WO2016003146A1 - Solution de poly(acide amique) résistant à la chaleur élevée et film de polyimide - Google Patents

Solution de poly(acide amique) résistant à la chaleur élevée et film de polyimide Download PDF

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Publication number
WO2016003146A1
WO2016003146A1 PCT/KR2015/006666 KR2015006666W WO2016003146A1 WO 2016003146 A1 WO2016003146 A1 WO 2016003146A1 KR 2015006666 W KR2015006666 W KR 2015006666W WO 2016003146 A1 WO2016003146 A1 WO 2016003146A1
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Prior art keywords
acid solution
polyamic acid
dianhydride
diamine compound
cte
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PCT/KR2015/006666
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English (en)
Korean (ko)
Inventor
민웅기
박효준
정학기
홍기일
Original Assignee
코오롱인더스트리 주식회사
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Priority claimed from KR1020150091870A external-priority patent/KR102248994B1/ko
Application filed by 코오롱인더스트리 주식회사 filed Critical 코오롱인더스트리 주식회사
Priority to CN201580035000.8A priority Critical patent/CN106536597A/zh
Priority to JP2016575755A priority patent/JP6715406B2/ja
Priority to US15/322,957 priority patent/US10538665B2/en
Priority to EP15815907.9A priority patent/EP3162838A4/fr
Publication of WO2016003146A1 publication Critical patent/WO2016003146A1/fr

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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
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions 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 C08L61/00 - C08L77/00
    • 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

Definitions

  • the present invention relates to a high heat-resistant polyamic acid and a polyimide film, and more particularly, to a high heat-resistant polyimide film having improved thermal dimensional stability and a polyamic acid solution polymerized using a diamine having carboxylic acid introduced therein.
  • Polyimide exhibits excellent heat resistance, mechanical properties, and electrical properties compared to other general-purpose resins and engineering plastics, and thus is useful as a useful material in the manufacture of electric, electronic parts, and other products requiring high heat resistance.
  • polyimide resins are used in a wide range of fields such as heat-resistant high-tech materials such as automobile materials, aviation materials, and spacecraft materials, and electronic materials such as insulation coating agents, insulating films, semiconductors, and TFT-LCD electrode protective films. It is also used as a display material, such as an optical fiber and a liquid crystal aligning film, and the transparent electrode film which contained the conductive filler in the film, or coated on the surface.
  • the polyimide polymerizes dianhydride and diamine in a solvent to synthesize a polyamic acid, and heats it to synthesize polyimide through dehydration and cyclization, or dehydration by chemical dehydration using a dehydrating agent.
  • Polyimides are synthesized using a cyclization reaction.
  • a cast method of applying a polyamic acid derivative, which is a polyimide precursor, to a carrier plate and curing the polyimide film to obtain a polyimide film is common.
  • the said cast method consists of the process of apply
  • polyimide is excellent in physical properties such as heat resistance when producing a film, but as a rigid rod structure, it is difficult to form a film is difficult to break and difficult to manufacture.
  • a composition containing paraphenylenediamine and pyromellitic acid dianhydride there is often a problem that foaming or film forming and peeling do not occur when applied on a support and heat treated.
  • the polyimide film shrinks or expands due to the characteristics of the film when the temperature is changed at a high temperature, and the width of the change is not always constant, and thus the use of the polyimide film has been limited in fields requiring thermal dimensional stability.
  • the thermal stability in the high temperature process must be premised. That is, in the case of a glass substrate commonly used as a substrate of the display element, the coefficient of thermal expansion is about 4ppm / °C, in order to replace the glass substrate, the thermal expansion coefficient of polyimide film must be at least 10ppm / °C or less do.
  • the present invention is to provide a high heat-resistant polyamic acid solution useful for forming a high heat-resistant film and further to provide a polyimide film having excellent thermal dimensional stability.
  • a diamine compound and a dianhydride compound includes a polymer, wherein the diamine compound comprises a diamine compound having a carboxylic acid functional group in 1 mol% to 10 mol% based on the total moles of the total diamine compound It provides a polyamic acid solution.
  • the polymer may be obtained by reacting a diamine compound and a dianhydride compound in a 1: 0.95 to 1: 1 molar ratio.
  • the diamine compound having a carboxylic acid functional group is 1,3-diaminobenzoic acid (DABA), 3,5-diaminophthalic acid (DAPA), and 4,4 It may include one or more selected from the group consisting of -diaminobiphenyl-3,3-tetracarboxylic acid (DATA).
  • DABA 1,3-diaminobenzoic acid
  • DAPA 3,5-diaminophthalic acid
  • 4,4 It may include one or more selected from the group consisting of -diaminobiphenyl-3,3-tetracarboxylic acid (DATA).
  • DATA -diaminobiphenyl-3,3-tetracarboxylic acid
  • the diamine compound may include 90 to 99 mol% of the aromatic diamine compound based on the total number of moles of the diamine compound.
  • the aromatic diamine compound is oxydianiline (ODA), paraphenylenediamine (pPDA), m-phenylenediamine (mPDA), p-methylenediamine (pMDA) and meta One or more compounds selected from the group consisting of methylenediamine (mMDA) or mixtures thereof.
  • ODA oxydianiline
  • pPDA paraphenylenediamine
  • mPDA m-phenylenediamine
  • pMDA p-methylenediamine
  • the dianhydride compound is pyromellitic dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride (PMDA)), benzophenone tetracarbide Cyclic dianhydride (BTDA), biphenyl tetracarboxylic dianhydride (BPDA), biscarboxyphenyl dimethyl silane dianhydride (SiDA), oxydiphthalic dianhydride (ODPA), bis dicarboxyphenoxy di
  • BPDA biphenyl tetracarboxylic dianhydride
  • SiDA biscarboxyphenyl dimethyl silane dianhydride
  • ODPA oxydiphthalic dianhydride
  • BDSDA phenyl sulfide dianhydride
  • SO 2 DPA sulfonyl diphthalic anhydride
  • the polymer may have a weight average molecular weight of 100,000 to 150,000.
  • the polyamic acid solution may have a viscosity of 50 to 200ps.
  • the polyimide film which is an imide of the polyamic acid solution according to the above embodiments, includes a polyimide crosslinked with an amide bond (-CONH-) between the main chain and the main chain. do.
  • the thermal expansion coefficient measured in the temperature range of 50 to 500 °C is 5ppm / °C or less, the thermal expansion coefficient increase index defined by the following equation 1 may be 10 or less.
  • 1 st CTE is the coefficient of thermal expansion obtained by the first measurement in the temperature range of 50 to 500 °C according to the TMA-method method
  • 2 nd CTE is the first measurement after cooling the first measured specimen to room temperature It is a coefficient of thermal expansion obtained by secondary measurement under the same conditions (however, 1 st CTE ⁇ 2 nd CTE is satisfied).
  • Polyimide film according to the embodiment may also be one of ASTM D882 standard tensile strength of 250 to 350 MPa, elastic modulus of 7.0 to 10.0GPa, elongation of 13 to 15%.
  • According to the present invention can provide a high heat-resistant polyamic acid solution that can easily form a high heat-resistant film, and furthermore, the polyimide film prepared using the same can exhibit excellent thermal dimensional stability.
  • a diamine compound and a dianhydride compound comprising a polymer, wherein the diamine compound comprises a diamine compound having a carboxylic acid functional group in 1 mol% to 10 mol% based on the total moles of the total diamine compound It provides a phosphorus polyamic acid solution.
  • the diamine compound contains the diamine compound which has a carboxylic acid functional group, it is a polyimide film excellent in thermal dimensional stability at the time of imidating and forming into a film from the obtained polyamic-acid solution. Can be easily obtained.
  • the carboxylic acid functional group included in the molecular chain of the diamine compound does not directly participate in the polymerization reaction with other diamines, but is thus used between side chains in the polymer.
  • the carboxylic acid functional groups derived from the residue are imidized and formed into a polyimide film, some of the carboxylic acid functional groups may be thermally decomposed at high temperature in the imidization process, but ultimately, It is possible to form network structures such as crosslinks, specifically amide bonds (-CONH-), between the main chains.
  • heat resistance in particular, thermal dimensional stability, can be remarkably improved as compared to the uncrosslinked polyimide. It can also improve mechanical properties.
  • Diamine having a carboxylic acid functional group to form such a cross-linking structure is preferably included 1 mol% to 10 mol% based on the total moles of the diamine compound, when added to less than 1 mol%, the part (connection point) that is connected between the main chain To crosslinking point) is too small compared to the original intended degree, there is a limit to the improvement of physical properties as expected, and if the content exceeds 10 mol%, the main chain forming the film is a ladder type linear arrangement, as intended.
  • the structure is not connected to each other but close to the net structure, which degrades the solubility of the polymer itself and, in severe cases, may precipitate as a solid in a solution or may cause a problem in that the film is broken during film formation due to local crosslinking. .
  • the thermal dimensional stability reflected in the polyimide film may be more excellent, and since the carboxylic acid functional groups are crosslinked in the film, tensile strength and elastic modulus of the entire film may be improved. Can be.
  • the diamine compound having a carboxylic acid functional group is 1,3-diaminobenzoic acid (DABA), 3,5-diaminophthalic acid (DAPA), 4,4-diaminobiphenyl It may include one or more selected from the group consisting of -3,3-tetracarboxylic acid (DATA), of which 4-diaminobiphenyl-3,3-tetracarboxylic acid (DATA) is used. Since it has two or more crosslinkable functional groups in the main chain, it may be most advantageous in terms of coefficient of thermal expansion and improvement of mechanical properties.
  • DABA 1,3-diaminobenzoic acid
  • DAPA 3,5-diaminophthalic acid
  • DATA 4,4-diaminobiphenyl
  • DATA 4-diaminobiphenyl-3,3-tetracarboxylic acid
  • 90 to 99 mol% of the diamine except for the diamine compound having a carboxylic acid functional group may be an aromatic diamine compound.
  • the aromatic diamine compound is selected from the group consisting of oxydianiline (ODA), paraphenylenediamine (pPDA), m-phenylenediamine (mPDA), p-methylenediamine (pMDA) and methmethylenediamine (mMDA). Preference is given to using at least two compounds or mixtures thereof.
  • the diamine and dianhydride may have a molar ratio of 1: 0.95 to 1: 1, more preferably 1: 0.96 to 1: 0.99, most preferably 1: 0.97 To 1: 0.98.
  • the mole number of diamine is 1, the molar number of dianhydride is less than 0.95.
  • the molecular weight is not good, so the basic physical properties of the film are not good. If the molar number of diamine is 1, the viscosity is too high. May occur.
  • the dianhydride compound is pyromellitic dianhydride (1,2,4,5-benzene tetracarboxylic dianhydride (PMDA)), benzophenone tetracarboxylic dianhydride Hydride (BTDA), biphenyl tetracarboxylic dianhydride (BPDA), biscarboxyphenyl dimethyl silane dianhydride (SiDA), oxydiphthalic dianhydride (ODPA), bis dicarboxyphenoxy diphenyl sulfide dianhydride It may be used alone or in combination of one or more selected from the group consisting of a lide (BDSDA) and sulfonyl diphthalic hydride (SO 2 DPA).
  • PMDA pyromellitic dianhydride
  • BTDA benzophenone tetracarboxylic dianhydride Hydride
  • BPDA biphenyl tetracarboxylic dianhydride
  • SiDA biscarboxypheny
  • Examples of the diamine compounds and dianhydride compounds are preferable ones in terms of heat resistance and mechanical properties, and the diamine compounds having carboxylic acid functional groups in combination with these compounds at a constant molar ratio facilitate film formation while maximizing heat resistance. It is possible to obtain a polyimide film having excellent mechanical properties.
  • the polyamic acid solution is m-cresol, N-methyl-2-pyrrolidone (NMP), dimethylformamide (DMF), dimethylacetamide (DMAc), dimethyl sulfoxide as an organic solvent. It may include one or more polar solvents selected from the side (DMSO), acetone, diethyl acetate.
  • the moisture content remaining in the solvent is preferably 1000 ppm or less in terms of preventing the deterioration of physical properties, and more preferably, the moisture content is 100 ppm or less.
  • the content of the solvent is preferably 50 to 95% by weight, more preferably 70 to 90% by weight of the total polyamic acid solution in order to obtain a viscosity suitable for film processing.
  • the polyamic acid solution of the present invention preferably contains a polyamic acid having a weight average molecular weight of 100,000 to 150,000, preferably a viscosity of 50 to 200 ps.
  • a polyamic acid solution of the present invention satisfies the above molecular weight and viscosity, the final film is prevented from warping and warping during processing, especially when exposed to high temperatures in the process when used for display element substrates. It is possible to minimize the dimensional change.
  • a polyimide film which is an imide of the polyamic acid solution described above, and comprises a polyimide crosslinked by an amide bond between the main chain and the main chain.
  • the polyimide film according to the present invention is obtained by imidating a polyamic acid solution which is a polymer of a diamine compound containing a diamine having a carboxylic acid functional group and a dianhydride compound, and a carboxylic acid functional group in a diamine having a carboxylic acid functional group. Does not directly participate in the polymerization reaction, and serves to crosslink the main chain and the main chain which are imidated in a high temperature process of imidating a polyamic acid. At this time, crosslinking may be by forming an amide bond.
  • the carboxylic acid functional group may thermally decompose in some high temperature air but substantially react with the amine functional group between the polyimide main chain and the main chain to form a crosslinking reaction at high temperature.
  • the degree of crosslinking of the polymer of the polyimide film is improved, thereby exhibiting properties such as high strength, high elasticity, and low shrinkage, and can easily form a film.
  • the polyimide film is a film having a thermal expansion coefficient measured at a temperature range of 50 to 500 ° C. or less and 5 ppm / ° C. or less, and a thermal expansion coefficient increasing index defined by Equation 1 below 10 or less.
  • 1 st CTE is the coefficient of thermal expansion obtained by the first measurement in the temperature range of 50 to 500 °C according to the TMA-method method
  • 2 nd CTE is the first measurement after cooling the first measured specimen to room temperature It is a coefficient of thermal expansion obtained by secondary measurement under the same conditions (however, 1 st CTE ⁇ 2 nd CTE is satisfied).
  • the coefficient of thermal expansion is a characteristic that numerically represents the change in the length of intermolecular or interatomic bonds as the temperature of the organic material increases with an average value of 5ppm / It is preferable that the thermal expansion coefficient increase index represented by Equation 1 is less than or equal to 10 ° C., in particular for thermal dimensional stability.
  • the coefficient of thermal expansion of polyimide film exceeds 5 ppm / °C or the coefficient of thermal expansion increase is more than 10 when used as a substrate film, it is likely to be warped or warped as it is exposed to high temperature in the process. Errors and dimensional changes can cause difficulties in practical use.
  • the measurement of the coefficient of thermal expansion is preferably measured by heating up to 50 to 500 °C at a rate of 5 to 10 °C per minute, 2 nd CTE immediately after cooling to room temperature to remove the thermal history after 1 st CTE measurement It is preferable to measure.
  • the room temperature may be defined as 25 ⁇ 50 °C.
  • the 2 nd coefficient of thermal expansion is measured under the same measurement conditions as that of the 1 st coefficient of thermal expansion, and if the film sample to be measured has a problem of absorbing moisture from external moisture, shrinkage behavior occurs in the temperature range where moisture flows, so that the CTE value is properly It should be noted that it cannot be measured.
  • the crosslinking between the polyimide main chain and the main chain satisfies high strength and high elasticity, specifically, the ASTM D882 standard tensile strength is 250 to 350 MPa, elastic modulus is 7.0 to 10.0 GPa , Polyimide film having an elongation of 13 to 15% can be provided.
  • the method for producing the polyimide film is not particularly limited, and (a) a diamine compound containing 1 mol% to 10 mol% of a diamine compound having a carboxylic acid functional group based on the total number of moles of the diamine compound; And copolymerizing the dianhydride compound to prepare a polyamic acid solution. (b) casting the polyamic acid solution of step (a) to the support to undergo imidization.
  • the method of preparing a polyamic acid solution through the step (a) is as described above, it will be omitted.
  • the reaction temperature is preferably -20 to 80 °C
  • the reaction time is preferably 2 to 48 hours.
  • the copolymerization reaction is more preferably carried out in an inert atmosphere such as argon or nitrogen.
  • a method of imidizing the polyamic acid solution by casting the polyamic acid solution in the step (b) is not limited thereto, and the method is not limited thereto, and thermal imidization, chemical imidization, or thermal imide
  • the compounding method and the chemical imidization method can be used in combination.
  • it is preferable to proceed only with the thermal imidization method in view of the fact that the molecular weight of the polymer, that is, the degree of polymerization is rapidly increased and the solubility decreases, that is, the solidification is prevented to prevent the film from breaking.
  • the thickness of the finally produced polyimide film is not specifically limited, It is preferable that it is the range of 10-20 micrometers, More preferably, it may be 10-15 micrometers.
  • DATA 4,4-diaminobiphenyl-3,3-tetracarboxylic acid
  • BPDA ric dianhydride
  • PMDA 1,2,4,5-benzene tetracarboxylic dianhydride
  • a polyimide film was obtained in the same manner as in Example 1, except that 42.12 g of p-PDA corresponding to 95 mol% of total diamine and 5.69 g of DATA corresponding to 5 mol% were used. However, at this time, the polyamic acid solution obtained in the preparation process of Example 2 had a solid content of 17 wt% and a viscosity of 135 ps.
  • a polyimide film was obtained in the same manner as in Example 1, except that 39.92 g of p-PDA corresponding to 90 mol% of diamine total mole number and 10.20 g of DATA corresponding to 10 mol% were used. However, at this time, the polyamic acid solution obtained in the manufacturing process of Example 3 had a solid content of 17 wt% and a viscosity of 138 ps.
  • a polyimide film was obtained in the same manner as in Example 1, except that 44.40 g of p-PDA corresponding to 99.1 mol% of diamine total moles and 0.93 g of DATA corresponding to 0.9 mol% were used. However, at this time, the polyamic acid solution obtained in the manufacturing process of Comparative Example 1 had a solid content of 17 wt% and a viscosity of 136 ps.
  • a polyimide film was obtained in the same manner as in Example 1, except that 39.48 g of p-PDA corresponding to 89 mol% of diamine total moles and 11.22 g of DATA corresponding to 11 mol% were used. At this time, the polyamic acid solution obtained in the preparation process of Comparative Example 2 had a solid content of 17 wt% and a viscosity of 140 ps.
  • the polyimide film was prepared in the same manner as in Example 1, except that 39.90 g of p-PDA corresponding to 85 mol% of diamine and 11.398 g of DATA corresponding to 15 mol% were used, but DATA was not dissolved in a solvent. Thus, the polyamic acid solution itself could not be obtained.
  • the coefficient of thermal expansion was measured twice according to TMA-Method using TMA (Perkin Elmer, Diamond TMA) and the temperature rising rate was 10 ° C / min and 100mN. At this time, the length of the specimen to be measured was measured by cutting width 4mm, length 23mm.
  • TMA Perkin Elmer, Diamond TMA
  • the temperature increase rate was raised to 500 ° C with a load of 10 ° C / min and 100mN
  • CTE was defined as the coefficient of thermal expansion of the film, and the number of measurement On the one hand it is called 1 st CTE). 1 st CTE measurement completed Cool to room temperature at 5 °C / min.
  • the coefficient of thermal expansion means a coefficient of linear expansion.
  • Equation 1 The obtained 1 st CTE and 2 nd CTE values were substituted into Equation 1 to calculate the coefficient of thermal expansion.
  • 1 st CTE is the coefficient of thermal expansion obtained by the first measurement in the temperature range of 50 to 500 °C according to the TMA-method method
  • 2 nd CTE is the first measurement after cooling the first measured specimen to room temperature It is a coefficient of thermal expansion obtained by secondary measurement under the same conditions (however, 1 st CTE ⁇ 2 nd CTE is satisfied).
  • Instron 5967 was used to measure tensile strength, modulus and elongation in accordance with ASTM-D882 standards.
  • the specimen size was 13mm * 100mm, Load cell 1KN, and tension rate was measured 7 times per specimen at 50mm / min and measured as the average value except the maximum and minimum values.
  • the polyimide film prepared according to the present invention was expected to ensure thermal dimensional stability.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne un solution de poly(acide amique) résistant à la chaleur élevée et un film de polyimide et permet d'obtenir un film de polyimide qui présente une stabilité dimensionnelle thermique améliorée par le fait de comprendre une solution de poly(acide amique) contenant un polymère d'un composé de diamine et d'un dianhydride, le polymère contenant un composé de diamine présentant un groupe fonctionnel carboxyle à raison de 1 % en mole à 10 % en mole sur base de la teneur totale en diamines ; et, en tant qu'imide correspondant, un polyimide dans lequel des chaînes principales sont réticulées entre elles par l'intermédiaire d'une liaison amide.
PCT/KR2015/006666 2014-06-30 2015-06-30 Solution de poly(acide amique) résistant à la chaleur élevée et film de polyimide WO2016003146A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201580035000.8A CN106536597A (zh) 2014-06-30 2015-06-30 高耐热聚酰胺酸溶液和聚酰亚胺膜
JP2016575755A JP6715406B2 (ja) 2014-06-30 2015-06-30 高耐熱ポリイミドフィルム
US15/322,957 US10538665B2 (en) 2014-06-30 2015-06-30 High heat-resistant polyamic acid solution and polyimide film
EP15815907.9A EP3162838A4 (fr) 2014-06-30 2015-06-30 Solution de poly(acide amique) résistant à la chaleur élevée et film de polyimide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20140081403 2014-06-30
KR10-2014-0081403 2014-06-30
KR10-2015-0091870 2015-06-29
KR1020150091870A KR102248994B1 (ko) 2014-06-30 2015-06-29 고내열 폴리아믹산 용액 및 폴리이미드 필름

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
JP2017155167A (ja) * 2016-03-03 2017-09-07 日立化成デュポンマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜
JP2017155168A (ja) * 2016-03-03 2017-09-07 日立化成デュポンマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜
JP2020183540A (ja) * 2020-07-09 2020-11-12 Ｈｄマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜
JPWO2020066561A1 (ja) * 2018-09-27 2021-03-11 富士フイルム株式会社 重合体の製造方法、及び重合体を製造するフロー式反応システム

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US5741599A (en) * 1995-10-12 1998-04-21 Pi Materials Research Laboratory Polyimide compositions for electrodeposition and coatings formed of the same
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US4778872A (en) * 1984-11-06 1988-10-18 Ube Industries, Ltd. Polyamic acid solution composition and polymide film made therefrom
US5741599A (en) * 1995-10-12 1998-04-21 Pi Materials Research Laboratory Polyimide compositions for electrodeposition and coatings formed of the same
US6790930B1 (en) * 1999-10-06 2004-09-14 Kaneka Corporation Process for producing polyimide resin
KR20050113235A (ko) * 2003-04-18 2005-12-01 가부시키가이샤 가네카 열경화성 수지 조성물, 이를 이용한 적층체 및 회로 기판
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017155167A (ja) * 2016-03-03 2017-09-07 日立化成デュポンマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜
JP2017155168A (ja) * 2016-03-03 2017-09-07 日立化成デュポンマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜
JPWO2020066561A1 (ja) * 2018-09-27 2021-03-11 富士フイルム株式会社 重合体の製造方法、及び重合体を製造するフロー式反応システム
JP7012866B2 (ja) 2018-09-27 2022-01-28 富士フイルム株式会社 重合体の製造方法、及び重合体を製造するフロー式反応システム
JP2020183540A (ja) * 2020-07-09 2020-11-12 Ｈｄマイクロシステムズ株式会社 樹脂組成物及びポリイミド樹脂膜

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