WO2018093118A1 - 폴리아미드계 블록 공중합체 필름 - Google Patents
폴리아미드계 블록 공중합체 필름 Download PDFInfo
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- WO2018093118A1 WO2018093118A1 PCT/KR2017/012888 KR2017012888W WO2018093118A1 WO 2018093118 A1 WO2018093118 A1 WO 2018093118A1 KR 2017012888 W KR2017012888 W KR 2017012888W WO 2018093118 A1 WO2018093118 A1 WO 2018093118A1
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- 0 CCC(*)(*(C)*)N(C(C1=C2C=C=IC=C1)=O)C2=O Chemical compound CCC(*)(*(C)*)N(C(C1=C2C=C=IC=C1)=O)C2=O 0.000 description 4
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N CN(C(c1c2cccc1)=O)C2=O Chemical compound CN(C(c1c2cccc1)=O)C2=O ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
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- 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
- Aromatic polyimide resins are mostly polymers having an amorphous structure and exhibit excellent heat resistance, chemical resistance, electrical properties, and dimensional stability due to their rigid chain structure. Such polyimide resins are widely used as electrical / electronic materials.
- polyimide resins have many limitations in use because they have a dark brown limitation due to CTC (charge transfer complex) formation of ⁇ electrons present in the imide chain.
- a method of introducing an aliphatic ring compound to inhibit resonance structure formation of ⁇ electrons has been proposed.
- the present invention is to provide a polyimide-based block copolymer film that is colorless transparent and exhibits excellent mechanical properties.
- a block copolymer comprising a first repeating unit represented by the following Chemical Formula 1 and a second repeating unit represented by the following Chemical Formula 2,
- Polyimide-based block copolymer films are provided that exhibit a transmittance of up to 13% for ultraviolet light at a wavelength of 388 nm at a thickness of 50 ⁇ 5 Hz:
- R 2 are each independently -H, -F, -CI, -Br, -I, -CF 3 / -CC1 3 , -CBr 3 / -CI 3 , -N0 2 ,-CN, -COCH 3 , -C0 2 C 2 H 5 / silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, aliphatic organic groups having 1 to 10 carbon atoms, or aromatic organic groups having 6 to 20 carbon atoms;
- nl and ml are each independently 0-3;
- Y 'L is the same or different from each other in each repeating unit, are each independently An aromatic organic group having 6 to 30 carbon atoms;
- X is an integer of 2 or more, and each repeating unit repeated two or more times by X may be the same or different from each other;
- Y 2 is the same or different at each repeating unit, and each independently includes an aromatic organic group having 6 to 30 carbon atoms;
- Z 2 is the same or different at each repeat unit and is a divalent linking group derived from at least one compound selected from the group consisting of diacyl halides, dicarboxylic acids and dicarboxylates, respectively.
- a polyimide block copolymer and a polyimide film including the same according to embodiments of the present invention will be described in detail.
- first component may also be referred to as the second component, and similarly, the second component may be referred to as the first component.
- a branched copolymer having three semi-aromatic substituents is introduced into a polyimide chain having a linear structure, and a block copolymer is obtained by applying two or more kinds of tetracarboxylic anhydrides. It was confirmed that the de-based block copolymer may be colorless and transparent and exhibit excellent UV blocking properties.
- the brancher may impart a network structure to the copolymer, and a network having a robust and stable structure may be formed by the block copolymerization of the repeating unit including the same.
- the polyimide block copolymer film may be suitably used as a base material for devices and devices requiring excellent UV blocking properties with colorless transparency.
- such a polyimide-based block copolymer film may be suitably used for a substrate for display, a protective film for display, a touch panel, in particular various foldable devices and devices.
- a block copolymer comprising a first repeating unit represented by the following Chemical Formula 1 and a second repeating unit represented by the following Chemical Formula 2,
- a polyimide-based block copolymer film which exhibits a transmittance (tmnsmittance) of up to 13% for ultraviolet light at a wavelength of 388 nm at a thickness of 50 ⁇ 5 ⁇ :
- R 2 are each independently -H, -F, -CI, -Br, -I, -CF 3 , -CC1 3 / -CBr 3 / -CI 3 , -N0 2 ,-
- CN -COCH 3 / -CO2C2H5
- nl and ml are each independently 0-3;
- ⁇ ⁇ is the same or different from each other and each independently includes an aromatic organic group having 6 to 30 carbon atoms;
- X is an integer of 2 or more, each repeating two or more times by X.
- the units may be the same or different from one another;
- Z i is the same or different at each repeat unit and is selected from the group consisting of triacyl halides, tricarboxylic acids and tricarboxylates, respectively.
- 10 ⁇ 2 is the same or different in each repeating unit.
- z 2 is the same or different at each repeat unit and is a divalent linking group derived from at least one compound selected from the group consisting of diacyl halides, dicarboxylic acids and dicarboxylates, respectively.
- the polyimide block copolymer film provided in the present invention includes a block copolymer including a first repeating unit represented by Formula 1 and a second repeating unit represented by Formula 2.
- the single bond means a case of simply opened.
- R 2 is each independently -H, -F, -C1,-
- nl and ml are each independently an integer of 0 to 3.
- Y 1 is the same or different from each other, and each independently includes an aromatic organic group having 6 to 30 carbon atoms.
- R b is independently -H, -F, -CI, -Br, -I, -CF 3, -CC1 3, -CBr 3, -CI3, -NO2, - CN, -COCH 3, -C0 2 C 2 H 5 / silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, aliphatic organic groups having 1 to 10 carbon atoms, or aromatic organic groups having 6 to 20 carbon atoms;
- p and q are each independently 1-4.
- X is an integer of 2 or more, and each repeating unit repeated two or more by X may be the same or different from each other.
- R i , R 2 , nl, ml, and ⁇ may be the same as or different from each other in each repeating unit repeated by X.
- X may be 2 to 4, or 2 to 3, or 2.
- the single bond refers to a case where E 1 , E 2 or E 3 is a chemical bond that simply connects the adjacent groups or repeating units.
- Z i is three semi-ungsung Branchers having substituents, which are the same or different from each other in each repeating unit, are tri-valent derived from at least one compound selected from the group consisting of triacyl halides, tricarboxylic acids and tricarboxylates, respectively. ) Is a coupler.
- ⁇ ⁇ is aromatic triacyl halide having 6 to 20 carbon atoms, carbon number
- Aromatic tricarboxylic acid having 6 to 20 carbon atoms Aromatic tricarboxylate having 6 to 20 carbon atoms, N-containing heteroaromatic triacyl halides having 4 to 20 carbon atoms, N-containing heteroaromatic tricarboxylic acids containing 4 to 20 carbon atoms, containing ⁇ containing 4 to 20 carbon atoms 3 derived from at least one compound selected from the group consisting of heteroaromatic tricarboxylates, alicyclic triacyl halides having 6 to 20 carbon atoms, alicyclic tricarboxylic acids having 6 to 20 carbon atoms, and alicyclic tricarboxylates having 6 to 20 carbon atoms; It may be an optional connector.
- X 1 may be a group selected from the group represented by the following structural formula.
- Z i is 1,3,5-benzenetricarbonyl trichloride, 1,2,4-benzenetricarbonyl trichloride (1,2,4- benzenetricarbonyl trichloride), 1,3,5-benzenetricarboxylic acid, 1,2,4-benzenetricarboxylic acid (1,2,4-benzenetTicarboxylic acid), trimethyl 1,3,5 -Derived from at least one compound selected from the group consisting of trimethyl 1,3,5-benzenetricarboxylate, and trimethyl 1,2,4-benzenetricarboxylate It may be a trivalent linking group.
- the first repeating unit may include a repeating unit represented by Formula 3 below:
- R 2 and R 4 are each independently -H, -F, -CI, -Br, -I, -CF 3 , -CC1 3 / -CBr 3 , -CI 3 , -N0 2 , -CN, -COCH 3 / -C0 2 C 2 H 5 / silyl group, an aliphatic organic group having 1 to 10 carbon atoms having 1 to 10 carbon atoms in the three aliphatic organic group, or, having 6 to 20 carbon atoms in the aromatic organic group, and;
- R 4 is each independently -CF 3 , -CC1 3 , -CBr 3 / -CI3, -F, -CI, -Br, -I, -NO2, -CN,-
- nl and ml are each independently 0-3; n2 and m2 are each independently 1-4;
- X is an integer of 2 or more, and each repeating unit repeated two or more times by X may be the same or different from each other;
- Z i is the same or different at each repeating unit and is a trivalent linking group each derived from a triacyl halide, tricarboxylic acid and at least one compound selected from the group consisting of. More preferably, the first repeating unit includes a repeating unit represented by the following formula; ⁇ ⁇ in Formula 5a is a repeating unit represented by Formula 5b, and X 2 is a repeating unit represented by Formula 5c:
- R 4 is independently -H, -F, -CI, -Br, -I, -CF 3 , -CC1 3 , -CBr 3 , -CI 3 , -NO 2 ,- CN, -COCH 3 / -CO2C2H5, a silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, an aliphatic organic group having 1 to 10 carbon atoms, or an aromatic organic group having 6 to 20 carbon atoms;
- nl and ml are each independently 0-3;
- n2 and m2 are each independently 1-4;
- xb and xc are each independently an integer of 1 or more. According to an embodiment of the present invention, in the first repeating unit, the repeating unit represented by Formula 5b and the repeating unit represented by Formula 5c may be included in an equivalent ratio of 1: 1.1 to 1: 2.0.
- the first repeating unit is provided with a repeating unit represented by the formula (5c) at a higher equivalent weight than the repeating unit represented by the formula (5b), sufficient expression of the ultraviolet blocking effect required in the present invention May be desirable.
- the repeating unit represented by the formula (5b) and the repeating unit represented by the formula (5c) is 1: 1.10 or more, or 1: 1.15 or more, or 1: 1.20 or more, or black 1: 1: 25 or more; And 1: 1: 2.00 or less, or 1: 1.75 or less, 1: 1.50 or less, black: 1: 1.45 or less, or 1: 1.40 or less, black: 1: 1.35 or less, black: 1: 1.30 or less It is preferable to be contained in a repeating unit.
- the polyimide block copolymer may include one or more repeating units represented by Formula 2.
- Y 2 is the same or different from each other, and each independently includes an aromatic organic group having 6 to 30 carbon atoms.
- Y 2 is a divalent organic group represented by the following structural formula:
- R b ' are each independently -H, -F, -CI, -Br, -I, -CF 3, -CC1 3, -CBr -CI3, -NO2, - CN, -COCH 3, - C0 2 C 2 H 5 , a silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, an aliphatic organic group having 1 to 10 carbon atoms, or an aromatic organic group having 6 to 20 carbon atoms;
- E 6 is a chemical bond that simply connects the groups or repeating units next to each other.
- Z 2 is derived from at least one compound selected from the group consisting of and the same or one or different from each other in each repeating unit, each of the diacyl halide, dicarboxylic acids and dicarboxylate It is a bivalent coupler.
- z 2 may be selected from the group represented by the following structural formula.
- the Z 2 isophthaloyl dichloride isophthalic acid (isophthalic acid), cyclonucleic acid -1,3-dicarbonyl chloride (cyclodoe-l, 3-dicarbonyl chloride), cyclo Nucleic acid-1,3-dicarboxylic acid, pyridine-3,5-dicarbonyl chloride, pyridine-3,5-dicarboxylic acid 3,5-dicarboxylic acid), pyrimidine-2,6-dicarbonyl chloride (pyrimidine-2,6- dicarbonyl chloride), pyrimidine-2,6-dicarboxylic acid, terephthaloyl chloride (TPC), terephthalic acid, cyclonucleic acid-1,4-dicarbonyl Cyclohexane-l, 4-dicarbonyl chloride, cyclohexane-1,4-dicarboxylic acid, pyridine-2,5-dicarbonyl chloride chlor
- the repeating unit contains two carbonyl groups Z 2 of the structure bonded to the meta position with respect to the central ring in the "examples, the two carbonyl groups in the above examples combined the para position with respect to the central ring Including a repeating unit containing Z 2 of the structure together may be advantageous to secure processability and mechanical properties simultaneously.
- the second repeating unit may include a repeating unit represented by Formula 4 below:
- R 6 are each independently -H, -F, -CI, -Br, -I, -CF 3 , -CC1 3 / -CBr 3 / -CI 3 , -N0 2 / -CN, -COCH 3 / -C0 2 C 2 H 5 / silyl group having three aliphatic organic groups having 1 to 10 carbon atoms, aliphatic organic groups having 1 to 10 carbon atoms, or aromatic organic groups having 6 to 20 carbon atoms;
- n3 and m3 are each independently 1-4;
- Z 2 is.
- the second repeating unit may include a repeating unit represented by Formula 6 below:
- R 6 are each independently -H, -F, -CL -Br, -I, -CF 3 , -CCk, -CBr 3 , -CI3, -NO2,-CN, -COCH3, -C0 2 C 2 H 5
- n3 and m3 are each independently 1 to 4
- the weight ratio of the first repeating unit to the second repeating unit may be 1: 0.25 to 1: 4 for the expression of the above effects.
- the increase ratio of the first repeating unit: the second repeating unit is 1: 0.25 or more, or 1: 0.30 or more, or 1: 0.35 or more
- black is 1: 0.40 or more, or 1: 0.45 or more, or 1: 0.50 or more, or 1: 0.55 or more, or 1: 0.60 or more
- black is 1: 0.65 or more
- black may be 1: 2.5 or less, or 1: 2.0 or less
- black may be 1: 1.5 or less.
- the weight ratio is 1: 0.25 to 1: 2 or 1: 0.25 to 1: 1.5
- 'black is 1: 0.65 to 1: 1.5 can work.
- Z i introduced into the first repeating unit is a branching agent for imparting a network structure to the copolymer, and by block copolymerization of the repeating unit including the same, a solid and stable structure of the copolymer Networks can be formed. Therefore, when the weight ratio of the first repeating unit is too low, the network structure may not be sufficiently formed in the copolymer, and the effect of improving physical properties may be insignificant. However, when the weight ratio of the first repeating unit is too high, gelation may occur during the polymerization process.
- the polyimide block copolymer may have a higher molecular weight than a polyimide resin having a general linear structure as it has a robust and stable network.
- the polyimide block co-polymer is 100,000 to 5,000,000 g / mol, preferably 200,000 to 1,000,000 g / mol, more preferably 300,000 to 750,000 g / mol, even more preferably 500,000 to 650,000 g / m It may have a weight average molecular weight thereof.
- the polyimide-based block copolymer forms the first repeating unit Mixing the compound in an appropriate solvent to initiate the reaction; Reacting by adding the compound forming the second repeating unit to the reaction mixture of the step; And adding compounds such as acetic anhydride and pyridine to the reaction mixture of the above step to induce a chemical imidization reaction.
- Low temperature solution polymerization, interfacial polymerization, melt polymerization, solid state polymerization, etc. may be used to prepare the polyimide block copolymer.
- the polyimide block copolymer film may be formed using the polyimide block copolymer. It may be prepared by conventional methods such as dry method and wet method.
- the polyimide block copolymer films, and forming a film by coating a solution containing the copolymer on any of the support may be obtained by the method of drying by evaporating the solvent from the film. If necessary, stretching and heat treatment may be performed on the polyimide film.
- the polyimide block copolymer films can be as prepared using the polyimide-based block copolymer notary exhibit excellent ultraviolet ray barrier property while colorless and transparent.
- the polyimide-based block copolymer comprising the following first repeating unit formed by applying two or more kinds of tetracarboxylic anhydride together with the brancher is more stable and has a longer polymer chain than a polyimide-based copolymer having a linear structure.
- Networks can exhibit significantly improved sun protection properties.
- the polyimide-based block copolymer film has a transmittance of 13% or less, or 10 to 13%, or 10 to 12.5%, or 12 to 13% to UV rays having a wavelength of 388 nm at a thickness of 50 ⁇ 5 Hz. transmittance).
- the polyimide block copolymer film may be suitably used as a base material for devices and devices requiring excellent UV blocking properties with colorless transparency.
- such polyimide-based block copolymer films can be used for substrates for displays, protective films for displays, touch panels, in particular It can be used suitably for foldable devices and devices.
- the polyimide-based block copolymer copolymer film according to the present invention exhibits excellent UV blocking properties and can be suitably used as a display substrate, a display protective film, a touch panel, and the like.
- FIG. 1 is an NMR spectrum of a polyimide copolymer obtained in Example 1.
- Figure 2 is a graph showing the results of measuring the total light transmittance of the polyimide film according to Example 4 and Comparative Example 2 . .
- FIG. 3 is a graph showing the total light transmittance—the measurement results for the polyimide film according to Example 5, Comparative Example 2 and Reference Example 2.
- FIG. 3 is a graph showing the total light transmittance—the measurement results for the polyimide film according to Example 5, Comparative Example 2 and Reference Example 2.
- reaction product was withdrawn to room temperature, followed by 0.99 equivalents (eq.) Of 2,2'-bis (trifluoromethyl) benzidine p ⁇ -bis ⁇ rifluoromethy benzidme, 1.01 equivalents (eq.) Of terephthal Loeyl chloride (terephthaloyl chloride, TPC) and 120 ml of dimethylacetamide were added, and the reaction was started at room temperature in a nitrogen atmosphere.
- terephthal Loeyl chloride terephthaloyl chloride, TPC
- reaction product was removed to room temperature, and then 0.99 equivalent (eq.) Of 2,2'-bis (trifluoromethyl) benzidine ( 2 , 2l- bis (trifluoromethyl) benzidine), 1.01 equivalent (eq. Terephthaloyl chloride (TPC) and 120 ml of dimethylacetamide were added, and the reaction was initiated at room temperature in a nitrogen atmosphere.
- TPC Terephthaloyl chloride
- a polyimide copolymer was obtained in the same manner as in Example 1 except that 4,4'-biphthalic anhydride (BPDA) was not added (weight average molecular weight 160,000 g / mol, first repeating unit: weight ratio of second repeating unit 1: 1).
- BPDA 4,4'-biphthalic anhydride
- reaction product was withdrawn to room temperature, followed by 0.99 equivalents (eq.) Of 2,2'-bis (trifluoromethyl) benzidine (2,2'-bis (trifluoromethyl) benzidine), 1.01 equivalents (eq Terephthaloyl chloride and 120 ml of dimethylacetamide were added and reaction was initiated at a temperature of phase silver in a nitrogen atmosphere.
- the film was prepared using the polyimide copolymer obtained in Example 1. Specifically, the polyimide copolymer was dissolved in dimethylacetamide to prepare a polymer solution of about 25% (w / V). The polymer solution was poured onto a glass substrate, and the thickness of the polymer solution was uniformly adjusted using a film applicator, followed by drying for 12 hours or more in a 100 ton vacuum oven to prepare a polyimide film having a thickness of 50 rn.
- a polyimide film having a thickness of 50 mm 3 was manufactured in the same manner as in Example 4, except that the polyimide copolymer obtained in Example 2 was used instead of the copolymer of Example 1.
- a polyimide film having a thickness of 50 was prepared in the same manner as in Example 4, except that the polyimide copolymer obtained in Example 3 was used instead of the copolymer of Example 1.
- a polyimide film having a thickness of 50 1 was manufactured by the same method as Example 4, except that the polyimide copolymer obtained in Comparative Example 1 was used instead of the copolymer of Example 1.
- Reference Example 2 A polyimide film having a thickness of 50 1 was manufactured by the same method as Example 4, except that the polyimide copolymer obtained in Comparative Example 1 was used instead of the copolymer of Example 1.
- a polyimide film having a thickness of 50 was prepared in the same manner as in Example 4, except that the polyimide copolymer obtained in Reference Example 1 was used instead of the copolymer of Example 1.
- Test Example 1 the polyimide copolymer obtained in Reference Example 1 was used instead of the copolymer of Example 1.
- the total light transmittance of the films according to Examples and Comparative Examples was measured using a UV-VIS-NIR Spectrophotometer (SolidSpec-3700, SHIMADZU).
- the film according to the embodiments exhibits significantly superior UV blocking properties than the film of Comparative Example 2.
- the film according to Reference Example 2 was found to have a transmittance value of 38.92% for ultraviolet rays having a 388 nm wavelength, and was confirmed to be inferior in UV blocking properties as compared with the films of the examples.
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Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP17871699.9A EP3412732A4 (en) | 2016-11-17 | 2017-11-14 | BLOCK COPOLYMER FILM BASED ON POLYIMIDE |
CN201780022643.8A CN109071944B (zh) | 2016-11-17 | 2017-11-14 | 基于聚酰亚胺的嵌段共聚物膜 |
JP2018548091A JP6638174B2 (ja) | 2016-11-17 | 2017-11-14 | ポリイミド系ブロック共重合体フィルム |
US16/091,269 US10717819B2 (en) | 2016-11-17 | 2017-11-14 | Polyimide-based block copolymer film |
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KR10-2017-0150902 | 2017-11-13 |
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