含芳胺或吡咯并吡咯二酮的聚合物合成及光电性能研究
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摘要
目前，全球面临的主要能源问题是化石燃料即将耗尽和能源危机,因此，21世纪全球的主要挑战是开发清洁、可持续利用能源和大力发展节能技术。有机太阳能电池(OSCs)因为能够有效利用清洁和可再生能源太阳能，所以很有希望替代化石燃料。有机发光二极管(OLED)，由于其在节能上的应用，也吸引了人们的极大关注。
本论文的出发点是：设计合成新型的有机太阳能供体材料和有机电致发光材料，系统研究材料分子结构与器件性能关系。研究内容主要包括：
1.设计合成一种侧链挂接吡咯并吡咯二酮受体的侧链供体-受体(D-A)聚合物光伏材料(PBDT-TDPP-S)。聚合物PBDT-TDPP-S具有良好溶解性和较低的HOMO能级(5.34eV)，同时，聚合物PBDT-TDPP-S具有较高和平衡的载流子迁移率。通过构建结构为ITO/PEDOT:PSS/PBDT-TDPP-S:PC71BM/LiF/Al的光伏器件，器件最大能量效率达到4.89%，其中，开路电压为0.84V,短路电流为10.04mA cm~(-2),更重要的是，器件填充因子达56%，是目前文献报道的侧链D-A型聚合物光伏材料最高值。
2.设计合成一种侧链主链同时连接吡咯并吡咯二酮受体的三元共聚物光伏材料(PTh-BDT-2DTDPP)。聚合物PTh-BDT-2DTDPP具有宽光谱响应(300-850nm)，通过构建结构为ITO/PEDOT:PSS/PTh-BDT-2DTDPP:PC61BM/LiF/Al的光伏器件，器件最大能量效率达到4.36%，其中，开路电压为0.78V,短路电流为10.47mAcm~(-2),填充因子达53%。
3.设计合成两种侧链挂接三苯胺或噻吩功能基的苯并二噻吩-苯并吡嗪共聚物光伏材料。侧链挂接三苯胺功能基聚合物(P2)展现出更好光伏性能。通过构建结构为ITO/PEDOT:PSS/Polymer:PC71BM/LiF/Al的光伏器件，基于P2:PC71BM光伏器件的最大能量效率达到3.43%，其中开路电压为0.80V,短路电流为9.20mAcm~(-2)，器件的能量效率为噻吩功能基修饰聚合物(P1)的2.29倍。
4.设计合成一系列侧链挂接空穴传输咔唑功能基、电子传输噁二唑功能基和端基挂接苯基异喹啉铱红光配合物的聚芴类电致磷光材料。系统研究空穴传输功能基和电子传输功能基对材料的影响。聚合物PFCz3OXD7Ir(咔唑:噁二唑=3:7(M/M))具有最好电致发光性能，通过构建结构为ITO/PEDOT/PFCz3OXD7Ir/LiF/Al的发光器件，其器件最大电流效率达到0.59cd/A，启动电压为6.0V,最大亮度为917cd/m2。
5.为了研究红色磷光配合物引入方式、电子供体咔唑功能基和电子受体噁二唑功能基对材料性能的影响，我们设计合成三种聚芴类电致磷光材料。通过构建结构为ITO/PEDOT/polymers/LiF/Al的发光器件，聚合物P1(红色磷光配合物挂接于芴的9位碳原子，侧链挂接空穴传输咔唑功能基和电子传输噁二唑功能基)具有最好性能，其器件最大电流效率达到0.72cd/A，最大亮度为1398cd/m~2，其电流效率和亮度为聚合物P2(磷光配合物挂接于聚合物端基，侧链挂接电子供体咔唑功能基和电子受体噁二唑功能基)性能的1.3和1.5倍。
A big global issue today is the upcoming depletion of fossil fuels and the energycrisis. Therefore, the challenges of21st century are to develop innovative materialsthat would provide new sources of clean sustainable energy and to develop newtechniques that can lead to efficient utilization of energy. Organic solar cells (OSCs)are a promising alternative to the fossil fuels for producing clean and renewableenergy from the sunlight and organic light-emitting diodes (OLEDs) have attracted agreat deal of attention because of their potential applications in energy-saving.This dissertation is focusing on the design and synthesis of new organicphotovoltaic materials and electroluminescent materials. The relationship between thestructure and the photoelectric properties were also studied. The results are as follows:
1. A novel conjugated polymer of PBDT-TDPP-S was synthesized, which contains adonor unit of benzo[1,2-b:4,5-b']dithiophene in main chain and an acceptor unitof diketopyrrolopyrrole in side chain. This kind of side-chain donor-acceptor(D-A) polymer exhibited better solution processability, lower HOMO level(5.34eV) and more balanced carrier mobility relative to its correspondingmain-chain D-A conjugated polymers. With a configuration of ITO/PEDOT:PSS/PBDT-TDPP-S:PC71BM/LiF/Al. A power conversion efficiency (PCE) of4.89%,an open-circuit voltage (Voc) of0.84V, a short-circuit current (Jsc) of10.04mAcm~(-2)and a fill factor (FF) of56.0%was achieved. Importantly, the FF is thehighest reported to date for side-chain D-A conjugated copolymers.
2. A new donor-acceptor-donor ternary copolymer PTh-BDT-2DTDPP wassynthesized, in which two diketopyrrolopyrrole units were simultaneouslyincorporated into the side and main chains. The PTh-BDT-2DTDPP exhibited abroad absorption spectrum from300nm to850nm.With a configuration of ITO/PEDOT:PSS/PTh-BDT-2DTDPP:PC61BM/LiF/Al. A maximum PCE of4.36%with a high Vocof0.78V, a Jscof10.47mA cm~(-2)and FF of53.0%was achieved.
3. Two donor/acceptor(D/A)-based benzo[1,2-b:4,5-b′]dithiophene-alt-2,3-biphenylquinoxaline copolymers were synthesized pending different functional groups(thiophene or triphenylamine) in the4-positions of phenyl rings. The poly(4,8-bis((2-ethyl-hexyl)oxy)benzo[1,2-b:4,5-b]dithiophene)-alt-(2,3-bis(4-bis(N,N-bis(4-(octyloxy)phenylamino)-1,1-biphen-4-yl)quinoxaline)(P2) exhibited betterphotovoltaic performance than poly(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5- b]dithiophene)-alt-(2,3-bis(4-(5-octylthiophen-2-yl) phenyl)quinoxaline)(P1) inthe bulk-heterojunction polymer solar cells with a configuration of ITO/PEDOT:PSS/polymers:[6,6]-phenyl-C71-butyric acid methyl ester (PC71BM)/LiF/Al. A PCE of3.43%, a Vocof0.80V and a Jscof9.20mA cm~(-2)were achievedin the P2-based cell. Importantly, this PCE level is2.29times higher than that inthe P1-based cell.
4. A series of donor(D)-acceptor(A)-based polyfluorene derivatives, which containcarrier-transporting units of carbazole and oxadiazole as the substitutes of the C-9position of fluorene and are end-capped with the red-emitting iridium bi(phenyl-isoquilonato)(picolinato) unit by unconjugated linkage, were synthesized andcharacterized. The molar ratios between the donor of carbazole and the acceptorof oxadiazole moieties were found to significantly influence photoluminescentefficiency, electrochemical and electroluminescent properties of these D-A-basedpolyfluorene derivatives. While the ratio increased to3:7, the PFCz3OXD7Irshowed the best device performance in the polymer light-emitting device with aconfiguration of ITO/PEDOT/polymers/LiF/Al. A turn-on voltage of6.0V, amaximum current efficiency of0.59cd/A and the highest luminance of917cd/m2were presented.
5. To study influence of the donor(D)-acceptor(A) units and pendent mode ofphosphorescent moiety on the opto-electronic properties for its resultingcopolymers, two D-A-based polyfluorene derivatives (P1and P2) pending thered-emitting iridium bi(phenylisoquilonato)(picolinato)[Ir(Piq)2(pic)] unit and apolyfluorene derivative (P3) only pending Ir(Piq)2(pic) unit were synthesizedand characterized, in which the donor of carbazole, the acceptor of oxadiazole aregrafted into the C-9position of fluorene, the Ir(Piq)2(pic) unit is pended intoeither the C-9position or the end of fluorene by unconjugated linkage,respectively. With a configuration of ITO/PEDOT/polymers/LiF/Al, the P1showed best electroluminescent properties. The maximum current efficiency of0.72cd/A and the highest luminance of1398cd/m2were obtained in theP1-based device, which are1.3and1.5times higher than those in the P2-baseddevice, respectively.
本论文的出发点是：设计合成新型的有机太阳能供体材料和有机电致发光材料，系统研究材料分子结构与器件性能关系。研究内容主要包括：
1.设计合成一种侧链挂接吡咯并吡咯二酮受体的侧链供体-受体(D-A)聚合物光伏材料(PBDT-TDPP-S)。聚合物PBDT-TDPP-S具有良好溶解性和较低的HOMO能级(5.34eV)，同时，聚合物PBDT-TDPP-S具有较高和平衡的载流子迁移率。通过构建结构为ITO/PEDOT:PSS/PBDT-TDPP-S:PC71BM/LiF/Al的光伏器件，器件最大能量效率达到4.89%，其中，开路电压为0.84V,短路电流为10.04mA cm~(-2),更重要的是，器件填充因子达56%，是目前文献报道的侧链D-A型聚合物光伏材料最高值。
2.设计合成一种侧链主链同时连接吡咯并吡咯二酮受体的三元共聚物光伏材料(PTh-BDT-2DTDPP)。聚合物PTh-BDT-2DTDPP具有宽光谱响应(300-850nm)，通过构建结构为ITO/PEDOT:PSS/PTh-BDT-2DTDPP:PC61BM/LiF/Al的光伏器件，器件最大能量效率达到4.36%，其中，开路电压为0.78V,短路电流为10.47mAcm~(-2),填充因子达53%。
3.设计合成两种侧链挂接三苯胺或噻吩功能基的苯并二噻吩-苯并吡嗪共聚物光伏材料。侧链挂接三苯胺功能基聚合物(P2)展现出更好光伏性能。通过构建结构为ITO/PEDOT:PSS/Polymer:PC71BM/LiF/Al的光伏器件，基于P2:PC71BM光伏器件的最大能量效率达到3.43%，其中开路电压为0.80V,短路电流为9.20mAcm~(-2)，器件的能量效率为噻吩功能基修饰聚合物(P1)的2.29倍。
4.设计合成一系列侧链挂接空穴传输咔唑功能基、电子传输噁二唑功能基和端基挂接苯基异喹啉铱红光配合物的聚芴类电致磷光材料。系统研究空穴传输功能基和电子传输功能基对材料的影响。聚合物PFCz3OXD7Ir(咔唑:噁二唑=3:7(M/M))具有最好电致发光性能，通过构建结构为ITO/PEDOT/PFCz3OXD7Ir/LiF/Al的发光器件，其器件最大电流效率达到0.59cd/A，启动电压为6.0V,最大亮度为917cd/m2。
5.为了研究红色磷光配合物引入方式、电子供体咔唑功能基和电子受体噁二唑功能基对材料性能的影响，我们设计合成三种聚芴类电致磷光材料。通过构建结构为ITO/PEDOT/polymers/LiF/Al的发光器件，聚合物P1(红色磷光配合物挂接于芴的9位碳原子，侧链挂接空穴传输咔唑功能基和电子传输噁二唑功能基)具有最好性能，其器件最大电流效率达到0.72cd/A，最大亮度为1398cd/m~2，其电流效率和亮度为聚合物P2(磷光配合物挂接于聚合物端基，侧链挂接电子供体咔唑功能基和电子受体噁二唑功能基)性能的1.3和1.5倍。
A big global issue today is the upcoming depletion of fossil fuels and the energycrisis. Therefore, the challenges of21st century are to develop innovative materialsthat would provide new sources of clean sustainable energy and to develop newtechniques that can lead to efficient utilization of energy. Organic solar cells (OSCs)are a promising alternative to the fossil fuels for producing clean and renewableenergy from the sunlight and organic light-emitting diodes (OLEDs) have attracted agreat deal of attention because of their potential applications in energy-saving.This dissertation is focusing on the design and synthesis of new organicphotovoltaic materials and electroluminescent materials. The relationship between thestructure and the photoelectric properties were also studied. The results are as follows:
1. A novel conjugated polymer of PBDT-TDPP-S was synthesized, which contains adonor unit of benzo[1,2-b:4,5-b']dithiophene in main chain and an acceptor unitof diketopyrrolopyrrole in side chain. This kind of side-chain donor-acceptor(D-A) polymer exhibited better solution processability, lower HOMO level(5.34eV) and more balanced carrier mobility relative to its correspondingmain-chain D-A conjugated polymers. With a configuration of ITO/PEDOT:PSS/PBDT-TDPP-S:PC71BM/LiF/Al. A power conversion efficiency (PCE) of4.89%,an open-circuit voltage (Voc) of0.84V, a short-circuit current (Jsc) of10.04mAcm~(-2)and a fill factor (FF) of56.0%was achieved. Importantly, the FF is thehighest reported to date for side-chain D-A conjugated copolymers.
2. A new donor-acceptor-donor ternary copolymer PTh-BDT-2DTDPP wassynthesized, in which two diketopyrrolopyrrole units were simultaneouslyincorporated into the side and main chains. The PTh-BDT-2DTDPP exhibited abroad absorption spectrum from300nm to850nm.With a configuration of ITO/PEDOT:PSS/PTh-BDT-2DTDPP:PC61BM/LiF/Al. A maximum PCE of4.36%with a high Vocof0.78V, a Jscof10.47mA cm~(-2)and FF of53.0%was achieved.
3. Two donor/acceptor(D/A)-based benzo[1,2-b:4,5-b′]dithiophene-alt-2,3-biphenylquinoxaline copolymers were synthesized pending different functional groups(thiophene or triphenylamine) in the4-positions of phenyl rings. The poly(4,8-bis((2-ethyl-hexyl)oxy)benzo[1,2-b:4,5-b]dithiophene)-alt-(2,3-bis(4-bis(N,N-bis(4-(octyloxy)phenylamino)-1,1-biphen-4-yl)quinoxaline)(P2) exhibited betterphotovoltaic performance than poly(4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5- b]dithiophene)-alt-(2,3-bis(4-(5-octylthiophen-2-yl) phenyl)quinoxaline)(P1) inthe bulk-heterojunction polymer solar cells with a configuration of ITO/PEDOT:PSS/polymers:[6,6]-phenyl-C71-butyric acid methyl ester (PC71BM)/LiF/Al. A PCE of3.43%, a Vocof0.80V and a Jscof9.20mA cm~(-2)were achievedin the P2-based cell. Importantly, this PCE level is2.29times higher than that inthe P1-based cell.
4. A series of donor(D)-acceptor(A)-based polyfluorene derivatives, which containcarrier-transporting units of carbazole and oxadiazole as the substitutes of the C-9position of fluorene and are end-capped with the red-emitting iridium bi(phenyl-isoquilonato)(picolinato) unit by unconjugated linkage, were synthesized andcharacterized. The molar ratios between the donor of carbazole and the acceptorof oxadiazole moieties were found to significantly influence photoluminescentefficiency, electrochemical and electroluminescent properties of these D-A-basedpolyfluorene derivatives. While the ratio increased to3:7, the PFCz3OXD7Irshowed the best device performance in the polymer light-emitting device with aconfiguration of ITO/PEDOT/polymers/LiF/Al. A turn-on voltage of6.0V, amaximum current efficiency of0.59cd/A and the highest luminance of917cd/m2were presented.
5. To study influence of the donor(D)-acceptor(A) units and pendent mode ofphosphorescent moiety on the opto-electronic properties for its resultingcopolymers, two D-A-based polyfluorene derivatives (P1and P2) pending thered-emitting iridium bi(phenylisoquilonato)(picolinato)[Ir(Piq)2(pic)] unit and apolyfluorene derivative (P3) only pending Ir(Piq)2(pic) unit were synthesizedand characterized, in which the donor of carbazole, the acceptor of oxadiazole aregrafted into the C-9position of fluorene, the Ir(Piq)2(pic) unit is pended intoeither the C-9position or the end of fluorene by unconjugated linkage,respectively. With a configuration of ITO/PEDOT/polymers/LiF/Al, the P1showed best electroluminescent properties. The maximum current efficiency of0.72cd/A and the highest luminance of1398cd/m2were obtained in theP1-based device, which are1.3and1.5times higher than those in the P2-baseddevice, respectively.
引文
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