CN104312576A - Piezochromic material, preparation method and applications thereof - Google Patents
Piezochromic material, preparation method and applications thereof Download PDFInfo
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- CN104312576A CN104312576A CN201410441099.9A CN201410441099A CN104312576A CN 104312576 A CN104312576 A CN 104312576A CN 201410441099 A CN201410441099 A CN 201410441099A CN 104312576 A CN104312576 A CN 104312576A
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- 239000000463 material Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims abstract description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 4
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000000605 extraction Methods 0.000 claims abstract description 3
- 230000008014 freezing Effects 0.000 claims abstract description 3
- 238000007710 freezing Methods 0.000 claims abstract description 3
- 238000010992 reflux Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000001228 spectrum Methods 0.000 claims description 9
- 238000001819 mass spectrum Methods 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000005311 nuclear magnetism Effects 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 4
- FRJJJIVFYAEQJM-UHFFFAOYSA-N C(C1=CC=CC=C1)=O.C1=CC=CC=2C3=CC=CC=C3NC12 Chemical compound C(C1=CC=CC=C1)=O.C1=CC=CC=2C3=CC=CC=C3NC12 FRJJJIVFYAEQJM-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 230000003252 repetitive effect Effects 0.000 claims description 2
- 238000005201 scrubbing Methods 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 230000008859 change Effects 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a piezochromic material, a preparation method and applications thereof. The preparation method comprises the following steps: adding 3 grams of carbazole, 3.3 grams of p-bromobenzaldehyde, 3.7 grams of potassium carbonate, 0.33 gram of 18-crown-6, 0.4 gram of cuprous iodide, and 18 mL of o-dichlorobenzene into a round-bottom flask (100 mL); vacuumizing under freezing, introducing nitrogen into the round-bottom flask for three times, stirring at a temperature of 180 DEG C, carrying out reflux for 48 hours; repeatedly washing the reaction system by a hydrochloric acid solution (5%), using dichloromethane to carry out extraction for three times, using waterless magnesium sulfate to dry the product, performing rotary evaporation to remove the solvent, and finally carrying out column chromatography isolation to obtain 3.9 grams of pure product, wherein the yield is 80%.
Description
Technical field
The invention belongs to technical field of chemistry, relate to a kind of piezochromic material its preparation method and application.
Background technology
External stimulus responsiveness material is significantly.Pressure is wherein a kind of important stimulation mode.The difference that material presents different glow colors and light and shade intensity is at various pressures commonly referred to as piezallochromy.Not yet find a kind of High Efficiency Luminescence efficiency that has in prior art, can respond 9.21GPa ambient pressure, have more photochromic and luminous intensity variations, pressure and peak position change present good linear relationship, and reversible loss-free piezochromic material.
Summary of the invention
In order to overcome the defect existed in prior art, the invention provides a kind of piezochromic material its preparation method and application, have studied the aggregation inducing character of material, piezallochromy character.Prepare high efficiency electroluminous device.Its technical scheme is as follows:
A kind of piezochromic material, its molecular formula is:
A preparation method for piezochromic material, comprises the following steps:
The preparation of intermediate a (Carbazole benzaldehyde): by 3g carbazole, 3.3g p-bromobenzaldehyde, 3.7g salt of wormwood 0.33g18-crown-6, the orthodichlorobenzene of 0.4g cuprous iodide and 18ml adds in the round-bottomed flask of 100ml, to vacuumize after logical nitrogen three times at 180 DEG C stirring and refluxing 48 hours under freezing.React the hydrochloric acid soln repetitive scrubbing reaction system of complete use 5%, through dichloromethane extraction three times, revolve desolventizing with after anhydrous magnesium sulfate drying, obtain sterling 3.9g through column chromatography for separation, productive rate is 80%.
The preparation of product C zCNDSB: by the Carbazole benzaldehyde of 813.9mg, 234.3mg adds in the flask of 50ml to benzyl cyanide, add after vacuumizing logical nitrogen three times under the 10ml trimethyl carbinol and the refining tetrahydrofuran solution of 5ml stir and be warming up to 46 DEG C, tetrahydrofuran solution and the 0.2ml TBAH of injecting 0.3mmol potassium tert.-butoxide rapidly reflect 30 minutes.Reacting complete pours in the methyl alcohol of acidifying with acetic acid by system, through column chromatography for separation after suction filtration, and productive rate 68%.
Further preferably, comprehensive sign is carried out to intermediate and final product, comprised hydrogen spectrum nuclear-magnetism, carbon spectrum nuclear-magnetism, mass spectrum, infrared, ultimate analysis, is specially: intermediate product a:1HNMR (500MHz, DMSO) δ 10.15 (s, 1H), 8.29 (d, J=7.7Hz, 2H), 8.22 (d, J=8.4Hz, 2H), 7.93 (d, J=8.3Hz, 2H), 7.54 (d, J=8.2Hz, 2H), 7.51 – 7.45 (m, 2H), 7.36 (d, J=10.9,3.9Hz, 2H). mass spectrum theoretical value 271.31; Measured value: 271.11.
Final product CzCNDSB:1HNMR (500MHz, CDCl3) δ 8.23 (d, J=8.5Hz, 4H), 8.19 (d, J=7.7Hz, 4H), 7.89 (s, 4H), 7.79 (d, J=8.5Hz, 4H), 7.76 (s, 2H), 7.56 (d, J=8.2Hz, 4H), 7.50 – 7.46 (m, 4H), 7.36 (t, J=7.4Hz, 4H); Mass spectrum theoretical value: C48H30N4:662.25, measured value: 662.81; Elemental Analysis theory: C, 86.98%; H, 4.56%; N, 8.45%, measured value: C, 86.91; H, 4.55; N, 8.46.
Piezochromic material of the present invention is preparing the application in organic electroluminescence device process.
Beneficial effect of the present invention: a kind of novel compacting off-color material of design and synthesis of the present invention, has high luminous efficiency.This material can respond 7.90GPa ambient pressure, and luminous peak position from 529 nano movables to 661 nanometers, can have more photochromic and luminous intensity variations.And pressure and peak position change present good linear relationship, reversible loss-free piezochromic material.We have also investigated its aggregation inducing character in addition, this material does not have fluorescence in organic solvent tetrahydrofuran, then shows stronger fluorescent emission in aqueous and in solid film.
Accompanying drawing explanation
Fig. 1 is the synthetic route of the preparation method of piezochromic material of the present invention;
Fig. 2 is the ultra-violet absorption spectrum that the present invention suppresses off-color material;
Fig. 3 is the aggregation inducing character research that the present invention suppresses off-color material;
Fig. 4 is that the present invention suppresses the initial of the powder of off-color material, after grinding, and the fluorescence emission spectrum after heating;
Fig. 5 be the present invention suppress off-color material at situ high pressure fluorescence spectrum, Fig. 5 a is the spectrogram of pressure process; Fig. 5 b is the spectrogram of stress-relief process; Fig. 5 c is emission wavelength and the fluorescence intensity variation relation figure with pressure.
Embodiment
Below in conjunction with the drawings and specific embodiments, technical scheme of the present invention is described in more detail.
With reference to Fig. 1, devise above-mentioned compacting photochromic molecule.We have carried out comprehensive sign to intermediate and final product, comprise hydrogen spectrum nuclear-magnetism, carbon spectrum nuclear-magnetism, and mass spectrum is infrared, ultimate analysis.Prove that we obtain target product.
One: aggregation inducing phenomenon
Can see CzCNDSB by Fig. 2, BC3TEB is at tetrahydrofuran (THF) dilute solution ultra-violet absorption spectrum.Wherein the maximum absorption wavelength of CzCNDSB is at 400nm.The absorbing wavelength of BC3TEB is at 352nm place.
Can see that material does not all have fluorescent emission in tetrahydrofuran solvent by Fig. 3.But when dripping water in its tetrahydrofuran solvent, produce obvious aggregation-induced emission effect.In CzCNDSB when the volume ratio of water is 70%, just can observe obvious fluorescent emission.
Two: compacting metachromatism
By Fig. 4 to see that CzCNDSB powder shows stronger yellow green light and launches, peak position is respectively at 527nm place.When by after with mortar grinder, spectrum generation red shift, emission maximum peak position is at 535nm, and enlarging markedly also appears in peak width at half height.After the peak position after grinding is stifling with methylene dichloride, launches peak position and become 515nm again.After M1 initial powder heats 170 DEG C and keeps 5 minutes, emission maximum peak position gets back to initial 527nm, and Fig. 4 is the initial of powder, after grinding, and the fluorescence emission spectrum after heating.
In order to study the compacting discoloration effect of bi-material better, we adopt situ high pressure technology, carry out situ high pressure fluorometric investigation to it.Along with pressure range increases to 7.90GPa from 0GPa.The emission maximum peak position of CzCNDSB material is the ruddiness of 661nm by the yellow green light red shift of 529nm, and luminous intensity occurs presenting decline trend.Then relief pressure, the emission maximum peak position of spectrum and emissive porwer return to original state again.Fig. 5 a is the change of CzCNDSB fluorescence spectrum in boost process, and 529nm red shift when fluorescence spectrum main peak position is 0GPa from pressure, to 661nm during 7.90GPa, amounts to red shift 132nm.Fig. 5 b is the change of pressure reduction CzCNDSB fluorescence spectrum, and along with pressure reduces gradually, 529nm is returned in spectrum main peak position again blue shift.Fluorescence photo under different pressures is enclosed in the lump.Even more noteworthy, pressure size and the change of maximum peak position present linear relationship, and this illustrative material has and is applied to pressure sensing potential.
The above; be only the present invention's preferably embodiment; protection scope of the present invention is not limited thereto; anyly be familiar with those skilled in the art in the technical scope that the present invention discloses, the simple change of the technical scheme that can obtain apparently or equivalence are replaced and are all fallen within the scope of protection of the present invention.
Claims (4)
1. a piezochromic material, is characterized in that, its molecular formula is:
2. a preparation method for piezochromic material, is characterized in that, comprises the following steps:
Intermediate a: the preparation of Carbazole benzaldehyde: by 3g carbazole, 3.3g p-bromobenzaldehyde, 3.7g salt of wormwood 0.33g18-crown-6, the orthodichlorobenzene of 0.4g cuprous iodide and 18ml adds in the round-bottomed flask of 100ml, to vacuumize after logical nitrogen three times at 180 DEG C stirring and refluxing 48 hours under freezing; React the hydrochloric acid soln repetitive scrubbing reaction system of complete use 5%, through dichloromethane extraction three times, revolve desolventizing with after anhydrous magnesium sulfate drying, obtain sterling 3.9g through column chromatography for separation, productive rate is 80%;
The preparation of product C zCNDSB: by the Carbazole benzaldehyde of 813.9mg, 234.3mg adds in the flask of 50ml to benzyl cyanide, add after vacuumizing logical nitrogen three times under the 10ml trimethyl carbinol and the refining tetrahydrofuran solution of 5ml stir and be warming up to 46 DEG C, tetrahydrofuran solution and the 0.2ml TBAH of injecting 0.3mmol potassium tert.-butoxide rapidly reflect 30 minutes; Reacting complete pours in the methyl alcohol of acidifying with acetic acid by system, through column chromatography for separation after suction filtration, and productive rate 68%.
3. the preparation method of piezochromic material according to claim 2, it is characterized in that, comprehensive sign has been carried out to intermediate and final product, comprise hydrogen spectrum nuclear-magnetism, carbon spectrum nuclear-magnetism, mass spectrum, infrared, ultimate analysis, be specially: intermediate product a:1HNMR (500MHz, DMSO) δ 10.15 (s, 1H), 8.29 (d, J=7.7Hz, 2H), 8.22 (d, J=8.4Hz, 2H), 7.93 (d, J=8.3Hz, 2H), 7.54 (d, J=8.2Hz, 2H), 7.51 – 7.45 (m, 2H), 7.36 (d, J=10.9, 3.9Hz, 2H). mass spectrum theoretical value 271.31, measured value: 271.11,
Final product CzCNDSB:1HNMR (500MHz, CDCl3) δ 8.23 (d, J=8.5Hz, 4H), 8.19 (d, J=7.7Hz, 4H), 7.89 (s, 4H), 7.79 (d, J=8.5Hz, 4H), 7.76 (s, 2H), 7.56 (d, J=8.2Hz, 4H), 7.50 – 7.46 (m, 4H), 7.36 (t, J=7.4Hz, 4H); Mass spectrum theoretical value: C48H30N4:662.25, measured value: 662.81; Elemental Analysis theory: C, 86.98%; H, 4.56%; N, 8.45%, measured value: C, 86.91; H, 4.55; N, 8.46.
4. piezochromic material according to claim 1 is preparing the application in organic electroluminescence device process.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349287A (en) * | 2016-08-29 | 2017-01-25 | 四川大学 | Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound |
| CN106671639A (en) * | 2017-01-25 | 2017-05-17 | 上海先幻新材料科技有限公司 | Secure file containing friction-modulated luminescent compound |
| CN108103582A (en) * | 2017-12-13 | 2018-06-01 | 江南大学 | A kind of low-temp reversible thermochromic crystals material, preparation method and the usage |
| CN108822040A (en) * | 2018-06-08 | 2018-11-16 | 吉林大学 | A kind of organic orange light small molecule, preparation method and its application in electroluminescent device based on phenanthro- imidazoles |
| CN109929536A (en) * | 2019-03-21 | 2019-06-25 | 浙江工业大学 | A kind of static pressure piezochromic material and preparation method thereof |
| CN109970623A (en) * | 2017-12-28 | 2019-07-05 | 武汉尚赛光电科技有限公司 | Derivative of tri-arylamine group and preparation method thereof, application and device |
| CN111087578A (en) * | 2019-12-31 | 2020-05-01 | 湖州师范学院 | Bistable state electrochromism polymer material and preparation method and application thereof |
| CN111560016A (en) * | 2020-05-11 | 2020-08-21 | 郑州铁路职业技术学院 | Method for extracting and separating coptisine from celandine |
| CN114478357A (en) * | 2022-04-15 | 2022-05-13 | 江苏新视界先进功能纤维创新中心有限公司 | Halogen bond-containing piezochromic aggregation-induced emission molecule |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003068462A (en) * | 2001-06-11 | 2003-03-07 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescence element and organic electroluminescence element using the same |
-
2014
- 2014-09-01 CN CN201410441099.9A patent/CN104312576B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003068462A (en) * | 2001-06-11 | 2003-03-07 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescence element and organic electroluminescence element using the same |
Non-Patent Citations (4)
| Title |
|---|
| JIA WENBIN等: "Synthesis and characterization of a novel cyanostilbene derivative and its initiated polymers: aggregation-induced emission enhancement behaviors and light-emitting diode applications", 《POLYMER CHEMISTRY》 * |
| LI YUPENG等: "Supramolecular Network Conducting the Formation of Uniaxially Oriented Molecular Crystal of Cyano Substituted Oligo(p-phenylene vinylene) and Its Amplified Spontaneous Emission (ASE) Behavior", 《CHEMISTRY OF MATERIALS》 * |
| LIU HONGZHANG等: "Study of the influences of molecular planarity and aluminum evaporation rate on the performances of electrical memory devices", 《JOURNAL OF MATERIALS CHEMISTRY C》 * |
| ZHANG YUJIAN等: "Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives", 《DYES AND PIGMENTS》 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349287B (en) * | 2016-08-29 | 2018-12-21 | 四川大学 | Quaternary phosphonium salt class compound with piezallochromy property and its preparation method and application |
| CN106349287A (en) * | 2016-08-29 | 2017-01-25 | 四川大学 | Quaternary phosphonium salts compound with piezochromism property and preparation method and application of quaternary phosphonium salts compound |
| CN106671639A (en) * | 2017-01-25 | 2017-05-17 | 上海先幻新材料科技有限公司 | Secure file containing friction-modulated luminescent compound |
| CN108103582A (en) * | 2017-12-13 | 2018-06-01 | 江南大学 | A kind of low-temp reversible thermochromic crystals material, preparation method and the usage |
| CN109970623B (en) * | 2017-12-28 | 2021-01-12 | 武汉尚赛光电科技有限公司 | Triarylamine derivative, preparation method, application and device thereof |
| CN109970623A (en) * | 2017-12-28 | 2019-07-05 | 武汉尚赛光电科技有限公司 | Derivative of tri-arylamine group and preparation method thereof, application and device |
| CN108822040A (en) * | 2018-06-08 | 2018-11-16 | 吉林大学 | A kind of organic orange light small molecule, preparation method and its application in electroluminescent device based on phenanthro- imidazoles |
| CN108822040B (en) * | 2018-06-08 | 2021-09-14 | 吉林大学 | Organic orange light micromolecule based on phenanthroimidazole, preparation method and application of organic orange light micromolecule in electroluminescent device |
| CN109929536A (en) * | 2019-03-21 | 2019-06-25 | 浙江工业大学 | A kind of static pressure piezochromic material and preparation method thereof |
| CN111087578A (en) * | 2019-12-31 | 2020-05-01 | 湖州师范学院 | Bistable state electrochromism polymer material and preparation method and application thereof |
| CN111087578B (en) * | 2019-12-31 | 2022-04-05 | 湖州师范学院 | Bistable state electrochromism polymer material and preparation method and application thereof |
| CN111560016A (en) * | 2020-05-11 | 2020-08-21 | 郑州铁路职业技术学院 | Method for extracting and separating coptisine from celandine |
| CN114478357A (en) * | 2022-04-15 | 2022-05-13 | 江苏新视界先进功能纤维创新中心有限公司 | Halogen bond-containing piezochromic aggregation-induced emission molecule |
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