含胺基聚芴类共轭高分子PFN及其衍生物作为发光二极管电子注入层的研究进展
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摘要
共轭聚合物[9,9-二辛基芴-9,9-双(N,N-二甲基胺丙基)芴](PFN)及其电解质衍生物具有与高功函数金属形成有效电子注入的能力,可以用作电子注入层与高功函数金属(如Al、Au等)组成复合阴极,应用在聚合物发光二极管(PLED)中。这类含新型复合阴极的PLED器件具有与目前广泛应用的低功函数金属(如Ba、Ca等)器件相同甚至更高的发光效率。该类电子注入型共轭聚合物及其前驱体只溶解于水、醇等极性溶剂中,而不溶于发光聚合物所易溶的非极性溶剂如甲苯、二甲苯或导电胶所含溶剂,这种特殊的性质可以保证电子注入层与发光层、电子注入层与导电胶层之间在印刷时不会发生互溶而被侵蚀的现象,使得利用高功函数金属的导电胶通过涂覆方式制备PLED的阴极并实现全印刷制造发光器件成为可能。目前,此类高分子材料合成及器件化已成为有机电子学研究的热点之一。本研究论述了国内外在以实现全印刷PLED为目标,以PFN及其衍生物作为电子注入材料方面的研究进展。
Ammonium - functionalized neutral polyfluorenes and their polyeletrolytes(PFN and their derivatives) show excellent electron injection capability.They can be utilized as electron injection layers in combination with the high work-function metals cathode Au or Al.It was found that devices with the PFN and their derivatives as electron injection materials and high work - function metals cathode Au or Al as cathode showed better performances in comparison with those using low work -function metals(Ba or Ca) cathode.The solubility of ammonium - functionalized polyfluorenes in polar solvents such as water or alcohol,rather than the non - polar solvents such as toluene and xylene,could guarantee the development of "All -Printed" organic electronics with silver paste.Currently,the synthesis and device fabrication based on the PFN and their derivatives have attracted much attention in the academic and industrial field.In this paper,the research progress of PFN and their derivatives used as electron injection materials in the application of PLEDs on domestic and foreign was described.
Ammonium - functionalized neutral polyfluorenes and their polyeletrolytes(PFN and their derivatives) show excellent electron injection capability.They can be utilized as electron injection layers in combination with the high work-function metals cathode Au or Al.It was found that devices with the PFN and their derivatives as electron injection materials and high work - function metals cathode Au or Al as cathode showed better performances in comparison with those using low work -function metals(Ba or Ca) cathode.The solubility of ammonium - functionalized polyfluorenes in polar solvents such as water or alcohol,rather than the non - polar solvents such as toluene and xylene,could guarantee the development of "All -Printed" organic electronics with silver paste.Currently,the synthesis and device fabrication based on the PFN and their derivatives have attracted much attention in the academic and industrial field.In this paper,the research progress of PFN and their derivatives used as electron injection materials in the application of PLEDs on domestic and foreign was described.
引文
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[29]LIN C Y,GARCIA A,NGUYEN T Q,et al.Effect of Thermal Annealing on Polymer Light - Emitting Diodes Utilizing Cationic Conjugated Polyelectrolytes as Electron Injection Layers[J].Journal of Physical Chemistry C, 2010,114(37):15786-15790.
[30]GARCIA A,BRZEZINSKI J Z,NGUYEN T Q.Cationic Conjugated Polyelectrolyte Electron Injection Layers: Effect of Halide Counterions[J].Journal of Physical Chemistry C,2009,113(7):2950 -2954.
[31]SEO J H,GUTACKER A,BAZAN G C,et al.Improved Injection in n - Type Organic Transistors with Conjugated Polyelectrolytes[J].Journal of the American Chemistry Society,2009,131(51):18220-18221.
[32]ZHANG L J,HE C,CHEN J W,et al.Bulk - Heterojunction Solar Cells with Benzotriazole - Based Copolymers as Electron Donors:Largely Improved Photovoltaic Parameters by Using PFN/Al Bilayer Cathode[J].Macromolecules, 2010,43(23):9771 -9778.
[33]HE Z C,WUHB,CAO Y,et al.Enhanced PowerConversion Efficiency in Polymer Solar Cells Using an Inverted Device Structure[J].Nature Photonics,2012,6 (9):591 -595.
[34]CAMPBELL,I H.et al.Controlling Schottky Energy Barriers in Organic Electronic Devices Using Self - assembled Monolayers[J].Physical Review B,1996,54 (20):14321 -14324.
[2]PETER H,RAGHU D.Printed and Thin Film Transistors and Memory 2009 - 2029[EB/OL].[2010 - 06 - 24]. http://www.IDTechEX.com.
[3]DEBOER D,HADIPOUR A,MANDOC M M,et al. Tuning of Metal Work Functions with Self - assembled Monolayers[J].Advanced Materials,2005,17(5):621 -625.
[4]EVANS S D,URANKAR E,ULMAN A,et al.Selfassembled Monolayers of Alkanethiols Containing a Polar Aromatic Group - effects of the Dipole Position on Molecular Packing,Orientation,and Surface Wetting Properties [J].Journal of the American Chemistry Society,1991, 113(11):4121 -4131.
[5]PARDO D A,JABBOUR G E,PEYGHAMBARIAN N. Application of Screen Printing in the Fabrication of Organic Light - emitting Devices[J].Advanced Materials, 2000,12(17):1249-1252.
[6]BIRNSTOCK J,BLASSDMG J,HUNZE A,et al.Screen - printed Passive Matrix Displays Based on Light - emitting Polymers[J].Applied Physics Letter,2001,78(24): 3905-3907.
[7]许伟.全印刷OLED显示屏技术崭露头角[N].中国电子,2008-05-20(11). XU Wei.All Printed OLED Display Screen Technology is Emerging[N].China Electronics News,2008 - 05 - 20 (11).
[8]HUANG F,CHENG Y J,ZHANG Y,et al.Crosslinkable Hole - Transporting Materials for Solution Processed Polymer Light - emitting Diodes[J].Journal of Material Chemistry,2008,18(38):4495 -4509.
[9]HUANG F,WU H B,CAO Y.Water/Alcohol Soluble Conjugated Polymers as Highly Efficient Electron Transporting/ Injection Layer in Optoelectronic Devices[J]. Chemical Society Reviews,2010,39(7):2500 -2521.
[10]ZENG W J,WU H B,ZHANG C,et al.Polymer Light - Emitting Diodes with Cathodes Printed from Conducting Ag Paste[J].Advanced Materials,2007,19(6):810 - 814.
[11]OHTANI J,MATSUMURA M,IKUTA K,et al.Organic Electroluminescent Element;Europe;EP056 300 9 B1 [P].1998-05-13
[12]HUNG L S,Tang C W,MASON M G.Enhanced Electron Injection in Organic Electroluminescence Device Using an Al/LiF Electrode[J].Applied Physics Lertters, 1997,70(2):152-154.
[13]YOON J,KIM J J,LEE T W,et al.Evidence of Band Bending Observed by Electroabsorption Studies in Polymer Light Emitting Device with Ionomer/Al or LiF / Al Cathode[J].Applied Physics Lertters,2000,76(16): 2152.
[14]ZHONG C M,DUAN C H,HUANG F,et al.Materials and Devices toward Fully Solution Processable Organic Light - Emitting Diodes[J].Chemistry of Materials, 2011,23(3);326-340.
[15]WU H B,HUANG F,MO Y Q,et al.Efficient Electron Injection from a Bilayer Cathode Consisting of Aluminum and Alcohol -/Water - Soluble Conjugated Polymers[J]. Advanced Materials,2004,16(20);1826-1830.
[16]WU H B,HUANG F,CAO Y,et al.High - Efficiency Electron Injection Cathode of Au for Polymer Light - emitting Devices[J].Organic Electronics,2005,6(3): 118-128.
[17]WU H B,HUANG F,CAO Y,et al.Efficient Electron Injection from Bilayer Cathode Consisting of Aluminum and Alcohol/Water - Soluble Conjugated Polymers[J]. Journal of the Society for Information Display,2005,13 (2):123-130.
[18]WU H B,HUANG F,CAO Y,et al.Efficient Electron Enjection from Bilayer Cathode with Aluminum as Cathode [J].Synthetical Metals,2005,153(1-3):197 - 200.
[19]HUANG F,WU H B,CAO Y,et al.Novel Electroluminescent Conjugated Polyelectrolytes Based on Polyfluorene [J].Chemistry of Materials,2004,16(4):708 -716.
[20]HUANG F,HOU L T,WU H B,et al.High - Efficiency, Environment -Friendly Electroluminescent Polymers with Stable High Work Function Metal as a Cathode:Green - and Yellow - Emitting Conjugated Polyfluorene Polyelectrolytes and Their Neutral Precursors[J].Journal of the American ??Chemistry Society,2004,126(31):9845 -9853.
[21]XIAO S,NGUYEN M,GONG X,et al.Stabilization of Semiconducting Polymers with Silsesquioxane[J].Advanced Functional Materials,2003,13(1):25 -29.
[22]SHEN H L,HUANG F,CAO Y,et al.Synthesis and Characterization of Polyfluorene Electrolytes as Green and Red Light - Emitting Layers for High - Efficiency PLEDs[J].Synthetical Metals,2005,153(1 -3):257 -260.
[23]ZHONG C M,LIU S J,HUANG F,et al.Highly Efficient Electron Injection from Indium Tin Oxide / Crosslinkable Amino - functionalized Polyfluorene Interface in Inverted Organic Light Emitting Devices[J].Chemistry of Materials,2011,23(21):4870 -4876.
[24]XUXF,HAN B,CHEN J W,et al.2,7 - Carbazole - 1,4 - phenylene Copolymers with Polar Side Chains for Cathode Modifications in Polymer Light - Emitting Diodes [J].Macromolecules,2011,44(11):4204 -4212.
[25]ZHANG Y.XUYH,CAO Y,et al.Synthesis and Optoelectronic Characterization of Conjugated Phosphorescent Polyelectrolytes with a Neutral Ir Complex Incorporated into the Polymer Backbone and Their Neutral Precursors [J].Journal of Material Chemistry,2007,17(10):992 - 1001.
[26]YANG R Q,WU H B,CAO Y,et al.Control of Cationic Conjugated Polymer Performance in Light Emitting Diodes by Choice of Counterion[J].Journal of the American Chemistry Society,2006,128(45):14422 - 14423.
[27]YANG R Q,GARCIA A,BAZAN G C,et al.Control of Interchain Contacts,Solid - state Fluorescence Quantum Yield,and Charge Transport of Cationic Conjugated Polyelectrolytes by Choice of Anion[J].Journal of the American Chemistry Society,2006,128(51):16532 - 16539.
[28]YANG R Q,XU Y H,BAZAN G C,et al.Conjugated Oligoelectrolyte Electron Transport/Injection Layers for Organic Optoelectronic Devices[J].Journal of the American Chemistry Society,2008,130(11 ):3282 - 3283.
[29]LIN C Y,GARCIA A,NGUYEN T Q,et al.Effect of Thermal Annealing on Polymer Light - Emitting Diodes Utilizing Cationic Conjugated Polyelectrolytes as Electron Injection Layers[J].Journal of Physical Chemistry C, 2010,114(37):15786-15790.
[30]GARCIA A,BRZEZINSKI J Z,NGUYEN T Q.Cationic Conjugated Polyelectrolyte Electron Injection Layers: Effect of Halide Counterions[J].Journal of Physical Chemistry C,2009,113(7):2950 -2954.
[31]SEO J H,GUTACKER A,BAZAN G C,et al.Improved Injection in n - Type Organic Transistors with Conjugated Polyelectrolytes[J].Journal of the American Chemistry Society,2009,131(51):18220-18221.
[32]ZHANG L J,HE C,CHEN J W,et al.Bulk - Heterojunction Solar Cells with Benzotriazole - Based Copolymers as Electron Donors:Largely Improved Photovoltaic Parameters by Using PFN/Al Bilayer Cathode[J].Macromolecules, 2010,43(23):9771 -9778.
[33]HE Z C,WUHB,CAO Y,et al.Enhanced PowerConversion Efficiency in Polymer Solar Cells Using an Inverted Device Structure[J].Nature Photonics,2012,6 (9):591 -595.
[34]CAMPBELL,I H.et al.Controlling Schottky Energy Barriers in Organic Electronic Devices Using Self - assembled Monolayers[J].Physical Review B,1996,54 (20):14321 -14324.