WO2015122567A1 - Nouveau composé de colorant, composé de résine photosensible, et filtre de couleur comprenant le composé de colorant - Google Patents

Nouveau composé de colorant, composé de résine photosensible, et filtre de couleur comprenant le composé de colorant Download PDF

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Publication number
WO2015122567A1
WO2015122567A1 PCT/KR2014/003594 KR2014003594W WO2015122567A1 WO 2015122567 A1 WO2015122567 A1 WO 2015122567A1 KR 2014003594 W KR2014003594 W KR 2014003594W WO 2015122567 A1 WO2015122567 A1 WO 2015122567A1
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substituted
group
unsubstituted
formula
compound
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PCT/KR2014/003594
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English (en)
Korean (ko)
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신명엽
플럭카르스텐
베르베리히마르틴
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제일모직 주식회사
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Publication of WO2015122567A1 publication Critical patent/WO2015122567A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/105—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a methine or polymethine dye
    • 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
    • G03F7/0041—Photosensitive materials providing an etching agent upon exposure
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • 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
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers

Definitions

  • This substrate relates to a novel dye compound, a photosensitive resin composition comprising the dye compound, and a color filter.
  • One embodiment of the present invention aims to provide a novel dye compound.
  • Another embodiment of the present invention is to provide a photosensitive resin composition comprising the dye compound.
  • Another embodiment of the present invention is to provide a color filter prepared using the photosensitive resin composition.
  • One embodiment of the present invention provides a compound represented by the following formula (1).
  • R1 to R8 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group , A substituted or unsubstituted amino group, -OR9, -NHC (O) R9, -C (O) OR10, or is represented by the following formula (2), at least one of R1, R2, and R8 is represented by the formula (2),
  • R9 and R10 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C12 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
  • R1 and R2 may be each independently or may be combined with each other to form a ring.
  • R11 to R13 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
  • n and m are each independently an integer of 0 to 10, but n + m is not 0,
  • X is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, -O-, or -NR'-, and R 'is hydrogen, a substituted or unsubstituted C1 to C5 alkylene group, or a carbonyl group (-C (O )-)ego,
  • Y is represented by a hydrogen atom, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or the following formula (3).
  • R14 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
  • R1 to R6 and R8 may be each independently represented by a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or Formula 2, and at least one of R1, R2, and R8 is represented by Formula 2 Displayed,
  • R7 may be cyano
  • R11 to R13 may be each independently a hydrogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
  • n and n are each independently an integer of 0 to 10, but m + n is not 0,
  • X may be a single bond or a substituted or unsubstituted C1 to C10 alkylene group
  • Y may be represented by a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or Formula 3, wherein in Formula 3, R14 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted group It may be a C6 to C20 aryl group.
  • Y may be represented by Formula 3.
  • the compound of Formula 1 may be represented by the following formula (4) or (5).
  • R25 to R26 and R29 to R32 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted group C6 to C20 aryl group,
  • R27 to R28 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group Or -OR37 (R37 is a hydrogen atom, a substituted or unsubstituted C1 to C12 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group),
  • R33 to R36 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
  • X is a single bond or a substituted or unsubstituted C1 to C10 alkylene group
  • n and m are integers from 0 to 10, but n + m is not zero.
  • R25 to R30 and R32 to R36 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R31 is a cyano group, n may be an integer of 0 have.
  • the compound may have a molar extinction coefficient of 50,000 M ⁇ 1 cm ⁇ 1 to 150,000 M ⁇ 1 cm ⁇ 1 in the wavelength range of 380 nm to 770 nm.
  • the compound may have a molar absorption coefficient of 70,000 M ⁇ 1 cm ⁇ 1 to 130,000 M ⁇ 1 cm ⁇ 1 in the wavelength range of 400 nm to 650 nm.
  • the compound may be a dye such as a red dye compound.
  • Another embodiment of the present invention provides a photosensitive resin composition comprising the dye compound.
  • the photosensitive resin composition may include (A) a compound according to the above embodiment, (B) a binder resin, (C) a reactive unsaturated compound, (D) an initiator, and (E) a solvent.
  • Yet another embodiment of the present invention provides a color filter manufactured using the photosensitive resin composition.
  • the dye compound according to the embodiment of the present invention may provide a photosensitive resin composition and a color filter having a large molar extinction coefficient and exhibiting excellent color characteristics even with a small amount of dye.
  • substituted to “substituted” means that at least one hydrogen atom of the functional group of the present invention is a halogen atom (F, Br, Cl or I), hydroxy group, nitro group, cyano group, amino group ( NH 2 , NH (R200) or N (R201) (R202), wherein R200, R201, and R202 are the same or different from each other, and are each independently C1 to C10 alkyl group), amidino group, hydrazine group, hydra A substituted group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted group It means that at least one hydrogen atom of the functional group of the
  • an "alkyl group” means a C1 to C20 alkyl group, specifically a C1 to C15 alkyl group
  • a "cycloalkyl group” refers to a C3 to C20 cycloalkyl group, specifically C3 To C18 cycloalkyl group
  • alkoxy group means C1 to C20 alkoxy group, specifically C1 to C18 alkoxy group
  • aryl group means C6 to C20 aryl group, specifically C6 to C18 aryl group
  • alkenyl group means C2 to C20 alkenyl group, specifically C2 to C18 alkenyl group
  • alkylene group means C1 to C20 alkylene group, specifically C1 To C18 alkylene group
  • an “arylene group” means a C6 to C20 arylene group, specifically, a C6 to C16 arylene group.
  • an "aliphatic organic group” means a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C1 to C20 alkylene group, a C2 to C20 alkenylene group, or a C2 to C20 group.
  • An alkynylene group specifically, a C1 to C15 alkyl group, a C2 to C15 alkenyl group, a C2 to C15 alkynyl group, a C1 to C15 alkylene group, a C2 to C15 alkenylene group, or a C2 to C15 alkynylene group
  • Alicyclic organic group "means a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C3 to C20 cycloalkylene group, a C3 to C20 cycloalkenylene group, or a C3 to C20 cycloalkynylene group
  • C2 to C15 cycloalkyl group containing 1 to 3 heteroatoms selected from the group consisting of O, S, N, P, Si, and combinations thereof in one ring C2 to C15 Icycloalkylene group, C2 to C15 cycloalkenyl group, C2 to C15 cycloalkenylene group, C2 to C15 cycloalkynyl group, C2 to C15 cycloalkynylene group, C2 to C15 heteroaryl group, or C2 to C15 heteroarylene group it means.
  • “combination” means mixed or copolymerized.
  • “copolymerization” means block copolymerization to random copolymerization, and “copolymer” means block copolymer to random copolymerization.
  • the molar extinction coefficient refers to the amount of light absorbed by one mole of the compound.
  • An extinction coefficient is a coefficient indicating the degree of absorption of a substance.
  • the proportional coefficient is expressed by ⁇ , which is called the molar extinction coefficient.
  • One embodiment provides a compound represented by Formula 1 below.
  • R1 to R8 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group , A substituted or unsubstituted amino group, -OR9, -NHC (O) R9, -C (O) OR10, or is represented by the following formula (2), at least one of R1, R2, and R8 is represented by the formula (2),
  • R9 and R10 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C12 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
  • R1 and R2 may be each independently or may be combined with each other to form a ring.
  • R11 to R13 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
  • n and m are each independently an integer of 0 to 10, provided that n + m is not 0,
  • X is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, -O-, or -NR'-, and R 'is hydrogen, a substituted or unsubstituted C1 to C5 alkylene group, or a carbonyl group (-C (O )-)ego,
  • Y is represented by a hydrogen atom, a halogen atom, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or the following formula (3).
  • R14 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
  • R1 to R6 and R8 may be each independently represented by a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or Formula 2, and at least one of R1, R2, and R8 is represented by Formula 2 Displayed,
  • R7 may be cyano
  • R11 to R13 may be each independently a hydrogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
  • n and n are each independently an integer of 0 to 5, but m + n is not 0,
  • X may be a single bond or a substituted or unsubstituted C1 to C10 alkylene group
  • Y may be represented by a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, or Formula 3, wherein in Formula 3, R14 is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 To C20 aryl group.
  • Y may be represented by Chemical Formula 3.
  • the compound represented by Formula 1 includes a functional group represented by Formula 2, wherein at least one of R1, R2, and R8 has a molar extinction coefficient that is 2 to 3 times greater than that of the compound that does not contain the same, thereby displaying It can be usefully used as a coloring agent in an element.
  • the compound of Formula 1 may be represented by the following formula (4) or (5).
  • R25 to R26 and R29 to R32 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted group C6 to C20 aryl group,
  • R27 to R28 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl Group, -OR37 (R37 is a hydrogen atom, a substituted or unsubstituted C1 to C12 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group),
  • R33 to R36 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
  • X is a single bond or a substituted or unsubstituted C1 to C10 alkylene group
  • n and m are each independently an integer of 0 to 10, provided that n + m is not zero.
  • R25 to R30 and R32 to R36 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R31 is a cyano group, n may be an integer of 0 have.
  • the compound may have a high molar extinction coefficient in the visible wavelength range.
  • a molar absorption coefficient of 50,000 M ⁇ 1 cm ⁇ 1 to 150,000 M ⁇ 1 cm ⁇ 1 in the wavelength range of 380 nm to 770 nm for example, 70,000 M ⁇ 1 cm ⁇ 1 to 130,000 M ⁇ in the wavelength range of 400 nm to 650 nm
  • It may have a molar extinction coefficient of 1 cm ⁇ 1 .
  • the compound according to the embodiment has a molar absorption coefficient within the range within the wavelength range, it is possible to express more vivid color in a small amount, excellent color characteristics such as brightness and contrast ratio when used as a colorant It is possible to manufacture display elements.
  • the compound may be a colorant such as a dye such as a red dye.
  • dyes are the most expensive of the components used in color filters. Therefore, in order to achieve a desired effect, such as high brightness or high contrast ratio, more expensive dyes have to be used.
  • the compound according to the embodiment as a dye in the color filter, it is possible to achieve excellent color characteristics such as high brightness, high contrast ratio even in a small amount, it is possible to reduce the production cost.
  • a photosensitive resin composition comprising the compound according to the above embodiment is provided.
  • the photosensitive resin composition includes (A) a compound according to the above embodiment, (B) a binder resin, (C) a reactive unsaturated compound, (D) an initiator, and (E) a solvent.
  • the compound according to this embodiment can act as a colorant, such as a dye, and can express excellent color properties.
  • the photosensitive resin composition may further include a red pigment, a yellow pigment, or a combination thereof in addition to the compound according to one embodiment as a colorant.
  • the red pigment may be a compound containing at least one azo group, and specifically, the C.I. Pigment Red 254, C.I. Pigment Red 242, C.I. Pigment Red 214, C.I. Pigment Red 221, C.I. Pigment Red 166, C.I. Pigment Red 220, C.I. Pigment Red 248, C.I. Pigment red 262, etc., These can be used individually or in mixture of 2 or more types.
  • the yellow pigment is a C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment yellow 150, etc., These can be used individually or in mixture of 2 or more types.
  • the compound according to the embodiment and the pigment may be used by mixing in a weight ratio of 5: 5 to 9.9: 0.1, for example, it may be used by mixing in a weight ratio of 6: 4 to 7: 3. When mixed in the weight ratio range, it can have a high contrast ratio while maintaining color characteristics.
  • the compound according to the embodiment may be included in an amount of 0.1% to 30% by weight based on the total amount of the photosensitive resin composition.
  • the binder resin may be an acrylic binder resin.
  • the acrylic binder resin is a copolymer of the first ethylenically unsaturated monomer and the second ethylenically unsaturated monomer copolymerizable therewith, and is a resin including one or more acrylic repeating units.
  • the first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.
  • the first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, such as 10 wt% to 40 wt%, based on the total amount of the acrylic binder resin.
  • the second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, ⁇ -methylstyrene, vinyltoluene, vinylbenzylmethyl ether, etc .; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds, such as vinyl acetate and a vinyl benzoate; Unsaturated carboxy
  • acrylic binder resin examples include (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate.
  • the weight average molecular weight of the binder resin may be 3,000 g / mol to 150,000 g / mol, such as 5,000 g / mol to 50,000 g / mol, such as 20,000 g / mol to 30,000 g / mol.
  • weight average molecular weight of the binder resin is within the above range, the physical and chemical properties of the photosensitive resin composition for color filters are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent when the color filter is manufactured.
  • the acid value of the binder resin may be 15 mgKOH / g to 60 mgKOH / g, such as 20 mgKOH / g to 50 mgKOH / g.
  • the acid value of the binder resin is within the above range, the resolution of the pixel pattern is excellent.
  • the binder resin may be included in an amount of 1 wt% to 40 wt%, such as 5 wt% to 20 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • the binder resin is included in the above range, the developability and the crosslinkability of the color filter may be improved to obtain excellent surface smoothness.
  • the reactive unsaturated compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
  • the reactive unsaturated compound has the ethylenically unsaturated double bond, it can form a pattern excellent in heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern forming step.
  • the reactive unsaturated compound examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (Meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, Pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylic Latent, dipentaerythritol
  • Examples of commercially available products of reactive unsaturated compounds are as follows.
  • Examples of the monofunctional ester of (meth) acrylic acid include, but are not limited to, Aronix M-101®, M-111®, M-114®, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nihon Kayaku Co., Ltd., KAYARAD TC-110S®, TC-120S®, etc .; And V-158® and V-2311® by Osaka Yuki Kagaku Kogyo Co., Ltd.
  • Examples of the difunctional ester of (meth) acrylic acid include, but are not limited to, Aronix M-210®, M-240®, M-6200®, manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nippon Kayaku Co., Ltd. KAYARAD HDDA®, HX-220®, R-604®, etc .; The V-260®, V-312®, and V-335 HP® by Osaka Yuki Chemical Co., Ltd. are mentioned.
  • Examples of the trifunctional ester of (meth) acrylic acid include Aronix M-309®, Copper M-400®, Copper M-405®, Copper M-450®, and Copper M, manufactured by Toagosei Kagaku Kogyo Co., Ltd.
  • the reactive unsaturated compound may be used after being treated with an acid anhydride in order to impart better developability.
  • the reactive unsaturated compound may be included in an amount of 1 wt% to 15 wt%, such as 5 wt% to 10 wt%, based on the total amount of the photosensitive resin composition.
  • a reactive unsaturated compound is contained in the said range, hardening arises at the time of exposure at a pattern forming process, and it is excellent in reliability, and is excellent in developability to an alkaline developing solution.
  • the initiator may use a photopolymerization initiator, a radical polymerization initiator, or a combination thereof.
  • an initiator generally used in the photosensitive resin composition for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, an oxime compound, or a combination thereof may be used. .
  • acetophenone-based compound examples include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, etc. are mentioned.
  • benzophenone-based compound examples include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4,4 '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone and the like.
  • thioxanthone-based compound examples include thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, and 2,4-diiso Propyl thioxanthone, 2-chloro thioxanthone, etc. are mentioned.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.
  • triazine-based compound examples include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s-triazine and 2- (3 ', 4'- Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-biphenyl 4,6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) -4,
  • Examples of the oxime compound include O-acyl oxime compound, 2- (O-benzoyl oxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (O-acetyl oxime) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, 0-ethoxycarbonyl- ⁇ -oxyamino-1-phenylpropan-1-one and the like Can be used.
  • O-acyl oxime compound examples include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) -butane- 1-one, 1- (4-phenylsulfanylphenyl) -butane-1,2-dione-2-oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1,2-dione 2-Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) -butan-1-one oxime- O-acetate or the like can be used.
  • the photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, or the like.
  • the radical polymerization initiator may be a peroxide compound, an azobis compound or the like.
  • peroxide compound examples include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, and acetylacetone peroxide; Diacyl peroxides such as isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide, bis-3,5,5-trimethylhexanoyl peroxide; Hydroperoxides such as 2,4,4, -trimethylpentyl-2-hydro peroxide, diisopropylbenzenehydro peroxide, cumene hydroperoxide and t-butylhydro peroxide; Dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane, 1,3-bis (t-butyloxyisopropyl)
  • azobis compounds examples include 1,1'-azobiscyclohexane-1-carbonitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2, -azobis ( Methylisobutyrate), 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), ⁇ , ⁇ '-azobis (isobutylnitrile) and 4,4'-azobis (4 Cyano valeric acid).
  • the initiator may be used together with a photosensitizer that absorbs light and becomes excited to transfer its energy to cause a chemical reaction.
  • photosensitizer examples include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, and the like. Can be mentioned.
  • the initiator may be included in an amount of 0.01 wt% to 10 wt%, such as 0.1 wt% to 5 wt%, based on the total amount of the photosensitive resin composition.
  • curing occurs during exposure in the pattern forming process to obtain excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and due to the unreacted initiator The fall of a transmittance
  • permeability can be prevented.
  • the solvent may be a compound having a compatibility with a compound, a binder resin, a reactive unsaturated compound, and an initiator, but not reacting, according to one embodiment.
  • the solvent examples include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glyco
  • glycol ethers such as ethylene glycol monoethyl ether, in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxy ethyl propionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates such as propylene glycol methylether acetate and propylene glycol propylether acetate can be used.
  • the solvent may be included in a balance, such as 40 wt% to 90 wt%, based on the total amount of the photosensitive resin composition.
  • a balance such as 40 wt% to 90 wt%, based on the total amount of the photosensitive resin composition.
  • the photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion to the substrate and the like.
  • a phenol novolak epoxy compound a tetramethyl biphenyl epoxy compound, a bisphenol-A epoxy compound, an alicyclic epoxy compound, or a combination thereof is mentioned.
  • the epoxy compound may be included in an amount of 0.01 to 20 parts by weight, such as 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition.
  • the epoxy compound is included in the above range, it is excellent in adhesion, storage properties and the like.
  • the photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.
  • a silane coupling agent having a reactive substituent such as a carboxyl group, methacryloyl group, isocyanate group, epoxy group, etc. in order to improve adhesion to the substrate.
  • silane coupling agent examples include trimethoxysilyl benzoic acid, ⁇ -methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, ⁇ -isocyanate propyl triethoxysilane, and ⁇ - Glycidoxy propyl trimethoxysilane, (beta)-(3, 4- epoxycyclohexyl) ethyl trimethoxysilane, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • the silane coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included in the above range, it is excellent in adhesion, shelf life and the like.
  • the photosensitive resin composition may further include a surfactant in order to improve coating properties and prevent defects, if necessary.
  • surfactant examples include, but are not limited to, BM-1000®, BM-1100® by BM Chemie, Inc .; Mecha Pack F 142D®, F 172®, F 173®, F 183®, etc. from Dai Nippon Inki Chemical Co., Ltd .; Prorad FC-135®, Copper FC-170C®, Copper FC-430®, Copper FC-431®, and the like from Sumitomo 3M Co., Ltd .; Saffron S-112®, copper S-113®, copper S-131®, copper S-141®, copper S-145® by Asahi Grass Co., Ltd .; Fluorine-based surfactants such as SH-28PA®, copper-190®, copper-193®, SZ-6032®, SF-8428®, etc. of Toray Silicone Co., Ltd. can be used.
  • the surfactant may be used in an amount of 0.001 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition.
  • the surfactant is included in the above range, coating uniformity is secured, staining does not occur, and wetting on the glass substrate is excellent.
  • the photosensitive resin composition may be added a certain amount of other additives such as antioxidants, stabilizers, etc. within a range that does not impair the physical properties.
  • a color filter manufactured using the photosensitive resin composition according to the embodiment is provided.
  • the pattern forming process in the color filter according to another embodiment is as follows.
  • Example 8 Formula a-8
  • Pigment Red 177 (C.I. 65300; 4,4'-Diamino- [1,1'-bianthracene] -9,9 ', 10,10'-tetraone):
  • the molar extinction coefficient refers to the amount of light absorbed by one mole of the compound, and the extinction coefficient is a coefficient indicating the extent to which the material absorbs light.
  • the molar extinction coefficient was determined using the absorbance of ⁇ max measured by UV-VIS equipment, the cell size used in the measuring equipment, and the concentration of the measurement solution.

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  • Architecture (AREA)
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  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Ceramic Engineering (AREA)

Abstract

L'invention concerne un composé représenté par la formule chimique (1).
PCT/KR2014/003594 2014-02-17 2014-04-24 Nouveau composé de colorant, composé de résine photosensible, et filtre de couleur comprenant le composé de colorant WO2015122567A1 (fr)

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KR1020140017960A KR101705757B1 (ko) 2014-02-17 2014-02-17 신규한 염료 화합물, 상기 염료 화합물을 포함하는 감광성 수지 조성물, 및 컬러 필터
KR10-2014-0017960 2014-02-17

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
US20160155954A1 (en) * 2014-11-25 2016-06-02 Samsung Electronics Co., Ltd. Compound for organic photoelectric device, and organic photoelectric device and image sensor including the same

Families Citing this family (5)

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JP7011055B2 (ja) 2017-10-27 2022-01-26 サムスン エスディアイ カンパニー，リミテッド 量子ドット含有組成物、量子ドット製造方法およびカラーフィルタ
KR102270495B1 (ko) * 2018-02-27 2021-06-29 삼성에스디아이 주식회사 양자점 함유 경화성 조성물, 상기 양자점 제조방법 및 컬러필터
KR102296792B1 (ko) 2019-02-01 2021-08-31 삼성에스디아이 주식회사 무용매형 경화성 조성물, 이를 이용하여 제조된 경화막, 상기 경화막을 포함하는 컬러필터, 디스플레이 장치 및 상기 경화막의 제조방법
KR102360987B1 (ko) 2019-04-24 2022-02-08 삼성에스디아이 주식회사 양자점 함유 경화성 조성물, 이를 이용한 수지막 및 디스플레이 장치
KR102504790B1 (ko) 2019-07-26 2023-02-27 삼성에스디아이 주식회사 양자점, 이를 포함하는 경화성 조성물, 상기 조성물을 이용하여 제조된 경화막, 상기 경화막을 포함하는 컬러필터, 디스플레이 장치

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JPH1130839A (ja) * 1997-07-09 1999-02-02 Konica Corp ハロゲン化銀写真感光材料
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JPH07261331A (ja) * 1994-03-22 1995-10-13 Konica Corp ハロゲン化銀写真感光材料
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US9786847B2 (en) * 2014-11-25 2017-10-10 Samsung Electronics Co., Ltd. Compound for organic photoelectric device, and organic photoelectric device and image sensor including the same

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KR20150098691A (ko) 2015-08-31
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TWI543978B (zh) 2016-08-01

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