WO2021132197A1 - Résine de polyimide, vernis et film de polyimide - Google Patents

Résine de polyimide, vernis et film de polyimide Download PDF

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Publication number
WO2021132197A1
WO2021132197A1 PCT/JP2020/047791 JP2020047791W WO2021132197A1 WO 2021132197 A1 WO2021132197 A1 WO 2021132197A1 JP 2020047791 W JP2020047791 W JP 2020047791W WO 2021132197 A1 WO2021132197 A1 WO 2021132197A1
Authority
WO
WIPO (PCT)
Prior art keywords
structural unit
mol
varnish
polyamic acid
compound
Prior art date
Application number
PCT/JP2020/047791
Other languages
English (en)
Japanese (ja)
Inventor
洋平 安孫子
三田寺　淳
Original Assignee
三菱瓦斯化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 三菱瓦斯化学株式会社 filed Critical 三菱瓦斯化学株式会社
Priority to CN202080089527.XA priority Critical patent/CN114867766A/zh
Priority to JP2021567461A priority patent/JPWO2021132197A1/ja
Priority to KR1020227021125A priority patent/KR20220123394A/ko
Publication of WO2021132197A1 publication Critical patent/WO2021132197A1/fr

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Classifications

    • 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
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • 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
    • 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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • 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

Definitions

  • the present inventors have found that a polyimide resin containing a combination of specific structural units can solve the above-mentioned problems, and have completed the invention.
  • the structural unit B is a structural unit (B31) derived from a compound represented by the following formula (b31), a structural unit (B32) derived from a compound represented by the following formula (b32), and a following formula (b33).
  • the imidazole compound is at least one selected from the group consisting of imidazole, 1,2-imidazole and 1-benzyl-2-methylimidazole.
  • the polyimide resin of the present invention may contain a structure other than the polyimide chain (a structure in which the structural unit A and the structural unit B are imide-bonded).
  • Examples of the structure other than the polyimide chain that can be contained in the polyimide resin include a structure containing an amide bond.
  • the polyimide resin of the present invention preferably contains a polyimide chain (a structure in which a structural unit A and a structural unit B are imide-bonded) as a main structure. Therefore, the ratio of the polyimide chain to the polyimide resin of the present invention is preferably 50% by mass or more, more preferably 70% by mass or more, still more preferably 90% by mass or more, and particularly preferably 99% by mass. % Or more, and may be 100% by mass.
  • the polyimide resin of the present invention contains a tetracarboxylic acid component containing the compound giving the above-mentioned structural unit A, a compound giving the above-mentioned structural unit (B1), and a diamine component containing the above-mentioned compound giving the structural unit (B2). Can be produced by reacting.
  • the polyimide resin of the present invention is preferably produced by a method of imidizing (dehydrating and ring-closing) the polyamic acid which is a precursor of the polyimide resin.
  • the tetracarboxylic acid component may contain a compound other than the compound that gives the constituent unit (A1), and examples of the compound include the above-mentioned aromatic tetracarboxylic dianhydride, alicyclic tetracarboxylic dianhydride, and fat. Examples thereof include group tetracarboxylic dianhydrides and derivatives thereof (tetracarboxylic dians, alkyl esters of tetracarboxylic dians, etc.).
  • the compound other than the compound given as the structural unit (A1) arbitrarily contained in the tetracarboxylic acid component may be one kind or two or more kinds.
  • the diamine component preferably contains 5 to 60 mol%, more preferably 10 to 40 mol%, and further preferably 20 to 30 mol% of the compound giving the structural unit (B1). Similarly, the diamine component preferably contains 40 to 95 mol%, more preferably 60 to 90 mol%, and even more preferably 70 to 80 mol% of the compound giving the structural unit (B2).
  • aprotonic solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 1,3-dimethylimidazolidinone, tetramethylurea and the like.
  • Amide-based solvents lactone-based solvents such as ⁇ -butyrolactone and ⁇ -valerolactone, phosphorus-containing amide-based solvents such as hexamethylphosphoric amide and hexamethylphosphintriamide, and sulfur-containing solvents such as dimethylsulfone, dimethylsulfoxide, and sulfolane.
  • Example 6 The amount of DABA was changed from 18.182 g (0.080 mol) to 13.636 g (0.060 mol), and the amount of 6FODA was changed from 6.725 g (0.020 mol) to 13.450 g (0.040 mol).
  • a polyamic acid varnish having a solid content concentration of 15% by mass was obtained in the same manner as in Example 4 except that the solid content was changed to. Subsequently, the obtained polyamic acid varnish was applied onto a glass plate by spin coating, held at 80 ° C. for 20 minutes on a hot plate, and then heated at 400 ° C. for 30 minutes in a hot air dryer under a nitrogen atmosphere (ascending). The solvent was evaporated at a temperature rate of 5 ° C./min) and further thermally imidized to obtain a polyimide film. The results are shown in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La résine de polyimide selon la présente invention a une unité structurale A dérivée d'un dianhydride d'acide tétracarboxylique et une unité structurale B dérivée d'une diamine. L'unité structurale B comprend une unité structurale (B1) dérivée d'un composé représenté par la formule (b1) et une unité structurale (B2) dérivée d'un composé représenté par la formule (b2). La présente invention concerne : une résine de polyimide qui peut former un film ayant une faible contrainte résiduelle, une excellente résistance à la chaleur et un faible coefficient de dilatation thermique linéaire ; un vernis contenant un acide polyamique qui est un précurseur de ladite résine de polyimide ; et un film de polyimide.
PCT/JP2020/047791 2019-12-27 2020-12-22 Résine de polyimide, vernis et film de polyimide WO2021132197A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202080089527.XA CN114867766A (zh) 2019-12-27 2020-12-22 聚酰亚胺树脂、清漆和聚酰亚胺薄膜
JP2021567461A JPWO2021132197A1 (fr) 2019-12-27 2020-12-22
KR1020227021125A KR20220123394A (ko) 2019-12-27 2020-12-22 폴리이미드 수지, 바니시 및 폴리이미드 필름

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019-239648 2019-12-27
JP2019239648 2019-12-27

Publications (1)

Publication Number Publication Date
WO2021132197A1 true WO2021132197A1 (fr) 2021-07-01

Family

ID=76572988

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/047791 WO2021132197A1 (fr) 2019-12-27 2020-12-22 Résine de polyimide, vernis et film de polyimide

Country Status (5)

Country Link
JP (1) JPWO2021132197A1 (fr)
KR (1) KR20220123394A (fr)
CN (1) CN114867766A (fr)
TW (1) TW202134318A (fr)
WO (1) WO2021132197A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023085041A1 (fr) * 2021-11-11 2023-05-19 三菱瓦斯化学株式会社 Résine de polyimide, vernis et film de polyimide

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11282157A (ja) * 1997-10-31 1999-10-15 Nippon Zeon Co Ltd ポリイミド系感光性樹脂組成物
WO2018097143A1 (fr) * 2016-11-24 2018-05-31 日産化学工業株式会社 Composition pour former un substrat de dispositif flexible
JP2019112632A (ja) * 2017-12-22 2019-07-11 ドゥーサン コーポレイション ポリアミック酸溶液及びこれを用いた透明ポリイミド樹脂フィルム
WO2020138360A1 (fr) * 2018-12-28 2020-07-02 三菱瓦斯化学株式会社 Copolymère d'imide-(acide amique) et son procédé de production, vernis et film de polyimide

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005232383A (ja) 2004-02-20 2005-09-02 Asahi Kasei Electronics Co Ltd ポリアミド酸誘導体
WO2014098235A1 (fr) 2012-12-21 2014-06-26 旭化成イーマテリアルズ株式会社 Précurseur de polyimide et composition de résine le contenant
TWI804465B (zh) * 2016-05-02 2023-06-11 日商三菱瓦斯化學股份有限公司 聚醯亞胺樹脂、聚醯亞胺樹脂組成物及聚醯亞胺薄膜

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11282157A (ja) * 1997-10-31 1999-10-15 Nippon Zeon Co Ltd ポリイミド系感光性樹脂組成物
WO2018097143A1 (fr) * 2016-11-24 2018-05-31 日産化学工業株式会社 Composition pour former un substrat de dispositif flexible
JP2019112632A (ja) * 2017-12-22 2019-07-11 ドゥーサン コーポレイション ポリアミック酸溶液及びこれを用いた透明ポリイミド樹脂フィルム
WO2020138360A1 (fr) * 2018-12-28 2020-07-02 三菱瓦斯化学株式会社 Copolymère d'imide-(acide amique) et son procédé de production, vernis et film de polyimide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023085041A1 (fr) * 2021-11-11 2023-05-19 三菱瓦斯化学株式会社 Résine de polyimide, vernis et film de polyimide

Also Published As

Publication number Publication date
CN114867766A (zh) 2022-08-05
KR20220123394A (ko) 2022-09-06
TW202134318A (zh) 2021-09-16
JPWO2021132197A1 (fr) 2021-07-01

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