CN105622938A - Polyimide, polyimide composition and preparation method thereof, alignment film and display device - Google Patents
Polyimide, polyimide composition and preparation method thereof, alignment film and display device Download PDFInfo
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- 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
- C08G73/1075—Partially aromatic polyimides
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- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
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- 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
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- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
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Abstract
The invention provides a polyimide, a polyimide composition and a preparation method thereof, an alignment film and a display device, belonging to the technical field of display and solving the problems of poor adhesion property, poor light transmittance and the like for the glass substrate in the film formed after the polyimide is coated on the substrate surface. The -Si-O-, the group of which the benzene ring contains an F side group, or the benzimidazole modified group is introduced into the main chain structure of the polyimide; and the modified group can obviously enhance the heat stability of the polyimide. The alignment film prepared from the polyimide composition has the advantages of favorable processability, favorable paintability, favorable flexibility and favorable adhesion property for the glass substrate, and can be stably used at 300 DEG C or below for a long time. The alignment film is suitable for various display devices.
Description
Technical field
The invention belongs to technique of display field, it is specifically related to a kind of polyimide, polyimide compositions and preparation method, alignment film, display unit.
Background technology
Along with the development of technique of display, people are more and more higher to the performance requriements of display screen, and wherein, the performance improving alignment film can improve the optical property of display screen significantly.
Existing alignment film is generally be coated with on the surface of the substrate by organic film, utilizes friction or other modes that the molecule of this film surface is directed, and the liquid crystal molecule inserted so that follow-up is by orientation. The polymkeric substance that can form this organic film comprises polyvinyl alcohol, polyoxyethylene glycol, polymeric amide, polyamic acid or polyimide, and wherein polyimide is owing to having the features such as excellent chemical stability and thermostability, is often used as alignment film material most.
Contriver finds that in prior art, at least there are the following problems: polyimide coating of the prior art on the surface of the substrate after film the adhesivity of glass substrate, light transmission etc. is not good, constrain its development in display field.
Summary of the invention
The present invention is directed to existing polyimide coating on the surface of the substrate after film to not good problems such as the adhesivity of glass substrate, light transmissions, it is provided that a kind of polyimide, polyimide compositions and preparation method, alignment film, display unit.
The technical scheme that solution the technology of the present invention problem adopts is:
A kind of polyimide, described polyimide is diamines and the polycondensate of two acid anhydrides, and described diamines comprises H2N-R1-NH2;
Wherein, R1In there is modified group, described modified group comprise-Si-O-,In any one or a few.
Preferably, described modified group comprises
Preferably, described modified group is linear modified group.
Preferably, described two acid anhydrides comprise any one or a few in 4,4'-(six fluorine isopropyl alkene) two phthalandione acid anhydrides, 3,3,4,4-biphenyl dianhydride, the 3-tertiary butyl two silyloxy Pyroglutaric acid.
Wherein, the structural formula of 4,4'-(six fluorine isopropyl alkene) two phthalandione acid anhydrides is:
Preferably, described H2N-R1-NH2For two aminopropyl tetramethyl disiloxane.
Wherein, two aminopropyl tetramethyl disiloxane molecular formula is: [NH2-(CH2)3-Si(CH3)2]2O��
Preferably, described diamines also comprises H2N-R2-NH2; Wherein, R2In have phenyl, ether base or containing 2-18 carbon alkyl in any one or a few.
Preferably, described H2N-R1-NH2With H2N-R2-NH2Mol ratio be 1: 9-4: 6.
Preferably, described H2N-R1-NH2For 2-(diamino-phenyl) benzoglyoxaline-5 amine, described H2N-R2-NH2Comprising mphenylenediamine and stearylamine, wherein the mol ratio of mphenylenediamine, stearylamine and 2-(diamino-phenyl) benzoglyoxaline-5 amine is 7: 2: 1.
Wherein, the structural formula of 2-(diamino-phenyl) benzoglyoxaline-5 amine is:
The present invention also provides a kind of polyimide compositions, comprises above-mentioned polyimide.
The present invention also provides the preparation method of a kind of above-mentioned polyimide compositions, comprises the following steps: add in solvent by described diamines and two acid anhydrides, starts polycondensation.
Preferably, described polyimide compositions solid content is 6-12%.
Preferably, described polyimide compositions solid content is 8%.
Preferably, the limiting viscosity of described polyimide compositions is 1.1-1.6dL/g.
Preferably, the limiting viscosity of described polyimide compositions is 1.4dL/g.
Preferably, the viscosity-average molecular weight of described polyimide compositions is 8000-12000.
Preferably, the viscosity-average molecular weight of described polyimide compositions is 10000.
Preferably, described H2N-R1-NH2For two aminopropyl tetramethyl disiloxane, the preparation process of described pair of aminopropyl tetramethyl disiloxane is as follows:
Adding ammonium sulfate in the mixing solutions of hexamethyldisiloxane and allylamine, reflux obtains the first intermediate product;
Adding t-butanol solution and the tetramethyl disiloxane of Platinic chloride in the first intermediate product, reflux obtains the 2nd intermediate product;
Adding dehydrated alcohol in the 2nd intermediate product, reflux obtains two aminopropyl tetramethyl disiloxane.
Its concrete synthetic route is as follows:
The present invention also provides a kind of alignment film, is made up of above-mentioned polyimide compositions.
The present invention also provides a kind of display unit, comprises above-mentioned alignment film.
Introducing in the backbone structure of the polyimide of the present invention containing the modified group containing fluorine side base on-Si-O-, benzoglyoxaline or phenyl ring, above-mentioned modified group can significantly improve the thermal stability of polyimide; Adopt the alignment film processing coating property that this polyimide compositions makes good, snappiness and and the adhesivity of glass substrate good, it can temperature use steady in a long-term less than 300 DEG C. The alignment film of the present invention is applicable to various display unit.
Accompanying drawing explanation
Fig. 1 is the polyimide compositions preparation flow schematic diagram of embodiments of the invention 4.
Embodiment
For making those skilled in the art understand the technical scheme of the present invention better, below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1:
The present embodiment provides a kind of polyimide, and described polyimide is diamines and the polycondensate of two acid anhydrides, and described diamines comprises H2N-R1-NH2;
Wherein, R1In there is modified group, described modified group comprise-Si-O-,In any one or a few.
The backbone structure of the polyimide of the present embodiment introduce containing the modified group containing F side base or benzoglyoxaline in-Si-O-, phenyl ring, wherein, the bond energy height of siloxane bond, thermostability when such polyimide coating becomes alignment film, forming process, snappiness and and the adhesivity of glass substrate good. Benzoglyoxaline modified group so that polyimide compositions has good advection, wetting property and orientation, can significantly improve thermostability, the light transmission of polyimide alignment film. The alignment film adopting this polyimide compositions to make can the temperature long-term stability below 300 DEG C use. The alignment film of the present invention is applicable to various display unit.
Embodiment 2:
The present embodiment provides a kind of polyimide compositions, comprises the polyimide of above-described embodiment 1. Wherein, polyimide compositions can also comprise solvent.
Embodiment 3:
The present embodiment provides a kind of concrete polyimide compositions, comprises following preparation process:
(1) the two aminopropyl tetramethyl disiloxane (being abbreviated as SiDA) of preparation:
Adding ammonium sulfate in the mixing solutions of hexamethyldisiloxane and allylamine, reflux obtains the first intermediate product;
Adding the t-butanol solution of Platinic chloride in the first intermediate product, reflux is also dripped and is added tetramethyl disiloxane, dropwises latter 130 DEG C and continues reaction 2.5 hours, and naturally cooling obtains the 2nd intermediate product;
Under room temperature, adding dehydrated alcohol in the 2nd intermediate product, reflux 2 hours, normal pressure steams low-boiling-point substance, and decompression (120 DEG C) is collected to evaporate and point namely obtained pair aminopropyl tetramethyl disiloxane.
Concrete synthetic route is as follows:
(2) polyimide compositions is prepared:
By two aminopropyl tetramethyl disiloxane (SiDA) and 4 of above-mentioned preparation, 4'-diaminodiphenyl oxide (ODA) is dissolved in N,N-DIMETHYLACETAMIDE (DMAc) solution according to the mol ratio of 3: 7, is at room temperature stirred to whole dissolving;
Then being joined by 3,3,4,4-biphenyl dianhydride (BPDA) in the above-mentioned DMAc solution of stirring in batches, after reinforced, under room temperature (in the present invention, room temperature refers to 20-25 DEG C) condition, reaction can obtain polyimide compositions in 5 hours.
Wherein, the reaction formula of SiDA and BPDA condensation polymerization reaction generation polyimide is as follows:
Wherein m, the n in polyimide backbone structure changes according to the change of the molar ratio of SiDA and ODA. Containing-Si-O-group and a large amount of benzene ring structure in the polyimide backbone structure of the method synthesis, thermostability when said structure can significantly improve polyimide coating, forming process, snappiness and and the adhesivity of glass substrate. This polyimide compositions is polyimide acid solution, and its solid content is 8%, and limiting viscosity is 1.4dL/g. The viscosity-average molecular weight adopting Ubbelohde viscometer to record this polyimide compositions is 10000. Applied into film and obtained polyimide alignment film through the hot-imide of 250 DEG C.
Embodiment 4:
The present embodiment provides a kind of concrete polyimide compositions, as shown in Figure 1, comprises following preparation process:
S1, mphenylenediamine (PDA) stearylamine (ODA), 2-(diamino-phenyl) benzoglyoxaline-5 amine (BIA) are dissolved according to the molar ratio of 7: 2: 1 in DMAc or N-Methyl pyrrolidone (NMP) solution and it are stirred to whole dissolving;
S2, then BPDA is joined in above-mentioned solution go, continue to stir and can obtain polyimide compositions in 6 hours.
This polyimide compositions solid content is 6%, and limiting viscosity is 1.1dL/g. The viscosity-average molecular weight adopting Ubbelohde viscometer to record this polyimide compositions is 8000. Applied into film and obtained polyimide alignment film through 300 DEG C of hot-imides.
Embodiment 5:
The present embodiment provides a kind of concrete polyimide compositions, comprises following preparation process:
PDA and ODA is dissolved according to mol ratio 1: 3 in DMAc or nmp solution, it is stirred to whole dissolving;
Six fluorine isopropyl alkene-bis-(Tetra hydro Phthalic anhydride) (6FDA) is joined in above-mentioned solution, continues stirring and can obtain polyimide compositions in 4 hours.
This polyimide compositions solid content is 12%, and limiting viscosity is 1.6dL/g. The viscosity-average molecular weight adopting Ubbelohde viscometer to record this polyimide compositions is 12000. Applied into film and obtained polyimide alignment film through 250 DEG C of hot-imides.
Embodiment 6:
The present embodiment provides a kind of concrete polyimide compositions, comprises following preparation process:
Diamines SiDA and ODA is dissolved in N,N-DIMETHYLACETAMIDE (DMAc) solution according to the mol ratio of 1: 9, is at room temperature stirred to whole dissolving;
Then by 4,4'-(six fluorine isopropyl alkene) two phthalandione acid anhydrides (wherein the mol ratio of two acid anhydrides and diamines is 1:1) joins in the above-mentioned DMAc solution of stirring in batches, reacts at ambient temperature and can obtain polyimide compositions in 5 hours after reinforced.
Embodiment 7:
The present embodiment provides a kind of concrete polyimide compositions, comprises following preparation process:
Diamines SiDA and ODA is dissolved in N,N-DIMETHYLACETAMIDE (DMAc) solution according to the mol ratio of 4: 6, is at room temperature stirred to whole dissolving;
Then the 3-tertiary butyl two silyloxy Pyroglutaric acid (wherein the mol ratio of two acid anhydrides and diamines is 1:1) is joined in the above-mentioned DMAc solution of stirring, react at ambient temperature after reinforced and can obtain polyimide compositions in 5 hours.
Embodiment 8
The present embodiment provides a kind of polyimide compositions, and the polyimide compositions of itself and embodiment 3 is similar, and the difference of itself and embodiment 3 is, the mol ratio of SiDA and ODA is 9: 1.
Embodiment 9
The present embodiment provides a kind of polyimide compositions, and the polyimide compositions of itself and embodiment 3 is similar, and the difference of itself and embodiment 3 is, the mol ratio of SiDA and ODA is 7: 3.
Embodiment 10
The present embodiment provides a kind of polyimide compositions, and the polyimide compositions of itself and embodiment 3 is similar, and the difference of itself and embodiment 3 is, the mol ratio of SiDA and ODA is 5: 5.
5% weightless temperature of polyimide (PI) alignment film of testing example 3, embodiment 8, embodiment 9, embodiment/10, the results are shown in Table 1.
5% weightless temperature of table 1 polyimide alignment film
| PI | Embodiment 8 | Embodiment 9 | Embodiment 10 | Embodiment 3 |
| Td5/�� | 496.7 | 480.6 | 477.7 | 460.3 |
5% weightless temperature of the polyimide alignment film of visible the present invention all more than 400 DEG C, the excellent heat stability of alignment film. Siloxane structure is introduced in polyimide system, the rigidity of system is made to reduce thus greatly improve the solubility property of polymeric amide, improve snappiness and the processing characteristics of Kapton, and the polyimide containing this structure is lower than the surface energy of other Kapton so that the adhesion property of all the other glass substrates improves.
Obviously, the embodiment of the various embodiments described above also can carry out many changes; Such as: H2N-R1-NH2With H2N-R2-NH2Molar ratio can regulate, diamines can also be have on phenyl, ether base, phenyl ring containing F side base or containing the alkyl etc. of 2-18 carbon.
Embodiment 11:
Present embodiments providing a kind of alignment film, it is made up of the polyimide compositions of above-described embodiment.
Embodiment 12:
Present embodiments providing a kind of display unit, it comprises any one alignment film above-mentioned. Described display unit can be: any product or parts with display function such as display panels, Electronic Paper, mobile phone, panel computer, televisor, indicating meter, notebook computer, digital phase frame, navigating instrument.
It should be appreciated that the illustrative embodiments that above enforcement mode is only used to the principle of the present invention is described and adopts, but the present invention is not limited thereto. , it is possible to make various modification and improvement, for those skilled in the art, without departing from the spirit and substance in the present invention these modification and improvement are also considered as protection scope of the present invention.
Claims (12)
1. a polyimide, it is characterised in that, described polyimide is diamines and the polycondensate of two acid anhydrides, and described diamines comprises H2N-R1-NH2;
Wherein, R1In there is modified group, described modified group comprise-Si-O-,In any one or a few.
2. polyimide according to claim 1, it is characterised in that, described modified group comprises
3. polyimide according to claim 1, it is characterised in that, described two acid anhydrides comprise any one or a few in 4,4'-(six fluorine isopropyl alkene) two phthalandione acid anhydrides, 3,3,4,4-biphenyl dianhydride, the 3-tertiary butyl two silyloxy Pyroglutaric acid.
4. polyimide according to claim 1, it is characterised in that, described H2N-R1-NH2For two aminopropyl tetramethyl disiloxane.
5. polyimide according to claim 1, it is characterised in that, described diamines also comprises H2N-R2-NH2; Wherein, R2In have phenyl, ether base or containing 2-18 carbon alkyl in any one or a few.
6. polyimide according to claim 5, it is characterised in that, described H2N-R1-NH2With H2N-R2-NH2Mol ratio be 1: 9-4: 6.
7. polyimide according to claim 5, it is characterised in that, described H2N-R1-NH2For 2-(diamino-phenyl) benzoglyoxaline-5 amine, described H2N-R2-NH2Comprising mphenylenediamine and stearylamine, wherein the mol ratio of mphenylenediamine, stearylamine, 2-(diamino-phenyl) benzoglyoxaline-5 amine is 7: 2: 1.
8. a polyimide compositions, it is characterised in that, comprise the polyimide described in the arbitrary item of claim 1-7.
9. the preparation method of a polyimide compositions, it is characterised in that, described polyimide compositions is polyimide compositions according to claim 8, comprises the following steps: add in solvent by described diamines and two acid anhydrides, starts polycondensation.
10. the preparation method of polyimide compositions according to claim 9, it is characterised in that, described H2N-R1-NH2For two aminopropyl tetramethyl disiloxane, the preparation process of described pair of aminopropyl tetramethyl disiloxane is as follows:
Adding ammonium sulfate in the mixing solutions of hexamethyldisiloxane and allylamine, reflux obtains the first intermediate product;
Adding t-butanol solution and the tetramethyl disiloxane of Platinic chloride in the first intermediate product, reflux obtains the 2nd intermediate product;
Adding dehydrated alcohol in the 2nd intermediate product, reflux obtains two aminopropyl tetramethyl disiloxane.
11. 1 kinds of alignment films, it is characterised in that, it is made up of polyimide compositions according to claim 8.
12. 1 kinds of display unit, it is characterised in that, comprise alignment film according to claim 11.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105906813A (en) * | 2016-06-05 | 2016-08-31 | 吉林大学 | Method for preparing regular block copolymerization polyimide siloxane single-layer film |
| CN106496261A (en) * | 2016-08-31 | 2017-03-15 | 成都正威新材料研发有限公司 | A kind of preparation method of silicone-containing diamidogen |
| CN109192879A (en) * | 2018-08-31 | 2019-01-11 | 京东方科技集团股份有限公司 | Flexible Displays cover board and preparation method thereof and flexible display apparatus |
| CN109293919A (en) * | 2017-07-24 | 2019-02-01 | 京东方科技集团股份有限公司 | Liquid crystal orientation film, preparation method, substrate and display device |
| CN109370614A (en) * | 2018-11-21 | 2019-02-22 | 中节能万润股份有限公司 | A kind of aligning agent for liquid crystal, liquid crystal orientation film and liquid crystal display element |
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| CN109293919B (en) * | 2017-07-24 | 2020-08-04 | 京东方科技集团股份有限公司 | Liquid crystal alignment film, preparation method thereof, substrate and display device |
| CN109192879A (en) * | 2018-08-31 | 2019-01-11 | 京东方科技集团股份有限公司 | Flexible Displays cover board and preparation method thereof and flexible display apparatus |
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