,d),8.21～8.27(4H,m)。
合成实施例12：化合物211的合成
合成方法同中间体1-1的合成，得到17g化合物211(产率23％)。
计算值C60H34:C,95.46；H,4.54；计算值：C,85.52；H.4.48。1H-NMR(400MHz,CDCl3)(ppm)δ＝7.42～7.45(8H,m),7.75～7.78(8H,s),7.92～7.98(12H,m),8.07～8.10(2H,d),8.22～8.28(4H,m)。
合成实施例13：化合物212的合成
合成方法同中间体1-1的合成，得到24g化合物212(产率34％)。
计算值C54H32N2:C,91.50；H,4.55；N,3.95；实际值：C,91.61；H,4.51。1H-NMR(400MHz,CDCl3)(ppm)δ＝7.28～7.31(4H,d),7.44～7.47(1H,m),7.54～7.57(2H,m),7.75～7.78(8H,s),7.92～7.98(4H,m),8.07～8.10(2H,d),8.21～8.33(11H,m)。
合成实施例14：化合物213的合成
合成方法同中间体1-1的合成，得到14g化合物213(产率17％)。
计算值C44H24N2:C,91.01；H,4.17；N,4.82；实际值：C,91.06；H,4.12。1H-NMR(400MHz,CDCl3)(ppm)δ＝7.61～7.64(2H,m),7.75～7.78(8H,s),7.92～7.98(4H,m),8.12～8.15(2H,d),8.18～8.14(4H,m),8.42～8.45(2H,d),8.85～8.88(2H,d)。
合成实施例15：
中间体15-1的合成：将280g(0.77mol)1,6-二溴芘加入至盛有2800ml乙酸的烧瓶中放入冰盐浴，将100ml硝酸加入至1000ml乙酸中，将配置好的硝酸液缓慢滴加至1,6-二溴芘的酸溶液中，保持反应温度不超过40度，滴加完毕后持续反应1小时，将反应液倒入大量冰水中，将PH值调为弱碱性后加乙酸乙酯萃取，有机相通过旋蒸使溶剂蒸发，得到156g中间体15-1(产率：45％)。
M1的合成同中间体1-1的合成，得到61.7g M1(产率:25％)。
中间体15-2的合成：合成方法同中间体1-1的合成，得到66.2g中间体15-2(产率:33％)。
中间体15-3的合成：合成方法同中间体1-1的合成，得到50g中间体15-3(产率:70％)。
中间体15-4的合成：将50g(0.08mol)的中间体38-3，22.4g(0.4mol)5当量铁粉，加入至醇1000ml，水300ml，浓盐酸5ml的混合溶液中，升温到回流，反应小时。反应完毕，加入乙酸乙酯萃取，有机相通过旋蒸使溶剂蒸发，柱层析得到29.35g中间体15-4(产率:65％)。
中间体15-5的合成：将29.35g(0.052mol)中间体38-4，10g浓硫酸与50ml水加入至烧瓶中放入冰盐浴，滴加7.2g亚硝酸钠与14ml水配制的水溶液，保持温度10摄氏度以下，滴加完毕后反应1h，将盛有3.3g硫酸铜新制的溴化亚铜溶液的烧瓶与水蒸气蒸馏装置连接，使蒸汽通过溶液，将所得溶液缓缓加入液面以下，蒸馏至馏分中不再析出产物为止，将馏出液过滤，加水洗涤后干燥，得到24.87g中间体15-5(产率:69％)。
化合物271的合成：合成方法同中间体1-1的合成，得到23.3g化合物271(产率:69％)。
计算值C72H44N2：C,92.28；H,4.73；N,2.99；实测值：C,92.31；H,4.72；N,2.97。1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.20-7.22(2H,s),7.30-7.33(12H,m),7.48-7.54(5H,m)，7.60-7.61(6H,m),7.67-7.68(8H，m)，7.70-7.73(5H，m)，7.89-7.90(1H，s)，8.25-8.26(2H，s)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例16
中间体16-1的合成：合成方法同中间体1-1的合成，得到35g中间体16-1(产率:37％)。
中间体16-2的合成：合成方法同中间体1-1的合成，得到37.28g中间体16-2(产率:73％)。
中间体16-3的合成：合成方法同中间体1-4的合成，得到24.3g中间体16-3(产率:54％)。
化合物272的合成：合成方法同化合物204的合成，得到20g化合物272(产率:69％)。
计算值C78H46N4：C,90.15；H,4.46；N,5.39；实测值：C,90.18；H,4.44；N,5.38。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.00-7.01(4H,d),7.08-7.09(4H,d),7.31-7.32(4H，d)7.39-7.40(8H,m)，7.54-7.55(4H，m)7.60-7.63(3H,d),7.67-7.68(4H，m)，7.70-7.73(5H，m)，7.89-7.90(1H，s)，7.91-7.92(4H，d)，8.00-8.02(2H，s)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例17
中间体17-1的合成：合成方法同中间体15-1的合成，得到116.9g中间体17-1(产率：45％)。
中间体17-2的合成：合成方法同中间体1-1的合成，得到49.3g中间体17-2(产率:33％)。
中间体17-3的合成：合成方法同中间体1-1的合成，得到40.4g中间体17-3(产率:70％)。
中间体17-4的合成：合成方法同中间体15-4的合成，得到24g中间体17-4(产率:65％)。
中间体17-5的合成：合成方法同中间体15-5的合成，得到20.6g中间体17-5(产率:69％)。
化合物273的合成：合成方法同中间体1-1的合成，得到17.8g化合物273(产率:72％)。
计算值C68H42N2：C,92.07；H,4.77；N,3.16；实测值：C,92.08；H,4.75；N,3.17。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.22-7.23(2H,d),7.31-7.32(6H,m),7.37-7.39(4H，m)，7.47-7.48(4H,m)，7.54-7.55(8H，d)7.60-7.63(2H,d),7.67-7.68(2H，d)，7.71-7.72(4H，m)，7.91-7.92(4H，d)，8.26-8.27(3H，d)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例18
中间体18-1的合成：合成方法同中间体15-1的合成，得到126g中间体18-1(产率：45％)。
原料M2的合成：合成方法同中间体1-1的合成，得到70g M2(产率:23％)。
中间体18-2的合成：合成方法同中间体1-1的合成，得到53.15g中间体18-2(产率:33％)。
中间体18-3的合成：合成方法同中间体1-1的合成，得到40.26g中间体18-3(产率:70％)。
中间体18-4的合成：合成方法同中间体15-4的合成，得到23.6g中间体18-4(产率:65％)。
中间体18-5的合成：合成方法同中间体15-5的合成，得到20.4g中间体18-5(产率:69％)。
化合物274的合成：合成方法同中间体1-1的合成，得到20.4g化合物274(产率:68％)。
计算值C76H46N4：C,89.91；H,4.57；N,5.52；实测值：C,89.88；H,4.59；N,5.53。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.00-7.08(4H,d),7.30-7.31(12H,m),7.38-7.40(2H，s)，7.46-7.47(2H,s)，7.54-7.55(5H，d)7.60-7.63(2H,d),7.67-7.68(2H，d)，7.71-7.77(9H，m)，7.89-7.90(3H，d)，8.26-8.27(2H，d)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例19
原料M3的合成：合成方法同中间体1-1的合成，得到55.6g M3(产率:24％)。
中间体19-1的合成：合成方法同中间体1-1的合成，得到41.2g中间体19-1(产率:34％)。
中间体19-2的合成：合成方法同中间体1-1的合成，得到40.3g中间体19-2(产率:70％)。
中间体19-3的合成：合成方法同中间体1-4的合成，得到29.6g中间体19-3(产率:55％)。
化合物275的合成：合成方法同中间体1-1的合成，得到5.7g化合物275(产率:23％)。
计算值C52H40N2：C,90.14；H,5.82；N,4.04；实测值：C,90.12；H,5.83；N,4.05。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝0.96-0.97(6H,s),1.67-1.68(4H,s),2.99-3.00(4H,m),7.22-7.23(1H,s),7.31-7.32(2H,d),7.37-7.39(4H，d)，7.47-7.48(2H,d)，7.54-7.55(4H，d)7.71-7.72(4H，m)，7.90-7.91(6H，d)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例20
原料M3的合成：合成方法同中间体1-1的合成，得到26.8g M3(产率:24％)。
中间体20-1的合成：合成方法同中间体1-1的合成，析得到42.9g中间体20-1(产率:69％)。
中间体20-2的合成：合成方法同中间体1-1的合成，得到23.4g中间体20-2(产率:36％)。
中间体20-3的合成：合成方法同中间体1-4的合成，得到16.1g中间体20-3(产率:53％)。
化合物276的合成：合成方法同中间体1-1的合成，得到12.8g化合物276(产率:71％)。
计算值C74H42N2O2：C,89.67；H,4.27；N,2.83；O,3.23；实测值：C,89.66；H,4.30；N,2.82；O,3.22。1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.11-7.13(2H,s),7.19-7.25(4H,d),7.32-7.33(4H，d)，7.38-7.42(9H,m)，7.49-7.54(7H，d)，7.63-7.67(3H，m)，7.71-7.72(4H，m)，7.91-7.92(4H，s)，8.25-8.26(2H，s)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例21
中间体21-1的合成：合成方法同中间体15-1的合成，得到166g中间体21-1(产率：46％)。
中间体21-2的合成：合成方法同中间体1-1的合成，得到65.88g中间体21-2(产率:34％)。
中间体21-3的合成：合成方法同中间体1-1的合成，得到53.88g中间体21-3(产率:69％)。
中间体21-4的合成：合成方法同中间体15-4的合成，得到32.62g中间体21-4(产率:67％)。
中间体21-5的合成：合成方法同中间体15-5的合成，得到30g中间体21-5(产率:69％)。
化合物277的合成：合成方法同中间体1-1的合成，得到25.1g化合物277(产率:69％)。
计算值C64H36N2S2：C,85.68；H,4.04；N,3.12；S,7.15；实测值：C,85.70；H,4.02；N,3.10；S,7.18。1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.31-7.33(4H，d)，7.38-7.39(4H,s)，7.53-7.54(6H，d)，7.71-7.72(4H，m)，7.78-7.86(4H，d)，7.91-7.92(6H，m)，7.99-8.00(2H，s)，8.25-8.26(3H，d)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例22
中间体22-1的合成：合成方法同中间体1-1的合成，得到29.8g中间体22-1(产率:35％)。
中间体22-2的合成：合成方法同中间体1-1的合成，得到28g中间体22-2(产率:73％)。
中间体22-3的合成：合成方法同中间体1-4的合成，得到18.62g中间体22-3(产率:52％)。
化合物278的合成：合成方法同中间体1-1的合成，得到15.2g化合物278(产率:72％)。
计算值C62H38N2：C,91.82；H,4.73；N,3.45；实测值：C,91.81；H,4.72；N,3.47；
1H-NMR(400MHZ,CDCl3)(ppm)δ＝7.22-7.23(1H，s)，7.32-7.38(9H,m)，7.48-7.49(2H，s)，7.53-7.54(6H，d)，7.60-7.63(3H，d)，7.67-7.68(6H，d)，7.71-7.73(5H，m)，7.89-7.90(1H，s)，8.25-8.26(2H，d)，9.00-9.02(2H，s)，9.21-9.23(1H，s)。
合成实施例23
合成方法同1-1。
计算值C40H22N2O实测值：546.17。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝8.83(1H,m),8.32-8.38(2H,m)8.06-8.18(5H,m),7.81-7.89(5H,m),7.58-7.71(6H,m),7.32-7.38(3H,m)。
合成实施例24
24-1合成方法同1-1。
24-2合成方法：将29-1加入到四氢呋喃中后将反应在氮气保护下降温至-78度后滴加丁基锂在此温度保温30分钟后将反应中滴加1,2-二溴乙烷，滴加完毕后然后将反应自然升温至室温，将反应滴加饱和氯化铵水溶液，分成后水相用乙酸乙酯萃取合并有机相后将有机溶剂蒸干后得到产品用甲苯重结晶，收率50％。
计算值C40H22N2O实测值：546.17。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝8.83(1H，m),8.38(1H,m),8.04-8.18(6H,m),7.81-7.91(6H,m),7.71(4H,dd),7.58(1H,m),7.35-7.41(3H,m)。
合成实施例25
合成方法同1-1
计算值:C40H22N2S实测值:562.15。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝8.83(1H，m)8.38-8.45(3H,m),7.98-8.12(6H,m),7.81-7.89(4H,m),7.71(4H,m),7.50-7.58(3H,m)7.35(1H,m)。
合成实施例26
合成方法同1-1。
计算值:C40H22N2S实测值:562.15。
1H-NMR(400MHZ,CDCl3)(ppm)δ＝8.83(1H,m),8.51(1H,m),8.31-8.38(2H,m),8.01-8.18(7H,m),7.81-7.89(5H,m),7.71(4H,dd),7.58(1H,m),7.35(1H,m)。
合成实施例27：化合物225的合成
化合物225的合成：合成方法同中间体1-1的合成，得到34g化合物225(收率67％)。
计算值C44H24O：C,92.93；H,4.25；实测值：C，92.68；H,4.31。
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.74～7.78(18H，m)，8.06～8.09(2H，d)，8.15～8.21(4H,m)。
合成实施例28：化合物249的合成
化合物249的合成：同中间体1-1的合成，得到23g化合物249(收率71％)。
计算值C44H24S：C,90.38；H,4.14；实测值：C,90.18；H,4.31。
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.74～7.77(8H,s)，7.85～7.91(6H，m)，8.06～8.12(6H，m)，8.16～8.22(4H，m)。
合成实施例29：
化合物252的合成：合成方法同中间体1-1的合成，得到30.5g化合物252(收率74％)。计算值C38H22：C,95.37；H,4.63；实测值:C,95.26；H,4.74。
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.28～7.31(4H，s)，7.74～7.77(8H，s)，7.86～7.92(4H，m)，8.06～8.09(2H，d)，8.16～8.22(4H，m)。
合成实施例30
中间体30-1的合成：同中间体1-1的合成，得到43g中间体255-1(收率71％)。
中间体30-2的合成；同中间体1-2的合成，得到28g中间体255-2(收率81％)。
化合物255的合成，同中间体1-1的合成，得到18g化合物255(收率68％)。
计算值C40H24：C,95.21；H,4.79；实测值：C,85.31；H,4.69。
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.51～7.54(2H,d)，7.59～7.62(1H，t)，7.74～7.77(5H，s)，7.86～7.92(6H，m)，8.16～8.22(7H，m)，8.95～8.98(2H，d)，9.16～9.19(1H，s)。
合成实施例31
化合物2586的合成：同中间体1-1的合成，得到27.4g化合物256(收率69％)。
计算值C57H32：C,95.50；H,4.50；实测值：C,95.42；H,4.58
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.31～7.34(2H，m),7.41～7.47(4H,m)，7.61～7.64(4H,m)，7.74～7.77(8H，s)，7.85～7.92(8H，m)，8.07～8.10(2H,d)，8.16～8.22(4H，m)。
合成实施例32
化合物269的合成：同中间体1-1的合成，得到24g化合物269(收率66.7％)。
计算值C44H24N2:C,91.01；H,4.17；N,4.82；实测值：C,91.05；H,4.10；N,4.84。
1H-NMR(300MHz,CDCl3)(ppm)δ＝7.51～7.54(2H,d)，7.74～7.77(8H，s)，7.92～7.98(6H，m)，8.04～8.07(2H，d)，8.16～8.22(4H，m)，8.91～8.94(2H，d)。
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108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。
实施例1-2至实施例1-11
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108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108以形成电子传输层之外。
表1
通过表1中的数据可以看出，本发明的空穴传输材料可以降低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189(蓝色荧光主体)和DPAVBi(蓝光掺杂剂，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。
实施例2-2至实施例2-9
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
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。
表2
通过表2中的数据可以看出，与现有材料ADN相比，本发明的蓝光主体可以降低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III所示，
其中，X为S；
R1、R2和R4-R10相同或不同，各自独立地为氢原子、未取代的C1-C10烷基、未取代的C1-C10烷氧基或未取代的苯基；
R11为未取代的菲啰啉基；L2为单键。
2.根据权利要求1所述的化合物，其特征在于，所述有机化合物选自以下化合物中的任意一种：
3.根据权利要求1-2中任一项所述的有机化合物在电子器件中的应用。
4.根据权利要求3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。
5.根据权利要求3或4所述的应用，其特征在于，所述电子器件为有机电致发光器件。
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