WO2019117445A1 - Copolymère de polyamide-imide et film de polyamide-imide comprenant celui-ci - Google Patents

Copolymère de polyamide-imide et film de polyamide-imide comprenant celui-ci Download PDF

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Publication number
WO2019117445A1
WO2019117445A1 PCT/KR2018/012129 KR2018012129W WO2019117445A1 WO 2019117445 A1 WO2019117445 A1 WO 2019117445A1 KR 2018012129 W KR2018012129 W KR 2018012129W WO 2019117445 A1 WO2019117445 A1 WO 2019117445A1
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WO
WIPO (PCT)
Prior art keywords
repeating unit
polyamide
imide
aromatic organic
formula
Prior art date
Application number
PCT/KR2018/012129
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English (en)
Korean (ko)
Inventor
유윤아
최형삼
김병국
엄영식
최성열
김상곤
장덕훈
Original Assignee
주식회사 엘지화학
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
Priority claimed from KR1020180121996A external-priority patent/KR102140287B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880064928.2A priority Critical patent/CN111183171B/zh
Priority to US16/757,484 priority patent/US11414520B2/en
Priority to JP2020518016A priority patent/JP7053066B2/ja
Publication of WO2019117445A1 publication Critical patent/WO2019117445A1/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
    • 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
    • C08G73/14—Polyamide-imides
    • 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 polyamide-imide copolymer and a polyamide-imide film containing the same.
  • the aromatic polyamide-imide resin is a polymer having mostly an amorphous structure and exhibits excellent heat resistance, chemical resistance, electrical properties, and dimensional stability due to its rigid chain structure.
  • Such polyamide-imide resins are widely used as materials for electric / electronic, aerospace, aviation and automobile.
  • the wholly aromatic polyamide-imide resin is mostly insoluble and unfavorable, so that molding and workability are deteriorated, and conventional processing equipment is difficult to use for resin processing.
  • the polyamide-imide resin when used as a flexible display material, it has excellent optical properties in addition to thermal and mechanical properties 2019/117445 1 »(: 1/10/0/0 018/012129
  • the present invention is to provide a polyamide-imide copolymer which is excellent in heat resistance and mechanical properties and exhibits excellent optical properties.
  • the present invention further provides a polyimide film comprising the polyamide-imide copolymer.
  • a positive resist composition comprising a first repeating unit represented by the following formula (1), a second repeating unit represented by the following formula (2), and a third repeating unit represented by the following formula Is from 10: 90 to 50: 50.
  • Seedlings 2 are the same or different from each other in each repeating unit, each independently in,, - [: 1, -, -1, _0 _ ( ⁇ 1 3, - (3 ⁇ 4, I 0 2, - ⁇ - 003 ⁇ 4, - ⁇ 2 (: 2 3 ⁇ 4, 1 to 10 carbon atoms in the silyl group, having 1 to 10 carbon atoms in an aliphatic organic group, or a group having 6 to 20 carbon atoms having three aliphatic organophosphorous Aromatic 2019/117445 1 »(: 1 ⁇ ⁇ 2018/012129
  • 111 and s are each independently an integer of 0 to 3;
  • each repeating unit independently includes one or more trifluoromethyl groups (including a divalent aromatic organic group having 6 to 30 carbon atoms including - The aromatic organic group is present alone; Two or more aromatic organic groups are bonded to each other to form a divalent condensed ring; Or two or more aromatic organic groups are a single bond, a fluorenylene group, -0
  • X 2 ' are the same or different from each other in each repeating unit, and each independently is a divalent aromatic organic group having 6 to 30 carbon atoms and containing at least one trifluoromethyl group (-O ⁇ 3 );
  • Seed 2 , Seed 2 ' , E 3 , ' , ⁇ and ' are each independently a single
  • a polyamide-imide film comprising the polyamide-imide copolymer.
  • a polyamide-imide copolymer and a polyamide-imide film containing the same according to embodiments of the present invention will be described in detail.
  • the terminology is used merely to refer to a specific embodiment and is not intended to limit the invention.
  • first component may also be referred to as a second component, and similarly, a second component may be referred to as a first component.
  • the weight average molecular weight means the weight average molecular weight in terms of polystyrene measured by the GPC method.
  • a detector such as a known analyzer and a refractive index detector may be used, and a column for analysis may be used. Temperature conditions, solvent, and f low rate.
  • a polyamide-imide resin composition comprising a first repeating unit represented by the above-mentioned formula (1), a second repeating unit represented by the following formula (2), and a third repeating unit represented by the following formula A copolymer is provided. 2019/117445 1 »(: 1/10/0/0 018/012129
  • the dollyamide-imide copolymer is applied to various fields, and it is required to satisfy various properties at the same time.
  • the thermal characteristics, mechanical properties and optical properties of the copolymer can be simultaneously improved by introducing two specific structures into the amide-derived repeating unit in the production of the polyamide-imide copolymer .
  • the diacyl halide, the dicarboxylic acid, and the dicarboxylate compound are respectively limited to a specific structure and the molar ratio thereof is limited in the production of the copolymer, the mechanical properties and thermal resistance of the coliamide- It was confirmed that the optical properties of the resin can be improved at the same time while maintaining a good level. In particular, it exhibits anisotropy and is easily applied to a flexible display or the like.
  • each repeating unit independently includes a divalent aromatic organic group having 6 to 30 carbon atoms and containing at least one trifluoromethyl group (- ⁇ 3 );
  • the aromatic organic group is present alone; Two or more aromatic organic groups are bonded to each other to form a divalent condensed ring; Or two or more aromatic organic groups may be replaced by a single bond, a fluorenylene group, -O-, - (- (-)) -,
  • the single bond means a chemical bond that simply connects the group on the lower side of the formula (1).
  • I 2 are the same or different in each repeat unit, independently within each, ⁇ , -01, -, -1, - ⁇ -001 3, O 3, - 01 3, in 02, -0 -
  • 111 and s each independently may be an integer of 0 to 3.
  • each repeating unit May be the same or different from each other in each repeating unit, and each independently may be an alicyclic organic group having 3 to 10 carbon atoms.
  • Each may be independently a single bond or - -.
  • the single bond means a chemical bond that simply connects the groups on either side of each substituent in the formula (1).
  • the first repeating unit may include a repeating unit represented by the following formula (1-1)
  • X 2 and 2 ' are the same or different from each other in each repeating unit, and each independently represents one or more trifluoromethyl groups
  • the second repeating unit and the third repeating unit are amide-derived repeating units.
  • the second repeating unit may include a repeating unit represented by the following formula (2-1):
  • the third repeating unit may include a repeating unit represented by the following formula (3-1)
  • the molar ratio of the second repeating unit to the third repeating unit is 10:90 to 50:50, and by satisfying the molar ratio, the thermal characteristics, mechanical properties, The characteristics can be improved at the same time.
  • the effect of improving the flexibiity according to the bonding structure at the meta position of the second repeating unit and the improvement effect of the mechanical properties due to the rigid characteristic according to the bonding structure of the para position of the third repeating unit So that the thermal properties, mechanical properties and optical properties of the copolymer can be simultaneously improved.
  • the polyamide-imide copolymer according to the present invention preferably has a molar ratio of the sum of the amide-derived second repeating unit and the third repeating unit to the imide-derived first repeating unit is from 5: 5 to 2: 8 (1: 1 to 1: 4), or 4.5: 5.5 to 3: 7 (about 1: 1.22 to 1: 2.33), or 4: 6 to 3: 7. Both the mechanical properties, the thermal characteristics and the optical properties of the polyamide-imide resin film can be improved to a high level by simultaneously satisfying the molar ratio of the above-mentioned second repeating unit and third repeating unit.
  • the polyamide-imide copolymer according to the present invention preferably has a molar ratio of the sum of the amide-derived second repeating unit and the third repeating unit to the imide-derived first repeating unit is from 3: 7 to 6: 4 And the mechanical properties, thermal characteristics and optical characteristics of the copolymer can be improved to a high level by simultaneously satisfying the molar ratio, the molar ratio condition of the above-mentioned low cutting repeating unit and the third repeating unit.
  • the second repeating unit when the molar ratio between the sum of the first repeating unit: the second repeating unit and the third repeating unit is 3: 7 to 4: 6, the second repeating unit:
  • the molar ratio of the repeating units may be 20:80 to 50:50, or 30:70 to 45:55, and more preferably 30:70.
  • the mechanical properties, thermal properties and optical properties of the polyamide-imide resin film can be improved to a high level.
  • the second repeating unit when the molar ratio of the sum of the second repeating unit and the third repeating unit to the first repeating unit is 4.5: 5.5 to 4: 6, the second repeating unit: And the molar ratio of the third repeating unit may be 20:80 to 40:60.
  • the polyamide-imide copolymer may further include, in addition to the first repeating unit, the second repeating unit and the third repeating unit, a fourth repeating unit represented by the following formula (4)
  • 'Are the same or different from each other in each repeating unit, each independently including a divalent aromatic organic group having 6 to 30 carbon atoms;
  • - are the same or different from each other in each repeating unit, and each independently is selected from the group consisting of -0, -0, -0, -1 , -
  • - 2 (: 2 3 ⁇ 4, a silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 1 to 10 carbon atoms, or a 6 to 20 carbon-aromatic organic group.
  • 112 and 2 may each independently be an integer of 0 to 3.
  • E 1 ' each independently may be a single bond or -NH-.
  • the polyamide-imide block copolymer including both the first repeating unit, the second repeating unit and the third repeating unit has a molar ratio of the second repeating unit and the third repeating unit described above, By satisfying the molar ratio of the repeating unit and the amide-derived second repeating unit and the third repeating unit within a specific range, it is possible to simultaneously improve the mechanical properties, thermal characteristics, and optical properties of the copolymer.
  • the polyamide-imide copolymer according to an embodiment of the present invention may have a weight average molecular weight of 10,000 to 1,000,000 g / mol, and preferably 15,000 to 800,000 g / mol.
  • the polyamide-imide copolymer further comprises the fourth repeating unit, the step of mixing the compound forming the first repeating unit in an appropriate solvent to initiate the reaction; Adding a compound forming the second
  • a polyamide-imide film comprising the above-mentioned polyamide-imide copolymer.
  • the inventors of the present invention have found that the thermal properties, mechanical properties and optical properties of the copolymer can be improved simultaneously by introducing a specific structure into the amide-derived repeating unit.
  • the imide-derived repeating unit first repeating unit
  • the amide-derived repeating unit second repeating unit and third repeating unit
  • the polyimide film comprising the polyamide-imide block copolymer can be used as a material of various molded articles having excellent thermal properties and simultaneously requiring high mechanical properties.
  • the polyimide film according to the present invention is easy to apply to an electric and electronic product, particularly, a flexible display.
  • the polyimide film has a thickness (Rth) of from 4,000 nm to 6,000 nm, and preferably from 4,000 nm to 5,500 nm or from 4,050 nm to 400 nm, measured at a wavelength of 400 nm to 800 nm, 5, 200 nm.
  • the thickness direction retardation (Rth) value in the above range it is possible to have excellent optical properties and realize anisotropy, which is easy to use in a flexible display or the like.
  • the retardation (Rth) in the thickness direction can be confirmed by a commonly known measuring method and measuring device.
  • AxoScan As an apparatus for measuring the retardation (Rth) in the thickness direction, AxoScan, a prism coupler (Pris sm Coupler) manufactured by AX0METRICS, and the like can be given.
  • the refractive index was measured in the 400 nm to 800 nm region of the copolymer film using a prism coupler (Pr i sm Coupler), and the refractive index value was measured by AxoScan .
  • the retardation in the thickness direction of the polyamide-imide resin film was measured using light having a wavelength of 400 nm to 800 nm under the conditions of a temperature of 25 ° C and a humidity of 40% Based on the retardation measurement value of the film (measured value by automatic measurement (automatic calculation) of the measuring apparatus).
  • the value of the " refractive index of the polyamide-imide resin film " used for measurement of the retardation (Rth) in the thickness direction includes a polyamide-imide resin for forming a film to be measured for retardation
  • the unstretched film is used as a measurement sample (when the film to be measured is an unstretched film, the film can be directly used as a measurement sample), a refractive index measuring apparatus In the in-plane direction (direction perpendicular to the thickness direction) of the measurement specimen at a temperature condition of 23 ° C using a light source of 400 to 800 nm using the trade name "NAR-1T SOLID" manufactured by Atago Co., And measuring the refractive index with respect to light having a wavelength of from 800 nm to 800 nm.
  • the refractive index in the in-plane direction of the film becomes constant in any direction in the plane, and by measuring the refractive index, 2019/117445 1 »(: 1 ⁇ ⁇ 2018/012129
  • the inherent refractive index (400 to 800 11111 ) of the polyamide-imide resin film is measured using an unoriented film, and the obtained measured value is used for measurement of retardation in the thickness direction described above.
  • the size of the isotropic polyamide-imide resin film, a film of the test sample is, if the size that can be used in the refractive index measuring device is not particularly limited, and a 13 thickness of mutation 1 (TM square (length and breadth 10 11) , ≪ / RTI >
  • the polyamide-imide film has a yellowing index ( 6) measured at a wavelength of 380 to 780 (TM) according to the following formula (1) for a sample having a thickness of 20 to 100 11 ⁇ 1.) is 2.0 to
  • the polyamide-imide film can be produced by a conventional method such as a dry method or a wet method using the polyamide-imide copolymer.
  • the polyamide-imide film can be obtained by coating a solution containing the copolymer on an arbitrary support to form a film, and drying the film by evaporating the solvent from the film. If necessary, stretching and heat treatment for the polyamide-imide film may be performed.
  • the polyamide-imide film according to the present invention can be used as a material for various molded articles requiring high mechanical and optical properties along with colorless transparency.
  • the polyimide-imide film containing the polyamide-imide block copolymer may be applied to a display substrate, a protective film for a display, a touch panel, a cover film of a flexible or folder-type device, or the like .
  • the polyamide-imide copolymer according to the present invention makes it possible to provide a polyimide-imide film which is excellent in thermal stability, excellent in mechanical properties, and can realize excellent optical properties.
  • the polyamide-imide block copolymer 1 containing the first repeating unit, the second repeating unit and the third repeating unit of the following structure was obtained by precipitating the reaction product and ethanol (1: 1, 80) Molecular weight about 200,00 / 1110 1).
  • the molar ratio of the second repeating unit to the third repeating unit was 50:50, and the mole ratio of the second repeating unit: the third repeating unit (2)) to the total of the first repeating unit: Is 20:80.
  • Production Example 9 a polyamide-imide copolymer was prepared by adjusting the amounts of monomers charged so as to satisfy the molar ratios (1) and (2) shown in Table 1 below. Production Example 9
  • the polyamide-imide copolymer obtained in the above Production Example was used in the above production example
  • Yellowing index was measured according to the method of ASTM D1925 using a UV-2600 UV-Vi s Spectrometer (SHIMADZU) for the polyamide-imide film samples (thickness 50 ⁇ 2_) prepared in Examples and Comparative Examples, The results are shown in Table 2.
  • the elastic modulus (GPa) 3 ⁇ 4 was measured at a strain rate of 12.5 mm / min using Zwi ch / Roel 1 z005 (5 kN), and the results are shown in Table 2 Respectively.
  • Thickness phase difference Rth (thickness direction retardation value, nm)
  • the refractive index values at 400 to 800 nm were calculated using Prism Coupler. Thereafter, as a measuring device, a trade name " AxoScan " manufactured by AX0METRICS Co., Ltd.
  • the retardation in the thickness direction was measured using light having a wavelength of 400 nm to 800 nm under the conditions of a temperature of 25 ° C and a humidity of 40%
  • the retardation value measured in the thickness direction was used to calculate the thickness of the film in terms of 10 and the retardation value per film.
  • the amide-imide copolymer can be improved in thermal, mechanical and optical properties simultaneously by incorporating two amide repeating units having a specific structure in a specific ratio in accordance with the present invention .

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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

Selon la présente invention, un copolymère de polyamide-imide permet d'obtenir un film de polyamide-imide qui possède à la fois une stabilité thermique et des propriétés mécaniques, qui sont excellentes, et peut mettre en œuvre une anisotropie.
PCT/KR2018/012129 2017-12-11 2018-10-15 Copolymère de polyamide-imide et film de polyamide-imide comprenant celui-ci WO2019117445A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201880064928.2A CN111183171B (zh) 2017-12-11 2018-10-15 聚酰胺-酰亚胺共聚物和包含其的聚酰胺-酰亚胺膜
US16/757,484 US11414520B2 (en) 2017-12-11 2018-10-15 Polyamide-imide copolymer and polyamide-imide film comprising the same
JP2020518016A JP7053066B2 (ja) 2017-12-11 2018-10-15 ポリアミド－イミド共重合体およびこれを含むポリアミド－イミドフィルム

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2017-0169717 2017-12-11
KR20170169717 2017-12-11
KR1020180121996A KR102140287B1 (ko) 2017-12-11 2018-10-12 폴리아미드-이미드 공중합체 및 이를 포함하는 폴리아미드-이미드 필름
KR10-2018-0121996 2018-10-12

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130029129A (ko) * 2011-05-18 2013-03-22 삼성전자주식회사 폴리(아미드-이미드) 블록 코폴리머, 이를 포함하는 성형품 및 상기 성형품을 포함하는 디스플레이 장치
KR101729731B1 (ko) * 2016-11-02 2017-04-25 에스케이씨 주식회사 인장신도가 개선된 무색 투명한 폴리아마이드-이미드 필름
KR20170054108A (ko) * 2015-11-09 2017-05-17 삼성전자주식회사 폴리(이미드-아미드) 코폴리머, 폴리(이미드-아미드) 코폴리머의 제조 방법, 및 상기 폴리(이미드-아미드)를 포함하는 성형품
WO2017179877A1 (fr) * 2016-04-11 2017-10-19 에스케이씨 주식회사 Film de polyamide-imide incolore et transparent et son procédé de fabrication
KR20170132459A (ko) * 2016-05-24 2017-12-04 주식회사 엘지화학 고강도 투명 폴리아미드이미드 및 이의 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130029129A (ko) * 2011-05-18 2013-03-22 삼성전자주식회사 폴리(아미드-이미드) 블록 코폴리머, 이를 포함하는 성형품 및 상기 성형품을 포함하는 디스플레이 장치
KR20170054108A (ko) * 2015-11-09 2017-05-17 삼성전자주식회사 폴리(이미드-아미드) 코폴리머, 폴리(이미드-아미드) 코폴리머의 제조 방법, 및 상기 폴리(이미드-아미드)를 포함하는 성형품
WO2017179877A1 (fr) * 2016-04-11 2017-10-19 에스케이씨 주식회사 Film de polyamide-imide incolore et transparent et son procédé de fabrication
KR20170132459A (ko) * 2016-05-24 2017-12-04 주식회사 엘지화학 고강도 투명 폴리아미드이미드 및 이의 제조방법
KR101729731B1 (ko) * 2016-11-02 2017-04-25 에스케이씨 주식회사 인장신도가 개선된 무색 투명한 폴리아마이드-이미드 필름

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