JPS6234957A - Novel methine dye - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [m and n are 0 or 1; q is 0-3; R1 and R2 are (substituted) alkyl; R3-R5 are H, alkyl, alkoxy, OH, (substituted) amino or halogen; R3 and R4, R4 and R5 or R3 and R5 may together form a condensed 6-membered ring; R6 is (substituted) alkyl, (substituted) aryl or heterocyclic group; Z1 and Z2 are atomic groups necessary for forming a 5-6- membered ring; L1 and L2 are (substituted) methine; X<-> is anion; p is 1 or 2, and is 1 when the compound forms an intramolecular salt]. EXAMPLE:The compound of formula II. USE:A filter, a laser-recording material, a dye and sensitizing pigment for photographic material. PREPARATION:The objective compound can be produced e.g. by reacting a heterocyclic guaternary salt derivative having active methyl group with a 4- methyl-2-thiocoumarin derivative and condensing the resultant intermediate of formula III with the intermediate of formula IV in the presence of a base.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel methine dye represented by the general formula [■].

-Yu In the set, m and n may be the same or different, and O or 'sq is 0. / represents 2 or 3.

R,, R2 may be the same or different (represents a substituted or unsubstituted alkyl group).

R3, R4, and R5 may be the same or different and each represents a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, a substituted or unsubstituted amino group, or a halogen atom, and R3 and R4, R4 and R5, or R3 and R5 may be fused together to form a membered ring. R6 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group.

Z□ and Z2 may be the same or different (,!
It represents a group of atoms necessary to form a membered ring or a six-membered ring, and these groups may further have substituents.

L□ and R2 represent a methine group or a substituted methine group.

Xo represents an anion.

P represents 1 or λ, and when the compound forms an inner salt, P is 1.

Each substituent of the compound represented by the general formula [I] is preferably the substituent shown below.

That is, R1 and R2 may be the same or different from each other. group, dodecyl group, octadecyl group, vinylmethyl group, cyclohexyl group, etc.) or substituted alkyl group (for example, as a substituent, carboxy group, sulfo group, cyan group, halogen atom (e.g. fluorine atom, chlorine atom, bromine atom), hydroxy group, alkoxycarbonyl group having up to r carbon atoms (e.g. methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group, benzyloxylcarbonyl group, etc.), alkoxy group having up to r carbon atoms (e.g. methoxy group, ethoxy group, benzyloxy group) , phenethyloxy group, etc.) Monocyclic aryloxy group having IO or less carbon atoms (e.g., phenoxy group, p-)
lyloxy group, etc.) acyloxy group having 3 or less carbon atoms (e.g., acetyloxy group, propionyloxy group, etc.),
Acyl groups (e.g. acetyl group, propionyl group, benzoyl group, mesyl group, etc.) having a carbon number of g or less, carbamoyl groups (e.g. carbamoyl group %NlN-dimethylcarbamoyl group, morpholinocarbonyl group, piperidinocarbonyl group, etc.), sulfamoyl groups ( For example, sulfamoyl group, N,N-dimethylcarbamoyl group, morpholinosulfonyl group, piperidinosulfonyl group, etc.) carbon g number t.

The following aryl groups (e.g. phenyl group, ≠-chlorophenyl group, μm methylphenyl group, α-naphthyl group, etc.)
An alkyl group having a carbon number of ir or less substituted with, etc.) is preferable.

R6 is R −
(2-pyridyl group, cochiazolyl group, etc.).

Zl and Z2 may be the same or different from each other and represent a group of nonmetallic atoms necessary to form a membered ring, and the ring is composed of, for example, a thiazole nucleus (e.g., thiazole, ψ-methylthiazole, μm phenyl Thiazole, !-methylthiazole, terphenylthiazole, μ, j-dimethylthiazole, U,, t-diphenylthiazole, μ,
(2-chenyl)thiazole, etc.), benzothiazole nuclei (e.g. benzothiazole, ≠-chlorobenzothiazole, r-chlorobenzothiazole, t-chlorobenzothiazole, 7-chlorobenzthiazole, ≠-methylbenzothiazole, j-methyl Benzothiazole, t-methylbenzothiazole, evening.

t-Dimethylbenzothiazole, terbromobenzothiazole, t-bromobenzothiazole, j-trifluoromethylbenzothiazole, j-phenylbenzothiazole, dermethoxybenzothiazole,! -methoxybenzothiazole, A-methoxybenzothiazole,! −
Carboxybenzothiazole! -cyanobenzothiazole, j-ter-fluorobenzothiazole, terethoxybenzothiazole, tetrahydrobenzothiazole, t,4-dimethoxybenzothiazole,! -hydroxybenzothiazole, t-hydroxybenzothiazole, etc.), naphthothiazole nuclei (e.g. naphtho-(/, 2-d:) thiazole, naphtho[, 2°/-d) thiazole, nand[2
,3-d]thiazole,! -methoxynaphtho(-2,7
-d) Thiazole, terethoxynaphtho ('*'-a)
thiazole, t-methoxynaphtho[/, 2-d]thiazole, 7-methoxynaphtho(/, 2-d)thiazole, etc.), oxazole nuclei (e.g. Hiro-methyloxazole, j-methyloxazole, ≠-phenyloxazole, ri, !-diphenyloxazole, μ-ethyloxazole, terdimethyloxazole, !-phenyloxazole, etc.), benzoxazole nuclei (e.g. benzoxazole, !-chlorobenzoxazole, termethylbenzoxazole, terphenylbenzoxazole, t) -Methylbenzoxazole, Yu, J-
dimethylbenzoxazole, *, l-dimethylbenzoxazole, j-methoxybenzoxazole, terethoxybenzoxazole, tafluorobenzoxazole, t-methoxybenzoxazole, j-hydroxybenzoxazole, t-hydroxybenzoxazole, etc.), naphthoxazole Nucleus (e.g. nuff) ('
l 2-d]oxazole, nand(,2,/-d]oxazole, napf)(,2,J-d)oxazole, etc.)
, selenazole core (e.g. selenazole, μm methylselenazole, J-phenylselenazole, ≠.

tadiphenylselenazole, etc.), benzoselenazole core (e.g. benzoselenazole, j-chlorobenzoselenazole, termethylbenzoselenazole, termethoxybenzoselenazole, terphenylbenzoselenazole, etc.), naphthoselenazole core (e.g. Naft (/,,
2-d) selenazole, naphtho(,2,/-d)selenazole, nand[λ+3-a]selenazole, etc.), thiazoline nucleus (e.g. thiazoline, ≠-methylthiazoline, l-phenylthiazoline, etc.), oxazoline nucleus (e.g. ), isoxazole nucleus (e.g. termethylisoxazo-w, etc.), benzisoxazole nucleus (e.g. benzisoxazole e),
), 3,3-dialkylindolenine nucleus (e.g. 3,3
-dimethylindolenine, J, 3. j-trimethylindolenine, terchloro-3,3-dimethylindolenine,! -ethoxycarbonyl-3,3-dimethylindolenine, etc.), copyridine nucleus (e.g., pyridine, !-methylpyridine, etc.), l-pyridine nucleus (e.g., pyridine, etc.)
, corquinoline nucleus (e.g. t-ethoxyquinoline, -
ethylquinoline, t-chloroquinoline, r-fluoroquinoline, etc.), ≠-quinoline nucleus (e.g. r-methylquinoline, j-fluoroquinoline, 6-chloroquinoline, etc.)
,'-isoquinoline nucleus (e.g. inquinoline etc.), benzotellurazole nucleus (e.g. benzotellurazole, r
-chlorobenzotellurazole, j-methylbenzotellurazole, j-methoxytellurazole, etc.) naphthoteruazole nucleus (e.g. 7) (/, 2-d) tellurazole, naphtho [2°/-d ) Tellurazole etc.)
is preferred.

As the ring formed by Z2, the following rings other than those mentioned above are also preferably used.

Benzimidazole core (e.g. l-methylbenzimidazole, l-ethylbenzimidazole, !-benzylbenzimidazole, tau 6-dimethyl-l-ethylbenzimitazole, !, 4-dichloro/, -(2-methoxyethyl)benzo imidazole, j-chloro-l-
Ethyl-tert-methylbenzimitazole, 6-dichloro-7-(2-phenylethyl)benzimidazole, chloro-l-ethyl-j-trifluoromethylbenzimidazole, 6-chloro-tercyano-l- Ethylbenzimidazole, 117-trimethylenebenzimidazole, /-(2-chloroethyl)benzimidazole, /-(,2,,2,2-trifluoroethyl)
-, t, [,2,J-d
:] imidazole, etc.) imidazoquinoline nucleus (e.g. l-
ethyl imidazo [μ, 1-b] quinoline, etc.) imidazo (
<z, tb) Quinoxaline core (e.g. /, 3-dimethylimidazo [≠.

t-b) Quinoxaline, /, 3-diethylimidazo [μ
, r-b] quinoxane, /, 3-diallylimidazo [pi, rb] quinoxaline, l, 3-diphenylimidazo [≠, t-b] quinoxaline, 2-chloro-7,3-diethylimidazo [≠, ! -b] Quinoxaline, 1.7-
dichloro-/, J-diethylimidazo [μ, t-b) quinoxaline, etc.) benzotellurazole nucleus (e.g. benzotellurazole, j-methylbenzotelluriazo-y, etc.)
Naphthoteruazole nucleus (e.g. Nando [/, 2-d]
(tellurazole, nut[co+'-d]tellurazole, etc.) -l ≠ as an unsubstituted or substituted amino group of R3, R4
- may be different (hydrogen atom, lower alkyl group having l-μ carbon atoms (e.g. methyl group, ethyl group, propyl group, butyl group, etc.), acyl group having 2 to g carbon atoms (e.g. acetyl group, propionyl group, benzoyl group, etc.) are preferred.

It is also preferable that R15 and R16 are connected to each other to form a ring or a six-membered ring.

Furthermore, it is also preferable that R15 and/or R16 bond to the benzene ring of the benzobyrylium nucleus to form a condensed ring or a t-membered ring.

The alkyl group for R3, R4, and R5 has carbon numbers 1 to q.
Lower alkyl groups (e.g., methyl, ethyl, isopropyl, butyl, etc.) are preferable, and alkoxy groups include alkoxy groups having carbon atoms of l to μ (e.g., methoxy, ethoxy, propoxy, butoxy, etc.). ) is preferred.

In addition to the above, R3, R4, and R5 include hydrokeys /
Also preferred are a j-cy group and a benzofused metal ring.

Ll and L2 represent a methine group or a substituted methine group, and substituents for the methine group include alkyl groups having carbon atoms of 1 to μ (e.g., methyl group, ethyl group, propyl group, butyl group, etc.), substituted alkyl groups. (Examples: evabenzyl group, phenethyl ts, z-): x-=lupropyl group, ≠-phenylbutyl group, etc.), and aryl groups having 6 to io carbon atoms (eg, phenyl group, naphthyl group, etc.) are preferred.

It is also preferable to crosslink between methine groups with a trimethylene group to form a 6-membered carbon ring on the methine chain.

Xo represents an anion, specifically chloride, bromide, iosito, thiocyanate, perchlorate,
Preferred are paratoluenesulfonate, methylsulfate, ethylsulfate, and tetrafluorose 2-ate.

The compound represented by general formula (I) can be synthesized by various synthetic methods, but for example, as shown in the reaction formula below,
An intermediate obtained by the reaction of a heterocyclic quaternary salt derivative having an active methyl group and a Hiro-methyl-corchiomarine derivative [
It can be synthesized by a condensation reaction between A) and intermediate CB) in the presence of a base.

17-1tr- In the above reaction formula, R1, R2, R3, R4, R5, R6
, Zl, Z2, P, m, n and q have the same meanings as explained in general formula (I).

Xl/X2 represents an anion and has the same meaning as X, Pl, P2
has the same meaning as P.

R7 represents a substituted or unsubstituted lower alkyl group.

Bases used in the condensation reaction include inorganic bases (e.g., sodium hydroxide, potassium hydroxide, sodium carbonate, etc.) and organic bases (e.g., pyridine, l-dimethylaminopyridine, triethylamine,
etc.) are used.

Methods for synthesizing intermediate [A] include methods other than those described above, such as Research Disclosure (Research D).
isclosure ) / 6j2k (volume 143 29
Page / 977), Japanese Patent Application Publication No. 2003-111002.

-7fhLILu publication, 4O-7j4! An example is the method disclosed in Publication #j.

The novel methine dye of the present invention has excellent fastness and is effective as a dye for filters and a dye for laser recording materials (optical disks, etc.), and is also effective as a dye for photographic materials and a sensitizing dye. These dyes also dye mixtures from groundwood pulp and bleached sulfite pulp as well as pure e-pulp and are virtually completely dyed.

Furthermore, these dyes can be excited with an excitation method such as the co-harmonic or third harmonic of an excimer laser - 1Nd:YAG laser to obtain laser light in the near-infrared to infrared region, and have good fastness. , which acts as a high-performance laser dye with high energy conversion efficiency.

Specific examples of the compound represented by the general formula CI) of the present invention are shown below, but the invention is not limited thereto.

-2 - 1J
ΔJ′e′
ζ--2
Next, examples of synthesizing the compounds according to the present invention will be explained in detail with reference to the following examples.

Example-1 (Synthesis of intermediate (A)) /-(3-ethyl-2-(C't-methyl-2H-
chromene-2-4+)y'n)methyl)benzothiazolium perchlorate 3-ethyl-2-methylbenzothiazolicum 1)-)luenesulfonate/7. Evening I and ≠-Methyl-Coach Okumari y1. After heating reaction of Il/ with trooc for tj hours,
Add 20ml of methanol-N to the reaction mixture, then add acetone<AO
ml was added to make a homogeneous solution.

After cooling to room temperature, 60% perchloric acid/j, 717 was added and stirred at room temperature to precipitate crystals. The crystals were collected by filtration, washed with a small amount of acetone, and then added to a mixed solvent of 20 methanol and 4 AO ml of acetone at room temperature, stirred for 30 minutes, collected by filtration, and washed with acetone to obtain the desired product r.

H) was obtained. (Yield 4Ao%) Brown crystal mp2r00c or more (decomposition)/-(2)
j-) Lifluoromethyl-3-ethyl-2-((pi-methyl-2H-chromene-J 4cm coylidene)methyl)-benzothiazolium p-)
Ruenesulfonate Tertrifluoromethyl-3-ethyl-comethylbenzothiazolium p-Toluenesulfonate 2.379
Tobi-Methyl-Coach Off Marine/, 09 1ro0c
After heating for 20 hours, methanol was added to the reaction mixture.
1. Then add 10ml of acetone. Oml of ethyl acetate was added to make a homogeneous solution.

When cooled to room temperature, crystals precipitated. After collecting the crystals by filtration and washing with a small amount of acetone, methano =, k /
01n1.7 y/Oml, ethyl acetate 2
The crystals were added to 0ml of mixed solvent, stirred for 4 minutes, collected by filtration, and washed with acetone to obtain the desired product 1. ≠71 was obtained.

(yield dat%), brown crystal mp2'72~273°C (decomposition)/-(
311-chloro-3-ethylleuco((gumethyl-,
2H-chromen-2-ylidene)methyl)-benzothiazolium p-toluenesulfonate! -Chlo4-3-ethyl-2-methylbenzochy3!
- azolium p-) luenesulfonate//, /9 and goomethyl-corchiofmarine s, H) for 2 hours at 0°C.
After 3 hours of heating reaction, 21 ml of methanol was added to the reaction mixture.
Next, zOml of acetone and ethyl acetate/jOml were added, and when the mixture was cooled to room temperature, crystals were precipitated. Filter the crystals,
After washing with a small amount of acetone, add 2 ml of methanol at room temperature.
l, acetone jOm1. Ethyl acetate/I//! The crystals were added to a mixed solvent of θd, stirred for 20 minutes, collected by filtration, and washed with acetone to obtain 7.2 g of the desired product. (Yield 2%) Brown crystals mp212-213°C (decomposition)/-(4
)j-methyl-3-ethyl-2-((≠-methyl-2H
-Chromen-2-ylidene)methyl)benzothiazolium nicro2-toj-methyl-3-ethyl-λ-methylbenzothiazolium p-toluenesulfonate λ. After heating reaction of 07 g and μm methyl-coch ocumarin/, 01/ at 7r00c for 2 hours, 10 ml of methanol was added to the reaction mixture. Next, 10 vol of acetone and 20 ml of ethyl acetate were added, and when the mixture was cooled to room temperature, crystals were precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then dissolved in methanol at room temperature for 20 m
1. Then, 4LOml of acetone was added to make a homogeneous solution.

A 60% aqueous perchloric acid solution jI was added thereto, and after stirring at room temperature for 30 minutes, the precipitated crystals were collected by filtration and washed with acetone to obtain 4t4g of the desired product. (Yield!t%) Brown crystal rrlp 270=27 Yu'C (decomposition)
/-(5) t-Methoxy-3-ethyl-2-((coumethyl-.2H-chromen-2-ylidene)methyl)benzothiazolium yosito! -Methoxy-3-ethyl-comethylba/dithiazolium p-toluenesulfonate λ, l! g Tobiichi Methyl-Cochocumarine 1. After heating and reacting Og with tro'c for 20 hours, methanol/krrt1. Acetone/2 ml was added to make a homogeneous solution. 7 g of sodium iodide (acetone tm/solution) was added dropwise to this solution and stirred at room temperature to precipitate crystals. Filter the crystals,
After washing with a small amount of acetone, the crystals were added to 20 g of water at room temperature, stirred for 13 minutes, filtered, and washed with acetone to obtain 0.2 g of the desired product. (Yield 31%) Brown crystal mp, 27J ~ 2740 (:' (decomposition)
/ -(6) J-ethylruyo((4'-methyl-
2H-chromene-yoylidene)methyl)-naphtho[co,l-d')thiazolium iosito 3-ethyl-yomethylnaphtho[λ+'-a) thiazolium p-) luenesulfonate co, 27I and dermethyl-coch After heating reaction of ocumaline/Og at /jθ0C for 21 hours, 1 ml of methanol and then 12 ml of acetone were added to the reaction mixture to form a homogeneous solution. 1 sodium iodide to this solution.

7p (water j-bath solution was added dropwise and stirred at room temperature for 1 hour, crystals precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then placed in 1 kml of room temperature sewage water and a mixed solvent of acetone/jml. After stirring for 13 minutes, the mixture was filtered and washed with acetone to obtain 1♂g of the target product.

(Yield xr%) 3 r- Brown crystal mp2100c or more (decomposition)/-(7)j
-ethyl-,2-((4L-methyl-2H-chromene-
λ-ylidene)methyl)natto C/, 2-d] thiazolium iosito 3-ethyl-2-methylnatto (/, J-d) thiazolium iosito 2.2177 and 1-methyl-2-thiocoumarin/, from Og/- (6) In the same way as the object o
, otg was obtained. (Yield 3.!%) Brown crystal mp1
4Ao~l daλ'c (decomposition) l-(8n t, J-dimethyl-3-ethylruyo((≠-methyl-2H-lytetramen-2-ylidene)methyl)-benzothiazolium p
-) Luenesulfonate tau 6-dimethyl-3-ethyl-comethylbenzothiazolium p-) Luenesulfonate 2g, og togu-1 methyl-2-thiocoumarin/3°2I/jO”c 1
After heating reaction for 7 hours, add 10ml of methanol to the reaction mixture.
Next, 1001 acetone and 500-500 ethyl acetate were added,
When cooled to room temperature, crystals precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then mixed with methanol and acetone at room temperature.
The crystals were added to a mixed solvent of 001 nl and 300 ml of ethyl acetate, stirred for 20 minutes, collected by filtration, and washed with acetone to obtain the target product It.277. (Yield 4/-%) Brown crystals m9201-203°C (decomposition)/-(9
)J-methyl-2((μmmethyl-2H-chromene-2
-ylidene) methyl) benzoxacillium perchlorate λ, 3-dimethylbenzoxacilium p-toluenesulfonate, z, tp and 7.2 g of μm methyl-corchiomarin were heated at 1 j O 0 C for IQ hours, and then the reaction mixture was added. Add methanol/rml and acetone/2ml,
A homogeneous solution was obtained. Add sodium perchlorate/2 to this solution.
When fl (aqueous solution) was added dropwise and stirred at room temperature, crystals were precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then poured into 10 ml of room temperature sewage water. Methanol/l//Orn11
The crystals were added to 20 vtl of ethyl acetate, stirred for 10 minutes, collected by filtration, and washed with ethyl acetate to obtain 0.39 of the desired product. (Yield/2%) Brown crystals mp2~, 27/'C (Decomposition) Example, 2 (Synthesis of compound)! -chloro3-dithyl-λ-((≠-methyl-xH-
Chromen-2-ylidene)methyl)-benzothiazolium p-)luenesulfonate.

tg and 3-ethyl-J-oxo-j-(3-methylbenzothiazolin-2-ylidene)-λ-methylthioμ,
j-dihydrothiazolium p-toluenesulfonate2. jtl/ and 3 ml of triethylamine were added to 100 rtl of acetonitrile, and the mixture was reacted by heating on a steam bath for 30 minutes.

After cooling, the precipitated crystals were collected by filtration and washed with acetone. Then methanol/chloroform: 2/lr (Vo
1. / Vo 1. ) was purified through silica gel column chromatography, and then recrystallized from a mixed solvent of tutanol/chloroform to obtain the desired product/,/
l/ was obtained. (Yield λ7.j%) Dark reddish brown crystals Melting point, 2≠t~2IO'C (decomposition) (ξ=i, ita x tO) Example 3 (synthesis of compound 3) 3-ethyl-t, X- Dimethyl-λ-((4'-methyl-2H-chromen-2-ylidene)methyl)benzothiazolium p-)luenesulfonate 2.19 and 3-ethyl-μmoxo-1-(1-methoxy-3 -methylbenzothiazolin-2-ylidene)-coethylthioμ
, j-dihydrothiaturium ethanesulfatoko, ≠
1 and triethylamine lrml in acetonitrile/rO
rnl and reacted for 30 minutes on a steam pass. After cooling, the precipitated crystals were collected by filtration and subjected to silica gel column chromatography (opening solvent methanol/chloroform "3/" (Vol/Vo
1) Purified as described above. The product was dissolved in methanol, sodium heiodide/09 was added thereto, and the precipitated crystals were collected by filtration and washed with methanol to obtain the desired product/Ill. (Yield≠Ir%) Dark brown crystals Melting point 23j~2ao0c Decomposition-J2- (ξ=ri, jtx764) Example (Compound/I)! -chloro-3-ethyl-co((4'-methyl-H
-chromene-coylidene)methyl)benzothiazolium p-toluenesulfonate l.

rp and 3-ethyl-≠-oxoter(-1(3-ethylnaphtho(/,,2-d)thiazoline-λ-ylidene)
ethylidene)-2-methylthio-q.

Tadihydrothiazolium p-) Lienesulfo-1)
--) 7.9111 and triethylamine rml were added to acetate and nitrile/10-, and the mixture was heated and reacted on a steam path for 30 minutes. After cooling, the precipitated crystals were collected by filtration and recrystallized from methanol-acetonitrile to obtain the desired product.
I got rli. (Yield J'1%) Dark reddish brown crystals Melting point 21rO6C or higher (ξ=4.lr3×10') 14A 3 - Example! (Compound l) 3-ethyl-Bt-dimethyl-2-((≠-methyl-,
2H-chromen-2-ylidene)methyl)-benzothiazorium p-)luenesulfonate λ,og and 3-ethyl-l-ochynta-(co(3-ethylbenzothiazolin-2-ylidene)ethylidene)-2 -Methylthioda, terdihydrothiaturium p-) 2.tg of luenesulfonate and 1 ml of triethylamine were added to 1 oorrtt of acetonitrile and reacted by heating on a steam path for 30 minutes. After cooling, the reaction mixture was chromatographed on silica gel (eluent methanol/chloroform = = J//7
(V O1/Vol)) After purification, methanol-
The desired products o and tg were obtained by recrystallization from acetonitrile. (Yield I%) Dark reddish brown crystals Melting point 247-0C Example 6 The following compounds were also synthesized in the same manner as in Examples 2-2.

J 6-

Claims (1)

[Claims] A methine dye represented by the following general formula [I]. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, m and n may be the same or different.
Or 1, q represents 0, 1, 2 or 3. R_1 and R_2 may be the same or different and each represents a substituted or unsubstituted alkyl group. R_3, R_4, and R_5 may each be the same or different and each represents a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, a substituted or unsubstituted amino group, or a halogen atom, and R_3 and R_4 and R_4 and R_5, or R_3 and R_5 may form a fused 6-membered ring. R_6
represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group. Z_1 and Z_2 may be the same or different and represent a group of atoms necessary to form a 5- or 6-membered ring, and these rings may further have a substituent. L_1 and L_2 represent a methine group or a substituted methine group. X^■ represents an anion. P represents 1 or 2, and P is 1 when the compound forms an inner salt. )