WO2017188153A1 - 樹脂組成物 - Google Patents

樹脂組成物 Download PDF

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Publication number
WO2017188153A1
WO2017188153A1 PCT/JP2017/016054 JP2017016054W WO2017188153A1 WO 2017188153 A1 WO2017188153 A1 WO 2017188153A1 JP 2017016054 W JP2017016054 W JP 2017016054W WO 2017188153 A1 WO2017188153 A1 WO 2017188153A1
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group
resin composition
resin
film
general formula
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PCT/JP2017/016054
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English (en)
French (fr)
Japanese (ja)
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橋本啓華
荘司優
奥田良治
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東レ株式会社
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Priority to CN201780016470.9A priority Critical patent/CN108779251B/zh
Priority to KR1020187026652A priority patent/KR102277707B1/ko
Priority to JP2017522685A priority patent/JP7003659B2/ja
Publication of WO2017188153A1 publication Critical patent/WO2017188153A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C08G73/22—Polybenzoxazoles
    • 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
    • C08K5/07—Aldehydes; Ketones
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/70—Manufacture or treatment of devices consisting of a plurality of solid state components formed in or on a common substrate or of parts thereof; Manufacture of integrated circuit devices or of parts thereof
    • H01L21/71—Manufacture of specific parts of devices defined in group H01L21/70
    • H01L21/768—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
    • H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
    • H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
    • H01L23/532—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body characterised by the materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/02—Bonding areas; Manufacturing methods related thereto
    • H01L2224/04—Structure, shape, material or disposition of the bonding areas prior to the connecting process
    • H01L2224/04105—Bonding areas formed on an encapsulation of the semiconductor or solid-state body, e.g. bonding areas on chip-scale packages
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/10—Bump connectors; Manufacturing methods related thereto
    • H01L2224/12—Structure, shape, material or disposition of the bump connectors prior to the connecting process
    • H01L2224/12105—Bump connectors formed on an encapsulation of the semiconductor or solid-state body, e.g. bumps on chip-scale packages
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/18—High density interconnect [HDI] connectors; Manufacturing methods related thereto
    • H01L2224/19—Manufacturing methods of high density interconnect preforms

Definitions

  • the present invention relates to a resin composition suitably used for a surface protective film such as a semiconductor element, an interlayer insulating film, and an insulating layer of an organic electroluminescent element.
  • resin compositions that can be cured at low temperatures include resins such as polyimide, polybenzoxazole, polybenzimidazole, and polybenzothiazole, and resin compositions containing a thermal crosslinking agent (Patent Document 1), alkali-soluble polyamideimide, light Positive type photosensitive polyamideimide resin composition containing an acid generator, a solvent and a crosslinking agent (Patent Document 2), an alkali-soluble polyimide, a quinonediazide compound, a thermal crosslinking agent, a thermal acid generator and an adhesion improver
  • Patent Document 3 A photosensitive polyimide resin composition
  • the resin compositions curable by heat treatment at a low temperature of 250 ° C. or lower as disclosed in Patent Documents 1 to 3 have problems in characteristics such as heat resistance and chemical resistance.
  • the present invention has the following configuration. That is, (A) An alkali-soluble compound comprising at least one selected from a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof, and having a benzoxazole precursor structure and an aliphatic group Resin, and (B) A resin composition containing a thermal acid generator and (E) an antioxidant.
  • alkali-soluble means a pre-baked film formed by the following method, It means that the dissolution rate when immersed in an alkaline aqueous solution described below is 50 nm / min or more. Specifically, a solution in which a resin is dissolved in ⁇ -butyrolactone is applied onto a silicon wafer and prebaked at 120 ° C. for 4 minutes to form a prebaked film having a thickness of 10 ⁇ m ⁇ 0.5 ⁇ m. It means that the dissolution rate obtained from the decrease in film thickness when immersed in a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 1 ° C. for 1 minute and then rinsed with pure water is 50 nm / min or more.
  • a component has a fluorine atom.
  • the formed film has water repellency, and when developed with an alkaline aqueous solution, the penetration of the alkaline aqueous solution into the interface between the film and the substrate is suppressed.
  • the aqueous alkaline solution used for development may be referred to as an alkaline developer.
  • the fluorine atom content in the component (A) is preferably 5% by mass or more from the viewpoint of suppressing the penetration of the alkaline aqueous solution into the interface between the film and the substrate, and 20% by mass from the viewpoint of solubility in the alkaline aqueous solution. The following is preferred.
  • the alkali-soluble resin as the component (A) has high heat resistance.
  • excellent characteristics can be obtained as a planarizing film, an insulating layer, a partition, a protective film, and an interlayer insulating film used in organic light emitting devices, display devices, and semiconductor elements.
  • a thing with little outgas amount is preferable.
  • a polybenzoxazole precursor, a polyimide precursor, a polyamideimide precursor, and a copolymer thereof are preferable examples.
  • the component (A) used in the present invention preferably has a structural unit represented by the following general formula (1). Moreover, you may have another structural unit further. Examples of other structural units in such a case include, but are not limited to, a structure having a skeleton in which two cyclic structures are bonded to a quaternary carbon atom constituting an imide structure or a cyclic structure, and a siloxane structure. Not. When it further has another structural unit, it is preferable to have 50 mol% or more of structural units represented by General formula (1) among the total number of structural units.
  • X and Y each independently represent a divalent to octavalent organic group having 2 or more carbon atoms.
  • R 1 and R 2 each independently represent hydrogen or a carbon number of 1 Represents an organic group of ⁇ 20, n represents an integer in the range of 10 to 100,000, r and s represent an integer in the range of 0 to 2, and p and q represent an integer in the range of 0 to 4. .
  • the component (A) has a benzoxazole precursor structure. By having the benzoxazole precursor structure, the photosensitivity performance is improved, and high extensibility can be imparted to the cured film obtained by curing the resin composition containing the component (A). Ring closure improves heat resistance and chemical resistance.
  • (A) component has an aliphatic group.
  • the aliphatic group preferably has at least one organic group of an alkylene group and an oxyalkylene group. Specific examples include an alkylene group, a cycloalkylene group, an oxyalkylene group, and an oxycycloalkylene group. Moreover, it is preferable that the said aliphatic group is what is represented by following General formula (2).
  • R 3 to R 6 each independently represents an alkylene group having 1 to 6 carbon atoms.
  • R 7 to R 14 are each independently hydrogen, fluorine, or alkyl having 1 to 6 carbon atoms.
  • X, y and z each independently represents an integer of 0 to 35.
  • the aliphatic group has a low UV absorption property, the introduction of the aliphatic group improves i-ray transmission and can simultaneously realize high sensitivity.
  • the weight average molecular weight of the component (A) used in the present invention is preferably 600 or more, and more preferably 900 or more, in that the cured film has high extensibility. Moreover, it is preferable that it is 2,000 or less at the point by which the solubility to an alkaline solution is maintained, It is more preferable that it is 1,800 or less, It is further more preferable that it is 1,500 or less.
  • the weight average molecular weight (Mw) can be confirmed using GPC (gel permeation chromatography). For example, it can be determined by measuring using N-methyl-2-pyrrolidone (hereinafter sometimes abbreviated as NMP) as a developing solvent and calculating in terms of polystyrene.
  • NMP N-methyl-2-pyrrolidone
  • the component (A) used in the present invention preferably has a structural unit represented by the general formula (1).
  • (OH) p -X- (COOR 1 ) r represents an acid residue.
  • X is a divalent to octavalent organic group having 2 or more carbon atoms, and is preferably an organic group having 5 to 40 carbon atoms containing an aromatic ring or an aliphatic group.
  • the acid component examples include dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis (carboxyphenyl) hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid.
  • dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis (carboxyphenyl) hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid.
  • tetracarboxylic acids such as acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyl tricarboxylic acid, pyromellitic acid, 3,3 ′, 4,4′-biphenyltetracarboxylic acid, 2,3,3 ′, 4′-biphenyl Tetracarboxylic acid, 2,2 ′, 3,3′-biphenyltetracarboxylic acid, 3,3 ′, 4,4′-diphenyl ether tetracarboxylic acid, 3,3 ′, 4,4′-benzophenone tetracarboxylic acid, 2 , 2 ', 3, 3'-Be Zophenone tetracarboxylic acid, 2,2-bis (3,4-dicarboxyphenyl) propane, 2,2-bis (2,3-dicarboxyphenyl) propane, 1,1-bis (3,4-dicarboxy) Phenyl) ethane, 1,1
  • R 15 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
  • R 16 and R 17 represent a hydrogen atom or a hydroxyl group.
  • These acids can be used as they are or as acid anhydrides, halides or active esters.
  • diamine used for component (A) examples include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1, 4-bis (4-aminophenoxy) benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4-aminophenoxy) biphenyl, bis ⁇ 4- (4-aminophenoxy) phenyl ⁇ ether, 1,4-bis (4-aminophenoxy) benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′- Diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'
  • R 15 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2 .
  • R 16 to R 19 each independently represents a hydrogen atom or a hydroxyl group.
  • diamines or the corresponding diisocyanate compounds can be used as diamines or the corresponding diisocyanate compounds, trimethylsilylated diamines.
  • the component (A) used in the present invention has an aliphatic group. And it is preferable to have an aliphatic group in Y in the said General formula (1). Furthermore, the aliphatic group is more preferably an aliphatic group represented by the general formula (2).
  • the component (A) used in the present invention may contain an aliphatic group having a siloxane structure as long as the heat resistance is not lowered, thereby improving the adhesion to the substrate.
  • the diamine component include those obtained by copolymerizing 1 to 15 mol% of bis (3-aminopropyl) tetramethyldisiloxane, bis (p-aminophenyl) octamethylpentasiloxane, and the like. .
  • the content of the acidic group at the end of the main chain of the alkali-soluble resin derived from the end-capping agent such as monoamine, acid anhydride, acid chloride, monocarboxylic acid is 100 mol% in total of the acid and amine components constituting the resin.
  • the content is preferably 2 to 25 mol%.
  • the cured film obtained by curing the resin composition of the present invention preferably has a ratio of the benzoxazole precursor structure ring-closed to polybenzoxazole of 30% or more due to the action of the component (B) described later.
  • 30% or more is closed, the amount of outgas is small, and a cured film having high heat resistance, high chemical resistance, and high elongation at break can be obtained.
  • the component (A) having a structural unit represented by the general formula (1) in the present invention preferably has a weight average molecular weight of 10,000 or more and 50,000 or less.
  • a weight average molecular weight of 10,000 or more is preferable because it can improve mechanical properties after curing, and more preferably 20,000 or more.
  • a weight average molecular weight of 50,000 or less is preferable because the developability with an aqueous alkali solution can be improved.
  • At least one weight average molecular weight may be within the above range.
  • the component (A) used in the present invention can be produced by a known method.
  • the polybenzoxazole precursor used in the present invention is composed of a benzoxazole precursor, and can be obtained, for example, by a condensation reaction of a bisaminophenol compound and a dicarboxylic acid. Specifically, a dehydrating condensing agent such as dicyclohexylcarbodiimide (DCC) is reacted with an acid, and a bisaminophenol compound is added thereto, or a solution of a bisaminophenol compound added with a tertiary amine such as pyridine is added to a dicarboxylic acid. For example, a solution of dichloride is dropped. Moreover, it may have an imide precursor structure or an imide structure. In that case, when the imide precursor structure in the polybenzoxazole precursor or the imide structure is 100 parts by mass, the content ratio of the benzoxazole precursor structure Is preferably 101 to 10000 parts by mass.
  • a dehydrating condensing agent such as dicyclohex
  • a benzoxazole precursor structure is introduced into the polyimide precursor by using a diamine having a benzoxazole precursor in advance or by applying the method for producing the polybenzoxazole precursor. Can do.
  • the imide precursor structure in the polyimide precursor is 100 parts by mass
  • the content of the benzoxazole precursor structure is preferably 1 to 99 parts by mass.
  • a method for producing the polyamideimide precursor used in the present invention for example, first, tricarboxylic acid is converted to acid anhydride, and the remaining carboxylic acid is reacted with an acid chloride or a dehydrating condensing agent such as dicyclohexylcarbodiimide (DCC). It can be synthesized by a method of reacting.
  • a benzoxazole precursor structure is introduced into the polyamideimide precursor by using a diamine having a benzoxazole precursor in advance or by applying the method for producing the polybenzoxazole precursor. be able to.
  • the imide precursor structure in the polyamideimide precursor is 100 parts by mass
  • the content of the benzoxazole precursor structure is preferably 50 to 10,000 parts by mass.
  • the thermal acid generator (B) used in the present invention has a thermal decomposition starting temperature of 140 ° C. or higher. Moreover, it is preferable that thermal decomposition start temperature is 220 degrees C or less, and it is more preferable that it is 200 degrees C or less.
  • the thermal decomposition start temperature here means a boiling point or a decomposition temperature, and the decomposition temperature is a temperature at which thermal decomposition starts before reaching the melting point.
  • thermal acid generator examples include sulfonic acid ester compounds and onium salts such as sulfonium salts.
  • the acid generated from the thermal acid generator has an acid dissociation constant of 2.0 from the viewpoint of the function as a catalyst for promoting the cyclization of the imide precursor and benzoxazole precursor of the component (A) and the crosslinking reaction.
  • the following strong acids are preferred.
  • sulfonic acid As the acid generated by thermal decomposition, sulfonic acid, boric acid and the like are preferable.
  • boric acid examples include tetrafluoroboric acid and tetrakis (pentafluorophenyl) boric acid.
  • R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms.
  • R 20 to R 22 each independently represents an aliphatic group having 1 to 12 carbon atoms or an aromatic group having 4 to 12 carbon atoms.
  • the group may have some hydrogen atoms substituted, and examples of the substituent include halogen groups such as an alkyl group, an acyl group, and a fluorine group.
  • onium salts include sulfonium salts and iodonium salts.
  • benzenesulfonic acid (4-hydroxyphenyl) dimethylsulfonium
  • benzenesulfonic acid (4-((methoxycarbonyl) oxy) phenyl) dimethylsulfonium
  • benzenesulfonic acid benzyl (4-hydroxyphenyl) methylsulfonium
  • benzene Benzyl sulfonate (4-((methoxycarbonyl) oxy) phenyl) methylsulfonium sulfonate
  • camphorsulfonic acid (4-hydroxyphenyl) dimethylsulfonium
  • Camphorsulfonic acid (4-((methoxycarbonyl) oxy) phenyl) dimethylsulfonium
  • (C) Preferred examples of the compound having at least two oxetanyl groups as the thermal crosslinking agent include “Denacol” ® EX-212L, Denacol EX-214L, Denacol EX-216L, Denacol EX-850L, Denacol EX -321L (above, manufactured by Nagase ChemteX Corporation), GAN, GOT (above, manufactured by Nippon Kayaku Co., Ltd.), “Epicoat” (registered trademark) 828, Epicoat 1002, Epicoat 1750, Epicoat 1007, YX8100-BH30 , E1256, E4250, E4275 (above, manufactured by Japan Epoxy Resins Co., Ltd.), “Epicron” (registered trademark) 850-S, Epicron HP-4032, Epicron HP-7200, Epicron HP-820, Epicron HP-4700, Epicron HP-4 70, Epicron HP4032 (above, manufactured by Dainippon Ink & Chemicals,
  • thermal crosslinking agents Two or more thermal crosslinking agents may be used in combination.
  • the resin composition of the present invention preferably further contains (D) a photosensitive compound.
  • (D) Photosensitivity can be imparted to the resin composition by containing a photosensitive compound.
  • Examples of the photosensitive compound include compounds having a group having a naphthoquinone diazide structure (hereinafter sometimes referred to as naphthoquinone diazide compounds), sulfonium salts, phosphonium salts, diazonium salts, iodonium salts, and the like. Furthermore, it can also contain a sensitizer etc. as needed.
  • both a 5-naphthoquinone diazide sulfonyl group and a 4-naphthoquinone diazide sulfonyl group are preferably used.
  • the 5-naphthoquinonediazide sulfonyl ester compound has an absorption extending to the g-line region of a mercury lamp and is suitable for g-line exposure and full-wavelength exposure.
  • the 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure.
  • the content of the adhesion improving agent after development is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of component (A). By setting it as such a range, the effect of each post-development adhesion improving agent can be fully expressed.
  • Examples of the compound represented by the general formula (7) include the following, but are not limited to the following structures.
  • the resin composition of the present invention may contain other post-curing adhesion improver in addition to the compound represented by the general formula (7).
  • Other post-cure adhesion improvers include alkoxysilane-containing aromatic amine compounds, aromatic amide compounds, or non-aromatic silane compounds. Two or more of these may be contained. By containing these compounds, it is possible to improve the adhesion to the base material after firing or curing.
  • alkoxysilane-containing aromatic amine compound and aromatic amide compound are shown below.
  • a compound obtained by reacting an aromatic amine compound and an alkoxy group-containing silicon compound may be used.
  • an aromatic amine compound and a group that reacts with an amino group such as an epoxy group or a chloromethyl group may be used.
  • the content of the other post-curing adhesion improver is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the component (A). By setting it as such a range, adhesiveness with the base material after baking or hardening can be improved. Further, it can also contain a compound that acts as an adhesion improving agent after development and an adhesion improving agent after curing, such as vinyltrimethoxysilane and vinyltriethoxysilane.
  • the resin composition of the present invention may contain other alkali-soluble resins in addition to the component (A).
  • alkali-soluble polyimide, polybenzoxazole, acrylic polymer copolymerized with acrylic acid, novolac resin, resole resin, polymer containing radical polymerizable monomer having alkali-soluble group, siloxane resin, cyclic olefin resin examples thereof include a resin having a cardo structure, that is, a skeleton structure in which two cyclic structures are bonded to a quaternary carbon atom constituting the cyclic structure.
  • Such a resin is soluble in an alkaline solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate.
  • an alkaline solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, and sodium carbonate.
  • the resin composition of the present invention preferably contains a solvent.
  • Solvents include N-methyl-2-pyrrolidone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2 -Polar aprotic solvents such as imidazolidinone, N, N'-dimethylpropyleneurea, N, N-dimethylisobutyramide, methoxy-N, N-dimethylpropionamide, tetrahydrofuran, dioxane, propylene glycol monomethyl ether, propylene Ethers such as glycol monoethyl ether, ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, ethyl acetate, butyl acetate, isobutyl acetate, prop
  • the dissolution order of each component is not particularly limited, and for example, there is a method of sequentially dissolving compounds having low solubility.
  • the rotational speed is preferably set within a range not impairing the performance of the photosensitive colored resin composition, and is usually 200 rpm to 2000 rpm. Even in the case of stirring, it may be heated as necessary, and is usually room temperature to 80 ° C.
  • components that tend to generate bubbles when stirring and dissolving such as surfactants and some post-development adhesion improvers, are added after the other components are dissolved, so that Dissolution failure can be prevented.
  • the resin film When the resin film has photosensitivity, it is irradiated with actinic radiation through a mask having a desired pattern on the film.
  • actinic radiation used for exposure includes ultraviolet rays, visible rays, electron beams, X-rays, etc., but in the present invention, g-rays (436 nm), h-rays (405 nm), i-rays (365 nm), which are general exposure wavelengths. It is preferable to use.
  • these alkaline aqueous solutions may contain polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol,
  • polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol,
  • One or more alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone may be contained.
  • alcohols such as ethanol and isopropyl alcohol, and esters such as eth
  • the resin film thus obtained is subjected to a thermal crosslinking reaction by applying a temperature of 140 ° C. to 280 ° C. to improve heat resistance and chemical resistance (this process may be referred to as a heat treatment process).
  • This heat treatment is carried out for 5 minutes to 5 hours by selecting the temperature and raising the temperature stepwise, or by selecting a temperature range and continuously raising the temperature. As an example, heat treatment is performed at 130 ° C. and 200 ° C. for 30 minutes each.
  • the curing conditions in the present invention are preferably 140 ° C. or higher and 280 ° C. or lower.
  • the curing condition is preferably 140 ° C. or higher, and more preferably 160 ° C. or higher in order to advance the thermal crosslinking reaction.
  • the present invention is particularly preferably 280 ° C. or lower in order to provide a cured film excellent by curing at a low temperature, and to suppress a malfunction caused by a thermal history of a semiconductor device to be described later and improve the yield.
  • the following is more preferable, and 220 ° C. or lower is further preferable.
  • a display device including a first electrode formed on a substrate and a second electrode provided to face the first electrode, specifically, for example, an LCD, an ECD, an ELD, an organic electroluminescent element It can be used for an insulating layer of the display device (organic electroluminescence device) used.
  • the cured film formed by curing the resin composition of the present invention has high adhesion to a semiconductor chip on which metal wiring is applied, and is also used as a sealing resin to an epoxy resin or the like. Since it has a high adhesive strength, it is suitably used as an interlayer insulating film provided on an adjacent base material (substrate) composed of two or more materials.
  • the resin composition of the present invention is also suitably used for coil parts of inductor devices.
  • the heating temperature for obtaining the cured film (B) is preferably heated at 320 ° C. unless the cured film is thermally decomposed.
  • the thermal decomposition temperature of the cured film can be analyzed by thermogravimetry (TGA).

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  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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JP2019172974A (ja) * 2018-03-26 2019-10-10 東レ株式会社 アルカリ可溶性樹脂溶液の製造方法
WO2020026937A1 (ja) * 2018-08-01 2020-02-06 東レ株式会社 樹脂組成物、樹脂シート、硬化膜、硬化膜の製造方法、半導体装置および表示装置
WO2021085321A1 (ja) * 2019-10-29 2021-05-06 東レ株式会社 樹脂組成物、樹脂シート、硬化膜、硬化膜の製造方法、半導体装置、有機ｅｌ表示装置および表示装置
EP3951498A1 (en) 2020-08-04 2022-02-09 Shin-Etsu Chemical Co., Ltd. Positive photosensitive resin composition, positive photosensitive dry film, method for producing positive photosensitive dry film, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP3951499A1 (en) 2020-08-04 2022-02-09 Shin-Etsu Chemical Co., Ltd. Negative photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP3974904A1 (en) 2020-09-24 2022-03-30 Shin-Etsu Chemical Co., Ltd. Photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP4063954A2 (en) 2021-03-23 2022-09-28 Shin-Etsu Chemical Co., Ltd. Positive photosensitive resin composition, positive photosensitive dry film, method for producing positive photosensitive dry film, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP4067999A1 (en) 2021-03-23 2022-10-05 Shin-Etsu Chemical Co., Ltd. Negative photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
WO2023042608A1 (ja) * 2021-09-15 2023-03-23 東レ株式会社 ポリイミド樹脂、感光性樹脂組成物、硬化物、有機ｅｌディスプレイ、電子部品、および半導体装置

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CN115232017A (zh) * 2021-03-15 2022-10-25 华为技术有限公司 一种化合物、一种树脂及其制备方法和应用

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TWI662063B (zh) * 2018-02-02 2019-06-11 新應材股份有限公司 感光性聚醯亞胺組成物及其所製成之光阻膜
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WO2021085321A1 (ja) * 2019-10-29 2021-05-06 東レ株式会社 樹脂組成物、樹脂シート、硬化膜、硬化膜の製造方法、半導体装置、有機ｅｌ表示装置および表示装置
EP3951498A1 (en) 2020-08-04 2022-02-09 Shin-Etsu Chemical Co., Ltd. Positive photosensitive resin composition, positive photosensitive dry film, method for producing positive photosensitive dry film, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP3951499A1 (en) 2020-08-04 2022-02-09 Shin-Etsu Chemical Co., Ltd. Negative photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP3974904A1 (en) 2020-09-24 2022-03-30 Shin-Etsu Chemical Co., Ltd. Photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
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EP4063954A2 (en) 2021-03-23 2022-09-28 Shin-Etsu Chemical Co., Ltd. Positive photosensitive resin composition, positive photosensitive dry film, method for producing positive photosensitive dry film, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
EP4067999A1 (en) 2021-03-23 2022-10-05 Shin-Etsu Chemical Co., Ltd. Negative photosensitive resin composition, patterning process, method for forming cured film, interlayer insulation film, surface protective film, and electronic component
WO2023042608A1 (ja) * 2021-09-15 2023-03-23 東レ株式会社 ポリイミド樹脂、感光性樹脂組成物、硬化物、有機ｅｌディスプレイ、電子部品、および半導体装置

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TWI732855B (zh) 2021-07-11
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CN108779251A (zh) 2018-11-09

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