CN107033141A - Compound containing Cardo structures and preparation method thereof - Google Patents
Compound containing Cardo structures and preparation method thereof Download PDFInfo
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- CN107033141A CN107033141A CN201710324201.0A CN201710324201A CN107033141A CN 107033141 A CN107033141 A CN 107033141A CN 201710324201 A CN201710324201 A CN 201710324201A CN 107033141 A CN107033141 A CN 107033141A
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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
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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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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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
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
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- Chemical Kinetics & Catalysis (AREA)
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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 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 and resistance to
The characteristic of excellent heat 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 as shown in formula (I).
A kind of preparation method of compound containing Cardo structures as shown in formula (I), it includes：
4,5- carbolines in the presence of alkali and phase transfer catalyst with 4- halos phthalonitrile to that fragrance occurs affine
Substitution reaction.
A kind of compound containing Cardo structures as shown in formula (II).
A kind of preparation method of the compound containing Cardo structures as shown in formula (II), by formula (I) compound 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 compound containing Cardo structures as shown in formula (III), it includes：Formula (II) is changed
Compound reacts 2~3d with acetic anhydride 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 polyimides containing Cardo structures as shown in formula (IV), it includes：By formula (III)
With armaticity diamine compound nucleophilic substitution reaction, the wherein amine compounds of armaticity two occur in aprotic dipolar solvents for compound
Thing 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.
The compound as shown in formula (III) further reacts the polyimides shown in obtained formula (IV), is also tied containing Cardo
Structure, is a kind of new polyimide polymer, and it has following characteristic：Dissolubility is excellent, can be dissolved in N, N- dimethylacetamides
The protonic solvents such as amine, N,N-dimethylformamide；Filming performance is excellent, and membrance casting condition is simple and gained film has well
Pliability；It has superior mechanical property and electrical property, and dielectric constant is only 1.78；In addition, also have it is 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 as shown in formula (I).
Present embodiment also provides the preparation method of compound shown in a kind of formula (I), and it includes：
4,5- carbolines in the presence of alkali and phase transfer catalyst with 4- halos phthalonitrile to that fragrance occurs affine
Substitution reaction.
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 on 4,5- carbolines leave away so that as nucleopilic reagent attack 4- halo phthalonitriles,
Obtain 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 130~150 DEG C, preferably 135~145 DEG C；Reaction time is 9~15h,
Preferably 10~12h.Inventor has found by theoretical research and practical exploration for many years, when the temperature and time of the reaction is upper
When in the range of stating, 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), its
Including：Hydrolysis is occurred into the presence of acids and bases for formula (I) compound.
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 4~5d.
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), its
Including：Formula (II) compound and acetic anhydride are reacted into 2~3d at 120~140 DEG C.
With acetic anhydride condensation reaction can occur for the adjacent dicarboxyl in formula (II) compound, form two shown in formula (III)
Acid anhydrides.Compound shown in formula (III) contains Cardo structures, and purity is high, and with high symmetry, available for processability
Excellent polyimides.
Further, the preparation method includes：By the dissolving of formula (II) compound in glacial acetic acid, in nitrogen or inert gas
Protection under, with acetic anhydride at 125~135 DEG C 2.3~2.7d of back flow reaction.
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 such polyamides is sub-
The solubility property and mechanical performance of amine are all increased dramatically.The quasi-polyimide dissolves in DMAC N,N' dimethyl acetamide, N, N-
The protonic solvents such as dimethylformamide, and with dielectric constant low (dielectric constant is only 1.78), good mechanical performance, suction
The characteristic such as aqueous low and heat endurance is strong.In addition, also having excellent filming performance, membrance casting condition is easy and gained film has
Good pliability.
Present embodiment also provides a kind of preparation method of the polyimides containing Cardo structures as 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：
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,
Mixed again with toluene and be warming up to 170~190 DEG C, after 3~5h of heating, remove toluene, it is post-treated after obtain shown in formula (IV)
Polyimides.
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 formula (I),
The preparation method of the compound includes：
By 4,5- carbolines (20mmol), 4- fluorine phthalonitrile (22mmol), 18 6 ethers of hat (5.15mmol) and potassium carbonate
(24mmol) is added in 25mL three-necked flask, is added 10mL DMF and 3ml toluene, is heated to
140 DEG C, 10h is reacted, reaction solution is poured into a large amount of frozen water, staticly settled, is washed with water after filtering, crude product is obtained.By institute
Obtained crude product is dissolved with acetonitrile, the solution obtained by filtering, is stood after filtrate is mixed with a large amount of distilled water, separates out yellow
Solid, filters and is washed with water, obtain compound of formula I.
Embodiment 1-2
The present embodiment provides the compound containing Cardo structures shown in a kind of formula (I), the preparation method bag of the compound
Include：
By 4,5- carbolines (20mmol), 4- fluorine phthalonitrile (22mmol), 12 4 ethers of hat (5.15mmol) and lithium carbonate
(24mmol) is added in 25mL three-necked flask, adds 10mL dimethyl sulfoxide (DMSO) and toluene, is heated to 130 DEG C, reaction
9h, reaction solution is poured into a large amount of frozen water, staticly settled, is washed with water after filtering, crude product is obtained.By resulting crude product
Dissolved with acetonitrile, the solution obtained by filtering is stood after filtrate is mixed with a large amount of distilled water, separate out yellow solid, filtering is simultaneously
It is washed with water, obtains compound of formula I.
Embodiment 1-3
The present embodiment provides the compound containing Cardo structures shown in a kind of formula (I), the preparation method bag of the compound
Include：
By 4,5- carbolines (20mmol), 4- fluorine phthalonitrile (22mmol), 15 5 ethers of hat (5.15mmol) and sodium carbonate
(24mmol) is added in 25mL three-necked flask, adds 10mL acetone and toluene, is heated to 150 DEG C, reacts 15h, will
Reaction solution is poured into a large amount of frozen water, is staticly settled, and is washed with water after filtering, obtains crude product.By resulting crude product second
Nitrile dissolves, the solution obtained by filtering, is stood after filtrate is mixed with a large amount of distilled water, separates out yellow solid, filters and use water
Washing, 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：
The potassium carbonate of 10mmol formula (I) compound and 0.4mmol is added in 500mL single necked round bottom flask, then added
Enter the mixed solution of 360mL second alcohol and waters, magnetic agitation is reacted after 96h at 86 DEG C, filtered while hot, filtrate is adjusted with watery hydrochloric acid
PH value is saved to 5.5, is staticly settled four days, there are a large amount of white solids to separate out, filtering distillation water washing obtains Formula II compound.
Embodiment 2-2
The present embodiment provides a kind of compound containing Cardo structures as shown in formula (II), and its preparation method includes：
The sodium carbonate of 10mmol formula (I) compound and 0.4mmol is added in 500mL single necked round bottom flask, then added
Enter the mixed solution of 360mL second alcohol and waters, magnetic agitation is reacted after 5d at 80 DEG C, filtered while hot, filtrate is adjusted with watery hydrochloric acid
PH value is staticly settled four days to 5, has a large amount of white solids to separate out, filtering distillation water washing, obtains Formula II compound.
Embodiment 2-3
The present embodiment provides a kind of compound containing Cardo structures as shown in formula (II), and its preparation method includes：
The lithium carbonate of 10mmol formula (I) compound and 0.4mmol is added in 500mL single necked round bottom flask, then added
Enter the mixed solution of 360mL second alcohol and waters, magnetic agitation is reacted after 4d at 90 DEG C, filtered while hot, filtrate is adjusted with watery hydrochloric acid
PH value is staticly settled four days to 6, has a large amount of white solids to separate out, filtering distillation water washing, obtains 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：
1.41mmol formulas (II) compound is added in 25ml beaker, 15mL glacial acetic acid is added, nitrogen is protected,
It is heated under magnetic agitation after all dissolvings, adds 5mL acetic anhydrides, is warming up to after 130 DEG C of 60 hours of backflow, while hot mistake
Filter, after filtrate cooling completely, pours into substantial amounts of absolute ether and separates out solid, staticly settle, filter, washed with a small amount of ether
Wash, Off-white solid, as formula III compound are dried in vacuo to obtain at 150 DEG C.
Embodiment 3-2
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula (III).Its preparation method bag
Include：
1.41mmol formulas (II) compound is added in 25ml beaker, 15mL glacial acetic acid is added, nitrogen is protected,
It is heated under magnetic agitation after all dissolvings, adds 5mL acetic anhydrides, is warming up to after 120 DEG C of 72 hours of backflow, while hot mistake
Filter, after filtrate cooling completely, pours into substantial amounts of absolute ether and separates out solid, staticly settle, filter, washed with a small amount of ether
Wash, Off-white solid, as formula III compound are dried in vacuo to obtain at 140 DEG C.
Embodiment 3-3
Present embodiment also provides a kind of compound containing Cardo structures as shown in formula (III).Its preparation method bag
Include：
1.41mmol formulas (II) compound is added in 25ml beaker, 15mL glacial acetic acid is added, nitrogen is protected,
It is heated under magnetic agitation after all dissolvings, adds 5mL acetic anhydrides, is warming up to after 140 DEG C of backflow 48h, filters while hot, filtrate
Completely after cooling, pour into substantial amounts of absolute ether and separate out solid, staticly settle, filter, washed with a small amount of ether, 160 DEG C
Under be dried in vacuo to obtain Off-white solid, as 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, after 4 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-a compounds.
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, after 5 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-b compounds.
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, after 3 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-c compounds.
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, after 4 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-d compounds.
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, after 4 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-e compounds.
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, after 4 hours of water removal, then except toluene 10 minutes, solution is poured into a large amount of methanol, filtered, dried at 80 DEG C of vacuum, i.e.,
Obtain formula IV-f compounds.
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 as 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：
The affine substitution of fragrance is occurred into the presence of alkali and phase transfer catalyst for 4,5- carbolines and 4- halos phthalonitrile
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 formula (I) compound, wherein the structure of the formula (I) compound 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 3 containing Cardo structures, it is characterised in that it includes：
Formula (II) compound and acetic anhydride are reacted into 2~3d at 120~140 DEG C, wherein 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 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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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006219397A (en) * | 2005-02-09 | 2006-08-24 | Jfe Chemical Corp | Method for producing 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride |
| JP2010235641A (en) * | 2009-03-30 | 2010-10-21 | Sony Chemical & Information Device Corp | Polyamic acid solution, polyimide, and optical device |
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- 2017-05-10 CN CN201710324201.0A patent/CN107033141A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006219397A (en) * | 2005-02-09 | 2006-08-24 | Jfe Chemical Corp | Method for producing 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride |
| JP2010235641A (en) * | 2009-03-30 | 2010-10-21 | Sony Chemical & Information Device Corp | Polyamic acid solution, polyimide, and optical device |
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Application publication date: 20170811 |