JPH04108864A - Trimethin compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [R1 to R4 are H, alkyl or aryl; R5 to R9 are H or monovalent group; (m) and (n) are 1-4; R10 is XR11, PO(OR12)2, CR13R14R15 or NR16R17 (R11 to R17 are H or monovalent group, provided that at least one of R13 to R15 is electron attractive group)]. EXAMPLE:A compound expressed by formula II. USE:An electron-donating colorless dye of recording material, medicine, agricultural chemical and dye and intermediate therefor. PREPARATION:A compound expressed by formula III or formula IV which is used as a raw material is made to react with the formula HXR11, HPO(OR12)2, HCR13R14R15 or HNR16R17 or salt thereof.

Description

Detailed Description of the Invention (Field of the Invention) The present invention is applicable to colorless electron-donating dyes for recording materials that utilize color development through contact between an electron-donating colorless dye and an electron-accepting compound, or for use in pharmaceuticals, agricultural chemicals, dyes, etc. and trimethine compounds useful as intermediates therefor.

(Prior Art) Recording materials using electron-donating colorless dyes and electron-accepting compounds are already well known as pressure-sensitive paper, thermal paper, light-sensitive pressure-sensitive paper, electrically conductive thermal recording paper, thermal transfer paper, and the like. For example, British Patent No. 2140449, U.S. Patent No. 4480052, U.S. Pat.
For details, see No. 60-123557.

As a recording material, in recent years (1) color density and color sensitivity (2)
) Research is being carried out to improve properties such as before use and the fastness of colored images.

For example, the blue coloring agent 3,3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide (i.e., crystal violet lactone) develops quickly and exhibits a deep blue color, but the light fastness of the colored image Plasticizer properties are extremely poor.

Therefore, in fruit and vegetable color recording materials, the color density is high;
There is a strong desire for a color forming agent that also provides good fastness of colored images.

(Objective of the Invention) The object of the present invention is to use it as an electron-donating colorless dye for recording materials, which has high color density, good fastness of colored images, and satisfies other requirements, or for pharmaceuticals and agricultural chemicals. An object of the present invention is to provide trimethine compounds useful as dyes and intermediates thereof.

(Structure of the Invention) The object of the present invention was achieved by developing a trimethine compound represented by the following general formula (1).

In the above formula, R1 to R4 are hydrogen atoms, alkyl groups, and aryl groups, R3 to R are hydrogen atoms or -valent groups, and m and n are 1
, R20 is -XR22' -PO(OR
22) 20CR20R20R20, -N R20R,.

(X represents a sulfur atom, and R1, to R20 represent a hydrogen atom or a -valent group. However, at least one of R20, R+i, and R8 represents an electron-withdrawing group.)

More preferably, R, -R, is a hydrogen atom, an alkyl group,
Alkoxy group, alkylthio group, alkoxycarbonyl group, aryl group, aryloxy group, arylthio group,
Aryloxycarbonyl group, cyano group, R22R,
is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group,
Aryloxy group, cyano group, nitro group, substituted amino group, hydroxy group, halogen atom, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group,
m and n are integers from 1 to 4, R20 is -XR22-P○
(OR22) 20 -CR20R20R20, -N Ft 20R.

In the above formula, X is a sulfur atom, R20 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, COR22, SO, R22
, N = CR20R20, N R20R20 [
R22 and R22 are hydrogen atoms, alkyl groups, aryl groups,
A heterocyclic group, R20, R23, RI 1% RI 1 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, c.

R14, So, R22 (R22 and R22 represent a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group)].

R20 represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. Furthermore, R and l may be linked to each other to form a 4- to 12-membered ring structure that may contain a hetero atom.

R1, R14, R, l represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a halogen atom, a cyano group, a nitro group, So, R22, COR22, NR20R, l [R71 and R23 are hydrogen atoms, alkyl groups, aryl groups, heterocyclic groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, hydroxy groups, N R20
R20, R+Is R! l, R8, R11 are hydrogen atoms, alkyl groups, aryl groups, heterocyclic groups, SOIR23,
COR22 (R22, R11 are hydrogen atoms, alkyl groups 2
．． represents an aryl group or a heterocyclic group]. Furthermore, R1,
R20 may be linked to each other to form a 4- to 12-membered ring structure that may contain a heteroatom.

R20 and R1 are hydrogen atoms, alkyl groups, aryl groups,
Heterocyclic group, So, R22, COR20, hydroxy group,
N R20R20 [R□, R3, is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a heterocyclic group, N R20R20, R20, R17,
R1,s R11 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, So, R22, COR22 (R22, R2
0 represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group]. Furthermore, R and R17 may be linked to each other to form a 4- to 12-membered ring structure that may contain a hetero atom.

In addition, an alkyl group, an aryl group, and a heterocyclic group further include an alkyl group, an alkoxy group, an aryl group, an aryloxy group,
It may have a substituent such as a halogen atom, nitro group, cyano group, substituted carbamoyl group, substituted sulfamoyl group, substituted amine group, substituted oxycarbonyl group, substituted oxysulfonyl group, alkylthio group, or arylsulfonyl group.

More specifically, among the substituents represented by R1-R1, hydrogen atoms, alkyl groups having 1 to 18 carbon atoms, 6 to 1
The aryl group of 2 is preferred.

R1-R4 are hydrogen atoms, methyl groups, ethyl groups, n
-propyl group, 1so-propyl group, n-butyl group, 1
so-butyl group, n-amyl group, is.

-Amyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-dodecyl group, n
-Octadecyl group, β-methoxyethyl group, β-ethoxyethyl group, γ-methoxypropyl group, γ-ethoxypropyl group, β-phenoxyethyl group, β-cyanoethyl group, β-chloroethyl group, β-hydroxyethyl group , cyclopentyl group, cyclohexyl group, tetrahydrofurfuryl group, phenyl group, tolyl group, chlorophenyl group,
Examples include methoxyphenyl group, benzyl group, phenethyl group, methylbenzyl group, chlorobenzyl group, and methoxybenzyl group.

Preferably, R1-R4 are not hydrogen atoms at the same time.

R7, R22R, and R4 are bonded to each other to form a ring which may contain a 5- to 8-membered heteroatom including the nitrogen atom to which they are bonded, such as pyrrolidine, piperidine, morpholine, thiomorpholine, A piperazine or caprolactam ring may be formed, and a benzene ring may also be included to form an indoline, hydroquinoline, or julolidine ring.

Among the substituents represented by R1-R7, hydrogen atoms, alkyl groups having 1 to 18 carbon atoms, alkoxy groups, alkylthio groups, alkoxycarbonyl groups, and 6 to 1 carbon atoms;
2, 7-aryl group, aryloxy group, arylthio group,
An aryloxycarbonyl group or a cyano group is preferred.

More specifically about R, -R, hydrogen atom, methyl group,
Ethyl group, propyl group, butyl group, amyl group, hexyl group, octyl group, octadecyl group, methoxypropyl group, ethoxypropyl group, phenoxyethyl group, cyclopentyl group, cyclohexyl group, aryl group, benzyl group, phenethyl group, phenyl group , 4-methylphenyl group,
3-methylphenyl group, 2-methylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-N,N-dimethylaminophenyl group, 3-N,N-dimethylaminophenyl group group, 2-N,
Examples include N-dimethylaminophenyl group, cyano group, methoxycarbonyl group, ethoxycarbonyl group, and methylthio group.

Furthermore, R, -R, may be linked to each other and to adjacent aryl groups or heterocyclic groups to form an alicyclic 4- to 12-membered ring structure that may contain a hetero atom, particularly 5 It is preferable to form a ~8-membered ring structure. Furthermore, this ring may have a substituent such as an alkyl group, an alkoxy group, or an aryl group.

In particular, it is preferable that R1 and R2 are each a hydrogen atom from the viewpoint of synthetic handling.

Among the substituents represented by R22R, hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, alkoxy groups, alkoxycarbonyl groups having 2 to 12 carbon atoms, acyloxy groups, aryl groups having 6 to 12 carbon atoms, Aryloxy group, aryloxycarbonyl group having 7 to 12 carbon atoms, hydroxy group, chlorine atom, bromine atom, fluorine atom,
Nitro group, cyano group, amino group, carbon number 1 to 12
mono- or dialkylamino group having 6 to 12 carbon atoms
mono- or diarylamino group with 1 to 12 carbon atoms
An acylamino group is preferred.

R22R, specifically hydrogen atom, methyl group, ethyl group, propyl group, butyl group, octyl group, phenyl group, tolyl group, benzyl group, phenethyl group, methoxy group, nidoxy group, propoxy group, butoxy group, octyloxy group , benzyloxy group, phenoxyethoxy group, phenoxy group, chlorine atom, bromine atom, fluorine atom, nitro group, cyano group, dimethylamino group, diethylamino group, acetylamino group, acetyloxy group, and methoxycarbonyl group.

R22R, is -NR, R22-NR, from the point of coloring wavelength.
R, meta position 0<preferable.

Among the substituents represented by R20, those having 20 or less carbon atoms are preferred.

Furthermore, R+s is -XR22 in terms of synthetic handling.
, -CR20R20R+i, -NR20R are preferred.

In particular, -CR20R20R20 is preferred from the viewpoint of stability of the leuco color former when used in recording materials.

R20 includes diethylphosphonyl group, dibutylphosphonyl group, diphenylphosphonyl group, di(4-tolyl)
Phosphonyl group, di(4-chlorophenyl)phosphonyl group, di(4-methoxyphenyl)phosphonyl group, di(4-
nitrophenyl)phosphonyl group, di(4-cyanophenyl)phosphonyl group, di(naphthalen-1-yl)phosphonyl group, di(naphthalen-2-yl)phosphonyl group, di(2゜4-dichlorophenyl)phosphonyl group, (4-
Chloro-3-methylphenyl)phosphonyl group, anilino group, 2-chloroanilino group, 2-methoxycarbonylanilino group, 2-nitroanilino group, 2-methoxyanilino group, 3-ethylanilino group, 4-fluoroanilino group , 4-butoxyanilino group, 214-dichloroanilino group, 2,5-dimethylanilino group, β-naphthylamino group, N-methylanilino group, N-butylanilino group, N
-7 cetylanilino group, pyridylamino group, quinolylamino group, cyclohexylamino group, indol-1-yl group, carbazol-1-yl group, succinylimide group,
Phthalimide group, acetylamino group, benzoylamino group, 2-methylbenzoylamino group, 4-methylbenzoylamino group, 4-chloropenzoylamino group, phenylsulfonylamino group, 4-methylphenylsulfonylamino group, 4-chlorophenylsulfonylamino group group, pyrrolidino group, piperidino group, morpholino group, piperazino group, phenylhydrazino group, N-hydroxy-N-phenylsulfonylamino group, N-hydroxy-N-4-chlorophenylsulfonylamino group, benzoylhydrazino group, phenylsulfonyl 1 .1-diacetylmethyl group, 1.1-dicyanomethyl group, 1-acetyl-1-benzoylmethyl group, 1.1
-dimethoxycarbonylmethyl group, 120-jethoxycarbonylmethyl group, 120-diphenyloxycarbonylmethyl group, 1.1-di-n-butoxycarbonylmethyl group, 1.1-di-t-butoxycarbonylmethyl group, 1. 1-dibenzyloxycarbonylmethyl group, 12
0-dioctyloxycarbonylmethyl group, 1-7cetyl-1-methoxycarbonylmethyl group, 1-acetyl-
1-ethoxycarbonylmethyl group, 1-7 cetyl-1-
iso-propoxycarbonylmethyl group, 1-acetyl-1-butoxycarbonylmethyl group, 1-7 cetyl 1
-hexyloxycarbonylmethyl group, 1-7 cetyl-1-octyloxycarbonylmethyl group, 1-7 cetyl-1-benzyloxycarbonylmethyl group, 1-acetyl-1-phenoxycarbonylmethyl group, 1-propionyl-1-methoxy Carbonylmethyl group, 1-acetyl-1-ethoxycarbonylethyl group, 1.1-diacetylmethyl group, 1-pivaloyl-1-methoxycarbonylmethyl group, 1-cyano-1-ethoxycarbonylmethyl group, 1-benzoyl-1 -ethoxycarbonylmethyl group, 1-acetyl-1-morpholinocarbonylmethyl group,
1-methoxycarbonyl-1-ethoxycarbonylmethyl group, 1.1-diphenylsulfonylmethyl group, 1-tolylsulfonyl-1-benzoylmethyl group, 1.1-di(trifluoromethylcarbonyl)methyl group, 120-
dipivaloylmethyl group, 1-furoyl-1-trifluoromethylcarbonylmethyl group, 1-thienylcarbonyl-1-trifluoromethylcarbonylmethyl group, 1.1
-Dicarbamoylmethyl group, 1-acetyl-1-phenylcarbamoylmethyl group, 1゜1-dibenzoylmethyl group, 1.1-dimethoxycarbonylethyl group, 1.1-
Jetoxycarbonylethyl group, 1.1-diphenyloxycarbonylethyl group, 1.1-di-n-butoxycarbonylethyl group, 1.1-di-t-butoxycarbonylethyl group, 1.1-dibenzyloxycarbonyl group Ethyl group, 1.1-dimethoxycarbonyl-n-propyl group, 120-dimethoxycarbonyl-n-butyl group, α,
α-dimethoxycarbonylbenzyl group, 1.1-dimethoxycarbonyl-1-methoxymethyl group, 1.1-jethoxycarbonyl-n-propyl group, 1.1-jethoxycarbonyl-1so-propyl group, 120-jethoxy Carbonyl-n-butyl group, 120-jethoxycarbonyl-1so-butyl group, 1.1-jethoxycarbonyl-tart-butyl group, α,α-jethoxycarbonylbenzyl group, β,β-jethoxycarbonylphenethyl group , 1.1-jethoxycarbonyl-1-arylmethyl group, 120-jethoxycarbonyl-1-acetaminomethyl group, 1゜1-jethoxycarbonyl-1-
Chloromethyl group, 1,1-jethoxycarbonyl-1-
Cyclopentylmethyl group, 120-jethoxycarbonyl-1-phthalimidomethyl group, 1.1-jethoxycarbonyl-2-ethoxycarbonylethyl group, 1.12
0. -1-jethoxycarbonylmethyl group, benzoylmethyl group, 4-chlorobenzoylmethyl group, 4-nitrobenzoylmethyl group, 1-chloro-1-acetylmethyl group, 1-chloro-1-methoxycarbonylmethyl group, 1
-bromo-1-benzoylmethyl group, nitromethyl group,
Examples include 1-nitroethyl group.

Next, specific examples of the trimethine compound of the present invention are shown, The present invention is not limited to these.

CH300σゝCOCH3 CH3HNOC CONHCH3 Shi3I+L7-ISO Shi4"9-" The trimethine compound according to the present invention has the following general formula (11
), (Il+) as raw materials, HXR22, HPO (OR22)20)
(Obtained by reacting with CR20R20R20, HN R20R20 or a salt thereof.

In the above formula, R, ~R,,R,, ~R, 22m, n have the above-mentioned meanings, and Y- represents an anion of an inorganic or organic acid necessary to form a dye, such as a chloride ion, Bromine ion,
), ion, sulfate ion, phosphate ion, perchlorate ion, acetate ion, benzenesulfonate ion, p-toluenesulfonate ion, methylsulfate ion, and the like.

The aforementioned HXR22HPO (OR22), , HCR+I
The salts of RIJR11, HN R20R20 are, for example, alkali metal salts, alkaline earth metal salts, ammonium salts or amine salts.

HXR22, HP○ (OR22), , HCR used
The amount of 22R22R22, HN R20R20 or a salt thereof is preferably 1 to 3 mol, particularly preferably 1 to 1.5 mol, per 1 mol of the compound of general formula (11) or (Ill'I).

The above reaction is preferably carried out in an organic solvent, such as alcohols, ethers, esters, aromatic hydrocarbons, halogenated hydrocarbons, and the like. Specific examples include methanol, ethanol, impropatol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, tetrahydrofuran, dioxane, ethyl acetate, toluene, xylene, methylene chloride, and the like. Among these, polar organic solvents are particularly preferred.

The amount of organic solvent used is preferably such that the solid content concentration is 10% or more, particularly 20%.

As a catalyst, an acidic catalyst such as an aliphatic carboxylic acid such as formic acid or acetic acid or an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid or perchloric acid may be added.

The reaction temperature is preferably 10 to 100°C, particularly 20 to 7°C.
0°C is preferred.

It is also preferable to carry out the reaction under an atmosphere of an inert gas such as nitrogen or argon gas from the viewpoint of preventing coloration of the liquid.

The compound of general formula (11) is Annalen der C
It is synthesized with reference to the method described in Hemie 623.204-216 (1959).

A preferred method for producing the compound of general formula (11) is a method in which a compound represented by the following general formula (IV) is reacted with a compound represented by the following general formulas (V) and (■1) in an acidic medium. be.

In the above formula, ~R+, m, and n have the above-mentioned meanings, and 2 represents a hydrogen atom or a carboxyl group.

Further, after reducing the reaction product represented by the following general formula (IX) obtained by reacting the compound represented by the general formula (■1) with the compound represented by the following general formula (■1), It can also be obtained by a method of adding an acid represented by HY (Y means the above).

In the above formula, R1 to R+, m, and n represent the above-mentioned meanings (however, in this case, R1 to R, =H).

In the method for producing general formula (IX), it is preferable to use water and/or an organic solvent as the reaction solvent, such as alcohols, ethers, esters,
Examples include aromatic hydrocarbons and halogenated hydrocarbons. In particular, methanol, ethanol,
Alcohols such as isopropanol or mixed solvents of water and alcohols are preferred. In this case, it is preferable to use an acidic or basic condensing agent. Acidic condensing agents include aliphatic carboxylic acids; basic condensing agents include amines such as pyridine, triethylamine, and triethanolamine;
Examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and sodium methoxide.

The above-mentioned reduction reaction is carried out by a known method, and in particular, ethers such as diethyl ether, tetrahydrofuran, and dioxane are used as a solvent, and metal hydrogen such as lithium aluminum hydride, sodium boron hydride, etc. are used as a reducing agent at a temperature of 0 to 100°C. It is preferable to use a chemical compound.

When purifying the compound of general formula (11), known methods,
For example, the reaction mixture is poured into water to precipitate crystals, and water and/or
Alternatively, a method of washing with an organic solvent and then drying is performed.

The compound of general formula (Il +
It can also be obtained by reducing the compound represented by

(Examples of the Invention) Examples are shown below, but the present invention is not limited thereto.

(Example 1) The compound of Example (1) was placed in a three-necked flask equipped with a stirrer, and 0.15 mof of 4-NN-dimethylaminobenzaldehyde, 4-N,
N-dimethylaminoacetophenone 0.15mol
, 28% sodium methoxide methanol solution 0.0
Measure out 5 mol of ethanol and stir for 10 hours while refluxing.

After cooling, the precipitated crystals were filtered, washed with methanol, and 1-
(4-N,N-dimethylaminobenzoyl)2- (4
-N,N-dimethylaminophenyl)ethylene 0.13
Obtained mol. Next, weigh out 0205 mol of lithium aluminum hydride and 500 mol of tetrahydrofuran, and while stirring at room temperature, add 0.1 mol of the above ketone.
1 is gradually added and further stirred at room temperature for 0.5 hour.

After cooling the reaction mixture and dropping 120 ml of water, a mixture of 0.1 ml of 70% perchloric acid and 200 ml of acetic acid was gradually added, followed by 1 j2 of water, and the precipitated crystals were filtered and washed with water to form the following compound ( X) was obtained.

Next, in another three-necked flask equipped with a stirrer, add 0.011 mol of sodium hydride and 40 methylene chloride.
Add 0.0% acetylacetone while stirring.
0105 mol was added dropwise. After stirring at room temperature for 5 minutes, 0.01 mol of compound (X) is gradually added, and the mixture is further stirred at 50°C for 1 hour. The reaction mixture was poured into water, filtered, and dried to obtain the desired product as pale yellow-white crystals (melting point 1
02-4°C).

(Example 2) Compound of Example (5) Weighed 0.011 mol of sodium hydride and 40% of tetrahydrofuran into a three-necked flask equipped with a stirrer, and added 0.0105% of diphenyl phosphite while stirring.
Add mol. After stirring at room temperature for 5 minutes, compound (X) 0. Gradually add 01 mol and then add 1 mol.
Stir the time. The reaction mixture was poured into water, filtered and dried to obtain the desired product as pale yellowish white crystals (melting point 135-7°C).

(Example 3) The reaction was carried out in the same manner as in Example 2, except that methyl anthranilate was used instead of diphenyl phosphite in Compound Example 2 of Specific Example (14),
The desired product was obtained as pale yellowish white crystals (melting point 20-4°C).

(Example 4) A reaction was carried out in the same manner as in Example 2, except that dimethyl malonate was used instead of diphenyl phosphite in Compound Example 2 of Example (20), and ethyl acetate di-n-hexane was used. By recrystallizing with a mixed solvent of -1=2, the desired product was obtained as white crystals (melting point 116-8°C).

(Example 5) The reaction was carried out in the same manner as in Example 2, except that methoxycarbonylacetone was used instead of diphenyl phosphite in Compound Example 2 of Example (22), and the target product was a pale yellowish white crystal ( (melting point 73-5°C).

(Example 6) The reaction was carried out in the same manner as in Example 2, except that benzyloxycarbonylacetone was used instead of diphenyl phosphite in Compound Example 2 of Example (24), and the target product was a pale yellowish white crystal. (Melting point 94-6℃)
obtained as.

(Example 7) The reaction was carried out in the same manner as in Example 2, except that phenylaminocarbonylacetone was used in place of the diphenyl phosphite in Compound Example 2 of Example (28), and the target product was pale yellowish white. Crystal (melting point 180-2℃
) was obtained.

(Example 8) The reaction was carried out in the same manner as in Example 2 except that dibenzyl malonate was used instead of diphenyl phosphite in Compound Example 2 of Compound Example (32). (melting point 102-4°C).

(Example 9) The reaction was carried out in the same manner as in Example 2 except that dimethyl methylmalonate was used in place of the diphenyl phosphite in Compound Example 2 of Example (46), and the target product was pale yellowish white crystals. (melting point: 110-2°C).

(Example 10) The following compound (
×1) 0°Olmol, diethyl malonate 0. Olmol,
Weigh out Ethyl Celsolve 30#β and heat it to 100°C.
Stir the time. The reaction mixture was poured into water, filtered and dried to obtain the desired product as pale yellowish white crystals (melting point 89-91°C).

Claims (2)

[Claims] (1) Trimethine compound represented by the following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) In the above formula, R_1 to R_4 are hydrogen atoms, alkyl groups, and aryl groups, and R_5 to R_9 are hydrogen atoms. or a monovalent group, m
, n is an integer from 1 to 4, R_1_0 is -XR_1_1
, -PO(OR_1_2)_2, -CR_1_3R_1
_4R_1_5, -NR_1_6R_1_7 (X represents a sulfur atom, R_1_1 to R_1_7 represent a hydrogen atom or a monovalent group. However, at least one of R_1_3, R_1_4, and R_1_5 represents an electron-withdrawing group). (2) In general formula (I), R_5 to R_7 are hydrogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkoxycarbonyl groups, aryl groups, aryloxy groups, arylthio groups, aryloxycarbonyl groups, and cyano groups, R_2 , R_3 is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a cyano group,
Nitro group, substituted amino group, hydroxy group, halogen atom, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, R_1_1 is hydrogen atom, alkyl group, aryl group, heterocyclic group, COR_1_2, SO_
2R_1_3, N=CR_2_0R_2_1, NR_2
_2R_2_3 [R_1_2, R_1_3 are hydrogen atoms, alkyl groups, aryl groups, heterocyclic groups, R_2_0,
R_2_1, R_2_2, R_2_3 are hydrogen atoms, alkyl groups, aryl groups, heterocyclic groups, COR_2_4, SO
_2R_2_5 (R_2_4, R_2_5 are hydrogen atoms,
represents an alkyl group, aryl group, or heterocyclic group],
R_1_2 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group (further, R_1_2 may be connected to each other to form a 4- to 12-membered ring structure that may contain a heteroatom), R_1_3, R_1_4, R_1_5 is a hydrogen atom,
Alkyl group, aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, halogen atom, cyano group, nitro group, SO_2R_2_6, COR_
2_7, NR_2_8R_2_9 [R_2_4, R_
2_7 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkylthio group,
Arylthio group, hydroxy group, NR_3_0R_3_
1, R_2_8, R_2_9, R_3_0, R_3_
1 is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, S
O_2R_3_2, COR_3_3(R_3_2, R_
3_3 represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group), and R_1_3 and R_1_4 may be linked to each other to form a 4- to 12-membered ring structure that may contain a hetero atom.] , R_1_6, R_1_7 are hydrogen atoms, alkyl groups, aryl groups, heterocyclic groups, SO_2R
_3_4, COR_3_5, hydroxy group, NR_3_
6R_3_7 [R_3_4, R_3_5 are hydrogen atoms,
Alkyl group, aryl group, alkoxy group, aryloxy group, heterocyclic group, NR_3_8R_3_9, R_3_
6, R_3_7, R_3_8, R_3_9 are hydrogen atoms,
Alkyl group, aryl group, heterocyclic group, SO_2R_4_
0, COR_4_1 (R_4_0 and R_4_1 represent a hydrogen atom, an alkyl group, an aryl group, and a heterocyclic group), and R_1_6 and R_1_7 are connected to each other to form a 4- to 12-membered ring structure that may contain a hetero atom. may be formed. ] The trimethine compound according to claim 1