EP-4737505-A1 - RESIN, PHOTOSENSITIVE COMPOSITIONS, CURED OBJECT, DISPLAY DEVICE, ELECTRONIC COMPONENT, AND METHOD FOR PRODUCING CURED OBJECT

EP4737505A1EP 4737505 A1EP4737505 A1EP 4737505A1EP-4737505-A1

Abstract

An object of the present invention is to provide a photosensitive composition capable of suppressing residues after development, to provide a photosensitive composition capable of obtaining a cured product included in a display device having excellent light emission characteristics capable of low voltage driving in obtaining a desired current density and excellent reliability of a light emitting element, and to provide a photosensitive composition capable of obtaining a cured product included in an electronic component excellent in migration resistance. There is provided a resin being one or more resins selected from the group consisting of a polyimide, a polyimide precursor, a polybenzoxazole, a polybenzoxazole precursor, a polyamideimide, a polyamideimide precursor, and a copolymer thereof, in which the resin has a first amine residue (DA1): an amine residue having a phenolic hydroxyl group, the first amine residue (DA1) has at least two cyclic structures having a phenolic hydroxyl group, and further has a specific structure linking them, and the resin satisfies a condition that a content of a fluorine element in the structure of the resin is 10,000 ppm by mass or less.

Inventors

TANIGAKI, YUGO
BABA, OSAMU
WADA, TATSUHO
SAEKI, AKINORI

Assignees

Toray Industries, Inc.

Dates

Publication Date: 20260506
Application Date: 20240621

Claims (20)

A resin being one or more resins selected from the group consisting of a polyimide, a polyimide precursor, a polybenzoxazole, a polybenzoxazole precursor, a polyamideimide, a polyamideimide precursor, and a copolymer thereof, wherein the resin has a first amine residue (DA1): an amine residue having a phenolic hydroxyl group, and the first amine residue (DA1) has at least two structures (Ia): a cyclic structure having a phenolic hydroxyl group, and a structure (IIa): a structure linking at least two of the structures (Ia), and the structure (IIa) is a sulfonyl group, an alkylene group, a condensed polycyclic structure, a hydrocarbon group including an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group including a carbonyloxy group, or a hydrocarbon group including a carbonyl amide group, and the resin satisfies the following condition (P1a): (P1a) a content of a fluorine element in the structure of the resin is 10,000 ppm by mass or less.
The resin according to claim 1, wherein the first amine residue (DA1) has an amine residue satisfying the following condition (S1x): (S1x) an amine residue has a C 1 symmetry axis as a molecular symmetry and does not have a C 2 symmetry axis.
The resin according to claim 1, further comprising a second amine residue (DA2): an amine residue having no phenolic hydroxyl group, and satisfying the following condition (α1) and/or condition (α2), wherein a total content ratio of the first amine residue (DA1) to all amine residues in the resin is 20 mol% or more and 90 mol% or less, and a total content ratio of the second amine residue (DA2) to all amine residues in the resin is 10 mol% or more and 80 mol% or less: (α1) the second amine residue (DA2) has at least two structures (Ib): a cyclic structure having no phenolic hydroxyl group, and a structure (IIb): a structure linking at least two of the structures (Ib), and the structure (IIb) is a sulfonyl group, an alkylene group, a condensed polycyclic structure, a hydrocarbon group including an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group including a carbonyloxy group, or a hydrocarbon group including a carbonyl amide group; (α2) the second amine residue (DA2) has a structure (IIIb): a silicone structure and/or a siloxane structure.
The resin according to claim 3, wherein the first amine residue (DA1) has an amine residue satisfying the following conditions (S1x), and/or the second amine residue (DA2) has an amine residue satisfying at least one of the following conditions (S1x) and (S2x): (S1x) an amine residue has a C 1 symmetry axis as a molecular symmetry and does not have a C 2 symmetry axis; (S2x) an amine residue has at least one of a chiral center, a chiral axis, a chiral plane, and a helical axis.
The resin according to claim 2 comprising a polyimide unit and a polyimide precursor unit, wherein a content ratio of a polyimide unit to a total of the polyimide unit and the polyimide precursor unit is 1.0 mol% or more and 30 mol% or less, and a content ratio of an amic acid ester structure to a total of an amic acid structure and an amic acid ester structure in the polyimide precursor unit is 40 mol% or more and 99 mol% or less.
The resin according to claim 2 comprising a polyimide unit and/or a polyimide precursor unit, and the resin has one or more selected from the group consisting of a polybenzoxazole unit, a polybenzoxazole precursor unit, a polyamideimide unit, and a polyamideimide precursor unit, wherein a total content ratio of a polybenzoxazole unit, a polybenzoxazole precursor unit, a polyamideimide unit, and a polyamideimide precursor unit to a total of a polyimide unit, a polyimide precursor unit, a polybenzoxazole unit, a polybenzoxazole precursor unit, a polyamideimide unit, and a polyamideimide precursor unit of the resin is 10 mol% or more and 90 mol% or less.
The resin according to claim 2, further satisfying at least one of the following conditions (P1b), (P1c), and (P1d) : (P1b) a content of a chlorine element in the structure of the resin is 30,000 ppm by mass or less; (P1c) a content of a bromine element in the structure of the resin is 30,000 ppm by mass or less; (P1d) a content of a sulfur element in the structure of the resin is 30,000 ppm by mass or less.
A photosensitive composition comprising a binder resin (A) and a photosensitive agent (C), and further comprising a radical polymerizable compound (B) and/or a crosslinking agent (F), wherein the binder resin (A) includes the resin according to claim 2.
The photosensitive composition according to claim 8, wherein the binder resin (A), the photosensitive agent (C), the radical polymerizable compound (B), or the crosslinking agent (F) has a fluorine atom, a chlorine atom, a bromine atom, a fluoride ion, a chloride ion, or a bromide ion in its structure, or the photosensitive composition further contains a component including a fluorine element, a chlorine element, or a bromine element and/or a component including a fluoride ion, a chloride ion, or a bromide ion, and the photosensitive composition satisfies the following condition (P1x) and the following condition (1x): (P1x) a total content of a fluorine element, a chlorine element, and a bromine element in the structure of the resin is 30,000 ppm by mass or less; (1x) a total content of a fluorine element, a chlorine element, and a bromine element in a total solid content of the photosensitive composition is 0.010 ppm by mass or more and 1,000 ppm by mass or less.
A photosensitive composition comprising a binder resin (A) and a photosensitive agent (C), and further comprising a radical polymerizable compound (B) and/or a crosslinking agent (F), wherein the binder resin (A) includes a resin (Ax): one or more resins selected from the group consisting of a polyimide, a polyimide precursor, a polybenzoxazole, a polybenzoxazole precursor, a polyamideimide, a polyamideimide precursor, and a copolymer thereof, and the resin (Ax) has a first amine residue (DA1): an amine residue having a phenolic hydroxyl group, and the first amine residue (DA1) has at least two structures (Ia): a cyclic structure having a phenolic hydroxyl group, and a structure (IIa): a structure linking at least two of the structures (Ia), and the structure (IIa) is a sulfonyl group, an alkylene group, a condensed polycyclic structure, a hydrocarbon group including an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group including a carbonyloxy group, or a hydrocarbon group including a carbonyl amide group, and the photosensitive composition satisfies the following condition (1a): (1a) a content of a fluorine element in a total solid content of the photosensitive composition is 1,000 ppm by mass or less.
The photosensitive composition according to claim 10, wherein the binder resin (A), the photosensitive agent (C), the radical polymerizable compound (B), or the crosslinking agent (F) has a chlorine atom, a bromine atom, a sulfur atom, a chloride ion, a bromide ion, or a sulfur-based anion as described below in its structure, or the photosensitive composition further contains a component including a chlorine element, a bromine element, or a sulfur element and/or a component including a chloride ion, a bromide ion, or a sulfur-based anion as described below, and the photosensitive composition satisfies at least one of the following conditions (1b), (1c), and (1d): sulfur-based anion: one or more ions selected from the group consisting of a sulfide ion, a hydrogen sulfide ion, a sulfate ion, and a hydrogen sulfate ion (1b) a content of a chlorine element in the total solid content of the photosensitive composition is 0.010 ppm by mass or more and 1,000 ppm by mass or less; (1c) a content of a bromine element in the total solid content of the photosensitive composition is 0.010 ppm by mass or more and 1,000 ppm by mass or less; (1d) a content of a sulfur element in the total solid content of the photosensitive composition is 0.010 ppm by mass or more and 1,000 ppm by mass or less.
The photosensitive composition according to any one of claims 8 to 11, further comprising a phenol compound (I), wherein the phenol compound (I) satisfies the following condition (β1), and the photosensitive composition satisfies the following condition (5): (β1) having at least two of the following structures (Ic) and the following structure (IIIc) structure (Ic): a cyclic structure having a phenolic hydroxyl group structure (IIIc): a structure linking at least two of the structures (Ic), the structure being a sulfonyl group, an alkylene group, a condensed polycyclic structure, a hydrocarbon group including an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group including a carbonyloxy group, or a hydrocarbon group including a carbonyl amide group; (5) a total content of the phenol compound (I) in the total solid content of the photosensitive composition is 0.010 ppm by mass or more and 10,000 ppm by mass or less.
The photosensitive composition according to claims 8 to 11, further comprising one or more resins selected from the group consisting of a phenolic resin, polyhydroxystyrene, a phenol group-containing epoxy resin, and a phenol group-containing acrylic resin.
The photosensitive composition according to any one of claims 8 to 11, wherein the photosensitive agent (C) contains a compound having a 1,2-naphthoquinonediazide-5-sulfonic acid ester structure and a compound containing a 1,2-naphthoquinonediazide-4-sulfonic acid ester structure.
The photosensitive composition according to any one of claims 8 to 11, further comprising water, and satisfying the following condition (3): (3) a content of water in the photosensitive composition is 0.010 mass% or more and 3.0 mass% or less.
The photosensitive composition according to any one of claims 8 to 11, further comprising a nitrogen-containing compound (H), wherein the nitrogen-containing compound (H) includes one or more selected from the group consisting of a cyclic amide compound, an amide compound, a cyclic urea compound, a urea compound, an oxazolidone compound, and an isoxazolidone compound, and the photosensitive composition satisfies the following condition (4): (4) a total content of a cyclic amide compound, an amide compound, a cyclic urea compound, a urea compound, an oxazolidone compound, and an isoxazolidone compound in the total solid content of the photosensitive composition is 0.010 mass% or more and 5.0 mass% or less.
The photosensitive composition according to any one of claims 8 to 11, further comprising a crosslinkable aromatic compound (J), wherein the crosslinkable aromatic compound (J) has at least two structures (Id): a cyclic structure in which a phenolic hydroxyl group and at least two crosslinkable groups are bonded, and at least two structures (IId): a cyclic structure having a phenolic hydroxyl group different from the structure (Id), and further has a structure (IIId): a structure linking at least two of the structures (IId), and the photosensitive composition satisfies the following condition (6): (6) a total content of the crosslinkable aromatic compound (J) in the total solid content of the photosensitive composition is 0.010 ppm by mass or more and 5,000 ppm by mass or less.
A cured product obtained by curing the photosensitive composition according to any one of claims 8 to 11.
A display device comprising the cured product according to claim 18.
An electronic component comprising the cured product according to claim 18.

Description

TECHNICAL FIELD The present invention relates to a resin, a photosensitive composition, a cured product, a display device, an electronic component, and a method for producing a cured product. BACKGROUND ART In recent years, efforts have been made to reduce cost and increase integration by improving efficiency of a semiconductor manufacturing process, and a semiconductor device that forms a multilayer metal redistribution wiring has attracted attention. A material used for an interlayer insulating layer in such multilayer metal redistribution wiring is required to have high migration resistance because reliability related to electrical insulation is required due to wiring miniaturization associated with high integration of the semiconductor device. Furthermore, development residue suppression during pattern formation of positive type or negative type by photolithography is also required. Further, in an organic electroluminescence (hereinafter, "organic EL") display as a display device, a pixel dividing layer or a thin film transistor (hereinafter, "TFT") planarization layer is formed at a position adjacent to or close to a light emitting element. Therefore, in order to improve reliability of the organic EL display, it is necessary to examine a configuration of the pixel dividing layer and the like and physical properties such as heat resistance of a material used for the pixel dividing layer and the like. In addition, in order to achieve high luminance and power saving of the organic EL display, excellent light emission characteristics capable of low voltage driving in obtaining a desired current density are required. As the display device, for example, a display device including a pixel dividing layer containing polyimide (see, for example, Patent Document 1) and an organic EL display (see, for example, Patent Document 2) in which a sum of contents of a metal element and/or a halogen element in a cured film falls within a specific range are known. PRIOR ART DOCUMENT PATENT DOCUMENTS Patent Document 1: Japanese Patent Laid-open Publication No. 2002-091343Patent Document 2: International Publication No. 2018/123853 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION However, the display device described in Patent Document 1 or Patent Document 2 still has a problem with light emission characteristics related to low voltage driving, reliability of a light emitting element, or migration resistance. In addition, the composition described in Patent Document 1 or Patent Document 2 has a problem in suppressing residues after development. An object of the present invention is to provide a photosensitive composition capable of suppressing residues after development, and to provide a display device that has excellent light emission characteristics capable of low voltage driving in obtaining a desired current density and has excellent reliability of the light emitting element. Further, another object of the present invention is to provide an electronic component excellent in migration resistance. SOLUTIONS TO THE PROBLEMS As a result of intensive studies to solve the above-described problems, it has been found that significant effects can be achieved by focusing on a fluorine element among halogen elements. In particular, the present inventors have found that the above-described problems can be solved by a specific configuration related to the content of the fluorine element in a resin contained in a composition used for forming a cured film or the content of the fluorine element in the composition, and have completed the present invention. The resin of the present invention, the photosensitive composition of the present invention, or the display device of the present invention has the following configurations [1] to [22]. [1] A resin being one or more resins selected from the group consisting of a polyimide, a polyimide precursor, a polybenzoxazole, a polybenzoxazole precursor, a polyamideimide, a polyamideimide precursor, and a copolymer thereof, in which the resin has a first amine residue (DA1): an amine residue having a phenolic hydroxyl group, and the first amine residue (DA1) has at least two structures (Ia): a cyclic structure having a phenolic hydroxyl group, and a structure (IIa): a structure linking at least two of the structures (Ia), andthe structure (IIa) is a sulfonyl group, an alkylene group, a condensed polycyclic structure, a hydrocarbon group including an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group including a carbonyloxy group, or a hydrocarbon group including a carbonyl amide group, andthe resin satisfies the following condition (P1a): (P1a) the content of a fluorine element in the structure of the resin is 10,000 ppm by mass or less.[2] The resin according