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WO2011162217A1 - Composition de résine colorée, filtre couleur, dispositif d'affichage à cristaux liquides et affichage el organique - Google Patents

Composition de résine colorée, filtre couleur, dispositif d'affichage à cristaux liquides et affichage el organique Download PDF

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Publication number
WO2011162217A1
WO2011162217A1 PCT/JP2011/064082 JP2011064082W WO2011162217A1 WO 2011162217 A1 WO2011162217 A1 WO 2011162217A1 JP 2011064082 W JP2011064082 W JP 2011064082W WO 2011162217 A1 WO2011162217 A1 WO 2011162217A1
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Prior art keywords
ring
substituent
group
resin composition
carbon atoms
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PCT/JP2011/064082
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English (en)
Japanese (ja)
Inventor
宗賢 藤原
迫　直樹
祥平 蓼沼
靖 志賀
石田　美織
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Mitsubishi Chemical Corp
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Mitsubishi Chemical Corp
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Priority to CN201180030503.8A priority Critical patent/CN102947733B/zh
Priority to JP2012521468A priority patent/JP5915526B2/ja
Priority to KR1020127022592A priority patent/KR20130091629A/ko
Publication of WO2011162217A1 publication Critical patent/WO2011162217A1/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
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • 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
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • 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
    • G02B5/201—Filters in the form of arrays
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters

Definitions

  • the present invention resides in a colored resin composition, a color filter, a liquid crystal display device and an organic EL display.
  • a color liquid crystal display device includes, as an example, a black matrix, a colored layer composed of a plurality of colors (usually three primary colors of red (R), green (G), and blue (B)), a transparent electrode, and an alignment layer.
  • the provided color filter substrate, a thin film transistor (TFT element), a counter electrode substrate provided with a pixel electrode and an alignment layer, and these substrates are opposed to each other with a predetermined gap, sealed with a sealing member, and liquid crystal is placed in the gap.
  • TFT element thin film transistor
  • TFT element counter electrode substrate provided with a pixel electrode and an alignment layer, and these substrates are opposed to each other with a predetermined gap, sealed with a sealing member, and liquid crystal is placed in the gap.
  • a transmissive liquid crystal display device that is roughly configured from a liquid crystal layer formed by injecting a material.
  • a reflective liquid crystal display device in which a reflective layer is provided between the color filter substrate and the colored layer.
  • an organic EL display has an organic EL element having a structure in which an organic EL light emitting layer is sandwiched between an anode and a cathode.
  • color display is possible using the organic EL element.
  • CCM method that combines an organic EL element that emits blue light and a color conversion layer (CCM layer) that performs color conversion from blue to green and blue to red, respectively.
  • the method of (1) is characterized in that high color reproducibility can be exhibited because organic EL elements of each color are used. Therefore, by placing color filters corresponding to the organic EL elements of each color, improvement in color reproducibility and improvement in contrast by absorbing reflected light can be expected. .
  • the combination method of the white organic EL and the color filter in (2) and the CCM method in (3) may use only one type of organic EL element that emits light of the same color. Unlike the EL display, it is not necessary to align the characteristics of the organic EL elements of each color, and the number of processes and materials can be reduced.
  • an organic EL device using a color filter and a color conversion method comprising a color conversion filter and an organic light emitter as constituent elements
  • heat resistance required in the color display manufacturing process weather resistance when used as a display
  • color filters created by the pigment dispersion method are the mainstream, and red, blue, or green pigments in the photosensitive resin solution have a particle size of 1 ⁇ m or less.
  • Non-patent Document 1 a method of finely dispersing the particle size of pigment particles to 1/2 or less of the coloration wavelength is known (Non-patent Document 1). Is shorter in coloration wavelength than other red and green pigments, and in this case, further fine dispersion is required, resulting in problems of cost increase and stability after dispersion.
  • Patent Document 1 discloses a color filter provided with a blue filter layer containing C-I Acid Blue 83 (triallylamine-based color material) and C-I Solvent Blue 67 (copper phthalocyanine-based color material). Are listed.
  • Patent Document 2 describes a color filter using a polymer containing a polymerizable triphenylmethane dye represented by the following formula.
  • At least one of R 1 in the above formula is a specific polymerizable group containing a carbon-carbon double bond
  • Patent Document 3 also describes a colored resin composition containing a color material represented by a specific structure.
  • Japanese Unexamined Patent Publication No. 2002-14222 Japanese Unexamined Patent Publication No. 2000-162429 Japanese Unexamined Patent Publication No. 2009-235392
  • An object of this invention is to provide the colored resin composition which satisfy
  • Another object of the present invention is to provide a color filter excellent in color purity and transmittance (brightness) of a blue pixel, an organic EL display with good blue purity, and a liquid crystal display device by using such a colored resin composition. To do.
  • the present inventors have found that the above problems can be solved by using a salt composed of a compound having a specific structure as a dye for forming a blue pixel of a color filter. That is, the first gist of the present invention resides in the colored resin composition shown in the following [1] to [3] (hereinafter sometimes referred to as “first colored resin composition”). [1] containing (A) a dye, (B) a solvent and (C) a binder resin, (A) A colored resin composition, wherein the dye contains a compound represented by the following formula (I).
  • (Z 1 ) m1- represents an m1-valent disulfonylimide anion.
  • m1 represents an integer of 1 to 4.
  • R 1 to R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 1 to R 6 may be linked to form a ring, and the ring may have a substituent.
  • R 7 and R 8 represent a hydrogen atom or an arbitrary substituent. R 7 and R 8 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring in the above formula (I) may further have an arbitrary substituent.
  • R 101 and R 102 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • R 101 and R 102 may be bonded to each other to form a ring, and the ring may have a substituent.
  • R 1 to R 8 , R 101 and R 102 have the same definitions as in the formula (I).
  • the benzene ring in the above formula (I-1) may further have an arbitrary substituent.
  • R 21 and R 22 each independently represents an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent.
  • a cycloalkyl group having 3 to 8 carbon atoms which may have R 21 and R 22 may be connected to each other to form a ring, and the ring may have a substituent.
  • [3] The colored resin composition according to [2], wherein at least one of R 21 and R 22 is a group containing a fluorine atom.
  • the second gist of the present invention resides in the colored resin composition shown in the following [4] to [6] (hereinafter sometimes referred to as “second colored resin composition”).
  • [4] containing (A) a dye, (B) a solvent and (C) a binder resin, (A) A colored resin composition, wherein the dye contains a compound represented by the following formula (II).
  • (Z 2 ) m2- represents an m2-valent disulfonylimide anion.
  • m2 represents an integer of 1 to 4.
  • R 11 to R 16 each independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 11 to R 16 may be linked to each other to form a ring, and the ring may have a substituent.
  • R 17 and R 18 each independently represents a hydrogen atom or an arbitrary substituent. R 17 and R 18 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring and indole ring in the above formula (II) may further have an arbitrary substituent.
  • R 11 to R 18 are the same as defined in the formula (II).
  • the benzene ring and indole ring in the above formula (II-1) may further have an arbitrary substituent.
  • R 31 and R 32 are each independently an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • a cycloalkyl group having 3 to 8 carbon atoms which may have R 31 and R 32 may be connected to each other to form a ring, and the ring may have a substituent.
  • [6] The colored resin composition according to the above [5], wherein at least one of R 31 and R 32 is a group containing a fluorine atom.
  • the third gist of the present invention resides in the colored resin composition shown in the following [7] to [9] (hereinafter sometimes referred to as “third colored resin composition”).
  • [7] containing (A) a dye, (B) a solvent, and (C) a binder resin, (A) A colored resin composition, wherein the dye contains a compound represented by the following formula (III).
  • (Z 3 ) m3- represents an m3-valent disulfonylimide anion.
  • m3 represents an integer of 1 to 4.
  • q represents an integer of 1 to 5.
  • R 501 and R 502 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • R 51 and R 52 each independently represents —O—, —S—, —N—, —Se— or —CR 503 R 504 —.
  • R 503 and R 504 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
  • R 503 may be linked to each other to form a ring, and the ring may have a substituent.
  • Rings Y 1 and Y 2 each independently represent an optionally substituted benzene ring or naphthalene ring. However, the benzene ring and naphthalene ring in the rings Y 1 and Y 2 do not have a nitro group or a perfluoro group as a substituent.
  • R 41 and R 42 each independently represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. And a cycloalkyl group having 3 to 8 carbon atoms which may have R 41 and R 42 may be connected to each other to form a ring, and the ring may have a substituent.
  • the fourth gist of the present invention resides in the colored resin composition shown in the following [10] to [12] (hereinafter sometimes referred to as “fourth colored resin composition”).
  • [10] containing (A) a dye, (B) a solvent, and (C) a binder resin, (A)
  • the dye contains a counter ion composed of a cation and an anion, the molecular weight of the anion is 150 or more and 600 or less, and the counter ion satisfies the following formulas (1) to (3):
  • a colored resin composition containing (A) a dye, (B) a solvent, and (C) a binder resin, (A)
  • the dye contains a counter ion composed of a cation and an anion, the molecular weight of the anion is 150 or more and 600 or less, and the counter ion satisfies the following formulas (1) to (3):
  • a colored resin composition containing (A) a dye, (B) a solvent,
  • IP cation represents the ionization potential of the cation
  • EA cation represents the electron affinity of the cation
  • IP anion represents the ionization potential (hartree) of the anion
  • EA anion represents the electron affinity of the anion.
  • R 61 to R 66 each independently have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or a substituent. Represents an aromatic ring group which may be substituted. Adjacent R 61 to R 66 may be connected to each other to form a ring, and the ring may have a substituent. R 67 and R 68 represent a hydrogen atom or an arbitrary substituent. R 67 and R 68 may be connected to each other to form a ring, and the ring may have a substituent. Further, the benzene ring in the above formula (I-2) CA may further have an arbitrary substituent.
  • R 601 and R 602 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. Represents an aromatic ring group which may be substituted, or a fluorine atom. R 601 and R 602 may be bonded to each other to form a ring, and the ring may have a substituent. ) [12] The colored resin composition according to [10], wherein the cation is represented by the following formula (II-2) CA.
  • R 71 to R 76 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring which may have a substituent. Represents a group. Adjacent R 71 to R 76 may be linked to form a ring, and the ring may have a substituent. R 77 and R 78 each independently represent a hydrogen atom or an arbitrary substituent. R 77 and R 88 may be connected to each other to form a ring, and the ring may have a substituent. Further, the benzene ring and indole ring in the above formula (II-2) CA may further have an arbitrary substituent. )
  • the colored resin composition shown in the above [1] to [12] further contains (D) a polymerizable monomer, (E) at least one of a photopolymerization initiation component and a thermal polymerization initiation component, and (F) a pigment. May be.
  • the present invention also resides in a color filter including pixels formed using the colored resin composition of the present invention, a liquid crystal display device, and an organic EL display.
  • the “colored resin composition of the present invention” is a general term for the “first to fourth colored resin compositions”.
  • a color filter having heat resistance required in the color display manufacturing process and excellent in color purity and transmittance of a blue pixel can be obtained.
  • the light emission of the organic EL display and the light emission of the backlight of the color filter can be taken out efficiently, and a liquid crystal display device and an organic EL display that achieve both high color reproducibility and high luminance.
  • the contrast of the liquid crystal display device can be improved.
  • (meth) acryl means “acryl and / or methacryl”, “acrylate and / or methacrylate” and the like, for example, “(meth) acrylic acid” "Means” acrylic acid and / or methacrylic acid ".
  • total solid content means all components of the colored resin composition of the present invention other than the solvent components described later.
  • C. I. Means a color index.
  • the colored resin composition of the present invention contains (A) a dye, (B) a solvent, and (C) a binder resin, and the (A) dye is any one of the following (a) to (d): To do. In any case, heat resistance is particularly superior to conventional dye compounds.
  • a compound represented by the following formula (I) (hereinafter sometimes referred to as “compound (I)”) is contained.
  • (Z 1 ) m1- represents an m1-valent disulfonylimide anion.
  • m1 represents an integer of 1 to 4.
  • R 1 to R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 1 to R 6 may be linked to form a ring, and the ring may have a substituent.
  • R 7 and R 8 represent a hydrogen atom or an arbitrary substituent. R 7 and R 8 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring in the above formula (I) may further have an arbitrary substituent.
  • R 101 and R 102 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • R 101 and R 102 may be bonded to each other to form a ring, and the ring may have a substituent.
  • (Z 2 ) m2- represents an m2-valent disulfonylimide anion.
  • m2 represents an integer of 1 to 4.
  • R 11 to R 16 each independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 11 to R 16 may be linked to each other to form a ring, and the ring may have a substituent.
  • R 17 and R 18 each independently represents a hydrogen atom or an arbitrary substituent. R 17 and R 18 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring and indole ring in the above formula (II) may further have an arbitrary substituent.
  • (Z 3 ) m3- represents an m3-valent disulfonylimide anion.
  • m3 represents an integer of 1 to 4.
  • q represents an integer of 1 to 5.
  • R 501 and R 502 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • R 51 and R 52 each independently represents —O—, —S—, —N—, —Se— or —CR 503 R 504 —.
  • R 503 and R 504 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
  • R 503 may be linked to each other to form a ring, and the ring may have a substituent.
  • Rings Y 1 and Y 2 each independently represent an optionally substituted benzene ring or naphthalene ring. However, the benzene ring and naphthalene ring in the rings Y 1 and Y 2 do not have a nitro group or a perfluoro group as a substituent.
  • the dye contains a counter ion comprising a cation and an anion, the anion has a molecular weight of 150 to 600, and the counter ion satisfies the following formulas (1) to (3) , Sometimes referred to as “compound (IV)”.
  • IP cation represents the ionization potential of the cation
  • EA cation represents the electron affinity of the cation
  • IP anion represents the ionization potential (hartree) of the anion
  • EA anion represents the electron affinity of the anion.
  • the colored resin composition of the present invention contains (A) a dye, (B) a solvent, and (C) a binder resin, preferably (D) a polymerizable monomer, (E) a photopolymerization initiating component, and / or thermal polymerization. Including the starting component, (F) pigment, and other components added as necessary.
  • Structural features of the compounds represented by the formulas (I) to (III) are as follows.
  • the compounds represented by the formulas (I) to (III) contained in the dye (A) in the present invention form a counter ion.
  • the properties of the cation and the anion affect the physical properties, particularly the heat resistance. This is due to the higher reactivity of cations and anions having a bias in charge than neutral molecules. Therefore, it is presumed that the heat resistance of the dye can be improved by reducing the reactivity of the cation and the anion. That is, in the cation and the anion, it is considered that the reactivity is lowered by delocalizing the electric charge and the heat resistance is improved.
  • a disulfonylimide anion is used as the anion.
  • the disulfonylimide anion is easy to produce because the ionic species is a sulfonamide group.
  • the anion is relatively stable.
  • the disulfonamide has a fluorine-containing substituent. In this case, it is considered that the anion is pulled toward the fluorine-containing substituent, whereby electric charges are dispersed as a whole molecule and a more stable structure is obtained.
  • none of the anions in the present invention absorbs in the visible region. Therefore, the influence on the transmittance (luminance) is small.
  • the color filter obtained by using the colored resin composition of the present invention has both transmittance (luminance) and heat resistance.
  • the 1st coloring resin composition of this invention contains the compound represented by following formula (I) as (A) dye.
  • the compound represented by the following formula (I) is excellent in heat resistance, and particularly preferable in terms of excellent blue purity and transmittance.
  • (Z 1 ) m1- represents an m1-valent disulfonylimide anion.
  • m1 represents an integer of 1 to 4.
  • R 1 to R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 1 to R 6 may be linked to form a ring, and the ring may have a substituent.
  • R 7 and R 8 represent a hydrogen atom or an arbitrary substituent. R 7 and R 8 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring in the above formula (I) may further have an arbitrary substituent.
  • R 101 and R 102 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • R 101 and R 102 may be bonded to each other to form a ring, and the ring may have a substituent.
  • R 1 to R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic ring group which may have a substituent.
  • alkyl group in R 1 to R 6 include linear, branched or cyclic alkyl groups, and the number of carbon atoms is usually 1 or more, and usually 8 or less, preferably 5 or less. . Specific examples include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, cyclohexyl group and the like.
  • Examples of the aromatic ring group in R 1 to R 6 include an aromatic hydrocarbon ring group and an aromatic heterocyclic group.
  • the aromatic hydrocarbon ring group may be a single ring or a condensed ring, and is not particularly limited as long as it has 5 to 18 carbon atoms to form the ring. Benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, fluorene ring, and the like.
  • the aromatic heterocyclic group may be a monocyclic ring or a condensed ring, and is not particularly limited as long as the number of carbon atoms forming the ring is 3 to 10.
  • one free atom Have a furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole Ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine
  • Adjacent R 1 to R 6 may be linked to form a ring, and the ring may have a substituent.
  • the ring may be a ring bridged with a heteroatom, and specific examples thereof include the following structures.
  • R 1 to R 6 are preferably each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or a substituent. It is a good phenyl group, or when adjacent R 1 to R 6 are connected to each other to form a ring. From the viewpoint of improving the heat resistance of the dye and the heat resistance of the resulting color filter being excellent, more preferably, it may have a C 1-8 alkyl group or substituent which may have a substituent. It is a phenyl group.
  • R 1 to R 6 are an optionally substituted alkyl group having 1 to 8 carbon atoms, it is presumed that the charges in the cation are dispersed by hyperconjugation and the cation is stabilized. Further, when R 1 to R 6 are phenyl groups which may have a substituent, the conjugated system is extended, so that the charge in the cation is dispersed and the cation is stabilized. As described above, it can be considered that as a result of stabilization of the cation, the heat resistance of the obtained color filter is further improved.
  • Examples of the substituent that the alkyl group, the aromatic ring group, and the ring formed by being linked to each other in R 1 to R 6 may have include the following (substituent group W).
  • (Substituent group W) Fluorine atom, chlorine atom, alkyl group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms, alkoxyl group having 1 to 8 carbon atoms, phenyl group, mesityl group, tolyl group, naphthyl group, cyano group, acetyloxy Group, alkylcarbonyloxy group having 2 to 9 carbon atoms, sulfonic acid amide group, sulfonealkylamide group having 2 to 9 carbon atoms, alkylcarbonyl group having 2 to 9 carbon atoms, phenethyl group, hydroxyethyl group, acetylamide group, A dialkylaminoethyl group formed by bonding an alkyl group
  • the alkyl group, aromatic ring group, and ring formed by connecting to each other in R 1 to R 6 may have, preferably an alkyl group having 1 to 8 carbon atoms, 2 to An alkoxyl group having 8 carbon atoms, a cyano group, an acetyloxy group, an alkyl carboxyl group having 2 to 8 carbon atoms, a sulfonic acid amide group, a sulfone alkylamide group having 2 to 8 carbon atoms, and a fluorine atom.
  • R 7 and R 8 represent a hydrogen atom or an arbitrary substituent.
  • the optional substituent include a halogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, and an optionally substituted aromatic ring group.
  • the o-position does not have a substituent or is substituted with a halogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the alkyl group having 1 to 8 carbon atoms is preferably an alkyl having 1 to 4 carbon atoms from the viewpoint of small steric hindrance.
  • R 7 and R 8 may be connected to each other to form a ring, and the ring may have a substituent.
  • substituent group W examples include those described in the above section (Substituent group W).
  • R 7 and R 8 are linked to form a ring, these may be a ring bridged with a heteroatom.
  • Examples of the structure of the linking moiety of R 7 and R 8 include the following. The structure of these connecting portions may have a substituent.
  • R 7 and R 8 are not connected to each other to form a ring from the viewpoint of high luminance.
  • the obtained color filter is purple, and from the viewpoint of high brightness, it is preferable that they are connected to each other to form a ring.
  • R 101 and R 102 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • Examples of the alkyl group and the aromatic ring group include those described in the above section (for R 1 to R 6 ).
  • Examples of the alkenyl group include those having usually 2 or more and usually 6 or less carbon atoms. Specific examples include vinyl group, allyl group, 1-butenyl group and the like.
  • R 101 and R 102 are connected to form a part of the ring, so that R 101 and R 102 are in a plane composed of the benzene ring adjacent to the sp2 carbon atom at the center of the triarylmethane structure. Since the bonded benzene rings have a twisted positional relationship, they have blue absorption, which improves the spectral characteristics of the colored resin composition for color filters using the same, and easily improves the contrast of the blue display member. Is preferable. Examples of the structure of the connecting portion of R 101 and R 102 include the following.
  • the structure of the connecting part of R 101 and R 102 may have a substituent.
  • substituent group W include those described in the above section (Substituent group W).
  • the benzene ring in the above formula (I) may further have an arbitrary substituent. That is, it may have substituents other than those specified in formula (I) within a range not impairing the effects of the present invention, but it is specified in formula (I) because it is easy to produce. It is preferable not to have any other substituent. Examples of such a substituent include the substituents described in the above section (Substituent Group W).
  • R 1 to R 8 , R 101 and R 102 have the same definitions as in the formula (I).
  • the benzene ring in the above formula (I-1) may further have an arbitrary substituent.
  • R 21 and R 22 each independently represents an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent.
  • a cycloalkyl group having 3 to 8 carbon atoms which may have R 21 and R 22 may be connected to each other to form a ring, and the ring may have a substituent.
  • R 21 and R 22 each independently represents an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent, or a substituent.
  • a cycloalkyl group having 3 to 8 carbon atoms which may have R 21 and R 22 may be connected to each other to form a ring, and the ring may further have a substituent.
  • substituent which the alkyl group, alkenyl group, cycloalkyl group and ring formed by connecting to each other in R 21 and R 22 may have include those described in the above (Substituent group W) section. Can be mentioned.
  • the substituent of the alkyl group alkenyl group or cycloalkyl group in R 21 and R 22 , the substituent of the fluorine atom is substituted in that the anion charge is more delocalized and the heat resistance of the dye is improved. It is preferable to have as.
  • R 21 and R 22 are preferably a group containing a fluorine atom, particularly a perfluoroalkyl group having 1 to 8 carbon atoms, in that the anion charge is dispersed and the anion is stabilized.
  • R 21 and R 22 are preferably a group containing a fluorine atom, particularly a perfluoroalkyl group having 1 to 8 carbon atoms, in that the anion charge is dispersed and the anion is stabilized.
  • an anion in the compound represented by the formula (I-1) that is, an anion represented by the following formula (I-1) A (hereinafter, represented by the formula (I-1)
  • the “anion in the compound” is sometimes referred to as a compound represented by the following formula (I′-1) A.
  • n and n ′ are an integer of 1 to 8, preferably an integer of 1 to 4.
  • n and n ′ may be the same or different.
  • Specific examples of the sulfonylimide anion when n and n ′ are the same include bis (trifluoromethanesulfone) imide, bis (pentafluorobutanesulfone) imide and the like.
  • sulfonylimide anion when n and n ′ are different include pentafluoroethanesulfone trifluoromethanesulfonimide, trifluoromethanesulfone heptafluoropropanesulfonimide, fluorobutanesulfone trifluoromethanesulfonimide, and the like.
  • R 21 and R 22 may be connected to each other to form a ring.
  • the group formed by linking R 21 and R 22 is particularly preferably a fluoroalkylene group having 2 to 12 carbon atoms. That is, the anion in the compound represented by the formula (I-1) is preferably an anion represented by the following formula (I′-2) A.
  • n ′′ represents an integer of 2 to 12
  • n ′′ is preferably 2 to 8 and more preferably 3 in terms of good heat resistance.
  • a dimer or a trimer may be formed by extending a linker from R 1 to R 6 and R 101 and R 102 .
  • the molecular weight of the compound represented by the formula (I) in the present invention is usually 570 or more, preferably 840 or more, and usually 2600 or less. It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.
  • the compound represented by the formula (I) is preferably 1% by weight or more, more preferably 3% by weight or more, and particularly preferably 5% by weight in the total solid content.
  • the content is preferably 50% by weight or less, more preferably 40% by weight or less, and particularly preferably 30% by weight or less. It is preferable for it to be less than or equal to the above upper limit because the curability of the coating film is unlikely to decrease and the film strength is sufficient. Moreover, since it is sufficient for coloring power to be more than the said minimum, since the chromaticity of a desired density
  • the content of all (A) dyes in the first colored resin composition is preferably 1% by weight or more, or preferably 30% by weight or less in the composition.
  • the content of compound (I) is preferably 30% by weight or more in the solid content of all (A) dyes.
  • the 2nd colored resin composition of this invention is preferable at the point which is excellent in the heat resistance of the color filter obtained, and has the high transmittance
  • (Z 2 ) m2- represents an m2-valent disulfonylimide anion.
  • m2 represents an integer of 1 to 4.
  • R 11 to R 16 each independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent. Adjacent R 11 to R 16 may be bonded to each other to form a ring, and the ring may have a substituent.
  • R 17 and R 18 each independently represents a hydrogen atom or an arbitrary substituent. R 17 and R 18 may be connected to each other to form a ring, and the ring may have a substituent.
  • the benzene ring and indole ring in the above formula (II) may further have an arbitrary substituent.
  • R 11 to R 16 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms which may have a substituent, or an aromatic ring group which may have a substituent.
  • Examples of the alkyl group having 1 to 8 carbon atoms and the aromatic ring group are the same as those described in the above section (for R 1 to R 6 ).
  • the preferred embodiment is also the same.
  • adjacent R 11 to R 16 that is, R 11 and R 12 , R 13 and R 14, and R 15 and R 16 may be connected to each other to form a ring, and the ring is substituted. It may have a group.
  • R 11 to R 16 When adjacent R 11 to R 16 are connected to form a ring, these may be a ring bridged with a heteroatom. Specific examples of this ring are the same as those described in the above section (for R 1 to R 6 ). The preferred embodiment is also the same.
  • R 17 and R 18 represent a hydrogen atom or an arbitrary substituent.
  • the optional substituent include those described in the above section (for R 7 and R 8 ).
  • the o-position does not have a substituent or is substituted with a halogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 17 and R 18 may be connected to each other to form a ring, and the ring may have a substituent.
  • substituent group W examples include those described in the above section (Substituent group W).
  • R 17 and R 18 are connected to each other to form a ring, these may be a ring bridged with a heteroatom, and specific examples thereof are described in the above-mentioned (for R 7 and R 8 ). It is the same as that.
  • the obtained color filter is purple, it is preferable that R 7 and R 8 are not connected to each other to form a ring from the viewpoint of high luminance.
  • the color filter to be obtained is red, it is preferable that they are connected to each other to form a ring from the viewpoint of high luminance.
  • R 11 to R 18 is an alkyl group having 1 to 8 carbon atoms substituted with a fluorine atom, from the viewpoint of excellent heat resistance of the obtained color filter.
  • R 11 to R 18 is an alkyl group having 1 to 8 carbon atoms substituted with a fluorine atom, from the viewpoint of excellent heat resistance of the obtained color filter.
  • the benzene ring and indole ring in the formula (II) may further have a substituent. That is, it may have a substituent other than that specified in formula (II) as long as the effect of the present invention is not impaired, but from the viewpoint of easy production, other than those specified in formula (II) It is preferable not to have the above substituent. Examples of such a substituent include the substituents described in the above section (Substituent Group W).
  • the compound represented by the formula (II) may be formed into a dimer or trimer by extending a linker from R 11 to R 18 , for example.
  • R 11 to R 18 are the same as defined in the formula (II).
  • the benzene ring and indole ring in the above formula (II-1) may further have an arbitrary substituent.
  • R 31 and R 32 are each independently an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent.
  • a cycloalkyl group having 3 to 8 carbon atoms which may have R 31 and R 32 may be connected to each other to form a ring, and the ring may have a substituent.
  • R 31 and R 32 are each independently an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. And a cycloalkyl group having 3 to 8 carbon atoms which may have R 31 and R 32 may be connected to each other to form a ring, and the ring may have a substituent.
  • R 31 and R 32 are the same as R 21 and R 22 in the formula (I-1), and preferred embodiments are also the same. That is, the anion in the compound represented by the formula (II-1) is preferably an anion represented by the formula (I′-1) A or (I′-2) A.
  • the molecular weight of the compound represented by the formula (II) in the present invention is usually 600 or more, preferably 750 or more, and usually 2800 or less. It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.
  • the compound represented by the formula (II) is preferably 1% by weight or more, more preferably 3% by weight or more, and particularly preferably 5% by weight in the total solid content.
  • the content is preferably 50% by weight or less, more preferably 40% by weight or less, and particularly preferably 30% by weight or less. It is preferable for it to be less than or equal to the above upper limit because the curability of the coating film is unlikely to decrease and the film strength is sufficient.
  • it is sufficient for coloring power to be more than the said minimum since it is sufficient for coloring power to be more than the said minimum, since the chromaticity of a desired density
  • the 2nd coloring resin composition of this invention only 1 type of compound (II) may be contained as (A) dye, and 2 or more types may be contained. Furthermore, one or more of other dyes may be contained, but the content of all (A) dyes in the second colored resin composition is preferably 1% by weight or more in the composition. Or preferably 30% by weight or less. In the second colored resin composition of the present invention, the content of the compound (II) is preferably 30% by weight or more in the solid content of the total (A) dye.
  • the 3rd coloring resin composition of this invention contains the compound represented by following formula (III) as (A) dye.
  • a compound represented by the following formula (III) is preferable in that the heat resistance and transmittance of the obtained color filter are excellent.
  • (Z 3 ) m3- represents an m3-valent disulfonylimide anion.
  • m3 represents an integer of 1 to 4.
  • q represents an integer of 1 to 5.
  • R 501 and R 502 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • R 51 and R 52 each independently represents —O—, —S—, —N—, —Se— or —CR 503 R 504 —.
  • R 503 and R 504 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
  • R 503 may be linked to each other to form a ring, and the ring may have a substituent.
  • Rings Y 1 and Y 2 each independently represent an optionally substituted benzene ring or naphthalene ring. However, the benzene ring and naphthalene ring in the rings Y 1 and Y 2 do not have a nitro group or a perfluoro group as a substituent.
  • (About q) q is an integer of 1 to 5, and 1 to 3 is particularly preferable from the viewpoint of good heat resistance of the dye.
  • R 501 and R 502 each independently represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • the aliphatic hydrocarbon group include a methyl group, an ethyl group, a vinyl group, an ethynyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a 2-propynyl group, a butyl group, Isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 1,3-butadienyl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-methylpentyl group, 2-methylpentyl group 2-pentene-4-ynyl group, hexyl group, iso
  • Examples of the substituent that the aliphatic hydrocarbon group may have include, for example, a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, aromatic hydrocarbon groups such as m-cumenyl group and p-cumenyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, Examples include alkoxy groups such as phenoxy group and benzyloxy group; halogen groups such as fluoro group, chloro group, bromo group and iodo group; and further, carboxy group, nitro group, cyano group and the like.
  • R 501 and R 502 are each preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms. Examples of the substituent that R 501 and R 502 may have include those described in the above section (Substituent group W).
  • R 51 and R 52 each independently represents —O—, —S—, —N—, —Se— or —CR 503 R 504 —.
  • R 503 and R 504 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms.
  • R 51 and R 52 are —CR 503 R 504 —, R 503s may be connected to each other to form a ring. Examples of the structure of the connecting portion of R 51 and R 52 include the following, but the present invention is not limited to these.
  • Rings Y 1 and Y 2 each independently represent an optionally substituted benzene ring or naphthalene ring.
  • a nitro group and a perfluoroalkyl group are excluded as substituents that the benzene ring and naphthalene ring in the rings Y 1 and Y 2 may have. This is because when the compound represented by the formula (III) has a nitro group or a perfluoroalkyl group as a substituent, it easily forms an aggregate in the composition or film, and the color obtained therefrom This is because the brightness of the filter tends to decrease.
  • nitro groups and perfluoroalkyl groups are easy to accept electrons from surrounding molecules, and as a result, the compounds represented by the formula (III) are likely to be decomposed, and the heat resistance of the color filter obtained using them is improved. This is because it tends to decrease.
  • the compound represented by the formula (III) may form a dimer or trimer from R 51 , R 52 , R 501 and R 502 by extending a linker.
  • the cation moiety has a cis-trans isomer, but any isomer may be used.
  • R 41 and R 42 each independently represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. And a cycloalkyl group having 3 to 8 carbon atoms which may have R 41 and R 42 may be connected to each other to form a ring, and the ring may have a substituent.
  • R 41 and R 42 each independently represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. And a cycloalkyl group having 3 to 8 carbon atoms which may have R 41 and R 42 may be connected to each other to form a ring, and the ring may have a substituent.
  • R 41 and R 42 are the same as R 21 and R 22 in the formula (I-1), and preferred embodiments are also the same.
  • R 41 and R 42 are preferably a group having a fluorine atom from the viewpoint that the charge of the anion is dispersed and the anion is stabilized, and particularly a perfluoroalkyl group having 1 to 8 carbon atoms. It is preferable. That is, the anion in the compound represented by the formula (III-1) is preferably an anion represented by the formula (I′-1) A or (I′-2) A.
  • the molecular weight of the compound represented by the formula (III) in the present invention is usually 550 or more, preferably 600 or more, and usually 2100 or less. It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.
  • the compound represented by the formula (III) is preferably 1% by weight or more, more preferably 3% by weight or more, and particularly preferably 5% by weight in the total solid content.
  • the content is preferably 50% by weight or less, more preferably 40% by weight or less, and particularly preferably 30% by weight or less. It is preferable for it to be less than or equal to the above upper limit because the curability of the coating film is unlikely to decrease and the film strength is sufficient. Moreover, since it is sufficient for coloring power to be more than the said minimum, since the chromaticity of a desired density
  • the 3rd coloring resin composition of this invention only 1 type of compound (III) may be contained as (A) dye, and 2 or more types may be contained. Furthermore, one or more of other dyes may be contained, but the content of all (A) dyes in the third colored resin composition is preferably 1% by weight or more in the composition. Or preferably 30% by weight or less. In the third colored resin composition of the present invention, the content of the compound (III) is preferably 30% by weight or more in the solid content of the total (A) dye.
  • the (A) dye contained in the fourth colored resin composition of the present invention contains a counter ion composed of a cation and an anion, the molecular weight of the anion is 150 or more and 600 or less, and the counter ion is represented by the following formula: Compound (IV) that satisfies the relationships (1) to (3).
  • IP cation represents the ionization potential of the cation
  • EA cation represents the electron affinity of the cation
  • IP anion represents the ionization potential (hartree) of the anion
  • EA anion represents the electron affinity of the anion.
  • Equation (2) represents the degree of electron localization in the cation in the counter ion
  • Equation (3) represents the degree of electron localization in the anion in the counter ion.
  • the anion and cation having closer electron localization tend to have stronger interaction between the anion and cation. That is, the formula (1) indicates a difference in the degree of localization between the anion and the cation, and means that the combinations are closer to each other.
  • the molecular weight of the anion is set to 150 or more and 600 or less.
  • the compound (IV) of the present invention may be appropriately selected from known materials so that the molecular weight of the anion is 150 or more and 600 or less and satisfies the above (1) to (3). .
  • the ionization potential and the electron affinity are optimized for the molecular structure at the calculation level of HF / 6-31G (D), and the obtained HOMO and LUMO energies are converted into the ionization potential and the electron affinity, respectively. (Hartley). In calculating the ionization potential and the electron affinity, cations and anions are calculated separately.
  • a dye satisfying the above formula (3) is selected from the dyes described in “Industrial Dyes—Chemistry, Properties, Applications— (Wiley-VCH, 2003, edited by Klaus Hunger)”. More specifically, compounds having a dye skeleton (Chromophore) such as triarylmethanes, cyanines, styryls and azines can be mentioned, and can be appropriately selected depending on a desired color.
  • a dye skeleton Chromophore
  • the anion candidates may be selected from the formula (2) and those having a molecular weight of 150 or more and 600 or less so as to satisfy the formula (1) in relation to the cation.
  • the molecular weight of the anion is usually 150 or more, preferably 200 or more, more preferably 250 or more, and usually 600 or less, preferably 500 or less. Within the above range, it is preferable in that the effect of the present invention can be obtained satisfactorily.
  • the molecular weight of the compound (IV) in the present invention is preferably 570 or more, more preferably 600 or more, and usually 3000 or less. It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.
  • the cation is preferably a compound represented by the following formula (I-2) CA or (II-2) CA.
  • R 61 to R 66 each independently have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, or a substituent. Represents an aromatic ring group which may be substituted. Adjacent R 61 to R 66 may be connected to each other to form a ring, and the ring may have a substituent. R 67 and R 68 represent a hydrogen atom or an arbitrary substituent. R 67 and R 68 may be connected to each other to form a ring, and the ring may have a substituent. Further, the benzene ring in the above formula (I-2) CA may further have an arbitrary substituent.
  • R 601 and R 602 have a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 6 carbon atoms, or a substituent. Represents an aromatic ring group which may be substituted, or a fluorine atom. R 601 and R 602 may be bonded to each other to form a ring, and the ring may have a substituent. )
  • R 71 to R 76 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring which may have a substituent. Represents a group. Adjacent R 71 to R 76 may be linked to form a ring, and the ring may have a substituent. R 77 and R 78 each independently represent a hydrogen atom or an arbitrary substituent. R 77 and R 88 may be connected to each other to form a ring, and the ring may have a substituent. Further, the benzene ring and indole ring in the above formula (II-2) CA may further have an arbitrary substituent. )
  • the embodiments of the compound represented by the above formula (I-2) CA and (II-2) CA are the cation in [compound represented by formula (I)] and the [compound represented by formula (II)], respectively. This is the same as the embodiment of the cation in.
  • the preferred embodiment is also the same. That is, R 61 to R 66 in the compound represented by the formula (I-2) CA are cation R 1 to R 6 , R 67 and R 68 in [Compound represented by the formula (I)]. , R 7 and R 8 and R 601 and R 602 are the same as the embodiments of R 101 and R 102 , respectively.
  • R 71 to R 76 in the compound represented by the formula (II-2) CA are cation R 11 to R 16 in the [compound represented by the formula (II)], and R 77 and R 88 are R
  • Each of the embodiments 17 and R 18 is the same.
  • the compound represented by the formula (I) and the compound represented by the formula (II) preferably further satisfy the relations of the formulas (1) to (3).
  • the compound (IV) is preferably added in an amount of 1% by weight or more, more preferably 3% by weight or more, particularly preferably 5% by weight or more, based on the total solid content. 50 wt% or less, more preferably 40 wt% or less, particularly preferably 30 wt% or less. It is preferable for it to be less than or equal to the above upper limit because the curability of the coating film is unlikely to decrease and the film strength is sufficient. Moreover, since it is sufficient for coloring power to be more than the said minimum, since the chromaticity of a desired density
  • the 4th colored resin composition of this invention only 1 type of compound (IV) may be contained as (A) dye, and 2 or more types may be contained. Furthermore, one or more of other dyes may be contained, but the content of all (A) dyes in the first colored resin composition is preferably 1% by weight or more in the composition. Or preferably 30% by weight or less. In addition, in the 4th colored resin composition of this invention, it is preferable that content of compound (IV) is 30 weight% or more in solid content of all the (A) dyes.
  • (C) Binder resin What preferable binder resin changes with the hardening means of a colored resin composition.
  • the colored resin composition of the present invention is a photopolymerizable resin composition
  • examples of the (C) binder resin include, for example, Japanese Patent Application Laid-Open No. 7-207211, Japanese Patent Application Laid-Open No. 8-259876, Japanese Laid-Open Patent Publication No. 10-300922, Japanese Laid-Open Patent Publication No. 11-14144, Japanese Laid-Open Patent Publication No. 11-174224, Japanese Laid-Open Patent Publication No. 2000-56118, Japanese Laid-Open Patent Publication No. 2003-233179, etc.
  • (C-1) An unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer with respect to the copolymer of the epoxy group-containing (meth) acrylate and another radical polymerizable monomer.
  • an alkali-soluble resin hereinafter referred to as “resin (C-1)” obtained by adding a polybasic acid anhydride to at least a part of a hydroxyl group generated by the addition reaction or the hydroxyl group generated by the addition reaction.
  • (C-2) Carboxyl group-containing linear alkali-soluble resin (C-2) (hereinafter sometimes referred to as “resin (C-2)”)
  • C-3) A resin obtained by adding an epoxy group-containing unsaturated compound to the carboxyl group portion of the resin (C-2) (hereinafter sometimes referred to as “resin (C-3)”).
  • C-4) (Meth) acrylic resin (hereinafter sometimes referred to as “resin (C-4)”)
  • C-5) Epoxy acrylate resin having a carboxyl group (hereinafter sometimes referred to as “resin (C-5)”)
  • the resin (C-1) is particularly preferable, and the resin will be described below.
  • the resins (C-2) to (C-5) may be anything as long as they are dissolved by an alkaline developer and are soluble to the extent that the intended development processing is performed. This is the same as that described as the same item in Japanese Patent Application Laid-Open No. 2009-025813. The preferred embodiment is also the same.
  • (C-1) An unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer with respect to the copolymer of the epoxy group-containing (meth) acrylate and another radical polymerizable monomer.
  • an epoxy group Unsaturated in 10 to 100 mol% of the epoxy groups of the copolymer with respect to a copolymer of 5 to 90 mol% of (meth) acrylate and 10 to 95 mol% of other radical polymerizable monomer examples thereof include a resin obtained by adding a monobasic acid, or an alkali-soluble resin obtained by adding a polybasic acid anhydride to 10 to 100 mol% of a hydroxyl group generated by the addition reaction.
  • epoxy group-containing (meth) acrylate examples include glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. ) Acrylate glycidyl ether and the like. Of these, glycidyl (meth) acrylate is preferred. These epoxy group-containing (meth) acrylates may be used alone or in combination of two or more.
  • the other radical polymerizable monomer copolymerized with the epoxy group-containing (meth) acrylate is not particularly limited as long as the effects of the present invention are not impaired.
  • vinyl aromatics, dienes, (meth) Examples include acrylic acid esters, (meth) acrylic acid amides, vinyl compounds, unsaturated dicarboxylic acid diesters, monomaleimides, and the like, and in particular, mono (meth) having a structure represented by the following formula (7) Acrylate is preferred.
  • the repeating unit derived from mono (meth) acrylate having a structure represented by the following formula (7) contains 5 to 90 mol% of repeating units derived from “other radical polymerizable monomers”. Those containing 10 to 70 mol% are more preferable, and those containing 15 to 50 mol% are particularly preferable.
  • R 89 represents a hydrogen atom or a methyl group
  • R 90 represents a structure represented by the following formula (8).
  • R 91 to R 98 each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 96 and R 98 may be connected to each other to form a ring.
  • the ring formed by connecting R 96 and R 98 is preferably an aliphatic ring, which may be saturated or unsaturated, and preferably has 5 to 6 carbon atoms.
  • the mono (meth) acrylate which has a structure represented by the said Formula (8) may be used individually by 1 type, and may use 2 or more types together.
  • the heat resistance and strength excellent in the colored resin composition can be improved.
  • the content of the repeating unit derived from at least one selected from the above monomer group is preferably 1 to 70 mol%, more preferably 3 to 50 mol%.
  • the copolymer of the epoxy group-containing (meth) acrylate and the other radical polymerizable monomer may include 5 to 90 mol% of repeating units derived from the epoxy group-containing (meth) acrylate, and the like. Are preferably composed of 10 to 95 mol% of repeating units derived from the radical polymerizable monomer, more preferably 20 to 80 mol% of the former and 80 to 20 mol% of the latter, and 30 to Those composed of 70 mol% and the latter 70 to 30 mol% are particularly preferred.
  • the addition amount of the polymerizable component and alkali-soluble component described later is sufficient, and the heat resistance and the strength of the film are sufficient, which is preferable.
  • the unsaturated monobasic acid (polymerizable component) and further the polybasic acid anhydride (alkali-soluble component) are reacted with the epoxy group portion of the epoxy group-containing copolymer synthesized as described above.
  • unsaturated monobasic acid added to an epoxy group a well-known thing can be used,
  • unsaturated carboxylic acid which has an ethylenically unsaturated double bond is mentioned.
  • Specific examples include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, ⁇ -position substituted with a haloalkyl group, an alkoxyl group, a halogen atom, a nitro group, or a cyano group.
  • monocarboxylic acids such as (meth) acrylic acid. Of these, (meth) acrylic acid is preferred. These may be used alone or in combination of two or more. By adding such components, polymerizability can be imparted to the binder resin used in the present invention.
  • These unsaturated monobasic acids are usually added to 10 to 100 mol% of the epoxy group of the copolymer, preferably 30 to 100 mol%, more preferably 50 to 100 mol%. It is preferable for it to be in the above range since the colored resin composition is excellent in stability over time.
  • a well-known method is employable as a method of adding unsaturated monobasic acid to the epoxy group of a copolymer.
  • a well-known thing can be used as a polybasic acid anhydride added to the hydroxyl group produced when an unsaturated monobasic acid is added to the epoxy group of a copolymer.
  • dibasic acid anhydrides such as maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, chlorendic anhydride; trimellitic anhydride, pyromellitic anhydride, benzophenone
  • examples thereof include anhydrides of three or more bases such as tetracarboxylic acid anhydride and biphenyltetracarboxylic acid anhydride.
  • succinic anhydride and tetrahydrophthalic anhydride are preferred.
  • These polybasic acid anhydrides may be used individually by 1 type, and may use 2 or more types together. By adding such a component, alkali solubility can be imparted to the binder resin used in the present invention.
  • polybasic acid anhydrides are usually added to 10 to 100 mol% of the hydroxyl group generated by adding an unsaturated monobasic acid to the epoxy group of the copolymer, preferably 20 to 90 mol. %, More preferably 30 to 80 mol%. Within the above range, the remaining film ratio and solubility during development are sufficient, which is preferable.
  • a well-known method is employable as a method of adding a polybasic acid anhydride to the said hydroxyl group.
  • glycidyl (meth) acrylate or a glycidyl ether compound having a polymerizable unsaturated group is added to a part of the generated carboxyl group. May be.
  • the structure of such a resin is described in, for example, Japanese Patent Application Laid-Open No. 8-297366 and Japanese Patent Application Laid-Open No. 2001-89533.
  • the above-mentioned binder resin (C-1) has a polystyrene equivalent weight average molecular weight (Mw) measured by GPC (gel permeation chromatography) of preferably 3000 to 100,000, particularly preferably 5000 to 50,000. Within the above range, heat resistance, film strength, and solubility in a developer are preferable. Further, as a measure of molecular weight distribution, the ratio of weight average molecular weight (Mw) / number average molecular weight (Mn) is preferably 2.0 to 5.0.
  • the acid value of the binder resin (C-1) is usually 10 to 200 mg-KOH / g, preferably 15 to 150 mg-KOH / g, more preferably 25 to 100 mg-KOH / g. If the acid value is too low, the solubility in the developer may be reduced. Conversely, if it is too high, film roughening may occur.
  • the content of the binder resin (C) in the colored resin composition is usually 0.1 to 80% by weight, preferably 1 to 60% by weight, based on the total solid content. Within the above range, the adhesion to the substrate is good, the permeability of the developer to the exposed area is moderate, and the surface smoothness and sensitivity of the pixels are good.
  • the colored resin composition of the present invention contains (B) a solvent as an essential component.
  • the solvent has a function of dissolving or dispersing each component contained in the colored resin composition and adjusting the viscosity.
  • the solvent (B) is not particularly limited as long as it can dissolve or disperse each component constituting the colored resin composition, and it is preferable to select a solvent having a boiling point in the range of 100 to 200 ° C. More preferably, it has a boiling point of 120 to 170 ° C.
  • solvents include the following. Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol-mono t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, methoxymethylpentanol, propylene Glycol monoalkyl ethers such as glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, tripropylene glycol monomethyl ether; Glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl
  • Ethers such as diethyl ether, dipropyl ether, diisopropyl ether, diamyl ether, ethyl isobutyl ether, dihexyl ether; Ketones such as acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone; Mono- or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin
  • solvents corresponding to the above include mineral spirits, Valsol # 2, Apco # 18 solvent, Apco thinner, Soal Solvent No. 1 and no. 2, Solvesso # 150, Shell TS28, Solvent, Carbitol, Ethylcarbitol, Butylcarbitol, Methylcellosolve, Ethylcellosolve, Ethylcellosolve acetate, Methylcellosolve acetate, Diglyme (all trade names) and the like.
  • solvents may be used alone or in combination of two or more.
  • glycol monoalkyl ethers are preferred from the viewpoint of the solubility of the dye (A) according to the present invention.
  • propylene glycol monomethyl ether is particularly preferable from the viewpoint of the solubility of various components in the composition.
  • glycolalkyl is further used as a solvent. It is more preferable to use a mixture of ether acetates. In a composition containing a pigment, glycol monoalkyl ethers have a high polarity, tend to aggregate the pigment, and may reduce storage stability such as increasing the viscosity of the colored resin composition. For this reason, it is preferable that the amount of glycol monoalkyl ether used is not excessively large.
  • the proportion of glycol monoalkyl ether in the solvent is preferably 5 to 50% by weight, more preferably 5 to 30% by weight. .
  • a solvent having a boiling point of 150 ° C. or higher it is also preferable to use a solvent having a boiling point of 150 ° C. or higher.
  • the content of such a high boiling point solvent is preferably 3 to 50% by weight, more preferably 5 to 40% by weight, and particularly preferably 5 to 30% by weight based on the total amount of the solvent (B). If the amount of the high-boiling solvent is too small, for example, a dye component may be precipitated and solidified at the tip of the slit nozzle to cause foreign matter defects, and if it is too much, the drying speed of the composition will be slowed down. There is a concern that the filter manufacturing process may cause problems such as tact defects in the vacuum drying process and pin marks of prebaking.
  • the solvent having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates or glycol alkyl ethers. In this case, a solvent having a boiling point of 150 ° C. or higher may not be included separately. .
  • the colored resin composition of the present invention may be used for color filter production by the ink jet method, but in color filter production by the ink jet method, the ink emitted from the nozzle is very small, from several to several tens pL. There is a tendency for the solvent to evaporate and the ink to concentrate and dry before landing on the periphery of the nozzle opening or in the pixel bank. In order to avoid this, it is preferable that the solvent has a high boiling point. Specifically, it is preferable that the solvent (B) contains a solvent having a boiling point of 180 ° C. or higher. In particular, it is preferable to contain a solvent having a boiling point of 200 ° C. or higher, particularly 220 ° C. or higher.
  • the high boiling point solvent whose boiling point is 180 degreeC or more is 50 weight% or more in (B) solvent.
  • the ratio of such a high boiling point solvent is less than 50% by weight, the effect of preventing evaporation of the solvent from the ink droplets may not be sufficiently exhibited.
  • the content of the (B) solvent is not particularly limited, but the upper limit is usually 99% by weight.
  • the concentration of each component excluding the (B) solvent becomes too small and may be inappropriate for forming a coating film.
  • the lower limit of the content of the solvent (B) is usually 75% by weight, preferably 80% by weight, and more preferably 82% by weight in consideration of viscosity suitable for coating.
  • the colored resin composition of the present invention preferably contains (D) a polymerizable monomer.
  • the polymerizable monomer is not particularly limited as long as it is a polymerizable low-molecular compound, but it may be an addition-polymerizable compound having at least one ethylenic double bond (hereinafter referred to as “ethylenic compound”). Is preferred).
  • the ethylenic compound is a compound having an ethylenic double bond that undergoes addition polymerization and cures by the action of a photopolymerization initiation component described later when the colored resin composition of the present invention is irradiated with actinic rays.
  • the (D) polymerizable monomer in this invention means the concept opposite to what is called a polymeric substance, and also includes a dimer, a trimer, and an oligomer other than a monomer in a narrow sense.
  • Examples of the ethylenic compound in the polymerizable monomer include unsaturated carboxylic acids such as (meth) acrylic acid; esters of monohydroxy compounds and unsaturated carboxylic acids; aliphatic polyhydroxy compounds and unsaturated carboxylic acids; Esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; Esterification of unsaturated carboxylic acids with polyvalent carboxylic acids and polyhydric hydroxy compounds such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds described above An ester obtained by the reaction; an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound and a (meth) acryloyl group-containing hydroxy compound;
  • Esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate , Pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) Examples include (meth) acrylic acid esters such as acrylate and glycerol (meth) acrylate.
  • the (meth) acrylic acid portion of these (meth) acrylic acid esters is replaced with an itaconic acid portion, a crotonic acid portion replaced with a crotonic acid portion, or a maleic acid ester replaced with a maleic acid portion, etc. Is mentioned.
  • ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid examples include hydroquinone di (meth) acrylate, resorcin di (meth) acrylate, pyrogallol tri (meth) acrylate and the like.
  • the ester obtained by the esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid and a polyvalent hydroxy compound may be a single substance or a mixture.
  • Representative examples are condensates of (meth) acrylic acid, phthalic acid, and ethylene glycol; condensates of (meth) acrylic acid, maleic acid, and diethylene glycol; condensation of (meth) acrylic acid, terephthalic acid, and pentaerythritol A condensate of (meth) acrylic acid, adipic acid, butanediol, and glycerin.
  • Examples of the ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth) acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic rings such as cyclohexane diisocyanate and isophorone diisocyanate.
  • Formula diisocyanates aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate, and (meth) acryloyl such as 2-hydroxyethyl (meth) acrylate and 3-hydroxy [1,1,1-tri (meth) acryloyloxymethyl] propane
  • aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate
  • (meth) acryloyl such as 2-hydroxyethyl (meth) acrylate and 3-hydroxy [1,1,1-tri (meth) acryloyloxymethyl] propane
  • examples of the ethylenic compound used in the present invention include (meth) acrylamides such as ethylene bis (meth) acrylamide; allyl esters such as diallyl phthalate; vinyl group-containing compounds such as divinyl phthalate. .
  • esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids are preferred, pentaerythritol or (meth) acrylic esters of dipentaerythritol are more preferred, and dipentaerythritol hexa (meth) acrylate is particularly preferred.
  • the ethylenic compound may be a monomer having an acid value.
  • the monomer having an acid value is, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and a non-aromatic carboxylic acid anhydride is reacted with an unreacted hydroxyl group of the aliphatic polyhydroxy compound.
  • a polyfunctional monomer having a group is preferable, and in this ester, the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol.
  • These monomers may be used alone, but since it is difficult to obtain a single compound in production, a mixture of two or more kinds may be used. Moreover, you may use together the polyfunctional monomer which does not have an acid group, and the polyfunctional monomer which has an acid group as (D) polymeric monomer as needed.
  • a preferable acid value of the polyfunctional monomer having an acid group is 0.1 to 40 mg-KOH / g, and particularly preferably 5 to 30 mg-KOH / g.
  • the development and dissolution characteristics are hardly deteriorated, and the production and handling are easy.
  • a more preferred polyfunctional monomer having an acid group is, for example, a mixture containing succinic acid ester of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentaacrylate as a main component. It is also possible to use this polyfunctional monomer in combination with another polyfunctional monomer.
  • the content of the polymerizable monomer (D) is usually 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more in the total solid content. Further, it is usually 80% by weight or less, preferably 70% by weight or less, more preferably 50% by weight or less, particularly preferably 40% by weight or less.
  • the ratio of the (D) polymerizable monomer to the (A) dye is usually 1% by weight or more, preferably 5% by weight or more, more preferably 10% by weight or more, and particularly preferably 20% by weight or more.
  • the amount is usually 200% by weight or less, preferably 100% by weight or less, and more preferably 80% by weight or less.
  • the colored resin composition of the present invention preferably contains (E) a photopolymerization initiation component and / or a thermal polymerization initiation component for the purpose of curing the coating film.
  • the curing method may be other than those using these initiators.
  • the colored resin composition of the present invention includes a resin having an ethylenic double bond as the component (C), or includes an ethylenic compound as the component (D), it directly absorbs light, or It is preferable to contain a photopolymerization initiating component that has a function of generating a polymerization active radical and / or a thermal polymerization initiating component that generates a polymerization active radical by heat.
  • the component (E) as a photopolymerization initiation component refers to a photopolymerization initiator (hereinafter also referred to as “(E1) component”), a polymerization accelerator (hereinafter, optionally referred to as “(E2) component”). ”)”
  • a sensitizing dye hereinafter also referred to as "(E3) component”).
  • the photopolymerization initiating component that may be contained in the colored resin composition of the present invention is usually (E1) a photopolymerization initiator, and (E2) a polymerization accelerator and (E3) sensitization that are added as necessary. It is a component having a function of generating a polymerization active radical by being used as a mixture with an additive such as a dye and directly absorbing light or being photosensitized to cause a decomposition reaction or a hydrogen abstraction reaction.
  • Examples of the photopolymerization initiator constituting the photopolymerization initiating component (E1) include titanocene derivatives described in JP-A Nos. 59-152396 and 61-151197. Hexaarylbiimidazole derivatives described in JP-A-10-300922, JP-A-11-174224, JP-A-2000-56118, and the like; -395053 and the like, halomethylated oxadiazole derivatives, halomethyl-s-triazine derivatives, N-aryl- ⁇ -amino acids such as N-phenylglycine, N-aryl- ⁇ -amino acid salts, N- Radical activators such as aryl- ⁇ -amino acid esters, ⁇ -aminoalkylphenone derivatives; Japanese Patent Application Laid-Open No. 2000-8006 It includes oxime ester derivatives and the like described in JP-like. Specific examples include photopolymerization initiators described in International Public
  • oxime ester derivatives examples include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (o-benzoyloxime), ethanone, 1- [9-ethyl-6- ( 2-methylbenzoyl) -9H-carbazol-3-yl], 1- (o-acetyloxime), and the like.
  • benzoin alkyl ethers anthraquinone derivatives
  • acetophenone derivatives such as 2-methyl- (4′-methylthiophenyl) -2-morpholino-1-propanone, 2-ethylthioxanthone, 2,4-diethylthioxanthone, etc.
  • examples also include thioxanthone derivatives, benzoate derivatives, acridine derivatives, phenazine derivatives, anthrone derivatives and the like.
  • ⁇ -aminoalkylphenone derivatives ⁇ -aminoalkylphenone derivatives, thioxanthone derivatives, and oxime ester derivatives are more preferable.
  • oxime ester derivatives are preferable.
  • Examples of the (E2) polymerization accelerator used as necessary include N, N-dialkylaminobenzoic acid alkyl esters such as N, N-dimethylaminobenzoic acid ethyl ester; 2-mercaptobenzothiazole, 2-mercapto Examples include mercapto compounds having a heterocyclic ring such as benzoxazole and 2-mercaptobenzimidazole; mercapto compounds such as aliphatic polyfunctional mercapto compounds.
  • (E3) a sensitizing dye is used for the purpose of increasing the sensitivity as required.
  • the sensitizing dye an appropriate one is used depending on the wavelength of the image exposure light source.
  • xanthene described in JP-A-4-221958 and JP-A-4-219756 A coumarin dye having a heterocyclic ring described in JP-A-3-239703, JP-A-5-289335, etc .; JP-A-3-239703, JP 3-ketocoumarin dyes described in each publication of JP-A-5-289335; pyromethene dyes described in JP-A-6-19240, etc .; JP-A 47-2528, JP Japanese Unexamined Patent Publication No.
  • Japanese Patent Publication No. 45-37377 Japanese Unexamined Patent Publication No. 48-84183, Japanese Unexamined Patent Publication No. 52-112681, Japanese Unexamined Patent Publication No. 58. No. 15503, Japanese Unexamined Patent Publication No. 60-88005, Japanese Unexamined Patent Publication No. 59-56403, Japanese Unexamined Patent Publication No. 2-69, Japanese Unexamined Patent Publication No. 57-168088, Japanese Special Examples thereof include dyes having a dialkylaminobenzene skeleton described in JP-A-5-107761, JP-A-5-210240, JP-A-4-288818, and the like.
  • the sensitizing dye may also be used alone or in combination of two or more.
  • the content of these (E) photopolymerization initiating components is usually 0.1% by weight or more, preferably 0.2% by weight or more, more preferably 0.8% by weight in the total solid content. It is 5% by weight or more, usually 40% by weight or less, preferably 30% by weight or less, more preferably 20% by weight or less. Within the above range, it is preferable in that the sensitivity to the exposure light is good and the solubility of the unexposed portion in the development is good.
  • thermal polymerization initiation component Specific examples of the thermal polymerization initiation component that may be contained in the colored resin composition of the present invention include azo compounds, organic peroxides, hydrogen peroxide, and the like. Of these, azo compounds are preferably used. More specifically, for example, a thermal polymerization initiating component described in International Publication No. 2009/107734 can be used. These thermal polymerization initiating components may be used alone or in combination of two or more.
  • the colored resin composition of the present invention comprises a surfactant, an organic carboxylic acid and / or an organic carboxylic acid anhydride, a thermosetting compound, a plasticizer, a thermal polymerization inhibitor, a storage stabilizer, a surface It may contain a protective agent, an adhesion improver, a development improver, and the like. Moreover, when it contains the below-mentioned (F) pigment, you may contain a dispersing agent and a dispersing aid.
  • these optional components for example, various compounds described in Japanese Patent Application Laid-Open No. 2007-113000 can be used.
  • the colored resin composition of the present invention may contain (F) a pigment within a range not impairing the effects of the present invention for the purpose of improving the heat resistance of the obtained color filter.
  • pigments for example, when forming color filter pixels, pigments of various colors such as blue and purple can be used.
  • examples of the chemical structure include organic pigments such as phthalocyanine, quinacridone, benzimidazolone, dioxazine, indanthrene, and perylene.
  • various inorganic pigments can be used.
  • specific examples of usable pigments are indicated by pigment numbers.
  • blue pigments examples include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.
  • a blue copper phthalocyanine pigment is preferable, and examples of the copper phthalocyanine pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6 and the like are preferable, and C.I. I. Pigment Blue 15: 6.
  • the colored resin composition of the present invention contains a blue pigment, it is 80% by weight or more, particularly 90% by weight or more, especially 95 to 100% by weight, based on the total content of the blue pigment.
  • I. Pigment Blue 15: 6 is preferable.
  • Examples of purple pigments include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
  • a purple dioxazine pigment is preferable, and as the dioxazine pigment, C.I. I. Pigment Violet 19 and 23 are preferable, and C.I. I. Pigment Violet 23. Therefore, when the colored resin composition of the present invention contains a violet pigment, it is 80% by weight or more, particularly 90% by weight or more, especially 95 to 100% by weight, based on the total content of the violet pigment.
  • I. Pigment Violet 23 is preferable. These may be used alone or in a combination of two or more in any combination and ratio.
  • the (F) pigment used in the colored resin composition of the present invention preferably has a small average primary particle diameter from the viewpoint of forming a high-contrast pixel.
  • the average primary particle diameter is 40 nm or less. Is preferable, and it is more preferable that it is 35 nm or less.
  • the average primary particle size is preferably 40 nm or less, more preferably 35 nm or less, and still more preferably 20 to 30 nm.
  • the average primary particle size is preferably 40 nm or less, more preferably 25 to 35 nm. From the viewpoint that the pigment is less likely to aggregate in the colored resin composition, it is preferable that the average primary particle size is not too small.
  • the average primary particle size of the (F) pigment is a value measured and calculated by the following method.
  • (F) a pigment is ultrasonically dispersed in chloroform, dropped onto a collodion film-attached mesh, dried, and a primary particle image of the pigment is obtained by observation with a transmission electron microscope (TEM). From this image, the particle diameter of each pigment particle is determined for a plurality of (usually about 200 to 300) pigment particles, where the diameter of each pigment particle is equivalent to an area circle equivalent diameter converted to the diameter of a circle having the same area.
  • the number average value is calculated according to the following formula to obtain the average particle size.
  • the particle diameter of each pigment particle X 1, X 2, X 3, X 4, ⁇ , X i, ⁇ X m
  • the content of the pigment in the colored resin composition is usually 80% by weight or less, preferably 50% by weight or less in the total solid content.
  • content with respect to 100 weight part of said (A) dye is 2000 weight part or less normally, Preferably it is 1000 weight part or less.
  • the colored resin composition of the present invention contains (F) a pigment
  • the dispersant in the present invention is not particularly limited as long as the pigment is dispersed and can maintain stability.
  • cationic, anionic, nonionic or amphoteric dispersants can be used, but polymer dispersants are preferred.
  • Specific examples include block copolymers, polyurethanes, polyesters, alkylammonium salts or phosphate esters of polymer copolymers, and cationic comb graft polymers. Of these dispersants, block copolymers, polyurethanes, and cationic comb graft polymers are preferred.
  • a block copolymer is preferable, and among them, a block copolymer composed of an A block having solvophilicity and a B block having a functional group containing a nitrogen atom is preferable.
  • the B block having a nitrogen atom-containing functional group includes a unit structure having a quaternary ammonium base and / or an amino group in the side chain, while the solvophilic A block includes a quaternary ammonium. Examples include a unit structure having no base and amino group.
  • the B block constituting the acrylic block copolymer has a unit structure having a quaternary ammonium base and / or an amino group, and has a pigment adsorption function. Further, when the B block has a quaternary ammonium base, the quaternary ammonium base may be directly bonded to the main chain, but may be bonded to the main chain via a divalent linking group. Good. Examples of such a block copolymer include those described in Japanese Patent Application Laid-Open No. 2009-025813. Moreover, the colored resin composition of the present invention may contain a dispersant other than those described above. Examples of other dispersants include those described in Japanese Patent Application Laid-Open No. 2006-343648, for example.
  • the content of the dispersant in the total solid content is 2 to 1000% by weight of the total content of the (F) pigment, In particular, it is preferably used so as to be in the range of 5 to 500% by weight, particularly 10 to 250% by weight. Within the above range, good pigment dispersibility can be ensured without affecting the heat resistance of the compounds (I) to (IV), and the pigment dispersion stability will be better. Is preferable.
  • the colored resin composition can be prepared by an appropriate method.
  • the (A) dye and (C) binder resin are combined with the (B) solvent and optional components used as necessary. It can be prepared by mixing.
  • (F) pigment as (A) dye
  • (A) dye containing (F) pigment is present in a solvent, in the presence of a dispersing agent and, if necessary, a dispersing aid.
  • (C) A part of the binder resin, for example, a paint shaker, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, and the like are mixed and dispersed while being pulverized to prepare a colored dispersion.
  • a dye for example, a paint shaker, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, and the like are mixed and dispersed while being pulverized to prepare a colored dispersion.
  • a dye for example, a paint shaker, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, and the like are mixed and dispersed while being pulverized to prepare a colored dispersion.
  • a dye for example, a paint shaker, a sand grinder, a ball mill, a roll mill, a stone mill
  • the colored resin composition of the present invention is usually in a state where all the constituent components are dissolved or dispersed in a solvent. Such a colored resin composition is supplied onto a substrate to form components such as a color filter, a liquid crystal display device, and an organic EL display.
  • a color filter a liquid crystal display device
  • an organic EL display a display of an organic EL.
  • the color filter of the present invention has a pixel formed from the colored resin composition of the present invention.
  • the method for forming the color filter of the present invention will be described below.
  • the pixel of the color filter can be formed by various methods. Here, although the case where it forms by the photolithographic method using a photopolymerizable colored resin composition is demonstrated to an example, a manufacturing method is not limited to this. First, on the surface of the substrate, if necessary, a black matrix is formed so as to partition a portion for forming pixels, and after applying the colored resin composition of the present invention on this substrate, pre-baking is performed. The solvent is evaporated to form a coating film.
  • each of red, green, and blue A color filter can be manufactured by forming a pixel pattern.
  • the substrate used for forming the pixels is not particularly limited as long as it is transparent and has an appropriate strength.
  • polyester resin, polyolefin resin, polycarbonate resin, acrylic resin, thermoplastic resin examples thereof include a sheet made, an epoxy resin, a thermosetting resin, and various glasses.
  • these substrates may be appropriately subjected to pretreatment as desired, such as thin film formation treatment with a silane coupling agent or urethane resin, surface treatment such as corona discharge treatment or ozone treatment, if desired.
  • a spinner method, a wire bar method, a flow coating method, a slit and spin method, a die coating method, a roll coating method, a spray coating method, and the like can be given.
  • the thickness of the coating film is usually 0.2 to 20 ⁇ m, preferably 0.5 to 10 ⁇ m, particularly preferably 0.8 to 5.0 ⁇ m as the film thickness after drying. Within the above range, it is preferable in that the gap can be easily adjusted in the pattern development or liquid crystal cell forming step, and a desired color can be easily expressed.
  • the radiation used in the exposure for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used, and radiation having a wavelength in the range of 190 to 450 nm is preferable.
  • the light source for using radiation having a wavelength of 190 to 450 nm used for image exposure is not particularly limited.
  • a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp Lamp light sources such as medium pressure mercury lamp, low pressure mercury lamp, carbon arc, fluorescent lamp; laser light sources such as argon ion laser, YAG laser, excimer laser, nitrogen laser, helium cadmium laser, semiconductor laser, and the like.
  • An optical filter can also be used when used by irradiating light of a specific wavelength.
  • the exposure dose of radiation is preferably 10 to 10,000 J / m 2 .
  • alkaline developer examples include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, Inorganic alkaline compounds such as potassium phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide; mono-di- or tri-ethanolamine, mono-di-, or tri -Methylamine, mono-, di-, or tri-ethylamine, mono-, or diisopropylamine, n-butylamine, mono-, di-, or tri-isopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium Hydroxide (TMAH)
  • TMAH tetramethylammonium Hydroxide
  • a water-soluble organic solvent such as isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, diacetone alcohol, or the like can be added to the alkali developer. In addition, it is usually washed with water after alkali development.
  • a water-soluble organic solvent such as isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, diacetone alcohol, or the like
  • the development processing method any method such as an immersion development method, a spray development method, a brush development method, and an ultrasonic development method can be used.
  • the development conditions are preferably 5 to 300 seconds at room temperature (23 ° C.).
  • the development temperature is usually 10 ° C. or higher, especially 15 ° C. or higher, more preferably 20 ° C. or higher, and usually 50 ° C. or lower, especially 45 ° C. or lower, more preferably 40 ° C. or lower. Is preferred.
  • the developing method can be any one of immersion developing method, spray developing method, brush developing method, ultrasonic developing method and the like.
  • a transparent electrode such as ITO is formed on the image as it is and used as a part of a component such as a color display or a liquid crystal display device.
  • a top coat layer such as polyamide or polyimide can be provided on the image as necessary.
  • the transparent electrode may not be formed.
  • ribs may be formed.
  • a column structure (photo spacer) by a photolithography method may be formed instead of the bead dispersion type spacer.
  • the liquid crystal display device of the present invention uses the above-described color filter of the present invention.
  • the liquid crystal display device of the present invention can be formed by the method described in “Liquid Crystal Device Handbook” (Nikkan Kogyo Shimbun, September 29, 1989, Japan Society for the Promotion of Science 142nd Committee).
  • Organic EL display When producing an organic EL display including the color filter of the present invention, for example, as shown in FIG. 1, on a blue color filter in which a blue pixel 20 is formed on a transparent support substrate 10 by the colored resin composition of the present invention.
  • a multicolor organic EL element 100 is manufactured by laminating the organic light-emitting body 500 through the organic protective layer 30 and the inorganic oxide film 40.
  • a transparent anode 50, a hole injection layer 51, a hole transport layer 52, a light emitting layer 53, an electron injection layer 54, and a cathode 55 are sequentially formed on the upper surface of the color filter.
  • a method of adhering the organic light-emitting body 500 formed on another substrate onto the inorganic oxide film 40 can be used.
  • the organic EL element 100 manufactured as described above can be applied to both a passive drive type organic EL display and an active drive type organic EL display.
  • the binder resin a thus obtained had a weight average molecular weight Mw measured by GPC of about 15000 in terms of polystyrene and an acid value of 78 mgKOH / g.
  • the structure of the binder resin a was as shown below (polymer compound containing the following four types of repeating units).
  • Reaction 6 Compound 9 (2.56 g, 23.9 mmol), Compound 10 (1,1,1-trifluoro-4-iodo) butane (TCI, 12.5 g, 52.5 mmol), potassium carbonate (7.25 g) 52.5 mmol) and N-methyl-2-pyrrolidone (50 ml) were stirred at 100 ° C. for 5 hours, then cooled to room temperature, diluted with ethyl acetate, filtered with suction and washed with ethyl acetate. The mother liquor was washed twice with water and then concentrated under reduced pressure. The oil was dissolved in toluene, washed 3 times with water, and washed with saturated brine.
  • Reaction 7 Thionyl chloride (14 ml) was added to a mixture of compound 11 (25 g) and toluene (100 ml), stirred at 80 ° C. for 1 hour, and then concentrated under reduced pressure to obtain acid chloride.
  • a mixture of anhydrous aluminum chloride (20.4 g) and 1,2-dichloroethane (100 ml) was cooled in an ice bath, and a solution of acid chloride in 1,2-dichloroethane (50 ml) was added dropwise. After stirring for 15 minutes, Compound 10 (21.1 g) was added dropwise, brought to room temperature, and then poured into ice water.
  • the pH was adjusted to 10 or more with 4N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform.
  • the chloroform layer was washed with 1N aqueous sodium hydroxide solution and filtered through Celite to remove insolubles. This was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Reaction 8 Phosphorus oxychloride (1.4 ml) was added to a mixture of compound A (3.38 g), compound 12 (1.71 g) and toluene (15 ml), and the mixture was stirred at 120 ° C. for 2 hours. After cooling to room temperature, 1N hydrochloric acid was added, stirred for 15 minutes, and extracted with chloroform. The chloroform layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • Reaction 9 Compound 13 (1.06 g) and acid blue 80 (0.70 g) were dissolved in methanol and concentrated under reduced pressure. The obtained solid was washed with a methanol / water (1/2) mixture solvent to obtain Compound D4 (1.34 g).
  • Reaction 10 A solution of compound 17 (10 g) in N, N-dimethylformamide (100 ml) was cooled in an ice bath, sodium hydride (60%, 4.3 g) was added, and after stirring for a while, compound 18 (6.5 g) ) was added in small portions. After stirring at room temperature for 5 hours, water was added, extracted with dichloromethane, and purified by silica gel column chromatography to obtain compound B (3.1 g).
  • ⁇ in the columns of formulas (1) to (3) means “applicable” in the range of each formula, and ⁇ means “not applicable” in the range of each formula.
  • * 2 In Table 1 above, ⁇ in the column of molecular weight means “applicable” in the range of molecular weight 150 to 600, and ⁇ means “not applicable” in the range of molecular weight 150 to 600.
  • the above dyes and other components were mixed at the ratios shown in Table 3 to prepare a colored resin composition.
  • the mixture was stirred for 1 hour or more until the dye was sufficiently dissolved, and finally filtered through a 5 ⁇ m piece filter to remove foreign matters.
  • the spectral transmittance was measured as described above, and the color difference ( ⁇ E * ab) from the chromaticity before baking, that is, the heat resistance was measured. Is shown in Table 4 below.
  • the pixels formed using the colored resin composition of the present invention have no significant reduction in luminance and have dramatically improved heat resistance.

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  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optical Filters (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine colorée qui répond aux exigences en termes de résistance thermique requises lors d'étapes relevant de la production d'un affichage couleur. L'invention concerne également, suite à l'utilisation de cette composition de résine colorée, un filtre couleur ayant une excellente pureté des couleurs et une excellente transmittance des pixels bleus, ainsi qu'un affichage EL organique et un dispositif d'affichage à cristaux liquides possédant une bonne pureté de couleur bleu. La composition de résine colorée comprend (A) un colorant, (B) un solvant, et (C) une résine liante, et le colorant (A) comprend un composé qui est un contre-ion de colorants anioniques et cationiques de disulfonylimide.
PCT/JP2011/064082 2010-06-23 2011-06-20 Composition de résine colorée, filtre couleur, dispositif d'affichage à cristaux liquides et affichage el organique Ceased WO2011162217A1 (fr)

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JP2012521468A JP5915526B2 (ja) 2010-06-23 2011-06-20 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌディスプレイ
KR1020127022592A KR20130091629A (ko) 2010-06-23 2011-06-20 착색 수지 조성물, 컬러 필터, 액정 표시 장치 및 유기 ｅｌ 디스플레이

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JP2014080584A (ja) * 2012-09-28 2014-05-08 Jsr Corp 着色組成物、カラーフィルタ及び表示素子
WO2015080217A1 (fr) * 2013-11-29 2015-06-04 三菱化学株式会社 Composition de résine colorée, filtre couleur, dispositif d'affichage à cristaux liquides, dispositif d'affichage électroluminescent organique
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JP2016075829A (ja) * 2014-10-08 2016-05-12 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物およびカラーフィルタ
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WO2013161616A1 (fr) * 2012-04-23 2013-10-31 大日本印刷株式会社 Dispersion d'un matériau coloré pour un filtre couleur, composition de résine colorée pour un filtre couleur, filtre couleur, dispositif d'affichage à cristaux liquides, et dispositif d'affichage électroluminescent organique
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CN102947733A (zh) 2013-02-27
TW201300468A (zh) 2013-01-01
JPWO2011162217A1 (ja) 2013-08-22
JP2016176076A (ja) 2016-10-06
KR20130091629A (ko) 2013-08-19
TWI486404B (zh) 2015-06-01

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