CN105753794A - 醇制备新型有机oled试剂的设计及其应用 - Google Patents

醇制备新型有机oled试剂的设计及其应用 Download PDF

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CN105753794A
CN105753794A CN201610201125.XA CN201610201125A CN105753794A CN 105753794 A CN105753794 A CN 105753794A CN 201610201125 A CN201610201125 A CN 201610201125A CN 105753794 A CN105753794 A CN 105753794A
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cdcl
alcohol
triazole
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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、醇和水在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

醇制备新型有机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醇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、醇和水在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、醇和水在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)，醇(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当量的苯甲醇、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53％，荧光量子产率为Φ＝0.27。
1HNMR(400MHz,CDCl3)δ5.63(s,2H),7.30-7.37(m,6H),7.39-7.44(m,2H),7.76-7.80(m,2H),7.87(s,1H).
实施例2，其具体合成步骤参考实施例1。
B收率为83％，荧光量子产率为Φ＝0.33。
1HNMR(400MHz,CDCl3)δ3.78(s,3H),5.55(s,2H),6.84-6.90(m,2H),7.29-7.36(m,3H),7.38-7.44(m,2H),7.78(dd,J＝8.4,1.6Hz,2H),7.84(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ55.2,58.2,114.1,125.9,127.4,128.3,128.8,129.5,130.4,131.3,147.9,159.6.
实施例3，其具体合成步骤参考实施例1。
C收率为55％，荧光量子产率为Φ＝0.34。
1HNMR(400MHz,CDCl3)δ5.08(dt,J＝6.4,1.2Hz,2H),5.29-5.35(m,2H),6.08-6.18(m,1H),7.31-7.38(m,1H),7.43(t,J＝7.6Hz,2H),7.78-7.80(m,2H),7.86(s,1H).
实施例4，其具体合成步骤参考实施例1。
D收率为33％，荧光量子产率为Φ＝0.43。
1HNMR(400MHz,CDCl3)δ5.25(d,J＝17.2Hz,1H),5.43(d,J＝10.0Hz,1H),6.33(d,J＝6.8Hz,1H),6.53-6.61(m,1H),7.27-7.38(m,6H),7.42(t,J＝7.4Hz,2H),7.77-7.81(m,2H),7.90(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ71.2,119.0,126.0,127.4,128.2,128.4,128.7,128.8,130.4,131.2,135.4,138.2,147.7.
实施例5，其具体合成步骤参考实施例1。
E收率为40％，荧光量子产率为Φ＝0.22。
1HNMR(400MHz,CDCl3)δ5.23(dd,J＝6.8,1.6Hz,2H),6.47(dt,J＝16.0,6.4Hz,1H),6.69(d,J＝16.0Hz,1H),7.22-7.37(m,4H),7.37-7.45(m,4H),7.77-7.79(m,2H),7.87(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ57.0,122.6,125.9,126.7,128.1,128.4,128.6,128.9,130.3,131.2,134.5,136.0,148.0.
实施例6，其具体合成步骤参考实施例1。
F收率为52％，荧光量子产率为Φ＝0.19。
1HNMR(400MHz,CDCl3)δ2.02(d,J＝6.8Hz,3H),5.88(q,J＝7.2Hz,1H),7.26-7.34(m,6H),7.41(t,J＝7.4Hz,2H),7.79(d,J＝7.2Hz,2H),7.86(s,1H).
实施例7，其具体合成步骤参考实施例1。
G收率分别为71％，荧光量子产率为Φ＝0.33。
1HNMR(400MHz,CDCl3)δ2.00(d,J＝6.8Hz,3H),2.31(s,3H),5.84(q,J＝6.8Hz,1H),7.13(d,J＝8.0Hz,2H),7.25(d,J＝7.6Hz,2H),7.32(t,J＝7.6Hz,1H),7.39-7.42(m,2H),7.76-7.80(m,2H),7.84(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ21.1,21.3,64.2,125.9,126.3,128.2,128.8,129.3,130.6,130.8,137.7,137.8,147.3.
实施例8，其具体合成步骤参考实施例1。
H收率为70％，荧光量子产率为Φ＝0.24。
1HNMR(400MHz,CDCl3)δ1.98(d,J＝6.8Hz,3H),2.43(s,3H),6.12(q,J＝7.2Hz,1H),7.16-7.19(m,3H),7.24-7.29(m,1H),7.32(t,J＝7.6Hz,1H),7.41(t,J＝7.6Hz,2H),7.77-7.81(m,2H),7.84(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ19.2,20.7,60.8,125.7,125.9,126.4,127.9,128.2,128.8,130.5,130.6,130.7,135.1,138.9,147.2.
实施例9，其具体合成步骤参考实施例1。
I收率为32％，荧光量子产率为Φ＝0.32。
1HNMR(400MHz,CDCl3)δ2.01(d,J＝7.2Hz,3H),6.25(q,J＝7.2Hz,2H),7.03-7.11(m,2H),7.19(td,J＝8.0,2.0Hz,1H),7.34(t,J＝7.4Hz,1H),7.42(t,J＝7.6Hz,2H),7.78-7.82(m,2H),7.88(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ20.7,57.72,57.76,115.4,115.6,124.40,124.42,125.9,127.37,127.40,128.3,128.4,128.8,129.5,129.6,130.4,131.0,147.6,160.7；19FNMR(376MHz,CDCl3)δ-114.7.
实施例10，其具体合成步骤参考实施例1。
J收率为72％，荧光量子产率为Φ＝0.22。
1HNMR(400MHz,CDCl3)δ1.99(d,J＝7.2Hz,3H),3.76(s,3H),5.83(q,J＝7.2Hz,1H),6.82-6.88(m,2H),7.28-7.34(m,3H),7.37-7.43(m,2H),7.76-7.80(m,2H),7.83(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ21.3,55.2,63.9,113.9,125.9,127.7,128.2,128.7,130.6,130.8,132.9,147.3,159.3.
实施例11，其具体合成步骤参考实施例1。
K收率为80％，荧光量子产率为Φ＝0.16。
1HNMR(400MHz,CDCl3)δ7.08(s,1H),7.26-7.36(m,11H),7.37-7.42(m,2H),7.77-7.81(m,2H),7.92(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ72.4,126.0,128.1,128.3,128.4,128.5,128.8,130.3,131.4,138.7,147.8.
实施例12，其具体合成步骤参考实施例1。
L收率为80％，荧光量子产率为Φ＝0.22。
1HNMR(400MHz,CDCl3)δ6.49(d,J＝8.0Hz,1H),6.61(d,J＝15.6Hz,1H),6.92(dd,J＝16.0,7.6Hz,1H),7.21-7.44(m,13H),7.78-7.82(m,2H),7.91(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ70.9,126.0,126.5,126.8,127.2,128.2,128.2,128.4,128.6,128.7,128.8,130.4,131.2,133.8,136.0,138.7,147.7.
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＝0.35。
1HNMR(400MHz,CDCl3)δ1.72(s,9H),7.30-7.7.35(m,1H),7.42(t,J＝7.2Hz,2H),7.77-7.82(m,3H)；13CNMR(100MHz,CDCl3,TMS):δ29.5,62.8,125.8,128.1,128.7,230.1,131.0,146.8.
实施例14，其具体合成步骤参考实施例1。
N收率为75％，荧光量子产率为Φ＝0.23。
1HNMR(400MHz,CDCl3)δ2.13(s,6H),7.06(d,J＝7.6Hz,2H),7.22-7.34(m,4H),7.41(t,J＝7.6Hz,2H),7.82(d,J＝7.2Hz,2H),7.89(s,1H)；13CNMR(100MHz,CDCl3)δ29.4,67.7,124.7,125.9,127.2,128.2,128.8,130.6,130.7,146.0,147.0.
实施例15，其具体合成步骤参考实施例1。
O收率为75％，荧光量子产率为Φ＝0.26。
1HNMR(400MHz,CDCl3)δ6.51(d,J＝7.6Hz,1H),6.62(d,J＝16.0Hz,1H),6.92(dd,J＝15.6,7.6Hz,1H),7.11-7.23(m,2H),7.26-7.38(m,9H),7.44(d,J＝7.6Hz,2H),8.02-8.05(m,2H)；13CNMR(100MHz,CDCl3,TMS):δ70.9,115.9,116.1,118.3,118.4,124.40,124.43,126.4,126.8,127.2,128.2,128.3,128.41,128.44,128.6,128.7,129.6,129.7,133.9,134.0,134.1,135.9,138.6,142.22,142.24,158.7,161.2；19FNMR(376MHz,CDCl3)δ-119.2
实施例16，其具体合成步骤参考实施例1。
P收率为79％，荧光量子产率为Φ＝0.31。
1HNMR(400MHz,CDCl3)δ6.47(d,J＝7.2Hz,1H),6.61(d,J＝15.6Hz,1H),6.91(dd,J＝16.0,8.0Hz,1H),7.10(t,J＝8.4Hz,2H),7.25(t,J＝7.2Hz,1H),7.31(t,J＝6.8Hz,3H),7.36(d,J＝4.4Hz,2H),7.42(d,J＝6.8Hz,2H),7.74-7.79(m,4H),7.86(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ70.9,115.7,115.9,126.4,126.57,126.60,126.8,127.2,127.67,127.75,128.2,128.3,128.6,128.7,130.9,133.9,135.9,138.6,146.9,161.6,164.0；19FNMR(376MHz,CDCl3)δ-113.2.
实施例17，其具体合成步骤参考实施例1。
Q收率为82％，荧光量子产率为Φ＝0.18。
1HNMR(400MHz,CDCl3)δ6.47(d,J＝8.0Hz,1H),6.61(d,J＝16.0Hz,1H),6.90(dd,J＝16.0,8.0Hz,1H),7.22-7.44(m,12H),7.73(d,J＝8.4Hz,2H),7.88(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ71.0,126.3,126.8,127.2,128.2,128.3,128.6,128.8,128.9,129.0,131.2,133.9,134.1,135.9,138.6,146.7.
实施例18，其具体合成步骤参考实施例1。
R收率为49％，荧光量子产率为Φ＝0.24。
1HNMR(400MHz,CDCl3)δ3.83(s,3H),6.47(d,J＝7.6Hz,1H),6.60(d,J＝16.0Hz,1H),6.87-6.96(m,3H),7.22-7.37(m,8H),7.43(d,J＝7.2Hz,2H),7.73(d,J＝8.8Hz,2H),7.84(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ55.3,70.7,114.2,123.1,126.6,126.8,127.2,127.3,128.15,128.19,128.6,128.7,130.7,133.8,136.0,138.8,147.6,159.8.
实施例19，其具体合成步骤参考实施例1。
S收率为63％，荧光量子产率为Φ＝0.21。
1HNMR(400MHz,CDCl3)δ2.39(s,3H),6.49(d,J＝7.6Hz,1H),6.61(d,J＝16.0Hz,1H),6.92(dd,J＝16.0,8.0Hz,1H),7.15(d,J＝7.6Hz,1H),7.23-7.3(m,9H),7.43(d,J＝7.2Hz,2H),7.59(d,J＝7.6Hz,1H),7.64(s,1H),7.90(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ21.4,70.8,123.1,126.5,126.6,126.8,127.2,128.18,128.21,128.6,128.70,128.72,129.2,130.2,131.3,133.8,136.0,138.5,138.7,147.9.
实施例20，其具体合成步骤参考实施例1。
T收率为45％，荧光量子产率为Φ＝0.30。
1HNMR(400MHz,CDCl3)δ6.48(d,J＝7.6Hz,1H),6.57(d,J＝16.0Hz,1H),6.88(dd,J＝15.6,7.6Hz,1H),7.22-7.38(m,8H),7.42(d,J＝6.8Hz,2H),7.68(s,2H)；13CNMR(100MHz,CDCl3,TMS):δ70.7,126.3,126.8,127.2,128.2,128.3,128.6,128.8,133.9,134.3,135.9,138.6.
实施例21，其具体合成步骤参考实施例1。
U收率为71％，荧光量子产率为Φ＝0.35。
1HNMR(400MHz,CDCl3)δ0.70(s,3H),0,87(dd,J＝2.0,6.8Hz,6H),0.93(d,J＝6.8Hz,3H),1.08-1.17(m,8H),1.24-1.36(m,8H),1.47-1.63(m,7H),1.81-1.88(m,1H),1.99-2.06(m,3H),2.12-2.19(m,1H),2.20-2.26(m,1H),2.53-2.60(m,1H),2.89-2.98(m,1H),4.39-4.50(m,1H),5.43-5.47(m,1H),7.33(t,J＝7.6Hz,1H),7.42(t,J＝7.6Hz,2H),7.76-7.81(m,2H),7.83(s,1H)；13CNMR(100MHz,CDCl3,TMS):δ11.9,18.7,19.4,21.0,22.6,22.8,23.8,24.3,28.0,28.2,28.7,29.7,31.8,31.9,35.8,36.2,36.8,37.8,38.8,39.5,39.7,42.3,50.1,56.1,56.7,65.0,122.6,125.8,128.2,128.8,130.3,130.7,139.9,147.0。

Claims (7)

1.醇制备新型有机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、醇和水在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)，醇(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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