CN116355226A - Organic phosphorescent material and preparation method and application thereof - Google Patents
Organic phosphorescent material and preparation method and application thereof Download PDFInfo
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- CN116355226A CN116355226A CN202310152312.3A CN202310152312A CN116355226A CN 116355226 A CN116355226 A CN 116355226A CN 202310152312 A CN202310152312 A CN 202310152312A CN 116355226 A CN116355226 A CN 116355226A
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- 239000000463 material Substances 0.000 title claims abstract description 103
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000013078 crystal Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 4
- CZPAJVBVULSLGG-UHFFFAOYSA-N 4-[(3r)-3-(trifluoromethyl)diazirin-1-ium-3-yl]benzoate Chemical compound C1=CC(C(=O)O)=CC=C1C1(C(F)(F)F)N=N1 CZPAJVBVULSLGG-UHFFFAOYSA-N 0.000 claims description 25
- 239000000843 powder Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- VGONBGNMPLIGHJ-UHFFFAOYSA-N 4,5,6-tris(4-bromophenyl)triazine Chemical compound C1=CC(Br)=CC=C1C1=NN=NC(C=2C=CC(Br)=CC=2)=C1C1=CC=C(Br)C=C1 VGONBGNMPLIGHJ-UHFFFAOYSA-N 0.000 claims description 10
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 6
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000003292 glue Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002776 aggregation Effects 0.000 claims description 4
- 238000004220 aggregation Methods 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims description 2
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 2
- 235000011009 potassium phosphates Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- CFKJKWKYGPECGI-UHFFFAOYSA-N OB(O)Oc1ccc(cc1)N(c1ccccc1)c1ccccc1 Chemical compound OB(O)Oc1ccc(cc1)N(c1ccccc1)c1ccccc1 CFKJKWKYGPECGI-UHFFFAOYSA-N 0.000 claims 1
- 229920001940 conductive polymer Polymers 0.000 claims 1
- 239000002178 crystalline material Substances 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000006617 triphenylamine group Chemical group 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- -1 2,4, 6-tris {4- [4- (diphenylamino) phenyl ] phenyl } -1,3, 5-triazine Chemical compound 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- BAAUANLCIHMZCK-UHFFFAOYSA-N N,N-diphenylaniline triazine Chemical class C1=CN=NN=C1.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BAAUANLCIHMZCK-UHFFFAOYSA-N 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013082 photovoltaic technology Methods 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
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- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
- C30B7/02—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions by evaporation of the solvent
- C30B7/06—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions by evaporation of the solvent using non-aqueous solvents
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Abstract
The application discloses an organic phosphorescent material, a preparation method and application thereof, and belongs to the field of luminescent materials. An organic phosphorescent material having a chemical structural formula (C) 75 H 53 N 6 ) n The method comprises the steps of carrying out a first treatment on the surface of the The organic phosphorescent material is needle-shaped crystal. The material is bright yellow needle-shaped crystal, monoclinic system and P2 1 The crystalline material has high luminous intensity and luminous performance under the excitation of ultraviolet lightThe stability is good; the fluorescence emission and phosphorescence emission wave bands of the material are positioned near 490nm, so that the defect that the light emission of an LED white light device at the wave band is weak can be overcome, and the material is expected to be applied to an imitation solar spectrum LED device.
Description
Technical Field
The application relates to an organic phosphorescent material, a preparation method and application thereof, and belongs to the field of luminescent materials.
Background
Luminescent materials, in particular illumination materials and display materials, have a wide range of applications in numerous fields, and are critical for the application of photovoltaic technology. In recent years, many phosphorescent materials have been developed to reduce the cost of lighting devices such as Light Emitting Diodes (LEDs), organic Light Emitting Diodes (OLEDs). White light LEDs are widely used in daily life due to their high efficiency, long life, good mechanical properties, etc. The traditional white light LED device is mostly prepared by adopting an LED chip matched with corresponding fluorescent powder, and the performance of the fluorescent powder greatly influences the overall performance of the white light LED device. And the traditional commercial fluorescent powder emits weak light in the blue-green light range, so how to synthesize the composite material with high-efficiency white light emission by doping a specific luminescent material has important significance.
Compared with inorganic luminescent materials, pure organic phosphorescent materials are widely focused in academia and industry in recent years due to the advantages of simple synthesis, abundant types, low toxicity, easy processing and the like. The pure organic luminescent material with pi-conjugated system is used as a novel functional material, can avoid using expensive rare earth elements, and has high quantum efficiency. Although development and test development of pure organic room temperature phosphorescent materials have been rapid in recent years, efficient, composite white-emitting pure organic room temperature phosphorescent materials have remained insufficient.
Disclosure of Invention
According to the first aspect of the application, an organic phosphorescent material is provided, the organic phosphorescent material comprises a triphenylamine derivative luminescent material with 1,3, 5-triazine as a matrix, a novel crystalline pure organic room temperature phosphorescent material TDBA-1 is constructed through non-covalent pi interaction, the novel crystalline pure organic room temperature phosphorescent material has the characteristics of good stability, environmental friendliness and excellent luminescence performance, a composite material assembled with commercial fluorescent powder can keep excellent luminescence performance, has strong fluorescence and phosphorescence emission near 490nm, has extremely high quantum efficiency, and can supplement the defect that commercial fluorescent powder emits light weakly in a blue light range, so that a white light LED material with excellent performance is prepared.
An organic phosphorescent material having a chemical structural formula (C) 75 H 53 N 6 ) n ；
The organic phosphorescent material is a single crystal;
n is infinity.
Optionally, the organic phosphorescent material belongs to a monoclinic system.
Optionally, the space group of the organic phosphorescent material is P2 1 /c。
Optionally, the unit cell parameters of the organic phosphorescent material are
β＝94.77°～95.77°，α＝γ＝90°。
Optionally, the organic phosphorescent material has a unit cell volume of
Z＝4，Dc＝1.062g/cm 3 。
Optionally, the organic phosphorescent material comprises TDBA monomer;
wherein each TDBA monomer is linked by a non-covalent C-H.pi.and pi.pi.interaction between the molecules, the TDBA molecules between layers being staggered along the C-axis, the molecules forming a tight H-type aggregation in space by self-assembly.
According to a second aspect of the present application, a method of preparing an organic phosphorescent material is provided. The pure organic room temperature phosphorescent material prepared by the invention has the advantages of easily available raw materials, no toxicity, no pollution, simple preparation method and application potential in the fields of illumination, display, luminescent devices and the like. The used 1, 4-dioxane solvent can be used as a template reagent to be filled in a pore canal of a crystal structure, and can generate multiple hydrogen bond interactions with TDBA molecules, thereby playing a role in stabilizing the structure.
The preparation method of the organic phosphorescent material comprises the following steps:
s1, obtaining a compound TDBA;
s2, mixing the materials containing the TDBA and the solvent I, and volatilizing to obtain the organic phosphorescent material.
Optionally, in step S2, the solvent i is at least one selected from 1, 4-dioxane, chloroform, dichloromethane, and tetrahydrofuran.
Optionally, the volume ratio of the mass of the TDBA to the solvent I is 0.05 g/mL-0.1 g/mL.
Alternatively, the conditions of volatilization are as follows:
the temperature is 20-100 ℃;
the time is 12-96 hours.
Optionally, after mixing in step S2, the mixture is filtered through a microfiltration membrane, the filtrate is allowed to evaporate slowly and filtered through a sand core funnel.
Optionally, step S1 includes the steps of:
coupling the mixture containing the tri (4-bromophenyl) triazine, the 4- (diphenylamino) phenylboronic acid, the metal catalyst, the alkaline reagent and the solvent II, washing, purifying and drying to obtain the TDBA.
Optionally, the molar ratio of the tris (4-bromophenyl) triazine to the 4- (diphenylamino) phenylboronic acid is 1:3.5 to 4.5.
Optionally, the molar ratio of the tris (4-bromophenyl) triazine to the metal catalyst is 1:0.05 to 0.1.
Optionally, the molar ratio of the tris (4-bromophenyl) triazine to the alkaline agent is 1:3.5 to 6.5.
Alternatively, the metal catalyst is selected from at least one of tetrakis (triphenylphosphine) palladium (II), palladium dichloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, and dichloro (1, 1-bis (diphenylphosphine) ferrocene) palladium.
Optionally, the alkaline reagent is at least one selected from cesium carbonate, potassium phosphate and sodium carbonate.
Optionally, the solvent II is at least one selected from 1, 4-dioxane, N-dimethylformamide and toluene.
Alternatively, the conditions for the coupling reaction are as follows:
the temperature is 75-90 ℃;
the time is 65-80 h.
Alternatively, the coupling reaction is carried out under an inert gas;
the inert gas is at least one selected from nitrogen, argon and helium.
According to one embodiment of the application, a synthesis method of a pure organic room temperature phosphorescent material containing triphenylamine derivative of a triazine parent is disclosed, wherein tris (4-bromophenyl) triazine and 4- (diphenylamino) phenylboronic acid are mixed according to a molar ratio of 1:4, adding a metal catalyst and an alkaline reagent to perform coupling reaction in a polar solvent. Rotary evaporating solvent, washing with ethanol/water for several times, purifying with n-hexane/dichloromethane as eluent by silica gel column chromatography, and drying to obtain organic luminescent material TDBA with the structural formula:
discloses a preparation method of a crystalline pure organic room temperature phosphorescent material with pi conjugated structure. The triazine-triphenylamine derivative containing nitrogen heteroatom is selected as an organic pi conjugated structure, and a compact H aggregation stacking mode is formed in space through the actions of C-H.pi and pi.pi, so that the triphenylamine derivative pure organic room-temperature phosphorescent material with higher luminous efficiency is obtained. The chemical structural general formula is (C) 75 H 53 N 6 ) n The structural unit of the catalyst belongs to monoclinic system, P2 1 Space group/c, prepared by volatilization method: the organic ligand is dissolved in 1, 4-dioxane (Diox) and volatilized slowly to obtain bright yellow crystal (TDBA-1), and the preparation method is simple, mild in synthesis condition and stable in structure.
According to a third aspect of the present application there is provided the use of an organic phosphorescent material. The prepared crystalline pure organic room temperature phosphorescent material is applied to the preparation of LED devices, the preparation method is simple, and the crystalline pure organic room temperature phosphorescent material and commercial fluorescent powder are compounded on an LED chip to emit pure white light, so that the luminous performance is stable. And the prepared white light LED device is nontoxic and pollution-free, and is favorable for recycling the prepared LED device.
The organic phosphorescent material and/or the organic phosphorescent material obtained by the preparation method are applied to the preparation of luminescent films and LED luminescent devices.
Optionally, the preparation of the luminescent film comprises the following steps:
grinding the mixture containing the organic phosphorescent material and the polymer, dissolving the mixture in chloroform, and spin-coating to obtain the luminescent film.
Optionally, the preparation of the LED light emitting device comprises the steps of:
mixing materials containing the organic phosphorescent material, fluorescent powder, packaging silica gel and the like to prepare slurry, and then coating the slurry on the surface of an LED chip to obtain the LED luminescent device.
Optionally, the polymer is at least one selected from polymethyl methacrylate, polybutyl methacrylate and polyvinylpyrrolidone.
Optionally, the mass ratio of the organic phosphorescent material to the polymer is 1:1 to 10.
Optionally, the fluorescent powder is selected from at least one of 550nm and 660nm which are commercially available.
Optionally, the mass ratio of the organic phosphorescent material to the fluorescent powder is 1:1 to 5.
According to one embodiment of the present application, the organic material is applied to the preparation of a light emitting thin film, and the specific preparation steps are as follows: the pure organic room temperature phosphorescent material and the polymer polymethyl methacrylate (PMMA) are doped, and the amorphous film prepared by dissolving and coating the film through chloroform still has good room temperature phosphorescent light-emitting characteristics and has the potential of preparing a light-emitting device. In addition, the organic material is applied to an LED light-emitting device, and the preparation method comprises the following specific steps: grinding the crystalline pure organic room temperature phosphorescent material into powder by using a mortar, mixing the powder with commercial fluorescent powder (550 nm,660 nm) according to a certain proportion, adding packaging silica gel, uniformly stirring, and performing vacuum defoaming to form fluorescent gel with uniformly dispersed fluorescent material. And uniformly coating the fluorescent glue on the surface of the blue light LED chip to form a fluorescent glue layer with a certain thickness, and after baking and curing, lighting the blue light LED chip to emit high-quality white light.
The beneficial effects that this application can produce include:
1) The organic phosphorescent material provided by the application is bright yellow needle-shaped crystal, is monoclinic system and is P2 1 The crystalline material has the advantages of high luminous intensity and stable luminous performance under the excitation of ultraviolet light; the fluorescence emission and phosphorescence emission wave bands of the material are positioned near 490nm, so that the defect that the light emission of an LED white light device at the wave band is weak can be overcome, and the material is expected to be applied to an imitation solar spectrum LED device.
2) The preparation method of the organic phosphorescent material has the advantages of simplicity, low production cost, mild reaction conditions and suitability for mass production. And the synthesized crystalline pure organic room temperature phosphorescent material has the advantages of simple preparation method, good crystallinity and high purity.
3) The application of the organic phosphorescent material provided by the application ensures that the performance of the composite luminescent film prepared by the organic phosphorescent material and the polymer PMMA is kept stable, so that the material has certain device potential; the prepared crystalline pure organic room temperature phosphorescent material is applied to the preparation of LED devices, the preparation method is simple, and the crystalline pure organic room temperature phosphorescent material and commercial fluorescent powder are compounded on an LED chip to emit pure white light, so that the luminous performance is stable. And the prepared white light LED device is nontoxic and pollution-free, and is favorable for recycling the prepared LED device.
Drawings
FIG. 1 is a synthetic route diagram of pure organic room temperature phosphorescent materials of triphenylamine derivatives of the invention.
FIG. 2 is a schematic diagram of the compound TDBA synthesized in example 1 1 H NMR spectrum.
Fig. 3 is a photograph of crystalline material TDBA-1.
FIG. 4 is a schematic diagram of the structure of the crystalline pure organic room temperature phosphorescent material synthesized in example 2, wherein (a) is the non-covalent C-H. Pi. And pi. Interaction between two adjacent TDBA molecules, and (b) is the stacking mode of the TDBA molecules in space.
Fig. 5 is a graph of fluorescence emission spectrum and lifetime decay of the pure organic room temperature phosphorescent material synthesized in example 1, wherein (a) is fluorescence emission spectrum and (b) is lifetime decay graph.
FIG. 6 is a graph showing fluorescence emission spectra and lifetime decay curves of the pure organic room temperature phosphorescent material synthesized in example 1 and PMMA composite film material, wherein (a) is fluorescence emission spectra and (b) is lifetime decay curve curves.
FIG. 7 is a chromaticity diagram of the commercially available phosphor selected in example 3.
Fig. 8 is a chromaticity diagram of the composite material of example 3.
Fig. 9 is a luminescent image of the device prepared in example 3, with device dimensions of 0.28mm by 0.35mm.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, both the starting materials and the catalysts in the examples of the present application were purchased commercially.
Wherein TDBA is 2,4, 6-tris {4- [4- (diphenylamino) phenyl ] phenyl } -1,3, 5-triazine.
The analytical method in the examples of the present application is as follows:
using XtaLAB Synergy R, hyPix diffractometer with Cu K alpha
Single crystal diffraction analysis was performed.
Fluorescence analysis was performed using an FLS1000 fluorescence spectrometer, a remote (EVERFINE) LEDspec light color electricity integrated measurement system.
Unless otherwise indicated, conventional testing methods or instrumental recommended testing methods are employed.
The yields in the examples of the present application were calculated as follows:
yield= (actual yield/theoretical yield) ×100%.
Example 1
Preparation of triphenylamine derivative containing 1,3, 5-triazine as matrix
Tris (4-bromophenyl) triazine (2.00 g,3.66 mmol), 4- (diphenylamino) phenylboronic acid (4.23 g,14.64 mmol), cesium carbonate (4.98 g,15.30 mmol) and tetrakis (triphenylphosphine) palladium (II) (0.6 g,0.52 mmol) were added to a Schleck flask (250 mL) equipped with a stirring magnet. Vacuum degassing was performed for 30 minutes, argon was pumped in under vacuum, and repeated three times, and then 120mL of degassed solvent 1, 4-dioxane was transferred into the flask. The solution was reacted under argon atmosphere at 85℃for 72 hours. After the reaction mixture was cooled to room temperature, the organic solvent was removed by rotary evaporation. The crude product was washed with ethanol (3X 100 mL) and distilled water (3X 200 mL). The crude product was purified by silica gel column chromatography using n-hexane/dichloromethane solvent to give 2.86g (2.75 mmol) of the pale yellow compound TDBA in 75% yield.
Example 2
Preparation of crystalline pure organic room temperature phosphorescent material emitting blue light
0.5g of the organic ligand TDBA obtained in example 1 was dissolved in a 1, 4-dioxane (Diox) solution (5-10 mL) at room temperature, and then filtered with a 0.22 μm microfiltration membrane, allowing the filtrate to evaporate slowly. And (3) after a few days, filtering by using a sand core funnel to obtain bright yellow needle-shaped crystals, namely the prepared crystalline organic phosphorescent material TDBA-1. The structure is determined by a single crystal diffractometer, and the test result shows that: its structural formula is C 75 H 53 N 6 Belonging to monoclinic system, the space group is P2 1 And/c, the unit cell parameters are
β=95.27 °, α=γ=90°, unit cell volume +.>
Z＝4，Dc＝1.062g/cm 3 The method comprises the steps of carrying out a first treatment on the surface of the Wherein each TDBA monomer is linked by a non-covalent C-H.pi.and pi.pi.interaction between the molecules, the TDBA molecules between layers being staggered along the C-axis, the molecules forming a tight H-type aggregation in space by self-assembly. The prepared crystalline pure organic material is excited under the ultraviolet light with the wavelength of 365nm, and the crystalline pure organic room temperature phosphorescence material emitting blue light is obtained.
Example 3
Preparation of blue light-emitting composite film, preparation of composite light-emitting film by solution coating method
The pure organic room temperature phosphorescent material (260 mg,0.25 mmol) prepared in example 1 and polymethyl methacrylate (PMMA) (260 mg) were first doped, ground into powder with a mortar, then dissolved in a small amount of chloroform solution, slightly shaken, and spin-coated on the quartz plate substrate surface after the reactants were completely dissolved to form a film. And exciting the prepared composite luminescent film under ultraviolet light with the wavelength of 365nm to obtain the pure organic composite luminescent film emitting blue light.
Example 4
Application of the pure organic room temperature phosphorescent material for emitting white light in a composite manner, the crystalline pure organic room temperature phosphorescent material prepared in example 2 is applied to preparation of an LED light-emitting device, and the preparation steps are as follows: 60mg of the crystalline pure organic room temperature phosphorescent material is ground into powder by a mortar, mixed with commercial fluorescent powder (550 nm,660nm of Jiangmen Co., ltd.) according to a certain proportion, then added with packaging silica gel, stirred uniformly, and subjected to vacuum defoamation to form the fluorescent gel with uniformly dispersed fluorescent material. The fluorescent glue is uniformly smeared on the surface of the blue light LED chip to form a fluorescent glue layer with a certain thickness, and after baking and curing, the blue light LED chip can emit high-quality white light (a high-quality white light LED light source is obtained).
Analytical example
As can be seen from the figure 2 of the drawings, 1 h NMR spectra demonstrated successful synthesis of compound TDBA; as can be seen from FIG. 5, the TDBA-1 phosphorescent material is used at room temperature and low temperature of 100KCan maintain strong phosphorescence emission performance; as can be seen from fig. 6, the TDBA-1 phosphorescent material is prepared into a thin film material after being compounded with the high molecular polymer PMMA, and still can maintain strong phosphorescent emission performance at room temperature and low temperature of 100K; as can be seen from fig. 7 and 8, the TDBA-1 phosphor material and the commercial phosphor powder are compounded to emit high-quality white light, and the high-quality white LED light source can be prepared.
The foregoing description is only a few examples of the present application and is not intended to limit the present application in any way, and although the present application is disclosed in the preferred examples, it is not intended to limit the present application, and any person skilled in the art may make some changes or modifications to the disclosed technology without departing from the scope of the technical solution of the present application, and the technical solution is equivalent to the equivalent embodiments.
Claims (10)
1. An organic phosphorescent material, characterized in that the organic phosphorescent material has a chemical structural formula (C) 75 H 53 N 6 ) n ；
The organic phosphorescent material is a single crystal;
n is infinity.
2. The organic phosphorescent material according to claim 1, characterized in that the organic phosphorescent material belongs to a monoclinic system;
preferably, the space group of the organic phosphorescent material is P2 1 /c；
Preferably, the unit cell parameters of the organic phosphorescent material are
β＝94.77°～95.77°，α＝γ＝90°；
Preferably, the organic phosphorescent material has a unit cell volume of
Z＝4，Dc＝1.062g/cm 3 。
3. The organic phosphorescent material according to claim 1, characterized in that the organic phosphorescent material comprises TDBA monomers;
wherein each TDBA monomer is linked by a non-covalent C-H.pi.and pi.pi.interaction between the molecules, the TDBA molecules between layers being staggered along the C-axis, the molecules forming a tight H-type aggregation in space by self-assembly.
4. A method for producing an organic phosphorescent material according to any one of claims 1 to 3, comprising the steps of:
s1, obtaining a compound TDBA;
s2, mixing the materials containing the TDBA and the solvent I, and volatilizing to obtain the organic phosphorescent material.
5. The process according to claim 4, wherein in step S2, the solvent I is at least one selected from the group consisting of 1, 4-dioxane, chloroform, methylene chloride and tetrahydrofuran;
preferably, the volume ratio of the mass of the TDBA to the solvent I is 0.05 g/mL-0.1 g/mL.
6. The method according to claim 4, wherein the volatilizing conditions are as follows:
the temperature is 20-100 ℃;
the time is 12-96 hours;
preferably, after mixing in step S2, filtering with a microfiltration membrane, allowing the filtrate to evaporate slowly, and filtering with a sand core funnel;
preferably, step S1 comprises the steps of:
coupling the mixture containing tris (4-bromophenyl) triazine, 4- (diphenylamino) phenylboric acid, a metal catalyst, an alkaline reagent and a solvent II, washing, purifying and drying to obtain the TDBA;
preferably, the molar ratio of the tris (4-bromophenyl) triazine to the 4- (diphenylamino) phenylboronic acid is 1:3.5 to 4.5;
preferably, the molar ratio of the tris (4-bromophenyl) triazine to the metal catalyst is 1:0.05 to 0.1;
preferably, the molar ratio of the tris (4-bromophenyl) triazine to the alkaline agent is 1:3.5 to 6.5;
preferably, the metal catalyst is selected from at least one of tetrakis (triphenylphosphine) palladium (II), palladium dichloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, dichloro (1, 1-bis (diphenylphosphine) ferrocene) palladium;
preferably, the alkaline reagent is at least one selected from cesium carbonate, potassium phosphate and sodium carbonate;
preferably, the solvent II is at least one selected from 1, 4-dioxane, N-dimethylformamide and toluene;
preferably, the conditions of the coupling reaction are as follows:
the temperature is 75-90 ℃;
the time is 65-80 hours;
preferably, the coupling reaction is carried out under an inert gas;
the inert gas is at least one selected from nitrogen, argon and helium.
7. Use of the organic phosphorescent material according to any one of claims 1 to 3 and/or the organic phosphorescent material obtained by the preparation method according to any one of claims 4 to 6 for preparing luminescent films, LED luminescent devices.
8. The use according to claim 7, wherein the preparation of the luminescent film comprises the steps of:
grinding the mixture containing the organic phosphorescent material and the polymer, dissolving the mixture in chloroform, and spin-coating to obtain the luminescent film.
9. The use according to claim 7, wherein the preparation of the LED light emitting device comprises the steps of:
and mixing the materials containing the organic phosphorescent material, the fluorescent powder and the conductive polymer glue to prepare slurry, and then coating the slurry on the surface of the LED chip to obtain the LED luminescent device.
10. The use according to claim 8, wherein the polymer is selected from at least one of polymethyl methacrylate, polybutyl methacrylate, polyvinylpyrrolidone;
preferably, the mass ratio of the organic phosphorescent material to the polymer is 1:1 to 10;
preferably, the fluorescent powder is selected from at least one of 550nm and 660nm which are commercially available;
preferably, the mass ratio of the organic phosphorescent material to the fluorescent powder is 1:1 to 5.
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