Resin composition, cured product, method for producing cured product, organic EL display device, display device, and compound

Abstract

To provide a resin composition with excellent heat resistance and substrate adhesion. [Solution] The present invention provides a resin composition comprising an alkali-soluble resin (a) and a compound (b) having at least two substructures represented by formula (1) within its molecule. TIFF2026059932000044.tif25165 (In formula (1), R 1 R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 2 (where * represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 2 to 20 carbon atoms which may have substituents, and * represents a bond.)

Description

[Technical Field]

[0001] The present invention relates to a resin composition that can be suitably used as a planarization layer or insulating layer in a display device such as an organic EL display device, and to a compound that can be contained in the resin composition. [Background technology]

[0002] Many products using organic electroluminescent (hereinafter referred to as "organic EL") display devices have been developed for display devices with thin displays, such as smartphones, tablet PCs, and televisions. Generally, an organic EL display device has a drive circuit, a planarization layer, a first electrode, an insulating layer, a light-emitting layer, and a second electrode on a substrate, and can emit light by applying a voltage between the opposing first and second electrodes. Among these, photosensitive resin compositions that can form patterns by ultraviolet light irradiation are generally used as the material for the planarization layer and the insulating layer.

[0003] On the other hand, a method of adding a thermal crosslinking agent to improve the film properties during heat curing of a resin composition is known. A typical thermal crosslinking agent that improves the film properties during heat curing of an alkali-soluble resin composition is one that contains methylol groups (see Patent Document 1). It is known that the above thermal crosslinking agent crosslinks when the alkali-soluble resin and methylol groups react during heat curing, improving the heat resistance of the cured product. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2006-313237 [Overview of the project] [Problems that the invention aims to solve]

[0005] However, the films formed by heat curing in the resin compositions using the above-mentioned crosslinking agents exhibited insufficient heat resistance and substrate adhesion properties. The objective of the present invention is to provide a resin composition that exhibits excellent heat resistance and substrate adhesion in the cured product after heating. [Means for solving the problem]

[0006] To solve the above problems, the resin composition of the present invention has the following configuration.

[0007] [1] A resin composition comprising an alkali-soluble resin (a) and a compound (b) having at least two substructures represented by formula (1) within its molecule.

[0008] [ka]

[0009] In formula (1), R 1 R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 2 * represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 2 to 20 carbon atoms which may have substituents, and * represents a bond.

[0010] [2] The resin composition according to [1], further comprising a photosensitive compound (c).

[0011] [3] The resin composition according to [1] or [2], wherein component (a) comprises one or more selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, copolymers thereof, polyhydroxystyrene, and copolymers of hydroxystyrene and styrene derivatives that do not have phenolic hydroxyl groups.

[0012] [4] R in formula (1) above 2 The resin composition according to any one of [1] to [3], wherein the aryl group having 6 to 20 carbon atoms may have substituents, or the heteroaryl group having 2 to 20 carbon atoms may have substituents.

[0013] [5] The R in the formula (1) 2 The aryl group having 6 to 20 carbon atoms which may have a substituent is an aryl group having 6 to 20 carbon atoms having a substituent with a Hammett's substituent constant σ p value of 0.4 or more, and the R in the formula (1) 2 The heteroaryl group having 2 to 20 carbon atoms which may have a substituent is a heteroaryl group having 2 to 20 carbon atoms having a substituent with a Hammett's substituent constant σ p value of 0.4 or more, and the resin composition according to any one of [1] to [4].

[0014] [6] The R in the formula (1) 1 is a hydrogen atom, and the resin composition according to any one of [1] to [5].

[0015] [7] At least one bond in the formula (1) is directly bonded to an aryl group having 6 to 20 carbon atoms of an aryl group having 6 to 20 carbon atoms which may have a substituent, or an aryl group having 2 to 20 carbon atoms of a heteroaryl group having 2 to 20 carbon atoms which may have a substituent, and the resin composition according to any one of [1] to [6].

[0016] ​​​​​​​​​​​​​​​​​​​​​​​​​[9] The resin composition according to any one of [1] to [8], wherein the component (b) contains at least one compound represented by one of the following structures.

[0020] [ka]

[0021] R 7 , R 9 , R 11 , R 13 , R 15 and R 17 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 8 , R 10 , R 12 , R 14 , R 16 and R 18 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6.

[0022] A cured product obtained by curing any of the resin compositions described in

[10] [1] to [9].

[0023]

[11] A step of forming a resin film on a substrate, the resin film being made of any of the resin compositions described in [1] to [9]. The process of exposing the resin film, A process of developing the exposed resin film, and A method for producing a cured product, comprising the step of heat-treating a developed resin film.

[0024]

[12] An organic EL display device having a drive circuit, a planarization layer, a first electrode, an insulating layer, an emissive layer and a second electrode on a substrate, An organic EL display device having the cured product described in

[10] for the planarization layer and / or the insulating layer.

[0025]

[13] At least metal wiring, the cured product described in

[10] , and a display device having a plurality of light-emitting elements, The light-emitting element is provided with a pair of electrode terminals on either one of its surfaces. The pair of electrode terminals are connected to a plurality of metal wires extending within the cured material. A display device in which multiple metal wires maintain electrical insulation due to the hardened material.

[0026]

[14] Compounds having a substructure represented by formula (2).

[0027] [ka]

[0028] In formula (2), R 3 and R 4 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 5 and R 6 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and * represents a bond.

[0029]

[15] A compound represented by any of the following structures.

[0030] [ka]

[0031] R 7 , R 9 , R 11 , R 13 , R 15 and R 17 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 8 , R 10 , R 12 , R 14 , R 16 and R 18 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6. [Effects of the Invention]

[0032] The resin composition of the present invention can form a cured product with excellent heat resistance and substrate adhesion after heating. [Brief explanation of the drawing]

[0033] [Figure 1] This is a cross-sectional view of an example of an organic EL display device. [Figure 2] This is a cross-sectional view of an example of a display device. [Figure 3] This is a schematic diagram of the manufacturing procedure for an organic EL display device. [Modes for carrying out the invention]

[0034] Embodiments of the present invention will be described in detail.

[0035] The resin composition of the present invention comprises an alkali-soluble resin (a) and a compound (b) having at least two substructures represented by formula (1) within its molecule.

[0036] [ka]

[0037] In formula (1), R 1 R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 2 * represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 2 to 20 carbon atoms which may have substituents, and * represents a bond.

[0038] <Alkali-soluble resin (a)> The photosensitive resin composition of the present invention contains an alkali-soluble resin (a) (hereinafter sometimes referred to as component (a)). Alkali solubility means that when a solution of the resin dissolved in γ-butyrolactone is applied to a silicon wafer, pre-baked at 120°C for 4 minutes to form a pre-baked film with a thickness of 10 μm ± 0.5 μm, the dissolution rate determined from the reduction in film thickness when the pre-baked film is immersed in a 2.38% by mass aqueous solution of tetramethylammonium hydroxide at 23 ± 1°C for 1 minute and then rinsed with pure water is 50 nm / min or more.

[0039] (a) Component is alkali soluble and therefore has hydroxyl groups and / or acidic groups in the structural units of the resin and / or at the ends of its main chain. Examples of acidic groups include carboxyl groups, phenolic hydroxyl groups, and sulfonic acid groups.

[0040] (a) The component may include, but is not limited to, known materials such as polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, polyamides, copolymers thereof, polyhydroxystyrene, copolymers of hydroxystyrene and styrene derivatives that do not have phenolic hydroxyl groups, acrylic resins, siloxane resins, cardo resins, and phenolic resins. Component (a) may contain two or more of these alkali-soluble resins.

[0041] Among these components (a), it is preferable that component (a) contains one or more selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, copolymers thereof, polyhydroxystyrene, and copolymers of hydroxystyrene and styrene derivatives that do not have phenolic hydroxyl groups, due to their high development adhesion and excellent heat resistance.

[0042] Furthermore, because the amount of outgassing at high temperatures is low, the long-term reliability when the cured product is used in an organic EL display device is high. Therefore, it is more preferable that component (a) contains one or more selected from polyimide, polyimide precursors, and copolymers thereof.

[0043] Furthermore, from the viewpoint of storage stability, it is more preferable that component (a) contains either polyhydroxystyrene or a copolymer of hydroxystyrene and a styrene derivative that does not have a phenolic hydroxyl group, or both.

[0044] Furthermore, from the viewpoint of further improving storage stability, it is more preferable that the total mass of component (a) contains 50% or more by mass of polyhydroxystyrene and copolymers of hydroxystyrene and styrene derivatives that do not have phenolic hydroxyl groups.

[0045] Here, polyimide precursors refer to resins that are converted to polyimide through heat treatment or chemical treatment, such as polyamic acid and polyamic acid esters. Polybenzoxazole precursors refer to resins that are converted to polybenzoxazole through heat treatment or chemical treatment, such as polyhydroxyamides.

[0046] The polyimide precursors, polybenzoxazole precursors, and polyamides described above consist substantially of only the specific structural units represented by formula (3) below, polyimides consist substantially of only the structural units represented by formula (4) below, and benzoxazoles consist substantially of only the structural units represented by formula (5) below. Here, the term "substantially" means that, due to purification processes such as the resin drying process, unintended trace amounts of cyclized structural units or trace amounts of uncyclized structural units that do not actually achieve complete cyclization may be included.

[0047] [ka]

[0048] In formula (3), X represents an organic group with 4 to 40 carbon atoms and 2 to 8 valencies, and Y represents an organic group with 6 to 40 carbon atoms and 2 to 11 valencies. 19 and R 21Each of these independently represents either a hydroxyl group or a sulfonic acid group. 20 and R 22 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group with 1 to 20 carbon atoms. Each of these independently represents an integer from 0 to 3, and v represents an integer from 0 to 6.

[0049] Polyimide precursors consist only of structural units represented by formula (3) where u ≥ 2.

[0050] The polybenzoxazole precursor is a structural unit represented by formula (3) in which u < 2 and v ≥ 2, and has multiple R 21 At least two of these structural units consist solely of hydroxyl groups.

[0051] Polyamide consists solely of structural units represented by formula (3) that do not correspond to either the polyimide precursor or the polybenzoxazole precursor mentioned above.

[0052] [ka]

[0053] In formula (4), E represents an organic group with 4 to 40 carbon atoms and 4 to 10 valencies, and G represents an organic group with 6 to 40 carbon atoms and 2 to 8 valencies. 23 and R 24 Each of these independently represents a carboxyl group, a sulfonic acid group, or a hydroxyl group. Each of x and y independently represents an integer between 0 and 6, where x + y > 0.

[0054] [ka]

[0055] In formula (5), J represents an organic group with 4 to 40 carbon atoms and 4 to 10 valencies, and L represents an organic group with 6 to 40 carbon atoms and 2 to 8 valencies. 30 and R 31Each of these independently represents a hydroxyl group. p and q each independently represent an integer from 0 to 6.

[0056] With respect to these copolymers, when the terms "polyimide," "polyimide precursor," "polybenzoxazole," "polybenzoxazole precursor," "polyamide," and "polymers thereof" are used, the term "polymers thereof" means copolymers consisting of two or more structural units selected from the group consisting of the structural units of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, and polyamide. In other words, in the above case, "polymers thereof" means having two or more structural units selected from the group consisting of the structural unit represented by formula (3), the structural unit represented by formula (4), and the structural unit represented by formula (5), which correspond to any of the structural units of polyimide precursor, polybenzoxazole precursor, or polyamide. Therefore, when referring to polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, and copolymers thereof, the term "polymers thereof" means copolymers composed of two or more structural units selected from the group consisting of the structural units of polyimides, polyimide precursors, polybenzoxazoles, and polybenzoxazole precursors.

[0057] The number of structural units in each of the polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, polyamides, and copolymers thereof is preferably 5 to 100,000.

[0058] In equation (3) above, X(R 19 ) t (COOR 20 ) u X represents an acid residue. An acid residue refers to a residue obtained by removing two carboxyl groups from an acid compound, where X is an organic group having 4 to 40 carbon atoms and being 2 to 8 valent, with a preference for 2 to 8 valent organic groups containing an aromatic ring or a cyclic aliphatic group.

[0059] Acid residues include dicarboxylic acid residues such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid; tricarboxylic acid residues such as trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid; pyromellitic acid, 3,3',4,4'-biphenyltetracarboxylic acid, 2,3,3',4'-biphenyltetracarboxylic acid, 2,2',3,3'-biphenyltetracarboxylic acid, 3,3',4,4'-benzophenonetetracarboxylic acid, 2,2',3,3'-benzophenonetetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, and 2,2-bis(2,3-dicarboxyphenyl) Examples of tetracarboxylic acid residues include tetracarboxylic acid residues such as tetracarboxylic acid (ruboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane, bis(2,3-dicarboxyphenyl)methane, bis(3,4-dicarboxyphenyl) ether, 1,2,5,6-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 2,3,5,6-pyridinetetracarboxylic acid, 3,4,9,10-perylenetetracarboxylic acid and aromatic tetracarboxylic acids with the structures shown below, as well as aliphatic tetracarboxylic acids such as butanetetracarboxylic acid and aliphatic tetracarboxylic acids containing cyclic aliphatic groups such as 1,2,3,4-cyclopentanetetracarboxylic acid. (a) Component is X(R) in formula (3). 19 ) t (COOR 20 ) u These residues may have two or more different types.

[0060] [ka]

[0061] R 25 R represents an oxygen atom, C(CF3)2 or C(CH3)2. 26 and R27 Each of these independently represents either a hydrogen atom or a hydroxyl group.

[0062] In the case of the residues of the above acid, if they are tricarboxylic acid, tetracarboxylic acid, or pentacarboxylic acid residues, one, two, or three carboxyl groups are present in formula (3) (COOR 20 This corresponds to ).

[0063] In the above equation (4), E(R 23 ) x represents a residue of an acid dianhydride. An acid dianhydride residue refers to a residue obtained by removing two acid anhydride structures from an acid dianhydride compound, where E is an organic group having 4 to 40 carbon atoms and tetravalent to decavalent, and among these, an organic group containing an aromatic ring or a cyclic aliphatic group is preferred.

[0064] Specifically, the residues of the acid dianhydrides include pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 2,3,3',4'-biphenyltetracarboxylic acid dianhydride, 2,2',3,3'-biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride, 2,2',3,3'-benzophenonetetracarboxylic acid dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, and bis(3,4-dicarboxyphenyl) Examples include aromatic tetracarboxylic dianhydrides such as ether dianhydrides, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorenic acid dianhydride, 9,9-bis{4-(3,4-dicarboxyphenoxy)phenyl}fluorenic acid dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, and acid dianhydrides with the structures shown below, as well as aliphatic tetracarboxylic dianhydrides such as butanetetracarboxylic dianhydride, and residues of aliphatic tetracarboxylic dianhydrides containing cyclic aliphatic groups such as 1,2,3,4-cyclopentanetetracarboxylic dianhydride. (a) Component is E(R) in formula (4) 23 ) x These residues may have two or more different types.

[0065] [ka]

[0066] R 25 R represents an oxygen atom, C(CF3)2 or C(CH3)2. 26 and R27 Each of these independently represents either a hydrogen atom or a hydroxyl group.

[0067] In the above equation (5), L(R 31 ) q represents a dicarboxylic acid residue. A dicarboxylic acid residue refers to a residue obtained by removing two carboxyl groups from a dicarboxylic acid compound, where L is an organic group having 6 to 40 carbon atoms and 2 to 8 valent values, with 2 to 8 valent organic groups containing aromatic rings or cyclic aliphatic groups being preferred.

[0068] Specific examples of dicarboxylic acid residues include phthalic acid, terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, triphenyl dicarboxylic acid, 2,5-franzicarboxylic acid, 2,5-thiophene dicarboxylic acid, 1,4-cyclohexane dicarboxylic acid, 2-fluoroterephthalic acid, 2-methoxyterephthalic acid, and 2-phenoxyterephthalic acid. Component (a) is L(R) in formula (5). 29 ) q These residues may have two or more different types.

[0069] In the above equation (3), Y(R 21 ) v (COOR 22 ) w and G(R) in the above formula (4) 24 ) y represents a diamine residue. A diamine residue refers to a residue obtained by removing two amino groups from a diamine compound. Y is an organic group having 6 to 40 carbon atoms and 2 to 11 valencies, with 2 to 11 valencies containing an aromatic ring or a cyclic aliphatic group being preferred. G is an organic group having 6 to 40 carbon atoms and 2 to 8 valencies, with 2 to 8 valencies containing an aromatic ring or a cyclic aliphatic group being preferred.

[0070] Specific examples of diamine residues include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1,4-bis(4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl} ether, and 1,4-bis(4-aminophenoxy)benzene. , 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-diethyl-4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-diethyl-4,4'-diaminobiphenyl, 2,2',3,3'-tetramethyl-4,4'-diaminobiphenyl, 3,3',4,4'-tetramethyl-4,4'-diaminobiphenyl, 2,2'-di(trifluoromethyl)-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 3,3'-diamino-4,4'-dihydroxy Biphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, bis(3-amino-4-hydroxyphenyl)propane, bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 9,9-bi The following can be included: (a) Component (3-amino-4-hydroxyphenyl)fluorene, 2,2'-bis(trifluoromethyl)-5,5'-dihydroxybenzidine, 3,5-diaminobenzoic acid, 3,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, and aromatic diamine residues such as compounds in which at least some of the hydrogen atoms of these aromatic rings are substituted with alkyl or halogen atoms; aliphatic diamine residues containing cyclic aliphatic groups such as cyclohexyldiamine and methylenebiscyclohexylamine; and diamine residues having the structure shown below. 21 )v (COOR 22 ) w and G(R 24 ) y in formula (4) may have two or more kinds of these residues.

[0071] [Chemical formula]

[0072] R 25 represents an oxygen atom, C(CF3)2 or C(CH3)2. R 26 ~R 29 each independently represents a hydrogen atom or a hydroxyl group.

[0073] J(R 28 ) p in the above formula (5) represents a residue of bisaminophenol. The residue of bisaminophenol refers to the residue obtained by removing two amino groups and two phenolic hydroxyl groups from a bisaminophenol compound. J is an organic group having 4 to 40 carbon atoms and 4 to 10 valences, and among them, an organic group having 4 to 10 valences containing an aromatic ring or a cycloaliphatic group is preferable.

[0074] Examples of the bisaminophenol residue include those similar to the residue of bisaminophenol among the residues of the above-mentioned diamines. Component (a) may have two or more kinds of these residues as J(R 30 ) p in formula (5).

[0075] In addition, the terminals of these resins may be capped with a monoamine, acid anhydride, acid chloride, monocarboxylic acid, or active ester compound having a known acidic group.

[0076] Known materials can be used as polyhydroxystyrene, including, for example, hydroxystyrene, dihydroxystyrene, allylphenol, coumaric acid, 2'-hydroxychalcone, resveratrol, and 4-hydroxystilbene. Polyhydroxystyrene may be obtained using two or more of these materials. Alternatively, polyhydroxystyrene may be polymerized using phenol derivatives having an unsaturated bond in which the phenolic hydroxyl group has been alkoxysubstituted, and after polymerization, the alkoxysubstituted substituent may be deprotected by the action of an acid or the like to return it to a phenolic hydroxyl group.

[0077] Furthermore, copolymers of hydroxystyrene and styrene derivatives lacking phenolic hydroxyl groups can be produced, for example, by addition polymerization of a phenol derivative having the aforementioned unsaturated bond and a styrene derivative lacking phenolic hydroxyl groups. Known materials can be used as the styrene derivative lacking phenolic hydroxyl groups, including, for example, styrene, aminostyrene, vinyltoluene, vinylbenzoic acid and its ester compounds, and styrenesulfonic acid. From the viewpoint of opening size change, styrene is preferred as the styrene derivative lacking phenolic hydroxyl groups.

[0078] As the acrylic resin, known materials can be used, but examples include methacrylic acid and acrylic acid, as well as their α-position haloalkyl, alkoxy, halogen, nitro, and cyano-substituted derivatives.

[0079] Examples of cardo resins include resins having a cardo structure, that is, a skeletal structure in which two cyclic structures are bonded to a quaternary carbon atom that constitutes a cyclic structure. A common cardo structure is one in which a benzene ring is bonded to a fluorene ring.

[0080] Examples of phenolic resins include known novolac phenolic resins and resol phenolic resins, which are obtained by polycondensing various phenols individually or in mixtures thereof with aldehydes such as formalin.

[0081] Examples of siloxane resins include known siloxane resins obtained by hydrolyzing and dehydrating one or more organosilanes selected from tetrafunctional organosilanes, trifunctional organosilanes, difunctional organosilanes, and monofunctional organosilanes.

[0082] <Compound (b) having a substructure represented by formula (1)> The resin composition of the present invention includes a compound (b) (hereinafter sometimes referred to as component (b)) having at least two substructures represented by formula (1) within the molecule.

[0083] [ka]

[0084] In formula (1), R 1 R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 2 * represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 2 to 20 carbon atoms which may have substituents, and * represents a bond. Here, in the notation for aryl groups having 6 to 20 carbon atoms that may have substituents, the number of carbon atoms in the substituents is not included. Similarly, in the notation for heteroaryl groups having 2 to 20 carbon atoms that may have substituents, the number of carbon atoms in the substituents is not included.

[0085] The resin composition of the present invention, by containing component (b), can improve the heat resistance and substrate adhesion of the cured product after heating. The mechanism of improved heat resistance is thought to be due to the reaction between component (b) and component (a), or between components (b) themselves, upon heating, which increases the molecular weight.

[0086] When satisfying the condition of having at least two or more substructures represented by the formula (1) as components in the molecule, the nitrogen atoms may overlap. For example, the substructure represented by the following formula (6) satisfies the condition of having at least two or more substructures represented by the formula (1) in the molecule.

[0087]

Chemical formula

[0088] In formula (6), R<000009^and R 4 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 5 and R 6 each independently represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 2 to 20 carbon atoms which may have a substituent, and * represents a bond.

[0089] In formula (1) and formula (6), examples of the substituent in the aryl group having 6 to 20 carbon atoms which may have a substituent or the heteroaryl group having 2 to 20 carbon atoms which may have a substituent include, but are not limited to, an alkyl group, a carboxy group, a hydroxy group, a cyano group, an alkoxy group, an aryl group, a heteroaryl group, an amino group, a trifluoromethyl group, a fluoro group, a bromo group, a chloro group, an iodo group, an acetyl group, a sulfo group, etc.

[0090] Examples of the aryl group having 6 to 20 carbon atoms include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, tetracene, fluoranthene, pyrene, perylene, chrysene, triphenylene, etc.

[0091] [[ID=Examples of heteroaryl groups having 2 to 20 carbon atoms include, but are not limited to, pyrrole, furan, thiophene, indole, isoindole, benzofuran, benzothiophene, pyrazole, imidazole, triazole, benzimidazole, benzotriazole, oxazole, thiazole, pyridine, pyrimidine, pyrazine, triazine, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, carbazole, dibenzofuran, phenazine, phenoxazine, and phenothiazine.

[0092] Furthermore, component (b) may have three or more substructures represented by formula (1), and from the viewpoint of heat resistance, it is preferable that component (b) has four or more substructures represented by formula (1), and more preferably six or more. There is no particular upper limit to the number of substructures represented by (1) contained in one molecule, but it is preferable that it is 10 or less.

[0093] Examples of compounds having a substructure represented by formula (1) are shown below, but are not limited to these.

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] Me represents a methyl group, Et represents an ethyl group, and i-Pr represents an isopropyl group.

[0100] Furthermore, from the standpoint of storage stability, R in formula (1) 2 Preferably, it is an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and more preferably, from the viewpoint of raw material availability, an aryl group having 6 to 10 carbon atoms that may have substituents, or a heteroaryl group having 2 to 10 carbon atoms that may have substituents.

[0101] Furthermore, from the perspective of further improving heat resistance, R in formula (1) 2 This is the Hammett rule substituent constant σ p A C6-C20 aryl group having a substituent with a value of 0.4 or greater, or a Hammett substituent constant σ p A heteroaryl group having 2 to 20 carbon atoms and a substituent with a value of 0.4 or greater is preferred. p The values ​​can be quoted from the Basic Edition of the Chemical Handbook, 5th Revised Edition (II-380p). σ p Examples of substituents with a value of 0.4 or higher include, but are not limited to, cyano groups, nitro groups, acetyl groups, trifluoromethyl groups, and carboxyl groups.

[0102] Furthermore, in addition to the perspective of heat resistance, as shown in reaction equation (7), R 1 Since modifying the alkyl group requires one step in synthesis, the R of formula (1) is preferred from the standpoint of ease of synthesis. 1 It is preferable that it is a hydrogen atom.

[0103] [ka]

[0104] In reaction equation (7), R 2 R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. 32 * represents an alkyl group with 1 to 10 carbon atoms, and * represents a bond.

[0105] Furthermore, from the viewpoint of storage stability, it is preferable that at least one bond in formula (1) is directly bonded to an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and from the viewpoint of raw material availability, an aryl group having 6 to 10 carbon atoms that may have substituents, or a heteroaryl group having 2 to 10 carbon atoms that may have substituents is more preferable. As a mechanism for improving storage stability, the direct bond of the aryl group or heteroaryl group causes the lone pair of electrons on the nitrogen atom to form a resonance structure with the aromatic ring, OR 1 This is thought to be because it suppresses the elimination of the group and reduces side reactions.

[0106] Furthermore, from the viewpoint of storage stability, it is preferable that component (b) contains a compound having a substructure represented by formula (2).

[0107] [ka]

[0108] In formula (2), R 3 and R 4 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 5 and R 6 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and * represents a bond.

[0109] Examples of compounds having the substructure represented by formula (2) include, but are not limited to, the following compounds.

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, n-Bu represents a n-butyl group, and t-Bu represents a tert-butyl group.

[0114] Furthermore, compounds having the substructure represented by formula (2) do not include compounds in which the substituent bonded to the α-position of the nitrogen atom is the same aromatic ring or heteroaromatic ring, as shown in formula (8).

[0115] [ka]

[0116] In formula (8), R 3 and R 4 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and * represents a bond.

[0117] Furthermore, from the viewpoint of improving the heat resistance of the cured product after heating, it is more preferable that component (b) contains at least one compound represented by one of the following structures.

[0118] [ka]

[0119] R 7 , R 9 , R 11 , R 13 , R 15 and R 17 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 8 , R 10 , R 12 , R 14, R 16 and R 18 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6. The explanation for aryl groups having 6 to 20 carbon atoms that may have substituents and heteroaryl groups having 2 to 20 carbon atoms that may have substituents is the same as in the explanation for formula (1) above.

[0120] The following compounds are specific examples of the above-mentioned group of compounds, but are not limited to these.

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] Me represents a methyl group, and Et represents an ethyl group.

[0125] Compounds having at least two substructures represented by formula (1) in their molecule can be obtained, for example, by reacting a compound having at least one primary amino group or at least two secondary amino groups in its molecule with various aldehydes under basic conditions, and further by reacting them with various alcohols under acidic conditions to obtain the R in formula (1). 1 Compounds in which the alkyl group has 1 to 10 carbon atoms can be obtained.

[0126] Compounds having at least one primary amino group in their molecule include isopropylamine, 2-amino-2-methylpropane, butylamine, isobutylamine, 3-aminopyrazole, 3-amino-1,2,4-triazole, cyclopentylamine, amylamine, aniline, 2-aminopyridine, 2-aminopyrazole, 2-aminopyrimidine, furfurylamine, cyclohexylamine, 2-aminothiazole, 2-amino-1,3,4-thiadiazole, Benzylamine, 2-Picolylamine, 2-Phenylethylamine, 2-Aminobenzoimidazole, 4-Bromoaniline, 4-Nitroaniline, 4-Methoxyaniline, 4-Ethylaniline, p-Toluidine, 3,4'-Diaminodiphenyl ether, 4,4'-Diaminodiphenyl ether, 3,4'-Diaminodiphenylmethane, 4,4'-Diaminodiphenylmethane, 1,4-Bis(4-Aminophenoxy)benzene, Benzidine, m-Phenylenediamine p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl} ether, 1,4-bis(4-aminophenoxy)benzene, 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-diethyl-4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-diethyl-4,4'-diaminobiphenyl Examples of such substances include, but are not limited to, 2,2',3,3'-tetramethyl-4,4'-diaminobiphenyl, 3,3',4,4'-tetramethyl-4,4'-diaminobiphenyl, 2,2'-di(trifluoromethyl)-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, p-xylenediamine, 1,2-cyclohexanediamine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, and ethylenediamine.

[0127] Examples of compounds having at least two secondary amino groups in their molecule include, but are not limited to, piperazine, 2-methylpiperazine, and N,N'-diphenyl-1,4-phenylenediamine.

[0128] Examples of various aldehydes include acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, pivalaldehyde, isopivalaldehyde, valeraldehyde, hexanal, heptanal, nonanal, decanal, 2-ethylbutyraldehyde, 2-ethylhexanal, benzaldehyde, furfural, 2-pyridinecarboxaldehyde, 3-pyridinecarboxaldehyde, and 4-pyridine. Zincarboxaldehyde, 2-thiophenecarboxaldehyde, p-tolualdehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 4-cyanobenzaldehyde, o-anisaldehyde, m-anisaldehyde, p-anisaldehyde, 2,4-dihydroxybenzaldehyde, 2-chlorobenzaldehyde, 3-chlorobenzaldehyde, 4-chlorobenzaldehyde, 2-fluorobenzaldehyde Fluorobenzaldehyde, 3-fluorobenzaldehyde, 4-fluorobenzaldehyde, 2-iodobenzaldehyde, 3-iodobenzaldehyde, 4-iodobenzaldehyde, 2,4,6-trimethylbenzaldehyde, piperonal, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde, 1-naphthaldehyde, 2-naphthaldehyde, 2-trifluoromethylbenzaldehyde Examples include, but are not limited to, dehydes, 4-trifluoromethylbenzaldehyde, 4-phenylbenzaldehyde, 2-bromobenzaldehyde, 3-bromobenzaldehyde, 4-bromobenzaldehyde, pentafluorobenzaldehyde, 2,4,6-trimethoxybenzaldehyde, 2-pyrrolecarbaldehyde, 1H-imidazole-2-carbaldehyde, and indole-3-carbaldehyde.

[0129] Examples of alcohols include, but are not limited to, methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, and 1-decanol.

[0130] Basic conditions can be met by carrying out the reaction in the presence of a known base, such as sodium hydroxide or potassium hydroxide. Acidic conditions can be met by carrying out the reaction in the presence of a known acid, such as hydrochloric acid.

[0131] In the present invention, from the viewpoint of improving heat resistance after curing, the content of component (b) is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of component (a). Furthermore, from the viewpoint of improving heat resistance after curing, the content of component (b) is preferably 60 parts by mass or less, more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, and particularly preferably 30 parts by mass or less, per 100 parts by mass of component (a).

[0132] <Photosensitive compound (c)> The resin composition of the present invention may contain a photosensitive compound (c) (hereinafter sometimes referred to as component (c)). From the viewpoint of increasing sensitivity, the content of component (c) is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of component (a). On the other hand, from the viewpoint of long-term reliability when the cured product of the present invention is used as the planarization layer and / or insulating layer of an organic EL display device, the content of component (c) is preferably 100 parts by mass or less per 100 parts by mass of component (a).

[0133] (c) The component may include a photoacid generator (c1) and a photopolymerization initiator (c2). The photoacid generator (c1) is a compound that generates acid upon light irradiation, and the photopolymerization initiator (c2) is a compound that undergoes bond cleavage and / or reaction upon exposure, generating radicals.

[0134] By including a photoacid generator (c1), acid is generated in the light-irradiated area, increasing its solubility in the alkaline aqueous solution, and a positive relief pattern can be obtained in which the light-irradiated area dissolves. Alternatively, by including the photoacid generator (c1) and an epoxy compound or thermal crosslinking agent described later, the acid generated in the light-irradiated area promotes the crosslinking reaction of the epoxy compound or thermal crosslinking agent, and a negative relief pattern can be obtained in which the light-irradiated area becomes insoluble. On the other hand, by including a photopolymerization initiator (c2) and a radical polymerizable compound described later, radical polymerization proceeds in the light-irradiated area, and a negative relief pattern can be obtained in which the light-irradiated area becomes insoluble. When the cured product of the present invention is used as a planarization layer and / or insulating layer of an organic EL display device, it is preferable that component (c) includes a photoacid generator (c1) that can obtain a positive relief pattern, from the viewpoint of being able to form a fine pattern.

[0135] The photoacid generator (c1) can, for example, contain a quinone diazide compound. The photosensitive resin composition of the present invention preferably contains two or more types of photoacid generators (c1), and when two or more types are included, a more sensitive photosensitive resin composition can be obtained.

[0136] The quinone diazide compounds may include those in which the sulfonic acid of quinone diazide is esterified to a polyhydroxy compound, those in which the sulfonic acid of quinone diazide is sulfonamide bonded to a polyamino compound, and those in which the sulfonic acid of quinone diazide is esterified and / or sulfonamide bonded to a polyhydroxypolyamino compound.

[0137] As the quinone diazidosulfonyl ester group, either the 5-naphthoquinone diazidosulfonyl group or the 4-naphthoquinone diazidosulfonyl group is preferably used. The quinone diazide compound may contain either one or both of the 4-naphthoquinone diazidosulfonyl group and the 5-naphthoquinone diazidosulfonyl group, or multiple types may be contained in combination. The 4-naphthoquinone diazidosulfonyl ester group has absorption in the i-line region of mercury lamps and is suitable for i-line exposure, while the 5-naphthoquinone diazidosulfonyl ester group has absorption extending to the g-line region of mercury lamps and is suitable for g-line exposure. Therefore, depending on the wavelength of light of the exposure apparatus, either one group or a combination of groups may be used as appropriate.

[0138] From the viewpoint of easily achieving high sensitivity, it is preferable that the quinone diazide compound contains a 4-naphthoquinone diazidosulfonyl ester group.

[0139] The above-mentioned quinone diazide compounds can be synthesized from a compound having a phenolic hydroxyl group and a quinone diazidesulfonic acid compound by any esterification reaction. Using these quinone diazide compounds improves resolution, sensitivity, and residual film ratio.

[0140] From the viewpoint of increasing sensitivity, the content of the photoacid generator (c1) is preferably 0.1 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 25 parts by mass or more, per 100 parts by mass of component (a). On the other hand, from the viewpoint of long-term reliability when the cured product of the present invention is used as the planarization layer and / or insulating layer of an organic EL display device, the content of the photoacid generator (c1) is preferably 100 parts by mass or less per 100 parts by mass of component (a).

[0141] Examples of photopolymerization initiators (c2) include benzyl ketal-based photopolymerization initiators, α-hydroxyketone-based photopolymerization initiators, α-aminoketone-based photopolymerization initiators, acylphosphine oxide-based photopolymerization initiators, oxime ester-based photopolymerization initiators, acridine-based photopolymerization initiators, titanocene-based photopolymerization initiators, benzophenone-based photopolymerization initiators, acetophenone-based photopolymerization initiators, aromatic ketoester-based photopolymerization initiators, and benzoic acid ester-based photopolymerization initiators. The photosensitive resin composition of the present invention may contain two or more types of photopolymerization initiators (c2). From the viewpoint of further improving sensitivity, it is even more preferable that the photopolymerization initiator (c2) contains an α-aminoketone-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, or an oxime ester-based photopolymerization initiator.

[0142] Examples of α-aminoketone-based photopolymerization initiators include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholinophenyl)-butan-1-one, and 3,6-bis(2-methyl-2-morpholinopropionyl)-9-octyl-9H-carbazole.

[0143] Examples of acylphosphine oxide-based photopolymerization initiators include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide.

[0144] Examples of oxime ester-based photopolymerization initiators include 1-phenylpropane-1,2-dione-2-(O-ethoxycarbonyl)oxime, 1-phenylbutane-1,2-dione-2-(O-methoxycarbonyl)oxime, 1,3-diphenylpropane-1,2,3-trione-2-(O-ethoxycarbonyl)oxime, 1-[4-(phenylthio)phenyl]octane-1,2-dione-2-(O-benzoyl)oxime, 1-[4-[4-(carboxyphenyl)thio]phenyl]propane-1,2-dione-2-(O-acetyl)oxime, and 1-[9- It may contain ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone-1-(O-acetyl)oxime, 1-[9-ethyl-6-[2-methyl-4-[1-(2,2-dimethyl-1,3-dioxolan-4-yl)methyloxy]benzoyl]-9H-carbazol-3-yl]ethanone-1-(O-acetyl)oxime, or 1-(9-ethyl-6-nitro-9H-carbazol-3-yl)-1-[2-methyl-4-(1-methoxypropane-2-yloxy)phenyl]methanone-1-(O-acetyl)oxime, etc.

[0145] From the viewpoint of increasing sensitivity, the content of the photopolymerization initiator (c2) is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the total of component (a) and the radical polymerizable compound described later. On the other hand, from the viewpoint of further improving resolution and reducing the taper angle, the content of the photopolymerization initiator (c2) is preferably 50 parts by mass or less per 100 parts by mass of the total of component (a) and the radical polymerizable compound described later.

[0146] <Radical polymerizable compounds> The resin composition of the present invention may contain a radical polymerizable compound. In particular, if the photosensitive resin composition contains a photopolymerization initiator (c2), it is essential to include a radical polymerizable compound. A radical polymerizable compound is a compound having multiple ethylenically unsaturated double bonds in its molecule. During exposure, radical polymerization of the radical polymerizable compound proceeds due to radicals generated from the aforementioned photopolymerization initiator (c2), and a negative pattern can be obtained by insolubilizing the light-irradiated area. Furthermore, by including a radical polymerizable compound, the photocuring of the light-irradiated area is accelerated, and sensitivity can be further improved. In addition, the crosslinking density after thermal curing is improved, which can improve the hardness of the cured product.

[0147] As radical polymerizable compounds, compounds having (meth)acryloyl groups that readily undergo radical polymerization are preferred. From the viewpoint of improving sensitivity during exposure and hardness of the cured product, compounds having two or more (meth)acryloyl groups in the molecule are more preferred. The double bond equivalent of the radical polymerizable compound is preferably 80 to 400 g / mol from the viewpoint of improving sensitivity during exposure and hardness of the cured product.

[0148] From the viewpoint of further improving sensitivity and reducing the taper angle, the content of the radical polymerizable compound is preferably 15% by mass or more, and more preferably 30% by mass or more, based on 100% by mass of the total of component (a) and the radical polymerizable compound. On the other hand, from the viewpoint of further improving the heat resistance of the cured product and reducing the taper angle, it is preferably 65% ​​by mass or less, and more preferably 50% by mass or less, based on 100% by mass of the total of component (a) and the radical polymerizable compound.

[0149] <Thermal Crosslinking Agent> The resin composition of the present invention may contain a thermal crosslinking agent as a compound that can improve the heat resistance of the cured product other than component (b). A thermal crosslinking agent refers to a compound having at least two functional groups selected from the group consisting of epoxy groups, methylol groups, alkoxymethyl groups, and oxetanyl groups in its molecule. By including a thermal crosslinking agent, crosslinking can occur between the thermal crosslinking agent and component (a), between the thermal crosslinking agent and component (b), or between the thermal crosslinking agents themselves, further improving the heat resistance, chemical resistance, and bending resistance of the cured product after heat curing.

[0150] From the viewpoint of further improving the chemical resistance and bending resistance of the cured product, the content of the thermal crosslinking agent is preferably 1 part by mass or more, preferably 5 parts by mass or more, and more preferably 10 parts by mass or more, per 100 parts by mass of component (a). Furthermore, from the viewpoint of the storage stability of the resin composition, the content of the thermal crosslinking agent is preferably 30 parts by mass or less per 100 parts by mass of component (a).

[0151] <Solvent> The resin composition of the present invention may contain a solvent. By including a solvent, it can be made into a varnish, which can improve its applicability.

[0152] As solvents, polar aprotic solvents such as γ-butyrolactone, ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tetrahydrofuran, dioxane, acetone, methyl ethyl Ketones, including diisobutyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, and diacetone alcohol; esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and ethyl lactate; ethyl 2-hydroxy-2-methylpropionate; 3-methoxypropyl Methyl pionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate,It may also contain n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, ethyl 2-oxobutanoate and other esters, aromatic hydrocarbons such as toluene and xylene, amides such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, N,N-dimethylpropanamide, N,N-dimethylisobutylamide, and 3-methyl-2-oxazolidinone. The solvent may contain two or more of these.

[0153] The solvent content is not particularly limited, but is preferably 100 to 3000 parts by mass, and more preferably 150 to 2000 parts by mass, per 100 parts by mass of the total resin composition excluding the solvent. Furthermore, the proportion of solvent with a boiling point of 180°C or higher in 100 parts by mass of the total solvent is preferably 20 parts by mass or less, and more preferably 10 parts by mass or less. By reducing the proportion of solvent with a boiling point of 180°C or higher to 20 parts by mass or less, the amount of outgassing after thermal curing can be further reduced, and the long-term reliability of the organic EL device can be further improved.

[0154] <Adhesion improver> The resin composition of the present invention may contain an adhesion improver. The adhesion improver may include known silane coupling agents, titanium chelating agents, aluminum chelating agents, and compounds obtained by reacting aromatic amine compounds with alkoxy group-containing silicon compounds. Two or more of these may be included. By including these adhesion improvers, the development adhesion to substrates such as silicon wafers, indium tin oxide (ITO), SiO2, and silicon nitride can be improved when developing the resin film. Furthermore, resistance to oxygen plasma and UV ozone treatments used for cleaning can be increased. The content of the adhesion improver is preferably 0.01 to 10% by mass of the total resin composition excluding the solvent.

[0155] <Surfactants> The resin composition of the present invention may contain a surfactant, which can improve wettability with the substrate. The surfactant may include known silicon-based surfactants, fluorine-based surfactants, acrylic-based and / or methacrylic-based surfactants.

[0156] If a surfactant is included, its content is preferably 0.001 to 1% by mass of the total resin composition excluding the solvent (100% by mass).

[0157] <Inorganic particles> The resin composition of the present invention may contain inorganic particles. Preferred specific examples of inorganic particles include, for example, silicon dioxide, titanium dioxide, barium titanate, alumina, and talc. The primary particle size of the inorganic particles is preferably 100 nm or less, and more preferably 60 nm or less.

[0158] The inorganic particle content is preferably 5 to 90 parts by mass in 100% by mass of the total resin composition excluding the solvent.

[0159] <Method for producing resin compositions> Next, a method for producing the resin composition of the present invention will be described. For example, the resin composition of the present invention can be obtained by dissolving components (a) and (b), and optionally, component (c), a radical polymerizable compound, a thermal crosslinking agent, a solvent, an adhesion improver, a surfactant, inorganic particles, etc.

[0160] Dissolution methods include stirring and heating. When heating, the heating temperature should preferably be set within a range that does not impair the performance of the resin composition, and is usually between room temperature and 80°C. In this specification, room temperature is defined as 25°C. Furthermore, the order in which each component is dissolved is not particularly limited; for example, compounds with lower solubility are dissolved sequentially. When stirring, the rotation speed should preferably be set within a range that does not impair the performance of the resin composition, and is usually between 200 rpm and 2000 rpm. Even when stirring, heating may be used as needed, and is usually between room temperature and 80°C. In addition, for components that tend to generate bubbles during stirring and dissolution, such as surfactants and some adhesion improvers, adding them last after dissolving the other components can prevent poor dissolution of other components due to bubble generation.

[0161] The obtained resin composition is preferably filtered using a filtration filter to remove dirt and particles. Examples of filter pore sizes include, but are not limited to, 0.5 μm, 0.2 μm, 0.1 μm, 0.07 μm, 0.05 μm, and 0.02 μm. The material of the filtration filter can be polypropylene (PP), polyethylene (PE), nylon (NY), or polytetrafluoroethylene (PTFE). Polyethylene and nylon are preferred among these. Furthermore, if the resin composition contains organic pigments, it is preferable to use a filtration filter with a pore size larger than the particle size of these pigments.

[0162] <Method for manufacturing hardened products> The present invention provides a method for producing a cured product, in which case the resin composition is photosensitive, and includes the steps of forming a resin film made of the resin composition of the present invention on a substrate, exposing the resin film to light, developing the exposed resin film, and heat-treating the developed resin film.

[0163] The process of forming a resin film made of the resin composition of the present invention on a substrate will now be described. In the present invention, the resin film can be obtained by applying the resin composition of the present invention to obtain a coated film of the resin composition and then drying it. A known substrate, such as a glass substrate, can be used.

[0164] Methods for applying the resin composition of the present invention include, for example, spin coating, slit coating, dip coating, spray coating, and printing. Among these, the slit coating method is preferred because it allows coating with a small amount of coating liquid, which is advantageous for cost reduction. The amount of coating liquid required for the slit coating method is, for example, about 1 / 5 to 1 / 10 of that required for the spin coating method. As for the slit nozzle used for coating, several manufacturers' products can be selected, such as the "Linear Coater" from Dainippon Screen Manufacturing Co., Ltd., the "Spinless" from Tokyo Ohka Kogyo Co., Ltd., the "TS Coater" from Toray Engineering Co., Ltd., the "Table Coater" from Chugai Ro Kogyo Co., Ltd., the "CS Series" and "CL Series" from Tokyo Electron Limited, the "In-line Slit Coater" from Thermatronics Trading Co., Ltd., and the "Head Coater HC Series" from Hirata Kiko Co., Ltd. The coating speed is generally in the range of 10 mm / second to 400 mm / second. The thickness of the coated film varies depending on the solid content concentration and viscosity of the resin composition, but it is usually applied so that the film thickness after drying is 0.1 to 10 μm, preferably 0.3 to 5 μm.

[0165] Prior to coating, the substrate to which the resin composition will be applied may be pre-treated with the adhesion promoter described above. Examples of pre-treatment methods include treating the substrate surface with a solution obtained by dissolving the adhesion promoter in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, or diethyl adipate at a concentration of 0.5 to 20% by mass. Examples of substrate surface treatment methods include spin coating, slit die coating, bar coating, dip coating, spray coating, and vapor treatment.

[0166] After application, perform vacuum drying as needed. The vacuum drying rate depends on factors such as the vacuum chamber volume, vacuum pump capacity, and the diameter of the piping between the chamber and the pump. However, it is preferable to set the vacuum drying rate to a condition where, for example, the pressure inside the vacuum chamber is reduced to 40 Pa after 60 seconds, even without a coated substrate. The typical vacuum drying time is often between 30 and 100 seconds, and the pressure reached inside the vacuum chamber at the end of vacuum drying is usually 100 Pa or less with a coated substrate. By reducing the pressure to 100 Pa or less, a dry state with reduced stickiness on the surface of the coated film can be achieved, thereby suppressing surface contamination and particle generation during subsequent substrate handling.

[0167] It is common practice to heat-dry the coated film after application or after vacuum drying. This process is also called pre-baking. Drying is done using a hot plate, oven, infrared, etc. When using a hot plate, the coated film is heated either directly on the plate or while being held on a jig such as proxy pins placed on the plate. The heating time is preferably from 1 minute to several hours. The heating temperature varies depending on the type and purpose of the coated film, but from the viewpoint of promoting solvent drying during pre-baking, 80°C or higher is preferred, and 90°C or higher is more preferred. On the other hand, from the viewpoint of reducing the progression of hardening during pre-baking, 150°C or lower is preferred, and 140°C or lower is more preferred.

[0168] Next, we will explain the process of freezing the resin film. The resin film of the present invention can form a pattern by adding component (c) to the resin composition. For example, a desired pattern can be formed by exposing the resin film to chemical rays by irradiating it through a photomask having the desired pattern, and then developing it.

[0169] Chemical beams used for exposure include ultraviolet light, visible light, electron beams, and X-rays. In this invention, it is preferable to use the i-line (365 nm), h-line (405 nm), and g-line (436 nm) of a mercury lamp. If the image has positive-type photosensitivity, the exposed area dissolves in the developer. If the image has negative-type photosensitivity, the exposed area hardens and becomes insoluble in the developer.

[0170] Next, we will explain the process of developing the exposed resin film.

[0171] A resin film containing component (c) in the resin composition of the present invention forms a desired pattern after exposure by removing the exposed areas with a developer if the resin composition is positive type, or the unexposed areas if it is negative type. Preferred developers are aqueous solutions of alkaline compounds such as tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine. To these alkaline aqueous solutions, one or more polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, γ-butyrolactone, and dimethylacrylamide, alcohols such as methanol, ethanol, and isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone may be added. Possible development methods include spraying, paddle development, immersion, and ultrasonic development.

[0172] Next, it is preferable to rinse the pattern formed by development with distilled water. Alcohols such as ethanol and isopropyl alcohol, or esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to the distilled water for rinsing.

[0173] Next, we will explain the process of heat-treating the developed resin film. A cured product is obtained by heat-treating the developed resin film. From the viewpoint of further reducing the amount of outgassing generated from the cured product, the heat treatment temperature is preferably 180°C or higher, more preferably 200°C or higher, even more preferably 230°C or higher, and particularly preferably 250°C or higher. On the other hand, from the viewpoint of improving the toughness of the film of the cured product, the temperature is preferably 500°C or lower, and more preferably 450°C or lower. Within this temperature range, the temperature may be increased in stages or continuously. From the viewpoint of further reducing the amount of outgassing, the heat treatment time is preferably 30 minutes or more. Also, from the viewpoint of improving the toughness of the film of the cured product, it is preferably 3 hours or less. For example, a method of heat treatment at 150°C and 250°C for 30 minutes each can be used, or a method of heat treatment while linearly increasing the temperature from room temperature to 300°C over 2 hours can be used. Alternatively, the process may be carried out without performing the steps of exposing the resin film and developing the exposed resin film, by forming a resin film made of the resin composition of the present invention on a substrate and then performing the steps of heat-treating the formed resin film. In that case, the step of heat-treating the formed resin film is the same as the step of heat-treating the developed resin film.

[0174] <Cured product> The cured product of the present invention is a cured product obtained by curing the resin composition of the present invention. By heat-treating the resin composition of the present invention, components with low heat resistance can be removed, thereby further improving heat resistance and chemical resistance.

[0175] Furthermore, the resin composition of the present invention can improve the heat resistance of the cured product by containing component (b). From the viewpoint of further reducing the amount of outgassing generated from the cured product, the heat treatment temperature is preferably 180°C or higher, more preferably 200°C or higher, even more preferably 230°C or higher, and particularly preferably 250°C or higher. On the other hand, from the viewpoint of improving the film toughness of the cured product, it is preferably 500°C or lower, and more preferably 450°C or lower. Within this temperature range, the temperature may be increased in stages or continuously. From the viewpoint of further reducing the amount of outgassing, the heat treatment time is preferably 30 minutes or more. Also, from the viewpoint of improving the film toughness of the cured product, it is preferably 3 hours or less. For example, a method of heat treatment at 150°C and 250°C for 30 minutes each can be used, or a method of heat treatment while linearly increasing the temperature from room temperature to 300°C over 2 hours can be used.

[0176] <Examples of applications for resin compositions and cured products> The resin composition and cured product of the present invention are suitably used as surface protection layers and interlayer insulating layers for semiconductor elements, insulating layers for organic electroluminescence (EL) elements, planarization layers for thin-film transistor (TFT) substrates used to drive display devices using organic EL elements, wiring protection insulating layers for circuit boards, on-chip microlenses for solid-state image sensors, and planarization layers for various display devices and solid-state image sensors. For example, they are suitable as surface protection layers and interlayer insulating layers for MRAM with low heat resistance, polymer memory (PFRAM) and phase-change memory (PCRAM, Ovonics Unified Memory: OUM), which are promising as next-generation memories. They can also be used as insulating layers for display devices including a first electrode formed on a substrate and a second electrode provided opposite the first electrode, such as LCDs, ECDs, ELDs, and display devices using organic electroluminescent elements (organic electroluminescent devices). The following explanation will use organic EL display devices, semiconductor devices, and semiconductor electronic components as examples.

[0177] <Organic EL display device> The organic EL display device of the present invention is an organic EL display device having a drive circuit, a flattening layer, a first electrode, an insulating layer, a light-emitting layer, and a second electrode on a substrate, wherein the flattening layer and / or the insulating layer has a cured product of the present invention.

[0178] FIG. 1 shows a cross-sectional view of an example of an organic EL display device. On a substrate 6, bottom-gate type or top-gate type TFTs (thin film transistors) 1 are provided in a matrix, and a TFT insulating layer 3 is formed so as to cover the TFTs 1. Further, a wiring 2 connected to the TFT 1 is provided on the TFT insulating layer 3. Furthermore, a flattening layer 4 is provided on the TFT insulating layer 3 in a state of embedding the wiring 2. The flattening layer 4 is provided with contact holes 7 reaching the wiring 2. Then, an ITO (transparent electrode) 5 is formed on the flattening layer 4 in a state of being connected to the wiring 2 through the contact holes 7. Here, the ITO 5 serves as an electrode of a display element (for example, an organic EL element). And an insulating layer 8 is formed so as to cover the periphery of the ITO 5. The organic EL element may be a top emission type that emits light from the side opposite to the substrate 6, or a bottom emission type that extracts light from the substrate 6 side. In this way, an active matrix type organic EL display device in which a TFT 1 for driving each organic EL element is connected can be obtained.

[0179] Such a TFT insulating layer 3, flattening layer 4 and / or insulating layer 8 can be formed by a step of forming a resin film made of a resin composition obtained by adding a component (c) to the resin composition of the present invention, a step of exposing the resin film, a step of developing the exposed resin film, and a step of heat-treating the developed resin film. An organic EL display device can be obtained by a manufacturing method having these steps, and it can be used for a display device having a thin display such as a smartphone, a tablet PC, a television, etc.

[0180] <Display devices other than organic EL display devices> A display device other than the organic EL display device of the present invention is a display device having at least a metal wiring, a cured product of the present invention, and a plurality of light-emitting elements. Each of the light-emitting elements has a pair of electrode terminals on one surface, and the pair of electrode terminals are connected to a plurality of the metal wirings extending in the cured product. The plurality of metal wirings are configured to maintain electrical insulation by the cured product.

[0181] The display device will be described with reference to FIG. 2 as an example of one aspect. In FIG. 2, a display device 9 has a plurality of light-emitting elements 10 arranged on a counter substrate 15, and a cured product 11 is arranged on the light-emitting elements 10. "On the light-emitting elements" means not only the surface of the light-emitting elements but also any position above the support substrate or the light-emitting elements. In the aspect shown in FIG. 2, a configuration in which a plurality of cured products 11 are further laminated on the cured product 11 arranged so as to contact at least a part of the light-emitting elements 10, and a total of three layers are laminated is illustrated, but the cured product 11 may be a single layer. The light-emitting element 10 has a pair of electrode terminals 14 on the surface opposite to the surface in contact with the counter substrate 13, and each electrode terminal 14 is connected to a metal wiring 12 extending in the cured product 11. In addition, as long as the plurality of metal wirings 12 extending in the cured product 11 are covered by the cured product 11, the cured product 11 also functions as an insulating layer, and thus has a configuration for maintaining electrical insulation. The configuration in which the metal wiring maintains electrical insulation means that the necessary parts of the electrical insulation of the metal wiring are covered by a cured product obtained by curing a photosensitive resin composition containing an alkali-soluble resin (a). In the present invention, the state where the insulating layer has electrical insulation means that the volume resistivity of the insulating layer is 10 12 Ω·cm or more. Further, the light-emitting element 10 is electrically connected to a driving element 16 added to a light-emitting element driving substrate 15 provided at a position facing the counter substrate 13 through the metal wirings 12 and 12c, and the light emission of the light-emitting element 10 can be controlled. In addition, the light-emitting element driving substrate 15 is electrically connected to the metal wiring 12 via, for example, a solder bump 18. Further, a barrier metal 17 may be provided to prevent diffusion of metals such as the metal wiring 12.

[0182] The compound of the present invention is a compound having a substructure represented by formula (2).

[0183] [ka]

[0184] In formula (2), R 3 and R 4 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 5 and R 6 Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and * represents a bond.

[0185] By incorporating a compound having the substructure represented by formula (2) into the resin composition, the heat resistance and substrate adhesion of the cured product after heating can be improved.

[0186] The description of the compound having the substructure represented by formula (2) is the same as that described in the description of the resin composition above.

[0187] Furthermore, the compound of the present invention is a compound represented by any of the following structures.

[0188] [ka]

[0189] R 7 , R 9 , R 11 , R 13 , R 15 and R 17 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R 8 , R 10 , R 12 , R 14 , R 16 and R 18Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6.

[0190] By incorporating the above compound into the resin composition, the heat resistance and substrate adhesion of the cured resin composition can be improved.

[0191] The description of the above-mentioned compounds is the same as that given in the description of the resin composition above. [Examples]

[0192] The present invention will be described below with reference to examples, but the present invention is not limited to these examples. Each evaluation in the examples was performed using the following method.

[0193] (1) Evaluation of heat resistance The varnishes prepared in the examples and comparative examples were applied to a 10 cm × 10 cm glass substrate by spin coating so that the film thickness after heat treatment (curing) was 4.0 μm. The substrates were pre-baked at 120°C for 2 minutes to create pre-baked films. The obtained pre-baked films were cured at 230°C for 60 minutes under a nitrogen atmosphere using a high-temperature clean oven INH-9CD-S manufactured by Koyo Thermo Systems Co., Ltd. The resulting cured material was scraped off with a spatula to obtain powder. The glass transition temperature (Tg) of the powder thus obtained was determined using a TG-DTA simultaneous measurement device DTG-60A (manufactured by Shimadzu Corporation) under the following measurement conditions. The glass transition temperature was classified as "S" if it was 200°C or higher, "A" if it was 195°C or higher but less than 200°C, "B" if it was 190°C or higher but less than 195°C, "C" if it was 185°C or higher but less than 190°C, "D" if it was 180°C or higher but less than 185°C, "E" if it was 100°C or higher but less than 180°C, and "F" if it was less than 100°C. <Measurement conditions> • Sample weight: 10 mg · Heating rate: 10 °C / min · Heating range: 20 - 400 °C · Under nitrogen atmosphere · Gas flow rate: 300 mL / min (2) Evaluation of substrate adhesion The varnishes prepared in the examples and comparative examples were spin-coated onto a 10 cm × 10 cm glass / ITO substrate so that the film thickness after heat treatment (curing) was 2.0 μm, pre-baked at 120 °C for 2 minutes to create a pre-baked film. The obtained pre-baked film was cured at 230 °C for 60 minutes in a nitrogen atmosphere using a high-temperature clean oven INH-9CD-S manufactured by Koyo Thermo System Co., Ltd. The cured product was cut into a grid pattern with 10 rows and 10 columns of a total of 100 squares at 1 mm intervals, and a 24-hour pressure cooker test (hereinafter referred to as PCT, using an EHS-221MD manufactured by Tabai Co., Ltd.) was performed. For the cured product after 24 hours of PCT treatment, peeling was performed using "Cellotape (registered trademark)" (manufactured by Nichiban Co., Ltd.), and the adhesion was evaluated based on the number of peeled squares out of 100. When the number of peeled squares was less than 10, it was evaluated as "A", when it was 10 or more and less than 30, it was evaluated as "B", and when it was 30 or more, it was evaluated as "C". The PCT treatment was performed under saturated conditions of 121 °C and 0.21 MPa.

[0194] (3) Evaluation of storage stability For the varnishes prepared in the examples and comparative examples, the viscosity (viscosity before storage) was measured immediately after the formulation using an E-type rotational viscometer (VISCOMETER TV-25 manufactured by TOKI SANGYO Co., Ltd.). The rotational speed of the viscometer was selected as the highest rotational speed among those having the measured viscosity within the range. Also, the varnishes obtained in each example were placed in a sealed container, and the viscosity after storage at 25 °C for 14 days was measured in the same manner, and the viscosity change rate (%) ( {|viscosity after storage - viscosity before storage| / viscosity before storage} × 100) was determined. When the viscosity change rate was less than 4%, it was determined as "S", when it was 4% or more and less than 6%, it was determined as "A", when it was 6% or more and less than 8%, it was determined as "B", when it was 8% or more and less than 10%, it was determined as "C", when it was 10% or more and less than 12%, it was determined as "D", and when it was 12% or more, it was determined as "E".

[0195] Synthesis Example 1: Synthesis of polyhydroxystyrene (a-1) To a mixture of 2400 g of tetrahydrofuran and 4.48 mL (5.4 mmol) of a 1.2 mol / L hexane solution of sec-butyllithium as an initiator, 111.9 g (0.64 mol) of 4-tert-butoxystyrene was added, and polymerization was carried out with stirring for 3 hours. Then, 12.82 g (0.4 mol) of methanol was added to terminate the polymerization. Next, to purify the polymer, the reaction mixture was poured into 3 L of methanol, and the precipitated polymer was dried. The obtained polymer was dissolved in 1.6 L of acetone, and 2 g of concentrated hydrochloric acid was added at 60°C and stirred for 7 hours to deprotect 4-tert-butoxystyrene and convert it to hydroxystyrene. After the reaction was complete, the solution was poured into water to precipitate the polymer, and the obtained precipitate was washed three times with water. After that, it was dried in a vacuum dryer at 50°C for 24 hours to obtain polyhydroxystyrene (a-1). The weight-average molecular weight (polystyrene equivalent) determined by GPC (Waters 2695, columns: TSK-GEL α-2500 and TSK-GEL α-4000 in series, column temperature: 40°C, developing solvent: tetrahydrofuran) was 20,500, and the degree of dispersion was 1.2.

[0196] Synthesis Example 2: Synthesis of a hydroxyl group-containing diamine compound (α) 18.3 g (0.05 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane was dissolved in 100 mL of acetone and 17.4 g (0.3 mol) of propylene oxide, and the mixture was cooled to -15°C. A solution of 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride dissolved in 100 mL of acetone was added dropwise. After the addition was complete, the mixture was allowed to react at -15°C for 4 hours, and then returned to room temperature. The precipitated white solid was filtered off and vacuum-dried at 50°C.

[0197] 30 g of solid was placed in a 300 mL stainless steel autoclave and dispersed in 250 mL of methyl cellosolve. 2 g of 5% by mass palladium-carbon was added. Hydrogen was then introduced using a balloon, and the reduction reaction was carried out at room temperature. After approximately 2 hours, the reaction was terminated when it was confirmed that the balloon no longer deflated. After the reaction was complete, the palladium compound catalyst was removed by filtration, and the mixture was concentrated using a rotary evaporator to obtain a hydroxyl group-containing diamine compound (α) represented by the following formula.

[0198] [ka]

[0199] Synthesis Example 3: Synthesis of Polyimide Precursor (a-2) Under a stream of dry nitrogen, 31.0 g (0.10 mol) of 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride was dissolved in 500 g of N-methylpyrrolidone (hereinafter referred to as NMP). To this, 30.23 g (0.050 mol) of the hydroxyl group-containing diamine compound (α) obtained in Synthesis Example 2, 4.0 g of 4,4'-diaminodiphenyl ether, and 1.24 g (0.0050 mol) of 1,3-bis(3-aminopropyl)tetramethyldisiloxane were added along with 50 g of NMP, and the mixture was reacted at 40°C for 2 hours. Next, 5.46 g (0.050 mol) of 3-aminophenol was added as a terminal encapsulant along with 5 g of NMP, and the mixture was reacted at 50°C for 2 hours. After that, a solution of 32.39 g (0.22 mol) of N,N-dimethylformamide diethyl acetal diluted with 50 g of NMP was added. After adding the solution, it was stirred at 50°C for 3 hours. After stirring, the solution was cooled to room temperature, and then added to 3 L of water to obtain a white precipitate. This precipitate was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 80°C for 24 hours to obtain a polyimide precursor (a-2), which is an alkali-soluble resin.

[0200] Synthesis Example 4: Synthesis of Acrylic Resin (a-3) 140.0 g of propylene glycol methyl ether acetate was charged into a pressure vessel equipped with a stirrer, thermometer, reflux condenser, and dropper pump. The reaction vessel was filled with nitrogen and the temperature was raised to 60°C. 16.67 g of styrene, 13.07 g of methyl methacrylate, 5.41 g of 2-hydroxymethyl methacrylate, 4.84 g of glycidyl methacrylate, and 2.00 g of azobisisobutyronitrile as a polymerization initiator were added dropwise over 6 hours using a dropper pump to carry out copolymerization. As a result, an acrylic resin (a-3) solution with a weight-average molecular weight of 9000 and a solid content concentration of 25% by weight was obtained.

[0201] Synthesis Example 5: Synthesis of quinone diazide compound (c-1) Under a stream of dry nitrogen, 21.22 g (0.05 mol) of TrisP-PA (trade name, manufactured by Honshu Chemical Industry Co., Ltd.) and 26.87 g (0.10 mol) of 5-naphthoquinone diazidosulfonylic acid chloride were dissolved in 450 g of 1,4-dioxane at room temperature. To this, 15.18 g of triethylamine mixed with 50 g of 1,4-dioxane was added dropwise, ensuring that the temperature in the system did not exceed 35°C. After addition, the mixture was stirred at 30°C for 2 hours. The triethylamine salt was filtered, and the filtrate was added to water. The precipitated material was then collected by filtration. This precipitate was dried in a vacuum dryer to obtain the quinone diazide compound (c-1) represented by the following formula.

[0202] [ka]

[0203] Synthesis Example 6: Synthesis of compound (b-1) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 3.45 g (0.040 mol) of piperazine was dissolved in 30 g of ethanol at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 5 minutes. Then, 8.91 g (0.082 mol) of benzaldehyde was added, and the mixture was stirred at 60°C for 2 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-1).

[0204] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 297 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 10.07 (s, 1H), 7.91-7.56 (m, 6H), 2.84 (s, 4H).

[0205] Synthesis Example 7: Synthesis of compound (b-2) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 3.45 g (0.040 mol) of piperazine was dissolved in 30 g of ethanol at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 5 minutes. Then, 4.76 g (0.082 mol) of propionaldehyde was added, and the mixture was stirred at 60°C for 4 hours. After stirring, the solution was added to 200 mL of water and stirred for 1 hour. The precipitated powder was washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-2).

[0206] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 201 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 4.60 (m, 1H), 2.84 (s, 4H), 1.58 (m, 2H), 0.89 (m, 3H).

[0207] Synthesis Example 8: Synthesis of compound (b-3) having at least two substructures represented by formula (1) within the molecule. Compound (b-3) was obtained in the same manner as in Synthesis Example 6, except that 8.91 g (0.082 mol) of benzaldehyde was replaced with 12.69 g (0.082 mol) of 3-nitrobenzaldehyde, and 30 g of ethanol was replaced with 70 g. The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 387 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 8.22 (m, 1H), 7.67 (m, 1H), 2.85 (s, 4H).

[0208] Synthesis Example 9 Synthesis of compounds (b-4) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 2.00 g (0.010 mol) of compound (b-2) was added to 40 g of hydrochloric acid aqueous solution adjusted to pH 2.0, and stirred at room temperature for 5 minutes. Then, 1.28 g (0.040 mol) of methanol was added, and the mixture was stirred at 40°C for 2 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-4). The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 229 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 4.33 (m, 1H) 3.30 (s, 3H), 2.71 (s, 4H), 1.56 (m, 2H), 0.87 (m, 3H).

[0209] Synthesis Example 10: Synthesis of compounds (b-5) having at least two substructures represented by formula (1) within the molecule. Compound (b-5) was obtained in the same manner as in Synthesis Example 6, except that 8.91 g (0.082 mol) of benzaldehyde was replaced with 12.69 g (0.082 mol) of 4-nitrobenzaldehyde, and 30 g of ethanol was replaced with 150 g. The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 387 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 10.16 (s, 1H), 8.39 (s, 2H), 8.07 (s, 2H), 3.00 (s, 4H).

[0210] Synthesis Example 11: Synthesis of compounds (b-6) having at least two substructures represented by formula (1) within the molecule. Compound (b-6) was obtained in the same manner as in Synthesis Example 6, except that 8.91 g (0.082 mol) of benzaldehyde was replaced with 11.44 g (0.082 mol) of p-anisaldehyde, and 30 g of ethanol was replaced with 60 g. The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 357 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 7.48 (m, 2H), 6.89 (m, 2H), 3.81 (s, 3H), 2.71 (s, 4H).

[0211] Synthesis Example 12: Synthesis of compounds (b-7) having at least two substructures represented by formula (1) within the molecule. Compound (b-7) was obtained in the same manner as in Synthesis Example 6, except that 3.45 g (0.040 mol) of piperazine was replaced with 4.00 g (0.040 mol) of 2-methylpiperazine. The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 311 [MH] - . 1 H NMR (400MHz, CDCl3) δ: 7.33 (m, 10H), 2.58 (m, 7H), 1.11 (s, 3H).

[0212] Synthesis Example 13: Synthesis of compounds (b-8) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 3.24 g (0.030 mol) of 1,4-phenylenediamine was dissolved in 90 g of ethanol at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 13.37 g (0.126 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 10 minutes. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-8). The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 531 [MH] - . 1 H NMR (400MHz, DMSO-d6) δ: 8.70 (s, 1H), 7.97 (m, 2H), 7.53 (m, 3H), 7.37 (s, 2H).

[0213] Synthesis Example 14: Synthesis of compounds (b-9) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 3.69 g (0.030 mol) of p-anisidine was dissolved in 40 g of ethanol at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 7.00 g (0.066 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 6 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-9). The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 334 [MH] - . 1 H NMR (400MHz, DMSO-d6) δ: 8.65 (s, 1H), 7.91 (m, 2H), 7.50 (t, 3H), 7.29 (d, 2H), 6.98 (d, 2H), 3.78 (s, 3H).

[0214] Synthesis Example 15: Synthesis of compound (b-10) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 2.98 g (0.030 mol) of cyclohexylamine and 40 g of ethanol were added at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 7.00 g (0.066 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 6 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-10). The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 310 [MH] - . 1H NMR (400MHz, DMSO-d6) δ: 8.41 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 1.00-1.50 (m, 11H).

[0215] Synthesis Example 16: Synthesis of compound (b-11) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 3.43 g (0.030 mol) of trans-1,4-cyclohexanediamine was dissolved in 40 g of ethanol at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 13.37 g (0.126 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 1 hour. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-11).

[0216] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, negative): m / z 537 [MH] - . 1 H NMR (400MHz, DMSO-d6) δ: 8.39 (s, 1H), 7.70 (m, 2H), 7.40 (m, 3H), 7.29 (d, 2H), 6.98 (d, 2H), 1.59-1.74 (m, 4H).

[0217] Synthesis Example 17: Synthesis of a compound (b-12) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 11.7 g (0.10 mol) of indole and 8.1 g (0.045 mol) of 9-fluorenone were dissolved in 25 g of methanol at room temperature. 0.5 g of 98% by mass concentrated sulfuric acid was added, and the mixture was stirred at 60°C for 24 hours. After stirring, 9.0 g of 50% sodium hydroxide aqueous solution was added to neutralize the mixture, and 40 g of water was added and the mixture was stirred. After stirring, the precipitated powder was collected by filtration, washed three times with methanol, and then dried in a vacuum dryer at 40°C for 24 hours to obtain fluorene compound (β) with the structure shown below. Under a stream of dry nitrogen, 11.9 g (0.030 mol) of the obtained fluorene compound (β) and 80 g of tetrahydrofuran were added at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 7.00 g (0.066 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 24 hours. After stirring, the solution was added to 600 mL of water and stirred for 1 hour. The precipitated powder was washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-12).

[0218] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 607 [MH] - . 1 H NMR(400MHz,DMSO-d6)δ:8.39(s,1H),7.98(d,1H),7.70(m,2H),7.62(d,1H),7.51(d ,1H),7.40(t,1H),7.27(m,3H),7.04(m,3H),6.90(s,1H),6.79(t,1H),6.32(t,1H).

[0219] [ka]

[0220] Synthesis Example 18: Synthesis of a compound (b-13) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 2.52 g (0.020 mol) of melamine was dissolved in 100 g of water and 20 g of ethanol at room temperature. 0.1 g of 50% sodium hydroxide aqueous solution was added, and the mixture was stirred at room temperature for 5 minutes. Then, 13.3 g (0.125 mol) of benzaldehyde was added, and the mixture was stirred at 60°C for 8 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-13).

[0221] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 761 [MH] - . 1 H NMR (400MHz, DMSO-d6) δ:7.20-7.40(m,5H),5.80(s,1H).

[0222] Synthesis Example 19 Synthesis of a compound (b-14) having at least two substructures represented by formula (1) within the molecule. Under a stream of dry nitrogen, 2.00 g (0.010 mol) of 4,4'-diaminodiphenyl ether was dissolved in 25 g of tetrahydrofuran at room temperature, and 0.1 g of 50% sodium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 10 minutes. Then, 4.46 g (0.042 mol) of benzaldehyde was added, and the mixture was stirred at 50°C for 6 hours. After stirring, the precipitated powder was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 40°C for 24 hours to obtain compound (b-14).

[0223] The obtained compounds were analyzed by LC-MS using LC-MS2020 (Shimadzu Corporation) and by hydrogen nuclear magnetic resonance spectroscopy. 1 The compound was confirmed to be the target compound by 1H NMR (JNM-ECZ400R; manufactured by JEOL Ltd.). LC-MS (ESI, nega): m / z 623 [MH] - . 1 H NMR (400MHz, DMSO-d6) δ: 8.65 (s, 1H), 7.94 (m, 2H), 7.52 (m, 3H), 7.35 (d, 2H), 7.10 (d, 2H).

[0224] In addition, "NIKALAC" (registered trademark) MX-270 (product name, manufactured by Sanwa Chemical Co., Ltd.) (bz-1) was used as a comparative example in this study. The structures of compounds (b-1) to (b-14) and compound (bz-1) are shown below.

[0225] [ka]

[0226] [ka]

[0227] The names of the compounds used in each example and comparative example are shown below. GBL: γ-Butyrolactone EL: Ethyl lactate PGME: Propylene glycol monomethyl ether PGMEA: Propylene glycol methyl ether acetate NMP: N-methylpyrrolidone Example 1 3.4 g of polyhydroxystyrene (a-1) and 0.50 g of compound (b-1) having at least two substructures represented by formula (1) in its molecule were dissolved in a mixture of 3.0 g of GBL, 6.0 g of EL, and 1.0 g of PGME. The mixture was then filtered through a 0.2 μm polytetrafluoroethylene filter to obtain resin composition 1. The heat resistance, substrate adhesion, and storage stability of the obtained resin composition were evaluated as described above.

[0228] Examples 2-19, Comparative Examples 1-3 A resin composition was obtained in the same manner as in Example 1, except that components (a), (b), (c) and the solvent were changed as shown in Table 1. The heat resistance, substrate adhesion, and storage stability of the obtained resin composition were evaluated as described above.

[0229] Table 1 shows the composition and evaluation results of each example and comparative example.

[0230] [Table 1] [Explanation of Symbols]

[0231] 1: TFT (Thin Film Transistor) 2: Wiring 3: TFT insulating layer 4: Flattening layer 5:ITO (transparent electrode) 6: Circuit board 7: Contact Hole 8: Insulating layer 9:Display device 10: Light-emitting element 11: Cured product 12, 12c: Metal wiring 13: Opposite substrate 14: Electrode terminal 15: Light-emitting element driving substrate 16: Driving element 17: Barrier Metal 18: Solder bump 19: Alkali-free glass substrate 20: First electrode (transparent electrode) 21: Auxiliary electrode 22: Insulating layer 23: Organic EL layer 24: Second electrode (non-transparent electrode)

Claims

1. A resin composition comprising an alkali-soluble resin (a) and a compound (b) having at least two substructures represented by formula (1) within its molecule. 【Chemistry 1】 (In formula (1), R １ R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. ２ (where * represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have substituents, or a heteroaryl group having 2 to 20 carbon atoms which may have substituents, and * represents a bond.)

2. The resin composition according to claim 1, further comprising a photosensitive compound (c).

3. The resin composition according to claim 1 or 2, wherein component (a) comprises one or more selected from the group consisting of polyimide, polyimide precursor, polybenzoxazole, polybenzoxazole precursor, copolymers thereof, polyhydroxystyrene, and copolymers of hydroxystyrene and styrene derivatives that do not have phenolic hydroxyl groups.

4. R in formula (1) above ２ The resin composition according to claim 1 or 2, wherein the aryl group having 6 to 20 carbon atoms may have substituents, or the heteroaryl group having 2 to 20 carbon atoms may have substituents.

5. R in formula (1) above ２ A C6-C20 aryl group which may have substituents is subject to the Hammett substituent constant σ ｐ An aryl group having 6 to 20 carbon atoms and a substituent with a value of 0.4 or more, and R in formula (1) above ２ A heteroaryl group having 2 to 20 carbon atoms, which may have substituents, has a Hammett substituent constant σ ｐ The resin composition according to claim 1 or 2, wherein the heteroaryl group having 2 to 20 carbon atoms has a substituent with a value of 0.4 or more.

6. R in formula (1) above １ The resin composition according to claim 1 or 2, wherein the atom is a hydrogen atom.

7. The resin composition according to claim 1 or 2, wherein at least one bond in formula (1) is directly bonded to a C6-C20 aryl group of an aryl group having C6-C20 which may have substituents, or to a C2-C20 heteroaryl group of an heteroaryl group having C2-C20 which may have substituents.

8. The resin composition according to claim 1 or 2, wherein the component (b) contains a compound having a substructure represented by formula (2). 【Chemistry 2】 (In formula (2), R ３ and R ４ each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R ５ and R ６ each independently represents an aryl group having 6 to 20 carbon atoms which may have a substituent or a heteroaryl group having 2 to 20 carbon atoms which may have a substituent, and * represents a bond.)

9. The resin composition according to claim 1 or 2, wherein the component (b) contains at least one compound represented by any of the following structures. 【Transformation 3】 (R ７ , R ９ , R １１ , R １３ , R １５ and R １７ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R ８ , R １０ , R １２ , R １４ , R １６ and R １８ Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6.

10. A cured product obtained by curing the resin composition according to claim 1 or 2.

11. A step of forming a resin film on a substrate made of the resin composition according to claim 1 or 2, The process of exposing the resin film, A process of developing the exposed resin film, and A method for producing a cured product, comprising the step of heat-treating a developed resin film.

12. An organic EL display device having a drive circuit, a planarization layer, a first electrode, an insulating layer, an emissive layer, and a second electrode on a substrate, An organic EL display device having the cured product described in claim 10 for the planarization layer and / or the insulating layer.

13. A display device having at least metal wiring, a cured product according to claim 10, and a plurality of light-emitting elements, The light-emitting element is provided with a pair of electrode terminals on either one of its surfaces. The pair of electrode terminals are connected to a plurality of metal wires extending within the cured material. A display device in which multiple metal wires maintain electrical insulation due to the hardened material.

14. A compound having a substructure represented by formula (2). 【Chemistry 4】 (In formula (2), R ３ and R ４ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R ５ and R ６ Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and * represents a bond.

15. A compound represented by one of the following structures. 【Transformation 5】 (R ７ , R ９ , R １１ , R １３ , R １５ and R １７ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R ８ , R １０ , R １２ , R １４ , R １６ and R １８ Each of these independently represents an aryl group having 6 to 20 carbon atoms that may have substituents, or a heteroaryl group having 2 to 20 carbon atoms that may have substituents, and n represents an integer from 1 to 6.

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