Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
  • G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/075—Silicon-containing compounds
  • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/20—Exposure; Apparatus therefor
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
  • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
  • H05B33/22—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
  • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
  • H10K59/10—OLED displays
  • H10K59/12—Active-matrix OLED [AMOLED] displays
  • H10K59/122—Pixel-defining structures or layers, e.g. banks
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
  • H10K59/10—OLED displays
  • H10K59/12—Active-matrix OLED [AMOLED] displays
  • H10K59/124—Insulating layers formed between TFT elements and OLED elements
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/10—Organic polymers or oligomers

Definitions

• the present invention relates to a photosensitive composition, a cured product, a display device, and a method for producing the cured product.
• OLED organic electroluminescence
• TFT thin film transistor
• photosensitive compositions include positive-type photosensitive compositions that contain polyimide as a resin (see, for example, Patent Document 1).
• materials with improved mechanical properties include compositions in which a flexible polyoxyalkylene structure is introduced into the main chain of polyimide (see, for example, Patent Document 2).
• compositions described in Patent Document 1 and Patent Document 2 have problems in combining sensitivity during exposure, suppression of residue after development, mechanical properties, and reliability of the light-emitting element. Therefore, further improvement in the properties of photosensitive compositions is desired.
• the present invention aims to provide a cured product that combines excellent sensitivity during exposure and suppression of residue after development, has excellent mechanical properties, and is to be provided in a display device having excellent reliability of the light-emitting element. Another object of the present invention is to provide a display device having excellent reliability of the light-emitting element.
• the photosensitive composition and display device of the present invention have the following configurations [1] to [20].
• a photosensitive composition comprising (A) a binder resin and (C) a photosensitizer, further comprising (H) an imide compound,
• the structure containing an imide bond in the structure (I) is an aromatic structure containing an imide bond, a condensed polycyclic structure containing an imide bond, an alicyclic structure containing an imide bond, an aliphatic structure containing an imide structure, a succinimide structure, a maleimide structure, or a nadimide structure
• the cyclic structure in the structure (I) is an aromatic structure or a condensed polycyclic structure
• the binder resin (A) contains one or more resins selected from the group consisting of: (A1x-1) resin: polyimide, (A1x-2) resin: polyimide precursor, (A1x-3) resin: polybenzoxazole, (A1x-4) resin: polybenzoxazole precursor, (A1x-5) resin: polyamideimide, (A1x-6) resin: polyamideimide precursor, (A1x-7) resin: polyamide, and copolymers thereof (hereinafter referred to as "polyimide-based resins having a weakly acidic group”);
• the polyimide resin having a weak acidic group has a primary amine residue (DA1): an amine residue having a phenolic hydroxyl group
• the primary amine residue (DA1) has at least two structures (Ia): cyclic structures having a phenolic hydroxyl group, and further has a structure (IIa): a structure connecting at least two of the structures (Ia); the (IIa)
• the (II) structure is an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• the (II) structure is an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a
• the (H) imide compound is an (H2z) compound: a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group, and the (II) structure is an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• the (H) imide compound is an (H2z) compound: a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxy
• the binder resin (A) contains a weakly acidic group-containing resin (A1), and the weakly acidic group-containing resin (A1) has a weakly acidic group (WA): one or more groups selected from the group consisting of a phenolic hydroxyl group, a hydroxyimide group, a hydroxyamide group, a silanol group, a 1,1-bis(trifluoromethyl)methylol group, and a mercapto group;
• the (A1) weakly acidic group-containing resin comprises (A1x) a resin having, in a structural unit of the resin, at least one structure selected from the group consisting of an imide structure, an amide structure, an oxazole structure, and a siloxane structure
• the (A1x) resin contains one or more resins selected from the group consisting of: (A1x-1) resin: polyimide, (A1x-2) resin: polyimide precursor, (A1x-3) resin: polybenzoxazole, (A
• the (A1x) resin has a fluorine-containing amine residue and/or a fluorine-containing carboxylic acid residue, and the fluorine-containing amine residue and the fluorine-containing carboxylic acid residue have at least two fluorine-containing aromatic structures and a group linking the at least two fluorine-containing aromatic structures,
• the binder resin (A) contains a weakly acidic group-containing resin (A1), and the weakly acidic group-containing resin (A1) has a weakly acidic group (WA): one or more groups selected from the group consisting of a phenolic hydroxyl group, a hydroxyimide group, a hydroxyamide group, a silanol group, a 1,1-bis(trifluoromethyl)methylol group, and a mercapto group;
• the (A) binder resin contains the (A1) weakly acidic group-containing resin and (A2) a resin not having a weakly acidic group
• the (A1) weakly acidic group-containing resin contains: (A1x) resin: a resin having, in its structural unit, one or more structures selected from the group consisting of an imide structure, an amide structure, an oxazole structure, and a siloxane structure; and/or (A1y) resin: a resin having, in its structural unit, a phenolic hydroxy
• the total content of the carboxylic acid compound and the carboxylic acid ester (I) in the total solid content of the photosensitive composition is 0.010% by mass or more and 5.0% by mass or less.
• R 21 and R 22 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
• R 23 and R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
• a and b each independently represent an integer of 2 to 8.
• c represents an integer of 0 to 4.
• the photosensitive composition according to any one of [1] to [13] above, further comprising water and satisfying the following condition (4): (4)
• the content of water in the photosensitive composition is 0.010% by mass or more and 3.0% by mass or less.
• the composition contains a radical polymerizable compound (B) and/or a crosslinking agent (F), and when the structure (I) or the structure (II) further has a radical polymerizable group, the composition contains the radical polymerizable compound (B),
• a display device comprising the cured product described in [17].
• a method for producing a cured product comprising the steps of: (1) forming a coating film of the photosensitive composition described in any one of [1] to [16] on a substrate; (2) irradiating the coating film of the photosensitive composition with actinic radiation through a photomask; (3) developing the coating film with a developer to form a pattern of the photosensitive composition; and (4) heating the pattern to obtain a cured pattern of the photosensitive composition.
• a display device having a substrate, a first electrode, a second electrode, a pixel dividing layer, a light-emitting layer, and a TFT planarization layer, wherein the pixel dividing layer and/or the TFT planarization layer contain an (XH)imide compound;
• the (XH) imide compound has at least two (XI) structures: a structure in which a structure containing an imide bond and a cyclic structure having a phenolic hydroxyl group and/or a fluorine-containing substituent are bonded to each other, and further has a (XII) structure: a structure connecting at least two of the (XI) structures.
• the photosensitive composition of the present invention can provide a cured product that has excellent sensitivity during exposure and suppresses residues after development, and has excellent mechanical properties.
• the display device of the present invention can provide a display device that has excellent reliability of light-emitting elements.
• FIG. 1 is a plan view showing a manufacturing process of steps 1 to 4 for a substrate of an organic EL display used in an evaluation of light-emitting characteristics.
• the photosensitive composition of the present invention will be described below. However, the present invention is not limited to the following embodiments, and various modifications are possible within the scope of the invention, as long as the object of the invention can be achieved and the gist of the invention is not deviated from.
• the main chain of a resin refers to the longest chain among the chains that constitute the resin containing structural units.
• the side chain of a resin refers to a chain that is branched from the main chain or bonded to the main chain and has a shorter chain length than the main chain among the chains that constitute the resin containing structural units.
• the end of a resin refers to a structure that seals the main chain, such as a structure derived from an end-capping agent.
• a hydrocarbon group or alkylene group that includes a "*** bond” or a "*** group” refers to a hydrocarbon group or alkylene group to which a "*** bond” or a "*** group” is bonded, or at least two hydrocarbon groups or at least two alkylene groups that are linked by a "*** bond” or a "*** group”.
• the photosensitive composition of the present invention has the above-mentioned configuration [1].
• the photosensitive composition of the present invention can provide a cured product having excellent sensitivity during exposure and suppression of residue after development, and excellent mechanical properties.
• the compound is compatible with the entire film, and the aromatic structure having a phenolic hydroxyl group in the above-mentioned (II) structure promotes alkali dissolution, and the cyclic structure having a fluorine-containing substituent and the organic residue component in the opening (unexposed part in the case of negative photosensitivity, exposed part in the case of positive photosensitivity) promote dissolution in the developer due to the interaction between the organic residue component in the opening (unexposed part in the case of positive photosensitivity) are thought to be effective in achieving excellent sensitivity during exposure and suppression of residue after development.
• the surface of the substrate is surface-modified by the compound, it is also thought that the effect of suppressing residue after development is effective due to the prevention of residue adhesion in the opening.
• the imide bond in the above (I) structure interacts with the imide bond or amide bond in resins such as polyimide and polybenzoxazole.
• these resins are in a locally oriented state due to the ⁇ electron interaction between the imide bond and resins having aromatic rings such as polyimide, polybenzoxazole, and their precursors, and the coordinate bond of the ⁇ electron with resins containing silicon atoms having 3d orbitals, which are empty atomic orbitals, such as polysiloxane.
• excellent mechanical properties are achieved because the crosslinking reaction between resins and the ring-closing reaction of resins proceed efficiently.
• the compound forms a crosslinked structure with resins as a crosslinking agent. Therefore, it is presumed that the above (I) structure or (II) structure contributes to the control of the polarization structure and charge balance in the cured product.
• the effect of excellent reliability of the light-emitting element is achieved by suppressing migration and aggregation of metals in electrodes and wiring. In other words, it is presumed that the excellent migration resistance effect will also be effective in electronic components, semiconductor devices, display devices, and metal-clad laminates.
• the photosensitive composition of the present invention contains (A) a binder resin.
• Binder resin is a heat-resistant resin that at least a part of which remains in a cured product obtained by curing the composition.
• Binder resin is preferably a resin that is cured by forming a crosslinked structure by reaction. The reaction is not particularly limited and may be by heating or by irradiation with energy rays, and a crosslinked structure may be formed by a crosslinking agent (F) described later.
• A) Binder resin is preferably a thermosetting resin.
• the (A) binder resin is preferably an alkali-soluble resin having an acidic group or an organic solvent-soluble resin having an organic solvent-soluble structure.
• the (A) binder resin is preferably a resin that is given positive or negative photosensitivity by the (C) photosensitizer described later and has solubility that allows the formation of a positive or negative pattern.
• the (A) binder resin more preferably has an acidic group in the structural unit of the resin.
• the acidic group is preferably a phenolic hydroxyl group, a hydroxyimide group, a hydroxyamide group, a silanol group, a 1,1-bis(trifluoromethyl)methylol group, a mercapto group, a carboxy group, a carboxylic anhydride group, or a sulfonic acid group, and furthermore from the viewpoint of improving sensitivity during exposure and suppressing residues after development, a carboxy group, a carboxylic anhydride group, or a sulfonic acid group is more preferable.
• the binder resin preferably has a radical polymerizable group, and more preferably has a radical polymerizable group in the structural unit of the resin.
• the radical polymerizable group preferably has an ethylenically unsaturated double bond group, and more preferably is a photoreactive group, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms.
• the photoreactive group is preferably a styryl group, a cinnamoyl group, a maleimide group, a nadiimide group, or a (meth)acryloyl group, and from the viewpoint of improving sensitivity during exposure and improving mechanical properties, a (meth)acryloyl group is more preferable.
• the alkenyl group having 2 to 5 carbon atoms or the alkynyl group having 2 to 5 carbon atoms is preferably a vinyl group, an allyl group, a 2-methyl-2-propenyl group, a crotonyl group, a 2-methyl-2-butenyl group, a 3-methyl-2-butenyl group, a 2,3-dimethyl-2-butenyl group, an ethynyl group, or a 2-propargyl group, and from the viewpoint of improving sensitivity during exposure and improving mechanical properties, a vinyl group or an allyl group is more preferable.
• the binder resin (A) preferably contains (A1) a weakly acidic group-containing resin and/or (A2) a resin having no weakly acidic groups.
• the (A) binder resin contains (A1) a weakly acidic group-containing resin
• the (A1) weakly acidic group-containing resin preferably has (WA) a weakly acidic group: one or more groups selected from the group consisting of a phenolic hydroxyl group, a hydroxyimide group, a hydroxyamide group, a silanol group, a 1,1-bis(trifluoromethyl)methylol group, and a mercapto group, and more preferably has (WA) a weakly acidic group in the structural unit of the resin.
• the (WA) weakly acidic group is preferably a phenolic hydroxyl group, a silanol group, or a 1,1-bis(trifluoromethyl)methylol group, and more preferably a phenolic hydroxyl group.
• the above-mentioned (A1) weakly acidic group-containing resin has a significant effect of improving sensitivity during exposure because the solubility of the exposed area is improved due to the moderate acidity of the (WA) weakly acidic group and the interaction with the (C) photosensitizer described below.
• the phenolic hydroxyl group of the (WA) weakly acidic group has a significant effect of suppressing residue after development due to its alkaline dissolution promoting effect.
• the phenolic hydroxyl group of the (WA) weakly acidic group can increase the dissolution contrast between exposed and unexposed areas due to its strong interaction with the (C) photosensitizer, and also improves the dissolution promoting effect in the exposed area, resulting in a significant effect of improving sensitivity during exposure and suppressing residue after development.
• the (A) binder resin contains a (A2) resin that does not have a weak acid group.
• the (A2) resin that does not have a weak acid group preferably has an acid group different from the (WA) weak acid group, and more preferably has an acid group different from the (WA) weak acid group in the structural unit of the resin.
• the (WA) acid group different from the weak acid group is more preferably a carboxy group, a carboxylic acid anhydride group, or a sulfonic acid group.
• the (A) binder resin contains the (A1) weakly acidic group-containing resin, and that the (A1) weakly acidic group-containing resin has a radically polymerizable group.
• the radically polymerizable group are as described above for the (A) binder resin.
• the (A) binder resin preferably contains (A1) a resin containing a weak acid group and/or (A2) a resin not having a weak acid group
• the (A1) resin containing a weak acid group preferably contains (A1x) a resin having one or more structures selected from the group consisting of imide structures, amide structures, oxazole structures, and siloxane structures (hereinafter, "imide structures, etc.") in the structural unit of the resin
• the (A2) resin not having a weak acid group preferably contains (A2x) a resin having a radical polymerizable group and/or (A2y) a resin not having a radical polymerizable group.
• the (A) binder resin contains the (A1) weakly acidic group-containing resin
• the (A) binder resin contains (A1) a weakly acidic group-containing resin and (A2) a resin without a weakly acidic group
• the (A1) weakly acidic group-containing resin contains (A1x) resin and/or (A1y) resin
• the (A2) resin without a weakly acidic group contains (A2x) resin and/or (A2y) resin.
• the photosensitive composition of the present invention preferably contains (A1) a weakly acidic group-containing resin and (A2) a resin that does not have a weakly acidic group
• the (A1) weakly acidic group-containing resin preferably contains (A1x) resin and/or (A1y) resin
• the (A2) resin that does not have a weakly acidic group preferably contains (A2x) resin and/or (A2y) resin.
• the (A1x) resin, (A1y) resin, (A2x) resin, and (A2y) resin each have a structure or group that constitutes a different resin, they shall be classified according to the classification method shown in Table 1-1 below. If a resin can fall into two or more of the (A1x) resin, (A1y) resin, (A2x) resin, and (A2y) resin, the classification method shall determine which resin it falls into.
• the (A) binder resin preferably contains (A1x) resin and/or (A1y) resin, more preferably contains (A1x) resin, and even more preferably contains (A1x) resin and (A1y) resin.
• the (A) binder resin also preferably contains (A1x) resin and/or (A1y) resin and further contains (A2x) resin, and more preferably contains (A1x) resin, (A1y) resin, and (A2x) resin.
• the (A) binder resin also preferably contains (A1x) resin, (A1y) resin, or (A2x) resin, and further contains (A2y) resin. From the viewpoint of improving the properties of each resin, the (A) binder resin also preferably contains two or more types selected from the group consisting of (A1x) resin, (A1y) resin, (A2x) resin, and (A2y) resin.
• the weakly acidic group-containing resin (A1) preferably contains a resin (A1x) from the viewpoints of improving sensitivity during exposure, improving mechanical properties, and improving the reliability of the light-emitting element.
• the resin (A1x) is, from the viewpoints of improving sensitivity during exposure, improving mechanical properties, and improving the reliability of the light-emitting element, preferably a resin (A1x-1) containing a polyimide, a polyimide precursor, a polybenzoxazole, a polybenzoxazole precursor, a polyamideimide, a polyamideimide precursor ...
• the resin (A1x) contains one or more selected from the group consisting of a doped styrene resin, a maleimide-triazine resin, a maleimide-oxazine resin, and copolymers thereof, and it is more preferable that the resin (A1x-1), a resin (A1x-2), a resin (A1x-3), a resin (A1x-4), a resin (A1x-5), a resin (A1x-6), a resin (A1x-7), and copolymers thereof (hereinafter, "polyimide resins having weak acid groups").
• the resin (A1x) contains a resin (A1x-1), a resin (A1x-3), and copolymers thereof. From the viewpoint of improving sensitivity during exposure, it is more preferable that the resin (A1x) contains a resin (A1x-2), a resin (A1x-4), and copolymers thereof.
• the resin (A1x) may be either a single resin or a copolymer thereof.
• the (A1x) resin has an imide structure, an amide structure, an oxazole structure, or a siloxane structure in the structural unit of the resin, which improves the mechanical properties.
• these structures capture metal impurities and ionic impurities that adversely affect electrical insulation, which is believed to suppress ion migration and electromigration and improve the reliability of the light-emitting device.
• the (A2x) resin and the (A2y) resin preferably contain one or more types selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, polyamideimide precursor, polyamide, maleimide resin, maleimide-styrene resin, maleimide-triazine resin, maleimide-oxazine resin, and copolymers thereof, and more preferably contain one or more types selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, polyamideimide precursor, polyamide, and copolymers thereof (hereinafter referred to as "polyimide-based resins having no weakly acidic groups").
• the weakly acidic group-containing resin (A1) contains a resin (A1x), from the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving the reliability of the light-emitting element, it is preferred that the resin (A1x) contains one or more types selected from the group consisting of the above-mentioned polyimide-based resins having a weakly acidic group, and that the resin (A1x) has an amine residue (WA) containing a weakly acidic group and/or a carboxylic acid residue (WA) containing a weakly acidic group.
• the resin (A1x) contains one or more types selected from the group consisting of the above-mentioned polyimide-based resins having a weakly acidic group, and that the resin (A1x) has an amine residue (WA) containing a weakly acidic group and/or a carboxylic acid residue (WA) containing a weakly acidic group.
• the (A) binder resin contains (A1) a weakly acidic group-containing resin, the (A1) weakly acidic group-containing resin has (WA) a weakly acidic group, and the (A1) weakly acidic group-containing resin contains (A1x) resin, It is preferred that the resin (A1x) contains one or more resins selected from the group consisting of the above-mentioned polyimide resins having a weak acidic group, and the resin (A1x) contains an amine residue (WA) having a weak acidic group and/or a carboxylic acid residue (WA) having a weak acidic group.
• the resin (A1x) has an amine residue containing a weak acidic group (WA) and/or a carboxylic acid residue containing a weak acidic group (WA), From the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving reliability of the light-emitting device, the resin (A1x) has a fluorine-containing amine residue and/or a fluorine-containing carboxylic acid residue, the fluorine-containing amine residue and the fluorine-containing carboxylic acid residue have at least two fluorine-containing aromatic structures and a group linking the at least two fluorine-containing aromatic structures, It is preferable that the group connecting at least two fluorine-containing aromatic structures has an ether bond.
• the (A1x) resin has the above-mentioned fluorine-containing amine residue and/or fluorine-containing carboxylic acid residue
• the above-mentioned fluorine-containing aromatic structure contains an aromatic structure having a trifluoromethyl group from the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving the reliability of the light-emitting device.
• one or more selected from the group consisting of (A1x-1) resin, (A1x-2) resin, (A1x-3) resin, (A1x-4) resin, (A1x-5) resin, (A1x-6) resin, and copolymers thereof have one or more selected from the group consisting of amine residues represented by general formula (11) and amine residues represented by general formula (13), and/or one or more selected from the group consisting of carboxylic acid residues represented by general formulas (11), (12), and (14).
• R 31 to R 38 each independently represent a 1,1-bis(trifluoromethyl)methylol group, a mercapto group, or a sulfonic acid group.
• R 39 to R 42 each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogenated alkyl group having 1 to 6 carbon atoms.
• R 61 to R 68 each independently represent a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, or an acyl group having 1 to 10 carbon atoms.
• X 11 to X 16 each independently represent a direct bond, a hydrocarbon group, a hydrocarbon group containing an ether bond, or an amide group to which a hydrocarbon group is bonded.
• Y 11 to Y 14 each independently represent a direct bond, an oxygen atom, a sulfur atom, a sulfonyl group, a hydrocarbon group, a hydrocarbon group containing an ether bond, a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• a, b, c, d, e, and f each independently represent an integer of 0 to 4.
• g, h, i, j, m, and n each independently represent an integer of 0 to 4.
• k and l each independently represent an integer of 0 to 3.
• o, p, q, r, s, t, u, and v each independently represent an integer of 0 to 3.
• w, x, y, and z each independently represent an integer of 0 to 6. Note that 1 ⁇ a+g ⁇ 4 and 1 ⁇ b+h ⁇ 4. Also, 1 ⁇ c+i ⁇ 4 and 1 ⁇ d+j ⁇ 4. Furthermore, 1 ⁇ e+m ⁇ 4 and 1 ⁇ f+n ⁇ 4. * 1 to * 13 each independently represent a bonding point in the resin.
• the halogen atom is preferably a fluorine atom.
• the halogenated alkyl group is preferably a fluorinated alkyl group.
• the hydrocarbon group, the hydrocarbon group containing an ether bond, and the hydrocarbon group in the amide group to which a hydrocarbon group is bonded are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, an arylene group having 6 to 15 carbon atoms, or an arylalkylene group having 10 to 20 carbon atoms.
• the hydrocarbon group in the hydrocarbon group and the hydrocarbon group containing an ether bond are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms of the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the above-mentioned substituents and structures may have a heteroatom, and may be either unsubstituted or substituted.
• the total content ratio of amine residues represented by general formula (11) and general formula (13) in the total amine residues of each resin, and/or the total content ratio of carboxylic acid residues represented by general formula (11), (12), and (14) in the total carboxylic acid residues, is preferably 10 mol% or more, more preferably 30 mol% or more, and even more preferably 50 mol% or more, from the viewpoint of improving the above-mentioned properties.
• the total content ratio of amine residues represented by general formula (11) and general formula (13) and/or the total content ratio of carboxylic acid residues represented by general formula (11), (12), and (14) is preferably 100 mol% or less, more preferably 90 mol% or less, and even more preferably 70 mol% or less, from the viewpoint of improving the above-mentioned properties.
• the binder resin (A) contains one or more resins selected from the group consisting of the polyimide resins having the above-mentioned weakly acidic group
• the polyimide resin having a weak acidic group preferably has a primary amine residue (DA1): an amine residue having a phenolic hydroxyl group, and more preferably the primary amine residue (DA1) has at least two (Ia) structures: cyclic structures having a phenolic hydroxyl group, and further has a (IIa) structure: a structure connecting at least two (Ia) structures.
• the cyclic structure in the (Ia) structure is preferably an aromatic structure or a condensed polycyclic structure, and more preferably an aromatic structure having 6 to 15 carbon atoms or a condensed polycyclic structure having 6 to 20 carbon atoms.
• the aromatic structure is preferably a biphenyl structure or a benzene structure.
• the condensed polycyclic structure is preferably a fluorene structure, an anthracene structure, or a naphthalene structure.
• the phenolic hydroxyl group in the (DA1) primary amine residue may react with a structure and/or group in the resin to form a benzoxazole ring. That is, in a resin having a benzoxazole ring in its structural unit, the benzoxazole ring may have a (DA1) primary amine residue.
• the (IIa) structure is preferably an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• the alkylene group, cycloalkylene group, or arylene group is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the hydrocarbon group in the hydrocarbon group containing an ether bond is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms in the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the binder resin (A) contains one or more resins selected from the group consisting of the polyimide resins having a weak acidic group
• the polyimide resin having a weak acidic group has a primary amine residue (DA1)
• the primary amine residue (DA1) has at least two of the structures (Ia) and (IIa)
• the structure (IIa) is the specific structure described above
• the imide compound (H) described below contains a compound (H2): a compound in which the cyclic structure in the structure (I) described below is an aromatic structure having a phenolic hydroxyl group.
• the primary amine residue (DA1) preferably has an amine residue represented by general formula (31) from the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving the reliability of the light-emitting device.
• R 71 and R 72 each independently represent a carboxy group, a mercapto group, or a sulfonic acid group.
• R 73 represents an alkyl group having 1 to 6 carbon atoms.
• R 74 and R 75 each independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, or an acyl group having 1 to 10 carbon atoms.
• X 31 and X 32 each independently represent a direct bond, a hydrocarbon group, a hydrocarbon group containing an ether bond, or an amide group to which a hydrocarbon group is bonded.
• Y 31 represents an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• a and b each independently represent an integer of 1 to 4.
• g and h each independently represent an integer of 0 to 3.
• o and p each independently represent an integer of 0 to 3.
• w represents an integer of 0 to 6. Note that 1 ⁇ a+g ⁇ 4 and 1 ⁇ b+h ⁇ 4.
• * 1 and * 2 each independently represent a bonding point in the resin.
• the hydrocarbon group in X 31 and X 32 , the hydrocarbon group containing an ether bond, and the hydrocarbon group in the amide group to which the hydrocarbon group is bonded are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, an arylene group having 6 to 15 carbon atoms, or an arylalkylene group having 10 to 20 carbon atoms.
• the hydrocarbon group in the hydrocarbon group and the hydrocarbon group containing an ether bond is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms of the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the above-mentioned substituents and structures may have heteroatoms, and may be either unsubstituted or substituted.
• the phenolic hydroxyl group in the amine residue represented by formula (31) may react with a structure and/or group in the resin to form a benzoxazole ring. That is, in a resin having a benzoxazole ring in its structural unit, the benzoxazole ring may have an amine residue represented by formula (31).
• the total content ratio of the amine residues represented by general formula (31) in all amine residues in a polyimide resin having a weak acidic group is preferably 10 mol% or more, more preferably 20 mol% or more, even more preferably 30 mol% or more, and particularly preferably 50 mol% or more, from the viewpoint of the effects of the invention described above.
• the total content ratio of the amine residues represented by general formula (31) is preferably 100 mol% or less, more preferably 90 mol% or less, and even more preferably 70 mol% or less, from the viewpoint of the effects of the invention described above.
• the polyimide-based resin having a weak acidic group further has (DA2) a secondary amine residue: an amine residue having no phenolic hydroxyl group and satisfies the following condition ( ⁇ 1) and/or condition ( ⁇ 2), and from the viewpoint of suppressing residues after development, it is more preferable that the polyimide-based resin having a weak acidic group further has (DA2) a secondary amine residue: an amine residue having no phenolic hydroxyl group and satisfies the following condition ( ⁇ 1) and/or condition ( ⁇ 2).
• the ( ⁇ 1) (DA2) secondary amine residue has at least two (Ib) structures: cyclic structures not having a phenolic hydroxyl group, and further has a (IIb) structure: a structure connecting at least two (Ib) structures, and the (IIb) structure is an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• the ( ⁇ 2) (DA2) secondary amine residue has a (IIIb) structure: a silicone
• the cyclic structure in the (Ib) structure is preferably an aromatic structure or a condensed polycyclic structure, and more preferably an aromatic structure having 6 to 15 carbon atoms or a condensed polycyclic structure having 6 to 20 carbon atoms.
• the aromatic structure is preferably a biphenyl structure or a benzene structure.
• the condensed polycyclic structure is preferably a fluorene structure, an anthracene structure, or a naphthalene structure.
• the alkylene group, cycloalkylene group, or arylene group in the (IIb) structure is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the hydrocarbon group in the hydrocarbon group containing an ether bond is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms in the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the silicone structure and siloxane structure in the (IIIb) structure are preferably bonded to at least two alkylene groups, and are divalent or higher structures via these alkylene groups.
• the divalent or higher structures are more preferably trivalent or higher, and even more preferably tetravalent or higher.
• the divalent or higher structures are preferably hexavalent or lower.
• the number of silicon atoms in the silicone structure and/or siloxane structure is preferably 2 or higher, more preferably 3 or higher, and even more preferably 4 or higher.
• the number of silicon atoms is preferably 15 or lower, more preferably 10 or lower, and even more preferably 8 or lower.
• the silicone structure is preferably a dialkyl silicone structure and/or a monoalkyl silicone structure
• the siloxane structure is preferably a monoalkyl siloxane structure.
• the number of carbon atoms in the alkyl group in the dialkyl silicone structure, monoalkyl silicone structure, and monoalkyl siloxane structure is preferably 1 or higher, more preferably 2 or higher, and even more preferably 3 or higher.
• the number of carbon atoms in the alkyl group is preferably 10 or lower, more preferably 8 or lower, and even more preferably 6 or lower.
• the total content ratio of (DA1) primary amine residues in all amine residues is preferably 20 mol% or more and 90 mol% or less
• the total content ratio of (DA2) secondary amine residues in all amine residues is preferably 10 mol% or more and 80 mol% or less.
• the total content ratio of (DA2) secondary amine residues in all amine residues is preferably 10 mol% or more, more preferably 20 mol% or more, even more preferably 30 mol% or more, and particularly preferably 40 mol% or more.
• the total content ratio of (DA2) secondary amine residues is preferably 80 mol% or less, more preferably 70 mol% or less, and even more preferably 60 mol% or less.
• the primary amine residue (DA1) described above has a phenolic hydroxyl group that promotes alkaline dissolution, resulting in significant improvements in sensitivity during exposure and suppression of residues after development.
• These structures also efficiently promote crosslinking reactions between resins and ring-closing reactions of resins, resulting in significant improvements in mechanical properties.
• These structures also promote the capture of metal impurities and ionic impurities that adversely affect electrical insulation, which is presumed to improve the reliability of light-emitting devices.
• the (A1x) resin has a radical polymerizable group.
• the radical polymerizable group is preferably obtained by reacting a part of the phenolic hydroxyl group and/or carboxyl group of the resin with a compound having a radical polymerizable group.
• the (A1x) resin contains an (A1x) resin that does not have a radical polymerizable group and an (A1x) resin that has a radical polymerizable group.
• the (A1x) resin that does not have a radical polymerizable group suppresses residue after development due to the acidic group or organic solvent-soluble structure, and has the ability to capture metal impurities and ion impurities, while the (A1x) resin that has a radical polymerizable group is thought to improve sensitivity during exposure and improve the degree of crosslinking of the film by promoting radical polymerization.
• outgassing is suppressed, and the effect of improving the reliability of the light-emitting element is remarkable.
• Such functional separation in the (A1x) resin results in a remarkable effect of improving multiple properties.
• the acid equivalent of the (A1x) resin is preferably 200 g/mol or more from the viewpoint of improving sensitivity during exposure.
• the acid equivalent of the (A1x) resin is preferably 600 g/mol or less from the viewpoint of suppressing residues after development.
• the exposure here refers to irradiation with active actinic rays (radiation), and examples of such irradiation include visible light, ultraviolet light, electron beams, and X-rays.
• exposure refers to irradiation with active actinic rays (radiation).
• the double bond equivalent of the (A1x) resin is preferably 200 g/mol or more from the viewpoint of suppressing residues after development.
• the double bond equivalent of the (A1x) resin is preferably 3,000 g/mol or less from the viewpoint of improving sensitivity during exposure.
• the polyimide resin having a weak acid group which is (A1x) resin
• the polyimide resin not having a weak acid group which is (A2x) resin or (A2y) resin
• these resins may be collectively referred to as polyimide resins.
• the polyimide precursor preferably has an amic acid ester structural unit and/or an amic acid amide structural unit.
• the polyimide precursor may also have an imide ring-closed structural unit in which a part of the amic acid structural unit, the amic acid ester structural unit, or the amic acid amide structural unit is ring-closed.
• the above polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, polyamideimide, and polyamideimide precursor may be copolymers with polyamide.
• the polyimide resin has a carboxylic acid residue having a fluorine atom and/or an amine residue having a fluorine atom.
• the total content ratio of the carboxylic acid residue having a fluorine atom and the amine residue having a fluorine atom in the total carboxylic acid residues and the total amine residues of each resin is preferably 10 mol% or more and 100 mol% or less, more preferably 30 mol% or more and 100 mol% or less, and even more preferably 50 mol% or more and 100 mol% or less.
• the preferred ranges for the total content ratio of the amine residues having a fluorine atom in the total amine residues and the total content ratio of the carboxylic acid residues having a fluorine atom in the total carboxylic acid residues are also the same as above.
• the weight average molecular weight of the polyimide resin is preferably 4,000 or more, more preferably 5,000 or more, even more preferably 7,000 or more, and particularly preferably 10,000 or more, calculated as polystyrene by gel permeation chromatography (hereinafter "GPC").
• the weight average molecular weight is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 30,000 or less, and particularly preferably 20,000 or less.
• Polyimide resins can be synthesized by known methods.
• the polyimide resin has a structure in which the resin terminal is sealed with a monoamine, a dicarboxylic anhydride, or a monocarboxylic acid derivative. From the viewpoint of improving sensitivity during exposure and improving mechanical properties, it is preferable that the polyimide resin has a radical polymerizable group and/or a heat-reactive group at the resin terminal that can react with the resin or other components.
• the radical polymerizable group and heat-reactive group at the resin terminal are preferably amine residues and/or carboxylic acid residues, and more preferably have a maleimide group or a nadimide group. Examples of acid monomers having these groups include maleic anhydride and nadic anhydride.
• the polyimide resin has a radical polymerizable group and/or a thermally reactive group at the end of the resin from the viewpoints of improving sensitivity during exposure, suppressing residues after development, suppressing residues after thermal curing, improving mechanical properties, and improving the reliability of the light-emitting device.
• the radical polymerizable group at the end of the resin is preferably one or more groups selected from the group consisting of styryl, cinnamoyl, maleimide, nadimide, (meth)acryloyl, alkenyl having 2 to 5 carbon atoms, and alkynyl having 2 to 5 carbon atoms.
• the thermally reactive group at the end of the resin is preferably one or more groups selected from the group consisting of phenolic hydroxyl, hydroxyimide, hydroxyamide, silanol, 1,1-bis(trifluoromethyl)methylol, mercapto, carboxy, carboxylic anhydride, sulfonic acid, alkoxyalkyl, hydroxyalkyl, epoxy, oxetanyl, and blocked isocyanate.
• the crosslinking reaction between the imide compound (H) and the polyimide resin described below is more likely to proceed, and the effects of the above invention are more pronounced.
• the polyimide has a polyimide unit
• the polyimide precursor has a polyimide precursor unit
• the polybenzoxazole has a polybenzoxazole unit
• the polybenzoxazole precursor has a polybenzoxazole precursor unit
• the polyamideimide has a polyamideimide unit
• the polyamideimide precursor has a polyamideimide precursor unit
• the polyamide has a polyamide unit
• a polyimide unit is a structural unit of a resin containing an amine residue and a carboxylic acid residue, and has two imide structures.
• a polyimide precursor unit is a structural unit of a resin containing an amine residue and a carboxylic acid residue, and has two amide acid structures, two amide acid ester structures, two amide acid amide structures, an amide acid structure and an amide acid ester structure, an amide acid structure and an amide acid amide structure, or an amide acid ester structure and an amide acid amide structure.
• An amide acid structure is a structure having one carboxylic acid amide bond and one carboxy group.
• An amide acid ester structure is a structure having one carboxylic acid amide bond and one carboxylic acid ester bond.
• An amide acid amide structure is a structure having one carboxylic acid amide bond and another carboxylic acid amide bond.
• a polybenzoxazole unit is a structural unit of a resin that contains an amine residue and a carboxylic acid residue and has two benzoxazole structures.
• a polybenzoxazole precursor unit is a structural unit of a resin that contains an amine residue and a carboxylic acid residue and has two hydroxyamide structures.
• a polyamideimide unit is a structural unit of a resin containing an amine residue and a carboxylic acid residue, the unit having an imide structure and an amide structure.
• a polyamideimide precursor unit is a structural unit of a resin containing an amine residue and a carboxylic acid residue, the unit having an amide structure and an amic acid structure, an amide structure and an amic acid ester structure, or an amide structure and an amic acid amide structure.
• the polyimide unit, polyimide precursor unit, polybenzoxazole unit, polybenzoxazole precursor unit, polyamideimide unit, polyamideimide precursor unit, and polyamide unit are all structural units that constitute a resin, and are repeating units having a repeating number of 2 or more.
• the repeating number of these units is preferably 2 or more, more preferably 5 or more, and even more preferably 10 or more. On the other hand, the repeating number is preferably 1,000 or less.
• Resins in which the content of polyimide units in the total of polyimide units and polyimide precursor units is 50 mol% or more are classified as polyimides. On the other hand, resins in which the content of polyimide units is less than 50 mol% are classified as polyimide precursors. Similarly, resins in which the content of polybenzoxazole units in the total of polybenzoxazole units and polybenzoxazole precursor units is 50 mol% or more are classified as polybenzoxazoles. On the other hand, resins in which the content of polybenzoxazole units is less than 50 mol% are classified as polybenzoxazole precursors.
• resins in which the content of polyamideimide units in the total of polyamideimide units and polyamideimide precursor units is 50 mol% or more are classified as polyamideimides.
• resins in which the content of polyamideimide units is less than 50 mol% are classified as polyamideimide precursors.
• the content ratio of polyimide units and polyimide precursor units can be calculated from the imide ring closure rate of the resin.
• the content ratio of polybenzoxazole units and polybenzoxazole precursor units can be calculated from the benzoxazole ring closure rate of the resin.
• the content ratio of polyamideimide units and polyamideimide precursor units can be calculated from the imide ring closure rate of the resin.
• a resin having two or more units selected from the group consisting of (1) polyimide units or their precursor units, (2) polybenzoxazole units or their precursor units, (3) polyamideimide units or their precursor units, and (4) polyamide units is classified into both resins based on the units.
• a resin having polyimide precursor units and polybenzoxazole precursor units is classified into both polyimide precursors and polybenzoxazole precursors.
• the structural unit in a resin corresponds to both a polyimide precursor unit and a polybenzoxazole precursor unit, for example, the structural unit is used when calculating the total content ratio of polyimide precursor units in the resin and the total content ratio of polybenzoxazole precursor units in the resin.
• the (A) binder resin satisfies the following condition (P1a). It is more preferable that the (A) binder resin further satisfies the following condition (P2a).
• the (A) binder resin is a polyimide-based resin
• the (A) binder resin satisfies the following condition (P1a), and more preferably the following condition (P2a), from the viewpoint of suppressing residues after development and improving the reliability of the light-emitting device.
• the content of fluorine element in the structure of the binder resin is preferably 0 ppm by mass or more, more preferably 0.010 ppm by mass or more, even more preferably 0.030 ppm by mass or more, even more preferably 0.050 ppm by mass or more, particularly preferably 0.070 ppm by mass or more, and most preferably 0.10 ppm by mass or more.
• the content of fluorine element is preferably 10,000 ppm by mass or less, more preferably 5,000 ppm by mass or less, even more preferably 1,000 ppm by mass or less, even more preferably 500 ppm by mass or less, particularly preferably 300 ppm by mass or less, and most preferably 100 ppm by mass or less. Furthermore, the content of fluorine element is preferably 50 ppm by mass or less, more preferably 30 ppm by mass or less, even more preferably 10 ppm by mass or less, even more preferably 5 ppm by mass or less, particularly preferably 3 ppm by mass or less, and most preferably 1 ppm by mass or less.
• the preferred range of the content of fluoride ions in the structure of the binder resin (A) is the same as the preferred range of the content of fluorine elements in the structure of the binder resin (A) described above.
• the binder resin (A) satisfies the above-mentioned condition (P1a), and more preferably satisfies the above-mentioned condition (P2a).
• the content of fluorine elements in the structure of the binder resin may be 0 ppm by mass.
• the content of fluoride ions in the structure of the binder resin may also be 0 ppm by mass.
• the content of fluorine element is a specific value or less in the photosensitive composition
• the content of fluorine element, fluoride ion, or anion containing fluorine element derived from these resins is a specific value or less, so that it is presumed that protons in the photosensitive composition are locally activated by interactions such as hydrogen bonds of each component in the photosensitive composition. Therefore, it is considered that the effect of suppressing residue after development becomes remarkable due to the dissolution promotion action in the developer.
• the reliability of the light-emitting element is improved by suppressing ion migration and electromigration caused by metal impurities and ion impurities that have an adverse effect on the light-emitting properties or electrical insulation. It is also presumed that the reliability of the display device is improved by suppressing migration and aggregation of metals in the electrodes or metal wiring.
• (A1x) resins other than polyimide resins having no weak acidic groups and (A2x) resins or (A2y) resins other than polyimide resins having no weak acidic groups will be collectively described.
• polysiloxanes are (A1x) resins because they have silanol groups and contain a siloxane structure in the structural unit of the resin.
• the polysiloxane preferably has an organosilane unit containing an acidic group, and from the viewpoint of improving sensitivity during exposure, it is more preferable that the polysiloxane has an organosilane unit containing a weakly acidic group (WA). From the viewpoint of improving sensitivity during exposure and suppressing residues after development, it is also preferable that the polysiloxane has an organosilane unit containing a carboxy group, a carboxylic anhydride group, or a sulfonic acid group. Examples and preferred descriptions regarding the acidic group and the weakly acidic group (WA) are as described above for the binder resin (A).
• the polysiloxane preferably has a radically polymerizable group, and it is more preferable that the polysiloxane has an organosilane unit containing a radically polymerizable group.
• the radically polymerizable group are as described above for the binder resin (A).
• the polysiloxane preferably has a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure, and more preferably has an organosilane unit containing a naphthyl group, an anthracenyl group, a biphenyl group, a phenyl group, a tolyl group, or a methoxyphenyl group.
• Maleimide resin is a resin that has at least two maleimide groups.
• Maleimide-styrene resin is a resin that has a maleimide group and units derived from a styrene derivative.
• Maleimide-triazine resin is a resin that has a maleimide group and units that contain a triazine structure.
• Maleimide-oxazine resin is a resin that has a maleimide group and units that contain an oxazine structure. These are resins that are different from polyimide-based resins.
• the (A1) weakly acidic group-containing resin preferably contains an (A1y) resin.
• the (A1y) resin preferably contains one or more selected from the group consisting of phenolic resins, polyhydroxystyrene, phenolic group-containing epoxy resins, and phenolic group-containing acrylic resins.
• the (A1y) resin may be either a single resin or a copolymer thereof.
• the (A1y) resin preferably has one or more types selected from the group consisting of: (y1) structural unit: a structural unit containing at least two phenolic hydroxyl groups; (y2) structural unit: a structural unit containing a phenolic hydroxyl group and an aromatic group; and (y3) structural unit: a structural unit containing a phenolic hydroxyl group and a structural unit containing a second aromatic group; and it is more preferable that the (A1y) resin has a (y1) structural unit and/or a (y2) structural unit. Furthermore, from the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving the reliability of the light-emitting device, the (A1y) resin preferably has a (y1) structural unit.
• the at least two phenolic hydroxyl groups in the (y1) structural unit are bonded to the same aromatic ring or different aromatic rings, preferably to different aromatic rings, and also preferably to different aromatic rings in a condensed polycyclic structure.
• the aromatic group in the (y2) structural unit is an aromatic group other than the aromatic ring to which the phenolic hydroxyl group is bonded.
• the second aromatic group in the (y3) structural unit is an aromatic group other than the aromatic ring to which the phenolic hydroxyl group is bonded.
• the second aromatic group is a term used to distinguish it from the aromatic group in the (y2) structural unit (meaning an aromatic group other than the aromatic ring to which the phenolic hydroxyl group is bonded).
• the phenolic resin is preferably a novolac resin, a resole resin, or a phenol aralkyl resin.
• the phenolic resin preferably has a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, an aromatic structure, or a heterocyclic structure.
• the polyhydroxystyrene preferably has units derived from a (meth)acrylic acid ester derivative containing a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure, or units derived from a styrene derivative.
• the phenol group-containing epoxy resin may be, for example, a resin obtained by reacting a polyfunctional epoxy compound with a phenol compound having an epoxy-reactive group, and is preferably a phenol group-containing cardo resin or a phenol group-containing epoxy-modified resin.
• the phenol group-containing epoxy-modified resin is preferably a phenol group-containing epoxy ester resin.
• the phenol group-containing cardo resin preferably has a condensed polycyclic structure or a condensed polycyclic heterocyclic structure.
• the phenol group-containing epoxy resin preferably has a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure.
• a phenol group-containing acrylic resin is a resin obtained by reacting an acrylic resin described below with a phenol compound having an addition reactive group.
• Another example is a resin obtained by radical copolymerization of a copolymerization component having a phenolic hydroxyl group with another copolymerization component such as a (meth)acrylic acid derivative.
• the phenol group-containing acrylic resin is a resin different from polyhydroxystyrene.
• the phenol group-containing acrylic resin preferably has a unit derived from a (meth)acrylic acid ester derivative containing a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure, or a unit derived from a styrene derivative.
• the condensed polycyclic structure, condensed polycyclic heterocyclic structure, aromatic structure, or heterocyclic structure in these resins is preferably a fluorene structure, an anthracene structure, a naphthalene structure, a tricyclo[5.2.1.0 2,6 ]decane structure, an adamantane structure, a xanthene structure, an isoindolinone structure, a biphenyl structure, a benzene structure, a bisphenol A structure, a bisphenol F structure, a bisphenol AF structure, an isocyanuric acid structure, or a triazine structure.
• the resin (A2) that does not have a weak acidic group preferably contains an (A2x) resin, and from the viewpoints of improving sensitivity during exposure and suppressing residue after development, it is preferable to further contain an (A2y) resin.
• the (A2x) resin preferably contains one or more types selected from the group consisting of a polycyclic side chain-containing resin, an acid-modified epoxy resin, and an acrylic resin.
• the (A2x) resin may be a single resin or a copolymer thereof.
• the (A2y) resin preferably contains one or more types selected from the group consisting of a polycyclic side chain-containing resin, an acid-modified epoxy resin, and an acrylic resin, from the viewpoints of improving sensitivity during exposure and suppressing residue after development.
• the (A2y) resin may be a single resin or a copolymer thereof.
• the polycyclic side chain-containing resin is preferably a cardo-based resin having a condensed polycyclic structure or a condensed polycyclic heterocyclic structure.
• the acid-modified epoxy resin is preferably an epoxy (meth)acrylate resin having a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure.
• the acrylic resin preferably has a unit derived from a (meth)acrylic acid ester derivative containing a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, or an aromatic structure, or a unit derived from a styrene derivative. It is also preferable to have a unit derived from a (meth)acrylic acid ester derivative having an epoxy group.
• the condensed polycyclic structure, the condensed polycyclic heterocyclic structure, or the aromatic structure in these resins is preferably a fluorene structure, an anthracene structure, a naphthalene structure, a tricyclo[5.2.1.0 2,6 ]decane structure, an adamantane structure, a xanthene structure, an isoindolinone structure, a biphenyl structure, or a benzene structure.
• the total content ratio of the (A1x) resins in the total 100% by mass of the (A) binder resin is preferably 10% by mass or more, more preferably 30% by mass or more, even more preferably 50% by mass or more, and particularly preferably 70% by mass or more, from the viewpoint of reducing the taper of the pattern shape, improving the mechanical properties, and improving the reliability of the light-emitting element.
• the total content ratio of the (A1x) resins is preferably 100% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less, from the viewpoint of suppressing residue after development.
• the total content ratio of the (A1y) resins is preferably 5.0% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more, from the viewpoint of suppressing residue after development, reducing the taper of the pattern shape, and improving the mechanical properties.
• the total content ratio of the (A1y) resins is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less, from the viewpoint of improving the mechanical properties.
• the total content of the (A2x) resin and the (A2x) resin is preferably 5.0% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more.
• the total content of the (A2x) resin and the (A2y) resin is preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less.
• the content ratio of the binder resin (A) in the total solid content of the photosensitive composition of the present invention is preferably 10 mass% or more from the viewpoint of improving the characteristics of each resin.
• the content ratio of the binder resin (A) is preferably 75 mass% or less from the viewpoint of improving the characteristics of each resin.
• the total solid content of the composition refers to the total mass of all components in the composition excluding the solvent.
• the solid content concentration can be calculated by heating 1 g of the composition at 150°C for 30 minutes to evaporate and dry, measuring the mass remaining after heating, and calculating the solid content concentration from the mass before and after heating.
• the photosensitive composition of the present invention preferably further contains (B) a radical polymerizable compound (hereinafter, "(B) compound") and/or (F) a crosslinking agent.
• the (B) compound refers to a compound having a radical polymerizable group. Examples and preferred descriptions regarding the radical polymerizable group are as described in the above (A) binder resin.
• the radical polymerizable group is preferably a (meth)acryloyl group from the viewpoints of promoting radical polymerization, improving sensitivity during exposure, and improving mechanical properties.
• the number of radical polymerizable groups possessed by the (B) compound is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more, from the viewpoints of improving sensitivity during exposure and improving mechanical properties.
• the number of radical polymerizable groups is preferably 12 or less, more preferably 10 or less, even more preferably 8 or less, and particularly preferably 6 or less, from the viewpoints of improving mechanical properties and improving the reliability of the light-emitting element.
• the content of the binder resin (A) is preferably 25 parts by mass or more, more preferably 35 parts by mass or more, and even more preferably 45 parts by mass or more, when the total of the binder resin (A) and the compound (B) is 100 parts by mass, from the viewpoints of reducing the taper of the pattern shape, improving the mechanical properties, and improving the reliability of the light-emitting element.
• the content of the binder resin (A) is preferably 85 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, from the viewpoints of improving the sensitivity during exposure and suppressing the residue after development.
• the content of the compound (B) is preferably 15 parts by mass or more, when the total of the binder resin (A) and the compound (B) is 100 parts by mass, from the viewpoints of improving the above-mentioned characteristics.
• the content of the compound (B) is preferably 75 parts by mass or less, from the viewpoints of improving the above-mentioned characteristics.
• the photosensitive composition of the present invention preferably further contains a (B) radical polymerizable compound from the viewpoints of improving sensitivity during exposure, suppressing residues after development, suppressing residues after thermal curing, improving mechanical properties, and improving the reliability of the light-emitting device.
• the (B) radical polymerizable compound preferably has one or more groups selected from the group consisting of a styryl group, a cinnamoyl group, a maleimide group, a nadimide group, a (meth)acryloyl group, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms.
• the photosensitive composition of the present invention preferably satisfies at least one of the following conditions ( ⁇ ), ( ⁇ ), and ( ⁇ ).
• the (B) compound contains the following (B1) compound and (B2) compound;
• the (B) compound contains the following (B3) compound and (B4) compound;
• the compound B) contains the following compound (B1) or compound (B2) and further contains the following compound (B3) or compound (B4):
• Compound (I-b2) Structure Condensed polycyclic structure , fused polycyclic heterocyclic structures, or aromatic structures.
• (II-b2) Structure Compound having a structure containing an aliphatic structure and further having at least two radical polymerizable groups
• the (B1) compound further has a (II-b1) structure: a structure containing an aliphatic structure.
• the (B3) compound and the (B4) compound are compounds different from the above-mentioned (B1) compound and (B2) compound, and do not have a structure containing a fused polycyclic alicyclic structure, an alicyclic structure, or a heterocyclic structure, nor a structure containing a fused polycyclic structure, a fused polycyclic heterocyclic structure, or an aromatic structure.
• the minimum number of atoms in the (I-b3) structure or the (I-b4) structure above refers to the minimum number of atoms, including carbon atoms and heteroatoms, between the carbonyl carbons of the two (meth)acryloyl groups.
• the atoms bonded to the carbon atoms and heteroatoms between the carbonyl carbons are not included in the calculation of the minimum number of atoms. For example, when an oxygen atom, a propylene group, and an oxygen atom are present between the carbonyl carbons, the minimum number of atoms is five.
• the minimum number of atoms refers to the minimum number of atoms, including carbon atoms and heteroatoms linking the carbonyl carbons of all the (meth)acryloyl groups. Similarly, the atoms bonded to the carbon atoms and heteroatoms linking the carbonyl carbons are not included in the calculation of the minimum number of atoms.
• (B) compounds not only improve the degree of crosslinking of the cured product by generating radicals during exposure or heating, but also improve the degree of crosslinking by reacting with the side chains or terminal radical polymerizable groups of the resin, resulting in a significant improvement in mechanical properties.
• (B) compounds having an aliphatic structure in the above (II-b1), (II-b2), (I-b3), or (I-b4) structures reduce the low molecular weight components derived from (B) compounds in the cured product, thereby suppressing ion migration and electromigration, and are also presumed to improve the reliability of light-emitting devices by suppressing the aggregation of metals in electrodes, etc.
• the (B) compound further contains a (B5) compound: a compound having a structure including a condensed polycyclic structure or a condensed polycyclic heterocyclic structure and further having at least two radically polymerizable groups.
• the (B5) compound is a compound different from the above (B2) compound and does not have the above (II-b2) structure.
• the (B) compound contains one or more compounds selected from the group consisting of the (B1) compound, the (B2) compound, the (B3) compound, the (B4) compound, and the (B5) compound.
• the preferred contents of these (B) compounds are the same as those described above.
• the photosensitive composition of the present invention contains a photosensitizer (C).
• the photosensitizer (C) refers to a compound that undergoes bond cleavage, reaction, or structural change upon exposure to generate another compound, thereby imparting positive or negative photosensitivity to the composition.
• the photosensitizer (C) preferably contains one or more selected from the group consisting of a naphthoquinone diazide compound (C1) (hereinafter, “compound (C1)”), a photopolymerization initiator (C2) (hereinafter, “compound (C2)”), a photoacid generator (C3) (hereinafter, “compound (C3)”), and a photobase generator (C4) (hereinafter, “compound (C4)”).
• a compound (C1) and/or a compound (C3) it is also preferable to further contain a compound (C2) or a compound (C4).
• the composition contains the compound (C2) and/or the compound (C3), and it is also preferable that the composition further contains the compound (C1) or the compound (C4).
• the content of the (C) photosensitizer is preferably 1.0 part by mass or more from the viewpoint of improving sensitivity during exposure, when the total of the (A) binder resin and the (B) compound is taken as 100 parts by mass.
• the content of the (C) photosensitizer is preferably 30 parts by mass or less from the viewpoint of suppressing residues after development.
• the (C1) compound refers to a compound that undergoes a structural change upon exposure to generate an indene carboxylic acid and/or a sulfoindene carboxylic acid.
• the inclusion of the (C1) compound is suitable for forming a positive pattern.
• the exposed portion of the film of the composition is selectively solubilized in an alkaline developer by the acidic compound resulting from the structural change of the (C1) compound, and therefore the effect of improving the resolution after development is remarkable.
• the (C1) compound is preferably a 1,2-naphthoquinone diazide-5-sulfonic acid ester (hereinafter, "5-ester”) or 1,2-naphthoquinone diazide-4-sulfonic acid ester (hereinafter, "4-ester”) of a compound having a phenolic hydroxyl group.
• the (C1) compound preferably contains a 5-ester
• the (C1) compound preferably contains a 4-ester.
• the (C1) compound more preferably contains a 5-ester and a 4-ester.
• the total content ratio of 5-ester groups and 4-ester groups in the total number of moles of phenolic hydroxyl groups, 1,2-naphthoquinone diazide-5-sulfonic acid ester groups (hereinafter, "5-ester groups”), and 1,2-naphthoquinone diazide-4-sulfonic acid ester groups (hereinafter, "4-ester groups") in the (C1) compound (hereinafter, "esterification rate”) is preferably 50 mol% or more, more preferably 55 mol% or more, and even more preferably 60 mol% or more, from the viewpoint of improving the resolution after development.
• the esterification rate is preferably 100 mol% or less, more preferably 90 mol% or less, even more preferably 80 mol% or less, and particularly preferably 70 mol% or less, from the viewpoint of improving the sensitivity during exposure. It is also preferable to mix two or more (C1) compounds having different esterification rates to achieve the above esterification rate.
• the total content ratio of compounds having one 5-ester group or one 4-ester group in the molecule and compounds having two 5-ester groups or two 4-ester groups in the molecule (hereinafter referred to as the "low ester substitution ratio") in a total of 100 mol% of (C1) compounds is preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more, from the viewpoint of improving sensitivity during exposure.
• the low ester substitution ratio is preferably 100 mol% or less, more preferably 95 mol% or less, and even more preferably 90 mol% or less, from the viewpoint of improving resolution after development.
• the low ester substitution ratio in a total of 100 mol% of the (C1) compound is preferably 0 mol% or more, more preferably 10 mol% or more, even more preferably 20 mol% or more, and particularly preferably 30 mol% or more, from the viewpoint of improving sensitivity during exposure.
• the low ester substitution ratio is preferably less than 60 mol%, more preferably 50 mol% or less, and even more preferably 40 mol% or less, from the viewpoint of suppressing residues after development.
• Examples of methods for producing compound (C1) include a method of esterifying a compound having a phenolic hydroxyl group with naphthoquinone diazide sulfonic acid, and a method of esterifying a compound having a phenolic hydroxyl group with naphthoquinone diazide sulfonic acid chloride.
• the naphthoquinone diazide sulfonic acid chloride is preferably 1,2-naphthoquinone diazide-5-sulfonic acid chloride or 1,2-naphthoquinone diazide-4-sulfonic acid chloride.
• the (C2) compound refers to a compound that generates radicals by bond cleavage and/or reaction upon exposure.
• the inclusion of the (C2) compound is suitable for forming a negative pattern. Even if the amount of radicals generated from the (C2) compound during exposure is small, the radical polymerization of the above-mentioned (B) compound and the like proceeds in a chain reaction, so that the effect of improving the sensitivity during exposure is remarkable.
• the (C2) compound is preferably a benzyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, a biimidazole compound, a phosphine oxide compound, an oxime ester compound, an acridine compound, a titanocene compound, a benzophenone compound, an acetophenone compound, an aromatic ketoester compound, or a benzoic acid ester compound, and from the viewpoint of improving sensitivity during exposure and improving mechanical properties, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, a biimidazole compound, a phosphine oxide compound, or an oxime ester compound is more preferable, and an oxime ester compound is even more preferable.
• ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, biimidazole compounds, phosphine oxide compounds, and oxime ester compounds have the effect of improving the degree of crosslinking of the cured product and promoting the ring-closing reaction of the resin due to the generation of radicals when heated and interactions between the hydroxyl group, amino group, imidazole structure, phosphine oxide structure, or oxime ester structure, resulting in a significant improvement in mechanical properties.
• the (C3) compound refers to a compound that generates an acid by bond cleavage and/or reaction upon exposure.
• the inclusion of the (C3) compound is suitable for negative pattern formation from the viewpoint of promoting cationic polymerization.
• a resin or the like has an acidic group protected by an acid-dissociable group, it is suitable for positive pattern formation from the viewpoint of liberating the acidic group upon exposure, and the effect of improving the sensitivity upon exposure is remarkable.
• Examples of the (C3) compound include ionic compounds and non-ionic compounds.
• the ionic compound is preferably a triorganosulfonium salt compound.
• the non-ionic compound is preferably a halogen-containing compound, a diazomethane compound, a sulfone compound, a sulfonate compound, a carboxylate compound, a sulfonimide compound, a phosphate compound, or a sulfonebenzotriazole compound.
• the (C4) compound refers to a compound that generates a base by bond cleavage and/or reaction upon exposure.
• the inclusion of the (C4) compound is suitable for negative pattern formation from the viewpoint of promoting anionic polymerization.
• a resin or the like has an acidic group protected by a base dissociable group, it is suitable for positive pattern formation from the viewpoint of liberating the acidic group upon exposure, and the effect of improving the sensitivity upon exposure is remarkable.
• Compounds include, for example, ionic compounds and non-ionic compounds.
• Ionic compounds are preferably diazabicycloalkene salt compounds, triazabicycloalkene salt compounds, ⁇ -keto quaternary ammonium salt compounds, benzyl quaternary ammonium salt compounds, guanidine salt compounds, or biguanide salt compounds.
• Ionic compounds preferably have a ketoprofen structure, an oxoxanthene structure, a benzofuran structure, or a naphthalene structure.
• Non-ionic compounds are preferably nitrobenzyl carbamate compounds, anthracenyl carbamate compounds, benzoin carbamate compounds, anthraquinone carbamate compounds, hydroxycinnamamide compounds, or coumarinamide compounds.
• the photosensitive composition of the present invention preferably further contains a colorant (D).
• the colorant (D) refers to a compound that causes coloring by absorbing light of a visible light wavelength (380 to 780 nm).
• the colorant (D) is preferably a pigment or a dye.
• the colorant (D) preferably contains a black agent or a mixture of two or more colorants.
• the black agent preferably contains an organic black pigment and/or an inorganic black pigment.
• the black color in the colorant (D) is as described in paragraphs [0284] to [0285] of WO 2019/087985.
• the content ratio of the colorant (D) in the total solid content of the photosensitive composition of the present invention is preferably 5.0% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more, from the viewpoints of suppressing external light reflection and improving the reliability of the element.
• the content ratio of the colorant (D) is preferably 70% by mass or less, more preferably 50% by mass or less, from the viewpoints of improving sensitivity during exposure and suppressing residues after development.
• the organic black pigment contains one or more types selected from the group consisting of benzofuranone-based black pigments, perylene-based black pigments, and azomethine-based black pigments
• the benzofuranone-based black pigment contains a compound having at least two benzofuran-2(3H)-one structures that may share a benzene ring or at least two benzofuran-3(2H)-one structures that may share a benzene ring, a geometric isomer thereof, a salt thereof, or a salt of a geometric isomer thereof
• the perylene-based black pigment contains a compound having a 3,4,9,10-perylenetetracarboxylic acid bisbenzimidazole structure, a geometric isomer thereof, a salt thereof, or a salt of a geometric isomer thereof
• the organic black pigment is preferably an anthraquinone-based black pigment, an aniline-based black pigment, an azo-based black pigment, or carbon black.
• the carbon black is preferably resin-coated, dye-coated, oxidized, surface-modified with an organic group having an ionic group, or surface-treated with a sulfonic acid group.
• the mixture of two or more colors of coloring agents contains a mixture of two or more colors of color pigments and/or a mixture of two or more colors of color dyes, and it is more preferable that the two or more colors include blue and/or purple, and also include red and orange, and that the color pigments are anthraquinone-based pigments, diketopyrrolopyrrole-based pigments, perylene-based pigments, isoindoline-based pigments, isoindolinone-based pigments, imidazolone-based pigments, quinacridone-based pigments, pyranthrone-based pigments, phthalocyanine-based pigments, indanthrone-based pigments, or dioxazine-based pigments, and that the color dyes are squarylium-based dyes, xanthene-based dyes, triarylmethane-based dyes,
• the average primary particle diameter of the pigment is preferably 20 nm or more from the viewpoint of improving the reliability of the element.
• the average primary particle diameter of the pigment is preferably 150 nm or less from the viewpoint of suppressing external light reflection and improving the reliability of the element.
• the inorganic black pigment contains one or more types selected from the group consisting of nitrides containing metal elements, carbides containing metal elements, and oxynitrides containing metal elements (hereinafter referred to as "specific inorganic black pigments").
• the metal element is one or more types selected from the group consisting of zirconium, vanadium, niobium, hafnium, and tantalum
• the inorganic black pigment contains one or more types selected from the group consisting of nitrides, carbides, and oxynitrides of zirconium, vanadium, niobium, hafnium, or tantalum
• the inorganic black pigment contains one or more types selected from the group consisting of zirconium nitrides, zirconium carbides, and zirconium oxynitrides from the viewpoint of improving sensitivity during exposure.
• Zirconium nitrides, zirconium carbides, and zirconium oxynitrides have high transmittance for wavelengths in the ultraviolet region, so the effect of improving sensitivity during exposure is remarkable.
• the specific inorganic black pigment preferably contains zirconium, vanadium, niobium, hafnium, or tantalum as a main component element.
• the main component element refers to the element that is contained most abundantly by mass among the constituent elements.
• the specific inorganic black pigment preferably contains an element different from the main component element, and more preferably contains B, Al, Si, Mn, Co, Ni, Fe, Cu, Zn, or Ag.
• the crystallite size of each compound particle, such as zirconium nitride particles, contained in a specific inorganic black pigment can be calculated from the half-width of the peak derived from the (111) plane in the X-ray diffraction spectrum using CuK ⁇ radiation as the X-ray source.
• the crystallite size is preferably 5.0 nm or more from the viewpoint of suppressing external light reflection and improving the reliability of the element.
• the crystallite size is preferably 60 nm or less from the viewpoint of improving sensitivity during exposure and suppressing external light reflection.
• the crystallite size of the particle powder, the crystallite size of the particles in the dispersion, and the crystallite size of the particles in the film can be determined based on the methods described in paragraphs [0172] to [0179] of WO 2021/182499.
• the pigment has a coating layer.
• the coating layer refers to a layer that covers the pigment surface, and examples of such layers include a layer formed by surface treatment with a silane coupling agent or coating treatment with a resin.
• the coating layer preferably has one or more types selected from the group consisting of a silica coating layer, a metal oxide coating layer, and a metal hydroxide coating layer.
• the photosensitive composition of the present invention preferably further contains a dispersant (E).
• the dispersant (E) refers to a compound having a structure that interacts with the pigment surface and a structure that inhibits the approach of pigments to each other. From the viewpoint of improving the dispersion stability of the pigment, the dispersant (E) preferably has a basic group, an acidic group, or a salt structure thereof, and more preferably has a basic group or a salt structure thereof.
• the photosensitive composition of the present invention preferably further contains a (B) compound and/or a (F) crosslinking agent.
• the (F) crosslinking agent refers to a compound having a crosslinkable group, a cationic polymerizable group, or an anionic polymerizable group capable of reacting with a resin or the like.
• the (F) crosslinking agent preferably has one or more groups selected from the group consisting of alkoxyalkyl groups, hydroxyalkyl groups, epoxy groups, oxetanyl groups, and blocked isocyanate groups (hereinafter, "specific crosslinkable groups").
• the alkoxyalkyl group is preferably an alkoxymethyl group or an alkoxyethyl group, more preferably a methoxymethyl group or a methoxyethyl group.
• the hydroxyalkyl group is preferably a methylol group or an ethylol group.
• the number of specific crosslinkable groups possessed by the (F) crosslinking agent is preferably 2 or more, more preferably 3 or more, even more preferably 4 or more, and particularly preferably 6 or more.
• the number of specific crosslinkable groups is preferably 12 or less, more preferably 10 or less, and even more preferably 8 or less.
• the content of the (F) crosslinking agent is preferably 1.0 part by mass or more, when the total of the (A) binder resin and the (B) compound is taken as 100 parts by mass, from the viewpoints of improving sensitivity during exposure and improving mechanical properties.
• the content of the (F) crosslinking agent is preferably 30 parts by mass or less, from the viewpoints of suppressing residues after development and improving mechanical properties.
• the photosensitive composition of the present invention preferably further contains a (F) crosslinking agent from the viewpoints of improving sensitivity during exposure, suppressing residues after development, suppressing residues after thermal curing, improving mechanical properties, and improving the reliability of the light-emitting device.
• the (F) crosslinking agent preferably has one or more groups selected from the group consisting of an alkoxyalkyl group, a hydroxyalkyl group, an epoxy group, an oxetanyl group, and a blocked isocyanate group.
• the (F) crosslinking agent contains (F1) compound: a compound having at least two phenolic hydroxyl groups and at least two specific crosslinkable groups, and/or (F2) compound: a compound having a structure including a heterocyclic structure and at least two specific crosslinkable groups.
• the preferred contents of these (F) crosslinking agents are the same as those described above.
• the (F1) compound preferably has at least two structures in which a phenolic hydroxyl group and a specific crosslinkable group are bonded to one aromatic structure, and more preferably has at least two structures in which a phenolic hydroxyl group and at least two specific crosslinkable groups are bonded to one aromatic structure.
• the heterocyclic structure in the (F2) compound is preferably a nitrogen-containing cyclic structure, more preferably a cyclic structure having at least two nitrogen atoms, and even more preferably an isocyanuric acid structure, a triazine structure, a glycoluril structure, an imidazolidone structure, a pyrazole structure, an imidazole structure, a triazole structure, a tetrazole structure, or a purine structure.
• the number of nitrogen atoms in the heterocyclic structure in the (F2) compound is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. On the other hand, the number of nitrogen atoms is preferably 6 or less, and more preferably 4 or less.
• the photosensitive composition of the present invention preferably further contains (G) inorganic particles.
• G) inorganic particles refer to particles containing an element selected from the group consisting of metal elements, metalloid elements, and semiconductor elements as a main component.
• the main component refers to the component that is contained most in the constituent components based on mass.
• (G) inorganic particles preferably have hydroxyl groups and/or silanol groups on the particle surface from the viewpoint of improving the reliability of the light-emitting device.
• (G) inorganic particles preferably contain one or more selected from the group consisting of silica particles, alumina particles, titania particles, vanadium oxide particles, chromium oxide particles, iron oxide particles, cobalt oxide particles, copper oxide particles, zinc oxide particles, zirconium oxide particles, niobium oxide particles, tin oxide particles, and cerium oxide particles from the viewpoint of improving the reliability of the light-emitting device, and more preferably contain silica particles from the viewpoint of suppressing external light reflection.
• the silica particles have a radical polymerizable group, a thermally reactive group, a hydroxy group, a silanol group, an alkoxysilyl group, an alkylsilyl group, a dialkylsilyl group, a trialkylsilyl group, a phenylsilyl group, or a diphenylsilyl group on the particle surface, and from the viewpoint of improving mechanical properties, it is even more preferable that the particles have a radical polymerizable group or a thermally reactive group on the particle surface. Examples and preferred descriptions regarding the radical polymerizable group are as described above in the (A) binder resin.
• silica particles are believed to capture metal impurities and ionic impurities that adversely affect electrical insulation due to the acidity and negative charge of the hydroxyl groups and/or silanol groups on the particle surface.
• the robust structure of the particles allows them to retain the captured impurities even after heat treatment or voltage application, which is believed to improve the reliability of light-emitting devices.
• the silica particles unevenly distributed on the surface of the cured product are believed to reduce the reflection and scattering of incident external light.
• the content of sodium element in the silica particles is preferably 1.0 ppm by mass or more from the viewpoint of improving the reliability of the light-emitting device.
• the content of sodium element in the silica particles is preferably 1,000 ppm by mass or less from the viewpoint of improving the reliability of the light-emitting device.
• Examples of the form of sodium element include ions (Na + ) and salts with silanol groups (Si—ONa).
• the content ratio of the (G) inorganic particles in the total solid content of the photosensitive composition of the present invention is preferably 5.0 mass% or more from the viewpoint of improving the reliability of the light-emitting device.
• the content ratio of the (G) inorganic particles is preferably 90 mass% or less from the viewpoint of suppressing residues after development.
• the photosensitive composition of the present invention further contains an (H) imide compound, and the (H) imide compound has at least two (I) structures: a structure in which a structure containing an imide bond and a cyclic structure having a phenolic hydroxyl group and/or a fluorine-containing substituent are bonded, and further has a (II) structure: a structure connecting at least two (I) structures (however, the above (A) binder resin is excluded). Note that the imide bond in the above (I) structure does not contain a hydroxyimide group.
• the atom bonded to the cyclic structure in the (I) structure may be either a nitrogen atom in the imide bond or another atom in the structure containing an imide bond. Note that the number of other atoms in the structure containing an imide bond bonded to the "*** structure" may be two or more.
• (H) imide compounds having these structures may be collectively referred to as specific (H) imide compounds.
• the structure containing an imide bond in the above (I) structure is preferably an aromatic structure containing an imide bond, a condensed polycyclic structure containing an imide bond, an alicyclic structure containing an imide bond, an aliphatic structure containing an imide structure, a succinimide structure, a maleimide structure, or a nadimide structure, and more preferably an aromatic structure containing an imide bond and having 6 to 15 carbon atoms, a condensed polycyclic structure containing an imide bond and having 6 to 20 carbon atoms, an alicyclic structure containing an imide bond and having 4 to 10 carbon atoms, an aliphatic structure containing an imide structure and having 1 to 6 carbon atoms, a succinimide structure, a maleimide structure, or a nadimide structure.
• the "*** structure” containing an imide bond refers to an "*** structure” to which an imide bond is bonded, or at least two "*** structures” linked by an imide bond.
• the atom bonded to the "*** structure” may be either the nitrogen atom in the imide bond or another atom in the structure containing an imide bond.
• the number of other atoms in the structure containing the imide bond that is bonded to the "*** structure” may be two or more.
• the cyclic structure in the above (I) structure is preferably an aromatic structure or a condensed polycyclic structure, more preferably an aromatic structure having 6 to 15 carbon atoms or a condensed polycyclic structure having 6 to 20 carbon atoms.
• the aromatic structure is preferably a biphenyl structure or a benzene structure.
• the condensed polycyclic structure is preferably a fluorene structure, an anthracene structure, a naphthalene structure, a tricyclo[5.2.1.0 2,6 ]decane structure, or an adamantane structure.
• the above (II) structure is preferably an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, a direct bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylic acid ester bond, an amide bond, a urea bond, a urethane bond, a carbonate ester bond, a halogenated alkylene group, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group, and more preferably an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sul
• the alkylene group, halogenated alkylene group, cycloalkylene group, or arylene group is preferably an alkylene group having 1 to 10 carbon atoms, a halogenated alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the hydrocarbon group in the hydrocarbon group containing an ether bond is preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms in the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the specific (H) imide compound contains an (H1) compound: a compound in which the cyclic structure in the (I) structure is a cyclic structure having a fluorine-containing substituent, and/or an (H2) compound: a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group.
• an (H1) compound a compound in which the cyclic structure in the (I) structure is a cyclic structure having a fluorine-containing substituent
• an (H2) compound a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group.
• the specific (H) imide compound preferably contains (H1x) compound: a compound in which the cyclic structure in the (I) structure is a cyclic structure having a fluorine-containing substituent and the (II) structure is an ether bond, and/or (H2y) compound: a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group and the (II) structure is an alkylene group or a halogenated alkylene group.
• (H1x) compound a compound in which the cyclic structure in the (I) structure is a cyclic structure having a fluorine-containing substituent and the (II) structure is an ether bond
• (H2y) compound a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group and the (II) structure is an alkylene group or a halogenated alkylene group.
• a (H1x) compound In terms of suppressing water absorption, improving mechanical properties, and improving the reliability of the light-emitting device, it is more preferable to contain a (H1x) compound, more preferably to contain a (H2y) compound, and more preferably to contain a (H2z) compound described below. Furthermore, in terms of improving the above characteristics, it is even more preferable to contain one or more compounds selected from the group consisting of (H1x) compounds, (H2y) compounds, and (H2z) compounds.
• the cyclic structure having a fluorine-containing substituent is preferably a cyclic structure having a trifluoromethyl group, more preferably an aromatic structure having a trifluoromethyl group or a condensed polycyclic structure having a trifluoromethyl group, from the viewpoints of improving sensitivity during exposure, suppressing residues after development, suppressing water absorption, improving mechanical properties, and improving the reliability of the light-emitting device.
• the specific (H) imide compound contains an (H2z) compound: a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group, and the (II) structure is an alkylene group, a sulfonyl group, a condensed polycyclic structure, a hydrocarbon group containing an ether bond, an ether bond, a sulfide bond, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a cycloalkylene group, an arylene group, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• an (H2z) compound a compound in which the cyclic structure in the (I) structure is an aromatic structure having a phenolic hydroxyl group, and the (II
• the binder resin (A) contains one or more resins selected from the group consisting of the polyimide resins having a weak acidic group
• the polyimide resin having a weak acidic group has a primary amine residue (DA1)
• the primary amine residue (DA1) has at least two of the structures (Ia) and (IIa)
• the structure (IIa) is the specific structure described above
• the imide compound (H) preferably contains a compound (H2), and from the viewpoints of improving the above-mentioned properties, the imide compound (H) more preferably contains a compound (H2z).
• the specific (H) imide compound preferably contains one or more compounds selected from the group consisting of compounds represented by general formulas (15) to (17) from the viewpoints of improving sensitivity during exposure, suppressing residues after development, improving mechanical properties, and improving the reliability of the light-emitting device.
• R 101 and R 102 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 10 carbon atoms.
• R 103 and R 104 each independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an acyl group having 1 to 10 carbon atoms, a 1,1-bis(trifluoromethyl)methylol group, a mercapto group, or a sulfonic acid group.
• R 105 to R 108 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a group forming a ring.
• R 105 and R 106 form a ring
• the number of carbon atoms of the ring members formed by R 105 and R 106 is 3 to 10.
• R 107 and R 108 form a ring
• the number of carbon atoms of the ring members formed by R 107 and R 108 is 3 to 10.
• the ring connected by the ring-forming group represents a monocyclic or condensed polycyclic hydrocarbon ring.
• the hydrocarbon ring has an alicyclic structure or an aromatic structure.
• R 109 represents a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogenated alkyl group having 1 to 6 carbon atoms.
• X 1 and X 2 each independently represent a direct bond, a hydrocarbon group, a hydrocarbon group including an ether bond, or an amide group to which a hydrocarbon group is bonded.
• Y1 represents a direct bond, an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a hydrocarbon group, a hydrocarbon group containing an ether bond, a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• a and b each independently represent an integer of 0 to 4.
• c and d each independently represent an integer of 0 to 4.
• e and f each independently represent an integer of 0 to 3.
• g represents an integer of 0 to 6. Note that 1 ⁇ a+c ⁇ 4 and 1 ⁇ b+d ⁇ 4.
• the dashed line portion represents a carbon-carbon single bond or a carbon-carbon double bond.
• the hydrocarbon group, the hydrocarbon group containing an ether bond, and the hydrocarbon group in the amide group to which the hydrocarbon group is bonded are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, an arylene group having 6 to 15 carbon atoms, or an arylalkylene group having 10 to 20 carbon atoms.
• the hydrocarbon group and the hydrocarbon group containing an ether bond are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms of the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• the above-mentioned substituents and structures may have heteroatoms and may be either unsubstituted or substituted.
• R 111 to R 114 and R 151 to R 154 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 10 carbon atoms.
• R 115 to R 118 and R 155 to R 158 each independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an acyl group having 1 to 10 carbon atoms, a 1,1-bis(trifluoromethyl)methylol group, a mercapto group, or a sulfonic acid group.
• R 119 to R 122 and R 159 to R 162 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a group forming a ring.
• R 119 and R 120 form a ring
• the number of carbon atoms of the ring members formed by R 119 and R 120 is 3 to 10.
• R 121 and R 122 form a ring
• the number of carbon atoms of the ring members formed by R 121 and R 122 is 3 to 10.
• R 159 and R 160 form a ring
• the number of carbon atoms of the ring members formed by R 159 and R 160 is 3 to 10.
• the number of carbon atoms of the ring members formed by R 161 and R 162 is 3 to 10.
• the rings connected by the ring-forming group represent a monocyclic or condensed polycyclic hydrocarbon ring.
• the hydrocarbon ring has an alicyclic structure or an aromatic structure.
• R 123 , R 124 , R 163 , and R 164 each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogenated alkyl group having 1 to 6 carbon atoms.
• W 3 and W 7 each independently represent a tetravalent to decavalent organic group.
• R 125 represents a group represented by general formula (18) or general formula (19).
• R 126 and R 166 each independently represent a phenolic hydroxyl group, a sulfonic acid group, or a mercapto group.
• X 3 to X 6 and X 7 to X 10 each independently represent a direct bond, a hydrocarbon group, a hydrocarbon group containing an ether bond, or an amide group to which a hydrocarbon group is bonded.
• Y3 , Y5 , Y7 , and Y9 each independently represent a direct bond, an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, a carboxylate bond, an amide bond, a urea bond, a urethane bond, a carbonate bond, a hydrocarbon group, a hydrocarbon group containing an ether bond, a condensed polycyclic structure, a condensed polycyclic heterocyclic structure, a hydrocarbon group containing a carbonyloxy group, or a hydrocarbon group containing a carbonylamide group.
• a, b, c, and d each independently represent an integer from 0 to 4.
• e, f, g, and h each independently represent an integer from 0 to 4.
• i, j, k, and l each independently represent an integer from 0 to 3.
• m and n each independently represent an integer from 0 to 6. Note that 1 ⁇ a+e ⁇ 4 and 1 ⁇ b+f ⁇ 4. Also, 1 ⁇ c+g ⁇ 4 and 1 ⁇ d+h ⁇ 4.
• o represents an integer from 2 to 8
• p represents an integer from 0 to 6, and 2 ⁇ o+p ⁇ 8.
• x represents an integer from 1 to 5.
• the dashed lines represent a carbon-carbon single bond or a carbon-carbon double bond.
• a, b, c, and d each independently represent an integer from 0 to 4.
• e, f, g, and h each independently represent an integer from 0 to 4.
• i, j, k, and l each independently represent an integer from 0 to 3.
• m and n each independently represent an integer from 0 to 6. Note that 1 ⁇ a+e ⁇ 4 and 1 ⁇ b+f ⁇ 4. Also, 1 ⁇ c+g ⁇ 4 and 1 ⁇ d+h ⁇ 4.
• p represents an integer from 0 to 6.
• y represents an integer from 1 to 5.
• the dashed portions represent carbon-carbon single bonds or carbon-carbon double bonds.
• the hydrocarbon group, the hydrocarbon group containing an ether bond, and the hydrocarbon group in the amide group to which a hydrocarbon group is bonded are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, an arylene group having 6 to 15 carbon atoms, or an arylalkylene group having 10 to 20 carbon atoms.
• the hydrocarbon group in the hydrocarbon group and the hydrocarbon group containing an ether bond are preferably an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 10 carbon atoms, or an arylene group having 6 to 15 carbon atoms.
• the number of carbon atoms of the hydrocarbon group containing a carbonyloxy group and the hydrocarbon group containing a carbonylamide group is preferably 1 to 15, and the hydrocarbon group is preferably an aliphatic structure, an alicyclic structure, an aromatic structure, a condensed polycyclic structure, or a condensed polycyclic heterocyclic structure.
• W 3 and W 7 preferably have an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 20 carbon atoms, or an aromatic structure having 6 to 30 carbon atoms.
• R 126 represents a phenolic hydroxyl group
• W 3 bonded to the phenolic hydroxyl group contains an aromatic structure in its structure.
• R 166 represents a phenolic hydroxyl group
• W 7 bonded to the phenolic hydroxyl group contains an aromatic structure in its structure.
• W 3 and W 7 may be called a carboxylic acid residue.
• x is preferably an integer of 2 to 4.
• y is preferably an integer of 2 to 4.
• the above-mentioned substituents and structures may have heteroatoms and may be either unsubstituted or substituted.
• the above-mentioned substituents and structures may have heteroatoms and may be either unsubstituted or substituted.
• R 127 to R 129 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 2 to 6 carbon atoms, or an aryl group having 6 to 15 carbon atoms.
• R 127 to R 129 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
• the above-mentioned substituents and structures may have a heteroatom, and may be either unsubstituted or substituted.
• the above (I) structure or (II) structure preferably further has a radical polymerizable group and/or a thermally reactive group from the viewpoints of improving sensitivity during exposure, suppressing residues after development, suppressing residues after thermal curing, improving mechanical properties, and improving the reliability of the light-emitting device.
• a radical polymerizable group examples and preferred descriptions regarding the radical polymerizable group are as described above for the (A) binder resin.
• the thermally reactive group is a group that is not included in the radical polymerizable group.
• the radical polymerizable group is preferably one or more groups selected from the group consisting of a styryl group, a cinnamoyl group, a maleimide group, a nadimide group, a (meth)acryloyl group, an alkenyl group having 2 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms.
• the radical polymerizable group in the (I) structure may be either a radical polymerizable group such as a maleimide structure or a nadimide structure, or another radical polymerizable group in a structure containing an imide bond.
• the thermally reactive group is preferably one or more groups selected from the group consisting of a phenolic hydroxyl group, a hydroxyimide group, a hydroxyamide group, a silanol group, a 1,1-bis(trifluoromethyl)methylol group, a mercapto group, a carboxy group, a carboxylic anhydride group, a sulfonic acid group, an alkoxyalkyl group, a hydroxyalkyl group, an epoxy group, an oxetanyl group, and a blocked isocyanate group.
• the hydroxyimide group is not included in the imide bond in the above (I) structure.
• the photosensitive composition of the present invention contains a specific (H) imide compound that does not have a radical polymerizable group and a thermally reactive group, and a specific (H) imide compound that has a radical polymerizable group and/or a thermally reactive group.
• the specific (H) imide compound having the above radically polymerizable group and/or heat-reactive group is presumed to form a crosslinked structure with resins and the like as a crosslinking agent. This suppresses sublimation during heat curing, resulting in a significant effect of suppressing residues after heat curing.
• the effect of improving the degree of crosslinking of the cured product and promoting the ring-closing reaction of the resin is obtained, resulting in a significant effect of improving mechanical properties.
• the above (I) structure contributes to the control of the polarization structure and charge balance in the cured product, and is presumed to suppress outgassing by improving the heat resistance of the cured product, improving the reliability of the light-emitting device.
• the molecular weight of the specific (H) imide compound is preferably 100 or more, more preferably 300 or more, even more preferably 500 or more, and particularly preferably 700 or more, from the viewpoints of suppressing residues after thermal curing, improving mechanical properties, and improving the reliability of the light-emitting device.
• the molecular weight is preferably less than 3,000, more preferably 2,000 or less, even more preferably 1,500 or less, and particularly preferably 1,000 or less, from the viewpoints of improving sensitivity during exposure and suppressing residues after development.
• the above (II) structure may have a repeating unit with a repeat number of 2 or more.
• the specific (H) imide compound is a compound different from the polyimide resin in the above (A) binder resin, and the molecular weight of the specific (H) imide compound is less than 3,000.
• the weight average molecular weight of the polyimide resin is 4,000 or more in polystyrene equivalent measured by GPC.
• the polyimide resin does not include a compound having a molecular weight of less than 3,000.
• the content of the specific (H) imide compound is preferably 0.000010 parts by mass or more, more preferably 0.00010 parts by mass or more, and even more preferably 0.00050 parts by mass or more, from the viewpoint of improving the sensitivity during exposure, suppressing residue after development, improving mechanical properties, and improving the reliability of the light-emitting element, when the total of the (A) binder resin and the (B) compound is 100 parts by mass. Furthermore, 0.0010 parts by mass or more is preferable, 0.0050 parts by mass or more is more preferable, 0.010 parts by mass or more is even more preferable, and 0.030 parts by mass or more is particularly preferable.
• the content of the specific (H) imide compound is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less, from the viewpoint of improving the reliability of the light-emitting element.
• 7.0 parts by mass or less is preferable, 5.0 parts by mass or less is more preferable, 3.0 parts by mass or less is even more preferable, 2.0 parts by mass or less is even more preferable, and 1.0 parts by mass or less is particularly preferable.
• the photosensitive composition of the present invention further contains (I) a carboxylic acid compound and a carboxylic acid ester, the (I) carboxylic acid compound and the carboxylic acid ester contain a compound represented by general formula (41), and satisfy the following condition (3): (3)
• the total content of the carboxylic acid compound and the carboxylic acid ester (I) in the total solid content of the photosensitive composition is 0.010% by mass or more and 5.0% by mass or less.
• R 21 and R 22 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
• R 23 and R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
• a and b each independently represent an integer of 2 to 8.
• c represents an integer of 0 to 4.
• the above-mentioned substituents and structures may have a heteroatom, and may be either unsubstituted or substituted.
• carboxylic acid compounds and carboxylic acid esters examples include 4-hydroxybutanoic acid, 5-hydroxypentanoic acid, 6-hydroxyhexanoic acid, 4-(4-hydroxybutyl)carbonyloxybutanoic acid, 5-(5-hydroxypentyl)carbonyloxypentanoic acid, 6-(6-hydroxyhexyl)carbonyloxyhexanoic acid, methyl 4-hydroxybutanoate, ethyl 4-hydroxybutanoate, butyl 4-hydroxybutanoate, methyl 5-hydroxypentanoate, ethyl 5-hydroxypentanoate, butyl 5-hydroxypentanoate, methyl 6-hydroxyhexanoate, ethyl 6-hydroxyhexanoate, butyl 6-hydroxyhexanoate, ethyl 4-(4-hydroxybutyl)carbonyloxybutanoate, ethyl 5-(5-hydroxypentyl)carbonyloxypentanoate, and e
• the total content of the (I) carboxylic acid compound and carboxylic acid ester in the total solid content of the photosensitive composition is preferably 0.030% by mass or more, more preferably 0.050% by mass or more, even more preferably 0.070% by mass or more, and particularly preferably 0.10% by mass or more.
• the total content of the (I) carboxylic acid compound and carboxylic acid ester is preferably 4.0% by mass or less, more preferably 3.5% by mass or less, and even more preferably 3.0% by mass or less.
• it is preferably 2.5% by mass or less, more preferably 2.0% by mass or less, even more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, particularly preferably 0.70% by mass or less, and most preferably 0.50% by mass or less.
• these compounds are thought to promote the surface modification action on the surface of the first electrode at the opening of the pixel division layer. Therefore, it is presumed that the effect of suppressing residue after development will be significant.
• these compounds function as catalysts that promote crosslinking reactions on aromatic rings in resins having aromatic rings such as polyimide, polybenzoxazole, and their precursors, ring-closing reactions of resins, and crosslinking reactions in resins having silanol groups such as polysiloxane, so that the effect of improving mechanical properties is significant.
• these compounds function as catalysts that promote crosslinking reactions in the film due to thermal reactions. Therefore, the improvement in the degree of crosslinking in the film contributes to improving heat resistance and suppressing outgassing, so that the effect of improving the reliability of the light-emitting element is significant.
• the photosensitive composition of the present invention contains the above polyimide-based resin
• the photosensitive composition of the present invention satisfies the above condition (3) from the viewpoint of improving the reliability of the light-emitting device.
• the photosensitive composition of the present invention satisfies the above condition (3)
• the polyimide-based resin contains a polyimide-based resin having a weak acidic group.
• the photosensitive composition of the present invention further contains one or more compounds selected from the group consisting of cyclic amide compounds represented by general formula (20), amide compounds represented by general formula (21), cyclic urea compounds represented by general formula (22), urea compounds represented by general formula (23), oxazolidone compounds represented by general formula (24), and isoxazolidone compounds represented by general formula (25) (hereinafter referred to as "specific nitrogen-containing compounds”), and satisfies the following condition (5).
• the total content of the cyclic amide compound represented by general formula (20), the amide compound represented by general formula (21), the cyclic urea compound represented by general formula (22), the urea compound represented by general formula (23), the oxazolidone compound represented by general formula (24), and the isoxazolidone compound represented by general formula (25) in the total solid content of the photosensitive composition is 0.010 mass% or more and 5.0 mass% or less.
• R 46 to R 56 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms.
• R 130 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a hydroxyalkoxy group having 1 to 6 carbon atoms, a hydroxy group, an amino group, a monoalkylamino group having 1 to 6 carbon atoms, or a dialkylamino group having 2 to 12 carbon atoms.
• R 131 to R 142 each independently represent an alkyl group having 1 to 6 carbon atoms.
• ⁇ , ⁇ , and ⁇ each independently represent an integer of 0 to 6.
• a, b, c, e, f, g, h, i, j, k, l, and m each independently represent an integer of 0 to 2.
• a is 0.
• b is 0.
• ⁇ is 0, c is 0.
• the above-mentioned substituents and structures may have heteroatoms, and may be either unsubstituted or substituted.
• nitrogen-containing compounds include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-butyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-dimethylpropionamide, N,N-dimethylisobutyramide, N,N-dimethyl-3-methoxypropionamide, N,N-dimethyl-3-butoxypropionamide, 1,3-dimethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone, N,N'-dimethylpropyleneurea, 1,1,3,3-tetramethylurea, and 1,1,3,3-tetraethylurea.
• the total content of the specific nitrogen-containing compounds in the total solid content of the photosensitive composition is preferably 0.030% by mass or more, more preferably 0.050% by mass or more, even more preferably 0.070% by mass or more, and particularly preferably 0.10% by mass or more, from the viewpoint of improving the mechanical properties and the reliability of the light-emitting device.
• the total content of the specific nitrogen-containing compounds is preferably 4.0% by mass or less, more preferably 3.5% by mass or less, and even more preferably 3.0% by mass or less, from the viewpoint of improving the mechanical properties and the reliability of the light-emitting device.
• it is preferably 2.5% by mass or less, more preferably 2.0% by mass or less, even more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, particularly preferably 0.70% by mass or less, and most preferably 0.50% by mass or less.
• the nitrogen-containing structure with unshared electron pairs captures metallic impurities and ionic impurities that adversely affect electrical insulation, suppressing ion migration and electromigration, and is presumed to improve the reliability of light-emitting devices.
• the specific nitrogen-containing compounds function as catalysts that promote crosslinking reactions on aromatic rings in resins with aromatic rings, such as polyimide, polybenzoxazole, and their precursors, ring-closing reactions of resins, and crosslinking reactions in resins with silanol groups, such as polysiloxane, resulting in a significant effect in improving mechanical properties.
• the photosensitive composition of the present invention contains the above polyimide-based resin
• the photosensitive composition of the present invention satisfies the above condition (5) from the viewpoint of improving the reliability of the light-emitting device.
• the photosensitive composition of the present invention satisfies the above condition (5), it is more preferable that the polyimide-based resin contains a polyimide-based resin having a weak acidic group.
• the photosensitive composition of the present invention further contains water and satisfies the following condition (4).
• the content of water in the photosensitive composition is 0.010% by mass or more and 3.0% by mass or less.
• the content of water in the photosensitive composition is preferably 0.030% by mass or more, more preferably 0.050% by mass or more, even more preferably 0.070% by mass or more, and particularly preferably 0.10% by mass or more, from the viewpoint of improving the sensitivity during exposure and improving the reliability of the light-emitting element.
• the content of water is preferably 2.5% by mass or less, more preferably 2.2% by mass or less, and even more preferably 2.0% by mass or less, from the viewpoint of improving the sensitivity during exposure and improving the reliability of the light-emitting element.
• it is preferably 1.7% by mass or less, more preferably 1.5% by mass or less, even more preferably 1.2% by mass or less, even more preferably 1.0% by mass or less, particularly preferably 0.70% by mass or less, and most preferably 0.50% by mass or less.
• the water mentioned above captures metallic impurities and ionic impurities that adversely affect electrical insulation due to interactions such as the dipole moment of water molecules and hydrogen bonds, which is believed to suppress ion migration and electromigration and improve the reliability of light-emitting devices.
• the photosensitive composition of the present invention preferably satisfies the following condition (1a).
• the photosensitive composition of the present invention more preferably further satisfies the following condition (2a).
• (1a) The content of elemental fluorine in the total solid content of the photosensitive composition is 1,000 ppm by mass or less.
• (2a) The content of fluoride ions in the total solid content of the photosensitive composition is 1,000 ppm by mass or less.
• the content of fluorine element in the total solid content of the photosensitive composition is preferably 0 ppm by mass or more, more preferably 0.010 ppm by mass or more, even more preferably 0.030 ppm by mass or more, even more preferably 0.050 ppm by mass or more, particularly preferably 0.070 ppm by mass or more, and most preferably 0.10 ppm by mass or more.
• the content of fluorine element is preferably 1,000 ppm by mass or less, more preferably 500 ppm by mass or less, even more preferably 300 ppm by mass or less, and particularly preferably 100 ppm by mass or less.
• the content of fluorine element is preferably 50 ppm by mass or less, more preferably 30 ppm by mass or less, even more preferably 10 ppm by mass or less, even more preferably 5 ppm by mass or less, particularly preferably 3 ppm by mass or less, and most preferably 1 ppm by mass or less.
• the preferred ranges of the content of fluoride ions in the total solid content of the photosensitive composition are the same as the preferred ranges of the content of elemental fluorine in the total solid content of the photosensitive composition described above.
• the photosensitive composition of the present invention has the above-mentioned configuration [3], from the viewpoint of the above-mentioned effects of the invention, it is preferable that the photosensitive composition of the present invention satisfies the above-mentioned condition (1a), and more preferably satisfies the above-mentioned condition (2a).
• the photosensitive composition of the present invention preferably satisfies the above condition (1a) from the viewpoint of the effects of the present invention, and more preferably satisfies the above condition (2a).
• the photosensitive composition of the present invention satisfies the above condition (1a), and more preferably satisfies the above condition (2a).
• the content of elemental fluorine in the total solid content of the photosensitive composition may be 0 ppm by mass.
• the content of fluoride ions in the total solid content of the photosensitive composition may also be 0 ppm by mass.
• the photosensitive composition of the present invention preferably contains a component containing elemental fluorine and/or a component containing fluoride ions in the structure of (A) binder resin, (C) photosensitizer, (B) compound, (F) crosslinking agent, or (H) imide compound.
• the component containing elemental fluorine is preferably a phenol compound, an alkyl fluoride compound, a cycloalkyl fluoride compound, or an aryl fluoride compound having a substituent containing an alkyl fluoride group.
• the component containing fluoride ions preferably contains an ammonium ion, a primary ammonium ion, a secondary ammonium ion, a tertiary ammonium ion, or a quaternary ammonium ion as a cationic species.
• the quaternary ammonium ion preferably has a linear or branched hydrocarbon group.
• the hydrocarbon group is preferably an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms.
• the content of compounds containing fluorine atoms in the structure or components containing fluorine elements in the photosensitive composition is set to a specific value or less, and it is presumed that the protons in the photosensitive composition are locally activated by interactions such as hydrogen bonds between the components in the photosensitive composition. Therefore, it is considered that the effect of suppressing residues at the bottom of the pattern becomes significant due to the dissolution promotion action in the developer.
• the polarization structure and charge balance in the cured product are controlled by intentionally setting the content of the above components to a specific value or less.
• the reliability of the light-emitting element is improved by suppressing ion migration and electromigration caused by metal impurities and ion impurities that have a negative effect on the light-emitting properties or electrical insulation. It is also presumed that the reliability of the display device is improved by suppressing migration and aggregation of metals in the electrodes or metal wiring.
• the photosensitive composition of the present invention preferably further contains a thermal color former, an oxidative color former, a dissolution promoter, an ink repellent, a sensitizer, a chain transfer agent, a polymerization inhibitor, a silane coupling agent, or a surfactant. These additives may be known.
• the photosensitive composition of the present invention preferably further contains a solvent.
• the solvent is preferably a compound having an acetate bond, a propionate bond, or a butyrate bond from the viewpoint of improving the dispersion stability of the pigment.
• the photosensitive composition film of the present invention is a semi-cured state (B stage) formed from the photosensitive composition of the present invention.
• the semi-cured state refers to a state in which the film has fluidity even though no crosslinked structure is formed or a crosslinked structure is formed by partial reaction.
• the coating film is dried under reduced pressure to remove the solvent, or the coating film is heated to 40 to 150°C and dried, and refers to a state in which the film is soluble in an alkaline solution or an organic solvent.
• the photosensitive composition film of the present invention preferably has a photosensitive composition film formed from the photosensitive composition of the present invention and a support.
• the photosensitive composition film has positive or negative photosensitivity. It is also preferable that the photosensitive composition film is capable of forming a free-standing film with a single film. It is preferable that the photosensitive composition film has adhesiveness, and it is also preferable that a plurality of members are joined. Being able to form a free-standing film with a single film means being able to form a film with a width of 1.5 cm or more, a length of 5.0 cm or more, and a thickness of 5.0 ⁇ m or more without a support. In other words, the photosensitive composition film is preferably a photosensitive composition coating capable of forming a free-standing film with a single film.
• the support is preferably a flexible substrate, but may also be a rigid substrate.
• the surface of the support facing the photosensitive film may be surface-treated with a silane coupling agent or the like.
• the thickness of the support is preferably 10 to 200 ⁇ m from the viewpoint of handling.
• the cured product of the present invention is obtained by curing the photosensitive composition of the present invention.
• Curing refers to the formation of a crosslinked structure by a reaction and the loss of fluidity of the film, or the state in which it is formed.
• the reaction may be by heating, by irradiation with energy rays, or the like, but is not particularly limited. Heating is preferred.
• the state in which a crosslinked structure is formed by heating and the film loses fluidity is called thermal curing. Heating conditions include, for example, heating at 150 to 500°C for 5 to 300 minutes.
• the cured product of the present invention may be obtained by curing the photosensitive film of the present invention.
• the optical density at the wavelength of visible light per 1 ⁇ m of film thickness of the cured product of the present invention is preferably 0.20 or more, more preferably 0.50 or more, and even more preferably 1.0 or more, from the viewpoint of suppressing external light reflection and improving the reliability of the element.
• the above optical density is preferably 3.0 or less, more preferably 2.0 or less, and even more preferably 1.5 or less, from the viewpoint of improving sensitivity during exposure and improving the reliability of the element.
• the optical density is preferably the optical density of the cured product obtained by heating and curing the composition.
• the dielectric loss tangent of the cured product of the present invention at a frequency of 1 GHz is preferably 0.00010 or more and 0.0100 or less from the viewpoint of improving the reliability of the element and reducing transmission loss.
• the dielectric loss tangent is a value measured by a resonator method using a split post dielectric resonator (SPDR).
• the dielectric constant of the cured product of the present invention at a frequency of 1 GHz is preferably 2.0 or more and 3.5 or less from the viewpoint of improving the reliability of the element and reducing transmission loss.
• the preferred ranges for the dielectric loss tangent and dielectric constant of the cured product of the present invention at frequencies of 10 GHz, 30 GHz, and 70 GHz are also the same as those described above.
• the water absorption rate of the cured product of the present invention is preferably 0.10% by mass or more, and more preferably 0.30% by mass or more.
• the water absorption rate is preferably 2.0% by mass or less, more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, even more preferably 0.70% by mass or less, and particularly preferably 0.50% by mass or less.
• the element of the present invention comprises the cured product of the present invention.
• the article of the present invention comprises the cured product of the present invention.
• Examples of the article include electronic components, electronic devices, mobile objects, buildings, or windows.
• Examples of the electronic components include semiconductor devices, antennas, display devices, metal-clad laminates, wiring boards, semiconductor packages, active components including semiconductor devices, or passive components.
• the photosensitive composition of the present invention is preferably used to form electronic components.
• the semiconductor devices include semiconductor devices having a fan-out wafer-level package structure, a fan-out panel-level package structure, or an antenna-in-package structure.
• Examples of the antenna include a microstrip line antenna or a strip line antenna.
• Examples of the display devices include an organic EL display, a quantum dot display, a micro light-emitting diode (hereinafter, "LED”) display, a mini LED display, or a liquid crystal display.
• Examples of the metal-clad laminate include a printed circuit board.
• the electronic component of the present invention comprises the cured product of the present invention.
• the display device of the present invention comprises the cured product of the present invention.
• the cured product of the present invention can have both excellent mechanical properties and excellent reliability of the light-emitting element. Therefore, the photosensitive composition of the present invention is preferably used to form an insulating layer of a metal wiring, a protective layer of a metal wiring, or an interlayer insulating layer of a metal wiring in an electronic component.
• the photosensitive composition of the present invention is also preferably used to form an interlayer insulating layer of a rewiring in a semiconductor device, and is also preferably used to form an insulating layer of a metal wiring, a protective layer of a metal wiring, or an interlayer insulating layer between a metal wiring and a ground wiring in an antenna, and is also preferably used to form a pixel division layer, a flattening layer of a TFT, a protective layer of a TFT, an interlayer insulating layer of a TFT, or a gate insulating layer in an organic EL display, a quantum dot display, or a micro LED display, and is also preferably used to form an insulating layer of a metal wiring, a protective layer of a metal wiring, or a solder resist layer of a metal wiring in a metal-clad laminate.
• the hollow structure of the present invention comprises the cured product of the present invention.
• the electronic component of the present invention preferably has the hollow structure of the present invention.
• the hollow structure of the present invention has a hollow structure supporting material and a hollow structure roofing material. From the viewpoint of improving heat resistance and reliability, the hollow structure supporting material and the hollow structure roofing material preferably contain the above-mentioned polyimide-based resin.
• the film thickness of the hollow structure supporting material is preferably 5 to 20 ⁇ m.
• the film thickness of the hollow structure roofing material is preferably 10 to 50 ⁇ m.
• the photosensitive composition of the present invention is preferably used for forming a hollow structure.
• ⁇ Display Device> The display device of the present invention will be described below. However, the present invention is not limited to the following embodiments, and various modifications can be made within the scope of the invention as long as the object of the invention can be achieved and the gist of the invention is not deviated from.
• the display device of the present invention has the above-mentioned configuration [20]. With the above-mentioned configuration, the display device of the present invention can provide a display device with excellent reliability of the light-emitting element. This is thought to be because the above-mentioned (XI) structure contributes to the control of the polarization structure and charge balance in the cured product. As a result, in addition to suppressing ion migration and electromigration caused by metal impurities and ion impurities that adversely affect the light-emitting characteristics, it is presumed that the effect of excellent reliability of the light-emitting element is achieved by suppressing migration and aggregation of metals in electrodes and wiring. In other words, it is presumed that the effect of excellent migration resistance in electronic components, semiconductor devices, display devices, or metal-clad laminates is also achieved.
• the (XH)imide compound in the cured product is preferably the (H)imide compound in the photosensitive composition described above, or a compound having a structure derived from the (H)imide compound.
• Examples and preferred descriptions of the (XI) structure and (XII) structure in the (XH)imide compound in the cured product are the same as the examples and preferred descriptions of the (I) structure and (II) structure in the (H)imide compound in the photosensitive composition described above.
• the substrate, first electrode, second electrode, pixel dividing layer, light-emitting layer, and TFT planarizing layer may be made of known materials.
• the cured product in the display device of the present invention preferably satisfies the following condition (X ⁇ ).
• (X ⁇ ) The content of the imide compound (XH) in the cured product is 0.0010 mass% or more and 5.0 mass% or less.
• the content of the (XH) imide compound in the cured product is preferably 0.0050% by mass or more, more preferably 0.0070% by mass or more, and even more preferably 0.010% by mass or more. Furthermore, 0.030% by mass or more is preferable, more preferably 0.050% by mass or more, even more preferably 0.070% by mass or more, and particularly preferably 0.10% by mass or more.
• the content of the (XH) imide compound is preferably 5.0% by mass or less, more preferably 4.5% by mass or less, and even more preferably 4.0% by mass or less. Furthermore, 3.5% by mass or less is preferable, more preferably 2.5% by mass or less, even more preferably 1.5% by mass or less, even more preferably 1.0% by mass or less, and particularly preferably 0.50% by mass or less.
• the display device of the present invention includes a cured product.
• the cured product in the display device of the present invention is preferably a cured product of a photosensitive composition, and more preferably contains a resin.
• the resin in the cured product preferably contains (XA1) a weakly acidic group-containing resin and/or (XA2) a resin not having a weakly acidic group.
• the (XA1) weakly acidic group-containing resin in the cured product is preferably the above (A1) weakly acidic group-containing resin or a resin having a structure derived from the resin.
• the (XA2) resin not having a weakly acidic group is preferably the above (A2) resin not having a weakly acidic group or a resin having a structure derived from the resin.
• Examples and preferred descriptions of the resin in the cured product are the same as the examples and preferred descriptions of the binder resin (A) above.
• the resin in the cured product may be either the (A) binder resin in the composition or a resin having a structure derived from the resin.
• the method for producing a cured product of the present invention includes (1) a step of forming a coating film of the photosensitive composition of the present invention on a substrate, (2) a step of irradiating the coating film of the photosensitive composition with active actinic rays through a photomask, (3) a step of developing using a developer to form a pattern of the photosensitive composition, and (4) a step of heating the pattern to obtain a cured pattern of the photosensitive composition.
• each method described in paragraphs [0453] to [0481] of International Publication No. 2019/087985 may be applied.
• the step of forming a coating film is preferably performed by applying and then pre-baking to form a film.
• the step of obtaining a cured pattern is preferably performed by heating the pattern to thermally cure it.
• the hydroxyl-containing diamine (HA) of the following structure used in Synthesis Examples 10 and 11 was synthesized by a known method based on the synthesis method described in Synthesis Example 1 in paragraphs [0374] to [0376] of WO 2016/056451.
• the resins obtained in Synthesis Examples 10 and 11 using the hydroxyl-containing diamine (HA) of the following structure are polyimide precursors having an amic acid ester structural unit, an amic acid structural unit, and an imide ring-closed structure.
• the structural units and structures of the resins obtained in each synthesis example and the resins used in each working example, reference example, and comparative example are summarized in Table 2-1.
• the fluorine content in the resin structure of each of the following resins exceeded 10,000 mass ppm: polyimide (PI-1) and (PI-3) to (PI-6); polyimide precursor (PIP-1) and (PIP-2); polybenzoxazole (PB-1); polybenzoxazole precursor (PBP-1); and polyamideimide (PAI-1).
• the fluorine content in the resin structure of each of the following resins was 0 mass ppm: polyimide (PI-2) and (PI-7) to (PI-9); polyimide precursor (PIP-3); and the resins in the other synthesis examples.
• pigment dispersions (Bk-1) to (Bk-3) with a solid content concentration of 15% by mass and colorant/dispersant 100/35 (mass ratio).
• the average primary particle diameter of the pigment in the obtained pigment dispersion is shown in Table 2-2.
• the average primary particle diameter of the pigment in the cured film, the crystallite size of the pigment in the pigment dispersion, and the crystallite size of the pigment in the cured film are also shown in Table 2-2.
• Synthesis Example 22 Synthesis of silica particle (SP-1) dispersion Based on the method described in paragraphs [0132] to [0134] and Synthesis Example 3 of International Publication No. 2022/196261, MEK-ST-40 was used as the silica particle dispersion, KBM-503 was used as the surface modifier, and MOP was used as the polymerization inhibitor to obtain a dispersion of silica particles (SP-1).
• the inorganic particles, silica particles (SP-1), have a functional group on the particle surface as a methacryloyl group, a distribution range of primary particle diameters of 10 to 16 nm, an average primary particle diameter of 12 nm, an aspect ratio range of 1.0 to 1.1, an average aspect ratio of 1.1, and a sodium element content of 100 ppm by mass.
• Tempax glass substrates manufactured by AGC Technoglass Co., Ltd.
• other substrates were used without pretreatment.
• the film thickness was measured using a surface roughness/contour shape measuring device (SURFCOM1400D; manufactured by Tokyo Seimitsu Co., Ltd.) under the conditions of a measurement magnification of 10,000 times, a measurement length of 1.0 mm, and a measurement speed of 0.30 mm/s.
• SURFCOM1400D surface roughness/contour shape measuring device
• a GPC analyzer (HLC-8220; manufactured by Tosoh Corporation) was used, and tetrahydrofuran or N-methyl-2-pyrrolidone was used as the fluidized bed.
• the weight average molecular weight in terms of polystyrene was measured at around room temperature based on "JIS K7252-3 (2008)”.
• the prepared silicon wafer with the resin film was divided into two, and one of the two was heated at 140°C for 30 minutes using a clean oven (CLH-21CD-S; manufactured by Koyo Thermo Systems Co., Ltd.) in a nitrogen atmosphere with an oxygen concentration of 20 mass ppm or less, and then further heated to 320°C for 60 minutes to completely close the imide ring (resin film after heating).
• the other was used as it was without heat treatment (resin film before heating).
• FT-720 infrared spectrophotometer
• a resin film having a thickness of 4 to 5 ⁇ m was prepared by the same method as above.
• the prepared silicon wafer with the resin film was divided into two, and one of the two was heated at 320° C. for 30 minutes using a buzzer hot plate (HPD-3000BZN; manufactured by AS ONE Corporation) to completely close the benzoxazole ring (resin film after heating).
• the other was used as it was without heat treatment (resin film before heating).
• the transmission infrared absorption spectrum of the resin film before and after heating was measured using an infrared spectrophotometer (FT-720; manufactured by Horiba, Ltd.).
• the imide ring closure rate of the polyimide precursors (PIP-1) to (PIP-3) was 10%, and the benzoxazole ring closure rate was 0%.
• the imide ring closure rate of the polyimide precursor (PIP-3) was 10%.
• the benzoxazole ring closure rate of the polybenzoxazole (PB-1) was 60%.
• the benzoxazole ring closure rate of the polybenzoxazole precursor (PBP-1) was 0%.
• the imide ring closure rate of the polyamideimide (PAI-1) was 100%, and the benzoxazole ring closure rate was 0%.
• the resin or composition was burned and decomposed in the combustion tube of the analyzer, the generated gas was absorbed in the absorption liquid, and a part of the absorption liquid was analyzed by ion chromatography. The absence of the content of the element indicates that the element was not detected.
• the content in the total solid content of the composition was calculated from the obtained measured value and the following formula.
• the content of fluoride ions in the composition was measured by ion chromatography under the following measurement conditions.
• the composition was added to ultrapure water and shaken at room temperature to extract ion components.
• the extract was treated with a solid-phase extraction cartridge, and then anion components were analyzed by ion chromatography.
• anion components could not be measured under the following ion chromatography analysis condition 1, they were measured under the following ion chromatography analysis condition 2.
• the absence of a description of the ion content indicates that the ion was not detected.
• the content in the total solid content of the composition was calculated from the obtained measurement value and the following formula.
• the water content in the composition was measured by volumetric titration based on “JIS K0113 (2005)” using a Karl Fischer moisture meter (MKS-520; manufactured by Kyoto Electronics Manufacturing Co., Ltd.) and a Karl Fischer reagent as a titration reagent.
• Sensitivity The resolution pattern of the film after development was observed using an FPD/LSI inspection microscope (OPTIPHOT-300; manufactured by Nikon Corporation). When a composition having positive photosensitivity was used, the optimum exposure dose (value of an i-line illuminometer) at which a space pattern corresponding to an opening can be formed with a dimensional width of 20 ⁇ m in a 20 ⁇ m line-and-space pattern was determined as an index of sensitivity.
• the exposure dose value of an i-line illuminometer
• the exposure dose at which a space pattern corresponding to an opening can be formed with a dimensional width of 18 ⁇ m in a 20 ⁇ m line-and-space pattern was determined as an index of sensitivity.
• the sensitivity was judged as follows, and A+, A, B+, B, C+, and C, which have a sensitivity of 90 mJ/cm 2 or less, were considered to be acceptable.
• A+ No residue A: The area where residue is present is 3% or less B+: The area where residue is present is more than 3% and less than 6% B: The area where residue is present is more than 6% and less than 10% C+: The area where residue is present is more than 10% and less than 15% C: The area where residue is present is more than 15% and less than 20% D: The area where residue is present is more than 20% and less than 50% E: The area where residue is present is more than 50% and less than 100%.
• a cured film of the composition was prepared on a 6-inch diameter SiO 2 /Si wafer with a film thickness of about 5 ⁇ m by the method described in Example 1 below.
• the cured film was peeled off from the SiO 2 /Si wafer using dilute hydrofluoric acid.
• the peeled off cured film was cut into strips with a width of 1.5 cm and a length of 9.0 cm.
• a tensile test was performed using a Tensilon (RTM-100; manufactured by Orientec Co., Ltd.) at a room temperature of 23.0° C. and a humidity of 45.0% RH at a tensile speed of 50 mm/min to measure the elongation at break.
• A+ Elongation at break is 30% or more.
• A: Elongation at break is 20% or more and less than 30%.
• B+ Elongation at break is 15% or more and less than 20%.
• B: Elongation at break is 10% or more and less than 15%.
• C+ Elongation at break is 7.5% or more and less than 10%.
• C: Elongation at break is 5.0% or more and less than 7.5%.
• the organic EL display prepared by the method described in Example 1 below was driven by direct current at 10 mA/ cm2 to emit light, and the presence of light emission defects such as non-light-emitting areas and uneven brightness was observed.
• the light-emitting element was heated to 80°C with the light extraction side facing up, and irradiated with light of wavelength 365 nm and illuminance 0.6 mW/ cm2 for 500 hours. After 500 hours, the organic EL display was driven by direct current at 10 mA/ cm2 to emit light, and the presence of changes in the light-emitting characteristics was observed.
• the light-emitting area after the durability test was measured when the light-emitting area before the durability test was set to 100%.
• the evaluation was performed as follows, and A+, A, B+, B, C+, and C, which are light-emitting area areas of 80% or more, were considered to be passed.
• A+ Light-emitting area is 100%
• the compounds (x-15) to (x-18) correspond to the above (II) structure having a repeating unit with a repeating number of 2 or more.
• compositions 1 to 100 were prepared according to the compositions shown in Tables 3-1 to 3-8.
• Tables 3-1 to 3-8 the values in parentheses indicate the parts by mass of the solid content of each component.
• a preparation not containing a pigment dispersion was first prepared, and then the pigment dispersion and the preparation were mixed to prepare the composition.
• the obtained composition solution was filtered through a 0.45 ⁇ m ⁇ filter before use.
• Example 1 Composition 1 was applied onto an ITO/Ag substrate using a spin coater (MS-A100; manufactured by Mikasa Co., Ltd.), and then prebaked for 120 seconds at 120° C. using a buzzer hot plate (HPD-3000BZN; manufactured by AS ONE Co., Ltd.) to prepare a prebaked film having a thickness of about 1.8 ⁇ m.
• a spin coater MS-A100; manufactured by Mikasa Co., Ltd.
• HPD-3000BZN manufactured by AS ONE Co., Ltd.
• the prepared prebaked film was spray-developed with a 2.38% by mass aqueous TMAH solution or cyclopentanone using a small photolithography developing device (AD-1200; manufactured by Takizawa Sangyo Co., Ltd.), and the time (Breaking Point; hereinafter, “BP”) until the prebaked film (unexposed area) was completely dissolved was measured.
• AD-1200 small photolithography developing device
• BP Breaking Point
• a prebaked film was prepared in the same manner, and the prepared prebaked film was patterned and exposed to the i-line (wavelength 365 nm), h-line (wavelength 405 nm), and g-line (wavelength 436 nm) of an ultra-high pressure mercury lamp using a double-sided alignment single-sided exposure device (Mask Aligner PEM-6M; manufactured by Union Optical Co., Ltd.) through a grayscale mask for sensitivity measurement (MDRM MODEL 4000-5-FS; manufactured by Opto-Line International Co., Ltd.).
• the film was developed with a 2.38 mass% TMAH aqueous solution using a small photolithography developing device (AD-1200; manufactured by Takizawa Sangyo Co., Ltd.) and rinsed with water for 30 seconds to prepare a developed film.
• the development time was 60 seconds, 90 seconds, or 120 seconds.
• a film exposed in the same manner as above was prepared, and after exposure, a small photolithography developing device (AD-1200; manufactured by Takizawa Sangyo Co., Ltd.) was used to develop the film with cyclopentanone and rinse with water for 30 seconds to prepare a developed film.
• the development time was 60 seconds, 90 seconds, or 120 seconds.
• the developed patterns were observed for all films with development times of 60 seconds, 90 seconds, and 120 seconds, and the optimal exposure amount (value of an i-line illuminometer) that can form a space pattern corresponding to an opening with a dimensional width of 20 ⁇ m in a 20 ⁇ m line and space pattern was determined. From these results, the optimal development time (60 seconds, 90 seconds, or 120 seconds) and the optimal exposure amount at that development time were determined. After exposure to the optimum exposure dose and development for the optimum development time, the pattern was thermally cured at 200°C for 60 minutes using a high-temperature inert gas oven (INH-9CD-S; manufactured by Koyo Thermo Systems) to produce a cured film with a thickness of approximately 1.2 ⁇ m.
• a high-temperature inert gas oven IH-9CD-S; manufactured by Koyo Thermo Systems
• the thermal curing conditions were as follows: in a nitrogen atmosphere with an oxygen concentration of 20 mass ppm or less, the temperature was raised to 200°C at a heating rate of 3.5°C/min, heat treatment was performed at 200°C for 60 minutes, and then cooling to 50°C.
• the cured film was analyzed by methods such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, gas chromatography mass spectrometry, liquid chromatography mass spectrometry, and time-of-flight secondary ion mass spectrometry, and the structural units of the resins contained in the cured film and the structures of the compounds contained in the cured film were analyzed.
• the cured film of composition 1 contains the following resins and compounds, and contains a resin having a structure derived from the resin contained in composition 1 and a compound having a structure derived from the compound contained in composition 1.
• (XA1) resin a resin having a phenolic hydroxyl group and having an imide structure in the structural unit; a resin having a phenolic hydroxyl group and having an amic acid ester structure, an amic acid structure, and an imide structure in the structural unit; a phenolic resin having a phenolic hydroxyl group in the structural unit.
• (XH) imide compound a compound having two (XI) structures: a structure in which a phthalimide structure and a benzene structure having a trifluoromethyl group are bonded, and further having a (XII) structure: an ether bond.
• FIG. 1 shows a schematic diagram of the substrate used.
• amorphous ITO was sputtered to form a 10 nm thick transparent conductive oxide layer on the upper layer of the APC layer, and a reflective electrode was formed as the first electrode portion 48 by etching.
• an auxiliary electrode portion 49 was also formed at the same time to extract the second electrode (FIG. 1 (1)).
• the obtained substrate was ultrasonically cleaned with "Semicoclean" (registered trademark) 56 (manufactured by Furuuchi Chemical Co., Ltd.) for 10 minutes, and washed with ultrapure water.
• composition 1 was applied and prebaked on this substrate by the above method, and the substrate was exposed to patterning through a photomask having a predetermined pattern, developed and rinsed, and then heated to be thermally cured.
• the development time was set to 60 seconds, 90 seconds, or 120 seconds, and the optimal development time (60 seconds, 90 seconds, or 120 seconds) and the optimal exposure amount at that development time were obtained in advance.
• the pattern was thermally cured at 200°C for 60 minutes.
• the thermal curing conditions were a nitrogen atmosphere with an oxygen concentration of 20 mass ppm or less, a temperature increase rate of 3.5°C/min to 200°C, a heat treatment at 200°C for 60 minutes, and then cooling to 50°C.
• a pixel division layer portion 50 in which rectangular openings with a width of 70 ⁇ m and a length of 70 ⁇ m are arranged at a pitch of 175 ⁇ m in the width direction and a pitch of 175 ⁇ m in the length direction, and each opening exposes the first electrode, was formed in a limited area of the substrate effective area ((2) in FIG. 1). The openings will ultimately become the light-emitting pixels of the organic EL display.
• the effective area of the substrate was 16 mm square, and the pixel dividing layer portion 50 was formed to a thickness of about 1.5 ⁇ m.
• an organic EL display was produced using the substrate on which the first electrode portion 48, the auxiliary electrode portion 49, and the pixel division layer portion 50 were formed.
• an organic EL layer portion 51 including a light-emitting layer was formed by a vacuum deposition method ((3) in FIG. 1). The degree of vacuum during deposition was 1 ⁇ 10 ⁇ 3 Pa or less, and the substrate was rotated relative to the deposition source during deposition.
• compound (HT-1) was deposited to a thickness of 10 nm as a hole injection layer
• compound (HT-2) was deposited to a thickness of 50 nm as a hole transport layer.
• compound (GH-1) was deposited to a thickness of 40 nm as a host material and compound (GD-1) was deposited to a thickness of 10 volume % in the light-emitting layer. Then, compound (ET-1) and compound (LiQ) were deposited to a thickness of 40 nm as electron transport materials at a volume ratio of 1:1.
• the compounds used in the organic EL layer were the same as those described in paragraphs [0599] to [0600] of WO 2017/057281.
• a cap-shaped glass plate was attached using an epoxy resin adhesive to seal the device, and four top-emission organic EL displays measuring 5 mm square were fabricated on one substrate. Note that the film thickness referred to here is the value displayed on a quartz crystal oscillator film thickness monitor.
• Examples 2 to 95 and Comparative Examples 1 to 5 The compositions shown in Tables 3-1 to 3-9 were used to carry out the same operations and evaluations as in Example 1. The evaluation results are shown in Tables 3-1 to 3-9. The content of fluorine element in the total solid content of the composition in Examples 1 to 53 and Comparative Examples 1 to 5 exceeded 1,000 ppm by mass. The content of fluorine element in the total solid content of the composition in Examples 54 to 90 was 0 ppm by mass. The content of fluorine element in the total solid content of the composition in Examples 91 to 95 was as shown in Table 3-7. In each Example, when a composition having positive photosensitivity was used, the development time was set to 60 seconds, 90 seconds, or 120 seconds.
• the optimum development time 60 seconds, 90 seconds, or 120 seconds
• the optimum exposure amount at that development time were determined.
• the pattern was thermally cured at 200° C. for 60 minutes.
• the thermal curing conditions were as follows: under a nitrogen atmosphere with an oxygen concentration of 20 mass ppm or less, the temperature was raised to 200 ° C. at a heating rate of 3.5 ° C. / min, and heat treatment was performed at 200 ° C. for 60 minutes, and then cooled to 50 ° C.
• the photomask in which the light-transmitting portion and the light-shielding portion were inverted was used as the photomask, and the development time was 1.3 times the measured BP.
• the developed pattern was thermally cured at 220 ° C. for 60 minutes.
• the thermal curing conditions were as follows: under a nitrogen atmosphere with an oxygen concentration of 20 mass ppm or less, the temperature was raised to 220 ° C. at a heating rate of 3.5 ° C. / min, and heat treatment was performed at 220 ° C. for 60 minutes, and then cooled to 50 ° C.
• Comparative examples 1 to 5 do not contain the specific (H) imide compound, and therefore have poor properties.
• non-alkali glass substrate 48 first electrode portion 49: auxiliary electrode portion 50: pixel division layer portion 51: organic EL layer portion including a light-emitting layer 52: second electrode portion

Landscapes

• Physics & Mathematics (AREA)
• Engineering & Computer Science (AREA)
• General Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Microelectronics & Electronic Packaging (AREA)
• Manufacturing & Machinery (AREA)
• Chemical & Material Sciences (AREA)
• Materials Engineering (AREA)
• Crystallography & Structural Chemistry (AREA)
• Inorganic Chemistry (AREA)
• Nanotechnology (AREA)
• Optics & Photonics (AREA)
• Materials For Photolithography (AREA)

Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

Family

ID=92146427

Family Applications (1)

Country Status (4)

Citations (7)

Family Cites Families (2)

• 2023
  • 2023-12-25 JP JP2024505539A patent/JPWO2024161862A1/ja active Pending
  • 2023-12-25 KR KR1020257021223A patent/KR20250143304A/ko active Pending
  • 2023-12-25 CN CN202380087239.4A patent/CN120380424A/zh active Pending
  • 2023-12-25 WO PCT/JP2023/046327 patent/WO2024161862A1/ja not_active Ceased

Patent Citations (7)

Also Published As

Similar Documents

Legal Events