Resin composition, cured product, display device, and semiconductor device

Abstract

The present invention addresses the problem of providing a resin composition that has excellent compatibility and excellent flatness. In order to solve the problem, the present invention provides a resin composition that contains one or more resins (component (A)) selected from the group consisting of a polyimide resin, a polybenzoxazole resin, precursors of these resins, and copolymers thereof, a resin that comprises a hydroxystyrene unit in a unit structure, a quinonediazide compound, and an organic solvent, wherein the component (A) has a divalent structural unit that is represented by formula (1) and is derived from a diamine. (In the formula, X represents a divalent hydrocarbon group having 1 to 15 carbon atoms, -O-, -S-, -SO2-, or a single bond; each of R1 and R2 independently represents -CH2-, -C(CH3)2-, -O -, -NHC(=O)-, or -C(=O)NH-; each t independently represents an integer of 0 or 1; and * represents an amide bond, an imide bond, or a bond part that is bonded to a nitrogen atom of an oxazole ring.)

Description

Resin composition, cured product, display device and semiconductor device

[0001] The present invention relates to a resin composition, more specifically to a resin composition suitable for applications such as a bank layer in an organic electroluminescence (hereinafter sometimes referred to as "organic EL") display device, a planarization layer in a driving thin film transistor (TFT) substrate in an organic EL display device, a surface protection layer, an interlayer insulating layer, and a rewiring layer in a semiconductor device, a wiring protection insulating layer in a circuit board, and an on-chip microlens or planarization layer for a solid-state imaging device, a cured product obtained by curing the resin composition, and a display device and a semiconductor device comprising the cured product.

[0002] Conventionally, photosensitive polyimides, which have excellent heat resistance, electrical insulation properties, mechanical properties, etc., and can be patterned by photolithography, have been widely used for bank layers of organic EL display devices, planarizing layers of TFT substrates, surface protective films of semiconductor elements, and interlayer insulating films of electronic components, and many proposals have been made so far (see, for example, Patent Document 1).

[0003] In general, an organic EL display device has a drive circuit, a planarization layer, a first electrode, a pixel division layer, a light-emitting layer, and a second electrode on a substrate, and can emit light by applying a voltage between the opposing first and second electrodes or by passing a current between them. Of these, photosensitive resin compositions that can be patterned by ultraviolet irradiation are generally used as materials for the planarization layer and the pixel division layer.

[0004] On the other hand, some photosensitive polyhydroxystyrene resins have been reported for use in interlayer insulating films (see, for example, Patent Document 2).

[0005] However, in recent years, the density of pixels and wiring has increased in organic EL display devices and semiconductor devices, and there is a demand for materials that are suitable for fine pattern processing and for flattening uneven object surfaces.

[0006] The inventors have devised a mixture of polyimide resin and polyhydroxystyrene resin as a material with excellent flatness. For purposes other than solving the problems of the present invention, several examples of mixing polyimide resin and polyhydroxystyrene have been reported (Patent Document 3).

[0007] JP 2002-91343 A JP 2009-47761 A JP 2005-352004 A

[0008] However, it has been found that the polyimide resins and polyhydroxystyrene resins described in Patent Documents 1 and 2 have a problem in that they do not provide sufficient flatness.

[0009] On the other hand, it has been found that the resin composition containing polyimide and polyhydroxystyrene described in Patent Document 3 has insufficient compatibility, and that the film becomes cloudy when developed after the formation of the coating film.

[0010] Therefore, an object of the present invention is to provide a resin composition that has excellent compatibility and good flatness.

[0011] The present invention has the following configuration: [1] A resin composition containing one or more resins (component (A)) selected from the group consisting of polyimide resins, polybenzoxazole resins, and precursors thereof, a resin (component (B)) containing a hydroxystyrene unit in its unit structure, a quinone diazide compound, and an organic solvent, wherein component (A) has a divalent structure represented by formula (1) derived from a diamine.

[0012]

[0013] (X is a divalent hydrocarbon group having 1 to 15 carbon atoms, -O-, -S-, -SO ２ represents - or a single bond, R １ and R ２ are each independently -CH ２ -, -C(CH ３ ) ２represents -, -O-, -NHC(=O)-, or -C(=O)NH-, each t independently represents an integer of 0 or 1, and * represents an amide bond, an imide bond, or a bond bonded to a nitrogen atom of an oxazole ring.) [2] The resin composition according to [1] above, wherein all or a part of component (A) is a polyimide resin or a polyimide precursor resin (component (A-1)), and all or a part of component (B) is at least one resin selected from the group consisting of polyhydroxystyrene and copolymers of polyhydroxystyrene and polystyrene. [3] The resin composition according to [1] above or [2] above, wherein X in the divalent structure represented by formula (1) is a divalent hydrocarbon group represented by formula (2) or formula (3).

[0014]

[0015] (R ３ represents an alkyl group having 1 to 3 carbon atoms, and when there are a plurality of such groups, they may be the same or different; a represents 1 or 2; b represents an integer of 1 to 3; R ４ and R ５ each independently represents a hydrocarbon group having 1 to 7 carbon atoms or a hydrogen atom, and * represents the point of attachment to the aromatic ring. ４ and R ５ do not have the same structure.) [4] The resin composition according to any one of [1] to [3] above, wherein the ratio ([W] / ([W]+[HS]) where [W] (mol) is the amount of units other than hydroxystyrene units contained in component (B) and [HS] (mol) is the amount of hydroxystyrene units is 0.12 or more and 0.30 or less. [5] The resin composition according to any one of [2] to [4] above, wherein component (A-1) contains, as the acid dianhydride residue, tetravalent groups having 8 to 40 carbon atoms and containing an alicyclic structure in their structure, in an amount of 20 to 100 mol % when the total amount of acid dianhydride residues contained in component (A-1) is 100 mol %. [6] The resin composition according to any one of [1] to [5] above, wherein the content of fluorine atoms present in the molecular structure of the resin of component (A) is 10,000 mass ppm or less. [7] The resin composition according to any one of [1] to [6] above, wherein X in the divalent structural unit represented by formula (1) is a divalent hydrocarbon group represented by formula (3).

[0016]

[0017] (R ４ and R ５ each independently represents a hydrocarbon group having 1 to 7 carbon atoms or a hydrogen atom, and * represents the point of attachment to the aromatic ring. ４ and R ５ do not have the same structure.) [8] The resin composition according to any one of [1] to [7] above, wherein the polydispersity of component (B) is 1.30 or less. [9] The resin composition according to any one of [1] to [8] above, wherein the divalent structure represented by formula (1) contained in component (A) is used in component (A) as a structural unit derived from a diamine, and accounts for 50 to 100 mol % when the total amount of diamines providing an imide bond, an amic acid structure, a benzoxazole precursor structure, or a benzoxazole ring is taken as 100 mol %.

[10] The resin composition according to any one of [1] to [9] above, wherein the proportion of component (B) is 10 mass % or more and 50 mass % or less when the total mass of components (A) and (B) is taken as 100 mass %.

[11] The resin composition according to any one of [1] to

[10] above, further comprising a crosslinker (component (E)) containing either or both of a methylol group and an alkoxymethyl group.

[12] The resin composition according to

[11] above, wherein, when the content of the (B) component is [B] (mass%) and the content of the (E) component is [E] (mass%), the relationship 1.0≦[B] / [E]≦2.5 is satisfied, where [B] (mass%) is the content of the (B) component and [E] (mass%) is the content of the (E) component, when the total amount of the resin composition is 100 mass%.

[13] The resin composition according to any one of [1] to

[12] above, wherein the (A) component contains a structure represented by formula (4).

[0018]

[0019] (R ６ represents a hydrocarbon group having 1 to 4 carbon atoms, which may be the same or different when there are a plurality of groups, l represents an integer of 1 to 3, and * represents a bonding site.)

[14] A cured product obtained by curing the resin composition according to any one of [1] to

[13] above.

[15] A display device comprising the cured product according to

[14] above.

[16] A semiconductor device comprising the cured product according to

[14] above.

[0020] According to the present invention, a resin composition can be obtained in which the coating film does not become cloudy after development and has excellent flatness.

[0021] 1 is a cross-sectional view showing an example of an organic EL display device including a cured product obtained by curing the resin composition of the present invention.

[0022] An embodiment of the present invention will now be described in detail.

[0023] The resin composition of the present invention contains one or more resins selected from the group consisting of polyimide resins, polybenzoxazole resins, and precursors thereof (hereinafter, sometimes referred to as "component (A)"), a resin containing a hydroxystyrene unit in its unit structure (hereinafter, sometimes referred to as "component (B)"), a quinone diazide compound, and an organic solvent, and is a resin composition in which component (A) has a divalent structure represented by formula (1) in its chemical structural formula, derived from a diamine.

[0024]

[0025] (X is a divalent hydrocarbon group having 1 to 15 carbon atoms, -O-, -S-, -SO ２ represents - or a single bond, R １ and R ２ are each independently -CH ２ -, -C(CH ３ ) ２ represents -, -O-, -NHC(=O)-, or -C(=O)NH-, each t independently represents an integer of 0 or 1, and * represents an amide bond, an imide bond, or a bond that bonds to a nitrogen atom of an oxazole ring.) <One or More Resins Selected from the Group Consisting of Polyimide Resins, Polybenzoxazole Resins, and Precursors Thereof (Component (A))> The resin composition of the present invention contains component (A).

[0026] In the present invention, the polyimide resin or polyimide precursor resin (hereinafter sometimes referred to as "component (A-1)") used as component (A) is a resin containing an imide bond or an amic acid structure (also referred to as an amide acid structure, and including amic acid esters; the same applies hereinafter) in the repeating unit, and is a resin containing more than 50 mol% of such repeating units when all repeating units in the molecular chain are taken as 100 mol%, and is typically a resin obtained as a dehydration condensate of a tetracarboxylic acid or a derivative thereof with a diamine or a derivative thereof. Note that in the present invention, a resin having an imidization rate of 80% or more, as described below, is referred to as a polyimide resin, and a resin having an imidization rate of 0% or more but less than 80% is referred to as a polyimide precursor.

[0027] In the present invention, the polybenzoxazole resin or polybenzoxazole precursor used as component (A) is a resin containing a benzoxazole structure or its precursor structure in a repeating unit, and is a resin containing more than 50 mol% of such repeating units when the total repeating units in the molecular chain are taken as 100 mol%, and is usually a resin obtained by dehydration condensation of a dicarboxylic acid or its derivative with a bisaminophenol or its derivative. Note that in the present invention, a resin having a ring closure rate of 80% or more to an oxazole ring is referred to as a polybenzoxazole resin, and a resin having a ring closure rate of 0% or more but less than 80% is referred to as a polybenzoxazole precursor.

[0028] In the present invention, component (A) may be two or more copolymer resins selected from polyimide, polyimide precursor, polybenzoxazole, and polybenzoxazole precursor, or may be a mixture of resins selected from the group consisting of polyimide resins, polybenzoxazole resins, and precursor resins thereof, or a mixture of the copolymer resin with a resin selected from the group consisting of polyimide resins, polybenzoxazole resins, and precursor resins thereof, or a mixture of such a resin with the copolymer resin.

[0029] Furthermore, component (A) may be a copolymer of a polymer other than polyimide, polyimide precursor, polybenzoxazole, and polybenzoxazole precursor, provided that the object of the present invention is not impaired. Examples of such polymers include polyamide, polyamide-imide, and polyester. However, the divalent structure represented by formula (1) contained in the polyimide resin, polybenzoxazole resin, and precursors thereof of component (A) is not considered to be a structural unit of polymers other than polyimides such as polyamide and polyamide-imide, polyimide precursors, polybenzoxazole, and polybenzoxazole precursors.

[0030] From the viewpoint of pattern filling, it is preferable to use the component (A-1) as the component (A), and from the viewpoint of flatness, it is more preferable to use a polyimide precursor resin.

[0031] The one or more resins selected from the group consisting of polyimide resins, polybenzoxazole resins, and precursors thereof in the component (A) used in the present invention are preferably constituted by a repeating unit represented by formula (5), formula (6), formula (19), or formula (20).

[0032]

[0033] (Y １ and Y ２ Y each independently represents an acid dianhydride residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms. ３ and Y ４ each independently represents an acid dianhydride residue, tricarboxylic acid residue, or dicarboxylic acid residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms. Z １ , and Z ２ each independently represents a diamine residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms. ３represents a divalent hydrocarbon group having 6 to 40 carbon atoms, which is bonded to the amide bond represented in formula (19) and contains a benzene ring having a hydroxyl group on the carbon adjacent to the carbon to which the amide bond is bonded. ４ represents an oxazole residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms. ７ , R ８ and R ９ each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a monovalent group having 2 to 10 carbon atoms and an ethylenically unsaturated double bond. r represents an integer of 0 to 2. s represents an integer of 0 to 2.) Here, it is expected that all or part of the amic acid structures in the structural units of the polyimide precursor resin will undergo ring closure upon curing. Also, it is expected that all or part of the benzoxazole precursor structures in the structural units of the polybenzoxazole precursor resin will undergo ring closure upon curing.

[0034] The component (A) used in the present invention can be synthesized by a known method.

[0035] The component (A) used in the present invention has a divalent structure represented by formula (1) in its chemical structure derived from a diamine. That is, the inclusion of such a structural unit improves compatibility with component (B). The fact that the component (A) is derived from a diamine can be confirmed by the presence of the divalent structure via an amide bond (an amide bond forming part of an amic acid structure or an amide bond forming part of an oxazole precursor structure), an imide bond, or a bond to a nitrogen atom of an oxazole ring.

[0036]

[0037] (X is a divalent hydrocarbon group having 1 to 15 carbon atoms, -O-, -S-, -SO ２ represents - or a single bond, R １ and R ２ are each independently -CH ２ -, -C(CH ３ ) ２represents -, -O-, -NHC(=O)-, or -C(=O)NH-, each t independently represents an integer of 0 or 1, and * represents an amide bond, an imide bond, or a bond to a nitrogen atom of an oxazole ring.) Of these, it is preferable that X in the structural unit of formula (1) is a divalent hydrocarbon group represented by formula (2) or formula (3). When the divalent hydrocarbon group represented by formula (2) and the divalent hydrocarbon group represented by formula (3) contain an asymmetric carbon, the asymmetric carbon may be in either the R-configuration or the S-configuration.

[0038]

[0039] (R ３ represents an alkyl group having 1 to 3 carbon atoms, and when there are a plurality of such groups, they may be the same or different; a represents 1 or 2; b represents an integer of 1 to 3; R ４ and R ５ each independently represents a hydrocarbon group having 1 to 7 carbon atoms or a hydrogen atom, and * represents the point of attachment to the aromatic ring. ４ and R ５ do not have the same structure.) When X in the structural unit of formula (1) is a divalent hydrocarbon group represented by formula (2) or formula (3), compatibility with component (B) is further improved, and furthermore, the flatness of the coating film after coating the resin composition is improved. From the viewpoint of flatness, it is preferable to adopt the structure represented by formula (3).

[0040] In the present invention, the structural unit represented by formula (1) contained in the component (A) is contained as a structural unit derived from a diamine.

[0041] Diamines that provide the structural unit represented by formula (1) include 2,2-bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, 1,1-bis(3-amino-4-hydroxyphenyl)cyclohexane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, 3,3'-diamino-4,4'-dihydroxybiphenyl, 9,9-bis(3-amino-4-hydroxyphenyl)fluorene, 2,2-bis[3-(3-aminobenzamido)-4-hydroxyphenyl]propane, and 2,2-bis[3-(4-aminobenzamido)-4-hydroxyphenyl]propane. Examples of hydroxyl group-containing diamines include, but are not limited to, pan, bis[3-(3-aminobenzamido)-4-hydroxyphenyl]sulfone, bis[3-(4-aminobenzamido)-4-hydroxyphenyl]sulfone, 1,1-bis[3-(3-aminobenzamido)-4-hydroxyphenyl]cyclohexane, 1,1-bis[3-(4-aminobenzamido)-4-hydroxyphenyl]cyclohexane, 9,9-bis[3-(3-aminobenzamido)-4-hydroxyphenyl]fluorene, 9,9-bis[3-(4-aminobenzamido)-4-hydroxyphenyl]fluorene, and diamines represented by formulas (7) to (18).

[0042]

[0043] The divalent structure represented by formula (1) contained in component (A) is preferably 50 to 100 mol %, more preferably 55 to 100 mol %, even more preferably 60 to 100 mol %, still more preferably 65 to 100 mol %, and particularly preferably 70 to 100 mol %, when the total amount of diamines used in component (A) to provide imide bonds, amic acid structures, benzoxazole precursor structures, and benzoxazole rings is taken as 100 mol %. By ensuring this range, compatibility with component (B) can be further improved.

[0044] Furthermore, component (A) may be a diamine other than the diamine that gives the divalent structure of formula (1), and specific examples of such diamines include aliphatic diamines and aromatic diamines. Aliphatic diamines refer to diamines that do not have an aromatic ring. Examples of such aliphatic diamines include aliphatic alkylenediamines containing alkylene ether groups such as alkylene groups, polyethylene ether groups, polyoxypropylene groups, and tetramethylene ether groups, alicyclic diamines, and aliphatic diamines having a siloxane structure.

[0045] Examples of aliphatic alkylenediamines include tetramethylenediamine, hexamethylenediamine, octamethylenediamine, decamethylenediamine, dodecamethylenediamine, 7-ethylhexadecanediamine, 7,12-dimethyloctadecanediamine, 8,13-dimethyloctadecanediamine, 8-methylnonadecanediamine, 9-methylnonadecanediamine, 7,12-dimethyloctadecanediamine-7,11-ene, 8,13-dimethyloctadecanediamine-8,12-ene, polymethylenediamines such as Diamine H20 (trade name, manufactured by Okamura Oil Mills Co., Ltd.), Jeffamine KH-511, Jeffamine ED-600, Jeffamine ED-900, Jeffamine ED-2003, and Jeffamine EDR. １４ 8. Jeffamine EDR １７ Examples of suitable diamines include diamines containing a polyethylene ether group such as D-6, polyoxypropylene diamines such as D-200, D-400, D-2000, D-4000, RP-409, and RP-2009, diamines containing a tetramethylene ether group such as RT-1000 and HT-1100, amino group-containing alkylene ether diamines such as HT-1000 and HE-1000 (all trade names, manufactured by HUNTSMAN Corporation), and dimer diamines such as "VERSAMINE (registered trademark) 551," "VERSAMINE (registered trademark) 552" (manufactured by BASF Corporation), "PRIAMINE (registered trademark) 1073," "PRIAMINE (registered trademark) 1074," and "PRIAMINE (registered trademark) 1075" (manufactured by Cargill).

[0046] Examples of alicyclic diamines include cyclohexyldiamine, methylenebiscyclohexylamine, norbornanediamine, and PRO-NBDA (trade name, manufactured by Mitsui Chemicals Fine Co., Ltd.).

[0047] Examples of aliphatic diamines having a siloxane structure include 1,3-bis(3-aminopropyl)tetramethyldisiloxane (SiDA) and bis(p-aminophenyl)octamethylpentasiloxane. When an aliphatic group having a siloxane structure is copolymerized within a range that does not reduce heat resistance, adhesion to the substrate can be improved.

[0048] Examples of aromatic diamines include diamines containing a sulfonic acid group such as a 3-sulfonic acid-4,4'-diaminodiphenyl ether group, diamines containing a thiol group such as a dimercaptophenylenediamine group, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 1,4-bis(4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis(4-aminophenoxy)biphenyl, phenyl, bis{4-(4-aminophenoxy)phenyl}ether, 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, etc. Examples of the aromatic diamine include, but are not limited to, any of aromatic diamines, diamines in which some of the hydrogen atoms in the aromatic ring are substituted with alkyl groups having 1 to 10 carbon atoms, and diamines having a nitrogen-containing heteroaromatic ring such as 4-diamino-1,3,5-triazine (guanamine), 2,4-diamino-6-methyl-1,3,5-triazine (acetoguanamine), and 2,4-diamino-6-phenyl-1,3,5-triazine (benzoguanamine).

[0049] In the above formula (5) and formula (6), Y １ and Y ２ each independently represents an acid dianhydride residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms. The acid dianhydride residue refers to a group obtained by removing two acid anhydride structures from an acid dianhydride compound.

[0050] In the above formula (19) and formula (20), Y ３ and Y ４ each independently represents an acid dianhydride residue, tricarboxylic acid residue, or dicarboxylic acid residue having 2 to 40 carbon atoms, which has any one of an aliphatic structure having 2 to 20 carbon atoms, an alicyclic structure having 4 to 40 carbon atoms, and an aromatic structure having 6 to 40 carbon atoms.

[0051] Y in the component (A) １ , Y ２ , Y ３ and Y ４ From the viewpoint of flatness, the tetracarboxylic acid or dianhydride thereof that gives the structure preferably contains an acid dianhydride residue having 8 to 40 carbon atoms and containing an alicyclic structure.

[0052] Examples of acid dianhydrides having 8 to 40 carbon atoms and containing an alicyclic structure include 1,2-dimethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride, 2,3,5-tricarboxy-2-cyclopentaneacetic acid dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride, and 2,3,4,5-tetrahydrofurantetracarboxylic acid dianhydride. , 3,5,6-tricarboxy-2-norbornaneacetic dianhydride, 1,3,3a,4,5,9b-hexahydro-5(tetrahydro-2,5-dioxo-3-furanyl)naphtho[1,2-c]furan-1,3-dione, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, and 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride can be mentioned.

[0053] The component (A) preferably contains the component (A-1), and when the total amount of acid dianhydride residues in the component (A-1) is taken as 100 mol %, the content of the acid dianhydride residues having 8 to 40 carbon atoms and containing an alicyclic structure is preferably 20 to 100 mol %.

[0054] Other Y １ , Y ２ , Y ３ and Y ４ Examples of the tetracarboxylic acid or dianhydride giving the structure include pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic 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, 1,2,5,6-naphthalenetetracarboxylic acid Examples of suitable dianhydrides include aromatic tetracarboxylic dianhydrides such as 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, and 3,4,9,10-perylenetetracarboxylic dianhydride; bis(3,4-dicarboxyphenyl)sulfone dianhydride, 4,4'-oxydiphthalic anhydride, 3,4'-oxydiphthalic anhydride, 2,2-bis(4-(3,4-dicarboxyphenoxy)phenyl)propane dianhydride, 2,2-bis(3-(3,4-dicarboxyphenoxy)phenyl)propane dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride; and compounds in which the aromatic rings of these compounds are substituted with alkyl groups; and aromatic acid dianhydrides such as acid dianhydrides having an amide group.

[0055] Y ３ and Y ４ Examples of tricarboxylic acid residues that give the structure include trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid.

[0056] Y ３ and Y ４ Examples of dicarboxylic acid residues that give the structure include terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid.

[0057] Furthermore, the component (A) is preferably one whose ends are capped with an end-capping agent such as a monoamine, an acid anhydride, a monoacid chloride, a monocarboxylic acid, or a monoactive ester.

[0058] Specific examples of such monoamines include those having a phenolic hydroxyl group such as 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol (OAP), 3-aminophenol (MAP), and 4-aminophenol (PAP). Specific examples of such monoamines include those having no phenolic hydroxyl group such as orthotoluidine, metatoluidine, paratoluidine, 2-ethylaniline, and 3-ethylaniline. Examples of such an amino acid include monoamines having an aliphatic hydrocarbon group such as phosphorus, 4-ethylaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 3,4-dimethylaniline, and 4-isopropylaniline, monoamines having a crosslinkable group such as 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 2-aminostyrene, 3-aminostyrene, and 4-aminostyrene, aniline, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, and 4-aminobenzenesulfonic acid. Two or more of these may be used.

[0059] Furthermore, among the acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds that can be used to end-catch the component (A), examples of those having a phenolic hydroxyl group include 3-hydroxyphthalic anhydride, 3-carboxyphenol, 4-carboxyphenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, and 1-hydroxy-5-carboxynaphthalene. Examples of compounds having a photocrosslinkable group include maleic anhydride, 5-norbornene-2,3-dicarboxylic anhydride (NA), itaconic anhydride, itaconic acid, maleic acid, acrylic acid, methacrylic acid, 3-phenylacrylic acid, crotonic acid, 1,2,3,6-tetrahydrophthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, and 3-methyl-4-cyclohexene-1,2-dicarboxylic anhydride. Other examples include acetic anhydride, succinic anhydride, phthalic anhydride, cyclohexanedicarboxylic anhydride, 3-carboxythiophenol, 4-carboxythiophenol, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, 4-carboxybenzenesulfonic acid, terephthalic acid, phthalic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, 2,6-dicarboxynaphthalene, trimellitic anhydride, and cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride. Furthermore, with respect to the above monocarboxylic acids, monoacid chloride compounds in which the carboxyl group of these monocarboxylic acids is converted to acid chloride may be used, or monoacid chloride compounds in which only one carboxyl group of the above dicarboxylic acids is converted to acid chloride may be used, or activated ester compounds obtained by reacting a monoacid chloride compound with N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboximide may be used. Two or more of these may also be used.

[0060] It is particularly preferred that the end-capping agent contains a structure represented by formula (4).

[0061]

[0062] (R ６ represents a hydrocarbon group having 1 to 4 carbon atoms, which may be the same or different when there are multiple groups, l represents an integer of 1 to 3, and * represents a bonding site.) Component (A) is end-capped with an end-capping agent that has the structure represented by formula (4) and is capable of end-capping component (A), thereby improving flatness. Furthermore, among these, the use of an end-capping agent having a crosslinkable group is preferred from the viewpoint of improving pattern filling.

[0063] Examples of end-capping agents capable of end-capping component (A) with the structure represented by formula (4) include those having an aliphatic hydrocarbon group such as the above-mentioned ortho-toluidine, meta-toluidine, para-toluidine, 2-ethylaniline, 3-ethylaniline, 4-ethylaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 3,4-dimethylaniline, and 4-isopropylaniline, and those having a crosslinkable group such as 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 2-aminostyrene, 3-aminostyrene, and 4-aminostyrene.

[0064] When the introduction ratio of imide bonds, amic acid structures, benzoxazole precursor structures, or structures derived from diamines bonded to benzoxazole rings contained in component (A) is less than 100 mol% relative to 100 mol% of the structural units derived from tetracarboxylic acid, it is preferable to use a monoamine as an end-capping agent. In this case, the introduction ratio of the end-capping agent for reacting with the carboxyl group terminals is preferably 1 mol% or more and 60 mol% or less relative to 100 mol% of the structural units derived from tetracarboxylic acid. By introducing the monoamine at a ratio of preferably 1 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, flatness can be improved. Furthermore, by introducing the monoamine at a ratio of preferably 60 mol% or less, more preferably 50 mol% or less, and even more preferably 40 mol% or less, pattern filling during the heat treatment step can be suppressed.

[0065] When the introduction ratio of the structural units derived from tetracarboxylic acid bonded to polyimide bonds, amic acid structures, benzoxazole precursor structures, or benzoxazole rings contained in the component (A) is less than 100 mol% relative to 100 mol% of the structural units derived from diamine, it is preferable to use an acid anhydride, monocarboxylic acid, monoacid chloride compound, or monoactive ester compound as the end-capping agent. In this case, the introduction ratio of the end-capping agent for reacting with the amino group terminals is preferably 1 mol% or more and 60 mol% or less relative to 100 mol% of the structural units derived from diamine. By setting this introduction ratio to preferably 1 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, flatness can be improved. On the other hand, by setting this introduction ratio to preferably 60 mol% or less, more preferably 50 mol% or less, and even more preferably 40 mol%, pattern filling during the heat treatment process can be suppressed.

[0066] On the other hand, it is desirable that the terminal blocking with the terminal blocking agent is carried out at a ratio of preferably 30 mol% or more, more preferably 50 mol% or more, and even more preferably 70 mol% or more, when the number of molecular terminals of component (A) is taken as 100 mol%. There is no particular upper limit to the terminal blocking ratio, but ideally 100 mol% of the molecular terminals are blocked. The state of the molecular terminals of component (A) can be determined by known methods, for example, spectroscopic methods such as NMR or chemical methods such as titration.

[0067] The weight-average molecular weight (Mw) of component (A) is preferably 3,000 to 100,000, as determined by gel permeation chromatography (GPC) using polystyrene standards. By setting the Mw to 100,000 or less, more preferably 80,000 or less, and even more preferably 60,000 or less, good solvent solubility and good solubility in developing solutions can be effectively achieved. Furthermore, by setting the weight-average molecular weight to 3,000 or more, more preferably 5,000 or more, and even more preferably 7,000 or more, high elongation at break can be effectively achieved. In the present invention, Mw is determined by the method described below.

[0068] Component (A) can be synthesized by known methods. Examples of methods for producing component (A) include reacting a tetracarboxylic dianhydride with a diamine compound in a polymerization solvent at low temperature; obtaining a diester from a tetracarboxylic dianhydride with an alcohol, then reacting the diester with an amine in the presence of a condensing agent; and obtaining a diester from a tetracarboxylic dianhydride with an alcohol, then converting the remaining dicarboxylic acid into an acid chloride and reacting it with an amine. The resin obtained by the above method may also be dehydrated and cyclized by heating or chemical treatment with an acid or base. To obtain a polybenzoxazole precursor or polybenzoxazole, a diamine compound having a hydroxyl group on the carbon adjacent to the carbon bonded to the amino group is used. The polymerized component (A) is preferably introduced into a large amount of deionized water or a mixture of methanol and deionized water, precipitated, filtered, dried, and isolated. This precipitation process removes unreacted monomers and oligomers such as dimers and trimers, improving the film properties and chemical resistance after thermal curing.

[0069] The polymerization solvent is not particularly limited as long as it can dissolve the raw material monomers, such as acid dianhydrides and diamines. Examples of the polymerization solvent include amides such as N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP), 1,3-dimethyl-2-imidazolidinone (DMI), 3-methoxy-N,N-dimethylpropanamide (MPA), 3-butoxy-N,N-dimethylpropanamide (BPA), N,N'-dimethylpropyleneurea (hereinafter, DMPU), N,N-dimethylisobutyramide (DMIB), N,N-dimethylpropionamide (DMPA), and 3-methyl-2-oxazolidinone; γ-butyrolactone (GBL); γ-valerol; Examples of suitable polymerization solvents include cyclic esters such as lactone, δ-valerolactone, γ-caprolactone, ε-caprolactone, and α-methyl-γ-butyrolactone, carbonates such as ethylene carbonate and propylene carbonate, glycols such as triethylene glycol, phenols such as m-cresol and p-cresol, esters such as methyl levulinate, ethyl levulinate, propyl levulinate, butyl levulinate, ethyl levulinate propylene glycol ketal, and ethyl levulinate glycerol ketal, acetophenone, sulfolane, dimethyl sulfoxide (hereinafter, DMSO), and dihydrolevoglucosenone (Cyrene, manufactured by Circa). The amount of the polymerization solvent used is preferably 100 to 1,900 parts by mass, and more preferably 150 to 950 parts by mass, per 100 parts by mass of component (A).

[0070] It is preferable that the component (A) contains substantially no fluorine atoms. Specifically, it is preferable that the content of fluorine atoms present in the molecular structure of the resin of the component (A) is 10,000 ppm by mass or less.

[0071] By making the component (A) substantially free of fluorine atoms, compatibility with the component (B) can be further improved. The component (A) substantially free of fluorine atoms can be obtained by synthesis using only monomers that do not contain fluorine atoms.

[0072] <Resin containing a hydroxystyrene unit in its unit structure (component (B))> The resin composition of the present invention contains component (B). Inclusion of component (B) can improve flatness. Here, the term "unit structure" refers to a substituted or unsubstituted ethylene group as a repeating unit. Note that component (B) can be a mixture of two or more types. Here, the hydroxystyrene unit refers to a repeating unit in an addition polymer formed from a monomer having an unsaturated double bond, and is obtained by cleavage of the double bond of the vinyl group of a vinylbenzene derivative having a phenolic hydroxyl group.

[0073] Resins containing hydroxystyrene units in their unit structure can be obtained by addition polymerization of vinylbenzene derivatives having phenolic hydroxyl groups. Examples of vinylbenzene derivatives having phenolic hydroxyl groups include hydroxystyrene, dihydroxystyrene, coumaric acid, 2'-hydroxychalcone, resveratrol, and 4-hydroxystilbene, and two or more of these may be used together.

[0074] Copolymers with units other than hydroxystyrene units can be obtained by copolymerizing the vinylbenzene derivative having a phenolic hydroxyl group with another monomer having a carbon-carbon unsaturated bond. Examples of the other monomer having a carbon-carbon unsaturated bond include maleimide compounds such as maleimide, N-methylmaleimide, N-ethylmaleimide, N-propargylmaleimide, N-(2-hydroxyethyl)maleimide, N-tert-butylmaleimide, N-phenylmaleimide, N-(4-hydroxyphenyl)maleimide, and N-(4-methoxyphenyl)maleimide, as well as acrylic compounds, methacrylic compounds, and styrene.

[0075] From the viewpoint of flatness, the resin composition of the present invention preferably uses, as component (B), at least one resin selected from the group consisting of polyhydroxystyrene and copolymers of polyhydroxystyrene and polystyrene. Alternatively, the resin composition may be a mixture of two or more types of polyhydroxystyrene, a mixture of copolymers of polyhydroxystyrene and polystyrene, or a mixture of polyhydroxystyrene and a copolymer of polyhydroxystyrene and polystyrene.

[0076] The resin composition of the present invention more preferably uses polyhydroxystyrene and a polystyrene copolymer as component (B), which further improves flatness.

[0077] Furthermore, in component (B), when the amount of units other than hydroxystyrene units is [W] (mol) and the amount of hydroxystyrene units is [HS] (mol), the ratio of the amount of styrene units to the sum of the amount of units other than hydroxystyrene units and the amount of hydroxystyrene units ([W] / ([W]+[HS])) is preferably 0.12 or more and 0.30 or less, more preferably 0.15 or more and 0.25 or less. By setting it in this range, the effect of improving flatness can be further enhanced without impairing compatibility with polyimide.

[0078] In the resin composition of the present invention, when the total mass of the (A) component and the (B) component is taken as 100 mass%, the proportion of the (B) component is preferably 10 mass% or more, more preferably 15 mass% or more, and even more preferably 20 mass% or more from the viewpoint of flatness, and is preferably 50 mass% or less, more preferably 40 mass% or less, and even more preferably 30 mass% or less from the viewpoint of pattern filling.

[0079] The weight average molecular weight of the (B) component can be determined in polystyrene equivalent terms by gel permeation chromatography (GPC). From the viewpoint of pattern filling during heat treatment, the weight average molecular weight is preferably 1,000 or more, more preferably 2,000 or more, and even more preferably 3,000 or more; from the viewpoint of flatness, the weight average molecular weight is preferably 10,000 or less, more preferably 8,000 or less, and even more preferably 7,000 or less.

[0080] From the viewpoint of suppressing pattern filling, the dispersity of component (B), defined as Mw / Mn where Mw is the weight average molecular weight of component (B) and Mn is the number average molecular weight, is preferably 1.30 or less, more preferably 1.20 or less, and even more preferably 1.15 or less. There is no particular lower limit, but it is 1.0 or more in light of the theoretical value.

[0081] <Quinone diazide compound> The resin composition of the present invention contains a quinone diazide compound. By containing the quinone diazide compound, an acid is generated in the light-irradiated portion, which increases the solubility of the light-irradiated portion in an alkaline aqueous solution, thereby forming a positive relief pattern in which the light-irradiated portion dissolves.

[0082] The quinone diazide compound is preferably a compound in which the sulfonic acid of naphthoquinone diazide sulfonic acid is bonded to a compound having a phenolic hydroxyl group via an ester bond. Examples of the compound having a phenolic hydroxyl group used here include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, and methyl Rentris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-PCHP, DML-PC, DML-PTBP, DML-34X, DML-EP , DML-POP, Dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriML-35XL, TML-BP, TML-HQ, TML -pp-BPF, TML-BPA, TMOM-BP, HML-TPPHBA, HML-TPHAP (product name, Honshu Chemical Industry Co., Ltd.), BIR-OC, BIP-PC, BIR-PC, BIR- PTBP, BIR-PCHP, BIP-BIOC-F, 4PC, BIR-BIPC-F, TEP-BIP-A, 46DMOC, 46DMOEP, TM-BIP-A (product names, Asahi Yokuzai Kogyo Co., Ltd. )), 2,6-dimethoxymethyl-4-tert-butylphenol, 2,6-dimethoxymethyl-p-cresol, 2,6-diacetoxymethyl-p-cresol, naphthol, tetrahydroxybenzophenone, methyl gallate, bisphenol A, bisphenol E, methylene bisphenol, BisP-AP (all trade names, Honshu Chemical Industry Co., Ltd.). Suitable examples of the quinone diazide compound used in the present invention include compounds obtained by introducing 4-naphthoquinone diazide sulfonic acid or 5-naphthoquinone diazide sulfonic acid into any of these compounds having a phenolic hydroxyl group via an ester bond, but other compounds can also be used.

[0083] 4-naphthoquinone diazide sulfonyl ester compounds have absorption in the i-line region of a mercury lamp and are suitable for i-line exposure. 5-naphthoquinone diazide sulfonyl ester compounds have absorption extending into the g-line region of a mercury lamp and are suitable for g-line exposure. In the present invention, either 4-naphthoquinone diazide sulfonyl ester compounds or 5-naphthoquinone diazide sulfonyl ester compounds can be preferably used, but it is preferable to select a 4-naphthoquinone diazide sulfonyl ester compound or a 5-naphthoquinone diazide sulfonyl ester compound depending on the wavelength of exposure. It is also possible to obtain naphthoquinone diazide sulfonyl ester compounds containing both 4-naphthoquinone diazide sulfonyl groups and 5-naphthoquinone diazide sulfonyl groups in the same molecule, or a mixture of 4-naphthoquinone diazide sulfonyl ester compounds and 5-naphthoquinone diazide sulfonyl ester compounds can be used.

[0084] The naphthoquinone diazide sulfonyl ester compound can be synthesized by an esterification reaction between a compound having a phenolic hydroxyl group and a naphthoquinone diazide sulfonic acid compound, and can be synthesized by a known method.

[0085] In the present invention, the content of the quinone diazide compound is preferably 0.01 to 50 parts by mass per 100 parts by mass of component (A). From the viewpoint of pattern formation, the content of the quinone diazide compound is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more, and from the viewpoint of maintaining heat resistance, the content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 35 parts by mass or less.

[0086] <Organic Solvent> The resin composition of the present invention contains an organic solvent.

[0087] Examples of the organic solvent include ethers, acetates, esters, ketones, aromatic hydrocarbons, amides, and alcohols.

[0088] Examples of ethers include 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, dipropylene glycol dimethyl ether, dipropylene glycol methyl-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran.

[0089] Examples of acetates include butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate (hereinafter sometimes referred to as "PGMEA"), 3-methoxybutyl acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methyl-1-butyl acetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate.

[0090] Examples of esters include alkyl lactate esters such as methyl 2-hydroxypropionate or ethyl 2-hydroxypropionate, and other esters such as ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, 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-methoxybutylpropionate, 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, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate.

[0091] Examples of the ketones include methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.

[0092] Examples of aromatic hydrocarbons include toluene and xylene.

[0093] Examples of the amides include N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide.

[0094] Examples of alcohols include butyl alcohol, isobutyl alcohol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol, and diacetone alcohol.

[0095] The amount of the organic solvent used is not particularly limited as it varies depending on the required thickness and the coating method to be used, but is preferably 100 to 2000 parts by mass, more preferably 150 to 900 parts by mass, per 100 parts by mass of the solid content of the resin composition, i.e., the other components excluding the organic solvent.

[0096] <Crosslinking agent containing either or both of a methylol group and an alkoxymethyl group (component (E))> From the viewpoint of suppressing pattern filling during heat treatment, the resin composition of the present invention preferably further contains a crosslinking agent containing either or both of a methylol group and an alkoxymethyl group (hereinafter, sometimes referred to as "component (E)"). Component (E) has at least two methylol groups or alkoxymethyl groups in its molecular structure to ensure crosslinkability. The crosslinking agent crosslinks component (A) or other components, and can increase the durability of the cured product while suppressing pattern filling during heat treatment.

[0097] Any known compound having at least two methylol or alkoxymethyl groups can be used as component (E). Preferred examples of such compounds include HMOM-TPPHBA and HMOM-TPHAP (trade names, manufactured by Honshu Chemical Industry Co., Ltd.), NIKALAC (registered trademark) MX-290, NIKALAC MX-280, NIKALAC MX-270, NIKALAC MX-279, NIKALAC MW-100LM, and NIKALAC MX-750LM (trade names, manufactured by Sanwa Chemical Co., Ltd.), each of which is available from the respective companies listed above.

[0098] Examples of the alkoxymethyl group include, but are not limited to, a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, and a butoxymethyl group.

[0099] In the resin composition of the present invention, the content of component (E) is preferably 5 parts by mass or more and 50 parts by mass or less, relative to 100 parts by mass of component (A). By making the content of component (E) 5 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more, relative to 100 parts by mass of component (A), the mechanical properties and heat resistance of the cured product are improved. Furthermore, by making the content of component (E) 50 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 30 parts by mass or less, relative to 100 parts by mass of component (A), a decrease in elongation of the cured product can be prevented.

[0100] Furthermore, when the total amount of the resin composition is taken as 100 mass%, the content of the (B) component is [B] (mass%) and the content of the (E) component is [E] (mass%), and it is preferable that the (E) component satisfy the relationship 1.0≦[B] / [E]≦2.5.

[0101] By satisfying the above conditions, it is possible to achieve both pattern filling and flatness.

[0102] <Other Crosslinking Agents> The resin composition of the present invention may contain a thermal crosslinking agent in addition to component (E). The other crosslinking agent refers to a compound having at least two thermally reactive functional groups, such as epoxy groups or oxetanyl groups, in the molecule. Such a crosslinking agent can crosslink component (A) or other components, thereby increasing the durability of the cured product.

[0103] Examples of compounds having at least two epoxy groups or oxetanyl groups include various known compounds. Preferred examples of such compounds having an epoxy group include VG3101L (trade name, manufactured by Printec Co., Ltd.), "TEPIC" (registered trademark) S, "TEPIC" G, and "TEPIC" P (all trade names, manufactured by Nissan Chemical Industries, Ltd.), "Epiclon" (registered trademark) N660, "Epiclon" N695, and HP7200 (all trade names, manufactured by Dainippon Ink and Chemicals, Inc.), "Denacol" (registered trademark) EX-321L (trade name, manufactured by Nagase ChemteX Corporation), NC6000, and EPPN502H. , NC3000 (all trade names, manufactured by Nippon Kayaku Co., Ltd.), "Epotohto" (registered trademark) YH-434L (trade name, manufactured by Tohto Kasei Co., Ltd.), EHPE-3150 (trade name, manufactured by Daicel Corporation), compounds having an oxetanyl group include OXT-121, OXT-221, OX-SQ-H, OXT-191, PNOX-1009, RSOX (all trade names, manufactured by Toagosei Co., Ltd.), "Etanacol" (registered trademark) OXBP, "Etanacol" OXTP (all trade names, manufactured by Ube Industries, Ltd.).

[0104] The content of the thermal crosslinking agent used in addition to component (E) is preferably 5 parts by mass or more and 50 parts by mass or less, relative to 100 parts by mass of the total amount of component (A). By making the content of such crosslinking agent 5 parts by mass or more, more preferably 10 parts by mass or more, and even more preferably 15 parts by mass or more, the mechanical properties and heat resistance of the cured product are improved. Furthermore, by making the content 50 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 30 parts by mass or less, a decrease in elongation of the cured product can be prevented.

[0105] <Surfactant> The resin composition of the present invention may further contain a surfactant. The surfactant is a compound having a hydrophilic structure and a hydrophobic structure.

[0106] By incorporating an appropriate amount of the surfactant, the surface tension of the resin composition can be adjusted, the leveling property during application can be improved, and the thickness uniformity of the coating film can be improved.

[0107] The surfactant is preferably a silicone surfactant, a polyoxyalkylene ether surfactant, or an acrylic resin surfactant.

[0108] Examples of the silicone surfactant include SH28PA, SH7PA, SH21PA, SH30PA, and ST94PA (all manufactured by Dow Corning Toray Co., Ltd.), and BYK (registered trademark) -301, -306, -307, -331, -333, -337, and -345 (all manufactured by BYK Japan KK).

[0109] Examples of the polyoxyalkylene ether surfactants include "Ftergent" (registered trademark) 212M, 209F, 208G, 240G, 212P, 220P, 228P, NBX-15, FTX-218, and DFX-218 (all manufactured by Neos Corporation).

[0110] Examples of the acrylic resin surfactant include "BYK" (registered trademark) -350, -352, -354, -355, -356, -358N, -361N, -392, -394, and -399 (all manufactured by BYK Japan KK).

[0111] The content of the surfactant is preferably 0.001% by mass or more and 1% by mass or less, when the total amount of the resin composition is 100% by mass. By making the content of the surfactant 0.001% by mass or more, more preferably 0.003% by mass or more, and even more preferably 0.005% by mass or more, it is possible to improve leveling properties during application. On the other hand, by making the content of the surfactant 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.03% by mass or less, it is possible to improve leveling properties during application.

[0112] <Method for Producing Resin Composition> A method for producing the resin composition of the present invention will be described using an example. However, the present invention is not limited to the resin obtained by this method. The resin composition of the present invention can be obtained, for example, by dissolving component (A), component (B), and a quinone diazide compound in an organic solvent.

[0113] Examples of dissolving methods include stirring and heating. When heating, the heating temperature is preferably set within a range that does not impair the performance of the resin composition, and is usually preferably 20° C. to 80° C. The order in which the components are dissolved is not particularly limited, and examples include a method in which the components are dissolved in order starting with the least soluble compound.

[0114] The obtained resin composition is preferably filtered using a filter to remove dust and particles. The filter pore size is, for example, 1 μm, 0.5 μm, 0.2 μm, 0.1 μm, 0.05 μm, etc., but is not limited thereto. The filter material may be polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), etc., and filtering using polyethylene or nylon is preferred.

[0115] <Cured Product> The cured product of the present invention is obtained by curing the resin composition of the present invention.

[0116] Examples of curing methods include heat treatment of a resin composition applied to a substrate. Examples of methods for applying a resin composition to a substrate include spin coating, slit coating, dip coating, spray coating, and printing. Heat treatment after application can remove residual solvents and components with low heat resistance, thereby improving the heat resistance and chemical resistance of the cured product. Furthermore, the inclusion of a crosslinking agent can promote a thermal crosslinking reaction through heat treatment, thereby improving the heat resistance and chemical resistance of the cured product. This heat treatment can be carried out, for example, by selecting a temperature and gradually increasing the temperature, or by selecting a temperature range and continuously increasing the temperature for 5 minutes to 5 hours. One example is a method in which heat treatment is carried out at 150°C and 250°C for 30 minutes each. Another example is a method in which the temperature is linearly increased from room temperature to 300°C over 2 hours. Heat treatment conditions in the present invention are preferably 180°C or higher, more preferably 200°C or higher, and even more preferably 230°C or higher. The heat treatment conditions are preferably 400° C. or less, more preferably 350° C. or less, and even more preferably 300° C. or less.

[0117] Furthermore, before curing, a film of the resin composition of the present invention can be formed on an object to be coated, such as a substrate, and the organic solvent can be dried as necessary. The film can then be exposed to light using a mask having a predetermined mask pattern, and then developed to perform patterning.

[0118] The cured product of the present invention can be used in electronic components such as organic electroluminescent (EL) display devices, liquid crystal display devices, semiconductor devices, and multilayer wiring boards. Specifically, it is suitable for applications such as partition walls for organic electroluminescent (EL) elements, planarizing layers for substrates with drive circuits for display devices using organic EL elements, color filters for liquid crystal devices, black matrices for liquid crystal devices, interlayer insulating films between rewirings of semiconductor devices or semiconductor components, passivation films for semiconductor devices, surface protective films for semiconductor devices, interlayer insulating films for multilayer wiring for high-density packaging, wiring protective insulating layers for circuit boards, on-chip microlenses for solid-state imaging devices, and planarizing layers for various displays and solid-state imaging devices. Examples of electronic devices having a surface protective film or interlayer insulating film containing the cured product of the present invention include MRAMs with low heat resistance. That is, the cured product of the present invention is suitable for use as a surface protective film for magnetoresistive memories (MRAMs). It can also be preferably used as partition walls or insulating layers for display devices such as liquid crystal displays and organic electroluminescent (EL) devices. The display device of the present invention can be incorporated into electronic devices or used as one of the modules that make up electronic devices. Examples of such electronic devices include mobile phones such as smartphones, tablet terminals, televisions, personal computers, digital signage, game consoles, AR (Augmented Reality) / VR (Virtual Reality) terminals, watches, portable music players, and calculators.

[0119] The resin composition of the present invention is suitably used for bank layers of organic EL display devices, planarizing layers of TFT substrates for driving organic EL display devices, wiring protection insulating layers of circuit boards, surface protection layers, interlayer insulating layers, and / or rewiring layers of semiconductor devices, on-chip microlenses of solid-state imaging devices, and planarizing layers for various displays and solid-state imaging devices.

[0120] 1 shows a cross-sectional view of an element portion of an example of an organic EL display element. In this example, when the cured product of the present invention is used for the planarizing layer 5 or the pixel dividing layer 8, the above-mentioned predetermined effects are particularly utilized.

[0121] The display device or semiconductor device of the present invention includes the cured product described above. In the display device of the present invention, the cured product of the present invention is used in the bank layer and / or the planarization layer of the TFT substrate, and in the semiconductor device of the present invention, when the cured product of the present invention is used in the surface protection layer, the interlayer insulating layer, and / or the rewiring layer, the cured product of the present invention can reduce the contact resistance of the electrodes after ashing, thereby providing a display device or semiconductor device with stable driving performance.

[0122] The present invention will be described below with reference to specific examples, but the present invention should not be construed as being limited to these examples.

[0123] [Measurement and Evaluation Methods] (1) Weight-Average Molecular Weight of Component (A) Measurement was carried out using a gel permeation chromatography (GPC) apparatus ("Waters" 2690-996, manufactured by Japan Waters K.K.) using N-methyl-2-pyrrolidone as the developing solvent, and the weight-average molecular weight (Mw) was calculated in terms of polystyrene.

[0124] (2) Weight-average molecular weight and dispersity of component (B) Measurement was carried out using a GPC apparatus ("Waters" 2690-996, manufactured by Nihon Waters K.K.) using tetrahydrofuran as a developing solvent, and the weight-average molecular weight (Mw) and number-average molecular weight (Mn) were determined in terms of polystyrene, and the dispersity (weight-average molecular weight / number-average molecular weight) was calculated.

[0125] (3) Imidization Rate A sample resin was dissolved in γ-butyrolactone to a concentration of 35% by mass. This solution was applied to a 4-inch silicon wafer by spin coating and prebaked at 120°C for 3 minutes to produce a 5 μm-thick resin film. This wafer with the resin film was divided into two, and one half was heat-treated in a clean oven (CLH-21CD-S, manufactured by Koyo Thermo Systems Co., Ltd.) at 140°C for 30 minutes under a nitrogen stream (oxygen concentration 20 ppm or less), and then further heated to 320°C for 1 hour to completely close the imide ring. The transmission infrared absorption spectra of the resin film before and after the heat treatment were measured using an infrared spectrophotometer (FT-720, manufactured by Horiba, Ltd.), and the absorption peak (1,780 cm) of the imide structure attributed to polyimide was observed. －１Near 1,377 cm －１ After confirming the existence of the 1,377 cm －１ The peak intensity ratio (before heat treatment: S, after heat treatment: T) near the peak intensity (S) was calculated by dividing the peak intensity (S) by the peak intensity (T) using the following formula, and this was taken as the content of imide groups in the polymer before heat treatment, i.e., the imidization rate.

[0126] Imidization rate (%) = (S / T) x 100 (4) Compatibility (Haze) A sample resin composition was applied to a 5 cm x 5 cm heat-resistant glass ("Tempax") so that the thickness of the resin composition film after pre-baking would be 3 μm. Next, the coating was pre-baked at 120°C for 2 minutes using a hot plate to obtain a dried substrate with the resin composition. The film thickness was measured using a film thickness measuring device ("Lambda Ace" STM-602, manufactured by Dainippon Screen Mfg. Co., Ltd.) under the condition of a refractive index of 1.63.

[0127] The substrate with the photosensitive resin composition after prebaking was treated with a 2.38% by mass aqueous solution of tetramethylammonium (hereinafter sometimes referred to as "TMAH") (manufactured by Tama Chemicals Co., Ltd.) so that the film loss was 0.5 μm. After treatment, the substrate was rinsed with distilled water and shaken dry. The haze of the resulting substrate with the resin composition was measured using a spectroscopic haze meter (Murakami Color Research Laboratory "HSP-150Vis"). Note that the higher the haze value, the poorer the compatibility.

[0128] (5) Flatness Evaluation (Surface Steps) Figure 2 shows a schematic explanatory diagram of the cross section of a flatness evaluation sample. The sample resin composition was applied by spin coating using a coating and developing apparatus (ACT-8 manufactured by Tokyo Electron Ltd.) onto a stepped substrate 11 having five parallel line patterns with a thickness (height) of 1.5 μm, a width of 5 μm, and a length of 4 mm, spaced 5 μm apart. The resulting film was prebaked at 120°C for 2 minutes to produce a prebaked film with a film thickness of approximately 2.9 μm in areas of the substrate not affected by the line patterns. The film thickness was measured using a Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd., under the condition of a refractive index of 1.63. Thereafter, the substrate was treated in the ACT-8 using a 2.38% by mass aqueous solution of TMAH (manufactured by Tama Chemicals Co., Ltd.) for a time period until the film thickness after the TMAH aqueous solution treatment reached 0.5 μm, and then rinsed with distilled water and spun dry to obtain a film with a film thickness of approximately 2.4 μm. At this time, the film thickness of the resin film in a portion of the substrate not affected by the line pattern was measured and used as the film thickness before heat treatment. Subsequently, the stepped substrate on which the resin film had been formed after the TMAH aqueous solution treatment was heat-treated in a high-temperature inert gas oven (INH-9CD-S; manufactured by Koyo Thermo Systems Co., Ltd.) at 250°C in a nitrogen atmosphere for 60 minutes to produce a cured film (cured product 12). The surface step heights of the resulting cured film, excluding the two outermost lines, were measured using a surface profiler (P-15; KLA-Tencor Corporation). The average heights (heights of the cured film, represented by h1 to h3 in Figure 2) were recorded as the surface step height (μm). The baseline for each step was defined as the line connecting the smallest film thicknesses of the recesses on the left and right of each mountain-like resin film portion where h1 to h3 were measured, as viewed from Figure 2. A specific example is described below. In Figure 2, the baseline was the line connecting the bottoms a1 and a2 of the step shape, and h1 was defined as the length from the top b1 of the step shape to the intersection of the baseline and a line drawn perpendicular to the substrate surface.h2 is defined as the length from the top b2 of the step shape to the intersection of a line drawn perpendicular to the substrate surface and the baseline, with the line connecting a2 and a3 as the baseline, and h3 is defined as the length from the top b3 of the step shape to the intersection of a line drawn perpendicular to the substrate surface and the baseline, with the line connecting a3 and a4 as the baseline.

[0129] (6) Pattern Retention Rate A sample resin composition was applied onto an 8-inch silicon wafer by spin coating using a coating and developing apparatus (ACT-8 manufactured by Tokyo Electron Limited). Then, the wafer was prebaked at 120°C for 2 minutes to prepare a prebaked film having a thickness of 3.0 µm. The film thickness was measured using a film thickness measuring device (Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd.) under the condition of a refractive index of 1.63.

[0130] This film was exposed to light using an exposure system (Nikon Corporation "NSR-2005i9C") through a mask having a pattern of circular contact holes with a diameter of 5 μm. After exposure, the film was developed using the coating and developing system described above with a 2.38 mass % TMAH aqueous solution (Tama Chemicals Co., Ltd.) as the developer for a development time such that the film loss in the unexposed areas was 0.5 μm. After development, the film was rinsed with distilled water and shaken off to dry, obtaining a pattern.

[0131] The resulting pattern was observed at 2000x magnification using a digital microscope (VHX-6000, manufactured by Keyence Corporation), and the opening diameter (φ1) of the 5 μm hole pattern was measured. The substrate with the dried photosensitive resin was then heat-treated in a high-temperature inert gas oven (INH-9CD-S, manufactured by Koyo Thermo Systems Co., Ltd.) at 250°C under a nitrogen atmosphere for 60 minutes to obtain a cured film. The opening diameter (φ2) of the 5 μm-wide hole pattern in the cured film was measured again, and the ratio of the opening diameter after heat treatment to the opening diameter before heat treatment (φ2 / φ1) was calculated as a percentage.

[0132] The abbreviations of the components used in the examples are shown below: HMOM-TPHAP: (compound shown in the chemical formula below, manufactured by Honshu Chemical Industry Co., Ltd.)

[0133]

[0134] TM-BIP-A: (compound shown in the chemical formula below, manufactured by Asahi Organic Materials Industry Co., Ltd.)

[0135]

[0136] TrisP-PA: (compound shown in the chemical formula below, manufactured by Honshu Chemical Industry Co., Ltd.)

[0137]

[0138] VG3101L: (compound represented by the following chemical formula, manufactured by Printec Co., Ltd.)

[0139]

[0140] GBL: γ-butyrolactone PGME: propylene glycol monomethyl ether MPA: 3-methoxy-N,N-dimethylpropanamide (KJ Chemicals Co., Ltd.) ODPA: 4,4'-oxydiphthalic anhydride MCTC: 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride TDA100: 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride OBBA: diphenyl ether-4,4'-dicarboxylic acid SiDA: 1,3-bis(3-aminopropyl)tetramethyldisiloxane (Tokyo Chemical Industry Co., Ltd.) BAP: 2,2-bis(3-amino-4-hydroxyphenyl)propane BAHF: 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane MAP: 3-aminophenol (Tokyo Chemical Industry Co., Ltd.) The synthesis of the compounds used in the examples and comparative examples is described below.

[0141] Synthesis Example 1: Synthesis of diamine (DAP-A) A 500 ml four-neck flask equipped with a stirrer, thermocouple, and dropping funnel was charged with 24.28 g (0.086 mol) of BisP-3MZ (4,4'-(3-methylcyclohexane-1,1-diyl)diphenol, manufactured by Honshu Chemical Industry Co., Ltd.) and 100 ml of glacial acetic acid, and the mixture was stirred. The internal temperature was raised to 50°C in a hot water bath. To this mixture, 2 ml (0.026 mol) of concentrated nitric acid was added dropwise over 1 hour, followed by ice cooling to lower the internal temperature to 13°C, and then 13.3 ml (0.149 mol) of concentrated nitric acid was added dropwise over 1 hour. Stirring was continued for 3 hours, and the precipitated yellow crystals were filtered, washed successively with 40 ml of glacial acetic acid and 80 ml of deionized water, and dried under reduced pressure to obtain the dinitro form.

[0142] Next, 50.27 g (0.135 mol) of the dinitro compound, 180 ml (3.71 mol) of hydrazine monohydrate, and 900 ml of ethanol were placed in a 2 L four-neck flask equipped with a stirrer, thermocouple, Dimroth condenser, and dropping funnel, and the mixture was stirred under ice cooling. 0.9 g of 5% palladium-carbon (Wako Pure Chemical Industries, Ltd.) suspended in 30 ml of ethanol was added dropwise over 1 hour. The solution was then refluxed for 2 hours, and the palladium-carbon was removed by filtration while washing with 300 ml of ethanol. All of the solvent was removed by heating under reduced pressure, and the residue was washed with 75 ml of ice-cold ethanol, filtered, and then washed with 75 ml of deionized water and 150 ml of diethyl ether, followed by drying under reduced pressure, to obtain diamine (DAP-A).

[0143] Synthesis Example 2: Synthesis of diamine (DAP-B) A dinitro compound was synthesized using 26.70 g (0.086 mol) of BisP-HTG (manufactured by Honshu Chemical Industry Co., Ltd.; 4,4′-(3,3,5-trimethylcyclohexylidene)bisphenol) instead of BisP-3MZ, and diamine (DAP-B) was obtained in the same manner as in Synthesis Example 1, except that 54.06 g (0.135 mol) of the dinitro compound was used.

[0144] Synthesis Example 3: Synthesis of diamine (DAP-C) A dinitro product was synthesized using 23.25 g (0.086 mol) of 4,4′-(1,3-dimethylbutylidene)diphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of BisP-3MZ, and diamine (DAP-C) was obtained in the same manner as in Synthesis Example 1 except that 48.65 g (0.135 mol) of the dinitro product was used.

[0145] Synthesis Example 4: Synthesis of diamine (DAP-D) A dinitro product was synthesized using 25.66 g (0.086 mol) of BisP-IOTD (manufactured by Honshu Chemical Industry Co., Ltd.; 4,4′-(2-ethylhexylidene)diphenol) instead of BisP-3MZ, and diamine (DAP-D) was obtained in the same manner as in Synthesis Example 1, except that 52.44 g (0.135 mol) of the dinitro product was used.

[0146] Synthesis Example 5: Synthesis of 2,2-bis[3-(3-aminobenzamido)-4-hydroxyphenyl]hexafluoropropane (HA) 18.3 g (0.05 mol) of BAHF was dissolved in 100 mL of acetone and 17.4 g (0.3 mol) of propylene oxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and the solution was cooled to −15°C. A solution of 20.4 g (0.11 mol) of 3-nitrobenzoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) dissolved in 100 mL of acetone was added dropwise to the solution. After the addition was completed, the mixture was stirred at −15°C for 4 hours and then returned to room temperature. The precipitated white solid was filtered and dried in vacuo at 50°C.

[0147] 30 g of the obtained white solid was placed in a 300 mL stainless steel autoclave and dispersed in 250 mL of methyl cellosolve, and 2.0 g of 5% palladium-carbon (manufactured by Wako Pure Chemical Industries, Ltd.) was added. Hydrogen was introduced into the autoclave using a balloon, and a 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 completed, the palladium compound catalyst was removed by filtration, and the mixture was concentrated using a rotary evaporator to obtain a diamine compound (HA).

[0148] Synthesis Example 6: Synthesis of diamine compound (HB) A diamine compound (HB) was obtained in the same manner as in Synthesis Example 5, except that 12.9 g (0.05 mol) of BAP was used instead of BAHF.

[0149] Synthesis Example 7 Synthesis of diamine compound (HC) A diamine compound (HC) was obtained in the same manner as in Synthesis Example 5, except that 15.0 g (0.05 mol) of DAP-C obtained in Synthesis Example 3 was used instead of BAHF.

[0150] The structures of the diamine compounds obtained in Synthesis Examples 1 to 7 are shown below.

[0151]

[0152] Synthesis Example 8: Synthesis of Polyimide (A-1) Under a dry nitrogen stream, 10.98 g (0.0425 mol) of BAP and 0.62 g (0.0025 mol) of SiDA were dissolved in 95 g of MPA. To this solution, 15.51 g (0.050 mol) of ODPA was added along with 10 g of MPA, and the mixture was stirred at 60°C for 2 hours. Then, 1.09 g (0.010 mol) of MAP was added as an end-capping agent along with 10 g of MPA, and the mixture was reacted at 60°C for 1 hour. The mixture was then stirred at 180°C for 4 hours. After stirring, the temperature was lowered from 180°C to room temperature, and the solution was poured into 2 L of deionized water. The precipitated polymer solid was collected by filtration. The mixture was further washed three times with 2 L of deionized water, and the collected polymer solid was dried in a vacuum dryer at 50°C for 72 hours to obtain polyimide (A-1).

[0153] Synthesis Example 9: Synthesis of Polyamic Acid (A-2) Under a dry nitrogen stream, 10.98 g (0.0425 mol) of BAP and 0.62 g (0.0025 mol) of SiDA were dissolved in 95 g of MPA. To this solution, 15.51 g (0.050 mol) of ODPA was added along with 10 g of MPA, and the mixture was stirred at 60°C for 2 hours. Then, 1.09 g (0.010 mol) of MAP was added as an end-capping agent along with 10 g of MPA, and the mixture was reacted at 60°C for 1 hour. The mixture was then stirred at 140°C for 4 hours. After stirring, the temperature was lowered from 140°C to room temperature, and the solution was poured into 2 L of deionized water. The precipitated polymer solid was collected by filtration. The mixture was further washed three times with 2 L of deionized water, and the collected polymer solid was dried in a vacuum dryer at 50°C for 72 hours to obtain polyamic acid (A-2), a form of a polyimide precursor.

[0154] Synthesis Example 10: Synthesis of Polyamic Acid (A-3) Polyamic acid (A-3), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 9, except that 0.93 g (0.010 mol) of aniline was used instead of 1.09 g (0.010 mol) of MAP.

[0155] Synthesis Example 11: Synthesis of Polyamic Acid (A-4) Polyamic acid (A-4), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 9, except that 1.17 g (0.010 mol) of 4-ethynylaniline was used instead of 1.09 g (0.010 mol) of MAP.

[0156] Synthesis Example 12: Synthesis of polyamic acid (A-5) Polyamic acid (A-5), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 11, except that 13.28 g (0.0425 mol) of a diamine compound (DAP-A) was used instead of 10.98 g (0.0425 mol) of BAP.

[0157] Synthesis Example 13: Synthesis of polyamic acid (A-6) Polyamic acid (A-6), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 11, except that 14.47 g (0.0425 mol) of the diamine compound (DAP-B) was used instead of 10.98 g (0.0425 mol) of BAP.

[0158] Synthesis Example 14: Synthesis of polyamic acid (A-7) Polyamic acid (A-7), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 11, except that 12.77 g (0.0425 mol) of a diamine compound (DAP-C) was used instead of 10.98 g (0.0425 mol) of BAP.

[0159] Synthesis Example 15: Synthesis of polyamic acid (A-8) Polyamic acid (A-8), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 11, except that 13.96 g (0.0425 mol) of a diamine compound (DAP-D) was used instead of 10.98 g (0.0425 mol) of BAP.

[0160] Synthesis Example 16: Synthesis of polyamic acid (A-9) Polyamic acid (A-9), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 13.21 g (0.050 mol) of MCTC was used instead of 15.51 g (0.050 mol) of ODPA.

[0161] Synthesis Example 17: Synthesis of polyamic acid (A-10) Polyamic acid (A-10), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 7.76 g (0.025 mol) of ODPA and 6.61 g (0.025 mol) of MCTC were used instead of 15.51 g (0.050 mol) of ODPA.

[0162] Synthesis Example 18: Synthesis of polyamic acid (A-11) Polyamic acid (A-11), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 12.41 g (0.040 mol) of ODPA and 2.64 g (0.010 mol) of MCTC were used instead of 15.51 g (0.050 mol) of ODPA.

[0163] Synthesis Example 19: Synthesis of polyamic acid (A-12) Polyamic acid (A-12), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 15.01 g (0.050 mol) of TDA100 was used instead of 15.51 g (0.050 mol) of ODPA.

[0164] Synthesis Example 20: Synthesis of Polyamic Acid Ester (A-13) Under a dry nitrogen stream, 21.10 g (0.0425 mol) of diamine compound (HB) and 0.62 g (0.0025 mol) of SiDA were dissolved in 95 g of MPA. To this solution, 15.51 g (0.050 mol) of ODPA was added along with 10 g of MPA, and the mixture was stirred at 60°C for 2 hours. Then, 1.17 g (0.010 mol) of 4-ethynylaniline as an end-capping agent was added along with 10 g of MPA, and the mixture was allowed to react at 60°C for 1 hour. After the temperature was lowered from 60°C to 40°C, a solution prepared by diluting 11.9 g (0.10 mol) of N,N-dimethylformamide dimethyl acetal with 10 g of MPA was added dropwise. After the dropwise addition, the mixture was stirred at 40°C for 2 hours. After stirring, the solution was poured into 2 L of deionized water, and the precipitated polymer solid was collected by filtration. The polymer solid was further washed three times with 2 L of deionized water, and then dried in a vacuum dryer at 50°C for 72 hours to obtain polyamic acid ester (A-13), which is a form of polyimide precursor.

[0165] Synthesis Example 21: Synthesis of polyamic acid ester (A-14) Polyamic acid ester (A-14), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 20, except that 22.89 g (0.0425 mol) of diamine compound (HC) was used instead of 21.10 g (0.0425 mol) of diamine compound (HB).

[0166] Synthesis Example 22: Synthesis of polyamic acid (A-15) Polyamic acid (A-15), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 1.49 g (0.010 mol) of 4-isopropylaniline was used instead of 1.17 g (0.010 mol) of 4-ethynylaniline.

[0167] Synthesis Example 23: Synthesis of polyamic acid (A-16) Polyamic acid (A-16), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 14, except that 1.21 g (0.010 mol) of 3-ethylaniline was used instead of 1.17 g (0.010 mol) of 4-ethynylaniline.

[0168] Synthesis Example 24: Synthesis of Polybenzoxazole Precursor (A-17) Under a dry nitrogen stream, 0.05 mol of a mixture of dicarboxylic acid derivatives obtained by reacting 12.91 g (0.05 mol) of OBBA with 13.51 g (0.10 mol) of 1-hydroxy-1,2,3-benzotriazole was dissolved in 95 g of MPA. To this solution, 13.52 g (0.045 mol) of a diamine compound (DAP-C) was added along with 10 g of MPA, and the reaction was carried out at 75°C for 12 hours. Then, 1.17 g (0.010 mol) of 4-ethynylaniline was added as an end-capping agent along with 15 g of MPA, and the mixture was stirred for an additional 12 hours to complete the reaction. The reaction mixture was filtered and then poured into a water / methanol solution (volume ratio: 3 / 1), yielding a white precipitate. The 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 polybenzoxazole precursor (A-17).

[0169] Synthesis Example 25: Synthesis of polyamic acid ester (A-18) Polyamic acid ester (A-18), which is one form of a polyimide precursor, was obtained in the same manner as in Synthesis Example 20, except that 25.69 g (0.0425 mol) of diamine compound (HA) was used instead of 21.10 g (0.0425 mol) of diamine compound (HB), and 1.09 g (0.010 mol) of MAP was used instead of 1.17 g (0.010 mol) of 4-ethynylaniline.

[0170] Table 1 shows the constituent components (molar ratio), weight average molecular weight (Mw), and imidization rate [%] of Synthesis Examples 8 to 25.

[0171]

[0172] Synthesis Example 26: Synthesis of Polyhydroxystyrene (B-1) A reaction vessel containing a stirrer was charged with 2,400 g of tetrahydrofuran as a solvent and cooled to -40°C. 2.56 g (0.04 mol) of sec-butyllithium was then added as an initiator to the resulting mixture. 105.75 g (0.6 mol) of p-t-butoxystyrene was added and the mixture was stirred for 1 hour to polymerize, followed by the addition of 12.82 g (0.4 mol) of methanol to terminate the polymerization. The reaction mixture was then poured into 3 L of methanol to purify the polymer, and the precipitated polymer was dried. The resulting 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 the p-t-butoxy groups and convert them to hydroxyl groups. After completion of the reaction, the solution was poured into water to precipitate the polymer. The resulting precipitate was washed three times with water and then dried in a vacuum dryer at 50°C for 24 hours to obtain the desired polyhydroxystyrene (B-1). The weight average molecular weight was 6,000 and the dispersity was 1.08.

[0173] Synthesis Example 27: Synthesis of polyhydroxystyrene-styrene copolymer (B-2) A polyhydroxystyrene-styrene copolymer (B-2) was obtained in the same manner as in Synthesis Example 26, except that 100.47 g (0.57 mol) of p-t-butoxystyrene and 3.13 g (0.03 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.09.

[0174] Synthesis Example 28: Synthesis of polyhydroxystyrene-styrene copolymer (B-3) A polyhydroxystyrene-styrene copolymer (B-3) was obtained in the same manner as in Synthesis Example 26, except that 95.18 g (0.54 mol) of p-t-butoxystyrene and 6.25 g (0.06 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0175] Synthesis Example 29: Synthesis of polyhydroxystyrene-styrene copolymer (B-4) A polyhydroxystyrene-styrene copolymer (B-4) was obtained in the same manner as in Synthesis Example 26, except that 93.06 g (0.53 mol) of p-t-butoxystyrene and 7.50 g (0.07 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0176] Synthesis Example 30: Synthesis of polyhydroxystyrene-styrene copolymer (B-5) A polyhydroxystyrene-styrene copolymer (B-5) was obtained in the same manner as in Synthesis Example 26, except that 89.89 g (0.51 mol) of p-t-butoxystyrene and 9.37 g (0.09 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0177] Synthesis Example 31: Synthesis of polyhydroxystyrene-styrene copolymer (B-6) A polyhydroxystyrene-styrene copolymer (B-6) was obtained in the same manner as in Synthesis Example 26, except that 84.61 g (0.48 mol) of p-t-butoxystyrene and 12.50 g (0.12 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0178] Synthesis Example 32: Synthesis of polyhydroxystyrene-styrene copolymer (B-7) A polyhydroxystyrene-styrene copolymer (B-7) was obtained in the same manner as in Synthesis Example 26, except that 79.31 g (0.45 mol) of p-t-butoxystyrene and 15.62 g (0.15 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0179] Synthesis Example 33: Synthesis of polyhydroxystyrene-styrene copolymer (B-8) A polyhydroxystyrene-styrene copolymer (B-8) was obtained in the same manner as in Synthesis Example 26, except that 74.03 g (0.42 mol) of p-t-butoxystyrene and 18.75 g (0.18 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.10.

[0180] Synthesis Example 34: Synthesis of polyhydroxystyrene-styrene copolymer (B-9) A polyhydroxystyrene-styrene copolymer (B-9) was obtained in the same manner as in Synthesis Example 26, except that 63.45 g (0.36 mol) of p-t-butoxystyrene and 25.00 g (0.24 mol) of styrene were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000 and the dispersity was 1.11.

[0181] Synthesis Example 35: Synthesis of Polyhydroxystyrene (B-10) Under a dry nitrogen stream, 105.75 g (0.6 mol) of p-t-butoxystyrene was dissolved in 100 g of tetrahydrofuran, and the temperature was raised to 83°C. 0.1 g of azobisisobutylnitrile was added three times at 3-hour intervals, and finally, polymerization was allowed to proceed with stirring for an additional 2 hours. The reaction solution was then poured into 1,200 g of hexane, and a white resin was precipitated. The resulting polymer was dissolved in 1.6 L of acetone, and 2 g of concentrated hydrochloric acid was added at 60°C and the mixture was stirred for 7 hours to deprotect the p-t-butoxy groups and convert them to hydroxyl groups. After completion of the reaction, the solution was poured into water to precipitate the polymer. The resulting precipitate was washed three times with water and then dried in a vacuum dryer at 50°C for 24 hours, yielding the target polyhydroxystyrene (B-10). The weight-average molecular weight was 7,000, and the dispersity was 1.98.

[0182] Synthesis Example 36: Synthesis of polyhydroxystyrene-phenylmaleimide copolymer (B-11) A polyhydroxystyrene-phenylmaleimide copolymer (B-11) was obtained in the same manner as in Synthesis Example 26, except that 95.18 g (0.54 mol) of p-t-butoxystyrene and 10.39 g (0.06 mol) of N-phenylmaleimide were used instead of 105.75 g (0.6 mol) of p-t-butoxystyrene. The weight average molecular weight was 6,000, and the dispersity was 1.13.

[0183] Synthesis Example 37: Synthesis of quinone diazide compound (C-1) Under a dry nitrogen stream, 21.23 g (0.05 mol) of TrisP-PA and 33.58 g (0.125 mol) of 4-naphthoquinone diazide sulfonyl chloride were dissolved in 450 g of 1,4-dioxane and the solution was allowed to cool to room temperature. To this solution, 12.65 g (0.125 mol) of triethylamine mixed with 50 g of 1,4-dioxane was added dropwise so that the reaction system did not exceed 35°C. After the dropwise addition, the mixture was stirred at 30°C for 2 hours. The triethylamine salt was filtered, and the filtrate was poured into water. The precipitate was then collected by filtration. This precipitate was dried in a vacuum dryer to obtain quinone diazide compound (C-1), which is a naphthoquinone diazide compound represented by the following formula:

[0184] The quinonediazide substitution rate of the quinonediazide compound (C-1), that is, the substitution rate of quinonediazide sulfonyl groups when the total amount of Q is taken as 100 mol %, was 83 mol %.

[0185]

[0186] [Example 1] Under yellow light, 7.5 g of polyimide (A-1) as component (A), 2.5 g of polyhydroxystyrene-styrene copolymer (B-3) as component (B), 2.0 g of quinone diazide compound (C-1) as quinone diazide compound, and 1.5 g of HMOM-TPHAP as component (E) were weighed out, and these were dissolved in a mixed solvent of 10.0 g of GBL and 40.0 g of PGME. The resulting solution was then filtered through a filter with a pore size of 1 μm to obtain resin composition W1.

[0187] [Examples 2 to 17] As shown in Table 2-1, resin compositions W2 to W17 were obtained in the same manner as in Example 1, except that polyamic acid ester (A-2) or polybenzoxazole precursor (A-17) was used as component (A) instead of polyimide (A-1).

[0188] [Examples 18 to 26] As shown in Table 2-2, resin compositions W18 to W26 were obtained in the same manner as in Example 1, except that polyamic acid (A-9) was used as component (A) instead of polyimide (A-1), and polyhydroxystyrene (B-1), polyhydroxystyrene-styrene copolymer (B-2), polyhydroxystyrene-styrene copolymer (B-4) or polyhydroxystyrene-styrene copolymer (B-10) was used as component (B).

[0189] [Example 27] As shown in Table 2-2, a resin composition W27 was obtained in the same manner as in Example 21, except that a polybenzoxazole precursor (A-17) was used as the component (A) instead of the polyimide (A-9).

[0190] Example 28 As shown in Table 2-2, a resin composition W28 was obtained in the same manner as in Example 7, except that a polyhydroxystyrene-phenylmaleimide copolymer (B-11) was used as the component (B).

[0191] [Examples 29 to 35] As shown in Table 2-3, resin compositions W29 to W35 were obtained in the same manner as in Example 4, except that polyhydroxystyrene (B-1) to polyhydroxystyrene-styrene copolymer (B-3), polyhydroxystyrene-styrene copolymer (B-6) to polyhydroxystyrene-styrene copolymer (B-10) were used as component (B), and component (E) was not included.

[0192] Example 36 As shown in Table 2-3, a resin composition W36 was obtained in the same manner as in Example 7, except that 1.5 g of TM-BIP-A was used as component (E) instead of 1.5 g of HMOM-TPHAP.

[0193] Example 37 As shown in Table 2-3, a resin composition W37 was obtained in the same manner as in Example 7, except that 1.5 g of VG3101L was used as component (E) instead of 1.5 g of HMOM-TPHAP.

[0194] Example 38 As shown in Table 2-3, a resin composition W38 was obtained in the same manner as in Example 7, except that the component (E) was not included.

[0195] Examples 39 to 43 Resin compositions W39 to W43 were obtained in the same manner as in Example 7, except that the amount of HMOM-TPHAP added as component (E) was changed as shown in Table 2-4.

[0196] [Examples 44 to 50] Resin compositions W44 to W50 were obtained in the same manner as in Example 1, except that under yellow light, polyamic acid ester (A-7) was used as component (A), polyhydroxystyrene-styrene copolymer (B-3) as component (B), quinone diazide compound (C-1) as component (B), and HMOM-TPHAP as component (E) were used in the amounts shown in Table 2-4.

[0197] The evaluation results for each example are shown in Tables 2-1 to 2-4.

[0198]

[0199]

[0200]

[0201]

[0202] [Comparative Example 1] Under yellow light, 5.0 g of polyamic acid ester (A-18) as component (A), 5.0 g of polyhydroxystyrene-styrene copolymer (B-3) as component (B), and 2.0 g of quinone diazide compound (C-1) as a quinone diazide compound were weighed out, and these were dissolved in a mixed solvent of 10.0 g of GBL and 40.0 g of PGME. The resulting solution was then filtered through a filter with a pore size of 1 μm to obtain resin composition W51.

[0203] Comparative Example 2 Resin composition W52 was obtained in the same manner as in Comparative Example 1, except that the amount of polyamic acid ester (A-18) as component (A) was changed to 7.5 g and the amount of polyhydroxystyrene-styrene copolymer (B-3) as component (B) was changed to 2.5 g.

[0204] [Comparative Example 3] Resin composition W53 was obtained in the same manner as in Comparative Example 1, except that 10 g of polyamic acid (A-7) was used as component (A) instead of 5.0 g of polyamic acid ester (A-18), and component (B) was not included.

[0205] Comparative Example 4 Resin composition W54 was obtained in the same manner as in Comparative Example 1, except that 10 g of polyamic acid ester (A-2) was used as the component (A) instead of 5.0 g of polyamic acid ester (A-13), and that component (B) was not included.

[0206] [Comparative Example 5] Resin composition W55 was obtained in the same manner as in Comparative Example 1, except that 10 g of polyhydroxystyrene (B-1) was used as the component (B) instead of 5.0 g of polyhydroxystyrene-styrene copolymer (B-3), and that the component (A) was not included.

[0207] The evaluation results of each comparative example are shown in Table 3.

[0208]

[0209] In Examples 1 to 50, good results were obtained in compatibility and flatness. In contrast, in Comparative Examples 1 and 2, in which a polyimide precursor not containing the divalent structure represented by formula (1) was used, compatibility was poor. Furthermore, in Comparative Examples 3 and 4, which did not contain component (B), and in Comparative Example 5, which did not contain component (A), flatness was poor.

[0210] 1: Substrate 2: TFT 3: TFT insulating layer 4: Wiring 5: Planarizing layer 6: Contact hole 7: First electrode 8: Pixel dividing layer 9: Organic EL layer 10: Second electrode 11: Step substrate 12: Cured product

Claims

1. A resin composition comprising one or more resins selected from the group consisting of polyimide resins, polybenzoxazole resins, and their precursors (hereinafter referred to as "component (A)"), a resin containing a hydroxystyrene unit in its unit structure (hereinafter referred to as "component (B)"), a quinone diazide compound, and an organic solvent, wherein component (A) has a divalent structure represented by formula (1) derived from a diamine. (X is a divalent hydrocarbon group having 1 to 15 carbon atoms, -O-, -S-, -SO ２ represents - or a single bond, R １ and R ２ are each independently -CH ２ -, -C(CH ３ ) ２ represents -, -O-, -NHC(=O)-, or -C(=O)NH-, each t independently represents an integer of 0 or 1, and * represents an amide bond, an imide bond, or a bond that binds to a nitrogen atom of an oxazole ring.

2. The resin composition according to claim 1, wherein all or part of component (A) is a polyimide resin or a polyimide precursor resin (hereinafter referred to as "component (A-1)"), and all or part of component (B) is at least one resin selected from the group consisting of polyhydroxystyrene and copolymers of polyhydroxystyrene and polystyrene.

3. The resin composition according to claim 1 or 2, wherein X in the divalent structure represented by formula (1) is a divalent hydrocarbon group represented by formula (2) or formula (3). (R ３ represents an alkyl group having 1 to 3 carbon atoms, and when there are a plurality of such groups, they may be the same or different; a represents 1 or 2; b represents an integer of 1 to 3; R ４ and R ５ each independently represents a hydrocarbon group having 1 to 7 carbon atoms or a hydrogen atom, and * represents the point of attachment to the aromatic ring. ４ and R ５ do not have the same structure.) 4. A resin composition according to claim 1 or 2, in which the ratio ([W] / ([W]+[HS]) of the amount of units other than hydroxystyrene units contained in component (B) as [W] (moles) to the amount of hydroxystyrene units as [HS] (moles) is 0.12 or more and 0.30 or less.

5. The resin composition according to claim 2, wherein component (A-1) contains, as the acid dianhydride residue, a tetravalent group having 8 to 40 carbon atoms and containing an alicyclic structure within its structure, in an amount of 20 to 100 mol % when the total amount of acid dianhydride residues in component (A-1) is taken as 100 mol %.

6. A resin composition according to claim 1 or 2, wherein the content of fluorine atoms present in the molecular structure of the resin of component (A) is 10,000 mass ppm or less.

7. The resin composition according to claim 1 or 2, wherein X in the divalent structural unit represented by formula (1) is a divalent hydrocarbon group represented by formula (3). (R ４ and R ５ each independently represents a hydrocarbon group having 1 to 7 carbon atoms or a hydrogen atom, and * represents the point of attachment to the aromatic ring. ４ and R ５ do not have the same structure.) 8. A resin composition according to claim 1 or 2, wherein the dispersity of component (B) is 1.30 or less.

9. The resin composition according to claim 1 or 2, wherein the divalent structure represented by formula (1) contained in component (A) is used in component (A) as a structural unit derived from diamine, and accounts for 50 to 100 mol % when the total amount of diamines having an imide bond, an amic acid structure, a benzoxazole precursor structure, or a benzoxazole ring is taken as 100 mol %.

10. A resin composition according to claim 1 or 2, in which the proportion of component (B) is 10% by mass or more and 50% by mass or less when the total mass of components (A) and (B) is 100% by mass.

11. The resin composition according to claim 1 or 2, further comprising a crosslinking agent containing either or both of a methylol group and an alkoxymethyl group (hereinafter referred to as "component (E)").

12. The resin composition according to claim 11, wherein the content of component (B) is [B] (mass %) and the content of component (E) is [E] (mass %) when the total amount of the resin composition is 100 mass %, and the relationship [B] / [E] is 1.0≦[B] / [E]≦2.

5.

13. A resin composition according to claim 1 or 2, wherein component (A) contains a structure represented by formula (4). (R ６ represents a hydrocarbon group having 1 to 4 carbon atoms, which may be the same or different when there are a plurality of them, l represents an integer of 1 to 3, and * represents a bond.

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

15. A display device comprising the cured product according to claim 14.

16. A semiconductor device comprising the cured product according to claim 14.

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