新型苯并咪唑衍生物的合成及金属离子调控的发光性质研究
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摘要
近年来，具有较高发光效率和优良载流子传输性能的苯并咪唑类化合物因其在光电材料领域具有广阔的应用前景而倍受研究者的重视。本论文基于苯并咪唑基本骨架设计合成了一系列新型苯并咪唑衍生物，通过金属离子调控实现了具有不同发光机理的新型有机金属发光材料，并利用理论计算方法研究了结构和性质的关系。主要研究内容概括如下：
1、合成了3种新型具有P^N螯合配位功能的苯并咪唑膦类配体(YPBI, Y=H,MO, PO)，并通过核磁、质谱、元素分析对其进行了表征。在三苯基膦辅助配体存在下，苯并咪唑膦配体与卤化亚铜CuIX (X=Cl、Br、I)反应得到9种新型一价铜化合物，通过质谱和元素分析确认了它们的组成。对其中6个配合物的单晶结构分析结果表明：它们的中心离子均形成了变形四面体配位构型。光学性质研究发现该类铜配合物通过取代基以及卤素调控能够实现从绿光到红光（557nm-612nm）的发射。以碘为配阴离子的铜配合物的固体粉末发光量子效率均在29%以上，其中Cu(HPBI)(PPh3)I的光致发光量子效率高达37.53%，是一种潜在的节能环保型高效磷光材料。
2、合成了具有大空间位阻的新型苯并咪唑膦氧类解聚配体（HL），利用ppy作为环金属配体，HL为解聚配体合成了（Pt-1）、（Ir-1）金属有机配合物，并通过核磁、质谱、元素分析和X-射线单晶衍射确证了它们的组成和结构。结果表明：Pt(II)分别与ppy和L通过N^C和O^N配位形成平面四方形结构，而Ir-1则应利用HL的N^C配位，形成了具有较弱反位效应的经式结构。铂和铱化合物均没有明显的分子间相互作用，均表现出较好的单分子磷光性质。Pt-1和Ir-1在溶液中的发光效率分别为31%和25%，固体粉末的发光效率分别为43.94%和6.23%。以Pt-1为发光材料制备了电致发光器件，其最大亮度为12020cd/m2，最大外量子效率、电流效率和功率效率分别为9.23%、25.86cd/A和25.81lm/W，结果表明Pt-1是一种性能优良的有机电致磷光材料。
3、合成了6种新型双羟基苯并咪唑类化合物，通过核磁、质谱、元素分析确认了结构；光学性质研究发现双羟基苯并咪唑类配体具有较好的激发态质子转移发光现象，部分化合物表现出优良的蓝光发射（425-443nm），最高发光量子效率为53%。合成了6种相应的锌配合物，通过质谱、元素分析确认了结构，并对其中2个配合物进行了单晶结构分析。结果表明锌配合物为五配位的类四方锥结构，并且分子内存在较强的配体间氢键作用。光学性质研究发现大部分锌配合物表现为金属离子微扰配体发光（IL）。但是，由于ZnE1配合物具有较强的配体间氢键作用（氢键O(2)-H O(3),1.679），其表现为具有较大斯托克斯位移（155nm）的激发态质子转移发光。
4、合成了以2-羟基苯乙酮类化合物为配体的6种新型九核铕簇合物，通过元素分析、红外和其中4个配合物的单晶结构分析对其组成和结构进行了确证。结果表明：该类簇合物的九个铕离子形成了具有公用顶点的二个四角锥结构。光学性质研究发现大部分簇合物激发波长位于可见光区（400nm-420nm），能够实现长波敏化的稀土铕离子的红色锐带发射。实验和DFT计算结果表明，取代基能够较好的对配体的能级进行调控，从而影响配体到中心铕离子的能量传递效率和该类簇合物的发光效率。
It is of great significance to develop photo-and electro-luminescent functionalmaterials. Recently, compounds based on benzimidazole derivatives have attractedconsiderable attention for their good light-emitting and charge transport properties.In this thesis, a series of new benzimidazole derivatives are designed and synthesized,which display different emission mechanism when they are coordinated to differentmetal ions. The phenomena are rationalized by supporting DFT computationalresults, which reveal the correlation between luminescent properties and electronicfeatures of the complexes. Our works are summarized as follows.
1. Nine mononuclear Cu(I) complexes of general formula Cu(YPBI)(PPh3)X havebeen synthesized by the reaction between CuX (X=Cl, Br, I), PPh3and2-(2’-diphenylphosphinophenyl)-1-phenylbenzimidazole derives (YPBI: Y=H, MO,PO) in a molar ratio of1/1/1in CH2Cl2solution. X-Ray crystal structure analysisreveals that the central Cu(I) ion is in a distorted tetrahedral coordination environment.The nine complexes in solid state exhibit strong phosphorescence covering the visiblespectrum from green to red (557nm-612nm). The luminescence quantum yield (Φ) ofcomplexes Cu(YPBI)(PPh3)I are higher than25%at room temperature, especially forCu(HPBI)(PPh3)I (Φ=37.53%), indicating that these novel complexes are promisingphosphorescent materials.
2. With the bulky benzoimidazole phosphine oxide (HL) as a new ancillary ligand,two new ppy-type phosphorescent complexes (Pt-1and Ir-1) have been synthesized.X-ray crystallographic studies reveal that the platinum(II) binds to L through aN^O-coordinating mode and forms a square-planar coordination geometry. However,the HL coordinates to iridium(III) with N^C-coordinating mode, resulting in theformation of meridinoal isomer with weak trans-effect. The crystal packings of Pt-1and Ir-1show that no apparent stacking interactions can be detected due to the stericeffect of the ancillary ligand. Both complexes exhibit characteristic phosphorescencein solution with highly quantum efficiencies (Pt-1:31%, Ir-1:25%) at roomtemperature, showing the first successful example of using benzoimidazole phosphine oxide as an ancillary ligand. Notably, Pt-1exhibits efficient green phosphorescencewith monomeric character in powder (Φ=43.94%). The OLED using Pt-1asphosphor exhibits a maximum brightness of12020cd m2at11V. Of particularsignificance, the device is able to achieve a maximum current efficiency (ηc) of25.86cd/A, external quantum efficiency (ηext) of9.23%and power efficiency (ηp) of25.81lm/W, which makes it a promising candidate as luminescent materials in OLEDs.
3. Six novel2-(2’-hydroxyphenyl)-4-hydroxybenzimidazole derivatives have beensynthesized and characterized by elemental analysis, MS and NMR. The compoundsexhibit bright fluorescence, via excited-state intramolecular proton transfer (ESIPT),revealing their potential applications as sensors, probes and optical materials. SixZn(II) complexes based on this kind of ligands have been prepared. X-raycrystallographic study shows that Zn2+ion has a usual five-coordinate environmentand adopts a distorted square pyramidal geometry. It’s worthy noting that there arestrong intramolecular hydrogen-bonds in the complexes, especially for the ZnE1.The photophysical studies show that, when the ligands are coordinated to Zn(II),most of the complexes exhibit normal intra-ligand fluorescence. However, ZnE1exhibits emission based on excited-state intramolecular proton transfer (ESIPT).
4. The reaction of2-hydroxybenzophenone derivatives with europium ions hasafforded a new family of luminescent nonanuclear Eu(III) clusters. Crystal structureanalysis of the clusters reveals that the metal core comprises two vertex-sharingsquare pyramidal units. Most of these complexes show emissions typical of Eu3+ionunder visible light excitation (400–420nm) at room temperature. Photophysicalcharacterization and DFT study reveal a correlation between luminescent efficienciesof Eu(III) complexes and the electronic features of the ligands, which in true can betuned by the nature of substituents in the4-position of the ligands. The ligands withfluorine substituent possess more suitable triplet energy levels, resulting in moreintensive luminescence.
1、合成了3种新型具有P^N螯合配位功能的苯并咪唑膦类配体(YPBI, Y=H,MO, PO)，并通过核磁、质谱、元素分析对其进行了表征。在三苯基膦辅助配体存在下，苯并咪唑膦配体与卤化亚铜CuIX (X=Cl、Br、I)反应得到9种新型一价铜化合物，通过质谱和元素分析确认了它们的组成。对其中6个配合物的单晶结构分析结果表明：它们的中心离子均形成了变形四面体配位构型。光学性质研究发现该类铜配合物通过取代基以及卤素调控能够实现从绿光到红光（557nm-612nm）的发射。以碘为配阴离子的铜配合物的固体粉末发光量子效率均在29%以上，其中Cu(HPBI)(PPh3)I的光致发光量子效率高达37.53%，是一种潜在的节能环保型高效磷光材料。
2、合成了具有大空间位阻的新型苯并咪唑膦氧类解聚配体（HL），利用ppy作为环金属配体，HL为解聚配体合成了（Pt-1）、（Ir-1）金属有机配合物，并通过核磁、质谱、元素分析和X-射线单晶衍射确证了它们的组成和结构。结果表明：Pt(II)分别与ppy和L通过N^C和O^N配位形成平面四方形结构，而Ir-1则应利用HL的N^C配位，形成了具有较弱反位效应的经式结构。铂和铱化合物均没有明显的分子间相互作用，均表现出较好的单分子磷光性质。Pt-1和Ir-1在溶液中的发光效率分别为31%和25%，固体粉末的发光效率分别为43.94%和6.23%。以Pt-1为发光材料制备了电致发光器件，其最大亮度为12020cd/m2，最大外量子效率、电流效率和功率效率分别为9.23%、25.86cd/A和25.81lm/W，结果表明Pt-1是一种性能优良的有机电致磷光材料。
3、合成了6种新型双羟基苯并咪唑类化合物，通过核磁、质谱、元素分析确认了结构；光学性质研究发现双羟基苯并咪唑类配体具有较好的激发态质子转移发光现象，部分化合物表现出优良的蓝光发射（425-443nm），最高发光量子效率为53%。合成了6种相应的锌配合物，通过质谱、元素分析确认了结构，并对其中2个配合物进行了单晶结构分析。结果表明锌配合物为五配位的类四方锥结构，并且分子内存在较强的配体间氢键作用。光学性质研究发现大部分锌配合物表现为金属离子微扰配体发光（IL）。但是，由于ZnE1配合物具有较强的配体间氢键作用（氢键O(2)-H O(3),1.679），其表现为具有较大斯托克斯位移（155nm）的激发态质子转移发光。
4、合成了以2-羟基苯乙酮类化合物为配体的6种新型九核铕簇合物，通过元素分析、红外和其中4个配合物的单晶结构分析对其组成和结构进行了确证。结果表明：该类簇合物的九个铕离子形成了具有公用顶点的二个四角锥结构。光学性质研究发现大部分簇合物激发波长位于可见光区（400nm-420nm），能够实现长波敏化的稀土铕离子的红色锐带发射。实验和DFT计算结果表明，取代基能够较好的对配体的能级进行调控，从而影响配体到中心铕离子的能量传递效率和该类簇合物的发光效率。
It is of great significance to develop photo-and electro-luminescent functionalmaterials. Recently, compounds based on benzimidazole derivatives have attractedconsiderable attention for their good light-emitting and charge transport properties.In this thesis, a series of new benzimidazole derivatives are designed and synthesized,which display different emission mechanism when they are coordinated to differentmetal ions. The phenomena are rationalized by supporting DFT computationalresults, which reveal the correlation between luminescent properties and electronicfeatures of the complexes. Our works are summarized as follows.
1. Nine mononuclear Cu(I) complexes of general formula Cu(YPBI)(PPh3)X havebeen synthesized by the reaction between CuX (X=Cl, Br, I), PPh3and2-(2’-diphenylphosphinophenyl)-1-phenylbenzimidazole derives (YPBI: Y=H, MO,PO) in a molar ratio of1/1/1in CH2Cl2solution. X-Ray crystal structure analysisreveals that the central Cu(I) ion is in a distorted tetrahedral coordination environment.The nine complexes in solid state exhibit strong phosphorescence covering the visiblespectrum from green to red (557nm-612nm). The luminescence quantum yield (Φ) ofcomplexes Cu(YPBI)(PPh3)I are higher than25%at room temperature, especially forCu(HPBI)(PPh3)I (Φ=37.53%), indicating that these novel complexes are promisingphosphorescent materials.
2. With the bulky benzoimidazole phosphine oxide (HL) as a new ancillary ligand,two new ppy-type phosphorescent complexes (Pt-1and Ir-1) have been synthesized.X-ray crystallographic studies reveal that the platinum(II) binds to L through aN^O-coordinating mode and forms a square-planar coordination geometry. However,the HL coordinates to iridium(III) with N^C-coordinating mode, resulting in theformation of meridinoal isomer with weak trans-effect. The crystal packings of Pt-1and Ir-1show that no apparent stacking interactions can be detected due to the stericeffect of the ancillary ligand. Both complexes exhibit characteristic phosphorescencein solution with highly quantum efficiencies (Pt-1:31%, Ir-1:25%) at roomtemperature, showing the first successful example of using benzoimidazole phosphine oxide as an ancillary ligand. Notably, Pt-1exhibits efficient green phosphorescencewith monomeric character in powder (Φ=43.94%). The OLED using Pt-1asphosphor exhibits a maximum brightness of12020cd m2at11V. Of particularsignificance, the device is able to achieve a maximum current efficiency (ηc) of25.86cd/A, external quantum efficiency (ηext) of9.23%and power efficiency (ηp) of25.81lm/W, which makes it a promising candidate as luminescent materials in OLEDs.
3. Six novel2-(2’-hydroxyphenyl)-4-hydroxybenzimidazole derivatives have beensynthesized and characterized by elemental analysis, MS and NMR. The compoundsexhibit bright fluorescence, via excited-state intramolecular proton transfer (ESIPT),revealing their potential applications as sensors, probes and optical materials. SixZn(II) complexes based on this kind of ligands have been prepared. X-raycrystallographic study shows that Zn2+ion has a usual five-coordinate environmentand adopts a distorted square pyramidal geometry. It’s worthy noting that there arestrong intramolecular hydrogen-bonds in the complexes, especially for the ZnE1.The photophysical studies show that, when the ligands are coordinated to Zn(II),most of the complexes exhibit normal intra-ligand fluorescence. However, ZnE1exhibits emission based on excited-state intramolecular proton transfer (ESIPT).
4. The reaction of2-hydroxybenzophenone derivatives with europium ions hasafforded a new family of luminescent nonanuclear Eu(III) clusters. Crystal structureanalysis of the clusters reveals that the metal core comprises two vertex-sharingsquare pyramidal units. Most of these complexes show emissions typical of Eu3+ionunder visible light excitation (400–420nm) at room temperature. Photophysicalcharacterization and DFT study reveal a correlation between luminescent efficienciesof Eu(III) complexes and the electronic features of the ligands, which in true can betuned by the nature of substituents in the4-position of the ligands. The ligands withfluorine substituent possess more suitable triplet energy levels, resulting in moreintensive luminescence.
引文
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