CN105801499A - 烯酮制备新型有机oled试剂的设计及其应用 - Google Patents

烯酮制备新型有机oled试剂的设计及其应用 Download PDF

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CN105801499A
CN105801499A CN201610237024.8A CN201610237024A CN105801499A CN 105801499 A CN105801499 A CN 105801499A CN 201610237024 A CN201610237024 A CN 201610237024A CN 105801499 A CN105801499 A CN 105801499A
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王飞军
张冬冬
王艳
马玉涛
胡庆霞
董浩浩
江鹏
施敏
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East China University of Science and Technology
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    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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Abstract

本发明涉及一种简便合成新型有机OLED试剂的新方法。所述的化合物是：以DCE为溶剂，0.1mol％的TsOH为催化剂，三氮唑、烯酮和水在80℃下反应48h，后经浓缩及柱层析得目标化合物。该方法反应简单，产率高，且无金属，绿色环保。产物作为新兴有机OLED，具有很高的量子收率。式I中，R1、R2可为芳基、氢等，R3、R4、R5可为烷基、芳基、氢等。

Description

烯酮制备新型有机OLED试剂的设计及其应用
技术领域
本发明涉及一种简便合成新型有机OLED试剂的新方法。
背景技术
OLED背光源是一种具有高亮度、广色域、耐冲压、低电压、轻薄和功耗低等特性的反射式二维面光源，其阴极金属层是高反射率的镜面反射层，因此OLED背光源不需要导光板、散光板等导光、匀光辅助光学配件，就可以将光发射层发出的光直接反射到LCD，很好地符合了LCD对背光源的要求，因此OLED有机会成为新时代液晶显示器背光源的主角。
这里，我们发明了第一例以烯酮与三氮唑反应制备新型有机OLED的方法，以DCE为溶剂，0.1mol％的TsOH为催化剂，三氮唑、烯酮和水在80℃下反应48h，一步便可得到目标化合物。该方法的一个显著的特点是反应简单，条件温和，产率较高，具有很高的原子经济性。据我们所知，通过一步合成方法来来构建有机OLED试剂的方法还未见报道。
发明内容
本发明涉及一种简便合成新型有机OLED试剂的新方法。所述的化合物是：以DCE为溶剂，0.1mol％的TsOH为催化剂，三氮唑、烯酮和水在80℃下反应48h，后经浓缩及柱层析得目标化合物。该方法反应简单，产率高，且无金属，绿色环保。产物作为新兴有机OLED，具有很高的量子收率。
在本发明一个优选的技术方案中，R1、R2可为芳基、氢等，R3、R4、R5可为烷基、芳基、氢等。
具体实施方式
其合成路线如下所示：
具体合成步骤如下：以1,2-二氯乙烷为溶剂，0.1％TsOH为催化剂，三氮唑(2当量)，取代烯酮(1当量)以及水(2当量)在80℃下反应48h，后经浓缩及柱层析得目标化合物。
本发明所合成的N2-烷基化的三氮唑，典型地包括下列结构式的化合物，但并不局限于此。
下面通过实施例对本发明作进一步阐述，其目的仅在于更好理解本发明的内容。因此，所举之例并不限制本发明的保护范围。
除有特别说明以外，实施例中所说的薄层层析(TLC)采用山东黄海化学试剂公司生产的型号为HSGF254的硅胶板；柱层析采用山东黄海化学试剂公司生产的300～400目的硅胶。
实施例1
A以1,2-二氯乙烷为溶剂，0.1mol％的对甲苯磺酸为催化剂，1当量环己烯酮、2.0当量的1-tosyl-1H-1,2,3-triazoles以及2.0当量的水在80℃下反应48h，后经浓缩及柱层析得目标化合物，收率为80％，荧光量子产率为Φ＝0.21。
1HNMR(400MHz,CDCl3)δ1.74-1.86(m,1H),2.00-2.10(m,1H),2.28-2.38(m,2H),2.45-2.50(m,2H),2.92(dd,J＝14.8,4.8Hz,1H),3.14(dd,J＝14.8,9.2Hz,1H),4.97-5.04(m,1H),7.32-7.38(m,1H),7.40-7.45(m,2H),7.75-7.79(m,2H),7.85(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ21.3,31.1,40.6,46.5,62.6,125.9,128.5,128.9,130.2,130.8,147.6,207.3.
实施例2，其具体合成步骤参考实施例1。
B收率为68％，荧光量子产率为Φ＝0.18。
1HNMR(400MHz,CDCl3)δ3.73(dd,J＝17.6,5.2Hz,1H),4.56(dd,J＝18.0,9.2Hz,1H),6.51(dd,J＝9.2,5.2Hz,1H),7.27-7.45(m,8H),7.46(t,J＝7.6Hz,2H),7.57(t,J＝7.6Hz,1H),7.71-7.75(m,2H),7.83(s,1H),7.98-8.02(m,2H)；13CNMR(100MHz,CDCl3,TMS):δ44.1,64.2,125.9,126.7,128.2,128.25,128.29,128.6,128.7,128.8,130.4,131.1,133.4,136.4,139.4,147.6,195.9.
实施例3，其具体合成步骤参考实施例1。
C收率为88％，荧光量子产率为Φ＝0.16。
1HNMR(400MHz,CDCl3)δ1.83-2.00(m,2H),2.02-2.12(m,1H),2.27-2.37(m,1H),2.38-2.49(m,2H),4.46-4.53(m,1H),5.61(dd,J＝13.6,6.4Hz,1H),7.29-7.35(m,1H),7.37-7.46(m,4H),7.50-7.57(m,1H),7.73-7.77(m,2H),7.80(s,1H),7.92-7.96(m,2H)；13CNMR(100MHz,CDCl3,TMS):δ24.4,30.7,33.5,52.5,67.2,125.8,128.3,128.57,128.61,128.8,130.4,130.7,133.2,136.0,147.4,200.0.
实施例4，其具体合成步骤参考实施例1。
D收率为30％，荧光量子产率为Φ＝0.11。
1HNMR(400MHz,CDCl3)δ4.96(dd,J＝14.4,4.4Hz,1H),5.70(dd,J＝14.8,10.4Hz,1H),6.54(dd,J＝10.4,4.4Hz,1H),7.33-7.39(m,6H),7.43(t,J＝7.2Hz,2H),7.76-7.80(m,2H),7.91(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ65.2,76.6,126.0,126.8,128.8,128.9,129.3,129.5,129.8,131.9,134.4,148.5.
实施例5，其具体合成步骤参考实施例1。
E收率为84％，荧光量子产率为Φ＝0.23。
1HNMR(400MHz,CDCl3)δ3.19(dd,J＝17.6,5.6Hz,1H),3.44(dd,J＝18.0,8.0Hz,1H),3.81(s,3H),5.51(dd,J＝8.0,5.6Hz,1H),6.86(d,J＝8.0Hz,2H),7.20(d,J＝7.8Hz,2H),7.49-7.53(m,5H),7.67-7.71(m,2H),7.84(d,J＝7.6Hz,2H),7.95(d,J＝7.6Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,56.0,60.8,114.0,127.5,128.6,128.7,128.8,129.2,130.4,131.7,133.1,136.7,148.4,157.8,200.1.
实施例6，其具体合成步骤参考实施例1。
F收率为65％，荧光量子产率为Φ＝0.24。
1HNMR(400MHz,CDCl3)δ2.19(s,3H),3.19(dd,J＝18.0,6.0Hz,1H),3.44(dd,J＝17.6,7.8Hz,1H),5.51(dd,J＝8.0,5.6Hz,1H),7.06(d,J＝8.0Hz,2H),7.15(d,J＝7.6Hz,2H),7.49-7.53(m,5H),7.71-7.67(m,2H),7.84(d,J＝8.0Hz,2H),7.95(d,J＝8.0Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ21.3,40.2,69.3,127.5,127.6,128.6,128.7,128.8,128.9,129.2,130.4,131.7,133.1,135.6,136.7,141.4,148.4,200.1.
实施例7，其具体合成步骤参考实施例1。
G收率分别为42％，荧光量子产率为Φ＝0.25。
1HNMR(400MHz,CDCl3)δ3.19(dd,J＝18.0,9.2Hz,1H),3.44(dd,J＝9.2,5.2Hz,1H),5.51(dd,J＝8.2,5.8Hz,1H),7.14(d,J＝8.0Hz,2H),7.35(d,J＝7.6Hz,2H),7.49-7.55(m,5H),7.75-7.78(m,2H),7.88(d,J＝8.9Hz,2H),8.00(J＝8.8Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,69.3,127.5,128.6,128.7,128.8,129.1,129.2,130.4,131.5,131.7,133.1,136.7,142.5,148.4,200.1.
实施例8，其具体合成步骤参考实施例1。
H收率为57％，荧光量子产率为Φ＝0.24。
1HNMR(400MHz,CDCl3)δ3.19(dd,J＝17.8,9.6Hz,1H),3.44(dd,J＝9.4,5.6Hz,1H),5.54(dd,J＝8.0,6.0Hz,1H),7.16-7.18(m,4H),7.49-7.53(m,5H),7.67-7.71(m,2H),7.84(d,J＝8.9Hz,2H),8.05(d,J＝9.0Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,69.3,115.4,127.5,128.6,128.7,128.8,129.2,129.3,130.4,131.7,133.1,136.7,140.0,148.4,160.1,200.1.
实施例9，其具体合成步骤参考实施例1。
I收率为40％，荧光量子产率为Φ＝0.16。
1HNMR(400MHz,CDCl3)δ3.19(dd,J＝18.0,9.2Hz,1H),3.64(dd,J＝9.2,5.2Hz,1H),5.80(dd,J＝9.2,5.2Hz,1H),7.01-7.09(m,2H),7.24(m,1H),7.49-7.55(m,6H),7.67-7.71(m,2H),7.84(d,J＝7.6Hz,1H),7.95(d,J＝7.8Hz,1H)；13CNMR(100MHz,CDCl3,TMS):δ39.5,65.5,122.7,127.5,127.6,128.1,128.6,128.7,128.8,129.2,129.9,130.4,131.1,131.7,132.6,136.7,143.5,148.4,200.1.
实施例10，其具体合成步骤参考实施例1。
J收率为59％，荧光量子产率为Φ＝0.25。
1HNMR(400MHz,CDCl3)δ3.29(dd,J＝17.6,9.2Hz,1H),3.44(dd,J＝10.2,5.8Hz,1H),5.89(dd,J＝10.2,5.8Hz,1H),7.14-7.18(m,3H),7.49-7.53(m,5H),7.65-7.71(m,3H),7.88(d,J＝7.8Hz,1H),7.90(d,J＝8.0Hz,1H)；13CNMR(100MHz,CDCl3,TMS):δ39.7,64.2,126.7,127.3,127.5,128.6,128.7,128.8,129.1,129.2,130.4,131.7,133.0,133.1,136.7,140.6,148.4,200.1.
实施例11，其具体合成步骤参考实施例1。
K收率为53％，荧光量子产率为Φ＝0.23。
1HNMR(400MHz,CDCl3)δ3.19(dd,J＝18.8,9.8Hz,1H),3.84(dd,J＝9.9,5.8Hz,1H),5.74(dd,J＝8.1,6.2Hz,1H),7.09(d,J＝8.9Hz,2H),7.49-7.53(m,5H),7.67-7.71(m,2H),7.82-7.84(m,4H),8.05(d,J＝9.0Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,69.3,120.3,127.5,128.6,128.7,128.8,129.2,129.9,130.4,131.5,131.7,133.1,136.7,143.4,148.4,200.1.
实施例12，其具体合成步骤参考实施例1。
L收率为50％，荧光量子产率为Φ＝0.25。
1HNMR(400MHz,CDCl3)δ3.39(dd,J＝17.0,10.2Hz,1H),3.64(dd,J＝10.0,6.8Hz,1H),5.79(dd,J＝9.2,6.8Hz,1H),7.07-7.18(m,2H),7.49-7.71(m,9H),7.85(d,J＝7.8Hz,2H),8.01(d,J＝8.8Hz,2H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,62.5,115.4,124.2,127.2,127.5,128.6,128.7,128.8,129.2,129.3,130.4,131.7,133.1,136.7,148.4,160.2,200.1.
实施例13，其具体合成步骤参考实施例1。
M收率为65％，荧光量子产率为Φ＝0.11。
1HNMR(400MHz,CDCl3)δ3.29(dd,J＝17.6,9.2Hz,1H),3.44(dd,J＝10.2,5.8Hz,1H),5.89(dd,J＝10.2,5.8Hz,1H),6.89-7.02(m,3H),7.33(m,1H),7.49-7.53(m,5H),7.68-7.72(m,2H),7.88(d,J＝8.0Hz,1H),7.99(d,J＝8.2Hz,1H)；13CNMR(100MHz,CDCl3,TMS):δ40.2,69.3,112.7,114.7,124.4,127.5,128.6,128.7,128.8,129.2,130.2,130.4,131.7,133.7,136.7,146.0,148.4,162.8,200.1。

Claims (7)

1.烯酮制备新型有机OLED试剂的设计及其应用，其结构如式I所示：
式I中，R1、R2可为芳基、氢等，R3、R4、R5可为烷基、芳基、氢等。
2.如权利要求1所述此类结构化合物，其特征在于，R1、R2可为芳基、氢等官能团，R3、R4、R5可为烷基、芳基、氢等,反应普适性强。
3.如权利1～2要求的N2-烷基化的三氮唑化合物，其特征在于，在制备过程中并没有采用了严格苛刻的反应条件催化剂，使制备方法非常廉价简单，且操作容易并达到了80％以上的原子经济性。
4.制备如权利要求1～4中任意一项所述的N2-烷基化的三氮唑化合物的方法，其特征在于，所说的制备方法是：以DCE为溶剂，0.1mol％的TsOH为催化剂，三氮唑、烯酮和水在80℃下反应48h，一步便可得目标化合物。
注：Ts为对甲苯磺酰基。
5.如权利4要求的N2-烷基化的三氮唑的制备方法，其特征在于，在制备过程中采用了较为温和的制备方法和较为廉价的原料。
6.如权利要求4所述的制备方法，其特征在于，所述的制备方法包括如下步骤：以1,2-二氯乙烷为溶剂，0.1％TsOH为催化剂，三氮唑(2当量)，烯酮(1当量)以及水(2当量)在80℃下反应48h，后经浓缩及柱层析得目标化合物。
7.如权利要求1所述此类结构化合物，其特征在于可作为有机OLED试剂，具有很强的量子产率。
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