CN104892645A - Cuprous complex phosphor material of methyl substitution benzoxazolyl pyridine - Google Patents
Cuprous complex phosphor material of methyl substitution benzoxazolyl pyridine Download PDFInfo
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- CN104892645A CN104892645A CN201510353135.0A CN201510353135A CN104892645A CN 104892645 A CN104892645 A CN 104892645A CN 201510353135 A CN201510353135 A CN 201510353135A CN 104892645 A CN104892645 A CN 104892645A
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- 239000000463 material Substances 0.000 title claims abstract description 70
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 6
- WELSCYIRWKBEBZ-UHFFFAOYSA-N 2-pyridin-2-yl-1,3-benzoxazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2O1 WELSCYIRWKBEBZ-UHFFFAOYSA-N 0.000 title 1
- 238000006467 substitution reaction Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 239000013078 crystal Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 235000000621 Bidens tripartita Nutrition 0.000 claims description 2
- 240000004082 Bidens tripartita Species 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 208000006637 fused teeth Diseases 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000005424 photoluminescence Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 abstract 2
- WHXBBKCQUJHZDF-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-1,3-benzoxazole Chemical compound N1=CC(C)=CC=C1C1=NC2=CC=CC=C2O1 WHXBBKCQUJHZDF-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- 238000012827 research and development Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses yellow green phosphorescence cuprous complex lighting material and a preparation method thereof. The phosphorescence complex is obtained by cuprous salt and ligand complex and its molecular structure is [Cu (5-Me-2-PBO) (PPh3)2] PF6, wherein 5-Me-2-PBO and PPh3 are electric neutral ligand 5-methyl-2-(2-benzoxazolyl) pyridine and triphenylphosphine. The complex has the advantages of micromolecule which is easy to purify and lighting efficiency is high and high thermal stability. The material is obtained by directly blending Cu (CH3CN) 4PF6 with dichloromethane solution of ligand and has the advantages of simplicity in process and equipment, obtainable raw materials and low cost. The material can be used as photoluminescence yellow green material and can be used as luminescent phosphor material composed of multiple organic material layers in an electroluminescence device.
Description
Technical field
The present invention relates to luminescent material technical field, relate to embedded photoluminescent material field and electroluminescent material field, particularly relate to field of organic electroluminescent materials.
Background technology
Luminescent material comprises photoluminescence and the large class Application Areas of electroluminescent two.Photoluminescence refers to that object is subject to the irradiation of external light source, thus the generation of acquisition energy excites and is finally directed at luminous phenomenon.Uv-radiation, visible ray and ir radiation etc. all can cause photoluminescence.Embedded photoluminescent material can be used for the aspects such as the scintillator in fluorometric analysis, traffic sign, tracking monitor, agricultural light conversion film, nuclear detection technology, the fluorescence optical collector in solar energy converting technology.Electroluminescent (electroluminescent, be called for short EL), refers to that luminescent material is under electric field action, and being subject to the phenomenon of electric current and exciting of electric field and luminescence, is a kind of luminescence process electric energy being directly converted to luminous energy.There is the material of this performance, automatically controlled luminescent device can be made into, such as photodiode (LED) and Organic Light Emitting Diode (Organic Light-Emitting Diode is called for short OLED).And the large series products of LED and OLED two, in the flat pannel display of advanced person and solid-state energy-saving illumination field, all there is very tempting application prospect, and shown its good industrialized development impetus at present.
Can produce electroluminescent solid material has a variety of, mainly comprises inorganic semiconductor material, organic small molecule material, macromolecular material and title complex small molecule material.Due to OLED there is energy-conservation, frivolous, free from glare, without ultraviolet, without infrared rays, driving voltage is low, the time of response is short, cold property is good, luminous efficiency is high, manufacturing process is simple, all solid state shock resistance is good, almost do not have the problem of visible angle, can manufacture on the substrate of unlike material, can make the many merits such as the product that can bend, and enjoys attracting attention of scientific and technological circle and industrial community in recent years.And along with the development of society, OLED technology (or by) colour TV, mobile phone, various indicating meter, various illumination with or the field such as display terminal of the military equipment such as decorative lamp, aircraft obtain using more and more widely.The electroluminescent material that can be used for OLED has fluorescent material and phosphor material two kinds.Because electroluminescent process produces the singlet excitons of 25% and the feature of 75% triplet exciton, and fluorescent material can only utilize singlet excitons, phosphor material then can utilize singlet excitons and triplet exciton and luminous simultaneously, and therefore the research and development of phosphor material seem particularly important.
The research and development object of phosphor material is all generally Metal-organic complex small molecule material instead of organic molecule, and reason is pure organic molecule, and at room temperature phosphorescence is very weak, can not detect phosphorescent emissions even at all.And title complex small molecule material can realize phosphorescent emissions easily, and can realize high efficiency luminescence, being also easy to preparation and purifying, being easy to be made into film, is therefore that a unique class is actually used in the phosphor material of OLED product luminescent layer at present.The phosphorescent substance that current OLED product adopts is the title complex containing the precious metal such as iridium, rhenium, and they have shown good use properties and market manifestation.But there is cost intensive in such precious metals complex, the especially problem of environmental risk.Therefore, research and development at present for base metal Cu (I) complex phosphorescence material receive much concern, Cu (I) title complex is very cheap, without environmental risk, Cu (I) complex luminescent material of therefore researching and developing novel excellent property is significant and good market application foreground.
More specifically analyze, OLED Huang/green phosphorescent material on sale is at present all the title complex of precious metal iridium and platinum etc., although they are existing performance preferably in performance, the price of its costliness also has influence on applying of OLED the finished product and market manifestation.With Cu (I) title complex as Huang/green phosphorescent material then long-standing (N.Armaroli, G.Accorsi, F.Cardinali, A.Listorti, Top.Curr.Chem.2007,280,69-115.), Cu (I) complex luminescent material of this cheapness can be prepared easily by Cu (I) ion and suitable organic ligand, does not just still reach application demand in its luminous intensity of OLED operating temperature range.Therefore Cu (I) title complex Huang/green phosphorescent material of development of new cheapness has great actual application value.
Summary of the invention
The object of this invention is to provide a kind of new yellow-green colour phosphorescence Cu (I) complex luminescent material and preparation method thereof.By the solution coordination reaction of Cu (I) ion and organic ligand, facilitate and prepared the Cu of luminescent properties and good thermal stability (I) complex luminescent material at an easy rate, its yellow-green colour phosphorescence luminous intensity is very large, and its decay of luminescence feature meets the requirement of OLED to material phosphorescence luminescent lifetime very much, is applied to the reduction that OLED emitting layer material is conducive to product cost.
One of technical scheme of the present invention, is to provide a kind of new yellow-green colour phosphorescence Cu (I) complex luminescent material, by Cu (CH
3cN)
4pF
6carry out coordination reaction with part to obtain, its molecular structure is [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6; 5-Me-2-PBO and PPh in formula
3be respectively electric neutrality part 5-methyl-2-(2-benzoxazole) pyridine and triphenylphosphine.
Described part 5-methyl-2-(2-benzoxazole) pyridine, be the combination of methyl substituted benzoxazole and pyridine, its molecular structure is such as formula (I):
O in described part in benzoxazole structure has neither part nor lot in coordination, and atom N in its atom N and pyridine structure and cuprous ion form Bidentate State.
Described luminescent material is for being triclinic(crystalline)system, and P-1 spacer, unit cell parameters is
α=86.215 (3) °, β=78.921 (2) °, γ=79.372 (4) °,
z=2, D
c=1.4320g/cm
3, crystal color is yellow; This luminescent material structure shows as ionic complex, and wherein hexafluoro-phosphate radical is counter anion, and positively charged ion is then by cuprous ion and part 5-Me-2-PBO, PPh
3the coordination cation that complexing is formed; In this coordination cation, cuprous ion adopts CuN
2p
2tetrahedral coordination mode, wherein two N come from benzoxazole group in a double-tooth chelate ligand 5-Me-2-PBO and pyridine groups respectively, and two P come from another two Phosphine ligands PPh
3; Its molecular structure is such as formula (II):
Described luminescent material is applied to yellow green light phosphor material, this material is subject to the UV-light of very wide wavelength region (300-550nm) or exciting of visible ray, very strong yellow-green light can be sent, its maximum emission wavelength is 560nm, chromaticity coordinates value is (0.4369,0.5309), luminescent lifetime is 5 microseconds.
Described yellow-green colour phosphorescent light-emitting materials is used as the luminescent layer phosphor material in the electroluminescent device of multilayer organic materials composition.
Technical scheme two of the present invention, is to provide a kind of yellowish green phosphorescence Cu (I) complex luminescent material [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6preparation method.This preparation method is by Cu (CH
3cN)
4pF
6there is coordination reaction with the dichloromethane solution mixing of two kinds of parts, finally revolve steaming and produce the crystal powder of product and realize.Its specific embodiments is divided into five steps:
(1) under room temperature by Cu (CH
3cN)
4pF
6powder is dissolved in methylene dichloride completely, obtains colorless cleared solution;
(2) under room temperature by PPh
3be dissolved in methylene dichloride, obtain colorless cleared solution;
(3) under room temperature, 5-Me-2-PBO is dissolved in methylene dichloride, fully stirs, obtain settled solution;
(4) will mix by three kinds of solution above, and fully stir generation coordination reaction;
(5) will react gained bright yellow solution to steam to dry at normal temperature decompression backspin, vacuum-drying, obtains crystalline glassy yellow powdered product.
In preparation method of the present invention, the mol ratio Cu (CH of described three kinds of reactants
3cN)
4pF
6: PPh
3: 5-Me-2-PBO is 1: 2: 1.
First beneficial effect of the present invention is provided yellowish green phosphorescence Cu (I) complex luminescent material [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6the benzoxazole group wherein introduced is conducive to molecular-excited state luminescence, Ni metal effectively promotes intersystem crossing to the existence of the charge transtion (MLCT) of part, and the existence of substituting group methyl etc., cause Cu (I) part existence around effectively sterically hindered, can the non-radiative decay of Inhibitory molecules excited state, part 5-Me-2-PBO and PPh
3be all the part of many aromatic rings, all there is very large rigidity characteristic, thus the phosphorescent emissions performance that had of this molecular material.This complex material had both possessed the cheap advantage with being easy to purifying, and had good solvability and thermostability, for the further application of luminescent material provides technical support.
Secondly beneficial effect of the present invention is yellowish green phosphorescence Cu (I) complex luminescent material [Cu (the 5-Me-2-PBO) (PPh of preparation
3)
2] PF
6method, have simple process, equipment used is simple, and raw material is simple and easy to get, and production cost is low, can obtain having the advantages such as the product of very high yield in a short period of time.
Accompanying drawing explanation
Fig. 1. phosphorescent complexes [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6the single crystal structure figure of molecule.
Fig. 2. phosphorescent complexes [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6molecule is in unit cell and the accumulation graph of peripheral space.
Fig. 3. phosphorescent complexes [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6x-ray powder diffraction: (a) be according in embodiment 2 single crystal structural data calculate obtain spectrogram; B () is the collection of illustrative plates of gained powder in the embodiment of the present invention 1.
Fig. 4. phosphorescent complexes [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6ultraviolet-ray visible absorbing (UV-Vis) spectrogram.
Fig. 5. title complex [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6the light emission spectrogram (right side) of crystallite sample under 420 nano wave length optical excitation; With measure under 560 nanometer supervisory wavelength excite spectrogram (left side).
Embodiment
The performance of implementation procedure of the present invention and material is illustrated by embodiment:
Embodiment 1
A large amount of Cu (I) title complex [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6the preparation of the crystallite sample: [Cu (CH taking 0.1mmol (37.3mg)
3cN)
4] PF
6be dissolved in 5mL CH
2cl
2in, then take the PPh of 4-Me-2-PBO and 0.2mmol (52.4mg) of 0.1mmol (21.3mg) successively
3, be dissolved in 5mL CH respectively
2cl
2in, by all three kinds of solution mixing (mol ratio Cu (CH of described three kinds of reactants
3cN)
4pF
6: PPh
3: 5-Me-2-PBO is 1: 2: 1), and stirring makes it fully coordination reaction to occur, and is finally filtered by gained bright yellow solution, and revolve all solvents of steaming removing, vacuum-drying, obtains glassy yellow crystal powder and is product, productive rate 96% (in Cu).
Embodiment 2
Synthesis Cu (I) title complex [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6monocrystalline: take 37mg Cu (CH
3cN)
4pF
6with the PPh of 53mg
3part is dissolved in after in 10mL methylene dichloride, the dichloromethane solution again 5mL being contained the 4-Me-2-PBO part of 22mg once adds in above-mentioned solution, stirring makes it to dissolve rear filtration completely, filtrate covers normal hexane and impels product crystallization, separates out a large amount of yellow bulk crystals after leaving standstill a couple of days.The yellow crystals selecting a 0.28mm × 0.23mm × 0.20mm size is used for x-ray crystal structure test.The molecular structure of this compound is illustrated in accompanying drawing 1, and its structure cell packed structures is illustrated in accompanying drawing 2.
To title complex [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6pure phase crystal prototype carried out a series of performance test.Steady-state fluorescence test has been carried out to material crystals of the present invention, result shows that this material is under different excitation wavelength effects, can launch strong yellow-green light, and chromaticity coordinates value is (0.4369,0.5309), concrete excitation spectrum and emmission spectrum are as shown in Figure 5.And the transient state fluorometric investigation of this material is shown, its luminescent lifetime is 5 microseconds, belongs to phosphorescent emissions.Visible, this material can be applicable to the yellow-green colour phosphor material that multi-wavelength excites, and is also suitable for very much the yellow-green colour phosphor material of OLED luminescent layer.
Claims (4)
1., based on a cuprous title complex yellow-green colour phosphor material for methyl substituted benzoxazole yl pyridines, it is characterized in that: the structural formula of luminescent material is [Cu (5-Me-2-PBO) (PPh
3)
2] PF
6, PPh in formula
3for electric neutrality Phosphine ligands triphenylphosphine; In formula, 5-Me-2-PBO is neutral heterocyclic ligand 5-methyl-2-(2-benzoxazole) pyridine, and this part is the combination of methyl substituted benzoxazole and pyridine, and its molecular structure is such as formula (I):
（I）；
Under room temperature, this complex luminescent material is triclinic(crystalline)system, P-1 spacer, and unit cell parameters is
α=86.215 (3) °, β=78.921 (2) °, γ=79.372 (4) °,
z=2, Dc=1.4320g/cm
3, crystal color is yellow; This luminescent material structure shows as ionic complex, and wherein hexafluoro-phosphate radical is counter anion, and positively charged ion is then by cuprous ion and part 5-Me-2-PBO, PPh
3the coordination cation that complexing is formed; In this coordination cation, cuprous ion adopts CuN
2p
2tetrahedral coordination mode, wherein two N come from benzoxazole group in a double-tooth chelate ligand 5-Me-2-PBO and pyridine groups respectively, and two P come from another two Phosphine ligands PPh
3; Its molecular structure is such as formula (II):
(II)。
2. the preparation method of cuprous title complex yellow-green colour phosphor material according to claim 1, the method comprises the following steps:
(1) under room temperature by Cu (CH
3cN)
4pF
6powder is dissolved in methylene dichloride completely, obtains colorless cleared solution;
(2) under room temperature by PPh
3be dissolved in methylene dichloride, obtain colorless cleared solution;
(3) under room temperature, 5-Me-2-PBO is dissolved in methylene dichloride, fully stirs, obtain settled solution;
(4) will mix by three kinds of solution above, and fully stir generation coordination reaction;
(5) will react gained bright yellow solution to steam to dry at normal temperature decompression backspin, vacuum-drying, obtains crystalline glassy yellow powdered product.
3. the preparation method of cuprous title complex yellow-green colour phosphor material according to claim 2, is characterized in that: the mol ratio Cu (CH of described three kinds of reactants
3cN)
4pF
6: PPh
3: 5-Me-2-PBO is 1: 2: 1.
4. the application of cuprous title complex yellow-green colour phosphor material according to claim 1, is characterized in that described luminescent material has maximum emission peak at 560nm place, can be used as embedded photoluminescent material, or is used as the light emitting layer luminesces material in multilayer electroluminescent device.
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|---|---|---|---|
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|---|---|---|---|
| CN201510353135.0A CN104892645A (en) | 2015-06-17 | 2015-06-17 | Cuprous complex phosphor material of methyl substitution benzoxazolyl pyridine |
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|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105713021A (en) * | 2016-04-18 | 2016-06-29 | 中国计量大学 | Methyl-substituted benzoxazolyl pyridine cuprous complex yellow/green phosphorescent material |
| CN107011888A (en) * | 2017-03-21 | 2017-08-04 | 中国计量大学 | A kind of cuprous complex luminescent material of the tetrahedral containing phenanthroline ligand of crystal formation |
| CN115873263A (en) * | 2022-12-27 | 2023-03-31 | 山东能源集团有限公司 | Metal organic framework material and preparation method and application thereof |
Citations (3)
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| CN105713021A (en) * | 2016-04-18 | 2016-06-29 | 中国计量大学 | Methyl-substituted benzoxazolyl pyridine cuprous complex yellow/green phosphorescent material |
| CN107011888A (en) * | 2017-03-21 | 2017-08-04 | 中国计量大学 | A kind of cuprous complex luminescent material of the tetrahedral containing phenanthroline ligand of crystal formation |
| CN115873263A (en) * | 2022-12-27 | 2023-03-31 | 山东能源集团有限公司 | Metal organic framework material and preparation method and application thereof |
| CN115873263B (en) * | 2022-12-27 | 2023-09-15 | 山东能源集团有限公司 | Metal organic framework material and preparation method and application thereof |
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