CN117659741A - Zinc oxide-based nanoparticle, preparation method thereof, ink and electroluminescent device - Google Patents
Zinc oxide-based nanoparticle, preparation method thereof, ink and electroluminescent device Download PDFInfo
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- CN117659741A CN117659741A CN202311477937.3A CN202311477937A CN117659741A CN 117659741 A CN117659741 A CN 117659741A CN 202311477937 A CN202311477937 A CN 202311477937A CN 117659741 A CN117659741 A CN 117659741A
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 title claims abstract description 226
- 239000011787 zinc oxide Substances 0.000 title claims abstract description 113
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000002105 nanoparticle Substances 0.000 title description 20
- 239000003446 ligand Substances 0.000 claims abstract description 31
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 18
- 150000001408 amides Chemical class 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 26
- 239000002159 nanocrystal Substances 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 21
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 17
- PJDOLCGOTSNFJM-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PJDOLCGOTSNFJM-UHFFFAOYSA-N 0.000 claims description 13
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- -1 amine compound Chemical class 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 6
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 claims description 6
- 239000005456 alcohol based solvent Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000004210 ether based solvent Substances 0.000 claims description 4
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 3
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 3
- 229940047889 isobutyramide Drugs 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940080818 propionamide Drugs 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 238000012986 modification Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 4
- 239000002245 particle Substances 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract 3
- PNHVEGMHOXTHMW-UHFFFAOYSA-N magnesium;zinc;oxygen(2-) Chemical compound [O-2].[O-2].[Mg+2].[Zn+2] PNHVEGMHOXTHMW-UHFFFAOYSA-N 0.000 description 50
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 239000002096 quantum dot Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 12
- 238000004806 packaging method and process Methods 0.000 description 12
- 238000007639 printing Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 238000007641 inkjet printing Methods 0.000 description 7
- 238000009210 therapy by ultrasound Methods 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 6
- 239000004696 Poly ether ether ketone Substances 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 6
- 239000011654 magnesium acetate Substances 0.000 description 6
- 229940069446 magnesium acetate Drugs 0.000 description 6
- 235000011285 magnesium acetate Nutrition 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002530 polyetherether ketone Polymers 0.000 description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000004246 zinc acetate Substances 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001362551 Samba Species 0.000 description 1
- 229910003363 ZnMgO Inorganic materials 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Abstract
The invention relates to the technical field of nanometer, and discloses zinc oxide-based nanometer particles, a preparation method thereof, ink and an electroluminescent device, wherein zinc oxide-based nanometer crystals comprise zinc oxide-based nanometer crystal bodies, and unsaturated carboxylic acid ligands and amide ligands are modified on the surfaces of the zinc oxide-based nanometer crystal bodies. According to the invention, the original hydroxyl and carboxyl ligands with short chain length on the surface of the zinc oxide-based nanocrystalline body are modified into unsaturated carboxylic acid and amide with long chain length, and the hydrogen bond effect is weakened, so that the zinc oxide-based nanocrystalline is not easy to agglomerate in the ink. Compared with the device prepared by adopting zinc oxide-based nanocrystalline without modification, the device prepared by the zinc oxide-based ink has the advantage that the maximum external quantum efficiency is greatly improved.
Description
Technical Field
The invention belongs to the technical field of nanometer, and particularly relates to zinc oxide-based nanometer particles, a preparation method thereof, ink and an electroluminescent device.
Background
Zinc oxide is a wide band gap ii-vi compound and is an important semiconductor material. The zinc oxide-based nano particles have strong electron transmission capability, the lowest unoccupied molecular orbital energy level of the zinc oxide-based nano particles is very matched with the work function of aluminum, and the zinc oxide-based nano particles are favorable for realizing the effective injection of electrons of an aluminum electrode. Meanwhile, the zinc oxide-based nano particles have the characteristics of high transparency and the like, and the characteristics enable the zinc oxide-based nano particles to be frequently used as electron transport materials of electroluminescent devices.
The application of inkjet printing techniques to the fabrication of quantum dot light emitting diodes is considered to be an effective way to address the high cost and to achieve large areas. However, the surface of the zinc oxide-based nano particles in the existing zinc oxide-based nano particle ink is provided with hydroxyl, carboxyl and other short-chain groups, so that the hydrogen bonding effect is strong, the zinc oxide-based nano particles in the zinc oxide-based nano particle ink are easy to agglomerate, a spray head is easy to block in the ink-jet printing process, the printing effect is influenced, and the luminous efficiency of a device is further influenced.
In view of this, it is necessary to develop a zinc oxide-based nanoparticle which is not easily agglomerated, ensuring smooth printing of the zinc oxide-based nanoparticle ink.
Disclosure of Invention
In view of the above, the present invention aims to provide a zinc oxide-based nanoparticle, a preparation method thereof, an ink, and an electroluminescent device.
According to a first aspect of the present invention, there is provided a zinc oxide-based nanocrystal comprising a zinc oxide-based nanocrystal body, the surface of which is modified with an unsaturated carboxylic acid ligand and an amide ligand. According to the invention, the original hydroxyl and carboxyl ligands with short chain length on the surface of the zinc oxide-based nanocrystalline body are modified into unsaturated carboxylic acid ligands and amide ligands with long chain length, and the hydrogen bond effect is weakened, so that the zinc oxide-based nanocrystalline is not easy to agglomerate in the ink.
As a preferable mode of the zinc oxide-based nanocrystal, the weight percentage of the ligand in the zinc oxide-based nanocrystal is 5wt% to 30wt%.
As a preferred embodiment of the zinc oxide-based nanocrystals described above, the unsaturated carboxylic acid as a ligand comprises an olefmic acid, preferably the olefmic acid is selected from the group consisting of acrylic acid and methacrylic acid;
the amide as the ligand includes at least one of formamide, acetamide, propionamide, butyramide or isobutyramide.
According to a second aspect of the present invention, there is provided a method for preparing zinc oxide-based nanocrystals, comprising the steps of:
s1, mixing 12-20wt% of initial zinc oxide-based nanocrystalline body and 2-10wt% of unsaturated carboxylic acid for reaction;
s2, reacting the reaction product of the step S1 with 0.5-1wt% of amine compound;
preferably, the unsaturated carboxylic acid comprises an alkenoic acid;
preferably, the olefmic acid is selected from acrylic acid, methacrylic acid.
As a preferable mode of the above-mentioned method for producing zinc oxide-based nanocrystals, the amine compound includes one of dimethylamine, diethylamine, dipropylamine, dibutylamine, N-ethylmethylamine, N-methyl N-propylamine.
According to a third aspect of the present invention, there is provided a zinc oxide-based ink comprising:
the zinc oxide-based nanocrystalline or the zinc oxide-based nanocrystalline prepared by the preparation method;
and alcohol solvents and ether solvents having successively higher boiling points.
As a preferable scheme of the zinc oxide-based ink, the mass content of the zinc oxide-based nanocrystalline is 2-3wt%.
As a preferable embodiment of the zinc oxide-based ink, the alcohol solvent includes 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, and perfluoro octanol; the ether solvent comprises tripropylene glycol methyl ether.
As a preferable scheme of the zinc oxide-based ink, the mass contents of the 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, perfluoro octanol and tripropylene glycol methyl ether are respectively 33-37wt%, 6-9wt%, 20-25wt%, 2-4wt% and 28-32wt%.
According to a fourth aspect of the present invention, there is provided an electroluminescent device characterized by comprising an electron transport layer prepared from the zinc oxide-based ink described above.
Compared with the prior art, the invention has at least the following advantages:
1. according to the invention, the original hydroxyl and carboxyl ligands with short chain length on the surface of the zinc oxide-based nanocrystalline body are modified into unsaturated carboxylic acid and amide with long chain length, and the hydrogen bond effect is weakened, so that the zinc oxide-based nanocrystalline has better dispersibility in ink and is not easy to agglomerate;
2. when the zinc oxide-based nanocrystalline is prepared, unsaturated carboxylic acid is added to replace the hydroxyl on the original zinc oxide-based nanocrystalline body, then amine compound is added to react with the carboxyl on the original zinc oxide-based nanocrystalline body to form amide ligand, so that the ligand on the surface of the zinc oxide-based nanocrystalline body is a long-chain segment ligand, the existence of the long-chain segment ligand can enable the spacing of the zinc oxide-based nanocrystalline to be better, and the problem of agglomeration of the traditional zinc oxide-based nanocrystalline due to hydrogen bonding is solved;
3. alcohol solvents and ether solvents with boiling points rising in sequence are adopted in the zinc oxide-based ink, and when the zinc oxide-based ink is subjected to ink jet printing, the solvents are evaporated according to gradient, so that the solvent is prevented from being evaporated at one time, the dispersibility of the zinc oxide-based nanocrystalline in the film forming process is ensured, and the film surface is smooth;
4. compared with the device prepared by adopting zinc oxide-based nanocrystalline which is not subjected to ligand modification, the device prepared by the electronic transmission layer prepared by the zinc oxide-based ink has the advantage that the maximum external quantum efficiency is greatly improved.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph of droplet size for printing zinc magnesium oxide ink of the present invention using an ink jet printer;
FIG. 2 is a diagram of the drop states of the zinc magnesium oxide ink of the present invention when printed using an ink jet printer;
FIG. 3 is a diagram of a hundred-point verification of printing of the zinc magnesium oxide ink of the present invention using an ink jet printer;
FIG. 4 is a waveform diagram of a printing process for printing the zinc magnesium oxide ink of the present invention using an ink jet printer;
FIG. 5 is a film side view of the electroluminescent device of example 1;
FIG. 6 is a film side view of the electroluminescent device of comparative example 1;
FIG. 7 is a film side view of an electroluminescent device of example 2;
FIG. 8 is a film side view of the electroluminescent device of comparative example 2;
FIG. 9 is a film side view of an electroluminescent device of example 3;
fig. 10 is a film side view of the electroluminescent device of comparative example 3.
Detailed Description
The technical solutions in the examples will be described in detail below in connection with the embodiments of the present invention. It should be noted that this embodiment is only a partial way, not an entire way.
At least one of the "when preceding or following a list of elements" as for example "is described herein modifies the entire list of elements without modifying individual elements of the list. Unless otherwise defined, all terms (including technical and scientific terms) in the specification can be defined as commonly understood by one of ordinary skill in the art. Terms defined in commonly used dictionaries should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein. Furthermore, unless expressly stated to the contrary, the words "comprise" and the words "comprising" when used in this specification mean the presence of stated features, regions, integers, steps, operations, elements, and/or components, but does not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof. Accordingly, the above phraseology is to be understood as meaning to include the stated elements, but not to exclude any other elements.
As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. The term "or" means "and/or".
It will be understood that, although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms.
As used herein, "about" or "approximately" includes the stated values and is meant to be within an acceptable range of deviation from the particular values as determined by one of ordinary skill in the art in view of the measurements in question and the errors associated with the measurement of the particular quantities (i.e., limitations of the measurement system). For example, "about" may mean that the deviation from the stated value is within one or more standard deviations, or within + -10%, + -5%.
As described in the background art, the surface of the zinc oxide-based nano particles in the existing zinc oxide-based nano particle ink is provided with hydroxyl groups, carboxyl groups and other short-chain groups, so that the hydrogen bond effect is strong, the zinc oxide-based nano particles in the zinc oxide-based nano particle ink are easy to agglomerate, a spray head is easy to block in the ink-jet printing process, the printing effect is influenced, and the luminous efficiency of a device is further influenced.
Based on this, in a first aspect of the present invention, there is provided a zinc oxide-based nanocrystal comprising a zinc oxide-based nanocrystal body having its surface modified with an unsaturated carboxylic acid ligand and an amide ligand. According to the invention, the original hydroxyl and carboxyl ligands with short chain length on the surface of the zinc oxide-based nanocrystalline body are modified into unsaturated carboxylic acid ligands and amide ligands with long chain length, and the hydrogen bond effect is weakened, so that the zinc oxide-based nanocrystalline is not easy to agglomerate in the ink.
The zinc oxide-based nanocrystalline body comprises zinc oxide nano particles doped or undoped with metal elements; preferably, the zinc oxide-based nanoparticle is ZnMgO, znLiMgO or znlialmo.
As a preferable mode of the zinc oxide-based nanocrystal, the weight percentage of the ligand in the zinc oxide-based nanocrystal is 5wt% to 30wt%. The inventors found that when the content of the above ligand is controlled within this range, it is possible to ensure not only that the zinc oxide-based nanocrystals do not agglomerate in the ink, but also that the zinc oxide-based nanocrystals themselves have a strong electron transport ability.
As a preferred embodiment of the zinc oxide-based nanocrystals described above, the unsaturated carboxylic acid as a ligand includes an acrylic acid, an methacrylic acid, a crotonic acid, a maleic acid, a fumaric acid, an itaconic acid, a cinnamic acid, and an unsaturated fatty acid such as linolenic acid or oleic acid, etc. Preferably, the olefmic acid is selected from acrylic acid, methacrylic acid. Such as at least one of 2-phenylacrylic acid, alpha-methacrylic acid, polymethacrylic acid, 3-dimethacrylate and the like.
The amide as the ligand includes at least one of formamide, acetamide, propionamide, butyramide or isobutyramide.
According to a second aspect of the present invention, there is provided a method for preparing zinc oxide-based nanocrystals, comprising the steps of:
s1, mixing 12-20wt% of initial zinc oxide-based nanocrystalline body and 2-10wt% of unsaturated carboxylic acid for reaction;
s2, reacting the reaction product of the step S1 with 0.5-1wt% of amine compound;
preferably, the unsaturated carboxylic acid comprises an alkenoic acid;
preferably, the olefmic acid is selected from acrylic acid, methacrylic acid.
In the step S1, ultrasonic treatment is adopted for 1-3 hours; in the step S2, stirring is carried out at normal temperature for 25-35min.
As a preferable mode of the above-mentioned method for producing zinc oxide-based nanocrystals, the amine compound includes one of dimethylamine, diethylamine, dipropylamine, dibutylamine, N-ethylmethylamine, N-methyl N-propylamine.
According to a third aspect of the present invention, there is provided a zinc oxide-based ink comprising:
the zinc oxide-based nanocrystalline or the zinc oxide-based nanocrystalline prepared by the preparation method;
and alcohol solvents and ether solvents having successively higher boiling points.
As a preferable scheme of the zinc oxide-based ink, the mass content of the zinc oxide-based nanocrystalline is 2-3wt%.
As a preferable embodiment of the zinc oxide-based ink, the alcohol solvent includes 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, and perfluoro octanol; the ether solvent comprises tripropylene glycol methyl ether.
As a preferable scheme of the zinc oxide-based ink, the mass contents of the 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, perfluoro octanol and tripropylene glycol methyl ether are respectively 33-37wt%, 6-9wt%, 20-25wt%, 2-4wt% and 28-32wt%.
Because zinc oxide-based nanocrystalline is dissolved in ethanol for standby, when the zinc oxide-based nanocrystalline is added into the solvent, the ethanol solvent of the zinc oxide-based solution needs to be distilled off, in order to avoid agglomeration of the zinc oxide-based nanocrystalline after the spin distillation and incapability of being dispersed in the solvent, partial tripropylene glycol methyl ether needs to be added into the zinc oxide-based nanocrystalline solution, ethanol needs to be distilled off for solvent replacement, then 3,5 trimethyl-1-hexanol, the rest tripropylene glycol methyl ether, n-butanol, dimethyl-2, 4-dipentyl alcohol and perfluoro octanol solvent are sequentially added, stirring is carried out for 2 hours in an atmosphere of normal temperature nitrogen protection, and a filter head of 0.22um is adopted for filtering 3 times, so that the zinc oxide-based ink is prepared for standby.
According to a fourth aspect of the present invention, there is provided an electroluminescent device comprising an electron transport layer prepared from the zinc oxide-based ink described above.
The present invention will be described in further detail with reference to specific examples and comparative examples, but the present invention is not limited to the following examples, and the implementation conditions adopted in the examples may be further adjusted according to different requirements of specific use, and the conditions not specified are conventional conditions in the industry.
Example 1
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
S4, mixing 16wt% of initial zinc oxide magnesium nanocrystalline body and 8wt% of 3, 3-dimethyl acrylic acid, and ultrasonically stirring for 2 hours to obtain a first reaction product;
s5, mixing the first reaction product obtained in the step S4 with 0.5 weight percent of 1, 4-butanediamine, and stirring for 30 minutes at normal temperature to obtain the modified zinc oxide magnesium nanocrystalline.
2. Zinc-magnesium oxide ink
According to the mass percentage, 2 percent of modified zinc magnesium oxide nanocrystalline (dissolved in ethanol), 35 percent of 3,5 trimethyl-1-hexanol, 30 percent of tripropylene glycol methyl ether, 7 percent of n-butanol, 23 percent of dimethyl-2, 4-dipentaerythritol and 3 percent of perfluoro octanol are prepared.
S1, adding a part of tripropylene glycol methyl ether solvent into a zinc oxide magnesium nanocrystalline solution, and removing an ethanol solvent by rotary evaporation;
s2, sequentially adding 3,5 trimethyl-1-hexanol, the rest tripropylene glycol methyl ether, n-butanol, dimethyl-2, 4-dipentaerythritol and perfluoro-octanol solvent, stirring for 2h in a normal temperature nitrogen protection atmosphere, and filtering for 3 times by a filter head of 0.22um to obtain zinc oxide-based ink for later use.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a red CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide-based ink is printed on the red CdSe quantum dot luminescent layer in an ink-jet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
Comparative example 1
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
2. Zinc-magnesium oxide ink
Comprises 90wt% of n-octanol, 5wt% of 2, 4-pentanediol and 5wt% of the zinc oxide magnesium nanocrystalline body.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a red CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide magnesium ink is printed on the red CdSe quantum dot luminescent layer in an ink-jet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
Example 2
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
S4, mixing 16wt% of initial zinc oxide magnesium nanocrystalline body and 8wt% of 3, 3-dimethyl acrylic acid, and ultrasonically stirring for 2 hours to obtain a first reaction product;
s5, mixing the first reaction product obtained in the step S1 with 0.5 weight percent of 1, 4-butanediamine, and stirring for 30min at normal temperature to obtain the modified zinc oxide magnesium nanocrystalline.
2. Zinc-magnesium oxide ink
According to the mass percentage, 2 percent of modified zinc magnesium oxide nanocrystalline (dissolved in ethanol), 35 percent of 3,5 trimethyl-1-hexanol, 30 percent of tripropylene glycol methyl ether, 7 percent of n-butanol, 23 percent of dimethyl-2, 4-dipentaerythritol and 3 percent of perfluoro octanol are prepared.
S1, adding a part of tripropylene glycol methyl ether solvent into a zinc oxide magnesium nanocrystalline solution, and removing an ethanol solvent by rotary evaporation;
s2, sequentially adding 3,5 trimethyl-1-hexanol, the rest tripropylene glycol methyl ether, n-butanol, dimethyl-2, 4-dipentaerythritol and perfluoro-octanol solvent, stirring for 2h in a normal temperature nitrogen protection atmosphere, and filtering for 3 times by a filter head of 0.22um to obtain zinc oxide-based ink for later use.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a green CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide-based ink is printed on the green CdSe quantum dot luminescent layer in an inkjet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
Comparative example 2
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
2. Zinc-magnesium oxide ink
Comprises 90wt% of n-octanol, 5wt% of 2, 4-pentanediol and 5wt% of the zinc oxide magnesium nanocrystalline body.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a green CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide magnesium ink is printed on the green CdSe quantum dot luminescent layer in an ink-jet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
Example 3
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
S4, mixing 16wt% of initial zinc oxide magnesium nanocrystalline body and 8wt% of 3, 3-dimethyl acrylic acid, and ultrasonically stirring for 2 hours to obtain a first reaction product;
s5, mixing the first reaction product obtained in the step S1 with 0.5 weight percent of 1, 4-butanediamine, and stirring for 30min at normal temperature to obtain the modified zinc oxide magnesium nanocrystalline.
2. Zinc-magnesium oxide ink
According to the mass percentage, 2 percent of modified zinc magnesium oxide nanocrystalline (dissolved in ethanol), 35 percent of 3,5 trimethyl-1-hexanol, 30 percent of tripropylene glycol methyl ether, 7 percent of n-butanol, 23 percent of dimethyl-2, 4-dipentaerythritol and 3 percent of perfluoro octanol are prepared.
S1, adding a part of tripropylene glycol methyl ether solvent into a zinc oxide magnesium nanocrystalline solution, and removing an ethanol solvent by rotary evaporation;
s2, sequentially adding 3,5 trimethyl-1-hexanol, the rest tripropylene glycol methyl ether, n-butanol, dimethyl-2, 4-dipentaerythritol and perfluoro-octanol solvent, stirring for 2h in a normal temperature nitrogen protection atmosphere, and filtering for 3 times by a filter head of 0.22um to obtain zinc oxide-based ink for later use.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a green CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide-based ink is printed on the green CdSe quantum dot luminescent layer in an inkjet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
Comparative example 3
1. Preparation of initial zinc oxide magnesium nanocrystalline body
S1, mixing 5mmol of tetramethyl ammonium hydroxide (TMAH) with 20ml of ethylene glycol methyl ether at room temperature, and stirring for 20min;
s2, mixing 3mmol of zinc acetate and 0.5mmol of magnesium acetate with 20ml of dimethyl sulfoxide, adding the mixture into the mixed solution in the S1, and stirring for 2 hours;
s3, carrying out ultrasonic treatment for 30min, purifying to obtain an initial zinc oxide magnesium nanocrystalline body, and dissolving the zinc oxide magnesium nanocrystalline body in an ethanol solution for later use.
2. Zinc-magnesium oxide ink
Comprises 90wt% of n-octanol, 5wt% of 2, 4-pentanediol and 5wt% of the zinc oxide magnesium nanocrystalline body.
3. Preparation of electroluminescent device
S1, providing a flexible substrate on which an ITO conductive layer is formed;
s2, sequentially spin-coating a PEDOT (polyether-ether-ketone) PSS layer, a TFB layer and a green CdSe quantum dot luminescent layer on the ITO conductive layer;
s3, the zinc oxide magnesium ink is printed on the green CdSe quantum dot luminescent layer in an ink-jet mode, and an electron transmission layer is formed;
s4, evaporating an Al layer on the electron transport layer;
s5, packaging by using packaging glue.
The zinc magnesium oxide ink of the embodiments 1-3 is subjected to ink jet printing by adopting an Omnijet-500 GB (nozzle model: samba cartridge) ink jet printer, the printing situation is shown in fig. 1-4, and from the droplet size (3.7 pl) chart of fig. 1, the droplet state of the ink jet printing of fig. 2 and the hundred-point verification chart of fig. 3, it can be seen that the ink droplets are small, the ink dots cannot overlap, and high-quality printing can be realized; as can be seen from the printing waveform diagram of fig. 4, the printing is smooth and suitable for inkjet printing at a relatively high speed.
After long-time continuous printing, the zinc magnesium oxide ink provided by the invention is found to not only not block a spray head, but also have no deviation in ink drop track, so that the zinc magnesium oxide ink provided by the invention is good in dispersibility.
Finally, the electroluminescent devices of examples 1 to 3 and comparative examples 1 to 3 were subjected to power-on test, and the test data are shown in Table 1 below.
TABLE 1
It can be seen that the R/G/B device prepared by using the modified zinc magnesium oxide has significantly improved current density, maximum current efficiency, brightness and maximum external quantum efficiency, especially the maximum EQE data, and the R-QLED has been improved from 18.2% to 23.4%; the G-QLED is improved from 5.7% to 8.3%; the B-QLED is promoted from 0.3% to 1.0%.
As shown in fig. 5 to 10, the film surface diagrams of the electroluminescent devices of examples 1 to 3 and comparative examples 1 to 3 were photographed by using a scanning electron microscope, and it can be seen that the film surfaces of the electroluminescent devices obtained in examples 1 to 3 of the present invention were uniform in light emission and did not have dark spots; while the electroluminescent devices of comparative examples 1 to 3 were non-uniform in film surface luminescence, and had dark spots. Compared with the device prepared by adopting zinc oxide-based nanocrystalline without modification, the device prepared by the zinc oxide-based ink has the advantage that the effect of the device is greatly improved.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The zinc oxide-based nanocrystalline is characterized by comprising a zinc oxide-based nanocrystalline body, wherein the surface of the zinc oxide-based nanocrystalline body is modified with an unsaturated carboxylic acid ligand and an amide ligand.
2. The zinc oxide-based nanocrystal of claim 1, wherein the weight percentage of the ligand in the zinc oxide-based nanocrystal is 5wt% to 30wt%.
3. Zinc oxide-based nanocrystals according to claim 1, characterized in that said unsaturated carboxylic acid as ligand comprises an alkenoic acid, preferably selected from acrylic acid, methacrylic acid;
the amide as the ligand includes at least one of formamide, acetamide, propionamide, butyramide or isobutyramide.
4. The preparation method of the zinc oxide-based nanocrystalline is characterized by comprising the following steps:
s1, mixing 12-20wt% of initial zinc oxide-based nanocrystalline body and 2-10wt% of unsaturated carboxylic acid for reaction;
s2, reacting the reaction product of the step S1 with 0.5-1wt% of amine compound;
preferably, the unsaturated carboxylic acid comprises an alkenoic acid;
preferably, the olefmic acid is selected from acrylic acid, methacrylic acid.
5. The method for preparing zinc oxide-based nanocrystals, according to claim 4, wherein said amine compound comprises one of dimethylamine, diethylamine, dipropylamine, dibutylamine, N-ethylmethylamine, N-methyl N-propylamine.
6. A zinc oxide-based ink, comprising:
a zinc oxide-based nanocrystal according to any one of claims 1 to 3, or a zinc oxide-based nanocrystal prepared by the preparation method according to any one of claims 4 to 5;
and alcohol solvents and ether solvents having successively higher boiling points.
7. The zinc oxide-based ink according to claim 6, wherein the mass content of the zinc oxide-based nanocrystals is 2 to 3wt%.
8. The zinc oxide-based ink according to claim 6, wherein the alcohol-based solvent comprises 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, perfluoro octanol; the ether solvent comprises tripropylene glycol methyl ether.
9. The zinc oxide-based ink according to claim 8, wherein the mass contents of 3,5 trimethyl-1-hexanol, n-butanol, dimethyl-2, 4 dipentyl alcohol, perfluoro octanol and tripropylene glycol methyl ether are 33-37wt%, 6-9wt%, 20-25wt%, 2-4wt%, 28-32wt%, respectively.
10. An electroluminescent device comprising an electron transport layer prepared from the zinc oxide-based ink of any one of claims 6-9.
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