WO2017145627A1 - Composé et filtre couleur - Google Patents

Composé et filtre couleur Download PDF

Info

Publication number
WO2017145627A1
WO2017145627A1 PCT/JP2017/002664 JP2017002664W WO2017145627A1 WO 2017145627 A1 WO2017145627 A1 WO 2017145627A1 JP 2017002664 W JP2017002664 W JP 2017002664W WO 2017145627 A1 WO2017145627 A1 WO 2017145627A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
compound
substituent
ring
parts
Prior art date
Application number
PCT/JP2017/002664
Other languages
English (en)
Japanese (ja)
Inventor
祐貴 野口
育郎 清都
Original Assignee
Dic株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to JP2017525428A priority Critical patent/JP6255634B1/ja
Publication of WO2017145627A1 publication Critical patent/WO2017145627A1/fr

Links

Classifications

    • 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
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • 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
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • 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
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
    • 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
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention for example, a triarylmethane compound capable of providing a colored product having a small hue change even when subjected to a thermal history at a high temperature for a long time when used as a colorant, and a color comprising the compound Regarding filters.
  • a color filter such as a liquid crystal display device has a red pixel portion (R), a green pixel portion (G), and a blue pixel portion (B).
  • Each of these pixel portions has a structure in which a thin film of a synthetic resin in which an organic pigment is dispersed is provided on a substrate, and organic pigments of red, green, and blue are used as the organic pigment.
  • an ⁇ -type copper phthalocyanine pigment (CI Pigment Blue 15: 6) is generally used, and the color is adjusted as necessary. Therefore, a small amount of purple organic pigment dioxazine violet pigment (CI Pigment Violet 23) is used in combination.
  • Organic pigments used in the production of color filters have characteristics that are completely different from those of conventional general-purpose applications, specifically, making display screens of liquid crystal display devices brighter (higher brightness) and the like. .
  • the dioxazine violet pigment is used in combination with the ⁇ -type copper phthalocyanine pigment, high brightness cannot be achieved. Therefore, particularly high brightness is particularly required for the organic pigment used in the blue pixel portion (B).
  • C.I. I. As CI Pigment Blue 1, a final color of BASF (FANAL BLUE D6340, D6390) having the following chemical structure is prominent.
  • I. Pigment Blue 1 is obtained by lake-forming Victoria Pure Blue BO, which is a basic triarylmethane dye, with a heteropoly acid such as phosphomolybdic acid or phosphotungsten molybdic acid.
  • Victoria Pure Blue BO which is a basic triarylmethane dye
  • a heteropoly acid such as phosphomolybdic acid or phosphotungsten molybdic acid.
  • C.I. I. Pigment Blue 1 has a cationic counter ion A ⁇ of Keggin type PMo x W 12-x O 40 .
  • triarylmethane dyes include halide anions, boron anions such as tetraphenylboron, organic carboxylate anions, inorganic sulfate anions, inorganic phosphate anions, aliphatic sulfonate anions, aromatic sulfonate anions, It is said that sulfonate anions corresponding to anthraquinone dyes, phthalocyanine dyes and indigo dyes can be used.
  • Patent Documents 7 and 8 the use of a compound composed of a salt formed of a triarylmethane having a specific structure and a heteropolyoxometalate anion having a specific structure for a blue pixel portion of a color filter has been studied.
  • Patent Document 9 a compound composed of a salt formed by dimerized triarylmethane and an anion is also used in the color filter blue pixel portion.
  • the problem to be solved by the present invention is to provide a colorant with little hue change even when it receives a heat history of 200 ° C. or more required for a manufacturing process at the time of producing a color filter.
  • a triarylmethane compound capable of providing a liquid crystal display device and the like capable of providing an excellent liquid crystal display with little hue change when used for preparing a blue pixel portion of a color filter, and a color filter containing the same are provided. There is to do.
  • the present inventors use a triarylmethane compound composed of a basic multivalent triarylmethane dye cation having a specific structure and a specific counter anion as a colorant for a color filter.
  • a triarylmethane compound composed of a basic multivalent triarylmethane dye cation having a specific structure and a specific counter anion as a colorant for a color filter.
  • the present invention provides a compound represented by the following general formula (I).
  • Z represents an a-valent aliphatic or aromatic hydrocarbon group which may have a substituent.
  • B c- represents a c-valent anion.
  • R 1 to R 3 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group, and R 1 and R 2 combine to form a ring structure May be.
  • A represents an aromatic group which may have a substituent or a heterocyclic group which may have a substituent.
  • a plurality of R 1 to R 3 and A may be the same or different.
  • a represents an integer of 2 or more, and b, c, and d represent an integer of 1 or more.
  • Y each independently represents a hydrogen atom or an arbitrary substituent.
  • R 6 and R 7 are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, or 2 to 2 carbon atoms which may have a substituent.
  • 6 represents an alkenyl group having 6 or an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, wherein R 6 and R 7 may be linked to each other to form a ring; The ring may have a substituent.
  • R 8 to R 10 are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, and 2 to carbon atoms which may have a substituent.
  • 6 represents an alkenyl group having 6 or an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, wherein R 8 to R 10 may be linked to each other to form a ring; The ring may have a substituent.
  • a color filter containing at least one selected from the compounds described above.
  • the triarylmethane compound of the present invention is a triarylmethane compound as represented by the specific general formula (I), even if it receives a heat history at a high temperature, the hue change of the colored material is small and the heat resistance can be greatly improved. In particular, there is a particularly remarkable technical effect that the heat resistance of a color filter such as a liquid crystal display device can be greatly improved.
  • the color filter of the present invention contains a triarylmethane compound as represented by the specific general formula (I) in the blue pixel portion, the color filter has a long hue change even when subjected to a thermal history at a high temperature. There is a particularly remarkable technical effect that a liquid crystal display device capable of displaying a brighter image over time can be provided.
  • the triarylmethane compound of the present invention is a compound represented by the following general formula (I).
  • Z represents an a-valent aliphatic or aromatic hydrocarbon group which may have a substituent.
  • B c- represents a c-valent anion.
  • R 1 to R 3 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group, and R 1 and R 2 combine to form a ring structure May be.
  • A represents an aromatic group which may have a substituent or a heterocyclic group which may have a substituent.
  • a plurality of R 1 to R 3 and A may be the same or different.
  • a represents an integer of 2 or more, and b, c, and d represent an integer of 1 or more.
  • Y each independently represents a hydrogen atom or an arbitrary substituent.
  • the compound of the general formula (I) of the present invention is a water-insoluble colorant and comprises a triarylmethane cation moiety and an anion.
  • R 1 to R 3 may be the same or different. Accordingly, the —NR 1 R 2 group may be left-right symmetric or left-right asymmetric.
  • R 1 and R 2 When adjacent R 1 and R 2 are combined to form a ring, these may be a ring bridged with a heteroatom. Specific examples of this ring include the following. These rings may have a substituent.
  • R 1 to R 3 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent from the viewpoint of chemical stability. It is preferable.
  • each Y is independently a hydrogen atom or an arbitrary substituent.
  • R 1 to R 3 are each independently a hydrogen atom; methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, Alkyl groups such as cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group and decyl group; any of aryl groups such as phenyl group, naphthyl group, thienyl group, furyl group and thiazolyl group More preferably.
  • R 1 to R 3 and Y represent an alkyl group or an aryl group
  • the alkyl group or aryl group may further have an arbitrary substituent.
  • Examples of the optional substituent that the alkyl group or aryl group may further have include the following [Substituent group R].
  • R 1 to R 3 are more preferably an alkyl group having 1 to 8 carbon atoms which may have a substituent, and more specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, or a butyl group. , Isobutyl group, sec-butyl group, pentyl group, hexyl group, 2-ethylhexyl group and other unsubstituted alkyl groups; 2-methoxyethyl group, 2-ethoxyethyl group and other alkoxyalkyl groups; 2-acetyloxyethyl group, etc. Cyanoalkyl groups such as 2-cyanoethyl group; fluoroalkyl groups such as 2,2,2-trifluoroethyl group, 4,4,4-trifluorobutyl group, and the like.
  • Y may be any group independently as long as the effects of the present invention are not impaired.
  • a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl may be used.
  • alkyl group, alkoxy group and aryl group may further have other optional substituents.
  • substituent group R what was described by the term of the said [substituent group R] is mentioned, for example.
  • adjacent Y may combine to form a ring structure.
  • Y in the present invention is most preferably a hydrogen atom in terms of high color purity.
  • the aromatic group and heterocyclic group in A are not particularly limited.
  • aromatics in the aromatic group in addition to benzene ring, condensed polycyclic aromatic hydrocarbons such as naphthalene ring, tetralin ring, indene ring, fluorene ring, anthracene ring, phenanthrene ring; biphenyl, terphenyl, diphenylmethane, triphenyl
  • chain polycyclic hydrocarbons such as methane and stilbene.
  • the chain polycyclic hydrocarbon may have a heteroatom such as O or S in the chain skeleton such as diphenyl ether.
  • heterocyclic ring in the heterocyclic group examples include 5-membered heterocycles such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole, and pyrazole; 6-membered heterocycles such as pyran, pyrone, pyridine, pyridazine, pyrimidine, and pyrazine; And condensed polycyclic heterocycles such as thionaphthene, indole, carbazole, coumarin, benzo-pyrone, quinoline, isoquinoline, acridine, phthalazine, quinazoline, quinoxaline and the like.
  • aromatic groups and heterocyclic groups may have a substituent. Examples of the substituent include those described in the above section [Substituent group R].
  • the group represented by the following general formula (IV), the following general formula (V), or the following general formula (VI) is preferable as the aromatic group or heterocyclic group in A from the viewpoint of heat resistance.
  • R 11 and R 12 each independently represent a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent, and R 11 and R 12 12 may combine to form a ring structure, each E 1 independently represents a hydrogen atom or an arbitrary substituent, and * represents a bond to a carbon atom.
  • R 13 and R 14 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent, and R 13 and R 14 14 may combine to form a ring structure, each E 2 independently represents a hydrogen atom or an arbitrary substituent, and * represents a bond to a carbon atom.
  • R 15 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group which may have a substituent.
  • X represents an oxygen atom, a nitrogen atom or a sulfur atom.
  • R 16 and R 17 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent, and R 16 and R 17 are bonded to form a ring; (A structure may be formed. * Represents a bond with a carbon atom.)
  • R 11 and R 12 may be the same or different. Accordingly, the —NR 11 R 12 group may be left-right symmetric or left-right asymmetric.
  • R 11 and R 12 When adjacent R 11 and R 12 are bonded to form a ring, these may be a ring bridged with a heteroatom. These rings may have a substituent.
  • R 11 and R 12 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent from the viewpoint of chemical stability. It is preferable. Among them, R 11 and R 12 are each independently a hydrogen atom; methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, Alkyl groups such as cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group and decyl group; any of aryl groups such as phenyl group, naphthyl group, thienyl group, furyl group and thiazolyl group More preferably.
  • R 11 and R 12 represent an alkyl group or an aryl group
  • the alkyl group or aryl group may further have an optional substituent.
  • the optional substituent that the alkyl group or aryl group may further have include those described in the above-mentioned [Substituent group R] section.
  • R 11 and R 12 are each more preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms which may have a substituent, and more specifically, a methyl group, an ethyl group, or a propyl group.
  • E 1 may be any group independently as long as the effects of the present invention are not impaired.
  • the alkyl group, alkoxy group and aryl group may further have other optional substituents.
  • an arbitrary substituent which the said alkyl group, an alkoxy group, and an aryl group may have further what was described by the term of the said [substituent group R] is mentioned, for example.
  • adjacent E 1 may be bonded to form a ring structure.
  • E 1 in the present invention is most preferably a hydrogen atom in terms of high color purity.
  • R 13 and R 14 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
  • alkyl group in R 13 and R 14 include linear, branched or cyclic alkyl groups, and the number of carbon atoms is usually 1 or more, and usually 8 or less, preferably 5 or less.
  • Specific examples include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, cyclohexyl group and the like.
  • Examples of the aryl group in R 13 and R 14 include an aromatic hydrocarbon ring group and an aromatic heterocyclic group.
  • the aromatic hydrocarbon ring group may be a single ring or a condensed ring, and is not particularly limited as long as it has 5 to 18 carbon atoms to form the ring.
  • the aromatic heterocyclic group may be a monocyclic ring or a condensed ring, and is not particularly limited as long as the number of carbon atoms forming the ring is 3 to 10.
  • R 13 and R 14 When adjacent R 13 and R 14 are combined to form a ring, these may be a ring bridged with a heteroatom. These rings may have a substituent.
  • R 13 and R 14 are preferably each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or an optionally substituted group. It is a phenyl group.
  • Examples of the substituent that the alkyl group, aryl group, and ring formed by connecting to each other in R 13 and R 14 may have include the following [Substituent group Q].
  • [Substituent group Q] Fluorine atom, chlorine atom, alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkoxyl group having 1 to 8 carbon atoms, phenyl group, mesityl group, tolyl group, naphthyl group, cyano group, acetyloxy Groups, alkylcarbonyloxy groups having 2 to 9 carbon atoms, sulfonic acid amide groups, sulfonealkylamide groups having 2 to 9 carbon atoms, alkylcarbonyl groups having 2 to 9 carbon atoms, Phenethyl group, hydroxyethyl group, acetylamide group, dialkylaminoethyl group formed by bonding an alkyl group having 1 to 4 carbon atoms, trifluoromethyl group, trialkylsilyl group having 1 to 8 carbon atoms, nitro group, carbon number 1 to 8 alkylthio groups.
  • the alkyl group, aryl group, and ring formed by connecting to each other in R 13 and R 14 may have, preferably an alkyl group having 1 to 8 carbon atoms, or 2 to 8 carbon atoms.
  • E 2 may be any group independently as long as the effects of the present invention are not impaired.
  • the alkyl group, alkoxy group and aryl group may further have other optional substituents.
  • an arbitrary substituent which the said alkyl group, an alkoxy group, and an aryl group may have further what was described by the term of the said [substituent group R] is mentioned, for example.
  • adjacent E 2 may be bonded to form a ring structure.
  • E 2 in the present invention is most preferably a hydrogen atom in terms of high color purity.
  • Examples of the alkyl group having 1 to 20 carbon atoms represented by R 15 in the general formula (VI) include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, linear alkyl groups such as n-heptyl group and n-octyl group; isopropyl group, sec-butyl group, tert-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-propyl A branched al
  • Examples of the aryl group represented by R 15 in the general formula (VI) include aryl groups having 6 to 14 carbon atoms such as a phenyl group, a naphthyl group, and a benzyl group.
  • examples of the substituent include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl
  • An alkyl group having 1 to 6 carbon atoms such as a group; a haloalkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; a hydroxy group;
  • X represents an oxygen atom, a nitrogen atom or a sulfur atom. From the viewpoint of ease of synthesis, a sulfur atom is preferred.
  • R 16 and R 17 may be the same or different. Accordingly, the —NR 16 R 17 group may be left-right symmetric or left-right asymmetric.
  • R 16 and R 17 When adjacent R 16 and R 17 are combined to form a ring, these may be a ring bridged with a heteroatom. These rings may have a substituent.
  • R 16 and R 17 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent from the viewpoint of chemical stability. It is preferable. Among them, R 16 and R 17 are each independently a hydrogen atom; methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, Alkyl groups such as cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group and decyl group; any of aryl groups such as phenyl group, naphthyl group, thienyl group, furyl group and thiazolyl group More preferably.
  • R 16 and R 17 represent an alkyl group or an aryl group
  • the alkyl group or aryl group may further have an optional substituent.
  • the optional substituent that the alkyl group or aryl group may further have include those described in the above-mentioned [Substituent group R] section.
  • the group represented by the general formula (VI) is preferably a group represented by the following formula. * Represents a bond with a carbon atom.
  • Z in the general formula (I) is an a-valent aliphatic or aromatic hydrocarbon group which may have a substituent.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic, may have an unsaturated bond, may have a substituent, and has an O in the carbon chain. , S, N may be included.
  • a carbonyl group, a carboxy group, an oxycarbonyl group, an amide group or the like may be contained, and a hydrogen atom may be further substituted with a halogen atom or the like.
  • the aromatic hydrocarbon group includes a monocyclic or polycyclic aromatic group, may have a substituent, and may be a heterocyclic ring containing O, S, and N.
  • condensed polycyclic aromatic hydrocarbons such as naphthalene ring, tetralin ring, indene ring, fluorene ring, anthracene ring, phenanthrene ring; chain polycyclic aromatic hydrocarbons such as biphenyl and terphenyl; 5-membered heterocycles such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole; 6-membered heterocycles such as pyran, pyrone, pyridine, pyrone, pyridazine, pyrimidine, pyrazine; benzofuran, thionaphthene, indole, carbazole, coumarin, And groups containing a condensed polycyclic heterocycle such as benzo-pyrone, quinoline, isoquinoline, acridine, phthalazine, quin
  • Z in the general formula (I) is an a-valent organic group in which a carbon atom directly bonded to N (nitrogen atom) does not have a ⁇ bond, and the organic group is at least a terminal directly bonded to N.
  • the aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N is linear, branched or cyclic unless the terminal carbon atom directly bonded to N has a ⁇ bond.
  • the carbon atom other than the terminal may have an unsaturated bond, may have a substituent, and the carbon chain contains O, S, and N. Also good.
  • a carbonyl group, a carboxy group, an oxycarbonyl group, an amide group or the like may be contained, and a hydrogen atom may be further substituted with a halogen atom or the like.
  • the aromatic group having an aliphatic hydrocarbon group in Z is a monocyclic or polycyclic aromatic group having an aliphatic hydrocarbon group having a saturated aliphatic hydrocarbon group at the terminal directly bonded to N. And may have a substituent, and may be a heterocyclic ring containing O, S, and N.
  • Z contains a cyclic
  • a bridged alicyclic hydrocarbon group is preferable from the viewpoint of skeleton fastness.
  • the bridged alicyclic hydrocarbon group means a polycyclic aliphatic hydrocarbon group having a bridged structure in the aliphatic ring and having a polycyclic structure, for example, norbornane, bicyclo [2,2,2]. Examples include octane and adamantane.
  • norbornane is preferable.
  • the group containing a benzene ring and a naphthalene ring is mentioned, for example, Among these, the group containing a benzene ring is preferable.
  • Z is preferably divalent from the viewpoint of easy availability of raw materials.
  • Z is a divalent organic group, an aromatic group in which two linear, branched, or cyclic alkylene groups having 1 to 20 carbon atoms or two alkylene groups having 1 to 20 carbon atoms such as xylylene groups are substituted.
  • Z include the following, but are not limited thereto. * Represents a bond with a nitrogen atom.
  • a plurality of R 1 to R 3 and A present in one molecule may be the same or different.
  • the color development site exhibits the same color development, so that the same color as the single color development site can be reproduced, which is preferable from the viewpoint of color purity.
  • at least one of R 1 to R 3 and A is a different substituent, a color obtained by mixing plural types of monomers can be reproduced and adjusted to a desired color. .
  • [B c- ] is a monovalent or higher anion.
  • [B c- ] is not particularly limited as long as it is a monovalent or higher anion, but preferred anions from the viewpoint of heat resistance are heteropolyoxometalate anions, anions represented by the following general formula (II), and the following general formula (III) And an anion represented by the formula (I) and a sulfonate anion.
  • R 6 and R 7 are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, or 2 to 2 carbon atoms which may have a substituent.
  • 6 represents an alkenyl group having 6 or an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, wherein R 6 and R 7 may be linked to each other to form a ring; The ring may have a substituent.
  • R 8 to R 10 are each independently an alkyl group having 1 to 8 carbon atoms which may have a substituent, and 2 to carbon atoms which may have a substituent.
  • 6 represents an alkenyl group having 6 or an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, wherein R 8 to R 10 may be linked to each other to form a ring; The ring may have a substituent.
  • the heteropolyacid anion is referred to as a heteropolyoxometalate anion.
  • a heteropoly acid is an inorganic acid having a relatively large molecular weight that does not contain an organic structure, and can exhibit unique properties not found in low-molecular inorganic acids or organic acids such as hydrochloric acid and sulfuric acid.
  • the first is to form a water-insoluble triarylmethane compound by rake formation with a cationic heteropolyacid.
  • Heteropolyacids do not contain organic structures or can contain relatively large molecular weights, including metals, so by selecting them appropriately, they can be derived from anionic structures even when exposed to high temperatures or light. It becomes possible to greatly suppress the alteration of the triarylmethane compound.
  • [B c- ] when it is desired to obtain a triarylmethane compound having higher heat resistance, for example, [B c- ] contains P (phosphorus) and Si (with W (tungsten) and O (oxygen) as essential elements.
  • a heteropolyoxometalate anion containing at least one kind of silicon) is preferred.
  • W (tungsten), Mo (molybdenum), O (oxygen) are essential elements, and a heteropolyoxometalate anion containing at least one of P (phosphorus) and Si (silicon) is improved in light resistance. This is more preferable.
  • Keggin type phosphotungstate ion ⁇ - (PW 12 O 40 ) 3 ⁇ Dawson type phosphotungstate ion ⁇ - (P 2 W 18 O 62 ) 6 ⁇ , ⁇ - (P 2 W 18 O 62 ) 6- , Keggin-type silicotungstate ion ⁇ - (SiW 12 O 40 ) 4- , ⁇ - (SiW 12 O 40 ) 4- , ⁇ - (SiW 12 O 40 ) 4- , and other examples ( P 2 W 17 O 61 ) 10 ⁇ , (P 2 W 15 O 56 ) 12 ⁇ , (H 2 P 2 W 12 O 48 ) 12 ⁇ , (NaP 5 W 30 O 110 ) 14 ⁇ , ⁇ - (SiW 9 O 34 ) 10 ⁇ , ⁇ - (SiW 10 O 36 ) 8 ⁇ , ⁇ - (SiW 11 O 39 ) 8 ⁇ , ⁇ - (SiW 11 O 39 ) 8 ⁇ and the like
  • the deficient Dawson-type phosphotungstic acid heteropolyoxometalate anion is (P 2 W 17 O 61 ) 10- .
  • heteropolyacids or alkali metal salts thereof examples include H 6 (P 2 Mo y W 18-y O 62 ), Na 6 (P 2 Mo y W 18-y O 62 ), and H 4 (SiMo Z W 12— Z O 40 ), Na 4 (SiMo Z W 12-Z O 40 ), H 10 (P 2 W 17 O 61 ), Na 10 (P 2 W 17 O 61 ), and the like can be used.
  • a heteropolyacid such as H 6 can be easily obtained, for example, according to the method described in Inorganic Chemistry, vol 47, p3679. Specifically, it can be obtained by dissolving an alkali metal tungstate and an alkali metal molybdate in water, adding phosphoric acid thereto, and heating to reflux for 5 to 10 hours while stirring with heating. The heteropolyacid thus obtained is reacted with an alkali metal chloride to form Na 6 (P 2 Mo y W 18-y O 62 ), which is a Dawson type heteropolyoxometalate alkali metal salt, in the same manner as described above. I can do it.
  • the number of molybdenum y in the heteropolyoxometalate anion is changed. It can be prepared in the range of 0-3.
  • an alkali metal molybdate salt is dissolved in water, hydrochloric acid is added thereto, and then an ⁇ 2-type deficient doson-type phosphotungstic alkali such as K 10 ( ⁇ 2-type P 2 W 17 O 61 ) is used. It can be obtained by adding a metal salt and stirring at 10 to 30 ° C. for 30 minutes to 2 hours.
  • the heteropolyacid thus obtained can be converted to a Dawson type heteropolyoxometalate alkali metal salt in the same manner as described above by reacting with an alkali metal chloride.
  • P 2 MoW 17 O 62 can be obtained by preparing ⁇ 2 type P 2 W 17 O 61 by hydrolysis from P 2 W 18 O 62 and reacting it with Mo. By doing so, it is possible to obtain the above-described heteropolyacid and its alkali metal salt having no distribution in the numerical value of y.
  • a heteropolyacid such as H 4 (SiMoW 11 O 40 ) or a heteropolyoxometalate alkali metal salt can be easily obtained according to the method described in, for example, Journal of American Chemical Society, 104 (1982), p3194. Specifically, it can be obtained by mixing and stirring a nitric acid aqueous solution and an alkali metal molybdate aqueous solution, adding K 8 ( ⁇ -type SiW 11 O 39 ) thereto, and stirring for 2 to 6 hours.
  • the heteropolyacid thus obtained can be converted to a Keggin heteropolyoxometalate alkali metal salt in the same manner as described above by reacting with an alkali metal chloride.
  • Heteropolyacids such as H 6 (P 2 W 18 O 62 ) and H 10 (P 2 W 17 O 61 ) can be easily obtained according to the method described in, for example, Inorganic Chemistry, vol 47, p3679. Specifically, it can be obtained by dissolving an alkali metal tungstate in water, adding hydrochloric acid and phosphoric acid thereto, and heating to reflux for 10 to 50 hours with heating and stirring.
  • the heteropolyacid can be converted to a Dawson type heteropolyoxometalate alkali metal salt by reacting with an alkali metal chloride.
  • the deficient Dawson-type heteropolyoxometalate alkali metal salt can be easily obtained using the former Dawson-type phosphotungstic acid heteropolyoxometalate alkali metal salt as a raw material, for example, according to the method described in Inorganic Synthesis, vol 27, p104. I can do it. Specifically, it can be obtained by dissolving an alkali metal salt of Dawson type phosphotungstic acid heteropolyoxometalate in water, adding an alkali metal hydrogencarbonate to this, and stirring while heating if necessary. .
  • R 6 and R 7 in the general formula (II) are optionally substituted alkyl groups having 1 to 8 carbon atoms, optionally substituted alkenyl groups having 2 to 6 carbon atoms, Represents a C3-C8 cycloalkyl group which may have a substituent.
  • substituents include those described in the above section [Substituent group R].
  • the anion charge is more delocalized, and the heat resistance of the coloring material is improved. It preferably has a fluorine atom as a substituent. That is, R 6 and R 7 are preferably perfluoroalkyl groups having 1 to 8 carbon atoms in that the anion charge is dispersed and the anion is stabilized. On the other hand, R 6 and R 7 may be connected to each other to form a ring. When forming a ring, the group formed by linking R 6 and R 7 is particularly preferably a fluoroalkylene group having 2 to 12 carbon atoms.
  • R 8 to R 10 in the general formula (III) are each an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, Represents a C3-C8 cycloalkyl group which may have a substituent.
  • substituents include those described in the above section [Substituent group R].
  • R 8 to R 10 are preferably perfluoroalkyl groups having 1 to 8 carbon atoms in that the anion charge is dispersed and the anion is stabilized.
  • R 8 to R 10 may be connected to each other to form a ring.
  • the group formed by linking R 8 to R 10 is particularly preferably a fluoroalkylene group having 2 to 12 carbon atoms.
  • sulfonate anion examples include aliphatic sulfonate anions which may have a substituent such as trifluoromethanesulfonic acid, methanesulfonic acid, pentanesulfonic acid, hexanesulfonic acid, heptanesulfonic acid, dodecanesulfonic acid, and camphorsulfonic acid. ; Benzenesulfonic acid, p-toluenesulfonic acid, 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, 2,6-naphthalenesulfonic acid, 1,3,6-naphthalenetrisulfonic acid, etc.
  • a is the number of chromogenic cation sites constituting the cation.
  • a is an integer of 2 or more.
  • the upper limit of a is not particularly limited, but a is preferably 4 or less, and more preferably 3 or less, from the viewpoint of ease of production.
  • b represents the number of cations in the molecular aggregate
  • d represents the number of anions in the molecular aggregate
  • b and d represent an integer of 1 or more.
  • the color material of the present invention is not limited to the case where each of b and d is 1 in the crystal or aggregate, and can take any natural number of 2, 3, 4,. From the viewpoint of heat resistance, it is preferable that at least a part of the coloring material of the present invention forms a molecular aggregate of b ⁇ 2. Moreover, it is preferable that at least a part of the coloring material of the present invention forms a molecular aggregate having d ⁇ 2 from the viewpoint of heat resistance.
  • a plurality of cations in the molecular aggregate may be one kind alone, or two or more kinds may be combined.
  • the anions present in the molecular aggregate may be one kind or a combination of two or more kinds.
  • the triarylmethane compound of the present invention can be easily produced, for example, by reacting the corresponding cation moiety chloride with the corresponding heteropolyacid or heteropolyoxometalate alkali metal salt.
  • the corresponding cation moiety chloride is used and a heteropolyacid is used
  • the corresponding cation moiety chloride is used by dehydrochlorination
  • the heteropolyoxometalate alkali metal salt is When used, it can be produced by salt substitution by dealkalizing metal chloride reaction.
  • the heteropolyacid is first converted to a heteropolyoxometalate alkali metal salt and then subjected to the dealkali metal chloride reaction, so that the salt substitution can be carried out more reliably, and the yield is improved.
  • This is preferable because not only the triarylmethane compound of the present invention can be obtained at a high level, but also the triarylmethane compound of the present invention can be obtained with less by-products and high purity.
  • the heteropolyoxometalate alkali metal salt can be used after being purified by recrystallization or the like.
  • the corresponding heteropolyoxometalate alkali metal salt can be obtained in a higher yield by reducing the solubility by cooling the reaction solution.
  • the amount of the anion source used for the heteropolyacid or heteropolyoxometalate alkali metal salt is charged so as to be an equimolar number depending on the ionic value. It is preferable to carry out the above reaction.
  • the triarylmethane compound of the present invention includes a step of rake (water insolubilization) with a heteropolyacid (or since it is raked (water insolubilization) with a heteropolyacid), it may be performed during or after the production process.
  • rake water insolubilization
  • a heteropolyacid or since it is raked (water insolubilization) with a heteropolyacid
  • it may be performed during or after the production process.
  • water in order to perform a more reliable reaction or to prevent the rake structure of the obtained compound from being destroyed, for example, metal ions or halogens such as purified water, ion-exchanged water, pure water, etc. It is preferable to use water with as little ion content as possible.
  • the triarylmethane compound of the present invention is a water-insoluble colorant.
  • the triarylmethane compound of the present invention thus obtained can be used as it is as a colorant for a synthetic resin or the like, but if necessary, the particle diameter can be adjusted by known and conventional pulverization or granulation.
  • the colorant can be optimal for various applications.
  • the colorant preferably has an average primary particle diameter of 100 nm or less because a clearer blue colored product can be easily obtained.
  • the average particle diameter of primary particles is measured as follows. First, the particle
  • the triarylmethane compound of the present invention is used for the production of a color filter pixel part because it has a small hue change and excellent heat resistance even after a thermal history at a high temperature in various known and commonly used applications.
  • the color filter of the liquid crystal display device capable of excellent image display with little hue change can be obtained.
  • the conventional cold cathode tube CCFL light source
  • white LED LED; Light Emitting Diode
  • three-color independent LED light source white organic EL (EL; Electro Luminescence)
  • EL Electro Luminescence
  • the triarylmethane compound of the present invention includes ⁇ -type copper phthalocyanine pigment, dioxazine pigment (CI Pigment Violet 23, CI Pigment Violet 37, CI Pigment Blue 80, etc.) and the like.
  • a synthetic resin that is liquid and water-insoluble at room temperature, such as a derivative, can be contained. Addition of these dispersants and resins also contributes to reduction of flocculation, improvement of dispersion stability, and improvement of viscosity characteristics of the dispersion.
  • the triarylmethane compound of the present invention itself has a hue suitable for the preparation of a color filter blue pixel part. If necessary, the ⁇ -type copper phthalocyanine pigment (C.I. By using 0.1 to 30 parts of Pigment Blue 15: 6) together, the hue can be optimized.
  • the triarylmethane compound of the present invention itself has heat resistance and light resistance suitable for the preparation of the color filter blue pixel portion, but if necessary, the antioxidant non-volatile per 100 parts of the triarylmethane compound. 0.1 to 10 parts per minute, and in particular 0.5 to 8 parts can be used.
  • the term “antioxidant” is a general term for additives that prevent oxidative degradation. Those that prevent oxidative degradation due to heat (antioxidants in a narrow sense) and those that prevent oxidative degradation due to light (mainly ultraviolet rays). (Referred to in the narrow sense as light stabilizers). *
  • antioxidants have the ability to trap radicals and prevent auto-oxidation (radical chain prevention) and the action to decompose hydroperoxide (peroxide) into harmless ones (peroxide decomposition action)
  • the former is called a primary antioxidant and the latter is called a secondary antioxidant.
  • primary antioxidants include phenolic (including hindered phenols) and amine (including hindered amines) antioxidants
  • secondary antioxidants include, for example, sulfur and phosphorus. Each of these antioxidants is typical.
  • the triarylmethane compound of the present invention itself has heat resistance suitable for the preparation of a color filter blue pixel portion, but if necessary, heat resistance and light resistance can be improved by using a cationic resin together. It can be raised one step further.
  • a cationic resin for example, an acrylic resin, a polyurethane resin, an epoxy resin, a polyamide resin, or the like is preferably used because the hue change is small even under a thermal history and the heat resistance of the color filter can be greatly improved.
  • the ratio of the triarylmethane compound and the cationic resin on the basis of mass of the non-volatile content is not particularly limited, but the non-volatile content of the latter resin is 0.1 to 10 parts per 100 parts of the former compound.
  • the content is preferably 0.5 to 5 parts, particularly 1 to 3 parts.
  • the triarylmethane compound of the present invention can be used for forming a color filter pixel portion by a conventionally known method.
  • a typical method for dispersing the triarylmethane compound of the present invention is a photolithography method, which includes a photocurable composition described later on the side where a black matrix of a transparent substrate for a color filter is provided. After applying to the surface, heating and drying (pre-baking), pattern exposure is performed by irradiating ultraviolet rays through a photomask to cure the photocurable compound at the location corresponding to the pixel portion, and then the unexposed portion This is a method of developing with a developer, removing the non-pixel portion, and fixing the pixel portion to the transparent substrate. In this method, a pixel portion made of a cured colored film of a photocurable composition is formed on a transparent substrate.
  • a photocurable composition to be described later is prepared, and the above-described operation is repeated to manufacture a color filter having red, green, and blue colored pixel portions at predetermined positions. be able to.
  • a blue pixel portion can be formed from the triarylmethane compound of the present invention.
  • a well-known and usual red pigment and green pigment can be used.
  • pigments for forming the red pixel portion for example, C.I. I. Pigment Red 177, 209, 242 and 254 are pigments for forming the green pixel portion, for example, C.I. I. Pigment Green 7, 10, 36, 47, 58 and the like.
  • a yellow pigment can be used in combination for forming the red pixel portion and the green pixel portion.
  • the entire color filter can be heat-treated (post-baked) in order to thermally cure the unreacted photocurable compound.
  • Examples of a method for applying a photocurable composition described later on a transparent substrate such as glass include a spin coating method, a roll coating method, and an ink jet method.
  • the drying conditions of the coating film of the photocurable composition applied to the transparent substrate vary depending on the type of each component, the blending ratio, and the like, but are usually about 50 to 150 ° C. for about 1 to 15 minutes.
  • light used for photocuring the photocurable composition it is preferable to use light in the wavelength region of 200 to 500 nm. Various light sources that emit light in this wavelength range can be used.
  • Examples of the developing method include a liquid filling method, a dipping method, and a spray method.
  • the transparent substrate on which the necessary color pixel portion is formed is washed with water and dried.
  • the color filter thus obtained is subjected to a heat treatment (post-baking) at 90 to 280 ° C. for a predetermined time by a heating device such as a hot plate or an oven, thereby removing volatile components in the colored coating film and simultaneously applying light.
  • the unreacted photocurable compound remaining in the cured colored film of the curable composition is thermally cured to complete the color filter.
  • the photocurable composition for forming the blue pixel portion of the color filter comprises the triarylmethane compound of the present invention, a dispersant, a photocurable compound, and an organic solvent as essential components, and if necessary, heat It can prepare by mixing these using a plastic resin.
  • a photocurable compound is used in preparing the photocurable composition.
  • a thermoplastic resin is used in combination, it is preferable to use an organic solvent that dissolves it.
  • the triarylmethane compound of the present invention As a method for producing the photocurable composition, the triarylmethane compound of the present invention, an organic solvent and a dispersant are used as essential components, and these are mixed and stirred and dispersed so as to be uniform. After preparing a dispersion for forming the pixel portion of the color filter, a photocurable compound and, if necessary, a thermoplastic resin or a photopolymerization initiator are added to the photocurable composition. The method to do is common.
  • dispersant and the organic solvent those described above can be used.
  • thermoplastic resin used for the preparation of the photocurable composition examples include urethane resins, acrylic resins, polyamide resins, polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, and the like. .
  • photocurable compound examples include 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, and 3-methylpentanediol diacrylate.
  • Bifunctional monomers such as acrylate, trimethylol propaton triacrylate, pentaerythritol triacrylate, tris [2- (meth) acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, etc.
  • High molecular weight such as low molecular weight polyfunctional monomer, polyester acrylate, polyurethane acrylate, polyether acrylate, etc. Polyfunctional monomers.
  • photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethyl ketal, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4′- Azidobenzal) -2-propane-2′-sulfonic acid, 4,4′-diazidostilbene-2,2′-disulfonic acid, and the like.
  • photopolymerization initiators examples include “Irgacure (trade name) -184”, “Irgacure (trade name) -369”, “Darocur (trade name) -1173” manufactured by Ciba Specialty Chemicals, and BASF Corporation. “Lucirin-TPO”, Nippon Kayaku Co., Ltd. “Kayacure (trade name) DETX”, “Kayacure (tradename) OA”, Stoffer “Bicure 10”, “Bicure 55”, Akzo Corporation “Trigonal PI” “Sandray 1000” manufactured by Sand, “Deep” manufactured by Upjohn, and “Biimidazole” manufactured by Kurokin Kasei.
  • a known and commonly used photosensitizer can be used in combination with the photopolymerization initiator.
  • the photosensitizer include amines, ureas, compounds having a sulfur atom, compounds having a phosphorus atom, compounds having a chlorine atom, nitriles or other compounds having a nitrogen atom. These can be used alone or in combination of two or more.
  • the blending ratio of the photopolymerization initiator is not particularly limited, but is preferably in the range of 0.1 to 30% with respect to the compound having a photopolymerizable or photocurable functional group on a mass basis. If it is less than 0.1%, the photosensitivity at the time of photocuring tends to decrease, and if it exceeds 30%, when the resist coating film is dried, crystals of the photopolymerization initiator are precipitated, and the coating film properties. May cause deterioration.
  • a photocurable composition for forming a color filter pixel portion can be obtained by adding an agent and, if necessary, further an organic solvent, and stirring and dispersing so as to be uniform.
  • the developer a known and commonly used organic solvent or alkaline aqueous solution can be used.
  • the photocurable composition contains a thermoplastic resin or a photocurable compound, and at least one of them has an acid value and exhibits alkali solubility
  • the color filter can be washed with an alkaline aqueous solution. It is effective for forming the pixel portion.
  • the method for producing the color filter pixel portion by photolithography was described in detail.
  • the color filter pixel portion prepared using the triarylmethane compound of the present invention is the other
  • a color filter may be manufactured by forming a blue pixel portion by a method such as an electrodeposition method, a transfer method, a micellar electrolysis method, a PVED (Photovoltaic Electrodeposition) method, an ink jet method, a reverse printing method, or a thermosetting method.
  • the color filter uses a photocurable composition of each color obtained by using a red pigment, a green pigment, and the triarylmethane compound of the present invention as an organic pigment, and encloses a liquid crystal material between a pair of parallel transparent electrodes.
  • the transparent electrode is divided into discontinuous fine sections, and a color selected from any one of red, green, and blue is provided for each of the fine sections divided into a grid by the black matrix on the transparent electrode. It can be obtained by providing filter colored pixel portions alternately in a pattern or by providing a transparent electrode after forming color filter colored pixel portions on a substrate.
  • the triarylmethane compound of the present invention can provide a dispersion having excellent sharpness and lightness, and for color filter applications, paints, plastics (resin molded products), printing inks, rubber, leather, textile printing, electrostatic image development
  • the present invention can also be applied to coloring toner, ink jet recording ink, thermal transfer ink, and the like.
  • reaction solution was poured into ice water, adjusted to pH 10 or higher with 15% aqueous sodium hydroxide solution, and extracted with chloroform.
  • the chloroform layer was washed with 5% aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate.
  • reaction solution was poured into ice water, adjusted to pH 10 or higher with 15% aqueous sodium hydroxide solution, and extracted with chloroform.
  • the chloroform layer was washed with 5% aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 7 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 8 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 9 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 10 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 11 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 12 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 13 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 16 was used instead of Compound 6.
  • An evaluation glass substrate was obtained in the same manner as in Example 1 except that Compound 17 was used instead of Compound 6.
  • the present invention can be synthesized by freely changing the A part effective in heat resistance by linking the linking group Z at a specific site. It is excellent in that the property can be further improved. For example, if the intermediate 1 or the intermediate 2 is synthesized, the part A can be easily changed. Furthermore, since the color is changed by changing the A portion, it can be adjusted to a desired color.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)

Abstract

L'invention concerne un matériau colorant qui subit peu de changement de teinte, même dans un historique de température de 200°C ou plus, qui est nécessaire pour des procédés de production de filtre couleur. L'invention concerne, par exemple : un composé de type triarylméthane qui, lorsqu'il est utilisé dans la préparation d'éléments de pixel de couleur bleue dans un filtre couleur, peut permettre d'obtenir un dispositif d'affichage à cristaux liquides apte à un excellent affichage à cristaux liquides présentant peu de changement de teinte et autres ; et un filtre couleur contenant le composé de type triarylméthane. Il a été trouvé que, lorsqu'un composé de type triarylméthane, composé d'un cation colorant de triarylméthane polymérisé basique, présentant une structure spécifique, et d'un contre-anion spécifique, est utilisé comme matériau colorant pour un filtre couleur, on observe peu de changement de teinte, même dans un historique de température dans la production d'un filtre couleur. Cette découverte conduit à la réalisation de la présente invention.
PCT/JP2017/002664 2016-02-25 2017-01-26 Composé et filtre couleur WO2017145627A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2017525428A JP6255634B1 (ja) 2016-02-25 2017-01-26 化合物及びカラーフィルタ

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-034327 2016-02-25
JP2016034327 2016-02-25

Publications (1)

Publication Number Publication Date
WO2017145627A1 true WO2017145627A1 (fr) 2017-08-31

Family

ID=59685487

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/002664 WO2017145627A1 (fr) 2016-02-25 2017-01-26 Composé et filtre couleur

Country Status (3)

Country Link
JP (1) JP6255634B1 (fr)
TW (1) TW201800495A (fr)
WO (1) WO2017145627A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018085391A1 (fr) * 2016-11-01 2018-05-11 Milliken & Company Leuco-polymères en tant qu'agents d'azurage dans des compositions d'entretien du linge
WO2019044096A1 (fr) * 2017-08-28 2019-03-07 Dic株式会社 Composé et filtre de couleur
JP2019089950A (ja) * 2017-11-15 2019-06-13 Dic株式会社 化合物及びカラーフィルタ
WO2020071041A1 (fr) * 2018-10-02 2020-04-09 株式会社Ｄｎｐファインケミカル Dispersion de matière colorante, composition de résine colorée et produit durci correspondant, filtre couleur et dispositif d'affichage
CN114127048A (zh) * 2019-07-25 2022-03-01 Dic株式会社 化合物

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE817398C (de) * 1945-12-14 1951-10-18 Gevaert Photo Prod Nv Verfahren zur Herstellung von gefaerbten photographischen Schichten
JPS5450030A (en) * 1977-09-05 1979-04-19 Basf Ag Double triphenylmethane dyestuff
DE3103110A1 (de) * 1981-01-30 1982-08-26 Basf Ag, 6700 Ludwigshafen Triazingruppenhaltige verbindungen
JPH0324166A (ja) * 1989-05-31 1991-02-01 Basf Ag トリフエニルメタン染料およびピペラジン誘導体
JP2005533341A (ja) * 2002-07-10 2005-11-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー トリアリールメタンを主成分とする電荷輸送組成物およびその電子デバイスにおける使用
JP2013010814A (ja) * 2011-06-28 2013-01-17 Toppan Printing Co Ltd 重合性二重結合を持つトリアリールメタン染料、トリアリールメタン染料を側鎖に持つ高分子化合物、カラーフィルタ用着色組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置
JP2013057054A (ja) * 2011-04-21 2013-03-28 Dainippon Printing Co Ltd 色材、及びその製造方法
WO2014061143A1 (fr) * 2012-10-18 2014-04-24 大日本印刷株式会社 Matériau colorant et procédé de production de celui-ci
JP2014214274A (ja) * 2013-04-26 2014-11-17 大日本印刷株式会社 色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE817398C (de) * 1945-12-14 1951-10-18 Gevaert Photo Prod Nv Verfahren zur Herstellung von gefaerbten photographischen Schichten
JPS5450030A (en) * 1977-09-05 1979-04-19 Basf Ag Double triphenylmethane dyestuff
DE3103110A1 (de) * 1981-01-30 1982-08-26 Basf Ag, 6700 Ludwigshafen Triazingruppenhaltige verbindungen
JPH0324166A (ja) * 1989-05-31 1991-02-01 Basf Ag トリフエニルメタン染料およびピペラジン誘導体
JP2005533341A (ja) * 2002-07-10 2005-11-04 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー トリアリールメタンを主成分とする電荷輸送組成物およびその電子デバイスにおける使用
JP2013057054A (ja) * 2011-04-21 2013-03-28 Dainippon Printing Co Ltd 色材、及びその製造方法
JP2013010814A (ja) * 2011-06-28 2013-01-17 Toppan Printing Co Ltd 重合性二重結合を持つトリアリールメタン染料、トリアリールメタン染料を側鎖に持つ高分子化合物、カラーフィルタ用着色組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置
WO2014061143A1 (fr) * 2012-10-18 2014-04-24 大日本印刷株式会社 Matériau colorant et procédé de production de celui-ci
JP2014214274A (ja) * 2013-04-26 2014-11-17 大日本印刷株式会社 色材分散液、カラーフィルタ用着色樹脂組成物、カラーフィルタ、液晶表示装置、及び有機発光表示装置

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018085391A1 (fr) * 2016-11-01 2018-05-11 Milliken & Company Leuco-polymères en tant qu'agents d'azurage dans des compositions d'entretien du linge
WO2019044096A1 (fr) * 2017-08-28 2019-03-07 Dic株式会社 Composé et filtre de couleur
JP2019089950A (ja) * 2017-11-15 2019-06-13 Dic株式会社 化合物及びカラーフィルタ
JP7027830B2 (ja) 2017-11-15 2022-03-02 Dic株式会社 化合物及びカラーフィルタ
WO2020071041A1 (fr) * 2018-10-02 2020-04-09 株式会社Ｄｎｐファインケミカル Dispersion de matière colorante, composition de résine colorée et produit durci correspondant, filtre couleur et dispositif d'affichage
JPWO2020071041A1 (ja) * 2018-10-02 2021-09-24 株式会社Ｄｎｐファインケミカル 色材分散液、着色樹脂組成物及びその硬化物、カラーフィルタ、並びに表示装置
JP7346435B2 (ja) 2018-10-02 2023-09-19 株式会社Ｄｎｐファインケミカル 色材分散液、着色樹脂組成物及びその硬化物、カラーフィルタ、並びに表示装置
CN114127048A (zh) * 2019-07-25 2022-03-01 Dic株式会社 化合物

Also Published As

Publication number Publication date
JP6255634B1 (ja) 2018-01-10
TW201800495A (zh) 2018-01-01
JPWO2017145627A1 (ja) 2018-03-01

Similar Documents

Publication Publication Date Title
JP6255634B1 (ja) 化合物及びカラーフィルタ
US8420860B2 (en) Compound and color filter
JP6040652B2 (ja) 化合物及びカラーフィルタ
TWI388630B (zh) 化合物及彩色濾光片
TWI630237B (zh) 彩色濾光片用著色樹脂組成物、色材分散液、彩色濾光片、液晶顯示裝置及有機發光顯示裝置
TWI628245B (zh) 彩色濾光片用色材分散液、色材、彩色濾光片、液晶顯示裝置及有機發光顯示裝置
JP5725357B2 (ja) 化合物及びカラーフィルタ
KR20170088939A (ko) 컬러 필터용 색재 분산액, 컬러 필터용 착색 수지 조성물, 색재, 컬러 필터, 액정 표시 장치 및 발광 표시 장치
JP2011180365A (ja) カラーフィルタ用青色顔料組成物、その製造方法、カラーフィルタ、及び液晶表示装置
JP6468407B1 (ja) 化合物及びカラーフィルタ
JP6098913B1 (ja) フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有するカラーフィルタ、着色組成物
JP6024343B2 (ja) カラーフィルタ用青色顔料組成物、カラーフィルタ用青色光硬化性組成物及びカラーフィルタ
JP7027830B2 (ja) 化合物及びカラーフィルタ
JP2020033521A (ja) 顔料組成物、着色組成物及びカラーフィルタ
WO2019044096A1 (fr) Composé et filtre de couleur
JP6493039B2 (ja) 化合物及びカラーフィルタ
JP2017014331A (ja) 化合物及びカラーフィルタ
JP6957909B2 (ja) 化合物及びカラーフィルタ
TW201525077A (zh) 著色組成物、著色組成物的製造方法、硬化膜、彩色濾光片、彩色濾光片的製造方法、固體攝像元件及液晶顯示裝置
WO2024116819A1 (fr) Filtre coloré et dispositif d'affichage

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2017525428

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17756069

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 17756069

Country of ref document: EP

Kind code of ref document: A1