CN112011033B - Hyperbranched polymer, preparation method thereof and LED application - Google Patents
Hyperbranched polymer, preparation method thereof and LED application Download PDFInfo
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- CN112011033B CN112011033B CN201910467624.7A CN201910467624A CN112011033B CN 112011033 B CN112011033 B CN 112011033B CN 201910467624 A CN201910467624 A CN 201910467624A CN 112011033 B CN112011033 B CN 112011033B
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- 229920000587 hyperbranched polymer Polymers 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000012298 atmosphere Substances 0.000 claims abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 125000005649 substituted arylene group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 230000005284 excitation Effects 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000006862 quantum yield reaction Methods 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 238000004220 aggregation Methods 0.000 abstract description 10
- 230000002776 aggregation Effects 0.000 abstract description 10
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical group C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000004519 grease Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000001376 precipitating effect Effects 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000005551 pyridylene group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- -1 furanylidene Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005760 substituted naphthylene group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 125000005663 substituted pyridylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
- H01L33/502—Wavelength conversion materials
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Abstract
The application discloses a hyperbranched polymer, and a preparation method and application thereof, and belongs to the technical field of high polymer materials. The hyperbranched polymer comprises a structural unit with a structural formula shown as a formula (I):
Description
Technical Field
The application relates to a hyperbranched polymer and a preparation method and application thereof, belonging to the technical field of high molecular materials.
Background
The LED is called as a fourth generation illumination light source or a green light source, has the characteristics of energy conservation, environmental protection, long service life, small volume and the like, and can be widely applied to the fields of various indications, display, decoration, backlight sources, common illumination, urban landscape illumination and the like. The most common approach to realize white LEDs is phosphor-to-white LED conversion, i.e., a layer of yellow phosphor is coated on a blue-light wafer to mix blue light and yellow light into white light. However, the conventional fluorophore has an aggregation-quenching (ACQ) phenomenon, which greatly limits its application in the solid-state tunable light-emitting switching LED.
The aggregation-induced emission (AIE) phenomenon refers to a property that a compound has weak fluorescence even no fluorescence is observed in a single-molecule state, while fluorescence is significantly enhanced in an aggregated state. The compound with AIE property effectively overcomes the defects and opens up a new way for solid luminescence. At present, the application of the hyperbranched polymer fluorescent powder with aggregation-induced emission property in the LED is rarely reported.
Disclosure of Invention
According to one aspect of the present application, there is provided a hyperbranched polymer having aggregation-induced emission properties that emits weak fluorescence in a solution state and strong fluorescence in a solid and aggregated state.
The hyperbranched polymer is characterized by comprising a structural unit with a structural formula shown as a formula (I):
wherein Ar is1And Ar2Independently selected from arylene or substituted arylene;
the substituents in the substituted arylene group are selected from-OH, -NH2、-CH3and-OCH3One kind of (1).
Optionally, the arylene group is selected from one of phenylene, naphthylene, pyridinylene, silolylene, and furanylene.
In the context of the present application, the expression "arylene" is intended to mean both the term "arylene" and the term "substituted arylene" arylene. For example, the above definition of "the arylene group is one selected from the group consisting of phenylene, naphthylene, pyridinylene, siloxanylene and furanylene" applies to the definition of the kind of the arylene group in the "substituted arylene group". Hereinafter, sometimes, for convenience, both are collectively referred to as "arylene".
In the context of the present application, the expression "arylene" means a group formed by the loss of one hydrogen atom from each of two carbon atoms in the molecule of an aromatic hydrocarbon compound and a heterocyclic compound having aromatic character. Here, the heterocyclic compound having aromatic character includes compounds based on pyridine, silole and furan.
Specifically, the pyridylene group means a group formed by losing one hydrogen atom each of any two carbon atoms in a pyridine molecule; the silole group means a group formed by losing one hydrogen atom from any two carbon atoms in a silole molecule; by furanylidene is meant a group formed by the loss of one hydrogen atom from each of any two carbon atoms in the furan molecule.
In the present application, the number of substituents in the substituted arylene group is not particularly limited, and may be selected according to actual needs. For example, in the case of a substituted phenylene group, the number of substituents can be 1 to 4; in the case of a substituted naphthylene group, the number of substituents may be 1 to 6; in the case of a substituted pyridylene group, the number of substituents may be 1 to 3.
In a preferred embodiment, in formula (I), Ar1And Ar2Are all phenylene radicals.
Optionally, the hyperbranched polymer has a number average molecular weight of 1600 to 10000 and a polydispersity index of 1.10 to 2.60.
Preferably, the hyperbranched polymer has a number average molecular weight of 4200 and a polydispersity index of 1.24.
Optionally, the hyperbranched polymer is composed of a structural unit having a structural formula shown in formula (I).
Preferably, the hyperbranched polymer consists of the same structural unit with a structural formula shown as a formula (I).
According to another aspect of the application, a preparation method of the hyperbranched polymer is provided, and the method has the advantages of simple process, mild conditions, strong operability, low cost, no toxicity and no harm.
The preparation method of the hyperbranched polymer is characterized by comprising the following steps:
carrying out Barbier polycondensation reaction on a mixture containing a reaction monomer, metal and an initiator at the temperature of 10-100 ℃ in an inactive atmosphere, and hydrolyzing to obtain the hyperbranched polymer;
wherein the reactive monomer is at least one selected from compounds having a structural formula shown in formula (II):
wherein，Ar1And Ar2Is as defined in formula (I); x1And X2Independently selected from fluorine, chlorine, bromine or iodine.
Alternatively, X1And X2Independently selected from chlorine or bromine, preferably chlorine.
In a preferred embodiment, in formula (II), Ar1And Ar2Are each phenylene, X1And X2Are all chlorine. In this case, the reactive monomer is 4,4' -dichlorobenzophenone.
In a preferred embodiment, the hyperbranched polymer is prepared by the process using 4,4' -dichlorobenzophenone as a reactive monomer. The hyperbranched polymer thus obtained may have a structural formula represented by formula (III) or formula (IV):
optionally, the metal is selected from at least one of magnesium, aluminum, tin, indium, zinc, bismuth, palladium, and samarium.
Optionally, the mixture comprises a solvent.
Preferably, the solvent is selected from tetrahydrofuran, diethyl ether, methyl tert-butyl ether, water or benzene, or a mixed solution of tetrahydrofuran and water in a volume ratio of 5:1, 4:1, 3:1, 2:1 and 1:1, or a mixed solution of tetrahydrofuran and benzene in a volume ratio of 2:1 and 1: 1.
Optionally, the initiator is selected from at least one of 1, 2-dichloroethane, 1, 2-dibromoethane, 1, 2-diiodoethane, methyl chloride, methyl bromide, methyl iodide, iodine, and red aluminum.
Optionally, the polycondensation reaction is conducted under a nitrogen atmosphere.
Optionally, the polycondensation reaction is carried out for 8 to 72 hours.
Preferably, the polycondensation reaction is carried out for a time with an upper limit selected from 72 hours, 64 hours, 56 hours, 48 hours, 40 hours, 32 hours, 24 hours, 16 hours and a lower limit selected from 8 hours, 16 hours, 24 hours, 32 hours, 40 hours, 48 hours, 56 hours, 64 hours.
More preferably, the polycondensation reaction is carried out at 45 ℃ for 24 hours.
Optionally, the molar ratio of the metal to the reactive monomer is 2.05:1 to 3: 1.
Preferably, the upper limit of the molar ratio of the metal to the reactive monomer is selected from 3:1, 2.95:1, 2.9:1, 2.85:1, 2.8:1, 2.75:1, 2.7:1, 2.65:1, 2.6:1, 2.55:1, 2.5:1, 2.45:1, 2.4:1, 2.35:1, 2.3:1, 2.25:1, 2.2:1, 2.15:1, 2.1:1, the lower limit is selected from 2.05:1, 2.1:1, 2.15:1, 2.2:1, 2.25:1, 2.3:1, 2.35:1, 2.4:1, 2.45:1, 2.5:1, 2.55:1, 2.6:1, 2.65:1, 2.7:1, 2.75:1, 2.8:1, 2.45:1, 2.5:1, 2.55:1, 2.6:1, 2.65:1, 2.7:1, 2.75:1, 2.1, 2.95:1, 2.1.
Optionally, the molar ratio of the initiator to the reactive monomer is 0.01:1 to 0.2: 1.
Preferably, the upper limit of the molar ratio of the initiator to the reactive monomer is selected from 0.2:1, 0.19:1, 0.18:1, 0.17:1, 0.16:1, 0.15:1, 0.14:1, 0.13:1, 0.12:1, 0.11:1, 0.1:1, 0.09:1, 0.08:1, 0.07:1, 0.06:1, 0.05:1, 0.04:1, 0.03:1, 0.02:1, and the lower limit is selected from 0.01:1, 0.02:1, 0.03:1, 0.04:1, 0.05:1, 0.06:1, 0.07:1, 0.08:1, 0.09:1, 0.1:1, 0.11:1, 0.12:1, 0.13:1, 0.14:1, 0.07:1, 0.15:1, 0.16:1, 0.19:1, 0.18:1, 0.17: 1.
Alternatively, the hydrolysis is carried out using a saturated aqueous ammonium chloride solution.
Alternatively, purification is carried out after the reaction is completed.
Optionally, the method of purifying comprises: precipitation method, dialysis method.
Optionally, the precipitation method comprises: precipitating the product obtained by the method for preparing the hyperbranched polymer in a precipitating agent.
Preferably, the precipitation is performed at least twice.
Preferably, the precipitant is selected from at least one of methanol, ethanol, propanol, acetone, n-hexane, petroleum ether and diethyl ether.
In a specific embodiment, the method of preparing the hyperbranched polymer comprises the steps of:
a) dispersing metal in a solvent under an inactive atmosphere, respectively adding a reaction monomer and an initiator, and then carrying out a Barbier polycondensation reaction under a closed condition at the temperature of 10-100 ℃ to obtain an original product liquid;
b) layering the original product liquid obtained in the step a) in dichloromethane and saturated ammonium chloride aqueous solution, washing and collecting organic layer extract, drying the organic layer extract, and concentrating to obtain a crude product;
c) precipitating and purifying the crude product obtained in the step b) in a precipitating agent twice, and drying the precipitate in vacuum to obtain the hyperbranched polymer.
According to still another aspect of the present application, there is provided a fluorescent material having a high efficiency of fluorescence emission property.
The fluorescent material is characterized by comprising at least one of the hyperbranched polymer and the hyperbranched polymer prepared by the method.
Optionally, at least one of the hyperbranched polymer and the hyperbranched polymer prepared by the method has a fluorescence quantum yield of not less than 5% in an excitation wavelength of 360-460 nm and in a range of 470-800 nm.
Optionally, the hyperbranched polymer is present in a form comprising an aggregate of nanoparticles, a solid powder, or a solid film.
The fluorescent material containing the hyperbranched polymer having the aggregation-induced emission property according to the present application includes a fluorescent material having a high efficiency in the state of nanoparticle aggregates, solid powder and solid thin film. The fluorescent material is in a solid state, takes 360-460 nm as an excitation wavelength, and has a fluorescence quantum yield of not less than 5% within a range of 470-800 nm.
According to yet another aspect of the present application, a white LED is provided.
The white light LED is characterized by comprising at least one of the hyperbranched polymer, the hyperbranched polymer prepared by the method and the fluorescent material.
Optionally, the white light LED is obtained by converting a blue light wafer through the hyperbranched polymer and/or the fluorescent material.
In one embodiment, the application of the fluorescent material comprising the hyperbranched polymer with aggregation-induced emission properties provided by the application in the white light LED can be smeared on a blue light wafer to prepare the white light LED.
Optionally, the white light LED can be obtained by mixing an appropriate amount of the fluorescent material containing the hyperbranched polymer with aggregation-induced emission properties with a binder, and coating the mixture on a blue light wafer with an optimal emission wavelength of 460 nm.
Optionally, the ratio of the fluorescent material containing the hyperbranched polymer with aggregation-induced emission properties to the binder is adjusted to obtain white LEDs with different CIE coordinates, wherein the mass ratio of the fluorescent material containing the hyperbranched polymer with aggregation-induced emission properties to the binder may be in a range of 10:1 to 1: 1.
The beneficial effects that this application can produce include:
1) the hyperbranched polymer provided by the application has aggregation-induced emission properties of emitting weak fluorescence in a solution state and emitting strong fluorescence in a solid and aggregated state.
2) The preparation method of the hyperbranched polymer provided by the application has the advantages of simple process, mild conditions, strong operability, low cost, no toxicity and no harm.
3) The fluorescent material provided by the application has high-efficiency fluorescence emission property, and can be efficiently converted into a white light LED by being coated on a blue light wafer.
Drawings
FIG. 1 shows the results of gel permeation chromatography measurements of hyperbranched polymers prepared in example 1 of the present application.
FIG. 2 shows the results of gel permeation chromatography measurements of hyperbranched polymers prepared in example 2 of the present application.
Fig. 3 is a performance test result of a white LED prepared by using the hyperbranched polymer phosphor 1 of example 1 to convert a blue light wafer.
Fig. 4 is a performance test result of a white LED prepared by converting the hyperbranched polymer phosphor 2 of example 2 into a blue light wafer.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the raw materials and reagents in the examples of the present application were purchased commercially, wherein the raw materials were purchased from sahn chemical technology (shanghai) ltd, and the reagents were purchased from national pharmaceutical chemicals ltd.
The analysis method in the examples of the present application is as follows:
LED performance testing was performed using Spectra Scan PR 655.
Gel permeation chromatography was performed using a Viscotek TDA 302 triple detector.
Examples
Example 1: preparation of hyperbranched polymer phosphor 1
This example provides a method for preparing polymer by Barbier polycondensation using 4,4' -dichlorobenzophenone as reactive monomer, comprising the following steps:
a100 mL double-neck flask is taken, a branch opening is coated with vacuum grease, a rubber plug is used for plugging the branch opening, and an insulating tape is used for tightly winding the branch opening, so that good air tightness is ensured. Magnesium chips (0.48g, 0.02mol) are added into a double-mouth flask from a straight mouth, magnetons are added, and a condenser tube and a straight air suction connector are sequentially connected (all the joints need to be coated with vacuum grease and clamped by plastic clamps). The processes of vacuumizing, hot air gun blowing and scalding, cooling and nitrogen gas introduction are repeated for three times. And after the nitrogen is introduced for the last time, closing the straight air extraction joint, connecting the balloon filled with the nitrogen, and opening the plug of the straight air extraction joint to communicate the nitrogen.
16mL of refined and dried tetrahydrofuran was added to the double-neck flask from the rubber stopper with a syringe, and magnetic stirring was turned on to disperse the magnesium chips uniformly, and condensed water was turned on. 4,4' -dichlorobenzophenone (2.0g, 0.008mol) was dissolved in 5mL of dry tetrahydrofuran and then charged into a two-necked flask. After stirring for 5min, 0.1mL of 1, 2-dibromoethane was injected. After injection, the rubber plug needle is sealed with vacuum grease. After 24 hours of reaction at 45 ℃, the reaction was stopped.
And (3) carrying out suction filtration on the obtained original product liquid, transferring the filtrate into a separating funnel, adding 30mL of dichloromethane and 30mL of saturated ammonium chloride aqueous solution, shaking, standing and layering. Washing the lower layer liquid twice with water, collecting the organic layer extract, adding anhydrous sodium sulfate, drying for 4h, vacuum filtering to obtain yellow clear filtrate, and spin-drying the solvent with a rotary evaporator to obtain the corresponding macromolecule crude product. And (3) precipitating and purifying the obtained macromolecular crude product in petroleum ether twice, performing suction filtration, collecting powder precipitate, and performing vacuum drying to obtain a purified macromolecular product which is solid powder and is marked as fluorescent powder 1.
The molecular weight and molecular weight distribution of the resulting product were determined by gel permeation chromatography.
Example 2: preparation of hyperbranched polymer fluorescent powder 2
This example provides a method for preparing polymer by Barbier polycondensation using 4,4' -dichlorobenzophenone as reactive monomer, comprising the following steps:
a100 mL double-neck flask is taken, a branch opening is coated with vacuum grease, a rubber plug is used for plugging the branch opening, and an insulating tape is used for tightly winding the branch opening, so that good air tightness is ensured. Magnesium chips (0.48g, 0.02mol) are added into a double-mouth flask from a straight mouth, magnetons are added, and a condenser tube and a straight air suction connector are sequentially connected (all the joints need to be coated with vacuum grease and clamped by plastic clamps). The processes of vacuumizing, hot air gun blowing and scalding, cooling and nitrogen gas introduction are repeated for three times. And after the nitrogen is introduced for the last time, closing the straight air extraction joint, connecting the balloon filled with the nitrogen, and opening the plug of the straight air extraction joint to communicate the nitrogen.
16mL of refined and dried tetrahydrofuran was added to the double-neck flask from the rubber stopper with a syringe, and magnetic stirring was turned on to disperse the magnesium chips uniformly, and condensed water was turned on. 4,4' -dichlorobenzophenone (2.0g, 0.008mol) was dissolved in 5mL of dry tetrahydrofuran and then charged into a two-necked flask. After stirring for 5min, 0.1mL of 1, 2-dibromoethane was injected. After injection, the rubber plug needle is sealed with vacuum grease. After 12 hours of reaction at 45 ℃, the reaction was stopped.
And (3) carrying out suction filtration on the obtained original product liquid, transferring the filtrate into a separating funnel, adding 30mL of dichloromethane and 30mL of saturated ammonium chloride aqueous solution, shaking, standing and layering. Washing the lower layer liquid twice with water, collecting the organic layer extract, adding anhydrous sodium sulfate, drying for 4h, vacuum filtering to obtain yellow clear filtrate, and spin-drying the solvent with a rotary evaporator to obtain the corresponding macromolecule crude product. And (3) precipitating and purifying the obtained macromolecular crude product in petroleum ether twice, performing suction filtration, collecting powder precipitate, and performing vacuum drying to obtain a purified macromolecular product which is solid powder and is marked as fluorescent powder 2.
The molecular weight and molecular weight distribution of the resulting product were determined by gel permeation chromatography.
Example 3: preparation of white light LED by using hyperbranched polymer fluorescent powder 1 to convert blue light wafer
The hyperbranched polymer fluorescent powder 1 prepared in the example 1 and the epoxy resin adhesive are mixed according to the mass ratio of 3:1, 4:1 and 5:1, and the mixture is coated on a blue light wafer with the optimal emission wavelength of 460nm to obtain the white light LED 1.
The performance test results of the obtained white light LED 1 are shown in fig. 3, wherein the CIE coordinates, the color rendering index and the color temperature include: (0.3413,0.2874) (80.2,4872), (0.3574,0.3073) (76.7,4181), (0.3751,0.3333) (77.4,3774).
Example 4: preparation of white light LED by using hyperbranched polymer fluorescent powder 2 to convert blue light wafer
The hyperbranched polymer fluorescent powder 2 prepared in the embodiment 2 and the epoxy resin adhesive are mixed according to the mass ratio of 3:1, 4:1 and 5:1, and the mixture is coated on a blue light wafer with the optimal emission wavelength of 460nm to obtain the white light LED 2.
The performance test results of the obtained white light LED 2 are shown in fig. 4, wherein the CIE coordinates, the color rendering index and the color temperature include: (0.3260,0.2869) (29.9,5934), (0.4564,0.3365) (88,2138), (0.4646,0.3484) (59.5,2141).
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (15)
1. The white light LED is characterized in that the white light LED is obtained by converting a blue light wafer through a hyperbranched polymer and/or a fluorescent material; the fluorescent material comprises the hyperbranched polymer;
the hyperbranched polymer comprises a structural unit with a structural formula shown as a formula (I):
wherein Ar is1And Ar2Independently selected from arylene or substituted arylene;
the substituents in the substituted arylene group are selected from-OH, -NH2、-CH3and-OCH3One of (1);
the hyperbranched polymer has a fluorescence quantum yield of not less than 5 within the range of 470-800 nm under the excitation wavelength of 360-460 nm;
the preparation method of the hyperbranched polymer comprises the following steps:
carrying out Barbier polycondensation reaction on a mixture containing a reaction monomer, metal and an initiator at the temperature of 10-100 ℃ in an inactive atmosphere, and hydrolyzing to obtain the hyperbranched polymer;
the reactive monomer is at least one of compounds with a structural formula shown as a formula (II):
wherein Ar is1And Ar2Is as defined in formula (I); x1And X2Independently selected from fluorine, chlorine, bromine or iodine.
2. The white LED of claim 1, wherein the arylene group is selected from one of phenylene and naphthylene.
3. The white light LED of claim 1, wherein the hyperbranched polymer has a number average molecular weight of 1600 to 10000 and a polydispersity index of 1.10 to 2.60.
4. The white LED of claim 1, wherein the hyperbranched polymer is composed of structural units having a structural formula shown in formula (I).
5. The white LED of claim 1, wherein the metal is selected from at least one of magnesium, aluminum, tin, indium, zinc, bismuth, palladium, and samarium.
6. The white LED of claim 1, wherein the mixture includes a solvent.
7. The white LED of claim 6, wherein the solvent is selected from tetrahydrofuran, diethyl ether, methyl tert-butyl ether, water or benzene, or a mixed solution of tetrahydrofuran and water in a volume ratio of 5:1, 4:1, 3:1, 2:1, 1:1, or a mixed solution of tetrahydrofuran and benzene in a volume ratio of 2:1, 1: 1.
8. The white LED of claim 1, wherein the initiator is selected from at least one of 1, 2-dichloroethane, 1, 2-dibromoethane, 1, 2-diiodoethane, methyl chloride, methyl bromide, methyl iodide, iodine, and red aluminum.
9. The white LED of claim 1, wherein the polycondensation reaction is carried out for 8 to 72 hours.
10. The white LED of claim 9, wherein the molar ratio of the metal to the reactive monomer is 2.05:1 to 3: 1.
11. The white LED of claim 9, wherein the molar ratio of the initiator to the reactive monomer is 0.01:1 to 0.2: 1.
12. The white LED of claim 9, wherein the hydrolysis is performed using a saturated aqueous solution of ammonium chloride.
13. The white LED of claim 1, wherein the purification is performed after the reaction is completed.
14. The white LED of claim 13, wherein the purification process comprises: precipitation method, dialysis method.
15. The white LED of claim 1, wherein the hyperbranched polymer is present in a form comprising an aggregate of nanoparticles, a solid powder, or a solid film.
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| CN106700036A (en) * | 2016-12-30 | 2017-05-24 | 中国石油大学(华东) | Macromolecule with aggregation-induced luminescence effect, and preparation method of macromolecule |
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| CN106632998A (en) * | 2016-12-30 | 2017-05-10 | 中国石油大学(华东) | Barbier-reaction-based method for preparing high molecules |
| CN106700036A (en) * | 2016-12-30 | 2017-05-24 | 中国石油大学(华东) | Macromolecule with aggregation-induced luminescence effect, and preparation method of macromolecule |
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