CN103606629A - Polymer light emitting diode including electron transport layer - Google Patents
Polymer light emitting diode including electron transport layer Download PDFInfo
- Publication number
- CN103606629A CN103606629A CN201310514056.4A CN201310514056A CN103606629A CN 103606629 A CN103606629 A CN 103606629A CN 201310514056 A CN201310514056 A CN 201310514056A CN 103606629 A CN103606629 A CN 103606629A
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- China
- Prior art keywords
- light emitting
- emitting diode
- polymer light
- polymer
- transport layer
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- 229920000642 polymer Polymers 0.000 title claims abstract description 56
- 239000000758 substrate Substances 0.000 claims abstract description 29
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims abstract description 10
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 9
- 230000005525 hole transport Effects 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
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- 229930192474 thiophene Natural products 0.000 claims description 13
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims description 11
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- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 239000010409 thin film Substances 0.000 claims description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 abstract description 22
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- XALSGPBBPQILAT-UHFFFAOYSA-N BrC1=C(C(=C(C2=C1N=NS2)Br)F)F Chemical compound BrC1=C(C(=C(C2=C1N=NS2)Br)F)F XALSGPBBPQILAT-UHFFFAOYSA-N 0.000 description 5
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- LUNNIRSRBUJDLV-UHFFFAOYSA-N CCCCCCCCCCCCC(CCCCCCCCCC)CC1=C(Br)SC(=C1)C1=C(F)C(F)=C(C2=CC(CC(CCCCCCCCCC)CCCCCCCCCCCC)=C(Br)S2)C2=C1SN=N2 Chemical compound CCCCCCCCCCCCC(CCCCCCCCCC)CC1=C(Br)SC(=C1)C1=C(F)C(F)=C(C2=CC(CC(CCCCCCCCCC)CCCCCCCCCCCC)=C(Br)S2)C2=C1SN=N2 LUNNIRSRBUJDLV-UHFFFAOYSA-N 0.000 description 3
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- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
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- ZZSABJUFMDPIBR-UHFFFAOYSA-N 5,6-difluoro-1,2,3-benzothiadiazole Chemical compound C1=C(F)C(F)=CC2=C1SN=N2 ZZSABJUFMDPIBR-UHFFFAOYSA-N 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- UIPXRWUFGRCZCN-UHFFFAOYSA-N 1,4-dibromo-2,3-difluoro-5,6-dinitrobenzene Chemical compound [O-][N+](=O)C1=C(Br)C(F)=C(F)C(Br)=C1[N+]([O-])=O UIPXRWUFGRCZCN-UHFFFAOYSA-N 0.000 description 1
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
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- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1483—Heterocyclic containing nitrogen and sulfur as heteroatoms
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- Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The invention discloses a polymer light emitting diode including an electron transport layer. The polymer light emitting diode sequentially comprises a substrate, an anode, a hole transport layer, a polymer light emitting layer, an electron transport layer and a cathode, wherein the material of the polymer light emitting layer is a conjugated polymer, with a general formula (I) structure, of benzothiadiazole. By adopting the polymer light emitting layer as an efficient light-emitting polymer, the polymer light emitting diode has high energy conversion efficiency and high carrier mobility.
Description
Technical Field
The invention relates to a photoelectric device, in particular to a light emitting diode.
Background
The polymer light-emitting diode has the characteristics of low material cost, low driving voltage, active light emission, wide viewing angle, low energy consumption and the like, has the advantages of easiness in large-area molding, capability of adjusting the light-emitting wavelength through molecular structure design and the like, can be widely applied to high-resolution full-color flat displays, and can also be applied to polymer solar cells.
When a forward bias is applied across the polymer light emitting diode, holes are injected from the anode into the valence band of the polymer light emitting layer and migrate toward the cathode, and electrons are injected from the cathode into the conduction band of the polymer light emitting layer and migrate toward the anode. The holes and electrons are mutually captured in the migration process and are compounded into excitons, the electrons in the exciton state undergo radiation transition, and energy is released in a photon form, so that electroluminescence is realized. However, the light emitting diode in the prior art still has some defects, the preparation process of the flexible light emitting diode is complex, the cost is high, and the light emitting performance of the prepared light emitting diode cannot meet the requirement, so that the research and development of an organic/polymer light emitting diode with better performance are hopeful, the efficiency is high, the preparation process is simple, and the cost is low.
Disclosure of Invention
The polymer light-emitting diode of the invention comprises a substrate, an anode, a hole transport layer, a polymer light-emitting layer, an electron transport layer and a cathode in sequence, wherein,
the material of the polymer light-emitting layer is a conjugated polymer of benzothiadiazole with a structure of general formula (I),
wherein R is1Is hydrogen or C1～C36Alkyl groups of (a); r2Is hydrogen or C1～C36Alkyl groups of (a); ar is one of thiophene, alkyl substituted thiophene, alkoxy substituted thiophene, bithiophene, alkyl substituted bithiophene and alkoxy substituted bithiophene; n =3 ~ 1000.
The preparation method of the conjugated polymer of the benzothiadiazole is to copolymerize a monomer of the benzothiadiazole with a thiophene monomer or an oligothiophene monomer.
Further preferably, the preparation method of the conjugated polymer of benzothiadiazole is to copolymerize the 5, 6-difluoro-benzothiadiazole monomer with the bitrithiophene monomer or the bitetrathiophene monomer, or to copolymerize the 4, 7-bithiophene-5, 6-difluoro-benzothiadiazole monomer with the thiophene monomer or the bithiophene monomer.
Compared with the prior art, the invention has the following advantages and effects: the conjugated polymer of the diazosulfide is used for manufacturing a light-emitting layer of a polymer light-emitting diode, so that the light-emitting diode has high energy conversion efficiency and high carrier mobility.
Drawings
Fig. 1 is a schematic structural diagram of a light emitting diode according to the present invention.
Detailed Description
In order to make the technical solution of the present invention more clearly understood by those skilled in the art, the following description of the specific embodiments is made with reference to the accompanying drawings.
As shown in fig. 1, the light emitting diode of the present invention includes a substrate 1, an anode 2, a hole transport layer 5, a polymer light emitting layer 3, an electron transport layer 6, and a cathode 4 in this order. Wherein,
the substrate 1 may be a hard substrate or a flexible substrate. The hard substrate is preferably glass, ceramic, metal, or the like; the flexible substrate is preferably a polymeric material such as polyethylene terephthalate, plexiglass, or the like.
The anode 2 is preferably Indium Tin Oxide (ITO) coated on top of the substrate by vacuum sputtering. The cathode 4 is preferably Ag conductive paste, and may be Ag thin film or Ba/Al thin film.
The hole transport layer 5 is preferably PEDOT or polyvinylcarbazole, and is formed on the surface of the anode by a method such as spin coating.
The electron transport layer 6 is preferably PFNR2，PFNR2Is a polymer with quaternary ammonium salt functional groups on side chains, and is a commonly used electron transport layer material in organic light-emitting diodes.
The polymer light emitting layer 3 is generally prepared by spin coating, printing, or the like.
The material of the polymer light-emitting layer 3 is a conjugated polymer of benzothiadiazole having a structure of general formula (I):
wherein R is1Is hydrogen or C1～C36Alkyl groups of (a); r2Is hydrogen or C1～C36Alkyl groups of (a); ar is one of thiophene, alkyl substituted thiophene, alkoxy substituted thiophene, bithiophene, alkyl substituted bithiophene and alkoxy substituted bithiophene; n =3 ~ 1000.
The preparation method of the conjugated polymer of the benzothiadiazole is to copolymerize a monomer of the benzothiadiazole with a thiophene monomer or an oligothiophene monomer.
The preparation method of the conjugated polymer of the benzothiadiazole is to copolymerize a 5, 6-difluoro-benzothiadiazole monomer and a bitrithiophene monomer or a bitrithiophene monomer, or to copolymerize a 4, 7-bithiophene-5, 6-difluoro-benzothiadiazole monomer and a thiophene monomer or a bithiophene monomer.
Example 1:
preparation of 1, 2-diamino-4, 5-difluoro-3, 6-dibromobenzene, reaction formula is as follows:
in a 500 ml two-neck flask, 2, 3-difluoro-5, 6-dinitro-1, 4-dibromobenzene (13.24 g, 36.57 mmol) and reduced iron powder (25.60 g, 457.14 mmol) were added, 200 ml glacial acetic acid was added under an inert atmosphere, and the mixture was heated to 45 ℃ for 4 hours.
After the reaction was completed and cooled to room temperature, it was poured into 200 ml of 5% by weight aqueous NaOH solution at 5 ℃ and extracted with dichloromethane 3 times, and the organic phase was saturated NaHCO3Washing with water solution for 2 times, drying with anhydrous magnesium sulfate, separating, removing solvent, and purifying with silica gel column to obtain off-white solid. Warp beam1HNMR，13CNMR, and elemental analysis tests showed the target product 1, 2-diamino-4, 5-difluoro-3, 6-dibromobenzene.
Example 2:
preparation of 5, 6-difluoro-4, 7-dibromobenzothiadiazole, the reaction formula is as follows:
in a 500 ml two-necked flask placed in an ice-water bath were charged 1, 2-diamino-4, 5-difluoro-3, 6-dibromobenzene (3.32 g, 11.00 mmol), 4.7 ml triethylamine and 150 ml anhydrous chloroform. Under inert atmosphere, chargingTo the stirred solution, 1.9 ml of thionyl chloride was added dropwise, followed by heating to 70 ℃ for reaction overnight. After the reaction, the reaction solution was poured into 250 ml of water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, separated, and then the solvent was removed, and separated and purified by silica gel column chromatography to obtain a white solid. Warp beam13CNMR, and elemental analysis tests showed the target product 5, 6-difluoro-4, 7-dibromobenzothiadiazole.
Example 3:
preparation of 4, 7-bis (4-alkylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole according to the following reaction scheme:
the preparation of 4, 7-bis (4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole is described as an example. In a 50 ml two-necked flask, 5, 6-difluoro-4, 7-dibromobenzothiadiazole (330 mg, 1.00 mmol), tributyl- (4- (2-decyltetradecyl) thiophen-2-yl) stannane (2.13 g, 3.00 mmol) were added, nitrogen was introduced for 30 minutes, then bis (triphenylphosphine) palladium dichloride 268 mg was added, and anhydrous toluene 15 ml was added under nitrogen protection, and the reaction was heated under reflux for two days. After the reaction was completed, the reaction mixture was cooled to room temperature, poured into 100 ml of water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, separated, the solvent was removed, separated by a silica gel column, and purified by recrystallization from ethanol to obtain a yellow solid. Warp beam1HNMR，13CNMR, and elemental analysis tests showed 4, 7-bis (4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole as the target product.
The preparation of 4, 7-bis (4- (2-hexyldecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole is further illustrated. In a 50 ml two-necked flask, 1.00 mmol of 5, 6-difluoro-4, 7-dibromobenzothiadiazole and 3.00 mmol of tributyl- (4- (2-hexyldecyl) thiophen-2-yl) alkyltin were charged, and the mixture was poured inAfter 30 minutes of nitrogen, 268 mg of bis (triphenylphosphine) palladium dichloride was added, and 15 ml of anhydrous toluene was added under nitrogen protection, and the reaction was refluxed for two days. After the reaction was completed, the reaction mixture was cooled to room temperature, poured into 100 ml of water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, separated, the solvent was removed, separated by a silica gel column, and purified by recrystallization from ethanol to obtain a yellow solid. Warp beam1HNMR，13CNMR, and elemental analysis tests showed 4, 7-bis (4- (2-hexyldecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole as the target product.
The preparation of 4, 7-bis (4-dodecylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole is further illustrated. In a 50 ml two-neck flask, 1.00 mmol of 5, 6-difluoro-4, 7-dibromobenzothiadiazole and 3.00 mmol of tributyl- (4-dodecylthiophen-2-yl) alkyltin are added, nitrogen is introduced for 30 minutes, then 268 mg of bis (triphenylphosphine) palladium dichloride is added, 15 ml of anhydrous toluene is added under the protection of nitrogen, and the reaction is heated and refluxed for two days. After the reaction was completed, the reaction mixture was cooled to room temperature, poured into 100 ml of water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, separated, the solvent was removed, separated by a silica gel column, and purified by recrystallization from ethanol to obtain a yellow solid. Warp beam1HNMR，13CNMR, and elemental analysis tests showed 4, 7-bis (4-dodecylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole as the target product.
The alkyl group in 4, 7-bis (4-alkylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole also includes: methyl, ethyl, n-hexyl, 2-ethylhexyl, 1-octylnonyl, and the like, but are not limited thereto.
Example 4:
preparation of 4, 7-bis (5-bromo-4-alkylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole according to the following reaction scheme:
the preparation of 4, 7-bis (5-bromo-4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole is described as an example. In a 50 ml one-neck flask were added 4, 7-bis (4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole (808 mg, 0.80 mmol) and 15 ml tetrahydrofuran, and bromosuccinimide (NBS) (315 mg, 1.76 mmol) was added with thorough stirring, and reacted at room temperature with exclusion of light for 24 hours. After the reaction, the reaction solution was added to water, extracted with dichloromethane, the organic phase was successively washed with saturated brine and water, dried over anhydrous sodium sulfate, the solvent was dried by spinning, and recrystallized with ethanol to obtain an orange-red solid. Warp beam1HNMR，13CNMR, and elemental analysis tests showed 4, 7-bis (5-bromo-4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole as the target product.
The alkyl group in 4, 7-bis (5-bromo-4-alkylthiophen-2-yl) -5, 6-difluoro-benzothiadiazole also includes: methyl, ethyl, n-hexyl, 2-ethylhexyl, n-dodecyl, 1-octylnonyl, 2-hexyldecyl, etc., but are not limited thereto.
Example 5:
preparation of Polymer 1, the reaction scheme is as follows:
to a 50 ml two-necked flask, 0.20 mmol each of 4, 7-bis (5-bromo-4- (2-decyltetradecyl) thiophen-2-yl) -5, 6-difluoro-benzothiadiazole and 2, 5-bis (trimethyltin) -thiophene, 6 mg of tris (dibenzylideneacetone) dipalladium and 12 mg of tri-o-tolylphosphine were added under an argon atmosphere, dissolved in 8 ml of m-xylene, and the reaction was stirred under reflux for 72 hours. After cooling, the polymer was precipitated with methanol, the dried product was extracted successively with methanol, ethyl acetate and chloroform, the chloroform solution was concentrated and precipitated in methanol, and finally the product was dried under vacuum to give a dark violet polymer 1. The resulting polymer had a number average molecular weight of 24000 and a weight average molecular weight of 33000.
Example 6:
preparation of Polymer 2, the reaction scheme is as follows:
the procedure is as in example 5. 5,5 '-bis (trimethyltin) -2, 2' -bithiophene was used instead of 2, 5-bis (trimethyltin) -thiophene. The resulting black polymer had a number average molecular weight of 25000 and a weight average molecular weight of 36000. The polymer film showed a UV absorption peak at 692nm with an absorption cut-off at 743 nm.
The manufacturing method of the light emitting diode comprises the following steps:
preparing a substrate 1, wherein the size of the substrate is the same, 15 mm is multiplied by 15 mm, the square resistance is about 20 ohm/□, in order to compare performance parameters of the prepared device, sequentially carrying out ultrasonic treatment on the substrate for 10 minutes by using acetone, micron-sized special semiconductor detergent, deionized water and isopropanol, cleaning the surface of the anode substrate, and then placing the substrate in a constant-temperature oven to stand for 4 hours for drying at 80 ℃.
And preparing an anode 2, wherein the anode of the light-emitting diode is made of indium tin oxide and is covered on the substrate by vacuum sputtering. And (3) bombarding the dried anode substrate by using an oxygen plasma etching instrument for 10 minutes by using plasma to remove the organic deposition film attached to the surface of the anode substrate, and improving the work function of the surface of the anode.
Preparing a hole transport layer 5, bombarding the dried anode substrate with an oxygen plasma etching instrument for 10 minutes by plasma to remove an organic deposition film attached to the surface of the anode substrate, improving the work function of the surface of the anode, and then placing the anode substrate on a spin coater (KW-4A type) to spin a hole transport layer PEDOT with the thickness of about 40 nanometers at a high speed: aqueous PSS (concentration about 1%, available from Bayer). The film thickness is controlled by the concentration of the solution and the spin-coating rotation speed. And (3) after film formation, transferring the anode substrate into a constant-temperature vacuum oven to be dried at the temperature of 80 ℃, removing residual solvent and hardening the film.
In addition, polyvinylcarbazole PVK may be selected as a material of the hole transport layer. Putting the PVK solid into a clean small bottle, transferring into a special glove box for nitrogen film formation, adding chlorobenzene to prepare a 1% solution, putting on a stirring table, stirring uniformly, and filtering with a 0.45-micron filter membrane to obtain a clear filtrate.
The polymer light emitting layer 3 is prepared, and the polymer light emitting layer prepared by the above method of the present invention is formed on the surface of the anode by a method such as spin coating or printing. The polymer light-emitting layer adopts the polymer material. Placing the polymer luminescent polymer in a clean vial, transferring into a special nitrogen film-forming glove box, dissolving with solvent to prepare a solution, placing on a stirring table, stirring uniformly, and filtering with a 0.45-micron filter membrane to obtain a clear filtrate. The polymer luminescent layer is deposited in a special anhydrous and oxygen-free glove box for nitrogen protection film forming, the polymer luminescent layer is prepared by adsorbing an anode substrate on a spin coater and performing high-speed spin coating, and the film thickness is controlled by adjusting the rotating speed of the spin coater. The optimal thickness of the polymer light-emitting layer is 70-90 nanometers, and the polymer light-emitting layer is actually measured and monitored by a surface profiler.
Preparation of the Electron transport layer 6 Using PFNR2The thickness of the electron transport layer was about 1 nm.
The cathode 4 is prepared by depositing a metal on the surface of the polymer light-emitting layer by vacuum deposition. Putting the device into a vacuum coating machine, and coating corresponding metal electrodes by conventional vacuum evaporation method with vacuum degree of 3 × 10-4And (pa) monitoring the film coating rate and the thickness of each layer of metal electrode film in real time by a quartz oscillator film thickness monitor. And evaporating an Ag metal film by adopting a vacuum evaporation method to prepare the cathode. The cathode can also be made by evaporating a Ba/Al metal film.
Another method for manufacturing the cathode is to uniformly coat a layer of conductive adhesive on the film of the polymer luminous layer, heat the film at 60 ℃ for 2 hours to accelerate solidification, and preferably coat Ag conductive adhesive as the cathode.
Compared with the prior art, the light-emitting diode has the following beneficial effects:
(1) the polymer light-emitting layer is used as a high-efficiency light-emitting polymer, so that the light-emitting diode has high energy conversion efficiency and high carrier mobility.
(2) The preparation process is simple and the preparation cost is low. In the prior art, the cathode of the organic light emitting diode needs to be manufactured under high vacuum, and the complicated process of vacuumizing, evaporation or sputtering is needed. By adopting the polymer luminescent layer, the device can be prepared only by uniformly coating the conductive adhesive on the surface of the polymer luminescent layer and solidifying, so that the manufacturing process of the polymer luminescent device and the display screen is greatly simplified, and the cost is reduced.
(3) The method is suitable for preparing the cathode of the flexible display screen. Since the cathode of the conventional organic light emitting diode is a metal thin film, the device may fail due to cathode peeling when bent to a large extent. In one embodiment of the invention, the conductive adhesive is used as a cathode material, the substrate is a polymer adhesive, and the cured conductive adhesive has considerable bonding strength and toughness and can be firmly combined even when bent greatly, so that the conductive adhesive is suitable for manufacturing a cathode of a flexible display screen.
The present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof, and it should be understood that various changes and modifications can be effected therein by one skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (8)
1. A polymer light emitting diode comprising an electron transport layer, comprising a substrate, an anode, a hole transport layer, a polymer light emitting layer, an electron transport layer and a cathode, which are sequentially stacked,
the material of the polymer light-emitting layer is a conjugated polymer of benzothiadiazole with a structure of general formula (I),
wherein R is1Is hydrogen or C1～C36Alkyl groups of (a); r2Is hydrogen or C1～C36Alkyl groups of (a); ar is one of thiophene, alkyl substituted thiophene, alkoxy substituted thiophene, bithiophene, alkyl substituted bithiophene and alkoxy substituted bithiophene; n =3 ~ 1000.
2. The polymer light emitting diode of claim 1, wherein the substrate can be a rigid substrate or a flexible substrate.
3. The polymer light emitting diode of claim 1, wherein the hard substrate is preferably glass, ceramic, metal, or the like.
4. The polymer light emitting diode of claim 1, wherein the flexible substrate is preferably polyethylene terephthalate, plexiglass, or the like.
5. The polymer light emitting diode of claim 1, wherein the anode is preferably indium tin oxide.
6. The polymer light emitting diode of claim 1, wherein the cathode is preferably Ag conductive paste, and may be Ag thin film or Ba/Al thin film.
7. The polymer light emitting diode of claim 1, wherein the hole transport layer is PEDOT or polyvinylcarbazole.
8. The polymer light emitting diode of claim 1, wherein the electron transport layer is PFNR2。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003041183A1 (en) * | 2001-11-07 | 2003-05-15 | Cambridge University Technical Services Limited | Electroluminescent device |
| CN1719637A (en) * | 2005-07-15 | 2006-01-11 | 华南理工大学 | Method for making cathode of organic/polymer LED |
| CN101516962A (en) * | 2006-07-31 | 2009-08-26 | 住友化学株式会社 | Polymer compound and polymer light-emitting device using the same |
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