CN110563946B - Fluorine-containing polyimide, method for producing same, flexible substrate, and display device - Google Patents

Fluorine-containing polyimide, method for producing same, flexible substrate, and display device Download PDF

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CN110563946B
CN110563946B CN201910788570.4A CN201910788570A CN110563946B CN 110563946 B CN110563946 B CN 110563946B CN 201910788570 A CN201910788570 A CN 201910788570A CN 110563946 B CN110563946 B CN 110563946B
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汪亚民
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
    • C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED

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Abstract

The invention discloses a fluorine-containing polyimide and a preparation method thereofA method, a flexible substrate and a display device are provided. The structural formula of the fluorine-containing polyimide is C-B- [ A]n-B-C, wherein a comprises a fluorine-containing dianhydride residue, B comprises a diamine residue, and C comprises a dianhydride residue. The fluorine-containing polyimide of the present invention has a light transmittance of about 85% at most visible light wavelengths.

Description

Fluorine-containing polyimide, method for producing same, flexible substrate, and display device
Technical Field
The present invention relates to polyimide, a method for manufacturing the same, a substrate, and a display device, and more particularly, to fluorine-containing polyimide, a method for manufacturing the same, a flexible substrate, and a display device.
Background
The substrate material of the existing flexible display panel mainly comprises Polyimide (PI). However, polyimide exhibits brown or yellow color, and thus has poor light transmission properties in the visible light band. For example, the transmittance for visible light of about 500nm is less than 40%, and the transmittance for visible light of about 400nm is close to 0%. Thus, there is still a need for improvement of the existing polyimides.
Therefore, it is necessary to provide a fluorine-containing polyimide, a method for manufacturing the same, a flexible substrate, and a display device, which solve the problems of the prior art.
Disclosure of Invention
In view of the above, the present invention provides a fluorine-containing polyimide, a method for manufacturing the same, a flexible substrate, and a display device, so as to solve the problem of poor light transmittance of the conventional polyimide.
It is an object of the present invention to provide a fluorine-containing polyimide having a light transmittance of about 85% at most of visible light wavelengths.
Another object of the present invention is to provide a method for producing a fluorine-containing polyimide, which comprises providing a specific compound to perform a specific reaction to form the fluorine-containing polyimide.
It is still another object of the present invention to provide a flexible substrate, wherein the material of the flexible substrate comprises the fluorine-containing polyimide according to any one of the embodiments of the present invention, so that the light transmittance of the flexible substrate can reach about 85% in most visible light wavelengths.
It is another object of the present invention to provide a display device including the flexible substrate according to any one of the embodiments of the present invention, so that the flexible substrate of the display device has sufficient light transmittance.
To achieve the above objects, one embodiment of the present invention provides a fluorine-containing polymerImide, wherein the structural formula of the fluorine-containing polyimide is C-B- [ A-B [ ]]n-C, wherein a comprises a fluorine-containing dianhydride residue, B comprises a diamine residue, and C comprises a monofunctional anhydride residue.
In one embodiment of the present invention, a has the following structural formula:
Figure GDA0002743052820000021
in one embodiment of the present invention, the structural formula of B is as follows:
Figure GDA0002743052820000022
in one embodiment of the present invention, C has the following structural formula:
Figure GDA0002743052820000023
another embodiment of the present invention provides a method for producing a fluorine-containing polyimide, including: the method for producing a fluorine-containing polyimide comprises the steps of: providing fluorine-containing diacids, diamines and monoacids; mixing said fluorine-containing diacid anhydride, said diamine, and said mono-anhydride to form a semi-finished product; and carrying out a cross-linking curing step on the semi-finished product to form fluorine-containing polyimide, wherein the structural formula of the fluorine-containing polyimide is C-B- [ A-B ]]n-C, wherein a comprises a fluorine-containing dianhydride residue, B comprises a diamine residue and C comprises a monofunctional anhydride residue.
In one embodiment of the invention, the fluorine-containing diacid anhydride comprises 3, 5-trifluoromethyl-p-1, 3-diether-diphthalic anhydride.
In one embodiment of the present invention, the diamine comprises 2, 4-trifluoromethyl-p-aniline.
In one embodiment of the invention, the mono-anhydride comprises phthalic anhydride.
In one embodiment of the present invention, the fluorine-containing polyimide has the following structural formula:
Figure GDA0002743052820000031
in one embodiment of the present invention, the cross-linking curing step comprises heating the semi-finished product at a temperature of 420 to 500 ℃ for 3 to 5 hours.
In another embodiment of the present invention, a flexible substrate is provided, which comprises a fluorine-containing polyimide according to any one of the embodiments of the present invention.
Another embodiment of the present invention provides a display device including the flexible substrate according to any one of the embodiments of the present invention.
Compared with the prior art, the fluorine-containing polyimide, the manufacturing method thereof, the flexible substrate and the display device provided by the invention have the advantages that the light transmittance is improved mainly by introducing fluorine-containing dianhydride residues into a new polymeric molecular structure.
In order to make the aforementioned and other objects of the present invention more comprehensible, preferred embodiments accompanied with figures are described in detail below:
drawings
FIG. 1 is a thermogravimetric analysis of a fluorine-containing polyimide of an example of the present invention.
FIG. 2 is a flowchart of a method for producing a fluorine-containing polyimide according to an embodiment of the present invention.
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. Furthermore, directional phrases used herein, such as, for example, upper, lower, top, bottom, front, rear, left, right, inner, outer, lateral, peripheral, central, horizontal, lateral, vertical, longitudinal, axial, radial, uppermost or lowermost, etc., refer only to the orientation 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.
The embodiment of the invention provides a fluorine-containing polyimideAmine, the structural formula of the fluorine-containing polyimide is C-B- [ A-B [ ]]n-C, wherein group a comprises a fluorine-containing dianhydride residue, group B comprises a diamine residue, and group C comprises a monofunctional anhydride residue. The fluorine-containing polyimide of the embodiment of the invention has n groups A and B which are repeatedly arranged, wherein n can be between 30 and 50000 for example. The group C acts primarily as a capping agent. The group B is grafted between the group a and the group C.
In one embodiment, the group a may have a benzene ring structure. In one example, the group a has the following structural formula:
Figure GDA0002743052820000041
in one embodiment, the group B may have a benzene ring structure. In one example, the group B has the following structural formula:
Figure GDA0002743052820000051
in one embodiment, the group C may have a benzene ring structure. In one example, the group C has the following structural formula:
Figure GDA0002743052820000052
in one embodiment, the fluorine-containing polyimide has the following structural formula:
Figure GDA0002743052820000053
here, it is to be mentioned that the fluorine-containing polyimide of the above formula (1) is subjected to analytical thermogravimetric analysis and light transmittance analysis. As shown in FIG. 1, the fluorine-containing polyimide of the examples of the present invention lost only 1% by weight at a high temperature (about 561 ℃ C.). On the other hand, the transmittance of the fluorine-containing polyimide of the embodiment of the invention can reach about 85% under most wavelengths (for example, the visible light range is about 390 to 780nm), which is far beyond the acceptable standard of 70% of the commercial standard.
In one embodiment, the fluorine-containing polyimide of the embodiment of the present invention can be used as a substrate material of a flexible display panel.
Referring to fig. 2, a method 20 for manufacturing fluorine-containing polyimide according to an embodiment of the present invention includes steps 21 to 23: providing fluorine-containing diacids, diamines and monoacids (step 21); mixing said fluorine-containing diacid anhydride, said diamine, and said mono-anhydride to form a semi-finished product (step 22); and carrying out a cross-linking curing step on the semi-finished product to form fluorine-containing polyimide, wherein the structural formula of the fluorine-containing polyimide is C-B- [ A-B ]]n-C, wherein a comprises a fluorine-containing dianhydride residue, B comprises a diamine residue and C comprises a monofunctional anhydride residue (step 23).
Step 21 of the method 20 for producing a fluorine-containing polyimide according to the embodiment of the present invention is: fluorine-containing diacids, diamines, and monoacids are provided. In this step 21, for example, 0.1 to 10mmol of fluorine-containing diacids, 0.1 to 10mmol of diamines and 0.1 to 5mmol of monoanhydrides are provided.
In one embodiment, the fluorine-containing anhydrides can have a benzene ring structure. In one example, the fluorine-containing diacid anhydride comprises 3, 5-trifluoromethyl-p-1, 3-diether-diphthalic anhydride having the following structural formula:
Figure GDA0002743052820000061
in one embodiment, the diamines may have a benzene ring structure. In one example, the diamines may comprise 2, 4-trifluoromethyl p-aniline, having the following formula:
Figure GDA0002743052820000062
in one embodiment, the mono-anhydrides can have a benzene ring structure. In one example, the mono-anhydride can comprise phthalic anhydride, having the following structural formula:
Figure GDA0002743052820000071
step 22 of the method 20 for producing a fluorine-containing polyimide according to the embodiment of the present invention is: mixing the fluorine-containing diacid anhydride, the diamine, and the mono-anhydride to form a semi-finished product. In this step 22, the semifinished product may be formed, for example, in the following manner. First, a mixture of fluorine-containing diacid anhydride and diamine is added to a solvent comprising N, N-Dimethylacetamide (DMAC) and N-methylpyrrolidone (N-methyl-2-pyrrolidone; NMP) to form a mixture. Thereafter, a monoanhydride is added to the mixture and uniformly mixed at room temperature for 24 to 96 hours to obtain the semi-finished product. In one example, the volume ratio of DMAC to NMP is between 0.2 and 2.
In one embodiment, the intermediate product has the following structural formula:
Figure GDA0002743052820000072
in one embodiment, the semi-finished product may be subjected to a bubble removal step, for example, a suction filtration (filter) may be performed in a vacuum environment for about 1 hour to remove bubbles in the semi-finished product; or may be left to stand at room temperature for about 2 to 4 hours to remove air bubbles from the semi-finished product.
Step 23 of the method 20 for producing a fluorine-containing polyimide according to the embodiment of the present invention is: performing a cross-linking curing step on the semi-finished product to form fluorine-containing polyimide, wherein the structural formula of the fluorine-containing polyimide is C-B- [ A-B ]]n-C, wherein group a comprises a fluorine-containing dianhydride residue, group B comprises a diamine residue and group C comprises a monofunctional anhydride residue. In one embodiment, the groups A, B and C in step 23 of the method 20 for preparing fluorine-containing polyimide according to the embodiment of the present invention can be obtained by referring to the embodiments of the present invention described aboveThe group a, the group B, and the group C in the fluorine-containing polyimide of the embodiment are not described in detail.
In one embodiment, the cross-linking curing step comprises heating the semi-finished product at a temperature of 420 to 500 ℃ for 1 to 5 hours. In one example, the cross-linking curing step may comprise at least one of a hard bake and a soft bake, for example. For example, the hard baking is carried out by directly raising the temperature to a specified temperature (for example, between 420 and 500 ℃) for 1 hour; the soft bake has multiple temperature plateaus, for example, heating to a first temperature plateau (e.g., between 200 and 250 ℃) for 20 to 30 minutes, then reheating to a second temperature plateau (e.g., between 300 and 350 ℃) for 20 to 30 minutes, and then reaching a third temperature plateau (e.g., between 420 and 500 ℃) for 3 hours. However, it should be noted that the above-mentioned temperature and time are only examples, and the crosslinking curing step is not limited to the above-mentioned temperature and time.
In one embodiment, after step 22 and before step 23, the semifinished product may be spin-coated, for example, on a substrate. Then, the semi-finished product is dried by a vacuum chamber dryer (vacuum chamber dryer) to remove the solvent of the semi-finished product. In one embodiment, step 23 may also be performed by a vacuum chamber dryer to remove the solvent from the semi-finished product and perform the cross-linking curing step.
In one embodiment, the method for producing a fluorine-containing polyimide according to the embodiment of the present invention can produce a fluorine-containing polyimide according to the embodiment of the present invention.
Also provided in embodiments of the present invention is a flexible substrate made of a material comprising the fluorine-containing polyimide according to any one of the embodiments of the present invention, such that the light transmittance of the flexible substrate can reach about 85% at most of visible light wavelengths.
The embodiment of the invention also provides a display device, wherein the display device comprises the flexible substrate according to any one of the embodiments of the invention, so that the flexible substrate of the display device has sufficient light transmittance.
The present invention has been described in relation to the above embodiments, which are only exemplary of the implementation of the present invention. It must be noted that the disclosed embodiments do not limit the scope of the invention. Rather, modifications and equivalent arrangements included within the spirit and scope of the claims are included within the scope of the invention.

Claims (3)

1. A method for producing a fluorine-containing polyimide, characterized by comprising: the method for producing a fluorine-containing polyimide comprises the steps of:
providing 0.1 to 10mmol of 3, 5-trifluoromethyl-p-1, 3-diether-diphthalic anhydride, 0.1 to 10mmol of 2, 4-trifluoromethyl-p-aniline and 0.1 to 5mmol of phthalic anhydride;
adding 3, 5-trifluoromethyl-p-1, 3-diether-diphthalic anhydride and 2, 4-trifluoromethyl-p-aniline to a solvent comprising N, N-dimethylacetamide and N-methylpyrrolidinone to form a mixture, and thereafter adding phthalic anhydride to the mixture and uniformly mixing at room temperature for 24 to 96 hours to form a semi-finished product having the following structural formula:
Figure 88619DEST_PATH_IMAGE002
wherein n is between 30 and 50000; and
performing a cross-linking curing step on the semi-finished product, and heating the semi-finished product at a temperature of 420-500 ℃ for 3-5 hours to form a fluorine-containing polyimide, wherein the fluorine-containing polyimide has a structural formula as follows:
Figure DEST_PATH_IMAGE003
。
2. a flexible substrate, characterized by: the material of the flexible substrate comprises the fluorine-containing polyimide produced by the method for producing a fluorine-containing polyimide according to claim 1.
3. A display device, characterized in that: the display device comprises the flexible substrate of claim 2.
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US20080262191A1 (en) * 2007-01-26 2008-10-23 Mizori Farhad G Methods for the preparation of imides, maleimides and maleimide-terminated polyimide compounds
CN102634020B (en) * 2011-09-19 2013-09-11 京东方科技集团股份有限公司 Prepolymer, oriented film, preparation method for oriented film, and liquid crystal display device
CN104558608B (en) * 2015-01-08 2016-09-14 江汉大学 A kind of polyimides and the preparation method of transparent membrane thereof
CN109422876A (en) * 2017-08-28 2019-03-05 苏州聚萃材料科技有限公司 Solution, Kapton and its application of polyamic acid
US20210191264A1 (en) * 2017-10-31 2021-06-24 Toray Industries, Inc. Negative photosensitive resin composition, cured film, and organic el display and manufacturing method therefor
CN107698761A (en) * 2017-11-03 2018-02-16 杭州超通科技有限公司 A kind of preparation method of polyimides
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CN110212090A (en) * 2019-05-23 2019-09-06 武汉华星光电半导体显示技术有限公司 A kind of PI substrate and preparation method thereof

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