CN112750954B - Electroluminescent diode device, preparation method thereof and display device - Google Patents

Electroluminescent diode device, preparation method thereof and display device Download PDF

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CN112750954B
CN112750954B CN202010210781.2A CN202010210781A CN112750954B CN 112750954 B CN112750954 B CN 112750954B CN 202010210781 A CN202010210781 A CN 202010210781A CN 112750954 B CN112750954 B CN 112750954B
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ligand
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CN112750954A (en
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眭俊
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Guangdong Juhua Printing Display Technology Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

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Abstract

The invention discloses an electroluminescent diode device, a preparation method thereof and a display device, wherein the electroluminescent diode device comprises a cathode, an electron transport layer, a first ligand layer, a luminescent layer, a second ligand layer, a hole transport layer and an anode; wherein the light emitting layer comprises quantum dots and surface ligands bound to the quantum dots; the material of the first ligand layer is an amide compound; the material of the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound. The first ligand layer can effectively prevent electrons from being injected into the light-emitting layer, the second ligand layer can effectively promote holes to be injected into the light-emitting layer, and the first ligand layer and the second ligand layer act together to balance the number of carriers in the light-emitting layer, so that the light-emitting performance of the device can be improved, and the service life and the stability of the device can be improved.

Description

Electroluminescent diode device, preparation method thereof and display device
Technical Field
The invention relates to the technical field of electronic display, in particular to an electroluminescent diode device, a preparation method thereof and a display device.
Background
The electroluminescent diode can directly convert electric energy into light energy, and is applied to various places needing illumination or display in daily production and life of human beings. The quantum dot light-emitting diode (QLED) uses quantum dots as a light-emitting active layer, has the advantages of saturated emergent light color and adjustable wavelength, and has high photoluminescence and electroluminescence quantum yield, and has obvious advantages compared with the traditional organic light-emitting diode (OLED).
A typical quantum dot light emitting diode includes: an anode layer, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a quantum dot light emitting layer (EML), an Electron Transport Layer (ETL), and a cathode layer. In the traditional technology, the HOMO energy level of organic micromolecules or polymers used by a hole transport layer is generally between 5.2 and 5.8, and the HOMO energy level of quantum dots used by a quantum dot light-emitting layer is generally more than 6.3, so that a large potential barrier needs to be spanned when holes are transported from the hole transport layer to the quantum dot light-emitting layer; in addition, the LUMO level of the inorganic nano oxide used in the electron transport layer is about 4, and the difference between the LUMO level of the inorganic nano oxide and the LUMO level of the quantum dot is small, so that a potential barrier which needs to be crossed when electrons are transported from the electron transport layer to the quantum dot light emitting layer is small. The combined action of the above factors causes the number of the holes and the electrons finally transmitted to the quantum dot luminescent layer to be unbalanced, so that the problems of charge of the quantum dots, non-radiative luminescence such as Auger recombination and the like are caused, and meanwhile, the redundant electrons can be transmitted to the hole transport layer to influence the performance and the service life of the hole transport layer.
Therefore, the current electroluminescent diode device, the manufacturing method thereof and the display device still need to be improved.
Disclosure of Invention
In view of the above problems, it is desirable to provide an electroluminescent diode device, a display device and a manufacturing method capable of balancing the number of carriers transmitted to a quantum dot light emitting layer.
The technical scheme for solving the technical problems is as follows.
An electroluminescent diode device comprising:
the cathode, the electron transport layer, the first ligand layer, the luminescent layer, the second ligand layer, the hole transport layer and the anode are sequentially stacked;
wherein the light emitting layer comprises quantum dots and surface ligands bound to the quantum dots;
the material of the first ligand layer is an amide compound;
the material of the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
In one embodiment, at least a portion of the material of the first ligand layer is in ligand exchange with the surface ligands; and/or
At least a portion of the material of the second ligand layer is in ligand exchange with the surface ligands.
In one embodiment, the amide compound is selected from: at least one of N-ethyl-5-methyl-2- (1-methylethyl) cyclohexanecarboxamide, 4-methoxybenzamide, 2, 4-dihydroxybenzamide, valeramide, and N, N, N ', N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine.
In one embodiment, the bidentate aliphatic compound is selected from: at least one of 1, 12-dimercaptododecane and 1, 12-diaminododecane; and/or
The bidentate aromatic compound is selected from: at least one of 2, 2-iminodibenzoic acid, 2-iminobenzhydrylamine, 2-iminodithiol, 1, 2-benzenedithiol, and 1, 3-benzenedithiol; and/or
The monodentate bidentate aliphatic compound is selected from: at least one of 12-aminododecane-1-thiol and 13-aminotridenoic acid.
In one embodiment, the quantum dots are core-shell structured quantum dots; the core material of the core-shell structure quantum dot is selected from: at least one of CdSe, CdS, ZnSe, ZnS, CdTe, CdZnS, CdZnSe, ZnSeS, ZnSeTe, ZnTeS, CdSeS, CdSeTe, CdTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdSeSTe, ZnSeTe, CdZnSeTe, InP, InAs and InAsP;
the shell material of the core-shell structure quantum dot is selected from: at least one of CdS, ZnSe, ZnS, CdSeS and ZnSeS.
In one embodiment, the surface ligand is selected from at least one of oleic acid, oleylamine and trioctylphosphine.
In one embodiment, the material of the electron transport layer is selected from: at least one of zinc oxide, barium oxide and titanium dioxide.
In one embodiment, the material of the hole transport layer is selected from: n, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), poly (N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine) (poly-TPD), Polyvinylcarbazole (PVK), 4 '-bis (9-Carbazole) Biphenyl (CBP), N' -diphenyl-N, N '- (1-naphthyl) -1, 1' -biphenyl-4, 4 '-diamine (NPB), 4' -tris (carbazol-9-yl) triphenylamine (TCTA), poly (9, 9-dioctylfluorene-CO-N- (4-butylphenyl) diphenylamine) (TFB), At least one of 4, 7-diphenyl-1, 10-phenanthroline (mCP) and 4, 4' -cyclohexylbis (N, N-bis (4-methylphenyl) aniline) (TAPC).
In addition, the invention also provides a preparation method of the electroluminescent diode device, which comprises the following steps:
sequentially forming a cathode, an electron transport layer, a first ligand layer, a luminescent layer, a second ligand layer, a hole transport layer and an anode on a substrate; or
Sequentially forming an anode, a hole transport layer, a second ligand layer, a luminescent layer, a first ligand layer, an electron transport layer and a cathode on a substrate;
wherein the light emitting layer comprises quantum dots and surface ligands bound to the quantum dots;
the first ligand layer is an amide compound;
the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
The invention also provides a display device comprising an electroluminescent diode device as described in any of the above embodiments; or, the electroluminescent diode device prepared according to the method for preparing an electroluminescent diode device described in any of the above embodiments.
According to the electroluminescent diode device provided by the invention, the amide compound is used as the first ligand layer, on one hand, the amide compound can effectively reduce the Fermi level of the electron transport layer, so that the LUMO level is reduced, the potential barrier which needs to be spanned by electron injection is increased, and the electron injection is hindered; on the other hand, the amide compound is easy to perform dense ligand exchange with the original surface ligand on the surface of the quantum dot shell layer, so that the dense wrapping of the ligand on the surface of the quantum dot shell layer is realized, and the electron injection of a light-emitting layer is further reduced.
And, the electroluminescent diode device further incorporates at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound as the second ligand layer. The compound can reduce the HOMO energy level of the quantum dot through the interface dipole effect, thereby reducing the hole injection barrier of the quantum dot and promoting the injection of holes. More importantly, the endpoints of the bidentate compound and the monodentate bidentate compound contain two functional groups, one end of each functional group can be tightly combined with the quantum dot shell layer, namely, at least one part of the material of the second ligand layer is subjected to ligand exchange with the original surface ligand on the surface of the quantum dot shell layer, so that the ligand is not easy to fall off, the surface ligand of the quantum dot is not reduced in the conversion process from a solution state to a solid film layer, and the injection of holes is further promoted; the other end can change the surface energy of the quantum dots, reduce the contact angle between the hole transport layer and the luminescent layer, reduce the interface defect between the two layers and increase the injection amount of the holes. The two ligand layers act together to effectively balance the number of carriers in the light-emitting layer, so that the light-emitting performance of the device is improved, and the service life of the device is prolonged.
Drawings
FIG. 1 is a schematic diagram of an embodiment of an electroluminescent diode device;
fig. 2 is a schematic diagram of a process of forming a first ligand layer, a light emitting layer and a second ligand layer in a method of manufacturing an electroluminescent diode device according to an embodiment;
reference numerals:
110: a substrate; 120: a cathode; 130: an electron transport layer; 140: a first ligand layer; 150: a light emitting layer; 160: a second ligand layer; 170: a hole transport layer; 180: a hole injection layer; 190: and an anode.
Detailed Description
To facilitate an understanding of the invention, the invention will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. "Multi", as used herein, means a combination of two or more items.
As shown in fig. 1, a schematic diagram of an electroluminescent diode device obtained according to example 1 includes: the cathode 120, the electron transport layer 130, the first ligand layer 140, the light emitting layer 150, the second ligand layer 160, the hole transport layer 170, and the anode 190 are sequentially stacked. Wherein the light emitting layer 150 includes quantum dots and surface ligands bound to the quantum dots. The material of the first ligand layer 140 is an amide compound, and the material of the second ligand layer 160 is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
More specifically, the electroluminescent diode device may further include a substrate 110, a hole injection layer 180, the cathode 120 being disposed on the substrate 110, the hole injection layer 180 being disposed between the hole transport layer 170 and the anode 190.
It is to be understood that the above device structure is an inverted structure commonly used in light emitting diodes, and it is not departing from the present invention if it is inverted layer by layer into an inverted structure. For example, the anode 190 is provided on the substrate 110, the hole injection layer 180 is provided on the anode 190, the hole transport layer 170 is provided on the hole injection layer 180, the second distribution layer 160 is provided on the hole transport layer 170, the light-emitting layer 150 is provided on the second distribution layer 160, the first distribution layer 140 is provided on the light-emitting layer 150, the electron transport layer 130 is provided on the first distribution layer 140, and the cathode 120 is provided on the electron transport layer 130.
The present invention only takes the inverted structure as an example to illustrate the electroluminescent diode device provided in the above embodiments, and the materials and functions of the layers of the inverted structure are not different.
The substrate 110 may include a rigid substrate such as glass, a metal foil, etc., which is commonly used, or a flexible substrate such as Polyimide (PI), Polycarbonate (PC), Polystyrene (PS), Polyethylene (PE), polyvinyl chloride (PV), polyvinyl pyrrolidone (PVP), polyethylene terephthalate (PET), etc., which mainly serves as a support.
The cathode 120 is disposed above the substrate 110, and mainly plays a role of conducting electrons, and the cathode 120 may be made of a common cathode conductive material, such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO) conductive glass or indium tin oxide, an indium zinc oxide electrode, other metal materials such as aluminum, silver, magnesium-silver alloy, and the like, and a conductive carbon material such as graphite, carbon nanotube, graphene, carbon fiber, and the like.
An electron transport layer 130 is disposed over the cathode 120, and the material of the electron transport layer 130 is selected from materials having electron transport properties, such as zinc oxide, barium oxide, titanium dioxide, tin dioxide, aluminum zinc oxide, indium tin oxide, and the like. As some specific examples, the material of the electron transport layer 130 may be selected from at least one of zinc oxide, barium oxide, and titanium dioxide.
The first ligand layer 140 is disposed above the electron transport layer 130, and the material thereof is an amide compound.
The amide compound refers to an organic compound containing an amide bond, and is preferably selected from amide small-molecular compounds, and the molecular weight of the amide small-molecular compounds is 10-1000. For example, the amide compound may be selected from: n-ethyl-5-methyl-2- (1-methylethyl) cyclohexanecarboxamide (C) 13 H 25 NO), 4-methoxybenzamide (C) 8 H 9 NO 2 ) 2, 4-dihydroxybenzamide (C) 7 H 7 NO 3 ) Valeramide (C) 5 H 11 NO), N, N, N ', N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine (C) 22 H 48 N 10 O 4 ) At least one of (1). As a specific example, N, N, N ', N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine (C) may be used 22 H 48 N 10 O 4 ) As the material of the first ligand layer 140. The amide group can greatly reduce the Fermi level of the electron transport layer, so that the LUMO and HOMO levels of the electron transport layer are reduced, and a higher potential barrier is required to be spanned by electrons from the LUMO level of the electron transport layer to the LUMO level of the quantum dot, so that electron injection is inhibited.
Further, the amide small molecules have a smaller molecular weight and are more densely distributed in space than the large molecules, and therefore, when at least a part of the material of the first ligand layer is ligand-exchanged with the surface ligands, that is, when the first ligand layer 140 is ligand-exchanged with the surface ligands originally present in the quantum dots of the light-emitting layer, a denser and larger amount of ligand exchange can be achieved. More ligands are loaded on the surface of the quantum dot shell layer, so that the injection of electrons can be effectively reduced.
The light emitting layer 150 is disposed above the first ligand layer 140, and the material of the light emitting layer 150 is a quantum dot with a core-shell structure. The core layer quantum dot material of the core-shell structure quantum dot can be selected from: CdSe, CdS, ZnSe, ZnS, CdTe, CdZnS, CdZnSe, ZnSeS, ZnSeTe, ZnTeS, CdSeS, CdSeTe, CdTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdSeSTe, ZnSeTe, CdZnSeTe, InP, InAs and InAsP, the shell quantum dot material of the core-shell structure quantum dot can be selected from at least one of: at least one of CdS, ZnSe, ZnS, CdSeS and ZnSeS. Compared with the traditional organic light-emitting diode, the quantum dot light-emitting diode has the advantages of saturated emergent light color and adjustable wavelength, so that the quantum dot light-emitting diode is considered to be a new generation display device with great potential for realizing industrialization.
The second ligand layer 160 is disposed over the light emitting layer 150. The material of the second ligand layer 160 is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
Bidentate aliphatic compounds, bidentate aromatic compounds refer to organic compounds having two identical substituents, such as mercapto, amino and carboxyl groups, attached to the carbon chain ends or to the benzene ring, e.g. 1, 12-dimercaptododecane (C) 12 H 26 S 2 ) 1, 12-diaminododecane (C) 12 H 28 N 2 ) 2, 2-iminodibenzoic acid (C) 14 H 11 NO 4 ) 2, 2-iminobenzhydrylamine (C) 12 H 13 N 3 ) 2, 2-iminodithiol (C) 12 H 11 NS 2 ) 1, 2-benzenedithiol (C) 6 H 6 S 2 ) And 1, 3-benzenedithiol (C) 6 H 6 S 2 ). Monodentate bidentate aliphatic compounds are organic compounds having two different substituents (e.g., mercapto, amino, and carboxyl) attached to each end of the carbon chain, such as 12-aminododecane-1-thiol (C) 12 H 27 NS) and 13-aminotridecanoic acid (C) 13 H 27 NO 2 ). As a specific example, at least one of 2, 2-iminobenzhydrylamine, 12-aminododecane-1-thiol, and 13-aminotridecanoic acid may be selected as the material of the second ligand layer 160.
More preferably, the material of the second ligand layer is 12-aminododecane-1-thiol.
One function of the substances is to reduce the HOMO energy level of the quantum dot, thereby reducing the potential barrier that holes need to cross from the hole transport layer 170 to the light emitting layer 150 and promoting the injection of the holes; the substance has another effect that two groups in the molecule can be connected with the quantum dot shell layer, namely at least one part of the material of the second ligand layer is subjected to ligand exchange with the surface ligand on the surface of the quantum dot, so that the defect density of the quantum dot shell layer is greatly reduced, and the binding energy of the substituent and the quantum dot shell layer is larger than that of the original ligand and the quantum dot shell layer, so that the ligand falling amount can be reduced when the quantum dot is converted into a solid film layer from a solution state. The material has another function that the contact angle between the hole transport layer 170 and the light-emitting layer 150 can be effectively reduced by the redundant groups on the surface, so that the defects between the two layers are reduced, the two layers are in closer contact, and the injection of holes is promoted.
The first ligand layer 140 can effectively block the injection of electrons, the second ligand layer 160 can effectively promote the injection of holes, and the two layers cooperate to balance the number of carriers in the light-emitting layer 150, so that the light-emitting performance of the device is improved, and the service life of the device is prolonged.
The material of the hole transport layer 170 may be selected from materials having a hole transporting effect, such as N, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), poly (N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine) (poly-TPD), Polyvinylcarbazole (PVK), 4 '-bis (9-Carbazole) Biphenyl (CBP), N' -diphenyl-N, N '- (1-naphthyl) -1, 1' -biphenyl-4, 4 '-diamine (NPB), 4', 4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), poly (9, 9-dioctylfluorene-CO-N- (4-butylphenyl) diphenylamine) (TFB), 4, 7-diphenyl-1, 10-phenanthroline (mCP), 4 '-cyclohexylbis (N, N-bis (4-methylphenyl) aniline) (TAPC) and poly (9, 9-dioctylfluorene-co-bis-N, N' phenyl-1, 4-Phenylenediamine) (PFB).
The material of the hole injection layer 180 may be selected from materials having a hole injection capability. The material can be selected fromPoly (3, 4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT: PSS), copper phthalocyanine (CuPc), 2,3,5, 6-tetrafluoro-7, 7 ', 8, 8' -tetracyanoquino-dimethane (F4-TCNQ), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazatriphenylene (HATCN), 4 ', 4' -tris (3-methylphenylamino) triphenylamine (m-MADATA), nickel oxide (NiO) x ) Tungsten trioxide (WO) 3 ) And molybdenum trioxide (MoO) 3 ) At least one of (1).
The anode 190 is disposed above the hole injection layer 180, and may be selected from materials capable of conducting holes, such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), conductive glass or indium tin oxide, and indium zinc oxide electrodes, and may also be other metal materials, such as gold, silver, aluminum, and the like.
An embodiment of the present invention also provides a method for manufacturing an electroluminescent diode device, which may be the electroluminescent diode device described above, and thus, may have all the features and advantages of the electroluminescent diode device described above. The method comprises the following steps.
Sequentially forming a cathode, an electron transport layer, a first ligand layer, a luminescent layer, a second ligand layer, a hole transport layer and an anode on a substrate; or
Sequentially forming an anode, a hole transport layer, a second ligand layer, a luminescent layer, a first ligand layer, an electron transport layer and a cathode on a substrate;
the light-emitting layer is a quantum dot light-emitting layer and comprises quantum dots and surface ligands combined with the quantum dots.
Preferably, at least a portion of the material of the first ligand layer is in ligand exchange with surface ligands of the quantum dots; and/or
At least a portion of the material of the second ligand layer is in ligand exchange with the surface ligands of the quantum dots.
Preferably, in the production method, a step of forming a hole injection layer is further included between the formation of the anode and the formation of the hole transport layer.
The material of the first ligand layer is an amide compound.
The material of the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
Wherein the electron transport layer, the hole transport layer and the hole injection layer are each independently formed by a method of evaporation, coating, spin coating or ink jet printing.
The first ligand layer, the light emitting layer and the second ligand layer are each independently formed by a method of coating, spin coating or ink jet printing.
The cathode and the anode are formed independently by evaporation.
Fig. 2 shows a schematic process diagram of sequentially forming a first ligand layer, a quantum dot light-emitting layer, and a second ligand layer on an electron transport layer.
It should also be understood that for the fabrication of the electroluminescent diode device with the front-side structure, the order of the fabrication of the anode, the hole injection layer, the hole transport layer, the second ligand layer, the light-emitting layer, the first ligand layer, the electron transport layer and the cathode need only be changed to form the anode, the hole injection layer, the hole transport layer, the second ligand layer, the light-emitting layer, the first ligand layer, the electron transport layer and the cathode on the substrate in sequence, which is not described herein in detail.
As a practical specific example, the preparation method may include the following steps.
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the metal oxide ink on the ITO cathode in a spin-coating mode, and carrying out annealing treatment after vacuum drying film forming to form the electron transmission layer. The metal oxide ink may be specifically a zinc oxide ink.
(2) The amide compound is dissolved in methanol and spin-coated on the electron transport layer by spin coating, and then the excess amide compound is washed away by using methanol to form a first ligand layer, and as a specific example, the amide compound is N, N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine.
(3) Preparing a luminescent layer on the first ligand layer, spin-coating the quantum dot ink on the first ligand layer, vacuum drying to form a film, and annealing to form the luminescent layer. The material of the luminescent layer is quantum dots with a core-shell structure. The surface of the quantum dot shell layer also contains a surface ligand, and the surface ligand can be at least one of oleic acid, oleylamine and trioctylphosphine.
(4) A second ligand layer is formed on the light-emitting layer. The material of the second ligand layer was dissolved in methanol and spin-coated on the light-emitting layer, and then the excess material of the second ligand layer was washed away using methanol to form a second ligand layer. The substance of the second ligand layer is at least one selected from the group consisting of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound.
(5) A hole transport layer is formed on the second ligand layer. The material of the hole transport layer may be evaporated on the second ligand layer.
(6) A hole injection layer is formed on the hole transport layer. The material of the hole injection layer may be evaporated on the hole transport layer.
(7) An anode is formed on the hole injection layer. The anode may be formed by evaporation.
(8) And (6) packaging.
On the other hand, the invention also provides a display device comprising the electroluminescent diode device or the electroluminescent diode device prepared by the preparation method of the electroluminescent diode device, and the display device has better luminous performance and longer service life. The display device may have all the features and advantages of the electroluminescent diode device or the method as described above.
For a better understanding and appreciation of the invention, reference is also made to the following more detailed examples, which are easier to be construed to practice. Embodiments and advantages of the present invention will also be apparent from the following description of specific examples.
The starting materials used in the following examples and comparative examples were all conventionally available from the market unless otherwise specified.
Example 1
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Dissolving N, N, N ', N' -tetra (N- (2-aminoethyl) propionamido) ethylenediamine in methanol, spin-coating the solution on the electron transport layer by spin coating at 3000rpm for 30s, and washing off the excess amide compound by using methanol to form a first ligand layer.
(3) Preparing a luminescent layer on the first ligand layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the first ligand layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(4) A second ligand layer is formed on the light-emitting layer. The bidentate aromatic compound 2, 2-imino benzhydrylamine is dissolved in methanol and spin-coated on the light-emitting layer, the rotation speed in the spin-coating process is 3000rpm, the spin-coating time is 20s, and then the excess 2, 2-imino benzhydrylamine is washed away by using methanol to form a second ligand layer.
(5) CBP was evaporated on the second ligand layer to form a hole transport layer having a thickness of 45 nm.
(6) Adding MoO 3 And evaporating the mixture on the hole transport layer to form a hole injection layer with the thickness of 35 nm.
(7) And evaporating metal aluminum on the hole injection layer to form an anode, wherein the thickness of the anode is 100 nm.
(8) And packaging to obtain the QLED device.
Example 2
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Dissolving N, N, N ', N' -tetra (N- (2-aminoethyl) propionamido) ethylenediamine in methanol, spin-coating the solution on the electron transport layer by spin coating at 3000rpm for 30s, and washing off the excess amide compound by using methanol to form a first ligand layer.
(3) Preparing a luminescent layer on the first ligand layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the first ligand layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(4) A second ligand layer is formed on the light-emitting layer. The monodentate bidentate aliphatic compound 12-aminododecane-1-thiol was dissolved in methanol and spin-coated on the light-emitting layer at 3000rpm for 20s during the spin-coating process, and then excess 12-aminododecane-1-thiol was rinsed off with methanol to form a second ligand layer.
(5) And spin-coating the TFB ink on the second ligand layer, and then vacuum-drying to form a film, thereby forming a hole transport layer with the thickness of 65 nm.
(6) And spin-coating PEDOT (PSS) ink on the hole transport layer to form a hole injection layer with the thickness of 30 nm.
(7) And evaporating metal aluminum on the hole injection layer to form an anode, wherein the thickness of the anode is 100 nm.
(8) And packaging to obtain the QLED device.
Example 3
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Dissolving N, N, N ', N' -tetra (N- (2-aminoethyl) propionamido) ethylenediamine in methanol, spin-coating the solution on the electron transport layer by spin coating at 3000rpm for 30s, and washing off the excess amide compound by using methanol to form a first ligand layer.
(3) Preparing a luminescent layer on the first ligand layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the first ligand layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(4) A second ligand layer is formed on the light-emitting layer. The bidentate aliphatic compound 1, 12-diaminododecane was dissolved in methanol and spin-coated on the light-emitting layer at 3000rpm for 20s during the spin-coating process, and then excess 1, 12-diaminododecane was rinsed off with methanol to form a second ligand layer.
(5) And spin-coating the TFB ink on the second ligand layer, and then vacuum-drying to form a film, thereby forming a hole transport layer with the thickness of 65 nm.
(6) And spin-coating PEDOT (PSS) ink on the hole transport layer to form a hole injection layer with the thickness of 30 nm.
(7) And evaporating metal aluminum on the hole injection layer to form an anode with the thickness of 100 nm.
(8) And packaging to obtain the QLED device.
Comparative example 1 (without first and second ligand layers)
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Preparing a luminescent layer on the electron transport layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the electron transport layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(3) A hole transport layer is formed on the light emitting layer. The TFB ink was spin-coated onto the second ligand layer and then vacuum dried to a film thickness of 65 nm.
(4) And spin-coating PEDOT (PSS) ink on the hole transport layer to form a hole injection layer with the thickness of 30 nm.
(5) And evaporating metal aluminum on the hole injection layer to form an anode, wherein the thickness of the anode is 100 nm.
(6) And packaging to obtain the QLED device.
COMPARATIVE EXAMPLE 2 (without second ligand layer)
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Dissolving N, N, N ', N' -tetra (N- (2-aminoethyl) propionamido) ethylenediamine in methanol, spin-coating the solution on the electron transport layer by spin coating at 3000rpm for 30s, and washing off the excess amide compound by using methanol to form a first ligand layer.
(3) Preparing a luminescent layer on the first ligand layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the first ligand layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(4) A hole transport layer is formed on the light emitting layer. The TFB ink was spin-coated onto the second ligand layer and then vacuum dried to a film thickness of 65 nm.
(5) And spin-coating PEDOT (PSS) ink on the hole transport layer to form a hole injection layer with the thickness of 30 nm.
(6) And evaporating metal aluminum on the hole injection layer to form an anode, wherein the thickness of the anode is 100 nm.
(7) And packaging to obtain the QLED device.
Comparative example 3 (without first ligand layer)
(1) Preparing an ITO cathode on a glass substrate in an evaporation mode; and spin-coating the zinc oxide ink on the ITO cathode in a spin-coating manner, vacuum drying to form a film, and then annealing at 120 ℃ for 15min to form an electron transmission layer with the thickness of 45 nm.
(2) Preparing a luminescent layer on the electron transport layer, spin-coating CdZnS (core material)/ZnS (shell material) quantum dot ink on the electron transport layer, vacuum drying to form a film, and annealing at 100 ℃ for 10min to form the luminescent layer with the thickness of 20 nm. The surface ligand of the quantum dot is oleic acid.
(3) A second ligand layer is formed on the light-emitting layer. The monodentate bidentate aliphatic compound 12-aminododecane-1-thiol was dissolved in methanol and spin-coated on the light-emitting layer at 3000rpm for 20s during the spin-coating process, and then excess 12-aminododecane-1-thiol was rinsed off with methanol to form a second ligand layer.
(4) And spin-coating the TFB ink on the second ligand layer, and then vacuum-drying to form a film, thereby forming a hole transport layer with the thickness of 65 nm.
(5) And spin-coating PEDOT (PSS) ink on the hole transport layer to form a hole injection layer with the thickness of 30 nm.
(6) And evaporating metal aluminum on the hole injection layer to form an anode, wherein the thickness of the anode is 100 nm.
(7) And packaging to obtain the QLED device.
The current efficiency and lifetime (T50@1000nit) results for the above examples and comparative examples are shown in table 1, using blue quantum dots as the experimental subjects.
TABLE 1
Figure BDA0002422727720000161
The present invention further provides other alternative material combinations for the first ligand layer and the second ligand layer and their corresponding current efficiencies and lifetimes, to illustrate the advantages of the amide-based compounds of the present invention as the first ligand layer and the bidentate aliphatic, aromatic and monodentate bidentate aliphatic compounds as the second ligand layer, as detailed in tables 2 and 3.
Wherein the first ligand layer of tables 2 and 3 are the molecular formulas of the respective materials, in comparison with the following: n-ethyl-5-methyl-2- (1-methylethyl) cyclohexanecarboxamide (C) 13 H 25 NO), 4-methoxybenzamide (C) 8 H 9 NO 2 ) 2, 4-dihydroxybenzamide (C) 7 H 7 NO 3 ) Valeramide (C) 5 H 11 NO), N, N, N ', N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine (C) 22 H 48 N 10 O 4 )。
The headings in tables 2 and 3 are the molecular formulas of the materials of the second ligand layer, in comparison to the following: 1, 12-Dimercaptododecane (C) 12 H 26 S 2 ) 1, 12-diaminododecane (C) 12 H 28 N 2 ) 2, 2-iminodibenzoic acid (C) 14 H 11 NO 4 ) 2, 2-iminobenzhydrylamine (C) 12 H 13 N 3 ) 2, 2-iminodithiol(s) (ii)C 12 H 11 NS 2 ) 1, 2-benzenedithiol (C) 6 H 6 S 2 ) 12-aminododecane-1-thiol (C) 12 H 27 NS) and 13-aminotridecanoic acid (C) 13 H 27 NO 2 )。
Table 2 shows the current efficiency of the blue quantum dots of each of the above examples.
TABLE 2
Figure BDA0002422727720000171
Table 3 shows the lifetimes of the blue quantum dots of the above examples.
TABLE 3
Figure BDA0002422727720000181
According to the electroluminescent diode device, the amide compound is introduced to serve as the first ligand layer, and the bidentate aliphatic compound, the bidentate aromatic compound or the monodentate double-ligand aliphatic compound is introduced to serve as the second ligand layer, so that the obtained electroluminescent diode device is good in current efficiency and long in service life. Specifically, in the above-described electroluminescent diode device, the amide-based compound is introduced as the first ligand layer, and thus the function of blocking electron injection into the light-emitting layer is achieved, and at least a part of the material forming the first ligand layer can be more sufficiently ligand-exchanged with the surface ligands of the quantum dots, thereby promoting the effect of blocking electron injection. The device also has the function of promoting the injection of a hole into a quantum dot light emitting layer by introducing a bidentate aliphatic compound, a bidentate aromatic compound or a monodentate dual-ligand aliphatic compound as a second ligand layer, and the compound can be combined with the quantum dot more tightly, so that the loss of the compound in the process of converting from a solution state to a solid film is reduced, and meanwhile, the group on the compound can reduce the contact angle between the second ligand layer and the hole transmission layer, and the injection of the hole is promoted. The synergistic effect of blocking the injection of electrons and promoting the injection of holes can more effectively balance the number of carriers in the light-emitting layer, thereby improving the light-emitting performance of the device and prolonging the service life of the device.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only represent a preferred embodiment of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (8)

1. An electroluminescent diode device, comprising:
the cathode, the electron transport layer, the first ligand layer, the luminescent layer, the second ligand layer, the hole transport layer and the anode are sequentially stacked;
wherein the light emitting layer comprises quantum dots and surface ligands bound to the quantum dots;
the material of the first ligand layer is an amide compound, the molecular weight of the amide compound is 10-1000, and at least one part of the material of the first ligand layer is in ligand exchange with the surface ligand;
the material of the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound, at least a portion of the material of the second ligand layer being in ligand exchange with the surface ligands; wherein the bidentate aliphatic compound is selected from: at least one of 1, 12-dimercaptododecane and 1, 12-diaminododecane, the bidentate aromatic compound being selected from: at least one of 2, 2-iminodibenzoic acid, 2-iminobenzhydrylamine, 2-iminodithiol, 1, 2-benzenedithiol, and 1, 3-benzenedithiol, said monodentate bidentate aliphatic compound selected from the group consisting of: at least one of 12-aminododecane-1-thiol and 13-aminotridenoic acid.
2. The electroluminescent diode device according to claim 1, wherein the amide-based compound is selected from the group consisting of: at least one of N-ethyl-5-methyl-2- (1-methylethyl) cyclohexanecarboxamide, 4-methoxybenzamide, 2, 4-dihydroxybenzamide, valeramide, and N, N, N ', N' -tetrakis (N- (2-aminoethyl) propionamido) ethylenediamine.
3. The electroluminescent diode device according to any one of claims 1 to 2, wherein the quantum dots are core-shell structure quantum dots;
the core material of the core-shell structure quantum dot is selected from: at least one of CdSe, CdS, ZnSe, ZnS, CdTe, CdZnS, CdZnSe, ZnSeS, ZnSeTe, ZnTeS, CdSeS, CdSeTe, CdTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdSeSTe, ZnSeTe, CdZnSeTe, InP, InAs and InAsP;
the shell material of the core-shell structure quantum dot is selected from: at least one of CdS, ZnSe, ZnS, CdSeS and ZnSeS.
4. The device according to any of claims 1 to 2, wherein the surface ligand is selected from the group consisting of: at least one of oleic acid, oleylamine and trioctylphosphine.
5. The electroluminescent diode device according to any one of claims 1 to 2, wherein the electron transport layer is made of a material selected from the group consisting of: at least one of zinc oxide, barium oxide and titanium dioxide.
6. The device according to any one of claims 1 to 2, wherein the hole transport layer is made of a material selected from the group consisting of: n, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine, poly (N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine), polyvinylcarbazole, 4 '-bis (9-carbazole) biphenyl, N' -diphenyl-N, N '- (1-naphthyl) -1, 1' -biphenyl-4, 4 '-diamine, 4' -tris (carbazol-9-yl) triphenylamine, poly (9, 9-dioctylfluorene-CO-N- (4-butylphenyl) diphenylamine), 4, 7-diphenyl-1, 10-phenanthroline and 4, 4' -cyclohexyl di (N, N-di (4-methylphenyl) aniline).
7. A method for preparing an electroluminescent diode device is characterized by comprising the following steps:
sequentially forming a cathode, an electron transport layer, a first ligand layer, a luminescent layer, a second ligand layer, a hole transport layer and an anode on a substrate; or
Sequentially forming an anode, a hole transport layer, a second ligand layer, a luminescent layer, a first ligand layer, an electron transport layer and a cathode on a substrate;
wherein the light emitting layer comprises quantum dots and surface ligands bound to the quantum dots;
the material of the first ligand layer is an amide compound, the molecular weight of the amide compound is 10-1000, and at least one part of the material of the first ligand layer is in ligand exchange with the surface ligand;
the material of the second ligand layer is selected from: at least one of a bidentate aliphatic compound, a bidentate aromatic compound and a monodentate bidentate aliphatic compound, at least a portion of the material of the second ligand layer being in ligand exchange with the surface ligands, wherein the bidentate aliphatic compound is selected from the group consisting of: at least one of 1, 12-dimercaptododecane and 1, 12-diaminododecane, the bidentate aromatic compound being selected from: at least one of 2, 2-iminodibenzoic acid, 2-iminobenzhydrylamine, 2-iminodithiol, 1, 2-benzenedithiol, and 1, 3-benzenedithiol, said monodentate bidentate aliphatic compound selected from the group consisting of: at least one of 12-aminododecane-1-thiol and 13-aminotridenoic acid.
8. A display device, comprising:
an electroluminescent diode device as claimed in any one of claims 1 to 6; or
The electroluminescent diode device prepared by the method for preparing an electroluminescent diode device according to claim 7.
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