CN106811191A - The light conversion film of the green glow dyestuff containing aggregation-induced emission property - Google Patents

The light conversion film of the green glow dyestuff containing aggregation-induced emission property Download PDF

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CN106811191A
CN106811191A CN201611224411.4A CN201611224411A CN106811191A CN 106811191 A CN106811191 A CN 106811191A CN 201611224411 A CN201611224411 A CN 201611224411A CN 106811191 A CN106811191 A CN 106811191A
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light conversion
green glow
conversion film
dyestuff
light
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周鹏程
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Publication of CN106811191A publication Critical patent/CN106811191A/en
Priority to PCT/CN2017/105307 priority patent/WO2018120968A1/en
Priority to TW106138221A priority patent/TWI642716B/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18Manufacture of films or sheets
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12Homopolymers or copolymers of methyl methacrylate
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0097Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/06Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12Homopolymers or copolymers of methyl methacrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00Applications
    • C08L2203/16Applications used for films
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051Heterocyclic 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)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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Abstract

Light conversion film the present invention relates to contain the green glow dyestuff of aggregation-induced emission (AIE) property, it is made up of with the macromolecule resin of solidification green glow dyestuff, the molecular structure such as formula (I) of the green glow dyestuff is described, the present invention is made light conversion film using the green glow dyestuff of aggregation-induced emission (AIE) property first, under blue light source, green glow can be launched, very strong fluorescence is shown after being made solid or PMMA films, dyestuff is in the strong luminous organic light transform film material that is applied to of solid-state with very big advantage.

Description

The light conversion film of the green glow dyestuff containing aggregation-induced emission property
Technical field
The present invention relates to light conversion film, and in particular to a class contains tetraphenyl ethylene group has aggregation-induced emission property Green glow dyestuff, optical conversion film is made by solution spin coating, be can be applied to plane and is shown.
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, CN105267059 A, CN103647003 A), 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, the present invention provides a kind of green glow dyestuff containing aggregation-induced emission (AIE) property Light conversion film, the macromolecule trees such as methyl methacrylate (PMMA) are dispersed in by the green glow dyestuff with aggregation-induced emission property Solidification is prepared for light conversion film in fat, and the present invention is first by this kind of AIE type dyes molecular application in organic light transform film material.
The light conversion film of the green glow dyestuff containing aggregation-induced emission (AIE) property, by green glow dyestuff and the high score for solidifying Subtree fat is constituted, and the molecular structure such as formula (I) of the green glow dyestuff 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:
Above-mentioned dye molecule is prepared by Suzuki coupling reactions:
The macromolecule resin of the solidification is acrylate, epoxy resin or polyurethane, and the light conversion film gross thickness is 1-100μm。
The preparation method of the light conversion film, be by above-mentioned green glow dyestuff with solidification macromolecule resin be dissolved in toluene after, Spin-coating film, dries solidify afterwards and prepares organic light transform film again, is fixed on backlight.
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.
The blue light source is liquid crystal panel, OLED or inorganic LED light source.
The present invention is made light conversion film using the green glow dyestuff of aggregation-induced emission (AIE) property first, in blue light source Under, green glow can be launched, very strong fluorescence is shown after being made solid or PMMA films, dyestuff is in the strong luminous application of solid-state There is very big advantage in organic light transform film material.
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 。1H NMR (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. the light conversion film of the green glow dyestuff of aggregation-induced emission (AIE) property is contained, by green glow dyestuff and the macromolecule for solidifying Resin group, the molecular structure such as formula (I) of the green glow dyestuff 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. light conversion film 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. light conversion film according to claim 2, R1, R2 are identical.
4. light conversion film according to claim 3, R1 and R2 is expressed as hydrogen, the tert-butyl group.
5. light conversion film 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. light conversion film according to claim 5, is the compound with having structure:
7. light conversion film according to claim 5, the macromolecule resin of the solidification is acrylate, epoxy resin or poly- Urethane, the light conversion film gross thickness is 1-100 μm.
8. the preparation method of any light conversion films of claim 1-7, is that green glow dyestuff is molten with the macromolecule resin of solidification In after toluene, then spin-coating film, drying solidify afterwards prepare organic light transform film, are fixed on backlight.
9. preparation method according to claim 8, the curing preparation method thereof is heat cure or ultraviolet light polymerization, the back of the body Light source is blue light source, and the macromolecule resin of solidification is methyl methacrylate macromolecule resin.
10. preparation method according to claim 9, the blue light source is liquid crystal panel, OLED or inorganic LED light Source.
CN201611224411.4A 2016-12-27 2016-12-27 The light conversion film of the green glow dyestuff containing aggregation-induced emission property Pending CN106811191A (en)

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CN201611224411.4A CN106811191A (en) 2016-12-27 2016-12-27 The light conversion film of the green glow dyestuff containing aggregation-induced emission property
PCT/CN2017/105307 WO2018120968A1 (en) 2016-12-27 2017-10-09 Light conversion film containing green light dye having aggregation-induced emission property
TW106138221A TWI642716B (en) 2016-12-27 2017-11-04 Light conversion film containing the aie nature green dye

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN109206728A (en) * 2017-07-03 2019-01-15 比亚迪股份有限公司 Stress color-changing composition, stress color-changing membrane and preparation method thereof and stress discoloration photovoltaic module
CN109233738A (en) * 2018-08-31 2019-01-18 江苏科技大学 Fluorescence adhesive and the preparation method and application thereof based on aggregation-induced emission mechanism

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