JP7818878B1 - Organic compounds, organic ionic compounds, polymerization initiators, photobase generators, and photosensitive compositions - Google Patents

Abstract

The present invention provides a novel organic compound and organic ionic compound with excellent light absorption properties. The organic compound according to an embodiment of the present invention has a structure represented by the following formula (1): In formula (1), ^R1 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group; ^R2 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group; and X represents an organic group having a heterocyclic skeleton containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring.

Description

The present invention relates to organic compounds, organic ionic compounds, polymerization initiators, photobase generators, and photosensitive compositions.

Organic compounds that are active against actinic rays such as ultraviolet light are widely used as effective components in photosensitive compositions. For example, organic compounds used as photopolymerization initiators, photoacid generators, or photobase generators are added to photosensitive compositions to promote and assist reactions such as polymerization and crosslinking of reactive compounds and/or resins.

For example, Patent Document 1 discloses a compound having a ketoprofen skeleton and proposes using decarboxylation of ketoprofen to generate a base, which then reacts (cures, etc.) with a reactive compound. Furthermore, Patent Document 2 proposes using a compound having a ketoprofen skeleton as a base generator and curing a photosensitive composition using decarboxylation.

Japanese Patent Application Laid-Open No. 2007-101685 JP 2010-84144 A

In order to improve the activity of the reactive compound in the photosensitive composition, the organic compound to be blended in the composition is required to have high absorption characteristics, but it is difficult to obtain a large absorbance and absorption coefficient with the compound having a ketoprofen skeleton as described above. Furthermore, in order to be used as a photobase generator, it is also required to be able to improve the curability and contrast when blended in the composition and the composition is cured.
One object of the present invention is to provide a novel organic compound having excellent light absorption properties, and an organic ionic compound that can be used as a photobase generator. Another object of the present invention is to provide a polymerization initiator and a photobase generator that can achieve excellent curability and contrast when applied to a photosensitive composition, and a photosensitive composition having excellent curability and contrast.

[1] An organic compound according to an embodiment of the present invention has a structure represented by the following formula (1):

In formula (1), ^R1 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group; ^R2 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group; and X represents an organic group having a heterocyclic skeleton containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring.
[2] In the above [1], the heterocyclic skeleton contains at least one heterocyclic ring selected from the group consisting of a substituted or unsubstituted furan ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted N-substituted pyrrole ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted N-substituted indole ring, and a substituted or unsubstituted benzothiophene ring.
[3] In the above [1] or [2], the above X is an organic group having at least one structure selected from the group consisting of the following structural formulas:
[4] In any one of the above [1] to [3], the above X is an organic group having at least one structure selected from the group consisting of the following structural formulas:
[5] The organic ionic compound according to an embodiment of the present invention has a structure represented by the following formula (1-A):

In formula (1-A), R ¹ represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group; R ² represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group; and X represents an organic group having a heterocyclic skeleton containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring. In formula (1-A), A ⁺ represents a cation of an organic base. The organic base is at least one compound selected from the group consisting of a primary amine, a secondary amine, a tertiary amine, a compound having an amidine skeleton, and a compound having a guanidine skeleton.
[6] In the above [5], the organic base is either a compound having an amidine skeleton or a compound having a guanidine skeleton.
[7] In the above [5] or [6], the A ⁺ is at least one cation selected from the group consisting of the following structural formulas:
[8] In any one of the above [5] to [7], the above X is an organic group having at least one structure selected from the group consisting of the following structural formulas:
[9] According to another aspect of the present invention, there is provided a polymerization initiator, which comprises at least one of the organic compounds described in any one of [1] to [4] above.
[10] According to yet another aspect of the present invention, there is provided a photobase generator, the photobase generator including at least one organic ionic compound according to any one of [5] to [8] above.
[11] According to yet another aspect of the present invention, there is provided a photosensitive composition comprising a reactive compound containing a vinyl compound and the polymerization initiator described in [9] above.
[12] According to yet another aspect of the present invention, there is provided a photosensitive composition comprising at least one reactive compound selected from the group consisting of an isocyanate compound, an epoxy compound, a silane compound, and a polyamic acid, and the photobase generator according to [10] above.

Embodiments of the present invention provide novel organic compounds with excellent light absorption properties, and novel organic ionic compounds that can be used as photobase generators. Another embodiment of the present invention provides polymerization initiators and photobase generators that can achieve excellent curability and contrast when applied to photosensitive compositions, as well as photosensitive compositions with excellent curability and contrast.

1 is an ultraviolet absorption spectrum of Compound 1-1A obtained in Synthesis Example 1-1 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-2A obtained in Synthesis Example 1-2 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-3A obtained in Synthesis Example 1-3 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-4A obtained in Synthesis Example 1-4 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-5A obtained in Synthesis Example 1-5 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-6A obtained in Synthesis Example 1-6 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-7A obtained in Synthesis Example 1-7 according to an embodiment of the present invention. 1 shows an ultraviolet absorption spectrum of Compound 1-8A obtained in Synthesis Example 1-8 according to an embodiment of the present invention. 1 shows an ultraviolet absorption spectrum of Compound 1-9A obtained in Synthesis Example 1-9 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-10A obtained in Synthesis Example 1-10 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-11A obtained in Synthesis Example 1-11 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-12A obtained in Synthesis Example 1-12 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-13A obtained in Synthesis Example 1-13 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-1B obtained in Synthesis Example 1-14 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-1C obtained in Synthesis Example 1-15 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound C-1A obtained in Synthesis Example C-1 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound C-2A obtained in Synthesis Example C-2 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound C-3A obtained in Synthesis Example C-3 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound C-4A obtained in Synthesis Example C-4 according to an embodiment of the present invention. 1 shows an ultraviolet absorption spectrum of Compound 1-14A obtained in Synthesis Example 1-16 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-15A obtained in Synthesis Example 1-17 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound 1-16A obtained in Synthesis Example 1-18 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Compound C-5A obtained in Synthesis Example C-5 according to an embodiment of the present invention. 1 is an ultraviolet absorption spectrum of Reference Example Compound R-1 according to an embodiment of the present invention.

Representative embodiments of the present invention are described below. However, the present invention is not limited to these embodiments. In this specification, "A and/or B" means either "A," "B," or "A and B."

As used herein, the term "organic" refers to a compound having a covalent bond formed between a carbon atom and a hydrogen atom. As used herein, "organic ionic compound" refers to a compound containing an organic cation and an anion as a counterion. The organic cation in an organic ionic compound is sometimes referred to as the "cation portion," and the portion that constitutes the counterion (anion) is sometimes referred to as the "anion portion." An "*" that may appear in a chemical formula represents a bond.

A. Overall Structure of Organic Compound and Organic Ionic Compound The organic compound according to an embodiment of the present invention has a structure represented by the following formula (1):
In formula (1), ^R1 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group. ^R2 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group. X represents an organic group having a heterocyclic skeleton containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring.

The organic compound according to an embodiment of the present invention is a novel organic compound. The organic compound according to an embodiment of the present invention has excellent light absorption properties due to the structure represented by formula (1) above. Furthermore, the organic compound can form an organic ionic compound as a salt with any appropriate base. As a result, the organic ionic compound is also a novel organic ionic compound. Therefore, embodiments of the present invention also encompass organic ionic compounds.

As described above, the organic compound according to an embodiment of the present invention can have excellent light absorption properties. Therefore, when the organic compound is irradiated with active energy rays, the organic compound decarboxylates, generating highly active radicals. As a result, the radicals generated from the organic compound according to an embodiment of the present invention react with the reactive compound, generating growing radicals in the reactive compound, thereby enabling continuous addition (polymerization) of the reactive compound. In this way, the organic compound according to an embodiment of the present invention enables efficient radical polymerization of any appropriate reactive compound and can effectively cure the reactive compound. In other words, the organic compound according to an embodiment of the present invention can be suitably used as a polymerization initiator. Therefore, embodiments of the present invention also encompass polymerization initiators. The organic compound according to the present invention can more preferably be used as a radical polymerization initiator.

The polymerization initiator according to an embodiment of the present invention contains at least one of the above organic compounds, and when the polymerization initiator is applied to a photosensitive composition, the curing properties and contrast of the photosensitive composition can be improved.

The organic ionic compound according to an embodiment of the present invention has a structure represented by the following formula (1-A).
In formula (1-A), R ¹ , R ² and X may be the same as those shown in formula (1). In formula (1-A), A ⁺ represents a cation of an organic base. The organic base is at least one compound selected from the group consisting of primary amines, secondary amines, tertiary amines, compounds having an amidine skeleton, and compounds having a guanidine skeleton.

As is clear from the above formula (1-A), the organic ionic compound is a compound formed by forming a salt between at least one compound from a specific group of organic compounds having a structure represented by the above formula (1) and any suitable base A. Therefore, since the organic ionic compound according to an embodiment of the present invention also has the same structure as the structure represented by the above formula (1), it can have excellent light absorption properties. More specifically, by irradiating the organic ionic compound with active energy rays, the organic ionic compound can decarboxylate and release base A. Alternatively, in an aqueous solution, the generated (released) base A can generate hydroxide ions in the system. As a result, the base and/or hydroxide ions generated from the organic ionic compound according to an embodiment of the present invention add to a reactive compound, anionizing the reactive compound and allowing the reactive compound to be continuously added (polymerized). In this way, the organic ionic compound according to an embodiment of the present invention enables efficient anionic polymerization of any suitable reactive compound and can effectively cure the reactive compound. That is, the organic ionic compound of the present invention can be suitably used as a photobase generator. Thus, embodiments of the present invention also encompass photobase generators.

The photobase generator according to an embodiment of the present invention contains at least one of the above-mentioned organic ionic compounds, and when the photobase generator is applied to a photosensitive composition, the curability and contrast of the photosensitive composition can be improved.

In this specification, absorption characteristics refer to the ability to absorb light in the ultraviolet wavelength range. Absorption characteristics can be confirmed, for example, by measuring the absorption spectrum in the wavelength range of 200 nm to 500 nm and calculating the maximum absorption wavelength and extinction coefficient from the absorption spectrum. Specific measurement methods and conditions for the absorption spectra of organic compounds and organic ionic compounds are as described in the Examples below.

In this specification, the term "curability" refers to an index showing the ease of curing of a photosensitive composition. The curability is expressed as the ratio of the degree of curing of a photosensitive composition containing the organic compound to the degree of curing of a photosensitive composition not containing the organic compound. The curability is expressed as the ratio of the degree of curing of a photosensitive composition containing the organic ionic compound to the degree of curing of a photosensitive composition not containing the organic ionic compound but containing only a base corresponding to the cation moiety of the organic ionic compound.
In this specification, the contrast is an index of the developability of a photosensitive composition. Therefore, the contrast is also referred to as developability. Specifically, the contrast can be confirmed as follows.
That is, first, a coating film of the photosensitive composition is prepared. The coating film is cured by exposure to light to form a cured film, and the weight (m1) of the cured film is measured. Subsequently, the cured film is further treated with a developer, and the weight (m2) of the remaining film (residual film) is measured. The value obtained by dividing m2 by m1 is designated a1. Meanwhile, a coating film is prepared from the photosensitive composition under the same conditions as above, and the weight (m3) of the unexposed coating film (unexposed coating film) is measured. The unexposed coating film is not exposed, and is treated with the same developer as above, and the weight (m4) of the remaining film (unexposed residual film) is measured. The value obtained by dividing m4 by m3 is designated a2. Based on the obtained a1 and a2, the contrast can be calculated by the following formula (M1):
Contrast (%)=(a1−a2)/a1×100 (M1)
Specific methods for preparing the composition, exposing the composition, and measuring the curability and contrast will be described in detail in the Examples below.

The organic compound and/or polymerization initiator according to embodiments of the present invention may be used in a photosensitive composition as described above. Similarly, the organic ionic compound and/or photobase generator according to embodiments of the present invention may be used in a photosensitive composition. Accordingly, embodiments of the present invention may include a photosensitive composition. The photosensitive composition may be used for any suitable application. The photosensitive composition according to embodiments of the present invention may be used in a variety of applications, such as photocurable coatings; photocurable adhesives; printed wiring boards; plating masks; solder resists; and various photoresist materials.

A-1. Organic Compound The organic compound according to the embodiment of the present invention will be specifically described.
As described above, the organic compound according to the embodiment of the present invention has a structure represented by the following structural formula (1).
In formula (1), R ¹ , R ² and X can each independently have the following structure.

^R1 is at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group. Specific examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alkyl group may preferably be a methyl group, an ethyl group, a propyl group, or a butyl group. The substituted phenyl group may be a phenyl group in which at least one hydrogen atom in an unsubstituted phenyl group has been substituted with any appropriate substituent. The number of substituents in the substituted phenyl group is not particularly limited and may be, for example, 1 to 5. Examples of the substituent include halogen atoms such as fluorine, chlorine, bromine, and iodine; and at least one group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxyl group, a nitro group, and a cyano group. The alkyl group having 1 to 4 carbon atoms may be, for example, a methyl group, an ethyl group, a propyl group, or a butyl group. The alkoxy group having 1 to 4 carbon atoms can be, for example, a methoxy group, an ethoxy group, a propoxy group, or a butoxy group.
^R1 is preferably at least one group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, and a substituted or unsubstituted phenyl group. ^R1 is more preferably a hydrogen atom, a methyl group, an ethyl group, or a phenyl group, even more preferably a hydrogen atom, a methyl group, or an ethyl group, and particularly preferably a hydrogen atom or a methyl group.

^R2 is at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group. The alkyl group having 1 to 8 carbon atoms and the substituted or unsubstituted phenyl group may be the same as those described above for ^R1 . The alkylcarbonyl group having 1 to 4 carbon atoms may specifically be an acetyl group, an ethylcarbonyl group, a propylcarbonyl group, or a butylcarbonyl group. The substituted or unsubstituted benzoyl group may be a benzoyl group in which at least one hydrogen atom in an unsubstituted benzoyl group has been substituted with any appropriate substituent. The number of substituents in the substituted benzoyl group is not particularly limited and may be, for example, 1 to 5. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine; and at least one organic group selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxyl group, a nitro group, and a cyano group. The alkyl group having 1 to 4 carbon atoms may be a methyl group, an ethyl group, a propyl group, or a butyl group. The alkoxy group having 1 to 4 carbon atoms may be a methoxy group, an ethoxy group, a propoxy group, or a butoxy group.
^R2 is preferably at least one group selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, an acetyl group, an ethylcarbonyl group, a propylcarbonyl group, a butylcarbonyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group. ^R2 is more preferably a hydrogen atom, a methyl group, an ethyl group, an acetyl group, a phenyl group, a benzoyl group, or a carboxymethyl group, even more preferably a hydrogen atom, a methyl group, an ethyl group, or a carboxymethyl group, and particularly preferably a hydrogen atom, a methyl group, or a carboxymethyl group.

X is an organic group (hereinafter also referred to as organic group X) having a heterocyclic skeleton containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring. The organic group X may contain any appropriate heterocyclic ring, so long as it has a heterocyclic skeleton containing at least one atom of an oxygen atom, a nitrogen atom, or a sulfur atom. The heterocyclic skeleton in the organic group X may typically contain at least one heterocyclic ring selected from the group consisting of a furan skeleton, a benzofuran skeleton, a pyrrole skeleton, an N-substituted pyrrole skeleton, an indole skeleton, an N-substituted indole skeleton, and a benzothiophene skeleton. In each of these heterocyclic rings, at least one hydrogen atom in the heterocyclic skeleton may be substituted. That is, in one embodiment, the heterocyclic skeleton in the organic group X may preferably include at least one heterocyclic ring selected from the group consisting of a substituted or unsubstituted furan ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted N-substituted pyrrole ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted N-substituted indole ring, and a substituted or unsubstituted benzothiophene ring.
Any appropriate group may be employed as the substituent. Examples of the substituent substituting a hydrogen atom in a heterocycle (excluding the hydrogen atom on the N of a substituted or unsubstituted N-substituted pyrrole ring and the hydrogen atom on the N of a substituted or unsubstituted N-substituted indole ring) include at least one group selected from the group consisting of an aliphatic hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyalkyl group having 1 to 8 carbon atoms, a halogen atom such as fluorine, chlorine, bromine, or iodine; a hydroxyl group, a nitro group, and a cyano group. The aliphatic hydrocarbon group having 1 to 4 carbon atoms may be, for example, any appropriate alkyl group, alkenyl group, alkynyl group, alkylidene group, or alkylidyne group. Specifically, the aliphatic hydrocarbon group having 1 to 4 carbon atoms may be, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a methylene group, an ethylene group, a propylene group, a butylene group, an ethenyl group, a propenyl group, a butenyl group, an ethynyl group, a propynyl group, a butynyl group, a vinyl group, a vinylene group, a vinylidene group, or a propargyl group. The substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, or a substituted or unsubstituted benzyl group. The alkoxy group having 1 to 8 carbon atoms may be, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, or an octyloxy group. The hydroxyalkyl group having 1 to 8 carbon atoms may be, for example, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, a hydroxyhexyl group, a hydroxyheptyl group, or a hydroxyoctyl group.
Examples of substituents substituting the hydrogen atom on N of a substituted or unsubstituted N-substituted pyrrole ring and the hydrogen atom on N of a substituted or unsubstituted N-substituted indole ring include aliphatic hydrocarbon groups having 1 to 8 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 12 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, hydroxyalkyl groups having 1 to 8 carbon atoms, alkylcarbonyl groups having 1 to 4 carbon atoms, and substituted or unsubstituted benzoyl groups. The substituents substituting the hydrogen atom on N of a substituted or unsubstituted N-substituted pyrrole ring and the hydrogen atom on N of a substituted or unsubstituted N-substituted indole ring may preferably be a methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group, methoxy group, ethoxy group, propoxy group, butoxy group, hexyloxy group, octyloxy group, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxyhexyl group, hydroxyoctyl group, acetyl group, or benzoyl group.

The organic group X may preferably be an organic group having at least one structure selected from the group consisting of the following structural formulas:

When the organic group X is at least one of the above structural formulas, the organic compound according to the present invention may have particularly excellent light absorption properties.
Formula (X2) is a furyl group bonded at position 2 or 3. In formula (X2), at least one of the three hydrogen atoms on the ring may be substituted.
Formula (X3) is a pyrrolyl group bonded at the 2- or 3-position. In formula (X3), at least one of the three hydrogen atoms on the ring may be substituted. Note that the hydrogen atom on the N is excluded from the three hydrogen atoms on the ring.
Formula (X4) is an N-methylpyrrolyl group bonded at position 2 or 3. In formula (X4), at least one of the three hydrogen atoms on the ring may be substituted.
Formula (X5) is a benzofuryl group bonded at position 2 or 3. In formula (X5), at least one of the five hydrogen atoms on the ring may be substituted.
Formula (X6) is a 3-methylindolyl group bonded at the 2-position. In formula (X6), at least one of the four hydrogen atoms on the ring may be substituted. The hydrogen atom on the N is excluded from the four hydrogen atoms on the ring.
Formula (X7) is a 2-methylindolyl group bonded at the 3-position. In formula (X7), at least one of the four hydrogen atoms on the ring may be substituted. The hydrogen atom on the N is excluded from the four hydrogen atoms on the ring.
Formula (X8) is an indolyl group bonded at the 2- or 3-position. In formula (X8), at least one of the five hydrogen atoms on the ring may be substituted. The hydrogen atom on the N atom is excluded from the five hydrogen atoms on the ring.
Formula (X9) is an N-methyl-indolyl group bonded at position 2 or 3. In formula (X9), at least one of the five hydrogen atoms on the ring may be substituted.
Formula (X10) is an N-methyl-3-methylindolyl group bonded at position 2. In formula (X10), at least one of the four hydrogen atoms on the ring may be substituted.
Formula (X11) is an N-methyl-2-methylindolyl group bonded at position 3. In formula (X11), at least one of the four hydrogen atoms on the ring may be substituted.
Formula (X12) is a benzothienyl group bonded at position 2 or 3. In formula (X12), at least one of the five hydrogen atoms on the ring may be substituted.
Formula (X13) is an organic group having a methoxy group (-OMe) at the 5-position of the organic group of formula (X5). Specifically, it is a 5-methoxybenzofuryl group bonded at the 2- or 3-position. In formula (X13), at least one of the four hydrogen atoms on the ring may be substituted.
In the organic groups represented by the structural formulas above, the substituents, if any, may be preferably methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzoyl group. The substituted phenyl group may have the same structure as the substituted phenyl group described above for ^R1 . The same applies to the substituted benzoyl group.

The organic group X may more preferably be at least one group selected from the group consisting of the following structural formulas:

Formula (X2a) is a furyl group bonded at the 2-position. Formula (X3a) is a pyrrolyl group bonded at the 2-position. Formula (X4a) is an N-methylpyrrolyl group bonded at the 2-position. Formula (X5a) is a benzofuryl group bonded at the 2-position. As described above, Formula (X6) is a 3-methylindolyl group bonded at the 2-position. Formula (X12a) is a benzothienyl group bonded at the 2-position. Formula (X13a) is an organic group having a methoxy group (-OMe) at the 5-position of Formula (X5a), and is a 5-methoxybenzofuryl group bonded at the 2-position. When the organic group X is at least one of the above, the organic compound may have particularly excellent absorption properties. Any of the organic groups having the structures represented by the above formulae (X2a), (X3a), (X4a), (X5a), (X6), (X12a) and (X13a) may have a substituent, as described above for the formulae (X2) to (X13).

In one embodiment, the organic group X may be an organic group having at least one structure selected from the group consisting of the following structural formulas:

In an organic compound, when the organic group X has at least one of the structures described above, the organic compound is used as a polymerization initiator and the polymerization initiator is applied to a photosensitive composition, resulting in particularly excellent curability and developability. In other words, an organic compound in which the organic group X has at least one of the structures described above can function as a particularly excellent polymerization initiator. Furthermore, an organic compound in which the organic group X has at least one of the structures described above can be particularly well suited for use as a radical polymerization initiator.

The organic compound represented by formula (1) has a terminal carboxyl group. As a result, the carboxyl group of the organic compound represented by formula (1) can become anionized to form a salt with any suitable base, forming an organic ionic compound. Organic ionic compounds are described in the next section.

A-2. Organic Ionic Compound The organic ionic compound according to the embodiment of the present invention may be composed of a cation moiety derived from any appropriate base and an anion moiety derived from the organic compound represented by formula (1), which serves as a counter ion. Specifically, the organic ionic compound has a structure represented by formula (1-A) below.

Generally, organic ionic compounds can be formulated with any suitable component (e.g., a reactive compound, etc.) and dissociated into ions upon dissolution. Here, dissociation of the organic ionic compound can provide an organic cation and an anion as a counterion. The organic ionic compounds according to embodiments of the present invention provide a cation (A ⁺ ) of an organic base A and an anion of an organic compound having the structure represented by formula (1) above (essentially a carboxylate anion of a carboxylic acid).

R ¹ , R ² and X in formula (1-A) are as described for R ¹ , R ² and X in formula (1).
In formula (1-A), A ⁺ is a cation of an organic base. Hereinafter, “A” may be referred to as organic base A.
The specific structure of the organic ionic compound according to the embodiment of the present invention will be specifically described below.

In one embodiment, the molar extinction coefficient ε of the organic ionic compound at the absorption maximum wavelength is preferably 1.8 x 10 ⁴ or more, more preferably 1.9 x 10 ⁴ or more, even more preferably 2.0 x 10 ⁴ or more, and particularly preferably 2.2 x 10 ⁴ or more. There is no particular upper limit to the molar extinction coefficient ε at the absorption maximum wavelength. The molar extinction coefficient ε of the organic ionic compound at a wavelength of 365 nm is preferably 1.8 x 10 ⁴ or more, more preferably 1.9 x 10 ⁴ or more, even more preferably 2.0 x 10 ⁴ or more, and particularly preferably 2.2 x 10 ⁴ or more. The gram extinction coefficient E of the organic ionic compound at the absorption maximum wavelength is preferably 40 or more, more preferably 50 or more, and even more preferably 55 or more. There is no particular upper limit to the gram extinction coefficient E at the absorption maximum wavelength. The gram absorption coefficient E of the organic ionic compound at a wavelength of 365 nm is preferably 25 or more, more preferably 30 or more, even more preferably 40 or more, and particularly preferably 50 or more. The molar absorption coefficient ε and the gram absorption coefficient E are calculated using the absorbance measured by a spectrophotometer and the concentration of the solution prepared in the measurement. The unit of the molar absorption coefficient is L/(mol cm), and the unit of the gram absorption coefficient is L/(g cm). Specific measurement methods are as described in the Examples below.

As described above, organic ionic compounds having a structure represented by formula (1-A) share a common skeleton with organic compounds having a structure represented by formula (1), and therefore may have excellent absorption characteristics. Specifically, as shown in Figures 1 to 15 and 20 to 22, these organic ionic compounds may have a maximum absorption wavelength in the vicinity of 345 nm to 380 nm. Therefore, these organic ionic compounds may be particularly effective when irradiated with light having a commonly used wavelength of 365 nm. However, this is not intended to limit the wavelengths of light to which the organic ionic compounds according to embodiments of the present invention can be applied.

The organic ionic compounds having the above absorption properties are not limited to the compounds corresponding to the illustrated figures. Organic compounds having a structure represented by formula (1) and organic ionic compounds having a structure represented by formula (1-A) can have excellent absorption properties.
When a conventional compound having a ketoprofen skeleton is used as a photobase generator, it can anionically polymerize a reactive compound, but good absorption characteristics may not be obtained. As a result, base may not be generated efficiently. In addition, even if the compound has a ketoprofen skeleton, there is a problem that it is difficult to obtain a photosensitive composition with excellent curability and to improve the contrast (developability) between the exposed and unexposed areas of the photosensitive composition.
In contrast, the organic ionic compound according to an embodiment of the present invention has a structure represented by formula (1-A) and has excellent light absorption properties as described above. Furthermore, since the organic ionic compound can effectively release a base upon irradiation with light, a photobase generator containing at least one of the organic ionic compounds can improve the curability and developability of a photosensitive composition.

(Organic group X)
In one embodiment, the organic group X may be an organic group having at least one structure selected from the group consisting of the following structural formulas:

In an organic ionic compound, when the organic group X has at least one of the above structures, the curability and developability are particularly excellent when the organic ionic compound is used as a photobase generator and the photobase generator is applied to a photosensitive composition. In other words, an organic ionic compound in which the organic group X has at least one of the above structures can function as a particularly excellent photobase generator.
For the explanation of the specific constitution of the organic group X having the structure represented by each of the structural formulae above, the explanation of the formulae (X2a), (X3a), (X4a), (X5a), (X6), (X12a), and (X13a) in the above section A-1 can be cited.

(organic base)
In formula (1-A), as described above, A ⁺ is a cation of the organic base A. The organic base A is at least one compound selected from the group consisting of a primary amine, a secondary amine, a tertiary amine, a compound having an amidine skeleton, and a compound having a guanidine skeleton.

The organic base A used in the embodiment of the present invention may have an acid dissociation constant (pK _a ) of the conjugate acid at 25°C of preferably 6 or more, more preferably 8 or more, and even more preferably 10 or more. The upper limit of the pK a is not particularly limited. When the pK a is within the above range, the organic ionic compound according to the embodiment of the present invention can generate a base particularly well when used as a photoacid generator and applied to a photosensitive composition. As a result, anionic polymerization of the photosensitive composition can be achieved more efficiently.

Any appropriate compound may be used as the primary amine, secondary amine, and tertiary amine. A primary amine is a compound having an —NH ₂ group. A secondary amine is a compound having an organic group in which one hydrogen atom of the —NH ₂ group in a primary amine is substituted with a hydrocarbon group. A tertiary amine is a compound having an organic group in which two hydrogen atoms of the —NH ₂ group in a primary amine are substituted with hydrocarbon groups. Any appropriate hydrocarbon group may be used as the hydrocarbon group. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Specific examples of the aliphatic hydrocarbon group include substituted or unsubstituted alkyl groups, alkenyl groups, and alkynyl groups having 1 to 10 carbon atoms. Specific examples of the aromatic hydrocarbon group include substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

The primary amine may preferably be methylamine, ethylamine, isopropylamine, n-butylamine, t-butylamine, pentylamine, isoamylamine, hexylamine, cyclohexylamine, heptylamine, octylamine, nonylamine, decylamine, aniline, 2,6-diisopropylaniline, propanolamine or 1,6-diaminohexane.
The secondary amine may preferably be dimethylamine, diethylamine, diisopropylamine, di-n-butylamine, di-t-butylamine, N-ethylmethylamine, dipentylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, bis(2-ethylhexyl)amine, dicyclohexylamine, pyrrolidine, piperidine, 2,6-dimethylpiperidine, piperazine, pyrrole, indole, N-(4-pyridylmethyl)ethylamine, diphenylamine, diethanolamine, N-methyldiethanolamine, 2-(ethylamino)ethanol, dioctanolamine, morpholine, 3-(diethylamino)propylamine, 2-[2-(dimethylamino)ethoxy]ethanol, bis(2-dimethylaminoethyl)ether, 2-(dimethylamino)ethyl methacrylate, or N-[3-(dimethylamino)propyl]methacrylamide.
The tertiary amine is preferably trimethylamine, triethylamine, diisopropylethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, dimethyldodecylamine, tridodecylamine, hexamethylenetetramine, triethylenediamine (DABCO: 1,4-diazabicyclo[2.2.0]octane), pyridine, 4-aminopyridine, 4-dimethylaminopyridine (DMAP), N,N-dimethylbenzylamine, triphenylamine, tribenzylamine, N-tert-butoxycarbonylpyrrolidine, pyrazole, triethanolamine, 2-(dimethylamino)ethanol, 2-(diethylamino)ethanol, 2-(diisopropylamino)ethanol, The amine may be ethanol, 2-(dibutylamino)ethanol, diisopropanolamine, 2-(dimethylamino)propanol, 2-(diethylamino)propanol, 1-dimethylamino-2-propanol, triisopropanolamine, dimethylaminoisopropanol, 6-dimethylamino-1-hexanol, trioctanolamine, tris(2-methoxymethoxyethyl)amine, tris[2-(2-methoxyethoxy)ethyl]amine, tris{2-(2-methoxyethoxymethoxy)ethyl}amine, tris[2-(1-methoxyethoxy)ethyl}amine, tris[2-(1-ethoxyethoxy)ethyl}amine, tris[2-(1-ethoxypropoxy)ethyl]amine, tris[2-{2-(2-hydroxyethoxy)ethoxy}ethyl]amine or triethanolamine triacetate.

The organic base is preferably either a compound having an amidine skeleton or a compound having a guanidine skeleton. These bases may have superior basicity and therefore may function particularly advantageously as a photobase generator in the photosensitive composition.

The compound having an amidine skeleton is a compound having a partial structure represented by the following general formula (Ia) in one molecule.
General formula: *-C(=NR ^x )-NR ^y R ^z ...(Ia)
In formula (Ia), R ^x , R ^y , and R ^z can each independently be a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms. When ^{R x} , R ^y , and R ^z are each a hydrocarbon group, they may be linked to each other via a carbon-carbon bond to form a cyclic structure. For example, compounds having an amidine skeleton can include compounds having a substituted or unsubstituted heterocyclic skeleton, compounds having substituted or unsubstituted fused rings, and compounds having substituted or unsubstituted fused heterocyclic rings. A specific example of a fused heterocyclic ring is an imidazole ring.

Specific examples of compounds having an amidine skeleton include imidazoles such as imidazole, 1-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-benzylimidazole, and benzimidazole; diazabicycloundecene (DBU: 1,8-diazabicyclo[5.4.0]undec-7-ene); and diazabicyclononene (DBN: 1,5-diazabicyclo[4.3.0]non-5-ene). The compound having an amidine skeleton may preferably be diazabicycloundecene or diazabicyclononene.

The compound having a guanidine skeleton is a compound having a partial structure represented by the following general formula (IIa) in one molecule.
General formula: *-NR ^x -C (=NR ^y )-NR ^z -* ... (IIa)
In formula (IIa), R ^x , R ^y , and R ^z may each independently be a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms. When R ^x , R ^y , and R ^z are each a hydrocarbon group, they may be linked to each other via a carbon-carbon bond to form a cyclic structure. For example, compounds having a guanidine skeleton may include compounds having a substituted or unsubstituted heterocyclic skeleton, compounds having substituted or unsubstituted fused rings, and compounds having substituted or unsubstituted fused heterocyclic rings. Furthermore, for example, in compounds having a guanidine skeleton, terminal N atoms may be linked to each other directly or via at least one carbon atom to form a cyclic structure.

Specific examples of compounds having a guanidine skeleton include guanidine, biguanide, 1,1,3,3-tetramethylguanidine, TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene), and MTBD (Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene). The compound having a guanidine skeleton may preferably be TBD or MTBD.

A 1 ⁺ may be any suitable cation of the above organic base A. A ^{1 +} may preferably be at least one cation selected from the group consisting of the following structural formulas:

When A ⁺ is at least one selected from the cations having the structural formula shown above, the organic ionic compound can have strong basicity. As a result, since the organic ionic compound contains at least one of the above cations as A ⁺ , it can generate a strong base very efficiently when irradiated with light. Therefore, when such a cation is used, the organic ionic compound can be particularly suitably used as a photobase generator. Note that the cation having the structure represented by formula (A-1) is a cation of DBU, the cation having the structure represented by formula (A-2) is a cation of DBN, and the cation having the structure represented by formula (A-3) is a cation of TBD.

A-3. Synthesis of Organic Compounds and Organic Ionic Compounds Organic compounds and organic ionic compounds according to embodiments of the present invention can be synthesized, for example, by the following reaction schemes. However, the following reaction schemes are not intended to limit the methods for producing organic compounds and organic ionic compounds according to embodiments of the present invention. Any appropriate reaction scheme can be employed as long as the final product (i.e., organic compound and/or organic ionic compound) is obtained.

In one embodiment, first, a compound represented by the following formula (10) is synthesized. The compound represented by formula (10) can be obtained, for example, as shown below, by reacting an acyl halide having a heterocyclic skeleton capable of constituting the organic group X with a substituted or unsubstituted benzene ring as starting materials (raw materials) in the presence of any appropriate catalyst (Reaction I-a).

In reaction Ia, X can be the organic group X described in section A-1. Therefore, the description in section A-1 can be used for the description of X (organic group).
^Y1 is a halogen (atom) constituting the acyl halide having the organic group X. ^Y2 is a substituent in the substituted or unsubstituted benzene ring. ^Y2 is, for example, a halogen. The halogens of ^Y1 and ^Y2 may each independently be fluorine, chlorine, bromine, or iodine. ^Y1 is preferably chlorine or bromine. ^Y2 is preferably fluorine.
The catalyst used in reaction Ia may be, for example, a metal halide, such as aluminum chloride.
The amounts of raw materials, catalysts, and additives added as needed can be appropriately adjusted depending on the purpose. Furthermore, reaction conditions (heating, cooling, reaction time, etc.) can also be adjusted appropriately depending on the types of raw materials, etc.

The compound represented by formula (10) can also be obtained, for example, as shown below, by reacting a heterocyclic compound (X′) capable of constituting any suitable organic group X with any suitable substituted or unsubstituted benzoyl halide compound as starting materials (raw materials) in the presence of any suitable catalyst (reaction I-b).

In reaction I-b, X′ has a heterocyclic skeleton that can constitute the organic group X. Specifically, X′ can be, for example, a compound having a pyrrole skeleton, a compound having an N-methylpyrrole skeleton, a compound having an indole skeleton, or a compound having an N-methylindole skeleton.
^Y3 and ^Y4 may each independently be a halogen atom. The halogen may be the same as that described above for ^Y1 and ^Y2 . ^Y3 may preferably be chlorine or bromine. ^Y4 may preferably be fluorine.
The catalyst used in reaction Ib may be the same as that used in reaction Ia above.
The amounts of raw materials, catalysts, and additives added as needed can be appropriately adjusted depending on the purpose. Furthermore, reaction conditions (heating, cooling, reaction time, etc.) can also be adjusted appropriately depending on the types of raw materials, etc.

In one embodiment, for example, as shown below, a compound represented by formula (11) may be obtained by indole synthesis using any suitable substituted or unsubstituted aminoacetophenone and any suitable substituted or unsubstituted halogenated acetophenone (haloacetophenone) as starting materials (raw materials) in the presence of any suitable solvent (Reaction I-c). The compound represented by formula (11) can be included in the compound represented by formula (10) above.

In Reaction I-c, ^Y5 and ^Y6 may each independently be a halogen atom. As the halogen, the same as those described above for ^Y1 and ^Y2 may be used. ^Y5 may preferably be chlorine or bromine. ^Y6 may preferably be fluorine.
The resulting compound represented by formula (11) may be further reacted with an alkylating agent (for example, methyl iodide) in the presence of any suitable base to alkylate the N atom on the indole ring.
The amounts of raw materials, catalysts, and additives added as needed can be appropriately adjusted depending on the purpose. The reaction conditions (heating, cooling, reaction time, etc.) can also be adjusted to any appropriate condition depending on the types of raw materials, etc.

Subsequently, the compound represented by formula (10) or (11) is reacted with any suitable compound having an amino group and a carboxy group (simply referred to as an amino acid) in the presence of any suitable base in any suitable solvent (Reaction II), thereby obtaining a compound having a structure represented by formula (1).

In reaction II, Y can be either Y ² in reaction Ia, Y ⁴ in reaction Ib, or Y ⁶ in reaction Ic, that is, Y can be any suitable halogen atom.
^R1 and ^R2 in Reaction II are the same as R1 and R2 in the organic compound having the structure represented by formula (1), which have been explained in Section A-1. In other words, ^R1 and ^R2 in the organic compound having the structure represented by formula ( ^{1 )} can be determined depending on the substituents in the amino acid used in Reaction II.
Examples of amino acids include glycine, N-methylglycine (sarcosine), alanine, phenylalanine, and N-phenylglycine.
Examples of the base used in Reaction II include inorganic metal salts such as alkali metal carbonates, alkali metal hydroxides, alkaline earth metal carbonates, alkaline earth metal hydroxides, etc. A representative example of the base is potassium carbonate.
The amounts of the compound represented by formula (10) or formula (11), the amino acid, the base, and any additives added as needed can be appropriately adjusted depending on the purpose. Furthermore, the reaction conditions (heating, cooling, reaction time, etc.) can also be adjusted appropriately depending on the types of raw materials, etc.

In this way, an organic compound having the structure represented by formula (1) can be obtained. From the obtained organic compound, an organic ionic compound can be obtained, for example, as follows:

An organic compound having a structure represented by formula (1) and any suitable organic base A are mixed in any suitable solvent and reacted under any suitable temperature conditions.
The organic base A is as explained in the above section A-2.
The amounts of the organic compound, organic base A, and solvent, as well as the reaction conditions (heating, cooling, reaction time, etc.) can be appropriately adjusted depending on the purpose. The reaction conditions can be, for example, room temperature (about 25° C.) and a reaction time within a range of, for example, 5 minutes to 5 hours.
In this manner, an organic ionic compound having a structure represented by formula (1-A) can be obtained.

B. Photobase Generator The photobase generator according to an embodiment of the present invention contains at least one of the above-described organic ionic compounds. As described above, the organic ionic compound according to an embodiment of the present invention can have excellent light absorption properties and can efficiently generate a base upon light irradiation, and therefore can be particularly suitably used as a photobase generator.
Specifically, by including an organic ionic compound having a structure represented by Formula (1-A), the photobase generator can have better absorption characteristics for light such as ultraviolet light than conventional photobase generators (e.g., base generators having a ketoprofen skeleton). Furthermore, by selecting an appropriate organic group X as the organic group X in the organic compound or the organic ionic compound and/or selecting an appropriate organic base as the organic base A, the photobase generator according to the present invention can exhibit superior performance as a photobase generator compared to conventional photobase generators. As a result, when blended with a reactive compound in a photosensitive composition, the photobase generator according to the present invention can proceed with a reaction under milder conditions than those of a photopolymerization initiator or a photoacid generator, and can be used as a component that enhances the curability of the composition. Therefore, the photobase generator according to the present invention can significantly improve the curability and contrast when applied to a photosensitive composition.

In one embodiment, the photobase generator contains at least one organic ionic compound having an organic group X selected from the group consisting of organic groups having structures represented by the above structural formulas (X2a), (X3a), (X4a), (X5a), (X6), (X12a), and (X13a). This configuration can achieve better curability and contrast for the photosensitive composition.

In one embodiment, the photobase generator contains at least one organic ionic compound having an organic base A having a structure represented by the above structural formula (A1), (A2), or (A3). When the photobase generator has such a configuration, the photosensitive composition can achieve superior curability and high contrast.

When the photobase generator according to an embodiment of the present invention is incorporated into a photosensitive composition, it may contain two or more of the above-described organic ionic compounds. Alternatively, the photobase generator may be used in combination with any suitable material other than the above-described organic ionic compounds that has photobase generating ability. When incorporated into a photosensitive composition, the photobase generator preferably contains only one organic compound having a structure represented by formula (1-A) above.

C. Photosensitive Composition A photosensitive composition according to one embodiment of the present invention contains a reactive compound and the above-described polymerization initiator. Because the photosensitive composition according to this embodiment contains the polymerization initiator described in Section A above (essentially an organic compound having a structure represented by the above formula (1)), radicals are efficiently generated in the reaction system upon light irradiation, and the reactive compound can be suitably polymerized and/or crosslinked by radical polymerization. As a result, the photosensitive composition according to this embodiment exhibits excellent curability when irradiated with light such as ultraviolet light, and can also exhibit excellent contrast when developed after light irradiation.

A photosensitive composition according to another embodiment of the present invention contains a reactive compound and the above-described photobase generator. Because the photosensitive composition according to this embodiment contains the photobase generator described in Section B above (essentially an organic ionic compound having a structure represented by Formula (1-A) above), it efficiently generates a base within the reaction system upon light irradiation, allowing the reactive compound to be suitably polymerized and/or crosslinked by anionic polymerization. As a result, the photosensitive composition according to this embodiment exhibits excellent curability when irradiated with light such as ultraviolet light, and can also exhibit excellent contrast when developed after light irradiation.

The reactive compound used in the photosensitive composition may be any suitable compound applicable to photosensitive compositions. In one embodiment of the photosensitive composition of the present invention, the reactive compound may include a vinyl compound. In another embodiment of the photosensitive composition of the present invention, the reactive compound may be at least one compound selected from the group consisting of an isocyanate compound, an epoxy compound, a silane compound, and a polyamic acid.

Vinyl compounds include any suitable compounds having one or more carbon-carbon double bonds in the molecule. Vinyl compounds preferably include (meth)acrylic compounds. In this specification, "(meth)acrylic" refers to at least one of "acrylic" and "methacrylic," i.e., it is a broader concept than "acrylic" and "methacrylic." A (meth)acrylic compound is a compound having one or more (meth)acryloyl groups in the molecule. Examples of (meth)acrylic compounds include monofunctional (meth)acrylic compounds and polyfunctional (meth)acrylic compounds. The (meth)acrylic compound may preferably be a polyfunctional (meth)acrylate. The (meth)acrylic compound may be a monomer, oligomer, or prepolymer.

Examples of monofunctional (meth)acrylic compounds include acrylic acid, methacrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, 1,1-dimethylethyl (meth)acrylate, pentyl (meth)acrylate, isoamyl (meth)acrylate, 1,1-dimethylpropyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 2-hydroxypropyl (meth)acrylate. acrylate, 4-hydroxybutyl (meth)acrylate, ethoxyethyl (meth)acrylate, isobornyl (meth)acrylate, ethyl diethylene glycol (meth)acrylate, benzyl (meth)acrylate, cresol (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, phenyl (meth)acrylate, phenoxyethyl (meth)acrylate, 7-amino-3,7-dimethyloctyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, and polyester mono(meth)acrylate.

Examples of polyfunctional (meth)acrylic compounds include difunctional (meth)acrylates, trifunctional (meth)acrylates, and tetrafunctional or higher functional (meth)acrylates. In one embodiment, the (meth)acrylic compound may preferably be a hexafunctional methacrylate compound.
Examples of bifunctional (meth)acrylates include di(meth)acrylates of alkanediols. Specific examples of bifunctional (meth)acrylates include 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, and 1,12-dodecanediol di(meth)acrylate.
Examples of trifunctional (meth)acrylates include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and polyester tri(meth)acrylate.
Examples of tetrafunctional (meth)acrylates include ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, and polyester tetra(meth)acrylate.
Examples of the pentafunctional (meth)acrylate include pentaerythritol penta(meth)acrylate and tripentaerythritol penta(meth)acrylate.
Examples of hexafunctional (meth)acrylates include dipentaerythritol hexa(meth)acrylate and tripentaerythritol hexa(meth)acrylate.
Examples of the hepta- or higher functional (meth)acrylate include octa(meth)acrylates such as tripentaerythritol hepta(meth)acrylate and tripentaerythritol octa(meth)acrylate, and tetra- or higher functional polyester poly(meth)acrylates.

An isocyanate compound is a compound that contains at least one isocyanate group (*-N=C=O) per molecule. By using an isocyanate compound as a reactive compound, a polymeric compound can be obtained by irradiating a photosensitive composition with light. Examples of polymeric compounds include polyurethane.

Specific examples of isocyanate compounds include linear aliphatic diisocyanate compounds such as hexamethylene diisocyanate; branched aliphatic diisocyanate compounds such as 2-methylpentane-1,5-diylbisisocyanate and trimethylhexamethylene diisocyanate; cyclic aliphatic isocyanate compounds such as isophorone diisocyanate, 1,4-diisocyanatocyclohexane, 1,3-bis(isocyanatomethyl)cyclohexane, and dicyclohexyl-4,4'-methane diisocyanate; crosslinked cyclic aliphatic diisocyanate compounds such as norbornane-2,6-diylbis(methylene)diisocyanate and norbornane-2,5-diylbis(methylene)diisocyanate; and 4,4'-diisocyanato-3,3'-dimethylbiisocyanate. Examples of the isocyanate compounds include aromatic isocyanate compounds such as phenyl, 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 2,2'-diphenylmethane diisocyanate, bibenzyl-4,4'-diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, tolylene diisocyanate, m-xylylene diisocyanate, 1,3-bis(2-isocyanato-2-propyl)benzene, 3,3'-dichloro-4,4'-diisocyanatobiphenyl, and 2,2-bis(4-isocyanatophenyl)hexafluoropropane; and isocyanates having a condensed ring aromatic such as 1,5-naphthylene diisocyanate. The isocyanate compounds may be used alone or in combination of two or more of the above.

To synthesize polyurethane, a photosensitive composition can be prepared using the above-mentioned isocyanate compound as well as any suitable polyol, which is a compound having at least two hydroxyl groups. Specific examples of polyols include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 2-methyl-1,2-propanediol, 1,4-butanediol, 1,5-pentanediol, 2-methyl-2,3-butanediol, 1,6-hexanediol, 1,2-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, 2-ethyl-hexanediol, 1,2-octanediol, 1,8-octanediol, 1,2-decanediol, 2 , 2,4-trimethylpentanediol, 2-butyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, glycerin, trimethylolpropane, 1,2,4-butanetriol, 2-methyl-1,2,4-butanetriol, 1,2,5-pentanetriol, 1,2,3,6-hexanetetrol, 1,4-sorbitan, pentaerythritol, diglycerin, ditrimethylolpropane, dipentaerythritol, D-threitol, tripentaerythritol, L-arabinitol, ribitol, xylitol, L-rhamnitol, D-glucitol, D-mannitol, galactitol, sorbitol, trehalol, sucrose, maltose, gentiobiose, lactose, melibiose, and the like, can be used alone or in combination of two or more.

An epoxy compound can be a compound that has at least one epoxy group in one molecule. Epoxy resins are also included in the category of epoxy compounds as long as they have at least one epoxy group in one molecule.

Specific examples of epoxy compounds include diglycidyl ether, spiroglycol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, butanediol diglycidyl ether, glycerin diglycidyl ether, glycidylpropoxytrimethoxysilane, allyl glycidyl ether, butyl glycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, alkylphenol glycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polyglycidyl methacrylate, glycerin polyglycidyl ether, diglycerin polyglycidyl ether, trimethylol Examples of epoxy compounds include bisphenol A epoxy resins, bisphenol F epoxy resins, bisphenol S epoxy resins, bisphenol AF epoxy resins, bixylenol epoxy resins, phenol novolac epoxy resins, tert-butyl-catechol epoxy resins, naphthalene epoxy resins, anthracene epoxy resins, naphthol epoxy resins, dicyclopentadiene epoxy resins, trisphenol epoxy resins, naphthol novolac epoxy resins, glycidylamine epoxy resins, glycidyl ester epoxy resins, glycidyl ether epoxy resins, cresol novolac epoxy resins, biphenyl epoxy resins, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane epoxy resins, cyclohexanedimethanol epoxy resins, naphthylene ether epoxy resins, trimethylol epoxy resins, and tetraphenylethane epoxy resins. The above epoxy compounds can be used alone or in combination of two or more. The epoxy compound preferably includes at least one compound selected from the group consisting of diglycidyl ether, spiroglycol diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polyglycidyl methacrylate, glycerin polyglycidyl ether, diglycerin polyglycidyl ether, trimethylolpropane polyglycidyl ether, sorbitol polyglycidyl ether, bisphenol A type epoxy resin, bisphenol F type epoxy resin, cresol novolac type epoxy resin, and biphenyl type epoxy resin.

When irradiated with light in a photosensitive composition in the presence of a photobase generator, a silane compound can undergo a sol-gel reaction to form a polysiloxane. Polysiloxane is a polymeric compound that has a siloxane bond (*-O-Si-*) in its main chain and organic groups in its side chains. Specifically, the silane compound can be an organosilane compound that has the above-mentioned siloxane bond and any suitable organic group at its terminal.

Any suitable silane compound having a siloxane bond can be used. Examples of silane compounds include monoalkylsilanes, monoalkoxysilanes, dialkylsilanes, dialkoxysilanes, trialkylsilanes, trialkoxysilanes, tetraalkylsilanes, tetraalkoxysilanes, and analogs thereof. The silane compound may be, for example, a dimer, oligomer, or prepolymer of the above. Specific examples of silane compounds include trimethylmethoxysilane, dimethyldimethoxysilane, methyltrimethoxysilane, tetramethoxysilane, trimethylethoxysilane, dimethyldiethoxysilane, methyltriethoxysilane, tetraethoxysilane, diphenyldimethoxysilane, phenyltrimethoxysilane, diphenyldiethoxysilane, phenyltriethoxysilane, hexyltrimethoxysilane, tetrapropoxysilane, tetrabutoxysilane, poly 3-(methyldimethoxysilyl)propyl methacrylate, poly 3-(methyldiethoxysilyl)propyl methacrylate, poly 3-(trimethoxysilyl)propyl methacrylate, poly 3-(triethoxysilyl)propyl methacrylate, vinyltrichlorosilane, and vinyltrimethoxysilane. Examples of suitable silane compounds include silane, vinyltriethoxysilane, vinyltris(β-methoxyethoxy)silane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropylmethyldimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-chloropropylmethyldimethoxysilane, and γ-chloropropylmethyldiethoxysilane. These silane compounds can be used alone or in combination of two or more.

Polyamic acid (also called polyamic acid) can be a compound that serves as a precursor to polyimide. Polyamic acid is composed of, for example, a condensation product of an acid dianhydride and a diamine compound. When a photosensitive composition contains polyamic acid and a photobase generator, polyimide can be synthesized.

Any suitable compound can be used as the dianhydride and diamine compound for synthesizing the polyamic acid. Examples of acid dianhydrides include 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3',3,4'-biphenyltetracarboxylic dianhydride, pyromellitic anhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride (BPAF), 3,4,9,10-perylenetetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 5-(di- Examples of the dianhydrides include tetracarboxylic acid dianhydrides such as 2,5-dioxotetrahydrofuryl-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-tetralin-1,2-dicarboxylic acid anhydride, tetrahydrofuran-2,3,4,5-tetracarboxylic acid dianhydride, 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,4-dimethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride, and analogs thereof. The dianhydrides may be used alone or in combination of two or more thereof.

Examples of diamine compounds include hexamethylenediamine, octamethylenediamine, 1,9-nonanediamine, 2-methyl-1,8-octanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, 1,2-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, 1,2-di(2-aminoethyl)cyclohexane, 1,3-di(2-aminoethyl)cyclohexane, 1,4-di(2-aminoethyl)cyclohexane, bis(4-aminocyclohexane), hexyl)methane, 2,6-bis(aminomethyl)bicyclo[2.2.1]heptane, 2,5-bis(aminomethyl)bicyclo[2.2.1]heptane, p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminobenzophenone, 4,4'-diaminobenzophenone, 3,4'-diaminobenzophenone, 3,3'-diaminodiphenylmethane, 4,4'-diaminodi Phenylmethane, 3,4'-diaminodiphenylmethane, 2,2-di(3-aminophenyl)propane, 2,2-di(4-aminophenyl)propane, 2-(3-aminophenyl)-2-(4-aminophenyl)propane, 2,2-di(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-di(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropane, 2-(3-aminophenyl)-2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropane, 1,1-di(3 Examples of the diamine compound include 1,4-diaminoanthracene, 1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 2,7-diaminonaphthalene, and 1,4-diaminoanthracene. The diamine compounds may be used alone or in combination of two or more thereof.

The photosensitive composition according to an embodiment of the present invention may contain any other suitable additives in addition to the reactive compound, polymerization initiator, and/or photobase generator. Examples of other additives include surfactants, plasticizers, fillers, leveling agents, antioxidants, UV absorbers, catalysts, dispersing aids, sensitizers, crosslinking agents, pigments, dyes, inorganic compounds, colorants, solvents, and polymerization inhibitors.

There are no particular limitations on the uses of the photosensitive composition, and it can be used in any appropriate application. For example, it can be used in a variety of applications, such as photocurable paints; photocurable inks; photocurable adhesives; printing plates; printing inks; dental compositions; holographic recording materials; recording materials such as image recording materials; printed wiring boards; color filters in display elements such as televisions, monitors, personal digital assistants, and digital cameras; plating masks; solder resists; magnetic recording materials; optical switches; electronic circuits; various photoresist materials; and insulating films, protective films, or sealants for various electronic materials.

In one embodiment, the amount of reactive compound and polymerization initiator in the photosensitive composition may be any appropriate ratio. The ratio of polymerization initiator to a total of 100 parts by weight of reactive compounds is preferably 0.05 parts by weight or more, more preferably 0.10 parts by weight or more, and even more preferably 0.15 parts by weight or more. On the other hand, the ratio of polymerization initiator to a total of 100 parts by weight of reactive compounds may be preferably 20 parts by weight or less, more preferably 10 parts by weight or less, and more preferably 5 parts by weight or less. Within this range, the effects of the photosensitive composition according to this embodiment of the present invention may be remarkable.

In another embodiment, the amount of reactive compound and photobase generator in the photosensitive composition may be any appropriate ratio. The ratio of the photobase generator to 100 parts by weight of the total reactive compounds is preferably 1 part by weight or more, more preferably 3 parts by weight or more, and even more preferably 5 parts by weight or more. On the other hand, the ratio of the photobase generator to 100 parts by weight of the total reactive compounds may be preferably 50 parts by weight or less, more preferably 40 parts by weight or less, and more preferably 30 parts by weight or less. Within this range, the effects of the photosensitive composition according to embodiments of the present invention may be remarkable.

The present invention will be explained in more detail below using examples, but the present invention is not limited to these examples. Measurement and evaluation methods used in the examples are as follows. Unless otherwise specified, "parts" and "%" in the examples are by weight.

[Ultraviolet absorption spectrum and extinction coefficient]
A methanol solution (0.02 g/L) of the organic ionic compound obtained in each synthesis example was prepared, and the absorption spectrum and absorbance were measured using a spectrophotometer (Hitachi High-Tech Science Corporation, product name "U-3900H"). From the obtained absorption spectrum, the maximum absorption wavelength (λmax) at wavelengths of 200 nm to 500 nm was read. The results are shown in Table 1. Furthermore, from the solution concentration and absorbance, the molar absorption coefficient ε (L·mol ⁻¹ ·cm ⁻¹ ) and gram absorption coefficient E (L·g ⁻¹ ·cm ⁻¹ ) at the maximum absorption wavelength and a wavelength of 365 nm, respectively, were calculated, and the results are also shown in Table 1. The ultraviolet absorption spectra of the organic ionic compounds obtained in each synthesis example are shown in FIGS. 1 to 24 . In the spectra shown in FIGS. 1 to 24 , the horizontal axis represents wavelength (nm) and the vertical axis represents absorbance.

The synthesis of each compound used in the Examples, Comparative Examples and Reference Examples is shown below.
Synthesis Example 1-1 Synthesis of Compound 1-1 and Compound 1-1A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
A four-neck flask was charged with 3.0 parts by weight of 2-furoyl chloride and 20.5 parts by weight of fluorobenzene, and 3.1 parts by weight of aluminum chloride was added at room temperature and mixed. The mixture was stirred overnight at 40°C. Next, the mixture was cooled to room temperature and added to 100.0 parts by weight of ice water, followed by separation into an organic layer and an aqueous layer. Next, the organic layer was washed with water, and the washed organic layer was concentrated under reduced pressure. As a result, 4.0 parts by weight of a compound (hereinafter referred to as Compound 1-1a) was obtained as a brown oil (yield 91.5%).
(Second reaction)
To a four-neck flask, 4.0 parts by weight of compound 1-1a obtained in the first reaction, 3.2 parts by weight of glycine, 5.8 parts by weight of potassium carbonate, 30.0 parts by weight of dimethyl sulfoxide (DMSO), and 5.0 parts by weight of water were added and stirred at 120°C for 3 hours. Next, this liquid was cooled to room temperature, and 50.0 parts by weight of water and 30 parts by weight of ethyl acetate were added. Insoluble matter was removed by filtration, and then the liquid was separated into an organic layer and an aqueous layer. 10.1 parts by weight of concentrated hydrochloric acid was added to the aqueous layer to make an acidic solution with a pH of 1 to 2, which was then extracted with ethyl acetate. 0.1 parts by weight of activated carbon was added to the extracted organic layer and stirred at room temperature for 5 minutes. Subsequently, the activated carbon was removed from the organic layer by filtration, and the mixture was concentrated under reduced pressure. Next, 5.0 parts by weight of methanol was added to the residue after vacuum concentration, and crystallization occurred. The precipitated crystals were filtered and dried to obtain 0.9 parts by weight of a compound having a structure represented by the following formula (1-1) (hereinafter referred to as compound 1-1) as a yellow solid (yield 17.1%).
(Third reaction)
0.3 parts by weight (1.22 mmol) of the obtained compound 1-1, 0.186 parts by weight (1.22 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 5.0 parts by weight of tetrahydrofuran (THF) were added to a sample bottle and stirred at room temperature for 0.5 hours. Next, the mixture was concentrated under reduced pressure to obtain a yellow-brown solid compound having a structure represented by the following formula (1-1A) (hereinafter referred to as compound 1-1A). The structures of the obtained compound 1-1 and compound 1-1A were each confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-1
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.74 (br: 1H), 8.02 (d: 1H), 7.82 (d: 2H), 7.27 (d: 1H), 6.94 (br: 1H), 6.73 (dd: 1H), 6.66 (d: 2H), 3.93 (s: 2H)
・Compound 1-1A
(400MHz, DMSO-d ₆ ) δ [ppm]: 8.00 (d: 1H), 7.81 (d: 2H), 7.24 (d: 1H), 6.72 (dd: 1H), 6.62 (dd: 2H), 6.30 (t: 1H), 3.52-3.50 (m: 2H), 3.44 (t: 2H), 3.37 (d: 2H), 3.24 (t: 2H), 2.73-2.71 (m: 2H), 1.88 (quin: 2H), 1.65-1.58 (m: 6H)

[Synthesis Example 1-2] Synthesis of Compound 1-2 and Compound 1-2A Compound 1-2 having a structure represented by the following formula (1-2) and Compound 1-2A having a structure represented by the following formula (1-2A) were synthesized in the same manner as in Synthesis Example 1-1, except that glycine was changed to DL-alanine. The yield of the obtained Compound 1-2 was 38.1%. The structures of Compound 1-2 and Compound 1-2A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-2
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.73 (br: 1H), 8.01 (d: 1H), 7.82 (d: 2H), 7.27 (d: 1H), 6.93 (d: 1H), 6.73 (dd: 1H), 6.65 (d: 2H), 4.14-4.07 (m: 1H), 1.42 (d: 3H)
・Compound 1-2A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.23 (br: 1H), 8.00 (d: 1H), 7.79 (d: 2H), 7.23 (d: 1H), 6.72 (dd: 1H), 6.61 (d: 2H), 6.54 (d: 1H), 3.5 2-3.51 (m: 2H), 3.44 (t: 2H), 3.24 (t: 2H), 2.73-2.70 (m: 2H), 1.88 (quin: 2H), 1.65-1.58 (m: 6H), 1.27 (d: 3H)

Synthesis Example 1-3 Synthesis of Compound 1-3 and Compound 1-3A Compound 1-3 having a structure represented by the following formula (1-3) and Compound 1-3A having a structure represented by the following formula (1-3A) were synthesized in the same manner as in Synthesis Example 1-1, except that glycine was changed to sarcosine (N-methylglycine). The yield of the obtained Compound 1-3 was 71.8%. The structures of Compound 1-3 and Compound 1-3A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.

・Compound 1-3
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.77 (br: 1H), 8.03 (d: 1H), 7.88 (d: 2H), 7.29 (d: 1H), 6.77 (d: 2H), 6.74 (dd: 1H), 4.24 (s: 2H), 3.08 (s: 3H)
・Compound 1-3A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.27 (br: 1H), 8.00 (d: 1H), 7.83 (d: 2H), 7.23 (d: 1H), 6.72 (dd: 1H), 6.63 (d: 2H), 3.67 (s: 2H), 3.5 1-3.49 (m: 2H), 3.43 (t: 2H), 3.20 (t: 2H), 3.02 (s: 3H), 2.69-2.67 (m: 2H), 1.86 (quin: 2H), 1.64-1.57 (m: 6H)

Synthesis Example 1-4 Synthesis of Compound 1-4 and Compound 1-4A Compound 1-4 having a structure represented by the following formula (1-4) and Compound 1-4A having a structure represented by the following formula (1-4A) were synthesized in the same manner as in Synthesis Example 1-1, except that 2-furoyl chloride was changed to 2-benzofurancarboxylic acid chloride. The yield of the obtained Compound 1-4 was 29.5%. The structures of the obtained Compound 1-4 and Compound 1-4A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-4
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.78 (br: 1H), 7.92 (d: 2H), 7.83 (d: 1H), 7.75 (d: 1H), 7.68 ( s: 1H), 7.53 (t: 1H), 7.37 (t: 1H), 7.07 (t: 1H), 6.70 (d: 2H), 3.97 (d: 2H)
・Compound 1-4A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.17 (br: 1H), 7.91 (d: 2H), 7.83 (d: 1H), 7.75 (d: 1H), 7.65 (s: 1H), 7.52 (t: 1H), 7.37 (t: 1H), 6.68 (d: 2H), 6.4 6 (t: 1H), 3.53-3.51 (m: 2H), 3.45 (t: 2H), 3.40 (d: 2H), 3.25 (t: 2H), 2.74-2.72 (m: 2H), 1.89 (quin: 2H), 1.66-1.61 (m: 6H)

Synthesis Example 1-5 Synthesis of Compound 1-5 and Compound 1-5A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
A four-neck flask was charged with 1.8 parts by weight of pyrrole and 50.0 parts by weight of methylene chloride, and the mixture was cooled to 5°C or below. While maintaining the temperature at 5°C or below, 3.7 parts by weight of anhydrous aluminum chloride was added to this liquid. Next, a solution of 5.0 parts by weight of 4-bromobenzoyl chloride dissolved in 10.0 parts by weight of methylene chloride was added dropwise at a temperature of 5°C or below. The mixture was stirred at 5°C or below for 1 hour and then at room temperature for 3 hours. Next, 100.0 parts by weight of this liquid was added to ice water at room temperature. Any particles adhering to the inner wall of the flask were dissolved with methanol and added to the ice water. The liquid was separated into an organic layer and an aqueous layer. The resulting organic layer was concentrated under reduced pressure, and then 10.0 parts by weight of water, 3.0 parts by weight of a 30% aqueous sodium hydroxide solution, and 20.0 parts by weight of methanol were added to the concentrated residue. This solution was stirred overnight at room temperature to decompose the unreacted acid chloride (4-bromobenzoyl chloride) and crystallize the reaction product. The precipitated crystals were then filtered, washed with water, and dried to obtain a compound (hereinafter referred to as Compound 1-5a) (yield: 50.8%).
(Second reaction)
To a four-neck flask, 2.8 parts by weight of the obtained compound 1-5a, 1.7 parts by weight of glycine, 3.1 parts by weight of potassium carbonate, 0.2 parts by weight of copper (I) iodide, 20.0 parts by weight of DMSO, and 2.0 parts by weight of water were added, and the mixture was stirred at 110°C for 2 hours. Next, this solution was cooled to room temperature, and 50.0 parts by weight of water was added, followed by 5.5 parts by weight of concentrated hydrochloric acid to adjust the pH to 1 to 2 to obtain an acidic solution. The precipitated solid was removed by filtration, and the filtrate was extracted with ethyl acetate. The extracted organic layer was concentrated under reduced pressure, and 30.0 parts by weight of water was added to precipitate crystals. The precipitated crystals were then filtered, washed with water, and dried to obtain compound 1-5 having a structure represented by the following formula (1-5) (yield: 30.3%). The structure of the obtained compound 1-5 was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the 1H-NMR spectrum are shown below.
(Third reaction)
A compound having a structure represented by the following formula (1-5A) (hereinafter referred to as compound 1-5A) was obtained in the same manner as in the third reaction of Synthesis Example 1-1, except that compound 1-5 was used instead of compound 1-1. The structure of the obtained compound 1-5A was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The result of the ¹ H-NMR spectrum is shown below.
・Compound 1-5
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.73 (br: 1H), 11.80 (s: 1H), 7.71 (d: 2H), 7.10 (dd: 1H), 6.77-6.72 (m: 2H), 6.64 (d: 2H), 6.22 (dd: 1H), 3.91 (s: 2H)
・Compound 1-5A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.78 (br: 1H), 7.68 (d: 2H), 7.07 (s: 1H), 6.75 (d: 1H), 6.59 (d: 2H), 6.21 (t: 1H), 6.04 (br: 1H), 3.5 2-3.50 (m: 2H), 3.44 (t: 2H), 3.34 (d: 2H), 3.25 (t: 2H), 2.73-2.71 (m: 2H), 1.88 (quin: 2H), 1.66-1.58 (m: 6H)

Synthesis Example 1-6 Synthesis of Compound 1-6 and Compound 1-6A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
To a four-neck flask, 5.0 parts by weight of 4-fluorobenzoyl chloride, 5.1 parts by weight of 1-methylpyrrole, and 50.0 parts by weight of methylene chloride were added. Next, while stirring this liquid, 4.6 parts by weight of anhydrous aluminum chloride was added in portions at room temperature, and the mixture was further stirred at room temperature for 1 hour. Next, at room temperature, this liquid was added to 100.0 parts by weight of ice water to separate the liquid. The organic layer was concentrated under reduced pressure, and then 15.0 parts by weight of methanol, 4.0 parts by weight of a 30% aqueous sodium hydroxide solution, and 10.0 parts by weight of water were added to the concentrated residue and stirred at room temperature to decompose unreacted 4-fluorobenzoyl chloride. Next, an additional 100.0 parts by weight of water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and the resulting organic layer was concentrated under reduced pressure to obtain a brown oily compound (hereinafter referred to as Compound 1-6a) (yield: 49.5%).
(Second and third reactions)
Compound 1-6 having a structure represented by the following formula (1-6) and compound 1-6A having a structure represented by the following formula (1-6A) were synthesized in the same manner as in Synthesis Example 1-1, except that compound 1-6a was used instead of compound 1-1a. The yield of compound 1-6 was 61.9%. The structures of the obtained compounds 1-6 and 1-6A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.
・Compound 1-6
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.69 (br: 1H), 7.62 (d: 2H), 7.13 (s: 1H), 6.71 (br: 1H), 6.60 (t: 3H), 6.12 (dd: 1H), 3.90 (s: 2H), 3.86 (s: 3H)
・Compound 1-6A
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.51 (br: 1H), 7.59 (d: 2H), 7.11 (t: 1H), 6.58-6.54 (m: 3H), 6.11 (dd: 1H), 6.00 (t: 1H), 3.85 (s: 3 H), 3.54-3.52 (m: 2H), 3.46 (t: 2H), 3.28-3.23 (m: 4H), 2.70-2.67 (m: 2H), 1.90 (quin: 2H), 1.67-1.59 (m: 6H)

Synthesis Example 1-7 Synthesis of Compound 1-7 and Compound 1-7A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
A four-neck flask was charged with 2.9 parts by weight of 2-aminoacetophenone, 4.7 parts by weight of 2-bromo-4'-fluoroacetophenone, and 29.0 parts by weight of N,N-dimethylformamide (DMF), and the mixture was stirred at 100°C for 3 hours. The resulting solution was then cooled to room temperature and added to 200.0 parts by weight of water. Extraction was performed with ethyl acetate to separate the organic and aqueous layers. The organic layer was then washed with water, and the washed organic layer was concentrated under reduced pressure. 10.0 parts by weight of acetonitrile was added to the concentrated residue to cause crystallization. The precipitated crystals were then filtered, washed with water, and dried to obtain a pale brown solid compound (hereinafter referred to as Compound 1-7a) (yield: 44.0%).
(Second and third reactions)
Compound 1-7 having a structure represented by the following formula (1-7) and compound 1-7A having a structure represented by the following formula (1-7A) were synthesized in the same manner as in Synthesis Example 1-1, except that compound 1-7a was used instead of compound 1-1a. The yield of compound 1-7 was 40.3%. The structures of the obtained compounds 1-7 and 1-7A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.

・Compound 1-7
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.72 (br: 1H), 11.34 (s: 1H), 7.63 (d: 3H), 7.40 (d: 1H), 7.24 ( t: 1H), 7.07 (t: 1H), 6.91 (br: 1H), 6.67 (d: 2H), 3.94 (s: 2H), 2.31 (s: 3H)
・Compound 1-7A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.34 (br: 1H), 7.61 (dd: 3H), 7.40 (d: 1H), 7.23 (t: 1H), 7.06 (t: 1H), 6.62 (d: 2H), 6.23 (t: 1H), 3.52-3.5 0 (m: 2H), 3.44 (t: 2H), 3.34 (d: 2H), 3.24 (t: 2H), 2.71-2.69 (m: 2H), 2.31 (s: 3H), 1.88 (quin: 2H), 1.66-1.58 (m: 6H)

Synthesis Example 1-8 Synthesis of Compound 1-8 and Compound 1-8A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
To a four-neck flask, 6.5 parts by weight of compound 1-7a obtained in Synthesis Example 1-7 and 32.5 parts by weight of THF were added, and 1.2 parts by weight of 60% sodium hydride was added in portions at room temperature, followed by stirring at room temperature for 5 minutes. Next, 4.7 parts by weight of methyl iodide was added dropwise at room temperature, and the mixture was stirred at room temperature for 3 hours. Next, this liquid was added to 200.0 parts by weight of water at room temperature, and extraction was performed with ethyl acetate to separate the organic layer and the aqueous layer. Next, the organic layer was washed with water, and the washed organic layer was concentrated under reduced pressure. This yielded a brown oily compound (hereinafter referred to as compound 1-8a).
(Second and third reactions)
Compound 1-8 having a structure represented by the following formula (1-8) and compound 1-8A having a structure represented by the following formula (1-8A) were synthesized in the same manner as in Synthesis Example 1-1, except that compound 1-8a was used instead of compound 1-1a. The yield of compound 1-8 was 65.2%. The structures of the obtained compounds 1-8 and 1-8A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.
・Compound 1-8
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.75 (br: 1H), 7.62 (d: 3H), 7.49 (d: 1H), 7.31 (t: 1H), 7.12 ( t: 1H), 7.03 (t: 1H), 6.66 (d: 2H), 3.95 (d: 2H), 3.68 (s: 3H), 2.12 (s: 3H)
・Compound 1-8A
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.95 (br: 1H), 7.61 (d: 1H), 7.57 (d: 2H), 7.48 (d: 1H), 7.29 (t: 1H), 7.11 (t: 1H), 6.61 (d: 2H), 6.39 (t: 1H), 3.67 (s: 3H) ), 3.52-3.50 (m: 2H), 3.44 (t: 2H), 3.34 (d: 2H), 3.24 (t: 2H), 2.71-2.68 (m: 2H), 2.13 (s: 3H), 1.88 (quin: 2H), 1.66-1.59 (m: 6H)

[Synthesis Example 1-9] Synthesis of Compound 1-9 and Compound 1-9A Compound 1-9 having a structure represented by the following formula (1-9) and Compound 1-9A having a structure represented by the following formula (1-9A) were synthesized in the same manner as in Synthesis Example 1-5, except that pyrrole was changed to 1-(p-toluenesulfonyl)-1H-indole. The yield of the obtained Compound 1-9 was 23.0%. The structures of the obtained Compound 1-9 and Compound 1-9A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-9
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.69 (br: 1H), 11.88 (s: 1H), 8.17 (d: 1H), 7.92 (d: 1H), 7.67 (d: 2H), 7.49 (d: 1H), 7.24-7.16 (m: 2H), 6.65 (d: 3H), 3.91 (s: 2H)
・Compound 1-9A
(400MHz, DMSO-d ₆ ) δ [ppm]: 8.16 (d: 1H), 7.90 (s: 1H), 7.65 (d: 2H), 7.50 (d: 1H), 7.23-7.14 (m: 2H), 6.62 (d: 2H), 5.95 (t: 1H), 3. 49-3.46 (m: 2H), 3.41 (t: 2H), 3.37 (d: 2H), 3.23 (t: 2H), 2.67-2.64 (m: 2H), 1.86 (quin: 2H), 1.65-1.57 (m: 6H)

[Synthesis Example 1-10] Synthesis of Compound 1-10 and Compound 1-10A Compound 1-10 having a structure represented by the following formula (1-10) and Compound 1-10A having a structure represented by the following formula (1-10A) were synthesized in the same manner as in Synthesis Example 1-6, except that 1-methylpyrrole was changed to 1-methylindole. The yield of the obtained Compound 1-10 was 15.2%. The structures of the obtained Compound 1-10 and Compound 1-10A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-10
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.70 (br: 1H), 8.20 (d: 1H), 7.99 (s: 1H), 7.68 (d: 2H), 7.54 ( d: 1H), 7.29 (t: 1H), 7.23 (t: 1H), 6.66 (d: 3H), 3.92 (s: 2H), 3.88 (s: 3H)
・Compound 1-10A
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.85 (br: 1H), 8.19 (d: 1H), 7.98 (s: 1H), 7.65 (d: 2H), 7.54 (d: 1H), 7.28 (t: 1H), 7.22 (t: 1H), 6.61 (d: 2H), 5.93 (t: 1H), 3.88 (s: 3H), 3.53-3.51 (m: 2H), 3.45 (t: 2H), 3.32 (d : 2H), 3.25 (t: 2H), 2.72-2.69 (m: 2H), 1.89 (quin: 2H), 1.66-1.59 (m: 6H)

[Synthesis Example 1-11] Synthesis of Compound 1-11 and Compound 1-11A Compound 1-11 having a structure represented by the following formula (1-11) and Compound 1-11A having a structure represented by the following formula (1-11A) were synthesized in the same manner as in Synthesis Example 1-1, except that 2-furoyl chloride was changed to 2-benzo[b]thiophenecarboxylic acid chloride. The yield of Compound 1-11 was 17.0%. The structures of the obtained Compound 1-11 and Compound 1-11A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-11
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.76 (br: 1H), 8.06 (dd: 3H), 7.81 (d: 2H), 7.54-7.45 (m: 2H), 7.02 (t: 1H), 6.71 (d: 2H), 3.96 (d: 2H)
・Compound 1-11A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.05 (br: 1H), 8.05 (dd: 3H), 7.79 (d: 2H), 7.53-7.45 (m: 2H), 6.68 (d: 2H), 6.40 (t: 1H), 3.54-3 .51 (m: 2H), 3.45 (t: 2H), 3.39 (d: 2H), 3.26 (t: 2H), 2.74-2.72 (m: 2H), 1.89 (quin: 2H), 1.66-1.59 (m: 6H)

[Synthesis Example 1-12] Synthesis of Compound 1-12 and Compound 1-12A Compound 1-12 having a structure represented by the following formula (1-12) and Compound 1-12A having a structure represented by the following formula (1-12A) were synthesized in the same manner as in Synthesis Example 1-6, except that 1-methylpyrrole was changed to benzo[b]thiophene. The yield of Compound 1-12 was 19.2%. The structures of the obtained Compound 1-12 and Compound 1-12A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-12
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.76 (br: 1H), 8.27 (s: 1H), 8.18-8.09 (m: 2H), 7.71 (d: 2H), 7.48-7.45 (m: 2H), 6.97 (br: 1H), 6.68 (d: 2H), 3.95 (d: 2H)
・Compound 1-12A
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.86 (br: 1H), 8.22 (s: 1H), 8.14-8.08 (m: 2H), 7.67 (d: 2H), 7.46-7.44 (m: 2H), 6.62 (d: 2H), 6.29 (t: 1H) ), 3.54-3.51 (m: 2H), 3.45 (t: 2H), 3.34 (d: 2H), 3.25 (t: 2H), 2.72-2.69 (m: 2H), 1.89 (quin: 2H), 1.66-1.60 (m: 6H)

Synthesis Example 1-13 Synthesis of Compound 1-13 and Compound 1-13A Organic compounds and organic ionic compounds were synthesized according to the following synthesis methods.
(Synthesis of Compound 1-13a)
To a four-neck flask, 25.0 parts by weight of DMF was added, and 22.0 parts by weight of phosphorus oxychloride was added dropwise at room temperature. After stirring at room temperature for 10 minutes, 5.0 parts by weight of 2-butylbenzofuran was added dropwise at room temperature, and the temperature was raised to 85°C. After stirring at 85°C for 2 hours, an additional 13.2 parts by weight of phosphorus oxychloride was added dropwise at 85°C, and the mixture was stirred at 85°C for an additional 2.5 hours. Next, this liquid was added to 200.0 parts by weight of ice water at room temperature, and extraction was performed with ethyl acetate to separate the organic and aqueous layers. The organic layer was then washed with water, and the washed organic layer was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (100% n-hexane) to obtain a pale yellow oily compound (hereinafter referred to as Compound 1-13a) (yield: 62.8%).
(Synthesis of Compound 1-13b)
To a four-neck flask, 3.1 parts by weight of compound 1-13a, 15.7 parts by weight of acetonitrile, and 0.2 parts by weight of 85% phosphoric acid were added, and 2.0 parts by weight of 35% hydrogen peroxide was added dropwise at 10°C or below. Subsequently, while maintaining the temperature at 10°C or below, 6.7 parts by weight of a 25% aqueous sodium chlorite solution was added dropwise. Thereafter, the temperature was raised to 35°C, and while observing the progress of the reaction, additional 25% aqueous sodium chlorite solution and 35% hydrogen peroxide were added. The total additional amounts were 6.0 parts by weight of a 25% aqueous sodium chlorite solution and 1.0 part by weight of a 35% hydrogen peroxide solution. After stirring for 1.5 hours at a reaction temperature of 35°C, 80.0 parts by weight of water was added, and crystallization occurred. The precipitated crystals were filtered, washed with water, and dried to obtain a compound (hereinafter referred to as compound 1-13b) (yield 76.1%).
(Synthesis of Compound 1-13c)
To a four-neck flask, 2.5 parts by weight of compound 1-13b, 25.0 parts by weight of toluene, and 2 drops of DMF were added, and 2.7 parts by weight of thionyl chloride was added dropwise at room temperature. The mixture was then heated to 80°C and stirred at 80°C for 1 hour. The reaction solution was then cooled to room temperature and concentrated under reduced pressure to obtain a brown oily compound (hereinafter referred to as compound 1-13c).
(First reaction, second reaction, and third reaction)
Compound 1-13 having a structure represented by the following formula (1-13) and compound 1-13A having a structure represented by the following formula (1-13A) were synthesized in the same manner as in Synthesis Example 1-1, except that 2-furoyl chloride was changed to compound 1-13c. The yield of the obtained compound 1-13 was 20.6%. The structures of the obtained compounds 1-13 and 1-13A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.
・Compound 1-13
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.75 (br: 1H), 7.62 (d: 3H), 7.37-7.29 (m: 2H), 7.24 (t: 1H), 6.98 (t: 1H), 6. 65 (d: 2H), 3.94 (d: 2H), 2.82 (t: 2H), 1.70-1.63 (m: 2H), 1.30-1.21 (m: 2H), 0.82 (t: 3H)
・Compound 1-13A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.18 (br: 1H), 7.61 (d: 1H), 7.57 (d: 2H), 7.36 (d: 1H), 7.31 (t: 1H), 7.23 (t: 1H), 6.60 (d: 2H), 6.35 (t: 1H), 3.53-3.51 (m: 2H), 3 .45 (t: 2H), 3.35 (d: 2H), 3.25 (t: 2H), 2.82 (t: 2H), 2.74-2.71 (m: 2H) ), 1.89 (quin: 2H), 1.70-1.59 (m: 8H), 1.30-1.21 (m: 2H), 0.82 (t: 3H)

[Synthesis Example 1-14] Synthesis of Compound 1-1B Compound 1-1B having a structure represented by the following formula (1-1B) was synthesized in the same manner as in Synthesis Example 1-1, except that 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) was changed to 1,5-diazabicyclo[4.3.0]-5-nonene (DBN). The yield of the obtained compound 1-1B was 15.6%. The structure of the obtained compound 1-1B was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-1B
(400MHz, DMSO-d ₆ ) δ [ppm]: 8.00 (d: 1H), 7.80 (d: 2H), 7.23 (d: 1H), 6.71 (dd: 1H), 6.62 (d: 2H), 6.28 (t: 1H), 3.56 (t: 2H), 3.36-3.33 (m: 4H), 3.28 (t: 2H), 2.78 (t: 2H), 2.00 (quin: 2H), 1.88 (quin: 2H)

[Synthesis Example 1-15] Synthesis of Compound 1-1C Compound 1-1C having a structure represented by the following formula (1-1C) was synthesized in the same manner as in Synthesis Example 1-1, except that 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) was changed to 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). The yield of the obtained compound 1-1C was 15.6%. The structure of the obtained compound 1-1C was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-1C
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.14 (br: 1H), 8.00 (d: 1H), 7.80 (d: 2H), 7.23 (d: 1H), 6.71 (dd: 1H), 6 .64 (d: 2H), 6.41 (t: 1H), 3.47 (d: 2H), 3.25 (t: 4H), 3.14 (t: 4H), 1.86 (quin: 4H)

Synthesis Example 1-16 Synthesis of Compound 1-14 and Compound 1-14A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
A four-neck flask was charged with 15.0 parts by weight of 2-furoyl chloride and 27.1 parts by weight of bromobenzene, and 16.7 parts by weight of aluminum chloride was added at room temperature and mixed. The mixture was heated to 80°C and then stirred at 80°C for 2 hours. 15 parts by weight of ethyl acetate was added to the mixture, and the mixture was cooled to room temperature. Next, 150 parts by weight of this mixture was added to ice water, and 40 parts by weight of ethyl acetate was added. The mixture was then separated into an organic layer and an aqueous layer. The resulting organic layer was concentrated under reduced pressure, and 150 parts by weight of cyclohexane was added to the concentrated residue. The mixture was cooled with ice water and crystallized. The precipitated crystals were filtered and dried to obtain 21.7 parts by weight of a gray-white solid compound (hereinafter referred to as Compound 1-14a) (yield: 75.4%).
(Second and third reactions)
Compound 1-14 having a structure represented by the following formula (1-14) and compound 1-14A having a structure represented by the following formula (1-14A) were synthesized in the same manner as in Synthesis Example 1-5, except that compound 1-14a was used instead of compound 1-5a and glycine was replaced with DL-2-phenylglycine. The yield of compound 1-14 was 43.4%. The structures of the obtained compounds 1-14 and 1-14A were each confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-14
(400MHz, DMSO-d ₆ ) δ [ppm]: 13.07 (br: 1H), 7.98 (d: 1H), 7.78 (d: 2H), 7.53 (d: 1H), 7.39 (t: 2H), 7.32 (t: 1H), 7.25 (d: 1H), 7.21 (d: 1H), 6.79 (d: 2H), 6.70 (dd: 1H), 5.27 (d: 1H)
・Compound 1-14A
(400MHz, DMSO-d ₆ ) δ [ppm]: 10.49 (br: 1H), 7.94 (d: 1H), 7.70 (d: 2H), 7.39 (d: 2H), 7.23 (t: 2H), 7.19 (d: 1H), 7.1 4 (t: 1H), 6.94 (d: 1H), 6.67 (dd: 1H), 6.55 (d: 2H), 4.52 (d: 1H), 3.52-3.50 (m: 2H), 3.43 (t: 2H). 3.21 (t: 2H), 2.66-2.64 (m: 2H), 1.88 (quin: 2H), 1.64-1.57 (m: 6H)

Synthesis Example 1-17 Synthesis of Compound 1-15 and Compound 1-15A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
Compound 1-15 having a structure represented by the following formula (1-15) and compound 1-15A having a structure represented by the following formula (1-15A) were synthesized in the same manner as in Synthesis Example 1-5, except that compound 1-14a was used instead of compound 1-5a and glycine was replaced with iminodiacetic acid. The yield of compound 1-15 was 15.6%. The structures of the obtained compounds 1-15 and 1-15A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.
・Compound 1-15
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.79 (br: 1H), 8.02 (d: 1H), 7.88 (d: 2H), 7.29 (d: 1H), 6.73 (dd: 1H), 6.67 (d: 2H), 4.23 (s: 4H)
・Compound 1-15A
(400MHz, DMSO-d ₆ ) δ [ppm]: 7.99 (br: 1H), 7.82 (d: 2H), 7.24 (br: 1H), 6.71 (dd: 1H), 6.51 (d: 2H), 4.00 (br: 4H), 3.43- 3.41 (m: 4H), 3.36 (t: 4H), 3.19-3.16 (m: 4H), 2.59-2.57 (m: 4H), 1.82 (quin: 4H), 1.63-1.56 (m: 12H)

Synthesis Example 1-18 Synthesis of Compound 1-16 and Compound 1-16A Organic compounds and organic ionic compounds were synthesized by the following synthesis methods.
(First reaction)
A four-neck flask was charged with 2.2 parts by weight of 2-hydroxy-5-methoxybenzaldehyde, 3.0 parts by weight of 2-bromo-4'-fluoroacetophenone, 2.1 parts by weight of potassium carbonate, and 15.0 parts by weight of acetonitrile, and the resulting mixture was heated to 80°C and stirred at 80°C for 2 hours. The resulting mixture was then cooled to room temperature, and 50 parts by weight of water was added to cause crystallization. The precipitated crystals were then filtered and washed with water. The crystals were added to 30 parts by weight of methanol, stirred, filtered, and dried, yielding 3.1 parts by weight of a grayish-white solid compound (hereinafter referred to as Compound 1-16a) (yield: 83.4%).
(Second and third reactions)
Compound 1-16 having a structure represented by the following formula (1-16) and compound 1-16A having a structure represented by the following formula (1-16A) were synthesized in the same manner as in Synthesis Example 1-1, except that compound 1-16a was used instead of compound 1-1a. The yield of compound 1-16 was 33.5%. The structures of compound 1-16 and compound 1-16A obtained were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound 1-16
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.74 (br: 1H), 7.92 (d: 2H), 7.65 (d: 1H), 7.59 (s: 2H), 7.29 (d : 1H), 7.12 (dd: 1H), 7.02 (br: 1H), 6.71 (d: 2H), 3.98 (d: 2H), 3.82 (s: 3H)
・Compound 1-16A
(400MHz, DMSO-d ₆ ) δ [ppm]: 7.88 (d: 2H), 7.65 (d: 1H), 7.55 (d: 2H), 7.29 (d: 1H), 7.10 (dd: 1H), 6.65 (d: 2H), 6.38 (t: 1H), 3.82 (s: 3H) ), 3.53-3.51 (m: 2H), 3.45 (t: 2H), 3.36 (d: 2H), 3.25 (t: 2H), 2.72-2.70 (m: 2H), 1.89 (quin: 2H), 1.66-1.59 (m: 6H)

[Synthesis Example C-1] Synthesis of Compound C-1 and Compound C-1A Compound C-1A represented by the following formula (C-1A) was synthesized in the same manner as in Synthesis Example 1-1, except that Compound 1-1 was changed to N-phenylglycine (a compound represented by the following formula (C-1)). The structure of the obtained Compound C-1A was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound C-1A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.58 (br: 1H), 7.03 (dd: 2H), 6.48 (t: 3H), 5.11 (br: 1H), 3.53-3.50 (m: 2H), 3.4 4 (t: 2H), 3.25 (t: 2H), 3.24 (s: 2H), 2.76-2.73 (m: 2H), 1.88 (quin: 2H), 1.66-1.59 (m: 6H)

[Synthesis Example C-2] Synthesis of Compound C-2 and Compound C-2A Compound C-2A represented by the following formula (C-2A) was synthesized in the same manner as in Synthesis Example 1-1, except that Compound 1-1 was changed to ketoprofen (a compound represented by the following formula (C-2)). The structure of the obtained Compound C-2A was confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound C-2A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.65 (br: 1H), 7.73-7.66 (m: 4H), 7.56 (t: 3H), 7.49 (d: 1H), 7.41 (t: 1H), 3.51-3.48 (m: 2H) ), 3.44-3.36 (m: 3H), 3.18 (t: 2H), 2.68-2.66 (m: 2H), 1.85 (quin: 2H), 1.63-1.52 (m: 6H), 1.28 (d: 3H)

Synthesis Example C-3 Synthesis of Compound C-3 and Compound C-3A Organic compounds and organic ionic compounds were synthesized according to the following synthesis methods.
(First Reaction and Second Reaction)
To a four-neck flask, 2.0 parts by weight of thiosalicylic acid and 40.0 parts by weight of 98% sulfuric acid were added, followed by 7.7 parts by weight of phenoxyacetic acid, which was added in portions at room temperature. This solution was stirred for 1 hour while maintaining the temperature at room temperature, and then stirred at 80°C for an additional 2 hours. Next, this solution was cooled to room temperature and added to 200.0 parts by weight of ice water. Next, this solution was heated to 100°C, stirred for 5 minutes, and then cooled to room temperature. The precipitated crystals were filtered, washed with water, and dried to obtain compound C-3 having a structure represented by the following formula (C-3) in the form of yellow crystals (yield 51.2%).
(Third reaction)
Next, compound C-3A represented by the following formula (C-3A) was synthesized in the same manner as in Synthesis Example 1-1, except that compound 1-1 was changed to the above compound C-3. The structures of the obtained compounds C-3 and C-3A were confirmed by ¹ H-NMR spectroscopy (DMSO-d ₆ ). The results of the ¹ H-NMR spectroscopy are shown below.
・Compound C-3
(400MHz, DMSO-d ₆ ) δ [ppm]: 13.19 (br: 1H), 8.47 (d: 1H), 7.87-7.82 (m: 3H), 7.78 (t: 1H), 7.59 (t: 1H), 7.48 (dd: 1H), 4.87 (s: 2H)
・Compound C-3A
(400MHz, DMSO-d ₆ ) δ [ppm]: 11.12 (br: 1H), 8.46 (d: 1H), 7.83 (d: 1H), 7.79-7.73 (m: 3H), 7.57 (t: 1H), 7.35 (dd: 1H), 4.30 (s : 2H), 3.52-3.49 (m: 2H), 3.44 (t: 2H), 3.22 (t: 2H), 2.70-2.68 (m: 2H), 1.87 (quin: 2H), 1.63-1.56 (m: 6H)

[Synthesis Example C-4] Synthesis of Compound C-4 and Compound C-4A Compound C-4 represented by the following formula (C-4) and Compound C-4A represented by the following formula (C-4A) were synthesized in the same manner as in Synthesis Example 1-1, except that glycine was changed to β-alanine. The yield of the obtained Compound C-4 was 28.0%. The structures of the obtained Compound C-4 and Compound C-4A were confirmed by ¹ H-NMR spectrum (DMSO-d ₆ ). The results of the ¹ H-NMR spectrum are shown below.
・Compound C-4
(400MHz, DMSO-d ₆ ) δ [ppm]: 12.32 (br: 1H), 8.01 (d: 1H), 7.83 (d: 2H), 7.27 (d: 1H), 6.77 (t: 1H), 6.73 (dd: 1H), 6.67 (d: 2H), 3.37 (t: 2H), 2.54 (t: 2H)
・Compound C-4A
(400MHz, DMSO-d ₆ ) δ [ppm]: 8.00 (s: 1H), 7.81 (d: 2H), 7.25 (d: 1H), 6.8 (br: 1H), 6.72 (dd: 1H), 6.62 (d: 2H), 3.51-3.49 (m: 2H), 3.43 (t: 2H), 3.24 (t: 4H), 2.74-2.72 (m: 2H), 2.20 (t: 2H), 1.87 (quin: 2H), 1.65-1.58 (m: 6H)

Synthesis Example C-5 Synthesis of Compound C-5 and Compound C-5A Organic ionic compounds were synthesized by the following synthesis method.
A four-neck flask was charged with 1.0 part by weight of 2-bromoacetylnaphthalene, 0.86 parts by weight of dimethyldodecylamine, and 5.0 parts by weight of acetonitrile, and the mixture was stirred at room temperature for 6 hours and then concentrated under reduced pressure. Next, 10 parts by weight of methanol, 0.61 parts by weight of N-phenylglycine, and 0.8 parts by weight of sodium methoxide were added to the residue after vacuum concentration, and the mixture was stirred at room temperature for 1 hour. Next, 10.0 parts by weight of ethyl acetate and 10 parts by weight of water were added to this liquid, and the organic and aqueous layers were separated by liquid separation. The organic layer was washed with water, and the washed organic layer was concentrated under reduced pressure to obtain 2.0 parts by weight of a brown solid compound having a structure represented by the following formula (C-5) (hereinafter referred to as Compound C-5) (yield: 93.5%). The structure of the obtained Compound C-5 was confirmed by 1H-NMR spectroscopy (DMSO-d ₆ ). The results of the ^1H -NMR spectroscopy are shown below.
・Compound C-5
(400MHz, DMSO-d ₆ ) δ [ppm]: 8.76 (s: 1H), 8.16 (d: 1H), 8.12 (d: 1H), 8.06 (d: 1H), 8.01 (d: 1H), 7.75 (t: 1H), 7.69 (t: 1H), 7.02 (t: 2H), 6.47 -6.44 (m: 3H), 5.42 (s: 2H), 5.06 (br: 1H), 3.63-3.59 (m: 2H), 3.32 (s: 6H), 1.75 (br: 2H), 1.29-1.22 (m: 20H), 0.85 (t: 3H)

[Reference example compound R-1]
As a component used in the Reference Example, a compound R-1 having a structure represented by the following formula (R-1) was prepared. Specifically, 1-[({1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethylidene}amino)oxy]ethan-1-one manufactured by Tokyo Chemical Industry Co., Ltd. was used as the compound R-1.

The preparation and evaluation of the photosensitive composition will be described below.
[Example 1] Urethane-based Photosensitive Composition (1) Preparation of Urethane-based Photosensitive Composition 1.0 part by weight of hexamethylene diisocyanate (manufactured by Tokyo Chemical Industry Co., Ltd., indicated as "HDI" in the table) and 1.5 parts by weight of polyethylene glycol 600 (manufactured by Tokyo Chemical Industry Co., Ltd., indicated as "PEG" in the table) as reactive compounds, and 5.0 parts by weight of tetrahydrofuran were placed in a container and mixed at room temperature to prepare a resin solution. Subsequently, 0.02 parts by weight of the organic ionic compound of Synthesis Example 1-1 (Compound 1-1A) as a photobase generator was added to 1.0 part by weight of the resin solution at room temperature and mixed to prepare a photosensitive composition.

(2) Exposure and Development of Urethane-Based Photosensitive Composition The obtained photosensitive composition was applied to a glass plate (manufactured by Matsunami Glass Industry Co., Ltd.) whose weight had been measured in advance using a spin coater (manufactured by Aiden Co., Ltd., product name "SC2005"). After application, the glass plate was dried on a hot plate at 60°C for 5 minutes to form a coating film (photosensitive layer). Two samples each with a coating film formed on the glass plate were prepared and their weights were measured.
The sample on which one coating film had been formed was exposed to light from a high-pressure mercury lamp (manufactured by Ushio Lighting Inc., product name "ML-251A/B") at 365 nm through a bandpass filter (manufactured by Ushio Lighting Inc.) under conditions of 735 mJ/ ^cm2 (illuminance 21 mW/ ^cm2 × 35 seconds) (this exposure condition is referred to as "Condition 1"; the same applies hereinafter except for Example 11). This gave a sample with an exposed coating film.
Next, a sample having a coating film after exposure (exposed sample) and a sample having a coating film that was not exposed (unexposed sample) were placed on a hot plate and heated at 120°C for 1 hour. The weights of the exposed sample and the unexposed sample after heating were measured, and the weight calculated by subtracting the weight of the glass plate before coating was taken as the "cured film weight (film weight)." The exposed sample was taken as the "exposed cured film weight," and the unexposed sample was taken as the "unexposed film weight."
Subsequently, the heated sample was cooled to room temperature, immersed in tetrahydrofuran at 26 to 28°C for 90 seconds, and then dried at 80°C. The weight of the sample after immersion was measured, and the weight calculated by subtracting the weight of the glass plate before coating was used as the "residual film weight." For the exposed sample, this is the "exposed residual film weight," and for the unexposed sample, this is the "unexposed residual film weight."
Next, instead of the photobase generator (organic ionic compound), the "theoretical amount of base generated" corresponding to the evaluated photobase generator was calculated, and the corresponding base was used to prepare a composition in the same manner as above. Note that the corresponding base is the base that constitutes the counter cation (cation moiety) of the organic ionic compound in each synthesis example. The theoretical amount generated is the theoretical amount of base that can be generated when a photobase generator is used for a reactive compound in the composition. This is the theoretical amount estimated as the base that can be generated by light irradiation, and is calculated by creating a calibration curve of the corresponding base.
Next, a theoretical amount of the corresponding base estimated as a base that can be generated by light irradiation was mixed with 1.0 part by weight of the resin solution to prepare a composition containing the corresponding base. As described above, a coating film of the composition was formed on a glass plate to prepare a sample. After heating the sample, the weight was measured, and the weight obtained by subtracting the weight of the glass plate before coating was defined as the "theoretical cured film weight." Furthermore, the weight obtained by subtracting the weight of the glass plate before coating from the weight of the sample after immersion was defined as the "theoretical remaining film weight."

(3) Evaluation Using the measured values obtained above, the curability and contrast were calculated according to the following formulas.
Exposure curability a1 (%) = weight of exposed remaining film ÷ weight of exposed cured film × 100
Unexposed curability a2 (%) = unexposed remaining film weight ÷ unexposed film weight x 100
Theoretical base curability a3 (%) = theoretical remaining film weight ÷ theoretical cured film weight × 100
Curability (%) = a1÷a3×100
Contrast (%) = (a1 - a2) ÷ a1 × 100
Based on the results of the curability and contrast calculated above, each was evaluated according to the following criteria. The results are shown in Tables 2 and 3.
A: (Good): The value is 70% or more.
B: (Acceptable): The value is 40% or more and less than 70%.
C: (Unacceptable): The value is less than 40%.

[Examples 2 to 10, 12 and Comparative Examples 1 to 4]
Photosensitive compositions were prepared in the same manner as in Example 1, except that the organic ionic compounds incorporated into the photosensitive compositions were changed to the photobase generators (organic ionic compounds) shown in Tables 2 and 3. Subsequently, the photosensitive compositions were subjected to the evaluations (2) and (3) above in the same manner as in Example 1. The results are shown in Tables 2 and 3.

[Example 11]
The evaluation was carried out in the same manner as in Example 1, except that the exposure conditions (referred to as Condition 2) were changed as follows.
Condition 2: Light from a high-pressure mercury lamp (manufactured by Ushio Lighting Inc., product name "ML-251A/B") was used for exposure without passing through a bandpass filter, with an integrated light quantity of 750 mJ/cm ² (illuminance 25 mW/cm ² × 30 seconds).

Example 13: Epoxy-based Photosensitive Composition (1) Preparation of Epoxy-based Photosensitive Composition 6.0 parts by weight of an epoxy resin (manufactured by Mitsubishi Chemical Corporation, designated "jER828" in the table) as a reactive compound, 2.0 parts by weight of a PMA-PMMA copolymer (manufactured by Sigma-Aldrich, designated "PMA-PMMA" in the table), and 36.0 parts by weight of tetrahydrofuran were placed in a container and mixed at 40°C. The mixture was then cooled to room temperature to prepare a resin solution. Subsequently, 0.01 part by weight of the organic ionic compound (compound 1-1A) from Synthesis Example 1-1 and 0.08 parts by weight of pentaerythritol tetra(3-mercaptopropionate) (manufactured by Tokyo Chemical Industry Co., Ltd., designated "PEMP" in the table) were added as photobase generators to 1.0 part by weight of the resin solution at room temperature and mixed to prepare an epoxy-based photosensitive composition.

(2) Exposure and Development of Epoxy-Based Photosensitive Composition In the same manner as in (2) of [Example 1] above, the obtained epoxy-based photosensitive composition was applied to a glass plate (manufactured by Matsunami Glass Industrial Co., Ltd.) whose weight had been measured in advance using a spin coater (manufactured by Aiden Co., Ltd., product name "SC2005"), followed by drying to form a coating film (photosensitive layer). Two samples each having a coating film formed on a glass plate were prepared, and their weights were measured.
Next, in the same manner as in (2) of [Example 1] above, the sample on which one coating film was formed was exposed to light using a high-pressure mercury lamp (manufactured by Ushio Lighting Inc., product name "ML-251A/B") under the above-mentioned condition 1. In this way, a sample having an exposed coating film was obtained.
Next, a sample having a coating film after exposure (exposed sample) and a sample having a coating film that was not exposed (unexposed sample) were placed on a hot plate and heated at 40°C for 1 hour. The weights of the exposed sample and the unexposed sample after heating were measured, and the weight calculated by subtracting the weight of the glass plate before coating was taken as the "cured film weight (film weight)." The exposed sample was taken as the "exposed cured film weight," and the unexposed sample was taken as the "unexposed film weight."
Subsequently, the heated sample was cooled to room temperature, immersed in tetrahydrofuran at 26 to 28°C for 30 seconds, and then dried at 80°C. The weight of the sample after immersion was measured, and the weight calculated by subtracting the weight of the glass plate before coating was used as the "residual film weight." For the exposed sample, this is the "exposed residual film weight," and for the unexposed sample, this is the "unexposed residual film weight."

(3) Evaluation Using the measured values obtained above, the curability and contrast were calculated according to the following formulas.
Exposure curability a1 (%) = weight of exposed remaining film ÷ weight of exposed cured film × 100
Unexposed curability a2 (%) = unexposed remaining film weight ÷ unexposed film weight x 100
Curability (%) = a1
Contrast (%) = (a1 - a2) ÷ a1 × 100
Based on the results of the curability and contrast calculated above, each was evaluated according to the following criteria. The results are shown in Tables 4 and 5.
A: (Good): The value is 70% or more.
B: (Acceptable): The value is 40% or more and less than 70%.
C: (Unacceptable): The value is less than 40%.
[Examples 14 to 23 and Comparative Example 5]
Photosensitive compositions were prepared in the same manner as in Example 13, except that the organic ionic compounds incorporated into the epoxy-based photosensitive compositions were changed to the photobase generators (organic ionic compounds) shown in Tables 4 and 5. Subsequently, the epoxy-based photosensitive compositions were subjected to the evaluations (2) and (3) above in the same manner as in Example 13. The results are shown in Tables 4 and 5.

Example 24: Radical Polymerization Photosensitive Composition (1) Preparation of Radical Polymerization Photosensitive Composition 3.0 parts by weight of dipentaerythritol hexaacrylate (manufactured by Tokyo Chemical Industry Co., Ltd., designated "DPHA" in the table) as a reactive compound, 0.38 parts by weight of PMA-PMMA copolymer (manufactured by Sigma-Aldrich, designated "PMA-PMMA" in the table), and 18.0 parts by weight of tetrahydrofuran were mixed at 40°C and cooled to room temperature to prepare a resin solution. Subsequently, 0.01 parts by weight of the organic compound of Synthesis Example 1-1 (Compound 1-1) was added as a radical polymerization initiator to 1.0 part by weight of the resin solution at room temperature and mixed to prepare a radical polymerization photosensitive composition.

(2) Exposure and Development of Radical Polymerization Photosensitive Composition In the same manner as in (2) of [Example 1] above, the obtained radical polymerization photosensitive composition was applied to a glass plate (manufactured by Matsunami Glass Industrial Co., Ltd.) whose weight had been measured in advance using a spin coater (manufactured by Aiden Co., Ltd., product name "SC2005"), followed by drying to form a coating film (photosensitive layer). Two samples each with a coating film formed on each glass plate were prepared, and their weights were measured.
Next, in the same manner as in (2) of [Example 1] above, the sample on which one coating film was formed was exposed to light using a high-pressure mercury lamp (manufactured by Ushio Lighting Inc., product name "ML-251A/B") under the conditions described above in Condition 1. This gave a sample having an exposed coating film.
Next, the weights of a sample having a coating film after exposure (exposed sample) and a sample having a coating film that was not exposed (unexposed sample) were measured, and the weight calculated by subtracting the weight of the glass plate before coating was designated as the "cured film weight (film weight)." The exposed sample is designated as the "exposed cured film weight," and the unexposed sample is designated as the "unexposed film weight."
Next, a sample having a coating film after exposure (exposed sample) and a sample having a coating film that has not been exposed (unexposed sample) were immersed in tetrahydrofuran at 26 to 28°C for 30 seconds, then dried at 80°C, and the weight of the sample after immersion was measured, and the weight calculated by subtracting the weight of the glass plate before coating was used as the "residual film weight." For the exposed sample, this is the "exposed remaining film weight," and for the unexposed sample, this is the "unexposed remaining film weight."

(3) Evaluation In the same manner as in (3) of Example 13 above, the curability and contrast were calculated using the measured values obtained in (2) above. Based on the calculated results of curability and contrast, evaluation was performed using the same criteria as in (3) of Example 13 above. The results are shown in Tables 6 and 7.

[Examples 25 to 33, Comparative Examples 6 to 9, and Reference Example 1]
Radical polymerization photosensitive compositions were prepared in the same manner as in Example 24, except that the organic compounds incorporated into the radical polymerization photosensitive compositions were changed to the radical polymerization initiators (organic compounds) listed in Tables 6 and 7. Subsequently, the radical polymerization photosensitive compositions were subjected to the evaluations (2) and (3) above in the same manner as in Example 24. The results are shown in Tables 6 to 7.

As shown in Examples 1 to 12, organic ionic compounds 1-1A to 1-7A, 1-11A, 1-1B, 1-1C, and 1-14A were shown to produce particularly good results in terms of the curability and contrast of the photosensitive composition. As a result, it was shown that organic ionic compounds 1-1A to 1-7A, 1-11A, 1-1B, 1-1C, and 1-14A can be particularly suitably used as photobase generators.

On the other hand, as shown in Tables 1 and 2-3, the photobase generators (organic ionic compounds) of Comparative Examples 1-4 do not have the structure represented by formula (1-A), do not have a maximum absorption wavelength near 365 nm, and do not have excellent light absorption characteristics. Furthermore, they also have poor curability and contrast in photosensitive compositions.

As such, it was found that the organic ionic compounds of Examples 1 to 12 are significantly superior as photobase generators compared to compounds C-1A to C-4A, which do not have the structure represented by formula (1-A) and are used in Comparative Examples 1 to 4, including conventional organic compounds.

Furthermore, as shown in Examples 13 to 23, even when an epoxy compound is used instead of a urethane compound as the reactive compound in the photosensitive composition, it was shown that particularly good results were obtained in terms of the curability and contrast of the photosensitive composition containing an organic ionic compound.

As shown in Examples 24 to 33, when the above organic compounds were used in combination with vinyl compounds ((meth)acrylic compounds) as reactive compounds, the organic compounds used in Examples 24 to 26 and 32 to 33 in particular exhibited curability and contrast comparable to or superior to that of Reference Example 1 (Compound R-1), which can generally be used as a radical polymerization initiator with good curability. As shown in Comparative Examples 6 to 9, the organic compounds used in Examples 27 to 31 (Compounds 1-4, 1-7, 1-8, 1-11, and 1-12) exhibited superior curability and contrast compared to compounds (C-1, C-2, C-4, and C-5) that do not have the structure represented by formula (1), demonstrating acceptable curability and contrast. Therefore, it is demonstrated that the organic compounds according to embodiments of the present invention can be suitably used as radical polymerization initiators.

An organic compound according to one embodiment of the present invention can successfully form an organic ionic compound. An organic compound according to another embodiment of the present invention is suitable for use as a polymerization initiator. An organic ionic compound according to yet another embodiment of the present invention is suitable for use as a photobase generator. A polymerization initiator according to another aspect of the present invention can be suitable for use in producing a photosensitive composition and a cured product using the photosensitive composition. A photobase generator according to yet another aspect of the present invention can be suitable for use in producing a photosensitive composition and a cured product using the photosensitive composition.

Claims (10)

An organic compound having a structure represented by the following formula (1):
In formula (1), R ¹ represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group;
^R2 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group;
X is one selected from the group consisting of the following structural formulas:
2. The organic compound of claim 1, wherein X is one selected from the group consisting of the following structural formulas:
An organic ionic compound having a structure represented by the following formula (1-A):
In formula (1-A), R ¹ represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a substituted or unsubstituted phenyl group;
^R2 represents at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzoyl group, and a carboxymethyl group;
X is a heterocyclic group containing at least one oxygen atom, nitrogen atom, or sulfur atom in the ring;
A ⁺ represents a cation of an organic base;
The organic base is at least one compound selected from the group consisting of primary amines, secondary amines, tertiary amines, compounds having an amidine skeleton, and compounds having a guanidine skeleton. The organic ionic compound according to claim 3 , wherein the organic base is either a compound having an amidine skeleton or a compound having a guanidine skeleton. 4. The organic ionic compound of claim 3 , wherein A ⁺ is at least one cation selected from the group consisting of the following structural formulas:
4. The organic ionic compound of claim 3 , wherein X is one selected from the group consisting of the following structural formulas:
3. A composition comprising at least one organic compound according to claim 1 or 2 .
Polymerization initiator. The composition contains at least one organic ionic compound according to any one of claims 3 to 6 .
Photobase generator. A vinyl compound,
The polymerization initiator according to claim 7 ,
Photosensitive composition. at least one reactive compound selected from the group consisting of an isocyanate compound, an epoxy compound, a silane compound, and a polyamic acid;
The photobase generator according to claim 8 ,
Photosensitive composition.