CN111072641A - Orange light thermal activation delayed fluorescence material and synthetic method and application thereof - Google Patents
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Abstract
The invention discloses an orange light thermal activation delayed fluorescence material and a synthesis method and application thereof, belonging to the technical field of organic photoelectric materials and devices. The orange light thermal activation delayed fluorescence material is DV-Cz-DCPP, is a thermal crosslinking TADF molecule, can avoid the use of a metal catalyst in the polymerization process, does not need further purification treatment, and simplifies the synthesis and purification process of a polymer. In the application, the redissolution process of the polymer can be avoided by an in-situ polymerization method, the polymer synthesis and the light-emitting layer film manufacturing process are combined into one, and the device manufacturing process is simplified; and the proportion of the content of the host and the guest can be accurately controlled, which is beneficial to improving the stability and the light-emitting quality of the white light device. The polymer film after the DV-Cz-DCPP is subjected to in-situ crosslinking has the characteristics of good film forming performance, good stability, strong solvent corrosion resistance and the like, is convenient for further spin coating of an electronic transmission material, provides guarantee for an all-wet device, improves the utilization rate of the material, reduces the cost and improves the productivity.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials and devices, and particularly relates to an orange light thermal activation delayed fluorescence material, and a synthesis method and application thereof.
Background
Organic electroluminescent diodes (OLEDs for short) have the advantages of high efficiency, low power consumption, wide viewing angle, flexibility, and capability of realizing large-area display, and become the main development direction of the next generation of solid-state lighting and information display. After decades of efforts of researchers, the luminous efficiency and stability of the OLED have met the requirements of middle and small-sized displays, and the OLED is widely applied to instruments and meters and high-end smart phones, and meanwhile, large-sized curved OLED televisions have already entered the market. The OLED which can meet the commercial application requirements at present is realized based on a multilayer device, the structure is relatively complex, an evaporation preparation process is needed, the production cost is high, and heterojunctions easily exist among functional layers; in comparison, the device which has a simple structure and can be processed by a full wet method can realize large-area display with low cost, and has wider application prospect.
Luminescent materials are a core part in OLEDs. The Thermally Activated Delayed Fluorescence (TADF) material realizes a utilization approach of cheap triplet excitons by using all organic materials on the premise of no metal heavy atoms, thereby realizing the theoretical internal quantum efficiency of 100 percent, creating a premise for the development of low-cost and high-efficiency devices, and simultaneously catering to an innovative era for the development of OLEDs. TADF materials have now been considered as third generation organic electroluminescent materials following the traditional fluorescent and phosphorescent materials. Up to now, a large number of highly efficient evaporation type TADF materials have been successfully developed and exhibit unprecedented advantages. However, there are few TADF materials available for wet processes, and therefore, the development of new wet-process TADF materials is of great research interest for further reducing the production cost of OLED devices.
At present, the TADF polymer material is suitable for processing wet solution OLED devices because of good wet film-forming property and good solvent corrosion resistance. Andrey et al (adv. mater.2015,27,7236-7240) for the first time reported that TADF polymer materials were prepared by metal-catalyzed polymerization of host and guest components, avoiding the influence of phase separation and achieving 100% exciton utilization. Adachi et al (adv. Mater.2016,28, 4019-. Subsequently, many researchers used the synthesis of TADF polymer materials for the preparation of high efficiency wet-process OLED devices.
However, almost all TADF polymers reported at present adopt a metal catalytic system, which makes the purification process difficult, and it is difficult to achieve precise control of the content of the host and the guest in the TADF polymers. Meanwhile, the development of efficient orange TADF is much lagged behind that of blue TADF, and the external quantum efficiency of orange TADF reported at present is far lower than that of blue TADF. In addition, the wet-process device processing process is complicated, a proper solvent is required to be screened to dissolve the polymer, and then a polymer film is obtained by a spin-coating heating annealing mode, so that the research on the all-wet-process OLED device is further limited.
Disclosure of Invention
The technical problem to be solved is as follows: the orange TADF is a thermal cross-linking TADF molecule, can be processed into a film in a hole transport layer through solution, and can be heated and annealed to form a polymer luminescent layer film with excellent film-forming performance and good solution corrosion resistance, so that a wet-process electron transport material can be further spin-coated on the luminescent layer to obtain an OLED device prepared by a full wet process.
The technical scheme is as follows: an orange light thermal activation delayed fluorescence material has a structural formula as follows:
the orange light thermal activation delayed fluorescence material is DV-Cz-DCPP, and the molecular structure analysis result is as follows:
nuclear magnetic hydrogen spectrum (500MHz, CDCl)3)：9.45(d,J＝8.6Hz,2H),8.79(s,2H),8.16(d,J＝8.4Hz,4H),7.61(d,J＝8.2Hz,8H),7.49-7.40(m,8H),7.35(t,J＝7.6Hz,4H),6.71-6.75(m,2H),5.74(d,J＝10.8Hz,2H),5.24-5.28(t,2H),5.18(s,4H)。
Mass spectrum: 874.52.
elemental analysis: c: 82.36, H: 4.38, N: 9.60.
the synthesis method of the orange light thermal activation delayed fluorescence material comprises the following steps:
(1) adding 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile into N, N-dimethylformamide, stirring and dissolving, then respectively adding cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxy carbazole, wherein the molar ratio of the cuprous iodide to the 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile is respectively 0.1, 2 and 2.2, reacting under the protection of nitrogen at the temperature of 140 ℃ for 24 hours, and after the reaction is finished, purifying a crude product by column chromatography to obtain a product A: 5, 6-bis (4- (3-methoxy-9 h-carbazol-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile;
(2) adding the product A obtained in the step (1) into chloroform, stirring and dissolving, and then dropwise adding a boron tribromide solution, wherein the molar ratio of the boron tribromide solution to the product A is 2: 1, the reaction temperature is 0 ℃, the reaction time is 3 hours, the reaction is quenched by methanol solution after the reaction is finished, and the organic solvent is dried by spinning to obtain a product B: 5, 6-bis (4- (3-hydroxy-9 h-carbazol-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile;
(3) adding the product B obtained in the step (2) into dry N, N-dimethylformamide, stirring and dissolving, and then adding a mixture of the product B and the N, N-dimethylformamide in a molar ratio of 3:1 for 20 minutes, adding a mixture of sodium hydride and product B in a molar ratio of 4:1, the reaction temperature is 60 ℃, and the reaction time is 24 hours; after the reaction is finished, purifying by column chromatography to obtain the orange light thermal activation delayed fluorescence material;
the reaction formula is as follows:
the orange light thermal activation delayed fluorescence material is applied to preparing a wet white light organic electroluminescent diode.
Preferably, the application comprises the steps of:
(1) cleaning the anode electrode, and respectively cleaning with distilled water, acetone and isopropanol; drying under a dust-free condition;
(2) spin-coating a hole luminescent layer on the anode at the rotating speed of 2000rpm, and then heating and annealing in a glove box filled with nitrogen after the spin-coating is finished;
(3) the hole transport layer is coated with a mixed material containing the thermal crosslinking main body units and the blue light and orange light thermal activation delayed fluorescence units in different proportions in a spinning mode, the rotating speed is 1500-3000rpm, and after the spinning is finished, thermal crosslinking is carried out in a glove box filled with nitrogen;
(4) and spin-coating an alcohol-soluble electron transport material on the luminescent layer to serve as an electron transport layer, and evaporating a cathode to obtain the wet white organic electroluminescent diode.
Preferably, the annealing temperature in the step (2) is 80-120 ℃.
Preferably, the temperature for thermal crosslinking in the step (3) is 150-.
Preferably, the thermally cross-linked host unit in step (3) is DV-CDBP, which has the following structural formula:
preferably, the blue light heat activation delayed fluorescence material in the step (3) is DV-MOC-DPS, and the structural formula is as follows:
the wet white organic electroluminescent diode is prepared by applying the orange light thermal activation delayed fluorescence material.
Has the advantages that: firstly, the orange TADF is a thermal crosslinking molecule, can avoid the use of metal catalysts in the polymerization process, does not need further purification treatment, and simplifies the synthesis and purification process of polymers. Secondly, the in-situ polymerization method can avoid the redissolution process of the polymer, combine the polymer synthesis process and the light-emitting layer film manufacturing process into a whole, and simplify the device manufacturing process. Thirdly, in the in-situ thermal polymerization process, the proportion of the content of the host and the guest can be accurately controlled, which is beneficial to improving the stability and the light-emitting quality of the white light device. Fourthly, the polymer film after in-situ crosslinking has the characteristics of good film forming performance, good stability, strong solvent corrosion resistance and the like, is convenient for further spin coating of the electronic transmission material, provides guarantee for all-wet devices, improves the utilization rate of the material, reduces the cost and improves the productivity.
Drawings
FIG. 1 is a schematic diagram of a wet-process white light emitting layer prepared by an in-situ polymerization method;
FIG. 2 is a schematic structural diagram of the prepared organic light emitting diode;
the numerical references in the figures represent the following: an ITO anode; 2. a hole transport layer; 3. a light emitting layer; 4. an electron transport layer; 5. a metal cathode.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below with reference to the specific contents of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
The materials used in the present invention are as follows:
wherein the materials DV-MOC-DPS and DV-CDBP were synthesized by the present inventors and published (J.Mater.chem.C., 2016,4,8973-8979), PEDOT: PSS and PO-T2T are commercially available.
Example 1
Preparation of orange TADF:
the structural formula is as follows:
the synthesis method comprises the following steps:
(1) adding 3g of 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile into a 100mL eggplant-shaped bottle dissolved with 30mL of N, N-dimethylformamide, stirring and dissolving, then respectively adding cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxy carbazole, wherein the molar ratio of the cuprous iodide to the 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile is respectively 0.1, 2 and 2.2, reacting under the protection of nitrogen, and the temperature is 140 ℃, and the reaction time is 24 hours. After the reaction is finished, purifying the crude product by a column chromatography method to obtain a product A: 5, 6-bis (4- (3-methoxy-9H-carbazolyl-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile, and an eluent is a mixed solution of petroleum ether and dichloromethane, wherein the yield is 64%.
(2) 1g of the product A obtained in the step (1) was put into a 100mL eggplant-shaped bottle containing 30mL of chloroform and stirred to dissolve the product A, and then the solution was slowly dropped into the bottle at a molar ratio of 2: 1, the reaction temperature is 0 ℃, and the reaction time is 3 hours. After the reaction is finished, quenching is carried out by using a methanol solution, and the organic solvent is dried by spinning to obtain a product B with the yield of 95 percent: 5, 6-bis (4- (3-hydroxy-9H-carbazolyl-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile.
(3) Adding 0.8g of the product B obtained in the step (2) into a 100mL eggplant-shaped bottle in which 30mL of dry N, N-dimethylformamide is dissolved, stirring and dissolving, adding sodium hydride with the molar ratio of 3:1 to the product B, reacting for 20 minutes, adding 4-chloro-methylstyrene with the molar ratio of 4:1 to the product B, reacting at 60 ℃ for 24 hours. After the reaction is finished, the crude product is purified by a column chromatography method to obtain the orange light thermal activation delayed fluorescence material, the eluant is a mixed solution of petroleum ether and dichloromethane, and the yield is 45%.
The reaction formula is as follows:
preparing a wet white OLED device:
the schematic structural diagram of the device is that ITO/PEDOT: PSS (30nm)/DV-CDBP: DV-MOC-DPS:DV-Cz-DCPP(40nm)/PO-T2T(40nm)/Cs2CO3(1nm)/Al (100nm), as shown in FIG. 2. The specific process of device preparation is as follows:
1. cleaning of Indium Tin Oxide (ITO) glass substrates: and ultrasonically cleaning ITO with a detergent, deionized water, ethanol, acetone and isopropanol respectively for 3 times, drying for 1 hour under the irradiation of an infrared lamp, and finally cleaning the ITO with ultraviolet ozone for half an hour for later use.
2. Spin coating of hole transport layer: and spin-coating an anode buffer layer PEDOT on the surface of the ITO at the rotating speed of 3000 rpm: PSS (poly (3, 4-vinyldioxythiophene) -poly (styrenesulfonic acid)) was 40nm in film thickness. The substrate was then dried on a 120 ℃ hot plate for 20 min.
3. Preparation of a light-emitting layer: after cooling to room temperature, 1, 2-dichloroethane containing 10mg/mL of a light-emitting material (DV-CDBP: DV-MOC-DPS: DV-Cz-DCPP in a mass ratio of 1:0.1:0.03, respectively) was spin-coated on a substrate containing PEDOT: PSS above, the rotation speed was 2000rpm, and the time was 30 seconds. Dried at 200 ℃ under nitrogen for 10 minutes and then cooled to room temperature.
4. Spin coating of the electron transport layer: an electron transport layer PO-T2T was spin-coated on the surface of the light-emitting layer at 2000rpm to a thickness of 40nm and a concentration of 5 mg/mL. The substrate was then dried on a 120 ℃ hot plate for 20 min.
5. Evaporation deposition of a cathode: are respectively provided with
And
by evaporation of Cs at a rate of2CO3And Al as a cathode.
And (3) testing the performance of the device: a Kethiey 2400 type semiconductor performance testing system is connected with an ST-86LA type screen brightness meter in a glove box to measure the brightness-current-voltage curve of the device. Meanwhile, a PR655 type spectrometer was used to test the electroluminescence spectra and color coordinates.
The resulting device performance was as follows: the lighting voltage was 4.5V, and the maximum luminance was 5612cd/m2Color seatThe maximum external quantum efficiency, denoted as (0.33,0.38), is 5.6%.
Example 2
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.1:0.02 respectively.
The resulting device performance was as follows: the lighting voltage was 4.1V, and the maximum luminance was 6015cd/m2The maximum external quantum efficiency is 6.5% with color coordinates (0.33, 0.41).
Example 3
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.12:0.03 respectively.
The resulting device performance was as follows: the starting voltage is 4.2V, and the maximum brightness is 8188cd/m2The maximum external quantum efficiency is 8.1% with color coordinates (0.33, 0.35).
Example 4
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.12:0.02 respectively.
The resulting device performance was as follows: the lighting voltage is 4.5V, and the maximum brightness is 7223cd/m2The maximum external quantum efficiency is 4.8% with color coordinates (0.33, 0.39).
The orange light thermal activation delayed fluorescence material provided by the invention and the synthesis method and the application thereof are described in detail above. The polymer film is obtained only by in-situ heating and crosslinking in the manufacturing process of the luminous layer, so that the polymer synthesis and purification process is simplified, and the device manufacturing process is simplified. Meanwhile, the proportion of the content of the host and the guest can be accurately controlled, and the light-emitting quality of the white light device is effectively improved. The invention and embodiments are illustrated herein with reference to specific examples, which are not intended to be limiting of the invention. Any simple modifications to the invention without departing from the principles of the invention are also within the scope of the claims of the invention.
Claims (10)
1. An orange light heat activation delayed fluorescence material is characterized in that the structural formula of the orange light heat activation delayed fluorescence material is as follows:
2. the method for synthesizing the orange light thermal activation delayed fluorescence material according to claim 1, wherein the method comprises the following steps:
(1) adding 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile into N, N-dimethylformamide, stirring and dissolving, then respectively adding cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxy carbazole, wherein the molar ratio of the cuprous iodide to the 5, 6-bis (4-bromophenyl) pyrazine-dicarbonitrile is respectively 0.1, 2 and 2.2, reacting under the protection of nitrogen at the temperature of 140 ℃ for 24 hours, and after the reaction is finished, purifying a crude product by column chromatography to obtain a product A: 5, 6-bis (4- (3-methoxy-9 h-carbazol-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile;
(2) adding the product A obtained in the step (1) into chloroform, stirring and dissolving, and then dropwise adding a boron tribromide solution, wherein the molar ratio of the boron tribromide solution to the product A is 2: 1, the reaction temperature is 0 ℃, the reaction time is 3 hours, the reaction is quenched by methanol solution after the reaction is finished, and the organic solvent is dried by spinning to obtain a product B: 5, 6-bis (4- (3-hydroxy-9 h-carbazol-9-yl) phenyl) pyrazine-2, 3-dicarbonitrile;
(3) adding the product B obtained in the step (2) into dry N, N-dimethylformamide, stirring and dissolving, and then adding a mixture of the product B and the N, N-dimethylformamide in a molar ratio of 3:1 for 20 minutes, adding a mixture of sodium hydride and product B in a molar ratio of 4:1, the reaction temperature is 60 ℃, and the reaction time is 24 hours; after the reaction is finished, purifying by column chromatography to obtain the orange light thermal activation delayed fluorescence material;
the reaction formula of the method is as follows:
3. the method for synthesizing the orange light thermal activation delayed fluorescence material as claimed in claim 2, wherein the eluent of the column chromatography in the step (1) and the step (3) is a mixed solution of petroleum ether and dichloromethane.
4. The application of the orange light thermal activation delayed fluorescence material as claimed in claim 1, wherein the orange light thermal activation delayed fluorescence material is used for preparing a wet white organic electroluminescent diode.
5. The application of the orange light thermal activation delayed fluorescence material as claimed in claim 4, characterized in that the application comprises the following steps:
(1) cleaning the anode electrode, and respectively cleaning with distilled water, acetone and isopropanol; drying under a dust-free condition;
(2) spin-coating a hole luminescent layer on the anode at the rotating speed of 2000rpm, and then heating and annealing in a glove box filled with nitrogen after the spin-coating is finished;
(3) the hole transport layer is coated with a mixed material containing the thermal crosslinking main body units and the blue light and orange light thermal activation delayed fluorescence units in different proportions in a spinning mode, the rotating speed is 1500-3000rpm, and after the spinning is finished, thermal crosslinking is carried out in a glove box filled with nitrogen;
(4) and spin-coating an alcohol-soluble electron transport material on the luminescent layer to serve as an electron transport layer, and evaporating a cathode to obtain the wet white organic electroluminescent diode.
6. The use of an orange-light thermally-activated delayed fluorescence material according to claim 5, wherein the annealing temperature in the step (2) is 80-120 ℃.
7. The use of an orange light thermally activated delayed fluorescence material as claimed in claim 5, wherein the temperature of thermal crosslinking in step (3) is 150-250 ℃.
8. The use of an orange light heat-activated delayed fluorescence material according to claim 5, wherein the thermally cross-linked host unit in step (3) is DV-CDBP, which has the following structural formula:
9. the use of the orange light heat-activated delayed fluorescence material according to claim 5, wherein the blue light heat-activated delayed fluorescence material in the step (3) is DV-MOC-DPS, and the structural formula is as follows:
10. the wet white organic electroluminescent diode manufactured based on the application of the orange light thermal activation delayed fluorescence material according to any one of claims 4 to 9.
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| CN111533679A (en) * | 2020-05-27 | 2020-08-14 | 盐城工学院 | Peripheral thermal-crosslinking branch group, thermal-crosslinking dendritic thermal-activation delayed fluorescent material and synthesis method and application thereof |
| CN111689892A (en) * | 2020-07-20 | 2020-09-22 | 中国科学院苏州纳米技术与纳米仿生研究所南昌研究院 | Luminescent material and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104830320A (en) * | 2015-05-24 | 2015-08-12 | 吉林大学 | Phenanthreneopyrazine derivative luminescent material and application thereof in electroluminescent device |
| US20190074447A1 (en) * | 2015-12-18 | 2019-03-07 | Kunshan Go-Visionox Opto-Electronics Co., Ltd. | Thermally activated delayed fluorescence material and application thereof in organic electroluminescence device |
| CN109503481A (en) * | 2018-12-17 | 2019-03-22 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence compound and preparation method thereof and organic electroluminescent diode apparatus |
| CN109593086A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109599504A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109593082A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109678844A (en) * | 2019-02-02 | 2019-04-26 | 苏州科技大学 | A kind of orange light hot activation delayed fluorescence material and organic electroluminescence device |
-
2019
- 2019-12-31 CN CN201911420357.4A patent/CN111072641B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104830320A (en) * | 2015-05-24 | 2015-08-12 | 吉林大学 | Phenanthreneopyrazine derivative luminescent material and application thereof in electroluminescent device |
| US20190074447A1 (en) * | 2015-12-18 | 2019-03-07 | Kunshan Go-Visionox Opto-Electronics Co., Ltd. | Thermally activated delayed fluorescence material and application thereof in organic electroluminescence device |
| CN109593086A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109599504A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109593082A (en) * | 2017-09-30 | 2019-04-09 | 北京鼎材科技有限公司 | A kind of new compound and the organic electroluminescence device using the compound |
| CN109503481A (en) * | 2018-12-17 | 2019-03-22 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence compound and preparation method thereof and organic electroluminescent diode apparatus |
| CN109678844A (en) * | 2019-02-02 | 2019-04-26 | 苏州科技大学 | A kind of orange light hot activation delayed fluorescence material and organic electroluminescence device |
Non-Patent Citations (1)
| Title |
|---|
| 孙开涌: "湿法热活化延迟荧光材料的设计合成及器件研究", 《东南大学博士学位论文》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533679A (en) * | 2020-05-27 | 2020-08-14 | 盐城工学院 | Peripheral thermal-crosslinking branch group, thermal-crosslinking dendritic thermal-activation delayed fluorescent material and synthesis method and application thereof |
| CN111533679B (en) * | 2020-05-27 | 2022-12-13 | 山西穿越光电科技有限责任公司 | Thermal crosslinking dendritic thermal activation delayed fluorescent material and synthesis and application thereof |
| CN111689892A (en) * | 2020-07-20 | 2020-09-22 | 中国科学院苏州纳米技术与纳米仿生研究所南昌研究院 | Luminescent material and application thereof |
| CN111689892B (en) * | 2020-07-20 | 2022-05-06 | 中国科学院苏州纳米技术与纳米仿生研究所南昌研究院 | Luminescent material and application thereof |
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