WO2007009331A1 - Procédé de fabrication de la cathode d’une diode émettrice de lumière organique/hautement moléculaire - Google Patents

Procédé de fabrication de la cathode d’une diode émettrice de lumière organique/hautement moléculaire Download PDF

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Publication number
WO2007009331A1
WO2007009331A1 PCT/CN2006/000978 CN2006000978W WO2007009331A1 WO 2007009331 A1 WO2007009331 A1 WO 2007009331A1 CN 2006000978 W CN2006000978 W CN 2006000978W WO 2007009331 A1 WO2007009331 A1 WO 2007009331A1
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Prior art keywords
cathode
emitting diode
light
polymer light
polymer
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PCT/CN2006/000978
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English (en)
Chinese (zh)
Inventor
Yong Cao
Wenjin Zeng
Fei Huang
Junbiao Peng
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South China Uni. Of Tech.
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Publication of WO2007009331A1 publication Critical patent/WO2007009331A1/fr

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/26—Light sources with substantially two-dimensional radiating surfaces characterised by the composition or arrangement of the conductive material used as an electrode
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys

Definitions

  • the invention relates to a photovoltaic device, in particular to a method for preparing a cathode of a polymer light-emitting diode, which is characterized in that the cathode is made of a metal conductive paste and is prepared by printing or the like.
  • the extinction molecular light-emitting diode has the advantages of material cost, low driving voltage, active illumination 'wide viewing angle, low energy consumption, etc. It is easy to form large-area molding, and the emission wavelength can be adjusted through molecular structure design, and can be widely applied. High resolution full color flat panel display can also be applied to polymer solar cells.
  • the existing polymer light-emitting diodes are mainly composed of a substrate, an anode, a polymer light-emitting layer and a cathode. Specifically, as shown in FIGS.
  • the existing polymer light-emitting diodes mainly consist of a substrate 1, an anode 2, a ruthenium molecular light-emitting layer 3 and a cathode 4 or a ceramic substrate 1, an anode 2, and a hole.
  • the transport layer 5, the ruthenium molecular light-emitting layer 3, the electron transport layer 6, and the cathode 4 are formed by laminating a metal substrate 1, an anode 2, a hole transport layer 5, a polymer light-emitting layer 3, a cathode 4, and the like in this order.
  • the anode of the polymer light-emitting diode is usually made of indium tin oxide (ITO) and is overlaid on the substrate by vacuum sputtering.
  • the polymer light-emitting layer is usually prepared by a method such as spin coating or printing.
  • the cathode is generally vapor-deposited on the surface of the polymer light-emitting layer by vacuum evaporation.
  • a hole transport layer 5 is interposed between the anode 2 and the light-emitting layer 3
  • an electron transport layer 6 is interposed between the light-emitting layer 3 and the cathode 4. Since the high liver light-emitting device is a multi-layered structure, the interface between the layers is very important.
  • the object of the present invention is to provide a method for preparing a cathode having a polymer light-emitting diode instead of a complicated process in the prior art, instead of a complicated process such as sputtering or vacuum evaporation.
  • the method for preparing a cathode of a polymer light-emitting diode according to the present invention is characterized in that a cathode of an in/polymer light-emitting diode is formed by a conductive paste of a high work function metal, and the conductive paste is made of a high work function metal powder. It is mixed with polymer adhesive.
  • the t) V polymer light-emitting diode is mainly composed of a substrate, an anode, a polymer light-emitting layer, and a cathode.
  • the coating method may be spin coating, screen printing, coating, printing or ink jet printing or the like.
  • the high work function metal is a high work function metal having a work function greater than or equal to 4.0 electron volts.
  • the high work function metal may be selected from gold, aluminum, copper, silver, indium, nickel, lead, tin or alloys thereof.
  • the substrate having the polymer light emitting diode is a hard substrate or a flexible substrate.
  • the hard substrate such as glass, ceramic, metal, or the like; the flexible substrate such as a polymer material such as polyethylene terephthalate, plexiglass, or the like.
  • the present invention can use a commercially available high-work function metal conductive paste as a cathode material having a #1/polymer light-emitting diode, and a cathode of a polymer light-emitting diode is formed by using a conventional coating method, and a polymer light-emitting diode is obtained.
  • the entire process of preparing the jl/ ⁇ molecular light-emitting diode more specifically includes the following steps: coating a hole injection/transport layer on the cleaned substrate a polymer light-emitting layer and an electron-injecting conjugated polymer such as poly[9,9-dioctylfluorene-9,9-(bis(3'-(N, N-dimethyl)-N-ethyl) Ammonium) propyl) hydrazine] dibromo PFBrNR 2, etc., its chemical structural formula is as follows:
  • a highly efficient luminescent polymer with electron injection from a high work function metal such as PFN-BTOZ (poly[9,9-dioctyl ⁇ - 9,9- (double (3'-(N, N-dimethyl) Base) an N-ethylammonium)propyl)pyrene-2,1,3-benzothiadiazole]dibromo) or PFN-DBT (poly[9,9-dioctylfluorene-9, 9-pair ( When N, N-dimethylaminopropyl) indole-4,.7-dithiophen-2-yl- 2,1-3-benzothiadiazole]), etc., it is not necessary to add a separate electron injecting layer.
  • a high work function metal such as PFN-BTOZ (poly[9,9-dioctyl ⁇ - 9,9- (double (3'-(N, N-dimethyl) Base) an N-ethyl
  • any simple printing film forming process such as spin coating, coating, screen printing or ink jet printing is selected thereon to form a uniform high work on the polymer film.
  • the conductive film of the function metal can form an electrode after the glue layer is solidified, and the whole production environment is the same as that of the polymer film, and is carried out in a nitrogen glove box, thereby eliminating the vacuum in the evaporation or sputtering process. The tedious steps of waiting.
  • A is a polar component containing a polar group or an ionic group, and has a combination of one or more of the following structures:
  • B is a component which does not contain a polar or ionic group, and has one or more of the following structures: — 0.5;
  • B also includes polyparaphenylene acetylene, polyspirophenylene, polyparaphenylene acetylene, polycarbazole, and the like;
  • One of the features of the present invention is to use a conductive paste of a high work function metal as an electrode or as a conductive bonding material.
  • the invention can realize the preparation of the cathode of the organic light-emitting diode device by the coating method of the commercially available high-function-function metal conductive paste, thereby realizing the all-printing light-emitting device based on the electron-injecting conjugated polymer and its precursor used. It has the ability to form an effective electron injection composite cathode with a high work function metal; such electron injecting conjugated polymers and their precursors are only soluble in polar solvents such as water and alcohol, and are insoluble in luminescent polymers and conductive pastes.
  • the metal powders such as silver, gold and copper are successfully used as the conductive medium and the metal is injected into the metal cathode, and the polymer adhesive which is not mutually soluble with the polymer film is selected, and is cured at room temperature or under low temperature heat curing conditions.
  • a cathode of an organic/antimony molecular light-emitting diode having a good interfacial bonding with a polymer film layer and having excellent electrical conductivity is prepared.
  • the invention has the following advantages:
  • the preparation process is simple and the production cost is low.
  • cathode fabrication of organic light-emitting diodes must be carried out under high vacuum, subject to a complicated process of vacuuming, vapor deposition or sputtering.
  • a cathode suitable for preparing a flexible display Since the cathode of a conventional organic light emitting diode is a metal thin film, it may cause device failure due to cathode peeling when it is greatly bent.
  • a conductive paste is used as a cathode material, and the substrate is a high-molecular adhesive. After solidification, it has considerable bond strength and toughness, and can be firmly bonded in a large degree of bending, so that it is suitable for the cathode of a flexible display.
  • FIG. 1 is a schematic structural view of a conventional ft/polymer light emitting diode
  • FIG. 2 is another schematic structural view of a conventional OLED/polymer light emitting diode
  • FIG. 3 is a schematic view showing another structure of a conventional polymer light-emitting diode
  • PFOBtl5 as a light-emitting layer
  • PFNR 2 as an electron transport layer
  • silver conductive paste as a cathode
  • Figure 5 is a green light-based material [9,9-dioctyl fluorene-2,1,3-benzothiadiazole] PFOBtl5 as a light-emitting layer, PFNR 2 as an electron transport layer, coated with silver conductive paste as a cathode An external quantum efficiency-current density curve of a V polymer light emitting diode;
  • Figure 6 is a red light-based material [9,9-dioctylfluorene-4,7-dithiophene-2,1,3-benzothiadiazole] PFODBT15 as a light-emitting layer, PFNR 2 as an electron transport layer, coated A current-tight luminance-voltage curve of a polymer light-emitting diode with a silver-coated conductive paste as a cathode;
  • Figure 7 is a red light-based material poly[9,9-dioctylfluorene-4,7-dithiophene-2,1,3-benzothiazepine]PFODBT15 as a light-emitting layer, PF 2 as an electron transport layer, coated An external quantum efficiency-current density curve of a polymer light-emitting diode with a silver-coated conductive paste as a cathode;
  • FIG. 9 is an external quantum efficiency-current density curve of a polymer light-emitting diode based on a blue light material poly[9,9-dioctyl ii]PFO as a light-emitting layer, PFNR 2 as an electron transport layer, and a silver conductive paste as a cathode.
  • Figure 10 is a green light-based material [9,9-dioctylfluorene-9,9-bis(dimethylaminopropyl)fluorene-2,1,3-benzothiadiazole-N- (4 —Phenyl) _4, 4, diphenylamine] PFNBT0.5TPA5 as the light-emitting layer, without the electron transport layer, directly coated with silver conductive paste as the cathode, the current density/luminescence brightness-voltage of the IV polymer light-emitting diode Graph.
  • Substrate porch size 15mm x l5mm, sheet resistance is about 20 ohms / ⁇ , in turn with acetone, ® * grade semiconductor special paint remover, deionized water, isopropyl alcohol sonication 10 clean anode substrate surface, Then, it was placed in a constant temperature oven at 80 Torr for 4 hours to dry.
  • the dried anode substrate is plasma bombarded with an oxygen plasma etching apparatus to remove the organic deposited film attached to the surface of the anode substrate, and the work function of the anode surface is increased, and then placed in a homogenizing machine (KW-4A type).
  • PEDOT: PSS 7 solution concentration about 1%, purchased from Bayer
  • the film thickness was measured by the concentration of the solution and the spin speed, and recorded by a surface profiler (Teriek Alpha-Tencor 500 type). After film formation, the anode substrate was transferred to a constant temperature vacuum oven for drying under 80 atmospheres to remove residual solvent and harden the film.
  • Polyvinylcarbazole PVK is also a conjugated polymer that acts as a hole transporting layer. Put the PVK solid in a clean vial, transfer it to a special glove box for nitrogen film formation (manufactured by American VAC Company), add chlorobenzene to a 1% solution, place it on a stirring table, stir it, and filter it with a 0.45 ⁇ m filter. The filtrate was clarified. According to the principle of work function matching, the PVK hole transport layer is selected depending on the selected polymer light-emitting polymer.
  • the polymer light-emitting polymer was placed in a clean vial, transferred to a special glove box for nitrogen film formation, dissolved in a solvent to prepare a solution, placed on a stirring table and stirred uniformly, and filtered through a 0.45 ⁇ m filter to obtain a clear filtrate.
  • the polymer PFNR 2 having a quaternary ammonium salt functional group in the side chain is an electron transporting material, and the preparation method thereof is described in Chinese Patent Application No. CN200310117518.5, which is placed in a clean vial and transferred to a special glove for protecting nitrogen vines.
  • 0.4% solution was dissolved in methanol with a small amount of acetic acid, placed on a stirring table and stirred uniformly, and filtered through a 0.45 ⁇ m filter to obtain a clear solution.
  • the film formation process of the above three polymers is carried out in a special glove box for anhydrous oxygen-free nitrogen protection film formation, which is prepared by high-speed spin coating of the anode substrate on the homogenizer, and the film thickness is adjusted by adjusting the rotation speed of the homogenizer.
  • the film thickness of the PVK hole transport layer is controlled at about 40 nm, and the optimum thickness of the polymer light-emitting layer is 70 to 90 nm, and the film thickness of the PF R 2 electron transport layer is about 1 nm, which is monitored by a surface profilometer.
  • the anode substrate after film formation is divided into two groups, one group is placed in a vacuum «machine using conventional vacuum evaporation method to vaporize the corresponding metal electrode (the plating chamber vacuum is 3 ⁇ 1 ( ⁇ 3 ⁇ 43 ⁇ 4 or less, ⁇ rate and each layer)
  • the thickness of the metal electrode film is monitored by a quartz vibrating film thickness monitor (SIM-IOO type, manufactured by Sycon Corporation) in real time.
  • the other group is uniformly coated with a layer of conductive adhesive on the polymer film. Heating at 60 ° C for 2 hours accelerated solidification. Both devices were measured using the same instrument for comparison.
  • the luminescence spectrum of the device was measured by a calibrated OREL company's Instaspec IV charge-coupled photodetector CCD; the luminescence intensity and external quantum efficiency of the device utilize a semi-conducting «quantity consisting of a Keit Mey 236 current-voltage source and a calibrated silicon photodiode The system measured; the external quantum efficiency and luminous intensity were calibrated with Labsphere IS080 integrating sphere and PR705 photometric spectrometer (Photoresearch), respectively.
  • the structure of the polymer/polymer light-emitting diode shown in Fig. 2 is based on the green light-emitting polymer poly[9,9-dioctylfluorene-2,1-3-benzothiadiazole] PFOBtl5 as the light-emitting layer. Polymer light emitting diode device.
  • the anode substrate which has been formed into a PEDOT film and the solvent is removed is transferred to a nitrogen glove box, adsorbed on a homogenizer, and the selected rpm is used to spin the coated PFOBtl5 solution onto the film to a thickness of about 80 nm.
  • Polymer luminescent layer are divided into three groups, B and C, in which A and B are matched with a good electron transfer material PFM 2, which is dropped on the polymer light-emitting layer, and the speed of the homogenizer is adjusted, and a thin layer is spin-coated.
  • the electron transport layer has a film thickness of about 1 nm.
  • a group A is selected from the two sets of anode substrates of the eight and B groups which have been spin-coated with the electron transport layer, and a layer of silver conductive paste is evenly coated on the polymer film, and heated for 60 hours to accelerate the curing.
  • a group of B was vapor-deposited by vacuum evaporation to form a cathode.
  • the third group C does not add an electron transport layer, and a cathode is formed by vapor-depositing a Ba/Al metal thin film on the polymer light-emitting layer by vacuum evaporation, and the two groups B and C are reference devices.
  • the polymer light-emitting devices of the three different cathode materials produced in the same batch described above were measured using the apparatus described above, and the obtained device performance parameters are listed in Table 1 and Figures 4 and 5 for comparison.
  • the structure shown in Fig. 2 is selected based on the red light-emitting polymer poly[9,9-dioctyl ⁇ _4,7-dithiophene-2,1,3-benzothiadiazole] PFODBT15 as the luminescent layer. There are; f / y polymer light-emitting diodes.
  • the PFODBT15 was placed in a clean vial, transferred to a nitrogen glove box, and toluene was added to a 1.5% solution. The mixture was placed on a stirring table and stirred, and filtered through a 0.45 ⁇ m filter to obtain a clear filtrate.
  • the anode substrate which has been formed into a PEDOT film and the solvent is removed is transferred to a nitrogen glove box, adsorbed on a homogenizer, and the rpm is selected, and the prepared PFODBT15 solution is dripped onto the film to a thickness of about 80 nm.
  • Polymer luminescent layer are divided into three groups A, B and C, in which the two groups A and B are dropped on the polymer light-emitting layer with the prepared electron transport material PFNR 2 to adjust the uniform ship speed and spin-coat a thin layer of electrons.
  • the transport layer has a film thickness of about 1 nm.
  • a group A is selected from the two sets of anode substrates of the eight and B groups which have been spin-coated with the electron transport layer, and a layer of silver conductive paste is evenly coated on the polymer film, and heated at 60 ° C for 2 hours to accelerate the curing.
  • the remaining group B was vacuum-deposited by vapor deposition of an Ag metal film to form a cathode.
  • the third group C does not add an electron transport layer, and a cathode is formed by vapor-depositing a Ba/Al metal thin film on the polymer light-emitting layer by vacuum evaporation, and the two groups B and C are reference devices.
  • the polymer light-emitting devices of the three different cathode materials prepared in the same batch described above were measured by the apparatus described above, and the obtained device performance parameters are shown in Table 2_ and Figures 6 and 7.
  • the structure shown in Fig. 2 is selected as a polymer light-emitting diode based on a blue light-emitting polymer poly [9' 9-dioctyl fluorene] PFO as a light-emitting layer.
  • the anode substrate which has been formed into a PEDOT film and solvent is transferred to a nitrogen glove box, adsorbed on a homogenizer, and selected to rotate a layer of a 40 nm polyvinylcarbazole PVK hole transport layer, and then The PFO solution of the scorpion was spin-coated thereon to form a polymer luminescent layer having a film thickness of about 80 nm.
  • These anode substrate numbers are divided into three groups of eight, B and C, in which the two groups of A and B are equipped with a good electron transfer material.
  • PFNR2 is dropped on the polymer light-emitting layer, and the speed of the homogenizer is adjusted, and the spin coating is thin.
  • the layer electron transport layer has a film thickness of about 1 nm.
  • a set of ruthenium is selected from two sets of anode substrates of ruthenium and iridium which have been spin-coated with an electron transport layer, and a layer of silver conductive paste is evenly coated on the polymer film, and accelerated at 60 ° C for 2 hours to accelerate curing.
  • the remaining group B was vacuum-deposited by vapor deposition of an Ag metal film to form a cathode.
  • the third group C does not add an electron transport layer, and a Ba/Al metal film is vapor-deposited on the polymer light-emitting layer by vacuum evaporation to form a cathode, and the B and C groups are reference devices.
  • the polymer light-emitting devices of the three different cathode materials produced in the same batch described above were measured using the apparatus described above, and the obtained device performance parameters are listed in Table 3 and Figures 8 and 9 for comparison.
  • the polymer light-emitting diode structure shown in FIG. 3 is selected based on the green light material [9, 9-dioctyl sulfonium-9,9-bis(dimethylaminopropyl) fluorene-2, 1, 3- Benzothiadiazole-N-(4-phenyl)-4,4,2-diphenylamine] PFNBT0.5TPA5
  • a V-polymer light-emitting diode device as a light-emitting layer, the substrate of which is made of plexiglass.
  • the anode substrate with PEDOT film and solvent removal is transferred to a nitrogen glove box, adsorbed on a homogenizer, and the selected rotation speed is used.
  • the prepared PVK solution is dripped onto the film and coated with a film thickness of about 40 nm. Hole transport layer, reuse
  • the PFNBT0.5TPA5 solution was spin-coated with a layer of polymer light-emitting layer on the PVK layer with a film thickness of about 80 nm.
  • anode substrate numbers are divided into three groups A, B and C, one of which is uniformly coated with a layer of silver conductive glue on the polymer film, and heated at 60 Torr for 2 hours to accelerate the curing; the remaining two groups B, C is vacuum-deposited by vapor deposition of Ag or Ba/Al metal thin films to form cathodes, and the two groups are reference devices.
  • the polymer light-emitting devices of the three different cathode materials produced in the same batch described above were measured using the apparatus described above, and the obtained device performance parameters are listed in Table 4 and Figure 10 for comparison.
  • the polymer light-emitting diode can also be prepared by using the green light-emitting material PFNBT0.5TPA5 with electron transport property and the Ag conductive paste as the cathode material.
  • the poly [2-methoxy-5-(2-ethylhexyloxy)-1,4-styrene-supported] MEH-PPV, green photopolymer polyphenyl-substituted styrene is used.
  • P-PPV and blue polymer poly [9, 9-bis-octyl] ⁇ PFO, other high-work function stable metal as the cathode, PFm 2 as the electron transport layer prepared by the polymer light-emitting diode device performance parameters are listed in Table 5;
  • silver can be directly injected from the silver to the light-emitting layer because it is combined with a polyelectrolyte having a positive (or negative) ionic group or a neutral precursor of a cationic polyelectrolyte. electronic.
  • other high-power function metals also have good effects (see Table 5).
  • These high-work-function metal conductive pastes can also be formed into a cathode by printing, but are not limited thereto.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Procédé de fabrication de la cathode d'une diode émettrice de lumière organique/hautement moléculaire, consistant au revêtement d’une pâte conductrice mélangeant des particules métalliques fonctionnelles haute performance et un agent adhésif hautement moléculaire sur la couche émettrice de lumière par filage, sérigraphie, impression à jet d'encre, etc. Ce procédé permet de remplacer la cathode de placage par évaporation à vide traditionnelle. Elle permet de fabriquer un écran d’affichage émetteur de lumière hautement moléculaire par impression entière. Cela permet de simplifier le processus et d’en abaisser le coût.
PCT/CN2006/000978 2005-07-15 2006-05-15 Procédé de fabrication de la cathode d’une diode émettrice de lumière organique/hautement moléculaire WO2007009331A1 (fr)

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CN 200510035789 CN1719637A (zh) 2005-07-15 2005-07-15 有机/高分子发光二极管的阴极的制备方法
CN200510035789.5 2005-07-15

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US8866134B2 (en) 2010-06-29 2014-10-21 Sumitomo Chemical Company, Limited Light-emitting device and photovoltaic cell, and method for manufacturing the same

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CN101916831B (zh) * 2010-06-30 2012-06-27 华南理工大学 一种全印刷方法制备有机电致发光显示屏的方法
CN102956828A (zh) * 2011-08-31 2013-03-06 李果华 一种免焊接的有机太阳电池组件连接新方法
CN102956829A (zh) * 2011-08-31 2013-03-06 李果华 一种制备有机太阳电池阴极的简便新方法
CN103094489A (zh) * 2012-11-30 2013-05-08 江苏威纳德照明科技有限公司 一种包括电子传输层的高分子发光二极管
CN103094485A (zh) * 2012-11-30 2013-05-08 江苏威纳德照明科技有限公司 一种高分子发光二极管
CN103606629A (zh) * 2013-10-26 2014-02-26 溧阳市东大技术转移中心有限公司 一种包括电子传输层的聚合物发光二极管
CN103606631A (zh) * 2013-10-26 2014-02-26 溧阳市东大技术转移中心有限公司 一种具有空穴传输层的聚合物发光二极管
CN105336854B (zh) * 2015-09-29 2018-05-18 北京交通大学 一种基于全湿法银对称电极聚合物电双稳器件
CN105428546A (zh) 2016-01-20 2016-03-23 京东方科技集团股份有限公司 一种qled及其制备方法、显示装置及其制备方法
CN106981588A (zh) * 2017-05-02 2017-07-25 深圳市华星光电技术有限公司 一种有机发光器件及其制造方法
CN109233440A (zh) * 2017-05-03 2019-01-18 上海幂方电子科技有限公司 一种用于溶液法制备有机半导体器件的缓冲层墨水
CN111244307B (zh) * 2018-11-29 2021-10-22 Tcl科技集团股份有限公司 一种量子点发光二极管及其制备方法
CN114843373A (zh) * 2022-01-27 2022-08-02 江苏日托光伏科技股份有限公司 一种htj电池的制备方法

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