WO2021042497A1 - Précurseur de polyimide, film de polyimide formé à partir de celui-ci, et procédé de préparation de film de polyimide - Google Patents

Précurseur de polyimide, film de polyimide formé à partir de celui-ci, et procédé de préparation de film de polyimide Download PDF

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Publication number
WO2021042497A1
WO2021042497A1 PCT/CN2019/115884 CN2019115884W WO2021042497A1 WO 2021042497 A1 WO2021042497 A1 WO 2021042497A1 CN 2019115884 W CN2019115884 W CN 2019115884W WO 2021042497 A1 WO2021042497 A1 WO 2021042497A1
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WO
WIPO (PCT)
Prior art keywords
polyimide
polyimide precursor
diamine
polyimide film
dianhydride
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PCT/CN2019/115884
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English (en)
Chinese (zh)
Inventor
汪亚民
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武汉华星光电半导体显示技术有限公司
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Publication of WO2021042497A1 publication Critical patent/WO2021042497A1/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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—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
    • 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 disclosure relates to a polyimide precursor, in particular to a polyimide film formed therefrom and a preparation method of the polyimide film.
  • Polyimide (PI) occupies a very important role in the field of electronic materials. Its application fields mainly include auxiliary materials for assembly in integrated circuits, packaging materials, passivation layers of components and interlayer insulation materials, etc.; flexible printing The base material of the circuit board; bonding material, etc.
  • OLED Organic Light-Emitting Diode
  • traditional PI materials are brown or yellow, and have poor light transmission properties in the visible light band. This is mainly due to the strong conjugated structure in the molecule to form tight inter-chain stacking, which makes it easy for electrons to be transferred from diamine residues to Residues of dianhydride.
  • the current permeability of the PI substrate material is not high, which causes difficulty in the alignment of the bottom-emission OLED, which has become an important factor in the reduction of production yield. Therefore, how to provide PI flexible substrate materials with high optical transmittance in addition to maintaining mechanical strength and high heat resistance is an important issue in the field of electronic materials.
  • the traditional PI material is brown or yellow, and has poor light transmission performance in the visible light band. This is mainly due to the strong conjugated structure in the molecule forming a tight inter-chain stacking, which makes it easy for electrons to be transferred from diamine residues to diamine residues. Anhydride residues. Therefore, the current permeability of the PI substrate material is not high, which causes difficulty in the alignment of the bottom-emission OLED, which has become an important factor in the reduction of production yield.
  • an object of the present disclosure is to provide a polyimide precursor, a polyimide film formed therefrom, and a preparation method of the polyimide film to provide high heat resistance and high Polyimide film with optical transmittance is used as a flexible substrate material.
  • the present disclosure provides a polyimide precursor, which includes a product formed from a diamine and a dianhydride; wherein the diamine includes a diamine containing a dioxazole structure.
  • the dianhydride includes a fluorine-containing dianhydride.
  • the diamine and the dianhydride are mixed in a ratio of 1:1.2 mol to 1.5:2.5 mol.
  • the diamine containing a dioxazole structure is represented by the chemical formula (1):
  • the product formed by diamine and diacid anhydride includes the repeating unit represented by the chemical formula (2),
  • n 20-100.
  • the present disclosure additionally provides a polyimide film formed from the above polyimide precursor.
  • the polyimide film includes a repeating unit represented by the chemical formula (3),
  • n 1000 ⁇ 2500.
  • the present disclosure additionally provides a method for preparing a polyimide film, which includes the following steps:
  • the S3 step further includes:
  • the method before the step S2, the method further includes the step of heating the polyimide precursor solution at 50°C to 110°C.
  • the present disclosure can provide a polyimide precursor and a polyimide film formed therefrom, wherein the polyimide precursor includes a product formed from a diamine and a dianhydride; the diamine includes A diamine containing a dioxazole structure, and the dianhydride includes a fluorine-containing dianhydride.
  • the polyimide film formed by the polyimide precursor has a dioxazole structure, it can not only reduce the intermolecular force, but also destroy the close packing of the polymer and reduce its crystalline performance; plus the introduction of The dianhydride containing fluorine atoms, the fluorine atoms themselves have high electronegativity, which can effectively reduce the conjugation effect of polyimide molecules, thereby increasing the transmission of the polyimide film while maintaining heat resistance Sex.
  • the present disclosure provides a polyimide precursor, a polyimide film formed therefrom, and a preparation method of the polyimide film.
  • the polyimide film contains the dioxazole structure, which can not only reduce the intermolecular force, but also destroy the close packing of the polymer and reduce its crystalline performance; plus the introduction of dianhydride containing fluorine atoms, fluorine atoms It has high electronegativity and can effectively reduce the conjugation effect of polyimide molecules, thereby improving the permeability of the polyimide film while maintaining heat resistance.
  • FIG. 1 shows a schematic diagram of a curing process of a polyimide film according to an embodiment of the present disclosure
  • FIG. 2 shows a graph of the thermal weight loss curve of a polyimide film according to an embodiment of the present disclosure
  • FIG. 3 shows a graph of light transmittance of a polyimide film according to one embodiment of the present disclosure.
  • the present disclosure provides a polyimide precursor, which includes a product formed from a diamine and a diacid anhydride; wherein the diamine includes a diamine containing a dioxazole structure.
  • Preparation Example 1 provides a preparation of a diamine containing a dioxazole structure as shown in the chemical formula (1).
  • Preparation Example 2 provides a preparation of a polyimide precursor.
  • the polyimide precursor has a repeating unit represented by the chemical formula (2).
  • n 20-100.
  • Preparation Example 3 provides a preparation of a polyimide film.
  • the polyimide film has a repeating unit shown in the chemical formula (3),
  • n 1000 ⁇ 2500.
  • the preparation method of the polyimide film includes the following steps:
  • S3 Heat the film to remove the solvent and make it crosslink and cure; wherein the S3 step further includes:
  • the polyimide precursor was added to 20 to 70 mL of NMP, heated to 50 to 110°C under an argon atmosphere, and reacted for 4 to 6 hours, and then cooled to 80°C to form a viscous solution.
  • the film is cured and cross-linked to obtain the highly cross-linked polyimide film with high transmittance.
  • the entire glass plate and the film are immersed in deionized water for 72 to 96 hours, the polyimide film is peeled, and the polyimide film is again dried in an oven at 80° C. to obtain a separated polyimide film.
  • FIG. 1 is a schematic diagram of a curing process of a polyimide film according to another embodiment of the present disclosure.
  • the crosslinking and curing process of the polyimide film is 3 to 5 hours; the heating rate is 4 to 10°C/min, and the maximum temperature is 420°C to 500°C.
  • Heating is divided into two methods: hard drying and soft drying. Hard drying is to directly raise the temperature to the highest temperature and keep the temperature down for about 1h; soft drying is to divide the constant temperature platform for 2 times or more, and finally to cool down; the polyimide film Hard bake and soft bake to remove the solvent and cross-link and cure.
  • the crosslinking and curing process of the polyimide film of the present disclosure is not limited to this.
  • Fig. 2 shows the thermal weight loss curve of the polyimide film according to one of the embodiments of the present disclosure.
  • the polyimide film of the present disclosure has a mass loss ⁇ 1% at a temperature below 583.6°C
  • Figure 3 shows the light transmittance curve of the polyimide film according to one of the embodiments of the present disclosure.
  • the transmittance of the polyimide film of the present disclosure at a wavelength of 550nm or more is ⁇ 80% ; It can be seen that the polyimide film of the present disclosure does have high heat resistance and high optical transmittance.
  • the present disclosure can provide a polyimide precursor and a polyimide film formed therefrom, wherein the polyimide precursor includes a product formed from diamine and dianhydride;
  • the diamine includes a diamine containing a dioxazole structure, and the dianhydride includes a fluorine-containing dianhydride.
  • the polyimide film formed by the polyimide precursor has a dioxazole structure, it can not only reduce the intermolecular force, but also destroy the close packing of the polymer and reduce its crystalline performance; plus the introduction of The dianhydride containing fluorine atoms, the fluorine atoms themselves have high electronegativity, which can effectively reduce the conjugation effect of polyimide molecules, thereby increasing the transmission of the polyimide film while maintaining heat resistance Sex.

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

Abstract

L'invention concerne un précurseur de polyimide, un film de polyimide formé à partir de celui-ci, et un procédé de préparation dudit polyimide. Le précurseur de polyimide comprend un produit formé à partir de diamine et de dianhydride ; la diamine comprend une diamine contenant une structure d'oxadiazole. Le film de polyimide formé à partir du précurseur de polyimide présente une transmittance élevée.
PCT/CN2019/115884 2019-09-03 2019-11-06 Précurseur de polyimide, film de polyimide formé à partir de celui-ci, et procédé de préparation de film de polyimide WO2021042497A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201910825816.0A CN110643040B (zh) 2019-09-03 2019-09-03 聚酰亚胺前驱物、以其形成之聚酰亚胺膜和该聚酰亚胺膜之制备方法
CN201910825816.0 2019-09-03

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WO2021042497A1 true WO2021042497A1 (fr) 2021-03-11

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WO (1) WO2021042497A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111303423A (zh) * 2020-04-01 2020-06-19 武汉华星光电半导体显示技术有限公司 聚酰亚胺基材及其制造方法、显示面板

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3621076A (en) * 1969-08-11 1971-11-16 Walter F De Winter Block polyheterocyclic polyimide elastomers having high thermal resistance
CN104827731A (zh) * 2014-08-29 2015-08-12 达迈科技股份有限公司 低介电常数聚酰亚胺膜及其制造方法
CN106928481A (zh) * 2017-04-06 2017-07-07 上海交通大学 聚酰亚胺薄膜的优化制备方法
CN107405907A (zh) * 2015-03-26 2017-11-28 东丽株式会社 树脂层叠膜及含有其的层叠体、tft基板、有机el元件滤色片，以及它们的制造方法
WO2018029766A1 (fr) * 2016-08-09 2018-02-15 東レ株式会社 Film multicouche en résine, stratifié contenant celui-ci, substrat tft, filtre coloré d'élément électroluminescent organique, et procédés de fabrication associés
CN109851785A (zh) * 2018-12-18 2019-06-07 苏州予信天材新材料应用技术有限公司 一种低吸湿、高耐热型聚酰亚胺增韧聚合物及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005303013A (ja) * 2004-04-12 2005-10-27 Toyobo Co Ltd フィルム状太陽電池
CN109070012A (zh) * 2016-02-26 2018-12-21 汉阳大学校产学协力团 基于热重排聚(苯并恶唑-酰亚胺)共聚物的超薄型复合膜及其制备方法
CN107759787B (zh) * 2017-11-29 2020-07-28 万华化学集团股份有限公司 一种聚酰亚胺材料的制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3621076A (en) * 1969-08-11 1971-11-16 Walter F De Winter Block polyheterocyclic polyimide elastomers having high thermal resistance
CN104827731A (zh) * 2014-08-29 2015-08-12 达迈科技股份有限公司 低介电常数聚酰亚胺膜及其制造方法
CN107405907A (zh) * 2015-03-26 2017-11-28 东丽株式会社 树脂层叠膜及含有其的层叠体、tft基板、有机el元件滤色片，以及它们的制造方法
WO2018029766A1 (fr) * 2016-08-09 2018-02-15 東レ株式会社 Film multicouche en résine, stratifié contenant celui-ci, substrat tft, filtre coloré d'élément électroluminescent organique, et procédés de fabrication associés
CN106928481A (zh) * 2017-04-06 2017-07-07 上海交通大学 聚酰亚胺薄膜的优化制备方法
CN109851785A (zh) * 2018-12-18 2019-06-07 苏州予信天材新材料应用技术有限公司 一种低吸湿、高耐热型聚酰亚胺增韧聚合物及其制备方法

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