KR20240090789A - Photosensitive resin composition, cured product, and image display device - Google Patents

Abstract

The purpose of the present invention is to provide a photosensitive resin composition capable of forming a cured product with excellent scratch resistance. Additionally, the present invention aims to provide a photosensitive resin composition with excellent low-temperature curability and photolithography properties in addition to the above-mentioned properties, a cured product obtained from the photosensitive resin composition, and an image display device comprising the cured product. The photosensitive resin composition of the present invention contains an alkali-soluble resin containing one or more types of repeating structural units X represented by the following general formula (1), and a crosslinking agent. (In the formula, R ¹ is hydrogen or a methyl group, R ² is a linking group having 1 or more carbon atoms, R ³ is an organic group or hydroxy group represented by the following general formula (2) bonded to the carbon atom of the linking group, and R ⁴ is It is a hydroxy group or an organic group bonded to the carbon atom of the linking group.) (In the formula, R ⁵ is a hydrocarbon group with a parent carbon number of 2 to 7, an organic group with a parent carbon number of 3 to 8 and also contains a hetero atom, Or, it is an organic group whose parent body has 2 to 7 carbon atoms and also has a carboxyl group.)

Description

Photosensitive resin composition, cured product, and image display device

The present invention relates to photosensitive resin compositions, cured products, and image display devices.

In recent years, with the miniaturization of electronic devices and technological advancements, large-scale integrated circuits (LSIs) have become highly integrated and multi-layered. To obtain such LSI and various precision parts, photolithography technology is widely used as a precision micro-processing technology. In this technology, a fine pattern can be formed on an object by chemical etching, electrolytic etching, etc. using a photosensitive resin composition (resist material).

Additionally, in a liquid crystal display device, a photo spacer is used to maintain the thickness of the liquid crystal layer sandwiched between the color filter side substrate and the thin film transistor (TFT) side substrate.

Photo spacers are generally formed by applying a photosensitive resin composition to a substrate, drying it, exposing it to light passing through a photomask with a predetermined fine pattern, and developing it.

For example, Patent Document 1 contains (A) an alkali-soluble resin, (B) a radical photopolymerization initiator, and (C) a photopolymerizable monomer, and the photopolymerizable monomer (C) is (C-1) isocyanuric acid. A negative photosensitive resin composition containing a photopolymerizable monomer having an acid skeleton and a photopolymerizable monomer having a (C-2) fluorene skeleton has been proposed.

In addition, Patent Document 2 includes (A) component: binder polymer, (B) component: photopolymerizable compound, (C) component: photopolymerization initiator, and (D) component: mercapto group-containing hydrogen donor, and the above ( B) A photosensitive resin composition used as a spacer forming material including a photopolymerizable compound having an ethylenically unsaturated group and an isocyanuric ring structure has been proposed.

Patent Document 1: Japanese Patent Laid-Open No. 2019-124929 Patent Document 2: International Publication No. 2013/115262

In recent years, from the viewpoint of improving product yield during product manufacturing, there has been a demand for a photosensitive resin composition that can form a cured product with excellent scratch resistance. In addition, from the viewpoint of the heat resistance of the device, a series of processes (hereinafter referred to as photolithography processes) of application of the photosensitive resin composition → (prebake) → exposure → development → (postbake) are performed at low temperatures (e.g. , 150°C or lower), that is, a photosensitive resin composition with excellent low-temperature curability is required. In addition, photosensitive resin compositions are required to have excellent photolithographic properties that can form patterns with narrow line widths or through holes with small opening diameters without defects.

However, the photosensitive resin compositions described in Patent Documents 1 and 2 do not sufficiently satisfy the above characteristics.

The purpose of the present invention is to provide a photosensitive resin composition capable of forming a cured product with excellent scratch resistance. Another object of the present invention is to provide a photosensitive resin composition excellent in low-temperature curability and photolithographic properties in addition to the above properties, a cured product obtained from the photosensitive resin composition, and an image display device comprising the cured product.

As a result of repeated studies to solve the above problems, the present inventors have discovered that the above object can be achieved by using a photosensitive resin composition containing the following alkali-soluble resin and a crosslinking agent, and have completed the present invention. .

The present invention relates to a photosensitive resin composition containing an alkali-soluble resin containing one or more types of repeating structural units X represented by the following general formula (1), and a crosslinking agent.

[Formula 1]

(In the formula, R ¹ is hydrogen or a methyl group, R ² is a linking group having 1 or more carbon atoms, R ³ is an organic group or hydroxy group represented by the following general formula (2) bonded to the carbon atom of the linking group, and R ⁴ is It is a hydroxy group or an organic group bonded to the carbon atom of the linking group.)

[Formula 2]

(In the formula, R ⁵ is a hydrocarbon group having a parent carbon number of 2 to 7, an organic group having a parent carbon number of 3 to 8 and containing a hetero atom, or an organic group having a parent carbon number of 2 to 7 and also having a carboxyl group. am.)

The linking group for R ² is preferably a hydrocarbon group having a parent carbon number of 1 to 10, or an organic group having a parent carbon number of 1 to 10 and containing a hetero atom.

The organic group of R ⁴ is one or more functional groups selected from the group consisting of an acryloyloxy group, methacryloyloxy group, acyloxy group, amideoxy group, alkoxy group, aryloxy group, amino group, and nitrogen-containing heterocycle. It is preferable that it is an organic group containing.

In addition, the linking group of R ² is a hydrocarbon group having a parent carbon number of 1 to 7, or an organic group having a parent carbon number of 1 to 7 and containing a hetero atom,

R ⁴ is a hydroxy group, an acryloyloxy group, or a methacryloyloxy group bonded to the carbon atom of the linking group of R ² ,

The above R ⁵ is preferably a hydrocarbon group having a parent carbon number of 2 to 7, or an organic group having a parent carbon number of 2 to 7 and a carboxyl group.

In addition, the linking group of R ² is a hydrocarbon group having a parent carbon number of 1 to 7, or an organic group having a parent carbon number of 1 to 7 and containing a hetero atom,

Said R ⁵ is an organic group represented by the following general formula (3),

The R ⁴ is preferably a hydroxy group, an acryloyloxy group, a methacryloyloxy group, or an organic group represented by the following general formula (4) bonded to the carbon atom of the linking group of the R ² .

[Formula 3]

(In the formula, R ⁶ and R ⁷ are each independently a parent hydrocarbon group having 1 to 6 carbon atoms, and the total parent carbon number of R ⁶ and R ⁷ is 3 to 8.)

[Formula 4]

(In the formula, R ⁸ is hydrogen or a methyl group, and R ⁹ is a parent hydrocarbon group having 1 to 5 carbon atoms, or an organic group having 1 to 5 parent carbon atoms and containing a hetero atom.)

In the alkali-soluble resin, the content of the repeating structural unit

The alkali-soluble resin preferably has an acid value of 10 to 120 mgKOH/g.

The alkali-soluble resin preferably has a weight average molecular weight of 5,000 to 40,000.

The crosslinking agent is preferably a heterocyclic compound having a heterocycle containing two or more nitrogen atoms.

The heterocyclic compound is preferably at least one selected from the group consisting of triazine-based compounds and/or condensates thereof, glycoluril-based compounds and/or condensates thereof, and imidazolidinone-based compounds and/or condensates thereof. do.

The heterocyclic compound preferably has one or more functional groups selected from the group consisting of amino group, N-(hydroxyalkyl) group, and N-(alkoxyalkyl) group.

The content of the cross-linking agent is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the alkali-soluble resin.

The photosensitive resin composition preferably contains an acid catalyst.

The photosensitive resin composition is preferably a resist material.

The cured product of the present invention is obtained from the photosensitive resin composition.

The cured material is preferably a photo spacer, a partition wall material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarization film material.

Additionally, the present invention relates to an image display device containing the above-mentioned cured product.

The alkali-soluble resin of the present invention contains one or more types of repeating structural units Its main characteristic is that it has a branching structure. The photosensitive resin composition of the present invention contains the alkali-soluble resin and a crosslinking agent, and can form a cured product with excellent scratch resistance due to the characteristic structure of the alkali-soluble resin and the crosslinking structure by the crosslinking agent. In addition, since the photosensitive resin composition of the present invention uses the alkali-soluble resin that exhibits high reactivity at the target temperature and further a highly reactive crosslinking agent, it has excellent low-temperature curability and can be used in the photolithography process at 150°C or lower, or 120°C or lower. , furthermore, it can be carried out in a low temperature environment of 100°C or lower. In addition, the photosensitive resin composition of the present invention can form patterns with a thin line width or through holes with a small opening diameter without any problems, and has excellent photolithographic properties. In addition, since the alkali-soluble resin has low reactivity at room temperature, the viscosity of the photosensitive resin composition of the present invention does not increase easily over time and has excellent storage stability.

The photosensitive resin composition of the present invention contains an alkali-soluble resin containing one or more types of repeating structural units X represented by the following general formula (1), and a crosslinking agent.

[Formula 5]

(In the formula, R ¹ is hydrogen or a methyl group, R ² is a linking group having 1 or more carbon atoms, R ³ is an organic group or hydroxy group represented by the following general formula (2) bonded to the carbon atom of the linking group, and R ⁴ is It is a hydroxy group or an organic group bonded to the carbon atom of the linking group.)

[Formula 6]

(In the formula, R ⁵ is a hydrocarbon group having a parent carbon number of 2 to 7, an organic group having a parent carbon number of 3 to 8 and containing a hetero atom, or an organic group having a parent carbon number of 2 to 7 and also having a carboxyl group. am.)

In the present invention, (meth)acrylic refers to acrylic or methacryl, (meth)acryloyl refers to acryloyl or methacryloyl, (meth)acrylic acid refers to acrylic acid or methacrylic acid, and (meth)acrylate means acrylate or methacrylate, respectively. In addition, in the present invention, the carbon number of the parent body refers to the carbon number of the main skeleton group excluding substituents.

In the general formula (1), R ² is a linking group having 1 or more carbon atoms, and is not particularly limited as long as it is a group having 1 or more carbon atoms that can connect R ³ and R ⁴ to the oxygen atom of the ester bond. The R ³ and the R ⁴ may be bonded to the same atom of the R ² or may be bonded to different atoms. Examples of the linking group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups (including cross-linked and condensed rings), aromatic hydrocarbon groups, and carbon atoms constituting the hydrocarbon groups. An organic group in which a part of is substituted with a heteroatom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.), and an organic group in which two or more of these are bonded, are included. In addition, the hydrocarbon group or the organic group may contain various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, and aryl group, etc.) or functional groups (e.g., ester bond, amide group, etc.) bond, ether bond, thioether bond, urethane bond, etc.).

The linking group is preferably a hydrocarbon group having a parent carbon number of 1 to 10, or an organic group having a parent carbon number of 1 to 10 and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.). In addition, the linking group is preferably a hydrocarbon group having a parent carbon number of 1 to 7, or an organic group having a parent carbon number of 1 to 7 and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.). desirable. In addition, when the linking group contains a hetero atom, the hetero atom of the linking group may be a portion other than the bonding portion with R ³ , a portion other than the bonding portion with R ^{4 ,} and an ester bond in the general formula (1). It has parts other than the bonding area with the oxygen atom. In addition, the linking group is a linear or branched aliphatic saturated or unsaturated hydrocarbon group with a parent carbon number of 2 to 7, an alicyclic saturated or unsaturated hydrocarbon group with a parent carbon number of 3 to 7, and a parent carbon number of 4 to 7. Also, a hydrocarbon group in which a methylene group and an alicyclic saturated or unsaturated hydrocarbon group are bonded, a hydrocarbon group in which the parent carbon number is 5 to 7 and a linear or branched aliphatic saturated or unsaturated hydrocarbon group is bonded to an alicyclic saturated or unsaturated hydrocarbon group, or the parent carbon number is It is more preferable that the group is 2 to 7 and is an organic group containing an ether bond.

In the general formula (1), R ³ is an organic group or a hydroxy group represented by the general formula (2) that is bonded to the carbon atom of the linking group of R ² . In the general formula (2), R ⁵ is a parent hydrocarbon group having 2 to 7 carbon atoms, a parent having 3 to 8 carbon atoms, and a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.) It is an organic group containing, or an organic group whose parent carbon number is 2 to 7 and also has a carboxyl group. The above R ⁵ is preferably a hydrocarbon group having a parent carbon number of 2 to 7, or an organic group having a parent carbon number of 2 to 7 and a carboxyl group. When R ⁵ has a carboxyl group, the number of carboxyl groups is not particularly limited, but is preferably 1 to 2. Examples of the hydrocarbon group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups (including cross-linked and condensed rings), aromatic hydrocarbon groups, and hydrocarbon groups in which two or more of these are combined. etc. can be mentioned. The hydrocarbon group or the organic group may include various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, and aryl group, etc.) or functional groups (e.g., ester bond, amide bond, It may have an ether bond, a thioether bond, a urethane bond, etc.).

The organic group represented by the general formula (2) is preferably one of the following organic groups from the viewpoint of obtaining a cured product with excellent scratch resistance and from the viewpoint of sensitivity and developability.

[Formula 7]

Furthermore, in the general formula (2), from the viewpoint of obtaining a cured product with excellent scratch resistance, and from the viewpoint of sensitivity and developability, it is preferable that R ⁵ is an organic group represented by the following general formula (3).

[Formula 8]

(In the formula, R ⁶ and R ⁷ are each independently a parent hydrocarbon group having 1 to 6 carbon atoms, and the total parent carbon number of R ⁶ and R ⁷ is 3 to 8.)

Examples of the hydrocarbon group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups, and alicyclic saturated or unsaturated hydrocarbon groups. The hydrocarbon group may have various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, and aryl group, etc.).

The above R ⁶ and R ⁷ are each independently a hydrocarbon group having a parent carbon number of 1 to 5, and it is preferable that the total parent carbon number of R ⁶ and R ⁷ is 3 to 7.

The organic group represented by the general formula (2) is preferably one of the following organic groups from the viewpoint of obtaining a cured product with excellent scratch resistance and from the viewpoint of sensitivity and developability.

[Formula 9]

In the general formula (1), R ⁴ is a hydroxy group or an organic group bonded to the carbon atom of the linking group of R ² . When R ⁴ is a hydroxy group, developability can be further improved. In addition, when R ⁴ is an organic group, properties derived from the organic group (for example, developability, adhesion, solubility, etc.) can be additionally imparted. The organic group is not particularly limited and includes, for example, a linear or branched aliphatic saturated or unsaturated hydrocarbon group, an alicyclic saturated or unsaturated hydrocarbon group (including cross-linked and condensed rings), an aromatic hydrocarbon group, and the above hydrocarbon group. Examples include organic groups in which some of the constituting carbon atoms are replaced with heteroatoms (for example, oxygen atoms, nitrogen atoms, and sulfur atoms), and organic groups in which two or more of these are bonded. In addition, the hydrocarbon group or the organic group may have various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, and aryl group, etc.) or functional groups (e.g., ester bond, amide bond, etc.) , ether bond, thioether bond, urethane bond, etc.).

From the viewpoint of high refractive index, high water resistance, chemical resistance, etc., the organic group of R ⁴ includes acryloyloxy group, methacryloyloxy group, acyloxy group, amideoxy group, alkoxy group, aryloxy group, It is preferable that it is an organic group containing at least one functional group selected from the group consisting of an amino group and a nitrogen-containing heterocycle, and it is more preferable that it is an acryloyloxy group, a methacryloyloxy group, or an organic group represented by any of the following formulas.

[Formula 10]

(Wherein, R ¹⁰ and R ¹¹ are each independently an organic group described in paragraph [0034].)

In addition, from the viewpoint of obtaining a cured product with excellent scratch resistance and low-temperature curability, R ⁴ is a hydroxy group, an acryloyloxy group, a methacryloyloxy group bonded to the carbon atom of the linking group of R ² or the general formula below: It is preferable that it is an organic group represented by (4).

[Formula 11]

(In the formula, R ⁸ is hydrogen or a methyl group, and R ⁹ is a parent hydrocarbon group having 1 to 5 carbon atoms, or an organic group having 1 to 5 parent carbon atoms and containing a hetero atom.)

In the general formula (4), R ⁹ is a parent hydrocarbon group having 1 to 5 carbon atoms, or a parent hydrocarbon group having 1 to 5 carbon atoms and a hetero atom (for example, an oxygen atom, a nitrogen atom, and a sulfur atom). etc.) is an organic group containing In addition, when the organic group contains a hetero atom, the hetero atom of the organic group is a portion other than the bonding portion with the nitrogen atom of the urethane bond in the general formula (4), and a (meth)acryloyloxy group. It has parts other than the bonding area with the oxygen atom. Examples of the hydrocarbon group include linear or branched aliphatic saturated or unsaturated hydrocarbon groups. The hydrocarbon group or the organic group may include various substituents (e.g., halogen group, hydroxy group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, and aryl group, etc.) or functional groups (e.g., ester bond, amide bond, It may have an ether bond, a thioether bond, a urethane bond, etc.). The above R ⁹ is preferably a parent hydrocarbon group having 1 to 5 carbon atoms, and more preferably an ethylene group or a propylene group.

Monomers that form the basis of repeating structural units other than the repeating structural unit Carboxyl group-containing monomers such as; monomers containing carboxylic anhydride groups such as maleic anhydride and itaconic anhydride; Methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, benzyl (meth)acrylate, lauryl (meth)acrylate, hydroxyethyl (meth)acrylate alkyl (meth)acrylates such as alkyl acrylate, hydroxypropyl (meth)acrylate, ethoxyethyl (meth)acrylate, and glycidyl (meth)acrylate; and alicyclic (meth)acrylates such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and dicyclopentenyl (meth)acrylate. Additionally, styrene, cyclohexyl maleimide, phenyl maleimide, methyl maleimide, ethyl maleimide, n-butyl maleimide, lauryl maleimide, and silicon-containing monomers may be used as copolymerization monomers. These monomers may be used individually, or two or more types may be used in combination.

The alkali-soluble resin of the present invention, for example, is obtained by polymerizing a monomer composition containing an epoxy group-containing (meth)acrylate, and reacting a polymer having an epoxy group in the side chain with a carboxyl group-containing compound to convert it into a side chain having a hydroxy group, And the method (1) of reacting a carboxylic anhydride with the hydroxy group, or reacting a compound having an ethylenically unsaturated group and a carboxyl group to a polymer having an epoxy group in the side chain obtained by polymerizing a monomer composition containing an epoxy group-containing (meth)acrylate. converting it into a side chain having a hydroxy group and an ethylenically unsaturated group, reacting the hydroxy group with a compound having a functional group that reacts with a hydroxy group such as an isocyanate group, and further adding ethylene to the ethylenically unsaturated group, such as a hydroxy group, a thiol group, and an amino group. It can be synthesized by method (2), etc., in which a compound having a carboxyl group and a functional group that reacts with a sexually unsaturated group is reacted.

The alkali-soluble resin may be a homopolymer composed of the repeating structural unit It may be a random copolymer, a block copolymer, an alternating copolymer, or a periodic copolymer composed of one or more types of repeating structural units X and other repeating structural units. From the viewpoint of low-temperature curability, sensitivity and developability, and storage stability, the alkali- ^soluble resin of the present invention comprises a repeating structural unit ³ is preferably a random copolymer containing at least a repeating structural unit X2, which is a hydroxy group bonded to the carbon atom of the linking group.

In the alkali-soluble resin, the content of the repeating structural unit %am.

The weight average molecular weight of the alkali-soluble resin is not particularly limited, but is preferably 5,000 to 40,000 from the viewpoint of sensitivity and developability, and more preferably 6,000 to 30,000. The weight average molecular weight is a value measured using gel permeation chromatography (GPC) in terms of polystyrene conversion, and is a value measured based on JIS 7252-4. The weight average molecular weight described in the examples described later is also a value obtained according to the description in this section.

The acid value of the alkali-soluble resin is not particularly limited, but is preferably 10 to 120 mgKOH/g, more preferably 20 to 80 mgKOH/g, from the viewpoint of enabling development in a short time even when using a weakly alkaline developer. .

The cross-linking agent is not particularly limited as long as it can react with the alkali-soluble resin to form a cross-linked structure, but from the viewpoint of obtaining a cured product with excellent scratch resistance and improving low-temperature curability and photolithography, it may contain two nitrogen atoms. It is preferable that it is a heterocyclic compound having a heterocycle containing the above, more preferably a triazine-based compound and/or its condensate, a glycoluryl-based compound and/or its condensate, and an imidazolidinone-based compound and/or It is at least one type selected from the group consisting of the condensate. In addition, the above compounds or their condensates contain an amino group, an N-(hydroxyalkyl) group, and an N-(alkoxyalkyl) group from the viewpoint of obtaining a cured product with excellent scratch resistance and improving low-temperature curability and photolithographic properties. It is preferable to have one or more functional groups selected from the group consisting of groups, and it is more preferable to have an N-(hydroxyalkyl) group and/or an N-(alkoxyalkyl) group.

Preferred specific examples of the crosslinking agent include fully or partially alkoxy (e.g. methoxy, ethoxy) methylated melamine and/or its condensate, fully or partially alkoxy (e.g. methoxy, ethoxy) methylated guanamine, and /or its condensate, fully or partially alkoxy (e.g. methoxy, ethoxy) methylated acetoguanamine and/or its condensate, fully or partially alkoxy methylated benzoguanamine and/or its condensate, fully or partially Alkoxy (eg, methoxy, ethoxy) methylated glycoluril and/or its condensate, fully or partially alkoxy methylated imidazolidinone and/or its condensate. The 'alkoxy' preferably has 1 to 4 carbon atoms. Preferred specific examples of such crosslinking agents include hexamethoxymethylmelamine, hexaethoxymethylmelamine, tetramethoxymethylmethylolmelamine, tetramethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylguanamine, and tetramethoxymethyl. Acetoguanamine, tetramethoxymethylbenzoguanamine, trimethoxymethylbenzoguanamine, tetraethoxymethylbenzoguanamine, tetramethylolbenzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) Glycoluril, 1,3,4,6-tetrakis(butoxymethyl)glycoluril, 4,5-dihydroxy-1,3-dimethoxymethyl-2-imidazolidinone, 4,5-dimethoxy -1,3-dimethoxymethyl-2-imidazolidinone, etc. are mentioned. These may be used alone, or two or more types may be used together.

In one embodiment, preferably, the crosslinking agent is selected from the group consisting of compounds represented by formula B1 and/or condensates thereof.

[Formula 12]

(In formula B1, R ^1b has 1 to 25 carbon atoms and is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group,

[Formula 13]

A monosubstituted amine represented by and

[Formula 14]

is selected from the group consisting of disubstituted amines represented by, and R ^2b to R ^8b are independently of each other a hydrogen atom, 1 to 10 carbon atoms, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted alkenyl group. (selected from group)

More preferably, the crosslinking agent in formula B1, R ^1b is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group,

[Formula 15]

A monosubstituted amine represented by and

[Formula 16]

is selected from the group consisting of disubstituted amines represented by , and R ^2b to R ^8b are each independently a compound selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and/or a condensate thereof.

In another embodiment, preferably, the crosslinking agent is selected from the group consisting of compounds represented by formula B2 and/or condensates thereof.

[Formula 17]

(In formula B2, R ^9b to R ^12b each independently have 1 to 10 carbon atoms and are selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted alkenyl group.)

More preferably, the crosslinking agent in formula B2 is a compound and/or a condensate thereof, wherein R ^9b to R ^12b are independently selected from substituted or unsubstituted alkyl groups.

In another embodiment, preferably, the crosslinking agent is selected from the group consisting of compounds represented by formula B3 and/or condensates thereof.

[Formula 18]

(In formula B3, R ^13b and R ^14b are each independently selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted alkenyl group, each having 1 to 10 carbon atoms, R ^15b and R ^16b are, independently of each other, hydrogen or have 1 to 10 carbon atoms and are selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted alkenyl group.)

More preferably, the crosslinking agent is, in formula B3, R ^13b and R ^14b are independently selected from substituted or unsubstituted alkyl groups, and R ^15b and R ^16b are independently selected from hydrogen, and substituted or It is a compound selected from the group consisting of unsubstituted alkyl groups and/or a condensate thereof.

More preferably, in formula B3, R ^15b and R ^16b are independently hydrogen.

Specific examples of the crosslinking agent include hexamethoxymethylmelamine, hexabutoxymethylmelamine, 1,3,4,6-tetrakis(methoxymethyl)glycoluril, 1,3,4,6-tetrakis(butoxymethyl) ) glycoluril, tetramethoxymethylbenzoguanamine, 4,5-dihydroxy-1,3-bis (alkoxymethyl) imidazolidin-2-one, and compounds represented by the following structural formulas and/or their A condensate may be mentioned.

[Formula 19]

The condensate preferably includes a polymer of the above compound, and more preferably includes a dimer, trimer, or higher order polymer of the above compound. The crosslinking agent may be the above compound and its condensate, that is, a mixture of the above compound and a polymer (i.e., dimer, trimer or higher order polymer) of the above compound. In another embodiment, the condensate may include at least one of dimers, trimers, and higher order polymers of the compounds. From another viewpoint, the cross-linking agent may have a weight average degree of polymerization relative to the compound greater than 1 and 3 or greater, preferably greater than 1 and 1.8 or less, more preferably 1.3 to 1.8, and even more preferably 1.5. It may have a weight average degree of polymerization of, but is not limited to these. Additionally, when the weight average degree of polymerization in the condensate of the above compound is 1, it means that the condensate is the compound itself. The weight average degree of polymerization is any value within the above range, preferably 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 3, 4 or larger, and more preferably, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, and more preferably 1.5.

The content of the cross-linking agent is not particularly limited, but from the viewpoint of sufficiently obtaining the effect of the present invention, it is preferably 10 to 100 parts by mass, more preferably 20 to 80 parts by mass, based on 100 parts by mass of the alkali-soluble resin. Preferably it is 30 to 50 parts by mass.

The photosensitive resin composition of the present invention preferably further contains an acid catalyst from the viewpoint of promoting the reaction between the alkali-soluble resin and the crosslinking agent. The acid catalyst may be a compound selected from Brønsted acid and/or Lewis acid, a salt thereof, or a solvate thereof. Examples of the acid catalyst include protonic acids or salts thereof such as dinonylnaphthalenedisulfonic acid, dinonylnaphthalene(mono)sulfonic acid, dodecylbenzenesulfonic acid, p-toluenesulfonic acid (PTS), phosphoric acid, sulfuric acid, and acetic acid. Solvates may be included, and are preferably p-toluenesulfonic acid, pyridinium-p-toluenesulfonic acid, or hydrates thereof. These may be used one type, or two or more types may be used together. Additionally, acid catalysts also include compounds that generate acids by light or heat (so-called acid generators). A commercially available acid generator can be used, and typical examples include onium salts containing sulfonium ions or iodonium ions as cation moieties.

The content of the acid catalyst is not particularly limited, but is preferably 0.1 to 5% by mass, more preferably 0.5 to 3% by mass, and even more preferably 1 to 2% by mass, based on the solid content of the photosensitive resin composition.

Although the photosensitive resin composition of this invention may contain a polymerizable monomer, it is preferable not to contain a polymerizable monomer from a viewpoint of storage stability.

The polymerizable monomer is not particularly limited and includes, for example, nonylphenylcarbitol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, and 2-ethylhexylcarbitol (meth)acrylate. monofunctional monomers such as latex, 2-hydroxyethyl (meth)acrylate, and N-vinylpyrrolidone, and polyfunctional aromatic vinyl monomers such as divinylbenzene, diallyl phthalate, and diallylbenzene phosphonate; (di)ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol di(meth)acrylate , pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate ) Acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and tri(meth)acrylate of tris(hydroxyethyl)isocyanurate, etc. multifunctional (meth)acrylate. and multifunctional monomers such as acrylates. These polymerizable monomers may be used individually, or two or more types may be used in combination.

When the photosensitive resin composition contains the polymerizable monomer, the content is preferably 30 to 100 parts by mass, more preferably 40 to 90 parts by mass, and still more preferably 50 parts by mass, based on 100 parts by mass of the alkali-soluble resin. ~80 parts by mass.

The photosensitive resin composition of the present invention may contain a photopolymerization initiator. The photopolymerization initiator is not particularly limited and includes, for example, benzoin and its alkyl ethers such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Acetphenones such as acetphenone, 2,2-dimethoxy-2-phenylacetphenone, and 1,1-dichloroacetphenone; Anthraquinones such as 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; Thioxanthone such as 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone; Ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; Benzophenones such as benzophenone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one or 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone- One; Acylphosphine oxides and xanthone types can be mentioned. These photopolymerization initiators may be used individually, or two or more types may be used in combination.

The content of the photopolymerization initiator is not particularly limited, but is preferably 0.1 to 10% by mass, more preferably 0.5 to 9% by mass, and even more preferably 1 to 8% by mass, based on the solid content of the photosensitive resin composition.

A photopolymerization initiation aid may be added to the photosensitive resin composition. As a photopolymerization initiation aid, for example, 1,3,5-tris(3-mercaptopropionyloxyethyl)-isocyanurate, 1,3,5-tris(3-mercaptobutyloxyethyl)-iso. trifunctional thiol compounds such as cyanurate (Kalens MT (registered trademark) NR1, manufactured by Showa Denko Co., Ltd.) and trimethylolpropanetris (3-mercaptopropionate); Tetrafunctional thiol compounds such as pentaerythritol tetrakis (3-mercaptopropionate) and pentaerythritol tetrakis (3-mercaptobutyrate) (Kalens MT (registered trademark) PEI, manufactured by Showa Denko) ; and polyfunctional thiols such as hexafunctional thiol compounds such as dipentaerythritol hexakis (3-propionate). These photopolymerization initiation aids may be used individually, or two or more types may be used in combination.

A thermal polymerization initiator may be added to the photosensitive resin composition. Examples of thermal polymerization initiators include cumene hydroperoxide, diisopropylbenzene peroxide, di-t-butyl peroxide, lauryl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, and t-butyl. Organic peroxides such as peroxy-2-ethylhexanoate and t-amylperoxy-2-ethylhexanoate; 2,2'-azobis(isobutyronitrile), 1,1'-azobis(cyclohexanecarbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl 2,2 Azo compounds such as '-azobis(2-methylpropionate), etc. can be mentioned. These thermal polymerization initiators may be used individually, or two or more types may be used in combination.

The photosensitive resin composition includes radically polymerizable oligomers such as unsaturated polyester, epoxy acrylate, urethane acrylate, and polyester acrylate; You may add a curable resin such as epoxy resin.

The photosensitive resin composition may contain a solvent. Examples of solvents include ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and 3-methoxybutyl acetate; Alcohols such as methanol, ethanol, isopropanol, n-butanol, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; Aromatic hydrocarbons such as toluene, xylene, and ethylbenzene; Chloroform, dimethyl sulfoxide, etc. can be mentioned. These solvents may be used individually, or two or more types may be used in combination. Additionally, the solvent content may be appropriately set according to the optimal viscosity when using the composition.

The photosensitive resin composition includes fillers such as aluminum hydroxide, talc, clay, and barium sulfate, surface conditioners (surfactants), dyes, pigments, anti-foaming agents, coupling agents, and leveling agents, to the extent that they do not impair the effect of the present invention. It may contain known additives such as agents, sensitizers, mold release agents, lubricants, plasticizers, antioxidants, ultraviolet absorbers, flame retardants, polymerization inhibitors, thickeners, and dispersants.

The photosensitive resin composition of the present invention can form a cured product with excellent scratch resistance and has excellent low-temperature curability and photolithographic properties, so it is preferably used as a resist material.

The cured product of the present invention can be obtained by curing the photosensitive resin composition. As a method of producing the cured product, for example, the photosensitive resin composition is injected into a mold (resin mold), or the photosensitive resin composition is coated on a substrate or various functional layers to form a desired shape. After this, a method of curing the photosensitive resin composition by irradiating light (for example, ultraviolet rays) may be used. The curing conditions are appropriately adjusted depending on the photosensitive resin composition to be used.

The cured product is preferably used as a photo spacer, partition material, lens material, interlayer insulating film material, protective film material, optical waveguide material, or planarization film material, and is particularly preferably used as a photo spacer.

The method of forming the photo spacer is not particularly limited, and for example, the photosensitive resin composition can be applied to a substrate such as glass or a transparent plastic film, dried to form a coating film, and then formed by photolithography. . In photolithography, for example, a photomask is placed on the coating film, the coating film is photocured by irradiating ultraviolet rays, an aqueous alkaline solution is spread on the coating film after ultraviolet irradiation, and the unexposed portion is dissolved and removed. The remaining exposed portion is washed with water and developed to form a photo spacer. After that, post-baking may be performed.

Example

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[Synthesis Example 1] Synthesis of alkali-soluble resin 1

According to the following production method, alkali-soluble resin 1 containing the following repeating structural units X1 and X2 was synthesized.

[Formula 20]

100 g of glycidyl methacrylate and 212 g of propylene glycol monomethyl ether acetate were placed in a glass flask equipped with a heating/cooling/stirring device, a reflux cooling pipe, and a nitrogen introduction pipe. After replacing the gaseous portion in the system with nitrogen, 17 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, heated at 80°C, and allowed to react at this temperature for 8 hours. . To the obtained solution, 53.2 g of acrylic acid, 1.0 g of triphenylphosphine, 0.02 g of hydroquinone, and 6.0 g of propylene glycol monomethyl ether acetate were added and reacted at 100°C for 16 hours. After the reaction, 3.7 g of succinic anhydride and 13.0 g of propylene glycol monomethyl ether acetate were further added to the reaction solution and reacted at 65°C for 6 hours to obtain a solution containing 45% by mass of alkali-soluble resin 1. As a result of measuring the molecular weight by GPC, the weight average molecular weight (Mw) of alkali-soluble resin 1 was 7,000. In addition, molecular weight measurement was performed by gel permeation chromatography (manufactured by Tosoh Corporation, product number: HLC-8120, column: dual connection of G-5000HXL and G-3000HXL, detector: RI, mobile phase: tetrahydrofuran). Hereinafter, the weight average molecular weight was measured using the same method. Additionally, the acid value of alkali-soluble resin 1 was 21 mgKOH/g. The molar ratio (theoretical value) of X1 and X2 is 15:85.

[Synthesis Example 2] Synthesis of alkali-soluble resin 2

In a reaction vessel equipped with a stirring device, a reflux cooling pipe, a nitrogen introduction pipe, and a thermometer, 20.0 g of 2-hydroxyethyl methacrylate and 60.0 g of propylene glycol were placed and dissolved while blowing nitrogen. After heating to 65°C, 2.4 g of 2,2'-azobis(2,4-dimethylvaleronitrile) (ADVN) was added, heated to 65°C, and reacted at this temperature for 8 hours to obtain alkali-soluble resin 2. A solution containing 25% by mass was obtained. As a result of measuring the molecular weight by GPC, the weight average molecular weight (Mw) of alkali-soluble resin 2 was 6,000.

[Synthesis Example 3] Synthesis of alkali-soluble resin 3

In a reaction vessel equipped with a stirring device, a reflux cooling pipe, a nitrogen introduction pipe, and a thermometer, 18.4 g of 2-hydroxyethyl methacrylate, 1.6 g of methacrylic acid, and 60.0 g of propylene glycol were placed and dissolved while blowing nitrogen. After heating to 65°C, 2.4 g of 2,2'-azobis(2,4-dimethylvaleronitrile) (ADVN) was added, heated to 65°C, and reacted at this temperature for 8 hours to obtain alkali-soluble resin 3. A solution containing 25% by mass was obtained. As a result of measuring the molecular weight by GPC, the weight average molecular weight (Mw) of alkali-soluble resin 3 was 6,000.

[Synthesis Example 4] Synthesis of alkali-soluble resin 4

20.0 g of 4-hydroxyphenyl methacrylate and 60.0 g of propylene glycol were placed in a reaction vessel equipped with a stirring device, a reflux cooling pipe, a nitrogen introduction pipe, and a thermometer, and were dissolved while blowing nitrogen. After heating to 65°C, 2.4 g of 2,2'-azobis(2,4-dimethylvaleronitrile) (ADVN) was added, heated to 65°C, and reacted at this temperature for 8 hours to obtain alkali-soluble resin 4. A solution containing 25% by mass was obtained. As a result of measuring the molecular weight by GPC, the weight average molecular weight (Mw) of alkali-soluble resin 4 was 7,000.

Examples 1 to 8 and Comparative Examples 1 to 10

[Preparation of photosensitive resin composition]

For each solution containing alkali-soluble resin 1, 2, 3 or 4, each raw material shown in Table 1 was mixed in the ratio shown in Table 1 to prepare a photosensitive resin composition. In addition, the unit of the numerical value for each component in Table 1 is parts by mass. Mixing was carried out at room temperature and with ultraviolet rays blocked to prevent the polymerization reaction from starting. Each raw material listed in Table 1 is as follows.

<Acrylic monomer>

Monomer 1: Aronics MT-3545 (manufactured by Toagosei, a monomer whose main component has 5 acrylic groups)

Monomer 2: Aronics M-923 (manufactured by Toagosei, a monomer whose main component has an isocyanuric skeleton with two acrylic groups)

Monomer 3: Viscot #802 (manufactured by Osaka Organic Chemical Industry, monomer with 7 to 9 acrylic groups as the main component)

Monomer 4: Light acrylate DCP-A (manufactured by Kyoeisha Chemical, bifunctional monomer having a tricyclo ring)

<Cross-linking agent>

Crosslinking agent 1: MX-750 (manufactured by Sanwa Chemical, melamine having an imino group and a methylol group)

Crosslinking agent 2: MX-730 (manufactured by Sanwa Chemical, melamine with an imino group and an ether-protected methylol group)

Crosslinking agent 3: MW-30 (Melamine with ether-protected methylol group, manufactured by Sanwa Chemical)

Crosslinking agent 4: MW-270 (Sanwa Chemical Co., Ltd., glycoluril with ether-protected methylol group)

Crosslinking agent 5: MX-002 (manufactured by Sanwa Chemical, melamine having an imino group and a methylol group)

<Acid catalyst>

p-toluenesulfonic acid

SP-606 (manufactured by ADEKA, photoacid generator)

<Photopolymerization initiator>

Irgacure OXE01 (manufactured by BASF Japan, optical radical initiator)

<Surface conditioner (surfactant)>

DOWSIL ^TM FZ-2122 (manufactured by Doré and Dow Corning, surfactant)

<Evaluation method>

[Pencil hardness]

Each photosensitive resin composition prepared in Examples 1 to 8 and Comparative Examples 1 to 10 was applied onto each 10 cm x 10 cm square glass substrate using a spin coater so that the finished film thickness was 2.0 μm, and dried using a vacuum dryer ( It was dried under reduced pressure at room temperature using VCD). The coating film was heated on a hot plate at 90°C for 2 minutes to completely remove the solvent. Thereafter, the obtained coating film was irradiated with light from an ultra-high pressure mercury lamp at 60 mJ/cm ² (illuminance at 365 nm: 20 mW/cm ² ). After that, a substrate with a cured film was produced by post-baking at 120°C for 30 minutes. On the obtained substrate with a cured film, a pencil was scratched about 1 cm by applying a weight of 750 g at an angle of 45 degrees, and the hardest point without scratches was taken as the pencil hardness. The pencil hardness is preferably B or higher, more preferably HB or higher, and even more preferably F or higher.

[Patterning phenomenon characteristics (photolithographic properties)]

Each photosensitive resin composition prepared in Examples 1 to 8 and Comparative Examples 1 to 10 was applied onto each 10 cm x 10 cm square glass substrate using a spin coater so that the finished film thickness was 2.0 μm, and dried using a vacuum dryer ( It was dried under reduced pressure at room temperature using VCD). The coating film was heated on a hot plate at 90°C for 2 minutes to completely remove the solvent. Thereafter, the obtained coating film was irradiated with light from an ultra-high pressure mercury lamp at 60 mJ/cm ² through an island-forming mask (illuminance at 365 nm: 20 mW/cm ² ). Additionally, exposure was performed with an interval (exposure gap) between the mask and the substrate of 200 μm. Afterwards, alkaline development was performed for 60 seconds using a developer of 0.5% potassium hydroxide aqueous solution. After washing with water, an island pattern was formed by post-baking at 120°C for 30 minutes. Then, the island pattern formed on the developed substrate was observed using a laser microscope. In addition, the patterning phenomenon characteristics were evaluated based on the following criteria.

○: Island patterns can be created without peeling or shape abnormalities.

△: An island pattern can be created, but peeling or shape abnormalities occur in some parts of the island.

×: Island pattern cannot be created.

[Storage stability]

Each photosensitive resin composition prepared in Example 1 and Comparative Example 2 was kept cool at 5°C for 8 and 24 days, and then the viscosity of each photosensitive resin composition returned to room temperature was measured to determine the viscosity increase rate. The photosensitive resin composition of Example 1 had a viscosity increase rate of 2.5% after 8 days and a viscosity increase rate of 3.4% after 24 days. The photosensitive resin composition of Comparative Example 2 had a viscosity increase rate of 12.9% after 8 days and a viscosity increase rate of 15.7% after 24 days.

[Table 1]

The photosensitive resin composition of the present invention is preferably used as a raw material for photo spacers, partition materials, lens materials, interlayer insulating film materials, protective film materials, optical waveguide materials, or planarization film materials.

Claims (17)

A photosensitive resin composition comprising an alkali-soluble resin containing at least one type of repeating structural unit X represented by the following general formula (1), and a crosslinking agent.
[Formula 1]

(In the formula, R ¹ is hydrogen or a methyl group, R ² is a linking group having 1 or more carbon atoms, R ³ is an organic group or hydroxy group represented by the following general formula (2) bonded to the carbon atom of the linking group, and R ⁴ is It is a hydroxy group or an organic group bonded to the carbon atom of the linking group.)
[Formula 2]

(In the formula, R ⁵ is a hydrocarbon group having a parent carbon number of 2 to 7, an organic group having a parent carbon number of 3 to 8 and containing a hetero atom, or an organic group having a parent carbon number of 2 to 7 and also having a carboxyl group. am.) According to paragraph 1,
The photosensitive resin composition wherein the linking group for R ² is a hydrocarbon group having a parent carbon number of 1 to 10, or an organic group having a parent carbon number of 1 to 10 and containing a hetero atom. According to paragraph 1,
The organic group of R ⁴ is one or more functional groups selected from the group consisting of an acryloyloxy group, methacryloyloxy group, acyloxy group, amideoxy group, alkoxy group, aryloxy group, amino group, and nitrogen-containing heterocycle. A photosensitive resin composition containing an organic group. According to paragraph 1,
The linking group of R ² is a hydrocarbon group having a parent carbon number of 1 to 7, or an organic group having a parent carbon number of 1 to 7 and containing a hetero atom,
R ⁴ is a hydroxy group, an acryloyloxy group, or a methacryloyloxy group bonded to the carbon atom of the linking group of R ² ,
The photosensitive resin composition wherein R ⁵ is a hydrocarbon group having a parent carbon number of 2 to 7, or an organic group having a parent carbon number of 2 to 7 and a carboxyl group. According to paragraph 1,
The linking group of R ² is a hydrocarbon group having a parent carbon number of 1 to 7, or an organic group having a parent carbon number of 1 to 7 and containing a hetero atom,
Said R ⁵ is an organic group represented by the following general formula (3),
The photosensitive resin composition wherein R ⁴ is a hydroxy group, an acryloyloxy group, a methacryloyloxy group, or an organic group represented by the following general formula (4) bonded to the carbon atom of the linking group of R ² .
[Formula 3]

(In the formula, R ⁶ and R ⁷ are each independently a parent hydrocarbon group having 1 to 6 carbon atoms, and the total parent carbon number of R ⁶ and R ⁷ is 3 to 8.)
[Formula 4]

(In the formula, R ⁸ is hydrogen or a methyl group, and R ⁹ is a parent hydrocarbon group having 1 to 5 carbon atoms, or an organic group having 1 to 5 parent carbon atoms and containing a hetero atom.) According to paragraph 1,
In the alkali-soluble resin, the content of the repeating structural unit X is 5 to 50 mol% based on all repeating structural units. According to paragraph 1,
The alkali-soluble resin is a photosensitive resin composition having an acid value of 10 to 120 mgKOH/g. According to paragraph 1,
The alkali-soluble resin is a photosensitive resin composition having a weight average molecular weight of 5000 to 40000. According to paragraph 1,
The photosensitive resin composition wherein the crosslinking agent is a heterocyclic compound having a heterocycle containing two or more nitrogen atoms. According to clause 9,
The heterocyclic compound is a photosensitive compound, which is at least one selected from the group consisting of triazine-based compounds and/or their condensates, glycoluril-based compounds and/or their condensates, and imidazolidinone-based compounds and/or their condensates. Resin composition. According to clause 9,
A photosensitive resin composition, wherein the heterocyclic compound has at least one functional group selected from the group consisting of an amino group, an N-(hydroxyalkyl) group, and an N-(alkoxyalkyl) group. According to paragraph 1,
The photosensitive resin composition wherein the content of the crosslinking agent is 10 to 100 parts by mass with respect to 100 parts by mass of the alkali-soluble resin. According to paragraph 1,
A photosensitive resin composition containing an acid catalyst. According to paragraph 1,
The photosensitive resin composition is a resist material. A cured product obtained from the photosensitive resin composition according to any one of claims 1 to 14. According to clause 15,
The cured product is a photo spacer, a partition material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarization film material. An image display device comprising the cured product according to claim 15.