CN109307566B - Mechanoluminescence device and preparation method thereof - Google Patents
Mechanoluminescence device and preparation method thereof Download PDFInfo
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- CN109307566B CN109307566B CN201811004066.2A CN201811004066A CN109307566B CN 109307566 B CN109307566 B CN 109307566B CN 201811004066 A CN201811004066 A CN 201811004066A CN 109307566 B CN109307566 B CN 109307566B
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- 238000005166 mechanoluminescence Methods 0.000 title claims abstract description 93
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 76
- 238000004806 packaging method and process Methods 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 16
- 239000011521 glass Substances 0.000 claims description 10
- -1 polyethylene terephthalate Polymers 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003292 glue Substances 0.000 claims description 2
- 230000007246 mechanism Effects 0.000 abstract description 8
- 238000011160 research Methods 0.000 abstract description 4
- 238000012546 transfer Methods 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 2
- 239000012965 benzophenone Substances 0.000 abstract description 2
- 230000003111 delayed effect Effects 0.000 abstract description 2
- 238000007725 thermal activation Methods 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 230000035882 stress Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 230000006355 external stress Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005390 triboluminescence Methods 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 230000001939 inductive effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
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Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L1/00—Measuring force or stress, in general
- G01L1/24—Measuring force or stress, in general by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/84—Systems specially adapted for particular applications
- G01N21/88—Investigating the presence of flaws or contamination
Abstract
The invention provides a mechanoluminescence device and a preparation method thereof, wherein the mechanoluminescence device comprises a mechanoluminescence layer made of an organic luminescent material with amorphous mechanoluminescence property, the organic luminescent material adopted by the mechanoluminescence layer comprises Charge Transfer (CT) molecules formed by connecting a benzophenone electron-withdrawing group and an arylamine electron-donating group, and the mechanoluminescence property can be more easily displayed by adjusting the strength of the CT state to adjust the color of mechanoluminescence, thereby being beneficial to the research on the mechanoluminescence mechanism and the widening of the application of the mechanoluminescence mechanism in different environments. In addition, the luminescent material provided by the invention has high luminescent quantum efficiency and typical Thermal Activation Delayed Fluorescence (TADF) property, and can be used for preparing photoelectric devices.
Description
Technical Field
The invention relates to the field of mechanoluminescence materials, in particular to application of a novel organic luminescent material containing diphenylphosphine oxide groups in the field of mechanoluminescence.
Background
Mechanoluminescence (ML) refers to a phenomenon in which a substance is excited by external force (e.g., grinding, rubbing, scratching, cutting, shearing, pulverizing, pressure, etc.), and is also called Triboluminescence (TL). Compared with other types of luminescent materials such as photoluminescence, chemiluminescence, electroluminescence and the like, the mechanoluminescence material has special property of inducing luminescence under the action of external force, has very sensitive optical response to external stress such as pressure, tension, shearing force, impact force and the like, and is widely applied to pressure-sensitive luminophores, forecast monitors, novel light source displays and pressure sensors.
The mechanoluminescence materials can be classified into inorganic mechanoluminescence materials, metal-organic mechanoluminescence materials and pure organic mechanoluminescence materials according to their compositions. The inorganic electroluminescent material has strong luminous brightness and high force response sensitivity, but the noble metal elements participate in the inorganic electroluminescent material to cause the price to be high and the toxicity to be high, and the luminescence of most of the inorganic electroluminescent material is limited in a red area, so that the development of the inorganic electroluminescent material is limited. The metal organic electroluminescent material can further widen the spectral range of electroluminescent, but the introduction of noble metals cannot be avoided all the time, and the cost cannot be reduced. Pure organic electroluminescent materials attract people's attention due to the advantages of simple synthesis, low cost, wide light-emitting range, various kinds, strong modifiability and the like. Pure organic/metal organic electroluminescent molecules are generally considered to have non-centrosymmetric structure and piezoelectric property, and the mechanoluminescence mechanism is not clear yet. Some researchers believe that the mechanism of pure organic/metal organic electroluminescence is that when a material is stimulated by external stress, the material is internally fractured, charges are formed on the fractured surface, the charges are compounded to form excitons, and the excitons are stimulated to emit light through radiation transition. However, almost all mechanoluminescence molecules have mechanoluminescence properties only in a crystalline state, and research and application of the mechanism are limited.
When the molecules are aggregated, the amorphous state is easier to obtain than the crystalline state, and the amorphous state of the luminescent material can be obtained by melting and annealing, so that the material can be attached to objects with various morphologies and can be used for detecting stress breakage. In addition, the aggregation state of the solid molecule tends to be transformed to the amorphous state under the external force stimulation of pressure, shearing force and the like, in the traditional pure organic mechanoluminescence molecule, the mechanoluminescence phenomenon appears when crystals are cracked, and the mechanoluminescence performance disappears when the aggregation state of the solid molecule is continuously transformed to the amorphous state. In contrast, molecules that have the electroluminescent property in the amorphous state retain this property at all times. Therefore, the development of a low T having a mechanoluminescence property in an amorphous stategThe stimuli-responsive organic luminescent material enables the mechanoluminescence property to be more easily expressed, and has important significance for research and introduction development of the mechanoluminescence mechanism.
Disclosure of Invention
The invention aims to provide a mechanoluminescence device which is an organic luminescent material with amorphous mechanoluminescence property, wherein the organic luminescent material contains diphenylphosphine (phosphine oxide) groups, and the intramolecular charge transfer capability can be adjusted by changing different groups, so that the color of the amorphous mechanoluminescence can be regulated and controlled.
Another object of the present invention is a method for the preparation of the above described mechanoluminescence device.
A third object of the present invention is to apply the above described mechanoluminescence device to surface stress breakage detection.
To achieve the above object, the present invention provides a mechanoluminescence device comprising a mechanoluminescence layer made of an organic light-emitting material having an amorphous mechanoluminescence property, the molecular formula of the organic light-emitting material being represented by the general formula (1):
general formula (1):
wherein R is selected from alkyl, halogen, alkoxy, nitro, amino, aldehyde group, cyano, aromatic ring or aromatic heterocyclic substituent.
When R is an aromatic ring or aromatic heterocyclic substituent, the structure is selected from the following structures:
wherein R is1And R2Identical or different, R1、R2Selected from hydrogen, alkyl, halogen, alkoxy, nitro, amino, aldehyde, cyano, phenyl, naphthyl, anthracenyl, carbazolyl, dianilino or phenothiazinyl.
The force-emitting device is a flexible force-emitting device.
The mechanoluminescence device comprises a two-layer structure, wherein a mechanoluminescence layer made of the organic luminescent material is coated on the surface of a base material layer; or the mechanoluminescence device comprises a three-layer structure, wherein the upper layer and the lower layer are respectively packaging layers, the middle layer is the mechanoluminescence layer made of the organic luminescent material, and the upper layer and the lower layer are sealed by ultraviolet curing glue.
The packaging layer is a polyethylene terephthalate film.
The outer layer of the mechanoluminescence device is made of spherical glass as a substrate material layer, and the inner layer of the spherical glass bulb is coated with the mechanoluminescence layer made of the organic luminescent material.
The force-emitting device is applied to surface stress breakage detection.
The preparation method of the force luminescent device is characterized by comprising the following steps: comprises the following steps: adding a proper amount of amorphous powder of the organic luminescent material on a heating table at the temperature of 120-160 ℃, and after the amorphous powder is completely melted, uniformly coating the amorphous powder on the substrate material layer to form a mechanoluminescence layer; or after the materials are completely melted, uniformly coating the packaging layer to form a mechanoluminescence layer, then covering another packaging layer, removing generated bubbles, cooling to room temperature, and packaging the two packaging layers by using ultraviolet curing adhesive.
The organic luminescent material adopted by the mechanoluminescence layer contains Charge Transfer (CT) molecules formed by connecting a benzophenone electron-withdrawing group and an arylamine electron-donating group, and the mechanoluminescence color can be regulated by regulating the intensity of the CT state, so that the mechanoluminescence property is easier to show, and the research on the mechanoluminescence mechanism and the application of the mechanoluminescence mechanism in different environments are facilitated. In addition, the luminescent material provided by the invention has high luminescent quantum efficiency and typical Thermal Activation Delayed Fluorescence (TADF) property, and can be used for preparing photoelectric devices.
To further illustrate the features and technical content of the present invention, please refer to the following drawings related to the present invention, which are for reference and illustration only and are not intended to limit the present invention.
Drawings
The following detailed description of the present invention will be provided in order to more clearly illustrate the technical solution and other advantages of the present invention, with reference to the accompanying drawings.
FIG. 1 is a photoluminescence spectrum of luminescent materials of examples 1 to 5 of the present invention;
FIG. 2 is a schematic structural diagram of a mechanoluminescence device produced from the luminescent materials of examples 1 to 5 of the present invention;
FIG. 3 is a photo-luminescence of a mechanoluminescence device produced from the luminescent materials of examples 1 to 5 of the present invention;
FIG. 4 is a photograph of a mechanoluminescence device produced from the luminescent materials of examples 2 to 5 of the present invention;
fig. 5 is a photograph of the spherical glass coated with the organic light emitting material of example 6 of the present invention for stress damage detection.
Detailed Description
The invention is a mechanoluminescence device comprising a mechanoluminescence layer made of an organic light-emitting material having an amorphous mechanoluminescence property, the molecular general formula of the organic light-emitting material being represented by the general formula (1):
general formula (1):
wherein R is selected from alkyl, halogen, alkoxy, nitro, amino, aldehyde group, cyano, aromatic ring or aromatic heterocyclic substituent.
When R is an aromatic ring or aromatic heterocyclic substituent, the structure is selected from the following structures:
wherein R is1And R2Identical or different, R1、R2Selected from hydrogen, alkyl, halogen, alkoxy, nitro, amino, aldehyde, cyano, phenyl, naphthyl, anthracenyl, carbazolyl, dianilino or phenothiazinyl.
The mechanoluminescence device comprises a two-layer structure, wherein a mechanoluminescence layer made of the organic luminescent material is coated on the surface of a base material layer. Or, the electroluminescent device is a sandwich-type three-layer structure, as shown in fig. 2, wherein the upper and lower layers are respectively encapsulation layers, the middle layer is a electroluminescent layer (ML) made of the organic electroluminescent material, and the upper and lower layers are sealed by ultraviolet curing adhesive. Preferably, the packaging layer is a polyethylene terephthalate film (PET), and the prepared force-emitting device is a flexible force-emitting device.
As shown in fig. 5, the external layer of the mechanoluminescence device is made of spherical glass as a base material layer, and the internal layer of the spherical glass bulb is coated with the mechanoluminescence layer made of the organic luminescent material. During detection, when a certain part of the outer surface of the spherical glass is stressed to cause damage (for example, cracks) to the spherical glass, the mechanoluminescence layer of the inner layer is also stressed to emit light, so that the position of the device subjected to stress damage can be judged, and the damage degree can be judged even through the luminous intensity.
The preparation method of the mechanoluminescence device comprises the following steps: adding a proper amount of amorphous powder of the organic light-emitting material on a heating table at the temperature of 120-160 ℃ (more preferably at the temperature of 120-140 ℃), and after the amorphous powder is completely melted, uniformly coating the amorphous powder on a base material layer; or after the materials are completely melted, uniformly coating the packaging layer, then covering another packaging layer, removing generated bubbles, cooling to room temperature, and packaging the two packaging layers by using ultraviolet curing adhesive.
The present invention will be further illustrated by the following specific examples, but the present invention is not limited to these specific examples.
Example 1
The structure of the organic luminescent material with the amorphous mechanoluminescence property is as follows:
the structure of the mechanoluminescence device is as follows: taking a PET transparent film with the thickness of 0.5mm and the size of 4 multiplied by 4cm as a flexible substrate, adding a proper amount of amorphous powder of the organic luminescent material on a hot table at 140 ℃, spreading and uniformly coating the amorphous powder on the PET substrate after the organic luminescent material is completely melted to form a mechanoluminescence layer, then covering a PET film with the same thickness and size, removing generated bubbles, cooling to room temperature, and packaging the device by using ultraviolet curing adhesive.
Example 2
The structure of the organic luminescent material with the amorphous mechanoluminescence property is as follows:
a mechanoluminescence device was prepared with reference to the device preparation procedure of example 1.
Example 3
The structure of the organic luminescent material with the amorphous mechanoluminescence property is as follows:
a mechanoluminescence device was prepared with reference to the device preparation procedure of example 1.
Example 4
The structure of the organic luminescent material with the amorphous mechanoluminescence property is as follows:
a mechanoluminescence device was prepared with reference to the device preparation procedure of example 1.
Example 5
The structure of the organic luminescent material with the amorphous mechanoluminescence property is as follows:
with reference to the device fabrication procedure of example 1, a mechanoluminescence device was fabricated on a hot stage at 120 ℃.
Example 6
The organic luminescent material with the property of amorphous force luminescence of the embodiment 2 is adopted, a proper amount of amorphous powder of the organic luminescent material is added on a hot table at 140 ℃, after the organic luminescent material is completely melted, the interior of spherical glass of the organic luminescent material is uniformly coated, and the organic luminescent material is cooled to room temperature, such as a picture before stress on the left side of a figure 5, and such as a picture on the right side of the figure 5 when the organic luminescent material is stressed to emit light.
Table 1 examples 1-5 photoluminescent wavelengths, mechanoluminescence wavelengths, glass transition temperatures
Photoluminescence spectra from examples 1-5 were collected with a CCD under excitation with uv light at 365 nm wavelength; the mechanoluminescence spectrum is acquired by scraping and pressing amorphous powder through a CCD, and all experiments are completed at room temperature.
In conclusion, the luminescent material synthesized by the invention has the amorphous force luminescent property, has very sensitive optical response to external stress such as tension, shearing force and the like, and the corresponding flexible force luminescent device has simple preparation method and process, can be repeatedly used and can be applied to a forecast monitor, a stress sensor and the like. As described above, the person skilled in the art can make other various corresponding changes and modifications according to the technical solution and the technical idea of the present invention, and all such changes and modifications should fall within the protection scope of the claims of the present invention.
Claims (8)
1. A mechanoluminescence device comprising a mechanoluminescence layer made of an organic light-emitting material having amorphous mechanoluminescence properties of the formula:
2. the mechanoluminescence device according to claim 1, characterized in that: the force-emitting device is a flexible force-emitting device.
3. The mechanoluminescence device according to claim 1, characterized in that: the mechanoluminescence device comprises a two-layer structure, wherein a mechanoluminescence layer made of the organic luminescent material is coated on the surface of a base material layer; or the mechanoluminescence device comprises a three-layer structure, wherein the upper layer and the lower layer are respectively packaging layers, the middle layer is the mechanoluminescence layer made of the organic luminescent material, and the upper layer and the lower layer are sealed by ultraviolet curing glue.
4. A mechanoluminescence device according to claim 3 characterized in that: the packaging layer is a polyethylene terephthalate film.
5. The mechanoluminescence device according to claim 1, characterized in that: the outer layer of the mechanoluminescence device is made of spherical glass as a substrate material layer, and the inner layer of the spherical glass bulb is coated with the mechanoluminescence layer made of the organic luminescent material.
6. Use of the mechanoluminescence device according to claim 1 or 5 for surface stress failure detection.
7. A method of manufacturing a mechanoluminescence device according to any one of claims 1 to 4, characterized by comprising the steps of: adding a proper amount of amorphous powder of the organic luminescent material on a heating table at the temperature of 120-160 ℃, and after the amorphous powder is completely melted, uniformly coating the amorphous powder on the substrate material layer to form a mechanoluminescence layer; or after the materials are completely melted, uniformly coating the packaging layer to form a mechanoluminescence layer, then covering another packaging layer, removing generated bubbles, cooling to room temperature, and packaging the two packaging layers by using ultraviolet curing adhesive.
8. A method of manufacturing a mechanoluminescence device according to claim 5, characterized by comprising the steps of: adding a proper amount of amorphous powder of the organic luminescent material on a heating table at the temperature of 120-160 ℃, and after the amorphous powder is completely melted, uniformly coating the amorphous powder on the substrate material layer to form the mechanoluminescence layer.
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| CN111442862A (en) * | 2020-04-24 | 2020-07-24 | 中国科学院宁波材料技术与工程研究所 | Stress dynamic monitoring method for aluminum alloy structural member |
| CN111959078A (en) * | 2020-08-05 | 2020-11-20 | 西北工业大学 | Flexible stress response device using flexible organic friction luminescent material and preparation method thereof |
| CN112213815B (en) * | 2020-09-25 | 2022-01-18 | 华南理工大学 | Flexible force-induced luminescent optical fiber, preparation method thereof and large strain sensing application device |
| CN114171704A (en) * | 2021-12-08 | 2022-03-11 | Tcl华星光电技术有限公司 | Flexible display panel and preparation method thereof |
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| CN108101941A (en) * | 2017-12-06 | 2018-06-01 | 深圳市华星光电技术有限公司 | Luminous organic material and its preparation method and application |
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| CN106565781A (en) * | 2016-10-20 | 2017-04-19 | 中山大学 | Phosphine-containing benzophenone organic light-emitting material, synthesis method and applications thereof |
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