WO2015141618A1 - 感光性樹脂組成物、硬化レリーフパターンの製造方法、並びに半導体装置 - Google Patents

感光性樹脂組成物、硬化レリーフパターンの製造方法、並びに半導体装置 Download PDF

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WO2015141618A1
WO2015141618A1 PCT/JP2015/057678 JP2015057678W WO2015141618A1 WO 2015141618 A1 WO2015141618 A1 WO 2015141618A1 JP 2015057678 W JP2015057678 W JP 2015057678W WO 2015141618 A1 WO2015141618 A1 WO 2015141618A1
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component
group
resin composition
mass
parts
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PCT/JP2015/057678
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English (en)
French (fr)
Japanese (ja)
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信裕 安西
大輔 笹野
尋子 古賀
泰平 井上
友裕 頼末
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旭化成イーマテリアルズ株式会社
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Priority to CN201580013242.7A priority Critical patent/CN106104381B/zh
Priority to JP2016508712A priority patent/JP6388640B2/ja
Priority to KR1020167022632A priority patent/KR101934171B1/ko
Publication of WO2015141618A1 publication Critical patent/WO2015141618A1/ja

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2012—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking

Definitions

  • the present invention is, for example, a photosensitive resin composition used for forming a relief pattern such as an insulating material of an electronic component, a passivation film, a buffer coat film and an interlayer insulating film in a semiconductor device, and a method for producing a cured relief pattern using the same.
  • the present invention relates to a semiconductor device having a cured relief pattern and a resin film having excellent adhesion to a polybenzoxazole resin.
  • resins such as polyimide having excellent heat resistance, electrical characteristics, and mechanical characteristics have been used for insulating materials for electronic components, and passivation films, surface protective films, interlayer insulating films, and the like of semiconductor devices.
  • resins such as polyimide the resin provided in the form of a photosensitive polyimide precursor can be easily formed into a heat-resistant relief pattern film by thermal imidization treatment by applying the precursor, exposing, developing, and curing. Can be formed.
  • the photosensitive polyimide precursor has a feature that the process can be greatly shortened as compared with the conventional non-photosensitive polyimide.
  • the interlayer insulation film forming process is performed separately by the former process manufacturer and the later process manufacturer, so that the resin such as polyimide is formed on the polybenzoxazole film formed in the previous process.
  • the conventional photosensitive resin composition has a problem in that when an additional film is formed on the polybenzoxazole film, the adhesiveness is insufficient, and thus peeling occurs after development and curing.
  • an adhesion assistant that improves the adhesion of the resin to the Si substrate and the Cu substrate has been conventionally known.
  • the adhesion assistant is used, there is a problem that the resolution or heat resistance of the relief pattern deteriorates.
  • the opening of the photosensitive resin pattern has a forward taper type whose side surface is gentler than the vertical to the bottom surface when patterning is completed, and preferably the taper angle is 80 ° or less.
  • a conventional photosensitive resin composition it is difficult to make the side surface of the opening portion into a forward taper type when patterning is completed.
  • the problem to be solved by the present invention is a cured film having excellent adhesion to a polybenzoxazole resin, a Si substrate and a Cu substrate, high resolution and heat resistance, and a side surface of the opening having a forward taper type.
  • a photosensitive resin composition for producing a cured resin, a method for producing a cured relief pattern using the photosensitive resin composition, a semiconductor device provided with the cured relief pattern, and a resin film having excellent adhesion to a polybenzoxazole resin It is to provide a laminate that is laminated on a resin substrate having a glass transition temperature of 250 ° C. or lower.
  • the inventors of the present invention provide a photosensitive resin composition obtained by specifying any one of a resin structure, a type of initiator, and a type of coupler, which is in close contact with a polybenzoxazole resin, a Si substrate, and a Cu substrate. It provides excellent curing, high resolution and heat resistance, and gives a cured relief pattern that has a tapered front side, and contains a specific resin and has a specific crosslink density and a specific 5% weight reduction.
  • the present inventors have found that a resin film having a temperature can be laminated on a resin substrate having a glass transition temperature of 250 ° C. or lower while being excellent in adhesiveness with a polybenzoxazole resin. That is, the present invention is as follows.
  • the following ingredients (A) Polyamide precursor polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyhydroxyamide, polyaminoamide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole that can be a polyoxazole precursor At least one resin selected from the group consisting of polybenzothiazole, and phenolic resin; (B) a photosensitive agent; and (C) at least one selected from the group consisting of a polyfunctional (meth) acrylate and a low molecular weight imide compound having a molecular weight of less than 1000;
  • a photosensitive resin composition comprising: [2]
  • the component (A) is a polyimide precursor consisting of polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole, and polybenzothiazole.
  • the component (A) is represented by the following general formula (A1): ⁇ Wherein, X 1 is a tetravalent organic group, Y 1 is a divalent organic group, l is an integer of 2 to 150, and R 1 and R 2 are each independently A hydrogen atom or a monovalent organic group capable of radical polymerization. However, R 1 and R 2 are not simultaneously hydrogen atoms.
  • component (C) is represented by the following general formula (C1): ⁇ Wherein R 3 is a single bond, a hydrogen atom or a monovalent to trivalent organic group, and R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, 10 cycloalkyl groups, aryl groups, alkoxy groups or halogen atoms, and m is an integer of 1 or more.
  • the component (A) is represented by the following general formula (A2): ⁇ Wherein X 2 is a tetravalent organic group, Y 2 is a divalent organic group, n is an integer of 2 to 150, and R 6 and R 7 are each independently A hydrogen atom, the following general formula (A3): (Wherein R 8 , R 9 and R 10 are each independently a hydrogen atom or an organic group having 1 to 3 carbon atoms, and p is an integer of 2 to 10) Or a saturated aliphatic group having 1 to 4 carbon atoms. However, R 6 and R 7 are not both hydrogen atoms at the same time.
  • the component (C) is represented by the following general formula (C2): ⁇ In the formula, R 11 is a single bond, a hydrogen atom or a monovalent to trivalent organic group; R 12 and R 13 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, 10 cycloalkyl groups, aryl groups, alkoxy groups or halogen atoms, and q is an integer of 2 to 4.
  • the component (B) is the following components (B1) and (B2): (B1) an oxime ester compound in which the 0.001 wt% solution has an i-ray absorbance of 0.15 to 0.5, and the 0.001 wt% solution has a g-ray absorbance and an h-ray absorbance of 0.2 or less; and (B2) An oxime ester compound in which the i-line absorbance of the 0.001 wt% solution is 0.1 or less and the g-ray absorbance or h-ray absorbance of the 0.001 wt% solution is 0.05 or more;
  • the photosensitive resin composition according to any one of [1] to [7], comprising at least one selected from the group consisting of: [9]
  • the component (B1) is represented by the following general formulas (B11) and (B12): ⁇ Wherein R 14 is a C 1 -C 10 fluorine-containing alkyl group, and R 15 , R 16 , and R 17 are each independently a C 1 -C 20 alkyl group, C 3 -C 20 A cycloalkyl group, a C 6 -C 20 aryl group, or a C 1 -C 20 alkoxy group, and r is an integer of 0-5. ⁇ ⁇ Wherein R 18 is a C 1 -C 30 divalent organic group, and R 19 -R 26 are each independently a C 1 -C 20 alkyl group or a C 3 -C 20 cycloalkyl group.
  • component (A) For 100 parts by mass of component (A), 0.1 to 20 parts by mass of the component (B); Component (C) 10 to 35 parts by mass; and component (D) 0.1 to 20 parts by mass;
  • the photosensitive resin composition as described in [11] or [12].
  • the photosensitive resin composition according to [13] comprising: [19] For 100 parts by mass of component (A), 0.1 to 20 parts by mass of the component (B); Component (C) 10 to 35 parts by mass; and component (E) 0.1 to 20 parts by mass;
  • the component (B1) is represented by the following general formulas (B11) and (B12): ⁇ Wherein R 14 is a C 1 -C 10 fluorine-containing alkyl group, and R 15 , R 16 , and R 17 are each independently a C 1 -C 20 alkyl group, C 3 -C 20 A cycloalkyl group, a C 6 -C 20 aryl group, or a C 1 -C 20 alkoxy group, and r is an integer of 0-5. ⁇ ⁇ Wherein R 18 is a C 1 -C 30 divalent organic group, and R 19 -R 26 are each independently a C 1 -C 20 alkyl group or a C 3 -C 20 cycloalkyl group.
  • the total content of the component (B1) and the component (B2) with respect to 100 parts by mass of the (AX) component is 0.1 to 10 parts by mass, according to any one of [20] to [23] Photosensitive resin composition.
  • Resin composition [26] The following ingredients: (AY) polyimide precursor; and (D) the following general formula (D1): ⁇ Wherein R 27 and R 28 are C 1 to C 4 alkyl groups, R 29 is a C 1 to C 6 divalent organic group, and R 30 is composed of nitrogen, oxygen, and sulfur.
  • An organic group of C 1 to C 20 bonded to a carbonyl group by an atom selected from the group, t is an integer selected from 1, 2, and 3, and u is an integer selected from 0, 1, and 2. And t and u satisfy the relationship t + u 3.
  • the component (AY) is represented by the following general formula (A2): ⁇ Wherein X 2 is a tetravalent organic group, Y 2 is a divalent organic group, n is an integer of 2 to 150, and R 6 and R 7 are each independently A hydrogen atom, the following general formula (A3): (Wherein R 8 , R 9 and R 10 are each independently a hydrogen atom or an organic group having 1 to 3 carbon atoms, and p is an integer of 2 to 10) Or a saturated aliphatic group having 1 to 4 carbon atoms. However, R 6 and R 7 are not both hydrogen atoms at the same time.
  • the component (A) is a polyimide precursor consisting of polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole, and polybenzothiazole.
  • the resin film according to [35] or [36] which is at least one selected resin.
  • [38] [35] A laminate in which the resin film according to any one of [37] is laminated on a resin substrate having a glass transition temperature of 200 ° C. or lower.
  • [39] [35] A laminate in which the resin film according to any one of [37] is laminated on a resin substrate having a glass transition temperature of 250 ° C. or lower.
  • a photosensitive film for producing a cured film having excellent adhesion to a polybenzoxazole resin, a Si substrate, and a Cu substrate, high resolution and heat resistance, and a side surface of an opening having a forward taper type.
  • Resin composition, method for producing a cured relief pattern using the photosensitive resin composition, a semiconductor device provided with the cured relief pattern, a resin film having excellent adhesion to a polybenzoxazole resin, and the resin film having a glass transition Provided is a laminate laminated on a resin substrate having a temperature of 250 ° C. or lower.
  • ⁇ Resin composition> Polyamide precursor polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyhydroxyamide, polyaminoamide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole that can be a polyoxazole precursor At least one resin selected from the group consisting of polybenzothiazole, and phenolic resin; (B) a photosensitive agent; and (C) at least one selected from the group consisting of a polyfunctional (meth) acrylate and a low molecular weight imide compound having a molecular weight of less than 1000; The resin composition containing is described.
  • component (A) component used in this composition is polyhydroxyamide, polyaminoamide which can be a polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyoxazole precursor which is a polyimide precursor, It is at least one resin selected from the group consisting of polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole, polybenzothiazole, and phenol resin.
  • a group consisting of polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole, polybenzothiazole At least one resin selected from the above is preferred.
  • the weight average molecular weight of these resins is preferably 1,000 or more and more preferably 5,000 or more in terms of polystyrene by gel permeation chromatography from the viewpoint of heat resistance after heat treatment and mechanical properties.
  • the upper limit of the weight average molecular weight is preferably 100,000 or less.
  • Component resin is preferably a photosensitive resin in order to form a relief pattern with the resin composition.
  • the photosensitive resin is a resin that forms a photosensitive resin composition and causes development by dissolution or non-dissolution in a subsequent development step when used together with the later-described (B) photosensitive agent.
  • Photosensitive resins include polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyamide, polyamidoimide, polyimide, polybenzoxazole, polybenzimidazole, and polybenzthiazole, which are polyimide precursors, after heat treatment. From the viewpoint that these resins are excellent in heat resistance and mechanical properties, polyimide precursors, polyamides, and / or polyimides are preferably used. These photosensitive resins should be selected according to the desired application from the viewpoint of whether to prepare a negative type or a positive type photosensitive resin composition together with the photosensitive agent (B) described later. Can do.
  • polyimide precursor In the resin composition of the present invention, from the viewpoint of heat resistance and photosensitivity, one of (A) resin, (AX) photosensitive polyimide precursor, and (AY) polyimide precursor is preferably represented by the following general formula (A1). ): ⁇ Wherein, X 1 is a tetravalent organic group, Y 1 is a divalent organic group, l is an integer of 2 to 150, and R 1 and R 2 are each independently A hydrogen atom or a monovalent organic group capable of radical polymerization. However, R 1 and R 2 are not simultaneously hydrogen atoms.
  • the polyamide has a structure represented by the following general formula (A2): ⁇ Wherein X 2 is a tetravalent organic group, Y 2 is a divalent organic group, n is an integer of 2 to 150, and R 6 and R 7 are each independently A hydrogen atom, the following general formula (A3): (Wherein R 8 , R 9 and R 10 are each independently a hydrogen atom or an organic group having 1 to 3 carbon atoms, and p is an integer of 2 to 10) Or a saturated aliphatic group having 1 to 4 carbon atoms. However, R 6 and R 7 are not both hydrogen atoms at the same time.
  • the tetravalent organic group represented by X 2 is preferably an organic group having 6 to 40 carbon atoms, more preferably a —COOR 6 group, from the viewpoint of heat resistance and photosensitive properties.
  • the —COOR 7 group and the —CONH— group are each an aromatic group or an alicyclic aliphatic group in the ortho position.
  • the tetravalent organic group represented by X 2 is more preferably the following formula: Although the structure represented by these is mentioned, it is not limited to these. Structure of X 2 may be two or more kinds in combination.
  • the divalent organic group represented by Y 2 is preferably an aromatic group having 6 to 40 carbon atoms from the viewpoint of heat resistance and photosensitive properties.
  • A represents a methyl group (—CH 3 ), an ethyl group (—C 2 H 5 ), a propyl group (—C 3 H 7 ), or a butyl group (—C 4 H 9 ).
  • Y 2 may be two or more kinds in combination.
  • R 8 in the general formula (A3) is preferably a hydrogen atom or a methyl group
  • R 9 and R 10 are preferably a hydrogen atom from the viewpoint of photosensitive properties.
  • p is preferably an integer of 2 to 10, more preferably an integer of 2 to 4, from the viewpoint of photosensitive characteristics.
  • Examples include an ester bond type and an ion bond type.
  • the former is a method of introducing a photopolymerizable group, that is, a compound having an olefinic double bond, into the side chain of the polyimide precursor by an ester bond, and the latter has a carboxyl group and an amino group of the polyimide precursor ( In this method, a photopolymerizable group is imparted by bonding an amino group of a (meth) acrylic compound via an ionic bond.
  • the polyimide precursor of the ester-linked firstly, a tetracarboxylic acid dianhydride containing tetravalent organic group X 2 described above, the photopolymerizable alcohols and optionally saturated aliphatic alcohols having an unsaturated double bond And a partially esterified tetracarboxylic acid (hereinafter also referred to as an acid / ester), and this and a diamine containing the divalent organic group Y 2 described above. Obtained by polycondensation.
  • tetracarboxylic dianhydrides containing a tetravalent organic group X 2 that are preferably used for preparing an ester-bonded polyimide precursor include pyromellitic anhydride, diphenyl ether-3, 3 ′, 4 , 4′-tetracarboxylic dianhydride, benzophenone-3,3 ′, 4,4′-tetracarboxylic dianhydride, biphenyl-3,3 ′, 4,4′-tetracarboxylic dianhydride, diphenyl Sulfone-3,3 ′, 4,4′-tetracarboxylic dianhydride, diphenylmethane-3,3 ′, 4,4′-tetracarboxylic dianhydride, 2,2-bis (3,4-phthalic anhydride) Acid) propane, 2,2-bis (3,4-phthalic anhydride) -1,1,1,3,3,3-hexafluoropropan
  • Examples of alcohols having a photopolymerizable unsaturated double bond that are preferably used for preparing an ester-linked polyimide precursor include 2-acryloyloxyethyl alcohol and 1-acryloyloxy-3-propyl.
  • methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, etc. are mixed as saturated aliphatic alcohols having 1 to 4 carbon atoms with alcohols having photopolymerizable unsaturated double bonds. Can also be used.
  • the preferred tetracarboxylic dianhydride described above and the preferred alcohol described above are mixed in a suitable reaction solvent at a temperature of 20 to 50 ° C. for 4 to 10 hours in the presence of a basic catalyst such as pyridine.
  • a basic catalyst such as pyridine.
  • the reaction solvent is preferably a solvent that completely dissolves the acid / ester body and the polyimide precursor that is an amide polycondensation product of this with a diamine component.
  • a solvent that completely dissolves the acid / ester body and the polyimide precursor that is an amide polycondensation product of this with a diamine component for example, N-methyl-2-pyrrolidone, N, N— Examples include dimethylacetamide, N, N-dimethylformamide, dimethyl sulfoxide, tetramethylurea, and ⁇ -butyrolactone.
  • reaction solvents include ketones, esters, lactones, ethers, halogenated hydrocarbons, hydrocarbons, etc., for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate.
  • an appropriate dehydration condensation agent such as dicyclohexylcarbodiimide, 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, 1 , 1-carbonyldioxy-di-1,2,3-benzotriazole, N, N′-disuccinimidyl carbonate and the like are added and mixed to convert the acid / ester into a polyanhydride.
  • the preferred divalent diamines containing organic group Y 1 was allowed to separate dissolved or dispersed in a solvent solution or dispersion was added dropwise to polyanhydrides, by engaged amide polycondensation, the photosensitive resin of interest Obtainable.
  • Preferred diamines containing a divalent organic group Y 1 include, for example, p-phenylene diamine, m-phenylene diamine, 4,4-diaminodiphenyl ether, 3,4′-diaminodiphenyl ether, 3,3′-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide, 3,4'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 3,3'- Diaminodiphenyl sulfone, 4,4'-diaminobiphenyl, 3,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 4,4'-diaminobenzophenone, 3,4'
  • a polyimide precursor is used as the resin of component (A).
  • (AX) photosensitive polyimide precursor or (AY) polyimide precursor 1,3-bis (3-aminopropyl) tetramethyldisiloxane, 1,3-bis (3- It is also possible to copolymerize diaminosiloxanes such as (aminopropyl) tetraphenyldisiloxane.
  • the water-absorbing by-product of the dehydrating condensing agent coexisting in the reaction solution is filtered off if necessary, and then a poor solvent such as water, an aliphatic lower alcohol, or a mixture thereof is removed.
  • the polymer component is added to the polymer component, and the polymer component is precipitated. Further, the polymer is purified by repeating redissolution, reprecipitation and the like, and vacuum drying is performed to obtain the target polyimide precursor. Isolate.
  • the polymer solution may be passed through a column packed with an anion and / or cation exchange resin swollen with a suitable organic solvent to remove ionic impurities.
  • the weight average molecular weight of the ester bond type polyimide precursor is preferably 8,000 to 150,000, and more preferably 9,000 to 50,000 in terms of polystyrene by gel permeation chromatography.
  • the weight average molecular weight is 8,000 or more, the mechanical properties are good, and when it is 150,000 or less, the dispersibility in the developer is good and the resolution performance of the relief pattern is good. Tetrahydrofuran and / or N-methyl-2-pyrrolidone is recommended as a developing solvent for gel permeation chromatography.
  • the molecular weight is determined from a calibration curve prepared using standard monodisperse polystyrene. As the standard monodisperse polystyrene, it is preferable to select an organic solvent standard sample STANDARD SM-105 manufactured by Showa Denko.
  • Photosensitizer As the photosensitizer, a compound conventionally used as a photopolymerization initiator for UV curing can be arbitrarily selected.
  • compounds that can be suitably used as a photosensitizer include benzophenone derivatives such as benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4′-methyldiphenyl ketone, dibenzyl ketone, and fluorenone; 2,2 ′ -Acetophenone derivatives such as diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone; thioxanthone derivatives such as thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone; benzil Benzyl derivatives such as benzyl dimethyl ketal and benzyl- ⁇ -me
  • the oximes used as photosensitizers are the following components (B1) and (B2): (B1) an oxime ester compound having a g-line absorbance and h-line absorbance of 0.2 or less and an i-line absorbance of 0.15 to 0.5 with respect to a 0.001 wt% solution; and (B2) 0.001 wt An oxime ester compound having a g-line absorbance or h-line absorbance of 0.05 or more and an i-line absorbance of 0.1 or less with respect to a% solution; It is preferably at least one selected from the group consisting of The absorbance of the oxime ester compound can be measured by dissolving the compound in N-methylpyrrolidone at a concentration of 0.001 wt% and using a 1 cm quartz cell and a normal spectrophotometer.
  • Preferred compounds as the component (B1) include, for example, Irgacure OXE03 (trade name, manufactured by BASF), Adekaoptomer NCI831 (trade name, manufactured by ADEKA), TR-PBG326 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd., trade name) ), HTPI 426 (manufactured by Heraeus, trade name), HTPI 428 (manufactured by Heraeus, trade name), or a mixture thereof.
  • the absorbance is not sufficient, and a large amount of initiator needs to be added for curing. In that case, since it becomes difficult to be influenced by oxygen inhibition on the surface of the coating film, the degree of surface hardening increases, and the opening after exposure and development does not become a forward tapered shape. Even when the i-ray absorbance exceeds 0.5, or when at least one of the g-ray absorbance and the h-ray absorbance exceeds 0.2, the absorbance is too high and surface hardening tends to proceed. The part does not have a forward tapered shape.
  • More preferred component (B1) is an oxime ester compound having an i-line absorbance of 0.15 to 0.35 in a 0.001 wt% solution, and more preferred components (B1) are represented by the following general formulas (B11) and (B12) :
  • R 14 is a C 1 -C 10 fluorine-containing alkyl group
  • R 15 , R 16 , and R 17 are each independently a C 1 -C 20 alkyl group, C 3 -C 20 A cycloalkyl group, a C 6 -C 20 aryl group, or a C 1 -C 20 alkoxy group
  • r is an integer of 0-5.
  • R 18 is a C 1 -C 30 divalent organic group
  • R 19 -R 26 are each independently a C 1 -C 20 alkyl group or a C 3 -C 20 cycloalkyl group.
  • ⁇ Is at least one selected from the group consisting of oxime ester compounds represented by:
  • the oxime ester compound (B2) also functions as a photopolymerization initiator.
  • the absorbance of the oxime ester compound (B2) can be measured in the same manner as in the case of the oxime ester compound (B1).
  • TR-PBG340 manufactured by Changzhou Strong Electronic New Materials Co., Ltd., trade name
  • a component (B2) when a compound having a g-ray absorbance and h-ray absorbance of less than 0.05 is used as a 0.001 wt% solution, the absorbance is not sufficient, so that a large amount of initiator needs to be added for curing. . In that case, since it becomes difficult to be influenced by oxygen inhibition on the surface of the coating film, the degree of surface hardening increases, and the opening after exposure and development does not become a forward tapered shape. Even in the case where the i-line absorbance exceeds 0.1, the absorbance is too high and surface hardening is likely to proceed, and the opening after exposure and development does not have a forward tapered shape.
  • the total amount of the component (B1) and the component (B2) used for 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor is in the range of 0.1 to 20 parts by mass. It is preferably in the range of 0.5 to 5 parts by mass.
  • the total amount of the (B1) component and the (B2) component is 0.1 parts by mass or more with respect to 100 parts by mass of the (A) resin, the (AX) photosensitive polyimide precursor, or the (AY) polyimide precursor. When it is excellent in photosensitivity and is 20 parts by mass or less, the forward taper property is excellent.
  • component (C) At least one selected from the group consisting of a polyfunctional (meth) acrylate and a low molecular weight imide compound having a molecular weight of less than 1000.
  • the component (C) comprises a polyfunctional (meth) acrylate and a low molecular weight imide compound having a molecular weight of less than 1000. It is at least one selected from the group.
  • “(Meth) acrylate” means acrylate or methacrylate.
  • Component (C) may be a polymerizable monomer.
  • the glass transition temperature of the homopolymer obtained by polymerizing only the component (C) is preferably 200 ° C. or higher.
  • isocyanuric acid tri (meth) acrylate isocyanuric acid tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate And dipentaerythritol hexa (meth) acrylate.
  • the low molecular weight imide compound having a molecular weight of less than 1000 is represented by the following general formula (C1): ⁇ Wherein R 3 is a single bond, a hydrogen atom or a monovalent to trivalent organic group, and R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, 10 cycloalkyl groups, aryl groups, alkoxy groups or halogen atoms, and m is an integer of 1 or more. ⁇ It is preferable that it is maleimide represented by these. In the formula (C1), m may be an integer of 2 or more or an integer of 3 or more.
  • the low molecular weight imide compound having a molecular weight of less than 1000 is represented by the following general formula (C2): ⁇ In the formula, R 11 is a single bond, a hydrogen atom or a monovalent to trivalent organic group; R 12 and R 13 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, 10 cycloalkyl groups, aryl groups, alkoxy groups or halogen atoms, and q is an integer of 2 to 4. ⁇ It is more preferable that it is maleimide represented by these.
  • a cured film having excellent adhesion after development on a polybenzoxazole resin can be obtained.
  • the mechanism by which the relief pattern on the polybenzoxazole resin is excellent in adhesion after development is not clear, in the heating step (about 100 ° C.) for drying the solvent when forming the coating film of the relief pattern, as the component (C)
  • the low molecular weight imide compound and the polybenzoxazole resin are stacked and interact at the resin interface, so that the developer soaks into the interface between the coating film and the polybenzoxazole resin during development, or solvates. It is inferred that dissolution is suppressed and as a result, peeling of the relief pattern is suppressed.
  • the low molecular weight imide compound examples include 1-phenylpyrrolidine-2,5-dione, succinimide, N-pentylsuccinimide, glutadine, 2,6 (1H, 3H) -pyridinedione, N-ethylmaleimide, Fluorimide, N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (2-chlorophenyl) maleimide, N- (4-methylphenyl) maleimide, N- (4-ethoxyphenyl) maleimide, N -Isopropylmaleimide, N-methylmaleimide, N- (2-nitrophenyl) maleimide, N- (2-methylphenyl) maleimide, 1- (2,4-dimethylphenyl) -3-pyrroline-2, 5-dione, 1- (1,1′-biphenyl-4-yl) -1H-pi 2,5-dione, N-cyclo
  • the low molecular weight imide compound preferably has a cyclic structure, and more preferably has an unsaturated bond in the cyclic structure.
  • low molecular weight imide compounds having an unsaturated bond in the cyclic structure as represented by the general formula (C1) or (C2), it has a maleimide structure that is planar and easily sterically stacks with benzoxazole.
  • the compound is more preferable from the viewpoint of adhesion after development on the polybenzoxazole resin.
  • a divalent maleimide is more preferable than a monovalent maleimide from the viewpoint that it is difficult to dissolve in a developer due to a crosslinking reaction.
  • divalent maleimides have less steric hindrance than trivalent maleimides and are easier to stack with polybenzoxazoles. Therefore, bismaleimide is more preferable from the viewpoint of adhesion with the polybenzoxazole resin.
  • bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, 4,4′-bismaleimide diphenylmethane, or polyphenylenemethanemaleimide suppresses shrinkage during curing of the photosensitive resin composition, and is a polyimide. Or from a viewpoint of improving adhesiveness with a polybenzoxazole resin, it is still more preferable.
  • the amount of component (C) is 1 to 40 parts by weight when the photosensitive resin composition contains 100 parts by weight of resin (A) and 0.1 to 20 parts by weight of component (B).
  • the amount is preferably 10 to 35 parts by mass.
  • the blending amount of the component (C) is less than 1 part by mass, the adhesion is insufficient, and when it exceeds 40 parts by mass, the cured relief pattern obtained from the composition becomes brittle, and a passivation film and a buffer coat film. It is not suitable for applications such as interlayer insulation films.
  • (D) Silicon-containing compound (D) The component is represented by the following general formula (D1): ⁇ Wherein R 27 and R 28 are C 1 -C 4 alkyl groups, R 29 is a C 1 -C 6 divalent organic group, and R 30 is selected from nitrogen, oxygen, and sulfur.
  • An organic group of C 1 to C 20 bonded to a carbonyl group by an atom, t is an integer selected from 1, 2, and 3, u is an integer selected from 0, 1, and 2, and t And u satisfy the relationship t + u 3.
  • R 30 specifically, Methylamino group, ethylamino group, n-propylamino group, n-butylamino group, n-hexylamino group, n-octylamino group, isopropylamino group, isobutylamino group, t-butylamino group, isoamylamino group, Mono- and dialamino groups such as cyclopentyl group, cyclohexylamino group, dimethylamino group, diethylamino group, dibutylamino group, dicyclohexylamino group; Aromatic ring-containing amino groups such as phenylamino group, benzylamino group, diphenylamino group; Heterocyclic-containing amino groups such as picolyl group, aminotriazyl group, furfurylamino group, morpholino group; Alkoxy groups such as methoxy group, ethoxy group,
  • the silicon-containing compound represented by the formula (D1) is obtained by a method in which an isocyanate compound is reacted with a silicon compound having an amino group, a method in which an amine, alcohol, or thiol is reacted with a silicon compound having an isocyanate group.
  • the compounding amount of the silicon-containing compound represented by the formula (D1) is 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. From the viewpoint of improving heat resistance and adhesion, it is more preferably 0.5 to 10 parts by mass.
  • By blending the silicon-containing compound represented by the formula (D1) with 0.1 part by mass or more with respect to 100 parts by mass of the (A) resin, the (AX) photosensitive polyimide precursor, or the (AY) polyimide precursor it is excellent. Adhesion is ensured, and excellent heat resistance is maintained by blending at 20 parts by mass or less.
  • Examples of the silicon-containing compound represented by the formula (D2) include 3-ureidopropyltriethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropylethoxydimethoxysilane, 3-ureidopropyldiethoxymethoxysilane, 3 -Ureidopropylmethyldiethoxysilane, 3-ureidopropylmethyldimethoxysilane, 3-ureidopropylethyldiethoxysilane, 3-ureidopropylethyldimethoxysilane, 3-ureidopropylethyldimethoxysilane, 3-ureidopropyldimethylethoxysilane, 3-ureidopropyldimethylmethoxysilane, etc. And mixtures thereof.
  • the compounding amount of the silicon-containing compound represented by the formula (D2) is 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. From the viewpoint of improving heat resistance and adhesion, it is more preferably 0.5 to 10 parts by mass.
  • a silicon-containing compound represented by the formula (D2) is further added to the resin composition. By doing so, the resolution can be improved while improving the adhesion and heat resistance of the relief pattern to be obtained.
  • examples of the C 1 -C 20 organic group include a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a tolyl group, a benzyl group, and the like.
  • examples include methoxysilylpropyl group, triethoxysilylpropyl group, methyldimethoxysilylpropyl group, methyldiethoxysilylpropyl group, triethoxysilylethyl group and the like.
  • R 35 for example, Methylamino group, ethylamino group, n-propylamino group, n-butylamino group, n-hexylamino group, n-octylamino group, isopropylamino group, isobutylamino group, t-butylamino group, isoamylamino group, Mono- and dialamino groups such as cyclopentyl group, cyclohexylamino group, dimethylamino group, diethylamino group, dibutylamino group, dicyclohexylamino group; Aromatic ring-containing amino groups such as phenylamino group, benzylamino group, diphenylamino group; Heterocyclic-containing amino groups such as picolyl group, aminotriazyl group, furfurylamino group, morpholino group; Alkoxy groups such as methoxy group, ethoxy
  • the compounding amount of the sulfur-containing compound is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. From the viewpoint of improving heat resistance and adhesion, the content is more preferably 0.5 to 10 parts by mass.
  • (E) By mixing the sulfur-containing compound with 0.1 part by mass or more with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor, excellent adhesion can be obtained. By being blended and blended at 20 parts by mass or less, excellent heat resistance is maintained.
  • the fat composition of the present invention may further contain components other than the components (A) to (E).
  • a solvent can be used.
  • the varnish-like negative photosensitive resin composition can be obtained by dissolving the components (A) to (E) in a solvent.
  • a polar organic solvent is preferably used from the viewpoint of solubility in the (A) resin, the (AX) photosensitive polyimide precursor, or the (AY) polyimide precursor.
  • N, N-dimethylformamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N, N-dimethylacetamide, dimethyl sulfoxide, diethylene glycol dimethyl ether, cyclopentanone, ⁇ -butyrolactone, ⁇ -Acetyl- ⁇ -butyrolactone, tetramethylurea, 1,3-dimethyl-2-imidazolinone, N-cyclohexyl-2-pyrrolidone and the like are used. These can be used alone or in combination of two or more.
  • the solvent is, for example, 30 to 1500 masses per 100 mass parts of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor, depending on the desired coating thickness and viscosity of the resin composition. In the range of 100 parts by weight, preferably in the range of 100 to 1000 parts by weight.
  • a solvent containing an alcohol is preferable.
  • alcohols include alcohols having an alcoholic hydroxyl group in the molecule and no olefinic double bond, and specific examples thereof include methyl alcohol, ethyl alcohol, n-propyl alcohol, and isopropyl alcohol.
  • Alkyl alcohols such as n-butyl alcohol, isobutyl alcohol and tert-butyl alcohol; lactic acid esters such as ethyl lactate; propylene glycol-1-methyl ether, propylene glycol-2-methyl ether, propylene glycol-1-ethyl ether Propylene glycol monoalkyl ethers such as propylene glycol-2-ethyl ether, propylene glycol-1- (n-propyl) ether, propylene glycol-2- (n-propyl) ether; Glycol methyl ether, ethylene glycol ethyl ether, mono-alcohols such as ethylene glycol -n- propyl ether; 2-hydroxyisobutyric acid esters, ethylene glycol, and dialcohols such as propylene glycol.
  • lactic acid esters such as ethyl lactate
  • propylene glycol-1-methyl ether propylene glycol-2-methyl ether
  • alkyl alcohols lactic acid esters, propylene glycol monoalkyl ethers, and 2-hydroxyisobutyric acid esters are preferable.
  • alkyl alcohol ethyl alcohol is preferable. More preferred are ethyl lactate, propylene glycol-1-methyl ether, propylene glycol-1-ethyl ether, and propylene glycol-1- (n-propyl) ether.
  • the content of the alcohol having no olefinic double bond in the entire solvent is preferably 5 to 50% by mass, More preferably, it is 10 to 30% by mass.
  • the storage stability of the resin composition is good, and when it is 50% by mass or less, (A) resin, (AX) The solubility of the photosensitive polyimide precursor or (AY) polyimide precursor is good.
  • the resin composition of the present invention may further contain a resin component other than the above-mentioned (A) resin, (AX) photosensitive polyimide precursor, and (AY) polyimide precursor.
  • a resin component other than the above-mentioned (A) resin, (AX) photosensitive polyimide precursor, and (AY) polyimide precursor examples include an epoxy resin, a siloxane resin, and an acrylic resin.
  • the blending amount of these resin components is preferably in the range of 0.01 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. .
  • the resin composition of the present invention may contain a photosensitive agent other than the components (B1) and (B2) described above, and a photosensitive agent other than the components (B1) and (B2).
  • a photopolymerization initiator usually used for UV curing can be arbitrarily selected.
  • the photopolymerization initiator usually used is not limited, but for example, Benzophenone derivatives such as benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl ketone, dibenzyl ketone, fluorenone; Acetophenone derivatives such as 2,2′-diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 1-hydroxycyclohexyl phenyl ketone; Thioxanthone derivatives such as thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone; Benzyl derivatives such as benzyl, benzyldimethyl ketal, benzyl- ⁇ -methoxyethyl acetal; Benzoin derivatives such as benzoin and benzoin methyl ether; 1-phenyl-1,2-butanedione-2- (o-me
  • the blending amount of the photosensitive agent is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor, From the viewpoint of the above, it is preferably 2 to 15 parts by mass.
  • hardenability can be obtained by mix
  • a sensitizer can be arbitrarily mix
  • the sensitizer include Michler's ketone, 4,4′-bis (diethylamino) benzophenone, 2,5-bis (4′-diethylaminobenzal) cyclopentane, and 2,6-bis (4′-diethylaminobenzal).
  • the amount of the sensitizer is (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor.
  • the amount is preferably 0.1 to 25 parts by mass with respect to 100 parts by mass of the body.
  • a monomer having a photopolymerizable unsaturated bond different from the component (C) can be blended in the resin composition.
  • a (meth) acryl compound that undergoes a radical polymerization reaction with a photopolymerization initiator is preferable, and is not limited, but ethylene glycol represented by diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, etc.
  • the amount of the monomer is (A) resin, (AX It is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the photosensitive polyimide precursor or (AY) polyimide precursor.
  • an adhesion assistant can be blended in the resin composition.
  • Adhesion aids include ⁇ -aminopropyldimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, 3- Methacryloxypropyldimethoxymethylsilane, 3-methacryloxypropyltrimethoxysilane, dimethoxymethyl-3-piperidinopropylsilane, diethoxy-3-glycidoxypropylmethylsilane, N- (3-diethoxymethylsilylpropyl) succinimide N- [3- (triethoxysilyl) propyl] phthalamic acid, benzophenone-3,3′-bis (N- [3-[3-[3- (triethoxysilyl) propyl]
  • the compounding amount of the adhesion assistant is based on 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor, or (AY) polyimide precursor. , Preferably in the range of 0.5 to 25 parts by mass.
  • thermal polymerization inhibitors include hydroquinone, N-nitrosodiphenylamine, p-tert-butylcatechol, phenothiazine, N-phenylnaphthylamine, ethylenediaminetetraacetic acid, 1,2-cyclohexanediaminetetraacetic acid, glycol etherdiaminetetraacetic acid, 2,6 -Di-tert-butyl-p-methylphenol, 5-nitroso-8-hydroxyquinoline, 1-nitroso-2-naphthol, 2-nitroso-1-naphthol, 2-nitroso-5- (N-ethyl-N- Sulfopropylamino) phenol, N-nitroso-N-phenylhydroxylamine ammonium salt, N-
  • the blending amount of the thermal polymerization inhibitor in the photosensitive resin composition is 0.005 to 12 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. It is preferable that it is the range of these.
  • a crosslinking agent may be added to the resin composition.
  • the crosslinking agent may crosslink the (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor when the relief pattern formed using the resin composition of the present invention is heat-cured. Or the crosslinking agent itself can form a crosslinked network.
  • the crosslinking agent can further enhance the heat resistance and chemical resistance of the cured film formed from the negative photosensitive resin composition.
  • amino resins and derivatives thereof are preferably used, and among them, urea resins, glycol urea resins, hydroxyethylene urea resins, melamine resins, benzoguanamine resins, and derivatives thereof are more preferably used.
  • Particularly preferred crosslinking agents are alkoxymethylated urea compounds and alkoxymethylated melamine compounds. Examples thereof include MX-290 (manufactured by Nippon Carbide), UFR-65 (manufactured by Nippon Cytec Co., Ltd.), and MW-390 (Manufactured by Nippon Carbide Corporation).
  • the blending amount of the crosslinking agent in the resin composition is (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide.
  • the amount is preferably 0.5 to 20 parts by mass, more preferably 2 to 10 parts by mass with respect to 100 parts by mass of the precursor. When the amount is 0.5 parts by mass or more, good heat resistance and chemical resistance are exhibited, and when it is 20 parts by mass or less, the storage stability is excellent.
  • an azole compound can be added to the resin composition in order to suppress discoloration of the substrate surface.
  • the azole compound 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole, 4-t-butyl-5 -Phenyl-1H-triazole, 5-hydroxyphenyl-1H-triazole, phenyltriazole, p-ethoxyphenyltriazole, 5-phenyl-1- (2-dimethylaminoethyl) triazole, 5-benzyl-1H-triazole, hydroxyphenyl Triazole, 1,5-dimethyltriazole, 4,5-diethyl-1H-triazole, 1H-benzotriazole, 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-3,5- Bis (
  • the compounding amount of the azole compound in the resin composition is 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor.
  • the amount is preferably 0.5 to 5 parts by mass from the viewpoint of photosensitivity.
  • the resin composition of the present invention is made of copper or When formed on a copper alloy, discoloration of the copper or copper alloy surface is suppressed, and when it is 10 parts by mass or less, the photosensitivity is excellent.
  • a hindered phenol compound can be added to the resin composition.
  • hindered phenol compounds include 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-butyl-hydroquinone, and octadecyl-3- (3,5-di-t-butyl-4.
  • 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) -1,3,5-triazine-2,4,6- (1H, 3H, 5H ) -Trione and the like are preferred.
  • the blending amount of the hindered phenol compound is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor. From the viewpoint of sensitivity, it is more preferably 0.5 to 10 parts by mass.
  • the blending amount of the hindered phenol compound with respect to 100 parts by mass of (A) resin, (AX) photosensitive polyimide precursor or (AY) polyimide precursor is 0.1 parts by mass or more, for example, on copper or copper alloy
  • the resin composition of the present invention is formed, discoloration / corrosion of copper or a copper alloy is prevented, and when it is 20 parts by mass or less, the photosensitivity is excellent.
  • the photosensitive resin composition of this invention is apply
  • a coating method a method conventionally used for coating a photosensitive resin composition, for example, a method of coating with a spin coater, bar coater, blade coater, curtain coater, screen printing machine, etc., spray coating with a spray coater A method or the like can be used.
  • the coating film made of the photosensitive resin composition can be dried.
  • a drying method methods such as air drying, heat drying with an oven or a hot plate, and vacuum drying are used.
  • drying of the coating film causes modification of (A) resin in the photosensitive resin composition, or imidization of (AX) photosensitive polyimide precursor, (AY) polyimide precursor (polyamic acid ester). It is desirable to perform under such conditions. Specifically, when air drying or heat drying is performed, the drying can be performed at 20 ° C. to 140 ° C. for 1 minute to 1 hour. Thus, a photosensitive resin layer can be formed on the substrate.
  • Step of exposing the photosensitive resin layer the photosensitive resin layer formed above is exposed through a photomask or reticle having a pattern using an exposure apparatus such as a contact aligner, a mirror projection, or a stepper.
  • an exposure apparatus such as a contact aligner, a mirror projection, or a stepper.
  • direct exposure is performed with an ultraviolet light source or the like.
  • post-exposure baking PEB
  • pre-development baking with any combination of temperature and time may be performed as necessary for the purpose of improving photosensitivity.
  • the range of baking conditions is preferably a temperature of 40 to 120 ° C. and a time of 10 seconds to 240 seconds, but is not limited to this range as long as the various characteristics of the photosensitive resin composition of the present invention are not impaired.
  • Step of developing the exposed photosensitive resin layer to form a relief pattern the unexposed portion of the exposed photosensitive resin layer is developed and removed.
  • a developing method for developing the photosensitive resin layer after exposure any of the conventionally known photoresist developing methods, for example, a rotary spray method, a paddle method, an immersion method with ultrasonic treatment, etc. A method can be selected and used.
  • post-development baking at any combination of temperature and time may be performed as necessary.
  • the developer used for development is preferably a good solvent for the photosensitive resin composition or a combination of the good solvent and the poor solvent.
  • the good solvent N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylacetamide, cyclopentanone, cyclohexanone, ⁇ -butyrolactone, ⁇ -acetyl- ⁇ -butyrolactone, etc. are preferable.
  • As the solvent toluene, xylene, methanol, ethanol, isopropyl alcohol, ethyl lactate, propylene glycol methyl ether acetate, water and the like are preferable.
  • the ratio of the poor solvent to the good solvent depending on the solubility of the polymer in the photosensitive resin composition.
  • two or more of each solvent for example, several types may be used in combination.
  • Step of forming a relief pattern by subjecting the relief pattern to heat treatment the relief pattern obtained by the above development is heated to dilute the photosensitive component, and (A) resin, (AX) The photosensitive polyimide precursor or (AY) polyimide precursor is converted into a cured relief pattern by heat curing.
  • a method of heat curing various methods such as a method using a hot plate, a method using an oven, and a method using a temperature rising oven capable of setting a temperature program can be selected.
  • the heating can be performed, for example, at 200 ° C. to 400 ° C. for 30 minutes to 5 hours.
  • As the atmospheric gas at the time of heat curing air may be used, or an inert gas such as nitrogen or argon may be used.
  • a semiconductor device provided with the hardening relief pattern obtained by the manufacturing method of the hardening relief pattern demonstrated above can also be provided. More specifically, it is possible to provide a semiconductor device having a base material that is a semiconductor element and a cured relief pattern of polyimide formed on the base material by the above-described cured relief pattern manufacturing method.
  • the present invention can also be applied to a method for manufacturing a semiconductor device using a semiconductor element as a base material and including the above-described method for manufacturing a cured relief pattern as part of the process.
  • the semiconductor device of the present invention has a cured relief pattern having a surface protective film, an interlayer insulating film, an insulating film for rewiring, a protective film for a flip chip device, or a bump structure by the method for producing a cured relief pattern described above. It can be formed as a protective film of a semiconductor device and can be manufactured by combining a method for manufacturing a cured relief pattern and a known method for manufacturing a semiconductor device.
  • the component (A) contained in the resin film may be the same as the resin described as the component (A) contained in the photosensitive resin composition or the resin composition.
  • the component (A) includes polyamic acid, polyamic acid ester, polyamic acid salt, polyamic acid amide, polyamide, polyamideimide, polyimide, polybenzoxazole, polybenzimidazole, and At least one resin selected from the group consisting of polybenzothiazole is preferred.
  • the component (A) is preferably contained in an amount of 50% by mass or more, more preferably 70% by mass or more, based on the total mass of all the components constituting the resin film. If necessary, a resin other than the component A may be contained in the resin film.
  • the weight average molecular weight of the resin contained in the resin film is preferably 1,000 or more in terms of polystyrene by gel permeation chromatography from the viewpoint of heat resistance and mechanical properties after heat treatment, and is 5,000 or more. It is more preferable that The upper limit of the weight average molecular weight is preferably 100,000 or less.
  • the crosslink density is the number of moles of chemically cross-linked functional groups contained in 1 cm 3 of the resin film.
  • Crosslinking is a method in which a monomer having a crosslinkable functional group is copolymerized in component (A), and these crosslinkable functional groups are reacted with each other; (A) component is chemically crosslinked with component (A).
  • the storage elastic modulus above the glass transition temperature increases according to the crosslinking density.
  • the crosslink density can be obtained by measuring the storage elastic modulus above the glass transition temperature of the resin film.
  • the storage elastic modulus above the glass transition temperature can be measured using, for example, a dynamic viscoelasticity measuring apparatus.
  • this relational expression does not necessarily hold strictly between the crosslinking density and the storage elastic modulus.
  • the number of crosslinkable functional groups contained in the resin film and the reaction rate thereof were confirmed while using a dynamic viscoelasticity measuring device, for example, to confirm that the storage elastic modulus above the glass transition temperature was increased.
  • the crosslinking density can be calculated therefrom.
  • the crosslink density of the resin film used in the present invention is 1.0 ⁇ 10 ⁇ 4 mol / cm 3 or more, 3.0 ⁇ 10 ⁇ 3 mol / cm 3 or less, preferably 3.0 ⁇ 10 ⁇ 4 mol / cm 3. 3 or more and 2.0 ⁇ 10 ⁇ 3 mol / cm 3 or less.
  • the crosslinking density is less than 1.0 ⁇ 10 ⁇ 4 mol / cm 3 , the adhesion between the resin film and the polybenzoxazole resin is not sufficient.
  • the resin film becomes brittle and is not suitable for uses such as a passivation film, a buffer coat film, and an interlayer insulating film assumed in the present invention.
  • the 5% weight loss temperature is obtained by raising the temperature at a rate of 10 ° C./min using a thermogravimetric measuring device under nitrogen.
  • the 5% weight loss temperature is less than 250 ° C., the heat resistance is too low, and it is not suitable for applications such as a passivation film, a buffer coat film, and an interlayer insulating film assumed in the present invention.
  • the 5% weight loss temperature exceeds 400 ° C., the adhesion with the polybenzoxazole resin is not sufficient.
  • the resin film can be obtained by, for example, applying a solution in which a component that is a precursor of the resin film is dissolved on the base material and heating at a temperature of 250 ° C. or lower. There may be an exposure step before heating. At this time, by setting the heating temperature to 250 ° C. or lower, the resin film is formed on a base material including a resin substrate having a glass transition temperature of 250 ° C. or lower, or the heating temperature is set to 200 ° C. or lower. Thereby, the said resin film can be formed on the base material containing the resin substrate whose glass transition temperature is 200 degrees C or less, and a laminated body can be obtained.
  • the resin composition of the present invention is useful for applications such as interlayer insulation of multilayer circuits, cover coats of flexible copper-clad plates, solder resist films, and liquid crystal alignment films, in addition to application to semiconductor devices as described above. is there.
  • Weight average molecular weight The weight average molecular weight (Mw) of resin was measured by the gel permeation chromatography method (standard polystyrene conversion). The column used for the measurement was Shodex (trade name) 805M / 806M series manufactured by Showa Denko KK, Shodex STANDARD SM-105 manufactured by Showa Denko KK was selected as the standard monodisperse polystyrene, and the developing solvent was N-methyl. -2-Pyrrolidone, and Shodex (trade name) RI-930 manufactured by Showa Denko was used as a detector.
  • a resin film precursor or a photosensitive resin composition is spin-coated on a 6-inch silicon wafer coated and cured with a polybenzoxazole resin, and dried to a thickness of about 10 ⁇ m.
  • This coating film was exposed by irradiating 1500 mJ / cm 2 energy with an i-line stepper NSR2005i8A (manufactured by Nikon Corporation) using a reticle with a test pattern.
  • the coating film formed on the wafer is spray-developed with a developing machine (D-SPIN636 type, manufactured by Dainippon Screen Mfg. Co., Ltd.) using cyclopentanone, rinsed with propylene glycol methyl ether acetate, and uncoated.
  • the exposed portion was developed and removed to obtain a relief pattern of the resin film precursor or the photosensitive resin composition.
  • the wafer with the relief pattern formed thereon is heat-treated at 200 to 300 ° C. for 2 hours in a nitrogen atmosphere using a temperature-programmed curing furnace (VF-2000 type, manufactured by Koyo Lindberg Co., Ltd., Japan) to obtain polybenzo
  • VF-2000 type manufactured by Koyo Lindberg Co., Ltd., Japan
  • the film thickness was measured using a Tencor P-15 type step gauge (manufactured by KLA Tencor).
  • the pattern shape and the width of the pattern portion were observed under an optical microscope and evaluated according to the following criteria: Good: The area of the opening of the obtained 20 ⁇ m pattern is 1 ⁇ 2 or more of the corresponding pattern mask opening area, and there is no peeling. Defect: The area of the opening is less than 1/2 of the corresponding pattern mask opening area, or there is peeling.
  • the photosensitive resin composition was spin-coated on a 6-inch silicon wafer and dried to form a 8.5 ⁇ m thick coating film.
  • This coating film was irradiated with energy of 500 mJ / cm 2 by Prisma GHI (manufactured by Ultratech, USA) through a mask with a test pattern.
  • the irradiated coating film is spray-developed with a developing machine (D-SPIN636 type, manufactured by Dainippon Screen Mfg. Co., Ltd.) using cyclopentanone, rinsed with propylene glycol methyl ether acetate, and unexposed areas. was removed by development to obtain a relief pattern.
  • D-SPIN636 type manufactured by Dainippon Screen Mfg. Co., Ltd.
  • the taper angle was evaluated by a method including the following steps 1 to 5: 1. Drawing the upper and lower sides of the opening (FIG. 1A); 2. Determining the height of the opening (FIG. 1B); 3. Draw a straight line (center line) parallel to the upper and lower sides through the central part of the height (FIG. 1C); 4). 4. Find the intersection (center point) between the center line and the opening pattern (FIG. 1D); A tangent line is drawn in accordance with the inclination of the pattern at the center point, and an angle formed by the tangent line and the lower side is regarded as a taper angle (FIG. 1E).
  • the above wafer was heated on a silicon wafer at 200 to 390 ° C. for 2 hours in a nitrogen atmosphere using a temperature rising programmed curing furnace (VF-2000, manufactured by Koyo Lindberg, Japan).
  • VF-2000 temperature rising programmed curing furnace
  • a cured relief pattern having a thickness of about 4 to 5 ⁇ m was obtained.
  • the relief pattern was subjected to film thickness measurement using a Tencor P-15 type step gauge (manufactured by KLA Tencor), and the taper angle of the line and space (1: 1) portion was determined in the same manner as described above.
  • the resin composition was spin-coated on a 6-inch silicon wafer and dried to form an 8.5 ⁇ m thick coating film.
  • This coating film was irradiated with energy of 500 mJ / cm 2 by Prisma GHI (manufactured by Ultratech, USA) using a mask with a test pattern.
  • the irradiated coating film is spray-developed with a developing machine (D-SPIN636 type, manufactured by Dainippon Screen Mfg. Co., Ltd.) using cyclopentanone, rinsed with propylene glycol methyl ether acetate, and unexposed areas. was removed by development to obtain a relief pattern.
  • D-SPIN636 type manufactured by Dainippon Screen Mfg. Co., Ltd.
  • the wafer on which this relief pattern was formed was heat-treated at 200 to 390 ° C. for 2 hours in a nitrogen atmosphere using a temperature-programmed curing furnace (VF-2000 type, manufactured by Koyo Lindberg Co., Japan).
  • VF-2000 type manufactured by Koyo Lindberg Co., Japan
  • a cured relief pattern of polyimide having a thickness of about 4 to 5 ⁇ m was obtained on a silicon wafer and a copper substrate, respectively.
  • the film thickness was measured using a Tencor P-15 type step gauge (manufactured by KLA Tencor). About the pattern obtained on Si, the pattern shape and the width
  • Tg glass transition temperature
  • a resin composition was spin-coated on a sputtered body obtained by sputtering 400 nm-thick Cu in this order so that the film thickness after curing was about 4 to 5 ⁇ m.
  • energy of 500 mJ / cm 2 was irradiated by a parallel light mask aligner PLA-501FA (manufactured by Canon Inc., Japan). This irradiation was not performed when the resin composition was not photosensitive.
  • the cured film was obtained by heating at 200 to 390 ° C. for 2 hours in a nitrogen atmosphere and thermosetting.
  • the obtained cured film was peeled from the wafer to obtain a cured tape.
  • the obtained cured tape was measured with a thermomechanical test apparatus (TMA-50 manufactured by Shimadzu Corporation) at a load of 200 g / mm 2 , a temperature rising rate of 10 ° C./min, and a temperature range of 20 to 500 ° C.
  • Tg glass transition temperature
  • the cured film was obtained by heating and curing at 200 ° C. to 390 ° C. for 2 hours in a nitrogen atmosphere.
  • the adhesion of the obtained cured film to Si or Cu was evaluated by a cross-cut test (JIS K5400). That is, scratches with a cutter knife so that 100 squares of 1 mm square can be formed on the coating film, a cellophane (registered trademark) tape is applied from above, and the cellophane is adhered until it is free from bubbles, and then peeled off. Evaluation was performed by counting the number of squares that remained on the substrate without adhering to the (registered trademark) tape.
  • thermogravimetric measuring device TGA-50 manufactured by Shimadzu Corporation. The temperature at which the weight was reduced by 5% from the initial value was determined.
  • the resulting reaction solution was added to 3 liters of ethyl alcohol to produce a precipitate consisting of a crude polymer.
  • the produced crude polymer was separated by filtration and dissolved in 1.5 liter of tetrahydrofuran to obtain a crude polymer solution.
  • the obtained crude polymer solution was dropped into 28 liters of water to precipitate a polymer, and the resulting precipitate was filtered off, and then vacuum dried to obtain a powdered polymer (polyimide precursor A (hereinafter referred to as “polymer A”). Also called))).
  • polyimide precursor A hereinafter referred to as “polymer A”. Also called
  • the photosensitive resin composition was prepared with the following method using the polyimide precursor A (polymer A) and the polyimide precursor B (polymer B), and the prepared composition was evaluated.
  • component (A) polymer A50g and polymer B50g, as component (B), Adekaoptomer NCI831 (manufactured by ADEKA, trade name, 0.001 wt% solution g-line, h-line, and i-line absorbance are respectively (0), 0.13, and 0.22), 2 g of (C), 10 g of 4,4′-bismaleimide diphenylmethane, 4 g of hexamethoxymethylmelamine, and 8 g of tetraethylene glycol dimethacrylate, (D) As components, 3 g of silicon-containing compound D-1 and 0.05 g of 2-nitroso-1-naphthol were dissolved in a mixed solvent consisting of 80 g of N-methylpyrrolidone (hereinafter
  • the viscosity of the resulting solution was adjusted to about 35 poise by further adding a small amount of the mixed solvent to obtain a photosensitive resin composition.
  • Polybenzoxazole (PBO) resin when the composition is applied to a silicon wafer according to the method for evaluating adhesion to (2) polybenzoxazole resin, dried, exposed, developed, and thermally cured at 200 ° C. The adhesion on the substrate was “good”.
  • Example 2 A negative photosensitive resin composition was prepared by changing the blending amount of 4,4′-bismaleimide diphenylmethane as the component (C) in Example 1 into 20 g in Example 1, and the same evaluation as in Example 1 was performed. went. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 3 the photosensitive resin composition was prepared by changing the component (C) in the present invention to bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, and evaluated in the same manner as in Example 1. went. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 4 A photosensitive resin composition was prepared by changing the blending amount of bis (3-ethyl-5-methyl-4-maleimidophenyl) methane as component (C) in Example 3 into 20 g in Example 3. Evaluation similar to 3 was performed. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 5 A photosensitive resin composition was prepared by changing the component (C) of Example 1 to N-phenylmaleimide in the present invention, and the same evaluation as in Example 1 was performed. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 6 the photosensitive resin composition was prepared by changing the component (C) in the present invention to N, N ′, N ′′-[nitrilotris (ethylene)] tris (maleimide). The same evaluation was performed. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 7 In Example 2, the component (C) in the present invention is changed to isocyanuric acid triacrylate, which is a polyfunctional methacrylate whose homopolymer has a glass transition temperature of 200 ° C. or higher, to prepare a photosensitive resin composition, The same evaluation as in Example 2 was performed. It was "good” as a result of evaluating the adhesiveness on a PBO resin base material. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Example 1 a negative photosensitive resin composition was prepared by removing 4,4′-bismaleimide diphenylmethane as the component (C) in the present invention, and the same evaluation as in Example 1 was performed. As a result of evaluating the adhesion on the PBO resin base material, it was “defective”. However, the thermosetting temperature of this composition was 200 degreeC at this time.
  • Adekaoptomer NCI831 (trade name, manufactured by ADEKA)
  • C1 4,4′-bismaleimide diphenylmethane
  • C2 Bis (3-ethyl-5-methyl-4-maleimidophenyl) methane
  • C3 N-phenylmaleimide
  • C4 N, N ′, N ′′-[nitrilotris (ethylene ]]
  • C5 Isocyanuric acid triacrylate
  • D1 Silicon-containing compound D-1
  • Example 8 As the (AX) component, polymer A 50 g and polymer B 50 g, as the component (B) Irgacure OXE03 (trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution are 0, 0, 2 g), tetraethylene glycol dimethacrylate 8 g and 2-nitroso-1-naphthol 0.05 g, and diphenylacetamide 5 g, N- (3- (triethoxysilyl) propyl) phthalamic acid 0.8 g.
  • Irgacure OXE03 trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution are 0, 0, 2 g
  • tetraethylene glycol dimethacrylate 8 g and 2-nitroso-1-naphthol 0.05 g tetraethylene glycol dimethacrylate 8 g and 2-nitroso-1-nap
  • Example 9 Polymer (A) 50 g and Polymer B 50 g as component (AX), Irgacure OXE03 2 g as component (B), 16 g of 4,4′-bismaleimide diphenylmethane, 8 g of tetraethylene glycol dimethacrylate and 2-nitroso-1-naphtho as component (C) 0.05 g of diphenylacetamide, 5 g of diphenylacetamide, 0.5 g of N- (3- (triethoxysilyl) propyl) phthalamic acid, and benzophenone-3,3′-bis (N- (3-triethoxysilyl) propylamide ) 0.5 g of -4,4'-dicarboxylic acid was dissolved in a mixed solvent (mass ratio 8: 2) consisting of N-methylpyrrolidone and ethyl lactate, and the amount of the solvent was adjusted so that the viscosity was about 35 poise.
  • a mixed solvent
  • Example 10 In Example 9, instead of 2 g of Irgacure OXE03 as component (B), Adekaoptomer NCI831 (manufactured by ADEKA, trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution is 0, A photosensitive resin composition solution was prepared in the same manner as in Example 9 except that 2 g (0.13 and 0.22) were used. This composition was evaluated in the same manner as in Example 8.
  • Adekaoptomer NCI831 manufactured by ADEKA, trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution is 0
  • a photosensitive resin composition solution was prepared in the same manner as in Example 9 except that 2 g (0.13 and 0.22) were used. This composition was evaluated in the same manner as in Example 8.
  • Example 11 In Example 9, as component (B), TR-PBG340 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd., trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution was 0.04, 0, respectively. A photosensitive resin composition solution was prepared in the same manner as in Example 9 except that 2 g (0.06 and 0.04) were used. This composition was evaluated in the same manner as in Example 8.
  • Example 8 As an alternative component of the component (B), TR-PBG304 (manufactured by Changzhou Power Electronics New Materials Co., Ltd., trade name, g-line, h-line, and i-line absorbance of 0.001 wt% solution was 0, respectively.
  • a photosensitive resin composition was prepared in the same manner as in Example 8, except that 4 g) were used. This composition was evaluated in the same manner as in Example 8.
  • Component- B1 Irgacure OXE03 (trade name, manufactured by BASF)
  • B2 Adekaoptomer NCI831 (made by ADEKA, trade name)
  • B3 TR-PBG340 (Changzhou Power Electronics New Materials Co., Ltd., trade name)
  • -Component (C)- C1 4,4'-Bismaleimide diphenylmethane-Alternative component-
  • B4 TR-PBG304 (manufactured by Changzhou Powerful Electronic New Materials Co., Ltd., trade name)
  • AY Polymer C 100 g as component (B), Irgacure OXE03 (trade name) manufactured by BASF as component (B), and 3 g of silicon-containing compound D-1 as component (D), a mixed solvent comprising N-methylpyrrolidone and ethyl lactate (A resin composition was obtained by adjusting the amount of the solvent so that it was dissolved in a mass ratio of 8: 2) and the viscosity was about 35 poise. The resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Tg glass transition temperature
  • Example 13 ⁇ Example 13> (AY) component A 50 g and polymer B 50 g, (B) component Irgacure OXE03 (trade name) 4 g, (D) component silicon-containing compound D-1 3 g, tetraethylene glycol dimethacrylate 8 g, 2- 0.05 g of nitroso-1-naphthol and 5 g of diphenylacetamide are dissolved in a mixed solvent composed of N-methylpyrrolidone and ethyl lactate (mass ratio 8: 2), and the viscosity is about 35 poise.
  • the resin composition was obtained by adjusting the amount of.
  • the resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Example 14 ⁇ Example 14> (AY) component A 50 g and polymer B 50 g, (B) component Irgacure OXE3 (trade name, manufactured by BASF) 4 g, (D) component silicon-containing compound D-1 3 g and A-1160 (3-ureido 3 g of a 50% by mass solution of propyltriethoxysilane (manufactured by Momentive) as a methanol solution, 8 g of tetraethylene glycol dimethacrylate, 0.05 g of 2-nitroso-1-naphthol, and 5 g of diphenylacetamide were added to N-methylpyrrolidone.
  • AY component A 50 g and polymer B 50 g
  • component Irgacure OXE3 trade name, manufactured by BASF 4 g
  • D component silicon-containing compound D-1 3 g and A-1160 (3-ureido 3 g of a 50% by mass solution of propyltriethoxysi
  • the resin composition was obtained by adjusting the quantity of a solvent so that it might melt
  • the resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Example 15 a cured film was formed and evaluated in the same manner as in Example 14 except that the heating temperature for curing was changed from 200 ° C to 390 ° C.
  • Example 17 A resin composition was obtained in the same manner as in Example 16 except that the component (C) was changed from 4,4′-bismaleimide diphenylmethane to bis (3-ethyl-5-methyl-4-maleimidophenyl) methane in Example 16. Got. The resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Tg glass transition temperature
  • Example 18 a resin composition was obtained in the same manner as in Example 16 except that 3 g of dicyclohexylthiourea was used as the (E) component instead of the (D) component.
  • the resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Example 12 0.5 g of N- (3- (triethoxysilyl) propyl) phthalamic acid and benzophenone-3,3′-bis (N- (3-triethoxysilyl) propyl are used as alternative components for component (D).
  • a resin composition was obtained in the same manner as in Example 12 except that 0.5 g of amide) -4,4′-dicarboxylic acid was used.
  • the resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Example 14 As an alternative component of component (D), 0.5 g of N- (3- (triethoxysilyl) propyl) phthalamic acid and benzophenone-3,3′-bis (N- (3-triethoxysilyl) A resin composition was obtained in the same manner as in Example 14 except that 0.5 g of propylamide) -4,4′-dicarboxylic acid was used. The resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Tg glass transition temperature
  • Example 15 As an alternative component of component (D), 0.5 g of N- (3- (triethoxysilyl) propyl) phthalamic acid and benzophenone-3,3′-bis (N- (3-triethoxysilyl) A resin composition was obtained in the same manner as in Example 15 except that 0.5 g of propylamide) -4,4′-dicarboxylic acid was used. The resin composition was evaluated by (5) measurement of glass transition temperature (Tg) of the cured film, (6) measurement of Si and Cu adhesion of the cured film, and (4) minimum opening pattern size evaluation method.
  • Tg glass transition temperature
  • B1 Irgacure OXE03 (trade name, manufactured by BASF)
  • B2 Adekaoptomer NCI831 (made by ADEKA, trade name)
  • C1 4,4′-bismaleimide diphenylmethane
  • C2 Bis (3-ethyl-5-methyl-4-maleimidophenyl) methane
  • D1 Silicon-containing compound D-1
  • D2 Silicon-containing compound D-1 / A-1160 (50% solution of 3-ureidopropyltriethoxysilane, manufactured by Momentive)
  • D3 N- (3- (triethoxysilyl) propyl) phthalamic acid / benzophenone-3,3′-bis (N- (3-triethoxysilyl) propylamide) -4,4′-dicarboxylic acid
  • Example 19 As component (A), 50 g of polymer A and 50 g of polymer B were added to Adekaoptomer NCI831 (trade name, 0.001 wt% solution g-line, h-line, and i-line absorbance were 0, 0.13, and 0.22), 10 g of 4,4′-bismaleimide diphenylmethane, 3 g of silicon-containing compound D-1 and 0.05 g of 2-nitroso-1-naphthol, together with N-methylpyrrolidone (hereinafter referred to as NMP) )
  • NMP N-methylpyrrolidone
  • the viscosity of the obtained solution was adjusted to about 35 poise by further adding a small amount of the mixed solvent to obtain a photosensitive resin composition.
  • the composition was applied to a silicon wafer according to the method for evaluating adhesion to the polybenzoxazole resin described in (2) above, dried, exposed, developed, and thermally cured at 200 ° C. to obtain a resin film.
  • the adhesion on the polybenzoxazole (PBO) resin substrate was “good”.
  • the above-mentioned (7) crosslinking density was determined to be 7.0 ⁇ 10 ⁇ 4 mol / cm 3 from the reaction rate, composition, and density of maleimide by IR.
  • the storage elastic modulus in 110 Hz and 300 degreeC was 0.08 GPa, and the above-mentioned (8) 5% weight reduction
  • decrease temperature was 340 degreeC.
  • Example 20 A photosensitive resin composition was prepared in the same manner as in Example 19 except that the amount of 4,4′-bismaleimide diphenylmethane added was changed to 20 g in Example 19.
  • the composition was applied to a silicon wafer according to the method for evaluating adhesion to the polybenzoxazole resin described in (2) above, dried, exposed, developed, and thermally cured at 200 ° C. to obtain a resin film.
  • the adhesion on the polybenzoxazole (PBO) resin substrate was “good”.
  • the above-mentioned (7) crosslinking density was determined to be 1.4 ⁇ 10 ⁇ 3 mol / cm 3 from the reaction rate, composition and density of maleimide by IR.
  • the storage elastic modulus in 110 Hz and 300 degreeC was 0.16 GPa, and the above-mentioned (8) 5% weight reduction
  • decrease temperature was 370 degreeC.
  • Example 6 A resin composition was prepared in the same manner as in Example 19 except that 4,4′-bismaleimide diphenylmethane was not added in Example 19, and a thermosetting resin film of the composition was obtained.
  • the adhesion on the polybenzoxazole (PBO) resin base material evaluated according to the method for evaluating the adhesion with the polybenzoxazole resin (2) described above was “poor”.
  • the above-mentioned (7) crosslinking density was determined to be 0 mol / cm 3 from the reaction rate, composition, and density of maleimide by IR.
  • the storage elastic modulus in 110 Hz and 300 degreeC was 0.02 GPa, and the above-mentioned (8) 5% weight reduction
  • the resin composition and resin film of the present invention can be suitably used in the field of photosensitive materials useful for the production of electrical / electronic materials such as semiconductor devices and multilayer wiring boards.

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PCT/JP2015/057678 2014-03-17 2015-03-16 感光性樹脂組成物、硬化レリーフパターンの製造方法、並びに半導体装置 WO2015141618A1 (ja)

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WO2017099019A1 (ja) * 2015-12-08 2017-06-15 富士フイルム株式会社 感放射線性樹脂組成物、硬化膜、パターン形成方法、固体撮像素子および画像表示装置
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