氮杂芴类有机/聚合物的设计、合成及其应用
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摘要
1987年,邓青云等首次报道了有机发光二极管器件,此后,因有机发光二极管具有重量轻、视角广、大面积柔性显示、响应速度快等优点,在平板显示和固体照明领域有机发光二极管备受瞩目。目前,主要有两种方式调控有机发光材料性能：一种是通过结构调控,结构调控是我们课题组1998年在美国化学会志上提出的p-n嵌段理论,即通过替换不同结构的化合物来调整其光电性能,这是目前主流的调控方法；第二种就是通过超分子弱作用,如氢键、π-π堆积作用、配位作用等来调节化合物的光电性能。我们尝试将这两种调控方式有机结合起来,以期获得性能更为优异的有机/聚合物材料。在本论文中,我们设计并合成了一系列基于氮杂芴类的有机小分子和聚合物,并通过超分子作用实现了对其光电性能的调控。
1.发现一种简便合成氮杂芴中间体的方法,构筑了一系列D-A型氮杂芴酮半导体,同时研究它们的单分子自组装行为
我们发现一种简便、快捷合成2,7-二溴-4,5-氮杂芴酮的方法,并对其机理进行初步研究。在此基础上,我们通过Stille偶联反应制备得到一系列D-A氮杂芴类衍生物,这些D-A氮杂芴类衍生物均表现出溶剂依赖荧光的特性。通过对这些化合物单分子自组装行为的研究,发现烷基链在构建有序结构中起着至关重要的作用,化合物6具有两个烷基链,这些烷基链相互穿插构筑了高度有序的结构。我们选择化合物6尝试制备了OFET器件。
2.通过超分子作用调控氮杂芴类聚合物的光电性能
芴基团上的两个碳原子被氮原子取代后形成了氮杂芴基团,因此氮杂芴基团和芴的空间拓扑结构极为相似。将氮杂芴引入到聚芴体系中可以形成一种极佳的模板去研究超分子共轭聚合物的构-效关系。基于此理念,我们合成一系列氮杂芴基的寡聚物和聚合物。这些氮杂芴基的寡聚物和聚合物都具有较高的热稳定性,氮杂芴寡聚物具有溶剂依赖荧光特性;氮杂芴基聚合物对质子酸具有极强的响应能力,其吸收光谱可红移40-60nm,并且氮杂芴基聚合物的光电性能还可以通过与金属离子的相互作用来调控。氮杂芴类聚合物是一类潜在的可应用于薄膜器件的超分子聚合物材料。
3.氮杂芴类聚合物的自组装和通过超分子作用实现白光器件
为了系统研究超分子自组装性能,我们将氮杂芴引入聚芴体系中形成氮杂芴聚合物。研究发现,由于氮杂芴聚合物中存在C-H…N超分子作用,在光谱、聚合物凝胶、水分散的纳米颗粒等方面与聚芴的性能差异很大。氮杂芴聚合物纳米颗粒在水溶液对质子酸具有很强的响应能力,说明它可能用于检测生物体内的pH值变化。由于存在着很强的氢键诱导的能量转移,氮杂芴聚合物作为发光层制备的OLED(?)件呈现出白光。
4.利用超分子作用实现溶液加工的白光器件
本部分设计、合成了两种结构相近的咔唑基氮杂芴衍生物(2a和2b),并以其为模板系统研究了超分子作用对于光电性能的调控。以2a作为发光层制备得到一种具有纯正白光的OLED器件,并在不同的驱动电压下色纯度基本保持不变。通过光谱的系统研究,我们认为白光是化合物2a自身的蓝光发射和其excimer黄光发射共同作用的结果。
Organic light-emitting diodes (OLEDs) have attracted increasing attentions for their application as flat-panel displays and solid-state lighting technology since the original works first reported by Tang and co-workers, due to their light weights, wide-viewing angles, high contrast, wide and cheap raw material source, self-emission properties, flexible large-area, fast response times, and so on. Many phosphorescent and fluorescent emitters based devices have been developed to meet the demands of full-color displays. The main approaches to adjust the photoelectric properties are classified into two general categories:one method to adjust the optoelectric properties is based on the modulation of different chemical structures, which was first reported by our group. The other promising approach that tunes the above properties is using supramolecular interactions, such as hydrogen bonding, π-π stacking interactions, coordination role. We try to combine these two different methods, in order to obtain more excellent performance of Organic/Polymeric Materials. In this paper, we designed and synthesized a series of diazafluorene-based organic molecules and polymers, and tuned their optoelectric properties by using supramolecular interactions.
1. The synthesis, properties and self-assembly of diazafluorene-based organic semiconductors
A mild and effective method to prepare2,7-dibromo-4,5-diazafluoren-9-one (3) has been described involving tandem oxidation and rearrangement reactions. Diazafluorenone-based donor-acceptor molecules via stille coupling reactions exhibit solvent-dependent fluorescence and excellent selfassembly behaviors at the solideliquid interface according to the characterization of scanning tunneling microscopy (STM). The monolayer of compounds6is a large uniform and highly ordered assembly structure. The van der Waals forces play a significant role in the formation of the molecular monolayers. Based on that, a simple OFET device was fabricated.
2. Synthesis and Characterization of Diazafluorene-based Oligofluorenes and Polyfluorenes
4,5-Diazafluorene (DAF) has the similar configuration with fluorene unit except for the replaction of two carbon atoms with nitrogen atoms, offering an ideal model of supramolecular conjugated polymers to investigate the structure-property relationship. Herein, a series of DAF-based oligofluorenes and polyfluorenes, including NFF, NF2F, F2NF, PFO-NO, PFO-N5, PFO-N15and PFO-N50, have been synthesized by Suzuki and/or Yamamato polymerization. The DAF can cause to reduce lowest unoccupied molecular orbital (LUMO) levels with the increasement content. All dioctyldiazafluorene-based copolymers show a improved solubility, high quantum yields, and good thermal stability. The diazafluorenone (DAFone)-based oligomers exhibit solvent-dependent fluorescence and DAF-based copolymers show optical response with a large red-shift (ca.40-60nm) of the absorption peakwhen they were protonated with trifluoroacetic acid. Their photoluminescent properties couldalso obviously changed with the introduction of metal ions. DAF are useful building blocks for suprmaolecular polymer semiconductors and thin films.
3. A Diazafluorene-containing Polyfluorene:Synthesis, Supramolecular Assembly and Their Optoelectronic Properties
Nitrogen heteroatomic fluorenes, diazafluorenes (DAFs), was incorporated into poly (9,9-dioctylfluorene)(PF8) to systematically investigate the effect of nitrogen heteroatomic substitution on supramolecular self-assembly property. As a result, the optical property of typical self-assembled aggregates, conjugated polymer gels (CPGs) and water-dispersible nanoparticles (CPNs), were significantly different to PF8for the C-H…N supramolecular interactions. Optical response of water-dispersible CPNs to proton acid provided new platform to explore theses nitrogen heterocyclic CPs in water or bio-system. Finally, for the stronger hydrogen-bonded-assisted energy transfer, the first DAF-containing polymer white light-emitting diode (WPLED) with CIE (0.26,0.30) was fabricated.
4. Solution-processible Diazafluorene-based Oligomers as a single emitting-component for white electroluminescence
A pure white organic light-emitting diode (WOLED) with a simple device architecture of indium tin oxide (ITO)/poly-(3,4-ethylenedioxythiophene):poly-(styrenesuphonic acid)(PEDOT:PSS)/compound2a/1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI)/LiF/Al was realized by using a single small molecule, compound2a as the light-emitting material. The device emits almost pure white light with stable CIE coordinates under different driving voltages. The white emission comes from the combination of the blue emission originating from compound2a and the long-wavelength orange emission originating from the excimer of compound2a.
1.发现一种简便合成氮杂芴中间体的方法,构筑了一系列D-A型氮杂芴酮半导体,同时研究它们的单分子自组装行为
我们发现一种简便、快捷合成2,7-二溴-4,5-氮杂芴酮的方法,并对其机理进行初步研究。在此基础上,我们通过Stille偶联反应制备得到一系列D-A氮杂芴类衍生物,这些D-A氮杂芴类衍生物均表现出溶剂依赖荧光的特性。通过对这些化合物单分子自组装行为的研究,发现烷基链在构建有序结构中起着至关重要的作用,化合物6具有两个烷基链,这些烷基链相互穿插构筑了高度有序的结构。我们选择化合物6尝试制备了OFET器件。
2.通过超分子作用调控氮杂芴类聚合物的光电性能
芴基团上的两个碳原子被氮原子取代后形成了氮杂芴基团,因此氮杂芴基团和芴的空间拓扑结构极为相似。将氮杂芴引入到聚芴体系中可以形成一种极佳的模板去研究超分子共轭聚合物的构-效关系。基于此理念,我们合成一系列氮杂芴基的寡聚物和聚合物。这些氮杂芴基的寡聚物和聚合物都具有较高的热稳定性,氮杂芴寡聚物具有溶剂依赖荧光特性;氮杂芴基聚合物对质子酸具有极强的响应能力,其吸收光谱可红移40-60nm,并且氮杂芴基聚合物的光电性能还可以通过与金属离子的相互作用来调控。氮杂芴类聚合物是一类潜在的可应用于薄膜器件的超分子聚合物材料。
3.氮杂芴类聚合物的自组装和通过超分子作用实现白光器件
为了系统研究超分子自组装性能,我们将氮杂芴引入聚芴体系中形成氮杂芴聚合物。研究发现,由于氮杂芴聚合物中存在C-H…N超分子作用,在光谱、聚合物凝胶、水分散的纳米颗粒等方面与聚芴的性能差异很大。氮杂芴聚合物纳米颗粒在水溶液对质子酸具有很强的响应能力,说明它可能用于检测生物体内的pH值变化。由于存在着很强的氢键诱导的能量转移,氮杂芴聚合物作为发光层制备的OLED(?)件呈现出白光。
4.利用超分子作用实现溶液加工的白光器件
本部分设计、合成了两种结构相近的咔唑基氮杂芴衍生物(2a和2b),并以其为模板系统研究了超分子作用对于光电性能的调控。以2a作为发光层制备得到一种具有纯正白光的OLED器件,并在不同的驱动电压下色纯度基本保持不变。通过光谱的系统研究,我们认为白光是化合物2a自身的蓝光发射和其excimer黄光发射共同作用的结果。
Organic light-emitting diodes (OLEDs) have attracted increasing attentions for their application as flat-panel displays and solid-state lighting technology since the original works first reported by Tang and co-workers, due to their light weights, wide-viewing angles, high contrast, wide and cheap raw material source, self-emission properties, flexible large-area, fast response times, and so on. Many phosphorescent and fluorescent emitters based devices have been developed to meet the demands of full-color displays. The main approaches to adjust the photoelectric properties are classified into two general categories:one method to adjust the optoelectric properties is based on the modulation of different chemical structures, which was first reported by our group. The other promising approach that tunes the above properties is using supramolecular interactions, such as hydrogen bonding, π-π stacking interactions, coordination role. We try to combine these two different methods, in order to obtain more excellent performance of Organic/Polymeric Materials. In this paper, we designed and synthesized a series of diazafluorene-based organic molecules and polymers, and tuned their optoelectric properties by using supramolecular interactions.
1. The synthesis, properties and self-assembly of diazafluorene-based organic semiconductors
A mild and effective method to prepare2,7-dibromo-4,5-diazafluoren-9-one (3) has been described involving tandem oxidation and rearrangement reactions. Diazafluorenone-based donor-acceptor molecules via stille coupling reactions exhibit solvent-dependent fluorescence and excellent selfassembly behaviors at the solideliquid interface according to the characterization of scanning tunneling microscopy (STM). The monolayer of compounds6is a large uniform and highly ordered assembly structure. The van der Waals forces play a significant role in the formation of the molecular monolayers. Based on that, a simple OFET device was fabricated.
2. Synthesis and Characterization of Diazafluorene-based Oligofluorenes and Polyfluorenes
4,5-Diazafluorene (DAF) has the similar configuration with fluorene unit except for the replaction of two carbon atoms with nitrogen atoms, offering an ideal model of supramolecular conjugated polymers to investigate the structure-property relationship. Herein, a series of DAF-based oligofluorenes and polyfluorenes, including NFF, NF2F, F2NF, PFO-NO, PFO-N5, PFO-N15and PFO-N50, have been synthesized by Suzuki and/or Yamamato polymerization. The DAF can cause to reduce lowest unoccupied molecular orbital (LUMO) levels with the increasement content. All dioctyldiazafluorene-based copolymers show a improved solubility, high quantum yields, and good thermal stability. The diazafluorenone (DAFone)-based oligomers exhibit solvent-dependent fluorescence and DAF-based copolymers show optical response with a large red-shift (ca.40-60nm) of the absorption peakwhen they were protonated with trifluoroacetic acid. Their photoluminescent properties couldalso obviously changed with the introduction of metal ions. DAF are useful building blocks for suprmaolecular polymer semiconductors and thin films.
3. A Diazafluorene-containing Polyfluorene:Synthesis, Supramolecular Assembly and Their Optoelectronic Properties
Nitrogen heteroatomic fluorenes, diazafluorenes (DAFs), was incorporated into poly (9,9-dioctylfluorene)(PF8) to systematically investigate the effect of nitrogen heteroatomic substitution on supramolecular self-assembly property. As a result, the optical property of typical self-assembled aggregates, conjugated polymer gels (CPGs) and water-dispersible nanoparticles (CPNs), were significantly different to PF8for the C-H…N supramolecular interactions. Optical response of water-dispersible CPNs to proton acid provided new platform to explore theses nitrogen heterocyclic CPs in water or bio-system. Finally, for the stronger hydrogen-bonded-assisted energy transfer, the first DAF-containing polymer white light-emitting diode (WPLED) with CIE (0.26,0.30) was fabricated.
4. Solution-processible Diazafluorene-based Oligomers as a single emitting-component for white electroluminescence
A pure white organic light-emitting diode (WOLED) with a simple device architecture of indium tin oxide (ITO)/poly-(3,4-ethylenedioxythiophene):poly-(styrenesuphonic acid)(PEDOT:PSS)/compound2a/1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI)/LiF/Al was realized by using a single small molecule, compound2a as the light-emitting material. The device emits almost pure white light with stable CIE coordinates under different driving voltages. The white emission comes from the combination of the blue emission originating from compound2a and the long-wavelength orange emission originating from the excimer of compound2a.
引文
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