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EP-4738009-A1 - PHOTOSENSITIVE RESIN COMPOSITION, CURED PRODUCT, AND ELECTRONIC COMPONENT

EP4738009A1EP 4738009 A1EP4738009 A1EP 4738009A1EP-4738009-A1

Abstract

An object of the present invention is to provide a cured product that is to be provided in an electronic component, and has excellent heat resistance, excellent adhesion to a metal material, particularly to copper, and excellent migration resistance. The gist of the present invention is to provide a photosensitive resin composition including a resin (A), a photosensitizer (B), a compound (C) represented by Formula (1), and a compound (D) represented by Formula (2).

Inventors

  • KANEKI, Takayuki
  • HIBINO, Chika
  • ARAKI, HITOSHI

Assignees

  • Toray Industries, Inc.

Dates

Publication Date
20260506
Application Date
20240621

Claims (16)

  1. A photosensitive resin composition comprising a resin (A), a photosensitizer (B), a compound (C) represented by Formula (1), and a compound (D) represented by Formula (2): (wherein R 1 to R 3 are each independently a hydrogen atom, NR 4 R 5 , or L(R 6 ) s ; L is a C 6-10 n-valent organic group having an aromatic ring; R 4 and R 5 are each independently a hydrogen atom, -CH 2 OH, -CH 2 OCH 3 , -CH 2 OCH 2 CH 2 CH 2 CH 3 , or - CH 2 OCH(CH 3 ) 2 ; R 6 is independently -CH 2 OH, -CH 2 OCH 3 , -CH 2 OCH 2 CH 2 CH 2 CH 3 , or -CH 2 OCH(CH 3 ) 2 ; n is an integer of 1 to 3; s is an integer of 0 to 2; and n-s is 1), (wherein R 7 is an oxygen atom or a sulfur atom; R 8 is a C 1-4 divalent organic group; R 9 is a methyl group or an ethyl group; and R 10 is a C 1-18 monovalent hydrocarbon group or a C 6-12 monovalent aromatic group, wherein the C 1-18 monovalent hydrocarbon group and the C 6-12 monovalent aromatic group may contain a heteroatom).
  2. The photosensitive resin composition according to claim 1, wherein all or part of the photosensitizer (B) is an oxime ester compound (B1-1).
  3. The photosensitive resin composition according to claim 1 or 2, wherein the compound (C) represented by Formula (1) is contained in an amount of 30 parts by mass or more and 1200 parts by mass or less with respect to 100 parts by mass of the compound (D) represented by Formula (2).
  4. The photosensitive resin composition according to claim 1 or 2, which satisfies α > β ≥ γ, satisfies 1.0 ≤ α/β ≤ 4.5, and satisfies 0.4 ≤ β/γ ≤ 5.0, assuming that the amount of the photosensitizer (B) contained in the photosensitive resin composition is α part(s) by mass, that the amount of the compound (C) represented by Formula (1) is β part(s) by mass, and the amount of the compound (D) represented by Formula (2) is γ part(s) by mass.
  5. The photosensitive resin composition according to claim 1 or 2, further comprising one or both of a compound represented by Formula (5) and a compound represented by Formula (6): (wherein, in Formula (5), R 15 , R 16 , and R 17 are each independently a C 1-6 alkyl group; in Formula (6), R 18 and R 19 are each independently a C 1-6 alkyl group; and R 20 is a hydrogen atom or a C 1-6 alkyl group).
  6. The photosensitive resin composition according to claim 1 or 2, wherein all or part of the compound (D) represented by Formula (2) is a compound having a structure represented by Formula (4): (wherein R 11 is a methyl group or an ethyl group; R 12 is a C 1-4 divalent organic group; and R 13 and R 14 are each independently a carbon atom (i.e., a methine group) or a nitrogen atom).
  7. The photosensitive resin composition according to claim 1 or 2, wherein all or part of the compound (C) represented by Formula (1) is a compound having a structure represented by Formula (3): (wherein R 60 to R 65 are each independently a hydrogen atom, -CH 3 , - CH 2 CH 2 CH 2 CH 3 , or -CH(CH 3 ) 2 ).
  8. The photosensitive resin composition according to claim 1 or 2, wherein all or part of the resin (A) is one or more resins selected from the group consisting of a polyimide precursor (A-1), a polyimide (A-2), a polybenzoxazole precursor (A-3), a polybenzoxazole (A-4), and copolymers thereof.
  9. The photosensitive resin composition according to claim 8, wherein the one or more resins selected from the group consisting of the polyimide precursor (A-1), the polyimide (A-2), the polybenzoxazole precursor (A-3), the polybenzoxazole (A-4), and the copolymers thereof contain(s) a phenolic hydroxyl group.
  10. The photosensitive resin composition according to claim 8, wherein all or part of the resin (A) is a polyimide precursor containing a repeating structural unit represented by Formula (7), or is a copolymer of the polyimide precursor. (wherein X 1 is a tetravalent group having a C 2-20 aliphatic structure, a C 4-20 alicyclic structure, or a C 4-40 aromatic structure; Y 1 is a divalent organic group having a C 2-20 aliphatic structure, a C 4-20 alicyclic structure, or a C 4-40 aromatic structure; and R 21 and R 22 are each independently a hydrogen atom, a C 1-20 alkyl group, or a monovalent organic group having an ethylene-type unsaturated double bond).
  11. The photosensitive resin composition according to claim 10, wherein the polyimide precursor has an esterification rate of 40 mol% or more and 80 mol% or less.
  12. The photosensitive resin composition according to claim 10, wherein all or part of the structure of X 1 in Formula (7) is a structure represented by Formula (8): [Chem. 7] (wherein, in Formula (8), * is a binding site that binds to an amide structure, a carboxylic acid structure, or a carboxylic acid ester structure).
  13. The photosensitive resin composition according to claim 1 or 2, wherein the photosensitive resin composition contains a halogen element(s) in an amount of 50 ppm or less.
  14. A cured product obtained by curing the photosensitive resin composition according to claim 1 or 2.
  15. An electronic component comprising the cured product according to claim 14.
  16. The electronic component according to claim 15, wherein the electronic component comprises: a silicon substrate, a silicon carbide substrate, or a gallium nitride substrate, wherein the cured product is provided on the substrate.

Description

Technical Field The present invention relates to a photosensitive resin composition, a cured product, and an electronic component. Background Art Polyimide resins, polybenzoxazole resins, and the like, which have excellent heat resistance and mechanical properties, have been widely used for surface protective films of and interlayer insulating films of semiconductor elements in electronic devices. In a case where a polyimide or a polybenzoxazole is used for a surface protective film or an interlayer insulating film, one method of forming a through-hole or the like is etching for which a positive photoresist is used. However, this method has a problem in that the method involves the steps of applying and peeling a photoresist, and is complicated. In view of this, a heat-resistant material provided with photosensitivity has been studied with a view to streamlining the working processes (see, for example, Patent Literature 1 to 3). On the other hand, in a case where a heat-resistant resin composition is used for semiconductor applications or the like, a film heat-cured remains as a permanent film inside a device, and thus, the physical properties of the cured film after the heating are very important. The cured film needs reliability related to high electrical insulation, and thus, also needs high migration resistance. In order to ensure the reliability of a semiconductor package, what is important is adhesion to a material formed on the surface of a semiconductor chip. In particular, in a case where the material is used, for example, as an insulating film between wiring layers in a wafer level package, the adhesion of the material to a metal material used for electrodes and wiring is important. A heat-resistant resin, owing to the rigid main chain structure, is generally considered not to have high strength of adhesion to a metal material. In particular, in the case of a cured resin film formed from a resin composition provided with photosensitivity, additives included in the composition, such as a photosensitizer, sensitizer, acid generator, and a solubility modifier, remain in the cured film even after the heat curing. Thus, the cured film has lower strength of adhesion than a cured film containing no additive. Specific examples of methods of improving adhesion to a metal material include: a positive photosensitive resin composition composed of an alkaline aqueous solution-soluble polymer, a photoacid generator, and a silane compound containing four or more specific functional groups each directly bound to an aluminium atom, titanium atom, or silicon atom (see Patent Literature 4); and a heat-resistant resin precursor composition composed of: a heat-resistant resin precursor such as a polyimide precursor; and a specific amino compound or a thiol derivative (see Patent Literature 5). Citation List Patent Literature Patent Literature 1: JP S49-115541 APatent Literature 2: JP S59-108031 APatent Literature 3: JP S59-219330 APatent Literature 4: JP 2008-276190 APatent Literature 5: JP 2007-39486 A Summary of Invention Technical Problem However, these resin compositions have problems with providing a cured product that has all of excellent heat resistance, adhesion to a metal material, particularly to copper, and migration resistance. Accordingly, there is a demand for further enhancement in the properties of a photosensitive composition. An object of the present invention is to provide a cured product that is to be included in an electronic component, and has excellent heat resistance, excellent adhesion to a metal material, particularly to copper, and excellent migration resistance. Solution to Problem In order to solve the above-described problems, the present invention relates to the following. [1] A photosensitive resin composition including a resin (A), a photosensitizer (B), a compound (C) represented by Formula (1), and a compound (D) represented by Formula (2): (R1 to R3 are each independently a hydrogen atom, NR4R5, or L(R6)s. L is a C6-10 n-valent organic group having an aromatic ring, R4 and R5 are each independently a hydrogen atom, -CH2OH, -CH2OCH3, -CH2OCH2CH2CH2CH3, or - CH2OCH(CH3)2, and R6 is independently -CH2OH, -CH2OCH3, - CH2OCH2CH2CH2CH3, or -CH2OCH(CH3)2. n is an integer of 1 to 3, s is an integer of 0 to 2, and n - s is 1.) (R7 is an oxygen atom or a sulfur atom. R8 is a C1-4 divalent organic group, and R9 is a methyl group or an ethyl group. R10 is a C1-18 monovalent hydrocarbon group or a C6-12 monovalent aromatic group, wherein the C1-18 monovalent hydrocarbon group and the C6-12 monovalent aromatic group may contain a heteroatom.)[2] The photosensitive resin composition according to [1], wherein all or part of the photosensitizer (B) is an oxime ester compound (B1-1).[3] The photosensitive resin composition according to [1] or [2], wherein the compound (C) represented by Formula (1) is contained in an amount of 30 parts by mass or more and 1200 parts by mass or less with respect to 1