JP2023125704A - Manufacturing method of optical element, optical element and photosensitive composition - Google Patents

Abstract

To provide a manufacturing method of optical element capable of inhibiting leak light of an optical element including a lens and a light blocking layer located on a lens peripheral edge and at least covering part of a curved surface of the lens, and a photosensitive composition usable for a manufacturing method of the optical element.SOLUTION: There is provided a manufacturing method of an optical element which includes a lens and a light blocking layer located on a lens peripheral edge and at least covering part of a curved surface of the lens. The method includes: applying a photosensitive composition on the curved surface of the lens to form a coating film; positionally and selectively exposing a site on the coating film where the light blocking layer is formed; developing the exposed coating film; and heating and curing the developed coating film. Examples used as the photosensitive composition include: a photosensitive composition containing alkali-soluble resin, photopolymerizable monomer, photoinitiator, light blocking agent and organic solvent, having specific thixotropy index and viscosity; or a photosensitive composition containing alkali-soluble resin, photo polymerizable monomer, photoinitiator, light blocking agent, thickener and organic solvent.SELECTED DRAWING: None

Description

The present invention relates to a method for manufacturing an optical element including a lens and a light-shielding layer, an optical element, and a photosensitive composition used for forming the light-shielding layer on the lens.

Lenses are used as optical elements in optical devices such as cameras, microscopes, semiconductor exposure devices, and binoculars.
In order to suppress flare, ghost, etc. caused by the reflection of incident light in such lenses, there is a technique to provide a matte film on the peripheral edge of the lens by plating or coating process (see Patent Document 1), and a black coloring photosensitive technique. A technique (see Patent Document 2) has been disclosed in which a coating film formed by applying a polyurethane resin composition to a lens is selectively exposed and developed to provide a light-shielding layer at the peripheral edge of the lens.

JP2020-109510A Japanese Patent Application Publication No. 2011-107588

As optical equipment becomes smaller, lenses are also becoming smaller, so a finer light-shielding layer and the like are desired. As in Patent Document 2, a light-shielding layer having a fine pattern shape is provided by positionally selectively exposing and developing a coating film formed by applying a negative black colored photosensitive resin composition to a lens. I can do it.
However, as in Patent Document 2, when a light-shielding layer is provided by position-selectively exposing and developing a coating film formed by coating a negative black colored photosensitive resin composition on a lens, the light-shielding layer , light leakage may occur where incident light is transmitted.
To be more specific, for example, as shown in FIG. 1, which is a schematic cross-sectional view showing an optical element 10 having a lens 1 and a light-shielding layer 2, a lens 1 is formed by applying a negative black colored photosensitive resin composition. By subjecting the coating film to position-selective exposure and development, a light-shielding layer 2 located at the periphery of the lens 1 and covering at least a part of the curved surface of the lens 1 is provided on the lens 1. The thickness of the light-shielding layer becomes thinner at a portion (slanted portion 2a) provided on a curved surface (that is, an inclined surface), and light leakage may occur. Note that light leakage is unlikely to occur at a portion (flat portion 2b) of the light shielding layer 2 provided on the plane (that is, horizontal plane) of the lens 1.
When light leakage occurs, flare, ghost, etc. may occur due to reflection of incident light.

The present invention has been made in view of the above-mentioned problems, and is capable of suppressing light leakage of an optical element including a lens and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens. The present invention aims to provide a method for producing an optical element that can be produced, a photosensitive composition that can be used in the method for producing the optical element, and an optical element using the photosensitive composition.

The present inventors prepared an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light-blocking agent (D), and an organic solvent (S). In this method, a photosensitive composition is used which has a thixotropy index expressed by the following formula (1) of 1.5 or more and a viscosity V2 of 6 cP or more at 25° C. and a rotational speed of 50 rpm in an E-type viscometer. Or, an alkali-soluble resin (A), a photopolymerizable monomer (B), a photoinitiator (C), a light shielding agent (D), a thickener (E), and an organic solvent (S). The inventors have discovered that the above-mentioned problems can be solved by using a photosensitive composition containing the following, and have completed the present invention. Specifically, the present invention provides the following.

A first aspect of the present invention is a method for manufacturing an optical element comprising a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens,
a coating film forming step of applying a photosensitive composition to the curved surface of the lens to form a coating film;
an exposure step of positionally selectively exposing a position in the coating film where the light shielding layer is formed;
A developing step of developing the coated film after exposure;
A thermosetting step of heating and curing the coated film after development,
The photosensitive composition includes an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S),
The photosensitive composition has a thixotropy index expressed by the following formula (1) of 1.5 or more at 25°C, and a viscosity V2 of 6 cP at 50 rpm in an E-type viscometer at 25°C. The above is the method for manufacturing an optical element.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotation speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. )

A second aspect of the present invention is a method for manufacturing an optical element comprising a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens,
a coating film forming step of applying a photosensitive composition to the curved surface of the lens to form a coating film;
an exposure step of positionally selectively exposing a position in the coating film where the light shielding layer is formed;
A developing step of developing the coated film after exposure;
A thermosetting step of heating and curing the coated film after development,
The photosensitive composition comprises an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic solvent. (S).

A third aspect of the present invention is a photosensitive composition used for forming a light-shielding layer on a lens consisting of a convex lens or a concave lens, which is located at the periphery of the lens and covers at least a part of the curved surface of the lens. ,
Contains an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S),
At 25°C, the thixotropy index represented by the following formula (1) is 1.5 or more,
The photosensitive composition has a viscosity V2 of 6 cP or more at 25° C. and a rotation speed of 50 rpm using an E-type viscometer.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotational speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. )

A fourth aspect of the present invention is a photosensitive composition used for forming a light-shielding layer on a lens consisting of a convex lens or a concave lens, which is located at the periphery of the lens and covers at least a part of the curved surface of the lens. ,
A photosensitive material containing an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic solvent (S) It is a sexual composition.

A fifth aspect of the present invention includes a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens,
The light-shielding layer is an optical element made of a cured product of the photosensitive composition according to the third or fourth aspect.

According to the present invention, there is provided a method for manufacturing an optical element capable of suppressing light leakage of an optical element including a lens and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens; A photosensitive composition that can be used in a method for manufacturing an element, and an optical element using the photosensitive composition can be provided.

FIG. 2 is a schematic cross-sectional view showing an optical element having a lens and a light-shielding layer. 1 is a schematic diagram showing an example of an optical element manufactured in Embodiment 1. FIG. FIG. 2 is a schematic cross-sectional view illustrating a method for manufacturing an optical element. FIG. 3 is a schematic cross-sectional view illustrating a method for evaluating the thickness of a light-shielding layer.

The present invention will be described below based on embodiments. Note that in this specification, a range expressed using "~" is defined as a range that includes numerical values or ratios at both ends.

(Embodiment 1)
The method for manufacturing an optical element of this embodiment is a method for manufacturing an optical element including a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens.
The method for manufacturing the optical element includes a coating film forming step of applying a photosensitive composition to a curved surface of a lens to form a coating film, and position-selectively exposing a position in the coating film where a light-shielding layer is to be formed. The method includes an exposure step, a development step of developing the exposed coating film, and a thermosetting step of heating and curing the developed coating film.
The photosensitive composition to be applied contains an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S). include.
Further, the photosensitive composition has a thixotropy index expressed by the following formula (1) of 1.5 or more at 25°C, and a viscosity V2 at a rotation speed of 50 rpm using an E-type viscometer at 25°C. It is 6cP or more.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotation speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. )

In the method for manufacturing an optical element of this embodiment, as shown in FIG. 2, an optical element 10 including a lens 1 and a light shielding layer 2 located at the periphery of the lens 1 and covering at least a part of the curved surface of the lens 1 is manufactured. do. FIG. 2 is a schematic diagram showing an example of an optical element manufactured in Embodiment 1. FIG. 1(a) is a cross-sectional view. FIG. 1(b) is a plan view. Note that the shapes of the lens 1 and the light shielding layer 2 in FIG. 2 are merely examples. The shapes of the lens 1 and the light shielding layer 2 in FIG. 2 can be changed to various shapes depending on the desired optical element 10.
The periphery of the lens 1 on which the light shielding layer 2 is located is the periphery when the thickness direction of the lens 1 (the direction in which light is incident) is the axis.

Here, by position-selectively exposing and developing a coating film formed by applying a photosensitive composition to the lens 1, a light-shielding layer is formed that is located at the periphery of the lens 1 and covers at least a part of the curved surface of the lens 1. 2, there is a problem that light leakage may occur at a portion (slanted portion 2a) of the light shielding layer 2 provided on the curved surface (that is, the sloped surface) of the lens 1. When light leakage occurs, there is a concern that flare, ghost, etc. may occur due to reflection of incident light.
However, in this embodiment, it includes an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S), At 25°C, the thixotropy index expressed by the above formula (1) is 1.5 or more, and at 25°C, the viscosity V2 at a rotation speed of 50 rpm in an E-type viscometer is 6 cP or more. By using this composition, the above-mentioned light leakage can be suppressed, as shown in the Examples described below.

Since the curved surface of the lens 1 at the peripheral edge of the lens 1 is inclined, when a photosensitive composition is applied to the curved surface (slanted surface) of the lens 1 at the peripheral edge of the lens 1 by a method such as spray coating to form a coating film, the photosensitive composition is The sexual composition easily flows along the slope of the curved surface of the lens 1.
When the photosensitive composition flows along the slope, a thin light-shielding layer 2 (slope portion 2a) is formed on the curved surface of the lens 1. It is presumed that in an optical element provided with a thin light-shielding layer 2, the light-shielding layer 2 cannot sufficiently absorb light, and light leakage is likely to occur. Note that in the portion of the light-shielding layer 2 that corresponds to the plane of the lens 1 (flat portion 2b), such a phenomenon in which the photosensitive composition flows along the slope of the curved surface of the lens 1 does not occur, so light leakage does not occur. Hard to occur.

On the other hand, in this embodiment, a coating film is formed using the above specific photosensitive composition. Therefore, the photosensitive composition tends to stay on the curved surface (slanted surface) of the lens 1 at the periphery of the lens 1 and is difficult to flow along the curved surface of the lens 1. As a result, a thick light shielding layer 2 (slope portion 2a) can be formed on the curved surface of the lens 1. In an optical element including a thick light-shielding layer 2, the light-shielding layer 2 sufficiently absorbs light and light leakage is suppressed. In addition, the light absorption ability of the light shielding layer 2 formed on the curved surface of the lens 1 (inclined part 2a) of the light shielding layer 2, and the light absorption ability of the part of the light shielding layer 2 corresponding to the plane of the lens 1 (flat part 2b) It is also possible to reduce the difference in light absorption ability.
Since light leakage is suppressed, the optical element 10 in which the light shielding layer 2 is formed on the lens 1 manufactured in this embodiment can be preferably used in optical equipment such as a camera, a microscope, and a semiconductor exposure apparatus.

Moreover, the above-mentioned specific photosensitive composition can be easily applied to coating methods such as spray coating, and has good handling properties.

The thixotropy index represented by the above formula (1) may be 1.5 or more. From the viewpoint of further suppressing light leakage, the thixotropy index is preferably 1.60 or more, more preferably 1.70 or more.
Further, the viscosity V2 may be 6 cP or more. From the viewpoint of further suppressing light leakage, the viscosity V2 is preferably 8 cP or more, and more preferably 12 cP or more.

The thixotropy index expressed by the above formula (1) and the above viscosity V2 can be set to desired values by adjusting the types and blending ratios of the essential components and optional components contained in the photosensitive composition, which will be described in detail later. be able to. For example, by adjusting the type and amount of the thickener used, the thixotropy index expressed by the above formula (1) and the viscosity V2 can be adjusted.

Each step will be described in detail below using FIG. 3. FIG. 3 is a schematic cross-sectional view illustrating a method of manufacturing the optical element 10.

<Coating film formation process>
In the coating film forming step, as shown in FIGS. 3(a) and 3(b), a photosensitive composition is applied to the curved surface of the lens 1 to form a coating film 2a.

The type of lens 1 is not particularly limited. In FIG. 3, a convex lens is shown as the lens 1, but a concave lens may also be used.
The material of the lens is also not particularly limited. Preferred lenses include glass lenses and resin lenses. Examples of the resin constituting the lens include polycarbonate, cycloolefin polymer, epoxy resin, and acrylic resin.
The thickness of the lens is also not particularly limited, but is, for example, 1 cm or less, preferably 100 μm or more and 2000 μm or less. Note that the thickness of the lens is the thickness of the thickest part. The diameter of the lens is not particularly limited, but is, for example, 40 mm or less, preferably 1 mm or more and 10 mm or less, and more preferably 1 mm or more and 5 mm or less.

In the coating film forming step, the photosensitive composition applied to the lens 1 includes an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), Contains an organic solvent (S).
Further, the photosensitive composition has a thixotropy index expressed by the following formula (1) of 1.5 or more at 25°C, and a viscosity V2 at a rotation speed of 50 rpm using an E-type viscometer at 25°C. It is 6cP or more.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotation speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. )
Hereinafter, essential or optional components of the photosensitive composition to be applied will be explained.

≪Photosensitive composition (black photosensitive composition)≫
<Alkali-soluble resin (A)>
The photosensitive composition contains an alkali-soluble resin (A) (hereinafter also referred to as component (A)). By blending the alkali-soluble resin (A) into the photosensitive composition, alkali developability can be imparted to the photosensitive composition.
Here, in this specification, the alkali-soluble resin refers to a resin having a functional group (for example, a phenolic hydroxyl group, a carboxy group, a sulfonic acid group, etc.) that imparts alkali solubility in the molecule.

The alkali-soluble resin (A) preferably includes a resin containing a photopolymerizable group such as an ethylenically unsaturated double bond in the molecule. In this case, when forming a cured product (light-shielding layer) using the photosensitive composition, crosslinking occurs between the alkali-soluble resin (A) and the photopolymerizable monomer (B). Therefore, even if the baking temperature for forming the cured product is as low as, for example, 120° C. or lower, further 100° C. or lower, or 95° C. or lower, it is easy to form a cured product with high solvent resistance.
Typical examples of photopolymerizable groups include functional groups having unsaturated double bonds such as vinyl groups, allyl groups, and (meth)acryloyl groups.

The alkali-soluble resin (A) preferably contains a resin (a-1) having a cardo structure in its molecule. The cardo structure will be described in detail later.
When using a resin having a cardo structure in the molecule, it is easy to obtain a photosensitive composition with excellent resolution, and it is easy to form a cured product using the photosensitive composition that has good adhesion to lenses.

[Resin with cardo structure (a-1)]
As the resin (a-1) having a cardo structure (hereinafter also referred to as cardo resin (a-1)), a resin having a cardo structure in the molecule and having a predetermined alkali solubility can be used. The cardo structure refers to a skeleton in which a second cyclic structure and a third cyclic structure are bonded to one ring carbon atom constituting the first cyclic structure. Note that the second cyclic structure and the third cyclic structure may be the same structure or different structures.
A typical example of the cardo structure is a skeleton in which two aromatic rings (for example, benzene rings) are bonded to the 9-position carbon atom of a fluorene ring.

The cardo resin (a-1) is not particularly limited, and conventionally known resins can be used. Among these, a resin represented by the following formula (a-1) is preferred. The resin represented by the following formula (a-1) has a (meth)acryloyl group in the molecule, as shown by the following formula (a-2). Therefore, the resin represented by the following formula (a-1) corresponds to a resin containing a photopolymerizable group in the molecule.

In formula (a-1), X ^a represents a group represented by formula (a-2) below. m1 represents an integer from 0 to 20.

In the above formula (a-2), R ^a1 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a halogen atom, and R ^a2 each independently represents a hydrogen atom or a methyl group. R ^a3 each independently represents a linear or branched alkylene group, m2 represents 0 or 1, and W ^a represents a group represented by the following formula (a-3).

In formula (a-2), R ^a3 is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 1 to 10 carbon atoms, and an alkylene group having 1 to 6 carbon atoms. are particularly preferred, and ethane-1,2-diyl, propane-1,2-diyl, and propane-1,3-diyl groups are most preferred.

Ring A in formula (a-3) represents an aliphatic ring which may be fused with an aromatic ring or may have a substituent. The aliphatic ring may be an aliphatic hydrocarbon ring or an aliphatic heterocycle.
Examples of the aliphatic ring include monocycloalkane, bicycloalkane, tricycloalkane, and tetracycloalkane.
Specific examples include monocycloalkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, and adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane.
The aromatic ring which may be fused to the aliphatic ring may be an aromatic hydrocarbon ring or an aromatic heterocycle, with an aromatic hydrocarbon ring being preferred. Specifically, a benzene ring and a naphthalene ring are preferred.

Suitable examples of the divalent group represented by formula (a-3) include the following groups.

The divalent group ^{X a} in formula (a-1) can be converted to a cardo by reacting a tetracarboxylic dianhydride giving the residue Z ^a with a diol compound represented by the following formula (a-2a). Introduced into resin (a-1).

In formula (a-2a), R ^a1 , R ^a2 , R ^a3 , and m2 are as described for formula (a-2). Ring A in formula (a-2a) is as described for formula (a-3).

The diol compound represented by formula (a-2a) can be produced, for example, by the following method.
First, after substituting the hydrogen atom in the phenolic hydroxyl group of the diol compound represented by the following formula (a-2b) with a group represented by -R ^a3 -OH according to a conventional method, if necessary, Glycidylation is performed using epichlorohydrin or the like to obtain an epoxy compound represented by the following formula (a-2c).
Next, the diol compound represented by formula (a-2a) is obtained by reacting the epoxy compound represented by formula (a-2c) with acrylic acid or methacrylic acid.
In formula (a-2b) and formula (a-2c), R ^a1 , R ^a3 , and m2 are as described for formula (a-2). Ring A in formula (a-2b) and formula (a-2c) is as described for formula (a-3).
Note that the method for producing the diol compound represented by formula (a-2a) is not limited to the above method.

Suitable examples of the diol compound represented by formula (a-2b) include the following diol compounds.

In the above formula (a-1), R ^a0 is a hydrogen atom or a group represented by -CO-Y ^a -COOH. Here, Y ^a represents a residue obtained by removing an acid anhydride group (-CO-O-CO-) from a dicarboxylic acid anhydride. Examples of dicarboxylic anhydrides include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, chlorendic anhydride, and methyltetrahydrophthalic anhydride. Examples include phthalic anhydride and glutaric anhydride.

Further, in the above formula (a-1), Z ^a represents a residue obtained by removing two acid anhydride groups from a tetracarboxylic dianhydride. Examples of tetracarboxylic dianhydride include tetracarboxylic dianhydride represented by the following formula (a-4), pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, and biphenyltetracarboxylic dianhydride. and biphenyl ether tetracarboxylic dianhydride.
Furthermore, in the above formula (a-1), m1 represents an integer of 0 or more and 20 or less.

（式（ａ－４）中、Ｒ^ａ４、Ｒ^ａ５、及びＲ^ａ６は、それぞれ独立に、水素原子、炭素原子数１以上１０以下のアルキル基及びフッ素原子からなる群より選択される１種を示し、ｍ３は、０以上１２以下の整数を示す。）

(In formula (a-4), R ^a4 , R ^a5 , and R ^a6 each independently represent one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a fluorine atom. (m3 represents an integer from 0 to 12.)

The alkyl group that can be selected as R ^a4 in formula (a-4) is an alkyl group having 1 or more and 10 or less carbon atoms. By setting the number of carbon atoms included in the alkyl group within this range, the heat resistance of the obtained carboxylic acid ester can be further improved. When R ^a4 is an alkyl group, the number of carbon atoms is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 4 or less, from the standpoint of easily obtaining cardo resin having excellent heat resistance. Particularly preferably 1 or more and 3 or less.
When R ^a4 is an alkyl group, the alkyl group may be linear or branched.

R ^a4 in formula (a-4) is more preferably a hydrogen atom or an alkyl group having 1 or more and 10 or less carbon atoms, each independently from the viewpoint that it is easy to obtain a cardo resin having excellent heat resistance. R ^a4 in formula (a-4) is more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group, and particularly preferably a hydrogen atom or a methyl group.
A plurality of R ^a4 's in formula (a-4) are preferably the same group because it is easy to prepare a highly pure tetracarboxylic dianhydride.

m3 in formula (a-4) represents an integer from 0 to 12. By setting the value of m3 to 12 or less, purification of the tetracarboxylic dianhydride can be facilitated.
From the viewpoint of easy purification of the tetracarboxylic dianhydride, the upper limit of m3 is preferably 5, and more preferably 3.
From the viewpoint of chemical stability of the tetracarboxylic dianhydride, the lower limit of m3 is preferably 1, and more preferably 2.
In formula (a-4), m3 is particularly preferably 2 or 3.

The alkyl group having 1 to 10 carbon atoms that can be selected as R ^a5 and R ^a6 in formula (a-4) is the same as the alkyl group having 1 to 10 carbon atoms that can be selected as R ^a4 . .
R ^a5 and R ^a6 are a hydrogen atom or a carbon atom number of 1 to 10 (preferably 1 to 6, more preferably 1 to 5, More preferably, it is an alkyl group of 1 or more and 4 or less, particularly preferably 1 or more and 3 or less, and particularly preferably a hydrogen atom or a methyl group.

Examples of the tetracarboxylic dianhydride represented by formula (a-4) include norbornane-2-spiro-α-cyclopentanone-α'-spiro-2''-norbornane-5,5'', 6,6''-tetracarboxylic dianhydride (also known as "norbornane-2-spiro-2'-cyclopentanone-5'-spiro-2''-norbornane-5,5'',6,6'') -tetracarboxylic dianhydride"), methylnorbornane-2-spiro-α-cyclopentanone-α'-spiro-2''-(methylnorbornane)-5,5'',6,6''-tetra Carboxylic dianhydride, norbornane-2-spiro-α-cyclohexanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride (also known as ``norbornane- 2-spiro-2'-cyclohexanone-6'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride"), methylnorbornane-2-spiro-α- Cyclohexanone-α'-spiro-2''-(methylnorbornane)-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclopropanone-α'- spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclobutanone-α'-spiro-2''-norbornane-5, 5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cycloheptanone-α'-spiro-2''-norbornane-5,5'',6,6' '-Tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclooctanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride , norbornane-2-spiro-α-cyclononanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclodecanone -α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cycloundecanone-α'-spiro-2' '-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclododecanone-α'-spiro-2''-norbornane-5,5' ',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclotridecanone-α'-spiro-2''-norbornane-5,5'',6,6''- Tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclotetradecanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-cyclopentadecanone-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α -(Methylcyclopentanone)-α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-α-(methylcyclohexanone) -α'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride and the like.

The content of the resin (a-1) having a cardo structure in the alkali-soluble resin (A) is not particularly limited, but is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 90% by mass or more. .

The mass average molecular weight of the cardo resin (a-1) is preferably 1,000 or more and 40,000 or less, more preferably 1,500 or more and 30,000 or less, and even more preferably 2,000 or more and 10,000 or less. By setting it as the said range, sufficient heat resistance and mechanical strength can be obtained for a cured film, while obtaining good developability.
In this specification, the mass average molecular weight Mw is a value measured by gel permeation chromatography (GPC) in terms of polystyrene.

[Novolak resin (a-2)]
From the viewpoint of imparting high heat resistance to the cured film that does not easily flow or deform due to heat, it is also preferable to include a novolak resin (a-2) as the alkali-soluble resin (A).
As the novolak resin (a-2), various novolak resins conventionally blended into photosensitive compositions can be used. The novolac resin (a-2) is preferably one obtained by addition condensation of an aromatic compound having a phenolic hydroxyl group (hereinafter simply referred to as "phenols") and an aldehyde under an acid catalyst.

(Phenols)
Examples of phenols used in producing the novolac resin (a-2) include phenol; cresols such as o-cresol, m-cresol, and p-cresol; 2,3-xylenol, 2,4-xylenol; , 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol and other xylenol; o-ethylphenol, m-ethylphenol, p-ethylphenol and other ethylphenols; 2 - Alkylphenols such as isopropylphenol, 3-isopropylphenol, 4-isopropylphenol, o-butylphenol, m-butylphenol, p-butylphenol, and p-tert-butylphenol; 2,3,5-trimethylphenol, and 3,4 , 5-trimethylphenol; polyhydric phenols such as resorcinol, catechol, hydroquinone, hydroquinone monomethyl ether, pyrogallol, and phloroglycinol; alkyl polyhydric phenols such as alkylresorcinol, alkylcatechol, and alkylhydroquinone. (Each alkyl group has 1 to 4 carbon atoms.); α-naphthol; β-naphthol; hydroxydiphenyl; and bisphenol A. These phenols may be used alone or in combination of two or more.

Among these phenols, m-cresol and p-cresol are preferred, and it is more preferred to use m-cresol and p-cresol in combination. In this case, various properties such as heat resistance of the cured film formed using the photosensitive composition can be adjusted by adjusting the blending ratio of both.
The blending ratio of m-cresol and p-cresol is not particularly limited, but the m-cresol/p-cresol molar ratio is preferably 3/7 or more and 8/2 or less. By using m-cresol and p-cresol in a ratio within this range, it is easy to obtain a photosensitive composition that can form a cured film with excellent heat resistance.

Also preferred is a novolac resin produced using a combination of m-cresol and 2,3,5-trimethylphenol. When such a novolac resin is used, it is particularly easy to obtain a photosensitive composition that can form a cured film that is difficult to flow or deform due to heat and has high heat resistance.
The blending ratio of m-cresol and 2,3,5-trimethylphenol is not particularly limited, but the m-cresol/2,3,5-trimethylphenol molar ratio is 70/30 or more and 95/5 or less. is preferred.

(Aldehydes)
Examples of aldehydes used in producing the novolac resin (a-2) include formaldehyde, paraformaldehyde, furfural, benzaldehyde, nitrobenzaldehyde, and acetaldehyde. These aldehydes may be used alone or in combination of two or more.

(acid catalyst)
Examples of acid catalysts used in producing the novolak resin (a-2) include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and phosphorous acid; formic acid, oxalic acid, acetic acid, diethyl sulfate, and Examples include organic acids such as para-toluenesulfonic acid; and metal salts such as zinc acetate. These acid catalysts may be used alone or in combination of two or more.

(molecular weight)
The lower limit of the weight average molecular weight (Mw) of the novolac resin (a-2) in terms of polystyrene is preferably 2000, more preferably 5000, from the viewpoint of heat resistance of the cured film formed using the photosensitive composition. 10,000 is particularly preferred, 15,000 is even more preferred, 20,000 is most preferred, the upper limit is preferably 50,000, more preferably 45,000, even more preferably 40,000, and most preferably 35,000.

As the novolak resin (a-2), at least two types of resins having different mass average molecular weights in terms of polystyrene may be used in combination. By using a combination of materials having different mass average molecular weights, it is possible to balance the developability of the photosensitive composition and the heat resistance of the cured film formed using the photosensitive composition.

[Modified epoxy resin (a-3)]
Polybasic acid anhydride, which is a reaction product of an epoxy compound (a-3a) and an unsaturated group-containing carboxylic acid (a-3b), is used as the alkali-soluble resin (A) in order to easily impart high water resistance to the cured film. Product (a-3c) may contain adduct (a-3). Such an adduct is also referred to as "modified epoxy resin (a-3)".
In addition, in the specification and claims of this application, a compound that falls under the above definition and does not fall under the above-mentioned resin having a cardo structure (a-1) is referred to as a modified epoxy resin (a-3). ).

The epoxy compound (a-3a), the unsaturated group-containing carboxylic acid (a-3b), and the polybasic acid anhydride (a-3c) will be explained below.

<Epoxy compound (a-3a)>
The epoxy compound (a-3a) is not particularly limited as long as it has an epoxy group, and may be an aromatic epoxy compound having an aromatic group or an aliphatic epoxy compound not containing an aromatic group. Often, aromatic epoxy compounds having aromatic groups are preferred.
The epoxy compound (a-3a) may be a monofunctional epoxy compound or a polyfunctional epoxy compound having two or more functionalities, and a polyfunctional epoxy compound is preferred.

Specific examples of the epoxy compound (a-3a) include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol AD epoxy resin, naphthalene epoxy resin, and biphenyl epoxy resin. Functional epoxy resin; glycidyl ester type epoxy resin such as dimer acid glycidyl ester and triglycidyl ester; tetraglycidyl amino diphenylmethane, triglycidyl-p-aminophenol, tetraglycidyl metaxylylene diamine, tetraglycidyl bisaminomethyl cyclohexane, etc. Glycidylamine type epoxy resin; heterocyclic epoxy resin such as triglycidyl isocyanurate; phloroglycinol triglycidyl ether, trihydroxybiphenyl triglycidyl ether, trihydroxyphenylmethane triglycidyl ether, glycerin triglycidyl ether, 2-[4- (2,3-epoxypropoxy)phenyl]-2-[4-[1,1-bis[4-(2,3-epoxypropoxy)phenyl]ethyl]phenyl]propane, and 1,3-bis[4- [1-[4-(2,3-epoxypropoxy)phenyl]-1-[4-[1-[4-(2,3-epoxypropoxy)phenyl]-1-methylethyl]phenyl]ethyl]phenoxy] Trifunctional epoxy resins such as -2-propanol; tetrafunctional epoxy resins such as tetrahydroxyphenylethane tetraglycidyl ether, tetraglycidyl benzophenone, bisresorcinol tetraglycidyl ether, and tetraglycidoxybiphenyl.

Furthermore, as the epoxy compound (a-3a), an epoxy compound having a biphenyl skeleton is preferable.
The epoxy compound having a biphenyl skeleton preferably has at least one biphenyl skeleton represented by the following formula (a-3a-1) in the main chain.
The epoxy compound having a biphenyl skeleton is preferably a polyfunctional epoxy compound having two or more epoxy groups.
By using an epoxy compound having a biphenyl skeleton, it is easy to obtain a photosensitive composition that has an excellent balance between sensitivity and developability and can form a cured film that has excellent adhesion to lenses.

（式（ａ－３ａ－１）中、Ｒ^ａ７は、それぞれ独立に、水素原子、炭素原子数１以上１２以下のアルキル基、ハロゲン原子、又は置換基を有してもよいフェニル基であり、ｊは１以上４以下の整数である。）

(In formula (a-3a-1), R ^a7 is each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a halogen atom, or a phenyl group which may have a substituent, j is an integer between 1 and 4.)

When R ^a7 is an alkyl group having 1 to 12 carbon atoms, specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group. group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert- Examples include octyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-undecyl group, and n-dodecyl group.

When R ^a7 is a halogen atom, specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

When R ^a7 is a phenyl group which may have a substituent, the number of substituents on the phenyl group is not particularly limited. The number of substituents on the phenyl group is 0 or more and 5 or less, preferably 0 or 1.
Examples of substituents include alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, aliphatic acyl groups having 2 to 4 carbon atoms, halogen atoms, cyano groups, and nitro Examples include groups.

（式（ａ－３ａ－２）中、Ｒ^ａ７及びｊは、式（ａ－３ａ－１）と同様であり、ｋは括弧内の構成単位の平均繰り返し数であって０以上１０以下である。） The epoxy compound (a-3a) having a biphenyl skeleton represented by the above formula (a-3a-1) is not particularly limited, but includes, for example, an epoxy compound represented by the following formula (a-3a-2). be able to.

(In formula (a-3a-2), R ^a7 and j are the same as in formula (a-3a-1), and k is the average repeating number of the structural unit in parentheses, which is 0 or more and 10 or less. .)

（式（ａ－３ａ－３）中、ｋは、式（ａ－３ａ－２）と同様である。） Among the epoxy compounds represented by the formula (a-3a-2), those represented by the following formula (a-3a-3) are particularly easy to obtain photosensitive compositions with an excellent balance between sensitivity and developability. Compounds such as

(In formula (a-3a-3), k is the same as in formula (a-3a-2).)

(Unsaturated group-containing carboxylic acid (a-3b))
In preparing the modified epoxy compound (a-3), the epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b) are reacted.
The unsaturated group-containing carboxylic acid (a-3b) is preferably a monocarboxylic acid containing a reactive unsaturated double bond such as an acrylic group or a methacryl group in the molecule. Examples of such unsaturated group-containing carboxylic acids include acrylic acid, methacrylic acid, β-styrylacrylic acid, β-furfurylacrylic acid, α-cyanocinnamic acid, and cinnamic acid. Further, the unsaturated group-containing carboxylic acid (a-3b) may be used alone or in combination of two or more types.

The epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b) can be reacted by a known method. As a preferable reaction method, for example, the epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b) are reacted with a tertiary amine such as triethylamine or benzylethylamine, dodecyltrimethylammonium chloride, tetramethylammonium chloride, Examples include a method of reacting in an organic solvent using a quaternary ammonium salt such as tetraethylammonium chloride or benzyltriethylammonium chloride, pyridine, or triphenylphosphine as a catalyst at a reaction temperature of 50°C or more and 150°C or less for several hours to several tens of hours. It will be done.

The ratio of the amounts used in the reaction between the epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b) is the epoxy equivalent of the epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b). The ratio to the carboxylic acid equivalent of a-3b) is usually preferably 1:0.5 to 1:2, more preferably 1:0.8 to 1:1.25, and 1:0.9 to 1:1. .1 is particularly preferred.
When the ratio of the amount of the epoxy compound (a-3a) used and the amount of the unsaturated group-containing carboxylic acid (a-3b) used is from 1:0.5 to 1:2 in terms of the above-mentioned equivalent ratio, the crosslinking efficiency is increased. This is preferable because it tends to improve.

(Polybasic acid anhydride (a-3c))
The polybasic acid anhydride (a-3c) is an anhydride of a carboxylic acid having two or more carboxyl groups.
Examples of the polybasic acid anhydride (a-3c) include, but are not limited to, maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, and methylhexahydro anhydride. Phthalic acid, methyltetrahydrophthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic dianhydride, 3-methylhexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, 3-ethylhexa Hydrophthalic anhydride, 4-ethylhexahydrophthalic anhydride, tetrahydrophthalic anhydride, 3-methyltetrahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride, 3-ethyltetrahydrophthalic anhydride, 4-ethyltetrahydrophthalic anhydride , a compound represented by the following formula (a-3c-1), and a compound represented by the following formula (a-3c-2). Further, the polybasic acid anhydrides (a-3c) may be used alone or in combination of two or more types.

（式（ａ－３ｃ－２）中、Ｒ^ａ８は、炭素原子数１以上１０以下の置換基を有してもよいアルキレン基を示す。）

(In formula (a-3c-2), R ^a8 represents an alkylene group which may have a substituent having 1 or more and 10 or less carbon atoms.)

The polybasic acid anhydride (a-3c) is preferably a compound having two or more benzene rings, since it is easy to obtain a photosensitive composition with an excellent balance between sensitivity and developability. Furthermore, the polybasic acid anhydride (a-3c) contains at least one of the compound represented by the above formula (a-3c-1) and the compound represented by the above formula (a-3c-2). is more preferable.

The method of reacting the epoxy compound (a-3a) with the unsaturated group-containing carboxylic acid (a-3b) and then reacting with the polybasic acid anhydride (a-3c) can be appropriately selected from known methods.
In addition, the usage ratio is determined by the number of moles of OH groups in the components after the reaction of the epoxy compound (a-3a) and the unsaturated group-containing carboxylic acid (a-3b) and the polybasic acid anhydride (a-3c). ) is usually 1:1 to 1:0.1, preferably 1:0.8 to 1:0.2. By setting it as the said range, it will be easy to obtain a photosensitive composition with good developability.

Further, the acid value of the modified epoxy resin (a-3) is preferably 10 mgKOH/g or more and 150 mgKOH/g or less, more preferably 70 mgKOH/g or more and 110 mgKOH/g or less, based on resin solid content. By setting the acid value of the resin to 10 mgKOH/g or more, sufficient solubility in the developer can be obtained, and by setting the acid value to 150 mgKOH/g or less, sufficient curability can be obtained, and the surface properties can be improved. It can be made good.

Furthermore, the weight average molecular weight of the modified epoxy resin (a-3) is preferably 1,000 or more and 40,000 or less, more preferably 2,000 or more and 30,000 or less. When the mass average molecular weight is 1000 or more, it is easy to form a cured film with excellent heat resistance and strength. In addition, when the molecular weight is 40,000 or less, it is easy to obtain a photosensitive composition that exhibits sufficient solubility in a developer.

[Acrylic resin (a-4)]
As the alkali-soluble resin (A), acrylic resin (a-4) is also preferred.
As the acrylic resin (a-4), one containing a structural unit derived from (meth)acrylic acid and/or a structural unit derived from other monomers such as (meth)acrylic acid ester can be used. (Meth)acrylic acid is acrylic acid or methacrylic acid. The (meth)acrylic ester is represented by the following formula (a-4-1), and is not particularly limited as long as it does not impede the purpose of the present invention.

In the above formula (a-4-1), R ^a9 is a hydrogen atom or a methyl group, and R ^a10 is a monovalent organic group. This organic group may contain a bond or substituent other than a hydrocarbon group such as a hetero atom. Further, this organic group may be linear, branched, or cyclic.

Substituents other than hydrocarbon groups in the organic group of R ^a10 are not particularly limited as long as the effects of the present invention are not impaired, and include halogen atoms, hydroxyl groups, mercapto groups, sulfide groups, cyano groups, isocyano groups, and cyanato groups. , isocyanato group, thiocyanato group, isothiocyanato group, silyl group, silanol group, alkoxy group, alkoxycarbonyl group, carbamoyl group, thiocarbamoyl group, nitro group, nitroso group, carboxy group, carboxylate group, acyl group, acyloxy group, sulfino group group, sulfo group, sulfonato group, phosphino group, phosphinyl group, phosphono group, phosphonato group, hydroxyimino group, alkyl ether group, alkylthioether group, aryl ether group, arylthioether group, amino group (-NH ₂ , -NHR, -NRR': R and R' each independently represent a hydrocarbon group). The hydrogen atom included in the above substituent may be substituted with a hydrocarbon group. Moreover, the hydrocarbon group contained in the above-mentioned substituent may be linear, branched, or cyclic.

Further, the organic group as R ^a10 may have a reactive functional group such as an acryloyloxy group, a methacryloyloxy group, an epoxy group, or an oxetanyl group.
For example, an acyl group having an unsaturated double bond, such as an acryloyloxy group or a methacryloyloxy group, is used in at least a portion of the epoxy group in the acrylic resin (a-4) containing a structural unit having an epoxy group. It can be produced by reacting unsaturated carboxylic acids such as acrylic acid and methacrylic acid.

R ^a10 is preferably an alkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and these groups may be substituted with a halogen atom, a hydroxyl group, an alkyl group, or a heterocyclic group. Further, when these groups contain an alkylene moiety, the alkylene moiety may be interrupted by an ether bond, a thioether bond, or an ester bond.

When the alkyl group is linear or branched, the number of carbon atoms is preferably 1 or more and 20 or less, more preferably 1 or more and 15 or less, particularly preferably 1 or more and 10 or less. Examples of suitable alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec -pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, n-decyl group, Examples include isodecyl group.

When the alkyl group is an alicyclic group or a group containing an alicyclic group, suitable examples of the alicyclic group contained in the alkyl group include monocyclic alicyclic groups such as a cyclopentyl group and a cyclohexyl group; , adamantyl group, norbornyl group, isobornyl group, tricyclononyl group, tricyclodecyl group, and tetracyclododecyl group.

Specific examples of the compound represented by formula (a-4-1) in the case where the compound represented by formula (a-4-1) has a chain group having an epoxy group as R ^a10 , Examples include (meth)acrylic acid epoxyalkyl esters such as glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 6,7-epoxyheptyl (meth)acrylate. .

Further, the compound represented by formula (a-4-1) may be an alicyclic epoxy group-containing (meth)acrylic ester. The alicyclic group constituting the alicyclic epoxy group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic group include a cyclopentyl group and a cyclohexyl group. Examples of the polycyclic alicyclic group include a norbornyl group, an isobornyl group, a tricyclononyl group, a tricyclodecyl group, and a tetracyclododecyl group.

Specific examples when the compound represented by formula (a-4-1) is an alicyclic epoxy group-containing (meth)acrylic ester include the following formulas (a-4-1a) to (a-4). -1o). Among these, in order to obtain appropriate developability, compounds represented by the following formulas (a-4-1a) to (a-4-1e) are preferable, and compounds represented by the following formulas (a-4-1a) to A compound represented by (a-4-1c) is more preferred.

In the above formula, R ^a20 represents a hydrogen atom or a methyl group, R ^a21 represents a divalent aliphatic saturated hydrocarbon group having 1 to 6 carbon atoms, and R ^a22 represents 2 having 1 to 10 carbon atoms. represents a valent hydrocarbon group, and t represents an integer of 0 or more and 10 or less. R ^a21 is preferably a linear or branched alkylene group, such as a methylene group, ethylene group, propylene group, tetramethylene group, ethylethylene group, pentamethylene group, or hexamethylene group. Examples of R ^a22 include methylene group, ethylene group, propylene group, tetramethylene group, ethylethylene group, pentamethylene group, hexamethylene group, phenylene group, cyclohexylene group, -CH ₂ -Ph-CH ₂ - (Ph is (representing a phenylene group) is preferred.

Further, the acrylic resin (a-4) may be one obtained by polymerizing monomers other than (meth)acrylic acid ester. Examples of such monomers include (meth)acrylamides, unsaturated carboxylic acids, allyl compounds, vinyl ethers, vinyl esters, and styrenes. These monomers can be used alone or in combination of two or more.

(Meth)acrylamides include (meth)acrylamide, N-alkyl(meth)acrylamide, N-aryl(meth)acrylamide, N,N-dialkyl(meth)acrylamide, N,N-aryl(meth)acrylamide, N- -Methyl-N-phenyl (meth)acrylamide, N-hydroxyethyl-N-methyl (meth)acrylamide, and the like.

Examples of unsaturated carboxylic acids include monocarboxylic acids such as crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, and itaconic acid; anhydrides of these dicarboxylic acids; and the like.

Examples of allyl compounds include allyl esters such as allyl acetate, allyl caproate, allyl caprylate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, allyl acetoacetate, and allyl lactate; allyloxyethanol; etc. Can be mentioned.

Examples of vinyl ethers include hexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, ethylhexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, chloroethyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether, 2-ethylbutyl vinyl ether, and hydroxyethyl vinyl ether. , diethylene glycol vinyl ether, dimethylaminoethyl vinyl ether, diethylaminoethyl vinyl ether, butylaminoethyl vinyl ether, benzyl vinyl ether, tetrahydrofurfuryl vinyl ether, and other alkyl vinyl ethers; vinyl phenyl ether, vinyl tolyl ether, vinyl chlorophenyl ether, vinyl-2,4-dichlorophenyl ether , vinyl aryl ethers such as vinyl naphthyl ether, vinyl anthrani ether, and the like.

Vinyl esters include vinyl butyrate, vinyl isobutyrate, vinyl trimethyl acetate, vinyl diethyl acetate, vinyl valerate, vinyl caproate, vinyl chloroacetate, vinyl dichloroacetate, vinyl methoxy acetate, vinyl butoxy acetate, and vinyl phenyl. Examples include acetate, vinyl acetoacetate, vinyl lactate, vinyl-β-phenylbutyrate, vinyl benzoate, vinyl salicylate, vinyl chlorobenzoate, vinyl tetrachlorobenzoate, vinyl naphthoate, and the like.

Styrenes include styrene; methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, isopropylstyrene, butylstyrene, hexylstyrene, cyclohexylstyrene, decylstyrene, benzylstyrene, chloromethylstyrene, trifluoromethylstyrene, ethoxy Alkyl styrenes such as methylstyrene and acetoxymethylstyrene; alkoxystyrenes such as methoxystyrene, 4-methoxy-3-methylstyrene and dimethoxystyrene; chlorostyrene, dichlorostyrene, trichlorostyrene, tetrachlorostyrene, pentachlorostyrene, bromostyrene, Halostyrenes such as dibromostyrene, iodostyrene, fluorostyrene, trifluorostyrene, 2-bromo-4-trifluoromethylstyrene, and 4-fluoro-3-trifluoromethylstyrene; and the like.

The amount of structural units derived from (meth)acrylic acid and the amount of structural units derived from other monomers in the acrylic resin (a-4) are not particularly limited as long as they do not impede the object of the present invention. The amount of structural units derived from (meth)acrylic acid in the acrylic resin (a-4) is preferably 5% by mass or more and 50% by mass or less, and 10% by mass or less, based on the mass of the acrylic resin (a-4). More preferably, the content is from % by mass to 30% by mass.

When the acrylic resin (a-4) has a structural unit having an unsaturated double bond, the amount of the structural unit having an unsaturated double bond in the acrylic resin (a-4) is 1% by mass or more The content is preferably 50% by mass or less, more preferably 1% by mass or more and 30% by mass or less, particularly preferably 1% by mass or more and 20% by mass or less.
When the acrylic resin (a-4) contains a structural unit having an unsaturated double bond in the amount within the above range, the acrylic resin can be incorporated into the crosslinking reaction within the resist film to make it uniform, resulting in a cured film. It is effective in improving the heat resistance and mechanical properties of

The mass average molecular weight of the acrylic resin (a-4) is preferably 2,000 or more and 50,000 or less, more preferably 3,000 or more and 30,000 or less. By setting it as the said range, there exists a tendency for the film-forming ability of a photosensitive composition and the developability after exposure to be well-balanced.

The content of the alkali-soluble resin (A) in the total solid content of the photosensitive composition is preferably 10% by mass or more and 75% by mass or less, more preferably 15% by mass or more and 65% by mass or less. When the content of the alkali-soluble resin (A) in the total solid content of the photosensitive composition is within the above range, the solid content of the photosensitive composition dissolves well in the developer in the unexposed area. Therefore, the solid content of the cured photosensitive composition is difficult to dissolve in the developer in the exposed area, making it easy to obtain a photosensitive composition with excellent developability and resolution.
Note that in this specification, the solid content refers to components other than the organic solvent.

<Photopolymerizable monomer (B)>
The photosensitive composition contains a photopolymerizable monomer (B). As the photopolymerizable monomer (B), a compound having an ethylenically unsaturated group is preferable. Compounds having such ethylenically unsaturated groups include monofunctional compounds and polyfunctional compounds.

Monofunctional compounds include (meth)acrylamide, methylol (meth)acrylamide, methoxymethyl (meth)acrylamide, ethoxymethyl (meth)acrylamide, propoxymethyl (meth)acrylamide, butoxymethoxymethyl (meth)acrylamide, N-methylol ( meth)acrylamide, N-hydroxymethyl(meth)acrylamide, (meth)acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamide- 2-Methylpropanesulfonic acid, tert-butylacrylamide sulfonic acid, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-phenoxy-2-hydroxypropyl (meth)acrylate, 2-(meth)acryloyloxy-2-hydroxypropyl phthalate, Glycerin mono(meth)acrylate, tetrahydrofurfuryl(meth)acrylate, dimethylaminoethyl(meth)acrylate, glycidyl(meth)acrylate, 2,2,2-trifluoroethyl(meth)acrylate, 2,2,3,3 -Tetrafluoropropyl (meth)acrylate, half (meth)acrylate of phthalic acid derivatives, etc. These monofunctional compounds can be used alone or in combination of two or more.

On the other hand, polyfunctional compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol Di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate Acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 2,2-bis(4-(meth)acryloxydiethoxyphenyl)propane, 2,2 -Bis(4-(meth)acryloxypolyethoxyphenyl)propane, 2-hydroxy-3-(meth)acryloyloxypropyl(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di( meth)acrylate, phthalic acid diglycidyl ester di(meth)acrylate, glycerin polyglycidyl ether poly(meth)acrylate, glycerin tri(meth)acrylate, urethane(meth)acrylate (i.e., tolylene diisocyanate, trimethylhexamethylene diisocyanate, or Polyfunctional products such as reaction products of hexamethylene diisocyanate, etc. and 2-hydroxyethyl (meth)acrylate), methylene bis(meth)acrylamide, (meth)acrylamide methylene ether, and condensates of polyhydric alcohols and N-methylol(meth)acrylamide. Examples include compounds, triacrylic formal, and the like. These polyfunctional compounds can be used alone or in combination of two or more.

In addition, in this specification, "(meth)acrylate" means both "acrylate" and "methacrylate", and "(meth)acrylic" means both "acrylic" and "methacrylic". , "(meth)acryloyl" means both "acryloyl" and "methacryloyl", and "(meth)acryloyloxy" means both "acryloyloxy" and "methacryloyloxy".

Among these photopolymerizable compounds having an ethylenically unsaturated group, polyfunctional compounds having three or more functional groups tend to improve the adhesion of the photosensitive composition to the lens and the strength of the photosensitive composition after curing. A compound is preferable, a polyfunctional compound having four or more functionalities is more preferable, and a polyfunctional compound having five or more functionalities is even more preferable.
Specifically, it is preferable to use a polyfunctional compound having five or more functionalities, and it is more preferable to use dipentaerythritol penta(meth)acrylate and/or dipentaerythritol hexa(meth)acrylate.

The content of the photopolymerizable monomer (B) in the total solid content of the photosensitive composition is preferably 1% by mass or more and 30% by mass or less, more preferably 5% by mass or more and 20% by mass or less.

<Photopolymerization initiator (C)>
The photopolymerization initiator (C) is not particularly limited, and conventionally known photopolymerization initiators can be used.
Examples of the photopolymerization initiator (C) include oxime ester compounds.
As the oxime ester compound, a compound having a partial structure represented by the following formula (c1) is preferable.

（式（ｃ１）中、
ｎ１は、０、又は１であり、
Ｒ^ｃ２は、一価の有機基であり、
Ｒ^ｃ３は、水素原子、置換基を有してもよい炭素原子数１以上２０以下の脂肪族炭化水素基、又は置換基を有してもよいアリール基であり、
＊は結合手である。）

(In formula (c1),
n1 is 0 or 1,
R ^c2 is a monovalent organic group,
R ^c3 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, or an aryl group that may have a substituent,
* is a bond. )

The compound having a partial structure represented by formula (c1) preferably has a carbazole skeleton, a fluorene skeleton, a diphenyl ether skeleton, or a phenyl sulfide skeleton.
The compound having a partial structure represented by formula (c1) preferably has one or two partial structures represented by formula (c1).

Examples of the compound having a partial structure represented by formula (c1) include a compound represented by formula (c2) below.

（式（ｃ２）中、Ｒ^ｃ１は、下記式（ｃ３）、（ｃ４）、又は（ｃ５）で表される基であり、
ｎ１は、０、又は１であり、
Ｒ^ｃ２は、一価の有機基であり、
Ｒ^ｃ３は、水素原子、置換基を有してもよい炭素原子数１以上２０以下の脂肪族炭化水素基、又は置換基を有してもよいアリール基である。）

(In formula (c2), R ^c1 is a group represented by the following formula (c3), (c4), or (c5),
n1 is 0 or 1,
R ^c2 is a monovalent organic group,
R ^c3 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aryl group which may have a substituent. )

（式（ｃ３）中、Ｒ^ｃ４及びＲ^ｃ５は、それぞれ独立に、１価の有機基であり、
ｎ２は、０以上３以下の整数であり、
ｎ２が２又は３の場合、複数のＲ^ｃ５は同一でも異なっていてもよく、複数のＲ^ｃ５は互いに結合して環を形成してもよい。
＊は結合手である。）

(In formula (c3), R ^c4 and R ^c5 are each independently a monovalent organic group,
n2 is an integer from 0 to 3,
When n2 is 2 or 3, the plurality of R ^c5s may be the same or different, and the plurality of R ^c5s may be bonded to each other to form a ring.
* is a bond. )

（式（ｃ４）中、Ｒ^ｃ６及びＲ^ｃ７は、それぞれ独立に、置換基を有してもよい鎖状アルキル基、置換基を有してもよい鎖状アルコキシ基、置換基を有してもよい環状有機基、又は水素原子であり、
Ｒ^ｃ６とＲ^ｃ７とは互いに結合して環を形成してもよく、
Ｒ^ｃ７とフルオレン骨格中のベンゼン環とが互いに結合して環を形成してもよく、
Ｒ^ｃ８は、ニトロ基、又は１価の有機基、であり、
ｎ３は、０以上４以下の整数であり、
＊は結合手である。）

(In formula (c4), R ^c6 and R ^c7 each independently represent a chain alkyl group which may have a substituent, a chain alkoxy group which may have a substituent, and a chain alkoxy group which may have a substituent. a cyclic organic group or a hydrogen atom,
R ^c6 and R ^c7 may be combined with each other to form a ring,
R ^c7 and the benzene ring in the fluorene skeleton may be bonded to each other to form a ring,
R ^c8 is a nitro group or a monovalent organic group,
n3 is an integer from 0 to 4,
* is a bond. )

（式（ｃ５）中、Ｒ^ｃ９は、１価の有機基、ハロゲン原子、ニトロ基、又はシアノ基であり、
Ａは、Ｓ又はＯであり、
ｎ４は、０以上４以下の整数であり、
＊は結合手である。）

(In formula (c5), R ^c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group,
A is S or O,
n4 is an integer from 0 to 4,
* is a bond. )

In formula (c3), R ^c4 is a monovalent organic group. R ^c4 can be selected from various organic groups within the range that does not impede the purpose of the present invention. The organic group is preferably a carbon atom-containing group, with one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
Suitable examples of R ^c4 include an alkyl group which may have a substituent having 1 to 20 carbon atoms, a cycloalkyl group which may have a substituent having 3 to 20 carbon atoms, and a carbon atom. A saturated aliphatic acyl group which may have a substituent of 2 or more and 20 or less, an alkoxycarbonyl group which may have a substituent of 2 or more and 20 or less carbon atoms, a phenyl group which may have a substituent , a benzoyl group which may have a substituent, a phenoxycarbonyl group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a phenylalkyl group which may have a substituent naphthyl group, optionally substituted naphthoyl group, optionally substituted naphthoxycarbonyl group, optionally substituted naphthyl alkyl group having 11 to 20 carbon atoms, substituted Examples include a heterocyclyl group which may have a group, and a heterocyclylcarbonyl group which may have a substituent.

Among R ^c4 , an alkyl group having 1 or more and 20 or less carbon atoms is preferred. The alkyl group may be linear or branched. In view of the good solubility of the compound represented by formula (c3) in the photosensitive composition, the number of carbon atoms in the alkyl group as R ^c4 is preferably 2 or more, more preferably 5 or more, and 7 The above is particularly preferable. In addition, from the viewpoint of good compatibility between the compound represented by formula (c3) and other components in the photosensitive composition, the number of carbon atoms in the alkyl group as R ^c4 is 15 or less. is preferable, and 10 or less is more preferable.

When R ^c4 has a substituent, suitable examples of the substituent include a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and 2 to 20 carbon atoms. aliphatic acyl group, aliphatic acyloxy group having 2 to 20 carbon atoms, phenoxy group, benzoyl group, benzoyloxy group, group represented by -PO(OR) ₂ (R is 1 to 6 carbon atoms) (alkyl group), halogen atom, cyano group, heterocyclyl group, etc.

When R ^c4 is a heterocyclyl group, the heterocyclyl group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. When R ^c4 is a heterocyclyl group, the heterocyclyl group is a 5- or 6-membered monocyclic ring containing one or more N, S, or O, or such monocycles are fused together, or such monocycles are fused with a benzene ring. It is a heterocyclyl group. When the heterocyclyl group is a condensed ring, the number of monocycles constituting the condensed ring is up to three. Examples of the heterocycle constituting such a heterocyclyl group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, Examples include isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran. It will be done.
When R ^c4 is a heterocyclyl group, examples of substituents that the heterocyclyl group may have include a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a cyano group, a nitro group, and the like.

Preferred specific examples of R ^c4 explained above include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, Examples include isopentyl group, neopentyl group, pentan-3-yl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, and 2-ethylhexyl group.
Further, from the viewpoint of good solubility of the compound represented by formula (c3) in the photosensitive composition, n-octyl group and 2-ethylhexyl group are preferable, and 2-ethylhexyl group is more preferable.

In formula (c3), R ^c5 is a monovalent organic group, a halogen atom, or a nitro group. R ^c5 can be selected from various organic groups within the range that does not impede the purpose of the present invention. The organic group is preferably a carbon atom-containing group, with one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
Examples of monovalent organic groups suitable as R ^c5 include alkyl groups, alkoxy groups, cycloalkyl groups, cycloalkoxy groups, saturated aliphatic acyl groups, alkoxycarbonyl groups, saturated aliphatic acyloxy groups, and those having substituents. phenyl group which may have a substituent, phenoxy group which may have a substituent, benzoyl group which may have a substituent, phenoxycarbonyl group which may have a substituent, benzoyloxy which may have a substituent group, a phenylalkyl group that may have a substituent, a naphthyl group that may have a substituent, a naphthoxy group that may have a substituent, a naphthoyl group that may have a substituent, Naphthoxycarbonyl group which may have a substituent, naphthoyloxy group which may have a substituent, naphthylalkyl group which may have a substituent, heterocyclyl group which may have a substituent, optional heterocyclylcarbonyl group, amino group substituted with 1 or 2 organic groups, morpholin-1-yl group, piperazin-1-yl group, halogen, nitro group, cyano group, HX ₂ C- or H ₂ Examples include substituents including a group represented by XC- (wherein each X is independently a halogen atom), and the like.

When R ^c5 is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. Further, when R ^c5 is an alkyl group, it may be a straight chain or a branched chain. Specific examples when R ^c5 is an alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group. , isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, Examples include n-decyl group and isodecyl group. Further, when R ^c5 is an alkyl group, the alkyl group may contain an ether bond (-O-) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include methoxyethyl group, ethoxyethyl group, methoxyethoxyethyl group, ethoxyethoxyethyl group, propyloxyethoxyethyl group, and methoxypropyl group.

When R ^c5 is an alkoxy group, the number of carbon atoms in the alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. Further, when R ^c5 is an alkoxy group, it may be a straight chain or a branched chain. Specific examples when R ^c5 is an alkoxy group include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, n -Pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec-octyloxy group , tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, and isodecyloxy group. Further, when R ^c5 is an alkoxy group, the alkoxy group may contain an ether bond (-O-) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include methoxyethoxy group, ethoxyethoxy group, methoxyethoxyethoxy group, ethoxyethoxyethoxy group, propyloxyethoxyethoxy group, and methoxypropyloxy group.

When R ^c5 is a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms in the cycloalkyl group or cycloalkoxy group is preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less. Specific examples when R ^c5 is a cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Specific examples when R ^c5 is a cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like.

When R ^c5 is a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the number of carbon atoms in the saturated aliphatic acyl group or saturated aliphatic acyloxy group is preferably 2 or more and 21 or less, more preferably 2 or more and 7 or less. Specific examples when R ^c5 is a saturated aliphatic acyl group include acetyl group, propanoyl group, n-butanoyl group, 2-methylpropanoyl group, n-pentanoyl group, 2,2-dimethylpropanoyl group, n -hexanoyl group, n-heptanoyl group, n-octanoyl group, n-nonanoyl group, n-decanoyl group, n-undecanoyl group, n-dodecanoyl group, n-tridecanoyl group, n-tetradecanoyl group, n-pentadecanoyl group Examples thereof include a noyl group and an n-hexadecanoyl group. Specific examples when R ^c5 is a saturated aliphatic acyloxy group include acetyloxy group, propanoyloxy group, n-butanoyloxy group, 2-methylpropanoyloxy group, n-pentanoyloxy group, 2, 2-dimethylpropanoyloxy group, n-hexanoyloxy group, n-heptanoyloxy group, n-octanoyloxy group, n-nonanoyloxy group, n-decanoyloxy group, n-undecanoyloxy group, n Examples include -dodecanoyloxy group, n-tridecanoyloxy group, n-tetradecanoyloxy group, n-pentadecanoyloxy group, and n-hexadecanoyloxy group.

When R ^c5 is an alkoxycarbonyl group, the number of carbon atoms in the alkoxycarbonyl group is preferably 2 or more and 20 or less, more preferably 2 or more and 7 or less. Specific examples when R ^c5 is an alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyl group. Oxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group group, n-octyloxycarbonyl group, isooctyloxycarbonyl group, sec-octyloxycarbonyl group, tert-octyloxycarbonyl group, n-nonyloxycarbonyl group, isononyloxycarbonyl group, n-decyloxycarbonyl group, and Examples include isodecyloxycarbonyl group.

When R ^c5 is a phenylalkyl group, the number of carbon atoms in the phenylalkyl group is preferably 7 or more and 20 or less, more preferably 7 or more and 10 or less. Further, when R ^c5 is a naphthylalkyl group, the number of carbon atoms in the naphthylalkyl group is preferably 11 or more and 20 or less, more preferably 11 or more and 14 or less. Specific examples when R ^c5 is a phenylalkyl group include benzyl group, 2-phenylethyl group, 3-phenylpropyl group, and 4-phenylbutyl group. Specific examples when R ^c5 is a naphthyl alkyl group include α-naphthylmethyl group, β-naphthylmethyl group, 2-(α-naphthyl)ethyl group, and 2-(β-naphthyl)ethyl group. . When R ^c5 is a phenylalkyl group or a naphthyl alkyl group, R ^c5 may further have a substituent on the phenyl group or naphthyl group.

When R ^c5 is a heterocyclyl group, the heterocyclyl group is the same as when R ^c4 in formula (c3) is a heterocyclyl group, and the heterocyclyl group may further have a substituent.
When R ^c5 is a heterocyclylcarbonyl group, the heterocyclyl group contained in the heterocyclylcarbonyl group is the same as when R ^c5 is a heterocyclyl group.

When R ^c5 is an amino group substituted with 1 or 2 organic groups, suitable examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, Saturated aliphatic acyl group having 2 to 21 carbon atoms, phenyl group which may have a substituent, benzoyl group which may have a substituent, 7 to 20 carbon atoms which may have a substituent The following phenylalkyl groups, optionally substituted naphthyl groups, optionally substituted naphthoyl groups, optionally substituted naphthylalkyl groups having 11 to 20 carbon atoms, and heterocyclyl groups Examples include groups. Specific examples of these suitable organic groups are the same as R ^c5 . Specific examples of amino groups substituted with 1 or 2 organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n- butylamino group, di-n-butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, naphthylamino group, acetylamino group, propanoylamino group, n-butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino group, n- Examples include decanoylamino group, benzoylamino group, α-naphthoylamino group, and β-naphthoylamino group.

When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c5 further has a substituent, the substituent includes a group represented by HX ₂ C- or H ₂ XC- (for example, HX a halogenated alkoxy group containing a group represented by ₂ C- or H ₂ XC-, a halogenated alkyl group containing a group represented by HX _{2 C-} or H 2 Alkyl group, alkoxy group having 1 to 6 carbon atoms, saturated aliphatic acyl group having 2 to 7 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, saturated fat having 2 to 7 carbon atoms Group acyloxy group, monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl group, piperazin-1-yl group , benzoyl group, halogen, nitro group, and cyano group. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c5 further has a substituent, the number of the substituent is not limited as long as it does not impede the object of the present invention, and is preferably 1 or more and 4 or less. When the phenyl group, naphthyl group, and heterocyclyl group contained in R ^c5 have a plurality of substituents, the plurality of substituents may be the same or different.

When the benzoyl group contained in R ^c5 further has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a 2-thenoyl group. (thiophen-2-ylcarbonyl group), furan-3-ylcarbonyl group, phenyl group, and the like.

Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and the like, with a fluorine atom being preferred.

Examples of substituents containing a group represented by HX ₂ C- or H ₂ XC- include a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC-, HX ₂ C- or H ₂ XC-; A group having a halogenated alkoxy group containing a group represented by -, a halogenated alkyl group containing a group represented by HX ₂ C- or H ₂ XC-, a group represented by HX ₂ C- or H ₂ XC- Examples include groups having a halogenated alkyl group containing a group, such as a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC-, or a group represented by HX ₂ C- or H ₂ XC- A group having a halogenated alkoxy group is more preferable.

The group having a halogenated alkyl group containing a group represented by HX ₂ C- or H 2 XC- is a group substituted with a halogenated alkyl group containing a group represented by HX ₂ C- _or H ₂ XC- aromatic groups (e.g., phenyl group, naphthyl group, etc.), cycloalkyl groups substituted with halogenated alkyl groups (e.g., _cyclopentyl group, cyclohexyl group, _etc. ) The aromatic group is preferably an aromatic group substituted with a halogenated alkyl group including a group represented by HX ₂ C- or H ₂ XC-.

_The group having a halogenated alkoxy group containing a group represented by HX ₂ C- or H 2 XC- is a group substituted with a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC- (e.g., phenyl group, naphthyl group, etc.), an alkyl group substituted with a halogenated alkoxy group (e.g., methyl group, ethyl group, etc.) containing a group represented by HX ₂ C- or H ₂ XC- , n-propyl group, i-propyl group, etc.), a cycloalkyl group substituted with a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC- (for example, cyclopentyl group, cyclohexyl group, etc.) ), and is preferably an aromatic group substituted with a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC-.

Also preferred as R ^c5 are a cycloalkylalkyl group, a phenoxyalkyl group which may have a substituent on the aromatic ring, and a phenylthioalkyl group which may have a substituent on the aromatic ring. The substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are the same as the substituents that the phenyl group included in R ^c5 may have.

Among monovalent organic groups, R ^c5 is an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, or a cycloalkylalkyl group, even if it has a substituent on an aromatic ring. Good phenylthioalkyl groups are preferred. As the alkyl group, an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, an alkyl group having 1 to 4 carbon atoms is particularly preferable, and a methyl group is the most preferable. preferable. Among the phenyl groups which may have substituents, methylphenyl is preferred, and 2-methylphenyl is more preferred. The number of carbon atoms in the cycloalkyl group contained in the cycloalkylalkyl group is preferably 5 or more and 10 or less, more preferably 5 or more and 8 or less, and particularly preferably 5 or 6. The number of carbon atoms in the alkylene group contained in the cycloalkylalkyl group is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2. Among the cycloalkylalkyl groups, a cyclopentylethyl group is preferred. The number of carbon atoms in the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2. Among the phenylthioalkyl groups which may have a substituent on the aromatic ring, 2-(4-chlorophenylthio)ethyl group is preferred.

In the group represented by formula (c3), when a plurality of R ^c5s exist and the plurality of R ^c5s combine with each other to form a ring, examples of the formed ring include a hydrocarbon ring, a heterocycle, etc. It will be done. Examples of the heteroatom contained in the heterocycle include N, O, and S. The ring formed by bonding a plurality of R ^c5 to each other is particularly preferably an aromatic ring. Such an aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocycle. As such an aromatic ring, an aromatic hydrocarbon ring is preferable. In formula (c3), a specific example where a plurality of R ^c5s combine with each other to form a benzene ring is shown below.

In the group represented by formula (c4), R ^c8 is a nitro group or a monovalent organic group. R ^c8 is bonded to a 6-membered aromatic ring different from the aromatic ring bonded to the group represented by -(CO) _n1 - on the condensed ring in formula (c4). In formula (c4), the bonding position of R ^c8 is not particularly limited. When the group represented by formula (c4) has one or more R ^c8 , one of the one or more R ^c8 is fluorene because the compound represented by formula (c4) is easily synthesized. It is preferable to bond to the 7th position of the skeleton. That is, when the group represented by formula (c4) has one or more R ^c8 , the group represented by formula (c4) is preferably represented by the following formula (c6). When there is a plurality of R ^c8s , the plurality of R ^c8s may be the same or different.

（式（ｃ６）中、Ｒ^ｃ６、Ｒ^ｃ７、Ｒ^ｃ８、ｎ３は、それぞれ式（ｃ４）におけるＲ^ｃ６、Ｒ^ｃ７、Ｒ^ｃ８、ｎ３と同様である。）

(In formula (c6), R ^c6 , R ^c7 , R ^c8 , and n3 are the same as R ^c6 , R ^c7 , R ^c8 , and n3 in formula (c4), respectively.)

When R ^c8 is a monovalent organic group, R ^c8 is not particularly limited as long as it does not impede the object of the present invention. The organic group is preferably a carbon atom-containing group, with one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
Preferable examples of R ^c8 being a monovalent organic group include the same groups as the preferable examples of the monovalent organic group as R ^c5 in formula (c3).

In formula (c4), R ^c6 and R ^c7 are a chain alkyl group which may have a substituent, a chain alkoxy group which may have a substituent, and a cyclic alkyl group which may have a substituent, respectively. It is an organic group or a hydrogen atom. R ^c6 and R ^c7 may be bonded to each other to form a ring. Among these groups, R ^c6 and R ^c7 are preferably chain alkyl groups which may have a substituent. When R ^c6 and R ^c7 are chain alkyl groups which may have a substituent, the chain alkyl group may be a straight chain alkyl group or a branched chain alkyl group.

When R ^c6 and R ^c7 are chain alkyl groups without substituents, the number of carbon atoms in the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, particularly 1 or more and 6 or less. preferable. Specific examples when R ^c6 and R ^c7 are chain alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group. , n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, n-decyl group, and isodecyl group. Further, when R ^c6 and R ^c7 are alkyl groups, the alkyl groups may contain an ether bond (-O-) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include methoxyethyl group, ethoxyethyl group, methoxyethoxyethyl group, ethoxyethoxyethyl group, propyloxyethoxyethyl group, and methoxypropyl group.

When R ^c6 and R ^c7 are chain alkyl groups having a substituent, the number of carbon atoms in the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, particularly preferably 1 or more and 6 or less. . In this case, the number of carbon atoms in the substituent is not included in the number of carbon atoms in the chain alkyl group. The chain alkyl group having a substituent is preferably linear.

The substituent that the alkyl group may have is not particularly limited as long as it does not impede the object of the present invention. Suitable examples of the substituent include an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, and an alkoxycarbonyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, fluorine atom, chlorine atom, and bromine atom are preferred. Examples of the cyclic organic group include a cycloalkyl group, an aromatic hydrocarbon group, and a heterocyclyl group. Specific examples of the cycloalkyl group are the same as the preferred examples when R ^c8 is a cycloalkyl group. Specific examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenylyl group, anthryl group, and phenanthryl group. Specific examples of the heterocyclyl group are the same as the preferred examples when R ^c8 is a heterocyclyl group. When R ^c8 is an alkoxycarbonyl group, the alkoxy group contained in the alkoxycarbonyl group may be linear or branched, and preferably linear. The number of carbon atoms in the alkoxy group contained in the alkoxycarbonyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.

When the chain alkyl group has a substituent, the number of substituents is not particularly limited. The preferred number of substituents varies depending on the number of carbon atoms in the chain alkyl group. The number of substituents is typically 1 or more and 20 or less, preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less.

When R ^c6 and R ^c7 are chain alkoxy groups without substituents, the number of carbon atoms in the chain alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, particularly 1 or more and 6 or less. preferable. Specific examples when R ^c6 and R ^c7 are chain alkoxy groups include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert -butyloxy group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, Examples include sec-octyloxy group, tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, and isodecyloxy group. Further, when R ^c6 and R ^c7 are alkoxy groups, the alkoxy groups may contain an ether bond (-O-) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include methoxyethoxy group, ethoxyethoxy group, methoxyethoxyethoxy group, ethoxyethoxyethoxy group, propyloxyethoxyethoxy group, and methoxypropyloxy group.

When R ^c6 and R ^c7 are chain alkoxy groups having substituents, the substituents that the alkoxy groups may have are the same as in the case where R ^c6 and R ^c7 are chain alkyl groups.

When R ^c6 and R ^c7 are cyclic organic groups, the cyclic organic group may be an alicyclic group or an aromatic group. Examples of the cyclic organic group include an aliphatic cyclic hydrocarbon group, an aromatic hydrocarbon group, and a heterocyclyl group. When R ^c6 and R ^c7 are cyclic organic groups, the substituents that the cyclic organic groups may have are the same as when R ^c6 and R ^c7 are chain alkyl groups.

When R ^c6 and R ^c7 are aromatic hydrocarbon groups, the aromatic hydrocarbon group is a phenyl group or a group formed by combining multiple benzene rings via carbon-carbon bonds. , is preferably a group formed by condensing a plurality of benzene rings. When the aromatic hydrocarbon group is a phenyl group or a group formed by bonding or condensing multiple benzene rings, the number of benzene rings contained in the aromatic hydrocarbon group is not particularly limited, It is preferably 3 or less, more preferably 2 or less, and particularly preferably 1. Preferred specific examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenylyl group, anthryl group, and phenanthryl group.

When R ^c6 and R ^c7 are aliphatic cyclic hydrocarbon groups, the aliphatic cyclic hydrocarbon groups may be monocyclic or polycyclic. The number of carbon atoms in the aliphatic cyclic hydrocarbon group is not particularly limited, but is preferably 3 or more and 20 or less, more preferably 3 or more and 10 or less. Examples of monocyclic cyclic hydrocarbon groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, norbornyl group, isobornyl group, tricyclononyl group, tricyclodecyl group, Examples include a tetracyclododecyl group and an adamantyl group.

When R ^c6 and R ^c7 are heterocyclyl groups, the same groups as the heterocyclyl group as R ^c5 in formula (c3) can be mentioned.

R ^c6 and R ^c7 may be bonded to each other to form a ring. The group formed by the ring formed by R ^c6 and R ^c7 is preferably a cycloalkylidene group. When R ^c6 and R ^c7 combine to form a cycloalkylidene group, the ring constituting the cycloalkylidene group is preferably a 5- to 6-membered ring, more preferably a 5-membered ring.

When forming a ring with R ^c7 and the benzene ring of the fluorene skeleton, the ring may be an aromatic ring or an aliphatic ring.

When the group formed by combining R ^c6 and R ^c7 is a cycloalkylidene group, the cycloalkylidene group may be fused with one or more other rings. Examples of rings that may be fused with a cycloalkylidene group include a benzene ring, a naphthalene ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a furan ring, a thiophene ring, a pyrrole ring, and a pyridine ring. ring, pyrazine ring, pyrimidine ring, and the like.

Among the R ^c6 and R ^c7 described above, examples of preferable groups include groups represented by the formula -A1-A2. In the formula, A1 is a linear alkylene group, and A2 is an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, or an alkoxycarbonyl group.

The number of carbon atoms in the linear alkylene group of A1 is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less. When A2 is an alkoxy group, the alkoxy group may be linear or branched, preferably linear. The number of carbon atoms in the alkoxy group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less. When A2 is a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is preferable, and a fluorine atom, a chlorine atom, or a bromine atom is more preferable. When A2 is a halogenated alkyl group, the halogen atom contained in the halogenated alkyl group is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. The halogenated alkyl group may be linear or branched, preferably linear. When A2 is a cyclic organic group, examples of the cyclic organic group are the same as the cyclic organic groups that R ^c6 and R ^c7 have as substituents. When A2 is an alkoxycarbonyl group, examples of the alkoxycarbonyl group are the same as the alkoxycarbonyl groups that R ^c6 and R ^c7 have as substituents.

Preferred specific examples of R ^c6 and R ^c7 include alkyl groups such as ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-heptyl group, and n-octyl group; 2-methoxyethyl group, 3-methoxy-n-propyl group, 4-methoxy-n-butyl group, 5-methoxy-n-pentyl group, 6-methoxy-n-hexyl group, 7-methoxy-n-heptyl group, 8-methoxy -n-octyl group, 2-ethoxyethyl group, 3-ethoxy-n-propyl group, 4-ethoxy-n-butyl group, 5-ethoxy-n-pentyl group, 6-ethoxy-n-hexyl group, 7- Alkoxyalkyl groups such as ethoxy-n-heptyl group and 8-ethoxy-n-octyl group; 2-cyanoethyl group, 3-cyano-n-propyl group, 4-cyano-n-butyl group, 5-cyano-n - Cyanoalkyl groups such as pentyl group, 6-cyano-n-hexyl group, 7-cyano-n-heptyl group, and 8-cyano-n-octyl group; 2-phenylethyl group, 3-phenyl-n-propyl group phenyl groups, such as 4-phenyl-n-butyl group, 5-phenyl-n-pentyl group, 6-phenyl-n-hexyl group, 7-phenyl-n-heptyl group, and 8-phenyl-n-octyl group Alkyl group; 2-cyclohexylethyl group, 3-cyclohexyl-n-propyl group, 4-cyclohexyl-n-butyl group, 5-cyclohexyl-n-pentyl group, 6-cyclohexyl-n-hexyl group, 7-cyclohexyl-n -heptyl group, 8-cyclohexyl-n-octyl group, 2-cyclopentylethyl group, 3-cyclopentyl-n-propyl group, 4-cyclopentyl-n-butyl group, 5-cyclopentyl-n-pentyl group, 6-cyclopentyl group Cycloalkylalkyl groups such as n-hexyl group, 7-cyclopentyl-n-heptyl group, and 8-cyclopentyl-n-octyl group; 2-methoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl group, 4-methoxy Carbonyl-n-butyl group, 5-methoxycarbonyl-n-pentyl group, 6-methoxycarbonyl-n-hexyl group, 7-methoxycarbonyl-n-heptyl group, 8-methoxycarbonyl-n-octyl group, 2-ethoxy Carbonylethyl group, 3-ethoxycarbonyl-n-propyl group, 4-ethoxycarbonyl-n-butyl group, 5-ethoxycarbonyl-n-pentyl group, 6-ethoxycarbonyl-n-hexyl group, 7-ethoxycarbonyl-n -heptyl group, and alkoxycarbonylalkyl groups such as 8-ethoxycarbonyl-n-octyl group; 2-chloroethyl group, 3-chloro-n-propyl group, 4-chloro-n-butyl group, 5-chloro-n- Pentyl group, 6-chloro-n-hexyl group, 7-chloro-n-heptyl group, 8-chloro-n-octyl group, 2-bromoethyl group, 3-bromo-n-propyl group, 4-bromo-n- Butyl group, 5-bromo-n-pentyl group, 6-bromo-n-hexyl group, 7-bromo-n-heptyl group, 8-bromo-n-octyl group, 3,3,3-trifluoropropyl group, and halogenated alkyl groups such as 3,3,4,4,5,5,5-heptafluoro-n-pentyl group.

As R ^c6 and R ^c7 , preferred groups among the above include ethyl group, n-propyl group, n-butyl group, n-pentyl group, 2-methoxyethyl group, 2-cyanoethyl group, 2-phenylethyl group, 2-cyclohexylethyl group, 2-methoxycarbonylethyl group, 2-chloroethyl group, 2-bromoethyl group, 3,3,3-trifluoropropyl group, and 3,3,4,4,5,5,5-hepta It is a fluoro-n-pentyl group.

In formula (c5), A is particularly preferably S, since it is easy to obtain a photopolymerization initiator with excellent sensitivity.

In formula (c5), R ^c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group.
When R ^c9 in formula (c5) is a monovalent organic group, it can be selected from various organic groups as long as it does not impede the object of the present invention. The organic group is preferably a carbon atom-containing group, with one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
Suitable examples of the case where R ^c9 in formula (c5) is an organic group include the same monovalent organic group as R ^c5 in formula (c3).

In R ^c9 , substituted with a group selected from the group consisting of a benzoyl group; a naphthoyl group; an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group. benzoyl group; nitro group; benzofuranylcarbonyl group which may have a substituent is preferred; benzoyl group; naphthoyl group; 2-methylphenylcarbonyl group; 4-(piperazin-1-yl)phenylcarbonyl group ;4-(phenyl)phenylcarbonyl group is more preferred.

Further, in formula (c5), n4 is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0 or 1. When n4 is 1, the bonding position of R ^c9 is preferably at the para position with respect to the bond where the phenyl group to which R ^c9 is bonded is bonded to an oxygen atom or a sulfur atom.

In formulas (c1) and (c2), the monovalent organic group as R ^c2 is not particularly limited as long as it does not impede the object of the present invention. The organic group is preferably a carbon atom-containing group, with one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred. The number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
Suitable examples of the monovalent organic group as R ^c2 include the same groups as the monovalent organic group as R ^c5 in formula (c3). Specific examples of these groups are the same as the group explained for R ^c5 in formula (c3).
Also preferable as R ^c2 are a cycloalkylalkyl group, a phenoxyalkyl group which may have a substituent on the aromatic ring, and a phenylthioalkyl group which may have a substituent on the aromatic ring. The substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are the substituents contained in R ^c5 in formula (c3) when the phenyl group, naphthyl group, and heterocyclyl group further have a substituent. Same as base.

Among the organic groups, R ^c2 is a substituent containing the group represented by HX ₂ C- or H ₂ XC-, an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, or A cycloalkylalkyl group and a phenylthioalkyl group which may have a substituent on the aromatic ring are preferred. Alkyl group, phenyl group which may have a substituent, number of carbon atoms in cycloalkyl group included in cycloalkylalkyl group, number of carbon atoms in alkylene group included in cycloalkylalkyl group, cycloalkylalkyl group, aromatic The number of carbon atoms in the alkylene group included in the phenylthioalkyl group that may have a substituent on the ring, or the phenylthioalkyl group that may have a substituent on the aromatic ring, is determined by the formula (c3 ) is similar to R ^c5 .

Furthermore, as R ^c2 , a group represented by -A3-CO-O-A4 is also preferable. A3 is a divalent organic group, preferably a divalent hydrocarbon group, and preferably an alkylene group. A4 is a monovalent organic group, preferably a monovalent hydrocarbon group.

When A3 is an alkylene group, the alkylene group may be linear or branched, preferably linear. When A3 is an alkylene group, the number of carbon atoms in the alkylene group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less, and particularly preferably 1 or more and 4 or less.

Suitable examples of A4 include an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms. Preferred specific examples of A4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group. , phenyl group, naphthyl group, benzyl group, phenethyl group, α-naphthylmethyl group, and β-naphthylmethyl group.

Preferred specific examples of the group represented by -A3-CO-O-A4 include 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 2-n-propyloxycarbonylethyl group, and 2-n-butyl group. Oxycarbonylethyl group, 2-n-pentyloxycarbonylethyl group, 2-n-hexyloxycarbonylethyl group, 2-benzyloxycarbonylethyl group, 2-phenoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl group, 3-ethoxycarbonyl-n-propyl group, 3-n-propyloxycarbonyl-n-propyl group, 3-n-butyloxycarbonyl-n-propyl group, 3-n-pentyloxycarbonyl-n-propyl group, 3 Examples include -n-hexyloxycarbonyl-n-propyl group, 3-benzyloxycarbonyl-n-propyl group, and 3-phenoxycarbonyl-n-propyl group.

（式（ｃ７）及び（ｃ８）中、Ｒ^ｃ１０及びＲ^ｃ１１は、それぞれ独立に、１価の有機基であり、
ｎ５は０以上４以下の整数であり、
Ｒ^ｃ１０及びＲ^ｃ１１がベンゼン環上の隣接する位置に存在する場合、Ｒ^ｃ１０とＲ^ｃ１１とが互いに結合して環を形成してもよく、
Ｒ^ｃ１２は、１価の有機基であり、
ｎ６は１以下８以下の整数であり、
ｎ７は１以上５以下の整数であり、
ｎ８は０以上（ｎ７＋３）以下の整数である。） Further, as R ^c2 , a group represented by the following formula (c7) or (c8) is also preferable.

(In formulas (c7) and (c8), R ^c10 and R ^c11 are each independently a monovalent organic group,
n5 is an integer from 0 to 4,
When R ^c10 and R ^c11 are present at adjacent positions on the benzene ring, R ^c10 and R ^c11 may be bonded to each other to form a ring,
R ^c12 is a monovalent organic group,
n6 is an integer of 1 or less and 8 or less,
n7 is an integer from 1 to 5,
n8 is an integer from 0 to (n7+3). )

The organic groups as R ^c10 and R ^c11 in formula (c7) are the same as R ^c8 in formula (c4). R ^c10 is a halogenated alkoxy group containing a group represented by HX ₂ C- or H ₂ XC-, a halogenated alkyl group containing a group represented by HX ₂ C- or H ₂ XC-, an alkyl group, or A phenyl group is preferred. When R ^c10 and R ^c11 combine to form a ring, the ring may be an aromatic ring or an aliphatic ring. Suitable examples of the group represented by formula (c7) in which R ^c10 and R ^c11 form a ring include naphthalen-1-yl group and 1,2,3,4- Examples include tetrahydronaphthalen-5-yl group.
In the above formula (c7), n7 is an integer of 0 or more and 4 or less, preferably 0 or 1, and more preferably 0.

In the above formula (c8), R ^c12 is an organic group. Examples of the organic group include the same groups as the organic group explained for R ^c8 in formula (c4). Among the organic groups, alkyl groups are preferred. The alkyl group may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less. Preferred examples of R ^c12 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and the like, and among these, a methyl group is more preferred.

In the above formula (c8), n7 is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1 or 2. In the above formula (c8), n8 is 0 or more and (n7+3) or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0.
In the above formula (c8), n8 is an integer of 1 or more and 8 or less, preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1 or 2.

In formula (c2), R ^c3 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aryl group which may have a substituent. Preferred examples of the substituent that R ^c3 may have when it is an aliphatic hydrocarbon group include a phenyl group and a naphthyl group.

In formulas (c1) and (c2), R ^c3 is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a 2-cyclopentylethyl group, a 2-cyclobutylethyl group, Preferred examples include a cyclohexylmethyl group, a phenyl group, a benzyl group, a methylphenyl group, a naphthyl group, and among these, a methyl group or a phenyl group is more preferred.

Preferred specific examples of the compound represented by formula (c2) and having a group represented by formula (c3) as R ^c1 include the following compounds.

Preferred specific examples of the compound represented by formula (c2) and having a group represented by formula (c4) as R ^c1 include the following compounds.

Preferred specific examples of the compound represented by formula (c2) and having a group represented by formula (c5) as R ^c1 include the following compounds.

As the oxime ester compound, the following oxime ester compound (C1a) is also preferred.

（式（Ｃ１ａ）中、Ｘ^０１は、下記式（Ｃ１ａ－１）：

で表される構造において、芳香族環上に結合する水素原子のうち、ｔ２＋ｔ３個の水素原子を除いた基であり、Ｘ^０２及びＸ^０３は、それぞれ独立に１価の有機基であり、Ｘ^０４及びＸ^０５は、それぞれ独立に水素原子、置換基を有してもよい炭素原子数１以上１１以下のアルキル基、又は置換基を有してもよいアリール基であり、ｔ０～ｔ３は、それぞれ独立に、０又は１であり、ｔ２及びｔ３の少なくとも一方は１であり、
式（Ｃ１ａ－１）中、Ｘ^０６は、カルバゾール環中の窒素原子にＣ－Ｎ結合で結合する１価の有機基であり、ｔ４及びｔ５は、それぞれ独立に０又は１であり、ｔ４及びｔ５の少なくとも一方は１である。） (Oxime ester compound (C1a))
The oxime ester compound (C1a) is a compound represented by the following formula (C1a).

(In formula (C1a), X ⁰¹ is the following formula (C1a-1):

In the structure represented by , it is a group excluding t2+t3 hydrogen atoms from among the hydrogen atoms bonded to the aromatic ring, X ⁰² and X ⁰³ are each independently a monovalent organic group, and X ⁰⁴ and X ⁰⁵ are each independently a hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent, and t0 to t3 are: Each independently is 0 or 1, and at least one of t2 and t3 is 1,
In formula (C1a-1 ⁾ , At least one of t5 is 1. )

In formula (C1a-1), X ⁰⁶ is a monovalent organic group bonded to the nitrogen atom in the carbazole ring through a CN bond. The monovalent organic group may contain heteroatoms such as O, S, N, P, Si, and halogen atoms. The number of carbon atoms in the organic group as X ⁰⁶ is not particularly limited. The number of carbon atoms in the organic group as X ⁰⁶ is, for example, preferably 1 or more and 50 or less, more preferably 1 or more and 30 or less, particularly preferably 1 or more and 20 or less.

Preferred examples of the organic group as X ⁰⁶ include alkyl groups, alkenyl groups, alkynyl groups, aliphatic cyclic hydrocarbon groups, aryl groups, aliphatic heterocyclic groups, heteroaryl groups, aliphatic acyl groups, and aromatic acyl groups. groups, and combinations of these groups. Preferred examples of combinations of these groups include aralkyl groups, cycloalkylalkyl groups, and the like.

When the organic group as X ⁰⁶ is an alkyl group, alkenyl group, or alkynyl group, these groups may be linear or branched. When the organic group as X ⁰⁶ is an aliphatic acyl group, the portion other than the carbonyl group in the aliphatic acyl group may be linear, branched, or cyclic. , or a combination of these structures.

The organic group as X ⁰⁶ may have a substituent. Examples of substituents that the organic group as ^X06 may have include alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and 3 to 10 carbon atoms. Cycloalkyl group, cycloalkoxy group having 3 to 10 carbon atoms, saturated aliphatic acyl group having 2 to 20 carbon atoms, alkoxycarbonyl group having 2 to 20 carbon atoms, cycloalkoxy group having 2 to 20 carbon atoms, Saturated aliphatic acyloxy group, phenyl group which may have a substituent, phenoxy group which may have a substituent, phenylthio group which may have a substituent, benzoyl group which may have a substituent, A phenoxycarbonyl group which may have a substituent, a benzoyloxy group which may have a substituent, a phenylalkyl group having 7 to 20 carbon atoms which may have a substituent, a phenylalkyl group which may have a substituent and naphthyl group that may have a substituent, naphthoxy group that may have a substituent, naphthoyl group that may have a substituent, naphthoxycarbonyl group that may have a substituent, naphthoyl that may have a substituent Oxy group, naphthylalkyl group having 11 to 20 carbon atoms which may have a substituent, heterocyclyl group which may have a substituent, heterocyclylcarbonyl group which may have a substituent, amino group, 1 or an amino group substituted with an organic group of 2, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, a cyano group, and the like.

Among the above groups as X ⁰⁶ , alkyl groups, aryl groups, and aralkyl groups are preferred from the viewpoint of ease of synthesis and availability of the oxime ester compound (C1a).

Specific examples when X ⁰⁶ is an alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group. , neopentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, and n-icosyl group. .

Suitable examples when X ⁰⁶ is an aryl group include a phenyl group, a naphthalen-1-yl group, a naphthalen-2-yl group, a 2-phenylphenyl group, a 3-phenylphenyl group, and a 4-phenylphenyl group. can be mentioned.

Suitable examples when X ⁰⁶ is an aralkyl group include benzyl group, phenethyl group, 3-phenyl-n-propyl group, 4-phenyl-n-butyl group, naphthalen-1-ylmethyl group, and naphthalene-2 -ylmethyl group is mentioned.

Among the specific examples of X ⁰⁶ explained above, methyl group, ethyl group, phenyl group, naphthalen-1-yl group, and naphthalen-2-yl group are preferable, and ethyl group and phenyl group are more preferable.

X ⁰¹ is not particularly limited as long as it is a group excluding t2+t3 hydrogen atoms from among the hydrogen atoms bonded to the aromatic ring in the structure represented by the above formula (C1a-1). The group represented by the above formula (C1a-1) is preferably a monovalent or divalent group represented by the following formulas (C1a-1a) to (C1a-1c).

In formulas (C1a-1a) to (C1a-1c), t4, t5, and X ⁰⁶ are the same as in formula (C1a-1). X ⁰⁷ is a divalent organic group bonded to the nitrogen atom in the carbazole ring through a CN bond. X ⁰⁷ is a divalent organic group containing an aromatic ring. Of the two bonds that X ⁰⁷ has, the other bond that is bonded to the carbazole ring in formulas (C1a-1a) and (C1a-1c) is bonded to the aromatic ring in X ⁰⁷ .
Note that X ⁰⁷ corresponds to a divalent group obtained by removing one hydrogen atom bonded to the aromatic ring from the monovalent organic group containing an aromatic ring as X ⁰⁶ described above.

Preferred specific examples of X ⁰⁷ are described below using formula (C1a-1a) as an example. The divalent group corresponding to X ⁰⁷ in the following structure is also preferable as X ⁰⁷ in formula (C1a-1c).

In formulas (C1a-1a) to (C1a-1c), the bonding position of the nitro group on the carbazole ring is not particularly limited.
Since the oxime ester compound (C1a) is easy to synthesize and obtain, the group represented by the formula (C1a-1a), the group represented by the formula (C1a-1b), and the group represented by the formula (C1a-1c) are used. Preferred examples of the group represented by the formula (C1a-1aa), the group represented by the formula (C1a-1ba), and the group represented by the formula (C1a-1ca) are exemplified, respectively. .

In formula (C1a), X ⁰² and X ⁰³ are each independently a monovalent organic group. Examples of suitable organic groups as X ⁰² and X ⁰³ include alkyl groups, alkoxy groups, cycloalkyl groups, cycloalkoxy groups, saturated aliphatic acyl groups, alkoxycarbonyl groups, saturated aliphatic acyloxy groups, A phenyl group that may have a substituent, a phenoxy group that may have a substituent, a benzoyl group that may have a substituent, a phenoxycarbonyl group that may have a substituent, a phenoxy group that may have a substituent Benzoyloxy group, phenylalkyl group which may have a substituent, naphthyl group which may have a substituent, naphthoxy group which may have a substituent, naphthoyl group which may have a substituent, substituted Naphthoxycarbonyl group which may have a substituent, naphthoyloxy group which may have a substituent, naphthylalkyl group which may have a substituent, heterocyclyl group which may have a substituent, substituent Examples include a heterocyclylcarbonyl group which may have , an amino group substituted with one or two organic groups, a morpholin-1-yl group, and a piperazin-1-yl group.

When X ⁰² and X ⁰³ are alkyl groups, the number of carbon atoms in the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. Furthermore, when X ⁰² and X ⁰³ are alkyl groups, they may be linear or branched. Specific examples when X ⁰² and X ⁰³ are alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n - pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, Examples include isononyl group, n-decyl group, and isodecyl group. Furthermore, when X ⁰² and X ⁰³ are alkyl groups, the alkyl groups may contain an ether bond (-O-) in the carbon chain. Examples of the alkyl group having an ether bond in the carbon chain include methoxyethyl group, ethoxyethyl group, methoxyethoxyethyl group, ethoxyethoxyethyl group, propyloxyethoxyethyl group, and methoxypropyl group.

When X ⁰² and X ⁰³ are alkoxy groups, the number of carbon atoms in the alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less. Furthermore, when X ⁰² and X ⁰³ are alkoxy groups, they may be linear or branched. Specific examples when X ⁰² and X ⁰³ are alkoxy groups include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group. group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec- Examples include octyloxy group, tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, and isodecyloxy group. Furthermore, when X ⁰² and X ⁰³ are alkoxy groups, the alkoxy groups may contain an ether bond (-O-) in the carbon chain. Examples of the alkoxy group having an ether bond in the carbon chain include methoxyethoxy group, ethoxyethoxy group, methoxyethoxyethoxy group, ethoxyethoxyethoxy group, propyloxyethoxyethoxy group, and methoxypropyloxy group.

When X ⁰² and X ⁰³ are a cycloalkyl group or a cycloalkoxy group, the number of carbon atoms in the cycloalkyl group or cycloalkoxy group is preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less. Specific examples when X ⁰² and X ⁰³ are cycloalkyl groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group. Specific examples when X ⁰² and X ⁰³ are cycloalkoxy groups include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, and cyclooctyloxy group. .

When X ⁰² and X ⁰³ are a saturated aliphatic acyl group or a saturated aliphatic acyloxy group, the number of carbon atoms in the saturated aliphatic acyl group or saturated aliphatic acyloxy group is preferably 2 or more and 21 or less, and 2 or more and 7 or less. More preferred. Specific examples when R ^c7 is a saturated aliphatic acyl group include acetyl group, propanoyl group, n-butanoyl group, 2-methylpropanoyl group, n-pentanoyl group, 2,2-dimethylpropanoyl group, n -hexanoyl group, n-heptanoyl group, n-octanoyl group, n-nonanoyl group, n-decanoyl group, n-undecanoyl group, n-dodecanoyl group, n-tridecanoyl group, n-tetradecanoyl group, n-pentadecanoyl group Examples thereof include a noyl group and an n-hexadecanoyl group. Specific examples when X ⁰² and X ⁰³ are saturated aliphatic acyloxy groups include acetyloxy group, propanoyloxy group, n-butanoyloxy group, 2-methylpropanoyloxy group, n-pentanoyloxy group , 2,2-dimethylpropanoyloxy group, n-hexanoyloxy group, n-heptanoyloxy group, n-octanoyloxy group, n-nonanoyloxy group, n-decanoyloxy group, n-undecanoyloxy group group, n-dodecanoyloxy group, n-tridecanoyloxy group, n-tetradecanoyloxy group, n-pentadecanoyloxy group, and n-hexadecanoyloxy group.

When X ⁰² and X ⁰³ are alkoxycarbonyl groups, the number of carbon atoms in the alkoxycarbonyl group is preferably 2 or more and 20 or less, more preferably 2 or more and 7 or less. Specific examples when X ⁰² and X ⁰³ are alkoxycarbonyl groups include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n- Heptyloxycarbonyl group, n-octyloxycarbonyl group, isooctyloxycarbonyl group, sec-octyloxycarbonyl group, tert-octyloxycarbonyl group, n-nonyloxycarbonyl group, isononyloxycarbonyl group, n-decyloxycarbonyl group group, and isodecyloxycarbonyl group.

When X ⁰² and X ⁰³ are phenylalkyl groups, the number of carbon atoms in the phenylalkyl group is preferably 7 or more and 20 or less, more preferably 7 or more and 10 or less. Furthermore, when X ⁰² and X ⁰³ are naphthylalkyl groups, the number of carbon atoms in the naphthylalkyl group is preferably 11 or more and 20 or less, more preferably 11 or more and 14 or less. Specific examples when X ⁰² and X ⁰³ are phenylalkyl groups include benzyl group, 2-phenylethyl group, 3-phenylpropyl group, and 4-phenylbutyl group. Specific examples when X ⁰² and X ⁰³ are naphthylalkyl groups include α-naphthylmethyl group, β-naphthylmethyl group, 2-(α-naphthyl)ethyl group, and 2-(β-naphthyl)ethyl group. can be mentioned. When X ⁰² and X ⁰³ are a phenylalkyl group or a naphthylalkyl group, R ^c7 may further have a substituent on the phenyl group or naphthyl group.

When X ⁰² and X ⁰³ are heterocyclyl groups, the heterocyclyl group is a 5- or 6-membered monocycle containing one or more N, S, O, or a combination of such monocycles, or a combination of such monocycles and a benzene ring. is a fused heterocyclyl group. When the heterocyclyl group is a condensed ring, the number of monocycles constituting the condensed ring is up to three. The heterocyclyl group may be an aromatic group (heteroaryl group) or a non-aromatic group. Examples of the heterocycle constituting such a heterocyclyl group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, Examples include isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran. It will be done. When R ^c7 is a heterocyclyl group, the heterocyclyl group may further have a substituent.

When X ⁰² and X ⁰³ are heterocyclyl carbonyl groups, the heterocyclyl group contained in the heterocyclyl carbonyl group is the same as when X ⁰² and X ⁰³ are heterocyclyl groups.

When X ⁰² and X ⁰³ are amino groups substituted with 1 or 2 organic groups, preferred examples of the organic group include an alkyl group having 1 to 20 carbon atoms, and a cyclo group having 3 to 10 carbon atoms. Alkyl group, saturated aliphatic acyl group having 2 to 21 carbon atoms, phenyl group that may have a substituent, benzoyl group that may have a substituent, number of carbon atoms that may have a substituent A phenylalkyl group having 7 or more and 20 or less, a naphthyl group that may have a substituent, a naphthoyl group that may have a substituent, or a naphthylalkyl group having 11 or more and 20 or less carbon atoms that may have a substituent. , and a heterocyclyl group. Specific examples of these suitable organic groups are the same as X ⁰² and X ⁰³ . Specific examples of amino groups substituted with 1 or 2 organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n- butylamino group, di-n-butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, naphthylamino group, acetylamino group, propanoylamino group, n-butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino group, n- Examples include decanoylamino group, benzoylamino group, α-naphthoylamino group, and β-naphthoylamino group.

When the phenyl group, naphthyl group, and heterocyclyl group contained in X ⁰² and X ⁰³ further have a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, and Alkoxy group, saturated aliphatic acyl group having 2 to 7 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, saturated aliphatic acyloxy group having 2 to 7 carbon atoms, 1 to 6 carbon atoms A monoalkylamino group having an alkyl group of 1 to 6 carbon atoms, a dialkylamino group having an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, a halogen, a nitro group, a cyano group, etc. Can be mentioned.

These substituents include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a saturated aliphatic acyl group having 2 to 7 carbon atoms, and a saturated aliphatic acyl group having 2 to 7 carbon atoms. an alkoxycarbonyl group, a saturated aliphatic acyloxy group having 2 to 7 carbon atoms, a monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, and a dialkylamino group having an alkyl group having 1 to 6 carbon atoms. When the substituent is a group, an ether bond (-O-) may be included in the carbon chain in these substituents.

When the phenyl group, naphthyl group ^{, and heterocyclyl group contained in X 02 and} is preferred. When the phenyl group, naphthyl group, and heterocyclyl group contained in X ⁰² and X ⁰³ have a plurality of substituents, the plurality of substituents may be the same or different.

As X ⁰² and X ⁰³ , a cycloalkylalkyl group, a phenoxyalkyl group that may have a substituent on the aromatic ring, and a phenylthioalkyl group that may have a substituent on the aromatic ring are also preferable. The substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are the same as those described above as the substituents that the phenyl group may have.

Among organic groups ^, X ⁰² and Good phenylthioalkyl groups are preferred. As the alkyl group, an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, an alkyl group having 1 to 4 carbon atoms is particularly preferable, and a methyl group is the most preferable. preferable. Among the phenyl groups which may have substituents, methylphenyl is preferred, and 2-methylphenyl is more preferred. The number of carbon atoms in the cycloalkyl group contained in the cycloalkylalkyl group is preferably 5 or more and 10 or less, more preferably 5 or more and 8 or less, and particularly preferably 5 or 6. The number of carbon atoms in the alkylene group contained in the cycloalkylalkyl group is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2. Among the cycloalkylalkyl groups, a cyclopentylethyl group is preferred. The number of carbon atoms in the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2. Among the phenylthioalkyl groups which may have a substituent on the aromatic ring, 2-(4-chlorophenylthio)ethyl group is preferred.

Furthermore, as X ⁰² and X ⁰³ , a group represented by -A ¹ -CO-O-A ² is also preferable. A ¹ is a divalent organic group, preferably a divalent hydrocarbon group, and preferably an alkylene group. A ² is a monovalent organic group, preferably a monovalent hydrocarbon group.

When A ¹ is an alkylene group, the alkylene group may be linear or branched, preferably linear. When A ¹ is an alkylene group, the number of carbon atoms in the alkylene group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less, and particularly preferably 1 or more and 4 or less.

Suitable examples of A ² include an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms. Preferred specific examples of ^A4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group. Examples include phenyl group, naphthyl group, benzyl group, phenethyl group, α-naphthylmethyl group, and β-naphthylmethyl group.

Preferred specific examples of the group represented by -A ¹ -CO-O-A ² include 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 2-n-propyloxycarbonylethyl group, 2-n -Butyloxycarbonylethyl group, 2-n-pentyloxycarbonylethyl group, 2-n-hexyloxycarbonylethyl group, 2-benzyloxycarbonylethyl group, 2-phenoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl group, 3-ethoxycarbonyl-n-propyl group, 3-n-propyloxycarbonyl-n-propyl group, 3-n-butyloxycarbonyl-n-propyl group, 3-n-pentyloxycarbonyl-n-propyl group , 3-n-hexyloxycarbonyl-n-propyl group, 3-benzyloxycarbonyl-n-propyl group, and 3-phenoxycarbonyl-n-propyl group.

式（Ｃ１ａ－ｉ）及び（Ｃ１ａ－ｉｉ）中、Ｘ^０８及びＸ^０９はそれぞれ有機基である。ｔ６は０以上４以下の整数である。Ｘ^０８及びＸ^０９がベンゼン環上の隣接する位置に存在する場合、Ｘ^０８及びＸ^０９が互いに結合して環を形成してもよい。ｔ７は１以上８以下の整数である。ｔ８は１以上５以下の整数である。ｔ９は０以上（ｔ８＋３）以下の整数である。Ｘ^０１０は有機基である。 As described above, X ⁰² and ^{X 03 are} preferably groups represented by the following formula (C1a-i) or (C1a-ii ⁾ .

In formulas (C1a-i) and (C1a-ii), X ⁰⁸ and X ⁰⁹ are each an organic group. t6 is an integer from 0 to 4. When X ⁰⁸ and X ⁰⁹ are present at adjacent positions on the benzene ring, X ⁰⁸ and X ⁰⁹ may be bonded to each other to form a ring. t7 is an integer from 1 to 8. t8 is an integer from 1 to 5. t9 is an integer from 0 to (t8+3). X ⁰¹⁰ is an organic group.

Examples of organic groups for X ⁰⁸ and X ⁰⁹ in formula (C1a-i) are the same as for X ⁰² and X ⁰³ . X ⁰⁸ is preferably an alkyl group or a phenyl group. When X ⁰⁸ is an alkyl group, the number of carbon atoms is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less, and most preferably 1. That is, most preferably X ⁰⁸ is a methyl group. When X ⁰⁸ and X ⁰⁹ combine to form a ring, the ring may be an aromatic ring or an aliphatic ring. Suitable examples of the group represented by formula (C1a-i) in which X ⁰⁸ and X ⁰⁹ form a ring include naphthalen-1-yl group and 1,2,3,4 -tetrahydronaphthalen-5-yl group and the like. In the above formula (C1a-i), t6 is an integer of 0 or more and 4 or less, preferably 0 or 1, and more preferably 0.

In the above formula (C1a-ii), X ⁰¹⁰ is an organic group. Examples of the organic group include the same groups as the organic groups explained for X ⁰² and X ⁰³ . Among the organic groups, alkyl groups are preferred. The alkyl group may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less. Preferred examples of X ⁰¹⁰ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and the like, and among these, a methyl group is more preferred.

In the above formula (C1a-ii), t8 is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1 or 2. In the above formula (C1a-ii), t9 is 0 or more and (t8+3) or less, preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0. In the above formula (C1a-ii), t7 is an integer of 1 or more and 8 or less, preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1 or 2.

In formula (C1a), X ⁰⁴ and X ⁰⁵ are each independently a hydrogen atom, an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent. be. Preferred examples of the substituent that X ⁰⁴ and X ⁰⁵ may have when they are an alkyl group include a phenyl group and a naphthyl group. In addition, when X ⁰⁴ and X ⁰⁵ are aryl groups, substituents that may be included include an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom. is preferably exemplified.

In formula (C1a), X ⁰⁴ and X ⁰⁵ include a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, phenyl group, benzyl group, methylphenyl group, naphthyl group, Preferred examples include a methyl group or a phenyl group, and among these, a methyl group or a phenyl group is more preferred.

As mentioned above, X ⁰¹ is preferably a group represented by the formula (C1a-1aa), a group represented by the formula (C1a-1ba), or a group represented by the formula (C1a-1ca).
When X ⁰¹ is a group represented by formula (C1a-1aa), preferred specific examples of the oxime ester compound represented by formula (C1a) include the following compounds.

When X ⁰¹ is a group represented by formula (C1a-1ba), preferred specific examples of the oxime ester compound represented by formula (C1a) include the following compounds.

When X ⁰¹ is a group represented by formula (C1a-1ca), preferred specific examples of the oxime ester compound represented by formula (C1a) include the following compounds.

Photopolymerization initiators (C) other than oxime ester compounds include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-methyl-1-[4-(methylthio) phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-dimethylaminophenyl)butan-1-one, 2-(4-methylbenzyl)-2-diethylamino-1 -(4-morpholinophenyl)butan-1-one, 2-methyl-1-phenyl-2-morpholinopropan-1-one, 2-methyl-1-[4-(hexyl)phenyl]-2-morpholinopropane- α-aminoketone compounds such as 1-one, 2-ethyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one; 1-phenyl-2-hydroxy-2-methylpropan-1-one , 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexylphenylketone α-hydroxyketone photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzyl methyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4 - Benzophenone photopolymerization initiators such as phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl, 4'-methyldiphenyl sulfide, 4,4'-bisdiethylaminobenzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone , isopropylthioxanthone, 2,4-diisopropylthioxanthone, and other thioxanthone-based photopolymerization initiators; 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-pipenyl-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, 2,4 Triazines such as -trichloromethyl-(4'-methoxystyryl)-6-triazine, 2-[4-(4-methoxystyryl)phenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine -based photopolymerization initiator; Carbazole-based photopolymerization initiator; 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-bis Imidazole, 2,2'-bis(2-bromophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-bis(2 -chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetra Phenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2, 2'-bis(2-bromophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dibromophenyl)-4,4' , 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-tribromophenyl)-4,4',5,5'-tetraphenyl-1, Examples include biimidazole photopolymerization initiators such as 2'-biimidazole; benzimidazoline photopolymerization initiators represented by the following formula.

The photopolymerization initiators can be used alone or in combination of two or more. By using two or more types in combination, it is easy to effectively utilize light rays with a wide range of wavelengths included in the exposure light, and it is also easy to adjust the sensitivity of the photosensitive composition to an appropriate range.

The content of the photopolymerization initiator (C) in the total solid content of the photosensitive composition is preferably 0.5% by mass or more and 15% by mass or less, and more preferably 1% by mass or more and 10% by mass or less.

When using a photopolymerization initiator other than the oxime ester compound in combination, the ratio of the mass of the oxime ester compound to the mass of the photopolymerization initiator (C) is preferably 50% by mass or more, and 50% by mass or more and 99% by mass or less. is more preferable, particularly preferably 70% by mass or more and 97% by mass or less, and most preferably 80% by mass or more and 95% by mass or less.
When the oxime ester compound is contained in an amount within the range of the photopolymerization initiator (C), it is particularly difficult to form a patterned cured product having a width wider than the desired width.

<Light blocking agent (D)>
The photosensitive composition contains a light blocking agent (D). The light shielding agent (D) may be an inorganic black pigment or an organic black pigment. The photosensitive composition may contain one kind or two or more kinds of light shielding agents (D).
By adjusting the type of light shielding agent (D), the blending ratio, etc., it is possible to form the light shielding layer 2 having a desired OD value (optical density). For example, the OD value (optical density) per 1 μm of thickness of the light shielding layer 2 is preferably 1.0 or more, more preferably 1.5 or more.

[Inorganic black pigment]
Carbon black is preferred as the inorganic black pigment. Other inorganic black pigments include titanium oxynitride, titanium nitride, fine particles mainly composed of silver-tin (AgSn) alloys, and metal oxides such as copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, and silver. , composite oxides, metal sulfides, metal sulfates, or metal carbonates.

As the carbon black, known carbon blacks such as channel black, furnace black, thermal black, and lamp black can be used.

As the carbon black, carbon black that has been treated to introduce acidic groups may be used.
Carbon black that has been treated to introduce acidic groups is carbon black into which acidic groups have been introduced. By using carbon black that has been treated to introduce acidic groups, the generation of development residues in the unexposed areas 5 can be suppressed. Therefore, in the obtained optical element 10, a decrease in the transmittance of the unexposed portion 5 of the lens 1 can be suppressed.
The acidic group introduced into carbon black is a functional group exhibiting acidity according to the Brønsted definition. Specific examples of acidic groups include carboxyl groups, sulfonic acid groups, and phosphoric acid groups. The acidic group introduced into carbon black may form a salt. The cation that forms a salt with an acidic group is not particularly limited as long as it does not impede the object of the present invention. Examples of cations include various metal ions, cations of nitrogen-containing compounds, ammonium ions, etc., and alkali metal ions such as sodium ions, potassium ions, lithium ions, and ammonium ions are preferred.
The number of acidic groups introduced into carbon black may be one or two or more.

The method of introducing acidic groups into carbon black is not particularly limited. Examples of methods for introducing acidic groups include the following methods.
1) A method of introducing sulfonic acid groups into carbon black by a direct substitution method using concentrated sulfuric acid, oleum, chlorosulfonic acid, etc., or an indirect substitution method using sulfite, bisulfite, etc.
2) A method of diazo coupling an organic compound having an amino group and an acidic group with carbon black.
3) A method of reacting an organic compound having a halogen atom and an acidic group with carbon black having a hydroxyl group by Williamson's etherification method.
4) A method of reacting an organic compound having a halocarbonyl group and an acidic group protected by a protecting group with carbon black having a hydroxyl group.
5) A method in which carbon black is subjected to a Friedel-Crafts reaction using an organic compound having a halocarbonyl group and an acidic group protected by a protecting group, and then deprotected.

Among these methods, method 2) is preferred because the treatment for introducing acidic groups is easy and safe. The organic compound having an amino group and an acidic group used in method 2) is preferably a compound in which an amino group and an acidic group are bonded to an aromatic group. Examples of such compounds include aminobenzenesulfonic acids such as sulfanilic acid and aminobenzoic acids such as 4-aminobenzoic acid.

The number of moles of acidic groups introduced into carbon black is not particularly limited as long as it does not impede the object of the present invention. The number of moles of acidic groups introduced into carbon black is preferably 1 mmol or more and 200 mmol or less, more preferably 5 mmol or more and 100 mmol or less, per 100 g of carbon black.

[Organic black pigment]
Examples of the organic black pigment include lactam pigments represented by the following formula (d1) and perylene pigments.

<Lactam pigment>
The lactam pigment is a compound represented by the following formula (d1).

In formula (d1), X ^d represents a double bond and is each independently an E form or a Z form as a geometric isomer, and R ^d1 each independently represents a hydrogen atom, a methyl group, a nitro group, a methoxy group, Indicates a bromine atom, chlorine atom, fluorine atom, carboxy group, or sulfo group. R ^d2 each independently represents a hydrogen atom, a methyl group, or a phenyl group. R ^d3 each independently represents a hydrogen atom, a methyl group, or a chlorine atom.
The compound represented by formula (d1) can be used alone or in combination of two or more.
R ^d1 is preferably bonded to the 6-position of the dihydroindone ring from the viewpoint of easy production of the compound represented by formula (d1), and R ^d3 is preferably bonded to the 4-position of the dihydroindone ring. is preferred. From the same viewpoint, R ^d1 , R ^d2 , and R ^d3 are preferably hydrogen atoms.
The compound represented by formula (d1) has EE form, ZZ form, and EZ form as geometric isomers, but it may be a single compound of any of these, or a mixture of these geometric isomers. It may be.
The compound represented by formula (d1) can be produced, for example, by the method described in International Publication No. 2000/24736 and International Publication No. 2010/081624.

In order to disperse the lactam pigment well in the photosensitive composition, the average particle diameter of the lactam pigment is preferably 10 nm or more and 1000 nm or less.

<Perylene pigment>
The perylene pigment is a compound having a perylene skeleton, and is not particularly limited as long as it is a pigment that exhibits black color.
Specific examples of perylene pigments include perylene pigments represented by the following formula (d2), perylene pigments represented by the following formula (d3), and perylene pigments represented by the following formula (d4). It will be done. As commercially available products, products such as BASF's product names K0084 and K0086, Pigment Black 21, 30, 31, 32, 33, and 34, etc. can be preferably used as perylene pigments.

式（ｄ２）中、Ｒ^ｄ１１及びＲ^ｄ１２は、それぞれ独立に炭素原子数１以上３以下のアルキレン基を表し、Ｒ^ｄ１３及びＲ^ｄ１４は、それぞれ独立に、水素原子、水酸基、メトキシ基、又はアセチル基を表す。

In formula (d2), R ^d11 and R ^d12 each independently represent an alkylene group having 1 to 3 carbon atoms, and R ^d13 and R ^d14 each independently represent a hydrogen atom, a hydroxyl group, a methoxy group, or an acetyl group. represents a group.

式（ｄ３）中、Ｒ^ｄ１５及びＲ^ｄ１６は、それぞれ独立に、炭素原子数１以上７以下のアルキレン基を表す。

In formula (d3), R ^d15 and R ^d16 each independently represent an alkylene group having 1 or more and 7 or less carbon atoms.

式（ｄ４）中、Ｒ^ｄ１７及びＲ^ｄ１８は、それぞれ独立に、水素原子、炭素原子数１以上２２以下のアルキル基であり、Ｎ，Ｏ、Ｓ、又はＰのヘテロ原子を含んでいてもよい。Ｒ^ｄ１７及びＲ^ｄ１８がアルキル基である場合、当該アルキル基は、直鎖状であっても、分岐鎖状であってもよい。

In formula (d4), R ^d17 and R ^d18 are each independently a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, and may contain a heteroatom of N, O, S, or P. . When R ^d17 and R ^d18 are alkyl groups, the alkyl groups may be linear or branched.

The compound represented by the above formula (d2), the compound represented by the formula (d3), and the compound represented by the formula (d4) are disclosed in, for example, JP-A No. 62-1753, Japanese Patent Publication No. 63-26784. It can be synthesized using the method described in the publication. That is, using perylene-3,5,9,10-tetracarboxylic acid or its dianhydride and amines as raw materials, a heating reaction is performed in water or an organic solvent. Then, the desired product can be obtained by reprecipitating the obtained crude product in sulfuric acid or recrystallizing it in water, an organic solvent, or a mixed solvent thereof.

In order to disperse the perylene pigment well in the photosensitive composition and form a cured product with low transmittance for light in a wide wavelength range, the volume average particle diameter of the perylene pigment should be 10 nm or more and 1000 nm or less. is preferable, 10 nm or more and 500 nm or less is more preferable, and 10 nm or more and 200 nm or less is particularly preferable.
Further, when the volume particle diameter of the perylene pigment is within the above range, it is easy to stably form a cured product having a smooth surface with a low arithmetic mean roughness Ra.

The form of the light shielding agent (D) used in preparing the photosensitive composition is not particularly limited. The light shielding agent (D) may be used as a powder or a dispersion. The light blocking agent (D) is preferably used in the preparation of the photosensitive composition as a dispersion.
As the dispersion liquid, a dispersion liquid containing two or more kinds of light shielding agents (D) may be used. Furthermore, two or more dispersions containing different types of light shielding agents may be used.

Examples of the dispersion medium include organic solvents such as propylene glycol monomethyl ether acetate, cellosolve acetate, 3-methoxybutyl acetate, methoxypropyl acetate, 2-methoxyethyl acetate, 3-ethoxyethyl propionate, and propylene glycol monomethyl ether propionate. can be used.

A dispersant may be used to stabilize the dispersion of the light shielding agent (D) in the dispersion liquid and to improve the dispersibility of the light shielding agent (D) in the photosensitive composition.
As the dispersant, it is preferable to use a polymer dispersant such as a polyethyleneimine type, urethane resin type, or acrylic resin type.
Among these, urethane resin-based dispersants are preferred because they have good solubility in developing solutions and are less likely to cause residues to adhere to lenses, development equipment, piping, etc. after development.
When using a dispersant, the content of the dispersant in the photosensitive composition is, for example, 5% by mass or more and 50% by mass or less, and 10% by mass or more and 40% by mass, based on the content of the light blocking agent (D). The following are preferred.
Note that corrosive gas caused by the dispersant may be generated from the cured product. For this reason, it is also an example of a preferred embodiment that the light shielding agent (D) is subjected to a dispersion treatment without using a dispersant.

The viscosity of the dispersion of the light blocking agent (D) is not particularly limited. The viscosity of the dispersion liquid is preferably 3 mPa·s or more and 200 mPa·s or less, as measured at 25° C. using an E-type viscometer.

The particle size of the light shielding agent (D) in the dispersion liquid is preferably 80 nm or more and 300 nm or less as a dispersed average particle size. The dispersed average particle diameter can be measured using a laser diffraction particle size distribution analyzer.

The content of the light shielding agent (D) in the total solid content of the photosensitive composition is preferably 5% by mass or more and 60% by mass or less, more preferably 10% by mass or more and 50% by mass or less, and 20% by mass or more and 40% by mass. The following are more preferred.

<Thickener (E)>
The photosensitive composition of this embodiment preferably contains one or more thickeners (E). When the photosensitive composition contains the thickener (E), it is easy to prepare a photosensitive composition having a V2 of 6 cP or more and a thixotropy index (V1/V2) of 1.5 or more.
As used herein, a thickener is a substance that increases the viscosity of a liquid. The thickener (E) is preferably a thickener that also imparts thixotropic properties. In addition, the above-mentioned alkali-soluble resin (A), photopolymerizable monomer (B), photopolymerization initiator (C), light blocking agent (D), and dispersing agent for the light blocking agent (D) are added to the thickener (E). is not applicable.

The thickener (E) is not particularly limited as long as it is a substance that can increase the viscosity of the photosensitive composition, and examples thereof include thickeners having a urea structure. A thickener having a urea structure is, for example, one in which urea structures (-NH-CO-NH-) are linked with various crosslinking molecules (eg, ethylene oxide or propylene oxide).
Moreover, fumed silica is also mentioned as the thickener (E). Fumed silica is a dry silica produced, for example, by flame pyrolysis of chlorosilane. Preferably, fumed silica is used with a thickener having a urea structure.

The content of the thickener (E) in the photosensitive composition is preferably 0.1% by mass or more and 5% by mass or less, and 0.3% by mass or more and 2% by mass or less in the total solid content of the photosensitive composition. More preferably, 0.5% by mass or more and 1% by mass or less is particularly preferred.

<Organic solvent (S)>
The photosensitive composition contains an organic solvent (S) for dilution. Examples of the organic solvent (S) include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol mono-n-butyl ether. -Propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n- Butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc. ) Alkylene glycol monoalkyl ethers; (poly)alkylenes such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, etc. Glycol monoalkyl ether acetates; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone; methyl 2-hydroxypropionate; Lactic acid alkyl esters such as ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropionic acid Ethyl, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, ethyl acetate , n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate , other esters such as ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N-methylpyrrolidone, N,N Amides such as -dimethylformamide and N,N-dimethylacetamide are included.

Among these, alkylene glycol monoalkyl ethers, alkylene glycol monoalkyl ether acetates, other ethers mentioned above, lactic acid alkyl esters, and other esters mentioned above are preferred; Other ethers and other esters mentioned above are more preferred. These solvents can be used alone or in combination of two or more.

Moreover, it is preferable that the organic solvent (S) includes an organic solvent having one or more hydroxyl groups in its molecular structure. The organic solvent having one or more hydroxyl groups in its molecular structure is preferably used together with alkylene glycol monoalkyl ether acetates.
Examples of organic solvents having one or more hydroxyl groups in the molecular structure include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and n-butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol. Examples include alcohols.

The content of the organic solvent (S) is preferably such that the solid content concentration of the photosensitive composition is 20% by mass or more, more preferably 30% by mass or more. The upper limit of the solid content concentration of the photosensitive composition is preferably 50% by mass or less, more preferably 40% by mass or less.

It contains an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S), ) has a thixotropy index of 1.5 or more, and has a viscosity V2 of 6 cP or more at 25° C. and 50 rpm in an E-type viscometer, and has a solid content concentration of 30 mass % or more, as shown in Examples, light leakage can be significantly suppressed.

<Other ingredients>
The photosensitive composition may contain various additives as necessary. Examples of additives include sensitizers, curing accelerators, fillers, adhesion promoters such as silane coupling agents, antioxidants, anti-aggregation agents, thermal polymerization inhibitors, antifoaming agents, surfactants, etc. .

<Method for preparing photosensitive composition>
The photosensitive composition is prepared by mixing the above components using a stirrer. In addition, in order to make the prepared photosensitive composition uniform, it may be filtered using a membrane filter or the like that can pass the components such as the light shielding agent (D).

In the coating film forming step, the method of coating the photosensitive composition on the lens 1 is not particularly limited, and for example, a non-contact coating device such as a spray coater or a dip coater can be used. Application using a spray coater (spray application), which tends to cause light leakage, is preferred since the effect is remarkable.

After applying the photosensitive composition, if necessary, the solvent is removed by drying to form the coating film 2a.
Note that the drying (heating) is preferably performed at a low temperature, for example, 100° C. or lower, preferably 80° C. or lower. By performing the process at such a low temperature, it is possible to prevent damage to resin lenses and the like. Drying may be performed under a reduced pressure atmosphere if necessary.

<Exposure process>
In the exposure step, as shown in FIG. 3C, positions 3 in the coating film 2a formed in the coating film forming step, where the light shielding layer 2 is to be formed, are positionally selectively exposed. In the exposure process, the coating film 2a is exposed by position-selectively irradiating active energy rays such as i-line (365 nm) and excimer laser light in accordance with the desired shape (pattern shape) of the light-shielding layer 2. I do. The position-selective exposure is performed, for example, through a negative mask 4 having a shape corresponding to the shape of the light-shielding layer 2 .
For exposure, a light source that emits ultraviolet rays, such as a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a xenon lamp, or a carbon arc lamp, can be used. Although the exposure amount varies depending on the composition of the photosensitive composition, it is preferably about 10 mJ/cm ² or more and 600 mJ/cm ² or less, for example.

<Developing process>
In the development step, the unexposed portion 5 of the coating film 2a exposed in the exposure step is developed with a developer such as an alkaline developer.
The developing method is not particularly limited, and a dipping method, a spray method, etc. can be used. Specific examples of the developer include organic ones such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts.

<Thermosetting process>
In the thermosetting step, the developed coating film is heated (baked). Thereby, as shown in FIG. 3(d), the developed coating film is heated and cured to form the light-shielding layer 2 (patterned cured product).

The baking temperature can be, for example, 120°C or lower, 100°C or lower, or even 95°C or lower. The lower limit of the baking temperature is not particularly limited as long as the coating film is well cured, but is preferably 80° C. or higher.
The baking time is not particularly limited, and baking is continued until the coating film is sufficiently cured. Typically, bake times of 15 to 60 minutes are preferred.

The thickness of the light shielding layer 2 formed is not particularly limited. The thickness of the light shielding layer 2 is preferably 0.05 μm or more, more preferably 1 μm or more. Although there is no particular upper limit to the thickness of the light shielding layer 2, it may be, for example, 50 μm or less, or 20 μm or less. The thickness of the light shielding layer 2 is preferably 10 μm or less.

(Embodiment 2)
The method for manufacturing an optical element according to the second embodiment is a method for manufacturing an optical element including a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens.
The method for manufacturing the optical element includes a coating film forming step of applying a photosensitive composition to a curved surface of a lens to form a coating film, and position-selectively exposing a position in the coating film where a light-shielding layer is to be formed. The method includes an exposure step, a development step of developing the exposed coating film, and a thermosetting step of heating and curing the developed coating film.
The above photosensitive composition comprises an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic and a solvent (S).
The method for manufacturing the optical element of Embodiment 2 will be described below, and the method for manufacturing the optical element of Embodiment 2 requires that the thickener (E) is an essential component in the photosensitive composition; It is not essential that the thixotropy index expressed by the above formula (1) is 1.5 or more at 25°C and the viscosity V2 at a rotation speed of 50 rpm in an E-type viscometer at 25°C is 6 cP or more. The rest is the same as in the first embodiment. Therefore, other than the explanation of the method for manufacturing the optical element according to Embodiment 2 described below (for example, each step, the optical element, the components and formulations contained in the photosensitive composition, the solid content concentration of the photosensitive composition, etc.) ), the explanation thereof will be omitted.

As described above, by position-selectively exposing and developing the coating film formed by applying the photosensitive composition to the lens 1, a light-shielding film located at the periphery of the lens 1 and covering at least a part of the curved surface of the lens 1 is formed. When the layer 2 is formed, there is a problem that light leakage may occur at a portion (slanted portion 2a) of the light shielding layer 2 provided on the curved surface (that is, the sloped surface) of the lens 1.
However, in this embodiment, the alkali-soluble resin (A), the photopolymerizable monomer (B), the photopolymerization initiator (C), the light shielding agent (D), the thickener (E), and the organic By using a specific photosensitive composition containing a solvent (S), the above-mentioned light leakage can be suppressed, as shown in the Examples described below.

In this embodiment, since the coating film is formed using the above-mentioned specific photosensitive composition, the photosensitive composition tends to stay on the curved surface (slanted surface) of the lens 1 at the periphery of the lens 1, and is Difficult to flow along. As a result, a thick light shielding layer 2 (slope portion 2a) can be formed on the curved surface of the lens 1. In an optical element including a thick light-shielding layer 2, the light-shielding layer 2 sufficiently absorbs light and light leakage is suppressed. In addition, the light absorption ability of the light-shielding layer 2 (slope portion 2a) formed on the curved surface of the lens 1 and the light absorption ability of a portion of the light-shielding layer 2 that corresponds to the plane of the lens 1 (flat portion 2b) It is also possible to reduce the difference.
Since light leakage is suppressed, the optical element 10 in which the light shielding layer 2 is formed on the lens 1 manufactured in this embodiment can be preferably used in optical equipment such as a camera, a microscope, and a semiconductor exposure apparatus.

The thixotropy index represented by the above formula (1) of the photosensitive composition used in this embodiment is preferably 1.5 or more, more preferably 1.60 or more, and 1.70 or more. It is more preferable that
Further, the viscosity V2 of the photosensitive composition used in this embodiment is preferably 6 cP or more, more preferably 8 cP or more, and even more preferably 12 cP or more.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the scope of the present invention is not limited to these Examples.

In Examples and Comparative Examples, Resin A-1, which is an alkali-soluble cardo resin, and Resin A-2, which is an alkali-soluble acrylic resin, were used as the alkali-soluble resin (A). Resin A-1 is a resin obtained in Preparation Example 1 below. Resin A-2 is a copolymer of methyl methacrylate, acrylic acid, and styrene, with a mass ratio of methyl methacrylate: acrylic acid: styrene = 40:40:20, and a mass average molecular weight Mw of 8000. .

(Preparation example 1)
First, in a 500 ml four-necked flask, 235 g of bisphenol fluorene type epoxy resin (epoxy equivalent: 235), 110 mg of tetramethylammonium chloride, 100 mg of 2,6-di-tert-butyl-4-methylphenol, and 72.0 g of acrylic acid. was charged and dissolved by heating at 90 to 100° C. while blowing air at a rate of 25 ml/min. Next, while the solution remained cloudy, the temperature was gradually increased to 120° C. to completely dissolve the solution. At this time, the solution gradually became transparent and viscous, but stirring was continued. During this time, the acid value was measured, and heating and stirring were continued until the acid value became less than 1.0 mgKOH/g. It took 12 hours for the acid value to reach the target value. Then, the mixture was cooled to room temperature to obtain a colorless, transparent, solid bisphenol fluorene type epoxy acrylate represented by the following formula.

Next, 600 g of 3-methoxybutyl acetate was added and dissolved in 307.0 g of the bisphenol fluorene type epoxy acrylate thus obtained, and then 3,3',4,4'-biphenyltetracarboxylic dianhydride was added. 80.5 g and 1 g of tetraethylammonium bromide were mixed, and the temperature was gradually raised to 110 to 115° C. for 4 hours to react. After confirming the disappearance of the acid anhydride group, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed and reacted at 90° C. for 6 hours to obtain resin A-1. Disappearance of acid anhydride groups was confirmed by IR spectrum. The mass average molecular weight of Resin A-1 measured by gel permeation chromatography was 3,100 in terms of polystyrene.

In Examples and Comparative Examples, B-1: dipentaerythritol hexaacrylate (DPHA) was used as the photopolymerizable monomer (B).

In the Examples and Comparative Examples, the following C-1 was used as the photopolymerization initiator (C).

In the Examples and Comparative Examples, the following D1-1 and D-2 as carbon black and the following D2-1 (lactam pigment) as an organic black pigment were used as the light shielding agent (D). Carbon black was used as a carbon black dispersion. A method for preparing a carbon black dispersion liquid is described below as Preparation Example 4. Further, the organic black pigment was used as an organic black pigment dispersion. A method for preparing an organic black pigment dispersion is described below as Preparation Example 5.
D1-1: Regal 250R, manufactured by Cabot (carbon black that has not been subjected to acid group introduction treatment)
D1-2: Carbon black into which benzenesulfonic acid groups obtained in Preparation Example 3 below were introduced.

(Preparation Example 3: Preparation of D1-2)
550 g of carbon black (Regal 250R, manufactured by Cabot), 31.5 g of sulfanilic acid, and 1000 g of ion-exchanged water were added to a reaction vessel equipped with a jacket and a stirring device and set at a jacket temperature of 60°C. After adding a solution of 12.6 g of sodium nitrite dissolved in 100 g of deionized water into the Blau mixer, the mixture in the mixer was stirred at 60° C. and 50 rpm for 2 hours to perform a diazo coupling reaction. Ta. After stirring, the contents of the mixer were cooled to room temperature. The carbon black contained in the contents of the mixer was then purified by diafiltration using deionized water. Benzenesulfonic acids derived from sulfanilic acid were not detected in the washing water, indicating that benzenesulfonic acid groups were introduced into the carbon black through the diazo coupling reaction. The purified carbon black was dried at 75° C. overnight and then pulverized to obtain carbon black (D1-2) into which benzenesulfonic acid groups were introduced.

(Preparation Example 4: Preparation of carbon black dispersion)
A carbon black dispersion was prepared using D1-1 and D1-2 as carbon black according to the following recipe.
15 g of carbon black, 4.5 g of a dispersant (BYK-167, manufactured by BYK Chemie Japan Co., Ltd.), and 50 g of propylene glycol monomethyl ether acetate (PGMEA) were mixed and stirred using a bead mill to form carbon black in propylene glycol monomethyl ether acetate. was dispersed. Thereafter, the mixture was diluted with propylene glycol monomethyl ether acetate so that the solid content concentration was 30% by mass to obtain a carbon black dispersion.

(Preparation Example 5: Preparation of organic black pigment dispersion)
An organic black pigment dispersion was obtained in the same manner as in Preparation Example 4, except that D2-1 as an organic black pigment was used instead of carbon black.

In the Examples and Comparative Examples, the following E-1 and E-2 were used as the thickener (E).
E-1: Thickener with urea structure (BYK-410, manufactured by BYK Chemie Japan Co., Ltd.)
E-2: Fumed silica thickener (BYK-405, BYK-Chemie Japan Co., Ltd.)

[Examples 1 to 8 and Comparative Examples 1 to 3]
Alkali-soluble resin (A), photopolymerizable monomer (B), photopolymerization initiator (C), light shielding agent (D), and thickener (E) of the type and mass parts listed in Table 1. The photosensitive compositions of Examples 1 to 8 and Comparative Examples 1 to 3 were prepared by uniformly dissolving and dispersing them in a solvent (S) so as to have the solid content concentration (mass%) shown in Table 1. Prepared. Note that the solvent (S) was propylene glycol monomethyl ether acetate (PGMEA). Further, the light blocking agent (D) was blended using a dispersion liquid so that the type and amount of the light blocking agent (D) were as shown in Table 1. Table 1 also lists the amount of dispersant.

The photosensitive compositions of the obtained Examples and Comparative Examples were measured using an E-type viscometer (TVE-35L viscometer, manufactured by Toki Sangyo Co., Ltd.) at 25°C. The viscosity (at a rotational speed of 5 rpm) and V2 (at a rotational speed of 50 rpm using an E-type viscometer) were measured, and the thixotropy index expressed by the following formula (1) was determined. The results are shown in Table 1.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotation speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. )

Using the obtained photosensitive compositions of Examples and Comparative Examples, light leakage, thickness of the light shielding layer (cured product), and OD value were evaluated according to the following methods. The results are shown in Table 1.

[OD value evaluation]
The photosensitive composition was applied onto a 10 cm ² glass substrate (Eagle XG, manufactured by Corning), and then heated (dried) at 80° C. for 120 seconds to form a coating film. Next, this coating film was irradiated with broadband light including i-line (365 nm) using a proximity exposure device (product name: TME-150RTO, manufactured by Topcon Corporation). The exposure amount was 100 mJ/cm ² . Then, it was heated (baked) on a hot plate at 90° C. for 30 minutes. The thickness of the formed light shielding layer (cured product) was 1.0 μm. The OD value of this light-shielding layer (cured product) was measured using D200-II (manufactured by Macbeth).

[Evaluation of film thickness of light shielding layer]
The coating film 12 was formed on the glass substrate 11 using the photosensitive composition by the method shown in FIG. 4, and the thickness of the coating film 12 was evaluated, thereby evaluating the film thickness of the light shielding layer.
Specifically, first, a glass substrate 11 (manufactured by Corning, Eagle
A photosensitive composition was applied onto the entire surface of this glass substrate 11 using a spray coater, and heated (dried) at 80° C. for 120 seconds to form a coating film 12.
Thereafter, the glass substrate 11 was held horizontally, and the film thickness x of the coating film 12 (thickness of the coating film 12 in the thickness direction of the glass substrate 11) was measured. The results are shown in Table 1. Since there is a correlation between the thickness x of the coating film 12 and the thickness of the light shielding layer, it can be said that, for example, the thicker the thickness x of the coating film 12, the thicker the light shielding layer.
The coating on the glass substrate 11 was performed when the coating film 12 was formed in the same manner as above except that the photosensitive composition was applied with the glass substrate 11 horizontal (the tilt angle was 0°). The test was carried out under conditions such that the film thickness of the film 12 (the film thickness of the coating film 12 in the thickness direction of the glass substrate 11) was 7 μm.

[Evaluation of light leakage]
After forming a coating film by heating (drying) at 80°C for 120 seconds, the entire surface of the coating film was irradiated (exposed) with broadband light including i-line (365 nm) using a double-sided printer "HMW-532D manufactured by Oak Co., Ltd." 100 mJ/cm ² ) and then heated at 90°C for 30 minutes to form a light shielding layer (cured film). A case where a light shielding layer is formed on a glass substrate 11 with an angle of 25°, plane light (lumen of light flux 130 lumens) is irradiated with the tilt angle kept at 25°, and no light transmitted through the light shielding layer is observed. ○ rating, Δ rating when a slight amount of light passing through the light shielding layer was observed, and × rating when light passing through the light shielding layer was clearly observed. The results are shown in Table 1.

According to Examples 1 to 8, the resin contained an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S). , a photosensitive composition having a thixotropy index represented by formula (1) of 1.5 or more at 25°C, and a viscosity V2 at 50 rpm in an E-type viscometer of 6 cP or more at 25°C. , or an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic solvent (S). It can be seen that by using the photosensitive composition containing the above, it is possible to form a light shielding layer with suppressed light leakage on the inclined surface of the glass substrate (and thus on the curved surface of the lens).

On the other hand, according to Comparative Examples 1 to 3, when a photosensitive composition that does not have the above specific thixotropic index and viscosity or a photosensitive composition that does not contain a thickener (E) is used, the slope It can be seen that the light shielding layer on the curved surface of the lens has a large amount of light leakage.

1 Lens 2 Light-shielding layer 2a Slanted part 2b Plane part 3 Position where light-shielding layer is formed 4 Negative mask 5 Unexposed part 10 Optical element 11 Glass substrate 12 Coating film

Claims (11)

A method for manufacturing an optical element comprising a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens, the method comprising:
a coating film forming step of applying a photosensitive composition to the curved surface of the lens to form a coating film;
an exposure step of positionally selectively exposing a position in the coating film where the light shielding layer is formed;
A developing step of developing the coated film after exposure;
A thermosetting step of heating and curing the coated film after development,
The photosensitive composition includes an alkali-soluble resin (A), a photopolymerizable monomer (B), a photoinitiator (C), a light shielding agent (D), and an organic solvent (S),
The photosensitive composition has a thixotropy index expressed by the following formula (1) of 1.5 or more at 25°C, and a viscosity V2 of 6 cP at 50 rpm in an E-type viscometer at 25°C. The above is the method for manufacturing an optical element.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotation speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. ) A method for manufacturing an optical element comprising a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens, the method comprising:
a coating film forming step of applying a photosensitive composition to the curved surface of the lens to form a coating film;
an exposure step of positionally selectively exposing a position in the coating film where the light shielding layer is formed;
A developing step of developing the coated film after exposure;
A thermosetting step of heating and curing the coated film after development,
The photosensitive composition comprises an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic solvent. (S) A method for manufacturing an optical element. The method for manufacturing an optical element according to claim 2, wherein the thickener (E) includes a thickener having a urea structure. The method for producing an optical element according to claim 1, wherein the solid content concentration of the photosensitive composition is 30% by mass or more. 5. The method for producing an optical element according to claim 1, wherein the organic solvent (S) includes an organic solvent having one or more hydroxyl groups in its molecular structure. A photosensitive composition used for forming a light-shielding layer on a lens consisting of a convex lens or a concave lens, which is located at the periphery of the lens and covers at least a part of the curved surface of the lens, the composition comprising:
Contains an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), and an organic solvent (S),
At 25°C, the thixotropy index represented by the following formula (1) is 1.5 or more,
A photosensitive composition having a viscosity V2 of 6 cP or more at 25° C. and a rotation speed of 50 rpm using an E-type viscometer.
V1/V2...(1)
(In formula (1), V1 is the viscosity at a rotational speed of 5 rpm in an E-type viscometer,
V2 is the viscosity at a rotational speed of 50 rpm in an E-type viscometer. ) A photosensitive composition used for forming a light-shielding layer on a lens consisting of a convex lens or a concave lens, which is located at the periphery of the lens and covers at least a part of the curved surface of the lens, the composition comprising:
A photosensitive material containing an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), a light shielding agent (D), a thickener (E), and an organic solvent (S) sexual composition. The photosensitive composition according to claim 7, wherein the thickener (E) includes a thickener having a urea structure. The photosensitive composition according to any one of claims 6 to 8, wherein the solid content concentration is 30% by mass or more. The photosensitive composition according to any one of claims 6 to 9, wherein the organic solvent (S) includes an organic solvent having one or more hydroxyl groups in its molecular structure. comprising a lens made of a convex lens or a concave lens, and a light shielding layer located at the periphery of the lens and covering at least a part of the curved surface of the lens,
An optical element, wherein the light-shielding layer is made of a cured product of the photosensitive composition according to any one of claims 6 to 10.

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