WO2024111131A1 - Ester d'acide polyamique, et composition de résine - Google Patents

Ester d'acide polyamique, et composition de résine Download PDF

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Publication number
WO2024111131A1
WO2024111131A1 PCT/JP2022/043636 JP2022043636W WO2024111131A1 WO 2024111131 A1 WO2024111131 A1 WO 2024111131A1 JP 2022043636 W JP2022043636 W JP 2022043636W WO 2024111131 A1 WO2024111131 A1 WO 2024111131A1
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Prior art keywords
polyamic acid
acid ester
group
structural unit
general formula
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PCT/JP2022/043636
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English (en)
Japanese (ja)
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真吾 田原
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Ｈｄマイクロシステムズ株式会社
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Priority to PCT/JP2022/043636 priority Critical patent/WO2024111131A1/fr
Priority to TW112137335A priority patent/TW202424050A/zh
Publication of WO2024111131A1 publication Critical patent/WO2024111131A1/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
    • 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

  • This disclosure relates to polyamic acid esters and resin compositions.
  • Such a protective film (cured film) using a polyimide resin can be obtained by applying a polyimide precursor or a resin composition containing a polyimide precursor onto a substrate, drying the applied resin film, and then heating the resulting film to cure it.
  • polyimide precursors such as polyamic acid esters are desirable because they can produce patterned cured films with highly accurate pattern shapes that correspond to pattern exposure.
  • the present disclosure has been made in consideration of the above-mentioned conventional circumstances, and aims to provide a polyamic acid ester and a resin composition containing the same that can produce a patterned cured film having a highly accurate pattern shape.
  • a polyamic acid ester comprising a structural unit (A) derived from a tetracarboxylic dianhydride and a structural unit (B) derived from a diamine compound, wherein at least a portion of the structural unit (A) has an unsaturated double bond, and when dissolved in a 3-methoxy-N,N-dimethylpropanamide solution having a solids concentration of 0.1% by mass, the polyamic acid ester has a light transmittance of 10% or more at 380 nm.
  • the structural unit (A) does not contain an aromatic ring or contains a structural unit (A1-2) in which the ratio of the number of aromatic rings contained in the tetracarboxylic acid dianhydride to the molecular weight of the tetracarboxylic acid dianhydride is less than 0.0068.
  • ⁇ 4> The polyamic acid ester according to ⁇ 2>, wherein a content of the structural unit (A1-1) in the structural unit (A) is 25 mol % or more with respect to the structural unit (A).
  • ⁇ 5> The polyamic acid ester according to ⁇ 3>, wherein a content of the structural unit (A1-2) in the structural unit (A) is 25 mol % or more with respect to the structural unit (A).
  • ⁇ 6> The polyamic acid ester according to any one of ⁇ 1> to ⁇ 5>, wherein the tetracarboxylic dianhydride includes at least one of compounds represented by the following chemical formulas (A-1) to (A-6):
  • X represents a tetravalent organic group
  • Y represents a divalent organic group.
  • R 6 and R 7 are each independently a hydrogen atom, a group represented by the following general formula (7), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R 6 and R 7 is a group represented by the following general formula (7).
  • the tetravalent organic group represented by X does not contain an aromatic ring, or if it contains an aromatic ring, the aromatic ring is not bonded to four carbonyl groups.
  • R 8 to R 10 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms, and q represents an integer of 1 to 10.
  • ⁇ 9> The polyamic acid ester according to any one of ⁇ 1> to ⁇ 8>, wherein the polyamic acid ester has a weight-average molecular weight of 20,000 or more.
  • ⁇ 10> The polyamic acid ester according to any one of ⁇ 1> to ⁇ 9>, wherein the polyamic acid ester has a light transmittance of 70% or more at 400 nm when dissolved in 3-methoxy-N,N-dimethylpropanamide having a solid content concentration of 0.1% by mass.
  • a resin composition comprising the polyamic acid ester according to any one of ⁇ 1> to ⁇ 10>.
  • the present disclosure provides a polyamic acid ester and a resin composition containing the same that can produce a patterned cured film having a highly accurate pattern shape.
  • 1 is a graph showing the light transmittance of solutions using polyamic acid esters 4, 10, and 12 to 14. 1 is a graph showing the light transmittance of solutions using polyamic acid esters 2, 4, 10, and 12.
  • the numerical range indicated using “to” includes the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages.
  • the upper or lower limit value of the numerical range may be replaced with a value shown in the examples.
  • each component may contain multiple types of corresponding substances. When multiple types of substances corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple substances present in the composition, unless otherwise specified.
  • the terms "layer” and “film” include cases where the layer or film is formed over the entire area when the area in which the layer or film is present is observed, as well as cases where the layer or film is formed over only a portion of the area.
  • the polyamic acid ester of the present disclosure contains a constituent unit (A) derived from a tetracarboxylic dianhydride and a constituent unit (B) derived from a diamine compound, at least a portion of the constituent unit (A) has an unsaturated double bond, and has a light transmittance of 10% or more at 380 nm when dissolved in 3-methoxy-N,N-dimethylpropanamide having a solids concentration of 0.1 mass %.
  • the polyamic acid ester of the present disclosure has excellent light transmittance because it has a light transmittance of 10% or more at 380 nm when dissolved in 3-methoxy-N,N-dimethylpropanamide having a solid content concentration of 0.1% by mass. Therefore, it is possible to form an excellent pattern shape by using a resin composition containing the polyamic acid ester.
  • the reasons for this are not clear, but are presumed to be as follows. First, when the light transmittance is less than 10%, when the photosensitive film containing the polyamic acid ester applied to the substrate or the like is subjected to pattern exposure, it is difficult for the light to reach the bottom of the photosensitive film.
  • the patterned cured film obtained tends to have a reverse taper shape
  • the photosensitive film is a positive type
  • the patterned cured film obtained tends to have a taper shape.
  • the polyamic acid ester and the resin composition containing the polyamic acid ester according to the present disclosure have excellent light transmittance, and therefore, when a photosensitive film containing the polyamic acid ester applied to a substrate or the like is subjected to pattern exposure, light is irradiated to the bottom of the photosensitive film, thereby making it possible to obtain a patterned cured film having a highly accurate pattern shape corresponding to the pattern exposure.
  • the polyamic acid ester of the present disclosure may be used in materials that require photosensitivity (e.g., negative or positive photosensitive resin compositions, preferably negative photosensitive resin compositions), or may be used in materials that do not require photosensitivity. Since the polyamic acid ester of the present disclosure has an unsaturated double bond, it is preferably used in materials that require photosensitivity.
  • the polyamic acid ester according to the present disclosure may have a light transmittance at 380 nm of 20% or more, 25% or more, or 50% or more when it is prepared as a 3-methoxy-N,N-dimethylpropanamide solution having a solid content concentration of 0.1% by mass.
  • the upper limit of the light transmittance at 380 nm is not particularly limited as long as it is 100%.
  • the method for measuring the light transmittance is, for example, as follows.
  • the polyamic acid ester powder is dissolved in 3-methoxy-N,N-dimethylpropanamide to a concentration of 0.1% by mass, and the solution is placed in a measurement cell.
  • the light transmittance at a specific wavelength e.g., a wavelength in the range of 300 nm to 500 nm
  • a spectrophotometer e.g., U-3900H, manufactured by Hitachi High-Tech Science Corporation.
  • the polyamic acid ester according to the present disclosure may have a light transmittance at 400 nm when prepared as a 3-methoxy-N,N-dimethylpropanamide solution having a solid content concentration of 0.1 mass % of the polyamic acid ester.
  • the upper limit of the light transmittance at 400 nm is not particularly limited as long as it is 100%.
  • the light transmittance can be adjusted as appropriate, for example, by changing the tetracarboxylic dianhydride and diamine compound. Specifically, there is a tendency to increase the aforementioned light transmittance value by methods such as reducing the amount of structural unit (A) derived from tetracarboxylic dianhydride containing an aromatic ring, reducing the proportion of aromatic rings in the entire structural unit (A), reducing the amount of structural unit (B) derived from diamine compound containing an aromatic ring, and reducing the proportion of aromatic rings in the entire structural unit (B).
  • the polyamic acid ester of the present disclosure is not particularly limited as long as it is a compound that contains structural units (A) and (B) at least some of which have unsaturated double bonds, and has the aforementioned light transmittance at 380 nm of 10% or more.
  • the tetracarboxylic dianhydride may be a compound containing two acid anhydride groups and bonded to each other via a single bond, a linking group, or a composite linking group formed by combining two or more types of linking groups.
  • the linking group include an alkylene group, a halogenated alkylene group, a phenylene group (not bonded to an acid anhydride group), a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R A ) 2 -; each R A independently represents a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si(R B ) 2 -O-) n ; each R B independently represents a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or 2 or
  • the structural unit (A) preferably contains an alicyclic structure.
  • the structural unit (A) may contain one alicyclic structure or two or more alicyclic structures.
  • two alicyclic rings may be bonded at two positions by at least one of a single bond and a linking group to form a five-membered or six-membered ring containing a linking group between the two alicyclic rings.
  • the alicyclic ring may have a substituent or may be unsubstituted. Examples of the substituent include an alkyl group, a fluorine atom, a halogenated alkyl group, a hydroxyl group, and an amino group.
  • Alicyclic structures include the tricyclodecane skeleton, cyclohexane skeleton, cyclopentane skeleton, cyclobutene skeleton, 1,3-adamantane skeleton, hydrogenated bisphenol A skeleton, hydrogenated bisphenol F skeleton, hydrogenated bisphenol S skeleton, and isobornyl skeleton.
  • the structural unit (A) may or may not contain an aromatic ring.
  • the number of aromatic rings is preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 1.
  • the aromatic rings may be linked by a single bond, or may be linked by a linking group, a composite linking group combining two or more linking groups, or the like.
  • the linking group include an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R A ) 2 -;
  • R A each independently represents a hydrogen atom, an alkyl group, or a phenyl group; a siloxane bond (-O-(Si(R B ) 2-O-) n ;
  • R B each independently represents a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or 2 or more).
  • two benzene rings may be linked at two points by at least one of a single bond and a linking
  • each aromatic ring may have a substituent or may be unsubstituted.
  • substituent on the aromatic ring include an alkyl group, a fluorine atom, a halogenated alkyl group, a hydroxyl group, and an amino group.
  • the polyamic acid ester of the present disclosure may contain one type of constituent unit (A), or may contain two or more types of constituent units (A). When two or more types of constituent units (A) are contained, the polyamic acid ester of the present disclosure may contain a constituent unit that includes an alicyclic structure and a constituent unit that includes an aromatic ring, or may contain a constituent unit that does not include an alicyclic structure or an aromatic ring, and a constituent unit that includes an aromatic ring.
  • At least a part of the structural unit (A) contained in the polyamic acid ester of the present disclosure has an unsaturated double bond and preferably satisfies the following (1) or (2).
  • the structural unit (A) contains a structural unit (A1-1) in which the two acid anhydride groups contained in the tetracarboxylic dianhydride are not bonded to an aromatic ring.
  • the structural unit (A) contains a structural unit (A1-2) that does not contain an aromatic ring, or in which the ratio of the number of aromatic rings contained in the tetracarboxylic dianhydride to the molecular weight of the tetracarboxylic dianhydride is less than 0.0068.
  • the structural unit (A1-1) may contain an aromatic ring that is not bonded to an acid anhydride group, provided that the two acid anhydride groups are not bonded to the aromatic ring. Even when the structural unit (A1-1) contains an aromatic ring, the aromatic ring is not bonded to the two acid anhydride groups, and another functional group, another structure, etc. is bonded to the two acid anhydride groups. This is presumably because the proportion of aromatic rings in the structural unit (A1-1) is reduced, and the light transmittance of the polyamic acid ester and the resin composition containing the same tends to improve. From the viewpoint of the light transmittance of the polyamic acid ester and the resin composition containing it, the structural unit (A1-1) preferably does not contain an aromatic ring that is not bonded to the two acid anhydride groups.
  • the structural unit (A1-1) preferably contains the aforementioned alicyclic structure from the viewpoint of durability when cured.
  • the structural unit (A1-1) may contain one alicyclic structure or two or more alicyclic structures.
  • the structural unit (A1-2) may be any unit as long as it does not contain an aromatic ring, or the ratio of the number of aromatic rings contained in the tetracarboxylic dianhydride to the molecular weight of the tetracarboxylic dianhydride is less than 0.0068.
  • the ratio of the number of aromatic rings contained in a tetracarboxylic dianhydride to the molecular weight of the tetracarboxylic dianhydride is also referred to as "aromatic ring content 1".
  • the aromatic ring content 1 may be 0.0060 or less, 0.0050 or less, 0.0040 or less, or may be 0, meaning that no aromatic rings are contained.
  • the tetracarboxylic dianhydride preferably contains at least one of the compounds represented by the following chemical formulas (A-1) to (A-6).
  • the compounds represented by the following chemical formulas (A-1) to (A-6) are preferred examples of the tetracarboxylic dianhydride constituting the structural unit (A1-1) and the tetracarboxylic dianhydride constituting the structural unit (A1-2).
  • the compound represented by the chemical formula (A-1) and the compound represented by the chemical formula (A-5) are tetracarboxylic dianhydrides containing an aromatic ring that is not bonded to two acid anhydride groups.
  • the compounds represented by the chemical formulas (A-2) to (A-4) and the compound represented by the chemical formula (A-6) are tetracarboxylic dianhydrides containing no aromatic ring.
  • the tetracarboxylic dianhydride preferably contains at least one of the compounds represented by the chemical formula (A-2), the compounds represented by the chemical formula (A-4), and the compounds represented by the chemical formula (A-6).
  • the structural unit (A) may have a structural unit (A2) in which two acid anhydride groups contained in a tetracarboxylic dianhydride are bonded to an aromatic ring.
  • A2 By including the structural unit (A2), the durability of the cured product is improved.
  • the aromatic ring content 1 may be 0.0045 or more, 0.0050 or more, or 0.0060 or more.
  • the upper limit may be, for example, 0.0100, 0.0080, or 0.0070.
  • the structural unit (A2) may contain groups represented by the following general formulas (A) to (E):
  • a and B each independently represent a single bond, a methylene group, a halogenated methylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-) or a silylene bond (-Si(R A ) 2 -; each of R A independently represents a hydrogen atom, an alkyl group or a phenyl group), and both A and B are not single bonds.
  • C represents a single bond, an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R A ) 2 -;
  • R A each independently represents a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si(R B ) 2 -O-) n ;
  • R B each independently represents a hydrogen atom, an alkyl group, or a phenyl group, and n is an integer of 1 or 2 or more), or a divalent group comprising at least two of these in combination.
  • C may also have a structure represented by formula (C1) below.
  • the alkylene group represented by C in general formula (E) is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably an alkylene group having 1 or 2 carbon atoms.
  • alkylene group represented by C in the general formula (E) include linear alkylene groups such as a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group; a methylmethylene group, a methylethylene group, an ethylmethylene group, a dimethylmethylene group, a 1,1-dimethylethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, an ethylethylene group, a 1-methyltetramethylene group, a 2-methyltetramethylene group, a 1-ethyltrimethylene group, a 2-ethyltrimethylene group, a 1,1-dimethyl branched alkylene groups such as ethyltrimethylene group, 1,2-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene
  • the halogenated alkylene group represented by C in general formula (E) is preferably a halogenated alkylene group having 1 to 10 carbon atoms, more preferably a halogenated alkylene group having 1 to 5 carbon atoms, and even more preferably a halogenated alkylene group having 1 to 3 carbon atoms.
  • Specific examples of the halogenated alkylene group represented by C in the general formula (E) include alkylene groups in which at least one hydrogen atom contained in the alkylene group represented by C in the above-mentioned general formula (E) is substituted with a halogen atom such as a fluorine atom or a chlorine atom.
  • a fluoromethylene group, a difluoromethylene group, a hexafluorodimethylmethylene group, etc. are preferred.
  • the alkyl group represented by R A or R B contained in the silylene bond or siloxane bond is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably an alkyl group having 1 or 2 carbon atoms.
  • Specific examples of the alkyl group represented by R A or R B include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, and the like.
  • the combination of A and B in formula (D) is not particularly limited, and a combination of a methylene group and an ether bond, a combination of a methylene group and a sulfide bond, a combination of a carbonyl group and an ether bond, and the like are preferred.
  • C is preferably a single bond, an ether bond, a carbonyl group, or the like.
  • the tetracarboxylic dianhydride of the structural unit (A2) may be pyromellitic dianhydride, 2,3,6,7-naphthalene tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 2,3,5,6-pyridine tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 3,4,9,10-perylene tetracarboxylic dianhydride, m-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, p-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, 1,1,1,
  • the content of the structural unit (A1-1) in the structural unit (A) and the content of the structural unit (A1-2) in the structural unit (A) are each independently preferably 25 mol% or more, more preferably 30 mol% or more, and even more preferably 40 mol% or more.
  • the upper limit is not particularly limited, and may be 100 mol%, 80 mol% or less, or 60 mol% or less.
  • At least a portion of the structural unit (A) has an unsaturated double bond.
  • the unsaturated double bond contained in the structural unit (A) may be present in the ester portion of the tetracarboxylic dianhydride.
  • the R of the -COOR group has an unsaturated double bond. It is preferable that R contains a group represented by the following general formula (7).
  • R 8 to R 10 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms; q represents an integer of 1 to 10.
  • the carbon number of the aliphatic hydrocarbon group represented by R 8 to R 10 in general formula (7) is 1 to 3, and preferably 1 or 2.
  • Specific examples of the aliphatic hydrocarbon group represented by R 8 to R 10 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, etc., and a methyl group is preferred.
  • R 8 to R 10 in the general formula (7) a combination in which R 8 and R 9 are hydrogen atoms and R 10 is a hydrogen atom or a methyl group is preferred.
  • q is preferably an integer from 1 to 10, more preferably an integer from 2 to 5, and even more preferably 2 or 3.
  • the polyamic acid ester contains a structural unit (B) derived from a diamine compound.
  • a structural unit (B) derived from a diamine compound.
  • the structural unit (B) may or may not contain an aromatic ring, but it is preferable for it to contain an aromatic ring from the viewpoint of durability when made into a cured product.
  • the structural unit (B) preferably contains a structural unit represented by the formula -NH-Y-NH-, where Y is a divalent organic group.
  • the divalent organic group represented by Y preferably has 6 to 25 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 12 to 14 carbon atoms.
  • the divalent organic group represented by Y may be a divalent aliphatic group or a divalent aromatic group. From the viewpoint of heat resistance and high elasticity, the divalent organic group represented by Y is preferably a divalent aromatic group.
  • divalent aromatic group represented by Y examples include groups represented by the following general formula (F) and the following general formula (G).
  • each R independently represents an alkyl group, an alkoxy group, a halogenated alkyl group, or a phenyl group, and each n independently represents an integer of 0 to 4.
  • D represents a single bond, or an alkylene group, a halogenated alkylene group, a carbonyl group, a sulfonyl group, an ether bond (-O-), a sulfide bond (-S-), a silylene bond (-Si(R A ) 2 -;
  • R A each independently represents a hydrogen atom, an alkyl group, or a phenyl group), a siloxane bond (-O-(Si(R B ) 2 -O-) n ;
  • R B each independently represents a hydrogen atom, an alkyl group, or a phenyl group, and n represents an integer of 1 or 2 or more), or a divalent group combining at least
  • the alkyl group represented by R in general formula (F) or general formula (G) is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and further preferably an alkyl group having 1 or 2 carbon atoms.
  • Specific examples of the alkyl group represented by R in general formula (F) or general formula (G) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.
  • the alkoxy group represented by R in the general formula (F) or the general formula (G) is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 5 carbon atoms, and further preferably an alkoxy group having 1 or 2 carbon atoms.
  • Specific examples of the alkoxy group represented by R in the general formula (F) or (G) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, and a t-butoxy group.
  • the halogenated alkyl group represented by R in the general formula (F) or (G) is preferably a halogenated alkyl group having 1 to 5 carbon atoms, more preferably a halogenated alkyl group having 1 to 3 carbon atoms, and further preferably a halogenated alkyl group having 1 or 2 carbon atoms.
  • Specific examples of the halogenated alkyl group represented by R in general formula (F) or general formula (G) include alkyl groups in which at least one hydrogen atom contained in the alkyl group represented by R in general formula (F) or general formula (G) is substituted with a halogen atom such as a fluorine atom or a chlorine atom.
  • a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, etc. are preferred.
  • n is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.
  • divalent aliphatic group represented by Y examples include linear or branched alkylene groups, cycloalkylene groups, divalent groups having a polyalkylene oxide structure, and divalent groups having a polysiloxane structure.
  • the linear or branched alkylene group represented by Y is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 1 to 15 carbon atoms, and even more preferably an alkylene group having 1 to 10 carbon atoms.
  • alkylene group represented by Y examples include a tetramethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a nonamethylene group, a decamethylene group, an undecamethylene group, a dodecamethylene group, a 2-methylpentamethylene group, a 2-methylhexamethylene group, a 2-methylheptamethylene group, a 2-methyloctamethylene group, a 2-methylnonamethylene group, and a 2-methyldecamethylene group.
  • the cycloalkylene group represented by Y is preferably a cycloalkylene group having 3 to 10 carbon atoms, and more preferably a cycloalkylene group having 3 to 6 carbon atoms.
  • Specific examples of the cycloalkylene group represented by Y include a cyclopropylene group, a cyclohexylene group, and the like.
  • the unit structure contained in the divalent group having a polyalkylene oxide structure represented by Y is preferably an alkylene oxide structure having 1 to 10 carbon atoms, more preferably an alkylene oxide structure having 1 to 8 carbon atoms, and even more preferably an alkylene oxide structure having 1 to 4 carbon atoms.
  • the polyalkylene oxide structure is preferably a polyethylene oxide structure or a polypropylene oxide structure.
  • the alkylene group in the alkylene oxide structure may be linear or branched.
  • the unit structure in the polyalkylene oxide structure may be of one type or two or more types.
  • Examples of the divalent group having a polysiloxane structure represented by Y include divalent groups having a polysiloxane structure in which a silicon atom in the polysiloxane structure is bonded to a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms bonded to a silicon atom in the polysiloxane structure include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-octyl group, a 2-ethylhexyl group, an n-dodecyl group, etc.
  • a methyl group is preferable.
  • the aryl group having 6 to 18 carbon atoms bonded to the silicon atom in the polysiloxane structure may be unsubstituted or substituted with a substituent.
  • substituent when the aryl group has a substituent include a halogen atom, an alkoxy group, and a hydroxy group.
  • aryl group having 6 to 18 carbon atoms include a phenyl group, a naphthyl group, and a benzyl group. Of these, a phenyl group is preferred.
  • the alkyl group having 1 to 20 carbon atoms or the aryl group having 6 to 18 carbon atoms in the polysiloxane structure may be of one type or of two or more types.
  • the silicon atom constituting the divalent group having a polysiloxane structure represented by Y may be bonded to the NH group in general formula (6) via an alkylene group such as a methylene group or an ethylene group, or an arylene group such as a phenylene group.
  • diamine compound of the structural unit (B) examples include 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 2,2'-difluoro-4,4'-diaminobiphenyl, p-phenylenediamine, m-phenylenediamine, p-xylylenediamine, m-xylylenediamine, 1,5-diaminonaphthalene, benzidine, 2,2'-bis(trifluoromethyl)benzidine, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 2,4'-diaminodiphenyl ether, 2,2'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,4
  • the polyamic acid ester having an unsaturated double bond may be, for example, a polyamic acid ester having a structural unit represented by the following general formula (6).
  • X represents a tetravalent organic group
  • Y represents a divalent organic group
  • R6 and R7 are each independently a hydrogen atom, a group represented by the following general formula (7), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R6 and R7 is a group represented by the following general formula (7), and the tetravalent organic group represented by X does not contain an aromatic ring, or if it contains an aromatic ring, the aromatic ring is not bonded to four carbonyl groups.
  • R 8 to R 10 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 3 carbon atoms; q represents an integer of 1 to 10.
  • the number of carbon atoms in the aliphatic hydrocarbon group represented by R6 and R7 in general formula (6) is 1 to 4, and preferably 1 or 2.
  • Specific examples of the aliphatic hydrocarbon group represented by R6 and R7 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and the like.
  • R 6 and R 7 are a group represented by the general formula (7), and it is more preferable that both of R 6 and R 7 are groups represented by the general formula (7).
  • General formula (7) has the same meaning as general formula (7) explained in relation to the structural unit (A).
  • Y has the same meaning as Y explained in relation to the structural unit (B).
  • X in the general formula (6) may be any of the linking groups and composite linking groups described in relation to the structural units (A1-1) and (A1-2).
  • the tetravalent organic group represented by X preferably has 4 to 25 carbon atoms, more preferably 4 to 13 carbon atoms, and even more preferably 6 to 12 carbon atoms.
  • the tetravalent organic group represented by X may contain an aromatic ring. If X contains an aromatic ring, the aromatic ring is not bonded to four carbonyl groups.
  • X corresponds to a residue derived from a tetracarboxylic dianhydride
  • specific examples of the tetracarboxylic dianhydride that is the source of the residue include the tetracarboxylic dianhydrides exemplified for the structural units (A1-1) and (A1-2).
  • the polyamic acid ester having an unsaturated double bond may further have a structural unit represented by the following general formula (6-1) in addition to the structural unit represented by the general formula (6).
  • X 1 represents a tetravalent organic group
  • Y represents a divalent organic group
  • R 6 and R 7 are each independently a hydrogen atom, a group represented by the following general formula (7), or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and at least one of R 6 and R 7 is a group represented by the following general formula (7), and the tetravalent organic group represented by X 1 contains an aromatic ring.
  • the four carbonyl groups in the general formula (6-1) are bonded to the aromatic ring contained in X 1 , and it is more preferable that the two carbonyl groups in the general formula (6-1) are bonded to one aromatic ring (first aromatic ring) contained in X 1 , and the remaining two carbonyl groups are bonded to another aromatic ring (second aromatic ring) contained in X 1 .
  • Y, R 6 and R 7 in formula (6-1) have the same meanings as Y, R 6 and R 7 in formula (6), respectively.
  • X1 in the general formula (6-1) include the general formulae (A) to (E) described in relation to the structural unit (A2).
  • X corresponds to a residue derived from a tetracarboxylic dianhydride
  • specific examples of the tetracarboxylic dianhydride that is the source of the residue include the tetracarboxylic dianhydrides described in relation to the structural unit (A2).
  • the polyamic acid ester may have other structural units than those represented by the general formula (6) and the general formula (6-1).
  • Examples of the other structural units include structural units in which neither R 6 nor R 7 in the general formula (6) and the general formula (6-1) is a group represented by the general formula (7).
  • the content of the structural unit represented by general formula (6) in the polyamic acid ester is preferably 25 mol% or more, more preferably 30 mol% or more, and even more preferably 40 mol% or more, based on the total structural units contained in the polyamic acid ester.
  • the total content of the structural units represented by general formula (6) and the structural units represented by general formula (6-1) in the polyamic acid ester is preferably 50 mol% or more, more preferably 80 mol% or more and 100 mol% or less, and even more preferably 90 mol% or more and 100 mol% or less, based on all the structural units contained in the polyamic acid ester.
  • the polyamic acid ester may be synthesized using a tetracarboxylic dianhydride and a diamine compound.
  • X corresponds to a residue derived from the tetracarboxylic dianhydride
  • Y corresponds to a residue derived from the diamine compound.
  • the polyamic acid ester may be synthesized using a tetracarboxylic acid instead of the tetracarboxylic dianhydride.
  • X is the same as X in general formula (6), and specific examples and preferred examples are also the same.
  • the polyamic acid ester can be obtained, for example, by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH in an organic solvent such as N-methyl-2-pyrrolidone to obtain a diester derivative, and then subjecting the diester derivative to a condensation reaction with a diamine compound represented by H 2 N-Y-NH 2 ; or by reacting a tetracarboxylic dianhydride with a diamine compound represented by H 2 N-Y-NH 2 in an organic solvent to obtain a polyamic acid, adding a compound represented by R-OH, and reacting the resulting polyamic acid in an organic solvent to introduce an ester group.
  • a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH in an organic solvent such as N-methyl-2-pyrrolidone to obtain a diester derivative, and then subjecting the diester derivative to a condensation reaction with a
  • Y in the diamine compound represented by H 2 N-Y-NH 2 is the same as Y in general formula (6), and specific examples and preferred examples are also the same.
  • R in the compound represented by R-OH represents a group represented by general formula (7) or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and specific examples and preferred examples are the same as R 6 and R 7 in general formula (6).
  • the tetracarboxylic dianhydride represented by formula (8), the diamine compound represented by H 2 N-Y-NH 2 , and the compound represented by R-OH may each be used alone or in combination of two or more.
  • a polyamic acid ester can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH to form a diester derivative, then reacting the diester with a chlorinating agent such as thionyl chloride to convert it to an acid chloride, and then reacting a diamine compound represented by H 2 N-Y-NH 2 with the acid chloride.
  • the polyamic acid ester can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a compound represented by R-OH to form a diester derivative, and then reacting the diamine compound represented by H 2 N-Y-NH 2 with the diester derivative in the presence of a carbodiimide compound. Furthermore, the polyamic acid ester can be obtained by reacting a tetracarboxylic dianhydride represented by the following general formula (8) with a diamine compound represented by H 2 N-Y-NH 2 to form a polyamic acid, isoimidizing the polyamic acid in the presence of trifluoroacetic anhydride, and then reacting with a compound represented by R-OH.
  • the compound represented by R-OH may be reacted in advance with a part of the tetracarboxylic dianhydride, and the partially esterified tetracarboxylic dianhydride may be reacted with the diamine compound represented by H 2 N-Y-NH 2 to form a polyamic acid.
  • Compounds represented by R-OH that are used in the synthesis of polyamic acid esters include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, etc.
  • the molecular weight of the polyamic acid ester is not particularly limited, and may be, for example, 10,000 to 200,000, 20,000 to 150,000, or 30,000 to 100,000 in weight average molecular weight.
  • the weight average molecular weight can be measured, for example, by gel permeation chromatography, and can be calculated using a standard polystyrene calibration curve.
  • the weight average molecular weight of the polyamic acid ester is preferably 20,000 or more, more preferably 30,000 or more, and even more preferably 40,000 or more.
  • the weight average molecular weight of the polyamic acid ester may be 200,000 or less, 150,000 or less, or 100,000 or less.
  • the weight average molecular weight of the polyamic acid ester is preferably 35,000 or more, more preferably 35,000 or more, and even more preferably 40,000 or more, from the viewpoint of obtaining a cured product with low stress.
  • the weight average molecular weight of the polyamic acid ester is preferably 50,000 or more, more preferably 60,000 or more, and even more preferably 70,000 or more, from the viewpoint of obtaining a cured product with low stress.
  • the stress when the polyamic acid ester is made into a cured film may be 30.0 MPa or less, 20.0 MPa or less, 5.0 MPa to 20.0 MPa, or 5.0 MPa to 15.0 MPa.
  • the stress of a cured film made from the polyamic acid ester can be measured as follows. First, 30 parts by mass of a polyamic acid ester and 70 parts by mass of a solvent (e.g., 3-methoxy-N,N-dimethylpropanamide) are mixed to obtain a resin composition. The obtained resin composition is applied onto a silicon wafer, and then the solvent is volatilized to obtain a coating film having a thickness of about 10 ⁇ m after curing. The obtained coating film is heated and cured at 350° C. for 1 hour in a nitrogen atmosphere to obtain a polyimide film (cured film). The residual stress of the cured polyimide film is measured at room temperature using a stress measuring device.
  • a solvent e.g., 3-methoxy-N,N-dimethylpropanamide
  • the resin composition of the present disclosure includes the polyamic acid ester of the present disclosure.
  • the resin composition may include other components other than the polyamic acid ester of the present disclosure.
  • the other components include resin components other than the polyamic acid ester of the present disclosure, polymerizable monomers, photopolymerization initiators, thermal polymerization initiators, solvents, sensitizers, stabilizers, coupling agents, surfactants, leveling agents, and rust inhibitors.
  • the resin components other than the polyamic acid ester of the present disclosure include polyamic acid esters other than the polyamic acid ester of the present disclosure and resin components other than the polyamic acid ester.
  • the resin composition of the present disclosure may be a photosensitive resin composition, or may be a thermosetting resin composition that is cured by heating.
  • the resin composition of the present disclosure may be, for example, a composition that can provide a cured product by irradiation with light, heating, etc.
  • a patterned cured product may be formed using the photosensitive resin composition.
  • the cured product obtained from the resin composition of the present disclosure can be used as an interlayer insulating film, a cover coat layer, or a surface protection film. Furthermore, the cured product can be used as a passivation film, a buffer coat film, etc. Using one or more selected from the group consisting of the above passivation films, buffer coat films, interlayer insulating films, cover coat layers, and surface protection films, etc., highly reliable electronic components such as semiconductor devices, multilayer wiring boards, various electronic devices, and stacked devices (multi-die fan-out wafer level packages, etc.) can be manufactured.
  • This solution was designated as the sBPDA solution.
  • 340 g of the sBPDA solution was placed in a 0.5-liter flask equipped with a stirrer and a thermometer, and then 29.7 g (250 mmol) of thionyl chloride was added dropwise using a dropping funnel while cooling with ice so that the reaction solution temperature was kept below 10° C. After the dropwise addition of thionyl chloride was completed, the mixture was stirred for 2 hours while cooling with ice to obtain a solution of acid chloride of sBPDA.
  • GPC gel permeation chromatography
  • This solution was designated as the sBPDA solution.
  • 65.3 g (170 mmol) of the compound (CpODA) represented by chemical formula (A-2) that had been dried in a dryer at 160° C. for 24 hours, 46.5 g (357 mmol) of 2-hydroxyethyl methacrylate, and 0.183 g of benzoquinone were dissolved in 369.5 g of 3-methoxy-N,N-dimethylpropanamide ("KJCMPA-100" (KJ Chemicals Co., Ltd.)), and after adding a catalytic amount of 1,8-diazabicycloundecene, the mixture was stirred at room temperature (25° C.) for 24 hours to carry out esterification, thereby obtaining a diester solution.
  • KJCMPA-100 3-methoxy-N,N-dimethylpropanamide
  • This solution was designated as a CpODA solution.
  • a CpODA solution In a 0.5-liter flask equipped with a stirrer and a thermometer, 170 g of the sBPDA solution and 170 g of the CpODA solution obtained above were placed.
  • the mixing ratio of CpODA to sBPDA (CpODA:sBPDA) was 0.5:0.5 in terms of the molar equivalents (mol Eq) of the acid anhydride groups.
  • 29.7 g of thionyl chloride was added dropwise using a dropping funnel so that the reaction solution temperature was kept at 10° C. or less.
  • polyamic acid ester 3 was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 3.
  • the weight average molecular weight of polyamic acid ester 3 calculated in terms of standard polystyrene was 28,000.
  • Polyamic acid ester 4 was obtained in the same manner as in the above (Synthesis of polyamic acid ester 3), except that the amount of PPD added was changed so that the molar ratio to the acid anhydride was 0.99.
  • polyamic acid ester 5 was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 5.
  • the weight average molecular weight of polyamic acid ester 5 calculated in terms of standard polystyrene was 25,000.
  • Polyamic acid ester 6 was obtained in the same manner as in the above (Synthesis of polyamic acid ester 5), except that the amount of PPD added was changed so that the molar ratio to the acid anhydride was 0.99.
  • This polyamic acid ester 7 solution was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 7.
  • the weight average molecular weight of polyamic acid ester 7 calculated in terms of standard polystyrene was 27,000.
  • Polyamic acid ester 8 was obtained in the same manner as in the above (Synthesis of polyamic acid ester 7), except that the amount of PPD added was changed so that the molar ratio to the acid anhydride was 0.99.
  • the weight average molecular weight of polyamic acid ester 8 calculated in terms of standard polystyrene was 39,000.
  • This polyamic acid ester 9 solution was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 9.
  • the weight average molecular weight of polyamic acid ester 9 calculated in terms of standard polystyrene was 20,000.
  • Polyamic acid ester 10 was obtained in the same manner as in the above (Synthesis of polyamic acid ester 9), except that the amount of PPD added was changed so that the molar ratio to the acid anhydride was 0.99.
  • the weight average molecular weight of polyamic acid ester 10 calculated in terms of standard polystyrene was 47,000.
  • This polyamic acid ester 11 solution was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 11.
  • the weight average molecular weight of polyamic acid ester 11 calculated in terms of standard polystyrene was 46,000.
  • Polyamic acid ester 12 was obtained in the same manner as in the above (Synthesis of polyamic acid ester 11), except that the amount of PPD added was changed so that the molar ratio to the acid anhydride was 0.99.
  • the weight average molecular weight of polyamic acid ester 12 calculated in terms of standard polystyrene was 89,000.
  • a solution prepared by dissolving 28.12 g (108.0 mmol) of 4,4′′-diamino-p-terphenyl (DATP), 35.884 g (454 mmol) of pyridine, and 0.082 g (0.757 mmol) of benzoquinone in 69.17 g of KJCMPA-100 was dropped into the solution of acid chlorides of CpODA and sBPDA while taking care not to allow the temperature of the reaction solution to exceed 10° C. by ice cooling, thereby obtaining a solution of polyamic acid ester 14.
  • This polyamic acid ester 14 solution was dropped into distilled water, and the precipitate was collected by filtration and dried under reduced pressure to obtain polyamic acid ester 14.
  • the weight average molecular weight of polyamic acid ester 14 calculated in terms of standard polystyrene was 45,000.
  • Resin compositions 1 to 14 were prepared using the above-mentioned polyamic acid esters 1 to 14. Each resin composition was prepared using 30 parts by mass of the polyamic acid ester and 70 parts by mass of 3-methoxy-N,N-dimethylpropanamide ("KJCMPA-100" (KJ Chemicals Corporation)) as a solvent.
  • KJCMPA-100 3-methoxy-N,N-dimethylpropanamide
  • the obtained resin composition was applied onto a 6-inch silicon wafer by spin coating, and heated on a hot plate at 100°C for 3 minutes to volatilize the solvent and obtain a coating film with a thickness of about 10 ⁇ m after curing. This was then heated and cured at 350°C for 1 hour in a nitrogen atmosphere using a vertical diffusion furnace manufactured by Koyo Lindberg to obtain a polyimide film (cured film).
  • the residual stress of the cured polyimide film was measured at room temperature using a thin film stress measurement device FLX-2320 manufactured by KLATencor. The results are shown in Table 1.
  • Table 1 shows the results of measuring the various physical properties when polyamic acid esters 1 to 14 were used.
  • acid anhydride 1 is the acid anhydride that constitutes the structural unit (A1-1) and the structural unit (A1-2)
  • acid anhydride 2 is the acid anhydride that constitutes the structural unit (A2).
  • the "-" in the column for acid anhydride 1 means that it is unused.

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Abstract

L'invention concerne un ester d'acide polyamique qui contient une unité structurale (A) dérivée d'un dianhydride d'acide tétracarboxylique, et une unité structurale (B) dérivée d'un composé diamine. Au moins une partie de ladite unité structurale (A) possède une double liaison insaturée. La transmittance de lumière de ３８０ｎｍ dans le cas d'une solution de ３－méthoxy－Ｎ，Ｎ－diméthylpropanamide à 0,1% en masse de concentration en matières solides, est supérieure ou égale à 10%.
PCT/JP2022/043636 2022-11-25 2022-11-25 Ester d'acide polyamique, et composition de résine WO2024111131A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006058324A (ja) * 2004-08-17 2006-03-02 Toyobo Co Ltd ネガ型感光性ポリイミド前駆体組成物
JP2018035340A (ja) * 2016-08-26 2018-03-08 Jnc株式会社 ポリエステルアミド酸及びこれを含有する感光性組成物
JP2018066017A (ja) * 2012-05-28 2018-04-26 宇部興産株式会社 ポリイミド前駆体及びポリイミド
JP2022021934A (ja) * 2020-07-22 2022-02-03 Ｈｄマイクロシステムズ株式会社 感光性樹脂組成物、硬化物、パターン硬化物の製造方法、及び電子部品
WO2022044999A1 (fr) * 2020-08-25 2022-03-03 富士フイルム株式会社 Composition de résine durcissable, produit durci, stratifié, procédé de production de produit durci, dispositif à semi-conducteurs ainsi que précurseur polyimide et procédé de production de celui-ci
JP2022173076A (ja) * 2021-05-07 2022-11-17 Jsr株式会社 液晶配向剤、液晶配向膜及びその製造方法、液晶素子、液晶表示装置、並びに重合体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006058324A (ja) * 2004-08-17 2006-03-02 Toyobo Co Ltd ネガ型感光性ポリイミド前駆体組成物
JP2018066017A (ja) * 2012-05-28 2018-04-26 宇部興産株式会社 ポリイミド前駆体及びポリイミド
JP2018035340A (ja) * 2016-08-26 2018-03-08 Jnc株式会社 ポリエステルアミド酸及びこれを含有する感光性組成物
JP2022021934A (ja) * 2020-07-22 2022-02-03 Ｈｄマイクロシステムズ株式会社 感光性樹脂組成物、硬化物、パターン硬化物の製造方法、及び電子部品
WO2022044999A1 (fr) * 2020-08-25 2022-03-03 富士フイルム株式会社 Composition de résine durcissable, produit durci, stratifié, procédé de production de produit durci, dispositif à semi-conducteurs ainsi que précurseur polyimide et procédé de production de celui-ci
JP2022173076A (ja) * 2021-05-07 2022-11-17 Jsr株式会社 液晶配向剤、液晶配向膜及びその製造方法、液晶素子、液晶表示装置、並びに重合体

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