CN108586740B - Polyimide containing fluorene or fluorenone structure and preparation method and application thereof - Google Patents
Polyimide containing fluorene or fluorenone structure and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses polyimide containing a fluorene or fluorenone structure, and a preparation method and application thereof. The polyimide material adopts aromatic diamine with a high-planarity structure containing fluorene or fluorenone and various tetracarboxylic acid dianhydrides as raw materials, and is prepared into a powder material or a film of polyimide through thermal imidization or chemical imidization. Because the lowest energy state structure of the diamine monomer has high planarity and stronger rigidity, the prepared polyimide molecular chains are tightly stacked, and the prepared polyimide film has excellent barrier property, higher glass transition temperature, thermal stability and lower thermal expansion coefficient. The synthesis method of the invention has simple and various processes, thus being suitable for industrial production. The polyimide disclosed by the invention can be widely applied to the high and new technology industry fields of microelectronics, military industry, aerospace, high-performance packaging and protection, electronic device packaging and the like.
Description
The application is the patent number 2016100180408, and the application date is: 2016, 1/12, the patent name is a division of polyimide containing fluorene or fluorenone structure and a preparation method and application thereof.
Technical Field
The invention relates to the field of material science, in particular to novel polyimide containing a fluorene or fluorenone structure and a preparation method thereof.
Technical Field
The flexible substrate is used as a supporting and protecting component of the whole flexible device, and the performance of the flexible substrate has important influence on the quality and the service life of the flexible display device. Therefore, great importance is attached to the development of flexible substrates at home and abroad. In summary, the performance of flexible display devices with respect to substrate materialsThe method mainly comprises the following steps: (1) has excellent heat resistance and high-temperature dimensional stability; (2) the flexibility is better; (3) has very excellent barrier property, wherein the LCD device requires that the WVTR value of the material is 10-2～10-1g/m2D, and the requirements for OLED devices are much higher. Generally, the service life of the OLED is more than 10000h, and WVTR and O are2TR values are respectively lower than 10-6g/m2D and 10-5cm3/m2D; (4) lower surface roughness.
According to the research progress of flexible display substrates at home and abroad, materials which can be used as substrates of flexible display devices at present comprise three major types of ultrathin glass, metal foils and polymer films. The polymer film has excellent comprehensive properties such as optical property, mechanical property and chemical property, can be prepared by adopting a roll-to-roll continuous production process, and has low cost, so that the polymer film has been widely regarded as a flexible substrate with wide prospects in recent years. However, the barrier property and high temperature dimensional stability of the flexible display device cannot meet the requirements of the flexible display device on the substrate material, which is a major problem that hinders the rapid development of the flexible display device.
Common polymer substrate materials mainly include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), Polycarbonate (PC), cyclic polyolefin (COC), Polyethersulfone (PES), and the like, but none of them can meet the demanding requirements of OLEDs for substrate materials. Polyimide (PI) is an organic polymer material containing an imide ring in a molecular structure, and the rigid imide ring endows the material with excellent comprehensive properties such as excellent high-temperature resistance, good mechanical properties, excellent chemical stability and the like, so that the PI becomes a preferred material of a flexible display device substrate.
At present, the key to the wide application of the PI flexible substrate is how to further improve the water and oxygen blocking performance of the film while maintaining the inherent thermal stability. Researchers have made composite materials by the main way of improving barrier properties of polyimide, such as introducing lamellar nanoparticles into polyimide, and extending permeation paths of oxygen and water vapor in polyimide to improve barrier properties (for example, patents CN 103589154 a, CN 103602065 a, CN 102532896A, etc.). No research has been made to improve the barrier properties of polyimide from the viewpoint of molecular structure design.
The technology constructs a novel polyimide material by introducing fluorene or fluorenone with planarity into polyimide; and the interaction between polymer molecular chains is enhanced by reducing the side chain structure, introducing polar groups and hydrogen bonds and the like, the molecular chain rigidity and the molecular chain stacking efficiency are improved, and the free volume is reduced, so that a high-performance polyimide material with excellent comprehensive performance and outstanding barrier property is obtained. The research of the system is mainly designed and synthesized on novel high-barrier polyimide containing fluorene or fluorenone structure with high molecular chain rigidity and small free volume, however, no research is carried out on the polyimide at present, so that the research on the design and synthesis of the novel high-barrier polyimide containing fluorene or fluorenone structure is necessary to be carried out.
Disclosure of Invention
The invention aims to provide a novel polyimide containing a fluorene or fluorenone structure.
Another object of the present invention is to provide a method for preparing the polyimide containing a fluorene or fluorenone structure.
The purpose of the invention is realized as follows: a novel polyimide containing fluorene or fluorenone structure has a general structural formula as follows:
wherein: n is 1-10000, and Y is selected from one or more than one of the following structural formulas:
wherein Z is
Ar1Selected from any one of the following structural formulas:
wherein Ar is2、Ar3、Ar4Selected from any one of the following structural formulas:
wherein Ar is5And Ar6Selected from any one of the following structural formulas:
the invention also aims to provide a preparation method of the polyimide containing the fluorene or fluorenone structure, which comprises the following reaction processes: in argon atmosphere, diamine containing a Y structure and dianhydride containing an X structure are dissolved in one or more mixed strong polar aprotic organic solvents of N-methylpyrrolidone, dimethyl sulfoxide, dimethyl sulfone, sulfolane, 1, 4-dioxane, N-dimethylacetamide, N-dimethylformamide, m-cresol and tetrahydrofuran according to a molar ratio of 1 (0.9-1.1), the total mass of the diamine containing the Y structure and the dianhydride containing the X structure accounts for 2-50% of the total mass of reaction materials, the reaction is stirred at minus 10-40 ℃ for 0.5-72 h to obtain homogeneous and viscous polyamic acid glue solution, and the polyamic acid glue solution is dehydrated through thermal imidization or chemical imidization to obtain the polyimide material.
The thermal imidization method comprises the following specific operation steps: and (3) scraping and coating the polyamic acid glue solution on a glass plate, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: and (2) heating the room temperature to 100 ℃, keeping the temperature for 0.8-3 h, heating the temperature from 100 ℃ to 200 ℃, keeping the temperature for 0.8-2 h, heating the temperature from 200 ℃ to 300 ℃, keeping the temperature for 0.8-2 h, heating the temperature from 300 ℃ to 350-500 ℃, keeping the temperature for 0.5-2 h, and cooling to obtain the polyimide film.
The chemical imidization method comprises the following specific operation steps: adding pyridine/acetic anhydride, triethylamine/acetic anhydride or sodium acetate/acetic anhydride as a dehydrating agent into the polyamic acid glue solution, heating and stirring, heating to 60-170 ℃, continuously stirring for 0.5-6 h, cooling to room temperature, pouring into methanol or acetone to obtain polyimide precipitate, filtering and drying to obtain polyimide powder, if a membrane material needs to be prepared, dissolving the polyimide powder in N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), N-dimethylacetamide (DMAc), N-Dimethylformamide (DMF), m-Cresol (m-Cresol) or Tetrahydrofuran (THF), heating to completely dissolve, then scraping the polyimide solution on a glass plate, drying in vacuum at 70-200 ℃ to remove the solvent, and cooling to obtain the polyimide membrane.
The preparation method of the polyimide containing the fluorene or fluorenone structure is simple and various in preparation process and low in condition requirement, so that the preparation method is suitable for industrial production. Because the diamine monomer has high planarity and stronger rigidity, the prepared polyimide has compact molecular chain stacking, thereby having excellent barrier property, higher glass transition temperature and thermal stability and lower thermal expansion coefficient. The polyimide containing fluorene or fluorenone structure can be used in the high and new technology industry fields of microelectronics, military industry, aerospace, high-performance packaging and protection, electronic device packaging and the like.
Drawings
FIG. 1 is an infrared spectrum of the monomer obtained in examples 1 to 5, wherein:
a corresponds to FAPDA/PMDA-PI
b corresponds to FUPDA/PMDA-PI
c corresponds to FPIPDA/PMDA-PI
d corresponding FEC2EPDA/PMDA-PI
e for FEC2APDA/PMDA-PI
From the infrared spectrum, at 1780 and 1710cm-1Around the imine ring is asymmetric and symmetric stretching vibration of carbonyl group, 725cm-1Nearby is bending vibration of carbonyl group on imine ring, 1360cm-1The vicinity is the stretching vibration of the imide ring. 1650cm-1The characteristic absorption peak of amide carbonyl group appears in the vicinity of the absorption peak, and the absorption peak is 1080-800 cm-1The nearby absorption peaks are the deformation vibration absorption peaks of Ar-H, which all show that the polyimides 1 to 5 of the examples have been successfully synthesized.
Detailed Description
The following examples are given to illustrate the invention in more detail, it being noted that the following examples are not to be construed as limiting the scope of the invention, and that those skilled in the art, on the basis of the above disclosure, may make insubstantial modifications and adaptations of the invention while remaining within the scope of the invention.
Example 1
4.3450g (0.01mol) N were added at room temperature2,N7Bis (4-aminophenyl) -9H-fluorone-2, 7-dicarbaxamide (FAPDA) and 43.51g (46.1ml) of N, N-dimethylformamide were charged into a 100ml three-necked flask, argon gas was introduced, the mixture was stirred, after complete dissolution, 2.1812g (0.01mol) of Pyromellitic dianhydrides (Pyromellitic dianhydride, PMDA) were added, and the reaction was continued for 6 hours with stirring to obtain a homogeneous, transparent and viscous polyamic acid paste. And then, coating the polyamic acid solution on a glass plate by scraping, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: heating the room temperature to 100 ℃, keeping the temperature for the whole process 1h → heating the 100 ℃ to 200 ℃, keeping the temperature for the whole process 1h → heating the 200 ℃ to 300 ℃, keeping the temperature for the whole process 1h → heating the 300 ℃ to 420 ℃, keeping the temperature for the whole process 1.5h, and taking out the polyimide film after cooling. The infrared spectrum of the polyimide film is shown in the figure I.
The molecular structural formula of the fully aromatic high-barrier polyimide (FAPDA/PMDA-PI) film in the embodiment is as follows:
example 2
4.78g (0.01mol) of 1,1' - (9-oxo-9H-fluoroene-2, 7-diyl) bis (3- (4-aminophenyl) urea) (FUPDA) and 45.51g (48.8ml) of N, N-dimethylformamide were charged into a 100ml three-necked flask at room temperature, argon gas was introduced, and after complete dissolution, 2.1812g (0.01mol) of Pyromellitic dianhydrides (Pyromellitic dianhydride, PMDA) were added and the reaction was continued for 6 hours with stirring to obtain a homogeneous, transparent and viscous polyamic acid solution. And then, coating the polyamic acid solution on a glass plate by scraping, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: heating the room temperature to 100 ℃, keeping the temperature for the whole process 1h → heating the 100 ℃ to 200 ℃, keeping the temperature for the whole process 1h → heating the 200 ℃ to 300 ℃, keeping the temperature for the whole process 1h → heating the 300 ℃ to 420 ℃, keeping the temperature for the whole process 1.5h, and taking out the polyimide film after cooling. The infrared spectrum of the polyimide film is shown in the figure I.
The molecular structural formula of the fully aromatic high-barrier polyimide (FUPDA/PMDA-PI) film in the embodiment is as follows:
example 3
5.3068g (0.01mol) N were added at room temperature1,N1' - ((9H-fluoroethene-2, 7-diyl) bis (4,1-phenylene)) bis (benzene-1, 4-diamine) (FPIPDA) and 49.92g (52.85ml) of N, N-dimethylformamide were added to a 100ml three-necked flask, and after introducing argon gas and stirring and complete dissolution, 2.1812g (0.01mol) of Pyromellitic dianhydride (Pyromellitic dianhydride, PMDA) was added and the reaction was continued with stirring for 6 hours to obtain a transparent viscous polyamic acid solution. Then the polyamic acid solution is coated on a glass plate by scraping, the glass plate is put in a vacuum oven and vacuumized, and the temperature rise program is that: heating the room temperature to 100 ℃, keeping the temperature for the whole process 1h → heating the 100 ℃ to 200 ℃, keeping the temperature for the whole process 1h → heating the 200 ℃ to 300 ℃, keeping the temperature for the whole process 1h → heating the 300 ℃ to 420 ℃, keeping the temperature for the whole process 1.5h, and taking out the polyimide film after cooling. The infrared spectrum of the polyimide film is shown in the figure I.
The molecular structural formula of the fully aromatic high-barrier polyimide (FPIPDA/PMDA-PI) film in this example is as follows:
example 4
5.2457g (0.01mol) ((9H-fluorone-2, 7-diyl) bis (oxy)) bis (ethane-2,1-diyl) bis (4-aminobenzoate) (FEC) were added at room temperature2EPDA) and 49.51g (52.4ml) of N, N-dimethylformamide are added into a 100ml three-necked flask, argon is introduced, the mixture is stirred and completely dissolved, 2.1812g (0.01mol) of pyromelitic dianhydrides (pyromellitic dianhydride, PMDA) are added, and the stirring reaction is continued for 6 hours, so that a homogeneous, transparent and viscous polyamic acid solution is obtained. And then, coating the polyamic acid solution on a glass plate by scraping, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: heating the room temperature to 100 ℃, keeping the temperature for the whole process 1h → heating the 100 ℃ to 200 ℃, keeping the temperature for the whole process 1h → heating the 200 ℃ to 300 ℃, keeping the temperature for the whole process 1h → heating the 300 ℃ to 420 ℃, keeping the temperature for the whole process 1.5h, and taking out the polyimide film after cooling. The infrared spectrum of the polyimide film is shown in the figure I.
The fully aromatic high-barrier polyimide (FEC) in this example2EPDA/PMDA-PI) film has the following molecular structural formula:
example 5
5.2261g (0.01mol) of N, N' - ((9H-fluoro-2, 7-diyl) bis (oxy)) bis (ethane-2,1-diyl) bis (4-aminobenzamide) (FEC) were added at room temperature2APDA) and 49.38g (52.3ml) of N, N-dimethylformamide were addedAfter the reaction mixture was completely dissolved in 100ml of a three-necked flask through introduction of argon gas, 2.1812g (0.01mol) of Pyromellitic dianhydrides (Pyromellitic dianhydride, PMDA) was added thereto and the reaction was continued for 6 hours under stirring to obtain a homogeneous, transparent and viscous polyamic acid solution. And then, coating the polyamic acid solution on a glass plate by scraping, then placing the glass plate in a vacuum oven, vacuumizing, and heating up: heating the room temperature to 100 ℃, keeping the temperature for the whole process 1h → heating the 100 ℃ to 200 ℃, keeping the temperature for the whole process 1h → heating the 200 ℃ to 300 ℃, keeping the temperature for the whole process 1h → heating the 300 ℃ to 420 ℃, keeping the temperature for the whole process 1.5h, and taking out the polyimide film after cooling. The infrared spectrum of the polyimide film is shown in the figure I.
The fully aromatic high-barrier polyimide (FEC) in this example2APDA/PMDA-PI) film has the following molecular structural formula:
Claims (9)
1. a polyimide material containing fluorene or fluorenone structure has a molecular structure general formula as follows:
wherein: n is 1-10000, and Y is selected from one or more than one of the following structural formulas:
wherein Z is
Or
；Ar4Selected from any one of the following structural formulas:
wherein X is selected from any one of the following structural formulas:
2. the polyimide material containing a fluorene or fluorenone structure according to claim 1, wherein: the polyimide material is prepared into film or powder.
3. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 1, wherein: in argon atmosphere, dissolving diamine containing a Y structure and dianhydride containing an X structure in a molar ratio of 1 (0.9-1.1) in a strong polar aprotic organic solvent, stirring and reacting at-10-40 ℃ for 0.5-72 h to obtain a homogeneous and viscous polyamic acid glue solution, and dehydrating the polyamic acid glue solution to obtain the polyimide material.
4. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 3, wherein: the total mass of diamine containing a Y structure and dianhydride containing an X structure accounts for 2-50% of the total mass of the reaction material.
5. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 3, wherein: the strong polar aprotic organic solvent is one or more of N-methylpyrrolidone, dimethyl sulfoxide, dimethyl sulfone, sulfolane, 1, 4-dioxane, N-dimethylacetamide, N-dimethylformamide, m-cresol and tetrahydrofuran.
6. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 3, wherein: the method for obtaining polyimide by dehydrating the polyamic acid glue solution is thermal imidization or chemical imidization.
7. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 6, wherein: the specific operation of thermal imidization is: firstly, the polyamic acid glue solution is spread on a glass plate by scraping, then the glass plate is placed in a vacuum oven, the vacuum is pumped, and the temperature rise program is as follows: and (2) heating the room temperature to 100 ℃, keeping the temperature for 0.8-3 h, heating the temperature from 100 ℃ to 200 ℃, keeping the temperature for 0.8-2 h, heating the temperature from 200 ℃ to 300 ℃, keeping the temperature for 0.8-2 h, heating the temperature from 300 ℃ to 350-500 ℃, keeping the temperature for 0.5-2 h, and cooling to obtain the polyimide film.
8. The method for preparing a polyimide material containing a fluorene or fluorenone structure according to claim 6, wherein: the specific operation of chemical imidization is as follows: adding pyridine/acetic anhydride, triethylamine/acetic anhydride or sodium acetate/acetic anhydride as a dehydrating agent into the polyamic acid glue solution, heating and stirring, heating to 60-170 ℃, continuously stirring for 0.5-6 h, cooling to room temperature, pouring into methanol or acetone to obtain polyimide precipitate, filtering and drying to obtain polyimide powder, dissolving the polyimide powder in N-methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), N-dimethylacetamide (DMAc), N-Dimethylformamide (DMF), m-Cresol (m-Cresol) or Tetrahydrofuran (THF), heating until the polyimide powder is completely dissolved, scraping the polyimide solution on a glass plate, drying in vacuum at 70-200 ℃ to remove the solvent, and cooling to obtain the polyimide film.
9. The polyimide material containing fluorene or fluorenone structure according to claim 1, wherein the polyimide material is applied to the fields of microelectronics, military industry, aerospace, high-performance packaging and protection, and electronic device packaging.
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| CN111253576A (en) * | 2019-12-15 | 2020-06-09 | 湖南工业大学 | Antibacterial material and preparation method and application thereof |
| CN113150445B (en) * | 2021-04-28 | 2022-06-24 | 江苏南方包装有限公司 | Water-blocking oxygen-blocking polyolefin material and preparation method and application thereof |
| CN113429601B (en) * | 2021-06-21 | 2023-03-31 | 浙江中科玖源新材料有限公司 | Preparation method of high-barrier polyimide film |
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- 2016-01-12 CN CN201610018040.8A patent/CN105440286B/en active Active
- 2016-01-12 CN CN201810328535.XA patent/CN108586740B/en active Active
- 2016-01-12 CN CN201810328534.5A patent/CN108503832A/en active Pending
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|---|---|---|---|---|
| JP2004250577A (en) * | 2003-02-20 | 2004-09-09 | Sumitomo Bakelite Co Ltd | Film-shaped adhesive, leadframe and semiconductor device equipped with film-shaped adhesive |
| JP2006335790A (en) * | 2005-05-31 | 2006-12-14 | Toray Ind Inc | Polyimide resin, heat-resistant resin-laminated film and laminated film with metal layer using the same |
| CN101178519A (en) * | 2006-11-08 | 2008-05-14 | Jsr株式会社 | Liquid crystal aligning agent and liquid crystal display device |
| CN102352039A (en) * | 2011-07-22 | 2012-02-15 | 中山大学 | Soluble functional polyimide based on fluorene structure as well as preparation method and application thereof |
| CN102408342A (en) * | 2011-07-22 | 2012-04-11 | 中山大学 | Fluorine-containing functional diamine monomer with large conjugated structure as well as synthesis method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108586740A (en) | 2018-09-28 |
| CN108503832A (en) | 2018-09-07 |
| CN105440286B (en) | 2018-03-09 |
| CN105440286A (en) | 2016-03-30 |
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