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WO2023038322A1 - Composition d'acide polyamique et polyimide préparé à partir de celle-ci - Google Patents

Composition d'acide polyamique et polyimide préparé à partir de celle-ci Download PDF

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Publication number
WO2023038322A1
WO2023038322A1 PCT/KR2022/012452 KR2022012452W WO2023038322A1 WO 2023038322 A1 WO2023038322 A1 WO 2023038322A1 KR 2022012452 W KR2022012452 W KR 2022012452W WO 2023038322 A1 WO2023038322 A1 WO 2023038322A1
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Prior art keywords
polyamic acid
acid composition
mol
dianhydride
monomer component
Prior art date
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Ceased
Application number
PCT/KR2022/012452
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English (en)
Korean (ko)
Inventor
황인환
박세주
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PI Advanced Materials Co Ltd
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PI Advanced Materials Co Ltd
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Priority to CN202280061248.1A priority Critical patent/CN117940486A/zh
Publication of WO2023038322A1 publication Critical patent/WO2023038322A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate

Definitions

  • polyimide (PI) resin refers to a highly heat-resistant resin prepared by solution polymerization of aromatic dianhydride and aromatic diamine or aromatic diisocyanate to prepare a polyamic acid derivative, followed by imidization by curing. refers to
  • Polyimide is a polymer material with thermal stability based on a rigid aromatic main chain, and has mechanical properties such as excellent strength, chemical resistance, weather resistance and heat resistance based on the chemical stability of the imide ring.
  • polyimide is in the limelight as a high-functional polymer material applicable to a wide range of industries such as electronics, communication, and optics due to its excellent electrical properties such as insulating properties and low permittivity.
  • An object of the present invention is to provide a polyamic acid composition and a polyimide film having excellent thermal properties such as dimensional stability and heat resistance while having high transparency.
  • the present invention can provide a polyamic acid composition and polyimide having excellent processability, excellent mechanical properties, as well as low weight loss and low expansion coefficient against heat due to a high glass transition temperature while having high transparency.
  • Polyimide (PI) resin is prepared by polymerization of aromatic dianhydride and aromatic diamine or aromatic diisocyanate to prepare a polyamic acid derivative, followed by imidization by curing.
  • Polyimide has excellent thermal stability based on a rigid aromatic backbone.
  • the transparency is so low that there is a limit to use in the electronic material field, especially in the display field requiring high transparency.
  • the present invention includes a compound having a special type of aromaticity in addition to a compound having 1 to 2 aromatic rings as a part of the dianhydride monomer component and / or diamine component constituting the polyimide, and by optimizing their content, A polyamic acid composition and polyimide having high transparency and excellent thermal properties can be provided.
  • the present invention is based on the glass transition temperature (Tg), which can predict thermal properties and also reflect mechanical properties. noticed.
  • the polyimide precursor may mean dianhydride and diamine excluding the solvent in the polyamic acid composition.
  • the present invention relates to a polyamic acid composition.
  • the polyamic acid composition includes a polyamic acid having a polymerization unit derived from a dianhydride monomer component and a diamine monomer component, and a solvent.
  • the fluorene skeleton may not generate a resonance effect due to electron transfer with the main chain of the dianhydride monomer component and/or the diamine monomer component.
  • the dianhydride monomer component may include a compound having a fluorene skeleton, and the compound having a fluorene skeleton among the dianhydride monomer components is 9,9-bis(3,4-dicarboxyphenyl) Can be fluorene dianhydride (BPAF) or 4,4'-(9H-fluorene-9,9 diyl)bis(4,1-phenylene))bis(4-aminobenzamide) (FDA-ADA) there is.
  • BPAF fluorene dianhydride
  • FDA-ADA 4,4'-(9H-fluorene-9,9 diyl)bis(4,1-phenylene))bis(4-aminobenzamide)
  • the upper limit of the content of the compound having a fluorene skeleton is less than 24 mol%, less than 23 mol%, less than 22 mol%, less than 21 mol%, less than 20 mol% with respect to the total dianhydride monomer component and diamine monomer component Less than 19 mol%, less than 18 mol%, less than 17 mol%, less than 16 mol%, less than 15 mol%, less than 14 mol%, less than 13 mol%, less than 12 mol%, less than 11 mol%, 10 mol% less than 9 mol%, less than 8 mol% or less than 7 mol%, with lower limits greater than 0.01 mol%, greater than 0.05 mol%, greater than 0.9 mol%, greater than 1 mol%, greater than 2 mol%, greater than 3 mol% or greater than 4 mol%.
  • the compound having a fluorene skeleton is 0.5 mol% to 30 mol%, 0.6 mol% to 25 mol%, 0.7 mol% to 23 mol%, 3 mol% to 10 mol%, 3 mol% to 10 mol%, based on the total polyimide precursor. mol % to 9 mol % or 3 mol % to 7 mol %.
  • the content of the compound having a fluorene skeleton in the dianhydride monomer component may be less than 15 mol%, for example, the upper limit of the content of the compound having a fluorene skeleton in the dianhydride monomer component is less than 14 mol%, less than 13 mol%, less than 12 mol%, less than 11 mol%, less than 10 mol%, less than 9 mol%, less than 8 mol%, less than 7 mol% or less than 6 mol%, with lower limits greater than 0.01 mol% and 0.05 mol%.
  • the compound having a fluorene skeleton among the dianhydride monomer components is 1 mol% to 10 mol%, 3 mol% to 10 mol%, 3 mol% to 9 mol%, or 3 mol% to 3 mol% with respect to the polyimide precursor 7 mol%.
  • the compound having a fluorene skeleton among the diamine monomer components is 1 mol% to 10 mol%, 3 mol% to 10 mol%, 3 mol% to 9 mol%, or 3 mol% to 7 mol% based on the polyimide precursor may be %.
  • a compound having a fluorene skeleton can contribute to high transparency of polyimide after curing, but weakens mechanical strength and thermal properties. Specifically, when the content of the compound having a fluorene skeleton in the polyamic acid composition increases, the mechanical strength and thermal expansion coefficient of the cured polyamide decrease, and the thermal decomposition temperature decreases, resulting in deterioration in mechanical and thermal properties. Therefore, in the present invention, by limiting the content of the compound having a fluorene skeleton to the above range, it is possible to prevent deterioration of mechanical strength and thermal properties while having high transparency.
  • the rigidity and crosslinking density of the aromatic main chain which can prevent a rapid decrease in glass transition temperature, can be maintained, so that after curing, mechanical strength and thermal properties are lowered can be minimized.
  • the glass transition temperature as described above it is possible to minimize deterioration in mechanical strength and thermal properties after curing of the polyamic acid composition, minimize flowability due to thermal deformation, and thus improve processability.
  • the dianhydride monomer component and the diamine monomer component other than the compound having a fluorene skeleton may each include a compound having one or two or more benzene rings.
  • the dianhydride monomer component and the diamine monomer component other than the compound having a fluorene skeleton may each include a compound having one or two benzene rings.
  • dianhydride monomer components compounds having one or two benzene rings are pyromellitic dianhydride (PMDA), 3,3',4,4'-biphenyltetracarboxylic dianhydride (s- BPDA), 2,3,3',4'-biphenyltetracarboxylic dianhydride (a-BPDA), 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA) , It may be at least one selected from the group consisting of oxydiphthalic dianhydride (ODPA) and 4,4-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA).
  • PMDA pyromellitic dianhydride
  • s- BPDA 3,3',4,4'-biphenyltetracarboxylic dianhydride
  • a-BPDA 2,3,3',4'-biphenyltetracarboxylic dian
  • the dianhydride monomer component other than the compound having a fluorene skeleton may include a compound having two benzene rings, and the compound having two benzene rings as the dianhydride monomer component is 3,3' ,4,4'-biphenyltetracarboxylic dianhydride (s-BPDA), 2,3,3',4'-biphenyltetracarboxylic dianhydride (a-BPDA), 3,3' ,4,4'-benzophenonetetracarboxylic dianhydride (BTDA), oxydiphthalic dianhydride (ODPA) and 4,4-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA) It may be at least one selected from the group consisting of.
  • s-BPDA 3,3' ,4,4'-biphenyltetracarboxylic dianhydride
  • a-BPDA 2,3,3',4'-biphenyl
  • the dianhydride monomer component having one or two benzene rings may be included in an amount of 80 mol% or more of the dianhydride monomer component.
  • the lower limit of the ratio of the dianhydride monomer component having one or two benzene rings among the dianhydride monomer components may be 82 mol% or more, 84 mol% or more, 86 mol% or more, or 88 mol% or more, The upper limit may be 99.9 mol% or less, 99.5 mol% or less, 99 mol% or less, or 98 mol% or less.
  • Compounds having one or two benzene rings among the diamine monomer components are 1,4-diaminobenzene (PPD), 1,3-diaminobenzene (MPD), 2,4-diaminotoluene, 2,6 -Diaminotoluene, 4,4'-diaminodiphenyl ether (ODA), 4,4-diaminobenzanilide (4,4-DABA), 2,2-dimethylbenzidine (M-TOLIDINE), 3, It may be at least one selected from the group consisting of 3-dimethylbenzidine (O-TOLIDINE) and 2,2'-bistrifluoromethylbenzidine (TFMB).
  • PPD 1,4-diaminobenzene
  • MPD 1,3-diaminobenzene
  • ODA 4,4'-diaminodiphenyl ether
  • 4,4-DABA 4,4-diaminobenzanilide
  • M-TOLIDINE 2,2-d
  • the diamine monomer component having one or two benzene rings may be included in an amount of 80 mol% or more of the diamine monomer component.
  • the lower limit of the ratio of the diamine monomer component having one or two benzene rings among the diamine monomer components may be 82 mol% or more, 84 mol% or more, 86 mol% or more, or 88 mol% or more, and the upper limit is 99.9 mol%. % or less, 99.5 mol% or less, 99 mol% or less, or 98 mol% or less.
  • the polyamic acid composition according to the present invention includes a solvent, and the solvent may be an organic solvent.
  • Solvents compatible with the polyimide precursor include N,N-diethylacetamide (DEAC), N,N-dimethylpropionamide (DMPA), 3-methoxy-N,N-dimethylpropanamide (KJCMPA)
  • NMP N-methyl-2-pyrrolidone
  • the solvent may be an organic solvent.
  • the solvent of the polyamic acid composition according to the present invention may have a boiling point of 150°C or higher.
  • the solvent of the polyamic acid composition may have a boiling point of 160°C or higher or 170°C or higher.
  • the lower limit of the boiling point of the solvent may be, for example, 155 ° C, 160 ° C, 165 ° C, 170 ° C, 175 ° C, 180 ° C, 185 ° C, 190 ° C, 195 ° C, 200 ° C or 201 ° C or higher
  • the upper limit may be, for example, 500°C, 450°C, 300°C, 280°C, 270°C, 250°C, 240°C, 230°C, 220°C, 210°C or 205°C or less.
  • the polyamic acid composition according to the present invention may have a solid content in the range of 5 to 30% by weight.
  • the solid content may be 7% by weight or more, 9% by weight or more, 10% by weight or more, 12% by weight or more, 14% by weight or more, or 15% by weight or more, and the upper limit is, for example, 30% by weight or less, 25% by weight or less % or less, 20% or less, 18% or less, 17% or less or 15% or less.
  • the present application can implement the desired physical properties and viscosity within the above range.
  • a conventional polyimide precursor polymerization method such as solution polymerization may be used.
  • the thermal expansion coefficient may be measured at 100 to 400 °C.
  • the CTE can use TA's thermomechanical analyzer Q400 model, and after manufacturing polyimide into a film, cutting it into a width of 2 mm and a length of 10 mm, applying a tension of 0.05 N in a nitrogen atmosphere, 10 ° C / After raising the temperature from room temperature to 500 ° C at a rate of min, the slope of the 100 ° C to 400 ° C section can be measured while cooling again at a rate of 10 ° C / min.
  • the polyamic acid composition according to the present application may have a glass transition temperature of 430° C. or more after curing, and for example, the lower limit of the glass transition temperature is 440° C. or more, 445° C. or more, 450° C. or more, or 455° C. °C or higher or 460 °C or higher.
  • the upper limit may be 600° C. or less.
  • the glass transition temperature may be measured at 10 °C/min using TMA for polyimide prepared by curing the polyamic acid composition.
  • the lower limit of the thermal decomposition temperature may be, for example, 550 °C or higher, 555 °C or higher, 560 °C or higher, or 565 °C or higher.
  • the upper limit may be, for example, 800°C, 750°C, 700°C, 650°C or 630°C or less.
  • the polyamic acid composition according to the present application may have light transmittance of 60% or more in a visible light region of 470 nm after curing.
  • the light transmittance can be measured using a UV/Vis spectrophotometer.
  • the light transmittance is 61% or more, 62% or more, 63% or more, 64% or more, 65% or more, 66% or more, 67% or more, 68% or more, 69% or more, 70% or more, 71% It may be 72% or more, 73% or more, 74% or more, 75% or more, 76% or more, 77% or more, or 80% or more, and the upper limit is not particularly limited, but may be 90% or less or 85% or less.
  • the polyamic acid composition may have an elongation of 15% or more after curing, for example, 17% or more, 19% or more, 21% or more, 23% or more, or 25% or more.
  • the upper limit is not particularly limited, but may be 40% or less.
  • the elongation can be measured by the ASTM D-882 method using Instron 5564 UTM equipment after curing the polyamic acid composition into a polyimide film, cutting it into a width of 10 mm and a length of 40 mm.
  • the polyamic acid composition may have a tensile strength of 230 MPa or more after curing.
  • the lower limit of the tensile strength may be, for example, 240 MPa or more, 250 MPa or more, 260 MPa or more, 270 MPa or more, 280 MPa or more, 290 MPa or more or 300 MPa or more, and the upper limit may be, for example, 550 MPa or less or It may be 530 MPa or less.
  • the elastic modulus and tensile strength were measured by the ASTM D-882 method using Instron 5564 UTM equipment after curing the polyamic acid composition to prepare a polyimide film, cutting it into a width of 10 mm and a length of 40 mm, and Tensile strength can be measured.
  • the cross head speed at this time can be measured under the condition of 50 mm/min.
  • the present invention provides a method for producing a polyimide, comprising forming a polyamic acid composition prepared according to the method for producing a polyamic acid composition on a support and drying to prepare a gel, and curing the gel.
  • the method for producing a polyimide of the present invention may include forming a film of the polyamic acid composition on a support, drying the film to prepare a gel, and curing the gel.
  • the polyamic acid composition formed on the support is dried at a temperature of 20 to 120 ° C for 5 to 60 minutes to prepare a gel film, and the gel film is heated from 1 to 8 ° C to 30 to 500 ° C. /min, heat treatment at 450 to 500 ° C for 5 to 60 minutes, and cooling to 20 to 120 ° C at a rate of 1 to 8 ° C / min.
  • Curing the gel film may be performed at 30 to 500 °C.
  • the step of curing the gel film is 30 to 400 ° C, 30 to 300 ° C, 30 to 200 ° C, 30 to 100 ° C, 100 to 500 ° C, 100 to 300 ° C, 200 to 500 ° C, or 400 to 500 ° C. may be performed at °C.
  • the polyimide film may have a thickness of 5 to 20 ⁇ m.
  • the polyimide film may have a thickness of 5 to 18 ⁇ m, 6 to 16 ⁇ m, 7 to 14 ⁇ m, 8 to 12 ⁇ m, or 9 to 11 ⁇ m.
  • the polyimide according to the present invention has excellent transparency and excellent thermal properties, it can be usefully used as a substrate such as a substrate for a device or a cover substrate for a display, and a film such as an optical film, an adhesive film, a tape or a protective film for a disk. can be usefully used.
  • the polyamic acid composition according to the present invention or the polyimide prepared using the same may be used as a transparent polyimide substrate for oxide TFT or a transparent polyimide substrate for LTPS.
  • the present invention can provide a transparent polyimide substrate for an oxide TFT manufactured using the polyamic acid composition or polyimide described above.
  • the present invention may provide a transparent polyimide substrate for LTPS manufactured using the polyamic acid composition or polyimide described above.
  • the polyamic acid composition according to the present invention and the polyimide including the same have excellent thermal properties such as dimensional stability and heat resistance while having high transparency.
  • the polyamic acid composition and the polyimide including the polyamic acid composition according to the present invention have high transparency and a high glass transition temperature, they have excellent mechanical properties and processability as well as low weight loss and low expansion coefficient with respect to heat.
  • N,N-dimethylpropionamide (DMPA) was introduced as a solvent while nitrogen was injected into a 500 ml reactor equipped with a stirrer and a nitrogen injection discharge pipe.
  • BPDA biphenyltetracarboxylic dianhydride
  • PPD para-phenylene diamine
  • 10 parts by weight of 9,9-bis (3,4-dicarboxyphenyl) fluorene dianhydride (9,9-Bis (3,4-dicarboxyphenyl) fluorene Dianhydride, BPAF) was divided into 3 times at 30 minute intervals. Then, stirring was continued for 120 minutes to prepare a polymerized polyamic acid composition.
  • a polyamic acid solution was prepared in the same manner as in Example 1, except that the monomer components and content ratios were adjusted as shown in Table 1.
  • a polyamic acid solution was prepared in the same manner as in Example 1, except that the monomers and content ratios were adjusted as shown in Table 1.
  • Example 1 One 100 15 Example 2 97 3 100 15 Example 3 95 5 100 15 Example 4 93 7 100 15 Example 5 90 10 100 15 Example 6 90 10 90 10 15 Example 7 90 10 100 15 Example 8 90 10 90 10 15 Example 9 90 5 5 90 5 5 15 Example 10 100 90 10 15 Example 11 100 93 7 15 Example 12 100 97 3 15 Example 13 100 99 One 15 Comparative Example 1 100 100 15 Comparative Example 2 85 15 100 15 Comparative Example 3 85 15 100 15 Comparative Example 4 85 15 85 15 15 15 15 Comparative Example 5 85 15 15 15 Comparative Example 6 100 85 15 15 15 BPDA: biphenyltetracarboxylic dianhydride BPAF: 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride FDA-ADA: 4,4'-(9H-fluorene-9,9di
  • Air bubbles were removed from the polyamic acid compositions prepared in Examples and Comparative Examples by high-speed rotation of 1,500 rpm or more. Then, the degassed polyamic acid composition was applied to the glass substrate using a spin coater. Thereafter, a gel film was prepared by drying at a temperature of 120 ° C. for 30 minutes under a nitrogen atmosphere, and the gel film was heated at a rate of 2 ° C / min to 450 ° C. After heat treatment at 450 ° C. for 60 minutes, 30 ° C. It was cooled at a rate of 2° C./min to obtain a 10 ⁇ m polyimide film.
  • the polyimide film was peeled from the glass substrate by dipping in distilled water.
  • the physical properties of the prepared polyimide film were measured using the following method, and the results are shown in Table 2 below.
  • Viscosity of the polyamic acid solutions prepared in Examples and Comparative Examples was measured using Haake's Rheostress 600 under conditions of a shear rate of 1/s, a temperature of 23° C., and a plate gap of 1 mm.
  • thermomechanical analyzer Q400 model was used, and after cutting the polyimide film into a width of 2 mm and a length of 10 mm, it was heated from room temperature to 500 ° C at a rate of 10 ° C / min while applying a tension of 0.05 N in a nitrogen atmosphere. After the temperature was raised, the slope of the section from 100 °C to 400 °C was measured while cooling at a rate of 10 °C/min.
  • the rapidly expanding point at 10 °C/min condition was measured as an on-set point using TMA.
  • the elastic modulus and tensile strength were measured by ASTM D-882 method using Instron 5564 UTM equipment. can The cross head speed at this time can be measured under the condition of 50 mm/min.
  • Example 1 3,300 66 3 460 568 28 468 9.0
  • Example 2 4,200 70 3 460 568 28 397 8.1
  • Example 3 4,100 72 4 455 565 25 342 7.9
  • Example 4 3,000 74 4 455 563 23 303 7.8
  • Example 5 3,000 77 10 450 563 22 275 7.1
  • Example 6 3,500 83 14 455 558 20 263 7.0
  • Example 7 3,100 76 8 460 560 25 301 6.9
  • Example 8 3,800 79 12 460 555 20 265 7.0
  • Example 9 5,200 76 12 450 553 22 290 7.3
  • Example 10 4,800 75 13 450 558 25 334 7.5
  • Example 11 4,400 73 10 455 560 25 340 7.5
  • Example 12 3,500 71 5 460 565 26 378 8.0
  • Example 13 3,500 66 3 460

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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)
  • Microelectronics & Electronic Packaging (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

La présente invention concerne une composition d'acide polyamique et un polyimide la comprenant et présentant d'excellentes propriétés thermiques telles qu'une stabilité dimensionnelle et une résistance à la chaleur tout en conservant une transparence élevée.
PCT/KR2022/012452 2021-09-09 2022-08-19 Composition d'acide polyamique et polyimide préparé à partir de celle-ci Ceased WO2023038322A1 (fr)

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CN202280061248.1A CN117940486A (zh) 2021-09-09 2022-08-19 聚酰胺酸组合物及由其制备的聚酰亚胺

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KR20210010571A (ko) * 2018-06-22 2021-01-27 미쓰이 가가쿠 가부시키가이샤 폴리아마이드산 및 이것을 포함하는 바니시, 필름, 터치 패널 디스플레이, 액정 디스플레이, 및 유기 el 디스플레이
KR102162042B1 (ko) * 2019-02-01 2020-10-06 윙고 테크놀로지 가부시키가이샤 폴리이미드 화합물 및 해당 폴리이미드 화합물을 포함하는 성형물
CN111072964A (zh) * 2019-12-31 2020-04-28 阜阳欣奕华材料科技有限公司 一种聚酰亚胺前体组合物及其制备方法和应用

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