CN107129494A - Compound containing Cardo structures and preparation method thereof - Google Patents
Compound containing Cardo structures and preparation method thereof Download PDFInfo
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- CN107129494A CN107129494A CN201710324176.6A CN201710324176A CN107129494A CN 107129494 A CN107129494 A CN 107129494A CN 201710324176 A CN201710324176 A CN 201710324176A CN 107129494 A CN107129494 A CN 107129494A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
-
- 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
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
Abstract
The invention provides compound containing Cardo structures and preparation method thereof, belong to polymeric material field.Three kinds of compounds that the present invention is provided, are the noval chemical compounds containing Cardo structures for finding and synthesizing first, and its structure has high symmetry, the polymer excellent available for processability.A kind of polyimides containing Cardo structures that the present invention is provided is a kind of new polyimide polymer, and with dissolubility is good, dielectric constant is low, mechanical performance is strong and the excellent characteristic of heat-resistant stability.The preparation method for the above-claimed cpd that the present invention is provided, synthetic route is simple, easily realize, and high income, the purity of obtained product are high.
Description
Technical field
The present invention relates to polymeric material field, in particular to a kind of compound and its system containing Cardo structures
Preparation Method.
Background technology
Polyimide material has prominent high temperature resistant, low temperature resistant, corrosion-resistant, radiation hardness, the characteristic of high insulation, its nothing
Poison, thermal coefficient of expansion is low, and dielectric properties and mechanical performance are excellent, can be applied to spacecraft and rocket device as high-temperature material
Material Field, can also be used as insulating protective layer as dielectric material in microelectronic component.
It is strong between the rigid backbone having by them and chain although polyimides has many excellent performances
Interaction so that polyimides has higher glass transition temperature, and poor solubility property, while cost is higher.
The content of the invention
It is an object of the invention to provide three kinds of compounds containing Cardo structures and preparation method thereof, these three chemical combination
Thing is all noval chemical compound, is the compound containing Cardo structures for finding and synthesizing first, and its structure has high symmetry,
The polymer excellent available for processability.
It is this another object of the present invention is to provide a kind of polyimides containing Cardo structures and preparation method thereof
Polyimides is a kind of new polyimide polymer, and with dissolubility is good, dielectric constant is low, mechanical performance is strong and
The excellent characteristic of heat-resistant stability.
In order to realize the above-mentioned purpose of the present invention, spy uses following technical scheme：
A kind of compound containing Cardo structures shown in formula I.
A kind of preparation method of the compound containing Cardo structures shown in Formulas I, it includes：
By 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes and 4- halo phthalonitriles in alkali and phase transfer catalysis (PTC)
Fragrant nucleophilic substitution reaction occurs in the presence of agent.
A kind of compound containing Cardo structures as shown in Formula II.
A kind of preparation method of the compound containing Cardo structures shown in Formula II, it includes：By compound of formula I in acid
Or hydrolysis occurs in the presence of alkali.
A kind of compound containing Cardo structures as shown in formula III.
A kind of preparation method of the compound containing Cardo structures shown in formula III, Formula II compound and acetic anhydride are existed
20~28h is reacted at 120~140 DEG C.
A kind of polyimides containing Cardo structures as shown in formula IV：
Wherein, Ar includes：
A kind of preparation method of the polyimides containing Cardo structures shown in formula IV, it includes：
Nucleophilic substitution reaction is occurred into aprotic dipolar solvents for formula III compound and armaticity diamine compound, its
Middle armaticity diamine compound includes：
Compared with prior art, beneficial effects of the present invention are：
Three kinds of compounds that the present invention is provided are to contain in the noval chemical compound for finding and synthesizing first, its structure
Cardo structures, and with high symmetry, the polymer excellent available for processability.The synthetic method of these three compounds
Simply, reaction yield height, product purity are big.
Compound further reacts the polyimides shown in obtained formula IV as shown in formula III, also containing Cardo structures,
It is a kind of new polyimide polymer, it has following characteristic：Dissolubility is excellent, can be dissolved in DMA,
The protonic solvents such as N,N-dimethylformamide；Filming performance is excellent, and membrance casting condition is simple and gained film has well soft
Toughness；It has superior mechanical property and electrical property；In addition, also having excellent heat-resisting and moisture-proof thermal oxidation.
Embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the present invention.It is unreceipted specific in embodiment
Condition person, the condition advised according to normal condition or manufacturer is carried out.Agents useful for same or the unreceipted production firm person of instrument, be
The conventional products that can be obtained by commercially available purchase.
Present embodiment provides a kind of compound containing Cardo structures shown in formula I.
Present embodiment also provides a kind of preparation method of compound shown in Formulas I, and it includes：
By 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes and 4- halo phthalonitriles in alkali and phase transfer catalysis (PTC)
Fragrant nucleophilic substitution reaction occurs in the presence of agent.
The structure of 9,9- bis--(4- hydroxy phenyls) -4,5- diaza fluorenes is shown as a formula V：
4- halo phthalonitriles, including 4- fluorine phthalonitrile, 4- chlore O-phthalic acids nitrile, 4- bromines phthalonitrile and 4-
Any one in iodine phthalonitrile, it is more preferred, it is 4- fluorine phthalonitriles.
Further, in fragrant nucleophilic substitution reaction, alkali includes potassium carbonate, lithium carbonate, sodium carbonate, saleratus, phosphoric acid
Any one in hydrogen potassium and sodium dihydrogen phosphate.These materials are strong base-weak acid salt, in the presence of phase transfer catalyst, alkali
Property enhancing, be conducive to making the reactive hydrogen in Formula V compound on phenolic hydroxyl group leave away, so as to be used as the adjacent benzene of nucleopilic reagent attack 4- halos
Dimethoxy nitrile, obtains compound shown in Formulas I.
Further, in fragrant nucleophilic substitution reaction, phase transfer catalyst be cyclic crown ether class compound, including 18 hat 6
Any one in 5 ethers is preced with ether, 12 4 ethers of hat and 15.The addition of phase transfer catalyst so that 4,5- carbolines and the adjacent benzene of 4- halos
Dimethoxy nitrile can be contacted fully, improve reaction speed and product yield.
Further, the reaction is carried out in aprotic dipolar solvents, and aprotic dipolar solvents include N, N- dimethyl methyls
Acid amides, dimethyl sulfoxide (DMSO), acetone, acetamide etc., it is more preferred, from DMF.
The reaction temperature when reaction is carried out is 70~90 DEG C, preferably 75~85 DEG C；Reaction time is 6~8h, preferably
For 6.5~7.5h.Inventor has found by theoretical research and practical exploration for many years, when the temperature and time of the reaction is above-mentioned
In the range of when, the high income of compound shown in the Formulas I of last gained.
Present embodiment also provides a kind of compound containing Cardo structures as shown in Formula II.
Present embodiment also provides a kind of preparation method of the compound containing Cardo structures as shown in Formula II, and it is wrapped
Include：Hydrolysis is occurred into the presence of acids and bases for compound of formula I.
The cyano group contained in compound of formula I, under acid or alkaline conditions, can occur hydrolysis, generate carboxyl, i.e.,
Obtain Formula II compound.Optionally, the reaction temperature of the reaction be 80~90 DEG C, the reaction time be 2~3d.
The reaction is preferably carried out in the presence of base, and alkali includes potassium carbonate, lithium carbonate, sodium carbonate, saleratus, phosphoric acid
Hydrogen potassium and sodium dihydrogen phosphate etc..
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula III.
Present embodiment also provides a kind of preparation method of the compound containing Cardo structures as shown in formula III, and it is wrapped
Include and Formula II compound and acetic anhydride are reacted into 20~28h at 120~140 DEG C.
With acetic anhydride condensation reaction can occur for the adjacent dicarboxyl in Formula II compound, form the dicarboxylic anhydride shown in formula III.
Compound shown in formula III contains Cardo structures, and purity is high, and with high symmetry, excellent available for processability is poly-
Acid imide.
Further, the preparation method includes：By Formula II compound under the protection of nitrogen or inert gas, with acetic anhydride
23~25h of back flow reaction at 125~135 DEG C.
Present embodiment also provides a kind of polyimides containing Cardo structures as shown in formula IV：
Wherein, Ar includes：
Contain phenodiazine fluorenyl groups in this quasi-polyimide shown in formula IV, its main chain, so that the quasi-polyimide
Solubility property and mechanical performance be all increased dramatically.The quasi-polyimide dissolves in DMAC N,N' dimethyl acetamide, N, N- bis-
The protonic solvents such as NMF, and with dielectric constant low (dielectric constant is only 1.78), good mechanical performance, water suction
Property the characteristic such as low and heat endurance is strong.In addition, also have excellent filming performance, membrance casting condition is easy and gained film have it is good
Good pliability.
Present embodiment also provides a kind of preparation method of the polyimides containing Cardo structures as shown in formula IV, its
Including：Nucleophilic substitution reaction is occurred into aprotic dipolar solvents for formula III compound and armaticity diamine compound, wherein virtue
Fragrance diamine compound includes：
In the preparation method, aprotic dipolar solvents include 1-METHYLPYRROLIDONE, dimethyl sulfoxide (DMSO), acetone and diformazan
Any one in base formamide.Further, in preferred embodiments of the present invention, contained using one-step synthesis method main chain
The method of nonplanar polyimides of Cardo structures includes：Under the protection of nitrogen or inert gas, by above-mentioned armaticity two
Amines is dissolved in aprotic dipolar solvents, is then mixed at normal temperatures with formula III compound after 20~30h, then
Mixed with toluene and be warming up to 170~190 DEG C, after 3~5h of heating, remove toluene, it is post-treated after obtain poly- shown in formula IV
Acid imide.
The feature and performance to the present invention are described in further detail with reference to embodiments：
Embodiment 1-1
The present embodiment provides the compound containing Cardo structures shown in a kind of Formulas I,
The preparation method of the compound includes：
By 10mmol 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes, 21mmol 4- fluorine phthalonitrile,
13mmol potassium carbonate and 18 6 ethers of hat are added in 100mL three-necked flask, and magnetic agitation is carried out under nitrogen protection,
Reacted under normal temperature and 80 DEG C of continuation 7 hours of reaction are warming up to after half an hour, poured into after frozen water and separate out, filtering is washed with water, slightly
Product ethyl alcohol recrystallization, obtains compound of formula I.
Embodiment 1-2
The present embodiment provides the compound containing Cardo structures shown in a kind of Formulas I, the preparation method bag of the compound
Include：
By 10mmol 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes, 21mmol 4- fluorine phthalonitrile,
13mmol lithium carbonate and 12 4 ethers of hat are added in 100mL three-necked flask, and magnetic agitation is carried out under nitrogen protection,
Reacted under normal temperature and 70 DEG C of continuation 8 hours of reaction are warming up to after half an hour, poured into after frozen water and separate out, filtering is washed with water, slightly
Product ethyl alcohol recrystallization, obtains compound of formula I.
Embodiment 1-3
The present embodiment provides the compound containing Cardo structures shown in a kind of Formulas I, the preparation method bag of the compound
Include：
By 10mmol 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes, 21mmol 4- fluorine phthalonitrile,
13mmol sodium carbonate and 15 5 ethers of hat are added in 100mL three-necked flask, and magnetic agitation is carried out under nitrogen protection,
Reacted under normal temperature and 90 DEG C of continuation 6 hours of reaction are warming up to after half an hour, poured into after frozen water and separate out, filtering is washed with water, slightly
Product ethyl alcohol recrystallization, obtains compound of formula I.
Embodiment 2-1
The present embodiment provides a kind of compound containing Cardo structures as shown in Formula II.
Its preparation method includes：
0.002mmol compound of formula I and 0.08mmol potassium carbonate is added in 500mL single port bottles, 200mL second is added
(volume ratio is 1 to the mixed solution of alcohol and water:1), flow back 50 hours, filter while hot at 86 DEG C, filter out to fall after insoluble impurity
Enter in beaker, add watery hydrochloric acid and adjust pH value to 1.5, have white solid precipitation, stand overnight, filter out white solid, and use water
Washing, crude product acetic acid and water mixed solution recrystallization, stand and separate out, filter out white solid, as Formula II compound.
Embodiment 2-2
The present embodiment provides a kind of compound containing Cardo structures as shown in Formula II.Its preparation method includes：
0.002mmol compound of formula I and 0.08mmol potassium hydroxide is added in 500mL single port bottles, 200mL is added
(volume ratio is 1 to the mixed solution of second alcohol and water:1), flowed back at 80 DEG C 72 hours, filter, filtered out after insoluble impurity while hot
Pour into beaker, add watery hydrochloric acid and adjust pH value to 1, have white solid precipitation, stand overnight, filter out white solid, and use water
Washing, crude product acetic acid and water mixed solution recrystallization, stand and separate out, filter out white solid, as Formula II compound.
Embodiment 2-3
The present embodiment provides a kind of compound containing Cardo structures as shown in Formula II.Its preparation method includes：
0.002mmol compound of formula I and 0.08mmol potassium hydroxide is added in 500mL single port bottles, 200mL is added
(volume ratio is 1 to the mixed solution of second alcohol and water:1), flowed back at 90 DEG C 24 hours, filter, filtered out after insoluble impurity while hot
Pour into beaker, add watery hydrochloric acid and adjust pH value to 2, have white solid precipitation, stand overnight, filter out white solid, and use water
Washing, crude product acetic acid and water mixed solution recrystallization, stand and separate out, filter out white solid, as Formula II compound.
Embodiment 3-1
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula III.
Its preparation method includes：
1.47mmol Formula II compound is added to the 25ml three-necked flasks containing 7mL acetic anhydrides, nitrogen protection, magnetic force
Stirring, after being flowed back 24 hours at 130 DEG C, is filtered, filtrate is poured into beaker while hot, and 14mL ice second is added in beaker
Acid, stands and separates out yellow solid, filtering, is dried at 150 DEG C of vacuum, produces formula III compound.
Embodiment 3-2
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula III, its preparation method bag
Include：
1.47mmol Formula II compound is added to the 25ml three-necked flasks containing 7mL acetic anhydrides, nitrogen protection, magnetic force
Stirring, after being flowed back 25 hours at 125 DEG C, is filtered, filtrate is poured into beaker while hot, and 14mL ice second is added in beaker
Acid, stands and separates out yellow solid, filtering, is dried at 150 DEG C of vacuum, produces formula III compound.
Embodiment 3-3
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula III, its preparation method bag
Include：
1.47mmol Formula II compound is added to the 25ml three-necked flasks containing 7mL acetic anhydrides, nitrogen protection, magnetic force
Stirring, after being flowed back 23 hours at 135 DEG C, is filtered, filtrate is poured into beaker while hot, and 14mL ice second is added in beaker
Acid, stands and separates out yellow solid, filtering, is dried at 150 DEG C of vacuum, produces formula III compound.
Embodiment 4-1
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-a：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of nitrogen, by 1mmol aromatic diamines, (formula a) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 25 DEG C, after being stirred 24 hours at 25 DEG C, toluene is added and is warming up to 180 DEG C,
Remove water after 4h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-a
Compound.
Embodiment 4-2
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-b：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of argon gas, by 1mmol aromatic diamines, (formula b) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 30 DEG C, after being stirred 20 hours at 30 DEG C, toluene is added and is warming up to 170 DEG C,
Remove water after 5h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-b
Compound.
Embodiment 4-3
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-c：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of argon gas, by 1mmol aromatic diamines, (formula c) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 20 DEG C, after being stirred 30 hours at 20 DEG C, toluene is added and is warming up to 190 DEG C,
Remove water after 3h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-c
Compound.
Embodiment 4-4
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-d：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of argon gas, by 1mmol aromatic diamines, (formula d) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 25 DEG C, after being stirred 25 hours at 25 DEG C, toluene is added and is warming up to 180 DEG C,
Remove water after 4h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-d
Compound.
Embodiment 4-5
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-e：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of argon gas, by 1mmol aromatic diamines, (formula e) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 25 DEG C, after being stirred 25 hours at 25 DEG C, toluene is added and is warming up to 180 DEG C,
Remove water after 4h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-e
Compound.
Embodiment 4-6
The present embodiment provides a kind of polyimides containing Cardo structures as shown in formula IV-f：
Wherein, Ar structure is：
Its preparation method includes：
Under the protection of argon gas, by 1mmol aromatic diamines, (formula f) is fully dissolved into 1-METHYLPYRROLIDONE under agitation
In, 1mmol formula III compound is added at 25 DEG C, after being stirred 25 hours at 25 DEG C, toluene is added and is warming up to 180 DEG C,
Remove water after 4h, then except toluene 10min, solution is poured into a large amount of methanol, filter, dried at 80 DEG C of vacuum, produce formula IV-f
Compound.
Although illustrate and describing the present invention with specific embodiment, but it will be appreciated that without departing substantially from the present invention's
Many other changes and modification can be made in the case of spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of compound containing Cardo structures shown in formula I
2. a kind of preparation method of the compound as claimed in claim 1 containing Cardo structures, it is characterised in that it includes：
By 9,9- bis--(4- hydroxy phenyls) -4,5- diazas fluorenes and 4- halos phthalonitrile in alkali and phase transfer catalyst
In the presence of occur fragrant nucleophilic substitution reaction.
3. the preparation method of the compound according to claim 2 containing Cardo structures, it is characterised in that the fragrance
In nucleophilic substitution reaction, the alkali is included in potassium carbonate, lithium carbonate, sodium carbonate, saleratus, potassium hydrogen phosphate and sodium dihydrogen phosphate
Any one.
4. the preparation method of the compound according to claim 2 containing Cardo structures, it is characterised in that the fragrance
In nucleophilic substitution reaction, the phase transfer catalyst includes any one in 18 6 ethers of hat, 12 4 ethers of hat and 15 5 ethers of hat.
5. a kind of compound containing Cardo structures as shown in Formula II
6. a kind of preparation method of the compound as claimed in claim 5 containing Cardo structures, it is characterised in that it includes：
Hydrolysis is occurred into the presence of acids and bases for compound of formula I, the structure of the compound of formula I is：
7. a kind of compound containing Cardo structures as shown in formula III
8. a kind of preparation method of the compound as claimed in claim 7 containing Cardo structures, it is characterised in that it includes：
Formula II compound and acetic anhydride are reacted into 20~28h at 120~140 DEG C, the structure of the Formula II compound is：
9. a kind of polyimides containing Cardo structures as shown in formula IV：
Wherein, Ar includes：
10. a kind of preparation method of the polyimides as claimed in claim 9 containing Cardo structures, it is characterised in that it is wrapped
Include：Nucleophilic substitution reaction is occurred into aprotic dipolar solvents for the formula III compound and armaticity diamine compound；
The structure of wherein described formula III compound is：
The armaticity diamine compound includes：
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110156990A (en) * | 2019-05-30 | 2019-08-23 | 武汉华星光电半导体显示技术有限公司 | A kind of polyimides compound, preparation method and applications |
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| CN104045638A (en) * | 2014-06-10 | 2014-09-17 | 兰州大学 | 4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof |
| CN106543174A (en) * | 2016-11-04 | 2017-03-29 | 兰州大学中卫高新技术研究院 | A kind of synthesis containing ether and the fluorene structured diacid monomer of phenodiazine and its polybenzimidazoles |
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2017
- 2017-05-10 CN CN201710324176.6A patent/CN107129494A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045638A (en) * | 2014-06-10 | 2014-09-17 | 兰州大学 | 4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof |
| CN106543174A (en) * | 2016-11-04 | 2017-03-29 | 兰州大学中卫高新技术研究院 | A kind of synthesis containing ether and the fluorene structured diacid monomer of phenodiazine and its polybenzimidazoles |
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| HUI LI ET AL: "《Novel high Tg, organosoluble poly(ether imide)s containing 4,5-diazafluorene unit: Synthesis and characterization》", 《EUROPEAN POLYMER JOURNAL》 * |
| HUI LI ET AL: "《Synthesis and properties of novel soluble and high Tg poly(ether imide)s from diamine containing 4,5‐diazafluorene and trifluoromethyl units》", 《POLYMER INTERNATIONAL》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110156990A (en) * | 2019-05-30 | 2019-08-23 | 武汉华星光电半导体显示技术有限公司 | A kind of polyimides compound, preparation method and applications |
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