CN113809248A - Composite material, preparation method thereof and quantum dot light-emitting diode - Google Patents
Composite material, preparation method thereof and quantum dot light-emitting diode Download PDFInfo
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- CN113809248A CN113809248A CN202010546265.7A CN202010546265A CN113809248A CN 113809248 A CN113809248 A CN 113809248A CN 202010546265 A CN202010546265 A CN 202010546265A CN 113809248 A CN113809248 A CN 113809248A
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- composite material
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- gas
- organic semiconductor
- semiconductor material
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- 239000002131 composite material Substances 0.000 title claims abstract description 89
- 239000002096 quantum dot Substances 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 110
- 239000004065 semiconductor Substances 0.000 claims abstract description 80
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 230000005525 hole transport Effects 0.000 claims description 72
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 40
- 239000002243 precursor Substances 0.000 claims description 36
- 238000010438 heat treatment Methods 0.000 claims description 26
- 239000007789 gas Substances 0.000 claims description 20
- -1 titanium ions Chemical class 0.000 claims description 19
- 239000005416 organic matter Substances 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229910052733 gallium Inorganic materials 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 238000000137 annealing Methods 0.000 claims description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 5
- 229910001449 indium ion Inorganic materials 0.000 claims description 5
- 229920000767 polyaniline Polymers 0.000 claims description 5
- 229920000128 polypyrrole Polymers 0.000 claims description 5
- 229910001432 tin ion Inorganic materials 0.000 claims description 5
- NHCDCRWRKBUWEC-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-(1-phenylcyclohexyl)aniline Chemical compound C1=CC(C)=CC=C1N(C1(CCCCC1)C=1C=CC=CC=1)C1=CC=C(C)C=C1 NHCDCRWRKBUWEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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- 239000010936 titanium Substances 0.000 claims description 4
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- PWFFDTZNRAEFIY-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1C1=CC(N)=CC=C1C1=CC=C(N)C=C1 PWFFDTZNRAEFIY-UHFFFAOYSA-N 0.000 claims description 3
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- CKHJYUSOUQDYEN-UHFFFAOYSA-N gallium(3+) Chemical compound [Ga+3] CKHJYUSOUQDYEN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 claims description 3
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 claims description 3
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- 230000005540 biological transmission Effects 0.000 abstract description 13
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- 238000012360 testing method Methods 0.000 description 11
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- 239000010408 film Substances 0.000 description 10
- 239000004246 zinc acetate Substances 0.000 description 10
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 3
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- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- VBXWCGWXDOBUQZ-UHFFFAOYSA-K diacetyloxyindiganyl acetate Chemical compound [In+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VBXWCGWXDOBUQZ-UHFFFAOYSA-K 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
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- 239000013078 crystal Substances 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
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- 239000011592 zinc chloride Substances 0.000 description 1
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
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- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
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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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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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
- 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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- 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
- H10K85/10—Organic polymers or oligomers
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- 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
- H10K85/30—Coordination compounds
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- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
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- 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
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Abstract
The invention belongs to the technical field of luminescent device materials, and particularly relates to a composite material, a preparation method thereof and a quantum dot light-emitting diode. The composite material comprises an organic semiconductor material, an organic molecule and metal ions, wherein the organic molecule has a structure shown in the following formula I, and carboxyl on the organic molecule is coordinated with the metal ions and is connected to the organic semiconductor material through the metal ions; in the formula I, R1Is- (CH)2)nN is an integer greater than or equal to 1. The composite material shortens the molecular distance of the organic semiconductor material, enhances the conjugated resonance effect among molecules, improves the intermolecular conduction capability of a hole in the organic semiconductor material, and improves the hole mobility, and meanwhile, the composite material can effectively improve the crystallinity through the doping of the organic molecules, so that the resistance of the composite material is reduced, and the hole transmission capability of the composite material is further enhanced.
Description
Technical Field
The invention belongs to the technical field of luminescent device materials, and particularly relates to a composite material, a preparation method thereof and a quantum dot light-emitting diode.
Background
Quantum Dots (QDs), also known as semiconductor nanocrystals, are typically composed of group II-VI or III-V elements with particle sizes smaller than or close to the exciton Bohr radius. At present, the development of quantum dot synthesis technology makes a significant breakthrough, wherein the research of II-VI group quantum dots represented by CdSe tends to be perfected, such as: photoluminescence efficiency is close to 100%, the width of a generated peak is as narrow as 20-30 nm, and the device efficiency and the device service life of the red and green quantum dots are close to commercial application requirements. Because the high-quality quantum dots are all prepared by a full-solution synthesis method, the method is very suitable for preparing a film by adopting solution processing modes such as spin coating, printing and the like. Therefore, quantum dot light emitting diodes (QLEDs) using quantum dot materials as quantum dot light emitting layers are expected to be powerful competitors to the next generation of new display technologies.
However, the electroluminescent device of quantum dot still has the problems of low efficiency, short lifetime, etc., and the solution method is commonly used to prepare high-performance QLED devices, and organic semiconductor materials are generally used as the Hole Transport Layer (HTL) of the QLED. However, the organic semiconductor material generally has the problems of low carrier mobility, large resistance and poor matching between the HOMO energy level and the quantum dot, so that hole injection is difficult, the interface barrier of the hole transport layer/the quantum dot light emitting layer is large, and charge interfaces accumulate more, thereby having very adverse effects on the efficiency and the service life of the QLED device.
Therefore, the prior art is in need of improvement.
Disclosure of Invention
An object of the present invention is to overcome the above-mentioned disadvantages of the prior art, and to provide a composite material and a method for preparing the same, which are intended to solve the technical problem that the hole transport property of an organic semiconductor material is not ideal.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a composite material, which comprises an organic semiconductor material, an organic molecule and metal ions, wherein the organic molecule has a structure shown in the following formula I, carboxyl on the organic molecule is coordinated with the metal ions, and the carboxyl is connected to the organic semiconductor material through the metal ions;
wherein R is1Is- (CH)2)nN is an integer greater than or equal to 1.
The composite material provided by the invention comprises an organic semiconductor material, and an organic molecule and a metal ion which are connected with the organic semiconductor material and shown in a formula I, wherein a carboxyl group of the organic molecule is coordinated with the metal ion, and the metal ion is simultaneously coordinated with a functional group of the organic semiconductor material, so that the organic molecule is connected with the organic semiconductor material, and the organic molecule is a dicarboxylic acid micromolecule, so that the organic molecule can be respectively connected with the organic semiconductor material through carboxyl groups at two ends, the organic semiconductor material is connected with each other, the molecular distance of the organic semiconductor can be shortened, the conjugated resonance effect between molecules is enhanced, the conduction capability of a hole between the molecules of the organic semiconductor material is improved, the hole mobility is improved, and the crystallinity of the composite material can be effectively improved through the doping of the organic molecule, thereby reducing the resistance of the composite material and further enhancing the hole transmission capability of the composite material.
The invention also provides a preparation method of the composite material, which comprises the following steps:
providing an organic semiconductor material, a dicarboxylic acid monoester organic matter shown as the following formula II and a metal ion precursor;
dissolving the organic semiconductor material, the dicarboxylic acid monoester organic matter and the metal ion precursor in a nonpolar solvent, and heating to obtain a mixed solution;
carrying out solid-liquid separation on the mixed solution to obtain the composite material;
wherein R is1Is- (CH)2)n-，R2is-O (CH)2)mCH3N is largeAn integer of 1 or more, and m is an integer of 0 or more.
The preparation method of the composite material provided by the invention comprises the steps of dissolving an organic semiconductor material, a dicarboxylic acid monoester organic matter shown in a formula II and a metal ion precursor in a nonpolar solvent for heating treatment, hydrolyzing the dicarboxylic acid monoester organic matter shown in the formula II to form an organic molecule shown in the formula I, dissolving the metal ion precursor to form metal ions, and thus in the composite material obtained by subsequent solid-liquid separation, the organic molecule can be coordinated with the metal ion through carboxyl groups at two ends and coordinated with the organic semiconductor material by utilizing the metal ion to coordinate with the organic semiconductor material, so that the organic molecule and the organic semiconductor material are connected with each other, the composite material obtained by the preparation method shortens the molecular distance of the organic semiconductor material, enhances the conjugated resonance effect among molecules, thereby improving the conduction capability among the molecules and the hole mobility, and simultaneously the crystallinity of the composite material can be effectively improved by doping the organic molecule, thereby reducing the resistance of the composite material and further enhancing the hole transmission capability of the composite material.
The invention also aims to provide a quantum dot light emitting diode, aiming at solving the technical problem that the hole transmission performance of the quantum dot light emitting diode is not ideal. In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a quantum dot light-emitting diode which comprises an anode, a cathode and a quantum dot light-emitting layer positioned between the anode and the cathode, wherein a hole transport layer is arranged between the anode and the quantum dot light-emitting layer, and the hole transport layer is composed of the composite material or the composite material prepared by the preparation method of the composite material.
The hole transport layer in the quantum dot light-emitting diode provided by the invention is composed of the specific composite material or the specific composite material prepared by the preparation method provided by the invention, the composite material has good crystal structure electrical properties, can improve hole mobility and enhance hole injection, the HOMO energy level of the composite material is well matched with the quantum dot light-emitting layer, effective combination of electrons and holes in the quantum dot light-emitting layer can be promoted, charge accumulation of the interface of the quantum dot light-emitting layer and the hole transport layer is reduced, and therefore, the light-emitting efficiency and the service life of a device are improved.
Drawings
FIG. 1 is a flow chart of a method of making a composite material according to an embodiment of the present invention;
fig. 2 is a schematic structural diagram of a quantum dot light-emitting diode according to an embodiment of the invention.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more clearly apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In one aspect, embodiments of the present invention provide a composite material, including an organic semiconductor material, an organic molecule, and a metal ion, where the organic molecule has a structure shown in formula I below, and a carboxyl group on the organic molecule is coordinated with the metal ion and is connected to the organic semiconductor material through the metal ion;
wherein R is1Is- (CH)2)nN is an integer greater than or equal to 1.
The composite material provided by the embodiment of the invention comprises an organic semiconductor material, and organic molecules and metal ions which are connected with the organic semiconductor material and are shown in a formula I, wherein a carboxyl group of the organic molecule is coordinated with the metal ions, and the metal ions are simultaneously coordinated with a functional group of the organic semiconductor material, so that the organic molecule is connected with the organic semiconductor material, the organic molecule is connected with two organic semiconductor materials through the carboxyl because the organic molecule is dicarboxylic acid micromolecules, the organic molecule is connected with the two organic semiconductor materials through the carboxyl, the molecular distance of the organic semiconductor materials can be shortened by connecting the organic semiconductor materials, the conjugated resonance effect between molecules is enhanced, the conduction capability of a hole between the molecules of the organic semiconductor materials is improved, the hole mobility is improved, and the crystallinity of the composite material can be effectively improved by doping the organic molecules, thereby reducing the resistance of the composite material and further enhancing the hole transmission capability of the composite material.
In one embodiment, R of the organic molecule1Is- (CH)2)n-, where n is 2 to 20; unbranched linear carbon chain R within the carbon number range1The organic semiconductor material can be better connected. Specifically, n is 4 to 9.
In one embodiment, the mass ratio of the organic molecules to the organic semiconductor material is (0.1-1): 30, of a nitrogen-containing gas; the organic molecules shown in the formula I are doped in the mass ratio range, so that the hole transport performance of the composite material can be better improved. Specifically, the mass ratio of the organic molecules to the organic semiconductor material is 1: 30.
in one embodiment, the molar ratio of the organic molecule to the metal ion is (1-3): 1. within this molar ratio range, the organic molecule can coordinate with the metal ion more efficiently.
In one embodiment, the organic semiconductor material is an organic hole transport material, and further, the organic semiconductor material is selected from organic hole transport materials containing amine groups, and the amine groups, which are functional groups, can be better coordinated with metal ions to be linked with the organic molecules. In particular, the organic semiconducting material is selected from poly (9, 9-dioctyl-fluorene-co-N- (4-butylphenyl) -diphenylamine) (TFB), polyarylamine, poly (N-vinylcarbazole), polyaniline, polypyrrole, one or more of N, N ' -tetrakis (4-methoxyphenyl) -benzidine (TPD), 4-bis [ N- (1-naphthyl) -N-phenyl-amino ] biphenyl (α -NPD), 4',4 ″ -tris [ phenyl (m-tolyl) amino ] triphenylamine (m-MTDATA), 4',4 ″ -tris (N-carbazolyl) -triphenylamine (TCTA), and 1, 1-bis [ (di-4-tolylamino) phenylcyclohexane (TAPC); the metal ions are selected from one or more of zinc ions, titanium ions, aluminum ions, indium ions, tin ions, zirconium ions and gallium ions. The metal ions can be coordinated with carboxyl of the organic molecule shown in the formula I and the functional group amine in the organic hole transport material, and two carboxyl of the formula I can be coordinated with the metal ions, so that one organic molecule can be connected with two organic hole transport material molecules, thereby connecting the organic hole transport materials with each other.
In one embodiment, the composite material of an embodiment of the present invention is composed of the above-described organic semiconductor material, organic molecules, and metal ions.
On the other hand, the embodiment of the invention also provides a preparation method of the composite material, as shown in fig. 1, the preparation method comprises the following steps:
s01: providing an organic semiconductor material, a dicarboxylic acid monoester organic matter shown in a formula II and a metal ion precursor;
s02: dissolving the organic semiconductor material, the dicarboxylic acid monoester organic matter and the metal ion precursor in a nonpolar solvent, and heating to obtain a mixed solution;
s03: carrying out solid-liquid separation on the mixed solution to obtain the composite material;
wherein R is1Is- (CH)2)n-，R2is-O (CH)2)mCH3N is an integer of 1 or more, and m is an integer of 0 or more.
According to the preparation method of the composite material provided by the embodiment of the invention, the organic semiconductor material, the dicarboxylic acid monoester organic matter shown in the formula II and the metal ion precursor are dissolved in the nonpolar solvent for heating treatment, the dicarboxylic acid monoester organic matter shown in the formula II is hydrolyzed to form the organic molecule shown in the formula I, and the metal ion precursor is dissolved to form the metal ion, so that in the composite material obtained by subsequent solid-liquid separation, the organic molecule is coordinated with the metal ion through carboxyl, and the metal ion is coordinated with the functional group of the organic semiconductor material through the metal ion, so that the organic molecule connects the organic semiconductor material with each other, the composite material obtained by the preparation method shortens the molecular distance of the organic semiconductor material, enhances the conjugated resonance effect among molecules, thereby enhancing the conduction capability among molecules, enhancing the hole mobility, and simultaneously the crystallinity of the composite material can be effectively improved through the doping of the organic molecule, thereby reducing the resistance of the composite material and further enhancing the hole transmission capability of the composite material.
In one embodiment, the composite material provided by the embodiment of the invention is obtained by the preparation method, and the composite material comprises an organic semiconductor material, an organic molecule shown as a formula I and a metal ion, wherein the organic molecule is connected with the organic semiconductor material, and two carboxyl groups on the organic molecule are connected with the organic semiconductor material through coordination with the metal ion; the specific preparation steps are as described above.
In the step S01, the dicarboxylic acid monoester represented by the formula II R1Wherein n is 2-20; r2Wherein m is 2-20. Unbranched linear R within the carbon number range1The organic semiconductor material can be better connected. Unbranched linear R within the carbon number range2The organic molecules forming the ambipolar group of formula I can be better hydrolyzed. The organic semiconductor material is an organic hole transport material, specifically, the organic hole transport material is selected from poly (9, 9-dioctyl-fluorene-co-N- (4-butylphenyl) -diphenylamine), polyarylamine, poly (N-vinylcarbazole), polyaniline, polypyrrole, N, N, N ', N' -tetrakis (4-methoxyphenyl) -benzidine, 4-bis [ N- (1-naphthyl) -N-phenyl-amino-]Biphenyl, 4' -tris [ phenyl (m-tolyl) amino group]One or more of triphenylamine, 4',4 "-tris (N-carbazolyl) -triphenylamine, and 1, 1-bis [ (di-4-tolylamino) phenylcyclohexane; the metal ion precursor is selected from one or more of a zinc ion precursor, a titanium ion precursor, an aluminum ion precursor, an indium ion precursor, a tin ion precursor, a zirconium ion precursor and a gallium ion precursor. The zinc ion precursor comprises: dimethyl zinc, diethyl zinc, zinc acetate, zinc acetylacetonate, zinc iodide, zinc bromide, zinc chloride, zinc fluoride, zinc carbonate, zinc cyanide,At least one of zinc nitrate, zinc oxide, zinc peroxide, zinc perchlorate, zinc sulfate, zinc oleate, zinc stearate, etc., but is not limited thereto. The titanium ion precursor includes: at least one of titanyl sulfate, titanium acetate, titanium tetrachloride, titanium tetrabromide, titanium trichloride, titanium triisopropoxide chloride, titanium tetrachlorobis (tetrahydrofuran) chloride, bis (mercaptocyclopentane) titanium tetrachloride, and the like, but is not limited thereto. The aluminum ion precursor includes: at least one of aluminum phosphate, aluminum acetate, aluminum acetylacetonate, aluminum iodide (aluminum iodide), aluminum bromide, aluminum chloride, aluminum fluoride, aluminum carbonate, aluminum cyanide, aluminum nitrate, aluminum oxide, aluminum peroxide, aluminum sulfate (aluminum sulfate), aluminum oleate, aluminum stearate, aluminum myristate, aluminum palmitate, and the like, but are not limited thereto. The indium ion precursor includes: at least one of indium phosphate, indium acetate, indium acetylacetonate, indium iodide, indium bromide, indium chloride, indium fluoride, indium carbonate, indium cyanide, indium nitrate, indium oxide, indium peroxide, indium sulfate, indium oleate, indium stearate, indium myristate, and indium palmitate, but not limited thereto. The tin ion precursor includes: at least one of stannous acetate, stannic chloride, stannous oxalate, triethylstannic bromide, stannic stearate, stannic acid, stannic iodide, stannic methanesulfonate, stannic fluorophosphate, stannic sulfate, stannic acetate, etc., but is not limited thereto. The zirconium ion precursor includes: at least one of zirconium acetate, zirconium acetylacetonate, zirconium chloride, zirconium bromide, zirconium nitrate, zirconium sulfate, zirconium carbonate, and the like, but is not limited thereto. The gallium ion precursor comprises: at least one of gallium phosphate, gallium acetate, gallium acetylacetonate, gallium iodide, gallium bromide, gallium chloride, gallium fluoride, gallium carbonate, gallium cyanide, gallium nitrate, gallium oxide, gallium peroxide, gallium sulfate, gallium oleate, gallium stearate, gallium myristate, gallium palmitate, and the like, but is not limited thereto.
In step S02, the organic semiconductor material, the dicarboxylic acid monoester organic substance, and the metal ion precursor are heated and dissolved in the non-polar solvent to obtain a mixed solution, and the dicarboxylic acid monoester organic substance is hydrolyzed to form the bipolar group organic molecule shown in formula I, wherein the heating conditions include: the temperature is 60-120 ℃, the time is 30 min-4 h, and the dicarboxylic acid monoester organic matter can be hydrolyzed better under the conditions. For example, the mixed solution is a fatty acid solution of monomethyl suberate and zinc acetate, and after hydrolysis by heating, monomethyl suberate is converted to suberic acid and then coordinated with metal ions. Wherein the nonpolar solvent comprises one or more of chloroform, chlorobenzene, n-hexane, n-octane, n-heptane and toluene.
In one embodiment, the mass ratio of the dicarboxylic acid monoester organic substance to the organic semiconductor material is (0.1-1): 30, of a nitrogen-containing gas; within the mass ratio range, the hole transport performance of the composite material can be better improved. Further, the molar ratio of the added dicarboxylic acid monoester organic matter to the metal ion precursor is (1-3): 1.
in step S03, the solid-liquid separation step includes an annealing crystallization treatment, for example, the solid-liquid separation step includes annealing crystallization at a temperature of 140 to 160 ℃, and further the annealing time is 20 to 40 min. In one embodiment, in order to obtain the composite material film, the mixed solution is deposited on a substrate and is subjected to annealing crystallization treatment, so that a composite material film layer is obtained, and the composite material film layer can be used as a hole transport film layer.
The composite material film layer obtained after annealing can improve the film forming crystallinity of the composite material, thereby improving the hole transmission. If the conventional hole transport layer HTL is not doped with any other materials, when the QLED device is prepared, the HTL is deposited on the hole injection layer HIL and then is heated to complete the crystallization reaction of the HTL film layer, and the HTL is not beneficial to the transmission of holes because the film resistance is higher in the crystallization process of the HTL which is made of organic semiconductor materials. By adopting the micromolecule doped organic semiconductor material of the bipolar group of the embodiment of the invention, the problem of HTL crystallinity can be effectively improved, and the formed composite material can be used as follows: the structure of the organic semiconductor material-metal ion-organic molecule shown in formula I-metal ion-organic semiconductor material is shown.
For organic semiconductor material molecules, the organic semiconductor material molecules are chain-shaped structures, large branched chains are arranged in the repeated structures of the organic semiconductor material molecules, the molecules are preferentially expanded in the transverse direction during crystallization, and the spacing between the molecules is further enlarged due to the fact that the branched chains are large in steric hindrance in the longitudinal direction, the molecular chains are in folding motion in the crystallization process, and the molecular force is not restrained in the longitudinal direction (like several bent lines, the occupied space is far larger than several straight lines superposed together). In the composite material obtained by the preparation method, after the organic molecules shown in the formula I are doped, the organic semiconductor materials can be connected in a chain structure better, so that the distance between the adjacent organic semiconductor materials is further reduced, the conjugated resonance effect between molecules can be enhanced, the intermolecular conduction capability is improved, and the hole mobility is improved.
The embodiment of the invention also provides an application of the composite material or the composite material obtained by the preparation method of the composite material as a hole transport material. The HOMO energy level of the composite material provided by the embodiment of the invention is well matched with the quantum dot light-emitting layer, so that the resistance is reduced, the hole mobility is improved, the conduction and recombination capability of holes at interfaces can be improved, and the transmission efficiency of carriers between the interfaces is improved, therefore, the composite material can be used as a hole transmission material, and is particularly used for a hole transmission layer of a quantum dot light-emitting diode.
Finally, the embodiment of the invention also provides a quantum dot light-emitting diode, which comprises an anode, a cathode and a quantum dot light-emitting layer positioned between the anode and the cathode, wherein a hole transport layer is arranged between the anode and the quantum dot light-emitting layer, and the hole transport layer is composed of the composite material or the composite material prepared by the preparation method of the composite material.
The electron injection of the QLED device is generally much stronger than the hole injection, resulting in poor charge balance of the device and severely affecting the device lifetime. In the embodiment of the invention, the unbranched linear chain dicarboxylic acid (organic molecules shown in formula I) is added into the HTL layer to be coordinated with the metal ions, so that the organic semiconductor material can be coordinated with the metal ions, and the organic semiconductor material is connected, the molecular distance of the organic semiconductor material is shortened, the conjugated resonance effect among molecules of the organic semiconductor material is enhanced, the conduction capability of a cavity among the molecules of the organic semiconductor material is improved, the cavity mobility of a semiconductor material layer is improved, and the cavity transmission capability is enhanced. Therefore, the hole transport layer in the quantum dot light emitting diode provided by the embodiment of the invention is composed of the specific composite material provided by the embodiment of the invention or the specific composite material prepared by the preparation method provided by the embodiment of the invention, the composite material has good electrical properties of a crystal structure, hole injection is enhanced, the HOMO energy level of the composite material is well matched with the quantum dot light emitting layer, effective combination of electron-hole in the quantum dot light emitting layer can be promoted, the hole and electron injection rate of the device can be balanced, and charge accumulation of the interface of the quantum dot light emitting layer and the hole transport layer can be reduced, so that the light emitting efficiency and the service life of the device can be improved.
In an embodiment, in the above device, a hole injection layer is further disposed between the hole transport layer and the anode. In another embodiment, an electron functional layer, such as an electron transport layer, or a stack of an electron injection layer and an electron transport layer, is disposed between the quantum dot light emitting layer and the cathode, wherein the electron injection layer is adjacent to the cathode.
The quantum dot light-emitting diode provided by the embodiment of the invention comprises an upright structure and an inverted structure.
In one embodiment, the front-mounted quantum dot light emitting diode comprises a laminated structure of an anode and a cathode which are oppositely arranged, a quantum dot light emitting layer arranged between the anode and the cathode, a hole transport layer arranged between the anode and the quantum dot light emitting layer, and the anode is arranged on a substrate. Further, a hole function layer such as a hole injection layer and an electron blocking layer can be arranged between the anode and the quantum dot light-emitting layer; an electron-transport layer, an electron-injection layer, a hole-blocking layer and other electron-functional layers can be arranged between the cathode and the quantum dot light-emitting layer. In some embodiments of the front structure device, the quantum dot light emitting diode includes a substrate, an anode disposed on a surface of the substrate, a hole injection layer disposed on a surface of the anode, a hole transport layer disposed on a surface of the hole injection layer, a quantum dot light emitting layer disposed on a surface of the hole transport layer, an electron transport layer disposed on a surface of the quantum dot light emitting layer, and a cathode disposed on a surface of the electron transport layer.
In one embodiment, an inverted structure quantum dot light emitting diode includes a stacked structure of an anode and a cathode disposed opposite each other, a quantum dot light emitting layer disposed between the anode and the cathode, a hole transport layer disposed between the anode and the quantum dot light emitting layer, and the cathode disposed on a substrate. Further, a hole function layer such as a hole injection layer and an electron blocking layer can be arranged between the anode and the quantum dot light-emitting layer; an electron-transport layer, an electron-injection layer, a hole-blocking layer and other electron-functional layers can be arranged between the cathode and the quantum dot light-emitting layer. In some embodiments of the device with an inverted structure, the quantum dot light emitting diode includes a substrate, a cathode disposed on a surface of the substrate, an electron transport layer disposed on a surface of the cathode, a quantum dot light emitting layer disposed on a surface of the electron transport layer, a hole transport layer disposed on a surface of the quantum dot light emitting layer, a hole injection layer disposed on a surface of the hole transport layer, and an anode disposed on a surface of the hole injection layer.
Correspondingly, the preparation method of the quantum dot light-emitting diode comprises the following steps:
e01: providing a substrate;
e02: the composite material or the composite material obtained by the preparation method provided by the embodiment of the invention is deposited on the substrate to obtain the hole transport layer.
Specifically, the preparation of the QLED device comprises the following steps:
(1) providing a substrate, and forming an anode on the substrate;
(2) forming a hole injection layer on the anode;
(3) a hole transport layer is formed on the hole injection layer and is composed of the composite material according to the embodiment of the present invention.
(4) Forming a quantum dot light emitting layer on the hole transport layer;
(5) depositing an electron transport layer on the quantum dot light emitting diode layer;
(6) a cathode is formed on the electron transport layer.
The substrate comprises a rigid, flexible substrate, specifically comprising glass, a silicon wafer, polycarbonate, polymethylmethacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, polyethersulfone, or a combination thereof.
The anode comprises a metal or alloy thereof such as nickel, platinum, vanadium, chromium, copper, zinc, or gold; a conductive metal oxide such as zinc oxide, indium oxide, tin oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or fluorine-doped tin oxide; or a combination of metals and oxides such as ZnO and Al or SnO2And Sb, but is not limited thereto, and may be any two or a combination of two or more of the above.
The hole injection layer comprises a conductive compound including polythiophene, polyaniline, polypyrrole, poly (p-phenylene), polyfluorene, poly (3, 4-ethylenedioxythiophene) polysulfonylstyrene (PEDOT: PSS), MoO3、WoO3、NiO、HATCN、CuO、V2O5CuS, or a combination thereof.
The hole transport layer can be a composite film layer prepared by the steps.
The quantum dots of the quantum dot light emitting layer are CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe of II-VI groups; or group III-V GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaGaAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InInInAlN, InLNAs, InAsInNSb, InAlGaAs, InLPSb; or group IV-VI SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, SnPbSTe; or a combination of any one or more of the above.
The electron transport layer is ZnO or TiO2、Alq3、SnO2、ZrO、AlZnO、ZnSnO、BCP、TAZ、PBD、TPBI、Bphen、CsCO3One or more of (a).
The cathode comprises a metal or alloy thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, or barium; the multilayer structure material includes a structure of a first layer of an alkali metal halide, an alkaline earth metal halide, an alkali metal oxide, or a combination thereof, and a metal layer, wherein the metal layer includes an alkaline earth metal, a group 13 metal, or a combination thereof. For example LiF/Al, LiO2Al, LiF/Ca, Liq/Al, and BaF2and/Ca, but not limited thereto.
The thickness of the bottom electrode is 20-200 nm; the thickness of the hole injection layer is 20-200 nm; the thickness of the hole transport layer is 30-180 nm; the total thickness of the quantum dot mixed luminescent layer is 30-180 nm. The thickness of the electron transmission layer is 10-180 nm; the thickness of the top electrode is 40-190 nm.
The invention is described in further detail with reference to a part of the test results, which are described in detail below with reference to specific examples.
Example 1
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, the hole transport layer 4 is made of a suberic acid-doped TFB composite material, the quantum dot light emitting layer 5 is made of CdZnSe/ZnSe quantum dots, the electron transport layer 6 is made of ZnO, and the cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. to the solution of TFB dissolved in chloroform solvent was added a certain amount of monomethyl suberate and a solution of zinc acetate in n-octanoic acid at room temperature. The mass ratio of the doped dicarboxylic acid monoester to the TFB material is 1:30, the molar ratio of the dicarboxylic acid monoester to the zinc acetate is 1:1, and the dicarboxylic acid monoester is completely hydrolyzed to form suberic acid by heating at 80 ℃ for 2h to obtain a solution 1.
2. And depositing the prepared solution 1 on a hole injection layer (PEDOT: PSS), spin-coating for 30s under the deposition condition of 3000r/min, and heating at 150 ℃ for 2h to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSe/ZnSe quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 3000 r/min.
4. Depositing an electron transport layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Example 2
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, the hole transport layer 4 is made of a succinic acid-doped TFB composite material, the quantum dot light emitting layer 5 is made of CdZnSe/ZnSe/CdZnS quantum dots, the electron transport layer 6 is made of ZnO, and the cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. at room temperature, a certain amount of monomethyl succinate and zinc acetate solution in n-octanoic acid was added to the TFB solution dissolved in chloroform solvent. The mass ratio of the doped dicarboxylic acid monoester to the TFB material is 1:30, the molar ratio of the dicarboxylic acid monoester to the zinc acetate is 1:2, and the dicarboxylic acid monoester is completely hydrolyzed to form succinic acid by heating at 80 ℃ for 3h to obtain a solution 1.
2. And depositing the prepared solution 1 on a hole injection layer (PEDOT: PSS), spin-coating for 30s under the deposition condition of 3000r/min, and heating at 140 ℃ for 2h to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSe/ZnSe/CdZnS quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 2000 r/min.
4. Depositing an electron transport layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Example 3
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, a hole transport layer 4 is made of a glutaric acid doped TFB composite material, a quantum dot light emitting layer 5 is made of CdZnSe/ZnSe/ZnS quantum dots, an electron transport layer 6 is made of ZnO, and a cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. to the TFB solution dissolved in chlorobenzene solvent was added a certain amount of monomethyl glutarate and zinc acetate in n-octanoic acid at room temperature. The mass ratio of the doped dicarboxylic acid monoester to the TFB material is 1:20, the molar ratio of the dicarboxylic acid monoester to the zinc acetate is 1:3, and the dicarboxylic acid monoester is completely hydrolyzed to form glutaric acid by heating at 80 ℃ for 2h to obtain a solution 1.
2. The prepared solution 1 was deposited on PEDOT: and (3) coating the PSS for 30s in a spinning mode under the deposition condition of 3000r/min, and heating at 150 ℃ for 40min to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSe/ZnSe/ZnS quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 4000 r/min.
4. Depositing an ETL layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Example 4
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, the hole transport layer 4 is made of a composite material of adipic acid doped with TFB, the quantum dot light emitting layer 5 is made of CdZnSeS/ZnS quantum dots, the electron transport layer 6 is made of ZnO, and the cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. to the TFB solution dissolved in toluene solvent was added a certain amount of monomethyl adipate and zinc acetate in n-octanoic acid at room temperature. The mass ratio of the doped dicarboxylic acid monoester to the TFB material is 1:15, the molar ratio of the dicarboxylic acid monoester to the zinc acetate is 1:3, and the dicarboxylic acid monoester is completely hydrolyzed to form adipic acid by heating at 90 ℃ for 2.5h to obtain a solution 1.
2. The prepared solution 1 was deposited on PEDOT: and (3) spin-coating the PSS for 30s under the deposition condition of 3000r/min, and heating at 150 ℃ for 2h to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSeS/ZnS quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 4000 r/min.
4. Depositing an ETL layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Example 5
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, a hole transport layer 4 is made of a composite material of suberic acid doped with 4,4' -tris (N-carbazolyl) -triphenylamine, a quantum dot light emitting layer 5 is made of CdZnSe/ZnSe quantum dots, an electron transport layer 6 is made of ZnO, and a cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. at room temperature, a certain amount of monomethyl suberate and indium acetate solution in N-octanoic acid was added to a solution of 4,4' -tris (N-carbazolyl) -triphenylamine dissolved in chloroform solvent. The mass ratio of the doped dicarboxylic acid monoester to the 4,4' -tris (N-carbazolyl) -triphenylamine material is 1:30, the molar ratio of the dicarboxylic acid monoester to indium acetate is 1:1, and the dicarboxylic acid monoester is completely hydrolyzed to form suberic acid by heating at 80 ℃ for 2h to obtain a solution 1.
2. And depositing the prepared solution 1 on a hole injection layer (PEDOT: PSS), spin-coating for 30s under the deposition condition of 3000r/min, and heating at 150 ℃ for 2h to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSe/ZnSe quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 3000 r/min.
4. Depositing an electron transport layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Example 6
The present embodiment provides a QLED device having a structure as shown in fig. 2, and the QLED device includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a quantum dot light-emitting layer 5, an electron transport layer 6, and a cathode 7 in this order from bottom to top. The substrate 1 is made of a glass sheet, the anode 2 is made of an ITO (indium tin oxide) substrate, and the hole injection layer 3 is made of PEDOT: PSS, the hole transport layer 4 is made of a composite material of octanedioic acid doped 4,4' -tris (N-carbazolyl) -triphenylamine, the quantum dot light emitting layer 5 is made of CdZnSe/ZnSe/ZnS quantum dots, the electron transport layer 6 is made of ZnO, and the cathode 7 is made of Al.
The preparation method of the device comprises the following steps:
1. at room temperature, a certain amount of monomethyl suberate and a certain amount of titanium acetate in N-octanoic acid solution were added to a solution of 4,4' -tris (N-carbazolyl) -triphenylamine dissolved in a chloroform solvent. The mass ratio of the doped dicarboxylic acid monoester to the 4,4' -tris (N-carbazolyl) -triphenylamine material is 1:30, the molar ratio of the dicarboxylic acid monoester to the titanium acetate is 1:1, and the dicarboxylic acid monoester is completely hydrolyzed to form suberic acid by heating at 80 ℃ for 2h to obtain a solution 1.
2. And depositing the prepared solution 1 on a hole injection layer (PEDOT: PSS), spin-coating for 30s under the deposition condition of 3000r/min, and heating at 150 ℃ for 2h to complete crystallization to obtain the hole transport layer.
3. And depositing CdZnSe/ZnSe/ZnS quantum dots on the hole transport layer, and spin-coating for 30s at a certain rotation speed of 3000 r/min.
4. Depositing an electron transport layer, namely a ZnO layer, spin-coating at 3000r/min for 30s, and heating at 80 ℃ for 30 min.
5. And then evaporating an Al electrode, and packaging by adopting electronic glue to obtain the QLED device.
Comparative example 1
This comparative example was prepared in the same manner as in example 1, except that the material of the hole transport layer was the undoped TFB material.
Comparative example 2
This comparative example was prepared in the same manner as example 2, except that the material of the hole transport layer was the undoped TFB material.
Comparative example 3
This comparative example was prepared in the same manner as in example 3, except that the material of the hole transport layer was the undoped TFB material.
Comparative example 4
This comparative example was prepared in the same manner as example 4, except that the material of the hole transport layer was the undoped TFB material.
Comparative example 5
This comparative example was prepared in the same manner as example 5, except that the material of the hole transport layer was an undoped 4,4',4 ″ -tris (N-carbazolyl) -triphenylamine material.
Comparative example 6
This comparative example was prepared in the same manner as example 6, except that the material of the hole transport layer was an undoped 4,4',4 ″ -tris (N-carbazolyl) -triphenylamine material.
Performance testing
The quantum dot light-emitting diodes prepared in the comparative examples 1 to 6 and the examples 1 to 6 were subjected to performance tests, and the test methods were as follows:
(1) external quantum dot efficiency:
the ratio of the number of electrons-holes injected into the quantum dots to the number of emitted photons, the unit is%, is an important parameter for measuring the quality of the electroluminescent device, and can be obtained by measuring with an EQE optical measuring instrument. The specific calculation formula is as follows:
in the formula etaeFor light output coupling efficiency, ηrIs the ratio of the number of recombination carriers to the number of injection carriers, chi is the ratio of the number of excitons generating photons to the total number of excitons, KRTo the rate of the radiation process, KNRIs the non-radiative process rate.
And (3) testing conditions are as follows: the method is carried out at room temperature, and the air humidity is 30-60%.
(2) Life of QLED device:
the time required for the luminance of the device to decrease to a certain proportion of the maximum luminance under constant current or voltage driving, the time for the luminance to decrease to 95% of the maximum luminance is defined as T95, and the lifetime is the measured lifetime. To shorten the test period, the device lifetime test is usually performed at high luminance by accelerating device aging with reference to the OLED device test, and the lifetime at high luminance is obtained by fitting an extended exponential decay luminance fitting formula, for example: lifetime at 1000nit is measured as T951000nit. The specific calculation formula is as follows:
in the formula T95LFor lifetime at low brightness, T95HMeasured lifetime at high brightness, LHFor acceleration of the device to maximum brightness, LLThe luminance of the green QLED device is 1000nit, A is an acceleration factor, for OLED, the value is usually 1.6-2, and the value of A is 1.7 by measuring the service life of a plurality of groups of green QLED devices under rated luminance in the experiment.
And (3) carrying out life test on the corresponding device by adopting a life test system, wherein the test conditions are as follows: the method is carried out at room temperature, and the air humidity is 30-60%.
(3) Hole mobility: the average rate of the carrier under the action of unit electric field reflects the transport capacity of the carrier under the action of electric field, and the unit is cm2V · s. The hole-type device can be obtained by preparing a corresponding pure hole type device and then measuring by adopting a space charge limited current method (SCLC). The pure hole device structure is as follows: anode/hole transport layer/cathode. The specific calculation formula is as follows:
in the formula, d is the thickness of the material of the hole transport layer to be determined, the unit is nm, F is the applied electric field, the unit is V/m, and L is the thickness of the whole device, and the unit is nm.
And (3) testing conditions are as follows: the method is carried out at room temperature, and the air humidity is 30-60%.
The test results are shown in table 1:
TABLE 1
As can be seen from table 1 above, the hole transport layer thin films of the examples of the present invention have significantly higher hole mobility than the respective corresponding hole transport layer thin films of the comparative examples. In addition, the external quantum efficiency and the service life of the quantum dot light-emitting diode provided by the embodiment of the invention are obviously higher than those of the quantum dot light-emitting diode in the corresponding comparative example, which shows that the quantum dot light-emitting diode provided by the embodiment of the invention has better luminous efficiency.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A composite material, comprising an organic semiconductor material, an organic molecule and a metal ion, wherein the organic molecule has a structure represented by the following formula I, and a carboxyl group on the organic molecule is coordinated to the metal ion and is linked to the organic semiconductor material through the metal ion;
wherein R is1Is- (CH)2)nN is an integer greater than or equal to 1.
2. The composite material of claim 1, wherein R of the organic molecule1Wherein n is 2-20; and/or the presence of a gas in the gas,
the mass ratio of the organic molecules to the organic semiconductor material is (0.1-1): 30, of a nitrogen-containing gas; and/or the presence of a gas in the gas,
the molar ratio of the organic molecules to the metal ions is (1-3): 1.
3. the composite material according to claim 1, wherein the organic semiconducting material is selected from the group consisting of poly (9, 9-dioctyl-fluorene-co-N- (4-butylphenyl) -diphenylamine), polyarylamines, poly (N-vinylcarbazole), polyaniline, polypyrrole, one or more of N, N ' -tetrakis (4-methoxyphenyl) -benzidine, 4-bis [ N- (1-naphthyl) -N-phenyl-amino ] biphenyl, 4',4 ″ -tris [ phenyl (m-tolyl) amino ] triphenylamine, 4',4 ″ -tris (N-carbazolyl) -triphenylamine, and 1, 1-bis [ (di-4-tolylamino) phenylcyclohexane; and/or the presence of a gas in the gas,
the organic semiconductor material is selected from organic hole transport materials containing amine groups; and/or the presence of a gas in the gas,
the metal ions are selected from one or more of zinc ions, titanium ions, aluminum ions, indium ions, tin ions, zirconium ions and gallium ions.
4. The composite material according to any one of claims 1 to 3, wherein the composite material consists of the organic semiconductor material, an organic molecule and a metal ion.
5. The preparation method of the composite material is characterized by comprising the following steps:
providing an organic semiconductor material, a dicarboxylic acid monoester organic matter shown as the following formula II and a metal ion precursor;
dissolving the organic semiconductor material, the dicarboxylic acid monoester organic matter and the metal ion precursor in a nonpolar solvent, and heating to obtain a mixed solution;
carrying out solid-liquid separation on the mixed solution to obtain the composite material;
wherein R is1Is- (CH)2)n-，R2is-O (CH)2)mCH3N is an integer of 1 or more, and m is an integer of 0 or more.
6. The method of claim 5, wherein R of the dicarboxylic acid monoester organic matter is1Wherein n is 2-20; and/or the presence of a gas in the gas,
r of the dicarboxylic acid monoester organic matter2Wherein m is 2-20.
7. The method for producing the composite material according to claim 5, wherein the mass ratio of the dicarboxylic acid monoester organic matter to the organic semiconductor material is (0.1 to 1): 30, of a nitrogen-containing gas; and/or the presence of a gas in the gas,
the molar ratio of the dicarboxylic acid monoester organic matter to the metal ion precursor is (1-3): 1.
8. the method of claim 5, wherein the conditions of the heat treatment comprise: the temperature is 60-120 ℃, and the time is 30 min-4 h; and/or the presence of a gas in the gas,
the solid-liquid separation comprises annealing crystallization at the temperature of 140-160 ℃.
9. A method for the production of a composite material according to any one of claims 5 to 8, the organic semiconductor material is selected from one or more of poly (9, 9-dioctyl-fluorene-co-N- (4-butylphenyl) -diphenylamine), polyarylamine, poly (N-vinylcarbazole), polyaniline, polypyrrole, N ' -tetrakis (4-methoxyphenyl) -benzidine, 4-bis [ N- (1-naphthyl) -N-phenyl-amino ] biphenyl, 4',4 ″ -tris [ phenyl (m-tolyl) amino ] triphenylamine, 4',4 ″ -tris (N-carbazolyl) -triphenylamine, and 1, 1-bis [ (di-4-tolylamino) phenylcyclohexane; and/or the presence of a gas in the gas,
the metal ion precursor is selected from one or more of a zinc ion precursor, a titanium ion precursor, an aluminum ion precursor, an indium ion precursor, a tin ion precursor, a zirconium ion precursor and a gallium ion precursor.
10. A quantum dot light-emitting diode comprising an anode, a cathode and a quantum dot light-emitting layer between the anode and the cathode, wherein a hole transport layer is arranged between the anode and the quantum dot light-emitting layer, and the hole transport layer is composed of the composite material according to any one of claims 1 to 4 or the composite material obtained by the preparation method according to any one of claims 5 to 9.
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