WO2019188432A1 - Composition de résine et composant électronique - Google Patents

Composition de résine et composant électronique Download PDF

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Publication number
WO2019188432A1
WO2019188432A1 PCT/JP2019/010901 JP2019010901W WO2019188432A1 WO 2019188432 A1 WO2019188432 A1 WO 2019188432A1 JP 2019010901 W JP2019010901 W JP 2019010901W WO 2019188432 A1 WO2019188432 A1 WO 2019188432A1
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Prior art keywords
group
resin composition
ene
resin
hept
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PCT/JP2019/010901
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English (en)
Japanese (ja)
Inventor
隆志 堤
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日本ゼオン株式会社
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Priority to KR1020207026849A priority Critical patent/KR102669132B1/ko
Priority to CN201980015060.1A priority patent/CN111770964B/zh
Priority to JP2020510662A priority patent/JP7512889B2/ja
Publication of WO2019188432A1 publication Critical patent/WO2019188432A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a resin composition and an electronic component, and more particularly to a resin composition that can be suitably used for forming an insulating film or the like used for an electronic component and an electronic component including a resin film made of the resin composition. is there.
  • Various display elements such as organic EL elements and liquid crystal display elements, integrated circuit elements, solid-state imaging elements, color filters, and electronic components such as black matrixes have surface protective films, element surfaces, Various resin films are provided as a planarizing film for planarizing wirings, an interlayer insulating film for insulating between wirings arranged in layers, and the like.
  • Patent Document 1 a resin composition containing a binder resin, a radiation-sensitive compound, an epoxy equivalent of 450 or less, a softening point of 30 ° C. or less, and a tetrafunctional or less epoxy crosslinking agent, and an aralkylphenol resin Has been proposed.
  • the resin composition according to Patent Document 1 it is possible to form a resin composition that can provide a resin film having high adhesion to the metal layer and excellent in developability and low moisture absorption.
  • the resin film obtained by using the resin composition as described above may be used to form a desired pattern shape according to the application.
  • the resin film be capable of forming a pattern shape with good resolution.
  • lithography is performed on the resin film to obtain a development pattern, and when the development pattern is cured to obtain a pattern, the pattern shape is changed before and after curing. It is necessary to be able to sufficiently suppress the change.
  • the resin film is also required to have excellent extensibility.
  • the resin film obtained using the above conventional resin composition cannot achieve both good resolution and sufficient stretchability.
  • the present invention provides a resin composition capable of forming a resin film excellent in resolution and extensibility, and a high-performance electronic component including a resin film formed using the resin composition. Objective.
  • the present inventor has intensively studied for the purpose of solving the above problems. According to the resin composition containing the cyclic olefin polymer having a polar group and the epoxy resin having an epoxy equivalent of a predetermined value or more, the inventor forms a resin film having excellent resolution and extensibility.
  • the present invention has been completed by newly finding the points that can be achieved.
  • the resin composition of this invention is the cyclic olefin polymer (A) which has a polar group, and an epoxy equivalent is 500 or more. It contains an epoxy resin (B).
  • an epoxy equivalent represents the gram number (g / eq.) Of resin containing 1 g equivalent of epoxy groups, and can be calculated
  • the epoxy resin (B) preferably contains a flexible skeleton and an aromatic group in the molecule. If the epoxy resin (B) contained in the resin composition contains a flexible skeleton and an aromatic group in the molecule, the resolution and extensibility of the resulting resin film can be further enhanced.
  • the content of the epoxy resin (B) is preferably 40 parts by mass or more and 100 parts by mass or less per 100 parts by mass of the cyclic olefin polymer (A). If content of an epoxy resin (B) is more than the said lower limit, the extensibility of a resin film can be improved further. Moreover, if content of an epoxy resin (B) is below the said upper limit, the resolution of a resin film can be improved further.
  • the resin composition of the present invention preferably further contains a crosslinking agent (C) containing a phenolic hydroxyl group and an alkoxymethyl group in the molecule.
  • a resin film having excellent chemical resistance can be formed.
  • the content of the crosslinking agent (C) is preferably 1 part by mass or more and 100 parts by mass or less per 100 parts by mass of the cyclic olefin polymer (A). If content of a crosslinking agent (C) is more than the said lower limit, the chemical resistance of a resin film can be improved further. Moreover, if content of a crosslinking agent (C) is below the said upper limit, the extensibility of a resin film can be improved.
  • the resin composition of the present invention further contains a photoacid generator (D). If the resin composition contains a photoacid generator (D), the resin film can be patterned by changing the solubility of the resin film in the developer by the action of the photoacid generator (D). Become.
  • the present invention is intended to advantageously solve the above-described problems, and the electronic component of the present invention is characterized by including a resin film made of any of the resin compositions described above. Since the resin film formed using the resin composition described above is excellent in resolution and extensibility, an electronic component including the resin film can sufficiently perform its intended function, and thus has high performance. It is.
  • the present invention it is possible to provide a resin composition capable of forming a resin film excellent in resolution and extensibility, and a high-performance electronic component including a resin film formed using the resin composition. it can.
  • the resin composition of the present invention can be used for forming a resin film.
  • a resin film can be used as, for example, a surface protective film, a planarizing film, and an interlayer insulating film in an electronic component manufactured according to the wafer level package technology.
  • the electronic component of this invention is equipped with the resin film obtained using the resin composition of this invention.
  • the resin composition of the present invention contains a cyclic olefin polymer (A) having a polar group, and an epoxy resin (B) having an epoxy equivalent of 500 or more, optionally, a crosslinking agent (C), and photoacid generation An agent (D) and the like may further be contained.
  • the resin composition of this invention contains the cyclic olefin polymer (A) which has a polar group, and the epoxy resin (B) whose epoxy equivalent is 500 or more, it is excellent in resolution and an extendibility.
  • a resin film can be formed. Conventionally, a resin film having good extensibility often has a high content ratio of a resin component having a low glass transition temperature. Even if a pattern is formed by lithography using the resin film, the resin film is subjected to a thermosetting process or the like. When provided, pattern collapse or the like occurred, and as a result, resolution was sacrificed due to the provision of extensibility.
  • the epoxy resin (B) having an epoxy equivalent of 500 or more in combination with the cyclic olefin polymer (A) having a polar group, the epoxy resin (B) having an epoxy equivalent of 500 or more is blended, whereby resolution and extensibility are obtained. It became possible to achieve both.
  • cyclic olefin polymer having a polar group (A) When the cyclic olefin polymer blended in the resin composition has a polar group, the strength of the resulting resin film can be increased.
  • the cyclic olefin polymer (A) having a polar group may have one or more polar groups. Furthermore, it is preferable that the cyclic olefin polymer (A) having a polar group has at least a protic polar group.
  • the cyclic olefin polymer (A) having a polar group has a protic polar group, it has solubility in a developer (in particular, an alkali developer described later), and the resin composition is
  • a developer in particular, an alkali developer described later
  • the crosslinking agent (C) described later is included, a resin film excellent in chemical resistance can be formed by being well crosslinked by the crosslinking agent (C).
  • the protic polar group means a group containing an atom belonging to Group 15 or Group 16 of the periodic table to which a hydrogen atom is directly bonded.
  • the atom belonging to Group 15 or 16 of the periodic table is preferably an atom belonging to Group 1 or 2 of Group 15 or 16 of the periodic table, more preferably an oxygen atom, a nitrogen atom or a sulfur atom. Particularly preferred is an oxygen atom.
  • protic polar groups include polar groups having oxygen atoms such as hydroxyl groups, carboxyl groups (hydroxycarbonyl groups), sulfonic acid groups, and phosphoric acid groups; primary amino groups, secondary amino groups A polar group having a nitrogen atom such as a primary amide group or a secondary amide group (imide group); a polar group having a sulfur atom such as a thiol group.
  • a polar group having an oxygen atom is preferable, and a carboxyl group is more preferable.
  • cyclic olefin polymer (A) may have only 1 type of protic polar groups, and may have 2 or more types.
  • the method of introducing the above-mentioned protic polar group into the cyclic olefin polymer (A) is not particularly limited. That is, the cyclic olefin polymer (A) includes, for example, a repeating unit derived from the cyclic olefin monomer (a) having a protic polar group, and optionally a repeating derived from the other monomer (b).
  • a polymer containing units may be used, or a polymer obtained by introducing a protic polar group into a cyclic olefin polymer having no protic polar group using a modifier, but the former is preferred. .
  • the cyclic olefin monomer (a) having a protic polar group is not particularly limited as long as it is a monomer having the above-mentioned protic polar group and a cyclic olefin structure.
  • Preferred examples include a monomer and a cyclic olefin monomer having a hydroxyl group.
  • Preferable examples of these monomers include various monomers described in International Publication No. 2015/141717.
  • a cyclic olefin monomer having a carboxyl group is preferable from the viewpoint of improving the solubility in a developing solution and improving the adhesion of the resin film to the substrate, and 4-hydroxycarbonyltetracyclo [6.2.1.1]. 3,6 . 0 2,7 ] dodec-9-ene (hereinafter also referred to as “TCDC”) is more preferable.
  • a cyclic olefin monomer (a) may be used individually by 1 type, or may be used in combination of 2 or more type.
  • cyclic olefin monomer having a carboxyl group examples include 2-hydroxycarbonylbicyclo [2.2.1] hept-5-ene, 2-methyl-2-hydroxycarbonylbicyclo [2.2.1] hept- 5-ene, 2-carboxymethyl-2-hydroxycarbonylbicyclo [2.2.1] hept-5-ene, 2-hydroxycarbonyl-2-methoxycarbonylmethylbicyclo [2.2.1] hept-5-ene 2-hydroxycarbonyl-2-ethoxycarbonylmethylbicyclo [2.2.1] hept-5-ene, 2-hydroxycarbonyl-2-propoxycarbonylmethylbicyclo [2.2.1] hept-5-ene, 2 -Hydroxycarbonyl-2-butoxycarbonylmethylbicyclo [2.2.1] hept-5-ene, 2 Hydroxycarbonyl-2-pentyloxycarbonylmethylbicyclo [2.2.1]
  • the content rate of the repeating unit derived from the cyclic olefin monomer (a) in the cyclic olefin polymer (A) is preferably 10 mol% or more, assuming that all repeating units are 100 mol%, and 20 mol. % Or more, more preferably 30 mol% or more, preferably 90 mol% or less, more preferably 80 mol% or less, and further preferably 70 mol% or less. preferable. If the ratio of the repeating unit derived from the cyclic olefin monomer (a) is 10 mol% or more, it is possible to increase the sensitivity during patterning using the resin film and to effectively suppress the development residue. If it is 90 mol% or less, the amount of the remaining film after development of the cyclic olefin polymer (A) can be sufficiently secured.
  • the other monomer (b) is not particularly limited as long as it is a monomer copolymerizable with the above-mentioned cyclic olefin monomer (a).
  • a monomer copolymerizable with the cyclic olefin monomer (a) a cyclic olefin monomer (b1) having a polar group other than a protic polar group, a cyclic olefin monomer having no polar group ( and monomers (b3) other than b2) and cyclic olefins.
  • various monomers (b1) to (b3) various monomers described in International Publication No. 2015/141717 can be used.
  • cyclic olefin monomers having a halogen atom
  • a cyclic olefin monomer (b1) having a polar group of N-phenyl-bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide hereinafter also referred to as “NBPI”.
  • NBPI cyclic olefin monomers having an N-substituted imide group.
  • cyclic olefin monomer having an N-substituted imide group examples include monomers represented by the following general formula (1) and general formula (2).
  • a monomer that can be represented by the following general formula (1) is preferable from the viewpoint of improving heat resistance and suppressing pattern flow.
  • R 1 represents a hydrogen atom, a cyclic or chain alkyl group having 1 to 16 carbon atoms, or an aryl group.
  • N represents an integer of 1 to 2.
  • R 2 is a divalent alkylene group having 1 to 3 carbon atoms
  • R 3 is a monovalent alkyl group having 1 to 10 carbon atoms
  • R 1 is an alkyl group or aryl group having 1 to 16 carbon atoms.
  • the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, linear alkyl groups such as n-pentadecyl group and n-hexadecyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl
  • Alkyl group 2-propyl group, 2-butyl group, 2-methyl-1-propyl group, 2-methyl-2-propyl group, 1-methylbutyl group, 2-methylbutyl group, 1-methylpentyl group, 1- And branched alkyl groups such as ethylbutyl group, 2-methylhexyl group, 2-ethylhexyl group, 4-methylheptyl group, 1-methylnonyl group, 1-methyltridecyl group and 1-methyltetradecyl group.
  • Specific examples of the aryl group include a phenyl group and a benzyl group.
  • an alkyl group and an aryl group having 6 to 14 carbon atoms are preferable, and an alkyl group and an aryl group having 6 to 10 carbon atoms are more preferable because of excellent heat resistance and solubility in an alkali developer.
  • the carbon number is less than the above lower limit, the compatibility with the crosslinking agent is poor. Further, if the carbon number exceeds the above upper limit value, the heat resistance is inferior, and when the resin film is patterned, the pattern may disappear due to melting by heat.
  • the monomer represented by the general formula (1) include bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N-phenyl-bicyclo [2.2. .1] Hept-5-ene-2,3-dicarboximide, N-methylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N-ethylbicyclo [2.2 .1] Hept-5-ene-2,3-dicarboximide, N-propylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N-butylbicyclo [2.2 .1] Hept-5-ene-2,3-dicarboximide, N-cyclohexylbicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N-adamantylbicyclo [2.2 .1] Hept-5-ene-2,3-di Ruboxyimide, N- (1- (1-
  • dodec-9-ene-4,5-dicarboximide N- (2,4-dimethoxyphenyl) -tetracyclo [6.2.1.1 3,6 . 0 2,7 ] dodec-9-ene-4,5-dicarboximide and the like. These may be used alone or in combination of two or more.
  • R 2 is a divalent alkylene group having 1 to 3 carbon atoms.
  • the divalent alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, a propylene group, and An isopropylene group is mentioned. Among these, a methylene group and an ethylene group are preferable because of good polymerization activity.
  • R 3 is a monovalent alkyl group having 1 to 10 carbon atoms or a monovalent halogenated alkyl group having 1 to 10 carbon atoms.
  • Examples of the monovalent alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, hexyl group, and cyclohexyl group. .
  • Examples of the monovalent halogenated alkyl group having 1 to 10 carbon atoms include a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, Examples include 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group, perfluorobutyl group, and perfluoropentyl group. Among these, because of excellent solubility in alkali developing solution, the R 3, methyl and ethyl are preferred.
  • the monomers represented by the above general formulas (1) and (2) can be obtained, for example, by an imidization reaction between a corresponding amine and 5-norbornene-2,3-dicarboxylic acid anhydride. .
  • the obtained monomer can be efficiently isolated by separating and purifying the reaction solution of the imidization reaction by a known method.
  • the content rate of the repeating unit derived from the other monomer (b) in the cyclic olefin polymer (A) is preferably 10 mol% or more, assuming that all repeating units are 100 mol%, and 20 mol. % Or more, more preferably 30 mol% or more, preferably 90 mol% or less, more preferably 80 mol% or less, and further preferably 70 mol% or less. preferable. If the ratio of the repeating unit derived from the other monomer (b) is 10 mol% or more, the dissolution contrast of the exposed part / unexposed part at the time of patterning using the resin film of the cyclic olefin polymer (A). If it is 90 mol% or less, the solubility in a developer, particularly an alkali developer, can be sufficiently secured, and the generation of development residues can be effectively suppressed.
  • a cyclic olefin polymer (A) can be prepared by performing the ring-opening polymerization according to a known method, addition polymerization, etc. about the monomer composition containing the various monomers mentioned above. Especially, it is preferable to perform ring-opening polymerization and to obtain a cyclic olefin polymer (A).
  • a ring-opening metathesis polymerization method according to the method described in International Publication No. 2010/110323 or the like can be suitably employed.
  • the obtained ring-opened polymer is further subjected to hydrogenation reaction, and at least the main A hydrogenated product obtained by hydrogenating at least part of the carbon-carbon double bonds contained in the chain is preferable.
  • the ratio of hydrogenated carbon-carbon double bonds is preferably 50% or more from the viewpoint of improving the heat resistance of the resin film. 70% or more, more preferably 90% or more, and particularly preferably 95% or more.
  • the “hydrogenation rate” can be measured according to the 1 H-NMR spectrum measurement method.
  • the epoxy resin (B) having an epoxy equivalent of 500 or more is a component that acts to enhance the resolution and extensibility of the resin film obtained using the resin composition.
  • the epoxy equivalent of the epoxy resin (B) needs to be 500 or more, preferably 900 or more, more preferably 950 or more, preferably 1500 or less, and more preferably 1250 or less. preferable. If the epoxy equivalent of an epoxy resin (B) is 900 or more, the extensibility of the resin film obtained using a resin composition can be improved further. Moreover, if the epoxy equivalent of an epoxy resin (B) is below the said upper limit, while suppressing generation
  • the epoxy resin (B) preferably contains a flexible skeleton and an aromatic group in the molecule.
  • the epoxy resin (B) contains both a flexible skeleton and an aromatic group, it is more effective to impart extensibility and impart resolution to the resulting resin film. It can be compatible.
  • the epoxy resin containing both the flexible skeleton and the aromatic group imparts flexibility to the resin film by the flexible skeleton, and also has heat resistance to the resin film by the aromatic group. It is inferred that this is due to the fact that Furthermore, since the epoxy resin (B) contains both the flexible skeleton and the aromatic group, chemical resistance can be improved in addition to the stretchability and resolution of the resin film.
  • the “flexible skeleton” is not particularly limited as long as it can exhibit flexibility, and includes a divalent linking group that is bonded to the linked structure at both ends.
  • the divalent linking group include an alkylene structure having 2 to 20 carbon atoms and an alkylene structure having an ether bond having 2 to 20 carbon atoms.
  • an alkylene structure having 2 to 20 carbon atoms an alkylene structure having 2 to 15 carbon atoms is preferable, and an alkylene structure having 2 to 10 carbon atoms is more preferable.
  • the alkylene group may be linear, branched or cyclic.
  • alkylene structure examples include ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene group, and cyclohexane.
  • a propylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a decahydronaphthanylene group, a norbornanylene group, an adamantanilene group and the like can be mentioned.
  • the alkylene structure is a halogen atom, alkyl group, alkoxy group, alkylidene group, amino group, silyl group, acyl group, acyloxy group, carboxy group, sulfo group, cyano group, nitro group, hydroxy group, mercapto group, oxo group. May have a substituent such as, but preferably does not have a substituent. The carbon number does not include the carbon number of the substituent.
  • Examples of the alkylene structure having an ether bond having 2 to 20 carbon atoms include an oxyalkylene structure, an alkyleneoxy structure, an oxyalkyleneoxy structure, an alkyleneoxyalkylene structure, and an alkyleneoxyalkyleneoxyalkylene structure.
  • the alkylene structure having an ether bond having 2 to 20 carbon atoms is preferably an alkylene structure having an ether bond having 2 to 15 carbon atoms, more preferably an alkylene structure having an ether bond having 2 to 10 carbon atoms.
  • the alkylene structure may be linear, branched or cyclic.
  • alkylene structure having such an ether bond examples include oxyethylene group, oxypropylene group, oxybutylene group, oxypentylene group, oxyhexylene group, oxyheptylene group, oxyoctylene group, oxynonylene group, oxydecylene group, oxyundecylene.
  • the oxyalkylene structure includes a halogen atom, alkyl group, alkoxy group, alkylidene group, amino group, silyl group, acyl group, acyloxy group, carboxy group, sulfo group, cyano group, nitro group, hydroxy group, mercapto group, oxo It may have a substituent such as a group, but preferably has no substituent. Here, the carbon number does not include the carbon number of the substituent.
  • Examples of the aromatic group contained in the epoxy resin (B) include an aromatic hydrocarbon ring group having 6 to 20 carbon atoms, and among them, a phenylene group is preferable.
  • the epoxy resin (B) is preferably a compound represented by the following general formula (3).
  • X represents a divalent linking group
  • Y 1 and Y 2 each independently represent the above-mentioned “flexible skeleton”
  • m represents an integer of 1-20. To express.
  • divalent linking group that can be X in the general formula (3) include a single bond, an oxygen atom, a carbon atom, or a sulfur atom.
  • X and Y 1 are different, and X and Y 2 are different.
  • a functional group such as a methyl group, a trifluoromethyl group, a carbonyl group, and a phenyl group may be further bonded to the divalent linking group as X.
  • Y 1 in the general formula (3) and Y 2 which may be present in plural may be the same or different, but are preferably the same.
  • m in the general formula (3) is preferably an integer of 1 to 10, more preferably an integer of 3 to 5.
  • the epoxy resin (B) satisfying the general formula (3) is not particularly limited, and can be synthesized, for example, according to the method disclosed in JP 2010-285627 A.
  • a suitable epoxy resin (B) marketed it is not specifically limited, For example, "YX7110B80" by Mitsubishi Chemical Corporation can be mentioned.
  • a kind of compound can be used individually or in combination of 2 or more types.
  • the content of the epoxy resin (B) in the resin composition is preferably 40 parts by mass or more, more preferably 60 parts by mass or more, and preferably 100 parts by mass or less, per 100 parts by mass of the cyclic olefin polymer (A). Less than the mass part is more preferable. If content of an epoxy resin (B) is more than the said lower limit, the extensibility of a resin film can be improved further. Moreover, if content of an epoxy resin (B) is below the said upper limit, the resolution of a resin film can be improved further.
  • the crosslinking agent (C) contains a phenolic hydroxyl group and an alkoxymethyl group in the molecule. Such a crosslinking agent (C) can form a crosslinked structure between the crosslinking agent molecules by heating and / or react with the cyclic olefin polymer (A) having a polar group to form a crosslinked structure. Therefore, the chemical resistance of the resin film can be increased by adding the crosslinking agent (C) to the resin composition.
  • the crosslinking agent (C) a phenol compound in which two or more alkoxymethyl groups are directly bonded to an aromatic ring is preferable.
  • an alkoxymethyl group a methoxymethyl group is preferable.
  • Examples of the phenol compound in which two or more alkoxymethyl groups are directly bonded to an aromatic ring include dimethoxymethyl such as 2,6-dimethoxymethyl-4-t-butylphenol and 2,6-dimethoxymethyl-p-cresol.
  • Substituted phenol compounds 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl (for example, trade name “TMOM-BP”, manufactured by Honshu Chemical Industry Co., Ltd.), 1,1-bis [3 , 5-di (methoxymethyl) -4-hydroxyphenyl] -1-phenylethane and the like; 4,4 ′, 4 ′′-(ethylidene) tris [2,6- (methoxymethyl) phenol ] (For example, trade name “HMOM-TPHAP”, manufactured by Honshu Chemical Industry Co., Ltd.)
  • TMOM-BP 5,5′-tetramethoxymethyl-4,4′- dihydroxybiphenyl
  • 4 ′, 4 ′′-(ethylidene) tris [2,6- (methoxymethyl) Phenol] (HMOM-TPHAP) is preferable, and these can be used alone or in combination
  • the content of the crosslinking agent (C) in the resin composition is preferably 100 parts by mass or less, more preferably 80 parts by mass or less, per 100 parts by mass of the cyclic olefin polymer (A), and 30 parts by mass. More preferably, the amount is 1 part by mass or more, more preferably 2 parts by mass or more, and still more preferably 5 parts by mass or more. If content of a crosslinking agent (C) is more than the said lower limit, the chemical resistance of a resin film can be improved further. Moreover, if content of a crosslinking agent (C) is below the said upper limit, the extensibility of a resin film can be improved.
  • the resin composition preferably further contains a photoacid generator (D).
  • a photoacid generator (D) When the resin composition contains a radiation-sensitive compound such as the photoacid generator (D), the resin film developer in the exposed portion is obtained by the action of the photoacid generator (D) when the resin film is exposed. The solubility of the resin film can be changed, whereby the resin film can be patterned. That is, when the resin composition contains a radiation sensitive compound such as the photoacid generator (D), the resin composition can function as a radiation sensitive resin composition.
  • the photoacid generator examples include azide compounds (such as quinonediazide compounds), onium salt compounds, halogenated organic compounds, ⁇ , ⁇ ′-bis (sulfonyl) diazomethane compounds, ⁇ -carbonyl- ⁇ ′-sulfonyldiazomethane compounds , Sulfone compounds, organic acid ester compounds, organic acid amide compounds, organic acid imide compounds, acetophenone compounds, and triarylsulfonium salts, azide compounds are preferred, and quinonediazide compounds are more preferred.
  • azide compounds such as quinonediazide compounds
  • onium salt compounds examples include halogenated organic compounds, ⁇ , ⁇ ′-bis (sulfonyl) diazomethane compounds, ⁇ -carbonyl- ⁇ ′-sulfonyldiazomethane compounds , Sulfone compounds, organic acid ester compounds, organic acid amide compounds, organic acid imide compounds, acetophenone compounds, and triaryl
  • a quinonediazide compound suitably used as a photoacid generator for example, an ester compound of a quinonediazidesulfonic acid halide and a compound having a phenolic hydroxyl group can be used.
  • the quinonediazide sulfonic acid halide used in the preparation of the ester compound include 1,2-naphthoquinonediazide-5-sulfonic acid chloride, 1,2-naphthoquinonediazide-4-sulfonic acid chloride, and 1,2-benzoquinonediazide-5. -Sulfonic acid chlorides.
  • Examples of the compound having a phenolic hydroxyl group used for the preparation of the ester compound include 1,1,3-tris (2,5-dimethyl-4-hydroxyphenyl) -3-phenylpropane, 4,4 ′-[1 -[4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol, 2,3,4-trihydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2- Bis (4-hydroxyphenyl) propane, tris (4-hydroxyphenyl) methane, 1,1,1-tris (4-hydroxy-3-methylphenyl) ethane, 1,1,2,2-tetrakis (4-hydroxy) Phenyl) ethane, novolak resin oligomer, compound having one or more phenolic hydroxyl groups and dicyclopentadiene They include oligomers obtained by copolymerizing and. These can be used individually by 1 type or in combination of 2 or
  • the content of the photoacid generator (D) in the resin composition is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and further 25 parts by mass or more per 100 parts by mass of the cyclic olefin polymer (A).
  • 100 parts by mass or less is preferable, 70 parts by mass or less is more preferable, and 50 parts by mass or less is still more preferable.
  • the content of the photoacid generator (D) is within this range, the cyclic olefin polymer in the exposed area and the unexposed area can be obtained with an appropriate exposure intensity when patterning using the resin film made of the resin composition. Since the difference in solubility of the developer (A) in the developer can be sufficiently increased, a clear pattern can be formed with good sensitivity.
  • the resin composition of the present invention may contain a solvent. That is, in the resin composition of the present invention, the cyclic olefin polymer (A), the epoxy resin (B), the crosslinking agent (C), and the optionally added photoacid generator (D) are dissolved in the solvent. And / or a resin liquid that is dispersed.
  • the solvent is not particularly limited, and known solvents for the resin composition, for example, solvents disclosed in International Publication No. 2015/141717 such as diethylene glycols containing diethylene glycol ethyl methyl ether can be used. As a solvent, it can use individually by 1 type or in mixture of multiple types.
  • the content of the solvent in the resin composition of the present invention is preferably 10 parts by mass or more and 10000 parts by mass or less, more preferably 50 parts by mass or more and 5000 parts by mass or less, per 100 parts by mass of the cyclic olefin polymer (A). More preferably, it is the range of 100 to 1000 mass parts.
  • the resin composition of the present invention may contain other additives other than the above, if desired, as long as the effects of the present invention are not inhibited.
  • other additives include cross-linking agents other than the cross-linking agent (C), silane coupling agents, surfactants, sensitizers, light stabilizers, antifoaming agents, pigments, dyes, and fillers.
  • crosslinking agent other than the crosslinking agent (C) include a crosslinking agent having a methylol group, a crosslinking agent having an oxetane group, and a crosslinking agent having a blocked isocyanate group.
  • the preparation method of the resin composition of this invention is not specifically limited, What is necessary is just to mix each component which comprises a resin composition by a well-known method.
  • the mixing method is not particularly limited, but it is preferable to mix a solution or dispersion obtained by dissolving or dispersing each component constituting the resin composition in a solvent. Thereby, the resin composition is obtained in the form of a solution or a dispersion (that is, a state of a resin liquid).
  • the mixing is not particularly limited, and is performed using a known mixer. Moreover, you may filter by a known method after mixing.
  • the solid content concentration of the resin liquid which is the resin composition of this invention is 1 mass% or more and 70 mass% or less normally, Preferably they are 5 mass% or more and 60 mass% or less, More preferably, they are 10 mass% or more and 50 mass% or less. It is as follows. If the solid content concentration is within the above-described range, the dissolution stability and coating property of the resin liquid, the film thickness uniformity and flatness of the formed resin film, and the like can be highly balanced.
  • the electronic component of the present invention includes a resin film made of the above-described resin composition of the present invention. And since the electronic component of this invention is equipped with the resin film which was sufficiently small in the development residue formed from the resin composition of this invention, and was excellent in the extendibility, it is high performance.
  • the electronic component of the present invention is not particularly limited, but the resin film made of the resin composition of the present invention is manufactured by wafer level package technology because it has a sufficiently small development residue and excellent extensibility. Electronic components are preferred.
  • an interlayer insulating film such as a rewiring interlayer insulating film or the like for insulating between wirings arranged in layers in a resin component made of the resin composition of the present invention. It is more preferable that it is used as what forms a).
  • An electronic component including a resin film is not particularly limited, and can be manufactured by forming a resin film on a substrate such as a silicon wafer on which a semiconductor element is mounted.
  • the method for forming the resin film on the substrate is not particularly limited.
  • the resin film includes, for example, a process of forming a film on a substrate (a film forming process) using a resin composition containing a solvent (that is, a resin liquid), and a process of obtaining a resin film by crosslinking the obtained film. (Crosslinking step) can be manufactured.
  • a step of exposing the film on the substrate with actinic radiation to obtain an exposure film (exposure step) between the film forming step and the crosslinking step, and developing and developing the exposure film By performing the process of obtaining a film (development process) in this order, a patterned resin film can be obtained.
  • exposure step exposing the film on the substrate with actinic radiation to obtain an exposure film
  • development process developing and developing the exposure film
  • a film is formed on the substrate using the resin composition according to a known method such as a coating method or a film lamination method.
  • the resin composition is coated according to a known method such as a spin coating method, and then dried by heating to remove the solvent to obtain a coating film.
  • the heating and drying conditions at this time vary depending on the types and blending ratios of the components, but the heating temperature is usually 30 to 150 ° C., preferably 60 to 120 ° C., and the heating time is usually 0.5 to 90 minutes. , Preferably 1 to 60 minutes, more preferably 1 to 30 minutes.
  • the resin composition is applied onto a B-stage film-forming substrate such as a resin film or a metal film, and then the solvent is removed by heat drying to obtain a B-stage film (coating film). Next, this B stage film is laminated on the substrate.
  • the heating and drying conditions at this time can be appropriately selected according to the type and mixing ratio of each component, but the heating temperature is usually 30 to 150 ° C., and the heating time is usually 0.5 to 90 minutes. sell.
  • Film lamination can be performed using a pressure laminator, a press, a vacuum laminator, a vacuum press, a roll laminator or the like.
  • the coating film on the substrate is irradiated with actinic radiation to obtain an exposure film. More specifically, in the exposure step, the coating film is irradiated with actinic radiation to form a latent image pattern.
  • the resin composition used when performing an exposure process contains radiation sensitive compounds, such as a photo-acid generator (D).
  • the resin composition contains the photoacid generator (D)
  • the solubility with respect to can be made different.
  • a method for obtaining a patterned resin film without blending the photoacid generator (D) into the resin composition for example, a method using laser processing using a CO 2 laser, a UV-YAG laser, or the like.
  • a method of forming a mask pattern on the resin film and performing dry etching, and a direct drawing method such as an ink jet method can be used.
  • the actinic radiation is not particularly limited as long as it can activate the photoacid generator (D) contained in the resin composition and change the solubility of the film in the developer.
  • light rays such as ultraviolet rays, single-wavelength ultraviolet rays such as g, h, and i rays, g-h-i mixed rays, KrF excimer laser light, ArF excimer laser light; particle beams such as electron beams; Etc. can be used.
  • a method of selectively irradiating these actinic radiations in a pattern to form a latent image pattern a conventional method may be followed. Irradiation conditions are appropriately selected depending on the actinic radiation to be used.
  • the irradiation amount is usually 10 to 5,000 mJ / cm 2 , preferably 50 to 2, preferably.
  • the range is 500 mJ / cm 2 and is determined according to the irradiation time and illuminance.
  • the resin film may be heat-treated at a temperature of about 60 to 130 ° C. for about 1 to 2 minutes as necessary.
  • the latent image pattern formed in the exposure process is developed and made visible.
  • an alkali developer can be used.
  • the alkaline developer can be prepared by dissolving an alkaline compound in an aqueous solvent.
  • an alkali metal salt, an amine, or an ammonium salt can be used.
  • the alkaline compound may be an inorganic compound or an organic compound.
  • alkali metal salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate and sodium metasilicate; ammonia water; primary amines such as ethylamine and n-propylamine; diethylamine Secondary amines such as di-n-propylamine; tertiary amines such as triethylamine and methyldiethylamine; quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide and choline Alcohol alcohols such as dimethylethanolamine and triethanolamine; pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] undec-7-ene, 1,5-diazabicyclo [4.3.0] nona-5 -En, N-Me Cyclic amines such as Rupiroridon; and the like.
  • alkaline compounds can be used alone or in combination of two or more.
  • an aqueous solvent for the alkaline aqueous solution water; water-soluble organic solvents such as methanol and ethanol can be used.
  • the alkaline aqueous solution may have a surfactant added in an appropriate amount.
  • the development temperature is usually selected from the range of 0 to 100 ° C., preferably 5 to 55 ° C., more preferably 10 to 30 ° C., and the development time is usually appropriately selected from the range of 30 to 180 seconds.
  • the developing film on which the target pattern is formed in this way can be rinsed with a rinsing liquid as necessary in order to remove development residues. After the rinsing treatment, it is preferable to remove the remaining rinsing liquid with compressed air or compressed nitrogen. Furthermore, in order to deactivate the photo-acid generator (D) contained in the resin composition as necessary, the development film can be irradiated with actinic radiation as described above. For irradiation with actinic radiation, the method exemplified in the formation of the latent image pattern can be used.
  • the developing film may be heated simultaneously with irradiation or after irradiation. Examples of the heating method include a method of heating an electronic component in a hot plate or an oven. The heating temperature is usually in the range of 80 to 300 ° C, preferably 100 to 200 ° C.
  • Crosslinking process a crosslinking reaction is performed on the film formed on the substrate in the film forming process or the developed film that has undergone the developing process.
  • Such crosslinking may be appropriately selected depending on the type of the crosslinking agent (C), but is usually performed by heating.
  • the heating method can be performed using, for example, a hot plate or an oven.
  • the heating temperature is usually 180 to 250 ° C.
  • the heating time is appropriately selected depending on the area and thickness of the film, equipment used, etc.
  • an oven is usually used for 5 to 60 minutes.
  • the case is usually in the range of 30 to 240 minutes. Heating may be performed in an inert gas atmosphere as necessary.
  • any inert gas may be used as long as it does not contain oxygen and does not oxidize the film.
  • examples thereof include nitrogen, argon, helium, neon, xenon, and krypton.
  • nitrogen and argon are preferable, and nitrogen is particularly preferable.
  • an inert gas having an oxygen content of 0.1% by volume or less, preferably 0.01% by volume or less, particularly nitrogen is suitable.
  • These inert gases can be used alone or in combination of two or more.
  • the thickness of the resin film that can be formed as described above is not particularly limited and may be appropriately set depending on the application, but is preferably 0.1 to 100 ⁇ m, more preferably 0.5 to 50 ⁇ m. More preferably, the thickness is 0.5 to 30 ⁇ m.
  • dodeca-9-ene 100 parts monomer mixture, 1,5-hexadiene 2.0 parts, (1,3-dimesitylimidazoline-2-ylidene) ( Tricyclohexylphosphine) benzylidene ruthenium dichloride (synthesized by the method described in Org. Lett., Vol. 1, p. 953, 1999) and 200 parts of diethylene glycol ethyl methyl ether made of nitrogen-substituted glass The polymerization reaction liquid was obtained by charging into a pressure-resistant reactor and making it react at 80 degreeC for 4 hours, stirring.
  • the obtained polymerization reaction liquid is put in an autoclave and stirred for 5 hours at 150 ° C. under a hydrogen pressure of 4 MPa to carry out a hydrogenation reaction, and contains a cyclic olefin polymer (A-1) having a protic polar group
  • a polymer solution was obtained.
  • the resulting cyclic olefin polymer (A-1) having a protic polar group had a polymerization conversion of 99.7%, a polystyrene-equivalent weight average molecular weight of 7,150, a number average molecular weight of 4,690, and a molecular weight distribution of 1 0.52 and the hydrogenation rate was 99.7%.
  • the solid content concentration of the polymer solution of the obtained cyclic olefin polymer (A-1) having a protic polar group was 34.4% by mass.
  • dodeca-9-ene 100 parts by weight of a monomer mixture, 1.0 part by weight of 1-hexene, (1,3-dimesitylimidazoline-2-ylidene) ( 0.06 part by mass of tricyclohexylphosphine) benzylidene ruthenium dichloride (synthesized by the method described in “Org. Lett., Vol. 1, page 953, 1999”) and 300 parts by mass of diethylene glycol ethyl methyl ether The polymer was charged in a substituted glass pressure-resistant reactor and reacted at 80 ° C. for 4 hours with stirring to obtain a polymerization reaction solution.
  • the obtained polymerization reaction liquid is put in an autoclave and stirred for 5 hours at 150 ° C. under a hydrogen pressure of 4 MPa to carry out a hydrogenation reaction, and contains a cyclic olefin polymer (A-2) having a protic polar group
  • a polymer solution was obtained.
  • the polymerization conversion rate of the obtained cyclic olefin polymer (A-2) having a protic polar group was 99.3% by mass
  • the polystyrene-equivalent weight average molecular weight was 20,600
  • the number average molecular weight was 11,500
  • the molecular weight distribution was The hydrogenation rate was 1.9.8 mol%, 1.79.
  • the solid content concentration of the polymer solution of the obtained cyclic olefin polymer (A-2) having a protic polar group was 25.3 mass%.
  • Example 1 Preparation of resin composition>
  • the cyclic olefin polymer (A) 291 parts of a polymer solution of the cyclic olefin polymer (A-1) having a protic polar group obtained in Synthesis Example 1 (100 parts as the cyclic olefin polymer (A-1)) ), 4,4 ′-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol (1 mol) and 1,2 as photoacid generator (D) -Mixture of 30 parts of condensate with naphthoquinonediazide-5-sulfonic acid chloride (2.5 mol), epoxy resin (B) having an epoxy equivalent of 1124 and methyl ethyl ketone (MEK) ("YX7110B80" manufactured by Mitsubishi Chemical Corporation) 63 parts (50 parts as an epoxy resin (B)) and 53 parts of diethylene glycol ethyl methyl
  • the resin composition was prepared by filtration through a polytetrafluoroethylene filter having a pore diameter of 0.45 ⁇ m. And various evaluation was performed according to the above using the obtained resin composition. The results are shown in Table 1.
  • “YX7110B80” manufactured by Mitsubishi Chemical Co., Ltd. used as an epoxy resin (B) having an epoxy equivalent of 500 or more has an aromatic group and a flexible skeleton in the molecule, and has an aromatic group.
  • Example 2 In Example 1, the crosslinking agent (C) (HMOM-TPHAP, 4,4 ′, 4 ′′-(ethylidene) tris [2,6- (methoxymethyl) phenol] containing a phenolic hydroxyl group and an alkoxymethyl group in the molecule Further, 50 parts of a 20% solution of ⁇ -butyrolactone of the following formula ( ⁇ ) (“HMOM-TPHAP-GB” manufactured by Honshu Chemical Co., Ltd.) (10 parts as a crosslinking agent (C)) is further blended, and diethylene glycol ethyl as a solvent A resin composition was prepared in the same manner as in Example 1 except that the amount of methyl ether was changed from 53 parts to 28 parts, and various evaluations were performed. The results are shown in Table 1.
  • Example 3 In Example 1, the mixture of epoxy resin (B) and MEK (Mitsubishi Chemical Co., Ltd., “YX7110B80”) was changed from 63 parts to 81 parts (65 parts as epoxy resin (B)), and the phenolic hydroxyl group in the molecule And an alkoxymethyl group-containing crosslinking agent (C) (“TMOM-BP” manufactured by Honshu Chemical Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl, the following formula ( ⁇ )
  • the resin composition was prepared in the same manner as in Example 1 except that 10 parts were further blended and the amount of diethylene glycol ethyl methyl ether as the solvent was changed from 53 parts to 86 parts, and various evaluations were performed. The results are shown in Table 1.
  • Example 4 In Example 1, the mixture of epoxy resin (B) and MEK (manufactured by Mitsubishi Chemical Corporation, YX7110B80) was changed from 63 parts to 94 parts (75 parts as epoxy resin (B)), and ⁇ -butyrolactone 20 of HMOM-TPHAP was changed. % Solution (Honshu Chemical Co., Ltd., “HMOM-TPHAP-GB”) 100 parts (20 parts as a cross-linking agent (C)) was added, and diethylene glycol ethyl methyl ether was changed from 53 parts to 31 parts. In the same manner as in Example 1, resin compositions were prepared and subjected to various evaluations. The results are shown in Table 1.
  • Example 5 As the cyclic olefin polymer (A), 232 parts of a polymer solution of the cyclic olefin polymer (A-1) having a protic polar group obtained in Synthesis Example 1 (80 parts as the cyclic olefin polymer (A-1)) And 79 parts of a polymer solution of the cyclic olefin polymer (A-2) having a protic polar group obtained in Synthesis Example 2 (20 parts as the cyclic olefin polymer (A-2)), a photoacid generator As (D), 4,4 ′-[1- [4- [1- [4-hydroxyphenyl] -1-methylethyl] phenyl] ethylidene] bisphenol (1 mol) and 1,2-naphthoquinonediazide-5- 35 parts of a condensate with sulfonic acid chloride (2.5 mol), 88 parts of a mixture of epoxy resin (B) and MEK (D),
  • a resin composition was prepared by filtration through a polytetrafluoroethylene filter.
  • preparation of a test piece was attempted.
  • the resin film was brittle and could not be peeled off from the wafer, the test piece could not be prepared and evaluated. I wouldn't.
  • the same evaluation as Example 1 was performed. The results are shown in Table 1.
  • a resin film excellent in resolution and extensibility can be formed.
  • a high-performance electronic component can be provided.

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Non-Metallic Protective Coatings For Printed Circuits (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

Cette composition de résine contient un polymère d'oléfine annulaire (A) ayant un groupe polaire, et une résine époxy (B) ayant un équivalent époxy supérieur ou égal à 500.
PCT/JP2019/010901 2018-03-30 2019-03-15 Composition de résine et composant électronique WO2019188432A1 (fr)

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CN111770964A (zh) 2020-10-13
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