含喹啉配体的铝和镓（Ⅲ）金属配合物的合成与电致发光特性研究
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摘要
有机电致发光材料是一种在电场激发下产生发光现象的物质。有机发光二极管是未来一种理想的平板显示器。尤其作为平板显示中的背光源及一般的固态照明有很大的应用前景。为此,人们在进一步优化器件的同时,也致力于合成具有优良性能的新材料,以提高电致发光效率。例如,合成具有高荧光效率、高电荷传输以及适当的HOMO/LUMO能级的材料。鉴于电子传输材料电子迁移率总体落后于空穴传输材料的空穴迁移率,导致器件效率降低的现状,本论文设计并合成了具有优良电子传输性能的有机半导体材料,采用稳态和瞬态的方法研究了目标产物的光、电性能。
1、合成了双(8-羟基喹啉)乙酰丙酮合铝配合物(Alq2A)。发现室温下,这种配合物无论在溶液、粉末还是固体膜状态下均具有较强的荧光发射。通过荧光量子效率计算,表明此种配合物具有比三(8-羟基喹啉)铝更高的荧光量子效率,约为6.75倍。通过量子化学模拟计算得知:此种配合物的发光主要是由于配体与配体之间的π-π*跃迁产生,配合物的铝中心对增强配体的荧光发射起重要作用。
2、作为合成Alq2A时出现的反应副产物,通过单晶X射线衍射分析,得到其分子结构。首先报道乙酰丙酮铝具有强烈的荧光性能和很高的荧光寿命。
3、用瞬态电致发光方法研究了Alq2A在有机发光二极管中载流子的传输特性。实验中采用了不同纯度的Alq2A材料进行研究,结果发现纯度对电子传输性能的影响很大。为了与Alq3的载流子迁移率进行对照,在同样的实验条件下研究了Alq3的载流子的电子迁移率。研究发现:Alq2A具有比Alq3更高的电子迁移率,且电子迁移率受纯度影响很大。
4、用稳态电流-电压特性考察Alq2A的发光性能以及定性研究其电子传输性能。分别以Alq2A和Alq3作为发光层的器件结构中,两个器件的发光光谱位置几乎不发生改变,发射峰位于513nm附近;Alq2A器件具有比Alq3器件更高的效率,前者比后者流明效率高75%,功率效率高165%。研究表明,导致Alq2A器件效率高的原因主要由以下三个因素决定:a.较高的电子迁移;b.较高的荧光量子效率; c.优良的成膜性能。此外,设计器件排除势垒对电荷注入的影响,间接证明Alq2A具有比Alq3更好的电子传输性能。
5、合成一种喹啉类镓的配合物-二(2-甲基-8-羟基喹啉)氯化镓(GaMq2Cl),这种配合物具有良好的热稳定性,其分解温度348℃;在紫外光的激发下,其粉体产生发射峰在471nm的蓝色荧光,以GaMq2Cl作为发光层制备了发光器件,实现了发射峰在502nm的蓝绿光电致发光。
通过以上研究,得到了一些有意义的结论:
(1)、第二配体乙酰丙酮的引入对铝配合物的光致发光效率及载流子传输性能有重要的影响。化合物中载流子传输的平衡对提高有机电致发光器件的发光性能具有极大的影响。使用载流子传输平衡和高效光致发光的材料都能得到高性能的有机电致发光器件。
(2)、在特定条件下得到的乙酰丙酮铝具有很强的荧光性能和荧光寿命,揭示分子结构并非是物质荧光性能的唯一决定因素。
(3)、由乙酰丙酮与8-羟基喹啉为配体的混配络合物的形成能力随中心金属离子Al和Ga的不同而有很大的差异,在实验所述条件下,Ga离子的存在,可能导致配体乙酰丙酮与8-羟基喹啉在配体内界不能相亲相溶,而产生相互排斥,故在相同实验条件下未生成与双(8-羟基喹啉)乙酰丙酮合铝相类似的结构。
Organic electroluminescent (EL) materials are the substances that give out lights when excited by electric field. Organic light-emitting diodes (OLED) is one of the most promising candidates for the next generation display technologies. Especially, OLEDs also have great potential for backlights in flat-panel displays and general solid state lighting application. Along with the implementation of further architectural refinements, the enhancement of the electroluminescence efficiency passes obviously through the synthesis of the new molecules possessing very dedicated capacities. For instance and good quantum yield, high charge mobility are generally required to achieve good device output. Considering low efficiency is resulted from the fact that electron-transporting materials exhibit poorer mobility than hole-transporting ones, we designed a series of emissive materials having the required charge transporting properties, and investigated their optical and electrical properties by steady and transient state measurement.
1. An aluminum complex, bis(8-hydroxyquinoline) acetylacetone aluminum (Alq2A) was synthesized, which has luminescence in solution, powder and solid state at room temperature. Its fluorescence quantum yields was determined to be 6.75 times that of Alq3. Analysis of the electronic structure of Alq2A calculated by quantum chemical simulation revealed that the fluorescent emission of Alq2A originates from ligand-centeredπ-π* transition. The Al (Ⅲ) centers play an important role in enhancing the fluorescent emission of the ligands.
2. Tris(acetylacetone) aluminum (Alacac), as a byproduct in the third chapter, was obtained and investigated. Its crystalline structure was determined from X-ray diffraction data on single crystals. It was discovered firstly that the complex has intense fluorescence and good fluorescence life.
3. The transport properties of charge carrier in bilayer organic light-emitting diodes were studied by transient electroluminescence. The electron mobility of Alq2A with different purity was found to be obviously dependent on its purity, i.e. higher purity led to higher electron mobility. The measurement of electron mobility of Alq3 indicated that the electron mobility of Alq2A is higher than that of Alq3.
4. The Electroluminescence performance of Alq2A-based OLED was investigated by steady-state current-voltage characteristics, and the electronic transport properties was proved furtherly by qualitative experiment. The emission of the Alq2A-based device peaks at 513 nm, similar to that of Alq3. Alq2A device has an approximately 75% higher current efficiency and 165% higher power efficiency than Alq3 structure. Alq2A complex shows a higher EL efficiency in steady-state EL studies, which is considered to be derived from: 1) improved electron mobility; 2) high fluorescene efficiency; and 3) good film-forming.
5. An 8-hydroxyquinoline complex, GaMq2Cl, was synthesized and purified by vacuum sublimation. Experimental results show that the complex was a thermally stable material, with decomposition temperature being 348℃. Its powder emitted intensive blue fluorescence with peak wavelength of 471nm under UV irradiation. GaMq2Cl-based device was fabricated, which emitted blue-greenish fluorescence with peak wavelength of 502nm.
The major results of this thesis were summarized as follows:
(1) The introduction of the second ligand acetylacetone has great effect on fluorescence quantum efficiency and electron transport property of aluminum complex containing 8-hydroxyquinoline. Organic electro- luminescence materials with balanced electron/hole injection and good carrier-transporting property and good photoluminescence can improve the performance of the fabricated OLEDs.
(2) Tris(acetylacetone) aluminum synthesized in given conditions has intense fluorescence and good fluorescence lifetime, indicating that molecular structure is not the only-factor affecting fluorescence property.
(3) The forming ability of mixed ligand complexes containing acetylacetone and 8-hydroxyquinoline differs in center ions Al and Ga, Corresponding Ga complex were not sythesized in the same conditions as for Al complex, indicating that acetylacetone and 8-hydroxyquinoline ligands can not dissolve in inner boundary in the presence of Ga ions.
1、合成了双(8-羟基喹啉)乙酰丙酮合铝配合物(Alq2A)。发现室温下,这种配合物无论在溶液、粉末还是固体膜状态下均具有较强的荧光发射。通过荧光量子效率计算,表明此种配合物具有比三(8-羟基喹啉)铝更高的荧光量子效率,约为6.75倍。通过量子化学模拟计算得知:此种配合物的发光主要是由于配体与配体之间的π-π*跃迁产生,配合物的铝中心对增强配体的荧光发射起重要作用。
2、作为合成Alq2A时出现的反应副产物,通过单晶X射线衍射分析,得到其分子结构。首先报道乙酰丙酮铝具有强烈的荧光性能和很高的荧光寿命。
3、用瞬态电致发光方法研究了Alq2A在有机发光二极管中载流子的传输特性。实验中采用了不同纯度的Alq2A材料进行研究,结果发现纯度对电子传输性能的影响很大。为了与Alq3的载流子迁移率进行对照,在同样的实验条件下研究了Alq3的载流子的电子迁移率。研究发现:Alq2A具有比Alq3更高的电子迁移率,且电子迁移率受纯度影响很大。
4、用稳态电流-电压特性考察Alq2A的发光性能以及定性研究其电子传输性能。分别以Alq2A和Alq3作为发光层的器件结构中,两个器件的发光光谱位置几乎不发生改变,发射峰位于513nm附近;Alq2A器件具有比Alq3器件更高的效率,前者比后者流明效率高75%,功率效率高165%。研究表明,导致Alq2A器件效率高的原因主要由以下三个因素决定:a.较高的电子迁移;b.较高的荧光量子效率; c.优良的成膜性能。此外,设计器件排除势垒对电荷注入的影响,间接证明Alq2A具有比Alq3更好的电子传输性能。
5、合成一种喹啉类镓的配合物-二(2-甲基-8-羟基喹啉)氯化镓(GaMq2Cl),这种配合物具有良好的热稳定性,其分解温度348℃;在紫外光的激发下,其粉体产生发射峰在471nm的蓝色荧光,以GaMq2Cl作为发光层制备了发光器件,实现了发射峰在502nm的蓝绿光电致发光。
通过以上研究,得到了一些有意义的结论:
(1)、第二配体乙酰丙酮的引入对铝配合物的光致发光效率及载流子传输性能有重要的影响。化合物中载流子传输的平衡对提高有机电致发光器件的发光性能具有极大的影响。使用载流子传输平衡和高效光致发光的材料都能得到高性能的有机电致发光器件。
(2)、在特定条件下得到的乙酰丙酮铝具有很强的荧光性能和荧光寿命,揭示分子结构并非是物质荧光性能的唯一决定因素。
(3)、由乙酰丙酮与8-羟基喹啉为配体的混配络合物的形成能力随中心金属离子Al和Ga的不同而有很大的差异,在实验所述条件下,Ga离子的存在,可能导致配体乙酰丙酮与8-羟基喹啉在配体内界不能相亲相溶,而产生相互排斥,故在相同实验条件下未生成与双(8-羟基喹啉)乙酰丙酮合铝相类似的结构。
Organic electroluminescent (EL) materials are the substances that give out lights when excited by electric field. Organic light-emitting diodes (OLED) is one of the most promising candidates for the next generation display technologies. Especially, OLEDs also have great potential for backlights in flat-panel displays and general solid state lighting application. Along with the implementation of further architectural refinements, the enhancement of the electroluminescence efficiency passes obviously through the synthesis of the new molecules possessing very dedicated capacities. For instance and good quantum yield, high charge mobility are generally required to achieve good device output. Considering low efficiency is resulted from the fact that electron-transporting materials exhibit poorer mobility than hole-transporting ones, we designed a series of emissive materials having the required charge transporting properties, and investigated their optical and electrical properties by steady and transient state measurement.
1. An aluminum complex, bis(8-hydroxyquinoline) acetylacetone aluminum (Alq2A) was synthesized, which has luminescence in solution, powder and solid state at room temperature. Its fluorescence quantum yields was determined to be 6.75 times that of Alq3. Analysis of the electronic structure of Alq2A calculated by quantum chemical simulation revealed that the fluorescent emission of Alq2A originates from ligand-centeredπ-π* transition. The Al (Ⅲ) centers play an important role in enhancing the fluorescent emission of the ligands.
2. Tris(acetylacetone) aluminum (Alacac), as a byproduct in the third chapter, was obtained and investigated. Its crystalline structure was determined from X-ray diffraction data on single crystals. It was discovered firstly that the complex has intense fluorescence and good fluorescence life.
3. The transport properties of charge carrier in bilayer organic light-emitting diodes were studied by transient electroluminescence. The electron mobility of Alq2A with different purity was found to be obviously dependent on its purity, i.e. higher purity led to higher electron mobility. The measurement of electron mobility of Alq3 indicated that the electron mobility of Alq2A is higher than that of Alq3.
4. The Electroluminescence performance of Alq2A-based OLED was investigated by steady-state current-voltage characteristics, and the electronic transport properties was proved furtherly by qualitative experiment. The emission of the Alq2A-based device peaks at 513 nm, similar to that of Alq3. Alq2A device has an approximately 75% higher current efficiency and 165% higher power efficiency than Alq3 structure. Alq2A complex shows a higher EL efficiency in steady-state EL studies, which is considered to be derived from: 1) improved electron mobility; 2) high fluorescene efficiency; and 3) good film-forming.
5. An 8-hydroxyquinoline complex, GaMq2Cl, was synthesized and purified by vacuum sublimation. Experimental results show that the complex was a thermally stable material, with decomposition temperature being 348℃. Its powder emitted intensive blue fluorescence with peak wavelength of 471nm under UV irradiation. GaMq2Cl-based device was fabricated, which emitted blue-greenish fluorescence with peak wavelength of 502nm.
The major results of this thesis were summarized as follows:
(1) The introduction of the second ligand acetylacetone has great effect on fluorescence quantum efficiency and electron transport property of aluminum complex containing 8-hydroxyquinoline. Organic electro- luminescence materials with balanced electron/hole injection and good carrier-transporting property and good photoluminescence can improve the performance of the fabricated OLEDs.
(2) Tris(acetylacetone) aluminum synthesized in given conditions has intense fluorescence and good fluorescence lifetime, indicating that molecular structure is not the only-factor affecting fluorescence property.
(3) The forming ability of mixed ligand complexes containing acetylacetone and 8-hydroxyquinoline differs in center ions Al and Ga, Corresponding Ga complex were not sythesized in the same conditions as for Al complex, indicating that acetylacetone and 8-hydroxyquinoline ligands can not dissolve in inner boundary in the presence of Ga ions.
引文
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