CN110669222B - Optically transparent material and preparation method thereof, polymer film and manufacturing method thereof - Google Patents
Optically transparent material and preparation method thereof, polymer film and manufacturing method thereof Download PDFInfo
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Abstract
The invention discloses an optically transparent material, which is modified polyhedral oligomer silsesquioxane, and has silicon atoms and germanium atoms; the silicon atom is connected with an n-alkyl chain, and the germanium atom is connected with an epoxycyclopentane group or a diphenylfluorenone epoxycyclopentane group with different carbon atoms. The invention provides an optical transparent material and a polymer film, which contain silicon and germanium atoms, and side chains of the optical transparent material are modified by epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups containing different carbon atoms to obtain oligomers with different molecular weights and dispersity so as to simultaneously meet the requirements of glass-shaped wear resistance and plastic-shaped flexibility. The preparation method of the optical transparent material and the preparation method of the polymer film are simple and easy to operate, and the preparation efficiency is effectively improved.
Description
Technical Field
The invention relates to the fields of display technology, chemistry and the like, in particular to an optical transparent material and a preparation method thereof, a polymer film and a manufacturing method thereof.
Background
Foldable display devices need to maintain structural integrity under high strains, which requires new optically transparent materials, while at the same time requiring some stiffness and friction resistance. Glass cannot be applied to high performance foldable displays due to its inherent rigidity and brittleness. Currently, one of the most common methods is to combine a protective stiffening layer and a plastic substrate to replace the traditional brittle glass as a cover plate for a foldable display. Such a two-layer composite film should have both glass-like abrasion resistance, plastic modulus and high elastic strain limit, which are critical for its application in flexible sheathing panels, and these properties are in conflict with each other. It is now common to use siloxane polymers as the hardened layer and flexible polyimides as the flexible base material, which can be bent, but the hardness and friction resistance are not satisfactory, and thus it is necessary to develop other kinds of polymers instead of siloxane polymers as the hardened layer.
Disclosure of Invention
In order to solve the technical problems: the invention provides an optical transparent material and a preparation method thereof, a polymer film and a manufacturing method thereof, wherein the optical transparent material contains silicon and germanium atoms, and side chains of the optical transparent material are modified by epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups containing different carbon atoms to obtain oligomers with different molecular weights and dispersity so as to simultaneously meet the requirements of glass-shaped wear resistance and plastic-shaped flexibility.
The technical scheme for solving the problems is as follows: the invention provides an optically transparent material which is a modified polyhedral oligomeric silsesquioxane having silicon atoms and germanium atoms; the silicon atom is connected with an n-alkyl chain, and the germanium atom is connected with an epoxycyclopentane group or a diphenylfluorenone epoxycyclopentane group with different carbon atoms.
In an embodiment of the present invention, the chemical structural formula of the optically transparent material is as follows:
in the chemical structural general formula, R is a normal alkyl chain; r' is an epoxycyclopentane group or a diphenylfluorenylepoxycyclopentane group containing different carbon atoms.
In one embodiment of the present invention, the chemical structure of the cyclopentane epoxide is as follows:
the structural formula of the dibenzo-epoxycyclopentane containing different carbon atoms is one of the following structural formulas:
the wavy line in the chemical structural formula of R 'is a connecting pair site of R' and the germanium atom.
The invention also provides a preparation method for preparing the optical transparent material, which is characterized by comprising the following steps: dissolving a first reactant in tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution; the first reactant is polyhedral oligomer silsesquioxane silanol, wherein a silicon atom in the polyhedral oligomer silsesquioxane silanol is connected with a normal alkyl chain, the second reactant is germanoxane, a germanium atom of the germanoxane is connected with a epoxycyclopentane group or a diphenylfluorene epoxycyclopentane group containing different carbon atoms, and the molar ratio of the first reactant to the second reactant is 1:1-2: 3; dripping triethylamine into the reaction solution to form a white suspension; continuously stirring the mixture for 12 hours to obtain a mixed solution; adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid; removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain the organic polymer, namely the optical transparent material.
In an embodiment of the present invention, the chemical formula of the first reactant is:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
The chemical structural formula of the second reactant is as follows:
in the chemical structural formula of the second reactant, Me is methyl, and R' is epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups containing different carbon atoms.
The invention also provides a polymer film for application to the stiffening layer of the cover plate, the polymer film being made of an optically transparent material as claimed in any one of claims 1 to 3.
In an embodiment of the invention, the cover plate further comprises a flexible substrate, the stiffening layer being provided on the flexible substrate.
The invention also provides a manufacturing method for manufacturing the polymer film, which comprises the following steps:providing said optically transparent material; dissolving the optical transparent material in tetrahydrofuran solution containing a photoinitiator, and shaking or ultrasonically shaking for 45 to 75 minutes to obtain colorless viscous solution; providing a substrate, and uniformly coating the colorless viscous solution on the surface of the substrate; drying at room temperature for 12-24 hr, drying at 40 deg.C under vacuum for 1-3 hr to obtain film, and further drying at light density of 100mW/cm2The total output energy of the ultraviolet light is 3J/cm2Irradiating the film primary product on the surface of the substrate by the ultraviolet lamp to obtain the final polymer film.
In one embodiment of the present invention, the weight percentage of the photoinitiator in the colorless viscous solution is 3 wt%.
The invention has the advantages that: the invention provides an optical transparent material and a polymer film, which contain silicon and germanium atoms, and side chains of the optical transparent material are modified by epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups containing different carbon atoms to obtain oligomers with different molecular weights and dispersity so as to simultaneously meet the requirements of glass-shaped wear resistance and plastic-shaped flexibility. The preparation method of the optical transparent material and the preparation method of the polymer film are simple and easy to operate, and the preparation efficiency is effectively improved.
Drawings
The invention is further explained below with reference to the figures and examples.
FIG. 1 is a block diagram of a cover plate of an embodiment of the present invention.
Reference numerals:
1 covering a plate; 2 a polymer film;
11 a flexible substrate; 12 hardened layer.
Detailed Description
The following description of the embodiments refers to the accompanying drawings for illustrating the specific embodiments in which the invention may be practiced. The directional terms used in the present invention, such as "up", "down", "front", "back", "left", "right", "top", "bottom", etc., refer to the directions of the attached drawings. Accordingly, the directional terms used are used for explanation and understanding of the present invention, and are not used for limiting the present invention.
In one embodiment, the optically transparent material of the present invention is a modified polyhedral oligomeric silsesquioxane having silicon atoms and germanium atoms; the silicon atom is connected with an n-alkyl chain, and the germanium atom is connected with an epoxycyclopentane group or a diphenylfluorenone epoxycyclopentane group with different carbon atoms.
The chemical structural general formula of the optical transparent material is as follows:
in the chemical structural general formula, R is a normal alkyl chain; r' is an epoxycyclopentane group or a diphenylfluorenylepoxycyclopentane group containing different carbon atoms.
Wherein, the chemical structural formula of the cyclopentane epoxide is as follows:
the structural formula of the dibenzo-epoxycyclopentane containing different carbon atoms is one of the following structural formulas:
the wavy line in the chemical structural formula of R 'is a connecting pair site of R' and the germanium atom.
In order to explain the present invention more clearly, the optically transparent material of the present invention will be specifically described below with reference to the preparation method.
Method example 1
The preparation method is used for preparing the optical transparent material and comprises the following steps.
Dissolving a first reactant in 30mL of tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution, wherein the molar ratio of the first reactant to the second reactant is 1:1-2: 3; the first reactant is polyhedral oligomeric silsesquioxane silanol, wherein silicon atoms in the polyhedral oligomeric silsesquioxane silanol are connected with a normal alkyl chain, and in the embodiment, the polyhedral oligomeric silsesquioxane silanol is 1.2 mmol; the second reactant is germanoxane, the germanium atom of which is connected with epoxycyclopentane groups or diphenylfluorenone epoxycyclopentane groups with different carbon atoms, and the germanoxane is 1.2 mmol. Furthermore, the chemical structural formula of the first reactant is as follows:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
The chemical structural formula of the second reactant is as follows:
in the chemical structural formula of the second reactant, Me is a methyl group, and R 'is an epoxycyclopentane group or a diphenylfluoreno epoxycyclopentane group containing different carbon atoms, in this embodiment, the structural formula of R' is selected:
dripping 3.6mmol of triethylamine into the reaction solution to form a white suspension; continuously stirring the mixture for 12 hours to obtain a mixed solution; adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid; removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain the organic polymer, namely the optical transparent material.
Application example 1
As shown in fig. 1, the present invention further provides a polymer film 2 applied to the hardened layer 12 of the cover plate 1, wherein the material of the polymer film 2 is the optically transparent material obtained by the method of example 1. The cover plate 1 further comprises a flexible substrate 11, the stiffening layer 12 being provided on the flexible substrate 11.
In order to explain the present invention more clearly, the polymer film 2 of the present invention will be described in detail below with reference to the manufacturing method.
The manufacturing method of the application embodiment is used for manufacturing the polymer film 2 and comprises the following steps:
providing said optically transparent material; dissolving the optical transparent material in tetrahydrofuran solution containing a photoinitiator, and shaking or ultrasonically shaking for 45 to 75 minutes to obtain colorless viscous solution, wherein the weight percentage of the photoinitiator in the colorless viscous solution is 3 wt%, the weight percentage of the tetrahydrofuran in the colorless viscous solution is 50 wt%, and the balance is the optical transparent material.
Providing a substrate, and uniformly coating the colorless viscous solution on the surface of the substrate; drying at room temperature for 12-24 hr, and further drying at 40 deg.c for 1-3 hr to obtain film product.
Then the optical density is 100mW/cm2The total output energy of the ultraviolet light is 3J/cm2The ultraviolet lamp irradiates the primary thin film on the surface of the substrate to obtain the final polymer thin film 2 which is marked as a first thin film.
Method example 2
The preparation method is used for preparing the optical transparent material and comprises the following steps.
Dissolving a first reactant in 30mL of tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution, wherein the molar ratio of the first reactant to the second reactant is 1:1-2: 3; the first reactant is polyhedral oligomeric silsesquioxane silanol, wherein silicon atoms in the polyhedral oligomeric silsesquioxane silanol are connected with a normal alkyl chain, and in the embodiment, the polyhedral oligomeric silsesquioxane silanol is 1.2 mmol; the second reactant is germanoxane, the germanium atom of which is connected with epoxycyclopentane groups or diphenylfluorenone epoxycyclopentane groups with different carbon atoms, and the germanoxane is 1.2 mmol. Furthermore, the chemical structural formula of the first reactant is as follows:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
The chemical structural formula of the second reactant is as follows:
in the chemical structural formula of the second reactant, Me is a methyl group, and R 'is an epoxycyclopentane group or a diphenylfluoreno epoxycyclopentane group containing different carbon atoms, in this embodiment, the structural formula of R' is selected:
dripping 3.6mmol of triethylamine into the reaction solution to form a white suspension; continuously stirring the mixture for 12 hours to obtain a mixed solution; adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid; and removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain an organic polymer, namely the optically transparent material, which is marked as a second material.
Application example 2
As shown in fig. 1, the present invention further provides a polymer film 2 applied to the hardened layer 12 of the cover plate 1, wherein the material of the polymer film 2 is the optically transparent material obtained by the method of example 2. The cover plate 1 further comprises a flexible substrate 11, the stiffening layer 12 being provided on the flexible substrate 11.
In order to explain the present invention more clearly, the polymer film 2 of the present invention will be described in detail below with reference to the manufacturing method.
The polymer film 2 obtained by the method of manufacturing the present application example in the same manner as described in application example 1 was denoted as a second film.
Method example 3
The preparation method is used for preparing the optical transparent material and comprises the following steps.
Dissolving a first reactant in 30mL of tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution, wherein the molar ratio of the first reactant to the second reactant is 1:1-2: 3; the first reactant is polyhedral oligomeric silsesquioxane silanol, wherein silicon atoms in the polyhedral oligomeric silsesquioxane silanol are connected with a normal alkyl chain, and in the embodiment, the polyhedral oligomeric silsesquioxane silanol is 1.2 mmol; the second reactant is germanoxane, the germanium atom of which is connected with epoxycyclopentane groups or diphenylfluorenone epoxycyclopentane groups with different carbon atoms, and the germanoxane is 1.8 mmol. Furthermore, the chemical structural formula of the first reactant is as follows:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
The chemical structural formula of the second reactant is as follows:
in the chemical structural formula of the second reactant, Me is a methyl group, and R 'is an epoxycyclopentane group or a diphenylfluoreno epoxycyclopentane group containing different carbon atoms, in this embodiment, the structural formula of R' is selected:
dripping 3.6mmol of triethylamine into the reaction solution to form a white suspension; continuously stirring the mixture for 12 hours to obtain a mixed solution; adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid; removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain the organic polymer, namely the optical transparent material.
As shown in fig. 1, the present invention further provides a polymer film 2 applied to the hardened layer 12 of the cover plate 1, wherein the material of the polymer film 2 is the optically transparent material obtained by the method of example 3. The cover plate 1 further comprises a flexible substrate 11, the stiffening layer 12 being provided on the flexible substrate 11.
In order to explain the present invention more clearly, the polymer film 2 of the present invention will be described in detail below with reference to the manufacturing method.
The method of manufacturing the polymer film 2 according to this application example was the same as that described in application example 1, and the obtained film was designated as a third film.
Method example 4
The preparation method is used for preparing the optical transparent material and comprises the following steps.
Dissolving a first reactant in 30mL of tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution, wherein the molar ratio of the first reactant to the second reactant is 1:1-2: 3; the first reactant is polyhedral oligomeric silsesquioxane silanol, wherein silicon atoms in the polyhedral oligomeric silsesquioxane silanol are connected with a normal alkyl chain, and in the embodiment, the polyhedral oligomeric silsesquioxane silanol is 1.2 mmol; the second reactant is germanoxane, the germanium atom of which is connected with epoxycyclopentane groups or diphenylfluorenone epoxycyclopentane groups with different carbon atoms, and the germanoxane is 1.6 mmol. Furthermore, the chemical structural formula of the first reactant is as follows:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
The chemical structural formula of the second reactant is as follows:
in the chemical structural formula of the second reactant, Me is a methyl group, and R 'is an epoxycyclopentane group or a diphenylfluoreno epoxycyclopentane group containing different carbon atoms, in this embodiment, the structural formula of R' is selected:
dripping 3.6mmol of triethylamine into the reaction solution to form a white suspension; continuously stirring the mixture for 12 hours to obtain a mixed solution; adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid; removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain the organic polymer, namely the optical transparent material.
As shown in fig. 1, the present invention further provides a polymer film 2 applied to the hardened layer 12 of the cover plate 1, wherein the material of the polymer film 2 is the optically transparent material obtained by the method of example 4. The cover plate 1 further comprises a flexible substrate 11, the stiffening layer 12 being provided on the flexible substrate 11.
In order to explain the present invention more clearly, the polymer film 2 of the present invention will be described in detail below with reference to the manufacturing method.
The method of manufacturing the polymer film 2 according to this application example was the same as that described in application example 1, and the obtained film was denoted as a fourth film.
The properties of the polymer films 2 obtained in application examples 1 to 4 were measured by performing a surface hardness test and an anti-friction test on the first to fourth films, and the results are shown in table 1 below.
Table 1 shows the surface hardness test and the anti-friction test data of the first to fourth films.
| Sample (I) | Hardness of pencil | Number of times of rub resistance |
| A first film | 7H | 4000 |
| Second film | 9H | 3000 |
| Third film | 7H | 3500 |
| Fourth film | 8H | 3000 |
As can be seen from Table 1, the polymer film 2 obtained by applying the preparation methods of examples 1 to 4 had pencil hardness of 7H to 9H and number of times of anti-rubbing of 3000 or more, and completely satisfied the requirements of glass-like abrasion resistance and plastic-like flexibility.
The present invention is not limited to the above preferred embodiments, and any modifications, equivalent substitutions and improvements made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. An optically transparent material which is a modified polyhedral oligomeric silsesquioxane having silicon atoms and germanium atoms; the silicon atom is connected with an n-alkyl chain, and the germanium atom is connected with an epoxycyclopentane group or a diphenylfluorene epoxycyclopentane group with different carbon atoms;
wherein, the chemical structure general formula of the optical transparent material is as follows:
in the chemical structural general formula, R is a normal alkyl chain; r' is an epoxycyclopentane group or a diphenylfluorenylepoxycyclopentane group containing different carbon atoms.
2. The optically transparent material of claim 1, wherein the chemical structure of the cyclopentane oxide is as follows:
the structural formula of the dibenzo-epoxycyclopentane containing different carbon atoms is one of the following structural formulas:
the wavy line in the chemical structural formula of R 'is a connecting pair site of R' and the germanium atom.
3. A method for producing an optically transparent material according to claim 1, comprising the steps of:
dissolving a first reactant in tetrahydrofuran, and adding a second reactant at room temperature to form a reaction solution;
the first reactant is polyhedral oligomer silsesquioxane silanol, wherein a silicon atom in the polyhedral oligomer silsesquioxane silanol is connected with a normal alkyl chain, the second reactant is germanoxane, and a germanium atom of the germanoxane is connected with epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups with different carbon atoms; the molar ratio of the first reactant to the second reactant is 1:1-2: 3;
dripping triethylamine into the reaction solution to form a white suspension;
continuously stirring the mixture for 12 hours to obtain a mixed solution;
adding distilled water into the mixed solution, and then extracting the mixed solution for multiple times by using normal hexane to obtain an extraction liquid;
removing the organic solvent in the extract liquor by a rotary evaporation method, and then cooling to room temperature to obtain the organic polymer, namely the optical transparent material.
4. The method of claim 3, wherein the first reactant has the chemical formula:
wherein in the chemical structural formula of the first reactant, R is a normal alkyl chain.
5. The method of claim 3, wherein the second reactant has the chemical formula:
in the chemical structural formula of the second reactant, Me is methyl, and R' is epoxycyclopentane groups or diphenylfluorene epoxycyclopentane groups containing different carbon atoms.
6. A polymer film for application to a hardened layer of a cladding sheet, wherein the material used for the polymer film is the optically transparent material of claim 1 or 2.
7. The polymer film of claim 6, wherein the cover plate further comprises a flexible substrate, the stiffening layer being disposed on the flexible substrate.
8. A method of making the polymer film of claim 7, comprising the steps of: providing said optically transparent material;
dissolving the optical transparent material in tetrahydrofuran solution containing a photoinitiator, and shaking or ultrasonically shaking for 45 to 75 minutes to obtain colorless viscous solution;
providing a substrate, and uniformly coating the colorless viscous solution on the surface of the substrate;
drying at room temperature for 12-24 hr, drying at 40 deg.C under vacuum for 1-3 hr to obtain film, and further drying at light density of 100mW/cm2The total output energy of the ultraviolet light is 3J/cm2Irradiating the film primary product on the surface of the substrate by the ultraviolet lamp to obtain the final polymer film.
9. The method of claim 8, wherein the photo-initiator is present in the colorless viscous solution in an amount of 3 wt%.
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| JP2006047504A (en) * | 2004-08-02 | 2006-02-16 | Dainippon Printing Co Ltd | Antireflective stack |
| US8968459B1 (en) * | 2013-12-11 | 2015-03-03 | Nei Corporation | Self-healing superhydrophobic coating composition and method of preparation |
| CN105209945A (en) * | 2013-05-17 | 2015-12-30 | 柯尼卡美能达株式会社 | Polarizing plate and display device provided with same |
| CN106146570A (en) * | 2015-02-11 | 2016-11-23 | 亚当·密茨凯维奇大学 | (dimethyl ethenyl germanium epoxide) substituted silsesquioxane in heptan and synthetic method thereof |
| CN106467706A (en) * | 2016-09-21 | 2017-03-01 | 东莞市联洲知识产权运营管理有限公司 | A kind of preparation method of environmentally friendly organic inorganic hybridization preservative protective film |
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| JP2006047504A (en) * | 2004-08-02 | 2006-02-16 | Dainippon Printing Co Ltd | Antireflective stack |
| CN105209945A (en) * | 2013-05-17 | 2015-12-30 | 柯尼卡美能达株式会社 | Polarizing plate and display device provided with same |
| US8968459B1 (en) * | 2013-12-11 | 2015-03-03 | Nei Corporation | Self-healing superhydrophobic coating composition and method of preparation |
| CN106146570A (en) * | 2015-02-11 | 2016-11-23 | 亚当·密茨凯维奇大学 | (dimethyl ethenyl germanium epoxide) substituted silsesquioxane in heptan and synthetic method thereof |
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