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JP-7854945-B2 - Resin composition, cured product, laminate, method for manufacturing cured product, and semiconductor device

JP7854945B2JP 7854945 B2JP7854945 B2JP 7854945B2JP-7854945-B2

Inventors

  • 野崎 敦靖
  • 嶋田 和人

Assignees

  • 富士フイルム株式会社

Dates

Publication Date
20260507
Application Date
20211224
Priority Date
20201228

Claims (18)

  1. At least one resin selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, and polyamideimide precursor , Contains polymerization initiator, The resin has a side chain containing a polymerizable group, The main chain of the resin and the polymerizable group are bonded via a linking group. The aforementioned linking group includes a urea bond, A resin composition in which the side chain has a structure represented by the following formula (1-1). In formula (1-1), R p1 represents a group containing at least one polymerizable group, R N each independently represents a hydrogen atom or a hydrocarbon group, L 1 represents a hydrocarbon group, or a group formed by bonding a hydrocarbon group with at least one group selected from the group consisting of -O-, -C(=O)-, -S-, -S(=O) 2- , and -NRN-, * represents a bonding site with the main chain, and the structure adjacent to * in L 1 in formula (1-1) is -O- or -C(=O)- .
  2. The resin composition according to claim 1, wherein the bonding site with the urea bond in formula (1-1) in L 1 of formula (1-1) is a hydrocarbon group.
  3. At least one resin selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, and polyamideimide precursor , Contains polymerization initiator, The resin has a polymerizable group structure, and includes a structure represented by the following formula (1-2): Resin composition. In formula (1-2), R p2 represents a group containing at least one polymerizable group, R N each independently represents a hydrogen atom or a hydrocarbon group, L 2 represents a hydrocarbon group, or a group formed by bonding a hydrocarbon group with at least one group selected from the group consisting of -O-, -C(=O)-, -S-, -S(=O) 2- , and -NR N- , and * represents a bonding site with another structure, and the structure adjacent to * in L 2 of formula (1-2) is -O- or -C(=O)-.
  4. The resin composition according to claim 3, wherein the bonding site with the urea structure in formula (1-2) at L2 in formula (1-2) is a hydrocarbon group.
  5. The resin composition according to claim 3, wherein the resin contains three or more structures represented by formula (1-2).
  6. The resin composition according to any one of claims 3 to 5, wherein the resin is at least one resin selected from the group consisting of a polyimide precursor containing repeating units represented by the following formula (2), a polyimide containing repeating units represented by the following formula (4), a polybenzoxazole precursor containing repeating units represented by the following formula (3), a polybenzoxazole containing repeating units represented by the following formula (x), a polyamideimide precursor represented by the following formula (PAI-2), and a polyamideimide containing repeating units represented by the following formula (PAI-3). In formula (2), A1 and A2 each independently represent an oxygen atom or -NH-, R111 represents a divalent organic group, R115 represents a tetravalent organic group, R113 and R114 each independently represent a hydrogen atom or a monovalent organic group, and at least one selected from the group consisting of R111 , R113 , R114 and R115 contains the structure represented by formula (1-2); In formula (4), R 131 represents a divalent organic group, and R 132 represents a tetravalent organic group, and at least one of R 132 and R 131 contains the structure represented by formula (1-2); In formula (3), R 121 represents a divalent organic group, R 122 represents a tetravalent organic group, R 123 and R 124 each independently represent a hydrogen atom or a monovalent organic group, and at least one selected from the group consisting of R 121 , R 122 , R 123 and R 124 contains the structure represented by formula (1-2); In formula (X), R 133 represents a divalent organic group, R 134 represents a tetravalent organic group, and at least one of R 134 and R 133 contains the structure represented by formula (1-2); In formula (PAI-2), R 117 represents a trivalent organic group, R 111 represents a divalent organic group, A 2 represents an oxygen atom or -NH-, R 113 represents a hydrogen atom or a monovalent organic group, and at least one selected from the group consisting of R 111 , R 113 , and R 117 contains the structure represented by formula (1-2); In formula (PAI-2), R 117 represents a trivalent organic group, and R 111 represents a divalent organic group, and at least one of R 111 and R 117 contains the structure represented by formula (1-2).
  7. The resin composition according to claim 3 , wherein the polyimide precursor contains repeating units represented by the following formula (2-2) and satisfies any of (1A), (1B), and (1C) below, and the polyamideimide precursor contains repeating units represented by the following formula (PAI-2-2) and satisfies any of (3A), (3B), and (3C) below; (1A) At least one of the structures including R 113 and R 114 in formula (2-2) is the structure represented by formula (1-2). (1B) R 111 includes the structure represented by formula (1-2). (1C) R 115 includes the structure represented by formula (1-2). (3A) The structure including R 113 in formula (PAI-2-2) is the structure represented by formula (1-2). (3B) R 111 contains the structure represented by formula (1-2) (3C) R 117 contains the structure represented by formula (1-2) In formula (2-2), A1 and A2 each independently represent an oxygen atom or -NH-, R111 represents a divalent organic group, R115 represents a tetravalent organic group, and R113 and R114 each independently represent a hydrogen atom or a monovalent organic group; In formula (PAI-2-2), R 117 represents a trivalent organic group, R 111 represents a divalent organic group, A 2 represents an oxygen atom or -NH-, and R 113 represents a hydrogen atom or a monovalent organic group.
  8. The resin composition according to any one of claims 1 to 7, wherein the polymerizable group in the resin is a radical polymerizable group.
  9. The resin composition according to any one of claims 1 to 8 , wherein the acid value of the resin is 0 mmol/g to 1.2 mmol/g.
  10. A resin composition according to any one of claims 1 to 9 , further comprising a polymerizable compound.
  11. A resin composition according to any one of claims 1 to 10 , further comprising a base-generating agent.
  12. A resin composition according to any one of claims 1 to 11 , used for forming an interlayer insulating film for redistribution layers.
  13. A cured product obtained by curing the resin composition according to any one of claims 1 to 12 .
  14. A laminate comprising two or more layers made of the cured material described in claim 13 , wherein a metal layer is included between any of the layers made of the cured material.
  15. A method for producing a cured product, comprising a film-forming step of applying a resin composition according to any one of claims 1 to 12 onto a substrate to form a film.
  16. A method for producing a cured product according to claim 15 , comprising an exposure step of selectively exposing the film and a developing step of developing the film using a developer to form a pattern.
  17. A method for producing a cured product according to claim 15 or 16 , comprising a heating step of heating the film to 50 to 450°C.
  18. A semiconductor device comprising the cured product described in claim 13 or the laminate described in claim 14 .

Description

This invention relates to a resin composition, a cured product, a laminate, a method for producing a cured product, and a semiconductor device. Cyclic resins such as polyimide are used in a variety of applications due to their excellent heat resistance and insulation properties. While not limited to these applications, examples in semiconductor devices for packaging include their use as insulating films, encapsulants, or protective films. They are also used as base films and coverlays for flexible substrates. For example, in the applications described above, cyclized resins such as polyimide are used in the form of a resin composition containing at least one of the cyclized resin such as polyimide and a precursor of the cyclized resin. Such a resin composition can be applied to a substrate, for example by coating, to form a photosensitive film, and then, if necessary, exposure, development, heating, etc., can be performed to form a cured product on the substrate. The precursors of the cyclized resin, such as polyimide precursors, are cyclized, for example, by heating, and become cyclized resins such as polyimide in the cured product. Since the resin composition can be applied by known coating methods, it can be said to have excellent manufacturing adaptability, such as a high degree of freedom in designing the shape, size, and application location of the resin composition when applied. In addition to the high performance of cyclized resins such as polyimides, the industrial application development of the above-mentioned resin composition is increasingly expected from the standpoint of such excellent manufacturing adaptability. For example, Patent Document 1 describes a photosensitive polyimide precursor composition characterized by containing (a) a polymer (A) mainly composed of a specific structural unit, (b) a compound (B) represented by a specific general formula, and (c) a photoinitiator and/or sensitizer and/or photoreactive monomer. Patent Document 2 describes an oxygen-scavenging polymer comprising a main polymer having a backbone and unsaturated side chains bonded to the backbone, wherein the side chains each contain at least one aliphatic carbon-carbon double bond or two or more carbon-carbon double bonds, and a catalyst, and a composition comprising the oxygen-scavenging polymer and a catalyst. Japanese Patent Application Publication No. 6-332178Special Publication No. 2010-538123 The main embodiments of the present invention will be described below. However, the present invention is not limited to the embodiments specified. In this specification, a numerical range represented by the symbol "~" means a range that includes the numbers written before and after "~" as the lower limit and upper limit, respectively. In this specification, the term "process" includes not only independent processes but also processes that are indistinguishable from other processes insofar as they achieve their intended function. In this specification, when groups (atomic groups) are not specified as substituted or unsubstituted, the notation includes both groups (atomic groups) with and without substituents. For example, "alkyl group" includes not only unsubstituted alkyl groups but also substituted alkyl groups. In this specification, "exposure" includes not only exposure using light but also exposure using particle beams such as electron beams and ion beams, unless otherwise specified. Examples of light used for exposure include the emission spectrum of mercury lamps, far ultraviolet light represented by excimer lasers, extreme ultraviolet (EUV) light, X-rays, electron beams, and other active light or radiation. In this specification, "(meth)acrylate" means both or either "acrylate" and "methacrylate,""(meth)acrylic" means both or either "acrylic" and "methacrylic," and "(meth)acryloyl" means both or either "acryloyl" and "methacryloyl." In this specification, Me in the structural formula represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. In this specification, total solids refers to the total mass of all components of the composition excluding the solvent. In this specification, solids concentration refers to the mass percentage of the components other than the solvent relative to the total mass of the composition. In this specification, unless otherwise specified, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) are values measured using gel permeation chromatography (GPC) and are defined as polystyrene equivalent values. In this specification, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) can be determined, for example, by using an HLC-8220 GPC (manufactured by Tosoh Corporation) and connecting Guard Column HZ-L, TSKgel Super HZM-M, TSKgel Super HZ4000, TSKgel Super HZ3000, and TSKgel Super HZ2000 (all manufactured by Tosoh Corporation) in series as columns. Unless otherwise speci