CN118284111A - Organic light emitting device, method of manufacturing the same, and display panel - Google Patents
Organic light emitting device, method of manufacturing the same, and display panel Download PDFInfo
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- CN118284111A CN118284111A CN202211732092.3A CN202211732092A CN118284111A CN 118284111 A CN118284111 A CN 118284111A CN 202211732092 A CN202211732092 A CN 202211732092A CN 118284111 A CN118284111 A CN 118284111A
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- organic light
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Abstract
The application provides an organic light emitting device, a preparation method thereof and a display panel. The organic light-emitting device comprises a first electrode, a first light-emitting unit, a charge generation layer, a second light-emitting unit and a second electrode which are sequentially stacked; the charge generation layer comprises an electron injection material and a hole generation material, the electron injection material comprises first gold nanoparticles, and the surfaces of the first gold nanoparticles are modified by N-heterocyclic carbene ligands. According to the organic light-emitting device, the preparation method thereof and the display panel, the surface potential is reduced by using the modification of the NHC ligand to reduce the work function of Au, so that the potential barrier injected into the organic light-emitting layer is reduced, and the electron injection in the tandem OLED is improved.
Description
Technical Field
The application relates to the technical field of organic light emitting, in particular to an organic light emitting device, a preparation method thereof and a display panel.
Background
Organic Light-Emitting Diode (OLED) is an emerging display and lighting technology, and has many advantages of high contrast, wide viewing angle, ultra-fast response, etc., and is widely used at present, but a certain challenge is still faced to realizing larger-scale commercial production.
The organic light-emitting diode prepared based on the solution method has outstanding advantages on a terminal display screen with large area and rich morphology because the organic light-emitting diode is suitable for a low-cost manufacturing process. However, organic light emitting materials have a shallow LUMO energy level and often require a low work function electron injection layer or cathode. The electron injection layer or cathode with a low work function is difficult to prepare by a solution method due to its low stability. Particularly in tandem organic light emitting diodes, electrons generated by the charge generating layer also need to be efficiently injected into the light emitting layer.
Disclosure of Invention
In view of the above, the present application provides an organic light emitting diode device capable of efficiently injecting electrons of an electron injection layer into a light emitting layer.
The present application provides an organic light emitting device, comprising:
A first electrode, a first light emitting unit, a charge generating layer, a second light emitting unit, and a second electrode, which are sequentially stacked;
The charge generation layer comprises an electron injection material and a hole generation material, the electron injection material comprises first gold nanoparticles, and the surfaces of the first gold nanoparticles are modified by N-heterocyclic carbene ligands.
In some embodiments, the hole generating material comprises:
At least one of second gold nanoparticles and third gold nanoparticles, wherein the surfaces of the second gold nanoparticles are not modified by ligands, and the surfaces of the third gold nanoparticles are combined with first ligands.
In some embodiments, the first ligand is selected from at least one of an acid ligand, a thiol ligand, an amine ligand, a phosphine oxide ligand, a phospholipid, a soft phospholipid, and a polyvinylpyridine.
In some embodiments, the N-heterocyclic carbene ligand is selected from at least one of the following structural formulas:
Wherein the N-heterocyclic carbene ligand coordinates with gold atoms on the surfaces of the gold nanoparticles through lone pair electrons on carbon atoms between two nitrogen atoms;
each occurrence of R 1 is independently selected from at least one of the following structural formulas:
R 2 and R 3 are each independently selected from H, alkyl or alkoxy groups containing 1 to 12 carbon atoms, amino, hydroxyl, mercapto, carboxyl.
In some embodiments, the first gold nanoparticle is selected from at least one of the following structures:
wherein n is a positive integer greater than 1, and Au represents gold nanoparticles.
In some embodiments, the N-heterocyclic carbene ligand is selected from at least one of the following structural formulas:
In some embodiments, the mass ratio of the electron injecting material to the hole generating material is 1 (0.2 to 5).
In some embodiments, the mass ratio of the electron injecting material to the hole generating material is 1 (0.5 to 2).
In some embodiments, the first gold nanoparticles have an average particle size of 2nm to 10nm, and/or
The second gold nanoparticles have an average particle size of 2nm to 10nm, and/or
The third gold nanoparticles have an average particle diameter of 2nm to 10nm.
In some embodiments, the first light emitting unit includes a first hole functional layer, a first light emitting layer, and a first electron functional layer, which are sequentially stacked, the first hole functional layer being disposed near the first electrode, the first electron functional layer being disposed near the charge generating layer; the second light-emitting unit comprises a second hole functional layer, a second light-emitting layer and a second electronic functional layer which are sequentially stacked, wherein the second hole functional layer is close to the charge generation layer, and the second electronic functional layer is close to the second electrode.
In some embodiments, the first hole-functional layer comprises a first hole-injection layer and a first hole-transport layer, the first electron-functional layer comprises a first electron-transport layer, the second hole-functional layer comprises a second hole-transport layer and a second hole-injection layer, and the second electron-functional layer comprises a first electron-injection layer and a second electron-transport layer;
The first electrode and the second electrode are respectively and independently selected from a doped metal oxide particle electrode, a composite electrode, a graphene electrode, a carbon nano tube electrode, a metal simple substance electrode or an alloy electrode, wherein the material of the doped metal oxide particle electrode is selected from one or more of indium doped tin oxide, fluorine doped tin oxide, antimony doped tin oxide, aluminum doped zinc oxide, gallium doped zinc oxide, indium doped zinc oxide, magnesium doped zinc oxide and aluminum doped magnesium oxide, the composite electrode is selected from AZO/Ag/AZO、AZO/Al/AZO、ITO/Ag/ITO、ITO/Al/ITO、ZnO/Ag/ZnO、ZnO/Al/ZnO、TiO2/Ag/TiO2、TiO2/Al/TiO2、ZnS/Ag/ZnS or ZnS/Al/ZnS, and the material of the metal electrode is selected from one or more of Ag, al, cu, au, mo, pt, ca and Ba; and/or
The materials of the first light-emitting layer and the second light-emitting layer are selected from one or more of organic light-emitting materials, wherein the organic light-emitting materials are selected from one or more of 4,4' -bis (N-carbazole) -1,1' -biphenyl, tris [2- (p-tolyl) pyridine iridium (III), 4' -tris (carbazole-9-yl) triphenylamine, tris [2- (p-tolyl) pyridine iridium, diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, blue light-emitting TBPe fluorescent materials, green light-emitting TTPX fluorescent materials, orange light-emitting TBRb fluorescent materials, red light-emitting DBP fluorescent materials, delayed fluorescent materials, TTA materials, heat-activated delayed materials, polymers containing B-N covalent bonds, hybrid local charge transfer excited state materials and excited compound luminescent materials; and/or
The first electron transport layer and the second electron transport layer each comprise an electron transport material, the electron transport materials are respectively and independently selected from at least one of metal oxide, doped metal oxide, II-VI semiconductor material, III-V semiconductor material and I-III-VI semiconductor material, and the metal oxide is selected from at least one of ZnO, baO, tiO 2、SnO2; the metal oxide in the doped metal oxide is at least one of ZnO and TiO 2、SnO2, the doping element is at least one of Al, mg, li, in, ga, and the II-VI semiconductor group material is at least one of ZnS, znSe, cdS; the III-V semiconductor group material is at least one of InP and GaP; the I-III-VI semiconductor material is at least one of CuInS and CuGaS; and/or
The material of the first electron injection layer is at least one selected from cesium carbonate, cesium fluoride, cesium azide and lithium fluoride; and/or
The first hole transport layer and the second hole transport layer each comprise a hole transport material independently selected from the group consisting of 4,4'-N, N' -dicarbazolyl-biphenyl (CBP), N '-diphenyl-N, N' -bis (1-naphthyl) -1,1 '-biphenyl-4, 4 "-diamine, N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4,4 '-diamine, N' -bis (3-methylphenyl) -N, N '-bis (phenyl) -spiro (spiro-TPD), N, N' -bis (4- (N, N '-diphenyl-amino) phenyl) -N, N' -diphenyl benzidine, 4 '-tris (N-carbazolyl) -triphenylamine, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, poly [ (9, 9 '-dioctylfluorene-2, 7-diyl) -co- (4, 4' - (N- (4-sec-butylphenyl) diphenylamine)) ], poly (4-butylphenyl-diphenylamine) (poly-TPD), polyaniline, polypyrrole, poly (p-phenylene vinylene), poly (p-phenylene vinylene), poly [ 2-methoxy-5- (2-ethylhexyl oxy) -1, 4-phenylenevinylene ] and poly [ 2-methoxy-5- (3 ',7' -dimethyloctyl oxy) -1, 4-phenylenevinylene ], copper phthalocyanines, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4' -bis (P-carbazolyl) -1,1' -biphenyl compounds, N ' -tetraarylbenzidine, PEDOT: at least one of PSS and derivatives thereof, poly (N-vinylcarbazole) (PVK) and derivatives thereof, polymethacrylate and derivatives thereof, poly (9, 9-octylfluorene) and derivatives thereof, poly (spirofluorene) and derivatives thereof, N ' -di (naphthalen-1-yl) -N, N ' -diphenyl benzidine, spironpb, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO 3, doped or undoped WO 3, doped or undoped V 2O5, doped or undoped P-type gallium nitride, doped or undoped CrO 3, doped or undoped CuO; and/or
The materials of the first hole injection layer and the second hole injection layer are selected from at least one of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene, PEDOT, PSS doped with s-MoO3 derivatives, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, tetracyanoquinodimethane, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide and copper oxide.
The application also provides a preparation method of the organic light-emitting device, which comprises the following steps:
Sequentially stacking a first electrode, a first light-emitting unit, a charge generation layer, a second light-emitting unit and a second electrode; or sequentially laminating to form a second electrode, a second light-emitting unit, a charge generation layer, a first light-emitting unit and a first electrode;
wherein the charge generation layer is formed by:
mixing an electron injection material and a hole generation material to obtain a mixed solution, wherein the electron injection material comprises first gold nanoparticles, and the surfaces of the first gold nanoparticles are modified by N-heterocyclic carbene ligands;
the mixed solution is formed on the first light emitting unit or the second light emitting unit by a solution method, and dried to obtain the charge generating layer.
The present application also provides a display panel including the organic light emitting device as described above or an organic light emitting device prepared by the above-described preparation method.
According to the organic light-emitting device, the preparation method thereof and the display panel, the modification of the NHC ligand is utilized to reduce the work function of Au, so that the potential barrier injected into the organic light-emitting layer is reduced, and the electron injection in the tandem OLED is improved.
Drawings
In order to more clearly illustrate the technical solutions of the present application, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural view of an organic light emitting device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of a display panel according to an embodiment of the application.
Detailed Description
The technical solutions of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application. It will be apparent that the described embodiments are only some, but not all, of the embodiments of the application. All other embodiments, based on the embodiments of the application, which a person skilled in the art would obtain without making any inventive effort, are within the scope of the application.
In the present application, unless expressly stated or limited otherwise, a first feature "above" or "below" a second feature may include both the first and second features directly, or may include both the first and second features not directly connected but contacted by additional features therebetween. Moreover, a first feature being "above," "over" and "on" a second feature includes the first feature being directly above and obliquely above the second feature, or simply indicating that the first feature is higher in level than the second feature. The first feature being "under", "below" and "beneath" the second feature includes the first feature being directly under and obliquely below the second feature, or simply means that the first feature is less level than the second feature. Furthermore, the terms "first," "second," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include one or more features.
The present application provides an organic light emitting device 100 including a first electrode 10, a first light emitting unit 20, a charge generating layer 50, a second light emitting unit 30, and a second electrode 40, which are sequentially stacked. Wherein the charge generation layer 50 includes an electron injection material and a hole generation material, the electron injection material includes gold nanoparticles, and the surface of the first gold nanoparticles is modified with an N-heterocyclic carbene ligand.
The charge generation layer 50 of the present application contains both an electron injection material and a hole generation material. The electron injection material comprises Au nano-particles with surfaces modified by NHC as a ligand. Typically, electron injection typically requires an electron injection material work function of less than 4.0 and hole injection requires a hole generation material work function of greater than 4.5. Work function is the energy of an electron located at the fermi level inside a solid just out of the surface, but the potential energy of electrons at different locations on the surface is different. Or, the work function is the distance from the vacuum level to the metal fermi level, which is represented by the potential energy of electrons, affecting the injection barrier.
Au has a large work function of about 5eV, while the LUMO (Lowest Unoccupied Molecular Orbital ) energy level of the organic light-emitting layer is about 2.5eV. Au is directly injected into the organic light emitting layer with an injection barrier of about 2.5eV. The application utilizes the modification of NHC ligand to regulate the work function of Au, and the regulation mainly comes from the dipole moment of NHC on one hand and the dipole action of Au-C bond on the other hand. Specifically, the application uses the directional arrangement of dipoles (forming an electrostatic field) to change the surface potential to lower the work function of Au. The dipole layer may be accomplished by a molecular directional arrangement having dipole moments. In practical applications, the dipole layer is generally used to explain the change of work function, and if the change of work function is measured directly, the dipole layer can be considered to be formed on the surface of the measured material. While NHC ligands are molecules with dipole moments that can lower the work function of the Au surface from about 5eV to about 3eV, thereby lowering the barrier to the organic light emitting layer and thus enhancing electron injection in tandem OLEDs.
In some embodiments, the N-heterocyclic carbene ligand is selected from at least one of the groups represented by the following structural formulae:
wherein each occurrence of R 1 is independently selected from at least one of the following structural formulas:
R 2 and R 3 are each independently selected from H, alkyl or alkoxy groups containing 1 to 12 carbon atoms, amino, hydroxyl, mercapto, carboxyl.
Specifically, the N-heterocyclic carbene ligand coordinates with the gold atom on the surface of the gold nanoparticle through the lone pair electron on the carbon atom between two nitrogen atoms. I.e., the N-heterocyclic carbene ligand is bound to the gold nanoparticle surface by a coordination reaction. The first gold nanoparticle may be expressed as:
Wherein n is a positive integer greater than 1, and Au represents gold nanoparticles. In some embodiments, the number of n is determined by the number of gold atoms on the gold nanoparticle surface. Each gold atom on the surface of the gold nanoparticle may be attached to a ligand.
In some embodiments, the N-heterocyclic carbene ligand is selected from at least one of the groups represented by the following structural formulae:
That is, the NHC ligand is mainly imidazole (or dihydroimidazole), tetrahydropyrimidine, benzimidazole ring, the substituent R1 on the N atom may be Me, et, iPr, tBu, cy, 2-Py, mes, ph, dipp, the substituents R2 and R3 on the ring may be H, alkyl or alkoxy group containing 1-12 carbon atoms, amino, hydroxyl, mercapto, carboxyl. It should be noted that, due to the high activity of NHC, precursors thereof, such as onium halides and carbonates, are usually selected for coordination with Au nanoparticles, and NHC is used as a coordinating group after the reaction.
In the present application, the hole generating material may be selected from materials commonly used in the art capable of generating holes. In some embodiments, anode materials commonly used in the art may be used as the hole generating material of the present application, for example, metal oxide particles, graphene, carbon nanotubes, metal simple substances or alloys, materials doped with metal oxide particles are selected from one or more of indium doped tin oxide, fluorine doped tin oxide, antimony doped tin oxide, aluminum doped zinc oxide, gallium doped zinc oxide, indium doped zinc oxide, magnesium doped zinc oxide and aluminum doped magnesium oxide, and materials of metals are selected from one or more of Ag, al, cu, au, mo, pt, ca and Ba.
The Au nanoparticle used as the hole injection material may have no ligand modification on the surface or may be ligand-modified. In some embodiments, the hole injection material comprises at least one of a second gold nanoparticle, the surface of which is not modified with a ligand, and a third gold nanoparticle, the surface of which is bound with a first ligand. The first ligand may be a non-N-heterocyclic carbene ligand. Specifically, the first ligand is at least one selected from an acid ligand, a thiol ligand, an amine ligand, a phosphine oxide ligand, a phospholipid, a soft phospholipid and a polyvinylpyridine. The acid ligand is at least one of decanoic acid, undecylenic acid, tetradecanoic acid, oleic acid and stearic acid; the mercaptan ligand is at least one selected from octaalkyl mercaptan, dodecyl mercaptan and octadecyl mercaptan; the amine ligand is at least one of oleylamine, octadecylamine and octamine; the phosphine ligand is selected from trioctylphosphine, and at least one of the phosphine oxide ligands trioctylphosphine oxide.
The work function of the gold nanoparticles which are not modified by the ligand and/or the third gold nanoparticles is larger than that of the first gold nanoparticles which are modified by the N-heterocyclic carbene ligand on the surface, so that the gold nanoparticles are suitable hole injection materials. Further, the Au nanoparticle has a good stability, and is suitable for preparing the charge generation layer 50 by a solution method. The role of the stabilizing ligand is to make the Au nano-particles have better dispersibility, and the stabilizing ligand includes but is not limited to thiol, carboxyl, amino and the like. The electronegativity of the end group of the stable ligand is larger and can be adsorbed on the surface of the Au nano-particle, thereby playing a role in stabilization. In addition, the hole injection material and the electron injection material in the present application have the same metal nanoparticles, which is advantageous in work function matching, and can be dispersed in the same solvent, thereby facilitating the solution process for preparing the charge generation layer 50.
Alternatively, the charge generation layer 50 may be formed in a solution method, and an electron injection material and a hole generation material are mixed in the charge generation layer 50. The preparation method of forming the charge generation layer 50 in a solution method includes the steps of: the electron injection material and the hole generation material are mixed according to a certain mass ratio to form dispersion liquid, the dispersion liquid is formed on a substrate in a solution method, the film is annealed for 5-200 min at 100-200 ℃ under inert gas after the film forming, the inert gas can be N 2, ar and other gases, and the dispersion solvent of the electron injection material and the hole generation material is one or more of common solvents, such as methanol, ethanol, isopropanol, N-butanol, N-hexanol, N-heptanol, cyclohexanone, tetrahydrofuran, acetonitrile, toluene, xylene, chlorobenzene, cyclohexylbenzene, tetrahydronaphthalene, methyl benzoate, ethyl benzoate, N-hexane and N-octane.
The charge generation layer 50 may contain other components in addition to the hole injection material and the electron injection material described above. The present application is not limited to the remaining components as long as the charge generation function is not destroyed.
In some embodiments, the mass ratio of electron injecting material to hole injecting material is 1 (0.2-5), e.g., 1:0.2, 1:0.25, 1:0.33, 1:0.5, 1:1, 0.5:1, 0.33:1, 0.25:1, 0.2:1.
In some embodiments, the mass ratio of electron injecting material to hole injecting material is 1 (0.5-2). For example, 1:0.5, 1:1, 0.5:1.
In some embodiments, the mass ratio of electron injecting material to hole injecting material is 1:1. When the mass ratio of the electron injection material to the hole injection material is 1:1, the charge generation and injection capability of the first charge generation layer is best.
In some embodiments, the first gold nanoparticles have an average particle size of 2nm to 10nm. When the average particle diameter of the first gold nanoparticles is too small, it is difficult to ensure conductivity due to quantum size effect, and when the average particle diameter is too large, film formation is not facilitated.
In some embodiments, the second gold nanoparticles have an average particle size of 2nm to 10nm. When the average particle diameter of the second gold nanoparticles is too small, it is difficult to ensure conductivity due to quantum size effect, and when the average particle diameter is too large, film formation is not facilitated.
In some embodiments, the third gold nanoparticles have an average particle size of 2nm to 10nm. When the average particle diameter of the surface modified by the stable ligand is too small, the conductivity is difficult to be ensured due to the quantum size effect, and when the average particle diameter is too large, the film formation is not facilitated.
In tandem OLEDs, the electrode between the two light emitting layers is replaced by a Charge Generating Unit (CGU), which needs to have a strong current generating capability at a small voltage, instead of the electrode, so that the driving voltage is reduced when the device is operated. Since the OLED is current driven, the CGU will limit the device current if it does not have strong charge generation and separation capability, allowing the device to have a larger driving voltage. The charge generation layer 50 comprises an electron injection material and a hole generation material, wherein the electron injection material adopts Au nanoparticles modified by N-heterocyclic carbene ligands, and a stable dipole layer is formed on the surface of Au by virtue of the Au nanoparticles, so that the injection barrier of electrons to the light-emitting layer is reduced; the hole generating material is Au nano particles which are not modified by NHC, the charge generating layer 50 assists hole injection when contacting with the hole injection layer due to the dual function and inherent high conductivity of Au, the hole injection enhancement can lead to rapid transport of generated holes, thus the charge separation capability is enhanced, and if the holes are not transported in time, the accumulation of holes can inhibit the generation of charges in turn.
Referring again to fig. 1, in some embodiments, the first light emitting unit 20 includes a first hole functional layer 21, a first light emitting layer 23, and a first electron functional layer 22 that are sequentially stacked. The first hole functional layer 21 is disposed between the first electrode 10 and the first light emitting layer 23, and the first electron functional layer 22 is disposed between the first light emitting layer 23 and the charge generating layer 50. The second light emitting unit 30 includes a second hole function layer 31, a second light emitting layer 33, and a second electron function layer 32, which are sequentially stacked. The second hole-functional layer 31 is disposed between the second light-emitting layer 33 and the charge-generating layer 50, and the second electron-functional layer 32 is disposed between the second electrode 40 and the second light-emitting layer 33. The first hole functional layer 21 includes a first hole injection layer 211 and/or a first hole transport layer 212, the first electron functional layer 22 includes a first electron transport layer 221, the second hole functional layer 31 includes a second hole transport layer 311 and a second hole injection layer 312, and the second electron functional layer 32 includes a first electron injection layer 321 and/or a second electron transport layer 322. In a specific embodiment, the first hole functional layer 21 includes a first hole injection layer 211 and a first hole transport layer 212 disposed between the first hole injection layer 211 and the first electrode 10, the first electron functional layer 22 includes a first electron transport layer 221, the second hole functional layer 31 includes a second hole transport layer 311 and a second hole injection layer 312 disposed between the second hole transport layer 311 and the charge generation layer 50, and the second electron functional layer 32 includes a first electron injection layer 321 and a second electron transport layer 322 disposed between the first electron injection layer 321 and the first electrode 10. In some embodiments, the first electron transport layer 221 and the second electron transport layer 322 may not be included. The light emitting device of the present application may be either a front-up device or an inverted device.
The charge generating layer 50 and the second hole injection layer 312 together form a charge generating unit, and timely inject carriers into the upper and lower light emitting units, so that charge separation efficiency and the injection capability of separated charges into the upper and lower light emitting units can be enhanced, and the efficiency and the service life of the device can be improved. And the luminous efficiency of the serial organic light emitting diode is improved.
In some embodiments, the first electrode 10 and the second electrode 40 are each independently selected from a doped metal oxide particle electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal simple substance electrode, or an alloy electrode, the material of the doped metal oxide particle electrode is selected from one or more of indium doped tin oxide, fluorine doped tin oxide, antimony doped tin oxide, aluminum doped zinc oxide, gallium doped zinc oxide, indium doped zinc oxide, magnesium doped zinc oxide, and aluminum doped magnesium oxide, the composite electrode is selected from AZO/Ag/AZO、AZO/Al/AZO、ITO/Ag/ITO、ITO/Al/ITO、ZnO/Ag/ZnO、ZnO/Al/ZnO、TiO2/Ag/TiO2、TiO2/Al/TiO2、ZnS/Ag/ZnS or ZnS/Al/ZnS, and the material of the metal electrode is selected from one or more of Ag, al, cu, au, mo, pt, ca and Ba.
In some embodiments, the materials of the first and second light emitting layers 23 and 33 are selected from organic light emitting materials selected from one or more of 4,4' -bis (N-carbazole) -1,1' -biphenyl tris [2- (p-tolyl) iridium (III), 4' -tris (carbazol-9-yl) triphenylamine tris [2- (p-tolyl) iridium pyridine, biaryl anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, blue-emitting TBPe fluorescent materials, green-emitting TTPX fluorescent materials, orange-emitting TBRb fluorescent materials, red-emitting DBP fluorescent materials, delayed fluorescent materials, TTA materials, thermally activated delayed materials, polymers containing B-N covalent bonds, hybrid local charge transfer excited state materials, and exciplex luminescent materials.
In some embodiments, both the first electron transport layer 221 and the second electron transport layer 322 comprise an electron transport material. The electron transport materials of the first electron transport layer 221 and the second electron transport layer 322 are each independently selected from at least one of a metal oxide, a doped metal oxide, a group II-VI semiconductor material, a group III-V semiconductor material, and a group I-III-VI semiconductor material, the metal oxide being selected from at least one of ZnO, baO, tiO 2、SnO2; the metal oxide in the doped metal oxide is at least one of ZnO and TiO 2、SnO2, the doping element is at least one of Al, mg, li, in, ga, and the II-VI semiconductor group material is at least one of ZnS, znSe, cdS; the III-V semiconductor material is at least one of InP and GaP; the I-III-VI semiconductor material is at least one selected from CuInS and CuGaS.
In some embodiments, the material of the first electron injection layer is selected from at least one of cesium carbonate, cesium fluoride, cesium azide, and lithium fluoride.
In some embodiments, the first hole transport layer 212 and the second hole transport layer 311 each comprise a hole transport material, the hole transport materials of the first hole transport layer 212 and the second hole transport layer 311 are each independently selected from the group consisting of 4,4'-N, N' -dicarbazolyl-biphenyl (CBP), N '-diphenyl-N, N' -bis (1-naphthyl) -1,1 '-biphenyl-4, 4 "-diamine, N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4,4 '-diamine, N' -bis (3-methylphenyl) -N, N '-bis (phenyl) -spiro (spiro-TPD), N' -bis (4- (N, N '-diphenyl-amino) phenyl) -N, N' -diphenyl benzidine, 4 '-tris (N-carbazolyl) -triphenylamine, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, poly [ (9, 9 '-dioctylfluorene-2, 7-diyl) -co- (4, 4' - (N- (4-sec-butylphenyl) diphenylamine)) ], (poly (4-butylphenyl-diphenylamine) (poly-TPD), polyaniline, polypyrrole, poly (p-phenylene vinylene), poly (phenylenevinylene), poly [ 2-methoxy-5- (2-ethylhexyloxy) -1, 4-phenylenevinylene ] and poly [ 2-methoxy-5- (3 ',7' -dimethyloctyloxy) -1, 4-phenylenevinylene ], copper phthalocyanine, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4' -bis (P-carbazolyl) -1,1' -biphenyl compound, N ' -tetraarylbenzidine, PEDOT: PSS and derivatives thereof, poly (N-vinylcarbazole) (PVK) and derivatives thereof, polymethacrylate and derivatives thereof, poly (9, 9-octylfluorene) and derivatives thereof, poly (spirofluorene) and derivatives thereof, N ' -bis (naphthalen-1-yl) -N, N ' -diphenylbenzidine, spironpb, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO 3, doped or undoped WO 3, doped or undoped V 2O5, doped or undoped P-type gallium nitride, doped or undoped CrO 3, cuO or undoped CuO.
In some embodiments, the material of the first hole injection layer 211 and the second hole injection layer 312 is selected from at least one of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene, PEDOT: PSS, PSS doped with s-MoO3 derivative, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, tetracyanoquinodimethane, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide.
The application also provides a preparation method of the organic light-emitting device, which comprises the following steps:
Sequentially stacking a first electrode, a first light-emitting unit, a charge generation layer, a second light-emitting unit and a second electrode; or sequentially laminating to form a second electrode, a second light-emitting unit, a charge generation layer, a first light-emitting unit and a first electrode;
wherein the charge generation layer is formed by:
And mixing the electron injection material and the hole generation material to obtain a mixed solution, wherein the electron injection material comprises first gold nanoparticles. The first gold nanoparticle may be the first gold nanoparticle described previously. The first gold nanoparticle may be formed by a coordination reaction with the gold nanoparticle using the N-heterocyclic carbene ligand described previously.
The mixed solution is formed on the first light emitting unit or the second light emitting unit by a solution method, and dried to obtain the charge generating layer. The solution method may be printing, ink-jet printing, coating, spin coating, or the like.
Referring to fig. 2, the present application also provides a display panel including the organic light emitting device 100 as described above or the organic light emitting device prepared as described above.
The present application will now be described in more detail by way of the following examples, which are intended to be illustrative of the application and not limiting thereof.
Example 1:
Preparation of component 1 (electron injection material): 0.1mmol of chloroauric acid (HAuCl 4) and 0.2mmol of tetraoctylammonium bromide were dissolved in 10mL of water, 2.5mL of toluene was added and stirred at room temperature for 20min, followed by separation to remove the aqueous phase. 1.2mmol of bis (tetraethyleneglycol monomethyl ether) sulfide was added, and 4.5mL of an aqueous solution of NaBH 4 (12 mmol of NaBH 4) was added under vigorous stirring, and after 30min the aqueous phase was separated off, the organic phase was distilled under reduced pressure and washed 2 times with pentane to give Au-NPs. 32mg of 1, 3-dimethylimidazolium iodide and 5.5mg of sodium t-butoxide were added to a mixture composed of 2mL of dry acetonitrile and 2mL of dry hexane and stirred under Ar for 30min, then 28.5mg of Au-NPs was dissolved in 0.5mL of acetonitrile and the above mixture was added, stirred overnight for ligand exchange, then acetonitrile was separated off, and extracted three times with acetonitrile in hexane to remove the excess ligand, followed by distillation under reduced pressure to a solid.
Preparation of component 2 (hole generating material): 36mL of aqueous chloroauric acid (containing 1.1mmol of HAuCl4) was mixed with 96mL of a toluene solution of tetraoctylammonium bromide (4.8 mmol of tetraoctylammonium bromide) and stirred vigorously until all of the chloroauric acid salt was transferred to the organic layer. Then 2.0mmol of dodecyl mercaptan was added. 30mL of an aqueous solution of NaBH 4 (12 mmol of NaBH 4) were slowly added to the above solution with vigorous stirring, after stirring for 3 hours, the organic phase was concentrated to 5mL after separation of the water, then the excess sulfhydryl was extracted with 200mL of ethanol, then centrifuged and a dark brown precipitate was obtained, washed four times with ethanol and then dried.
Preparation of charge generation layer ink: the solids obtained from component 1 and component 2 were mixed according to a ratio of 1:1 in mass ratio dispersed in xylene as an ink for device fabrication.
Preparing a device: cleaning an ITO anode substrate, and then treating the substrate for 15min under the UV condition to increase the work function and wettability of the substrate; spin-coating PEDOT with the thickness of 30nm to PSS on the treated ITO substrate and baking for 20min at 150 ℃ in an air atmosphere; spin-coating TFB as a hole transport layer on a PEDOT-PSS substrate with a thickness of 30nm, and then baking at 180 ℃ for 60min in a nitrogen environment; spin-coating a 60nm thick polymer light-emitting layer F8BT on a substrate, baking at 150 ℃ for 10min, spin-coating a 10nm thick electron transport layer PFN-Br, annealing at 150 ℃ for 20min, spin-coating the ink prepared above for 20nm thick film, annealing at 150 ℃ for 20min to obtain a charge generation layer, spin-coating a 20nm thick PMA thereon, annealing at 150 ℃ for 20min to obtain a second hole injection layer, spin-coating TFB as a hole transport layer, and baking at 180 ℃ for 60min; then spin-coating a 60nm thick polymer light-emitting layer F8BT on the substrate, baking at 150 ℃ for 10min, finally vacuum evaporating LiF of 1nm and Al of 100nm thickness, finally packaging and annealing at 80 ℃ for 30min.
Example 2: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 5:1, and the other preparation methods were the same as in example 1.
Example 3: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 1:5, and the other preparation methods were the same as in example 1.
Example 4: the ligand precursor added during the reaction in component 1 was replaced with 1, 3-diisopropylimidazolium iodide (R1 is isopropyl), and the other preparation method was the same as in example 1.
Example 5: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 2:1, and the other preparation methods were the same as in example 1.
Example 6: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 1:2, and the other preparation methods were the same as in example 1.
Example 7: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 5.1:1, and the other preparation methods were the same as in example 1.
Example 8: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 1:5.1, and the other preparation methods were the same as in example 1.
Comparative example 1: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 10:1, and the other preparation methods were the same as in example 1.
Comparative example 2: the mass ratio of component 1 to component 2 in the charge generation layer 50 was 1:10, and the other preparation methods were the same as in example 1.
The light emitting device performance of examples 1 to 8 and comparative examples 1 and 2 was tested.
The driving voltage and current efficiency are measured by using a Friedel-crafts FPD optical characteristic measuring device, through an efficiency testing system built by a LabView control QE PRO spectrometer, keithley 2400 and Keithley 6485, parameters such as voltage, current, brightness, luminescence spectrum and the like are measured, and the driving voltage and current efficiency are obtained through calculation. The corresponding driving voltage and current efficiency at 1000nit with the current density of 10mA/cm 2 are obtained from an efficiency test system built by Keithley 6485.
The service life T95@1000nit is tested by adopting a 128-path service life testing system customized by Guangzhou New FOV company, the system architecture is that a 2mA constant current source drives a light emitting device, a photodiode detector and the testing system test the brightness (photocurrent) change of the light emitting device, a luminance meter tests and calibrates the brightness (photocurrent) of the light emitting device to obtain the time when the initial brightness of the light emitting device is attenuated to 95%, and the time when the initial brightness of the light emitting device is attenuated to 95% is converted to the aging time under 1000nit to obtain the service life T95@1000nit.
The test results of drive voltage, current efficiency, and T95 are referred to in the table one.
List one
According to examples 1 to 8 and comparative examples 1 and 2 of the present application, when the mass ratio of the electron injecting material and the hole generating material in the charge generating layer 50 is 1 (0.2 to 5) and the vicinity thereof, the driving voltage is significantly reduced compared with the device not within the guard period. When the mass ratio of the electron injection material to the hole generation material is 1 (0.2-5), the current density and the device lifetime are also improved. Further, when the mass ratio of the electron injecting material to the hole generating material is 1 (0.5 to 1), the driving voltage of the device is further reduced, the lifetime and the efficiency are further improved, indicating that the electron injecting capability into the light emitting layer is improved. Also, as is clear from a comparison of examples 1 to 8 with comparative examples 1 and 2, when the proportion of any one of the components is excessively high, the charge separation ability thereof is lowered due to its unidirectional charge transport ability, and the device performance is deteriorated.
The foregoing has provided a detailed description of embodiments of the application, with specific examples being set forth herein to provide a thorough understanding of the application. Meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present application, the present description should not be construed as limiting the present application.
Claims (13)
1. An organic light emitting device, comprising:
A first electrode, a first light emitting unit, a charge generating layer, a second light emitting unit, and a second electrode, which are sequentially stacked;
The charge generation layer comprises an electron injection material and a hole generation material, the electron injection material comprises first gold nanoparticles, and the surfaces of the first gold nanoparticles are modified by N-heterocyclic carbene ligands.
2. The organic light-emitting device according to claim 1, wherein the hole-generating material comprises:
At least one of second gold nanoparticles and third gold nanoparticles, wherein the surfaces of the second gold nanoparticles are not modified by ligands, and the surfaces of the third gold nanoparticles are combined with first ligands.
3. The organic light-emitting device according to claim 2, wherein the first ligand is selected from at least one of an acid ligand, a thiol ligand, an amine ligand, a phosphine oxide ligand, a phospholipid, a soft phospholipid, and a polyvinylpyridine.
4. The organic light-emitting device of claim 1, wherein the N-heterocyclic carbene ligand is selected from at least one of the following structural formulas:
Wherein the N-heterocyclic carbene ligand coordinates with gold atoms on the surfaces of the gold nanoparticles through lone pair electrons on carbon atoms between two nitrogen atoms;
each occurrence of R 1 is independently selected from at least one of the following structural formulas:
R 2 and R 3 are each independently selected from H, alkyl or alkoxy groups containing 1 to 12 carbon atoms, amino, hydroxyl, mercapto, carboxyl.
5. The organic light-emitting device of claim 4, wherein the first gold nanoparticle is selected from at least one of the following structures:
wherein n is a positive integer greater than 1, and Au represents gold nanoparticles.
6. The organic light-emitting device of claim 4, wherein the N-heterocyclic carbene ligand is selected from at least one of the following structural formulas:
7. The organic light-emitting device according to any one of claims 1 to 6, wherein a mass ratio of the electron injection material to the hole generation material is 1 (0.2 to 5).
8. An organic light-emitting device according to any one of claims 1 to 6, wherein a mass ratio of the electron injecting material to the hole generating material is 1 (0.5 to 2).
9. The organic light-emitting device according to claim 2, wherein the first gold nanoparticles have an average particle diameter of 2nm to 10nm, and/or
The second gold nanoparticles have an average particle size of 2nm to 10nm, and/or
The third gold nanoparticles have an average particle diameter of 2nm to 10nm.
10. The organic light-emitting device according to claim 9, wherein the first light-emitting unit includes a first hole functional layer, a first light-emitting layer, and a first electron functional layer, which are sequentially stacked, the first hole functional layer being disposed close to the first electrode, the first electron functional layer being disposed close to the charge generation layer;
The second light-emitting unit comprises a second hole functional layer, a second light-emitting layer and a second electronic functional layer which are sequentially stacked, wherein the second hole functional layer is close to the charge generation layer, and the second electronic functional layer is close to the second electrode.
11. The organic light-emitting device according to claim 10, wherein the first hole-functional layer comprises a first hole-injecting layer and a first hole-transporting layer, the first electron-functional layer comprises a first electron-transporting layer, the second hole-functional layer comprises a second hole-transporting layer and a second hole-injecting layer, and the second electron-functional layer comprises a first electron-injecting layer and a second electron-transporting layer;
The first electrode and the second electrode are respectively and independently selected from a doped metal oxide particle electrode, a composite electrode, a graphene electrode, a carbon nano tube electrode, a metal simple substance electrode or an alloy electrode, wherein the material of the doped metal oxide particle electrode is selected from one or more of indium doped tin oxide, fluorine doped tin oxide, antimony doped tin oxide, aluminum doped zinc oxide, gallium doped zinc oxide, indium doped zinc oxide, magnesium doped zinc oxide and aluminum doped magnesium oxide, the composite electrode is selected from AZO/Ag/AZO、AZO/Al/AZO、ITO/Ag/ITO、ITO/Al/ITO、ZnO/Ag/ZnO、ZnO/Al/ZnO、TiO2/Ag/TiO2、TiO2/Al/TiO2、ZnS/Ag/ZnS or ZnS/Al/ZnS, and the material of the metal electrode is selected from one or more of Ag, al, cu, au, mo, pt, ca and Ba; and/or
The materials of the first light-emitting layer and the second light-emitting layer are selected from one or more of organic light-emitting materials, wherein the organic light-emitting materials are selected from one or more of 4,4' -bis (N-carbazole) -1,1' -biphenyl, tris [2- (p-tolyl) pyridine iridium (III), 4' -tris (carbazole-9-yl) triphenylamine, tris [2- (p-tolyl) pyridine iridium, diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, blue light-emitting TBPe fluorescent materials, green light-emitting TTPX fluorescent materials, orange light-emitting TBRb fluorescent materials, red light-emitting DBP fluorescent materials, delayed fluorescent materials, TTA materials, heat-activated delayed materials, polymers containing B-N covalent bonds, hybrid local charge transfer excited state materials and excited compound luminescent materials; and/or
The first electron transport layer and the second electron transport layer each comprise an electron transport material, the electron transport materials are respectively and independently selected from at least one of metal oxide, doped metal oxide, II-VI semiconductor material, III-V semiconductor material and I-III-VI semiconductor material, and the metal oxide is selected from at least one of ZnO, baO, tiO 2、SnO2; the metal oxide in the doped metal oxide is at least one of ZnO and TiO 2、SnO2, the doping element is at least one of Al, mg, li, in, ga, and the II-VI semiconductor group material is at least one of ZnS, znSe, cdS; the III-V semiconductor group material is at least one of InP and GaP; the I-III-VI semiconductor material is at least one of CuInS and CuGaS; and/or
The material of the first electron injection layer is at least one selected from cesium carbonate, cesium fluoride, cesium azide and lithium fluoride; and/or
The first hole transport layer and the second hole transport layer each comprise a hole transport material independently selected from the group consisting of 4,4'-N, N' -dicarbazolyl-biphenyl (CBP), N '-diphenyl-N, N' -bis (1-naphthyl) -1,1 '-biphenyl-4, 4 "-diamine, N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4,4 '-diamine, N' -bis (3-methylphenyl) -N, N '-bis (phenyl) -spiro (spiro-TPD), N, N' -bis (4- (N, N '-diphenyl-amino) phenyl) -N, N' -diphenyl benzidine, 4 '-tris (N-carbazolyl) -triphenylamine, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, poly [ (9, 9 '-dioctylfluorene-2, 7-diyl) -co- (4, 4' - (N- (4-sec-butylphenyl) diphenylamine)) ], poly (4-butylphenyl-diphenylamine) (poly-TPD), polyaniline, polypyrrole, poly (p-phenylene vinylene), poly (p-phenylene vinylene), poly [ 2-methoxy-5- (2-ethylhexyl oxy) -1, 4-phenylenevinylene ] and poly [ 2-methoxy-5- (3 ',7' -dimethyloctyl oxy) -1, 4-phenylenevinylene ], copper phthalocyanines, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4' -bis (P-carbazolyl) -1,1' -biphenyl compounds, N ' -tetraarylbenzidine, PEDOT: at least one of PSS and derivatives thereof, poly (N-vinylcarbazole) (PVK) and derivatives thereof, polymethacrylate and derivatives thereof, poly (9, 9-octylfluorene) and derivatives thereof, poly (spirofluorene) and derivatives thereof, N ' -di (naphthalen-1-yl) -N, N ' -diphenyl benzidine, spironpb, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO 3, doped or undoped WO 3, doped or undoped V 2O5, doped or undoped P-type gallium nitride, doped or undoped CrO 3, doped or undoped CuO; and/or
The materials of the first hole injection layer and the second hole injection layer are selected from at least one of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene, PEDOT, PSS doped with s-MoO3 derivatives, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine, tetracyanoquinodimethane, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide and copper oxide.
12. A method of manufacturing an organic light emitting device, comprising:
Sequentially stacking a first electrode, a first light-emitting unit, a charge generation layer, a second light-emitting unit and a second electrode; or sequentially laminating to form a second electrode, a second light-emitting unit, a charge generation layer, a first light-emitting unit and a first electrode;
wherein the charge generation layer is formed by:
mixing an electron injection material and a hole generation material to obtain a mixed solution, wherein the electron injection material comprises first gold nanoparticles, and the surfaces of the first gold nanoparticles are modified by N-heterocyclic carbene ligands;
the mixed solution is formed on the first light emitting unit or the second light emitting unit by a solution method, and dried to obtain the charge generating layer.
13. A display panel comprising the organic light-emitting device according to any one of claims 1 to 11 or an organic light-emitting device produced by the method for producing an organic light-emitting device according to claim 12.
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| CN118284111A true CN118284111A (en) | 2024-07-02 |
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