JP7826658B2 - Photosensitive composition, cured film using the same, optical filter, image display device, solid-state imaging device, and infrared sensor - Google Patents

Description

The present invention relates to a photosensitive composition, a cured film using the same, an optical filter, an image display device, a solid-state imaging device, and an infrared sensor.

Video cameras, digital cameras, and mobile devices with camera functions use solid-state color imaging elements such as CCDs (charge-coupled devices) and CMOSs (complementary metal-oxide semiconductors). The light-receiving section of these solid-state imaging elements uses silicon photodiodes that are sensitive to infrared light, so visibility correction is required, and an infrared-cutting filter or similar is used. Infrared-cutting filters are manufactured using, for example, compositions containing infrared-absorbing compounds.

Traditionally, infrared cut filters have been used as flat films, but in recent years, studies have been conducted to form patterns of infrared cut filters using photolithography. However, the infrared-absorbing compounds used in infrared cut filters and the like have low heat resistance, which poses a problem in that their near-infrared absorption ability decreases during the heating process (post-baking) that occurs during pattern formation. On the other hand, films with high heat resistance have problems with poor developability and pattern formation ability.

Various efforts have been made to solve the above problems. For example, Patent Document 1 discloses a thermosetting resin composition containing two types of cyanine compounds, an epoxy resin with a specific structure, and an epoxy resin curing agent as a resin composition that can be used to produce an infrared cut filter with excellent processability and heat resistance. Furthermore, Patent Documents 2 and 3 disclose photosensitive resin compositions for near-infrared absorbers that can produce fine patterns, containing a phthalocyanine compound with an absorption maximum wavelength in the near-infrared region, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

JP 2015-34252 A JP 2010-160380 A International Publication No. 2020/054719

However, none of the compositions described in Patent Documents 1, 2, and 3 satisfy all of the requirements for developability, pattern formability, and heat resistance.

The objective of the present invention is to provide a photosensitive composition that can form a cured film with excellent developability, pattern formability, and heat resistance.

The present invention relates to a photosensitive composition comprising an infrared-absorbing compound (A), an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and a benzophenone-based sensitizer (E), wherein the content of the benzophenone-based sensitizer (E) is 100 to 500 parts by mass per 100 parts by mass of the photopolymerization initiator (D).

The present invention provides a photosensitive composition that can form a cured film that has excellent developability, pattern formability, and heat resistance. The present invention also provides cured films, optical filters, image display devices, solid-state imaging devices, and infrared sensors.

FIG. 1 is a schematic cross-sectional view of an image display device provided with the cured film of the present invention. FIG. 2 is a schematic cross-sectional view of a solid-state imaging device provided with the cured film of the present invention. FIG. 3 is a schematic cross-sectional view of an infrared sensor provided with the cured film of the present invention.

The following describes in detail embodiments of the photosensitive composition of the present invention. Note that the present invention is not limited to the following embodiments, and can be modified within the scope of the problems that can be solved.

In the present invention, unless otherwise specified, "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" means "acryloyl and/or methacryloyl", "acrylic and/or methacrylic", "acrylic acid and/or methacrylic acid", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide", respectively. Furthermore, "C.I." means Color Index (C.I.; published by The Society of Dyers and Colourists). The polymerizable unsaturated group is an ethylenically unsaturated double bond.
The molecular weight of the compound in the present invention is a calculated value or a molecular weight measured by ESI-MS (electrospray ionization mass spectrometry) for low molecular weight compounds whose molecular weight can be specified, and is a polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography using tetrahydrofuran as a solvent for compounds having a molecular weight distribution.
A monomer is a compound that can form a resin by polymerization. A monomer refers to a compound having a polymerizable unsaturated group, and a monomer unit refers to a partial structure of the resin after polymerization that is derived from the monomer.

<Photosensitive composition>
One embodiment of the present invention is a photosensitive composition, which comprises an infrared absorbing compound (A), an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and a benzophenone-based sensitizer (E), wherein the content of the benzophenone-based sensitizer (E) is 100 to 500 parts by mass relative to 100 parts by mass of the photopolymerization initiator (D).

The components that are or can be included in one embodiment of the photosensitive composition are described in detail below.

[Infrared absorbing compound (A)]
The photosensitive composition of the present invention contains an infrared absorbing compound (A).

The infrared absorbing compound (A) is a compound having an absorption maximum in a wavelength range of 700 to 2,000 nm, and may be a pigment (also referred to as a near-infrared absorbing pigment) or a dye (also referred to as a near-infrared absorbing dye). Alternatively, a near-infrared absorbing pigment and a near-infrared absorbing dye may be used in combination. From the viewpoint of heat resistance, a near-infrared absorbing pigment is preferred.
In the present invention, the near-infrared absorbing pigment preferably has a solubility in 100 g of propylene glycol monomethyl ether acetate at 25° C. of less than 2 g, more preferably less than 1 g, and particularly preferably 0.5 g or less.

Examples of the infrared absorbing compound (A) include cyanine compounds, phthalocyanine compounds, naphthalocyanine compounds, indigo compounds, immonium compounds, anthraquinone compounds, pyrrolopyrrole compounds, squarylium compounds, and croconium compounds. Among these, from the viewpoint of heat resistance, naphthalocyanine compounds, pyrrolopyrrole compounds, and squarylium compounds are preferred, and naphthalocyanine compounds and squarylium compounds are more preferred.

Cyanine compounds are described in WO 2006/006573, WO 2010/073857, JP 2013-241598, JP 2016-113501, JP 2016-113504, etc.; phthalocyanine compounds are described in JP 4-23868, JP 06-192584, JP 2000-63691 Naphthalocyanine compounds are described in JP-A-11-152414, JP-A-2000-86919, JP-A-2009-29955, JP-A-2018/186490, etc.; indigo compounds are described in JP-A-2013-230412, etc.; immonium compounds are described in JP-A-2005-3361 Anthraquinone compounds are disclosed in JP-A-62-903 and JP-A-1-172458, etc.; pyrrolopyrrole compounds are disclosed in JP-A-2009-263614, JP-A-2010-90313 and JP-A-2011-068731; squarylium compounds are disclosed in JP-A-2009-263614, JP-A-2010-90313 and JP-A-2011-068731, etc. Examples of compounds include those described in JP 2011-132361 A, JP 2016-142891 A, WO 2017/135359 A, WO 2018/225837 A, JP 2019-001987 A, WO 2020/054718 A, etc.; examples of croconium compounds include those described in WO 2019/021767 A, etc.

(Squarylium compounds)
The squarylium compound is preferably a compound represented by the following general formula (2).
General formula (2)

(In general formula (2), R ¹ to R ⁴ each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, —OR ¹⁰ , —COR ¹¹ , —COOR ¹² , —OCOR ¹³ , —NR ¹⁴ R ¹⁵ , —NHCOR ¹⁶ , —CONR ¹⁷ R ¹⁸ , —NHCONR ¹⁹ R ²⁰ , —NHCOOR ²¹ , —SR ²² , —SO ₂ R ²³ , —SO ₂ OR ²⁴ , —NHSO ₂ R ²⁵ , —SO ₂ NR ²⁶ R ²⁷ , —B(OR ²⁸ ) ₂ , and —NHBR ²⁹ R ^30. R ^{R 10} to R ³⁰ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. When R ¹² of -COOR ¹² is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carbonate group) or may be in the form of a salt. When R ²⁴ of -SO ₂ OR ²⁴ is a hydrogen atom (i.e., a sulfo group), the hydrogen atom may be dissociated (i.e., a sulfonate group) or may be in the form of a salt. R ¹ and R ² , and R ³ and R ⁴ may be bonded to each other to form a ring.

Examples of the substituent include a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group,
Examples thereof include —OR ¹⁰⁰ , —COR ¹⁰¹ , —COOR ¹⁰² , —OCOR ¹⁰³ , —NR ¹⁰⁴ R ¹⁰⁵ , —NHCOR ¹⁰⁶ , —CONR ¹⁰⁷ R ¹⁰⁸ , —NHCONR ¹⁰⁹ R ¹¹⁰ , —NHCOOR ¹¹¹ , —SR ¹¹² , —SO ₂ R ¹¹³ , —SO ₂ OR ¹¹⁴ , —NHSO ₂ R ¹¹⁵ and —SO ₂ NR ¹¹⁶ R ¹¹⁷ .
R ¹⁰⁰ to R ¹¹⁷ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. When R ¹⁰² of -COOR ¹⁰² is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carbonate group) or may be in the form of a salt. When R ¹¹⁴ of -SO ₂ OR ¹¹⁴ is a hydrogen atom (i.e., a sulfo group), the hydrogen atom may be dissociated (i.e., a sulfonate group) or may be in the form of a salt.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, and particularly preferably 1 to 8. The alkyl group may be linear, branched, or cyclic.
The number of carbon atoms in the alkenyl group is preferably from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8. The alkenyl group may be linear, branched, or cyclic.
The number of carbon atoms in the alkynyl group is preferably from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8. The alkynyl group may be linear, branched, or cyclic.
The aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 15 carbon atoms, and particularly preferably 6 to 10 carbon atoms.
The alkyl portion of the aralkyl group is the same as the alkyl group described above. The aryl portion of the aralkyl group is the same as the aryl group described above. The aralkyl group preferably has 7 to 40 carbon atoms, more preferably 7 to 30 carbon atoms, and particularly preferably 7 to 25 carbon atoms.
The heteroaryl group is preferably a monocyclic ring or a fused ring, more preferably a monocyclic ring or a fused ring having 2 to 8 rings, and particularly preferably a monocyclic ring or a fused ring having 2 to 4 rings. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3. The heteroatom constituting the ring of the heteroaryl group is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. The heteroaryl group is preferably a 5-membered or 6-membered ring. The number of carbon atoms constituting the ring of the heteroaryl group is preferably 3 to 30, more preferably 3 to 18, and particularly preferably 3 to 12.
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, and aralkyl group may have a substituent or may be unsubstituted. Examples of the substituent include the "substituents" described above.

From the viewpoint of light resistance and heat resistance, the squarylium compound is more preferably a compound represented by the following general formula (3).
General formula (3)

(In general formula (3), R ⁵ to R ⁸ each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, —OR ⁵⁰ , —COR ⁵¹ , —COOR ⁵² , —OCOR ⁵³ , —NR ⁵⁴ R ⁵⁵ , —NHCOR ⁵⁶ , —CONR ⁵⁷ R ⁵⁸ , —NHCONR ⁵⁹ R ⁶⁰ , —NHCOOR ⁶¹ , —SR ⁶² , —SO ₂ R ⁶³ , —SO ₂ OR ⁶⁴ , —NHSO ₂ R ⁶⁵ or —SO ₂ NR ⁶⁶ R ⁶⁷ , —B(OR ⁶⁸ ) ₂ , and —NHBR ⁶⁹ R ^70. R ^{R 50} to R ⁷⁰ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. When R ⁵² of -COOR ⁵² is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carbonate group) or the group may be in the form of a salt. When R ⁶⁴ of -SO ₂ OR ⁶⁴ is a hydrogen atom (i.e., a sulfo group), the hydrogen atom may be dissociated (i.e., a sulfonate group) or the group may be in the form of a salt. R ⁵ and R ⁶ , and R ⁷ and R ⁸ may be bonded to each other to form a ring.

"Substituent" has the same meaning as "substituent" above.

Specific examples of squarylium compounds are shown below. However, the present invention is not limited to these.

(Pyrrolopyrrole Compound)
The pyrrolopyrrole compound is preferably a compound represented by the following general formula (4).

General formula (4)

(In general formula (4), R ^1x and R ^1y each independently represent an alkyl group, an aryl group, or a heteroaryl group, R ² and R ³ each independently represent a hydrogen atom or a substituent, R ² and R ³ may be bonded to each other to form a ring, R ⁴ represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -BR ^4x R ^4y , or a metal atom, R ⁴ may be covalently bonded or coordinately bonded to at least one selected from the group consisting of R ^1x , R ^1y , and R ³ , and R ^4x R ^4y each independently represent a substituent. General formula (4) is described in JP 2009-263614 A, JP 2011-68731 A, and WO 2015/166873.

R ^1x and R ^1y are each independently preferably an aryl group or a heteroaryl group, and more preferably an aryl group. The alkyl groups, aryl groups, and heteroaryl groups represented by R ^1x and R ^1y may have a substituent or may be unsubstituted. Examples of the substituent include an alkoxy group, a hydroxy group, a halogen atom, a cyano group, a nitro group, -OCOR ¹¹ , -SOR ¹² , and -SO ₂ R ^{13. R 11} to R ¹³ each independently represent a hydrocarbon group or a heteroaryl group. Examples of the substituent include the substituents described in paragraphs 0020 to 0022 of JP 2009-263614 A. Among these, preferred examples of the substituent include an alkoxy group, a hydroxy group, a halogen atom, a cyano group, a nitro group, -OCOR ¹¹ , -SOR ¹² , and -SO ₂ R ¹³ . The groups represented by R ^1x and R ^1y are preferably alkoxy groups having a branched alkyl group, or aryl groups having a group represented by —OCOR ¹¹ as a substituent. The branched alkyl group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms.

At least one of ^R2 and ^R3 is preferably an electron-withdrawing group, and more preferably ^R2 represents an electron-withdrawing group and ^R3 represents a heteroaryl group. The heteroaryl group is preferably a 5- or 6-membered ring. The heteroaryl group is preferably a monocyclic or fused ring, preferably a monocyclic or fused ring having 2 to 8 rings, and more preferably a monocyclic or fused ring having 2 to 4 rings. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3, more preferably 1 to 2. Examples of heteroatoms include a nitrogen atom, an oxygen atom, and a sulfur atom. The heteroaryl group preferably has one or more nitrogen atoms. The ^two R2s in general formula (4) may be the same or different. The two ^R3s in general formula (4) may be the same or different.

^R4 is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a group represented ^{by -BR4xR4y} , more preferably a hydrogen atom, an alkyl group, an aryl group, or a group represented by ^{-BR4xR4y ,} and particularly preferably a group represented by ^-BR4xR4y . The substituent represented by ^R4xR4y is preferably a halogen atom, ^an alkyl ^group , an alkoxy group, an aryl group, or a heteroaryl group, more preferably an alkyl group, an aryl group, or a heteroaryl group, and particularly preferably an aryl group. These groups may further have a substituent. The two ^R4s in general formula (4) may be the same or different.

Specific examples of pyrrolopyrrole compounds are shown below. In the following structural formulas, Me represents a methyl group, and Ph represents a phenyl group. Examples of pyrrolopyrrole compounds include the compounds described in paragraphs [0016] to [0058] of JP 2009-263614 A, paragraphs [0037] to [0052] of JP 2011-68731 A, paragraphs [0014] to [0027] of JP 2014-130343 A, and paragraphs [0010] to [0033] of WO 2015/166873 A. However, the present invention is not limited to these.

(Naphthalocyanine compounds)
The naphthalocyanine compound is preferably a compound represented by the following general formula (5).

General formula (5)

(In general formula (5), R ¹ to R ²⁴ each independently represent a halogen atom, a nitro group, a nitrile group, a carboxyl group, a sulfone group, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, an arylthio group which may have a substituent, an alkylamino group which may have a substituent, an arylamino group which may have a substituent, or a sulfamoyl group which may have a substituent.)
Z is a polymer moiety containing a monomer unit represented by general formula (6) or a phosphorus compound moiety represented by general formula (7), and * is a bond to Al.

General formula (6)

(In general formula (6), X represents —CONH—R ²⁵ —, —COO—R ²⁶ —, —CONH—R ²⁷ —O—, —COO—R ²⁸ —O—, R ²⁵ to R ²⁸ represent an alkylene group or an arylene group in which carbon atoms may be linked by —O—, —CO—, —COO—, —OCO—, —CONH—, or —NHCO—; and R ³¹ represents hydrogen or a methyl group.)

General formula (7)

(In general formula (7), R ²⁹ and R ³⁰ each independently represent a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryloxy group which may have a substituent, and R ²⁹ and R ³⁰ may be bonded to each other to form a ring.)

Specific examples of naphthalocyanine compounds are shown below, but the present invention is not limited to these.

The infrared absorbing compound (A) can be used alone or in combination of two or more types. When two or more types are used in combination, it is preferable to use at least two compounds with different maximum absorption wavelengths. This broadens the waveform of the absorption spectrum compared to when a single type of infrared absorbing compound (A) is used, allowing near-infrared radiation to be absorbed over a wide wavelength range.

From the viewpoint of near-infrared absorption, the content of the infrared absorbing compound (A) is preferably 1 to 15 parts by mass, and more preferably 4 to 12 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Alkali-soluble resin (B)]
The photosensitive composition of the present invention contains an alkali-soluble resin (B). This allows for the formation of a cured film with excellent developability, pattern formability, and heat resistance. The alkali-soluble resin (B) may be any resin that dissolves in an alkaline developer, and any known resin may be used.

(Alkali-soluble resin (B1))
The photosensitive composition of the present invention preferably contains, as the alkali-soluble resin (B), an alkali-soluble resin (B1) containing an alicyclic hydrocarbon-containing monomer unit (b1) having a homopolymer glass transition temperature (hereinafter also referred to as Tg) of 80°C or higher and an aromatic ring-containing monomer unit (b2) having a homopolymer glass transition temperature of 80°C or higher.

The Tg may be a measured Tg obtained by actual measurement. Specifically, the measured Tg may be a value measured by differential scanning calorimetry (DSC).
However, if measurement is difficult due to decomposition of the resin, the calculated Tg obtained by the following formula is applied.
1/Tg=W ₁ /Tg ₁ +W ₂ /Tg ₂ +...+W _n /Tg _n
Here, the resin to be calculated is assumed to be a copolymer of n types of monomer components _W1 to _Wn , where _Wn is the weight fraction of the nth monomer, and _Tgn is the glass transition temperature (absolute temperature) of the homopolymer of the nth monomer. The glass transition temperature of the homopolymer of each monomer (hereinafter also referred to as homopolymer) is the value shown in "Polymer Handbook, Third Edition, John Wiley & Sons, 1989" edited by Brandrup, J., and Immergut, E. H.
When two or more alicyclic hydrocarbon-containing monomers or two or more aromatic ring-containing monomers are used, the Tg of the homopolymer of at least one alicyclic hydrocarbon-containing monomer is 80°C, and the Tg of the homopolymer of at least one aromatic ring-containing monomer is 80°C.

[Alicyclic hydrocarbon-containing monomer unit (b1) having a homopolymer glass transition temperature of 80°C or higher]
Examples of monomers forming the alicyclic hydrocarbon-containing monomer unit (b1) having a homopolymer glass transition temperature of 80° C. or higher include isobornyl acrylate, isobornyl methacrylate, adamantyl acrylate, adamantyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2-ethyl-2-adamantyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, dicyclopentanyl acrylate, dicyclopentanyl methacrylate, etc. Of these, isobornyl methacrylate, adamantyl methacrylate, and dicyclopentanyl methacrylate are preferred.

[Aromatic ring-containing monomer unit (b2) having a homopolymer glass transition temperature of 80°C or higher]
Examples of the monomer forming the aromatic ring-containing monomer unit (b2) having a homopolymer glass transition temperature of 80° C. or higher include styrene, α-methylstyrene, vinylnaphthalene, etc. Among these, styrene and α-methylstyrene are preferred.

From the viewpoint of pattern formability and heat resistance, the total content of the alicyclic hydrocarbon-containing monomer unit (b1) and the aromatic ring-containing monomer unit (b2) is preferably 10 to 90 mol %, and more preferably 40 to 80 mol %, of all structural units of the alkali-soluble resin (B1).

From the viewpoints of pattern formability and heat resistance, the ratio of the alicyclic hydrocarbon-containing monomer unit (b1) to the aromatic ring-containing monomer unit (b2) is preferably 20:80 to 80:20, and more preferably 40:60 to 60:40.

[Polymerizable unsaturated group-containing monomer unit (b3)]
From the viewpoint of pattern formability and heat resistance, the alkali-soluble resin (B1) preferably contains a polymerizable unsaturated group-containing monomer unit (b3).

Methods for incorporating polymerizable unsaturated group-containing monomer units (b3) into alkali-soluble resin (B1) include, for example, methods (i) to (iii) shown below.

<Method (i)>
There is a method (i) in which the alkali-soluble resin (B1) has an epoxy group-containing monomer unit, and a carboxyl group of a carboxyl group-containing monomer is added to the epoxy group of the epoxy group-containing monomer unit.

Examples of monomers that form epoxy group-containing monomer units include glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate. Of these, glycidyl (meth)acrylate is preferred from the standpoint of reactivity.

Examples of carboxyl group-containing monomers include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid. Of these, acrylic acid and methacrylic acid are preferred.

From the standpoint of developability, a unit obtained by adding a carboxyl group of a carboxyl group-containing monomer to the epoxy group of an epoxy group-containing monomer unit and then reacting this with an acid anhydride is also useful as the polymerizable unsaturated group-containing monomer unit (b3).

Examples of acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride.

<Method (ii)>
There is a method (ii) in which the alkali-soluble resin (B1) has a carboxyl group-containing monomer unit, and an epoxy group of an epoxy group-containing monomer is added to the carboxyl group of the carboxyl group-containing monomer unit.

<Method (iii)>
There is a method (iii) in which the alkali-soluble resin (B1) has a hydroxyl group-containing monomer unit, and the hydroxyl group of the hydroxyl group-containing monomer unit is reacted with an isocyanate group of an isocyanate group-containing monomer.

Examples of hydroxyl group-containing monomers include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3-, or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate.

Examples of isocyanate group-containing monomers include 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, and 1,1-bis[methacryloyloxy]ethyl isocyanate.

From the viewpoints of pattern formability and heat resistance, the content of the polymerizable unsaturated group-containing monomer unit (b3) is adjusted so that the double bond equivalent of the alkali-soluble resin (B1) is preferably from 200 to 1,000, more preferably from 200 to 800, and particularly preferably from 200 to 700.
The double bond equivalent is the weight per mole of the ethylenically unsaturated double bond in the resin, and can be calculated by the following formula.
Double bond equivalent weight = weight of resin (g) / amount of ethylenically unsaturated double bonds in resin (mol)

[Other monomer units (b4)]
The alkali-soluble resin (B1) may contain other monomer units (b4) in addition to (b1) to (b3).

Examples of the monomer forming the other monomer unit (b4) include (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, and ethoxypolyethylene glycol (meth)acrylate;
hydroxyl group-containing (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2-, 3-, or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate;
Polyether mono(meth)acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to a hydroxyalkyl(meth)acrylate, and polyester mono(meth)acrylates obtained by addition of poly(γ-valerolactone), poly(ε-caprolactone), and/or poly(12-hydroxystearic acid);
epoxy group-containing (meth)acrylates such as glycidyl (meth)acrylate, methyl glycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate;
Unsaturated carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid;
(meth)acrylamides such as (meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, diacetone(meth)acrylamide, or acryloylmorpholine;
vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether;
vinyl fatty acid vinyl compounds such as vinyl acetate or vinyl propionate;
Phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimidocoumarin, 4,4'-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, N,N'-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N-(1-pyrenyl)maleimide, N-(2,4,6-trichlorophenyl)maleimide N-substituted maleimides such as N-(4-aminophenyl)maleimide, N-(4-nitrophenyl)maleimide, N-benzylmaleimide, N-bromomethyl-2,3-dichloromaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-[4-(2-benzimidazolyl)phenyl]maleimide, and 9-maleimidoacridine;
Examples thereof include phosphate group-containing (meth)acrylates such as 2-(meth)acryloyloxyethyl acid phosphate and compounds obtained by reacting the hydroxyl group of the above-mentioned hydroxyl group-containing (meth)acrylate with a phosphate esterifying agent such as phosphorus pentoxide or polyphosphoric acid.

From the viewpoints of pattern formability and heat resistance, the content of alkali-soluble resin (B1) is preferably 40 parts by mass or more, and more preferably 60 parts by mass or more, per 100 parts by mass of alkali-soluble resin (B).

The alkali-soluble resin (B1) can be used alone or in combination of two or more types.

From the viewpoint of heat resistance, the weight average molecular weight (Mw) of the alkali-soluble resin (B1) is preferably 5,000 to 40,000, and more preferably 5,000 to 30,000.

From the viewpoint of developability, the acid value of the alkali-soluble resin (B1) is preferably 20 to 80 mgKOH/g, more preferably 30 to 65 mgKOH/g, and particularly preferably 40 to 60 mgKOH/g.

(Alkali-soluble resin (B2))
The photosensitive composition of the present invention may contain, as the alkali-soluble resin (B), an alkali-soluble resin (B2) other than the alkali-soluble resin (B1) within a range that does not impair the effects of the present invention.

The content of alkali-soluble resin (B) is preferably 1 to 80 parts by mass, more preferably 5 to 60 parts by mass, and even more preferably 10 to 50 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Polymerizable compound (C)]
The photosensitive composition of the present invention contains a polymerizable compound (C).

Examples of the polymerizable compound (C) include monomers and oligomers having a photopolymerizable unsaturated group. Examples of the photopolymerizable unsaturated group include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, and (meth)acryloyloxy groups. Examples of the polymerizable compound (C) include lactone-modified polymerizable compounds, polymerizable compounds having an acid group, polymerizable compounds having a hydroxyl group, polymerizable compounds having a urethane bond, and other polymerizable compounds.

(Lactone-modified polymerizable compound)
From the viewpoint of heat resistance, the photosensitive composition of the present invention preferably contains a lactone-modified polymerizable compound.

A lactone-modified polymerizable compound is a compound that has a lactone-modified structure within the molecule. Lactone-modified polymerizable compounds can be obtained by esterifying a polyhydric alcohol such as trimethylolethane, ditrimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaethylthritol, tripentaerythritol, glycerin, diglycerol, or trimetrolmelamine with (meth)acrylic acid and ε-caprolactone or another lactone compound. The lactone-modified polymerizable compound is preferably a compound represented by the following general formula (8):

General formula (8)

In general formula (8), all six R's are groups represented by the following general formula (9), or one to five of the six R's are groups represented by the following general formula (9), and the remaining are groups represented by the following general formula (10).

General formula (9)

In general formula (9), R ¹ represents a hydrogen atom or a methyl group, m is an integer of 1 or 2, and * represents a bond to the oxygen atom of general formula (8).

General formula (10)

In general formula (10), R ¹ represents a hydrogen atom or a methyl group, and * represents a bond to the oxygen atom of general formula (8).

Lactone-modified polymerizable compounds are commercially available as the KAYARAD DPCA series manufactured by Nippon Kayaku Co., Ltd., and examples thereof include DPCA-20 (a compound in which m=1 in the above general formulas (8) to (10), the number of groups represented in general formula (9)=2, and all R ^1s are hydrogen atoms), DPCA-30 (a compound in which m=1 in the above general formulas (8) to (10), the number of groups represented in general formula (9)=3, and all R ^1s are hydrogen atoms), DPCA-60 (a compound in which m=1 in the above general formulas (8) to (10), the number of groups represented in general formula (9)=6, and all R ^1s are hydrogen atoms), and DPCA-120 (a compound in which m=2 in the above general formulas (8) to (10), the number of groups represented in general formula (9)=6, and all R ^1s are hydrogen atoms).

From the viewpoint of coating film resistance, the lactone-modified polymerizable compound is preferably a compound in which, in the above general formulas (8) to (10), m=1, the number of groups represented by general formula (9)=2 to 6, and all of R ¹ 's are hydrogen atoms, and more preferably a compound in the above general formulas (8) to (10), m=1, the number of groups represented by general formula (9)=2 or 3, and all of R ¹ 's are hydrogen atoms.

From the viewpoint of heat resistance, the content of the lactone-modified polymerizable compound is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, and even more preferably 20 to 60 parts by mass, per 100 parts by mass of polymerizable compound (C).

(Polymerizable Compound Having an Acid Group)
From the viewpoint of developability and pattern formability, the photosensitive composition of the present invention preferably contains a polymerizable compound having an acid group. Examples of the acid group of the polymerizable compound having an acid group include a sulfonic acid group, a carboxyl group, and a phosphate group. Among these, a carboxyl group is preferred.

Examples of the polymerizable compound having an acid group include esters of dicarboxylic acids and free hydroxyl group-containing poly(meth)acrylates of polyhydric alcohols and (meth)acrylic acid; and esters of polycarboxylic acids and monohydroxyalkyl(meth)acrylates.
Examples of polyhydric alcohols include ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, and dipentaerythritol.
Examples of dicarboxylic acids include malonic acid, succinic acid, maleic acid, glutaric acid, phthalic acid, itaconic acid, and the like.
Examples of polycarboxylic acids include trimellitic acid and pyromellitic acid.
Examples of monohydroxyalkyl (meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, pentaerythritol triacrylate, and 2-hydroxy-3-acryloyloxypropyl methacrylate.

Commercially available polymerizable compounds having an acid group include Viscoat #2500P manufactured by Osaka Organic Chemical Industry Co., Ltd., and Aronix M-5300, M-5400, M-5700, M-510, M-520, and M-521 manufactured by Toagosei Co., Ltd.

From the viewpoint of developability and pattern formability, the content of the polymerizable compound having an acid group is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, and even more preferably 20 to 60 parts by mass, per 100 parts by mass of the polymerizable compound (C).

(Polymerizable compound having a hydroxyl group)
From the viewpoint of developability and pattern formability, the photosensitive composition of the present invention preferably contains a polymerizable compound having a hydroxyl group.

Examples of polymerizable compounds having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, reaction products of epoxy group-containing compounds and carboxy(meth)acrylate, and hydroxyl group-containing polyol polyacrylate.

From the viewpoint of developability and pattern formability, the content of the polymerizable compound having a hydroxyl group is preferably 1 to 80 parts by mass, more preferably 5 to 70 parts by mass, and even more preferably 10 to 60 parts by mass, per 100 parts by mass of polymerizable compound (C).

(Polymerizable compound having a urethane bond)
From the viewpoint of pattern formability, the photosensitive composition of the present invention preferably contains a polymerizable compound having a urethane bond as the polymerizable compound (C).

Examples of polymerizable compounds having a urethane bond include urethane (meth)acrylates obtained by reacting a (meth)acrylate having a hydroxyl group with a polyfunctional isocyanate, and urethane (meth)acrylates obtained by reacting a polyhydric alcohol with a polyfunctional isocyanate and then reacting it with a (meth)acrylate having a hydroxyl group.

Examples of the (meth)acrylate having a hydroxyl group include the polymerizable compounds having a hydroxyl group.

Examples of the polyfunctional isocyanate include aromatic diisocyanates such as tolylene diisocyanate, diphenylmethylene diisocyanate, and xylene diisocyanate; aliphatic diisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate; and their biuret derivatives, isocyanate nurate derivatives, and trimethylolpropane adducts.

From the viewpoint of developability, it is also preferable that the polymerizable compound having a urethane bond further has an acid group. Examples of the acid group include a sulfonic acid group, a carboxyl group, and a phosphate group. Of these, a carboxyl group is preferred.

To introduce an acid group into a polymerizable compound having a urethane bond, for example, first react the (meth)acrylate having a hydroxyl group with the polyfunctional isocyanate. Then, a mercapto compound having a carboxyl group is added to the product.

Examples of the mercapto compounds having a carboxyl group include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, o-mercaptobenzoic acid, 2-mercaptonicotinic acid, and mercaptosuccinic acid.

From the viewpoint of pattern formability, the number of polymerizable unsaturated groups in the polymerizable compound having a urethane bond is preferably 3 to 15, and more preferably 5 to 12.

From the viewpoint of pattern formability, the content of the polymerizable compound having a urethane bond is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, and even more preferably 20 to 60 parts by mass, per 100 parts by mass of the polymerizable compound (C).

(Other polymerizable compounds)
Other polymerizable compounds include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxytetraethyleneglycol (meth)acrylate, phenoxyhexaethyleneglycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tricyclodecanyl (meth)acrylate, (meth)acrylic acid ester of methylolated melamine, epoxy (meth)acrylate, various acrylic acid esters and methacrylic acid esters such as urethane acrylate, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, acrylonitrile, and the like.

Other commercially available polymerizable compounds include, for example, KAYARAD R-128H, R526, PEG400DA, MAND, NPGDA, R-167, HX-220, R-551, R712, R-604, R-684, GPO-303, TMPTA, DPHA, DPEA-12, DPHA-2C, D-310, and D-330 manufactured by Nippon Kayaku Co., Ltd., and Aronix M-303, M-305, M-306, M-309, M-310, M-321, M-325, M-350, M-360, M-313, M-315, M-400, M-402, M-403, M-404, and M-4 manufactured by Toagosei Co., Ltd. Examples include Viscoat #310HP, #335HP, #700, #295, #330, #360, #GPT, #400, and #405 manufactured by Osaka Organic Chemicals Co., Ltd., NK Ester A-9300, ABE-300, A-DOG, A-DCP, and A-BPE-4 manufactured by Shin-Nakamura Chemical Co., Ltd., EBECRYL 40, 130, 140, and 145 manufactured by Daicel-Allnex Co., Ltd., AH-600 and AT-600 manufactured by Kyoeisha Chemical Co., Ltd., and OGSOL EA-0200 and 0300 manufactured by Osaka Gas Chemicals Co., Ltd.

The polymerizable compound (C) can be used alone or in combination of two or more types.

The content of the polymerizable compound (C) is preferably 1 to 60 parts by mass, and more preferably 2 to 50 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Photopolymerization initiator (D)]
The photosensitive composition of the present invention contains a photopolymerization initiator (D), which allows the photosensitive composition to be cured by irradiation with active energy rays.

(Photopolymerization initiator (D1) represented by general formula (1))
The photosensitive composition of the present invention preferably contains, as the photopolymerization initiator (D), a photopolymerization initiator (D1) represented by general formula (1) (hereinafter, also simply referred to as photopolymerization initiator (D1)).

General formula (1)

R ₁ and R ₂ each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
The alkyl group having 1 to 8 carbon atoms may be linear, branched, or cyclic, or may be a combination of these, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a cyclohexylmethyl group, a cyclohexylmethyl group, etc. Of these, from the viewpoints of suppressing water stains and pattern shape, a linear alkyl group having 3 to 8 carbon atoms is preferred, and a linear alkyl group having 4 to 6 carbon atoms is more preferred.

_R3 represents a hydrogen atom or any monovalent substituent.
Examples of the monovalent substituent include alkyl groups having 1 to 20 carbon atoms, such as methyl and ethyl groups; alkoxy groups having 1 to 20 carbon atoms, such as methoxy and ethoxy groups; halogen atoms such as F, Cl, Br, and I; acyl groups having 1 to 20 carbon atoms; alkyl ester groups having 1 to 20 carbon atoms; alkoxycarbonyl groups having 1 to 20 carbon atoms; halogenated alkyl groups having 1 to 20 carbon atoms, aromatic ring groups having 4 to 20 carbon atoms; amino groups; aminoalkyl groups having 1 to 20 carbon atoms; hydroxyl groups; nitro groups; cyano groups; optionally substituted benzoyl groups; and optionally substituted thenoyl groups. Examples of the substituents that the benzoyl group or thenoyl group may have include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and alkoxycarbonyl groups having 1 to 10 carbon atoms. Among these, from the viewpoint of radical generation efficiency, a hydrogen atom and a nitro group are preferred, and a hydrogen atom is more preferred.

Methods for producing the photopolymerization initiator (D1) represented by general formula (1) include those described in, for example, JP-T-2019-507108 and JP-T-2019-528331.

Specific examples of the photopolymerization initiator (D1) represented by general formula (1) are shown below. However, the present invention is not limited to these.

Among the compounds of chemical formulas (11) to (13), the photopolymerization initiator of chemical formula (11) is preferred from the viewpoint of pattern formation properties.

The photopolymerization initiator (D1) represented by general formula (1) can be used alone or in combination of two or more types.

(Photopolymerization initiator (D2) other than the photopolymerization initiator (D1) represented by general formula (1))
The photosensitive composition of the present invention may contain, as the photopolymerization initiator (D), a photopolymerization initiator (D2) other than the photopolymerization initiator (D1) represented by general formula (1) (hereinafter also referred to as other photopolymerization initiator (D) or photopolymerization initiator (D2)).

The photopolymerization initiator (D2) is not particularly limited as long as it is a compound that can initiate polymerization of the polymerizable compound (C) by light, and any known photopolymerization initiator can be used.

Specific examples of the photopolymerization initiator (D2) include acetophenone compounds such as 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino)phenyl]-2-(phenylmethyl)-1-butanone, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone;
Benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzil dimethyl ketal; benzophenone compounds such as benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone;
triazine compounds such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine;
acylphosphine oxide compounds such as 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and diphenyl-2,4,6-trimethylbenzoylphosphine oxide;
Oxime compounds such as 1,2-octanedione, 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)], or ethanol, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime);
2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-bromophenyl))4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o,p-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(m-methoxyphenyl)biimidazole, 2,2'-bis Examples of biimidazole compounds include (o,o'-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-nitrophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-methylphenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(o-trifluorophenyl)-4,4',5,5'-tetraphenylbiimidazole.

Commercially available photopolymerization initiators (D2) include, for example, Omnirad 907, 369, 379EG, 819, 1312, 1314, 1316, and TPO manufactured by IGM Resins, IRGACURE OXE-01, 02, 03, and 04 manufactured by BASF Japan, Adeka Arcles N-1919, NCI-730, 831, and 930 manufactured by ADEKA, and TRONLY manufactured by Changzhou Strong New Materials Co., Ltd. Examples include TR-PBG-301, 304, 305, 309, 314, 345, 358, 380, 365, 610, 3054, and 3057, SPI-02, 03, 04, 05, 06, and 07 manufactured by Samyang Corporation, and DFI-020, 306, and EOX-01 manufactured by Daito Chemix Co., Ltd.

The photopolymerization initiator (D2) can be used alone or in combination of two or more types.

The content of photopolymerization initiator (D) is preferably 0.5 to 20 parts by mass, and more preferably 1 to 10 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Benzophenone-based sensitizer (E)]
The photosensitive coloring composition of the present invention contains a benzophenone-based sensitizer (E). Specifically, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc. are used.

Commercially available products include "CHEMARK DEABP" (4,4'-bis(diethylamino)benzophenone, manufactured by Chemark Chemical Co.).

These benzophenone-based sensitizers (E) can be used alone or in combination of two or more in any ratio as needed.

The content of photopolymerization initiator (D) and benzophenone sensitizer (E) must be 100 to 500 parts by weight of benzophenone sensitizer (E) per 100 parts by weight of photopolymerization initiator (D). Furthermore, the content of benzophenone sensitizer (E) is preferably 200 to 300 parts by weight per 100 parts by weight of photopolymerization initiator (D). If the content is less than 200 parts by weight, the adhesion of the formed pattern to the substrate will be poor. If it exceeds 500 parts by weight, problems with developability and pattern formation may occur, and brightness may decrease after heat treatment at 230°C.

[Sensitizers (E2) other than benzophenone-based sensitizers (E)]
Furthermore, the photosensitive coloring composition of the present invention may contain a sensitizer other than the benzophenone-based sensitizer (E).
Examples of sensitizers other than the benzophenone-based sensitizer (E) include chalcone derivatives, unsaturated ketones typified by dibenzalacetone and the like, 1,2-diketone derivatives typified by benzil and camphorquinone and the like, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin, and the like. Examples of the ruthenium complex include ruthenium complexes, ruthenium esters ...

Among sensitizers other than the benzophenone-based sensitizer (E), particularly suitable sensitizers include thioxanthone derivatives and carbazole derivatives. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl-N-ethylcarbazole, etc. can be used.

Commercially available products include "KAYACURE DETX-S" (2,3-diethylthioxanthone, manufactured by Nippon Kayaku Co., Ltd.).

Further examples include, but are not limited to, sensitizers described in "Dye Handbook" edited by Okawara Makoto et al. (Kodansha, 1986), "Chemistry of Functional Dyes" edited by Okawara Makoto et al. (CMC, 1981), "Special Functional Materials" edited by Ikemori Chuzaburo et al., and "Special Functional Materials" (CMC, 1986). Sensitizers that absorb light in the ultraviolet to near-infrared range may also be included.

Sensitizers other than the benzophenone-based sensitizer (E) can be used alone or in a mixture of two or more types in any ratio as needed.

[Colorant (F)]
The photosensitive composition of the present invention may contain a colorant (F), which makes it possible to control the transmittance of each wavelength region of the color filter and improves color separation.

The colorant (F) may be either a pigment or a dye, and these may be used in combination.

(Pigment)
The pigment is preferably a compound classified as a pigment in the Color Index.
Red pigments include, for example, C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2 , 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 1 84, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260 , 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844. Among these, from the viewpoints of heat resistance, light fastness, and transmittance, C.I. Pigment Red 48: 1,122,177,224,242,269,254,291,295,296, pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844 are preferred, C.I. Pigment Red 177,254,291,295,296, pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844 are more preferred.

Examples of orange pigments include C.I. Pigment Orange 36, 38, 43, 64, 71, and 73.

Yellow pigments include, for example, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 1 27,128,129,138,139,147,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,192,193,194,196,198,199,213,214,231,233, and the pigments described in JP-A-2012-226110. Among these, C.I. Pigment Yellow 138, 139, 150, 185, 231, 233 and the pigments described in JP-A 2012-226110 are preferred.

Examples of green pigments include C.I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, and 63. Of these, C.I. Pigment Green 36, 58, 59, 62, and 63 are preferred.

Examples of blue pigments include C.I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Of these, C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, and 15:6 are preferred.

Examples of purple pigments include C.I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. Of these, C.I. Pigment Violet 19 and 23 are preferred.

Specific examples of black pigments include C.I. Pigment Black 1, 6, 7, 12, 20, and 31. Additionally, at least two or more pigments selected from red pigments, yellow pigments, blue pigments, green pigments, and purple pigments may be used as black colorants.

Inorganic pigments include, for example, titanium oxide, barium sulfate, zinc oxide, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, iron blue, chromium oxide green, cobalt green, umber, and synthetic iron black.

(dye)
Examples of dyes include acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, etc. Also included are derivatives of these dyes and lake pigments obtained by converting dyes into lakes.

The acid dye preferably has an acidic group such as a sulfonic acid or carboxylic acid. Also preferred are salt-forming compounds that are salts of an acid dye with a nitrogen-containing compound such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or a primary amine compound. Also preferred are salt-forming compounds that are salts of an acid dye with a resin component having these functional groups. Furthermore, the salt-forming compounds can be sulfonamidated to modify them into sulfonic acid amide compounds, which makes it easier to obtain photosensitive compositions with excellent resistance (light resistance, solvent resistance).
In addition, a salt-forming compound of an acid dye and a compound having an onium salt group is also preferred because it has excellent resistance (light resistance, solvent resistance). The compound having an onium salt group is preferably a resin having a cationic group.

While basic dyes can be used as is, salt-forming compounds that form salts with organic acids, perchloric acid, or their metal salts are preferred. Salt-forming compounds of basic dyes are preferred due to their excellent resistance (lightfastness and solvent resistance) and affinity with pigments. Furthermore, in salt-forming compounds of basic dyes, the anion component that acts as a counterion is preferably an organic sulfonic acid, organic sulfuric acid, a fluorine-containing phosphorus anion compound, a fluorine-containing boron anion compound, a cyano-containing nitrogen anion compound, an anion compound having a conjugate base of an organic acid with a halogenated hydrocarbon group, or a salt-forming compound formed with an acid dye. Furthermore, salt-forming compounds that contain polymerizable unsaturated groups in the molecule further improve resistance.

The chemical structure of dyes can be, for example, azo dyes, disazo dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), quinoneimine dyes (oxazine dyes, thiazine dyes, etc.), azido dyes, Examples of dye structures include dyes derived from dyes selected from the group consisting of quinone dyes, polymethine dyes (oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and metal complex dyes thereof.

Among these, from the viewpoint of color properties such as hue, color separation, and color unevenness, dye structures derived from dyes selected from azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferred, and dye structures derived from dyes selected from xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are more preferred.

The colorant (F) can be used alone or in combination of two or more types.

The content of colorant (F) is preferably 1 to 70 parts by mass, and more preferably 10 to 60 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

(Fine Pigment)
The pigment is preferably micronized before use. The micronization method is not particularly limited, and for example, wet milling, dry milling, or solution precipitation can be used. Among these, salt milling treatment using a kneader method, which is a type of wet milling, is preferred. The average primary particle size of the micronized pigment determined by TEM (transmission electron microscope) is preferably 5 to 90 nm. From the viewpoints of dispersibility and contrast ratio, the average primary particle size is more preferably 10 to 70 nm.

Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt, and water-soluble organic solvent is mechanically kneaded while heated using a kneader, two-roll mill, three-roll mill, ball mill, attritor, sand mill, or other kneading machine, and then the water-soluble inorganic salt and water-soluble organic solvent are removed by rinsing with water. The water-soluble inorganic salt acts as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling. By optimizing the conditions for salt milling pigment, it is possible to obtain pigments with extremely fine primary particle diameters and a narrow, sharp particle size distribution.

Examples of water-soluble inorganic salts include sodium chloride, potassium chloride, and sodium sulfate, with sodium chloride (table salt) being preferred from the standpoint of cost. From the perspectives of both processing efficiency and production efficiency, the amount of water-soluble inorganic salt used is preferably 50 to 2,000 parts by weight, and more preferably 300 to 1,000 parts by weight, per 100 parts by weight of pigment.

The water-soluble organic solvent functions to moisten the pigment and water-soluble inorganic salt. It is not particularly limited as long as it is soluble (miscible) in water and does not substantially dissolve the inorganic salt used. However, because the temperature rises during salt milling and the solvent becomes more likely to evaporate, high-boiling solvents with a boiling point of 120°C or higher are preferred for safety reasons. Examples of water-soluble organic solvents that can be used include 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, and liquid polypropylene glycol. The amount of water-soluble organic solvent used is preferably 5 to 1,000 parts by weight, and more preferably 50 to 500 parts by weight, per 100 parts by weight of the pigment.

If necessary, a resin may be added to the salt milling treatment. There are no particular limitations on the type of resin, and examples include natural resins, modified natural resins, synthetic resins, and synthetic resins modified with natural resins. Of these, resins that are solid at room temperature, insoluble in water, and partially soluble in the organic solvents listed above are preferred. The amount of resin added is preferably 2 to 200 parts by weight per 100 parts by weight of the pigment.

[Dispersion resin (G)]
The photosensitive composition of the present invention may contain a dispersing resin (G).

The dispersing resin (G) is preferably a resin having an adsorption group that has a high affinity for the infrared absorbing compound (A). The adsorption group preferably has one or more of a basic group and an acidic group.

Examples of basic groups include primary amino groups, secondary amino groups, tertiary amino groups, quaternary ammonium bases, and groups containing nitrogen atoms such as nitrogen-containing heterocycles.

Examples of acidic groups include carboxyl groups, phosphate groups, and sulfonic acid groups.

Examples of resin types for the dispersing resin (G) include urethane resins, polycarboxylates and other polycarboxylate esters, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylate ammonium salts, polycarboxylate alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylate esters and their modified products, amides and salts formed by the reaction of poly(lower alkylene imines) with polyesters having free carboxyl groups, (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohols, polyvinylpyrrolidone, and other water-soluble resins and water-soluble polymers, polyesters, modified polyacrylates, ethylene oxide/propylene oxide adducts, and phosphate esters.

Examples of the structure of the dispersing resin (G) include a random structure, a block structure, a graft structure, a comb structure, and a star structure. Of these, from the viewpoint of dispersion stability, a block structure or a comb structure is preferred.

Commercially available dispersion resins (G) include, for example, Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164, or Anti-Terra-U203, 204, or BYK-P, manufactured by BYK-Chemie Japan. 104, P104S, 220S, or Lactimon, Lactimon-WS, or Bykumen, etc., and SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000 manufactured by Lubrizol Japan , 76500, etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc. manufactured by BASF Japan Ltd., and Ajisu manufactured by Ajinomoto Fine-Techno Co., Ltd. Examples of resins include PA111, PB711, PB821, PB822, and PB824, as well as those described in JP 2008-029901 A, JP 2009-155406 A, JP 2010-185934 A, JP 2011-157416 A, WO 2008/007776, JP 2008-029901 A, JP 2009-155406 A, JP 2010-185934 A, JP 2011-157416 A, JP 2009-251481 A, JP 2007-23195 A, and JP 1996-143651 A.

Dispersion resin (G) can be used alone or in combination of two or more types.

From the viewpoint of dispersion stability, the content of the dispersing resin (G) is preferably 3 to 200 parts by mass, and more preferably 5 to 100 parts by mass, per 100 parts by mass of the infrared absorbing compound (A).

[Dye derivative (H)]
The photosensitive composition of the present invention may contain a dye derivative (H).

The dye derivative (H) is not particularly limited, and examples thereof include dye derivatives having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. Examples of the dye derivative (H) include compounds having an acidic substituent such as a sulfo group, a carboxy group, or a phosphate group, and amine salts thereof, compounds having a basic substituent such as a sulfonamide group or a tertiary amino group at the terminal, and compounds having a neutral substituent such as a phenyl group or a phthalimidoalkyl group.
Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, indole pigments such as benzoisoindole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.

Specific examples of diketopyrrolopyrrole dye derivatives include those disclosed in JP 2001-220520 A, WO 2009/081930 A, WO 2011/052617 A, WO 2012/102399 A, and WO 2017-156397 A; examples of phthalocyanine dye derivatives include those disclosed in JP 2007-226161 A, WO 2016/163351 A, JP 2017-165820 A, and Japanese Patent No. 5753266 A; and examples of anthraquinone dye derivatives include those disclosed in JP 63-264 A. 674, JP-A-09-272812, JP-A-10-245501, JP-A-10-265697, JP-A-2007-079094, WO 2009/025325, as quinacridone dye derivatives, JP-A-48-54128, JP-A-03-9961, JP-A-2000-273383, as dioxazine dye derivatives, JP-A-2011-162662, as thiazine indigo dye derivatives, JP-A-2007-314785, as triazine Examples of benzoisoindole dye derivatives include those disclosed in JP-A-61-246261, JP-A-11-199796, JP-A-2003-165922, JP-A-2003-168208, JP-A-2004-217842, and JP-A-2007-314681; examples of benzoisoindole dye derivatives include those disclosed in JP-A-2009-57478; examples of quinophthalone dye derivatives include those disclosed in JP-A-2003-167112, JP-A-2006-291194, JP-A-2008-31281, and JP-A-2012-226 Examples of known dye derivatives include those described in JP-A-110, JP-A-2012-208329 and JP-A-2014-5439 as naphthol dye derivatives, JP-A-2001-172520 and JP-A-2012-172092 as azo dye derivatives, JP-A-2004-307854 as acidic substituents, and JP-A-2002-201377, JP-A-2003-171594, JP-A-2005-181383, JP-A-2005-213404, etc. Although these documents may refer to dye derivatives as derivatives, pigment derivatives, dispersants, pigment dispersants, or simply compounds, the compounds having substituents such as acidic groups, basic groups, and neutral groups in the organic dye residues are synonymous with dye derivatives.

The dye derivative (H) can be used alone or in combination of two or more types.

The content of the dye derivative (H) is preferably 1 to 20 parts by mass, and more preferably 2 to 10 parts by mass, per 100 parts by mass of the infrared absorbing compound (A).

[Thermosetting compound (I)]
The photosensitive composition of the present invention may contain a thermosetting compound (I), which reacts with the thermosetting compound (I) during the heating step, increasing the crosslink density and improving the heat resistance.

The thermosetting compound (I) may be a low molecular weight compound or a high molecular weight compound such as a resin. Examples of the thermosetting compound (I) include epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenol compounds. Of these, epoxy compounds and oxetane compounds are preferred.

(Epoxy compound (I1))
Examples of the epoxy compound (I1) include polycondensates of bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.), polycondensates of phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, etc.), and polycondensates of phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, etc.). Examples of suitable epoxy resins include polymers of phenols and ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.), polycondensates of phenols and aromatic dimethanols (benzenedimethanol, α,α,α',α'-benzenedimethanol, biphenyldimethanol, α,α,α',α'-biphenyldimethanol, etc.), polycondensates of phenols and aromatic dichloromethyls (α,α'-dichloroxylene, bischloromethylbiphenyl, etc.), polycondensates of bisphenols and various aldehydes, glycidyl ether epoxy resins obtained by glycidylating alcohols, alicyclic epoxy resins, heterocyclic epoxy resins, aliphatic epoxy resins, glycidylamine epoxy resins, and glycidyl ester epoxy resins.

Commercially available products include, for example, Epicoat 807, 815, 825, 827, 828, 190P, and 191P manufactured by Yuka Shell Epoxy Co., Ltd., and TECHMORE manufactured by Mitsui Chemicals, Inc. Examples include VG3101L, EPPN-201, 501H, 502H, EOCN-102S, 103S, 104S, and 1020 manufactured by Nippon Kayaku Co., Ltd., Epicoat 1004 and 1256, JER1032H60, 157S65, 157S70, 152, and 154 manufactured by Japan Epoxy Resins Co., Ltd., Celoxide 2021 and EHPE-3150 manufactured by Daicel Chemical Industries, Ltd., Denacol EX-211, 212, 252, 313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, 711, and 721 manufactured by Nagase ChemteX Corporation, and TEPIC-L, H, and S manufactured by Nissan Chemical Industries, Ltd.

From the viewpoint of the heat resistance of the cured film, the content of epoxy compound (I1) is preferably 0.5 to 50 parts by mass, and more preferably 1 to 40 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

(Oxetane Compound (I2))
The oxetane compound (I2) is a known compound having an oxetane group. Examples of the oxetane compound include monofunctional oxetane compounds, bifunctional oxetane compounds, and trifunctional or higher functional oxetane compounds.

Examples of monofunctional oxetane compounds include (3-ethyloxetan-3-yl)methyl acrylate, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-ethyl-3-(2-methacryloxymethyl)oxetane, and 3-ethyl-3-{[3-(triethoxysilyl)propoxy]methyl}oxetane.

Commercially available products include, for example, OXE-10 and 30 manufactured by Osaka Organic Chemical Industry Co., Ltd., and Aron Oxetane OXT-101 and 212 manufactured by Toagosei Co., Ltd.

Examples of bifunctional oxetane compounds include 4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl), 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 1,4-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}benzene, di[1-ethyl(3-oxetanyl)]methyl ether, di[1-ethyl(3-oxetanyl)]methyl ether 3-ethyl-3-hydroxymethyloxetane, 3- Ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(2-phenoxymethyl)oxetane, 3,7-bis(3-oxetanyl)-5-oxa-nonane, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, dicyclopentenyl bis(3-ethyl- 1,4-bis(3-ethyl-3-oxetanylmethyl)ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, polyethylene glycol bis(3-ethyl-3-oxetanylmethyl)ether, ethylene oxide (EO) modified bis(3-ethyl-3-oxetanylmethyl)ether Examples include bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, propylene oxide (PO)-modified bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, EO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, PO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, and EO-modified bisphenol F (3-ethyl-3-oxetanylmethyl) ether.

Commercially available products include OXBP and OXTP manufactured by Ube Industries, Ltd., and Aron Oxetane OXT-121 and OXT-221 manufactured by Toagosei Co., Ltd.

Examples of trifunctional or higher oxetane compounds include pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexa(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, and caprolactone-modified dipentaerythritol. Examples include erythritol hexa(3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane tetrakis(3-ethyl-3-oxetanylmethyl) ether, resins containing oxetane groups (such as the oxetane-modified phenol novolac resin described in Japanese Patent No. 3783462), and polymers obtained by radical polymerization of (meth)acrylic monomers such as the aforementioned OXE-30.

The content of the oxetane compound (I2) is preferably 0.5 to 50 parts by mass, and more preferably 1 to 40 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

Melamine compounds are compounds that have a melamine ring structure. Methylol-type or ether-type melamine compounds are preferred, and melamine compounds with an average of 5.0 or more methylol groups and/or ether groups per melamine ring are more preferred. Having an appropriate number of methylol groups or ether groups makes it easier to achieve just the right amount of heat resistance.

Commercially available products include, for example, Nikalac MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, MS-001, MX-002, MX-730, MX-750, MX-708, MX-706, MX-042, MX-45, MX-500, MX-520, MX-43, MX-417, and MX-410 manufactured by Sanwa Chemical Co., Ltd., and Cymel 232, 235, 236, 238, 285, 300, 301, 303, 350, and 370 manufactured by Nippon Cytec Industries Co., Ltd.

Among these, products with an average number of methylol groups and/or ether groups per melamine ring of 5.0 or more, such as Nikalac MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, and MX-45 manufactured by Sanwa Chemical Co., Ltd., and Cymel 232, 235, 236, 238, 300, 301, 303, and 350 manufactured by Nippon Cytec Industries Co., Ltd., are preferred in terms of increasing crosslink density.

Thermosetting compounds (I) can be used alone or in combination of two or more types.

[Curing agent (curing accelerator)]
The photosensitive composition of the present invention can be used in combination with a curing agent (curing accelerator) to aid in the curing of the thermosetting compound (I). Examples of the curing agent include amine compounds, acid anhydrides, active esters, carboxylic acid compounds, and sulfonic acid compounds. Examples of the curing agent include amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, and 4-methyl-N,N-dimethylbenzylamine), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride), blocked isocyanate compounds (e.g., dimethylamine), imidazole derivatives, bicyclic amidine compounds, and salts thereof (e.g., imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (for example, triphenylphosphine, etc.), S-triazine derivatives (for example, 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine·isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine·isocyanuric acid adduct, etc.).

Hardening agents can be used alone or in combination of two or more types.

The content of the curing agent is preferably 0.01 to 15 parts by mass per 100 parts by mass of the thermosetting compound (I).

[Thiol-based chain transfer agent (J)]
The photosensitive composition of the present invention may contain a thiol-based chain transfer agent (J). When the thiol-based chain transfer agent (J) is used in combination with the photopolymerization initiator (D), it generates thiyl radicals that are less susceptible to polymerization inhibition by oxygen during radical polymerization after light irradiation, thereby improving the photosensitivity of the photosensitive composition.

The thiol chain transfer agent (J) is preferably a multifunctional thiol having two or more thiol groups (SH groups), and more preferably a multifunctional thiol having four or more thiol groups. Increasing the number of functional groups makes it easier for the film to be photocured from the surface to the deepest part.

Examples of polyfunctional thiols include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthioglycolate, Examples include erythritol tetrakisthiopropionate, trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, and 2-(N,N-dibutylamino)-4,6-dimercapto-s-triazine. Preferred examples include ethylene glycol bisthiopropionate, trimethylolpropane tristhiopropionate, and pentaerythritol tetrakisthiopropionate.

The thiol chain transfer agent (J) can be used alone or in combination of two or more types.

The content of the thiol chain transfer agent (J) is preferably 1 to 10 parts by mass, and more preferably 2 to 8 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition. When an appropriate amount is added, photosensitivity is improved and wrinkles are less likely to form on the surface of the cured film.

[Polymerization inhibitor (K)]
The photosensitive composition of the present invention may contain a polymerization inhibitor (K).

Examples of the polymerization inhibitor (K) include alkyl catechol compounds such as catechol, resorcinol, 1,4-hydroquinone, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, 4-ethylcatechol, 2-propylcatechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-t-butylcatechol, 3-t-butylcatechol, 4-t-butylcatechol, and 3,5-di-t-butylcatechol; 2-methylresorcinol, 4-methylresorcinol, 2-ethylresorcinol, 4-ethylresorcinol, 2-propylresorcinol, 4-propylresorcinol, and 2-n alkylresorcinol compounds such as 4-n-butylresorcinol, 2-t-butylresorcinol, and 4-t-butylresorcinol; alkylhydroquinone compounds such as methylhydroquinone, ethylhydroquinone, propylhydroquinone, t-butylhydroquinone, and 2,5-di-t-butylhydroquinone; phosphine compounds such as tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, and tribenzylphosphine; phosphine oxide compounds such as trioctylphosphine oxide and triphenylphosphine oxide; phosphite compounds such as triphenylphosphite and trisnonylphenylphosphite; pyrogallol; and phloroglucinol.

The content of the polymerization inhibitor (K) is preferably 0.01 to 0.4 parts by mass per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Ultraviolet absorber (L)]
The photosensitive composition of the present invention may contain an ultraviolet absorber (L).

The ultraviolet absorber (L) is an organic compound that has ultraviolet absorbing properties, and examples thereof include benzotriazole-based organic compounds, triazine-based organic compounds, benzophenone-based organic compounds, salicylic acid ester-based organic compounds, cyanoacrylate-based organic compounds, and salicylate-based organic compounds.

Benzotriazole compounds include, for example, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, 2-[2-hydroxy-3,5-bis(α, α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-dimethylethyl)-4-hydroxy, C7-9 branched and linear alkyl ester mixture, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol, methyl 3-(3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethylene glycol 300 reaction products, 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-t-butyl Examples of suitable hydroxybenzoates include octyl-4-methylphenol, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, octyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, and 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate.

Commercially available products include, for example, TINUVIN P, PS, 234, 326, 329, 384-2, 900, 928, 99-2, and 1130 manufactured by BASF Japan; Adekastab LA-29, LA-31RG, LA-32, and LA-36 manufactured by ADEKA; KEMISORB 71, 73, 74, 79, and 279 manufactured by Chemipro Chemical; and RUVA-93 manufactured by Otsuka Chemical.

Triazine compounds include, for example, 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-1,3,5-triazine, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, and the reaction product of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine with (2-ethylhexyl)glycidic acid ester. Examples include 2,4-bis[2-hydroxy-4-butoxyphenyl]-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(hexyloxy)phenol, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol, and 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine.

Commercially available products include, for example, KEMISORB 102 manufactured by Chemipro Chemicals, TINUVIN 400, 405, 460, 477, 479, and 1577ED manufactured by BASF Japan, Adekastab LA-46 and LA-F70 manufactured by ADEKA Corporation, and CYASORB UV-1164 manufactured by Sun Chemical.

Examples of benzophenone compounds include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid-3-hydrate, 2-hydroxy-4-n-octoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, and 2-hydroxy-4-methoxy-2'-carboxybenzophenone.

Commercially available products include, for example, KEMISORB 10, 11, 11S, 12, and 111 manufactured by Chemipro Chemicals, SEESORB 101 and 107 manufactured by Shipro Chemicals, Adekastab 1413 manufactured by ADEKA Corporation, and UV-12 manufactured by Sun Chemical.

Examples of salicylate ester compounds include phenyl salicylate, p-octylphenyl salicylate, and p-tert-butylphenyl salicylate.

The content of the ultraviolet absorber (L) is preferably 5 to 70 parts by mass per 100 parts by mass of the total of the photopolymerization initiator (D) and the ultraviolet absorber (L).

[Antioxidant (M)]
The photosensitive composition of the present invention can contain an antioxidant (M). The antioxidant (M) prevents yellowing of the photopolymerization initiator (D) and thermosetting compound (I) in the photosensitive coloring composition due to oxidation during the thermal process of thermal curing or ITO annealing. In particular, when the concentration of the infrared absorbing compound (A) in the photosensitive composition is high, the content of the polymerizable compound (C) is relatively reduced, and if the amount of the photopolymerization initiator (D) is increased or a thermosetting compound is added to address this, the cured film is likely to yellow. Therefore, the inclusion of an antioxidant prevents yellowing of the cured film due to oxidation during the heating process. The antioxidant (M) is preferably a compound that does not contain a halogen atom.

Examples of the antioxidant (M) include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds. Among these, hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferred.

Examples of hindered phenol antioxidants include 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,1,3-tris-(2'-methyl-4'-hydroxy-5'-t-butylphenyl)-butane, 4,4'-butylidene-bis-(2-t-butyl-5-methylphenol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)stearyl propionate, pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 3,9-bis[2-[3-( 3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,3,5-tris(3,5-di-t-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3-hydroxy-4-t-butyl-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 2,2'-methylenebis(6-t-butyl-4-ethylphenol), 2,2'-thiodiethylbis-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, N,N-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), i-octyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 4,6-bis(dodecylthiomethyl)-o-cresol, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoethyl ester, 4,6-bis(octylthiomethyl)-o-cresol, bis[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propionic acid]ethylenebisoxybisethylene, 1,6-hexanediolbis[3-(3,5- Examples include di-t-butyl-4-hydroxyphenyl)propionate, 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, 2,2'-thio-bis-(6-t-butyl-4-methylphenol), 2,5-di-t-amyl-hydroquinone, 2,6-di-t-butyl-4-nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 2,2'-methylene-bis-(6-(1-methyl-cyclohexyl)-p-cresol), and 2,4-dimethyl-6-(1-methyl-cyclohexyl)-phenol.

Commercially available products include, for example, Adekastab AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, and AO-330 manufactured by ADEKA Corporation; KEMINOX 101, 179, 76, and 9425 manufactured by Chemipro Corporation; IRGANOX 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 245, 259, 3114, 5057, and 565 manufactured by BASF Japan; and Cyanox CY-1790 and CY-2777 manufactured by Sun Chemical Company.

Examples of hindered amine antioxidants include tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 2,2 , 6,6-tetramethyl-4-piperidyl methacrylate, polycondensation product of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], ester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol and 3,5,5-trimethylhexanoic acid, N,N'-4,7-tetramethyl- Bis[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino}-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, decanedioic acid bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) ester, reaction products of 1,1-dimethylethyl hydroperoxide with octane, bis(1,2,2,6,6-pentamethyl-4-pyridyl)[[3,5-bis(1,1dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate methyl 1,2,2,6,6-pentamethyl-4-pyridyl sebacate ester, poly[[6-morpholino-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], 2,2,6,6-tetramethyl-4-piperidyl-C12-21 and C18 unsaturated fatty acid esters, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, etc.

Commercially available products include, for example, Adeka STAB LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, LA-77G, LA-81, LA-82, LA-87, LA-402F, and LA-502XP manufactured by ADEKA Corporation; KAMISTAB 29, 62, 77, and 94 manufactured by Chemipro Chemicals; Tinuvin 111FDL, 123, 144, 249, 292, and 5100 manufactured by BASF Japan; and Cyasorb UV-3346, UV-3529, and UV-3853 manufactured by Sun Chemical Co., Ltd.

Examples of phosphorus-based antioxidants include di(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexyl phosphite, tris(2,4-di-t-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra(C12-C15 alkyl)-4,4'-isopropylidene diphenyl diphosphite, diphenyl mono (2-ethylhexyl) phosphite, diphenyl isodecyl phosphite, tris(isodecyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-t-butylphenyl)-4,4-biphenyl diphosphonate, tris(tridecyl) phosphite, phenyl isooctyl phosphite, phenyl isodecyl phosphite, phenyl di(tridecyl) phosphite, diphenyl isooctyl phosphite, diphenyl tridecyl phosphite, 4,4'-isopropylidene diphenol alkyl phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris(biphenyl) phosphite, di(2,4-di-t-butylphenyl)pentaerythritol diphosphite, di(nonylphenyl)pentaerythritol diphosphite, phenyl bisphenol A pentaerythritol diphosphite, tetratridecyl 4,4'-butylidenebis(3-methyl-6-t-butylphenol) diphosphite, hexatridecyl Examples include 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, sodium bis(4-t-butylphenyl)phosphite, sodium 2,2-methylene-bis(4,6-di-t-butylphenyl)-phosphite, 1,3-bis(diphenoxyphosphonyloxy)-benzene, and ethyl bis(2,4-di-t-butyl-6-methylphenyl)phosphite.

Commercially available products include, for example, Adekastab PEP-36, PEP-8, HP-10, 2112, 1178, 1500, C, 135A, 3010, and TPP manufactured by ADEKA Corporation, IRGAFOS 168 manufactured by BASF Japan, and Hostanox P-EPQ manufactured by Clariant Chemicals.

Examples of sulfur-based antioxidants include 2,2-bis{[3-(dodecylthio)-1-oxopropoxy]methyl}propane-1,3-diylbis[3-(dodecylthio)propionate], 3,3'-thiobisditridecylpropionate, 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]-o-cresol, and 2,4-bis[(laurylthio)methyl]-o-cresol.

Commercially available products include, for example, Adeka Stab AO-412S and AO-503 manufactured by ADEKA Corporation, and KEMINOX PLS manufactured by Chemipro Kasei Co., Ltd.

Antioxidants (M) can be used alone or in combination of two or more types.

The content of antioxidant (M) is preferably 0.5 to 5.0 parts by mass per 100 parts by mass of the nonvolatile content of the photosensitive composition. When an appropriate amount is included, the transmittance, spectral characteristics, and sensitivity are improved.

[Leveling agent (N)]
The photosensitive composition of the present invention may contain a leveling agent (N). This further improves the wettability to a substrate during application and the drying property. Examples of the leveling agent (N) include silicone surfactants, fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.

Examples of silicone surfactants include linear polymers consisting of siloxane bonds and modified siloxane polymers in which organic groups have been introduced into the side chains or terminals.

Commercially available products include, for example, BYK-300, 306, 310, 313, 315N, 320, 322, 323, 330, 331, 333, 342, 345, 346, 347, 348, 349, 370, 377, 378, 3455, UV3510, and 3570 manufactured by BYK-Chemie, and FZ-7002 and 211 manufactured by Dow Corning Toray. Examples include 0, 2122, 2123, 2191, 5609, and Shin-Etsu Chemical Co., Ltd.'s X-22-4952, X-22-4272, X-22-6266, KF-351A, KF-354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-4515, KF-6004, and KP-341.

Examples of fluorosurfactants include surfactants or leveling agents with fluorocarbon chains.

Commercially available products include Surflon S-242, 243, 420, 611, 651, and 386 manufactured by AGC Seimi Chemical Co., Ltd.; Megafac F-253, 477, 551, 552, 555, 558, 560, 570, 575, and 576, R-40-LM, R-41, RS-72-K, and DS-21 manufactured by DIC Corporation; FC-4430 and 4432 manufactured by Sumitomo 3M Limited; EF-PP31N09, EF-PP33G1, and EF-PP32C1 manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.; and Futergent 602A manufactured by Neos Corporation.

Nonionic surfactants include, for example, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristyl ether, polyoxyethylene octyldodecyl ether, polyoxyalkylene alkyl ether, polyoxyphenylenedistyrenated phenyl ether, polyoxyethylene tribenzyl phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyalkylene alkenyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, and sorbitan tristearate. acrylate, sorbitan monooleate, sorbitan trioleate, sorbitan sesquioleate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan triisostearate, polyoxyethylene sorbitan tetraoleate, glycerol monostearate, glycerol monooleate, polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene glycol monooleate, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, alkyl alkanolamide, alkyl imidazoline, etc.

Commercially available products include Emulgen 103, 104P, 106, 108, 109P, 120, 123P, 130K, 147, 150, 210P, 220, 306P, 320P, 350, 404, 408, 409PV, 420, 430, 705, 707, 709, 1108, 1118S-70, 1135S-70, 1150S-60, 2020G-HA, 2025G, and LS- manufactured by Kao Corporation. 106, LS-110, LS-114, MS-110, A-60, A-90, B-66, PP-290, LATEMURU PD-420, PD-430, PD-430S, PD-450, Rheodor SP-L10, SP-P10, SP-S10V, SP-S20, SP-S30V, SP-O10V, SP-O30V, Super SP-L10, AS-10V, AO-10V, AO-15V, TW-L120, TW-L106, TW-P120, TW-S120V, TW-S320V, TW-O120V, TW-O106V, TW-IS399C, Super TW-L120, 430V, 440V, 460V, MS-50, MS-60, MO-60, MS-165V, Emanon 1112, 3199V, 3299V, 3299RV, 4110, CH-25, CH-40, C Examples include H-60(K), Amit 102, 105, 105A, 302, 320, Aminone PK-02S, L-02, Homogenol L-95, ADEKA Corporation's Adeka Pluronic (registered trademark) L-23, 31, 44, 61, 62, 64, 71, 72, 101, 121, TR-701, 702, 704, 913R, and Kyoeisha Chemical Co., Ltd.'s (meth)acrylic acid (co)polymer Polyflow No. 75, No. 90, No. 95.

Examples of cationic surfactants include alkylamine salts, alkyl quaternary ammonium salts such as lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, and cetyltrimethylammonium chloride, and their ethylene oxide adducts.

Commercially available products include, for example, Acetamine 24, Cortamine 24P, 60W, and 86P Concentrate, manufactured by Kao Corporation.

Examples of anionic surfactants include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine styrene-acrylic acid copolymers, and polyoxyethylene alkyl ether phosphate esters.

Commercially available products include, for example, Futergent 100 and 150 manufactured by Neos Corporation, and Adeka Hope YES-25, Adekacol TS-230E, PS-440E, and EC-8600 manufactured by ADEKA Corporation.

Examples of amphoteric surfactants include alkyl betaines such as lauric acid amidopropyl betaine, lauryl betaine, cocamidopropyl betaine, stearyl betaine, and alkyl dimethylaminoacetic acid betaine, and alkyl amine oxides such as lauryl dimethylamine oxide.

Commercially available products include Kao Corporation's Anhithol 20AB, 20BS, 24B, 55AB, 86B, 20Y-B, and 20N.

Leveling agents (N) can be used alone or in combination of two or more types.

The content of the leveling agent (N) is preferably 0.001 to 2.0 parts by mass, and more preferably 0.005 to 1.0 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition. When an appropriate amount is included, the balance between the coatability and adhesion of the photosensitive composition is further improved.

[Storage stabilizer (O)]
The photosensitive composition of the present invention may contain a storage stabilizer (O). This stabilizes the viscosity of the photosensitive composition over time. Examples of the storage stabilizer (O) include quaternary ammonium chlorides such as benzyl trimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, organic phosphines such as t-butylpyrocatechol, tetraethylphosphine and tetraphenylphosphine, and phosphites.

The content of the storage stabilizer (O) is preferably 0.1 to 10 parts by mass per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Adhesion improver (P)]
The photosensitive composition of the present invention may contain an adhesion improver (P). This improves the adhesion between the cured film and the substrate, and also makes it easier to form narrow patterns by photolithography.

Examples of the adhesion improver (P) include silane coupling agents. Examples of silane coupling agents include vinyl silanes such as vinyltrimethoxysilane and vinyltriethoxysilane; (meth)acrylic silanes such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane; epoxy silanes such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane and N-2-(aminoethyl) Examples of silane coupling agents include aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane hydrochloride; mercapto compounds such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; styryl compounds such as p-styryltrimethoxysilane; ureido compounds such as 3-ureidopropyltriethoxysilane; sulfides such as bis(triethoxysilylpropyl)tetrasulfide; and isocyanates such as 3-isocyanatepropyltriethoxysilane.

The adhesion improver (P) can be used alone or in combination of two or more types.

The content of the adhesion improver (P) is preferably 0.01 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the nonvolatile content of the photosensitive composition.

[Organic solvent (Q)]
The photosensitive composition of the present invention may contain an organic solvent (Q).

Examples of organic solvents (Q) include 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, and n-butyl Alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol Examples of the propylene glycol monomethyl ether include diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters. Among these, from the viewpoints of pigment dispersibility and alkali-soluble resin solubility, glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone are preferred.

The organic solvent (Q) can be used alone or in combination of two or more types.

[Method for producing photosensitive composition]
The photosensitive composition of the present invention can be produced by, for example, adding an infrared absorbing compound (A), a dispersing resin (G), an organic solvent (Q), and the like and performing a dispersion treatment to produce a dispersion. The dispersion can then be mixed with an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and the like. The timing of blending each material is arbitrary. The dispersion process can also be performed multiple times.

Dispersing machines used for the dispersion process include, for example, two-roll mills, three-roll mills, ball mills, horizontal sand mills, vertical sand mills, annular bead mills, and attritors.

The average dispersed particle size (secondary particle size) of the infrared absorbing compound (A) in the dispersion is preferably 30 to 200 nm, and more preferably 40 to 200 nm. Having an appropriate particle size makes it easier to obtain a photosensitive composition with high dispersion stability.

The average dispersed particle size (secondary particle size) is measured, for example, using Nikkiso's Microtrac UPA-EX150, which employs dynamic light scattering (FFT power spectrum) with particle permeability set to absorption mode, particle shape set to non-spherical, and the D50 particle size taken as the average diameter. The organic solvent used for dispersion should be used as the dilution solvent for measurement, and it is preferable to measure samples treated with ultrasound immediately after sample preparation, as this tends to yield results with little variation.

The photosensitive composition is preferably subjected to centrifugation, filtration using a sintered filter or membrane filter, or other means to remove coarse particles of 5 μm or larger, preferably coarse particles of 1 μm or larger, and even more preferably coarse particles of 0.5 μm or larger, as well as any contaminated dust. The photosensitive composition of the present invention preferably contains substantially no particles of 0.5 μm or larger, and more preferably contains no particles of 0.3 μm or smaller.

<Cured film>
The cured film of the present invention can be obtained by curing a film formed using the photosensitive composition of the present invention through a treatment such as exposure to light.

[Method of producing cured film]
The method for producing the cured film is not particularly limited, and the cured film can be produced, for example, by carrying out the following steps: (1) applying a photosensitive composition onto a substrate to form a layer of the composition; (2) exposing the layer to light in a pattern through a mask; (3) developing the unexposed portions with an alkali to form a patterned cured film; and (4) heat-treating (post-baking) the pattern.

The method for producing the cured film will be described in detail below.
(Step (1))
In the step (1) of forming a composition layer, the photosensitive composition is applied onto a substrate by a method such as spin coating, roll coating, slit coating, casting coating, or inkjet coating, and then dried (prebaked) at a temperature of 50 to 120°C for 10 to 120 seconds using an oven, a hot plate, or the like, as necessary.
Examples of the substrate include a glass substrate and a silicon substrate. The silicon substrate may have an imaging element such as a CCD or a CMOS formed on its surface. If necessary, an undercoat layer may be provided on the substrate to improve adhesion with an upper layer, prevent diffusion of substances, and flatten the substrate surface.
The coating is preferably carried out so that the layer has a thickness of 0.05 to 10 μm after drying, and more preferably 0.3 to 5 μm.

(Step (2))
In the exposure step, the layer obtained in step (1) is exposed to light in a specific pattern through a mask using an exposure device such as a stepper, thereby obtaining a cured film.
Examples of radiation used for exposure include ultraviolet rays such as g-rays, h-rays, and i-rays.

(Step (3))
The cured film obtained in step (2) is subjected to an alkali development treatment, whereby the composition layer in the unexposed areas is eluted in an alkaline aqueous solution, leaving only the cured areas, thereby obtaining a patterned cured film.
Examples of the developer include alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene.
The concentration of the developer is preferably from 0.001 to 10 parts by mass, more preferably from 0.01 to 1 part by mass.
The pH of the alkaline developer is preferably 11 to 13, more preferably 11.5 to 12.5. When used at an appropriate pH, roughening and peeling of the pattern is suppressed, and the remaining film rate after development is improved.

Developing methods include, for example, the dipping method, spraying method, and puddling method. The development temperature is preferably 15 to 40°C. After alkaline development, it is preferable to wash with pure water.

(Step (4))
The heat treatment (post-baking) is performed by heating the patterned cured film obtained in step (3) to sufficiently cure it. The heating temperature for post-baking is preferably 100 to 300° C., more preferably 150 to 250° C. The heating time is preferably about 2 minutes to 1 hour, more preferably about 3 minutes to 30 minutes.

<Optical filter>
The cured film of the present invention can be used for optical filters. In particular, it can be preferably used as an infrared cut filter. It can also be used as an infrared transmission filter. The optical filter of the present invention can be produced by the same method as the above-mentioned cured film.

<Image display device>
The cured film of the present invention can be used in an image display device. The form in which it is used in an image display device is not particularly limited, and it can be used as a color filter or a black matrix.
Examples of the black matrix include a black border provided on the periphery of an image display device such as a solid-state imaging device or a liquid crystal display device, a grid-like and/or stripe-like black portion between red, blue, and green pixels, and a dot-like and/or linear black pattern for TFT light shielding.

An example of an image display device of the present invention will now be described. The image display device comprises the cured film of the present invention and a light source. Examples of light sources include cold cathode fluorescent lamps (CCFLs) and white LEDs, but in the present invention, it is preferable to use white LEDs because they broaden the red reproduction range. Figure 1 is a schematic cross-sectional view showing an example of the configuration of an image display device equipped with the cured film of the present invention. The image display device 10 shown in Figure 1 comprises a pair of transparent substrates 11 and 21 arranged at a distance from each other, with liquid crystal LC sealed between them.

A TFT (thin film transistor) array 12 is formed on the inner surface of the first transparent substrate 11, and a transparent electrode layer 13 made of, for example, ITO is formed on top of that. An alignment layer 14 is provided on the transparent electrode layer 13. A polarizer 15 is also formed on the outer surface of the transparent substrate 11.

On the other hand, a color filter 22 is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments that make up the color filter 22 are separated by a black matrix (not shown).

If necessary, a transparent protective film (not shown) is formed to cover the color filter 22, and a transparent electrode layer 23 made of, for example, ITO is formed on top of that. An alignment layer 24 is provided to cover the transparent electrode layer 23.

A polarizing plate 25 is formed on the outer surface of the transparent substrate 21. A backlight unit 30 is provided below the polarizing plate 15.

The liquid crystal LC is aligned according to the drive mode, such as TN (Twisted Nematic), STN (Super Twisted Nematic), IPS (In-Plane Switching), VA (Vertical Alignment), or OCB (Opticaly Compensated Birefringence). A TFT (thin film transistor) array 12 is formed on the inner surface of the first transparent substrate 11, and a transparent electrode layer 13 made of, for example, ITO is formed thereon. An alignment layer 14 is provided on the transparent electrode layer 13. A polarizer 15 is formed on the outer surface of the transparent substrate 11.

On the other hand, a color filter 22 is formed on the inner surface of the second transparent substrate 21. The red, green, and blue filter segments that make up the color filter 22 are separated by a black matrix (not shown).

If necessary, a transparent protective film (not shown) is formed to cover the color filter 22, and a transparent electrode layer 23 made of, for example, ITO is formed on top of that. An alignment layer 24 is provided to cover the transparent electrode layer 23.

A polarizing plate 25 is formed on the outer surface of the transparent substrate 21. A backlight unit 30 is provided below the polarizing plate 15.

White LED light sources include those with a fluorescent filter formed on the surface of a blue LED and those with a fluorescent material contained in the resin package of a blue LED, and have a wavelength (λ3) in the range of 430 nm to 485 nm at which the emission intensity is maximized, a wavelength (λ4) in the range of 530 nm to 580 nm at which the emission intensity is maximized, and a wavelength (λ5) in the range of 600 nm to 650 nm at which the emission intensity is maximized, and the ratio (I4/I3) of the emission intensity I3 at wavelength λ3 to the emission intensity I4 at wavelength λ4 is between 0.2 and 0.4. Therefore, a white LED light source (LED1) having spectral characteristics in which the ratio (I5/I3) of the emission intensity I3 at wavelength λ3 to the emission intensity I5 at wavelength λ5 is 0.1 or more and 1.3 or less, or a white LED light source (LED2) having a wavelength (λ1) at which the emission intensity is maximum in the range of 430 nm to 485 nm, a second emission intensity peak wavelength (λ2) in the range of 530 nm to 580 nm, and spectral characteristics in which the ratio (I2/I1) of the emission intensity I1 at wavelength λ1 to the emission intensity I2 at wavelength λ2 is 0.2 or more and 0.7 or less is preferred.

Specific examples of LED1 include NSSW306D-HG-V1 (manufactured by Nichia Corporation) and NSSW304D-HG-V1 (manufactured by Nichia Corporation).

Specific examples of LED2 include NSSW440 (manufactured by Nichia Corporation) and NSSW304D (manufactured by Nichia Corporation).

<Solid-state imaging element>
The cured film of the present invention can be used for a solid-state imaging device. The form of use for the solid-state imaging device is not particularly limited, but for example, a form can be mentioned in which a substrate has a plurality of photodiodes constituting the light-receiving area of the solid-state imaging device (such as a CCD image sensor, a CMOS image sensor, or an organic CMOS image sensor) and a light-receiving element made of polysilicon or the like, and the cured film of the present invention is provided on the light-receiving element forming surface side or the opposite side of the forming surface. Figure 2 is a schematic cross-sectional view showing an example of the configuration of a solid-state imaging device provided with the cured film of the present invention.

As shown in FIG. 2, the solid-state imaging device 200 comprises a rectangular solid-state imaging element 201 and a transparent cover glass 203 that is held above the solid-state imaging element 201 and seals the solid-state imaging element 201. Furthermore, a lens layer 211 is provided on top of the cover glass 203 via a spacer 104. The lens layer 211 is composed of a support 213 and a lens material 212. When stray light enters the peripheral region of the lens layer 211, the light diffusion weakens the light-collecting effect of the lens material 212, reducing the amount of light that reaches the imaging unit 202. Stray light also generates noise. For this reason, the peripheral region of the lens layer 211 is provided with a cured film 214 of the present invention to block light.

The solid-state imaging element 201 photoelectrically converts the optical image formed on the imaging section 202, which serves as its light-receiving surface, and outputs it as an image signal. This solid-state imaging element 201 is equipped with a laminated substrate 205, which is made up of two substrates stacked together. The laminated substrate 205 consists of a rectangular chip substrate 206 and a circuit substrate 207 of the same size, with the circuit substrate 207 stacked on the back surface of the chip substrate 206.

The imaging unit 202 is located in the center of the surface of the chip substrate 206. Furthermore, if stray light enters the peripheral region of the imaging unit 202, dark current (noise) will be generated from the circuitry within this peripheral region. Therefore, this peripheral region is shielded from light by the provision of the hardened film (light-shielding) 215 of the present invention.

Multiple electrode pads 208 are provided on the surface edge of the chip substrate 206. The electrode pads 208 are electrically connected to the imaging unit 202 via signal lines (not shown) provided on the surface of the chip substrate 206.

External connection terminals 209 are provided on the back surface of the circuit board 207, approximately below each electrode pad 208. Each external connection terminal 209 is connected to each electrode pad 208 via a through-electrode 210 that vertically penetrates the laminated substrate 205. Each external connection terminal 209 is also connected via wiring (not shown) to a control circuit that controls the driving of the solid-state imaging element 201, an image processing circuit that performs image processing on the imaging signal output from the solid-state imaging element 201, and the like.

<Infrared sensor>
The cured film of the present invention can be used in an infrared sensor. Fig. 3 is a schematic cross-sectional view showing an example of the configuration of an infrared sensor including the cured film of the present invention. The infrared sensor 300 shown in Fig. 3 includes a solid-state image sensor 310.

The imaging area provided on the solid-state imaging device 310 is configured by combining an infrared cut filter 311 and a color filter 312 .
The infrared cut filter 311 transmits light in the visible light range (for example, light with a wavelength of 400 to 700 nm) and blocks light in the infrared range (for example, light with a wavelength of 800 to 1300 nm).
The color filter 312 is a color filter formed with pixels that transmit and absorb light of specific wavelengths in the visible light range, and for example, a color filter formed with red (R), green (G), and blue (B) pixels is used.

Between the infrared transmission filter 313 and the solid-state imaging element 310, a resin film 314 that is capable of transmitting light of the wavelength that has passed through the infrared transmission filter 313 is disposed.
The infrared transmission filter 313 is a filter that has visible light blocking properties and transmits infrared rays of a specific wavelength, and the cured film of the present invention containing the infrared absorbing compound (A) described above can be used for the infrared transmission filter 313. The infrared transmission filter 113 preferably blocks light with a wavelength of 400 to 830 nm and transmits light with a wavelength of 900 to 1,300 nm, for example.

Microlenses 315 are arranged on the incident light side of the color filters 312 and infrared transmission filters 313. A planarization film 316 is formed to cover the microlenses 315.

In the embodiment shown in Figure 3, a resin film 314 is arranged, but an infrared transmission filter 313 may be formed instead of the resin film 314.

The cured film of the present invention can be used as a light-shielding film on the edges and/or sides of the surface of the infrared cut filter 311, and when used on the inner walls of an infrared sensor, it can prevent internal reflection and/or the incidence of unwanted light on the light-receiving section, improving sensitivity.

This infrared sensor can simultaneously capture image information, making it possible to perform motion sensing that recognizes the movement of an object. Furthermore, this infrared sensor can also acquire distance information, making it possible to capture images that include 3D information. Furthermore, this infrared sensor can also be used as a biometric authentication sensor.

The cured film of the present invention can also be used as a colored spacer. For example, when a spacer is used in a TFT-type LCD, light incident on the TFT can cause the TFT to malfunction as a switching element, and colored spacers are used to prevent this. Colored spacers can be formed in the same manner as the black matrix described above, except that a mask for colored spacers is used.

The cured film of the present invention can also be used in applications such as micro LEDs (light emitting diodes) and micro OLEDs (organic light emitting diodes). Although not particularly limited, the cured film can be suitably used for optical filters and optical films used in micro LEDs and micro OLEDs, as well as for components that impart light blocking properties and antireflection properties.
Examples of micro LEDs and micro OLEDs include those described in JP-A-2015-500562 and JP-A-2014-533890.

The cured film of the present invention can also be used in applications such as quantum dot displays. It is not particularly limited, but is suitable for use in optical filters and optical films used in quantum dot displays, as well as components that provide light-blocking and anti-reflection properties.

The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. Note that "parts" and "%" are "parts by mass."
In the present invention, the nonvolatile content or the concentration of the nonvolatile content refers to the mass remaining after leaving the sample to stand in an oven at 180° C. for 30 minutes.

Before going into the examples, we will explain each measurement method.

The resin's weight average molecular weight (Mw), number average molecular weight (Mn), acid value (mg KOH/g), and amine value (mg KOH/g) were measured as follows:

(Average molecular weight of alkali-soluble resin and dispersing resin)
The number-average molecular weight (Mn) and weight-average molecular weight (Mw) of the alkali-soluble resin and dispersion resin were measured by gel permeation chromatography (GPC) equipped with an RI detector. The instrument used was an HLC-8220GPC (manufactured by Tosoh Corporation). Two separation columns were connected in series, and both columns were packed with "TSK-GEL SUPER HZM-N" packings. The oven temperature was 40°C, and the eluent was a tetrahydrofuran (THF) solution. The measurement was performed at a flow rate of 0.35 ml/min. The sample was dissolved in a solvent consisting of 1 wt% of the above eluent and 20 microliters was injected. The molecular weight is a polystyrene equivalent value.

(Acid value of alkali-soluble resin and dispersing resin)
80 ml of acetone and 10 ml of water were added to 0.5 to 1 g of alkali-soluble resin and dispersed resin solution, and the mixture was stirred to dissolve uniformly. The solution was titrated using an automatic titrator ("COM-555", manufactured by Hiranuma Sangyo Co., Ltd.) with a 0.1 mol/L aqueous KOH solution as the titrant to measure the acid value (mg KOH/g). The acid value per unit of nonvolatile content of the resin was then calculated from the acid value of the resin solution and the concentration of nonvolatile content of the resin solution.

(Amine value of dispersing resin)
The amine value of the dispersing resin is the total amine value (mgKOH/g) measured in accordance with the method of ASTM D 2074 and converted into nonvolatile content.

<Production of infrared absorbing compound (A)>
(Infrared absorbing compound (A-1))
400 parts of toluene were mixed with 40.0 parts of 1,8-diaminonaphthalene, 32.2 parts of 3,5-dimethylcyclohexanone, and 0.087 parts of p-toluenesulfonic acid monohydrate, and the mixture was heated and stirred in a nitrogen gas atmosphere and refluxed for 3 hours. Water produced during the reaction was removed from the reaction system by azeotropic distillation. After completion of the reaction, the dark brown solid obtained by distilling the toluene was extracted with acetone and purified by recrystallization from a mixed solvent of acetone and ethanol. The obtained brown solid was dissolved in a mixed solvent of 240 parts of toluene and 160 parts of n-butanol, and 13.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione was added. The mixture was heated and stirred in a nitrogen gas atmosphere and refluxed for 8 hours. Water produced during the reaction was removed from the reaction system by azeotropic distillation.
After completion of the reaction, the solvent was distilled, and 200 parts of hexane was added to the obtained reaction mixture while stirring. The obtained black-brown precipitate was filtered off, washed successively with hexane, ethanol, and acetone, and dried under reduced pressure to obtain an infrared absorbing compound (A-1) represented by the following chemical formula (14). 50 parts of the obtained infrared absorbing compound (A-1), 500 parts of sodium chloride, and 60 parts of diethylene glycol were charged into a stainless steel gallon kneader (manufactured by Inoue Seisakusho), and kneaded at 60°C for 12 hours. Next, the kneaded mixture was poured into warm water and stirred for 1 hour while heating to about 80°C to obtain a slurry. The mixture was filtered and washed with water to remove the sodium chloride and diethylene glycol, and then dried overnight at 80°C and pulverized to obtain a finely divided infrared absorbing compound (A-1).

Chemical formula (14)

(Infrared absorbing compound (A-2))
400 parts of toluene were mixed with 40.0 parts of 1,8-diaminonaphthalene, 50.1 parts of 2-hydroxy-9-fluorenone, and 0.087 parts of p-toluenesulfonic acid monohydrate, and the mixture was heated and stirred in a nitrogen gas atmosphere and refluxed for 3 hours. Water produced during the reaction was removed from the system by azeotropic distillation. After completion of the reaction, the dark brown solid obtained by distilling the toluene was extracted with acetone and purified by recrystallization from a mixed solvent of acetone and ethanol. The obtained brown solid was dissolved in a mixed solvent of 240 parts of toluene and 160 parts of n-butanol, and 13.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione was added. The mixture was heated and stirred in a nitrogen gas atmosphere and refluxed for 8 hours. Water produced during the reaction was removed from the system by azeotropic distillation. After completion of the reaction, the solvent was distilled, and 200 parts of hexane was added to the resulting reaction mixture while stirring. The obtained black-brown precipitate was filtered off, washed successively with hexane, ethanol, and acetone, and dried under reduced pressure, thereby obtaining an infrared absorbing compound (A-2) represented by the following chemical formula (15).
The infrared absorbing compound (A-1) was pulverized in the same manner as above to obtain an infrared absorbing compound (A-2).

Chemical formula (15)

(Infrared absorbing compound (A-3))
In a reaction vessel, 890 parts of n-amyl alcohol, 137 parts of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), 178 parts of 2,3-dicyanonaphthalene, and 40 parts of anhydrous aluminum chloride were mixed and stirred, and after heating, the mixture was refluxed at 136°C for 5 hours. The reaction solution was cooled to 30°C while stirring, and poured into a mixed solvent consisting of 5,000 parts of methanol and 10,000 parts of water while stirring, to obtain a blue slurry. This slurry was filtered, washed with a mixed solvent consisting of 2,000 parts of methanol and 4,000 parts of water, and dried to obtain a compound represented by the following chemical formula (16).
Five parts of diphenyl phosphate was added to 200 parts of N-methylpyrrolidone, and the mixture was thoroughly stirred and mixed, and then heated to 50° C. To this solution, 10 parts of a compound represented by the following chemical formula (16) was added little by little, and the mixture was stirred at 90° C. for 120 minutes. Thereafter, this reaction solution was poured into 2000 parts of water, and the produced precipitate was filtered, washed with water, and dried, thereby obtaining an infrared absorbing compound (A-3) represented by the following chemical formula (17).
The infrared absorbing compound (A-1) was pulverized in the same manner as above to obtain an infrared absorbing compound (A-3).

(Infrared absorbing compound (A-4))
According to the description of WO 2019/058882, an infrared absorbing compound (A-4) represented by the following chemical formula (18) was obtained.
The infrared absorbing compound (A-1) was pulverized in the same manner as above to obtain an infrared absorbing compound (A-4).

Chemical formula (18)

<Production of alkali-soluble resin (B)>
(Alkali-soluble resin (B1-1) solution)
A separable four-neck flask was equipped with a thermometer, a condenser, a nitrogen gas inlet tube, and a stirrer. 100 parts of propylene glycol monomethyl ether acetate (hereinafter, PGMAc) was placed in a reaction vessel, and the vessel was heated to 120°C while injecting nitrogen gas into it. At the same temperature, a mixture of 12.0 parts (30 mol%) of styrene (hereinafter, St), 40.9 parts (40 mol%) of glycidyl methacrylate (hereinafter, GMA), 38.0 parts (30 mol%) of dicyclopentanyl methacrylate (hereinafter, DCPMA), and 1.0 part of azobisisobutyronitrile as a polymerization initiator was added dropwise from the dropping tube over 2.5 hours to carry out a polymerization reaction.
Next, the atmosphere in the flask was replaced with air, and 20.7 parts (100 mol% equivalent of glycidyl groups) of acrylic acid (hereinafter referred to as AA) were charged with 0.3 parts of trisdimethylaminomethylphenol and 0.3 parts of hydroquinone, and the mixture was reacted for 5 hours at 120° C. This caused the epoxy group derived from GMA to react with the carboxyl group of AA, generating hydroxyl groups and introducing polymerizable unsaturated group-containing monomer unit (b3) (hereinafter referred to as GMA+AA).
Further, 17.5 parts of tetrahydrophthalic anhydride (hereinafter referred to as THPA) (50 mol% equivalent of the generated hydroxyl groups) and 0.5 parts of triethylamine were added and reacted at 120°C for 4 hours. This caused an esterification reaction between the hydroxyl groups derived from GMA + AA and TPHA, and fatty acid anhydride-modified polymerizable unsaturated group-containing monomer units (b3) (hereinafter referred to as GMA + AA + TPHA) were introduced. Thereafter, PGMAc was added so that the nonvolatile content became 20%, and an alkali-soluble resin (B1-1) solution was prepared.

(Solutions of alkali-soluble resins (B1-2) to (B1-14) and (B2-1) to (B2-3))
The types and amounts of the compounds were changed to achieve the compositions and mole percentage ratios shown in Table 1, and alkali-soluble resins (B1-2) to (B1-14) and alkali-soluble resins (B2-1) to (B2-3) were synthesized. PGMAc was added to adjust the non-volatile content to 20%.

MAA+GMA in Table 1 represents a polymerizable unsaturated group-containing monomer unit (b3) in which the epoxy group of glycidyl methacrylate is added to the carboxyl group derived from methacrylic acid (MAA), a monomer unit contained in an alkali-soluble resin.

The acid value ranges of the alkali-soluble resins shown in Table 1 are as follows:
A: 40 mg KOH/g or more and 60 mg KOH/g or less B: 30 mg KOH/g or more and less than 40 mg KOH/g, or more than 60 mg KOH/g and 65 mg KOH/g or less C: 20 mg KOH/g or more and less than 30 mg KOH/g, or more than 65 mg KOH/g and 80 mg KOH/g or less D: Less than 20 mg KOH/g, or more than 80 mg KOH/g

The ranges of double bond equivalent weights of the alkali-soluble resins shown in Table 1 are as follows.
A: 200 or more and 700 or less B: More than 700 and 800 or less C: More than 800 and 1000 or less D: Less than 200 or more than 1000

<Production of Colorant (F)>
(Finely divided green pigment (F-1))
100 parts of C.I. Pigment Green 58, 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded for 6 hours at 70° C. This kneaded mixture was added to 3,000 parts of warm water, and stirred for 1 hour with a high-speed mixer while heating to 70° C. to form a slurry. After repeated filtration and washing with water to remove the sodium chloride and diethylene glycol, the mixture was dried overnight at 80° C. and pulverized to obtain a finely divided green pigment (F-1).
(Finely divided green pigment (F-2))
100 parts of C.I. Pigment Green 63, 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded for 6 hours at 70° C. This kneaded mixture was added to 3,000 parts of warm water, and stirred for 1 hour with a high-speed mixer while heating to 70° C. to form a slurry. After repeated filtration and washing with water to remove the sodium chloride and diethylene glycol, the mixture was dried overnight at 80° C. and pulverized to obtain a finely divided green pigment (F-2).

<Production of Dispersion Resin (G)>
(Dispersion resin (G-1) solution)
A reactor equipped with a gas inlet tube, condenser, stirring blade, and thermometer was charged with 40 parts of methyl methacrylate, 10 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine as a catalyst. The mixture was stirred at 50°C for 1 hour while flowing nitrogen, and the system was purged with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate as an initiator, 5.6 parts of cuprous chloride as a catalyst, and 100 parts of PGMAc were charged. The temperature was raised to 110°C under a nitrogen stream to initiate polymerization of the first block (B block). After 4 hours of polymerization, a sample was taken of the polymerization solution and the nonvolatile content was measured. Based on the nonvolatile content, it was confirmed that the polymerization conversion was 98% or higher. Next, 50 parts of PGMAc, 40 parts of dimethylaminoethyl methacrylate as a second block (A block) monomer, and 10 parts of methacryloyloxyethylbenzyldimethylammonium chloride were charged into the reactor. The mixture was stirred while maintaining the temperature at 110°C under a nitrogen atmosphere, and the reaction was continued. Two hours after the addition, the polymerization solution was sampled and the nonvolatile content was measured. It was confirmed that the polymerization conversion rate of the second block (A block) was 98% or higher, calculated from the nonvolatile content. The reaction solution was then cooled to room temperature to terminate the polymerization. GPC measurement revealed that the polymer had a mass average molecular weight of 20,000, a molecular weight distribution Mw/Mn of 1.4, and a reaction conversion rate of 98.5%. In this way, a dispersion resin (G-1) with an amine value per nonvolatile content of 169.8 mgKOH/g was obtained. After cooling to room temperature, approximately 2 g was sampled and dried by heating at 180°C for 20 minutes to measure the nonvolatile content. PGMAc was added so that the nonvolatile content became 30 parts by mass, thereby preparing a dispersion resin (G-1) solution.

(Dispersion resin (G-2) solution)
A reactor equipped with a gas inlet tube, a condenser, a stirring blade, and a thermometer was charged with 30 parts of methyl methacrylate, 30 parts of n-butyl methacrylate, 20 parts of hydroxyethyl methacrylate, and 13.2 parts of tetramethylethylenediamine, and the mixture was stirred at 50°C for 1 hour while flowing nitrogen, thereby replacing the atmosphere in the system with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of PGMAc were charged, and the temperature was raised to 110°C under a nitrogen stream to initiate polymerization of the first block (B block). After 4 hours of polymerization, a sample was taken from the polymerization solution and the nonvolatile content was measured. It was confirmed that the polymerization conversion rate was 98% or higher, calculated from the nonvolatile content.
Next, 61 parts of PGMAc and 20 parts of 1,2,2,6,6-pentamethylpiperidyl methacrylate (Fancryl FA-711MM, manufactured by Hitachi Chemical Co., Ltd.) as a second block (A block) monomer were added to this reactor, and the reaction was continued by stirring while maintaining the temperature at 110°C under a nitrogen atmosphere. Two hours after the addition of 1,2,2,6,6-pentamethylpiperidyl methacrylate, a sample of the polymerization solution was taken and the nonvolatile content was measured. It was confirmed that the polymerization conversion rate of the second block (A block) was 98% or higher, calculated from the nonvolatile content, and the reaction solution was cooled to room temperature to terminate the polymerization. The solution was diluted with PGMAc so that the nonvolatile content was 30% by nonvolatile content measurement, yielding a dispersion resin (G-2) solution with an amine value per nonvolatile content of 57 mgKOH/g and a number average molecular weight (Mn) of 4,500.

<Preparation of Dispersion>
(Dispersion 1)
The following raw materials were mixed and stirred to a uniform consistency, then dispersed in an Eiger mill (Eiger Japan Co., Ltd., "Mini Model M-250 MKII") using zirconia beads with a diameter of 0.5 mm for 3 hours, and then filtered through a filter with a pore size of 1.0 μm to prepare Dispersion 1. The organic solvent (Q-1) was PGMAc.
Infrared absorbing compound (A-1): 9.38 parts Dispersion resin (G-1): 18.75 parts Organic solvent (Q-1): 71.88 parts

(Dispersions 2 to 6)
Dispersions 2 to 6 were prepared in the same manner as Dispersion 1, except that the raw materials and amounts shown in Table 2 were changed.

<Production of Photosensitive Composition>
[Example 1]
(Photosensitive composition 1)
The following raw materials were mixed and stirred, and then filtered through a filter having a pore size of 1.0 μm to obtain Photosensitive Composition 1.
Dispersion 1: 12.80 parts Alkali-soluble resin (B1-1) solution: 26.34 parts Polymerizable compound (C): 6.75 parts Photopolymerization initiator (D1-1): 0.30 parts Benzophenone-based sensitizer (E-1): 0.75 parts Leveling agent (N): 1.00 parts Organic solvent (Q): 52.06 parts

[Examples 2 to 32, Comparative Examples 1 to 7]
(Photosensitive compositions 2 to 39)
Photosensitive compositions 2 to 39 were prepared in the same manner as in Example 1, except that the photosensitive composition 1 in Example 1 was changed to the raw materials and amounts shown in Tables 3-1 to 3-4.

The details of each ingredient listed in Tables 3-1 to 3-4 are as follows:

[Polymerizable compound (C)]
C-1: Aronix M-402 (manufactured by Toagosei Co., Ltd., a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate)
C-2: Aronix M-450 (manufactured by Toagosei Co., Ltd., a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate)
Equal amounts of (C-1) and (C-2) were mixed to prepare a polymerizable compound (C).

[Photopolymerization initiator (D)]
(Photopolymerization initiator (D1) represented by general formula (1))
D1-1: Photopolymerization initiator of the above-mentioned chemical formula (12) D1-2: Photopolymerization initiator of the above-mentioned chemical formula (13)

(Other Photopolymerization Initiators (D2))
D2-1: Omnirad 369 (manufactured by IGM Resins, acetophenone-based photopolymerization initiator)
D2-2: Omnirad 907 (manufactured by IGM Resins, acetophenone-based photopolymerization initiator)
D2-3: Omnirad TPO (manufactured by IGM Resins, acylphosphine oxide photopolymerization initiator)
D2-4: IRGACURE OXE-04 (manufactured by BASF Japan, oxime-based photopolymerization initiator)

[Benzophenone-based sensitizer (E)]
E-1: 4,4'-bis(diethylamino)benzophenone

[Sensitizer (E2) other than benzophenone-based sensitizer (E)]
E2-1: 2,4-diethylthioxanthone

[Leveling agent (N)]
N-1: BYK-330 (manufactured by BYK-Chemie)
N-2: Megafac F-554 (DIC Corporation)
One part each of (N-1) and (N-2) was mixed and dissolved in 98 parts of PGMAc to prepare a mixed solution, which was used as a leveling agent (N).

[Organic solvent (Q)]
Q-1: Propylene glycol monomethyl ether acetate 40 parts Q-2: Cyclohexanone 20 parts Q-3: Propylene glycol monomethyl ether 40 parts The above (Q-1) to (Q-3) were mixed in the above-mentioned parts by mass to obtain organic solvent (Q).

<Evaluation of Photosensitive Composition>
The resulting photosensitive compositions 1 to 39 (Examples 1 to 32 and Comparative Examples 1 to 7) were evaluated for developability, pattern formability, and heat resistance by the following methods. The evaluation results are shown in Table 4.

[Evaluation of developability]
The obtained photosensitive composition was applied by spin coating to a 100 mm x 100 mm, 0.7 mm thick glass substrate (Corning Eagle 2000) so that the dried film thickness would be 2.0 μm, and then dried on a hot plate at 70°C for 1 minute. The substrate was then cooled to room temperature and exposed to ultraviolet light using a high-pressure mercury lamp at an illuminance of 30 mW/ ^cm2 and 50 mJ/ ^cm2 through a photomask with a 100 μm wide stripe pattern. After cooling to room temperature, the substrate was spray-developed using an aqueous developer containing 0.12% nonionic surfactant and 0.04% potassium hydroxide at 23°C, washed with ion-exchanged water, and air-dried.
The pattern was observed under an optical microscope to evaluate the presence or absence of development residues in the unexposed areas and pattern defects. The evaluation criteria are as follows, with 3 or more being practical.
5: After a development time of 70 seconds, there was no development residue in the unexposed areas and no pattern defects.
4: After a development time of 70 seconds, slight development residue was observed in the unexposed area and/or slight pattern defects were observed.
3: After a development time of 70 seconds, a small amount of development residue was observed in the unexposed area and/or a small amount of pattern loss was observed.
2: After a development time of 70 seconds, development residues were observed in the unexposed areas and/or pattern defects were observed.
1: Pattern defects occurred at a development time of 40 seconds.

[Evaluation of Pattern Formability (1): Adhesion]
The obtained photosensitive composition was applied by spin coating to a 100 mm long x 100 mm wide, 0.7 mm thick glass substrate (Corning Eagle 2000) so that the film thickness after drying was 2.0 μm, and then dried on a hot plate at 70 ° C. for 1 minute. Next, after cooling the substrate to room temperature, it was exposed to light using a high-pressure mercury lamp at an illuminance of 30 mW/cm ² and 40 mJ/cm ² through a photomask with a stripe pattern of 5 μm width intervals. Thereafter, the substrate was spray-developed using an organic alkaline developer NMD-3 (Tokyo Ohka Kogyo Co., Ltd.) at 23 ° C., washed with ion-exchanged water, air-dried, and heated in a clean oven at 230 ° C. for 30 minutes to obtain a substrate for adhesion evaluation. Spray development was performed for each photosensitive composition coating for the shortest time possible to form a pattern without residual development, and this was determined to be the appropriate development time.
Of the patterns on the substrate for evaluating adhesion, fine line patterns with widths of 5 to 25 μm were observed under an optical microscope to confirm the minimum line width of the remaining fine line patterns. The evaluation criteria are as follows, with 3 or more being practical.
5: Fine lines of 10 μm or less remain.
4: Fine lines of 15 μm or more remain.
3: Fine lines of 20 μm or more remain.
2: Fine lines of 25 μm or more remain.
1: No fine lines remain.

[Evaluation of Pattern Formability (2): Linearity]
The substrate prepared in the pattern formability evaluation (1) was evaluated by measuring the maximum and minimum line widths of 10 stripe patterns using a Nikon ECLIPSE LV100POL Model optical microscope and calculating the average. The evaluation criteria are as follows, with a score of 3 or higher being practical.
5: The difference between the maximum and minimum line widths is less than 0.5 μm. 4: The difference between the maximum and minimum line widths is 0.5 μm or more and less than 1.0 μm. 3: The difference between the maximum and minimum line widths is 1.0 μm or more and less than 1.5 μm. 2: The difference between the maximum and minimum line widths is 1.5 μm or more and less than 2.0 μm. 1: The difference between the maximum and minimum line widths is 2.0 μm or more.

[Heat resistance evaluation]
The obtained photosensitive composition was applied to a glass substrate (Corning Eagle 2000) measuring 100 mm long x 100 mm wide and 0.7 mm thick using a spin coater to give a dry film thickness of 3.0 μm, and then dried on a hot plate for 1 minute at 70° C. Next, after cooling to room temperature, the substrate was exposed to light using a high-pressure mercury lamp at an illuminance of 30 mW/cm ² and 40 mJ/cm ² to obtain a substrate for evaluating heat resistance.
The absorbance of the obtained substrate for heat resistance evaluation was measured at the maximum absorption wavelength and an incident angle of 0° C. using a spectrophotometer (U-4100 manufactured by Hitachi High-Technologies Corporation), and this was taken as the initial value.
The heat resistance evaluation substrate was then heated to 210°C for 20 minutes, cooled, and the absorbance was measured again, and this was used as the value after the heat resistance test. The heat resistance was calculated using the following formula. The evaluation criteria are as follows, with 3 or more being practical.
Residual rate = (absorbance after heat resistance test) ÷ (initial absorbance) × 100
5: Residual rate is 97% or more 4: Residual rate is 95% or more but less than 97% 3: Residual rate is 93% or more but less than 95% 2: Residual rate is 90% or more but less than 93% 1: Residual rate is less than 90%

10 Image display device 11 Transparent substrate 12 TFT array 13 Transparent electrode layer 14 Alignment layer 15 Polarizer 21 Transparent substrate 22 Color filter 23 Transparent electrode layer 24 Alignment layer 25 Polarizer 30 Backlight unit 31 White LED light source LC Liquid crystal

200 Solid-state imaging device 201 Solid-state imaging element 202 Imaging section 203 Cover glass 204 Spacer 205 Laminated substrate 206 Chip substrate 207 Circuit board 208 Electrode pad 209 External connection terminal 210 Through electrode 211 Lens layer 212 Lens material 213 Support 214 Hardened film 215 Hardened film

300 Infrared sensor 310 Solid-state imaging element 311 Infrared cut filter 312 Color filter 313 Infrared transmission filter 314 Resin film 315 Microlens 316 Flattening film

Claims (9)

A photosensitive composition comprising an infrared absorbing compound (A), an alkali-soluble resin (B ), a polymerizable compound (C), a photopolymerization initiator (D), and a benzophenone-based sensitizer (E),
the alkali-soluble resin (B) comprises an alkali-soluble resin (B1) containing an alicyclic hydrocarbon-containing monomer unit (b1) having a homopolymer glass transition temperature of 80°C or higher and an aromatic ring-containing monomer unit (b2) having a homopolymer glass transition temperature of 80°C or higher;
the total content of the alicyclic hydrocarbon-containing monomer unit (b1) and the aromatic ring-containing monomer unit (b2) is 40 to 80 mol % relative to 100 mol % of all structural units of the alkali-soluble resin (B1);
The photosensitive composition has a content of the benzophenone-based sensitizer (E) of 100 to 500 parts by mass relative to 100 parts by mass of the photopolymerization initiator (D). 2. The photosensitive composition according to claim 1 , wherein the alkali-soluble resin (B1) has an acid value of 30 to 65 mgKOH/g. 3. The photosensitive composition according to claim 1, wherein the content of the infrared absorbing compound (A) is 1 to 15 parts by mass per 100 parts by mass of the nonvolatile content of the photosensitive composition. The photosensitive composition according to any one of claims 1 to 3 , wherein the photopolymerization initiator (D) comprises a photopolymerization initiator represented by the following general formula (1):
General formula (1)

(In the general formula (1), R ₁ and R ₂ each independently represent a hydrogen atom or a group having 1 to 10 carbon atoms.)
_R3 represents a hydrogen atom or a monovalent substituent. A cured film obtained by curing the photosensitive composition according to any one of claims 1 to 4 . An optical filter comprising the cured film according to claim 5 . An image display device comprising the optical filter according to claim 6 . A solid-state imaging device comprising the cured film according to claim 5 . An infrared sensor comprising the cured film according to claim 5 .