CN111303010A - Organic room temperature phosphorescent material containing imide structure, preparation method and application thereof - Google Patents
Organic room temperature phosphorescent material containing imide structure, preparation method and application thereof Download PDFInfo
- Publication number
- CN111303010A CN111303010A CN201911083476.5A CN201911083476A CN111303010A CN 111303010 A CN111303010 A CN 111303010A CN 201911083476 A CN201911083476 A CN 201911083476A CN 111303010 A CN111303010 A CN 111303010A
- Authority
- CN
- China
- Prior art keywords
- room temperature
- phosphorescent material
- material containing
- imide structure
- temperature phosphorescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- 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
-
- 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
- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Indole Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses an organic room temperature phosphorescent material containing an imide structure, a preparation method and application thereof, belonging to the technical field of organic materials1Is H, C1‑C4One of aliphatic alkyl, hydroxyl, amino, nitro, cyano, aldehyde group, carboxyl, halogen, halogenated alkyl or methoxy; r2The organic room temperature phosphorescent material has good electron transmission performance and high fluorescence quantum efficiency, is suitable for preparing a luminescent layer or an electron transmission layer in an organic electroluminescent device, and can be cultured to obtain various single crystals. In addition, the luminescent material of the present invention is also suitable for chemical applications,Biological detection, biological imaging, anti-counterfeiting and other fields.
Description
Technical Field
The invention relates to the technical field of organic materials, in particular to an organic room temperature phosphorescent material containing an imide structure, a preparation method and application thereof.
Background
The organic room temperature phosphorescent material has important application prospects in various aspects, such as biological imaging, sensing, anti-counterfeiting and the like. At present, some reports have been made on organic room temperature phosphorescent materials, however, there is no clear rule on how to design and synthesize organic room temperature phosphorescent materials, which greatly restricts the application of the organic room temperature phosphorescent materials. According to the existing report, the common design strategy is to design the molecule with D-A structure to enhance the intersystem crossing of the molecule, and obtain the organic room temperature phosphorescent material by adopting a crystalline structure, a host-guest structure or a polymer doping mode.
The carbonyl has strong electron-withdrawing ability and strong intersystem crossing ability, and the currently reported material with the D-A structure mainly takes the carbonyl as an electron acceptor. However, this greatly limits the richness of the material design. The imide structure also has strong electronegativity and has important application in the photoelectric field. However, the design of organic room temperature phosphorescent materials based on imide structures has been rarely reported. Although Room Temperature Phosphorescent (RTP) materials have been reported and applied to anti-counterfeiting at present, the reported RTP materials generally have the problems of long synthesis steps, heavy metal content, low preparation efficiency, difficulty in large-scale preparation and the like, and the types of molecules are very few and are mainly concentrated in the halogen group, the noble metal and the like. Therefore, the design, synthesis and efficient preparation of the new RTP molecule have important value.
Disclosure of Invention
The first purpose of the invention is to provide an organic room temperature phosphorescent material containing an imide structure, which realizes high-efficiency chlorine and long service life.
The second purpose of the invention is to provide a preparation method of an organic room temperature phosphorescent material containing an imide structure, which has simple process, high yield and easy purification, and can adjust the luminescence wavelength and the luminescence life of the final product by introducing different functional groups.
The third purpose of the invention is to apply the organic room temperature phosphorescent material containing the imide structure to a luminescent layer and an electron transport layer in an organic electroluminescent device or simultaneously use the organic room temperature phosphorescent material as a luminescent layer material and an electron transport material, thereby simplifying the structure of the organic electroluminescent device.
In order to achieve the purpose, the invention provides the following scheme:
the invention provides an organic room temperature phosphorescent material containing an imide structure, which has a structural formula shown as a formula I:
in the formula I, R1Is H, C1-C4One of aliphatic alkyl, hydroxyl, amino, nitro, cyano, aldehyde group, carboxyl, halogen, halogenated alkyl or methoxy;
R2is a nitrogen heterocyclic electron donor group.
Preferably, C1-C4The fatty alkyl group is
One kind of (1).
Preferably, R2Is one of the following structures:
the invention also provides a preparation method of the organic room temperature phosphorescent material containing the imide structure, which comprises the following steps:
(1) putting 4-bromophthalic anhydride and aniline derivatives into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with boric acid corresponding to a nitrogen-containing heterocyclic electron donor, heating and refluxing in a tetrahydrofuran solution by adopting a Suzuki reaction and using palladium tetratriphenylphosphine as a catalyst, and reacting overnight to obtain a product.
Preferably, the molar ratio of the intermediate to the boric acid corresponding to the nitrogen-containing heterocyclic electron donor in step (2) is 1: 1.2.
Preferably, the reaction temperature in step (2) is 60 ℃.
The invention also provides another preparation method of the organic room temperature phosphorescent material containing the imide structure, which comprises the following steps:
(1) putting 4-bromophthalic anhydride and aniline derivatives into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with a nitrogen-containing heterocycle electron donor, performing C-N coupling Buchwald-Hartwig reaction, heating and refluxing in a toluene solution by using a palladium catalyst, and reacting for 24 hours to obtain a product.
Preferably, the molar ratio of the intermediate to the nitrogen-containing heterocyclic electron donor in step (2) is 1: 1.5.
Preferably, the reaction temperature in step (2) is 110 ℃.
In the above-mentioned production method, the crude product obtained after the completion of the reaction is purified by a method such as recrystallization, column chromatography or sublimation.
The invention also provides application of the organic room temperature phosphorescent material containing the imide structure in chemical/biological detection, biological imaging, preparation or as an anti-counterfeiting material.
The invention also provides a method for applying the organic room temperature phosphorescent material containing the imide structure to a luminescent layer and an electron transport layer in an organic electroluminescent device or simultaneously using the organic room temperature phosphorescent material as a luminescent layer material and an electron transport material so as to simplify the structure of the organic electroluminescent device.
The invention discloses the following technical effects:
the invention prepares a series of imide materials with room temperature phosphorescence characteristics, in the prepared materials, some molecules can obtain a plurality of different single crystal structures, and the single crystal structures can be mutually converted, thereby realizing the adjustment of the fluorescence emission wavelength of the materials and the intensity and the service life of the room temperature phosphorescence. In addition, the material prepared by the invention obtains 8 single crystals through cultivation, and the single crystals are the most in the currently known organic compounds. The fluorescence and room temperature phosphorescence are greatly influenced by conformation by researching different single crystals, and the mechanism of the room temperature phosphorescence is further researched.
The organic room temperature phosphorescent material has good electron transmission performance and high fluorescence quantum efficiency, is suitable for preparing a luminescent layer or an electron transmission layer in an organic electroluminescent device, and can be cultured to obtain various single crystals. In addition, the luminescent material is also suitable for being applied to the fields of chemistry, biological detection, biological imaging, anti-counterfeiting and the like.
The preparation method has simple process and easy purification, and the synthesized material has good luminescence property. In addition, at room temperature, after the ultraviolet lamp is removed, the prepared organic room temperature phosphorescent material containing the imide structure can still continuously emit light, has longer service life, and has potential application in aspects of biological imaging, anti-counterfeiting and the like.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without inventive exercise.
FIG. 1 is a solid absorption spectrum of different single crystals of the product of example 1 according to the invention;
FIG. 2 is a spectrum of different single crystal structures of the product of example 1 of the present invention;
FIG. 3 is a graph of lifetime corresponding to different single crystal structure spectra of the product of example 1 of the present invention;
FIG. 4 is a NMR spectrum of the product of example 1 of the present invention;
FIG. 5 is a NMR spectrum of the product of example 2 of the present invention;
FIG. 6 is a NMR spectrum of the product of example 3 of the present invention;
FIG. 7 is a NMR spectrum of the product of example 4 of the present invention;
FIG. 8 is a NMR spectrum of the product of example 5 of the present invention;
FIG. 9 is a photograph of a cell image of the product of example 2 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments 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 of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in further detail below.
Example 1
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
4-Bromophthalic anhydride (5g,22mmol) was added to a dry three-necked flask, followed by aniline (2.45g,26mmol), 150mL glacial acetic acid was added, heating was continued until the glacial acetic acid refluxed, the reaction was overnight, and the resulting product was poured into water and filtered under suction to give the crude product. Adopting dichloromethane and n-hexane (1:2) as chromatographic solution, and separating with silica gel chromatographic column to remove impurities to obtain intermediate 4.8g with yield of 73%;
adding the obtained intermediate into a three-necked bottle (1.5g,5mmmol), dissolving by using tetrahydrofuran (100mL), introducing nitrogen for half an hour, adding a catalyst of tetratriphenylphosphine palladium, adding a potassium carbonate (1.38g,10mmol) aqueous solution, adding 3-carbazole phenylboronic acid (1.73g,6mmol) after 10 minutes, heating and refluxing overnight, extracting the obtained product by using dichloromethane, drying, then spin-drying the dried extract by using a rotary evaporator, dispersing the obtained crude product in silica gel, using dichloromethane and n-hexane (1:2) as chromatographic liquid, and separating by using a silica gel chromatographic column to obtain 1.5g of the product with the yield of 64%.
Example 2
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
adding 4-bromophthalic anhydride (5g,22mmol) into a dry three-necked bottle, adding aniline (2.45g,26mmol), adding 150mL glacial acetic acid, heating until the glacial acetic acid is refluxed, reacting overnight, pouring the obtained product into water, performing suction filtration to obtain a crude product, separating by using dichloromethane and n-hexane (1:2) as chromatographic liquids, and removing impurities by using a silica gel chromatographic column to obtain an intermediate 4.8g with the yield of 73%;
adding the obtained intermediate into a three-necked bottle (1.5g,5mmmol), dissolving by using toluene (100mL), introducing nitrogen for half an hour, adding potassium carbonate (1.38g,10mmol), adding a toluene solution of palladium acetate and tributylphosphine, finally adding phenoxazine (1.1g,6mmol), reacting for 24 hours, extracting the obtained product by using dichloromethane, drying, then spin-drying the dried extract by using a rotary evaporator, dispersing the obtained crude product in silica gel, using dichloromethane and n-hexane (1:2) as chromatographic liquid, and separating by using a silica gel chromatographic column to obtain 1g of the product with the yield of 50%.
Example 3
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
adding 4-bromophthalic anhydride (5g,22mmol) into a dry three-necked bottle, adding p-trifluoromethylaniline (4.26g,26mmol), adding 150mL glacial acetic acid, heating until the glacial acetic acid is refluxed, reacting overnight, pouring the obtained product into water, performing suction filtration to obtain a crude product, and separating and removing impurities by using a silica gel chromatographic column by using dichloromethane and n-hexane (1:2) as chromatographic liquid to obtain an intermediate 7.17g with the yield of 88%;
the obtained intermediate was put into a three-necked flask (2.0g,5.4mmmol), dissolved with tetrahydrofuran (100mL), then purged with nitrogen for half an hour, added with palladium tetratriphenylphosphine as a catalyst, and added with an aqueous solution of potassium carbonate (1.38g,10mmol), after 10 minutes, added with 3-carbazolphenylboronic acid (2.33g,8.11mmol), heated under reflux overnight, the obtained product was extracted with dichloromethane, dried, then the dried extract was spin-dried with a rotary evaporator, the obtained crude product was dispersed in silica gel, and the product was isolated with dichloromethane and n-hexane (1:2) as a chromatography liquid with silica gel chromatography to obtain 2.3g, 80% yield.
Example 4
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
adding 4-bromophthalic anhydride (5g,22mmol) into a dry three-necked bottle, adding p-trifluoromethylaniline (4.26g,26mmol), adding 150mL glacial acetic acid, heating until the glacial acetic acid is refluxed, reacting overnight, pouring the obtained product into water, performing suction filtration to obtain a crude product, and separating and removing impurities by using a silica gel chromatographic column by using dichloromethane and n-hexane (1:2) as chromatographic liquid to obtain an intermediate 7.17g with the yield of 88%;
the obtained intermediate was put into a three-necked flask (2.0g,5.4mmmol), dissolved with tetrahydrofuran (100mL), then purged with nitrogen for half an hour, added with palladium tetratriphenylphosphine as a catalyst, and added with an aqueous solution of potassium carbonate (1.38g,10mmol), after 10 minutes, added with 3-carbazolphenylboronic acid (2.33g,8.11mmol), heated under reflux overnight, the obtained product was extracted with dichloromethane, dried, then the dried extract was spin-dried with a rotary evaporator, the obtained crude product was dispersed in silica gel, and the product was isolated with dichloromethane and n-hexane (1:2) as a chromatography liquid with silica gel chromatography to obtain 2.47g, 86% yield.
Example 5
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
adding 4-bromophthalic anhydride (5g,22mmol) into a dry three-necked bottle, adding p-bromoaniline (4.55g,26mmol), adding 150mL of glacial acetic acid, heating until the glacial acetic acid is refluxed, reacting overnight, pouring the obtained product into water, performing suction filtration to obtain a crude product, and separating and removing impurities by using a silica gel chromatographic column by using dichloromethane and n-hexane (1:2) as chromatographic liquid to obtain an intermediate 6.88g with the yield of 82%;
adding the obtained intermediate into a three-necked bottle (2g,5.25mmmol), dissolving by using tetrahydrofuran (100mL), introducing nitrogen for half an hour, adding a catalyst of tetratriphenylphosphine palladium, adding a potassium carbonate (1.38g,10mmol) aqueous solution, adding 3-carbazole phenylboronic acid (1.51g,5.25mmol) after 10 minutes, heating and refluxing overnight, extracting the obtained product by using dichloromethane, drying, then spin-drying the dried extract by using a rotary evaporator, dispersing the obtained crude product in silica gel, using dichloromethane and n-hexane (1:2) as chromatographic liquids, and separating by using a silica gel chromatographic column to obtain 2.28g of the product, wherein the yield is 80%, and the purity is more than 99%.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.
Claims (10)
1. An organic room temperature phosphorescent material containing an imide structure is characterized in that: the structural formula is shown as formula I:
in the formula I, R1Is H, C1-C4One of aliphatic alkyl, hydroxyl, amino, nitro, cyano, aldehyde group, carboxyl, halogen, halogenated alkyl or methoxy;
R2is a nitrogen heterocyclic electron donor group.
2. The organic room temperature phosphorescent material containing the imide structure as claimed in claim 1, wherein: c1-C4The fatty alkyl group is
One kind of (1).
3. The organic room temperature phosphorescent material containing the imide structure as claimed in claim 1, wherein: r2Is one of the following structures:
4. a method for preparing an organic room temperature phosphorescent material containing an imide structure as claimed in any one of claims 1 to 3, which comprises the following steps:
(1) putting 4-bromophthalic anhydride and aniline derivatives into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with boric acid corresponding to a nitrogen-containing heterocyclic electron donor, heating and refluxing in a tetrahydrofuran solution by adopting a Suzuki reaction and using palladium tetratriphenylphosphine as a catalyst, and reacting overnight to obtain a product.
5. The method for preparing an organic room temperature phosphorescent material containing an imide structure according to claim 4, wherein the method comprises the following steps: the molar ratio of the intermediate to the boric acid corresponding to the nitrogen-containing heterocyclic electron donor in the step (2) is 1: 1.2.
6. The method for preparing an organic room temperature phosphorescent material containing an imide structure according to claim 4, wherein the method comprises the following steps: the reaction temperature in step (2) was 60 ℃.
7. The method for preparing the organic room temperature phosphorescent material containing the imide structure according to any one of claims 1 to 3, which is characterized by comprising the following steps:
(1) putting 4-bromophthalic anhydride and aniline derivatives into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate;
(2) mixing the intermediate obtained in the step (1) with a nitrogen-containing heterocycle electron donor, performing C-N coupling Buchwald-Hartwig reaction, heating and refluxing in a toluene solution by using a palladium catalyst, and reacting for 24 hours to obtain a product.
8. The method for preparing an organic room temperature phosphorescent material containing an imide structure as claimed in claim 7, wherein the method comprises the following steps: the molar ratio of the intermediate to the nitrogen-containing heterocycle electron donor in the step (2) is 1: 1.5.
9. The method according to claim 7, wherein the method comprises the following steps: the reaction temperature in step (2) was 110 ℃.
10. Use of an organic room temperature phosphorescent material containing an imide structure as claimed in any one of claims 1 to 3 in chemical/biological detection, biological imaging, preparation or as an anti-counterfeiting material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911083476.5A CN111303010B (en) | 2019-11-07 | 2019-11-07 | Organic room-temperature phosphorescent material containing imide structure, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911083476.5A CN111303010B (en) | 2019-11-07 | 2019-11-07 | Organic room-temperature phosphorescent material containing imide structure, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111303010A true CN111303010A (en) | 2020-06-19 |
| CN111303010B CN111303010B (en) | 2023-05-09 |
Family
ID=71158192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911083476.5A Active CN111303010B (en) | 2019-11-07 | 2019-11-07 | Organic room-temperature phosphorescent material containing imide structure, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111303010B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112979527A (en) * | 2021-03-04 | 2021-06-18 | 上海交通大学 | Halogenimide material with long-wavelength room-temperature phosphorescence emission and application |
| CN113045478A (en) * | 2021-03-01 | 2021-06-29 | 常州大学 | Phthalimide organic luminescent material with aggregation-induced luminescence and linear force stimulation-luminescence color change response and application thereof |
| CN113637196A (en) * | 2021-07-12 | 2021-11-12 | 深圳大学 | Room-temperature phosphorescent material based on polyacrylonitrile doping and preparation method and application thereof |
| CN115433118A (en) * | 2022-09-23 | 2022-12-06 | 中科检测技术服务(广州)股份有限公司 | Organic luminescent material containing imide structure and preparation method and application thereof |
| CN115572340A (en) * | 2022-10-25 | 2023-01-06 | 重庆理工大学 | Imide polymer room temperature phosphorescent material with crystallization performance, and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106715644A (en) * | 2014-09-17 | 2017-05-24 | 辛诺拉有限公司 | Organic molecules for use as emitters |
| CN106831745A (en) * | 2016-12-30 | 2017-06-13 | 上海天马有机发光显示技术有限公司 | A kind of electroluminescent organic material and organic photoelectric device |
| CN107936950A (en) * | 2017-11-14 | 2018-04-20 | 华南师范大学 | A kind of luminous organic material and its synthetic method and application that overlength Room Temperature Phosphorescence is caused with power |
| CN109734649A (en) * | 2019-02-19 | 2019-05-10 | 中国科学院化学研究所 | One kind is based on the imido small organic molecule efficient room temperature phosphor material of virtue and its preparation and application |
| KR20190101894A (en) * | 2018-02-23 | 2019-09-02 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| CN110408383A (en) * | 2018-04-28 | 2019-11-05 | 香港科技大学深圳研究院 | With distortion to pure organic room temperature phosphorimetry material and its preparation method and application of-receptor structure |
| CN110437211A (en) * | 2019-07-15 | 2019-11-12 | 南京邮电大学 | A kind of thermal activation delayed fluorescence material and its preparation method and application |
-
2019
- 2019-11-07 CN CN201911083476.5A patent/CN111303010B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106715644A (en) * | 2014-09-17 | 2017-05-24 | 辛诺拉有限公司 | Organic molecules for use as emitters |
| CN106831745A (en) * | 2016-12-30 | 2017-06-13 | 上海天马有机发光显示技术有限公司 | A kind of electroluminescent organic material and organic photoelectric device |
| CN107936950A (en) * | 2017-11-14 | 2018-04-20 | 华南师范大学 | A kind of luminous organic material and its synthetic method and application that overlength Room Temperature Phosphorescence is caused with power |
| KR20190101894A (en) * | 2018-02-23 | 2019-09-02 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| CN110408383A (en) * | 2018-04-28 | 2019-11-05 | 香港科技大学深圳研究院 | With distortion to pure organic room temperature phosphorimetry material and its preparation method and application of-receptor structure |
| CN109734649A (en) * | 2019-02-19 | 2019-05-10 | 中国科学院化学研究所 | One kind is based on the imido small organic molecule efficient room temperature phosphor material of virtue and its preparation and application |
| CN110437211A (en) * | 2019-07-15 | 2019-11-12 | 南京邮电大学 | A kind of thermal activation delayed fluorescence material and its preparation method and application |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113045478A (en) * | 2021-03-01 | 2021-06-29 | 常州大学 | Phthalimide organic luminescent material with aggregation-induced luminescence and linear force stimulation-luminescence color change response and application thereof |
| CN113045478B (en) * | 2021-03-01 | 2022-06-17 | 常州大学 | Phthalimide organic luminescent material with aggregation-induced luminescence and linear force stimulation-luminescence color change response and application thereof |
| CN112979527A (en) * | 2021-03-04 | 2021-06-18 | 上海交通大学 | Halogenimide material with long-wavelength room-temperature phosphorescence emission and application |
| CN112979527B (en) * | 2021-03-04 | 2022-11-08 | 上海交通大学 | Halogenimide material with long-wavelength room-temperature phosphorescence emission and application |
| CN113637196A (en) * | 2021-07-12 | 2021-11-12 | 深圳大学 | Room-temperature phosphorescent material based on polyacrylonitrile doping and preparation method and application thereof |
| CN115433118A (en) * | 2022-09-23 | 2022-12-06 | 中科检测技术服务(广州)股份有限公司 | Organic luminescent material containing imide structure and preparation method and application thereof |
| CN115572340A (en) * | 2022-10-25 | 2023-01-06 | 重庆理工大学 | Imide polymer room temperature phosphorescent material with crystallization performance, and preparation method and application thereof |
| CN115572340B (en) * | 2022-10-25 | 2023-06-13 | 重庆理工大学 | Imide polymer room-temperature phosphorescent material with crystallization performance, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111303010B (en) | 2023-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111303010A (en) | Organic room temperature phosphorescent material containing imide structure, preparation method and application thereof | |
| CN110407710B (en) | Triphenylamine derivative pure organic room temperature phosphorescent material and preparation method thereof | |
| CN113249116B (en) | Fluorescent organic-inorganic silicon oxide liquid crystal material and preparation method thereof | |
| CN112679518B (en) | Pure organic room temperature phosphorescent material based on thiochromanone derivative and preparation method and application thereof | |
| JPH06271519A (en) | Production of 5-aminolevulinic acid | |
| CN114105955A (en) | Fluorospirotriphenylamine derivative compound and preparation method and application thereof | |
| CN113816966A (en) | Guest material of phosphorescent material, phosphorescent material and method for regulating luminescent property of phosphorescent material | |
| CN109734649B (en) | Organic small-molecule efficient room-temperature phosphorescent material based on aromatic imide and preparation and application thereof | |
| CN113896675A (en) | Organic luminescent material based on carbazole-triphenylamine derivative and preparation method thereof | |
| CN114957093A (en) | Organic matter with room temperature phosphorescence and preparation method and application thereof | |
| CN113174253B (en) | Doped luminescent material independent of doping proportion and preparation method and application thereof | |
| CN112979527B (en) | Halogenimide material with long-wavelength room-temperature phosphorescence emission and application | |
| CN114349609A (en) | Synthetic method of hexabenzocoronene dimer | |
| JP7161219B2 (en) | Phosphor and its use | |
| CN113956254A (en) | Organic photoelectric material based on perylene bisimide derivative and preparation method thereof | |
| CN108558595B (en) | P-phenylene ethylene bridged trimer indene derivative and preparation method thereof | |
| CN109608402B (en) | Imidazole derivative ionized compound and preparation method thereof | |
| CN110407718B (en) | Benzoylimide derivative with triphenylamine as donor, and preparation and application thereof | |
| CN111574538A (en) | D-A type near-infrared organic luminescent material and preparation method and application thereof | |
| CN110938017A (en) | Organic molecular material with long afterglow effect based on benzene ring unit and preparation method thereof | |
| CN115057883B (en) | Two-dimensional perovskite white light material and preparation method and application thereof | |
| CN115073457B (en) | Naphthalene bisimine derivative and preparation method and application thereof | |
| CN113880870B (en) | Pyridine fluorine boron fluorescent dye compound and preparation method thereof | |
| CN117069741B (en) | Polymorphic luminescent type thermal activation delayed fluorescent molecule and preparation method and application thereof | |
| CN110105370B (en) | Preparation method of dithieno-benzene diimide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |