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JP-7856781-B2 - Photosensitive resin composition, method for manufacturing a cured relief pattern, and semiconductor device.

JP7856781B2JP 7856781 B2JP7856781 B2JP 7856781B2JP-7856781-B2

Inventors

  • 高 靖馳
  • 小倉 知士
  • 岩間 翔太

Assignees

  • 旭化成株式会社

Dates

Publication Date
20260511
Application Date
20231025
Priority Date
20221028

Claims (15)

  1. (A) A polyimide precursor having a repeating structure represented by the following formula (1): {During the ceremony, X1 is a tetravalent organic group, Y1 is a divalent organic group, m is an integer greater than or equal to 1, R1 and R2 are each independently a hydrogen atom, a radical polymerizable group, or a compound of the following formula (2): ( B ) A photosensitive resin composition comprising a photoradical initiator .
  2. The photosensitive resin composition according to claim 1, wherein R3 is a monovalent organic group having 3 or fewer carbon atoms.
  3. The photosensitive resin composition according to claim 1 or 2, wherein R3 , R4 , and Rz do not contain radical polymerizable groups.
  4. The photosensitive resin composition according to claim 1 or 2, wherein R1 and R2 in formula (1) are each independently a hydrogen atom, a radical polymerizable group represented by the following formula (3), or an organic group represented by the formula (2) : (In the formula, R5 is a hydrogen atom or a monovalent organic group having 1 to 10 carbon atoms, R6 , R7 , and R8 are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, and p is an integer from 1 to 10.)
  5. The photosensitive resin composition according to claim 4, wherein R1 in formula (1) is a group represented by formula (3), and R7 and R8 do not contain radical polymerizable groups.
  6. The photosensitive resin composition according to claim 4, wherein in formula (1), the group represented by formula (3) is contained in an amount of 20 to 80 mol% relative to the sum of R1 and R2 .
  7. The photosensitive resin composition according to claim 1 or 2, wherein one of R3 , R4 , and Rz is a hydrogen atom.
  8. The Y1 is the photosensitive resin composition according to claim 1 or 2, represented by the following formula (5) or formula (6): (In the formula, R 13 independently represents one of the following: a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.) (In the formula, R 14 each independently represents either a hydrogen atom or a methyl group.)
  9. The photosensitive resin composition according to claim 1 or 2, wherein the X1 is a group derived from at least one selected from the group consisting of the following formulas (7) to (12): .
  10. The photosensitive resin composition according to claim 9, wherein X1 is a group derived from at least one selected from the group consisting of formulas (7), (8), and (10).
  11. The structure is represented by the following formula (13): {The definitions of X1 , Y1 , R1 , and R2 in the formula are the same as in formula (1) above.} The photosensitive resin composition according to claim 1 or 2, wherein, after molecular dynamics calculations using Forcite, the lowest empty molecular orbital (LUMO) calculated with Dmol3 is -3.00 to -2.59 eV, and the band gap between the highest occupied molecular orbital (HOMO) and the LUMO is 1.52 to 2.00 eV.
  12. The photosensitive resin composition according to claim 1 or 2 , wherein the cured film obtained by coating and exposing a wafer and then thermally curing it at a temperature of 280°C in a nitrogen atmosphere has a Young's modulus of 6 GPa or more.
  13. (1) A step of forming a photosensitive resin layer on a substrate by applying the photosensitive resin composition according to claim 1 or 2 onto the substrate, (2) A step of exposing the photosensitive resin layer, (3) A step of developing the photosensitive resin layer after exposure to form a relief pattern, (4) A step of forming a hardened relief pattern by heat treatment of the relief pattern, A method for manufacturing a hardened relief pattern, including [the specified element].
  14. A cured relief pattern comprising a cured product of the photosensitive resin composition according to claim 1 or 2 .
  15. A semiconductor device having the cured relief pattern described in claim 14.

Description

The present invention relates to a polyimide precursor, a photosensitive resin composition containing the polyimide precursor, a method for producing a cured relief pattern obtained by curing the photosensitive resin composition, a cured relief pattern, and a semiconductor device and display device having the cured relief pattern. Conventionally, polyimide resins possessing excellent heat resistance, electrical properties, and mechanical properties have been used as insulating materials for electronic components, and as passivation films, surface protective films, and interlayer insulating films for semiconductor devices. Among these polyimide resins, those provided in the form of photosensitive polyimide precursor compositions allow for the easy formation of heat-resistant cured relief pattern films through thermal imidization treatment involving coating, exposure, development, and curing of the composition. Such photosensitive polyimide precursor compositions offer the advantage of significantly shortening the manufacturing process compared to conventional non-photosensitive polyimide materials. As semiconductor miniaturization progresses, an Extreme Low-κ (ELK) layer with a low dielectric constant is being introduced into semiconductor devices to suppress signal delay. To reduce the dielectric constant of the ELK layer, materials with a porous structure are used. However, a problem with such materials is their low mechanical strength. As a result, for example, in a solder reflow process requiring a high temperature of 260°C, the ELK layer may be damaged by stress applied to it from bumps on the semiconductor surface. From the viewpoint of i-line transmittance and low stress for pattern protective films used as protective films for interlayer insulating films, for example, Patent Document 1 describes a polyimide precursor having a specific structure with polymerizable groups in its side chains for forming a low-stress cured film. On the other hand, in recent years, the mounting methods for semiconductor devices onto printed circuit boards have also changed from the perspective of improving integration density and functionality, as well as miniaturizing chip size. From the conventional mounting method using metal pins and lead-tin eutectic solder, structures in which a polyimide coating directly contacts the solder bumps are now being used, such as BGA (Ball-Gripped Array) and CSP (Chip-Size Packaging), which enable higher density mounting. When forming such bump structures, the coating requires high heat resistance and mechanical properties. Japanese Patent Publication No. 2014-201696 The following describes in detail embodiments for carrying out the present invention (hereinafter referred to as "this embodiment"). It should be noted that the present invention is not limited to the following embodiments, and can be implemented in various modifications within the scope of its gist. In this embodiment, the photosensitive resin composition comprises (A) a polyimide precursor, (B) a photopolymerization initiator, optionally (C) a crosslinking agent, (D) a solvent, and optionally other components. Each component will be described in order below. Furthermore, throughout this specification, structures represented by the same symbols in a general formula may be identical or different from each other if multiple such structures exist in a molecule. <Polyimide precursor composition> (A) Polyimide precursor As the polyimide precursor used in the photosensitive resin composition, a polyamic acid ester containing repeating units represented by the following general formula (1) is used. In the formula, X1 is a tetravalent organic group, Y1 is a divalent organic group, m is an integer of 1 or more, and R1 and R2 are each independently a hydrogen atom, a radical polymerizable group, or the following formula (2): (In the formula, R3 , R4 , and Rz are each independently monovalent organic groups having 2 to 20 carbon atoms that do not contain fluorine, or if one of R3 , R4 , and Rz is a hydrogen atom, the others are monovalent organic groups having 2 to 20 carbon atoms that do not contain fluorine atoms, and at least one has a branched chain or a cyclic structure.) An organic group represented by this formula, or a monovalent organic group having 2 to 20 carbon atoms that does not have a radical polymerizable group. In this embodiment, multiple polyamic acid esters represented by general formula (1) may be mixed. Alternatively, polyamic acid esters obtained by copolymerizing polyamic acid esters represented by general formula (1) may be used. In general formula (1), the tetravalent organic group represented by X 1 is not particularly limited, but is preferably an organic group having 6 to 40 carbon atoms, and more preferably the -COOR 1 group, the -COOR 2 group and the -CONH- group are aromatic groups or alicyclic aliphatic groups located in the ortho position relative to each other. In general formula (1), a specific ex