CN111303010B - 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
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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 materials, wherein the structural formula of the organic room temperature phosphorescent material containing the imide structure is shown as a formula I, and R is as follows 1 H, C of a shape of H, C 1 ‑C 4 One of fatty alkyl, hydroxy, amino, nitro, cyano, aldehyde, carboxyl, halogen, haloalkyl or methoxy; r is R 2 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 used for culturing a plurality of different 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.
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 prospect in many aspects, such as biological imaging, sensing, anti-counterfeiting and the like. At present, some reports exist on the organic room temperature phosphorescent materials, however, how to design and synthesize the organic room temperature phosphorescent materials has no clear rule, which greatly restricts the application of the organic room temperature phosphorescent materials. According to the prior report, a common design strategy is to enhance intersystem crossing of molecules by designing molecules with a D-A structure, and obtain an organic room temperature phosphorescent material by adopting a crystallization structure, a host-guest structure or a polymer doping mode.
The carbonyl group has strong electron withdrawing capability and strong intersystem crossing capability, and the material with the D-A structure reported at present mainly takes the carbonyl group as an electron acceptor. However, this greatly constrains the richness of the material design. The imide structure also has strong electronegativity and has important application in the field of photoelectricity. However, there are few reports on the design of organic room temperature phosphorescent materials based on imide structures. Although some Room Temperature Phosphorescence (RTP) materials have been reported and applied to anti-counterfeiting, the reported RTP materials generally have the problems of long synthesis steps, heavy metal content, low preparation efficiency, difficulty in mass preparation and the like, and few molecular species are mainly concentrated on halogen groups, noble metals and the like. The design and synthesis of efficient preparation of new RTP molecules has important value.
Disclosure of Invention
The first object of the present invention is to provide an organic room temperature phosphorescent material containing an imide structure which achieves high efficiency chlorine and long lifetime.
The second object of the present invention is to provide a method for preparing an organic room temperature phosphorescent material having an imide structure, which is simple in process, high in yield, easy to purify, and can adjust the light emission wavelength and the light emission lifetime of the final product by introducing different functional groups.
The third object of the present invention is to apply the organic room temperature phosphorescent material containing imide structure to the light emitting layer, the electron transporting layer or to use the organic room temperature phosphorescent material as the light emitting layer material and the electron transporting material in the organic electroluminescent device, thereby simplifying the structure of the organic electroluminescent device.
In order to achieve the above object, the present invention provides the following solutions:
the invention provides an organic room temperature phosphorescent material containing an imide structure, which has a structural formula shown as formula I:
in the formula I, R 1 H, C of a shape of H, C 1 -C 4 One of fatty alkyl, hydroxy, amino, nitro, cyano, aldehyde, carboxyl, halogen, haloalkyl or methoxy;
R 2 is a nitrogen-containing heterocyclic electron donor group.
Preferably C 1 -C 4 Fatty alkyl radicals as
One of them.
Preferably, R 2 Is 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) Adding 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, adopting a Suzuki reaction, using tetraphenylphosphine palladium as a catalyst, heating and refluxing in a tetrahydrofuran solution, and reacting overnight to obtain a product.
Preferably, the molar ratio of the intermediate to 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) Adding 4-bromophthalic anhydride and aniline derivatives into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate;
(2) And (3) mixing the intermediate obtained in the step (1) with a nitrogen-containing heterocyclic electron donor, adopting a C-N coupling Buchwald-Hartwig reaction, using a palladium catalyst, heating and refluxing in a toluene solution, and reacting for 24 hours to obtain a product.
Preferably, the molar ratio of the intermediate to the nitrogen-containing heterocyclic electron donor in the step (2) is 1:1.5.
Preferably, the reaction temperature in step (2) is 110 ℃.
In the above preparation method, the crude product obtained after the reaction is finished is purified by recrystallization, column chromatography, sublimation or the like.
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 the luminescent layer and the electron transport layer in the organic electroluminescent device or simultaneously using the organic room temperature phosphorescent material as the luminescent layer material and the electron transport material, thereby simplifying 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 characteristic, and in the prepared materials, some molecules are found to obtain various different single crystal structures, and the single crystal structures can be mutually converted, so that the adjustment of the fluorescence light-emitting wavelength of the materials, the intensity of room temperature phosphorescence and the service life of the materials is realized. In addition, the material prepared by the invention is cultured to obtain 8 single crystals, and the single crystals are the most variety of the currently known organic compounds. The fluorescence and room temperature phosphorescence are greatly affected by the conformation through researching different single crystals, and the mechanism of 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 used for culturing to obtain various different 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 disclosed by the invention is simple in process and easy to purify, and the synthesized material has good luminous performance. In addition, after the ultraviolet lamp is removed at room temperature, the prepared organic room-temperature phosphorescent material containing the imide structure can still continuously emit light, has long service life, and has the potential of application in the 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 of the prior art, the drawings that are needed in the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph showing solid absorption spectra of different single crystals of the product of example 1 of the present invention;
FIG. 2 is a spectrum of a different single crystal structure of the product of example 1 of the present invention;
FIG. 3 is a graph of lifetime corresponding to spectra of different single crystal structures of the product of example 1 of the present invention;
FIG. 4 is a hydrogen nuclear magnetic resonance spectrum of the product of example 1 of the present invention;
FIG. 5 is a hydrogen nuclear magnetic resonance spectrum of the product of example 2 of the present invention;
FIG. 6 is a hydrogen nuclear magnetic resonance spectrum of the product of example 3 of the present invention;
FIG. 7 is a hydrogen nuclear magnetic resonance spectrum of the product of example 4 of the present invention;
FIG. 8 is a hydrogen nuclear magnetic resonance spectrum of the product of example 5 of the present invention;
FIG. 9 is a cell image of the product of example 2 of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In order that the above-recited objects, features and advantages of the present invention will become more readily apparent, a more particular description of the invention will be rendered by reference to the appended drawings and appended detailed description.
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 (5 g,22 mmol) was added to a dry three-necked flask followed by aniline (2.45 g,26 mmol), 150mL of glacial acetic acid was added, heated to reflux with glacial acetic acid, reacted overnight, and the resulting product was poured into water and suction filtered to give the crude product. Separating and removing impurities by using dichloromethane and n-hexane (1:2) as chromatographic liquid and using a silica gel chromatographic column to obtain 4.8g of intermediate with the yield of 73%;
the obtained intermediate was added to a three-necked flask (1.5 g,5 mmol), dissolved with tetrahydrofuran (100 mL), then purged with nitrogen for half an hour, and then, catalyst, tetrakis triphenylphosphine palladium, and aqueous potassium carbonate (1.38 g,10 mmol) were added, and after 10 minutes, 3-carbazolylphenylboronic acid (1.73 g,6 mmol) was added, and heated under reflux overnight, the obtained product was extracted with methylene chloride, dried, and then the dried extract was dried by spin-drying using a rotary evaporator, and the obtained crude product was dispersed in silica gel, and separated with a silica gel column using methylene chloride and n-hexane (1:2) as a chromatographic liquid to obtain 1.5g of the product in 64% yield.
Example 2
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
4-bromophthalic anhydride (5 g,22 mmol) was added to a dry three-necked flask, then aniline (2.45 g,26 mmol) was added, 150mL of glacial acetic acid was added, the mixture was heated to reflux of glacial acetic acid, the reaction was carried out overnight, the obtained product was poured into water, the crude product was obtained by suction filtration, dichloromethane and n-hexane (1:2) were used as chromatography liquid, and impurities were removed by silica gel chromatography column to obtain 4.8g of intermediate in 73% yield;
the resulting intermediate was added to a three-necked flask (1.5 g,5 mmol), dissolved with toluene (100 mL), then purged with nitrogen for half an hour, then potassium carbonate (1.38 g,10 mmol), then a toluene solution of palladium acetate and tritt-butylphosphine, finally phenoxazine (1.1 g,6 mmol) was added, the reaction was carried out for 24 hours, the resulting product was extracted with methylene chloride, dried, and then the dried extract was dried by spin-drying using a rotary evaporator, and the resulting crude product was dispersed in silica gel, separated with a silica gel column using methylene chloride and n-hexane (1:2) as a chromatographic liquid to give 1g of the product in 50% yield.
Example 3
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
4-bromophthalic anhydride (5 g,22 mmol) was added to a dry three-necked flask, then para-trifluoromethylaniline (4.26 g,26 mmol) was added, 150mL of glacial acetic acid was added, heated to reflux of glacial acetic acid, reacted overnight, then the obtained product was poured into water, suction filtered to obtain a crude product, dichloromethane and n-hexane (1:2) were used as chromatography liquid, and impurities were removed by silica gel chromatography column to obtain intermediate 7.17g, yield 88%;
the resulting intermediate was added to a three-necked flask (2.0 g,5.4 mmol), dissolved with tetrahydrofuran (100 mL), followed by half an hour with nitrogen, and then added with catalyst tetra-triphenylphosphine palladium, and with aqueous potassium carbonate (1.38 g,10 mmol), after 10 minutes 3-carbazoleborophenylacid (2.33 g,8.11 mmol) was added, heated under reflux overnight, the resulting product was extracted with methylene chloride, dried, and then the dried extract was dried by spin-drying in a rotary evaporator, the resulting crude product was dispersed in silica gel, and separated with a silica gel column using methylene chloride and n-hexane (1:2) as a chromatographic liquid to give 2.3g of the product in 80% yield.
Example 4
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
4-bromophthalic anhydride (5 g,22 mmol) was added to a dry three-necked flask, then para-trifluoromethylaniline (4.26 g,26 mmol) was added, 150mL of glacial acetic acid was added, heated to reflux of glacial acetic acid, reacted overnight, then the obtained product was poured into water, suction filtered to obtain a crude product, dichloromethane and n-hexane (1:2) were used as chromatography liquid, and impurities were removed by silica gel chromatography column to obtain intermediate 7.17g, yield 88%;
the resulting intermediate was added to a three-necked flask (2.0 g,5.4 mmol), dissolved with tetrahydrofuran (100 mL), followed by half an hour with nitrogen, and then added with catalyst tetra-triphenylphosphine palladium, and with aqueous potassium carbonate (1.38 g,10 mmol), after 10 minutes 3-carbazoleborophenylacid (2.33 g,8.11 mmol) was added, heated under reflux overnight, the resulting product was extracted with methylene chloride, dried, and then the dried extract was spin-dried using a rotary evaporator, the resulting crude product was dispersed in silica gel, and separated with a silica gel column using methylene chloride and n-hexane (1:2) as chromatography to give 2.47g of the product in 86% yield.
Example 5
The preparation route of the organic room temperature phosphorescent material containing the imide structure in the embodiment is as follows:
4-bromophthalic anhydride (5 g,22 mmol) was added to a dry three-necked flask, then p-bromoaniline (4.55 g,26 mmol) was added, 150mL of glacial acetic acid was added, the mixture was heated to reflux of glacial acetic acid, the reaction was carried out overnight, the obtained product was poured into water, the crude product was obtained by suction filtration, dichloromethane and n-hexane (1:2) were used as chromatography liquids, and impurities were removed by silica gel chromatography column to obtain intermediate 6.88g, yield 82%;
the intermediate obtained was put into a three-necked flask (2 g,5.25 mmol), dissolved with tetrahydrofuran (100 mL), then purged with nitrogen for half an hour, and then, the catalyst, tetrakis triphenylphosphine palladium, and the aqueous solution of potassium carbonate (1.38 g,10 mmol) were added, after 10 minutes, 3-carbazolylphenylboronic acid (1.51 g,5.25 mmol) was added, heated under reflux overnight, the obtained product was extracted with methylene chloride, dried, and then the dried extract was spin-dried with a rotary evaporator, and the obtained crude product was dispersed in silica gel, and separated with a silica gel column using methylene chloride and n-hexane (1:2) as a chromatographic liquid to obtain 2.28g of the product with a yield of 80% and a purity of 99% or more.
The above embodiments are only illustrative of the preferred embodiments of the present invention and are not intended to limit the scope of the present invention, and various modifications and improvements made by those skilled in the art to the technical solutions of the present invention should fall within the protection scope defined by the claims of the present invention without departing from the design spirit of the present invention.
Claims (5)
1. An organic room temperature phosphorescent material containing imide structure, which is characterized in that: the structural formula is shown as formula I:
in the formula I, R 1 Is one of H, halogen and haloalkyl;
R 2 is one of the following structures:
the structural formula of the organic room temperature phosphorescent material containing imide structure is not
2. A method for preparing the imide structure containing organic room temperature phosphorescent material of claim 1, comprising the steps of:
(1) Putting 4-bromophthalic anhydride and an aniline derivative into a reaction bottle, dissolving with glacial acetic acid, and refluxing overnight to obtain an intermediate, wherein the aniline derivative is one of aniline, halogen-substituted aniline and halogenated alkyl-substituted aniline;
(2) Mixing the intermediate obtained in the step (1) with 3-carbazole phenylboronic acid, adopting a Suzuki reaction, using tetraphenylphosphine palladium as a catalyst, heating and refluxing in a tetrahydrofuran solution, and reacting overnight to obtain a product.
3. The method for preparing the organic room temperature phosphorescent material containing an imide structure according to claim 2, wherein the method comprises the following steps: the molar ratio of the intermediate to the 3-carbazole phenylboronic acid in the step (2) is 1:1.2.
4. The method for preparing the organic room temperature phosphorescent material containing an imide structure according to claim 2, wherein the method comprises the following steps: the reaction temperature in step (2) was 60 ℃.
5. The use of an organic room temperature phosphorescent material containing imide structures as claimed in claim 1 in chemical/biological detection, biological imaging, preparation or as a security material.
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| 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 |
| 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 |
| 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 |
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