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KR-20260068062-A - Resin composition, cured product, display device

KR20260068062AKR 20260068062 AKR20260068062 AKR 20260068062AKR-20260068062-A

Abstract

The present invention aims to provide a resin composition capable of forming a film that has high sensitivity during pattern processing and high reliability when applied to an organic EL display device, and proposes a resin composition comprising either or both of polyhydroxystyrene and a copolymer of hydroxystyrene and a styrene derivative not having phenolic hydroxyl groups (component (A)), a photosensitive compound (component (B)), an aromatic compound having at least one aromatic C-H bond and at least three phenolic hydroxyl groups within one aromatic ring (component (C)), and a crosslinking compound (component (D)).

Inventors

  • 니시오카, 히로키
  • 고모리, 유스케
  • 니시야마, 마사히토

Assignees

  • 도레이 카부시키가이샤

Dates

Publication Date
20260513
Application Date
20240902
Priority Date
20230908

Claims (19)

  1. Either or both of polyhydroxystyrene and copolymers of hydroxystyrene and styrene derivatives not having phenolic hydroxyl groups (hereinafter referred to as “Component (A)”), Photosensitive compound (component (B)), An aromatic compound having at least one aromatic CH bond and at least three phenolic hydroxyl groups within one aromatic ring (hereinafter referred to as “Component (C)”) and A resin composition containing a crosslinkable compound (hereinafter referred to as “Component (D)”).
  2. A resin composition according to claim 1, wherein component (A) contains a structural unit represented by formula (1) in its molecular structure. (In Equation (1), n represents an integer between 1 and 5.)
  3. A resin composition according to claim 1 or 2, wherein the styrene derivative not having a phenolic hydroxyl group is styrene.
  4. A resin composition according to claim 1 or 2, wherein (A) all or part of the component is a copolymer of hydroxystyrene and a styrene derivative not having a phenolic hydroxyl group.
  5. A resin composition according to claim 4, wherein the content of a structural unit derived from a styrene derivative not having a phenolic hydroxyl group is 5 mol% or more and 40 mol% or less, relative to 100 mol% of the total structural unit of component (A).
  6. A resin composition according to claim 1 or 2, wherein (C) all or part of the component is a compound comprising a hydroxyl group such that when two hydroxyl groups bonded to the compound are selected, the relationship of the substitution positions of the two hydroxyl groups is an ortho position or a para position.
  7. A resin composition according to claim 1 or 2, wherein all or part of component (C) is a compound having a structure represented by (C)' formula (2). (In Equation (2), n represents an integer from 2 to 4, and * represents a bonding point with a substituent.)
  8. A resin composition according to claim 1 or 2, wherein (A) the weight average molecular weight of the component is 3,000 or more and 20,000 or less.
  9. A resin composition according to claim 1 or 2, wherein (A) the dispersion degree of the component is 1.1 or higher and 2.0 or lower.
  10. A resin composition according to claim 1 or 2, wherein the molecular weight of component (C) is 126 or more and 300 or less.
  11. A resin composition according to claim 1 or 2, wherein the content of component (C) per 100 parts by mass of component (A) is 20 parts by mass or more and 60 parts by mass or less.
  12. A resin composition according to claim 1 or 2, wherein (D) all or part of the component is a compound containing five or more methylol groups.
  13. A resin composition according to claim 1 or 2, wherein (D) all or part of the component is a compound containing a triazine structure.
  14. A resin composition according to claim 1 or 2, wherein the content of component (D) per 100 parts by mass of component (A) is 20 parts by mass or more and 50 parts by mass or less.
  15. A resin composition according to claim 1 or 2, further comprising a coloring agent (hereinafter referred to as “(E) component”).
  16. In paragraph 15, (E) a resin composition in which all or part of the components are compounds having a xanthenic structure.
  17. A resin composition according to claim 1 or 2, further comprising one or more types ((F) component) selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, polyamideimide precursor, and copolymers thereof.
  18. A cured product obtained by curing the resin composition described in paragraph 1 or 2.
  19. A display device having a cured material as described in paragraph 18.

Description

Resin composition, cured product, display device The present invention relates to a resin composition, a cured product using the same, and a display device. More specifically, the invention relates to a cured product suitable for a surface protective film of a semiconductor device, an interlayer insulating film, a pixel division layer of an organic electroluminescence (hereinafter referred to as EL) device, a planarization film of a thin film transistor (hereinafter referred to as TFT) substrate for driving a display device using an organic EL device, a wiring protective insulating film of a circuit board, an on-chip microlens of a solid-state imaging device, a planarization film for various displays and solid-state imaging devices, and a solder resist for a circuit board, and a resin composition for forming the same. In display devices having thin displays, such as smartphones, tablet PCs, and televisions, many products using organic electroluminescence (hereinafter "organic EL") display devices are being developed. Generally, an organic EL display device has a driving circuit, a planarization layer, a first electrode, a pixel division layer, a light-emitting layer, and a second electrode on a substrate, and can emit light by applying a voltage between the first electrode and the second electrode that are opposite each other. Among these, a photosensitive resin composition capable of forming a pattern by ultraviolet irradiation is generally used as a material for the planarization layer and a material for the pixel division layer. In photosensitive resin compositions used for these applications, high sensitivity is required to shorten exposure time due to reasons such as increasing substrate size and improving productivity, in addition to providing high reliability to organic EL display devices or semiconductor devices. In response to these requirements, a photosensitive resin composition using a polyimide-based resin has been devised as a technology capable of providing high reliability (e.g., Patent Document 1). In addition, as a technology for increasing sensitivity, mixing a polyimide resin or a polybenzoxazole resin with a novolak resin in the photosensitive resin composition is being considered (e.g., Patent Document 2). Figure 1 is a schematic diagram of the manufacturing procedure for an organic EL display device. The present invention will be described in detail below. <Any or both of polyhydroxystyrene and copolymers of hydroxystyrene and styrene derivatives not having phenolic hydroxyl groups (hereinafter referred to as “Component (A)”)> The resin composition of the present invention contains either or both of the following as component (A): polyhydroxystyrene, which is a polymer of hydroxystyrene that may or may not have a substituent on a benzene ring or a vinyl group (hereinafter referred to as “(A-1) component”); and a copolymer of hydroxystyrene, which is a polymer of hydroxystyrene that may or may not have a substituent on a benzene ring or a vinyl group, and a styrene derivative that does not have a phenolic hydroxyl group (hereinafter referred to as “(A-2) component”). (A) The component is synthesized by a known method. For example, component (A-1) can be obtained by addition polymerization of hydroxystyrene, which may or may not have a substituent on a benzene ring or vinyl group. Examples of phenol derivatives having unsaturated bonds include hydroxystyrene, dihydroxystyrene, coumaric acid, 2-hydroxychalcone, resveratrol, and 4-hydroxystilbene. Two or more of these may be used as polyhydroxystyrenes. In addition, the phenolic hydroxyl groups included in components (A-1) and (A-2) may be polymerized using a monomer protected by a protecting group, for example, an alkoxy group, during the monomer stage, and after polymerization, the protecting group may be deprotected by the action of an acid or the like to be returned to a phenolic hydroxyl group. In addition, component (A-2) can be obtained by addition polymerization of, for example, the hydroxystyrene described above and a styrene derivative that does not have a phenolic hydroxyl group. Examples of styrene derivatives that do not have phenolic hydroxyl groups include styrene, aminostyrene, vinyltoluene, vinylbenzoic acid and its ester compounds, and styrenesulfonic acid. Among styrene derivatives that do not have phenolic hydroxyl groups, it is preferable to use styrene in terms of changes in opening dimensions. Examples of addition polymerization methods include radical polymerization and anionic polymerization. With radical polymerization, a polymer with a dispersion greater than 2.0 can be obtained, and a polymer with a dispersion of 2.0 or less can be obtained by purification using methods such as reprecipitation or gel permeation chromatography. On the other hand, with anionic polymerization, a polymer with a dispersion of 1.5 or less can be obtained directly. In addition, it is desirable that component (A) contains a structural