CN106867507A - A kind of green glow dyestuff with aggregation-induced emission property - Google Patents
A kind of green glow dyestuff with aggregation-induced emission property Download PDFInfo
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- CN106867507A CN106867507A CN201611224162.9A CN201611224162A CN106867507A CN 106867507 A CN106867507 A CN 106867507A CN 201611224162 A CN201611224162 A CN 201611224162A CN 106867507 A CN106867507 A CN 106867507A
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- green glow
- glow dyestuff
- dyestuff
- expressed
- hydrogen
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- 239000000975 dye Substances 0.000 title claims abstract description 53
- 238000004220 aggregation Methods 0.000 title claims abstract description 8
- 230000002776 aggregation Effects 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229920002521 macromolecule Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 238000007711 solidification Methods 0.000 claims description 8
- 230000008023 solidification Effects 0.000 claims description 8
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001723 curing Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000013007 heat curing Methods 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- -1 poly- ammonia Ester Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 17
- 238000006862 quantum yield reaction Methods 0.000 abstract description 6
- 238000012360 testing method Methods 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UGFMBZYKVQSQFX-UHFFFAOYSA-N para-methoxy-n-methylamphetamine Chemical compound CNC(C)CC1=CC=C(OC)C=C1 UGFMBZYKVQSQFX-UHFFFAOYSA-N 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000001514 detection method Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000007867 post-reaction treatment Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000008901 benefit Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000007739 conversion coating Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 238000013019 agitation Methods 0.000 description 1
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- XHXMPURWMSJENN-UHFFFAOYSA-N coumarin 480 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C XHXMPURWMSJENN-UHFFFAOYSA-N 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 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 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of green glow dyestuff with aggregation-induced emission property, the green glow dyestuff, with the structure as shown in formula (I), photophysical property test to it shows, molecule shown in formula (1) has fluorescence quantum yield high in solid-state, can apply and use green glow light conversion film material.
Description
Technical field
The new organic color shown the present invention relates to be used for plane changes membrane material, and in particular to a class contains tetraphenyl ethylene
Group has the green glow dyestuff of aggregation-induced emission property, and film is made by solution spin coating, can be applied to plane and shows.
Background technology
With display industry technology continuous breakthrough and the market demand increasingly increase, flat-panel monitor with its small volume,
Lightweight, power consumptive province, radiate the series of advantages such as small, Electro Magnetic Compatibility is good and emerge rapidly, the master as 21 century Display Technique
Stream.Flat-panel monitor plays very important effect into color mode in its production process, and its quality directly determines flat
The color developing effect of panel display, production cost and service life.
Current flat-panel monitor realizes that the mainstream technology of colored display is prepared by printing red, green, blue fluorescent material with three basic colour
Device, however, because the life-span of fluorescent material with three basic colour and the dough softening differ greatly, it is easy to cause the inclined of color monitor
Color, and the manufacture craft of three primary colors device is more complicated, it is relatively costly.In order to solve these problems, people open and propose one
The new approaches for planting color conversion are " color-by blue "." color-by blue " technology is made using the blue emitting phophor with single high brightness
It is backlight, the blue light that backlight sends shows by being transformed into feux rouges and green glow after color conversion coatings film so as to realize that RGB is full-color
Show.This technology can not only greatly simplify the production technology of electroluminescent flat-panel screens, improve the color stable of display
Property and uniformity, and the production cost of display can also be significantly reduced.For color conversion coatings film material can be divided into it is inorganic and
Organic two major class.It has been investigated that, relative to inorganic fluorescent powder, not only there is organic transition material color conversion higher to imitate
Rate, color also more saturation, such that it is able to realize broader colour gamut, and raw material is cheap and easy to get, it is easier to carry out cutting out for molecule
With modification obtaining more preferable display effect.
The nineties in 20th century, it is green light material that Leising team uses Coumarins dyestuff Coumarin 102,
Lumogen F300 are prepared for green, red light conversion film for red dye is dispersed in PMMA, obtain red more than 10%
Light conversion efficiency (bibliography：Adv.Mater.,1997,9(1),33-36).Recent year research team is also to organic light
(bibliography is reported in the preparation for changing film：Optoelectronics Letters,2010,6(4),245-248,
CN105267059A, CN103647003A), obtain colour gamut extensively, the organic light transform film of light high conversion rate.
Organic fluorescence color conversion coatings film is usually that the organic fluorescent dye with different colours is passed through into ultra-violet curing or heat
The modes such as solidification are evenly dispersed in macromolecular solid body thin film, then with the Blue backlight source excitation organic fluorescence color of high brightness
The dye molecule in film is changed to realize the transformation of color, the blue light of the feux rouges being converted to, green glow and background forms the three of light
Primary colours are planted, the full-color EL display of electroluminescent cell may finally be realized.
However, be susceptible to assemble and cause fluorescent quenching between the organic dye molecule for generally using, in filminess
Hardly light, therefore in these light conversion film materials, organic dyestuff is usually to be disperseed with very low concentration (some thousandths of)
In transparent macromolecule resin, too low concentration frequently can lead to incomplete absorption of the film to light, it is desirable to obtain sufficient light
Conversion effect must just increase the thickness of film, so as to cause the increase of whole display panel thickness.
This loyal academician of the Tang of Hong Kong University of Science and Thchnology proposes the concept of aggregation-induced emission (AIE), the molecule of this kind of AIE types
In solid-state with quantum yield very high, molecule its solid state quantum yield (QY) constituted with diazosulfide and tetraphenyl ethylene
89% (bibliography is reached：Chem.Commun., 2011,47,8847-8849), this quasi-molecule is widely used in biology
Fluorescence probe, ion detection, oled emitting layer materials etc., but its application in organic light transform film material does not appear in the newspapers but
Road, high quantum production rate of the AIE types molecule in solid-state makes its application in this field have natural advantage.
The content of the invention
For above-mentioned light conversion film material, the present invention provides a kind of green glow with aggregation-induced emission (AIE) property and contaminates
Material molecule, solidification is prepared for light conversion film in being dispersed in the macromolecule resins such as methyl methacrylate (PMMA), the present invention
First by this kind of AIE type dyes molecular application in organic light transform film material.
A kind of green glow dyestuff with aggregation-induced emission property, its molecular structure such as formula (I) is described,
Wherein, R1 and R2 are independently expressed as hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen；Ar is independently expressed as
The substituted or unsubstituted carbon-to-carbon double bond of alkyl or the C6-C30 phenyl ring or heterocycle of three key overseas Chinese federations or non-overseas Chinese federation, between n=0-3
Integer.
It is preferred that：Wherein, R1 and R2 are independently expressed as hydrogen, C1-C4 alkyl or alkoxy, and Ar is independently expressed as carbon-to-carbon
The phenyl ring or heterocycle aromatic ring of the C6-C20 of double or triple bonds overseas Chinese federation or non-overseas Chinese federation, the integer between n=0-2.
It is preferred that：R1, R2 are identical.
It is preferred that：R1 and R2 are expressed as hydrogen, the tert-butyl group.
It is preferred that：Wherein, R1 and R2 are preferably expressed as hydrogen, the tert-butyl group, and Ar is independently expressed as and is not limited to listed below
Aromatic ring or heterocycle, the integer between n=0-2：
Compound described in formula (I) is preferably the compound with having structure：
The synthesis of green glow dyestuff GA1：
The first step is used and phenylmethane derivative and benzophenone derivative condensation prepare the tetraphenyl ethylene of bromo.
Second step carries out the borate that substitution reaction prepares tetraphenyl ethylene using butyl lithium.
3rd step prepares target dye molecule GA1 by Suzuki coupling reactions.
The synthesis of green glow dyestuff GA2：
The first step prepares the diazosulfide that double phenyl replace by Suzuki coupling reactions.
Second step carries out bromo-reaction using bromine.
3rd step prepares target dye molecule GA2 by Suzuki coupling reactions.
Light conversion film, is made up of above-mentioned green glow dyestuff with the macromolecule resin of solidification.
The macromolecule resin of the solidification is acrylate, epoxy resin or polyurethane.
The light conversion film gross thickness is 1-100 μm.
Application of the above-mentioned green glow dyestuff in light conversion film.
The application is then spin-coating film, drying after above-mentioned green glow dyestuff is dissolved in into toluene with the macromolecule resin of solidification
Solidify afterwards prepare organic light transform film, are fixed on backlight, are applied to during plane shows, to realize full-color display.
The curing preparation method thereof is heat cure or ultraviolet light polymerization.
The backlight is blue light source, and the macromolecule resin of solidification is methyl methacrylate (PMMA) high score subtree
Fat.
Experiment shows, with the CCF films of GA1 and GA2 preparations to background blue light (λmax≈ 450nm) there are absorption well, transmitting
The light for going out is green glow, the weaker (QY of GA1 and GA2 fluorescence in the solution<50%) shown after, being made solid or PMMA films
Very strong fluorescence, first by AIE type dyes molecular application in organic light transform film material, dyestuff is in strong luminous of solid-state for the present invention
Organic light transform film material is applied to very big advantage.
Brief description of the drawings
The synthetic route schematic diagram of Fig. 1 green glow dyestuff GA1 of the present invention
The synthetic route schematic diagram of Fig. 2 green glow dyestuff GA2 of the present invention；
Ultraviolet-visibles of Fig. 3 green glow dyestuff GA1 of the present invention in toluene, dichloromethane and PMMA films and solid-state is inhaled
Receive spectrum
Fluorescence emissions of Fig. 4 green glow dyestuff GA1 of the present invention in toluene, dichloromethane and PMMA films and solid-state
Spectrum；
Ultraviolet-visibles of Fig. 5 green glow dyestuff GA2 of the present invention in toluene, dichloromethane and PMMA films and solid-state is inhaled
Receive spectrum；
Fluorescence emissions of Fig. 6 green glow dyestuff GA2 of the present invention in toluene, dichloromethane and PMMA films and solid-state
Spectrum；
Light conversion film prepared by Fig. 7 green glow dyestuff GA1 of the present invention.
Specific embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
The synthesis of green glow dyestuff GA1：
The first step is used and phenylmethane derivative and benzophenone derivative condensation prepare the tetraphenyl ethylene of bromo.
Second step carries out the borate that substitution reaction prepares tetraphenyl ethylene using butyl lithium.
3rd step prepares target dye molecule GA1 by Suzuki coupling reactions.
The synthesis of green glow dyestuff GA2：
The first step prepares the diazosulfide that double phenyl replace by Suzuki coupling reactions.
Second step carries out bromo-reaction using bromine.
3rd step prepares target dye molecule GA2 by Suzuki coupling reactions.
The synthesis of the green glow dyestuff GA1 of embodiment 1：
(1) synthesis of compound 3a
Synthesis step：Compound 1a (commercially available) (5.61g, 20mmol) is dissolved in anhydrous THF (100mL) under nitrogen protection,
Reaction solution is cooled under 0 DEG C, stirring and is slowly added dropwise butyl lithium (2.2M, 14mL), low temperature stirring 1h is continued after dripping, then
To compound 2a (commercially available) (10.45g, 40mmol) is added in reaction solution, continue low temperature stirring 1h.Then reaction solution is risen into room
Temperature is stirred overnight.
Post-reaction treatment：Reaction solution is poured into water after having reacted, EA (100mL*3) extraction point liquid merges organic layer, uses
Evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product is directly used in next step and reacts without purifying.
(2) synthesis of compound 4a
Synthesis step：The compound 3a crude products for obtaining back under nitrogen protection are dissolved in dry toluene (50mL), then
To adding TSOH in reaction solution.H2O (380mg, 2mmol), is heated to back flow reaction 12 hours, and TLC detection compounds 3a has reacted
Entirely.Post-reaction treatment：Stop reaction, reaction solution is poured into water, EA (100mL*2) extraction point liquid merges organic layer, with anhydrous
Evaporated under reduced pressure after sodium sulphate drying.Crude product obtains lurid compound 4a (5.7g, yield 54.5%) through column chromatography.1H NMR
(400MHz, CHLOROFORM-d) δ=7.23-7.15 (m, 2H), 7.15-7.04 (m, 7H), 7.04-6.83 (m, 8H), 1.29-
1.25(m,9H),1.24(s,13H)。
(3) synthesis of compound 5a
Synthesis step：By compound 4a (5.7g, 10.9mmol), Pd (dppf) Cl under nitrogen protection2(400mg, 5%),
Duplex pinacol borate (4.2g, 16.4mmol), potassium acetate (2.1g, 21.8mmol) is dissolved in anhydrous 1,4- dioxane
(70mL), is then heated to reaction solution reflux temperature and reacts 12 hours under agitation, and TLC detection compounds 4a reactions are complete.
Post-reaction treatment：Stop reaction, reaction solution be poured into water, EA (100mL*2) extraction point liquid merges organic layer,
With evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product obtains lurid compound 5a (5.7g, yield 54.5%) through column chromatography
。1HNMR (400MHz, CHLOROFORM-d) δ=7.52 (d, J=8.1Hz, 2H), 7.11-7.01 (m, 10H), 6.97-6.88
(m,5H),1.32(s,9H),1.26-1.23(m,21H)。
(4) synthesis of GA1
Synthesis step：To addition compound 5a (627mg, 1.1mmol), compound 6a (commercially available) in 250mL reaction flasks
(147mg,0.5mmol),Pd2(dba)3(51mg, 5%), tri-butyl phosphine (22mg, 10%), K2CO3(304mg,
2.2mmol), toluene (5mL) and water (1mL).Nitrogen purge 3 times, is heated to 100 DEG C, keeps this temperature, and reaction 12 is small
When, TLC detection compounds 5a reactions are complete.
Post-reaction treatment：Stop heating, be cooled to 20 DEG C, reaction solution is poured into water, ethyl acetate (50mL*2) extraction
Divide liquid, merge organic layer, with evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product obtains lurid compound GA1 through column chromatography
(0.35g, yield 68.6%).
1H NMR (400MHz, CHLOROFORM-d) δ=7.74 (s, 2H), 7.72 (d, J=1.8Hz, 4H), 7.17 (s,
2H), 7.15 (d, J=3.8Hz, 4H), 7.13-7.08 (m, 16H), 7.02 (d, J=8.3Hz, 4H), 6.96 (d, J=8.3Hz,
4H),1.25(s,36H)。
The synthesis of the green glow dyestuff GA1 of embodiment 2：
(1) synthesis of compound 3b
Synthesis step：To addition compound 6a (commercially available) (2.93g, 10mmol), compound 2b in 250mL reaction flasks
(commercially available) (2.68g, 22mmol), tetra-triphenylphosphine palladium (1.15g, 5%), K2CO3(4.14g, 30mmol), toluene (100mL) and
Water (20mL).Nitrogen purge 3 times, is heated to 80 DEG C, keeps this temperature, reacts 8 hours, TLC detection compounds 6a reactions
Completely.
Post-reaction treatment：Stop heating, be cooled to 20 DEG C, reaction solution is poured into water, EA (100mL*3) extraction point liquid,
Merge organic layer, with evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product through column chromatography obtain lurid compound 3b (2.3g,
Yield 79.8%).1H NMR (400MHz, CHLOROFORM-d) δ=7.97 (d, J=7.2Hz, 4H), 7.80 (s, 2H),
7.61-7.53(m,4H),7.51-7.43(m,2H)。
(2) synthesis of compound 4b
Synthesis step：Compound 3b (2.3g, 8.0mmol) is dissolved in 50mL chloroforms, is stirred at room temperature lower to drop in reaction solution
Liquid feeding bromine (2.82g, 17.6mmol), continues to be stirred overnight at room temperature after completion of dropping, and TLC detection compounds 3b reactions are complete.
Post-reaction treatment：Reaction solution is poured into the aqueous solution of sodium bisulfite of saturation, dichloromethane (50mL*3) extraction
Divide liquid, merge organic layer, with evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product obtains lurid compound 4b through column chromatography
(2.2g, yield 49.3%).1H NMR (400MHz, CHLOROFORM-d) δ=7.86 (d, J=8.4Hz, 4H), 7.78 (s,
2H), 7.68 (d, J=8.4Hz, 4H).
(3) synthesis of GA2
Synthesis step：To in 250mL reaction flasks add compound 4b (223mg, 0.5mmol), 5a (627mg,
1.1mmol),Pd2(dba)3(51mg, 5%), tri-butyl phosphine (22mg, 10%), K2CO3(304mg, 2.2mmol), toluene
(5mL) and water (1mL).Nitrogen purge 3 times, is heated to 100 DEG C, keeps this temperature, reacts 12 hours, TLC detection chemical combination
Thing 4b reactions are complete.
Post-reaction treatment：Stop heating, be cooled to 20 DEG C, reaction solution is poured into water, ethyl acetate (50mL*2) extraction
Divide liquid, merge organic layer, with evaporated under reduced pressure after anhydrous sodium sulfate drying.Crude product obtains lurid compound GA2 through column chromatography
(0.42g, yield 71.6%).1H NMR (400MHz, CHLOROFORM-d) δ=8.03 (d, J=8.3Hz, 4H), 7.86-
7.81 (m, 2H), 7.74 (d, J=8.4Hz, 4H), 7.42 (d, J=8.3Hz, 4H), 7.15-7.08 (m, 22H), 6.98 (dd, J
=8.4,15.7Hz, 8H), 1.27 (s, 18H), 1.26 (s, 18H).
The photophysical property test of embodiment 3 green glow dyestuff GA1 and GA2：
Green glow dyestuff GA1 and GA2 photophysical property test in the solution are that corresponding dyestuff is dissolved in into toluene or dichloro
Methane, the concentration of solution is 1 × 10-5Mol/L, the CCF films based on dyestuff are that the PMMA of dyestuff and corresponding proportion is dissolved in into first
Prepared by benzene, spin-coated and then drying, the photophysical property of dye film is that dyestuff is dissolved in after spin coating after THF prepares film to survey
.With the CCF films of GA1 and GA2 preparations to background blue light (λmax≈ 450nm) there is absorption well, the light launched is green glow,
Weaker (the QY of GA1 and GA2 fluorescence in the solution<50%) very strong fluorescence is shown after, being made solid or PMMA films, is had
There are typical AIE properties, the present invention is first by AIE type dyes molecular application in organic light transform film material, and dyestuff is strong in solid-state
The luminous organic light transform film material that is applied to very big advantage.
Claims (10)
1. a kind of green glow dyestuff with aggregation-induced emission property, its molecular structure such as formula (I) is described,
Wherein, R1 and R2 are independently expressed as hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen；Ar is independently expressed as alkyl
Substituted or unsubstituted carbon-to-carbon double bond or the C6-C30 phenyl ring or heterocycle of three key overseas Chinese federations or non-overseas Chinese federation, it is whole between n=0-3
Number.
2. green glow dyestuff according to claim 1, wherein, R1 and R2 is independently expressed as hydrogen, C1-C4 alkyl or alcoxyl
Base, Ar is independently expressed as the phenyl ring or heterocycle aromatic ring of the C6-C20 of carbon-to-carbon double bond or three key overseas Chinese federations or non-overseas Chinese federation, n=0-2
Between integer.
3. green glow dyestuff according to claim 2, R1, R2 are identical.
4. green glow dyestuff according to claim 3, R1 and R2 is expressed as hydrogen, the tert-butyl group.
5. green glow dyestuff according to claim 1, wherein, R1 and R2 is expressed as hydrogen, the tert-butyl group, Ar be independently expressed as
One of lower listed aromatic ring, the integer between n=0-3：
6. green glow dyestuff according to claim 5, is the compound with having structure：
7. the synthetic method of the green glow dyestuff GA1 described in claim 6, using following steps：
The first step is used and phenylmethane derivative and benzophenone derivative condensation prepare the tetraphenyl ethylene of bromo,
Second step carries out the borate that substitution reaction prepares tetraphenyl ethylene using butyl lithium,
3rd step prepares target dye molecule GA1 by Suzuki coupling reactions.
8. the synthetic method of the green glow dyestuff GA2 described in claim 6, using following steps：
The first step prepares the diazosulfide that double phenyl replace by Suzuki coupling reactions,
Second step carries out bromo-reaction using bromine,
3rd step prepares target dye molecule GA2 by Suzuki coupling reactions.
9. application of any described green glow dyestuffs of claim 1-6 in light conversion film, is by above-mentioned green glow dyestuff and solidification
Macromolecule resin be dissolved in toluene after, then spin-coating film, drying solidify afterwards prepare organic light transform film, are fixed on backlight,
It is applied to during plane shows, to realize full-color display.
10. application according to claim 9, the macromolecule resin of the solidification is acrylate, epoxy resin or poly- ammonia
Ester, the curing preparation method thereof is heat cure or ultraviolet light polymerization, and the backlight is blue light source.
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| CN201611224162.9A CN106867507A (en) | 2016-12-27 | 2016-12-27 | A kind of green glow dyestuff with aggregation-induced emission property |
| PCT/CN2017/105309 WO2018120970A1 (en) | 2016-12-27 | 2017-10-09 | Green light dye with aggregation-induced emission property |
| TW106138215A TWI676656B (en) | 2016-12-27 | 2017-11-04 | Having an aggregation-inducing properties of green luminescent dye and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018120968A1 (en) * | 2016-12-27 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | Light conversion film containing green light dye having aggregation-induced emission property |
| WO2018120970A1 (en) * | 2016-12-27 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | Green light dye with aggregation-induced emission property |
| CN110343081A (en) * | 2019-07-31 | 2019-10-18 | 湘潭大学 | A kind of fluorescence anhydride compound and its preparation method and application with aggregation-induced emission property |
| CN114106015A (en) * | 2021-10-11 | 2022-03-01 | 深圳大学 | Novel near-infrared two-region emission aggregation-induced luminescent material, and preparation method and application thereof |
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| CN113308129B (en) * | 2020-02-26 | 2022-01-14 | 四川大学 | Homogeneous polycrystalline symmetrical bis (tetraphenylethylene) fluorescent compound preparation method and crystal thereof |
| CN114621159B (en) * | 2022-04-06 | 2023-04-18 | 电子科技大学 | Diazosulfide-based fluorescent material, fluorescent polymer, fluorescent nanoparticles, and preparation method and application thereof |
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| CN102858911A (en) * | 2010-03-01 | 2013-01-02 | 香港科技大学 | Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives |
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| CN104673275B (en) * | 2013-10-15 | 2016-08-31 | 香港科技大学深圳研究院 | A kind of activation luminescent material and preparation method thereof |
| CN104877665B (en) * | 2013-12-19 | 2017-01-11 | 香港科技大学深圳研究院 | Luminescent material having aggregation-induced emission, method of making and application thereof |
| CN105315988A (en) * | 2015-01-12 | 2016-02-10 | 中南大学 | Fluorochrome for cytolysosome positioning and preparation method and application thereof |
| CN106867507A (en) * | 2016-12-27 | 2017-06-20 | 广东阿格蕾雅光电材料有限公司 | A kind of green glow dyestuff with aggregation-induced emission property |
| CN106811191A (en) * | 2016-12-27 | 2017-06-09 | 广东阿格蕾雅光电材料有限公司 | The light conversion film of the green glow dyestuff containing aggregation-induced emission property |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018120968A1 (en) * | 2016-12-27 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | Light conversion film containing green light dye having aggregation-induced emission property |
| WO2018120970A1 (en) * | 2016-12-27 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | Green light dye with aggregation-induced emission property |
| CN110343081A (en) * | 2019-07-31 | 2019-10-18 | 湘潭大学 | A kind of fluorescence anhydride compound and its preparation method and application with aggregation-induced emission property |
| CN110343081B (en) * | 2019-07-31 | 2022-09-27 | 湘潭大学 | Fluorescent anhydride compound with aggregation-induced emission property and preparation method and application thereof |
| CN114106015A (en) * | 2021-10-11 | 2022-03-01 | 深圳大学 | Novel near-infrared two-region emission aggregation-induced luminescent material, and preparation method and application thereof |
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