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WO2019044872A1 - Composé lié à la rhodamine - Google Patents

Composé lié à la rhodamine Download PDF

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Publication number
WO2019044872A1
WO2019044872A1 PCT/JP2018/031869 JP2018031869W WO2019044872A1 WO 2019044872 A1 WO2019044872 A1 WO 2019044872A1 JP 2018031869 W JP2018031869 W JP 2018031869W WO 2019044872 A1 WO2019044872 A1 WO 2019044872A1
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group
general formula
compound
preferable
represented
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English (en)
Japanese (ja)
Inventor
隆二 加藤
正美 榎木
克史 鈴木
哲司 村瀬
重明 今關
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Nihon University
Fujifilm Wako Pure Chemical Corp
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Nihon University
Fujifilm Wako Pure Chemical Corp
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Priority to JP2019539559A priority Critical patent/JPWO2019044872A1/ja
Publication of WO2019044872A1 publication Critical patent/WO2019044872A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes

Definitions

  • the present invention relates to a novel compound used for a color filter or the like, and a coloring composition comprising the compound.
  • color filters used in color liquid crystal display devices and color image pickup tube elements are filter segments (pixels) in the form of fine bands (stripes) formed of filter layers of respective colors formed on the surface of a transparent substrate such as glass. Are arranged in parallel or in cross, or in which fine filter segments are arranged in a fixed arrangement in vertical and horizontal directions.
  • the quality items required for color filters include lightness and contrast ratio. For example, since color filters with low lightness have low light transmittance and a dark screen, it is required to increase the lightness of the color filters. In addition, a color filter with a low contrast ratio causes a blurred screen, and therefore, a high contrast is required.
  • rhodamine dyes used for color filters
  • coloring compositions for color filters containing xanthene dyes Patent Document 2
  • Non-Patent Document 1 a compound in which rhodamine derivatives having an isothiocyanate group are linked
  • Patent Document 3 a compound in which pentacyclic xanthylium derivatives are linked, and the like have been reported.
  • rhodamine dyes represented by rhodamine B can suppress the fluorescence yield by forming an association in a high concentration solution, but under low concentration conditions, the association is It was not formed and could not suppress the fluorescence yield. Then, this invention makes it a subject to provide the rhodamine type-dye which can form an aggregate also in low concentration conditions, and can suppress a fluorescence yield.
  • a compound represented by the following general formula (1) (hereinafter sometimes abbreviated as the compound of the present invention).
  • R 1 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Y 1 represents -O- or -NH-
  • a 1 represents And a linear alkylene group of 1 to 12 carbon atoms which may have a substituent, and the substituent is a hydroxy group, an alkyl group of 1 to 6 carbon atoms, or a group represented by the following general formula (2)
  • Represents (In General Formula (2), R 7 represents a hydrogen atom or a methyl group, Y 2 represents -O- or -NH-, and A 2 represents a single bond or a linear alkylene having 1 to 6 carbon atoms Represents a group)
  • An - represents an anion; two R 1, two R 2, two R 3, two R 4, two R 5, two R 6, two Y 1 and two An -,
  • a 1 is a group represented by the following general formula (3).
  • R 8 represents a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms or a group represented by the general formula (2)
  • n 1 represents an integer of 0 to 5
  • n 2 represent an integer of 1 to 6
  • n 3 represents an integer of 0 to 5
  • n 3 R 8 and n 3 n 1 may be the same or different.
  • the total number of carbons in the general formula (3) (excluding the number of carbons in R 8 ) is 1 to 12.
  • a colored composition comprising the compound according to any one of the above [1] to [5] (hereinafter sometimes abbreviated as the colored composition of the present invention).
  • a coloring composition for color filter comprising the compound according to any one of the above [1] to [5].
  • the compound of the present invention is capable of forming an aggregate under low concentration conditions, which was difficult with conventional rhodamine dyes, and exhibits an excellent effect of suppressing the fluorescence yield. Therefore, the compound of the present invention is used for forming colored pixels such as color filters used in liquid crystal display (LCD) and solid-state imaging devices (CCD, CMOS etc.), printing ink, inkjet ink, and coating In particular, it is suitable for color filters of liquid crystal display devices. Further, it can be molded into a sheet, a film, a bottle, a cup or the like by a conventionally known molding method and used as a colored resin molded product.
  • LCD liquid crystal display
  • CCD solid-state imaging devices
  • FIG. 16 is a graph showing the results of absorbance measurement for the compound of the present invention (rhodamine-linked compound: compound 7) obtained in Experimental Example 3 and Rhodamine B.
  • FIG. 3 the solid line represents the result of Compound 7, and the broken line represents the result of Rhodamine B. It is a graph which shows the result of the light absorbency measurement with respect to the compound (rhodamine coupling compound: compound 8) of this invention obtained by Experimental example 4, and rhodamine B.
  • the solid line represents the result of Compound 8 and the broken line represents the result of Rhodamine B.
  • FIG. 16 is a graph showing the results of absorbance measurement for the compound of the present invention (rhodamine-linked compound: compound 10) obtained in Experimental Example 5 and Rhodamine B.
  • FIG. 5 the solid line represents the result of Compound 10, and the broken line represents the result of Rhodamine B. It is a graph which shows the result of the light absorbency measurement with respect to the compound (rhodamine coupling compound: compound 12) of this invention obtained by Experimental example 6, and rhodamine B.
  • the solid line represents the result of Compound 12, and the broken line represents the result of Rhodamine B.
  • R 1 to R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Y 1 represents -O- or -NH-
  • a 1 represents And a linear alkylene group of 1 to 12 carbon atoms which may have a substituent, and the substituent is a hydroxy group, an alkyl group of 1 to 6 carbon atoms, or a group represented by the following general formula (2)
  • Represents (In General Formula (2), R 7 represents a hydrogen atom or a methyl group, Y 2 represents -O- or -NH-, and A 2 represents a single bond or a linear alkylene having 1 to 6 carbon atoms Represents a group)
  • An - represents an anion; two R 1, two R 2, two R 3, two R 4, two R 5, two R 6, two Y 1 and two An -, respectively Represents the same thing.
  • the alkyl group having 1 to 6 carbon atoms in R 1 to R 6 in the general formula (1) may be linear, branched or cyclic, and among them, linear or branched Is preferred, and linear is more preferred. Further, among the alkyl group having 1 to 6 carbon atoms, one having 1 to 4 carbon atoms is preferable.
  • R 1 and R 6 in the general formula (1) a hydrogen atom, a methyl group and an ethyl group are preferable, a hydrogen atom and a methyl group are more preferable, and a hydrogen atom is particularly preferable. Moreover, it is preferable that R 1 and R 6 are the same substituent.
  • R 2 and R 5 in the general formula (1) an alkyl group having 1 to 6 carbon atoms is preferable, and a linear or branched alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group and an ethyl group are preferable. Is more preferred, and ethyl is particularly preferred. Moreover, it is preferable that R 2 and R 5 are the same substituent.
  • R 3 and R 4 in the general formula (1) a hydrogen atom and a linear or branched alkyl group having 1 to 4 carbon atoms are preferable, a hydrogen atom, a methyl group and an ethyl group are more preferable, and a hydrogen atom And the ethyl group is more preferable, and the ethyl group is particularly preferable. Moreover, it is preferable that R 3 and R 4 are the same substituent.
  • Y 1 in the general formula (1) -O- is preferable.
  • the C 1 to C 12 linear alkylene group in the “C 1 to C 12 linear alkylene group which may have a substituent (s)” in A 1 of the general formula (1) has 2 to 8 carbon atoms Are preferable, and those having 2 to 5 carbon atoms are more preferable. Specifically, methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group are mentioned.
  • ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene and octamethylene are preferable, and ethylene, trimethylene, tetramethylene and pentamethylene are more preferable.
  • the number of substituted linear-containing linear alkylene groups having 1 to 12 carbon atoms in A 1 of General Formula (1) is usually 1 to 5, preferably 1 to 3, more preferably 1 or 2, particularly preferably It has one substituent.
  • the substituent is a hydroxy group, an alkyl group having 1 to 6 carbon atoms, or a group represented by the general formula (2). When two or more substituents are present, the substituents may be the same or different, but preferably all of the substituents are the same.
  • alkyl group having 1 to 6 carbon atoms in the substituent examples include the same ones as the alkyl group having 1 to 6 carbon atoms in R 1 to R 6 in the general formula (1), and preferable examples are also the same.
  • Y 2 in the general formula (2) -O- is preferable. Further, Y 2 in the general formula (2) is preferably the same as Y 1 in the general formula (1), and it is more preferable that both Y 1 and Y 2 be —O—.
  • the linear alkylene group having 1 to 6 carbon atoms in A 2 of the general formula (2) is preferably one having 1 to 3 carbon atoms. Specific examples thereof include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group and a hexamethylene group. A methylene group, an ethylene group and a trimethylene group are preferable, and a methylene group is more preferable.
  • a 2 in the general formula (2) a single bond and a linear alkylene group having 1 to 3 carbon atoms are preferable, and a single bond and a methylene group are more preferable.
  • Preferred examples of the group represented by the general formula (2) include groups represented by the following general formula (2-1). (In general formula (2-1), R 7 and A 2 are the same as above.)
  • Preferred specific examples among the groups represented by the general formula (2-1) include groups represented by the following formulas (101) to (108), and among them, the groups represented by the formulas (101) to (104)
  • the group represented by the formula (102) or (104) is more preferable, and the group represented by the formula (104) is particularly preferable.
  • a substituent of “a C 1 to C 12 linear alkylene group which may have a substituent (s)” in A 1 of General Formula (1) a hydroxy group, a linear or branched C 1 carbon atom, An alkyl group of to 4 and a group represented by formula (2-1) are preferred; a hydroxy group and a group represented by formulas (101) to (108) are more preferable; a hydroxy group and a group represented by formula (101) to (104) More preferred are the groups shown); hydroxy groups are particularly preferred.
  • linear alkylene group having 1 to 12 carbon atoms which may have a substituent in A 1 of General Formula (1) include, for example, a group represented by the following General Formula (3).
  • R 8 represents a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms or a group represented by the general formula (2)
  • n 1 represents an integer of 0 to 5
  • n 2 represent an integer of 1 to 6
  • n 3 represents an integer of 0 to 5
  • n 3 R 8 and n 3 n 1 may be the same or different.
  • the total number of carbons in the general formula (3) (excluding the number of carbons in R 8 ) is 1 to 12.
  • Examples of the alkyl group having 1 to 6 carbon atoms in R 8 in the general formula (3) include the same alkyl groups having 1 to 6 carbon atoms in R 1 to R 6 in the general formula (1). It is the same.
  • R 8 in the general formula (3) a hydrogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 4 carbon atoms, and a group represented by the general formula (2-1) are preferable; hydrogen An atom, a hydroxy group and a group represented by the formulas (101) to (108) are more preferable; a hydrogen atom, a hydroxy group and a group represented by the formulas (101) to (104) are more preferable; More preferred is a hydrogen atom.
  • n 1 in the general formula (3) is preferably an integer of 0 to 3, more preferably 0 or 1, and particularly preferably 1;
  • R 8 is not a hydrogen atom (R 8 is In the case of a hydroxy group, an alkyl group having 1 to 6 carbon atoms or a group represented by the general formula (2), an integer of 1 to 3 is preferable, 1 or 2 is more preferable, and 1 is particularly preferable.
  • n 2 in the general formula (3) is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and particularly preferably 2; R 8 is not a hydrogen atom (R When 8 is a hydroxy group, an alkyl group having 1 to 6 carbon atoms or a group represented by the general formula (2), an integer of 1 to 3 is preferable, 1 or 2 is more preferable, and 1 is particularly preferable.
  • n 3 in the general formula (3) an integer of 0 to 3 is preferable, 0 or 1 is more preferable, and 1 is particularly preferable.
  • the total number of carbons in the general formula (3) (excluding the number of carbons in R 8 ) is preferably 2 to 8, and more preferably 2 to 5.
  • the total number indicates the number calculated by the formula “(n 1 +1) ⁇ n 3 + n 2 ”.
  • R 9 represents a hydrogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 4 carbon atoms, or a group represented by the general formula (2-1);
  • n 4 represents an integer of 0 to 3
  • n 5 represents an integer of 1 to 4; and when R 9 is not a hydrogen atom, n 4 and n 5 are each independently And represents an integer of 1 to 3.
  • the linear or branched alkyl group having 1 to 4 carbon atoms as R 9 in General Formula (5) includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and an isobutyl group, A sec-butyl group and a tert-butyl group are mentioned, and a methyl group and an ethyl group are preferable.
  • a hydrogen atom, a hydroxy group and a group represented by the formulas (101) to (108) are preferable; a hydrogen atom, a hydroxy group and a group represented by the formulas (101) to (104) Hydrogen atom and hydroxy group are more preferable; hydrogen atom is particularly preferable.
  • n 4 in the general formula (5) is preferably 0 or 1, and particularly preferably 1;
  • R 9 is not a hydrogen atom (R 9 is a hydroxy group, linear or branched) 1 or 2 is more preferable, and 1 is particularly preferable in the case of the following alkyl group having 1 to 4 carbon atoms or the group represented by the general formula (2-1).
  • n 5 in the general formula (5) is preferably an integer of 1 to 3, particularly preferably 2; R 9 is not a hydrogen atom (R 9 is a hydroxy group, linear Alternatively, in the case of a branched alkyl group having 1 to 4 carbon atoms or a group represented by the general formula (2-1), 1 or 2 is more preferable, and 1 is particularly preferable.
  • R 9 is not a hydrogen atom, n 4 and n 5 are preferably identical.
  • Specific examples of the group represented by the general formula (5) include, for example, -(CH 2 ) 2 -,-(CH 2 ) 3 -,-(CH 2 ) 4 -,-(CH 2 ) 5 -,-(CH 2 ) 6 -,-(CH 2 ) 7 -,-( CH 2) 8 -; -CH 2 -CH (OH) -CH 2 -, - CH 2 -CH (OH) - (CH 2) 2 -, - CH 2 -CH (OH) - (CH 2) 3 -, - (CH 2) 2 -CH (OH) - (CH 2) 2 -, - (CH 2) 2 -CH (OH) - (CH 2) 3 -, - (CH 2) 3 -CH (OH) - (CH 2) 3 -; -CH 2 -CH (CH 3) -CH 2 -, - CH 2 -CH (CH 3) - (CH 2) 2 -, - CH 2 -CH (CH 3)
  • a group according to group A and a group according to group B are preferred; -(CH 2 ) 2 -,-(CH 2 ) 3 -,-(CH 2 ) 4 -,-(CH 2 ) 5 -,-(CH 2 ) 6 -,-(CH 2 ) 7 -,-( CH 2) 8 -, - CH 2 -CH (OH) -CH 2 -, - CH 2 -CH (OH) - (CH 2) 2 -, - CH 2 -CH (OH) - (CH 2) 3 - ,-(CH 2 ) 2 -CH (OH)-(CH 2 ) 2 -,-(CH 2 ) 2 -CH (OH)-(CH 2 ) 3 -,-(CH 2 ) 3 -CH (OH) -(CH 2 ) 3- , a group according to group A and a group according to group B are preferred; -(CH 2 ) 2 -,-(CH 2 ) 3 -,-(CH
  • any anion may be used, and specifically, for example, a halide ion; an aryl group having a substituent with electron withdrawing ability, a sulfonyl group having a substituent with electron withdrawing ability, haloalkyl And anions containing a group or a halogeno group; halogen oxo acid anions; or sulfonate anions (hereinafter sometimes abbreviated as anions according to the present invention).
  • the halide ion for example fluoride ion (F -), chloride ion (Cl -), bromide ion (Br -), iodide ion (I -) and the like, chloride Organic ions are preferred.
  • the anionic portion of the anions comprising a sulfonyl group or a haloalkyl group having an aryl group, an electron withdrawing substituent having an electron-withdrawing group, for example a sulfonic acid anion, a nitrogen anion (N - And quaternary boron anions, nitrate ions, phosphate ions and the like, and sulfonate anions, nitrogen anions and quaternary boron anions are preferable, and quaternary boron anions are more preferable.
  • examples of the anion moiety in the anion containing a halogeno group include a quaternary boron anion, a phosphorus anion, an antimony anion and the like, and a phosphorus anion and an antimony anion are preferable, and a phosphorus anion is more preferable.
  • examples of the electron withdrawing substituent in the aryl group having an electron withdrawing substituent or the sulfonyl group having an electron withdrawing substituent include, for example, a haloalkyl group having 1 to 3 carbon atoms, a halogeno Groups, nitro groups and the like, and among them, haloalkyl groups having 1 to 3 carbon atoms and halogeno groups are preferable, and halogeno groups are particularly preferable.
  • the haloalkyl group having 1 to 3 carbon atoms as the electron withdrawing group is, for example, chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, pentachloroethyl group, 2 Chloroalkyl groups such as -chloropropyl group, 3-chloropropyl group, 2-chloro-2-propyl group, heptachloropropyl group; bromomethyl group, tribromomethyl group, 2-bromoethyl group, 2,2,2-trichloromethyl group Bromoalkyl groups such as bromoethyl group, pentabromoethyl group, 2-bromopropyl group, 3-bromopropyl group, 2-bromo-2-propyl group, heptabromopropyl group, etc .; iodomethyl group, triiodomethyl group, 2- Iodoethyl
  • Iodoalkyl group fluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 3- And fluoroalkyl groups such as fluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group and heptafluoropropyl group.
  • Perhalogeno alkyl groups such as pentafluoroethyl group and heptafluoropropyl group are preferable, perfluoroalkyl groups such as trifluoromethyl group, pentafluoroethyl group and heptafluoropropyl group are more preferable, and trifluoromethyl group is particularly preferable .
  • the electron-withdrawing substituent in the aryl group having an electron-withdrawing substituent among the above specific examples, those having a strong electron-withdrawing power are preferable, and specifically, a trifluoromethyl group , A fluoro group and a nitro group are preferable, and a fluoro group is more preferable.
  • the electron-withdrawing substituent in the sulfonyl group having an electron-withdrawing substituent among the above specific examples, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, fluoro Groups are preferred.
  • a phenyl group, a naphthyl group etc. are mentioned as an aryl group in the aryl group which has a substituent with electron withdrawing property, for example, A phenyl group is preferable.
  • aryl group having a substituent with electron withdrawing property in the anion according to the present invention include, for example, those represented by the following general formulas (11) and (12).
  • R 41 represents a haloalkyl group having 1 to 3 carbon atoms, a halogeno group or a nitro group, m represents an integer of 1 to 5 and m R 41 are identical or different) May
  • k represents an integer of 1 to 7
  • R 41 is the same as above, and k R 41 may be the same or different.
  • Examples of the haloalkyl group having 1 to 3 carbon atoms of R 41 in the general formula (11) include the same as the haloalkyl group having 1 to 3 carbon atoms as an electron-withdrawing substituent in the anion according to the present invention, Preferred ones are also the same.
  • halogeno group R 41 in the general formula (11), fluoro group, chloro group, bromo group, iodo group and the like, fluoro group is preferred.
  • R 41 in the general formula (11) are the same as the preferred examples of the electron withdrawing substituent in the above-described aryl group having an electron withdrawing substituent.
  • R 41 is a halogeno group, preferably an integer of 2 ⁇ 7;
  • R 41 is a case of the nitro group, preferably an integer of 1 to 3, 1 is more preferred;
  • R 41 is In the case of a haloalkyl group, an integer of 1 to 7 is preferable, and an integer of 1 to 3 is more preferable.
  • Specific examples of the group represented by the general formula (11) include trifluoromethylphenyl group, di (trifluoromethyl) phenyl group, tri (trifluoromethyl) phenyl group, monofluorophenyl group, difluorophenyl group , Trifluorophenyl group, perfluorophenyl group, monochlorophenyl group, dichlorophenyl group, trichlorophenyl group, perchlorophenyl group, monobromophenyl group, dibromophenyl group, tribromophenyl group, perbromophenyl group, monoiodophenyl group, Diiodophenyl group, triiodophenyl group, periodophenyl group, nitrophenyl group, dinitrophenyl group, trinitrophenyl group etc. may be mentioned, and difluorophenyl group, trifluorophenyl group, perfluorophenyl group etc. are
  • Specific examples of the group represented by the general formula (12) include trifluoromethylnaphthyl group, di (trifluoromethyl) naphthyl group, tri (trifluoromethyl) naphthyl group, monofluoronaphthyl group, difluoronaphthyl group , Trifluoronaphthyl group, perfluoronaphthyl group, monochloronaphthyl group, dichloronaphthyl group, trichloronaphthyl group, perchloronaphthyl group, monobromonaphthyl group, dibromonaphthyl group, tribromonaphthyl group, perbromonaphthyl group, monoiodonaphthyl group Groups, diiodonaphthyl groups, triiodonaphthyl groups, periodonaphthyl groups, nitronaphthy
  • the aryl group having an electron-withdrawing substituent in the anion according to the present invention is preferably a group represented by the general formula (11), and more specifically, a trifluoromethylphenyl group, a nitrophenyl group , Dinitrophenyl group, trinitrophenyl group, monofluorophenyl group, difluorophenyl group, trifluorophenyl group and perfluorophenyl group are preferable, and difluorophenyl group, trifluorophenyl group, nitrophenyl group and perfluorophenyl group are more preferable.
  • a perfluorophenyl group is particularly preferred.
  • the sulfonyl group having an electron-withdrawing substituent in the anion according to the present invention is, for example, -SO 2 -CF 3 , -SO 2 -C 2 F 5 , -SO 2 -C 3 F 7 , -SO 2- F, -SO 2 -Cl, -SO 2 -Br, -SO 2 -I and the like can be mentioned.
  • haloalkyl group in the anion according to the present invention examples include haloalkyl groups having 1 to 3 carbon atoms, among which a perhaloalkyl group is preferable.
  • Preferred are a fluoromethyl group, a pentafluoroethyl group and a heptafluoropropyl group.
  • halogeno group in the anion which concerns on this invention a fluoro group, a chloro group, a bromo group, an iodo group etc. are mentioned, A fluoro group is preferable.
  • examples of the anion containing an aryl group having an electron-withdrawing substituent, a sulfonyl group having an electron-withdrawing substituent, a haloalkyl group or a halogeno group include 13) to those shown in (19).
  • R 41 and m are the same as above, and m R 41 may be the same or different.
  • R 41 and k are the same as above, and k R 41 may be the same or different.
  • R 41 and k are the same as above, and k R 41 may be the same or different.
  • each of R 42 to R 45 independently represents a haloalkyl group having 1 to 3 carbon atoms, a halogeno group or a nitro group
  • m 2 to m 5 each independently represent 1 to 5 M 2 R 42 , m 3 R 43 , m 4 R 44 and m 5 R 45 may be identical to or different from each other.
  • R 46 represents a haloalkyl group having 1 to 3 carbon atoms or a halogeno group, and four R 46 may be the same as or different from each other.
  • R 47 and R 48 each independently represent a haloalkyl group having 1 to 3 carbon atoms or a halogeno group, and R 47 and R 48 each represent a halogenated alkylene having 2 to 3 carbon atoms May form a group
  • R 49 represents a phosphorus atom or an antimony atom
  • X represents a halogeno group
  • all six Xs are the same.
  • R 41 and m in the general formula (13) examples include those described in the following table.
  • the m R 41 groups are independent of one another, but are preferably the same.
  • Examples of the combination of R 41 and k in the general formulas (14) and (15) include those described in the following table.
  • the k R 41 are independent of each other, but preferably the same.
  • Examples of the haloalkyl group having 1 to 3 carbon atoms as R 42 to R 45 in the general formula (16) include the same as the haloalkyl group having 1 to 3 carbon atoms as an electron-withdrawing substituent in the anion according to the present invention And the preferred ones are the same.
  • Examples of the halogeno group in R 42 to R 45 of the general formula (16) include a fluoro group, a chloro group, a bromo group, an iodo group and the like, and a fluoro group is preferable.
  • Examples of the haloalkyl group having 1 to 3 carbon atoms as R 46 in the general formula (17) include the same ones as the haloalkyl group having 1 to 3 carbon atoms as an electron-withdrawing substituent in the anion according to the present invention. The same is true.
  • halogeno group at R 46 of the general formula (17), fluoro group, chloro group, bromo group, iodo group and the like, fluoro group is preferred.
  • Preferred specific examples of the anion represented by the general formula (17) include, for example, BF 4 ⁇ , CF 3 BF 3 ⁇ , C 2 F 5 BF 3 ⁇ , C 3 F 7 BF 3 ⁇ , (CF 3 ) 4 B -, (C 2 F 5) 4 B -, (C 3 F 7) 4 B - , and the like.
  • Examples of the haloalkyl group having 1 to 3 carbon atoms as R 47 and R 48 in the general formula (18) include the same as the haloalkyl group having 1 to 3 carbon atoms as an electron-withdrawing substituent in the anion according to the present invention And the preferred ones are the same.
  • a fluoro group, a chloro group, a bromo group, an iodo group etc. are mentioned as a halogeno group in R 47 and R 48 of General formula (18), A fluoro group is preferable.
  • Examples of the halogenated alkylene group having a carbon number of 2 to 3 formed by R 47 and R 48 in the general formula (18) include a tetrafluoroethylene group, a hexafluoropropylene group and the like, and a hexafluoropropylene group is preferable. .
  • a bis (trifluoromethane sulfonyl) imide anion is preferable.
  • halogeno group in X of General formula (19) a fluoro group, a chloro group, a bromo group, an iodo group etc. are mentioned, A fluoro group is preferable.
  • PF 6 ⁇ As preferable specific examples of the anion represented by the general formula (19), for example, PF 6 ⁇ , SbF 6 ⁇ and the like can be mentioned, and PF 6 ⁇ is preferable.
  • halogen oxo acid anion in the anion which concerns on this invention a hypochlorite anion, a chlorite anion, a chlorate anion, a perchlorate anion etc. are mentioned, for example, A perchlorate anion is preferable.
  • sulfonate anion in the anion according to the present invention include, for example, an alkylsulfonic acid anion having 1 to 20 carbon atoms such as methanesulfonic acid anion; and a halogenated alkyl having 1 to 20 carbon atoms such as trifluoromethanesulfonic acid anion.
  • alkylsulfonic acid anion having 1 to 20 carbon atoms
  • a halogenated alkyl having 1 to 20 carbon atoms such as trifluoromethanesulfonic acid anion.
  • examples thereof include sulfonic acid anions and benzenesulfonic acid anions having a substituent such as benzenesulfonic acid anion and toluenesulfonic acid anion or unsubstituted ones.
  • the anion represented by An ⁇ of the general formula (1) is preferable, and a halide ion; and an aryl group having a substituent with electron withdrawing ability, a sulfonyl group having a substituent with electron withdrawing
  • An anion containing a haloalkyl group or a halogeno group is more preferred.
  • chloride ions and anions represented by general formulas (16) to (19) are preferable, and chloride ions and anions represented by general formula (16), (18) or (19) are more preferable,
  • the chloride ion and the anion represented by the general formula (18) or (19) are more preferable, and the chloride ion and the one represented by the general formula (19) are particularly preferable.
  • chloride ion, bis (trifluoromethanesulfonyl) imide anion, tetrakis (pentafluorophenyl) boron (IV) anion, PF 6 - are more preferable, and chloride ion, tetrakis ( Pentafluorophenyl) boron (IV) anion, PF 6 - is more preferred, chloride ion, PF 6 - is still more preferred, and chloride ion is particularly preferred.
  • Preferred Embodiments of the Compound of the Present Invention include compounds represented by the following general formula (1-2).
  • R 1 to R 6 , R 8 , Y 1 , An - and n 1 to n 3 are the same as above; two R 1 , two R 2 , two R 3 , two R 4 , two R 5 , two R 6 , two Y 1 and two An ⁇ each represent the same thing; n 3 R 8 and n 3 n 1 are Each may be the same or different.
  • Preferred specific examples of the compound represented by the general formula (1-2) include compounds represented by the following general formula (1-3).
  • R 1 to R 6 , R 8 , Y 1 , An ⁇ , n 1 and n 2 are the same as above; two R 1 , two R 2 , two R 3 , two R 4 , two R 5 , two R 6 , two Y 1 and two An ⁇ each represent the same.
  • Preferred specific examples of the compound represented by the general formula (1-3) include compounds represented by the following general formula (1-4).
  • R 1 to R 3 , R 9 , An ⁇ , n 4 and n 5 are the same as above; four R 1 , four R 2 , four R 3 and two an - represents the same respectively).
  • Preferred specific examples of the compound represented by the general formula (1-4) include compounds represented by the following general formula (1-5).
  • R 1 ′ represents a hydrogen atom or a methyl group
  • R 2 ′ represents a linear or branched alkyl group having 1 to 4 carbon atoms
  • R 3 ′ Represents a hydrogen atom, or a linear or branched alkyl group having 1 to 4 carbon atoms
  • R 10 represents a hydrogen atom, a hydroxy group or a group represented by formulas (101) to (108);
  • An ⁇ , n 4 and n 5 are the same as above; 4 R 1 ′, 4 R 2 ′, 4 R 3 ′ and 2 An ⁇ each represent the same thing.
  • R 1 ′ in the general formula (1-5) a hydrogen atom is preferable.
  • the linear or branched alkyl group having 1 to 4 carbon atoms as R 2 ′ in the general formula (1-5) includes the linear or branched carbon number in R 9 of the general formula (5)
  • the same thing is mentioned with a 1-4 alkyl group, and a preferable thing is also the same.
  • R 2 ′ in the general formula (1-5) a methyl group and an ethyl group are preferable, and an ethyl group is more preferable.
  • the linear or branched alkyl group having 1 to 4 carbon atoms as R 3 ′ in the general formula (1-5) includes the linear or branched carbon number in R 9 of the general formula (5)
  • the same thing is mentioned with a 1-4 alkyl group, and a preferable thing is also the same.
  • R 3 ′ in the general formula (1-5) a hydrogen atom, a methyl group or an ethyl group is preferable, a hydrogen atom or an ethyl group is more preferable, and an ethyl group is particularly preferable.
  • R 1 ′ to R 3 ′ in the general formula (1-5) examples include those described in Table 1 below.
  • a hydrogen atom, a hydroxy group and a group represented by the formulas (101) to (104) are preferable, and a hydrogen atom, a hydroxy group and a group represented by the formula (102) or (104) Group is more preferable, a hydrogen atom and a hydroxy group are more preferable, and a hydrogen atom is particularly preferable.
  • Preferred examples of the combination of R 1 ′ to R 3 ′, R 10 , n 4 and n 5 in the general formula (1-5) include, for example, the preferred combinations of R 1 ′ to R 3 ′ described in Table 1 above; R 10 described in Table 2, a combination of the preferred combination of n 4 and n 5 may be mentioned.
  • R 1 ′ to R 3 ′, R 10 , n 4 and n 5 in the general formula (1-5) include, for example, combinations 1 to 40 described in Table 3 below, among which combinations 1 to 25 Are preferred, combinations 5, 10, 15, 20 and 25 are more preferred, and combination 15 is particularly preferred.
  • a chloride ion, bis (trifluoromethanesulfonyl) imide anion, tetrakis (pentafluorophenyl) boron (IV) anion, PF 6 ⁇ may be mentioned.
  • Chloride ion, tetrakis (pentafluorophenyl) boron (IV) anion, PF 6 ⁇ is preferable, chloride ion, PF 6 ⁇ is more preferable, and chloride ion is particularly preferable.
  • the compounds of the present invention can be produced by the methods shown below. That is, the compound represented by the general formula (1) can be obtained by reacting the compound represented by the following general formula (21) with the compound represented by the following general formula (31) (Reaction [1]) .
  • Preferred specific examples of the compound represented by the general formula (21) include compounds represented by the following general formula (22). (In the general formula (22), R 1 to R 3 and An - are the same as above; two R 1 , two R 2 and two R 3 respectively represent the same.)
  • Preferred specific examples of the compound represented by the general formula (22) include compounds represented by the following general formula (23).
  • R 1 ′ to R 3 ′ and An ⁇ are the same as above; two R 1 ′, two R 2 ′ and two R 3 ′ represent the same thing respectively .
  • Preferred combinations of R 1 ′ to R 3 ′ in the general formula (23) include the same combinations as the preferred combinations of R 1 ′ to R 3 ′ described in Table 1 above.
  • An ⁇ used in combination with the combination described in Table 1 above a chloride ion, bis (trifluoromethanesulfonyl) imide anion, tetrakis (pentafluorophenyl) boron (IV) anion, PF 6 ⁇ may be mentioned.
  • Preferred specific examples of the compound represented by the general formula (31) include compounds represented by the following general formula (32).
  • R 8 , Y 1 and n 1 to n 3 are the same as above; two Y 1 represent the same; n 2 R 8 and n 2 n 1 May be the same or different.
  • Preferred specific examples of the compound represented by the general formula (32) include compounds represented by the following general formula (33).
  • R 8 , Y 1 , n 1 and n 2 are the same as above; two Y 1 represent the same.
  • Preferred specific examples of the compound represented by the general formula (33) include compounds represented by the following general formula (34). (In the general formula (34), R 9 , n 4 and n 5 are the same as above.)
  • Preferred specific examples of the compound represented by the general formula (34) include compounds represented by the following general formula (35). (In the general formula (35), R 10 , n 4 and n 5 are the same as above.)
  • Specific examples of the compound represented by the general formula (35) include ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and the like. 7-heptanediol, 1,8-octanediol, 1,2,3-propanetriol (glycerin), 1,2,4-butanetriol, 1,2,5-pentanetriol, 1,3,5-pentanetriol And 1,3,6-hexanetriol, 1,4,7-heptanetriol and the following compound group A.
  • the compound represented by the general formula (21) and the compound represented by the general formula (31) are generally contained in a solvent in the presence of a dehydration condensation agent, generally 0 ° C. or more and 80 ° C. or less, preferably The reaction may be carried out at 10 ° C. to 50 ° C. for usually 1 hour to 48 hours, preferably 10 hours to 24 hours.
  • the solvent examples include ethers such as diethyl ether, diisopropyl ether, ethyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; eg acetone, dimethyl ketone, methyl ethyl ketone, diethyl ketone, 2-hexanone, tert-butyl methyl Ketones such as ketone, cyclopentanone and cyclohexanone; halogenated hydrocarbons such as chloromethane, chloroform, dichloromethane, dichloroethane, trichloroethane, carbon tetrachloride and chlorobenzene; carbonized such as n-hexane, benzene, toluene and xylene Hydrogens; esters such as ethyl acetate, butyl acetate, methyl propionate and the like; nitriles such
  • the amount of the reaction solvent to be used is generally 0.1 mL or more and 50 mL or less, preferably 0.5 mL or more and 10 mL or less, per 1 mmol of the compound represented by the general formula (21).
  • any one which is generally used as a dehydration condensation agent may be used.
  • inorganic dehydration agents such as phosphorus pentoxide and anhydrous zinc chloride; eg, dicyclohexyl carbodiimide, diisopropyl carbodiimide, 1-ethyl-3-
  • Carbodiimides such as (3-dimethylaminopropylcarbodiimide) hydrochloride; for example, polyphosphoric acid, acetic anhydride, sulfuric acid, carbonyldiimidazole, p-toluenesulfonic acid etc. may be mentioned, with preference given to carbodiimides.
  • the amount of the dehydrating condensing agent to be used is generally 1 equivalent or more and 20 equivalents or less, preferably 1 equivalent or more and 10 equivalents or less, relative to the number of moles of the compound represented by the general formula (21).
  • a catalyst such as dimethylaminopyridine may be used to improve the efficiency of the dehydration condensation agent.
  • the amount of the catalyst used is usually 0.1 equivalents or more and 10 equivalents or less based on the number of moles of the compound represented by the general formula (21).
  • the amount of the compound represented by the general formula (31) is generally 0.1 equivalent or more and 1 equivalent or less, preferably 0.2 equivalent or more, relative to the number of moles of the compound represented by the general formula (21) It is less than equivalent weight.
  • the compound represented by the general formula (1) obtained by the above reaction [1] may be further subjected to a salt exchange reaction.
  • the salt exchange reaction is carried out by contacting the salt of a desired anion with a compound represented by the general formula (1) in a solvent.
  • the above-mentioned salt exchange reaction is carried out usually at 0 ° C. to 80 ° C., preferably 10 ° C. to 50 ° C., usually 10 minutes to 24 hours, preferably 30 minutes to 10 hours.
  • Examples of the solvent in the above salt exchange reaction include organic solvents such as methanol, ethanol, isopropyl alcohol (IPA), tetrahydrofuran (THF), dioxane, N, N-dimethylformamide (DMF), dichloromethane, dichloroethane, ethyl acetate and the like. Among them, ethanol, dichloromethane and ethyl acetate are preferred. These may be used alone or in combination of two or more.
  • the amount of the reaction solvent used is usually 0.1 mL or more and 100 mL or less, preferably 1 mL or more and 50 mL or less, per 1 mmol of the compound represented by the general formula (1).
  • a salt of the desired anion in the above-mentioned salt exchange reaction it may be suitably selected according to a thing desired as an anion which a final product has, for example, alkali metal salt of a desired anion, or an inorganic acid is mentioned.
  • the salt which consists of alkali metals, such as a desired anion and sodium, potassium, lithium, is mentioned.
  • the alkali metal salt is preferably potassium or lithium.
  • the amount of the alkali metal salt used is usually 2 equivalents or more and 3 equivalents or less, preferably 2 equivalents or more and 2.5 equivalents or less, with respect to the number of moles of the compound represented by the general formula (1).
  • Examples of the above-mentioned inorganic acids include mineral acids such as hydrochloric acid, hydrogen bromide, hydrogen iodide, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, hexafluorophosphoric acid, hexafluoroantimonic acid, etc. Perchloric acid, hexafluorophosphoric acid and hexafluoroantimonic acid are preferable, and hexafluorophosphoric acid is more preferable.
  • the amount of the inorganic acid used is usually 2 equivalents or more and 50 equivalents or less, preferably 2 equivalents or more and 10 equivalents or less, relative to the number of moles of the compound represented by the general formula (1).
  • the salt of the desired anion in the above salt exchange reaction is an alkali metal salt
  • the compound represented by the general formula (1) is reacted with an alkali metal salt of the desired anion in the presence of hydrochloric acid in a solvent to give a chloro salt. It is preferable to obtain the compound represented by the general formula (1) salt-exchanged to the desired anion via
  • the amount of the hydrochloric acid used is usually 2 equivalents or more and 50 equivalents or less, preferably 2 equivalents or more and 10 equivalents or less, relative to the number of moles of the compound represented by the general formula (1).
  • the salt of the desired anion in the salt exchange reaction is an inorganic acid
  • the compound represented by the general formula (1) may be reacted with the inorganic acid in a solvent.
  • the pressure during each reaction according to the method for producing a compound of the present invention described above is not particularly limited as long as a series of reactions are carried out without failure, and for example, it may be carried out at normal pressure.
  • reaction products and products obtained after each reaction according to the method for producing the compound of the present invention described above may be isolated by general post-treatment procedures and purification procedures usually performed in the field, as necessary. Specifically, for example, the reaction product and the product obtained by filtration, washing, extraction, concentration under reduced pressure, recrystallization, distillation, column chromatography and the like may be isolated.
  • the coloring composition of the present invention contains at least one compound of the present invention. Since the coloring composition of the present invention uses the compound of the present invention in which the fluorescence yield is suppressed as a dye, it is possible to form an excellent colored cured film in which the fluorescence emission is suppressed. Therefore, the coloring composition of the present invention is used for forming colored pixels such as color filters used in liquid crystal displays (LCDs) and solid-state imaging devices (CCDs, CMOS, etc.), printing inks, inkjet inks, and paints, etc. It can be used, and in particular, it is suitable for color filters of liquid crystal display devices.
  • LCDs liquid crystal displays
  • CCDs, CMOS, etc. solid-state imaging devices
  • the colored composition of the present invention can be formed into a sheet, a film, a bottle, a cup or the like by a conventionally known forming method and used as a colored resin formed product. Therefore, it can be used also for uses, such as glasses and a color contact lens, and it can be used similarly by setting it as a multilayer structure with well-known resin. In addition, it can be used, for example, in applications such as optical films, hair coloring agents, labeling substances for compounds and biological substances, materials for organic solar cells, and the like.
  • the coloring composition of the present invention may contain, in addition to the compound of the present invention, additives commonly used in the field according to each application.
  • the coloring composition of the present invention when used as a coloring resin application, the coloring composition of the present invention preferably contains at least one compound of the present invention and is mixed with other resins.
  • the other resin is not particularly limited, and examples thereof include polyolefin resin, polystyrene resin, polyester resin, polyamide resin, polyurethane resin, polycarbonate resin, epoxy resin, acrylic resin, acrylonitrile resin and the like.
  • the mixing ratio should just be suitably set according to the color of the coloring resin calculated
  • the coloring composition of the present invention can be used as a lubricant, an antistatic agent, an ultraviolet light inhibitor, in addition to the compound of the present invention and, if necessary, other resins, to the extent that the objects and effects of the present invention are not impaired.
  • Additives commonly used in this field such as antioxidants, light stabilizers, dispersants, processing stabilizers, processing aids, impact modifiers, fillers, reinforcing agents, flameproofing agents, plasticizers, foaming agents, etc. It may contain an agent.
  • the coloring composition of the present invention when used for forming a colored pixel, contains at least one compound of the present invention, and a polymerization initiator, a binder resin and a radically polymerizable monomer or oligomer Is preferable, and if necessary, pigments, solvents, silane coupling agents, crosslinking agents and the like may be contained.
  • the content of the compound of the present invention in the coloring composition of the present invention is 1% by mass to 50% by mass, preferably 5% by mass to 30% by mass, with respect to the mass of the coloring composition of the present invention.
  • the mass of the coloring composition of this invention here means the mass of the solid component except a solvent, and, in the following, this invention represents the same meaning.
  • a conventionally known thermal polymerization initiator or photopolymerization initiator generally used in this field can be used, and a photopolymerization initiator is preferable.
  • diethoxyacetophenone 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1 -One, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propane-1- Acetophenones such as 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoins such as benzoin, benzoin isopropyl ether and benzoin isobutyl ether; 2,4,6
  • the said polymerization initiator may be individual or may contain 2 or more types.
  • the content is 1% by mass to 50% by mass, preferably 5% by mass to 30% by mass, with respect to the mass of the coloring composition of the present invention.
  • binder resin for example, an ethylenically unsaturated monomer having at least one carboxy group or hydroxy group, or an ethylenically unsaturated monomer having the ethylenically unsaturated monomer and an aromatic hydrocarbon group or an aliphatic hydrocarbon group Copolymers thereof, those having an epoxy group at side chains or ends of the copolymers, those having an acrylate added thereto, and the like. These may be individual or may combine 2 or more types.
  • ethylenically unsaturated monomer having a carboxy group examples include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, benzyl methacrylate, crotonic acid, ⁇ -chloroacrylic acid, ethacrylic acid, cinnamic acid and the like; maleic acid , Unsaturated dicarboxylic acids (anhydrides) such as maleic anhydride, fumaric acid, itaconic acid, itaconic acid, citraconic acid, citraconic acid, citraconic anhydride, mesaconic acid, etc .; unsaturated polyvalent carboxylic acids (anhydrides) having 3 or more valences , 2-acryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl 2-hydroxypropylphthalic acid, 2-acrylo
  • the content of the binder resin is 10% by mass to 50% by mass, preferably 20% by mass to 50% by mass, with respect to the mass of the coloring composition of the present invention.
  • Examples of the radically polymerizable monomer or oligomer include polyethylene glycol diacrylate (having an ethylene group number of 2 to 14), polyethylene glycol dimethacrylate (having an ethylene group number of 2 to 14), and trimethylolpropane.
  • any pigment may be used as long as it is a pigment used to produce a red, blue or green coloring pattern, and examples thereof include phthalocyanine pigments.
  • examples of the phthalocyanine-based pigment include those containing magnesium, titanium, iron, cobalt, nickel, copper, zinc, and aluminum as a central metal, and specific examples thereof include CI pigment red 1 and CI pigment red 2 and CI.
  • Pigment red 5 CI pigment red 17, CI pigment red 31, CI pigment red 32, CI pigment red 41, CI pigment red 122, CI pigment red 123, CI pigment red 144, CI pigment red 149, CI pigment red 166, CI Pigment red 168, CI pigment red 170, CI pigment red 171, CI pigment red 175, CI pigment red 176, CI pigment red 177, CI pigment red 178, CI pigment red 179, CI pigment red 180, CI pigment red 185, CI Pigment red 187, CI pigment red 202, CI pigment red 206, CI pigment red 207, CI pigment red 209, CI pigment red 214, CI pigment red 220, CI pigment red 221, CI pigment red 224, CI pigment red 242, CI pigment red 243, CI pigment red 254, CI pigment red 255, CI pigment red 262, CI pigment red 264, CI pigment red 272, CI pigment blue 15, CI pigment blue 15: 1, CI pigment blue 15
  • the content of the pigment is 10% by mass to 50% by mass, preferably 10% by mass to 30% by mass, based on the mass of the colored composition of the present invention.
  • the coloring composition of the present invention contains the above pigment, it preferably contains a pigment dispersant.
  • the pigment dispersant include polyamidoamine and salts thereof, polycarboxylic acids and salts thereof, high molecular weight unsaturated acid ester, modified polyurethane, modified polyester, modified polyacrylate, modified polymethacrylate, acrylic copolymer, methacrylic
  • the copolymer includes naphthalenesulfonic acid formalin condensate, polyoxyethylene alkyl phosphate, polyoxyethylene alkylamine, alkanolamine and the like.
  • the pigment dispersants may be used alone or in combination of two or more. The content thereof is usually 1% by mass to 80% by mass, preferably 10% by mass to 60% by mass, with respect to the mass of the pigment.
  • the solvent may be appropriately selected according to the components contained in the coloring composition of the present invention. Specifically, for example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate , Butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, ethyl 3-oxypropionate, methyl 3-methoxypropionate, 3-methoxypropionate, 3-methoxypropionate, 3-methoxypropionate, 3-methoxy
  • the said silane coupling agent is used when couple
  • silane coupling agent conventionally known ones generally used in this field can be used, and as the reactive organic functional group, for example, epoxy group, thiol group, hydroxy group, amino group, ureido group, vinyl group And silane coupling agents having an acryloyl group or the like.
  • the silane coupling agent may be used in an amount of usually 0.1% by mass to 10% by mass, preferably 1% by mass to 5% by mass, in the reaction solution.
  • the crosslinking agent is not particularly limited as long as it can perform film curing by a crosslinking reaction, and is, for example, at least one selected from (a) epoxy resin, (b) methylol group, alkoxymethyl group and acyloxymethyl group. Phenol compounds substituted by at least one substituent selected from melamine compounds, guanamine compounds, glycoluril compounds or urea compounds, (c) methylol groups, alkoxymethyl groups and acyloxymethyl groups substituted by two substituents And naphthol compounds or hydroxyanthracene compounds. Among them, polyfunctional epoxy resins are preferable.
  • the content of the crosslinking agent is 10% by mass to 50% by mass, preferably 20% by mass to 50% by mass, based on the mass of the coloring composition of the present invention.
  • the coloring composition of the present invention may contain a polymerization inhibitor, a surfactant, an additive and the like in addition to those described above, and they are not particularly limited as long as they are known per se, and the amount used It is not limited as long as it is an amount generally used in this field.
  • the coloring composition of the present invention is prepared by mixing the above-mentioned components.
  • the coloring composition of the present invention can be molded into a desired shape by using a mold and a rolling machine according to a molding method known per se. Specifically, for example, injection molding (injection molding), compression molding, injection compression molding, extrusion molding, blow molding, calendar molding, inflation molding, T-die molding, transfer molding, etc. It can be molded into a desired shape by the molding method of
  • the coloring composition of the present invention may be applied to other materials (metal, glass, wood, paper, bricks, concrete, polymer material, etc.) by a coating and sticking method known per se, or with other materials. You can also paste them together. Specifically, for example, it can be applied to other materials by a slit coating method, an inkjet method, a spin coating method, a cast coating method, a roll coating method, a screen printing method, or the like.
  • the colored composition of the present invention is coated on a substrate such as a glass substrate by a method known per se
  • a colored cured film can be obtained by photocuring and / or thermosetting the coated surface.
  • the drying method is not particularly limited as long as it is a method known per se, and for example, a hot plate, an oven, an infrared heater, etc. is used, and usually 50 ° C. or more and 200 ° C. or less, preferably 50 ° C. or more 150 C. for 60 seconds or more and 5 hours or less, preferably 60 seconds or more and 1 hour or less.
  • the photo-curing method is not particularly limited as long as it is a method known per se, and is performed by irradiating active energy rays such as ultraviolet rays and electron beams to the coated surface.
  • active energy rays such as ultraviolet rays and electron beams
  • a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, an LED lamp etc. is used as a light source, and usually 200 nm to 400 nm, preferably 320 nm to 380 nm ultraviolet light, usually 100 mJ / cm 2 or more 3000 mJ / cm 2 or less, preferably done by irradiation with 500 mJ / cm 2 or more 2000 mJ / cm 2 or less of the exposure amount.
  • the heat curing method is not particularly limited as long as it is a method known per se, and for example, a hot plate, an oven, an infrared heater or the like is used, and usually 100 ° C. or more and 300 ° C. or less, preferably 150 ° C. or more It is carried out by heating at 250 ° C. or less, usually for 0.1 hours or more and 10 hours or less, preferably 0.1 hours or more and 5 hours or less.
  • Example 1 Synthesis of Rhodamine-Linked Compound (Compound 3)
  • Rhodamine B Compound 1: manufactured by Wako Pure Chemical Industries, Ltd.
  • THF tetrahydrofuran
  • ethylene glycol Compound 2: manufactured by Wako Pure Chemical Industries, Ltd.
  • DMAP 4-dimethylaminopyridine
  • WSC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • reaction solution was washed with water and concentrated under reduced pressure to evaporate the solvent from the reaction solution to obtain a dark red solid.
  • the solid was purified by a silica gel column to obtain 0.5 g (yield 10%) of a rhodamine-linked compound (compound 3) as a dark red solid.
  • Example 2 Synthesis of Rhodamine-Linked Compound (Compound 5 ) 0.4 g (5.0 mmol) of 1,3-propanediol (Compound 4: manufactured by Wako Pure Chemical Industries, Ltd.) instead of ethylene glycol was used at room temperature for 24 hours In the same manner as in Example 1 except that the reaction was carried out, 0.7 g (yield 14%) of a dark red solid rhodamine-linked compound (compound 5) was obtained.
  • Example 3 Synthesis of Rhodamine-Linked Compound (Compound 7) 75 mL of dichloromethane instead of THF, 0.5 g (5.0 mmol ) of 1,4-butanediol (Compound 6: Wako Pure Chemical Industries, Ltd.) instead of ethylene glycol In the same manner as in Example 1 except that the reaction was carried out at room temperature for 22 hours, 0.9 g (yield 18%) of a rhodamine-linked compound (Compound 7) as a dark red solid was obtained.
  • Example 4 Synthesis of Rhodamine-Linked Compound (Compound 8)
  • 0.3 g (0.3 mmol) of the rhodamine linked compound (compound 7) obtained in Example 3 and 10 mL of dichloromethane were added and dissolved.
  • 0.1 g (0.6 mmol) of potassium hexafluorophosphate (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the reaction was performed at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water. The solvent was distilled off from the reaction solution by vacuum concentration to obtain 0.2 g (yield 54%) of a dark red solid rhodamine-linked compound (compound 8) having a hexafluorophosphate anion.
  • Example 6 Synthesis of Rhodamine-Linked Compound (Compound 12) Instead of THF, 75 mL of dichloromethane was used, and 0.5 g (5.0 mmol ) of glycerin (Compound 11: manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of ethylene glycol. In the same manner as in Example 1, 0.4 g (yield 8%) of a dark red solid rhodamine-linked compound (Compound 12) was obtained.
  • Rhodamine B The absorption characteristic of Rhodamine B was evaluated as follows. That is, 1 mg (2 ⁇ 10 ⁇ 6 mol) of Rhodamine B (manufactured by Wako Pure Chemical Industries, Ltd.) was placed in a vial (glass bottle), and 20 mL of ethanol was added thereto. 0.1 mL of the obtained solution was put into another vial (glass bottle), and the solvent was air-dried using argon gas. 10 mL of water was placed in an air-dried vial (glass bottle) to prepare an aqueous solution of rhodamine B (concentration: 1 ⁇ 10 ⁇ 6 M). The resulting aqueous solution was placed in a cell with an optical path length of 1 cm, and the absorbance was measured using a spectrophotometer (product name: V-670, manufactured by JASCO Corporation).
  • the resulting aqueous solution was placed in a cell with an optical path length of 1 cm, and the absorbance was measured using a spectrophotometer (product name: V-670, manufactured by JASCO Corporation).
  • the measurement results of Experimental Example 1 are shown by solid lines in FIG.
  • FIG. 1 what normalized the measurement result of the comparative example 1 to the peak intensity of experiment example 1 is represented by FIG. 1 with a broken line.
  • the vertical axis in FIG. 1 represents the absorbance (in Example 1), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 2 Absorption Characteristic Evaluation of Compound 5
  • the compound 5 was prepared in the same manner as in Experimental Example 1 except that 0.2 mg (2 ⁇ 10 ⁇ 7 mol) of the compound 5 obtained in Example 2 was used instead of the compound 3. Absorbance characteristics were evaluated (concentration: 4 ⁇ 10 ⁇ 6 M).
  • the measurement result of Experimental example 2 is shown by a solid line in FIG.
  • What normalized the measurement result of the comparative example 1 to the peak intensity of Experimental example 2 is represented by a broken line in FIG.
  • the vertical axis in FIG. 2 represents the absorbance (in Experimental Example 2), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 3 Absorption Characteristic Evaluation of Compound 7
  • the compound 7 was prepared in the same manner as in Experimental Example 1 except that 0.1 mg (1 ⁇ 10 ⁇ 7 mol) of the compound 7 obtained in Example 3 was used instead of the compound 3. Absorbance characteristics were evaluated (concentration: 2 ⁇ 10 ⁇ 6 M).
  • the measurement result of Experimental Example 3 is shown by a solid line in FIG.
  • What normalized the measurement result of the comparative example 1 to the peak intensity of Experimental example 3 is represented by a broken line in FIG.
  • the vertical axis in FIG. 3 represents the absorbance (in Experimental Example 3), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 4 Absorption Characteristic Evaluation of Compound 8
  • the compound 8 was prepared in the same manner as in Experimental Example 1 except that 0.03 mg (3 ⁇ 10 ⁇ 8 mol) of the compound 8 obtained in Example 4 was used instead of the compound 3. Absorbance characteristics were evaluated (concentration: 0.5 ⁇ 10 ⁇ 6 M).
  • the measurement result of Experimental Example 4 is shown by a solid line in FIG.
  • FIG. 4 what normalized the measurement result of the comparative example 1 to the peak intensity of Experimental example 4 is represented by FIG. 4 with a broken line.
  • the vertical axis in FIG. 4 represents the absorbance (in Experimental Example 4), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 5 Absorption Characteristic Evaluation of Compound 10
  • the compound 10 was prepared in the same manner as in Experimental Example 1 except that 0.2 mg (2 ⁇ 10 ⁇ 7 mol) of the compound 10 obtained in Example 5 was used instead of the compound 3. Absorbance characteristics were evaluated (concentration: 4 ⁇ 10 ⁇ 6 M).
  • the measurement result of Experimental example 5 is shown by a solid line in FIG.
  • FIG. 5 what normalized the measurement result of the comparative example 1 to the peak intensity of Experimental example 5 is represented by FIG. 5 with a broken line.
  • the vertical axis in FIG. 5 represents the absorbance (in Experimental Example 5), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 6 Absorption Characteristic Evaluation of Compound 12
  • the compound 12 was prepared in the same manner as in Experimental Example 1 except that 0.4 mg (4 ⁇ 10 ⁇ 7 mol) of the compound 12 obtained in Example 6 was used instead of the compound 3. Absorbance characteristics were evaluated (concentration: 8 ⁇ 10 ⁇ 6 M).
  • the measurement result of Experimental Example 6 is shown by a solid line in FIG.
  • What normalized the measurement result of the comparative example 1 to the peak intensity of Experimental example 6 is represented by a broken line in FIG.
  • the vertical axis in FIG. 6 represents the absorbance (in Experimental Example 6), and the horizontal axis (nm) represents the wavelength.
  • Experimental Example 7 Evaluation of Fluorescence Property Regarding the aqueous solution of Compound 7 (concentration: 2 ⁇ 10 ⁇ 6 M) prepared in Experimental Example 3 and the aqueous solution of Compound 10 prepared in Experimental Example 5 (concentration: 4 ⁇ 10 ⁇ 6 M)
  • the fluorescence yield was measured using an absolute PL quantum yield measurement apparatus (product name: Quantaurus-QY C11347-01, manufactured by Hamamatsu Photonics K.K.).
  • the measurement results of Experimental Example 7 are shown in Table 4.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Optical Filters (AREA)
  • Pyrane Compounds (AREA)

Abstract

La présente invention aborde le problème de la production d'un colorant à base de rhodamine qui est capable de supprimer le rendement de fluorescence et de former un agrégat même dans des conditions de faible concentration. La présente invention concerne un composé représenté par la formule générale (1). [Dans la formule générale (1), les R1 à R6 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1-6, Y1 représente -O- ou -NH-, A1 représente un groupe alkylène linéaire en C1-12 qui peut posséder un substituant, le substituant représentant un groupe hydroxy, un groupe alkyle en C1-6, ou un groupe représenté par la formule générale (2) (dans la formule générale (2), R7 représente un atome d'hydrogène ou un groupe méthyle, Y2 représente -O- ou -NH -, et A2 représente une liaison simple ou un groupe alkylène linéaire en C1-6), An- représente un anion, et ses deux R1, ses deux R2, ses deux R3, ses deux R4, ses deux R5, ses deux R6, ses deux Y1, et ses deux An- représentent chacun la même chose].
PCT/JP2018/031869 2017-08-31 2018-08-29 Composé lié à la rhodamine Ceased WO2019044872A1 (fr)

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Publication number Priority date Publication date Assignee Title
JP2022056354A (ja) * 2020-09-29 2022-04-08 保土谷化学工業株式会社 キサンテン色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

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