CN105504281A - High-barrier function polyimide containing naphthaline structure and preparation method and application thereof - Google Patents
High-barrier function polyimide containing naphthaline structure and preparation method and application thereof Download PDFInfo
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- CN105504281A CN105504281A CN201610002976.1A CN201610002976A CN105504281A CN 105504281 A CN105504281 A CN 105504281A CN 201610002976 A CN201610002976 A CN 201610002976A CN 105504281 A CN105504281 A CN 105504281A
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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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Abstract
The invention discloses a high-barrier function polyimide containing a naphthaline structure and a preparation method and application thereof. The polyimide adopts aromatic diamine with the high-planarity naphthaline structure and various kinds of dianhydride as raw materials, and the polyimide is prepared through thermal imidization or chemical imidization. Due to the fact that the lowest energy state structure of a diamine monomer has the high planarity, obtained polyimide molecular chains are compactly stacked and have the excellent barrier performance. The polyimide has the high rigidity and has the high glass-transition temperature, thermal stability and the lower coefficient of thermal expansion. The synthesis method is simple and varied in technology, and therefore the method is applicable to industrial production. The polyimide can be widely applied to the field of high and new technology industries such as high-performance packaging, protection and electronic device packaging.
Description
Technical field
The present invention relates to material science, particularly a kind of high barrier function polyimide containing naphthalene structure and its preparation method and application.
Technical background
Organic electroluminescence device (OLED) is since birth, and just with its performance, color sensation, the perfectly advantage such as visual angle, infinitely-great contrast gradient enjoy the favor of industry specialists and human consumer more accurately; Further, utilize flexible polymer substrate to encapsulate OLED, can realize flexible, folding, even wearable flexible display technologies, therefore, OLED is considered to one of display device of new generation desirable, the most most with prospects.But there is life-span shorter bottleneck in it, this is because at present use polymer substrate material well can not intercept water in air and oxygen, and the organic function layer of OLED is very responsive to the oxygen G&W in air, be easy to layering and corrosion occur, the luminous efficiency of device and stability is caused to reduce, work-ing life shortens, and in addition, flexible solar battery encapsulation and some electronic devices field also also exist this problem.Therefore the very excellent flexible polymeric materials of barrier property must be selected to encapsulate device, could meet the strict demand of product life, this makes the new encapsulation technology of research and development and packaged material become a large focus of the industry development such as OLED and flexible solar battery.
At present, conventional high-barrier polymer materials has polyvinylidene dichloride (PVDC), ethylene-vinyl alcohol copolymer (EVOH), polymeric amide (PA), the thermoplastic polyester etc. that polyvinyl alcohol (PVA) and polyethylene terephthalate (PET) and PEN (PEN) represent, but they all cannot meet the requirement of OLED to substrate material harshness.Polyimide (PI) is owing to having outstanding high temperature resistant and low-temperature performance; Mechanical property is good, physical strength is high; Creep resisting ability is strong, and frictional behaviour is excellent; Unique photoelectric properties, excellent insulating property; Chemical stability is good, organic solvent-resistant, radiation resistance, barrier property are excellent, becomes one of OLED flexible substrate polymkeric substance optimal selection.
But the main path that current researchist improves the barrier property of polyimide prepares polyimide nano-composite material or carries out surface-coated to polyimide.But no matter be in polyimide, introduce sheet nanoparticle, barrier property (as patent CN104494249A, CN104817710A) is improved to extend the permeation pathway of gas molecule in polyimide, or the barrier property (as patent CN104284776A, CN104385731A, CN104846350A, CN104254442A etc.) of polyimide is improved by surface-coated high-barrier coating, capital affects the over-all properties of polyimide packaging film, and packaging process is become more numerous and diverse.But from Molecular Structure Design angle, the barrier property of polyimide can not only be improved, the over-all properties of polyimide can also be improved and simplify packaging process.This technology, by introducing the naphthalene nucleus with planarity in polyimide, constructs the polyimide material that a class is novel; And by reducing the interaction between side-chain structure, polymer molecular chain such as enhancing such as method such as introducing polar group and hydrogen bond etc., raising molecular chain rigidity and molecular chain pile up efficiency, reduce free volume, thus the high-performance polyimide material that acquisition one class excellent combination property, barrier property are outstanding.This architectural study focus on that design and synthesis molecule chain rigidity is high, that free volume is little is novel containing naphthalene structure high-barrier polyimide, but, not yet there is people to conduct a research to it at present, be therefore necessary to carry out the research of the novel design and synthesis containing naphthalene structure high-barrier polyimide.
Summary of the invention
The object of this invention is to provide a kind of high barrier function polyimide containing naphthalene structure.
Another object of the present invention is to the preparation method that the above-mentioned high barrier function polyimide containing naphthalene structure is provided.
The object of the present invention is achieved like this: a kind of high barrier function polyimide containing naphthalene structure, and its general structure is:
Wherein: the n one that to be 1 ~ 10000, Y be in following general structure:
Wherein, Ar
1be selected from any one in following structural:
Ar
2be selected from any one in following structural:
Ar
3be selected from any one in following structural:
Ar
4be selected from any one in following structural:
Ar
5be selected from any one in following structural:
X is the one in following structural formula:
Another object of the present invention is the preparation method providing the above-mentioned high barrier function polyimide containing naphthalene structure, the reaction process of the method is: in argon gas atmosphere, by the diamines containing Y structure with the dianhydride containing X structure in molar ratio for 1:(0.9 ~ 1.1) be dissolved in N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), dimethyl sulfone, tetramethylene sulfone, 1, 4-dioxane, N, N-N,N-DIMETHYLACETAMIDE, N, dinethylformamide, meta-cresol, in the strong polar non-proton organic solvent of one or more mixing in tetrahydrofuran (THF), , at-10 ~ 40 DEG C of stirring reaction 0.5 ~ 72h, obtain homogeneous phase, the polyamic acid glue of thickness, and polyamic acid glue is dewatered obtain the polyimide of high barrier.
The concrete operation step of described hot-imide method is: first by polyamic acid glue blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 0.8 ~ 2h of constant temperature after room temperature to 100 DEG C, the whole process 0.8 ~ 2h of constant temperature after being warming up to 200 DEG C from 100 DEG C, the whole process 0.8 ~ 2h of constant temperature after being warming up to 300 DEG C from 200 DEG C, after being warming up to 350 DEG C ~ 500 DEG C from 300 DEG C, the whole process 0.5 ~ 2h of constant temperature, can take out polyimide film after cooling.
The concrete operations of chemical imidization are: in polyamic acid glue, add pyridine/diacetyl oxide, or triethylamine/diacetyl oxide, or sodium acetate/diacetyl oxide is as dewatering agent, heat up and stir, be heated to 60 ~ 170 DEG C and continue stirring 0.5 ~ 6h, pour into after being cooled to room temperature in methyl alcohol or acetone and obtain polyimide precipitation, filtration drying, namely polyimide powder is obtained, then polyimide powder is dissolved in N-Methyl pyrrolidone (NMP), dimethyl sulfoxide (DMSO) (DMSO), N, N-N,N-DIMETHYLACETAMIDE (DMAc), N, dinethylformamide (DMF), in meta-cresol (m-Cresol) or tetrahydrofuran (THF) (THF), after being heated to dissolve completely, by polyimide solution blade coating on a glass, solvent is removed in 70 ~ 200 DEG C of vacuum-dryings, polyimide film can be taken out after cooling.
The preparation method of the high barrier function polyimide containing naphthalene structure that invention proposes, preparation technology is simple and various, and conditional request is low, is thus suitable for industrial production.Because the diamine monomer synthesizing this quasi-polyimide has rigid planar structure, this polyimide material is made to have excellent barrier property, higher second-order transition temperature and thermostability, and lower thermal expansivity.Polyimide disclosed in this invention can be widely used in microelectronics, military project, aerospace, high-performance packaging and the new high-tech industry field such as protection and electron device package.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of embodiment 1 ~ 5 resulting polymers, wherein:
The corresponding NPDA/PMDA-PI of a
The corresponding NADPA/PMDA-P of b
The corresponding NOC of c
3oPA/PMDA-PI
The corresponding PDANA/PMDA-PI of d
The corresponding NDEPA/PMDA-PI of e
Can see from infrared spectrogram, 1780 and 1720cm
-1near be the asymmetric of carbonyl on imide ring and symmetrical stretching vibration, 725cm
-1near be the flexural vibration of carbonyl on imide ring, 1380cm
-1near be the stretching vibration of imide ring.1730cm
-1there is the charateristic avsorption band of ester carbonyl group in place, 1653cm
-1there is the charateristic avsorption band of amidocarbonylation in place, 1617cm
-1, and 1503cm
-1there is the phenyl ring skeleton stretching vibration absorption peak of feature in place, 1278cm
-1neighbouring absorption peak is the formation vibration absorption peak of Ar-H, 1198cm
-1there is the charateristic avsorption band of ehter bond in place, 1172cm
-1there is the charateristic avsorption band of ester group in place, 827cm
-1place is the characteristic absorbance frequency that contraposition two replaces Ar-H, and these all illustrate that embodiment 1 ~ 5 is all successfully synthesized.
Embodiment
Provide example below so that the present invention will be described in more detail; it is important to point out that following examples can not be interpreted as the restriction to invention protection domain; some nonessential improvement and adjustment that the person skilled in the art in this field makes the present invention according to foregoing invention content, must belong to protection scope of the present invention.
Embodiment 1
Under room temperature, by 3.1040g (0.01mol) 4,4'-(naphthalene-2,7-diyl) dianiline (NPDA) and 38.8g (41ml) N, dinethylformamide is added in the there-necked flask of 100ml, pass into argon gas, stir, after dissolving completely, add 2.1812g (0.01mol) Pyromelliticdianhydride (pyromellitic acid anhydride, PMDA), continue stirring reaction 6h, obtain the polyamic acid solution of homogeneous phase transparent thickness.Again by polyamic acid solution blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 1h of constant temperature after constant temperature whole process 1h → 300 DEG C are warming up to 400 DEG C after constant temperature whole process 1h → 200 DEG C are warming up to 300 DEG C after constant temperature whole process 1h → 100 DEG C are warming up to 200 DEG C after room temperature to 100 DEG C, can take out polyimide film after cooling.The infrared spectrogram of this polyimide film is as shown in annex one.
The molecular structural formula of high-barrier polyimide (NPDA/PMDA-PI) film of the complete fragrant type in the present embodiment is as follows:
Embodiment 2
Under room temperature, by 5.4865g (0.01mol) N
1, N
4-bis (3'-amino-[1,1'-biphenyl]-4-yl) terephthalamide (NADPA) and 69.012g (73.1ml) N, dinethylformamide is added in the there-necked flask of 100ml, pass into argon gas, stir, after dissolving completely, add 2.1812g (0.01mol) Pyromelliticdianhydride (pyromellitic acid anhydride, PMDA), continue stirring reaction 6h, obtain the polyamic acid solution of homogeneous phase transparent thickness.Again by polyamic acid solution blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 1.5h of constant temperature after constant temperature whole process 1h → 300 DEG C are warming up to 420 DEG C after constant temperature whole process 1h → 200 DEG C are warming up to 300 DEG C after constant temperature whole process 1h → 100 DEG C are warming up to 200 DEG C after room temperature to 100 DEG C, can take out polyimide film after cooling.The infrared spectrogram of this polyimide film is as shown in annex one.
The molecular structural formula of high-barrier polyimide (NADPA/PMDA-PI) film of the complete fragrant type in the present embodiment is as follows:
Embodiment 3
Under room temperature, by 4.5856g (0.01mol) 4,4'-(((naphthalene-2,7-diylbis (oxy))-bis-(butane-4,1-diyl))-bis (oxy)) dianiline (NOC
3and 51.7g (54.7ml) N OPA), dinethylformamide is added in the there-necked flask of 100ml, pass into argon gas, stir, after dissolving completely, add 2.1812g (0.01mol) Pyromelliticdianhydride (pyromellitic acid anhydride, PMDA), continue stirring reaction 6h, obtain the polyamic acid solution of homogeneous phase transparent thickness.Again by polyamic acid solution blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 1h of constant temperature after constant temperature whole process 1h → 300 DEG C are warming up to 400 DEG C after constant temperature whole process 1h → 200 DEG C are warming up to 300 DEG C after constant temperature whole process 1h → 100 DEG C are warming up to 200 DEG C after room temperature to 100 DEG C, can take out polyimide film after cooling.The infrared spectrogram of this polyimide film is as shown in annex one.
High-barrier polyimide (the NOC of the complete fragrant type in the present embodiment
3oPA/PMDA-PI) molecular structural formula of film is as follows:
Embodiment 4
Under room temperature, by 4.4651g (0.01mol) N
1, N
4-bis (5-aminonaphthalen-1-yl) terephthalamide (PDANA) and 59.8g (63.3ml) N, dinethylformamide is added in the there-necked flask of 100ml, pass into argon gas, stir, after dissolving completely, add 2.1812g (0.01mol) Pyromelliticdianhydride (pyromellitic acid anhydride, PMDA), continue stirring reaction 6h, obtain the polyamic acid solution of homogeneous phase transparent thickness.Again by polyamic acid solution blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 1h of constant temperature after constant temperature whole process 1h → 300 DEG C are warming up to 400 DEG C after constant temperature whole process 1h → 200 DEG C are warming up to 300 DEG C after constant temperature whole process 1h → 100 DEG C are warming up to 200 DEG C after room temperature to 100 DEG C, can take out polyimide film after cooling.The infrared spectrogram of this polyimide film is as shown in annex one.
The molecular structural formula of high-barrier polyimide (PDANA/PMDA-PI) film of the complete fragrant type in the present embodiment is as follows:
Embodiment 5
Under room temperature, by 4.2647g (0.01mol) bis (4-aminobenzyl) naphthalene-2,6-dicarboxylate (NDEPA) and 58.0g (61.4ml) N, dinethylformamide is added in the there-necked flask of 100ml, pass into argon gas, stir, after dissolving completely, add 2.1812g (0.01mol) Pyromelliticdianhydride (pyromellitic acid anhydride, PMDA), continue stirring reaction 6h, obtain the polyamic acid solution of homogeneous phase transparent thickness.Again by polyamic acid solution blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 0.5h of constant temperature after constant temperature whole process 1h → 300 DEG C are warming up to 350 DEG C after constant temperature whole process 1h → 200 DEG C are warming up to 300 DEG C after constant temperature whole process 1h → 100 DEG C are warming up to 200 DEG C after room temperature to 100 DEG C, can take out polyimide film after cooling.The infrared spectrogram of this polyimide film is as shown in annex one.
The molecular structural formula of high-barrier polyimide (NDEPA/PMDA-PI) film of the complete fragrant type in the present embodiment is as follows:
Claims (9)
1., containing a high barrier function polyimide material for naphthalene structure, its general formula of molecular structure is:
Wherein: n be 1 ~ 10000, Y be selected from following general structure one or more:
Wherein, Ar
1be selected from any one in following structural:
Ar
2be selected from any one in following structural:
Ar
3be selected from any one in following structural:
Ar
4be selected from any one in following structural:
Ar
5be selected from any one in following structural:
X is the one in following structural formula:
2., according to claim 1 containing the high barrier function polyimide material of naphthalene structure, it is characterized in that: polyimide material can be prepared into high-isolation film or powder.
3. according to claim 1 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: in argon gas atmosphere, by the diamines containing Y structure with the dianhydride containing X structure in molar ratio for 1:(0.9 ~ 1.1) be dissolved in strong polar non-proton organic solvent, at-10 ~ 40 DEG C of stirring reaction 0.5 ~ 72h, obtain the polyamic acid glue of homogeneous phase, thickness, and polyamic acid glue is dewatered obtain the polyimide of high barrier.
4. according to claim 3 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: the diamines containing Y structure accounts for 2 ~ 50% of reaction mass total mass with the dianhydride total mass containing X structure.
5. according to claim 3 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: strong polar non-proton organic solvent is N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), dimethyl sulfone, tetramethylene sulfone, 1,4-dioxane, N, one or more mixture in N-N,N-DIMETHYLACETAMIDE, DMF, meta-cresol, tetrahydrofuran (THF).
6. according to claim 3 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: the method that the dehydration of polyamic acid glue obtains polyimide can be hot-imide or chemical imidization.
7. according to claim 6 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: the concrete operations of hot-imide are: first by polyamic acid glue blade coating on a glass, again sheet glass is placed in vacuum drying oven, vacuumize, heating schedule is: the whole process 0.8 ~ 3h of constant temperature after room temperature to 100 DEG C, the whole process 0.8 ~ 2h of constant temperature after being warming up to 200 DEG C from 100 DEG C, the whole process 0.8 ~ 2h of constant temperature after being warming up to 300 DEG C from 200 DEG C, the whole process 0.5 ~ 2h of constant temperature after being warming up to 350 DEG C ~ 500 DEG C from 300 DEG C, polyimide film can be taken out after cooling.
8. according to claim 6 containing the preparation method of the high barrier function polyimide material of naphthalene structure, it is characterized in that: the concrete operations of chemical imidization are: in polyamic acid glue, add pyridine/diacetyl oxide, or triethylamine/diacetyl oxide, or sodium acetate/diacetyl oxide is as dewatering agent, heat up and stir, be heated to 60 ~ 170 DEG C and continue stirring 0.5 ~ 6h, pour into after being cooled to room temperature in methyl alcohol or acetone and obtain polyimide precipitation, filtration drying, namely polyimide powder is obtained, then polyimide powder is dissolved in N-Methyl pyrrolidone (NMP), dimethyl sulfoxide (DMSO) (DMSO), N, N-N,N-DIMETHYLACETAMIDE (DMAc), N, dinethylformamide (DMF), in meta-cresol (m-Cresol) or tetrahydrofuran (THF) (THF), after being heated to dissolve completely, by polyimide solution blade coating on a glass, solvent is removed in 70 ~ 200 DEG C of vacuum-dryings, polyimide film can be taken out after cooling.
9. the high barrier function polyimide material containing naphthalene structure according to claim 1, is characterized in that it can be applicable to microelectronics, military project, aerospace, high-performance packaging and protection and electron device package new high-tech industry field.
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Cited By (5)
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| CN108976419A (en) * | 2018-07-31 | 2018-12-11 | 湖南工业大学 | A kind of aromatic series super-branched polyimide and its preparation method and application containing naphthalene structure |
| CN109134272A (en) * | 2018-07-31 | 2019-01-04 | 湖南工业大学 | A kind of Triamine monomer and its preparation method and application centered on the structure by naphthylamines |
| CN112739747A (en) * | 2018-08-07 | 2021-04-30 | 杜邦电子公司 | Polymers for use in electronic devices |
| CN115490854A (en) * | 2022-09-05 | 2022-12-20 | 江西有泽新材料科技有限公司 | Low-dielectric, high-heat-resistant and low-water-absorption high-performance polyimide, and preparation method and application thereof |
| CN112739747B (en) * | 2018-08-07 | 2024-05-14 | 杜邦电子公司 | Polymer for use in electronic devices |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976419A (en) * | 2018-07-31 | 2018-12-11 | 湖南工业大学 | A kind of aromatic series super-branched polyimide and its preparation method and application containing naphthalene structure |
| CN109134272A (en) * | 2018-07-31 | 2019-01-04 | 湖南工业大学 | A kind of Triamine monomer and its preparation method and application centered on the structure by naphthylamines |
| CN112739747A (en) * | 2018-08-07 | 2021-04-30 | 杜邦电子公司 | Polymers for use in electronic devices |
| JP2021534271A (en) * | 2018-08-07 | 2021-12-09 | デュポン エレクトロニクス インコーポレイテッド | Polymers for use in electronic devices |
| JP7444851B2 (en) | 2018-08-07 | 2024-03-06 | デュポン エレクトロニクス インコーポレイテッド | Polymers for use in electronic devices |
| CN112739747B (en) * | 2018-08-07 | 2024-05-14 | 杜邦电子公司 | Polymer for use in electronic devices |
| CN115490854A (en) * | 2022-09-05 | 2022-12-20 | 江西有泽新材料科技有限公司 | Low-dielectric, high-heat-resistant and low-water-absorption high-performance polyimide, and preparation method and application thereof |
| CN115490854B (en) * | 2022-09-05 | 2024-01-30 | 江西有泽新材料科技有限公司 | Polyimide with low dielectric, high heat resistance and low water absorption and high performance, and preparation method and application thereof |
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Application publication date: 20160420 |