TW201100358A - Novel triarylmethane compound - Google Patents

Abstract

Disclosed is a dye composition which has high clarity and color developability, while exhibiting excellent fastnesses such as heat resistance, wet heat resistance and water resistance. Specifically disclosed are a triarylmethane compound represented by formula (1) and an oil-based or aqueous dye composition that contains the triarylmethane compound. (In formula (1), Ar1, Ar2 and Ar3 each independently represents an aromatic residue having a carbon atom that is bonded to the central carbon atom; and X- represents a bis(trifluoromethanesulfonyl)imide anion or a tris(trifluoromethanesulfonyl)methide anion.)

Description

201100358 VI. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a novel triarylmethane compound. * [Prior Art] Triarylmethane dyes are characterized by very vivid color and high color rendering. They are used as various materials for purple, blue or green colored materials, water-based inks, oil-based inks, and inkjet inks. Color filters are widely used in inks, etc.: (4) on the way. In general, the properties required for colored materials vary depending on each application. However, most of the applications require bright colors and high color rendering properties, and the coloring matter is firmer against light and heat. As a triarylmethane dye, an anionic dye having a cationic group such as a quaternary nitrogen in a structure; and an anionic dye such as a sulfone group introduced into a cationic dye structure; No matter which color rendering property is superior, on the other hand, there are disadvantages such as poor light resistance, heat resistance, moisture resistance, and water resistance. Therefore, the present invention is expected to have the sharpness and color developability of a triarylmethane dye, and has a high fast dye, but no dye having such properties has been found. Patent Document 1 describes a cationic triaryl sulfonium compound and a chloride of a gas ion or an aryl acid ion, but the inventors of the present invention have studied the 'tri-glycan methane described in the patent document. The compound is resistant to light, γ, heat, and water resistance is insufficient. Further, Patent Document 2 discloses an example of a compound having no specific compound of a triaryl-based cationic dye having a thiol-based ion, and no light resistance, heat resistance, moist heat resistance, water resistance, etc. The record of firmness. λ, commercially available as a cation of 147486.doc 201100358, a gas-based or oxalic acid ion, but the results of studies by the inventors et al.: the known triphenylmethane compounds Light resistance, heat resistance, moist heat resistance, and water resistance are insufficient. [PRIOR ART DOCUMENT] [Patent Document 1] [Patent Document 1] Japanese Patent Laid-Open No. 2008-304766 [Patent Document 2] Japanese Patent Laid-Open No. Hei. No. Hei. No. Hei. The purpose of the present invention is to provide a novel leucotriazole compound having excellent sharpness and color rendering properties as described above, and having excellent fastness such as light resistance, heat resistance, resistance to (four), and water resistance. And an oily or aqueous dye composition using the compound. [Technical means for solving the problem] * The inventors of the present invention conducted intensive studies to solve the above problems, and as a result, found that the cationic triaryl methane and a specific anion vapor maintain the vividness of the triarylmethyl (10) dye. The color rendering property and the light resistance, heat resistance, resistance >""", heat and water resistance are drastically improved, and the present invention has been completed. That is, the present invention relates to: (1) A triarylmethane compound [Chemical Formula 1] which is represented by the general formula (1): 147486.doc 201100358

Ar3 (1) (In the formula (1), 'Ari, Ai*2, and Ar3 each independently represent an aromatic residue bonded to a medium-stone anodic atom by a carbon atom'. The χ-system represents bis(trifluoromethanesulfonate) An amine anion or a tris(trifluoromethanesulfonate) methide anion); (2) a triarylmethane compound such as (1) which is represented by the formula (2): [Chemical 2]

(In the formula (2), each independently represents a hydrogen atom, a carbon group having 1 to 6 carbon atoms, a phenyl group or a benzyl group, and each of R7a to R2Qa independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a dentate atom; Χ- has the same meaning as the above formula (1)" (3) A triarylmethane compound of (2), wherein χ is a tris(trifluoromethanesulfonate) anthracene anion; (4) as in (1) A diarylmethane compound represented by the formula (3): 147486.doc 201100358

= llRlb~R4b independently represent a chlorine atom, a carbon number of 1~... a group, a radical or a radical 'R5b~Rl6b each independently represents a chlorine atom, a carbon atom of 1 to 6 or a halogen atom, and 1715 does not represent a halogen atom. , a carbon number of 1 to 6 dialkyl, a functional atom or an amine group, X- has the same meaning as the above formula (1) (7) such as (4) a triaryl-methyl compound, wherein χ. is three (three gas (6) an oily dye composition which contains, as in (1) to (5), a diarylmethane compound and an oil-soluble organic solvent; (7) an aqueous dye composition containing, for example, 〇) to (5) Ren- Xiang Ge diarylmethyl fragrant compound and aqueous medium. [Effect of the Invention] The diaryl decane compound of the present invention is excellent in sharpness and color fastness as described above, and if an oily or aqueous dye composition is formed and the dye coloring body is processed, it is displayed as compared with the prior product. More excellent fastness. Namely, the triaryldecane compound of the present invention can be used for dye coloring] 47486.doc 201100358 and can be applied to a wide range of applications such as ink for shirt coloring ink or ink for inkjet. [Embodiment] The diarylmethane compound of the present invention is represented by the above formula (丨). In the formula (1), An, the core 2 and the shot 3 each independently represent an aromatic residue bonded to a central carbon atom by a carbon atom. Ο Ο As the aromatic residue of the formula (1), the core 2, and the aromatic residue in the third embodiment, for example, an aromatic smoke residue such as a phenyl group, a naphthyl group, an onion group, a phenanthryl group, a ketone group or a benzoxyl group may be mentioned. An aromatic such as a bite base, a t-base, a (tetra)-based group, a cylinyl group, an iso-indolyl group, a base group, a pseudo-inducing group, a mercapto group, a carbaryl group, a thiophene group, and a fluoroyl group. Heterocyclic residues, etc. are particularly good compared to phenyl or Cai. The phenyl group or the naphthyl group of the formula (1) may have a substituent, and the substituent is not particularly limited, and examples thereof include an aliphatic hydrocarbon residue, an aromatic residue, a cyano group, and an isocyano group. Thiocyanate, isothiocyanate, contigyl, fluorenyl, halogen atom, thiol, substituted or unsubstituted amine group, alkyl aryl group, aryl group, aryl (tetra)oxy group which may have a substituent , a few groups, an amine methyl group, a base, an oxygenated group, an aromatic oxygen group, and the like. In the formula (1), χ represents bis(trifluoromethanesulfonate) imide anion or tris(trifluoromethyl hydrazine) methide anion, of which tris (three gas continuation) methyl group is preferred. Anion. As the triarylmethane compound of the present invention, in terms of excellent fastness such as heat resistance, heat and moisture resistance, and water resistance, it is preferred that Rla~foot of the formula (2) in the above formula (2) Independently represents a chlorine atom, an alkyl group of a carbon number, a phenyl group or a benzyl group, and R7a to R2〇a each independently represent a hydrogen atom, a carbon 147486.doc 201100358, an alkyl group of 1 to 6, a halogen atom. 2) 中中- indicates a bis(trifluoromethanesulfonyl)imide anion or a bis(trifluoromethane) anthracene anion, especially a tris(trifluoromethanesulfonate) anthracenide anion. In Rla~1^ of the formula (2), examples of the alkyl group of the carbon number 6 include a mercapto group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group, and a ring. An alkyl group such as a hexyl group, a 1-ethylpropyl group, a fluorene-methyl group, an anthracene or a 2-dimercaptopropyl group; the alkyl group such as hexanyl may have a substitution|, and the K-go group is not particularly limited as Examples of the alkyl group having 1 to 6 carbon atoms of the substituent include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a 2-sulfoethyl group, a carboxyethyl group, and a cyanoethyl group. An oxyethyl group, an ethoxyethyl group, a butoxyethyl group, a trifluoromethyl group, a pentafluoroethyl group, a phenyl fluorenyl group, etc., a phenyl group or a benzyl group in the formula (2) The substituent may have, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group or the like (carbon number 5) alkyl group, a fluorine atom, a halogen atom such as a chlorine atom, a bromine atom or an iodine atom, a sulfonic acid group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a third butoxy group, a hexyloxy group or the like (carbon number: 6) alkoxylate a hydroxyl group such as a hydroxyethyl group or a hydroxypropyl group (carbon number 〖~histyl group; oxiranyloxy group, ethoxyethyl group, ethoxy propyl group, butoxyethyl group, etc. (carbon number 1 to 5) Alkoxy (carbon number 1 to 5) alkyl; 2-hydroxyethoxy group and the like hydroxyl (carbon number 1 to 5) alkoxy group; 2-methoxyethoxy group, 2-ethoxyethoxy group Etc. (carbon number: 1 to 5) alkoxy (carbon number: 1 to 5) alkoxy; 2-sulfoethyl, carboxyethyl, cyanoethyl, etc. Rla~1^3 of formula (2) Preferred is a hydrogen atom, an unsubstituted carbon group i to 6 alkyl group, an unsubstituted phenyl group, or an unsubstituted group. Section yl 147486.doc 201100358 formula (2) of R7a~R2Qa, include: a hydrogen atom, _ atom, or non-carbon atoms of 1~6 unsubstituted alkyl of formula (2) in the R7a~R20a.

^ Anti-double A-sign, 1 1 1J JJ 歹I 曱 曱, ethyl, propyl, τ, isobutyl, pentyl, cyclodecyl, hexyl, cyclohexyl base. The mercapto group may have a substituent, and the substituent is not particularly limited. Examples of the alkyl group having a carbon number of 6 having a substituent include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, and a 2-sulfoethyl group. ,

Carboxyethyl, cyanoethyl, decyloxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, and the like. In the formula (2), examples of the halogen atom include fluorine, gas bromine, and the like. Further, the bis-alkyl-based compound of the present invention is preferably a compound of the above formula (3) in terms of excellent fastness such as heat resistance, moist heat resistance and water resistance. In the formula (3), R lb to Ra each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group, and each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, and Rm represents hydrogen. An atom, an alkyl group having 1 to 6 carbon atoms, a γ atom or an amine group. Further, in the formula (3), the parent represents a bis(trifluoromethanesulfonyl)imide anion or a tris(trifluorosulfonium sulfonate) methide anion, and particularly preferably a tris(trifluorosulfonium sulfonium) ruthenium compound. Anion. Rb to "in the formula (3)" is an alkyl group having a carbon number of 丨6, and examples thereof include a mercapto group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclodecyl group, a hexyl group, and a cyclohexyl group. An alkyl group such as 1-ethylpropyl, 1-methylpropyl, hydrazine, or dimethylpropanyl. The alkyl group may have a substituent, and the substituent is not determined separately. Examples of the alkyl group having 1 to 6 carbon atoms having a substituent include, for example, 147486.doc 201100358, ethyl group, and propyl group. , butyl butyl, 2-phenylethyl, ethyl, cyanoethyl, decyloxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, penta-ethyl, Phenylmethyl and the like. In the examples of R1 to R4b in the formula (3), the substituent or the group may have a substituent, and the substituent is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. (6) to c5) alkyl group such as tributyl or pentyl group, halogen atom such as fluorine atom, chlorine atom, bromine atom or iodine atom, sulfonic acid group, methoxy group, ethoxy group, propoxy group, butoxy group, a (C1~C6) alkoxy group such as a tributoxy group or a hexyloxy group; a hydroxy (C1 to C5) alkyl group such as a hydroxyethyl group or a hydroxypropyl group; a decyloxyethyl group, an ethoxyethyl group or an ethoxy group; a (C1 to C5) alkoxy (C1 to C5) alkyl group such as a propyl group or a butoxyethyl group; a hydroxyl group (C1 to C5) alkoxy group such as a 2-hydroxyethoxy group; 2 - an ethoxyethoxy group or the like (C1 - C5) alkoxy group (C1 - C5) alkoxy group; 2 - sulfoethyl group, carboxyethyl group, cyanoethyl group or the like. Rb~'s rule of the formula (3) "' is preferably a hydrogen atom, an unsubstituted phenyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, or an unsubstituted benzyl group. Rn of the formula (3) The alkyl group as a carbon number in Rm may, for example, be an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, a cyclopentyl group, a hexyl group or a cyclohexyl group. The substituent is not particularly limited, and examples of the alkyl group having 1 to 6 carbon atoms having a substituent include a hydroxyethyl group, a propyl group, a butyl group, and a 2-hydroxy group. , stilbene ethyl, cyanoethyl, T oxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, etc. In R5b~R17b of formula (3), Examples of the halogen atom include fluorine, chlorine, 147486.doc •10·201100358 bromine, iodine, etc. The amine group in Rm of the formula (3) may have a substituent, and examples of the substituent include a carbon number! The alkyl group, the phenyl group or the aryl group may further have a substituent. The substituent is not particularly limited. Examples of the alkyl group having 1 to 6 carbon atoms having a substituent include, for example, hydroxy group. Ethyl ethyl, hydroxypropyl, hydroxybutyl, 2-stone, ethyl, thioethyl, arylethyl, methoxyethyl, ethoxy", butoxyethyl, trifluoro, Base, pentafluoroethyl and the like. In the case of phenyl hydrazine or a benzyl group, examples of the substituent include a methyl group, an ethyl propyl group, an isopropyl group, a butyl group, a tert-butyl group, a decyl group and the like (9) to C5). A fluorine atom, a gas atom, a (tetra), a moth atom, etc., a repeating acid group, an oxy group, an ethoxy group, a propoxy group, a butoxy group, a third butoxy group, a hexyloxy group, etc. (C1 to C6) An alkoxy group; a base group (C1 to C5); a methoxyethyl group, an ethoxyethyl group, an ethoxypropyl group, a butoxyethyl group, etc. C1~C5) alkoxy (C1~C5) thiol; 2_ alkoxy group and the like (C1~C5) alkoxy; 2_methoxyethoxy, 2-ethoxyethoxy Etc. (9) to C5) an alkoxy group (CBuC5) alkoxy group; 2_thylethyl, decylethyl, cyanoethyl and the like. As R5b to Rl6b of the formula (3), a hydrogen atom, a (10) group, or an unsubstituted alkyl group Rm of a carbon number ’ is preferable as a hydrogen atom or an amine group. The triaryl calcined compound of the present invention can be obtained, for example, by a known synthesis method described in "Theory of Manufacturing Dye Chemistry" (page 781) issued by Hiroshi Aya, published by Technobu Co., Ltd., or by the following means. In combination: a commercially available product in which X- is a gas anion is added with a corresponding salt or acid for salt exchange. 147486.doc 201100358 In the case of synthesizing the triaryldecane compound of the present invention by salt exchange, it can be obtained by dissolving a compound which is a gas anion in a reaction solvent (for example, water, or methanol) , ethanol, isopropanol 'propyl _ ' Ν, Ν dimethyl dimethyl carbamide (hereinafter abbreviated as DMF), Ν-methyl-2-° ratio D ketone (hereinafter abbreviated as ΝΜρ) and other water-soluble polarities Solvents, these solvents can be used alone or in combination, adding the corresponding salt or acid 〇. 5~3 equivalents, at a specific temperature (for example, 〇~100. stirring under the ,, can be easily synthesized) and removed The precipitated crystals are specifically exemplified in Table 1 below. The ear of the triaryl calcined compound represented by the formula (3) is shown in Table 2 below. However, the invention is not limited to the above. 147486.doc 12- 201100358

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Ο ca o ca ca 0 «α. 0 ca o CQ. 0 ex Μ £ « awwa !Β wwwaaw ffi a WBWW « ffi ffi WWMX » Β w WKW w ffi w » SX as K ffi W w ffi ffi Ed MM ffl a S3 Β w K w ffl w KWMWWB w Κ w ® K waww « w WK ww Μ ffi B S3 ffl K w K wa ffi w BW Μ a W w « wawwww K ffi 53 XM w W ww K sww S3 a W » a « S ffl a KM ffi S3 MW ίΰ a WM wwwwua « W w WW w ffi S s K ww » M aaa WW w tc s ffl w B « » ww » w £ K Μ ffi K ffi ww * awsww sec-Bu sec -Bu H White PQ nb £ Λ .UX 1 1 secBu eec'Bu eecBu dmb S d ά a « ha φ 0 M mn ά PQ k CQ ο S sec-Bu mnhamh £ 2 tS • us ί X 1 eecrBu eecrBti sec. Bu eec_Bu D η α 0 ss CQ ά « bm •P dk SS 0 u Φ o HH « K φ Η H u „ I « H • H « KHH id EC ffi w S3 tc « aaw M ww »2 a 03⁄4 s 〇 a Oi cd ε <s 05 9> O o 〇 is o 裘os 147486.doc -17- 201100358 X Ο CQ d S3 ΰ CQ o CD ΰ CQ o GQ CQ d CQ a CO ϋ CQ ΰ c〇ϋ CQ CQ 17b κ ww W (NI z 丨N(Me)2 ! N(Et)2 1----- N(Et)2 ffi NH2 NH2 NH2 1 NH2 w ffi N(Me)2 N(Me)2 N (Me)2 N(Me)2 N(Me)2 N(Me)2 N(Me)2 N(Me)2 N(Me)2 N(Me)2 1 2 W wwwaw W a K ww KW ww ω Aaw W w W w W wa W W S3 wawwwwwwwwwsw M a W w W awaw uniform r-< κ w WK ww « www 1 wwawwww tc wwwww S3 τ·^ WM ζΗ ffi K wwww ffi www 5 wn waww X aww M 宕fH W wawwwwwwwww ffl w ffl wwwwwwwww K a pQ tH ffi ffi ffi wwwawwwwww ffi wwww ffi wwwwwww Λ W w K wwaww ffi w ω s 1 ww a> 1 waw ffl wwa ffi ww with ffi wa Ά waww ffi w M wwwa KK Www ffi ww in w ηχ- /-N ΓΟ Sw/ Λ ww KM wwwwwwwwww ffi K w ffi K » ww ffl wa ffl 汔www X ww K w K wwwawwww ffi M ffi www M w ffi Φ ffl w ffi wawwaw M waawa ffi 0) s 1 ffi ffl w ffi wawww ffi ww K w id ffi w 1 Φ s Φ s 1 Φ swwwwwwwwa K uniform o ω S os 0) δ aw ffi w w K aw a> 1 m W n~Bu n-Bu i-Pr i-Pr CvHex | CyHex Μ Q> s Φ Φ 1 1 1 ww K w ffi www W w 1 1 m n-Bu n-Bu W « 1 1 s 1 φ s 1 w ffi wwwwwwa) 1 wn~Bu n-Bu i-Pr i-Pr CyHex CyHex Λ φ sos φ 0> 1 www K a ffi •i-» W 1 1 n-Bu n-Bu m compound No. M w € so ΠΊΓ1 »Ή w 14b words i-1 16b »H fH 2 20b 21b 22b 24b 1 25b 1 pack -18- 147486.doc 201100358

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a CP 〇CQ Ο GQ d CQ ϋ CQ o CQ a CQ d CO a GQ d CQ b CQ 0 CQ d CD ds 1M g 2: C^lg CM i of 2 e Art (N az <N aws 〇s 5S Wso (N ww 9 f 〇W o WSSO <N ffl g W 9 C<l 2 wu (N a S tN K ss I wws 2: 2 o (N wo KB zfi S <N w 9 z <N 2 wwoz 1 <N wow K a 汔I «Ν ΐΰ W ζ 沄WWS <Ν 沄SW ο SS Μ s s 53 w 〇ss ffi o N w 沄SK gws Ά (N § w Q wo 2 W a O <N wo 2 03⁄4 W gw S w 〇K w K wwwwwwwwwwwwwww WWWW w W aw WKK wwww ffi wwww ffl wwwaw MW κ ΰ K wwwa K ww ¢1 wwwwwwwwww ffi www ffi κ a W wwwaw ffl www K w K wwwaw ffl w K www W Μ W κ ffi KK ffi wwww ffl wwww M wwwwwww ω aw WWW ww ffl wwwww ffi w ffi wwwwswwwwwwww WWW ww ffi w K ww K www ffl www ffi wwwwawww WWW wwww M ffi ww ffi w ffl wwwaawwwww ffi ffi KW κ W Ww K w M wwwwwwwawwwwwwww M ww W Μ W waw MW awww Wwwwwwwwwwawwam W wwwww K a M awwwwawwwwwawwa WWW awww WK wwkwwwwkw ffi wwwawww WWW ww ffl w ffi ws K s % 0 PQ CQ d PQ k <nmk (A m tii island ws CQ hmd *H u •iH so 1 s s CO v> 3 Pp 8 CO port (0 WS ss W 0 Pp b ώ O. ♦ M sw 占 M msd PQ d W wmba PQ mwwws Cp a 3 Pp a 〆υ δ W 3 Pp k PQ h W δ 2 K δ w 占 knm CQ PQ y CO ?* Pp Φ <0 W 甶闰a 甲 h ώ •u (3⁄4 • ms δ w $ S3 PQ co km QQ 〆υ S w 0 m ά PW b £ £ •HS w占wm 3 (3⁄4 h Pp d W w Fp bamhmm W w 0 φ h ά ο W wd (3⁄4 dmd W wg 卜t> i 宕CO 00 00 兵兵 CO 00 GO Pack〇 0 Xi 00 运 CO containing 〇〇 σ> α 赛Oi 均σ>诌α> CD Λ 147486.doc •21 · 201100358 CQ Ο CQ ϋ CQ ΰ CO ΰ CQ o CQ o CQ ϋ c〇o CQ o oo d CQ {N a O <N wasasw 〇w ο (N 任II a S 05 a 9 tn i <N a O ca w § (N 沄g W a B cq aswo (N wsa % C^J 8 2 wsz Szw 3 azazs <N 3 a 2 s S IM "3 β c^ Θ 2: β 8 wwawww ffi wa ffl w ffl μ w W aw W wwwwwaw ffi w ffi ww W ww W w ffi wwww W wwwwwwwwwww ffl aawawww M Wwaw ffi w K w W www ffi wwww in ww M www ffi www Ά W wa 53 wwwwwawwaw K w M www W w ffi KW ffl ww HI wwa ffi awww ffi wa W ww ffi www ffl w tu « wwww « www S3 W wwwwwwwwww K « wwwwwwaw ffi aawwwwwwwwwawaw irj ffl ww W a K wwww K wwwwww ® w ffi K ffl μ w W wwww K wa ffi wwww ffi w ffl ww ffi ww W w M ffi wa ffl wwawwwwws | A PQ name GO CQ 〆Ϊ WW 3 PQ fl A d £.2 s IS | PQ bs 3 PQ v to Si Pp φ <Λ s Pp Φ <n £"^ iJ^ W m 3 ffl d S « ά s 〆2 w W d ά ma WW smh » d to $ ο s PQ CQ k (0 port Pp CO d PQ u % s〆Q m W fl S3 ΰ £ £ 2 s | w 占CQ 0Q名kw 3 CQ us !3 P3 k CO £-^ w W 3 W d :3 Cf d 〆ssw 3 Pp Fi ?3 a d δ mw MW s PQ hd PQ ti tJ- ο rH | rH 〇 o o oo € 〇O yun oi rH if rH iH 5 fH g § uniform rH rH s rH old 汔rK rH tH nai iH rH S3 147486.doc -22- 201100358 In Tables 1 and 2, with respect to the substituent r, Me represents a thiol group, Et represents an ethyl group, Ph represents a phenyl group, Bz represents a benzyl group, and CF3 represents a trifluoromethyl group, n-Bu. Represents n-butyl group, sec_Bu represents a second butyl group, i_Pr represents an isopropyl group, and CyHex represents a cyclohexyl group. Further, in the case of α, it is a tris(trifluoromethanesulfonate) methide anion, and when it is in the case of β, it represents a bis(trifluoromethane) imine anion. The triarylmethane compound of the present invention is used as an oil-based dye composition or an aqueous dye composition, and is used in various coloring compositions such as paints, aqueous inks, oil-based inks, inks for inkjet, and inks for color filters. The oily music composition and the aqueous dye composition can be used for coloring materials such as plain paper, coat paper, plastic film, plastic substrate, and the like. Further, examples of the method of imparting the dye composition of the present invention to a material to be colored include various printing methods such as offset printing, letterpress printing, flexographic printing, and inkjet printing, or spin coating. Coating method such as machine or roll coater. ❹ As described in the present invention, the triarylmethane compound of the present invention and the oil-soluble organic solvent are contained in the case of the oily dye composition, and the triarylmethane compound of the present invention is contained in the case of the aqueous dye. And aqueous media. The oily or aqueous dye composition of the present invention preferably contains the triarylmethane compound of the present invention in an amount of from 2 to 4 parts by weight, more preferably from 0.5 to 20 parts by weight. /. . Further, in the oily or aqueous dye composition of the present invention, in order to adjust the color tone or the like, a colored material other than the above formula (1) may be added as needed. Examples of the color material that can be added include an acid dye, a reactive dye, a direct dye, a cationic dye, a basic 147486.doc -23· 201100358 miscellaneous material, a water-soluble dye, a disperse dye, a solvent organic pigment, and a black pigment. Etc., it can be added in the state of being dissolved in a dye. The state or dispersion of the aqueous dye composition of the present invention is exemplified by water or water. Soluble water, ^, for example, methanol, U, such as one - isopropanol, butanol, isobutyl, second butanol, pentanol, benzyl alcohol and other alcohols; Ethylene, -diol MU ##—Ethylene glycol, triethyl... " B-known, polypropylene glycol, glycerol, trimethyl propyl propylene, 1,3-pentanediol, 15_戍_ ether, ethanediol ·Ethylene glycol single Yin-alcohol single-check, two-two-two-three-B, 1 stay, known as early methyl ether, diethylene glycol monobutyl ether, di-monoethylidene, triethylene glycol monobutyl scale, dipropylene glycol monomethyl Shouting diols and other organisms; amines such as ethanolamine, diethanol diethanolamine, and porphyrin; ketone ketone, guanidine dimethyl + sitting (four). As for the oil-based dye composition of the present invention, the tri-aryl compound of the above formula (1) can be dissolved or dispersed in at least one kind of oil-soluble organic compound.

Prepared in a bath. Examples of the oil-soluble organic solvent that can be used include alcohols such as ethanol, pentanol, octanol, cyclohexanol, and tetrafluoropropanol, and ethylene glycol mono(tetra) and diethyltriol. a diol derivative such as triethylene triol monobutyl ether, propanol monoethyl ether, dipropylene glycol monomethyl ketone, dipropylene glycol monoethyl sulphate, triethanol monoethyl sulphate, ethylene glycol diacetate vinegar, propylene glycol diacetate vinegar Anthracene such as ethyl ethyl ketone or cyclohexyl ketone; ethers such as butyl benzene bond and node bond 'hexidine oxime' ethyl acetate, butyl acetate, ethyl benzoate, and succinic acid butyl ^ (4) 'Vinegar such as lauric acid vinegar; acetonitrile, DFM, diterpenoid 147486.doc •24- 201100358 Polar sulfone, sulfolane, NMP, 2_pyrrolidone and other polar organic solvents. These solvents may be used singly or in combination of two or more. As the dispersing sword which can be used for the oily dye composition, there are mentioned: twelve-burning sodium sulfonate, sodium laurate, a formaldehyde condensate of naphthalenesulfonic acid, alkyl naphthalene, a bismuth (tetra) compound, hibiscus oil a known anionic surfactant such as a condensate of rhyme, an ammonium salt of polyoxyethylene sulfonate, an ammonium polyoxyethylene alkyl phenyl ether sulfate, a polyoxyalkyl ether phosphate, and the like; From ethylene 0 naphthalene derivatives, α, aliphatic alcohol esters of ethylenically unsaturated carboxylic acids, etc., styrene, styrene derivatives, acrylic acid, acrylic acid derivatives, methacrylic acid, methacrylic acid derivatives, cis-butyl Aenedioic acid, maleic acid derivative, maleic anhydride, maleic anhydride derivative, itaconic acid, itaconic acid derivative, fumaric acid, fumaric acid derivative, etc. The block copolymer having less than two kinds of monomers, or the random copolymerization, or the surface molecular dispersant such as the salt, etc., is preferably 10 to 100 by weight with respect to the dispersed pigment compound. % uses one or more of these types. If necessary, add polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether together with the dispersing agent at 0 pigment knife and/or after dispersion. A well-known nonionic surfactant such as a copolymer of ethylene oxide and propylene oxide, or a known antifoaming agent based on oxime or acetylene. As a method of dispersing a pigment in fine particles, a method using a sand mill (bead mill), a roll mill, a ball mill, a paint shaker, an ultrasonic disperser, a microfluidizer, or the like can be mentioned. Among these, a sand mill (bead mill) is preferred. Further, in the sand mill (bead mill), the pigment is pulverized, and it is preferred to increase the pulverization efficiency by using beads having a small particle size, increasing the filling ratio of the beads of 147486.doc -25 - 201100358, and the like. The treatment is carried out under the conditions, and after the pulverization treatment, the elementary particles are removed by filtration, centrifugation or the like. The dye composition of the present invention may further contain a surface conditioner, an antiseptic antifungal agent, a pH adjuster, and the like as other additives. Examples of the surface conditioning agent include polyoxazine or polydimethyl sulphate & 7 stanozane surfactant; and as an antiseptic and antifungal agent, sodium decarboxylate or sodium benzoate may be mentioned. Smaller than sodium thiones, sulphur sulphur, u_benzoxanthine, sulphonate-3, ketone amine salt, etc.; as a pH adjuster, sodium hydroxide hydroxide The hydroxides such as potassium and hydrazine are metal-based, and the tertiary amines such as tris-2, diethanolamine, 4-glycolamine, and diethylethanolamine are specifically added and can be added as needed. Further, in order to improve the fixability of the pigment to the colored body in the oily or aqueous dye composition of the present invention, it is preferred to contain a polyamine or a polyamine which is compatible with the medium in the composition within a necessary range. Carbamate type, polyfluorene type, % milk type or polyacrylic resin. Further, in order to improve the fixability, a monomer, an oligomer or a polymerization initiator having an ethylenically unsaturated group may be contained in an essential range. The oily or aqueous composition of the present invention can be prepared by dissolving or dispersing and mixing the above components in a solvent. EXAMPLES Hereinafter, the present invention will be specifically described by examples, but the present invention is not limited to the examples. Further, in the examples, "parts" means "parts by weight" unless otherwise specified. The decomposition temperatures of the various compounds obtained in the examples were determined by TG/DTA. χ, moist heat resistance or water resistance 147486.doc, 26-201100358, etc. The chromaticity (L value, a value, b value) of the dye colored body was measured and evaluated by the following colorimetric measuring device. The measurement device name is as follows. 1. TG/DTA (indicating simultaneous measurement of thermal weight): . The name of the product manufactured by Seik〇 Instruments (tg/DAT 220) 2. Colorimetric measuring device: Uv_3 manufactured by Shimadzu Corporation (shares) 150 Example 1 (Table 1 In the synthesis of the compound No. la in the formula (100), 2 parts of the basic blue 7 (manufactured by Tokyo Chemical Industry Co., Ltd., decomposition temperature: 21 7 ° C) of the following formula (100) was dissolved in 150 parts of water, and stirred while stirring. A solution of 21 parts of a diced salt of tris(trifluoromethanesulfonate) methoxide was dissolved in 30 parts of acetonitrile. After mixing for 3 hours, the precipitated crystals were taken out by filtration, washed with water, and dried to obtain 1.5 parts of a blue crystal (triarylmethane compound of the present invention). Decomposition temperature: 256. (Example: Synthesis of Compound ν〇·2a in Table 1) Two parts of the blue (7) of the following formula (1 〇〇) were dissolved in 5 parts of water, and were added while being mixed. A solution obtained by dissolving 1 _2 parts of potassium bis(trifluoromethanesulfonate)imide in 10 parts of water, and after stirring for 3 hours, the precipitated precipitate was taken out by filtration, washed with water, and dried to obtain blue. Color crystal (triaryl fluorene compound of the present invention) 0.7 parts. Decomposition temperature: 240 ° C. Example 3 Preparation of oily dye composition and dye coloring body 'Dissolved 0.5 parts in 10 parts of tetrafluoropropanol The oily dye composition was prepared by the compound No. la and the compound N〇2a obtained in the above examples. The obtained oily dye composition was spin-coated on a polycarbonate substrate and dried at 80 C for 30 minutes to prepare a dye. Coloring body 147486.doc -27· 201100358 Further, in the following Table 5 and 矣〇丄/1, Comparative Example I in the garment 9 shows the use of the basic blue 7 of the following formula (100). • Test results of those who prepare dye colorants. [Chemical 4]

Moisture and Heat Resistance Test 1 The dye coloring body obtained by the above method was placed in a constant temperature wetting machine of 851:, 85% RH for 4 () hours. The color difference was determined by the following equation using a spectrophotometer, a C light source as a standard light, and a 2 degree angle of view, for the dye coloring l value, a value, and b value before and after the test. Further, the smaller the chromatic aberration, the more excellent the change in hue is. Chromatic aberration - [(L value before test - L value after test) 2 + (a value before test - value a after test) 2+ (b value before test - b value after test) 2] 1/2 Heat resistance test The measured values and color differences of the medium color measurement are shown in Tables 3 to 6 below. The color measurement results of Compound No. 1 a are shown in Table 3 below. (Table 3) L value a value b value before test 84.15 -6.23 -24.43 after test 84.90 -6.37 -23.26 before and after test -0.75 0.14 -1.17 147486.doc •28- 201100358 The color measurement results of compound No. 2a are shown in In Table 4 below. (Table 4) L value a value b value Before test 82.71 -6.45 -27.04 After test 83.37 -7.33 -25.84 Difference before and after test -0.66 0.88 -1.20 The color measurement results of Comparative Example 1 are shown in Table 5 below. ·

(Table 5) L value a value b value before test 79.62 -5.19 -31.95 after test 89.70 -4.29 -11.66 before and after test -10.08 -0.90 -20.29 Compound No. will be obtained according to Table 3 to Table 5 above, and Comparative Example 1 The results of the color difference are shown in Table 6 below. (Table 6) la, Compound No. 2a Compound No. la Compound No. 2a Comparative Example 1 〇 Color difference 1.4 1.6 22.7 According to the results of Table 6, it was confirmed that the dye coloring body of Comparative Example 1 was tested. The color difference between the front and the back is 22.7, which is not a value of a large amount. In contrast, the color difference of the dye coloring matter of the present invention is 丨4 Angstrom 1.4 and 1.6 shows a very small value, and thus the thirst resistance is extremely excellent. · 'Finance test 1 will be placed in the warm water of TC for 5 minutes in the above method. Use spectrophotometer, summer 5 10 as the standard light C light source, 2 degree angle of view, The color difference L value, a value, and b value of the dyes of the dyes before and after the test were obtained by the following formula 147486.doc -29. 201100358. In addition, the smaller the color difference, the less the change in hue. The better the color difference = [(L value before test - L value after test) 2+ (a value before test - value a after test) 2+ (b value before test - b value after test) 2] 1/2. The measured values and color differences of the color measurement in the water resistance test are shown in the following Tables 7 to 10. The color measurement results of the compound No. 1 a are shown in the following Table 7. (Table 7) Test before the test Before and after the difference L value a value b value 84.15 -6.23 -24.43 84.96 -6.12 -22.60 -0.81 -0.11 -1.83 The color measurement results of compound No. 2a are shown in Table 8 below. (Table 8) Test before test Before and after the difference L value a value b value 82.71 -6.45 -27.04 86.43 -6.08 -20.67 -3.72 -0.37 -6.37 The color measurement results of Comparative Example 1 are shown in Table 9 below. (Table 9) Test before test After the test, the difference L value a value b value 79.62 -5.19 -31.95 99.26 -0.58 -1.53 19.64 -4.61 -30.42 The results of the color difference of the compound N〇. la, and the comparative example 1 are obtained according to the above Tables 7 to 9. In the following Table 1 化合物. Compound No. 2a 1474S6.doc • 30- 201100358 (Table 10) Color difference compound No. la 2.0 Compound No. 2a 7.4 Comparative Example 1 36.7 It is clear from the results of Table 10 that Comparative Example 1 The color difference of the dye coloring body before and after the test was 36.7, which showed a very large value. On the other hand, the color difference of the dye colored body of the present invention was 2, 0 and 7.4, which showed a very small value, and thus the water resistance was extremely excellent. Synthesis of Compound No. 5a in Table 1) 2 parts of Basic Blue 26 (manufactured by Tokyo Chemical Industry Co., Ltd., decomposition temperature: 223 ° C) of the following formula (101) was dissolved in 2 parts of DMF and stirred. A solution obtained by dissolving 2 to 5 parts of a diced salt of tris(trifluoromethanesulfonate) methoxide in 20 parts of DMF was added, and after stirring for 2 hours, the solution was filtered, and water was added to the obtained filtrate. Crystallized, washed with water, dried, and obtained in purple Crystallization (triarylmethane compound of the present invention) was carried out in an amount of 267 ° C. [Chemical 5]

147486.doc •31·201100358 Example 5 Preparation of Oily Dye Composition and Dye Colorant An oily dye composition was prepared by dissolving 0.5 part of the compound No. 5a obtained in the above Example 4 in 10 parts of tetrafluoropropanol. . The resulting oily dye composition was spin coated onto a polycarbonate substrate at 8 Torr. The dye coloring body was prepared by drying under the arm for 3 minutes. Further, Comparative Example 2 in the following Table 12 shows the evaluation results of the dye-colored body prepared in the same manner using the blue color 26 of the above formula (丨〇丄). The heat and humidity test 2 is the same as the heat and humidity resistance test 1. The measured values and color differences of the color measurement are shown in the following table. The color measurement results of Compound No. 5a are shown in the following Tables. (Table 11) L value a value b value before test 86.08 - 6.87 -21.15 After test 86.24 - 6.86 -20.84 Before and after test -0.16 -0.01 -0.31 The color measurement results of Comparative Example 2 are shown in Table 12 below (Table 12) L value a value b value before test 85.54 -9.17 -21.25 88.60 after test 8.40 -15.42 difference before and after test -3.06 -0.77 -5.83 The color difference of compound No. 5a and comparative example will be obtained according to Table 11 and Table 12 above. The results are shown in Table 13. 147486.doc -32- 201100358 (Table 13) Color difference compound No. 5a 0.3 Comparative Example 2 6.6 It is clear from the results of Table 13 that the color difference of the dye coloring body of Comparative Example 2 before and after the test was 6.6, indicating a very large value 'relative Here, the dye coloring matter of the present invention has a color difference of 0.3 and shows a very small value, so that it is extremely excellent in moist heat resistance.

Water resistance test 2 The test method is the same as the water resistance test. The measured values and color differences of the color measurement are shown in Tables 14 to 16 below.

The color measurement results of Compound No. 5a are shown in Table 14 below. (Table 14) Before the test After the test The difference between the test and the L value 86.66 88.62 -1.96 a value -6.78 -3.64 -3.14 b value -20.34 -11.89 -8.45 The color measurement results of Comparative Example 2 are shown in Table 5 below. (Table 15) L value a value b value 85.57 -9.17 -21.25 94.55 3,92 -1.28 -8.98 -13.09 -19.97 Test before and after the test before and after the test; according to Table 14 and Table 15 above to find the compound No. 5a and comparison The results of the color difference of Example 2 are shown in Table 16 below. 147486.doc -33- 201100358 (Table 16) Color difference compound No. 5a 9.2 Comparative Example 2 25.5 It is clear from the results of Table 16 that the color difference of the dyed color body of Comparative Example 2 before and after the test showed a very large value of 25.5. Here, the dye coloring matter of the present invention has a color difference of 9.2 which shows a very small value, and thus is extremely excellent in water resistance. Example 6 (Synthesis of Compound No. 45a in Table 1) Two parts of the dye of the following formula (102) were dissolved in a mixed solution of 30 parts of water and 75 parts of methanol, and added to 2 parts of DMF while being mixed. A solution obtained by dissolving 2,48 parts of a cerium salt of tris(trifluoromethanesulfonate) hydrazide in a mixed solution of 12 parts of methanol. After heating and stirring at 60 °C for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain a blue crystal (triarylmethane compound of the present invention) of 1.3 parts. Decomposition temperature: 262 ° C. [Chemical 6]

Et2NN^N f^vY^NEt2

cT

147486.doc •34- (102) 201100358 Example 7 (Synthesis of Compound No. 57a in Table 1) 2.5 parts of the dye of the following formula (103) was dissolved in a mixed solution of 2 parts of water and 38 parts of decyl alcohol. A solution obtained by dissolving 2.87 parts of a diced salt of tris(trifluoromethanesulfonate) methoxide in a mixed solution of 2 parts of DMF and 12 parts of methanol was added while stirring. After heating and stirring at 60 °C for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain a blue crystal (triarylmethane compound of the present invention) of 2·8 parts. Decomposition temperature: 269 ° C. [Chemistry 7]

NEt2 c! (103)

Example 8 (Synthesis of Compound No. 69a in Table 1) 3 parts of the dye of the following formula (104) was dissolved in a mixed solution of 10 parts of water and 53 parts of methanol, and added to 3 parts of DMF while stirring. A solution of 2.94 parts of a diced salt of tris(trifluoromethanesulfonate) methide was dissolved in a mixed solution of 25 parts of methanol. After heating and stirring at 60 °C for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain 3.5 parts of a blue crystal (triaryl decane compound of the present invention). Decomposition temperature: 267 ° C. 147486.doc -35- 201100358 [Chem. 8]

Example 9 (Synthesis of Compound No. lb in Table 2) One part of the peacock oxalate salt of the following formula (105) (decomposition temperature: 175 ° C) was dissolved in 50 parts of water, and stirred while stirring. A solution of 2 parts of cerium salt of tris(trifluoromethyl hydrazine) hydrazide was dissolved in 5 parts of DMF. After stirring for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain 0.5 parts of a dark green crystal (triaryl decane compound of the present invention). Decomposition temperature: 190 °C. Example 10 (Synthesis of Compound No. 3b in Table 2) 5 parts of basic blue (decomposition temperature: i90 ° C) of the following formula (106) was dissolved in 500 parts of water and stirred while being added thereto. A solution obtained by dissolving 2 parts of cerium salt of tris(trifluoromethanesulfonate) hydrazide in #dmF. After stirring for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain 7 parts of a blue crystal (triarylmethane compound of the present invention). Decomposition temperature: 230 〇C. Example 11 (Synthesis of Compound No. 5b in Table 2) 147486.doc • 36- 201100358 An experimental purple 3 of the following formula (107) (decomposition temperature: 2 〇 5. 〇 5 parts dissolved in 500 parts of water) While stirring, a solution obtained by dissolving a salt of tris(difluoromethanesulfonate) methoxide in a portion thereof is added, and after stirring for 3 hours, the precipitated crystals are taken out by filtration, washed with water, and dried to obtain Purple crystal (triarylmethane compound of the present invention) 12 parts. Decomposition temperature: 240 ° C. Example 12 Preparation of oily dye composition and dye colorant 〇 ^ ^ Dissolved in 10 parts of tetrahydropropanol 5 parts of the compound No. lb, the compound No. 3b, and the compound No. 5b obtained in the above respective examples, to prepare an oily dye composition. The obtained oily dye composition was spin-coated on a polyacid acid substrate. The dye colored body was prepared by drying at 80 ° C for 30 minutes. Comparative Example 3 shown in Tables 17 and 18 below used the peacock oxalate salt of the following formula (105), and Comparative Example 4 was used. The basic blue 1 of the formula (1〇6) and the comparative example 5 are the following formula (107). Violet 3, and the dye prepared in the same manner as color bodies ^. [Formula 9] 0

147486.doc •37· (105) 201100358 [化 ίο]

(106) [Chem. 11]

(107) Water resistance test 3 The dye coloring body obtained by the above method was placed in 7 liters (3c of warm water for 2 seconds. Using a spectrophotometer to measure the color of the dye before and after the test as a standard light c light source and a 2 degree viewing angle Color [value ' a value, b value, the color difference is obtained by the following formula. In addition, the smaller the color difference is, the smaller the change in hue is, and the more excellent. The color difference = [(pre-test L value - L value after test) 2 + (pre-test & value_a value after test) 2+ (b value before test - b value after test) 2] 1/2. The measured value and color difference of the color measurement in the water resistance test are shown in Table 17 below. To Table 23. 147486.doc • 38· 201100358 Compounds (Table 17) The results of the color difference ib before and after the test are shown in Table 17 below. L value 93.25 93.58 -0.33 a value -10.94 -8.79 - 2.15 b value - 6.37 '5.62 -0.75 Ο The color measurement results of compound No. 3b are shown in Table 8 below (Table 18) L value a value b value before test 92.12 -11.73 -10.53 after test 92.44 -10.16 - 9.37 Difference before and after test -0.32 -1.57 -1.16 The color measurement results of compound N 〇. 5b are shown below. (Table 19) L value a value b value before test 77.97 19.33 -32.25 After test 79.58 16.61 -28.95 Difference before and after test -1.61 2.72 -3.30 The color measurement results of Comparative Example 3 are shown in Table 20 below.

(Table 20) L value a value b value before test 89.77 - 10.94 -4.49 After test 100.22 -0.21 -0.41 Before and after test -10.45 -10.73 -4.0S The color measurement results of Comparative Example 4 are shown in Table 21 below. (Table 21) L value a value before test 95.83 -7.27 After test 100.16 -0.13 Test before and after the difference -4.33 -7.14 Value 934845 b5.0.5. 147486.doc -39- 201100358 The color measurement results of Comparative Example 5 are shown below In Table 22. (Table 22) L value before test A value b value 75.14 15.62 -37.06 After test 99.65 0.21 -1.13 Test before and after the difference -24.51 15.41 -35.93 Compound No. lb, No. 3b, No will be obtained according to Table 17 to Table 22 above. The results of the color difference of 5b and Comparative Examples 3, 4 and 5 are shown in Table 23 below. (Table 23) Color difference compound No. lb 2.3 Compound No. 3b 2.0 Compound No. 5b 4.6 Comparative Example 3 15.5 Comparative Example 4 10.0 Comparative Example 5 46.1 It is clear from the results of Table 23 that the dye colored body of Comparative Example 3 was before and after the test. The color difference of 15.5 shows a large value. In contrast, the dye coloring body of the compound No. 1b of the present invention having the same cationic portion has a color difference of 2 3 and exhibits a small value, so that the water resistance is extremely excellent. Similarly, the dye colorants of Comparative Examples 4 and 5 had a color difference of 1 Å before and after the test, and the sputum showed a large value. In contrast, the dyes of the compounds of the present invention N〇. 31? and No. 5b were colored. The color difference of the body is 2.0 and 4.6 shows a very small value. Example 13 (Synthesis of Compound No. 53b in Table 2) 2.31 parts of the dye of the following formula (108) was dissolved in a mixed solution of 2 parts of water and 120 parts of methanol, and was added while being added to 4.2. A solution of 2.30 parts of a diced salt of tris(trifluoromethanesulfonate) methoxide dissolved in DMF. After stirring for 3 hours, the precipitated crystals were taken out by filtration, washed with water, and dried, 147486.doc -40 - 201100358 to obtain 3.64 parts of blue crystals (Compound No. 53b). Decomposition temperature: 231. . . [化 12]

9c N(n_Bu)2 (103) Example 14 (Synthesis of Compound No. 2lb in Table 2). 3.1 parts of the dye of the following formula (109) was dissolved in a mixed solution of 150 parts of water and 72 parts of decyl alcohol. While stirring, a solution obtained by dissolving 3.55 parts of a ruthenium salt of tris(trifluoromethanesulfonate) methide in 6.3 parts of a mixed solution of DMF and 16 parts of methanol was added. After heating and stirring at 40 °C for 3 hours, the precipitated crystals were collected by filtration, washed with water and dried to give 1.63 parts of a blue crystal (Comp. No. 21b). Decomposition temperature: 234 ° C. [Chem. 13]

147486.doc -41 - 201100358 Example 15 (Synthesis of Compound No. 33b in Table 2) 1.0 part of the dye of the following formula (110) was dissolved in a mixed solution of 100 parts of water and 40 parts of decyl alcohol while stirring A solution of 1.3 parts of a cerium salt of tris(trifluorosulfonium sulfonate) hydrazide dissolved in a mixed solution of 3.2 parts of DMF and 8 parts of decyl alcohol was added. After heating and stirring at 30 °C for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to obtain a crystal of blue crystals (Comp. No. 33b). Decomposition temperature: 232 ° C. [Chem. 14]

Example 16 (Synthesis of Compound No. 69b in Table 2)

1.0 part of the dye of the following formula (111) was dissolved in a mixed solution of 100 parts of water and 40 parts of decyl alcohol, and while being stirred, was added to a mixed solution of 3.2 parts of DMF and 8 parts of decyl alcohol to dissolve tris (trifluoromethyl). A solution of 0.65 parts of the sulfonate methionate. After heating and stirring at 40 °C for 3 hours, the precipitated crystals were taken out by filtration, washed with water and dried to give 0.73 parts of a blue crystal (Comp. No. 69b). Decomposition temperature: 277 ° C 147486.doc -42- 201100358 [Chem. 15]

As described above, it is clear that the triarylmethane compound represented by the above formula (I) of the present invention is excellent in heat resistance according to the comparison of the decomposition temperature thereof, and the material colored body has characteristics excellent in moist heat resistance and water resistance, and the present invention The triarylmethyl-based dye-based color filter ink or inkjet ink has a wide industrial range and has high industrial value. 〇基染之等 147486.doc

Claims (1)

201100358 VII. Patent application scope: 1. A triarylmethane compound represented by the formula (1) [Chemistry 16] Αιγ Ar2 Ar3 X (1) (in the formula (1) 'ΑΓι, Ai*2 and A1·3 Separately, the carbon atom is bonded to Ο. The aromatic residue of the carbon atom, χ- indicates bis(trifluoromethanesulfonate) anion or bis(difluoroanthracene) methide anion). For example, the diarylmethane compound of the formula 1 is represented by the formula (2): [Chem. 17] ν ^ τ a~R "Individually represent hydrogenogen +, carbon number r base, stupid $this, breast mat, basic base or base group" "independently, respectively, 147486.doc 201100358 ', 卞' χ meaning The upper return type is the same). 3-. The sulphate compound of claim 3, wherein Χ is a tris(trifluorosulfonium sulfonate) methide anion. It is represented by the general formula (3). 4. The triarylmethane compound of claim 1 is: [Chem. 18] (In the formula (7), Rb1 to R4b each independently represent a hydrogen atom, an alkyl group having a carbon number, a phenyl group or a sulfhydryl group, and R5b to R6b, respectively, independently represent a hydrogen atom, a filament having a carbon number of 1 to 6 or a self-atomic atom. "Expression of a hydrogen atom, a carbon number of a carbon atom, a good atom or an amine group, and the meaning of X_ is the same as the above formula (1).) 5. The compound of claim 4, wherein the aryl group is three (three gases).醢 醢) 曱 化物 阴离子 阴离子 6 6 6 6 6 6 6 6 6 6 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 油 有 有 有 有7. An aqueous dye composition comprising an -aryl alcohol-containing compound according to any one of items 1 to 5 and an aqueous medium. 147486.doc 201100358 IV. Designated representative figure : (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: Αγι^,Αγζ Χ_ Ar3 ( 1) 147486.doc