WO2017013090A1 - Composé de colorant, et matière de colorant le comprenant - Google Patents

Composé de colorant, et matière de colorant le comprenant Download PDF

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Publication number
WO2017013090A1
WO2017013090A1 PCT/EP2016/067122 EP2016067122W WO2017013090A1 WO 2017013090 A1 WO2017013090 A1 WO 2017013090A1 EP 2016067122 W EP2016067122 W EP 2016067122W WO 2017013090 A1 WO2017013090 A1 WO 2017013090A1
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Prior art keywords
group
substituted
compound
compound according
groups
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PCT/EP2016/067122
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English (en)
Inventor
Hyunsu Lee
Sangmin Han
Iljo Choi
Eunha Jeong
Seunghwan Lee
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Solvay SA
Iridos Ltd
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Solvay SA
Iridos Ltd
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Priority to JP2018502632A priority Critical patent/JP6908587B2/ja
Priority to KR1020187004603A priority patent/KR102527494B1/ko
Priority to CN201680042686.8A priority patent/CN107850835A/zh
Publication of WO2017013090A1 publication Critical patent/WO2017013090A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • a colorant compound, and a colorant material comprising the same
  • the present invention relates to novel colorant compounds based on triarylmethane substructure, and methods for preparing the same.
  • the present invention also concerns colorant compositions for color filter comprising the same, and display devices equipped with such color filter.
  • Color filters are widely used in various applications, particularly used in display devices, such as liquid crystal display (LCD) and organic light-emitting display (OLED) and the like. Due to rapid progression of the display
  • a color composition having a colorant material comprising a pigment and/or a dye is often used.
  • Pigment usually shows better stability against heat and/or environment, but an achievable brightness is often insufficient compared with dye.
  • dye when dye is used as the color filter colorant, satisfactory brightness of the color filter may be attained, but its stability, especially thermal stability, and/or contrast ratio are often insufficient.
  • a dyestuff having a triarylmethane structure is believed to be a good candidate for the color filter application.
  • its stability especially thermal stability, is not high enough to endure high-temperature process(es) of color filter fabrication.
  • PCT International patent application publication No. WO 2012/144521 Al suggests a colorant dispersion liquid, a colored resin composition for use in color filters, a color filter formed using said colored resin composition for use in color filters; and a liquid crystal display device and an organic light-emitting display device that have said color filter.
  • the colorant dispersion liquid containing a colorant of the dimerized triarylmethane structure having the chemical formula below.
  • the purpose of the present invention is to provide a novel compound comprising triarylmethane substructure with an excellent thermal stability.
  • Another purpose is to provide a colorant compound, especially a blue colorant compound, which endures high-temperature process of color filter fabrication in display application as well as exhibits sufficient brightness and/or contrast ratio.
  • the compounds of the present invention show outstanding thermal stability. It has also been found that the compounds according to the present invention can be advantageously used for the formation of color filter having excellent brightness and/or contrast ratio.
  • alkyl groups is understood to denote in particular a straight chain, branched chain, or cyclic hydrocarbon groups usually having from 1 to 20 carbon atoms.
  • alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Some or all of the hydrogen atoms of the alkyl group may or may not be substituted with other groups, such as halogen atom, amino groups or hydroxyl groups.
  • alkoxy groups is understood to denote in particular a straight chain, branched chain, or cyclic hydrocarbon group usually having from 1 to 20 carbon atoms, preferably from 1 to 8 carbon atoms, singularly bonded to oxygen (Alk-O-).
  • aryl groups is understood to denote in particular any functional group or substituent derived from an aromatic ring.
  • the aryl groups can have 6 to 20 carbon atoms (preferably 6 to 12 due to its easiness of synthesis at a low cost) in which some or all of the hydrogen atoms of the aryl group may or may not be substituted with other groups, especially halogen atom, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, thioalkoxy groups, heterocycles, amino groups or hydroxyl groups.
  • the aryl groups are preferably optionally substituted phenyl groups, naphthyl groups, anthryl group and phenanthryl group.
  • heterocycles is understood to denote in particular a cyclic compound, which has at least one heteroatom as a member of its one or more rings. Frequent heteroatoms within the ring include sulfur, oxygen and nitrogen.
  • the heterocycles can be either saturated or unsaturated, aromatic or non-aromatic, and may be 3-membered, 4-membered, 5-membered, 6-membered or 7-membered ring.
  • the heterocycles can be further fused with other one or more ring systems.
  • heterocycles examples include pyrrolidines, oxolanes, thiolanes, pyrroles, furans, thiophenes, piperidines, oxanes, thianes, pyridines, pyrans, pyrazoles, imidazoles, and thiopyrans, and their derivatives.
  • the heterocycles can further be substituted by other groups, such as alkyl groups, alkoxy groups, aryl groups, thioalkoxy groups, amino groups or aryloxy groups as defined above.
  • halogenated is understood to denote in particular at least one of the hydrogen atoms of the following chemical group has been replaced by a halogen atom, preferably selected from fluorine and chlorine, more preferably fluorine. If all of the hydrogen atoms have been replaced by halogen atoms, the halogenated chemical group is perhalogenated.
  • halogenated alkyl groups include (per)fluorinated alkyl groups such as (per)fluorinated methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl; and for instance -CF 3 , -C 2 F 5 , heptafluoroisopropyl (-CF(CF 3 ) 2 ), hexafluoroisopropyl (-CH(CF 3 ) 2 ) or -CF 2 (CF 2 ) 4 CF 3 .
  • millbase composition is understood to denote in particular an intermediate composition which comprises at least a part of components to be included in a final composition for forming a color filter.
  • the final composition for forming a color filter can be formulated by combining the millbase composition with other components.
  • the millbase composition often comprises at least colorant components to be included in the final composition for forming a color filter.
  • One aspect of the present invention concerns a compound having the formula (I) below:
  • X is independently oxygen atom, -NH-, or sulfur atom. Especially, X is preferably sulfur atom.
  • Rl 1 is independently selected from the group consisting of hydrogen atom, alkyl groups, and aryl groups.
  • the alkyl groups and aryl groups may be substituted with other groups. It is preferred that the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
  • the alkyl groups may be substituted with one or more halogen atoms, in particular with fluorine atom, or with amino group.
  • the aryl groups may be substituted with one or more halogen atoms, such as fluorine atom, optionally fluorinated alkyl groups having 1 to 4 carbon atoms, optionally fluorinated alkoxy groups having 1 to 4 carbon atoms, and hydroxyl group.
  • Rl 1 is independently selected from the aryl groups substituted with alkyl group or halogen atom.
  • Rl 1 includes halogenated benzenes, such as fluorinated benzenes and chlorinated benzenes, alkyl-substituted benzenes, and alkoxy-substituted benzenes, but the present invention is not limited thereto.
  • R21 is independently selected from the group consisting of hydrogen atom, alkyl groups, and aryl groups.
  • the alkyl groups and aryl groups may be substituted with other groups. It is preferred that the alkyl groups have 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
  • the alkyl groups may be substituted with one or more halogen atoms, in particular with fluorine atom, or with amino group.
  • the aryl groups may be substituted with one or more halogen atoms, such as fluorine atom, optionally fluorinated alkyl groups having 1 to 4 carbon atoms, optionally fluorinated alkoxy groups having 1 to 4 carbon atoms, and hydroxyl group.
  • R21 is independently selected from the aryl groups substituted with alkyl group or halogen atom.
  • Particular examples of R21 includes halogenated benzenes, such as fluorinated benzenes and chlorinated benzenes, alkyl-substituted benzenes, and alkoxy-substituted benzenes, but the present invention is not limited thereto.
  • each R31, R32, R33, R34, R35, R36, R37, and R38 is independently selected from the group consisting of hydrogen atom, halogen atom, alkyl groups, alkoxy groups, cyano group, nitro group, sulfonyl group, and hydroxyl group.
  • the alkyl groups and alkoxy groups may be substituted with other groups.
  • R34 and R35 may be bound together to form -0-, -NH-, -S-, or -SO 2 -. It is preferred that R31 to R38 are hydrogen atom.
  • each R41, R42, R43, and R44 is independently selected from the group consisting of hydrogen atom, alkyl groups, and aryl groups.
  • the alkyl groups and aryl groups may be substituted with other groups. Examples thereof include optionally substituted alkyl groups having 1 to 10 carbon atoms, such as ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, hexyl group, 2-ethylhexyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, and 2,2,2- trifluoroethyl group, but the present invention is not limited thereto.
  • a fluorine- containing groups in particular an alkyl group or an aryl group substituted by at least one fluorine atom, may be used in the present invention.
  • Each R41 and R42, or R43 and R44 may be bound together to form a ring structure.
  • Such ring structure may comprise one or more heteroatoms, such as nitrogen, sulfur and oxygen. Examples of the ring comprise the following structure, but the present invention is not limited thereto:
  • R41 to R44 are ethyl group.
  • L denotes a linking group to connect two or more same or different triarylmethane substructures.
  • L has valency of "n" which is understood to stand for the number of triarylmethane substructures in the molecule.
  • the linking group "L” in the present invention comprises at least one aromatic ring. Such aromatic rings can be further substituted by substituents.
  • the nitrogen atom of the amine group of the heterocycle substructure in the formula (I) can be connected to any atom in the substituent of the aromatic ring of the L or be directly connected to the atom which constitutes the aromatic ring of the L.
  • aromatic ring examples include hydrocarbon-based aromatic rings, such as benzene ring, naphthalene ring, tetralin ring, indene ring, fluorene ring, anthracene ring, phenanthrene ring, biphenyl, and terphenyl, and
  • heterocyclic aromatic rings including 5-membered rings, such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole, and pyrazole; 6-membered rings, such as pyran, pyridine, pyridazine, pyrimidine, and pyrazine; and fused rings, such as benzofuran, thionaphthene, indole, carbazole, cumarine, quinoline, isoquinoline, acridine, quinazoline, and quinoxaline; but the present invention is not limited thereto.
  • Such aromatic ring may be further substituted by any substituents.
  • substituents include halogen atoms, such as fluorine atom, chlorine atom, and bromine atom, alkyl groups, carboxyl group, and amino groups, but the present invention is not limited thereto.
  • "L” comprises hydrocarbon-based aromatic rings with 6 to 14 carbon atoms. More preferably, “L” comprises benzene group, or naphthalene group, particularly benzene group. Particular examples of “L” include the following structures, but the present invention is not limited thereto:
  • n stands for the number of triarylmethane substructures, and as such, is an integer of 2 or more, “n” is often no more than 4, more preferably no more than 3. It is particularly preferred when “n” is 2.
  • a stands for the valency of the counter-anion "An,” and thus, is an integer of 1 or more, “a” may be an integer of 1. "a” is preferably an integer of 2 or more, more preferably 2 or 3, most preferably 2.
  • n stands for the number of cationic part
  • b stands for the number of anionic part
  • each is an integer of 1 or more
  • n and b can be suitably selected depending on the number of cationic triarylmethane substructures ("n") and the valency of the counter-anion ("a").
  • n cationic triarylmethane substructures
  • a valency of the counter-anion
  • An denotes any counter-anion.
  • Type of the counter-anion is not particularly limited in the present invention, and can be organic anions, or inorganic anions.
  • An a" is preferably selected from the group consisting of halides, borate anions, carboxylate anions, sulfate anions, sulfonate anions, sulfonimide anions, phosphate anions, and any combination thereof.
  • the anionic compounds comprising at least one sulfonate group, especially those comprising two or more sulfonate groups, are particularly preferred in the present invention.
  • the counter-anion (An) may comprise anionic dye or pigment compounds which comprise at least one anionic functional group, such as carboxylate group, sulfate group, phosphate group, and sulfonate group.
  • anionic functional group such as carboxylate group, sulfate group, phosphate group, and sulfonate group. Examples of the dyes and the pigments can be found in PCT international patent application publication No. WO 2012/144521 Al and
  • the compound of the present invention preferably comprises the divalent cation having the formula (II- 1) or ( ⁇ -2) below:
  • each X, Rl 1, R21, R31 to R38, and R41 to R44 have the same meaning as defined in the above.
  • each R51, R52, R53, and R54 is independently selected from the group consisting of hydrogen atom, halogen atom, alkyl groups, alkoxy groups, cyano group, nitro group, sulfonyl group, and hydroxyl group.
  • the alkyl groups and aryl groups may be substituted with other groups.
  • alkyl groups having 1 to 10 carbon atoms such as ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, hexyl group, 2-ethylhexyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-cyanoethyl group, and 2,2,2- trifluoroehtyl group, but the present invention is not limited thereto.
  • Another aspect of the present invention concerns a method of preparing the compound of the present invention. Such a method includes reacting the compound of formula (III) and the compound of formula (IV) below:
  • each X, L, Rl 1, R21, R31 to R38, R41 to R44, and "n" has the same meaning as defined in the above.
  • the desired counter-anion may be introduced as necessary.
  • the compound of the present invention is advantageously used as a blue colorant, of which use can be optionally combined with at least one further dye or pigment. Therefore, further aspect of the present invention provides a colorant material comprising the compound according to the invention, and optionally at least another dye or pigment. Examples of the dyes and of the pigments can be found in PCT international patent application publication No. WO 2012/144521 Al and Japanese patent application publication No. JP 2014- 108975 A, respectively, both are incorporated herein by reference by their entireties.
  • the compound of the present invention can be used as a colorant material in combination with a blue pigment, such as ⁇ -type copper phthalocyanine particles or a violet pigment such as pigment violent(PV)-23, the pigment optionally containing at least one sulfonate group.
  • a blue pigment such as ⁇ -type copper phthalocyanine particles or a violet pigment such as pigment violent(PV)-23
  • the pigment optionally containing at least one sulfonate group.
  • the compound of the present invention can be suitably used for the formation of color filter. Accordingly, still further aspect of the present invention concerns a composition for forming color filter, comprising the compound or the colorant material according to the invention.
  • the composition may optionally comprise at least one component selected from the group consisting of a pigment, a dye, a binder, a dispersion aid or dispersant, a polymerizable monomer, a solvent, an inhibitor, a polymerization initiator, and any combination thereof.
  • the composition for forming color filter may be a millbase composition for color filter.
  • the millbase composition preferably comprises (A) a colorant material; (B) a solvent; and (C) a binder, wherein the colorant material (A) comprises the compound of the invention or the colorant material of the present invention.
  • the present invention also relates to a color filter comprising the
  • color filters may be prepared by lithographic methods, especially through the following steps: combining the millbase composition according to the present invention with other additional components to form a composition for forming color filter, applying the composition for forming color filter on a substrate, drying, exposing and developing.
  • the color filters are applicable for preparation of display devices, such as a liquid crystal display device, a light-emitting display device, or a solid-state image sensing device such as a charge coupled device (CCD) and the like.
  • display devices such as a liquid crystal display device, a light-emitting display device, or a solid-state image sensing device such as a charge coupled device (CCD) and the like.
  • CCD charge coupled device
  • the present invention therefore also relates to the use of the compound of the present invention as a colorant, preferably as a blue colorant, and to the use of the compound or of the colorant material of the present invention for preparation of color filters, and in particular for forming the blue portion of color filters.
  • Still further aspect of the present invention concerns the compound having the formula (III) below :
  • each X, L, Rl 1, R21, and "n" has the same meaning as defined in the above.
  • the Compound 2 (15 g, 23.33 mmol) was dissolved in 150 ml of 2N NaOH, and refluxed for 15 hours. After completion of the reaction, the temperature was cooled down to room temperature. After adding 150 ml of DCM, extraction was conducted two times. The organic layer was dried with MgS04 and filtered. After concentration under reduced pressure, the Compound 3 was obtained.
  • the Compound 5 (5 g, 3.78 mmol) and bis(trifluoromethane)sulfonimide lithium salt (2.71 g, 9.46 mmol) were dissolved in 100 ml of MeOH, and stirred for 2 hours at room temperature. 500 ml of H 2 0 was slowly added drop-wise to the mixture under stirring. The produced solid was filtered, and washed with 50 ml of H 2 0 three times to obtain the Compound 6.
  • Heat resistance test The film obtained from (4) was introduced to oven and baked at the temperature of 240 °C for 40 min. The baking at the temperature of 240 °C for 40 min. was repeated two more times. ⁇ , ⁇ , Ay, and ⁇ E*ab were measured by comparing the respective value before and after each baking at 240 °C for 40 min.
  • the compound according to the present invention exhibit greatly improved heat resistance (AE*ab) over the comparative compound. Moreover, the compound according to the invention shows higher brightness as well as contrast ratio than then comparative compound.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

La présente invention comprend de nouveaux composés de colorant présentant une sous-structure de triarylméthane, des procédés de préparation de ceux-ci, et des matières de colorants les comprenant.
PCT/EP2016/067122 2015-07-20 2016-07-19 Composé de colorant, et matière de colorant le comprenant Ceased WO2017013090A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2018502632A JP6908587B2 (ja) 2015-07-20 2016-07-19 着色剤化合物及びこれを含む着色剤材料
KR1020187004603A KR102527494B1 (ko) 2015-07-20 2016-07-19 착색 화합물, 및 이를 포함하는 착색제 물질
CN201680042686.8A CN107850835A (zh) 2015-07-20 2016-07-19 着色剂化合物、及包含该着色剂化合物的着色剂材料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2015-0102683 2015-07-20
KR1020150102683A KR20170010969A (ko) 2015-07-20 2015-07-20 착색 화합물, 및 이를 포함하는 착색제 물질

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WO2017013090A1 true WO2017013090A1 (fr) 2017-01-26

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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
WO2018180918A1 (fr) * 2017-03-31 2018-10-04 株式会社Ｄｎｐファインケミカル Composition de résine colorante photosensible, produit durci de celle-ci, filtre coloré et dispositif d'affichage
JP6450057B1 (ja) * 2017-03-31 2019-01-09 株式会社Ｄｎｐファインケミカル 感光性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
WO2019031292A1 (fr) * 2017-08-10 2019-02-14 株式会社Ｄｎｐファインケミカル Composition de résine colorante photosensible, produit durci de celle-ci, filtre coloré et dispositif d'affichage

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JP2018522983A (ja) 2018-08-16
KR20170010969A (ko) 2017-02-02
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