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WO2015133649A1 - Nouveau composé et composition colorée photosensible - Google Patents

Nouveau composé et composition colorée photosensible Download PDF

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Publication number
WO2015133649A1
WO2015133649A1 PCT/JP2015/056982 JP2015056982W WO2015133649A1 WO 2015133649 A1 WO2015133649 A1 WO 2015133649A1 JP 2015056982 W JP2015056982 W JP 2015056982W WO 2015133649 A1 WO2015133649 A1 WO 2015133649A1
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Prior art keywords
group
substituted
halogen atom
carbon atoms
unsubstituted
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PCT/JP2015/056982
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English (en)
Japanese (ja)
Inventor
裕介 久保田
祐史 小田
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Adeka Corp
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Adeka Corp
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Priority to KR1020167011637A priority Critical patent/KR102326662B1/ko
Priority to JP2016506213A priority patent/JPWO2015133649A1/ja
Priority to CN201580002455.XA priority patent/CN106133066B/zh
Publication of WO2015133649A1 publication Critical patent/WO2015133649A1/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
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • 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
    • C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
    • 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
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • 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
    • 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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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

  • the present invention relates to a novel compound suitable for a dye which is designed to have a desired hue, has a good performance as a light absorber, and has improved heat resistance. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the dye, and a color filter that uses the colored photosensitive composition.
  • Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc.
  • Various compounds that absorb light having a wavelength of ⁇ 1100 nm are used as light absorbers. These light absorbers are required to have particularly sharp light absorption, that is, excellent waveform controllability such as a small half-value width of ⁇ max and that the function is not lost by light or heat. Yes.
  • RGB liquid crystal display
  • Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of color filters using dyes has become active.
  • color filters used in solid-state imaging devices have been required to have thin colored patterns from the viewpoint of improving image quality, and in order to reduce the thickness, it is necessary to increase the dye density in terms of color density. .
  • a large amount of dye must be added even when the molar absorption coefficient of the dye is low.
  • heat treatment post bake
  • Patent Document 1 discloses a dye monomer and a polymer thereof
  • Patent Document 2 discloses a hologram recording material containing a dye having a polymerizable group
  • Patent Document 3 discloses A two-photon absorption optical recording material containing a dye having a polymerizable group is disclosed
  • Patent Document 4 discloses a photosensitive coloring composition containing a triarylmethane dye monomer having a polymerizable group in an anion. Is disclosed.
  • the compounds having a polymerizable group described in these documents are not satisfactory in terms of solvent resistance and heat resistance.
  • an object of the present invention is to provide a novel compound that is excellent in solvent resistance and heat resistance, has excellent waveform controllability in a light absorption spectrum, and is suitable for a dye.
  • Another object of the present invention is to provide a colored photosensitive composition (colored alkali-developable photosensitive composition) using the above dye.
  • Another object of the present invention is an optical filter using the colored photosensitive composition (colored alkali-developable photosensitive composition), particularly suitable for an image display device such as a liquid crystal display panel without reducing luminance. It is to provide a color filter.
  • a compound having a specific structure is excellent in heat resistance, excellent in solvent resistance in a colored photosensitive composition (colored alkali-developable photosensitive composition), Knowing that the light absorption spectrum has excellent waveform controllability, and that the colored photosensitive composition (colored alkali-developable photosensitive composition) does not decrease the luminance of the optical filter (particularly the color filter), and does not decrease the liquid crystal display.
  • the present inventors have found that it is suitable for a color filter for an image display device such as a panel and reached the present invention. This invention is made
  • R 1 and R 11 , R 2 and R 12 , R 5 and R 13 , R 6 and R 14 , R 9 and R 15, and R 10 and R 16 may be linked to form a 6-membered ring.
  • R 11 and R 12 , R 13 and R 14 , and R 15 and R 16 may be linked to form a 3- to 6-membered heterocyclic ring
  • R 3 and R 4 and R 7 and R 8 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 to form a ring.
  • X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 ;
  • R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom.
  • An q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • any one or more of R 11 , R 12 , R 13 , R 14 , R 15 and R 16 is a hydrogen atom.
  • this invention provides the coloring photosensitive composition containing the dye (A) containing the said compound, the polymeric compound (B) which has an ethylenically unsaturated bond, and a photoinitiator (C). .
  • this invention provides the color filter for display devices which comprises the hardened
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 in the compound represented by the general formula (I) are each independently a hydrogen atom or Represents a halogen atom, A cyano group, a nitro group, a hydroxyl group, or an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms with a halogen atom, An alkoxy group having 1 to 8 carbon atoms substituted or unsubstituted by a halogen atom, An aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom, An aryloxy group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom, An arylthio
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. The same applies to all halogen atoms in the following description.
  • alkyl group having 1 to 8 carbon atoms substituted with a cyano group a nitro group, a hydroxyl group or a halogen atom
  • a part or all of the hydrogen atoms in the alkyl group having 1 to 8 carbon atoms may be a cyano group.
  • Examples of the unsubstituted alkoxy group having 1 to 8 carbon atoms include methyloxy group, ethyloxy group, iso-propyloxy group, butyloxy group, sec-butyloxy group, tert-butyloxy group, iso-butyloxy group, amyloxy group, iso -Amyloxy group, tert-amyloxy group, hexyloxy group, 2-hexyloxy group, 3-hexyloxy group, cyclohexyloxy group, 4-methylcyclohexyloxy group, heptyloxy group, 2-heptyloxy group, 3-heptyloxy group Group, iso-heptyloxy group, tert-heptyloxy group, 1-octyloxy group, iso-octyloxy group, tert-octyloxy group and the like.
  • Examples of the alkoxy group having 1 to 8 carbon atoms substituted with a halogen atom include groups in which part or all of the hydrogen atoms in the alkoxy group having 1 to 8 carbon atoms are substituted with a halogen atom. It is done.
  • Examples of the unsubstituted aryl group having 6 to 20 carbon atoms include a phenyl group and a naphthyl group.
  • aryl group having 6 to 20 carbon atoms substituted with a halogen atom part or all of the hydrogen atoms in the above unsubstituted aryl group having 6 to 20 carbon atoms are substituted with a halogen atom.
  • Examples of the unsubstituted aryloxy group having 6 to 20 carbon atoms include a phenyloxy group and a naphthyloxy group.
  • aryloxy group having 6 to 20 carbon atoms substituted with a halogen atom part or all of the hydrogen atoms in the above unsubstituted aryloxy group having 6 to 20 carbon atoms are substituted with halogen atoms.
  • Examples of the unsubstituted arylthio group having 6 to 20 carbon atoms include a phenylthio group and a naphthylthio group.
  • arylthio group having 6 to 20 carbon atoms substituted with a halogen atom part or all of the hydrogen atoms in the above unsubstituted arylthio group having 6 to 20 carbon atoms are substituted with a halogen atom.
  • Examples of the unsubstituted arylalkenyl group having 8 to 20 carbon atoms include benzyl group, phenethyl group, diphenylmethyl group, triphenylmethyl group and the like.
  • arylalkenyl group having 8 to 20 carbon atoms substituted with a halogen atom part or all of the hydrogen atoms in the above unsubstituted arylalkenyl group having 8 to 20 carbon atoms is substituted with a halogen atom.
  • Examples of the unsubstituted arylalkyl group having 7 to 20 carbon atoms include a styryl group and a cinnamyl group.
  • arylalkyl group having 7 to 20 carbon atoms substituted with a halogen atom a part or all of the hydrogen atoms in the unsubstituted arylalkyl group having 7 to 20 carbon atoms is substituted with a halogen atom.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group or a nitro group, Substituted with nitro group, carboxyl group, sulfonic acid group, hydroxyl group or halogen atom, substituted with carboxyl ester, sulfonic acid group ester, carboxyl salt or sulfonic acid salt, or unsubstituted An alkyl group having 1 to 8 carbon atoms, Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group A phenyl group which is substituted or unsubstituted with a salt or a salt of a sul
  • Examples of the unsubstituted alkyl group having 1 to 8 carbon atoms include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso -Amyl group, tert-amyl group, hexyl group, 2-hexyl group, 3-hexyl group, cyclohexyl group, 1-methylcyclohexyl group, heptyl group, 2-heptyl group, 3-heptyl group, iso-heptyl group, tert -Heptyl group, 1-octyl group, iso-octyl group, tert-octyl group and the like.
  • a part or all of the above alkyl group may be substituted with a nitro group, a carboxyl group, a sulfonic acid group, a hydroxyl group or a halogen atom, or an ester of a carboxyl group, an ester of a sulfonic acid group, or a salt of a carboxyl group Alternatively, it may be substituted with a salt of a sulfonic acid group.
  • the carboxyl group ester include esters having 1 to 4 carbon atoms such as methyl ester, ethyl ester, iso-propyl ester, and butyl ester.
  • the carboxyl group salt or the sulfonic acid group salt include alkali metal salts such as lithium salt, sodium salt and potassium salt, and amine salts such as ammonium salt, ethanolamine salt, diethanolamine salt and triethanolamine salt.
  • Part or all of the above phenyl group and benzyl group may be substituted with a halogen atom, a cyano group, a vinyl group, a nitro group, a carboxyl group, or a sulfonic acid group, and an ester of a carboxyl group or an ester of a sulfonic acid group , A salt of a carboxyl group or a salt of a sulfonic acid group may be substituted.
  • the ester and the salt include the above examples.
  • R 1 and R 11 , R 2 and R 12 , R 5 and R 13 , R 6 and R 14 , R 9 and R 15, and R 10 and R 16 may be linked to form a 6-membered ring.
  • R 11 and R 12 , R 13 and R 14 , and R 15 and R 16 may be linked to form a 3- to 6-membered heterocyclic ring
  • R 3 and R 4 and R 7 and R 8 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 to form a ring. It may be.
  • Examples of the 6-membered ring that can be formed by linking include a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, and an isoquinoline ring.
  • Examples of the 3- to 6-membered heterocyclic ring that can be formed by coupling include piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline Ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring and the like. These 6-membered rings and heterocyclic rings may be condensed or substituted with other rings.
  • X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 ;
  • R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom.
  • Examples of the alkoxy group having 1 to 8 carbon atoms or the alkoxy group having 1 to 8 carbon atoms substituted with a halogen atom include those described above.
  • pAn q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • Examples of the anion represented by An q- include monovalent ions such as chloride ions, bromide ions, iodide ions and fluoride ions; perchlorate ions, chlorate ions and thiocyanates.
  • Inorganic anions such as acid ion, hexafluorophosphate ion, hexafluoroantimonate ion, tetrafluoroborate ion; methanesulfonate ion, dodecylsulfonate ion, benzenesulfonate ion, toluenesulfonate ion, trifluoromethanesulfone Acid ion, naphthalene sulfonate ion, diphenylamine-4-sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino-5-nitrobenzenesulfonate ion, phthalocyanine sulfonate ion, polymerizable substitution
  • Sulfonic acid type anions Octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphone
  • Organic phosphates such as acid ions , Bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4-ethylcyclohexanesulfonate ion, tetrakis (pentafluorophenyl) borate ion, tris (fluoroalkylsulfonyl) carboanion, etc.
  • a benzene disulfonic acid ion, a naphthalene disulfonic acid ion, etc. are mentioned, for example.
  • quencher anions that have the function of deexciting (quenching) active molecules in the excited state
  • ferrocenes having an anionic group such as a carboxyl group, phosphonic acid group, or sulfonic acid group on the cyclopentadienyl ring.
  • Metallocene compound anions such as luteocene can also be used as necessary.
  • p is selected so that the charge is neutral throughout the molecule.
  • quencher anion examples include, for example, JP-A-60-234892, JP-A-5-43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886.
  • Examples of the anion represented by An q- in the general formula (I) include a monovalent organic sulfonic acid anion, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4- Ethylcyclohexanesulfonate ion, benzenedisulfonate ion, and naphthalenedisulfonate ion are preferable from the viewpoint of heat resistance, and bistrifluoromethylsulfonylimide ion is more preferable.
  • R 4 and R 7 are a hydroxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, or a carbon atom number 1 to 1 optionally substituted with a halogen atom.
  • An alkoxy group of 8 is preferable, a halogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom is more preferable, and a halogen atom is still more preferable.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are groups other than hydrogen atoms, from the viewpoint of solvent solubility, the number of carbon atoms substituted or unsubstituted with polar groups, particularly hydroxyl groups. 1-8 alkyl groups are preferred.
  • X is preferably an oxygen atom or a sulfur atom from the viewpoint of availability.
  • the manufacturing method of the compound represented with the said general formula (I) is not specifically limited, For example, when X in the said general formula (I) is an oxygen atom, it can manufacture according to following Reaction Formula. In addition, also when X is other than an oxygen atom, it can manufacture according to the following manufacturing method. It can also be produced according to a known method described in Journal of Organic Chemistry (2009), 74 (8), 3183-3185.
  • the compound represented by the general formula (I) is used as a colored alkali-developable photosensitive composition described below, as well as an optical filter used for a display or an optical lens, a silver salt photographic photosensitive material, a dyed material, and a paint. Used for optical recording dyes and the like.
  • the colored photosensitive composition of the present invention will be described.
  • a colored photosensitive composition or a colored alkali-developable composition described later is appropriately described as a colored composition.
  • the colored photosensitive composition of the present invention comprises a dye (A) containing the compound of the present invention (hereinafter also referred to as dye (A)), a polymerizable compound (B) having an ethylenically unsaturated bond (providing alkali developability).
  • the dye (A) used in the present invention only needs to contain at least one compound of the present invention, and can be used alone or in combination.
  • a known dye can be used as the dye (A).
  • Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes. , Phthalocyanine dyes, cyanine dyes, and the like. These may be used in combination.
  • the content of the compound of the present invention is preferably 50 to 100% by mass, more preferably 70 to 100% by mass.
  • content of the compound of this invention is smaller than 50 mass%, the solubility to a solvent may fall or heat resistance may fall.
  • the content of the dye (A) in the colored composition of the present invention is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass. If the content of the dye (A) is less than 0.01% by mass, a color having a desired concentration may not be obtained in the cured product of the colored composition of the present invention. In some cases, precipitation of the dye (A) may occur.
  • the polymerizable compound (B) having an ethylenically unsaturated bond is not particularly limited, and those conventionally used in photosensitive compositions can be used.
  • ethylene, propylene, butylene, isobutylene can be used.
  • Unsaturated polybasic acids such as polyfunctional (meth) acrylates; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate; A1-No.
  • A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
  • the polyfunctional acrylate which has an acid value which is a reaction product of a dibasic acid anhydride is mentioned.
  • These polymerizable compounds can be used alone or in admixture of two or more, and when used in admixture of two or more, they are copolymerized in advance and used as a copolymer. May be.
  • the colored composition of the present invention as the polymerizable compound (B) having an ethylenically unsaturated bond, a polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts alkali developability.
  • a polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts alkali developability When ') (hereinafter also referred to as an alkali-developable compound (B') having an ethylenically unsaturated bond) is used, the colored photosensitive composition of the present invention becomes a colored alkaline-developable photosensitive composition.
  • alkali-developable compound (B ′) having an ethylenically unsaturated bond examples include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, Butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl ( (Meth) acrylates such as (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate; N-vinylpyrroli
  • a polyphenylmethane type epoxy resin having a functional epoxy group, obtained by allowing an unsaturated monobasic acid to act on an epoxy group such as an epoxy compound represented by the following general formula (II), and further reacting with a polybasic acid anhydride Resins can be used. These monomers can be used individually by 1 type or in mixture of 2 or more types.
  • the alkali developable compound (B ′) having an ethylenically unsaturated bond preferably contains 0.2 to 1.0 equivalent of an unsaturated group.
  • X 1 is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO—, or a substituent represented by the following formula (A), (B) or (C), wherein the alkylidene group may be substituted with a halogen atom
  • R 31 , R 32 , R 33 and R 34 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and m is an integer of 0 to 10.
  • Y 2 represents a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom
  • Y 1 represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
  • alkenyl group having 2 to 10 carbon atoms or a halogen atom the alkyl group, alkoxy group and alkenyl group in Y 1 may be substituted with a halogen atom, and b is an integer of 0 to 5.
  • Y 3 and Y 4 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom.
  • Examples of the unsaturated monobasic acid that acts on the epoxy group of the epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, and the like. Examples thereof include hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.
  • the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic acid anhydride, trialkyl
  • the reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group 1 of the epoxy adduct is It is preferable that the ratio of the acid anhydride structure of the polybasic acid anhydride is 0.1 to 1.0.
  • the reaction of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride can be performed according to a conventional method.
  • a monofunctional or polyfunctional epoxy compound may be used together with the alkali-developable compound having an ethylenically unsaturated bond. It can.
  • the alkali-developable compound having an ethylenically unsaturated bond preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the use amount of the monofunctional or polyfunctional epoxy compound satisfies the acid value. It is preferable to select as follows.
  • Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
  • the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a colored alkali-developable photosensitive composition with better characteristics can be obtained.
  • the bisphenol type epoxy compound an epoxy compound represented by the above general formula (I) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
  • glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
  • novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as phthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, dimer acid glycidyl ester; Glycidylamines such as diphenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy
  • the polymerizable compounds (B) having an ethylenically unsaturated bond (including the alkali developable compound (B ′) having the ethylenically unsaturated bond), from the viewpoint of compatibility, alkali developability and heat resistance, Unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene; (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid , Fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allylic acetic acid, cinnamic acid, sorbic acid or mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (Meth) acryloyl]
  • the content of the polymerizable compound (B) having the ethylenically unsaturated bond is the content of the present invention.
  • 30 to 99% by mass, particularly 60 to 95% by mass is preferable. If the content of the polymerizable compound (B) having an ethylenically unsaturated bond is less than 30% by mass, the mechanical strength of the cured product is insufficient and cracks occur, or if it has alkali developability, development failure occurs. If it is larger than 99% by mass, curing due to exposure becomes insufficient and tackiness occurs, and if it has alkali developability, the development time becomes long and the cured part may be damaged by alkali. There is a case.
  • Photopolymerization initiator (C) As the photopolymerization initiator (C), conventionally known compounds can be used. For example, benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzoin, benzyldimethyl ketal, 1-benzyl- 1-dimethylamino-1- (4′-morpholinobenzoyl) propane, 2-morpholyl-2- (4′-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethyl Anthraquinone, 4-benzoyl-4'-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4'-isopropyl) benzoylpropane, 4-
  • N-1414, N-1717, N-1919, and PZ-4. 8 (manufactured by (Corporation) ADEKA Corporation) NCI-831, NCI-930, IRGACURE369, IRGACURE907, IRGACURE OXE 01, IRGACURE OXE 02 (BASF (Co.) Co., Ltd.).
  • photopolymerization initiators (C) from the viewpoint of sensitivity and color tone, 2-morpholylu 2- (4′-methylmercapto) benzoylpropane, 9-n-butyl-3,6-bis (2′-morpholinoisopetite). Royl) carbazole is preferred, and 2-morpholylu 2- (4′-methylmercapto) benzoylpropane is more preferred.
  • the content of the photopolymerization initiator (C) is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass in the colored composition of the present invention.
  • the content of the photopolymerization initiator (C) is less than 0.1% by mass, curing by exposure may be insufficient.
  • the initiator (C) is contained in the resin composition. May precipitate.
  • the coloring composition of the present invention may further contain a color material (D) other than the compound of the present invention.
  • D color material
  • These color materials can be used alone or in admixture of two or more.
  • Examples of the color material (D) include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, quinacridone compounds, Antanthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinophthalone compound, naphthalene tetracarboxylic acid; azo dye, metal complex compound of cyanine dye; lake pigment; furnace method, Carbon black obtained by channel method or thermal method, or carbon black such as acetylene black, ketjen black or lamp black; A product prepared and coated with an epoxy resin, a carbon black previously dispersed with a resin in a solvent, adsorbed with 20 to 200 mg / g of resin, and a carbon black
  • Inorganic pigments or organic pigments can be used.
  • pigments can also be used.
  • a known dye As the coloring material (D), a known dye can be used.
  • Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, Examples thereof include phthalocyanine dyes and cyanine dyes.
  • the content of the coloring material (D) is preferably 0 to 350 parts by mass, more preferably 100 parts by mass of the polymerizable compound (B) having an ethylenically unsaturated bond. Is 0 to 250 parts by mass. When it exceeds 350 parts by mass, the light transmittance of the colored composition of the present invention, particularly the cured product using the colored alkali-developable photosensitive composition, and the color filter for display device is lowered, and the luminance of the display device is lowered. Therefore, it is not preferable.
  • a solvent can be further added to the colored composition of the present invention.
  • the solvent is usually a solvent capable of dissolving or dispersing each of the above components (the dye (A) containing the compound of the present invention, etc.) as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl Ketones such as isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; acetic acid Ester solvents such as methyl, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl a
  • ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like have good compatibility between the resist and the photopolymerization initiator (C) in the colored composition. preferable.
  • the amount of the solvent used is such that the concentration of the composition other than the solvent is preferably 5 to 30% by mass, and if it is less than 5% by mass, it is difficult to increase the film thickness. Yes, it is not preferable because it cannot absorb light of a desired wavelength sufficiently, and when it is larger than 30% by mass, the storage stability of the composition due to the precipitation of the composition may be reduced, or the handling may be reduced because the viscosity is improved. There is.
  • the coloring composition of the present invention can further contain an inorganic compound.
  • the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable.
  • the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 0, relative to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond.
  • These inorganic compounds can be used alone or in combination of two or more. These inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
  • a dispersant can be added.
  • any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
  • the coloring composition of the present invention includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Conventional additives such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid, a coagulation inhibitor, a catalyst, an effect accelerator, a cross-linking agent, and a thickener can be added.
  • thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • plasticizer such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • adhesion promoter such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid
  • the colored composition of the present invention optional components other than the dye (A), the polymerizable compound (B) having the ethylenically unsaturated bond, and the photopolymerization initiator (C) (however, the colorant (D) and
  • the content of the solvent (excluding the solvent) is appropriately selected according to the purpose of use and is not particularly limited, but is preferably a total with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. And 50 parts by mass or less.
  • the colored composition of the present invention improves the properties of the cured product comprising the colored composition of the present invention by using another organic polymer together with the polymerizable compound (B) having the ethylenically unsaturated bond.
  • the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
  • Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
  • polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included.
  • the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond.
  • a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like can be used in combination with the colored composition of the present invention.
  • a chain transfer agent or sensitizer a sulfur atom-containing compound is generally used.
  • Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
  • the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
  • anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
  • silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, an isocyanate group, a methacryloyl group, or an epoxy group, such as KBE-9007, KBM-502, and KBE-403, can be used. A silane coupling agent is preferably used.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
  • the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed.
  • an oligomer component may be formed.
  • hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
  • alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
  • the coloring composition of the present invention is a known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. It can be applied on the supporting substrate. Further, once applied on a supporting substrate such as a film, it can be transferred onto another supporting substrate, and the application method is not limited.
  • the active light source used for curing the colored composition of the present invention one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc. And xenon arc.
  • the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
  • the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs light in the visible to infrared region is added.
  • the colored composition of the present invention (or a cured product thereof) is a liquid crystal display panel for color display such as a photocurable paint or varnish, a photocurable adhesive, a printed board or a color TV, a PC monitor, a portable information terminal, a digital camera, etc.
  • the colored composition of the present invention in particular the colored alkali-developable photosensitive composition, is used for the purpose of forming a pixel of a color filter, and in particular a color filter for a display device for an image display device such as a liquid crystal display panel or an organic EL. It is useful as a photosensitive composition for forming.
  • the color filter for display device of the present invention may have red, green, blue, orange, purple and black optical elements in addition to the cured product of the present invention.
  • the color filter for display device includes (1) a step of forming a coating film of the colored composition of the present invention (particularly a colored alkali-developable photosensitive composition) on a substrate, and (2) a predetermined pattern shape on the coating film. Preferably formed by a step of irradiating actinic light through a mask having, (3) a step of developing a film after exposure with a developer (particularly an alkali developer), and (4) a step of heating the film after development. Is done.
  • the colored composition of the present invention is also useful as a colored composition for an ink jet system or a transfer system without a development step.
  • a color filter used in a liquid crystal display panel or the like is manufactured by repeating the above steps (1) to (4) using a coloring composition of the present invention or other combination and combining patterns of two or more colors. Can do.
  • Example 1 Compound No. 13, no. 25, no. 26 and no. Synthesis of 35 ⁇ Step 1> 0.01 mol of the following compound S-1, 0.02 mol of monoethylaminophenol and 0.03 mol of sulfuric acid were mixed and stirred at 140 ° C. for 8 hours. The reaction solution was added dropwise to an aqueous sodium hydroxide solution, the organic matter was extracted with toluene, washed three times with water, and then the solvent was distilled off from the organic layer. The residue was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 0.005 mol of a leuco body (yield 52%).
  • Step 2> After charging and stirring 2.56 g (0.005 mol) of the leuco body obtained in Step 1, 19.75 g of water and 3.95 g of hydrochloric acid, 9.27 g of 35 mass% iron chloride aqueous solution was charged and stirred at 80 ° C. for 8 hours. . After cooling to room temperature, chloroform was added, the aqueous layer was taken out and washed with water, and then neutralized with an aqueous sodium hydrogen carbonate solution. 4.79 g (0.01 mol) of bis (trifluoromethanesulfonyl) imide potassium was added to perform salt exchange, and then the solvent was distilled off from the obtained organic layer.
  • Example 2 and Comparative Example 2 Preparation of colored alkali-developable photosensitive composition ⁇ Step 1> Preparation of alkali-developable photosensitive composition (B) 30.33 g of ACA Z251 (manufactured by Daicel Cytec Co., Ltd.) and Aronix M-450 (manufactured by Toagosei Co., Ltd.) 11.04 g, 1.93 g of Irgacure 907 (manufactured by BASF) as the component (C), 20.08 g of PGMEA as the component (E), and FZ2122 (manufactured by Dow Corning Toray) as the other components. 01 g was mixed and stirred until insoluble matter disappeared to obtain an alkali-developable photosensitive composition.
  • Step 2> Preparation of dye solution As the component (A), 0.10 g of the compound described in [Table 3] and 1.90 g of PGMEA were added respectively, and the mixture was stirred to dissolve. 1-No. 2 and comparative dye solution No. 1-No. 2.
  • Step 3 Preparation of colored alkali-developable photosensitive composition 5.0 g of the alkali-developable photosensitive composition obtained in Step 1 is mixed with 1.0 g of the dye solution obtained in Step 2 and the comparative dye solution. And stirring until uniform, the colored alkali-developable photosensitive composition No. 1-No. 2 and comparative colored alkali-developable photosensitive composition No. 2 1-No. 2 was obtained.
  • Example 3 and Comparative Example 3 Evaluation of heat resistance by firing The colored alkali-developable photosensitive composition No. obtained in Example 2 was used. 1 and no. 2 and comparative colored alkali-developable photosensitive composition No. 2 obtained in Comparative Example 2. 1 and no. Each of 2 was coated on a glass substrate under conditions of 410 rpm ⁇ 7 seconds and dried on a hot plate (90 ° C., 90 seconds). The obtained coating film was exposed (150 mJ / cm 2 ) with an ultrahigh pressure mercury lamp. The coated film after exposure was baked under conditions of 230 ° C. ⁇ 30 min. The color difference ( ⁇ E ab * ) before and after firing was examined. The better the heat resistance, the higher the color difference value. The results are shown in [Table 4].

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Abstract

　La présente invention concerne : un nouveau composé présentant d'excellentes résistance aux solvants et résistance à la chaleur, ainsi que d'excellentes propriétés de réglage de forme d'onde dans son spectre d'absorption optique, et qui est approprié pour un colorant ; et une composition colorée photosensible (composition colorée photosensible pouvant être développée dans un alcali) et un filtre coloré utilisant le composé (colorant) ; un composé représenté par la formule générale (1), en particulier un composé dans lequel l'un de R4 et R7ou les deux dans la formule générale (1) sont des groupes hydroxyle ou des atomes d'halogène, ou des groupes alkyle en C1-8 substitués par un atome d'halogène ou des groupes alcoxy en C1-8 qui peuvent être substitués par un atome d'halogène, utilisé en tant que colorant. Les détails spécifiques de la formule générale (1) sont tels que décrits dans la description.
PCT/JP2015/056982 2014-03-06 2015-03-10 Nouveau composé et composition colorée photosensible Ceased WO2015133649A1 (fr)

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JP7046777B2 (ja) * 2017-11-10 2022-04-04 東友ファインケム株式会社 着色硬化性樹脂組成物、カラーフィルタ及び表示装置
TWI748137B (zh) * 2017-11-10 2021-12-01 南韓商東友精細化工有限公司 著色硬化性樹脂組成物、彩色濾光片及顯示裝置
WO2020162335A1 (fr) * 2019-02-05 2020-08-13 株式会社Adeka Composé de xanthène
JP7555704B2 (ja) * 2019-02-05 2024-09-25 東友ファインケム株式会社 着色樹脂組成物
TWI889665B (zh) * 2020-02-13 2025-07-11 南韓商東友精細化工有限公司 著色樹脂組合物、彩色濾光片及顯示裝置
CN113341645A (zh) * 2020-02-18 2021-09-03 东友精细化工有限公司 着色树脂组合物、滤色器及显示装置

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