CN106701063B - A kind of controllable organic solid-state luminescent material, preparation method and applications - Google Patents
A kind of controllable organic solid-state luminescent material, preparation method and applications Download PDFInfo
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- CN106701063B CN106701063B CN201611178294.2A CN201611178294A CN106701063B CN 106701063 B CN106701063 B CN 106701063B CN 201611178294 A CN201611178294 A CN 201611178294A CN 106701063 B CN106701063 B CN 106701063B
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
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- 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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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention belongs to organic solid-state field of light emitting materials, in particular to novel structure compound assembles the crystalline, luminescent material to be formed, and emission wavelength is long, can issue strong feux rouges, and wavelength is in 600 ~ 700 nm ranges, and visual strong, interference is small, has a wide range of application.It, which shines, to realize apparent switching effect with environmental stimuli, and crystalline, luminescent, pressure can make its quenching easily, by simply heating or volatile organic solvent is stifling that its luminescence activity can be made to restore rapidly, its luminous intensity and wavelength can restore completely, and can realize reversible, repetition, show the Intelligentized regulating and controllings properties such as repeatable well " light write-in ", " light erasing ".
Description
Technical field
Invention is related to a kind of regulatable novel organic solid-state illuminated switch material, belongs to optics intellectual material research neck
Domain.
Background technique
Organic solid-state luminescent material is widely used in Organic Light Emitting Diode (OLED), and optical electron device, photochemistry pass
Sensor, dyestuff, fluorescent whitening agent, fluorescent paint, laser dye etc. construct grinding for High Efficiency Solid-State luminescent material in recent years
Study carefully and is widely paid close attention to.The regulatable organic solid luminescent material of spectrum is due in photoelectric device and biomarker etc. simultaneously
Field has broad application prospects and is concerned, and is just more and more paid attention to.Because this kind of luminescent material is in chemistry
And/or physical method acts on its lower fluorescence emission wavelengths and can change, and is novel stimuli responsive type intellectual material, in crowd
It is multi-field that there is potential application, such as optical information storage, trademark anti-counterfeit, reversible writing media and microstress sensing etc..However,
The report with the regulatable gathering induced luminescence material of solid state fluorescence is still less at present, the system of especially polynary response, and
There is still a need for further apparent for response mechanism.
Summary of the invention
The present invention provides a kind of red solid compound N3, under ultraviolet light irradiation, can issue very bright feux rouges；It is applied when to it
After adding certain pressure, N3 becomes dark gray solid, does not shine；At this point, after being heated to 175 DEG C to it again (or with methanol, dichloromethane
Alkane, acetone and other organic solvent are stifling), furvous solid reddens rapidly, sends out feux rouges very strong after ultraviolet light irradiation.Therefore, chemical combination
Object N3 has great potential using value in terms of organic solid-state shines and opens the light intellectual material.
The purpose of the present invention is to provide a kind of synthesis simply, has regulatable novel organic solid-state illuminated switch
(SLS) material.The purpose of the present invention is what is be achieved through the following technical solutions:
(1) it by 2- methyl naphtho- [1,2-d] thiazole, is added in reaction flask, temperature is set as 100-140 DEG C, and neighbour two is added
Chlorobenzene, is heated to just complete molten, and 1,3- propane sulfonic acid lactones is added dropwise in aphthothiazoles solution, 8h is reacted, is cooled to
Room temperature, for the beige solid of precipitation after acetone washing, filtering, vacuum drying obtains aphthothiazoles propane sulfonic acid inner salt；
(2) it by aphthothiazoles propane sulfonic acid inner salt, diphenylamino -4- benzaldehyde, is placed in 50mL three-necked bottle, adds anhydrous
Ethyl alcohol, and the catalysis of 1-5 drop piperidines is added dropwise, it is warming up to 60-90 DEG C, flow back 5h, is cooled to room temperature, has red solid precipitation, through washing
After washing, filtering, vacuum drying obtains target product N3.
(3) crystalline product of N3 different shape
It is recrystallized to give from different solvents, red solid is dissolved in mixed solvent methylene chloride/methanol, the two volume
Than difference, obtained crystal habit is different, and luminescent color and intensity also generate notable difference, wherein when the two volume ratio is 1/7,
Obtained crystal is shiny red, and strong light, when volume ratio is 7/1, obtained crystal is kermesinus, is shone weak, volume ratio 1/3
When, monocrystalline can be turned out, is after tested anorthic system, strong light.
(4) the fluorescent emission observation and test method of N3 crystalline, luminescent material
Directly observe in the UV lamp: the N3 crystal being prepared is placed under 365nm ultraviolet lamp, observes strong feux rouges
Transmitting is red fluorescence；
Fluorescence spectrum test: crystal N3 is fixed on quartz plate with vaseline, is surveyed on sepectrophotofluorometer
Examination, excitation wavelength 510nm, emission spectrum scanning are 520~800nm.
(4) the luminous controllable performance test of N3 crystalline, luminescent material
N3 red crystals are taken, grind 5min in Yu Shiying mortar, until being faint in color；Take the powder of part furvous in quartz
On piece is placed in heating furnace, is heated at different temperatures and is observed or test after five minutes；A part of furvous powder is separately taken to be placed in
It observes or tests after fumigating 5min in container full of methanol organic solvent atmosphere.
Red samples 2 after furvous sample 1 and heating after taking the red solid N3 of equivalent, grinding are (or through organic molten
Red samples after agent is smoked), fluorescence spectrum test is carried out to it respectively, observes the variation of fluorescence intensity；And to three kinds of samples into
The experiment of row powder x-ray diffraction, analyzes its diffraction peak intensity situation of change；In addition, observing three kinds by scanning electron microscope
The form and molecular particle size size of sample.
The fluorescence spectrum needs are tested on sepectrophotofluorometer to be obtained, and diffraction peak intensity need to be in X-ray powder
Test obtains on diffractometer, and the form and particle size of sample need to be observed to obtain by scanning electron microscope.
The present invention will be used for the luminous change by environmental stimuli (such as: grinding, heating, organic solvent are smoked) regulating compound
Change, is applied especially to intellectual material.
Detailed description of the invention
Fig. 1 is aphthothiazoles and the synthetic route chart of sulfonate derivatives N3.
Fig. 2 is different shape N3 (left: to play primary state；In: ground sample；Right: >=140 DEG C of heating samples, (a) is in fluorescent lamp
Under photo it is (left: red；In: furvous；It is right: red)；(b) photo under 365nm ultraviolet lamp is (left: to glow；In: no
It shines；It is right: to glow).
Fig. 3 is N3 (left: 1/7 in different proportion methylene chloride/methanol；In: 7/1) polycrystalline and its monocrystalline (right side) being precipitated in
(a) and the photo under 365nm ultraviolet lamp (b) under natural light.
Fig. 4 is the fluorescence spectrum of N3 at various pressures.
Fig. 5 is the fluorescence spectrum of N3 at different temperatures.
Fig. 6 is the fluorescence spectrum of the N3 after different solvents are smoked.
Fig. 7 is the fluorescence intensity change of N3 after ground-solvent is smoked, and photo is shot under 365nm ultraviolet lamp.
Specific embodiment
Following tests and example are for further illustrating but being not limited to the present invention.
Novel organic solid-state illuminated switch material is the compound and synthesis step made of being crystallized as compound N 3 are as follows:
2- methyl naphtho- [1,2-d] thiazole 1.99g (10mmol) is weighed, is added in 100mL three-necked bottle, temperature is set as
130 DEG C, o-dichlorohenzene is added, is heated to just complete molten.It weighs 1,3- propane sulfonic acid lactones 1.22g (10mmol), is added dropwise to
In aphthothiazoles solution, 8h is reacted, is cooled to room temperature, the beige solid of precipitation is dried in vacuo after acetone washing, filtering
To aphthothiazoles propane sulfonic acid inner salt 2.60g.
Aphthothiazoles propane sulfonic acid inner salt 0.32100g (1mmol), diphenylamino -4- benzaldehyde 0.27300g are weighed again
(1mmol) is placed in 50mL three-necked bottle, adds 15mL dehydrated alcohol, and a few drop piperidines catalysis are added dropwise.79 DEG C are warming up to, is returned
Flow 5h.It is cooled to room temperature, has red solid precipitation, after washed, filtering, vacuum drying obtains target product N3.Target chemical combination
Object is aphthothiazoles and sulfonate derivatives N3, structure are as follows:
The structure of the compound N 3 is composed with nuclear magnetic resonance (NMR) and mass spectrum (MS) identification:1H NMR(400MHz,
CDCl3/CD3OD=3:2): δ 8.64 (d, J=8.8Hz, 1H), 8.12-8.18 (m, 2H), 8.04-8.08 (m, 1H), 7.90-
7.97 (m, 2H), 7.80-7.86 (m, 4H), 7.36-7.40 (m, 4H), 7.19-7.25 (m, 6H), 7.03 (d, J=8.8Hz,
2H), 5.46-5.51 (t, J=8Hz, 2H), 3.21-3.24 (t, J=5.6Hz, 2H), 2.73 (m, 2H)13C NMR(100MHz,
CDCl3/CD3OD=3:2): δ 170.80,153.16,150.38,145.94,137.14,134.52,132.73,130.99,
130.11,130.06,128.57,127.30,126.78,126.17,125.92,122.79,121.38,119.83,118.83,
108.53,50.93,47.15,25.48.MS(ESI+)m/z:calcd for C34H29N2O3S2:577.1614(M+),found
577.1870(M+), yield 79%, 95% or more product purity.
The crystalline product of N3 different shape
It is recrystallized to give from different solvents, red solid is dissolved in mixed solvent methylene chloride/methanol, the two volume
Than difference, obtained crystal habit is different, and luminescent color and intensity also generate notable difference, wherein when the two volume ratio is 1/7,
Obtained crystal is shiny red, and strong light, when volume ratio is 7/1, obtained crystal is kermesinus, is shone weak, volume ratio 1/3
When, monocrystalline can be turned out, shiny red is after tested anorthic system, strong light.
The fluorescent emission of N3 crystalline, luminescent material is observed and test method
Directly observe in the UV lamp: the N3 crystal being prepared is placed under 365nm ultraviolet lamp, observes strong feux rouges
Transmitting is red fluorescence；
Fluorescence spectrum test: crystal N3 is fixed on quartz plate with vaseline, is surveyed on sepectrophotofluorometer
Examination, excitation wavelength 510nm, emission spectrum scanning are 520~800nm.
The luminous controllable performance test of N3 crystalline, luminescent material
N3 red crystals are taken, grind 5min in Yu Shiying mortar, until being faint in color；Take the powder of part furvous in quartz
On piece is placed in heating furnace, is heated at different temperatures and is observed or test after five minutes；A part of furvous powder is separately taken to be placed in
It observes or tests after fumigating 5min in container full of methanol organic solvent atmosphere.
Red samples 2 after furvous sample 1 and heating after taking the red solid N3 of equivalent, grinding are (or through organic molten
Red samples after agent is smoked), fluorescence spectrum test is carried out to it respectively, observes the variation of fluorescence intensity；And to three kinds of samples into
The experiment of row powder x-ray diffraction, analyzes its diffraction peak intensity situation of change；In addition, observing three kinds by scanning electron microscope
The form and molecular particle size size of sample.
The luminescent properties difference of different proportion in the mixed solvent crystalline product N3
Red solid N3 is weighed, is dissolved in the methylene chloride/methanol (1/7,7/1, v/v) of different proportion respectively, to
After solvent is evaporated completely, two different colors of polycrystalline will be precipitated.And by solvent evaporation method in methylene chloride/methanol (1/3, v/
V) monocrystalline (Fig. 3) of N3 is turned out in.As it can be seen that recrystallizing only by different solvents, obtained N3 crystal shows different
Color, luminescent color and intensity show notable difference, and crystal obtained in methylene chloride/methanol (1/7) and methylene chloride/
Monocrystalline obtained in methanol (1/3) issues the fluorescence of shiny red, but the crystal color that methylene chloride/methanol (7/1) obtains is dim,
It shines weak.
Solid state N 3 " light erasing " performance of pressure controlling
Red solid N3 is weighed, different pressures are applied to N3 by digital powder compressor, then place it in quartzy fluorescence
Cuvette on piece, it is excitation wavelength that 510nm is arranged on sepectrophotofluorometer.Excitation and transmite slit are adjusted to 5,10nm.?
520~900nm range is scanned, and obtains fluorescence spectrum (Fig. 4) of the N3 under by different pressures.It can be seen that solid chemical compound
N3 issues relatively strong strong fluorescence in 683nm, and to compound pressurized treatments, the fluorescence spectrum of test discovery compound N 3 is with pressure
Power increases the obvious red shift of meeting, and intensity decreases, and when pressure increases to 7MPa, compound fluorescence is quenched completely, and wavelength is red
Move on to 720nm or so.As it can be seen that N3 shows switching effect to pressure, pressurization can make N3 lose luminescence activity completely.
Solid state N 3 " light write-in " performance of temperature regulation
Dark gray N3 sample after claiming grinding, and it is heated, then the sample after heating is placed in quartzy fluorescence cuvette
On piece, it is excitation wavelength that 510nm is arranged on sepectrophotofluorometer.Excitation and transmite slit are adjusted to 5,10nm.520~
900nm range is scanned, and obtains the fluorescence spectrum (Fig. 5) of N3 at different temperatures.The N3 fluorescence quenched in (2) by external pressure
It can be restored by heating.It can be seen from Fig. 5 that the fluorescence intensity of 720nm enhances with heating to compound N 3, and at 125 DEG C, fluorescence
Intensity increases by 6 times, and as temperature continues to rise (>=140 DEG C), N3 fluorescence sharply enhances, and orchid moves on to 680nm, changes colour with compacting
Preceding fluorescence emission wavelengths are close.As it can be seen that heating is easy to that the fluorescence of quenching is made to be restored.
Solid state N 3 " light write-in " performance of volatile solvent regulation
Dark gray N3 sample after weighing grinding, puts it into the small burning full of methanol (methylene chloride, acetone etc.) steam
In cup, become red completely to color sample after one minute, then place it in quartzy fluorescence cuvette on piece, in fluorescence spectrophotometer light
Setting 510nm is excitation wavelength on degree meter.Excitation and transmite slit are adjusted to 5,10nm.It is scanned in 520~900nm range,
Obtain the fluorescence spectrum (Fig. 6) of the N3 after different organic solvents are smoked.
In addition to heat, the fluorescent characteristic that volatile solvent can also be N3 quenching is restored well.In experiment, with first
For alcohol, methylene chloride and acetone, the result that is satisfied with.As long as solid powder is put into volatile organic solvent atmosphere
In, dim solid N3 gradually reddens, and luminescent properties are restored, transformation time length and solvent volatility, atmosphere density
It is related.
Restorability light " On-Off-On " performance of different modes regulation
Pressure-heat, pressurization-solvent is stifling, can realize 3 fluorescence of compound N " On-Off-On " effect easily.
Take appropriate red solid N3 in mortar, be ground to red powder becomes dark gray completely, it is interesting that again by it
It is placed on full of (or being heated to furvous solid) in the closed small beaker of methanol steam, solid color rapidly goes to red.Experiment
It is middle that pressurization (>=2MPa)-heating (>=140 DEG C)-pressurization (>=2MPa)-is heated into (>=140 DEG C) process back and forth, compound
The luminescence activity of N3 there is no variation, still available luminescent properties well (Fig. 7).
The same stifling process of pressurization-solvent is repeatedly reciprocal, also obtains same effect, and pressurization-volatile solvent is fumigated-added
During pressure-volatile solvent is stifling, pressure is >=2MPa (attached drawing 4), volatile solvent refer to that methanol, methylene chloride, acetone etc. are (attached
Fig. 6), it fumigates and refers to sample is placed in the container full of solvent vapour, switch over.Show 3 luminescence process of compound N and right
Environmental stimuli reaction has invertibity.Showing compound under environmental stimuli, molecular structure itself does not change, but point
Accumulation mode between son changes, i.e., this process is physical process rather than chemical change process.
Claims (8)
1. a kind of application of controllable organic solid-state luminescent material on controllable illuminated switch, luminescent condition are ultraviolet or visible
Light, tunable medium be environmental stimuli realize the material it is luminous whether and meanwhile adjust luminous intensity, play answering on illuminated switch
With, which is characterized in that the material belongs to crystalline, luminescent material, and compound is aphthothiazoles and sulfonate derivatives N3, structure
Are as follows:
2. application according to claim 1, which is characterized in that the environmental stimuli includes that pressure, temperature, volatility are molten
Agent is stifling or one of solvent recrystallization or a variety of.
3. application according to claim 2, which is characterized in that the pressure limit is 0-7MPa.
4. application according to claim 2, which is characterized in that the temperature range is 40-170 DEG C.
5. application according to claim 2, which is characterized in that volatile solvent is first during the volatile solvent is stifling
Alcohol or methylene chloride or acetone steam.
6. application according to claim 2, which is characterized in that solvent is methylene chloride and first in the solvent recrystallization
The mixed solvent of alcohol, wherein the volume ratio of methylene chloride and methanol is 1/7-7/1.
7. application according to claim 1, which is characterized in that the environmental stimuli can also add for pressure-heat-
Pressure-heating or pressurization-volatile solvent fumigate the-stifling mode of pressurization-volatile solvent；Wherein pressure-heat-pressurization-adds
To hanker, pressure is >=2MPa, temperature be >=140 DEG C, it switches over；Pressurization-volatile solvent fumigates-pressurization-volatile solvent
In stifling, pressure is >=2MPa, volatile solvent refer to methanol, methylene chloride or acetone, it is stifling refer to for sample to be placed in be full of
In the container of solvent vapour, switch over.
8. application according to claim 1, which is characterized in that the preparation method of aphthothiazoles and sulfonate derivatives N3 is
By 2- methyl naphtho- [1,2-d] thiazole, 1,3- propane sultone and diphenylamino -4- benzaldehyde are that main Material synthesis obtains
It arrives, synthetic method is as follows:
(1) it by 2- methyl naphtho- [1,2-d] thiazole, being added in reaction flask, temperature is set as 100-140 DEG C, o-dichlorohenzene is added,
It is heated to just complete molten, 1,3- propane sultone is added dropwise in aphthothiazoles solution, 8h is reacted, is cooled to room temperature,
For the beige solid of precipitation after acetone washing, filtering, vacuum drying obtains aphthothiazoles propane sulfonic acid inner salt；
(2) it by aphthothiazoles propane sulfonic acid inner salt, diphenylamino -4- benzaldehyde, is placed in 50mL three-necked bottle, adds anhydrous second
Alcohol, and the catalysis of 1-5 drop piperidines is added dropwise, is warming up to 60-90 DEG C, and flow back 5h, is cooled to room temperature, and has a red solid precipitation, washed,
After filtering, vacuum drying obtains target product N3.
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| CN104716268A (en) * | 2013-12-17 | 2015-06-17 | 北京维信诺科技有限公司 | Organic electroluminescence device and preparing method thereof |
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| CN104716268A (en) * | 2013-12-17 | 2015-06-17 | 北京维信诺科技有限公司 | Organic electroluminescence device and preparing method thereof |
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