CN113444068B - Organic luminescent material and preparation method and application thereof - Google Patents
Organic luminescent material and preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 99
- 238000002360 preparation method Methods 0.000 title abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000001514 detection method Methods 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000007514 bases Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 235000011181 potassium carbonates Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910002666 PdCl2 Inorganic materials 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 26
- 238000006862 quantum yield reaction Methods 0.000 abstract description 22
- 239000007788 liquid Substances 0.000 abstract description 17
- 239000003086 colorant Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000002189 fluorescence spectrum Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- -1 aryl pyrrole derivative Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- PAMBVPQLDDXPCQ-UHFFFAOYSA-N boric acid;n,n-diphenylaniline Chemical compound OB(O)O.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PAMBVPQLDDXPCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 230000009967 tasteless effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- CHODTZCXWXCALP-UHFFFAOYSA-N 5-bromoquinoline Chemical compound C1=CC=C2C(Br)=CC=CC2=N1 CHODTZCXWXCALP-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
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- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention provides an organic luminescent material which has a structure shown in a formula I. The preparation method comprises the following steps: taking IV compound and V compound as raw materials, reacting at 40-130 ℃ in the presence of catalyst and alkali compound to obtain the organic luminescent material shown in formula I. The organic luminescent material has higher quantum yield in solid state and liquid state, can show different luminescent colors in different solvents, and can be used for encryption, anti-counterfeiting or solvent detection.
Description
Technical Field
The invention belongs to the field of functional materials, relates to an organic luminescent material, a preparation method and application thereof, and particularly relates to an organic luminescent material with solvent discoloration and high quantum yield in solid and liquid states, and a preparation method and application thereof.
Background
The organic luminescent material is widely applied to the fields of biological imaging, sensors, light emitting diodes, anti-counterfeiting encryption and the like. However, most fluorescent materials can emit light well only in solution, and once the fluorescent materials are aggregated or become solid, the fluorescence disappears, and the phenomenon is called Aggregation-used Quenching (ACQ), which brings trouble to the application of the fluorescent materials. In recent years, scientists in China have discovered a new material with properties opposite to ACQ, namely, stronger fluorescence in an aggregated state, called "Aggregation-Induced Emission" (AIE).
Although the application of ACQ molecules or AIE molecules in biosensing, organic optoelectronic systems, and diagnosis and treatment has been greatly advanced, both can exhibit bright fluorescence only in a single state (solid or solution state) and emit light singly. The development of solid-liquid luminescent materials is urgently needed to fill the gap of luminescent materials. However, the existing method for preparing the solid-liquid luminescent material has complex operation and low yield, and cannot realize large-scale industrial production. Among optical materials, a light-emitting material having a high fluorescence quantum yield is preferred.
Therefore, a simple, efficient, environment-friendly and practical synthetic route is developed to prepare the solid-liquid organic luminescent material with high quantum yield and excellent performance, and the method has very important research significance and application prospect.
With the rapid development of scientific technology, the people level is continuously improved, high-quality life is increasingly pursued, and attention is paid to distinguishing genuine products from counterfeit products, so that the encryption and anti-counterfeiting technology becomes more important in actual life, and the problem that counterfeit and counterfeit products are urgently needed to be solved in life is effectively solved. Therefore, the development of strong anti-counterfeiting technologies is urgent, and one of the solutions is to develop color-changeable fluorescent materials.
CN107759504A discloses a fluorescent material with strong luminescence in both solid and solution states and good solvent effect, and a preparation method and application thereof. Specifically, the invention provides an aryl pyrrole derivative fluorescent material with strong fluorescence emission of solid and solution two phases, represented by a general formula (TPP-R): wherein R is an electron-withdrawing group, and is an aldehyde group, a cyano group or an ester group. The invention also provides a preparation method of the aryl substituted pyrrole derivative fluorescent material, the prepared fluorescent material has higher fluorescence quantum efficiency in solid-liquid state and obvious solvent effect, and one fluorescent material has different luminescence characteristics in different aggregation forms due to the medium-polarity electron-absorbing groups. The fluorescent material with strong luminescence characteristics in solid and solution states has good application prospects in organic light-emitting diodes, chemical detection, biological detection and other aspects. However, the preparation method of the invention is complex, and the solid-liquid quantum yield of the prepared fluorescent material needs to be further improved.
Therefore, in the art, it is expected to develop an organic light emitting material having high quantum yield in both solid-liquid state and simple and efficient preparation method.
Disclosure of Invention
In order to solve the problem that the existing organic luminescent material can only emit light in a single state (solid or liquid) and the luminescent color is invariable, aiming at the defects of the prior art, the invention aims to provide an organic luminescent material and a preparation method and application thereof, and particularly provides an organic luminescent material with solvent discoloration and high quantum yield in both solid and liquid states and a preparation method and application thereof. The synthetic route of the invention is simple, the condition is mild, and the prepared organic luminescent material has high fluorescence quantum yield and has the prospect of industrial application.
In the present invention, the high quantum yield means that the quantum yield of the organic light emitting material in a liquid state can reach 98.9%, and the quantum yield in a solid state can reach 30.5%.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic light emitting material, which has a structure shown in formula I:
wherein R is1、R2、R4、R6、R9、R10Each independently selected from any one of hydrogen, alkyl containing hetero atom, aryl, halogen, alkenyl, heteroaryl or cycloalkyl, and R9And R10At least one of them is
R7、R8Each independently selected from any one of hydrogen, alkyl containing hetero atom, aryl, sulfonyl, tertiary butyl, heteroaryl or halogen.
The organic luminescent material has higher quantum yield in solid state and liquid state, can show different luminescent colors by fumigating different solvents, and can realize multiple encryption effect compared with the traditional encryption anti-counterfeiting material. The organic luminescent material can be used for manufacturing patterns with encryption and anti-counterfeiting functions. In addition, the material can be used for detecting and identifying the solvent, and particularly can be used for detecting mass colorless and tasteless solvents, so that a large amount of manpower and material resources are saved.
Preferably, the organic light emitting material has a structure represented by formula II or formula III:
in a second aspect, the present invention provides a method for preparing an organic light emitting material according to the first aspect, wherein the method for preparing the organic light emitting material takes a compound of formula IV and a compound of formula v as raw materials, and the reaction formula is as follows:
wherein R is1-R6、R9、R10Each independently selected from any one of hydrogen, alkyl containing hetero atom, aryl, halogen, alkenyl, heteroaryl or cycloalkyl, and R3And R5At least one of them being a bromine atom or an iodine atom, R9And R10At least one of them is
R7、R8Each independently selected from any one of hydrogen, alkyl containing hetero atom, aryl, sulfonyl, tertiary butyl, heteroaryl or halogen.
The synthetic route of the reaction system is short, the atom economy of the raw materials is high, the efficiency is excellent, the reaction yield of the product isoindolinone-triphenylamine derivative is up to 92 percent, and the breakthrough progress of the chemical synthesis of the system is realized.
In the present invention, R3And/or R5Is a bromine atom or an iodine atom, which has higher reactivity than a chlorine atom.
The compounds of formula IV of the present invention can be prepared by the following synthetic routes:
wherein R is1-R6Each independently selected from any one of hydrogen, alkyl containing hetero atom, aryl, halogen, alkenyl, heteroaryl or cycloalkyl, and R3And R5At least one of them is a bromine atom or an iodine atom.
The preparation method comprises the following steps:
taking a reaction tube with the specification of 10mL, adding 2mL of toluene as a solvent, and weighing a compound VI (0.2mmol), acetic anhydride (0.8mmol) and a catalyst Pd (CF)3COO)2(0.02mmol) under the protection of inert gas, adding into the reaction tubes respectively, and sealing the reaction tubes. Stirring and reacting for 12h under the condition of 130 ℃ oil bath, detecting by adopting thin-layer chromatography (TLC), cooling to room temperature after the reaction is finished, filtering by using kieselguhr to obtain filtrate, washing solid particles obtained by filtering for a plurality of times by using ethyl acetate, combining washing liquid in the filtrate, distilling the filtrate by using a rotary evaporator to remove toluene and ethyl acetate to obtain a crude product, and recrystallizing the crude product to obtain the compound IV.
Preferably, the molar ratio of the compound of formula IV to the compound of formula V is 1 (1-5), such as 1:1, 1:2, 1:3, 1:4, or 1:5, etc.
Preferably, the catalyst of the reaction comprises a divalent palladium catalyst and/or a tetravalent palladium catalyst, preferably Pd (PPh)3)4、Pd2(dba)3、PdCl2(PPh3)2、PdCl2Or Pd (OAc)2Any one or a combination of at least two of them.
Preferably, the molar ratio of the compound of formula IV to the catalyst is 1 (0.01-1), such as 1:0.01, 1:0.05, 1:0.1, 1:0.2, 1:0.3, 1:0.4, 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9, or 1:1, and the like.
Preferably, the solvent for the reaction includes any one or a combination of at least two of an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent, a halogenated alkane solvent, an alcohol solvent, an ester solvent, a ketone solvent, a sulfoxide solvent, an amide solvent, or a nitrile solvent, preferably any one or a combination of at least two of N, N-dimethylformamide, N-dimethylacetamide, methanol, isopropanol, toluene, acetonitrile, dichloroethane, chloroform, acetone, or dimethylsulfoxide.
Preferably, a basic compound is added to the solvent.
Preferably, the basic compound comprises any one of potassium carbonate, potassium bicarbonate, sodium carbonate, triethylamine or pyridine or a combination of at least two thereof.
Preferably, the concentration of the basic compound in the solvent is 0.05 to 5mol/L, such as 0.05mol/L, 0.1mol/L, 0.5mol/L, 1mol/L, 2mol/L, 3mol/L, 4mol/L, or 5mol/L, and the like.
Preferably, the molar ratio of the compound of formula IV to the basic compound is 1 (1-5), such as 1:1, 1:2, 1:3, 1:4, or 1:5, and the like.
Preferably, the reaction is carried out under a protective gas.
Preferably, the reaction temperature is 40-130 ℃, such as 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃, 100 ℃, 110 ℃,120 ℃ or 130 ℃ etc.. If the reaction temperature is lower than 40 ℃ or higher than 130 ℃, the reaction yield may be less than 10%.
As a preferred technical scheme of the invention, the preparation method comprises the following steps: the organic luminescent material shown in the formula I is obtained by taking an IV compound and a compound of the formula V as raw materials in a molar ratio of 1 (1-5) and reacting at 40-130 ℃ in a system with a catalyst and a basic compound, wherein the molar ratio of the compound of the formula IV to the catalyst is 1 (0.01-1), and the molar ratio of the compound of the formula IV to the basic compound is 1 (1-5).
In a third aspect, the invention provides the use of the organic light emitting material of the first aspect in encryption, anti-counterfeiting or solvent detection.
Compared with the prior art, the invention has the following beneficial effects:
(1) the organic luminescent material has higher quantum yield in both solid and liquid states (the quantum yield in the liquid state is as high as 98.9%, and the quantum yield in the solid state is as high as 30.5%), and different luminescent colors can be shown by fumigating different solvents. The organic luminescent material can be used for manufacturing patterns with encryption and anti-counterfeiting functions, and can also be used for detecting and identifying solvents, particularly large-scale colorless and tasteless solvents, so that a large amount of manpower and material resources are saved.
(2) The synthesis route of the reaction system is short, the atom economy of the raw materials is high, the efficiency is superior, the reaction yield of the product organic luminescent material is up to 92 percent, and the breakthrough progress of the chemical synthesis of the system is realized.
Drawings
Fig. 1A is a diagram showing ultraviolet absorption spectra of the organic light emitting material prepared in example 1 in a solution state in different solvents.
Fig. 1B is a solution state fluorescence spectrum of the organic light emitting material prepared in example 1 in different solvents.
Fig. 2A is a photograph of the organic light emitting material prepared in example 1 in different solvents.
Fig. 2B is a CIE 1976 chromaticity diagram of the organic light emitting material prepared in example 1 in different solvents.
Fig. 3A is an ultraviolet absorption spectrum of the organic light emitting material prepared in example 1 in a solid state.
Fig. 3B is a fluorescence spectrum of the organic light emitting material prepared in example 1 in a solid state.
Fig. 4A is a solution-state uv absorption spectrum of the organic light emitting material prepared in example 2 in different solvents.
Fig. 4B is a solution state fluorescence spectrum of the organic light emitting material prepared in example 2 in different solvents.
Fig. 5A is a photograph of the organic light emitting material prepared in example 2 in different solvents.
Fig. 5B is a CIE 1976 chromaticity diagram of the organic light emitting material prepared in example 2 in different solvents.
Fig. 6A is an ultraviolet absorption spectrum of the organic light emitting material prepared in example 2 in a solid state.
Fig. 6B is a fluorescence spectrum in a solid state of the organic light emitting material prepared in example 2.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention. It should be noted that the reaction conditions, reagents, experimental methods, etc. of the following examples are common general knowledge of those skilled in the art, except for those specifically mentioned. The data given in the examples below include specific operating and reaction conditions and products, the purity of which was determined by nuclear magnetism.
The reagents used in the invention are all commercial analytical pure reagents. The compound of formula V used in the present invention is purchased from Bidi medicine and has CAS number 267221-88-5.
Example 1
In this embodiment, an organic light emitting material is provided, which has a structure shown in formula ii:
the reaction formula is as follows:
the preparation method comprises the following steps:
a10 mL reaction tube was taken, toluene and methanol (volume ratio 1:1, 2mL in total) were added as solvents, and isoindolinone compound 1a (0.2mmol), triphenylamine borate compound 2a (0.3mmol), and catalyst Pd (PPh)3)4(0.02mmol) and potassium carbonate (0.4mmol) were added to the reaction tube under inert gas protection, respectively, and the reaction tube was sealed. The reaction was stirred for 16h in an oil bath at 110 ℃ and Thin Layer Chromatography (TLC) was used) Detecting, cooling to room temperature after the reaction is finished, filtering with diatomite to obtain filtrate, washing with ethyl acetate for several times to obtain solid particles, combining the washing solutions in the filtrate, distilling the filtrate through a rotary evaporator, removing methanol, toluene and ethyl acetate to obtain a crude product, and performing flash column chromatography on the crude product to obtain a pure product, namely the organic luminescent material, wherein the yield is 92%.
The nuclear magnetic results of the organic luminescent material prepared in this example are as follows:
1H-NMR(400MHz,CDCl3):δ8.83(dd,J＝4.1,1.7Hz,1H),8.17(dd,J＝8.4,1.7Hz,1H),7.96-7.85(m,3H),7.70(dd,J＝10.8,7.6Hz,2H),7.61(t,J＝7.7Hz,1H),7.48(d,J＝8.3Hz,2H),7.36(dd,J＝8.3,4.2Hz,1H),7.23-7.17(m,4H),7.09(dd,J＝8.2,5.1Hz,6H),6.99(t,J＝7.3Hz,2H),5.15(d,J＝2.2Hz,1H),4.34(d,J＝2.1Hz,1H)；13C-NMR(100MHz,CDCl3) δ 166.31,150.04,146.99,146.37,143.98,143.68,143.09,136.36,135.26,132.82,131.59,129.87,128.46,128.31,128.25,127.23,127.09,126.68,125.23,123.64,123.01,122.37,122.24,120.73,117.26,89.07, hrms (esi): calculated value C36H25N3O[M+H]+516.6240, actual value 516.6243.
The ultraviolet absorption spectrum of the organic light-emitting material in solution state in different solvents in this example is shown in fig. 1A, and the fluorescence spectrum of the organic light-emitting material in solution state in different solvents in this example is shown in fig. 1B. As can be seen from fig. 1A, the maximum absorption peak of the organic light-emitting material is 365nm, and as can be seen from fig. 1B, the fluorescence emission wavelength of the organic light-emitting material in toluene is 440nm, the fluorescence emission wavelength in tetrahydrofuran is 475nm, the fluorescence emission wavelength in dichloromethane is 500nm, the fluorescence emission wavelength in N, N-dimethylformamide is 525nm, and the fluorescence emission wavelength in dimethylsulfoxide is 540 nm. In addition, the fluorescence quantum yield of the organic luminescent material of the embodiment in the toluene solvent was 98.9%, and the fluorescence lifetime was 1.9 ns.
The photographs of the organic light emitting material of the present example in different solvents and the CIE 1976 chromaticity diagram are shown in fig. 2A and 2B, respectively.
The solid organic light-emitting material of this example was subjected to ultraviolet absorption spectroscopy and fluorescence spectroscopy, and the ultraviolet absorption spectrum and the fluorescence spectrum thereof are shown in fig. 3A and 3B, respectively. As can be seen from fig. 3A, the maximum absorption wavelength of the solid organic light emitting material is 400 nm. As can be seen from fig. 3B, the fluorescence emission wavelength of the organic light emitting material was 520nm, and further, the fluorescence quantum yield was 30.5% and the fluorescence lifetime was 14.4 ns.
Example 2
In this embodiment, an organic light emitting material is provided, which has a structure shown in formula iii:
the reaction formula is as follows:
the preparation method comprises the following steps:
a10 mL reaction tube was taken, toluene and methanol (volume ratio 1:1, 2mL) were added as solvents, and isoindolinone compound 1b (0.2mmol), triphenylamine borate compound 2a (0.3mmol), and catalyst Pd (PPh)3)4(0.02mmol) and potassium carbonate (0.4mmol) were added to the reaction tube under inert gas protection, respectively, and the reaction tube was sealed. Stirring and reacting for 16h under the condition of 110 ℃ oil bath, detecting by adopting thin-layer chromatography (TLC), cooling to room temperature after the reaction is finished, filtering by using kieselguhr to obtain filtrate, washing solid particles obtained by filtering for a plurality of times by using ethyl acetate, combining washing liquids in the filtrate, distilling the filtrate by using a rotary evaporator to remove methanol, toluene and ethyl acetate to obtain a crude product, and carrying out flash column chromatography on the crude product to obtain a pure product, namely the organic luminescent material, wherein the yield is 87%.
The nuclear magnetic results of the organic light emitting material prepared in this example are as follows:
1H-NMR(400MHz,CDCl3)：δ8.90(d,J＝2.7Hz,1H),8.43(d,J＝8.5Hz,1H),8.00(d,J＝7.5Hz,1H),7.81(t,J＝7.0Hz,2H),7.70–7.63(m,2H),7.59(t,J＝7.4Hz,1H),7.40–7.29(m,7H),7.22(d,J＝6.8Hz,6H),7.09(t,J＝7.2Hz,2H),5.23(d,J＝1.7Hz,1H),4.52(d,J＝1.6Hz,1H)；13C-NMR(100MHz,CDCl3) Delta 166.18,149.38,146.40,146.11,143.56,142.71,140.34,135.38,133.57,130.88,130.76,130.06,129.41,128.96,128.20,128.12,128.03,126.57,125.39,123.45,122.35,121.98,121.46,120.15,118.93,88.94, HRMS (ESI) calculated C36H25N3O[M+H]+516.6240, actual value 516.6241.
The solution ultraviolet absorption spectra of the organic light emitting material in different solvents of this embodiment are shown in fig. 4A, and the solution fluorescence spectra of the organic light emitting material in different solvents of this embodiment are shown in fig. 4B. As can be seen from FIG. 4A, the maximum absorption peak of the organic light emitting material is 365nm, and as can be seen from FIG. 4B, the fluorescence emission wavelength of the organic light emitting material in toluene is 450nm, the fluorescence emission wavelength in tetrahydrofuran is 480nm, the fluorescence emission wavelength in methylene chloride is 500nm, the fluorescence emission wavelength in N, N-dimethylformamide is 525nm, and the fluorescence emission wavelength in dimethyl sulfoxide is 545 nm. In addition, the organic light emitting material of the present example has a fluorescence quantum yield of 82.9% in a toluene solvent and a fluorescence lifetime of 2.2 ns.
Photographs of the organic light emitting material of the present example in different solvents and CIE 1976 chromaticity diagrams are shown in fig. 5A and 5B, respectively.
The solid organic light-emitting material of this example was subjected to ultraviolet absorption spectroscopy and fluorescence spectroscopy, and the ultraviolet absorption spectrum and the fluorescence spectrum thereof are shown in fig. 6A and 6B, respectively. As can be seen from fig. 6A, the maximum absorption wavelength of the solid organic light emitting material is 460 nm. As can be seen from fig. 6B, the fluorescence emission wavelength of the solid organic light emitting material was 515nm, and further, the fluorescence quantum yield thereof was 20.3% and the fluorescence lifetime was 4.7 ns.
From the test results of example 1 and example 2, it can be seen that the organic light emitting material prepared by the present invention has a two-state (solid and liquid) high quantum yield light emitting property, and the unique solvent discoloration property of the light emitting material can be used for data encryption as well as solvent detection.
Application example 1
The organic luminescent material prepared in example 1 was used in pattern encryption anti-counterfeiting: the toluene solution of organic luminescent material is sprayed on paper to write digital 8 pattern, after the solvent is volatilized, the pattern is observed under 365nm ultraviolet lamp, and the pattern is blue. The upper half of "8" was sprayed with a toluene solution of an organic light emitting material, and the lower half was sprayed with ethanol of an organic light emitting material, followed by observation under a 365nm ultraviolet lamp, with the upper half of "8" being blue and the lower half being yellow.
Application example 2
The organic luminescent material prepared in example 1 was used in pattern encryption anti-counterfeiting: the toluene solution of organic luminescent material is sprayed on paper to write a 'solvent' pattern, and the pattern is blue when the toluene solvent is volatilized and observed under a 365nm ultraviolet lamp. Spraying different solvents in a closed box by using a nano spraying instrument, and turning on a 365nm ultraviolet lamp. The results show that: the kind of solvent can be accurately distinguished from the pattern color.
Comparative example 1
Comparative example 1 differs from example 1 only in that isoindolinone compound 1a is replaced with an equal amount of 5-bromoquinoline, and the other conditions are the same as in example 1.
The reaction formula is as follows:
the fluorescence quantum yield of the material prepared in comparative example 1 in toluene solvent was 57.4%, and the fluorescence lifetime was 2.8 ns. The solid material prepared in comparative example 1 had a fluorescence quantum yield of 2.3% and a fluorescence lifetime of 0.7 ns.
The applicant states that the present invention is illustrated by the above examples to the organic light emitting material of the present invention, the preparation method and the application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must rely on the above examples to be implemented. It will be apparent to those skilled in the art that various modifications and variations of the isoindolinone-triphenylamine core of the present invention, equivalent substitutions of the selected raw materials, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (15)
1. An organic light-emitting material, wherein the organic light-emitting material has a structure represented by formula II or formula III:
2. the method for preparing the organic light-emitting material according to claim 1, wherein the compound of formula IV and the compound of formula V are used as raw materials to react to produce the organic light-emitting material shown in formula I, and the reaction formula is as follows:
wherein R is1、R2、R4、R6Are each hydrogen, R3、R5Each independently is hydrogen, bromine atom or iodine atom, and R3And R5One is hydrogen, the other is bromine or iodine, R9、R10Each independently selected from hydrogen or
And R is9And R10One of which is hydrogen and the other is
R7、R8Are all hydrogen.
3. The method according to claim 2, wherein the molar ratio of the compound of formula IV to the compound of formula V is 1 (1-5).
4. The method of claim 2, wherein the catalyst for the reaction comprises a divalent palladium catalyst and/or a tetravalent palladium catalyst.
5. The method according to claim 4, wherein the catalyst for the reaction is Pd (PPh)3)4、Pd2(dba)3、PdCl2(PPh3)2、PdCl2Or Pd (OAc)2Or a combination of at least two thereof.
6. The method of claim 4, wherein the molar ratio of the compound of formula IV to the catalyst is 1 (0.01-1).
7. The method according to claim 2, wherein the solvent for the reaction comprises any one or a combination of at least two of N, N-dimethylformamide, N-dimethylacetamide, methanol, isopropanol, toluene, acetonitrile, dichloroethane, chloroform, acetone, and dimethylsulfoxide.
8. The method according to claim 7, wherein a basic compound is added to the solvent.
9. The method according to claim 8, wherein the basic compound comprises any one of potassium carbonate, potassium bicarbonate, sodium carbonate, triethylamine, or pyridine, or a combination of at least two thereof.
10. The production method according to claim 8, wherein the concentration of the basic compound in the solvent is 0.05 to 5 mol/L.
11. The method according to claim 8, wherein the molar ratio of the compound of formula IV to the basic compound is 1 (1-5).
12. The method of claim 2, wherein the reaction is carried out under a protective gas.
13. The method according to claim 2, wherein the reaction temperature is 40 to 130 ℃.
14. The method of any one of claims 2-13, wherein the method is: the organic luminescent material shown in the formula I is obtained by taking an IV compound and a compound of the formula V as raw materials in a molar ratio of 1 (1-5) and reacting at 40-130 ℃ in a system with a catalyst and a basic compound, wherein the molar ratio of the compound of the formula IV to the catalyst is 1 (0.01-1), and the molar ratio of the compound of the formula IV to the basic compound is 1 (1-5).
15. Use of the organic luminescent material according to claim 1 for encryption, anti-counterfeiting or solvent detection.
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