CN106632262A - 一类含咔唑骨架的三芳基吡啶衍生物及其制备方法与应用 - Google Patents

一类含咔唑骨架的三芳基吡啶衍生物及其制备方法与应用 Download PDF

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CN106632262A
CN106632262A CN201611074704.9A CN201611074704A CN106632262A CN 106632262 A CN106632262 A CN 106632262A CN 201611074704 A CN201611074704 A CN 201611074704A CN 106632262 A CN106632262 A CN 106632262A
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苑睿
窦鹏飞
王超
宛瑜
王海营
吴翚
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Abstract

本发明涉及一类含咔唑骨架的三芳基吡啶衍生物及其制备方法与应用。本发明通过Witting‑Horner和Suzuki偶联反应合成了六个基于咔唑和2,4,6‑三芳基吡啶的D–π–A分子，并对这些化合物的光电性质和用途做了初步研究。结果表明：连接有咔唑片段的三芳基吡啶化合物能发射蓝绿荧光，具有合适的HOMO、LUMO能级，具有电子传输能力和空穴传输能力，可开发为有机电致发光材料。

Description

一类含咔唑骨架的三芳基吡啶衍生物及其制备方法与应用
技术领域
本发明属于化学合成技术领域，特别涉及一类新型咔唑-三芳基取代吡啶衍生物的合成及光、电、热稳定性等性质以及作为蓝绿荧光化合物的用途。
背景技术
近年来，咔唑已广泛应用于光电材料、医药、农药、染料等领域。咔唑及其衍生物属于富电子体系，不仅具有较大的共轭体系还具有较强的载流子传输能力，可作为倍受人类关注的一类新型光电材料。随着工业技术的发展，咔唑及其衍生物在新型光电材料的合成及应用中将发挥越来越重大的作用。
对咔唑的修饰一般是对其3，6，9-位或其他位碳原子上进行取代修饰，可得到多类光电材料。从分子结构上分，咔唑类光电材料大致为有机小分子和高分子聚合物两大类。其中小分子光电材料，以咔唑为电子给体(D)、乙烯基作为π电子桥与电子受体连接(A)，构成具有“D-π-A”结构构型的有机配体的例子不多，而“D-π-A”结构构型是优秀光电材料的重要骨架。
发明内容
本发明提供了一类含有咔唑骨架的三芳基吡啶衍生物及其制备方法与应用，共合成了六个基于咔唑(Donor)和2，4，6-三芳基吡啶(Acceptor)的D-π-A分子，并通过紫外吸收光谱和荧光发射光谱测试了其光学性质，通过循环伏安法测试了其电化学性质，通过热重和差热分析法测试了其热性质，通过高斯程序的密度泛理论基组计算化合物的最优化结构和化合物的HOMO、LUMO的分布状况。
技术方案：一类含咔唑骨架的三芳基吡啶衍生物，结构式为：
其中，R10为H或R11为H或R12为H或或
一类制备所述的咔唑骨架三芳基吡啶衍生物的方法，以4-(9H-咔唑-9-基)苯甲醛与为原料通过Witting-Horner偶联反应合成得到其中R7为H或CH2PO(OEt)2、R8为H或CH2PO(OEt)2、R9为H或CH2PO(OEt)2；R10为H或R11为H或R12为H或
反应以DMF为溶剂，乙醇钠为催化剂，室温下反应。
一类制备所述的咔唑骨架三芳基吡啶衍生物的方法，以4-(9H-咔唑-9-基)苯甲醛与苯甲醛为原料通过羟醛缩合反应合成得到
所述的咔唑骨架三芳基吡啶衍生物作为电致发光器件的应用。
有益效果
本发明通过Witting-Horner、Suzuki偶联反应和羟醛缩合反应合成了六个基于咔唑和2，4，6-三芳基吡啶的D-π-A分子，并对这些化合物的光电性质和用途做了初步研究。结果表明：连接有咔唑片段的三芳基吡啶化合物能发射蓝绿荧光，具有合适的HOMO、LUMO能级，具有电子传输能力和空穴传输能力，可开发为有机电致发光材料。本发明提供的化合物同时具有电子传输能力和空穴传输能力并具有较高发光效率的化合物，进而在器件制备的过程中，这类化合物在单层器件中可以同时兼作发光层、电子传输层和空穴传输层，或在双层器件兼作发光层和空穴传输层，或发光层和电子传输层，对发光材料的结构设计有很大的参考意义。
附图说明
图1产物11c-11e和13在二氯甲烷溶液中的紫外吸收光谱。
图2二氯甲烷中11c-11e和13的荧光发射光谱。
图3化合物11f的循环伏安图。
具体实施方式
1、中间产物4-10的合成方法参照参考文献Maninder Singh，Vineet Kumar Soni，Rituraj Mishra，Narayanan D.Kurur.Relaxation editing using long-lived statesand coherences for analysis of mixture.Analytical Chemistry.2016，88，3004-3008.或Jia-Xiang Yang，Xu-Tang Tao，Chun Xue Yuan，Yun Xing Yan，Lei Wang，ZhiLiu，Yan Ren，Min Hua Jiang.A facile synthesis and properties of multicarbazolemolecules containing multiple vinylene bridges.Journal of American ChemicalSociety，2005，127，10，3728.中的记载。
(a)2％NaOH aq；(b)NaOH，NH4OAc，CH3CH2OH，100℃；(c)NBS，CCl4；(d)P(OEt)3，160℃
2、新型咔唑-三芳基吡啶蓝绿发光有机小分子11的合成方法：
1)中间产物咔唑片段的合成方法：化合物3，即4-(9H-咔唑-9-基)苯甲醛的合成方法参照参考文献Xiao Li，Tie-Nan Zang，Hai-Jun Chi，Yan Dong，Guo-Yong Xiao，Dong-YuZhang，Multifunctional phosphorescent iridium(III)complexes based on 2-phenylbenzothiazole derivative for highly efficient organic light-emittingdiodes.Dyes and Pigments.2014，106，51-57.中记载。
(a)t-BuOK，DMF，110℃，30min
2)含吩咔唑骨架的三芳基吡啶衍生物11的合成方法：
(a)EtONa，DMF，r.t.
在装有化合物10(5mmol)的圆底烧瓶中加入溶有4-(9H-咔唑-9-基)苯甲醛3(5mmol)的DMF溶液5mL，再缓慢滴加含乙醇钠(5mmol)的DMF溶液10mL，室温下反应5h，过滤，用无水乙醇冲洗得粗产物，粗产物通过柱层析纯化(淋洗液石油醚∶乙酸乙酯＝20∶1)，得化合物11。
3、含咔唑骨架三芳基吡啶化合物13的合成方法：
(a)2％NaOH aq；(b)NaOH，NH4OAc，CH3CH2OH，100℃
称取(9H-咔唑-9-基)苯甲醛3(10mmol)、苯甲醛12(10mmol)加入装有2％NaOH水溶液(100ml)的圆底烧瓶中，室温搅拌30min后，升温至60℃反应6h，TLC薄层色谱跟踪，反应结束后冷却，去离子水淋洗2-3次，干燥，得淡黄色固体；将该淡黄色固体和苯甲醛12(10mmol)倒入到装有NaOH(40mmol)粉末的研钵中，研磨30min，得黄色粉末，将黄色粉末加入到溶解有10g乙酸铵的乙醇(100ml)溶液的圆底烧瓶中，加热回流10h后，冷却至室温，抽滤，去离子水淋洗2-3次，柱层析(淋洗液石油醚∶乙酸乙酯＝50∶1)，得到白色固体13。
4、光学性质
1)紫外吸收光谱
化合物11c-11e和13均配成5×10-6mol/L二氯甲烷溶液，测得的紫外吸收光谱如图1所示。
化合物在290nm处左右的吸收峰归属于K带或者B带吸收，是因为分子共轭体系中电荷从咔唑转移到三芳基吡啶而引起的π→π*跃迁和苯环的振动相重叠引起的。而在300-400nm的吸收峰归属于R带吸收，是三芳基吡啶骨架N原子上的孤对电子向π*反键轨道跃迁的结果，可简单表示为n→π*。此外，根据紫外光谱图，我们测定了化合物11c-11e和13的能量带宽Eg。
2)荧光发射光谱
化合物11c-11e和13配制成浓度为5×10-6mol/L的二氯甲烷溶液，以340nm为激发波长，测得的荧光发射光谱如图2所示。
化合物荧光发射峰在400-450nm，表现为蓝色发光。随着分子共轭链的加长，最大荧光发射峰发射红移，咔唑基团的引入，化合物荧光强度强于简单苯基的引入。通过图2和表1，我们发现具有较大分子共轭结构的咔唑-三芳基吡啶衍生物的荧光量子效率最高，这可能是由于随着分子共轭程度增加，荧光强度得到加强，同时9-苯基咔唑醛的旋转角度与三芳基吡啶骨架形成了较好的夹角，使化合物刚性增强。
以硫酸奎宁为标准(Φ＝0.55)，在二氯甲烷溶液中分别测定了化合物11c-11e和13的荧光量子产率0.20-0.51，见表1。此外，我们还研究了化合物11c-11e和13的溶剂效应，如表1所示，随着溶剂极性的增大，极性溶剂分子的偶极使溶质分子的极性增强，因而在极性溶剂中π→π*跃迁所需能量减小，荧光发射波长发生红移。
5、电化学性质
室温下采用循环伏安法，以铂电极为工作电极与对电极，饱和甘汞电极为参比电极，在二氯甲烷溶剂中，以四丁基六氟磷酸铵(0.1mol/L n-Bu4NPF6)为支持电解质测试了化合物11c-11e和13的电化学性质。如图3所示。
化合物11c-11e和13都有一个可逆的氧化峰。以化合物11f为例，其第一氧化峰为0.31V。计算所得的HOMO能量(-4.65to-5.15eV)，说明化合物11c-11e和13具有一定的空穴传输性能。同时其较低的LUMO能量(-1.65to-2.13eV)和较小的能带间隙使得化合物很容易被注入电子。
6、热稳定性
利用热重(TGA)和差热分析法(DSC)研究了化合物11c-11e和13的热性质，数据见表1。结果表明，这类化合物均具有较高的热分解温度(154～272℃)和玻璃态转变温度(30～120℃)。在电致发光器件的制作中，有一定的应用潜力。
表1化合物11c-11e和13光电性质
[a]The fluorescence quantum yields(Φ)were measured in CH2Cl2usingquinine sulfate(Φ＝0.55)as standard.
[b]DFT/B3LYP calculated values.
[c]Optical energy gaps calculated from the edge of the electronicabsorption band.
[d]Oxidation potential in CH2Cl2(10-3mol·L-1)containing 0.1mol·L-1(n-C4H9)4NPF6with a scan rate of 100mV·s-1.
[e]EHOMO was calculated by Eox+4.4V，and ELUMo＝EHOMO-Eg
[f]Measured by TG-DTA analysis under N2at a heating rate of 10℃·min-1.

Claims (5)

1.一类含咔唑骨架的三芳基吡啶衍生物，其特征在于，结构式为：
其中，R10为H或R11为H或R12为H或
2.一类制备权利要求1中所述的咔唑骨架三芳基吡啶衍生物的方法，其特征在于，以4-(9H-咔唑-9-基)苯甲醛与为原料通过Witting-Horner偶联反应合成得到其中R7为H或CH2PO(OEt)2、R8为H或CH2PO(OEt)2、R9为H或CH2PO(OEt)2；R10为H或R11为H或R12为H或
3.如权利要求2所述的制备咔唑骨架三芳基吡啶衍生物的方法，其特征在于，反应以DMF为溶剂，乙醇钠为催化剂，室温下反应。
4.一类制备权利要求1中所述的咔唑骨架三芳基吡啶衍生物的方法，其特征在于，以4-(9H-咔唑-9-基)苯甲醛与苯甲醛为原料通过羟醛缩合反应合成得到
5.权利要求1中所述的咔唑骨架三芳基吡啶衍生物作为电致发光器件的应用。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727253A (zh) * 2018-05-10 2018-11-02 江苏师范大学 芳环-三芳基吡啶化合物及其制备方法和应用
CN113461914A (zh) * 2021-06-21 2021-10-01 上饶师范学院 一种含2,6-二苯基-4-芳基吡啶结构的D-π-A型聚合物荧光材料及其合成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1701111A (zh) * 2002-03-22 2005-11-23 出光兴产株式会社 用于有机电致发光器件的材料以及使用该材料的有机电致发光器件
CN102311693A (zh) * 2010-07-05 2012-01-11 上海海鹰粘接科技有限公司 一种环保型船舶用防污涂料及其制备方法
CN104744348A (zh) * 2015-02-13 2015-07-01 华侨大学 多取代吡啶衍生物及其制备方法
US20150318510A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1701111A (zh) * 2002-03-22 2005-11-23 出光兴产株式会社 用于有机电致发光器件的材料以及使用该材料的有机电致发光器件
CN102311693A (zh) * 2010-07-05 2012-01-11 上海海鹰粘接科技有限公司 一种环保型船舶用防污涂料及其制备方法
US20150318510A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
CN104744348A (zh) * 2015-02-13 2015-07-01 华侨大学 多取代吡啶衍生物及其制备方法

Cited By (2)

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