CN104813233A - Photosensitive resin composition for color filter and color filter using same - Google Patents

Photosensitive resin composition for color filter and color filter using same Download PDF

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Publication number
CN104813233A
CN104813233A CN201380060623.1A CN201380060623A CN104813233A CN 104813233 A CN104813233 A CN 104813233A CN 201380060623 A CN201380060623 A CN 201380060623A CN 104813233 A CN104813233 A CN 104813233A
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CN
China
Prior art keywords
unsubstituted
substituted
color filter
resin composition
photosensitive resin
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CN201380060623.1A
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Chinese (zh)
Inventor
金南光
崔世荣
形敬熙
李有珍
韩圭奭
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Cheil Industries Inc
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Cheil Industries Inc
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Publication of CN104813233A publication Critical patent/CN104813233A/en
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
    • C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—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
    • 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
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

The invention discloses a photosensitive resin composition for a color filter including (A) a coloring agent containing perylene-based dye indicated by chemical formula 1, (B) an acryl-based binder resin, (c) a photopolymerization initiator, (D) a photopolymerizable monomer, and (E) a solvent; and color filter using the same.

Description

For the photosensitive resin composition of color filter and the color filter of the described photosensitive resin composition of use
Technical field
The present invention relates to the color filter of a kind of photosensitive resin composition for color filter and the described photosensitive resin composition of use.
Background technology
In the recent period, because the use of big screen LCD (liquid crystal display, LCD) significantly increases, so more and more need the performance improveing it.Because color filter is the most important factor realizing color in multiple parts of liquid crystal display, so there is the active research increasing color filter process window for throughput rate.In addition, in order to increase the colour purity of large-size screen monitors liquid crystal display (LCD), the photosensitive resin composition prepared by increasing colorant concentration is used to manufacture color filter.Therefore, need photosensitive resin composition to have low developing powder to increase throughput rate and output in a manufacturing process, although and need still have splendid susceptibility when being seldom exposed to light.
Color filter uses photosensitive resin composition, is manufactured by methods such as dyeing, electrophoretic deposition (electrophoreticdeposition, EPD), printing, pigment dispersions, wherein by three kinds or be greater than three kinds of colors and be applied in transparent substrates.In the recent period, pigment dispersion method is adopted more energetically.
But the color filter manufactured by pigment dispersion method has restriction because of pigment particle size in brightness and contrast ratio.
On the other hand, imageing sensor is the part for filmed image in portable phone camera or digital still camera (digital stillcamera, DSC).Depending on manufacturing process and methods for using them, imageing sensor can be divided into charge-coupled device (CCD) (charge-coupled device, CCD) imageing sensor and complementary metal oxide semiconductor (CMOS) (complementary metal oxide semiconductor, CMOS) imageing sensor.The up-to-date color filter for charge-coupled device (CCD) or complementary metal oxide semiconductor (CMOS) be installed in color imaging device has 2 microns or be less than the pattern dimension of 2 microns, is 1/100 to 1/200 of the pattern dimension of the conventional color filter pattern for LCD.Therefore, resolution increase and pattern residue to reduce be the key factor of decision maker performance.
In order to form the pattern of the color filter for imageing sensor, need a kind of photosensitive resin composition by forming compared with small-particle.
Summary of the invention
Technical matters
One embodiment of the present of invention provide a kind of photosensitive resin composition for color filter, and it has high-dissolvability and splendid chemical resistance.
The color filter that another embodiment of the present invention provides a kind of use to manufacture for the photosensitive resin composition of color filter.
Technical solution
One embodiment of the present of invention provide a kind of photosensitive resin composition for color filter, comprise (A) colorant, comprise by following chemical formula 1 Biao Shi perylene class dyestuff; (B) acryl based binder resin; (C) photopolymerization initiator; (D) photopolymerizable monomer; And (E) solvent.
[chemical formula 1]
(in chemical formula 1,
R 1to R 10be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylene oxide group, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C2 to C20 alkenylene, substituted or unsubstituted C2 to C20 alkynylene, substituted or unsubstituted C3 to C20 cycloalkylidene, the sub-cycloalkenyl group of substituted or unsubstituted C3 to C20, the sub-cycloalkynyl radical of substituted or unsubstituted C3 to C20, the sub-Heterocyclylalkyl of substituted or unsubstituted C2 to C20, the sub-heterocycloalkenyl of substituted or unsubstituted C2 to C20, the sub-heterocycle alkynyl of substituted or unsubstituted C2 to C20, substituted or unsubstituted C6 to C30 arlydene, the sub-aryloxy group (aryloxylene group) of substituted or unsubstituted C6 to C30,-S-or-S-S-, its restrictive condition is R 1to R 10in at least one be-S-or-S-S-, and
R 11to R 20be same to each other or different to each other, and be hydrogen atom, halogen atom, cyano group, hydroxyl, ether, amido or amine deriveding group, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 thiazolinyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 naphthenic base, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl radical, substituted or unsubstituted C2 to C20 Heterocyclylalkyl, substituted or unsubstituted C2 to C20 heterocycloalkenyl, substituted or unsubstituted C2 to C20 heterocycle alkynyl, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C6 to C30 aryloxy group.)
Perylene class dyestuff can comprise at least one that select from the compound represented by following chemical formula 2 and chemical formula 3.
[chemical formula 2]
[chemical formula 3]
(in chemical formula 2 and chemical formula 3,
R 21and R 25be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C6 to C30 arlydene ,-S-or-S-S-, its restrictive condition is R 21and R 25in at least one be-S-or-S-S-,
R 22and R 26substituted or unsubstituted C1 to C20 alkylidene independently of one another,
R 23, R 24, R 27, R 28, R 29, R 30and R 32substituted or unsubstituted C1 to C20 alkyl independently of one another,
R 31-S-or-S-S-,
N 1to n 3the integer in 0 to 5 scopes independently of one another.)
Colorant can comprise pigment further.
Pigment can comprise C.I. red pigment 254, C.I. red pigment 255, C.I. red pigment 264, C.I. red pigment 270, C.I. red pigment 272, C.I. red pigment 177, C.I. red pigment 89, C.I. yellow uitramarine 139, C.I. yellow uitramarine 138, C.I. yellow uitramarine 150 or its combination.
It is 1: 10 to 10: 1 perylene class dyestuff and pigment that colorant can comprise weight ratio.
Photosensitive resin composition for color filter can comprise 0.01 % by weight to 60 % by weight colorant (A); 0.5 % by weight to 20 % by weight acryl based binder resin (B); 0.1 % by weight to 20 % by weight photopolymerization initiator (C); 0.5 % by weight to 20 % by weight photopolymerizable monomer (D); And balance solvent (E).
The color filter that another embodiment of the present invention provides a kind of use to manufacture for the photosensitive resin composition of color filter.
Other embodiments of the invention comprise in the following specific embodiments.
Beneficial effect
Photosensitive resin composition for color filter has high-dissolvability and splendid chemical resistance, and therefore can be effectively applied to color filter.
Best mode
Hereinafter, embodiments of the invention are described in detail.But these embodiments are exemplary, and the present invention is not limited to this, and the present invention is only limited by claim.
In this manual, when not providing specifically defined to otherwise, " be substituted " and refer to by halogen atom (F, Cl, Br, I), hydroxyl, C1 to C20 alkoxy, nitro, cyano group, amido, imino group, azido, amidino groups, diazanyl, hydrazono-, carbonyl, carbamyl, mercapto, ester group, ether, carboxyl or its salt, sulfonic group or its salt, phosphoric acid or its salt, C1 to C20 alkyl, C2 to C20 thiazolinyl, C2 to C20 alkynyl, C6 to C30 aryl, C3 to C20 naphthenic base, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl radical, C2 to C20 Heterocyclylalkyl, C2 to C20 heterocycloalkenyl, C2 to C20 heterocycle alkynyl or its combination at least one substituting group instead of compound at least one hydrogen replace.
In this manual, when not providing specifically defined to otherwise, " amine deriveding group " refers to NH in amine 2at least one hydrogen replaced by halogen atom, hydroxyl, carboxyl, ether, sulfonate group, sulfonic group, sulfoamido, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy or substituted or unsubstituted C6 to C30 aryl.
In this manual, when not providing specifically defined to otherwise, " ether " refers to that ROR ' (wherein, R and R ' is same to each other or different to each other, and is substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 naphthenic base or substituted or unsubstituted C6 to C30 aryl).
In this manual, when not providing specifically defined to otherwise, " mixing " refers in ring compound, to comprise at least one heteroatoms N, O, S or P one.
In this manual, when not providing specifically defined to otherwise, " (methyl) acrylate " refers to " acrylate " and " methacrylate ".
(A) colorant, (B) acryl based binder resin, (C) photopolymerization initiator, (D) photopolymerizable monomer and (E) solvent is comprised according to the photosensitive resin composition for color filter of an embodiment.
(A) colorant
Colorant is by following chemical formula 1 Biao Shi perylene class dyestuff.
[chemical formula 1]
To solvent, there is splendid solubility by chemical formula 1 Biao Shi perylene class dyestuff.Yin Ci ， perylene class dyestuff has splendid compatibility with other component of the photosensitive resin composition being configured for color filter, and therefore contributes to the photosensitive resin composition for the preparation of color filter.
Specifically, in chemical formula 1, R 1to R 10be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylene oxide group, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C2 to C20 alkenylene, substituted or unsubstituted C2 to C20 alkynylene, substituted or unsubstituted C3 to C20 cycloalkylidene, the sub-cycloalkenyl group of substituted or unsubstituted C3 to C20, the sub-cycloalkynyl radical of substituted or unsubstituted C3 to C20, the sub-Heterocyclylalkyl of substituted or unsubstituted C2 to C20, the sub-heterocycloalkenyl of substituted or unsubstituted C2 to C20, the sub-heterocycle alkynyl of substituted or unsubstituted C2 to C20, substituted or unsubstituted C6 to C30 arlydene, the sub-aryloxy group of substituted or unsubstituted C6 to C30,-S-or-S-S-.Herein, R 1to R 10in at least one can be-S-or-S-S-.
R 1to R 10all the linking group of Lian Jie perylene compounds main chain, R 11to R 20end group, and R 1to R 10in at least one can be-S-or-S-S-linking group.Linking group can be hot degradable linking group.First, linking group is because of R 11to R 20end group can produce the high-dissolvability about a kind of solvent, and dissolves during the heat curing that secondly can be formed in color filter pattern, is separated subsequently, and therefore loses the solubility about other solvent, obtain splendid chemical resistance with end group.Therefore, when using according to an embodiment perylene compounds, solubleness about a kind of solvent increases, and the photosensitive resin composition that can contribute to for the preparation of color filter, but deterioration during being dissolved in the heat curing of color filter manufacturing process, and therefore can improve the chemical resistance about other solvent used in other technique.
Specifically, R 9and R 10in at least one can be-S-or-S-S-, or R 1to R 8in at least one can be-S-or-S-S-.
In chemical formula 1, R 11to R 20be same to each other or different to each other, and be hydrogen atom, halogen atom, cyano group, hydroxyl, ether, amido or amine deriveding group, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 thiazolinyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 naphthenic base, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl radical, substituted or unsubstituted C2 to C20 Heterocyclylalkyl, substituted or unsubstituted C2 to C20 heterocycloalkenyl, substituted or unsubstituted C2 to C20 heterocycle alkynyl, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C6 to C30 aryloxy group.
Wherein, R 11to R 18can be preferably hydrogen atom, and R 19and R 20may be the same or different and can be halogen atom, cyano group, hydroxyl, ether, amido or amine deriveding group, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 naphthenic base, substituted or unsubstituted C2 to C20 Heterocyclylalkyl, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C6 to C30 aryloxy group.Substituting group and solvent have high interaction, and can obtain the high-dissolvability about described solvent.
Perylene class dyestuff can comprise at least one that select from the compound represented by following chemical formula 2 and chemical formula 3 particularly.
[chemical formula 2]
[chemical formula 3]
In chemical formula 2, R 21and R 25be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C6 to C30 arlydene ,-S-or-S-S-, its restrictive condition is R 21and R 25in at least one be-S-or-S-S-.
In chemical formula 2, R 22and R 26can be substituted or unsubstituted C1 to C20 alkylidene independently of one another.
In chemical formula 2 and chemical formula 3, R 23, R 24, R 27, R 28, R 29, R 30and R 32can be substituted or unsubstituted C1 to C20 alkyl independently of one another.
In chemical formula 3, R 31can be-S-or-S-S-.
In chemical formula 3, n 1to n 3it can be each integer between 0 to 5.
Perylene class dyestuff can be orchil.
Perylene class dyestuff is because of the R in above-mentioned chemical formula 1 as described above 11to R 20end group and there is splendid organic solubility to solvent, and therefore not there is particle in solution state or there is the minimum particle that elementary diameter is less than or equal to a few nanometer, and be different from the high-durability of the pigment with particle.Yin Ru perylene class dyestuff can compensate the deterioration of contrast ratio and brightness, and the deterioration of contrast ratio and brightness is the problem of the pigment dispersion method mainly for the manufacture of color filter.
The thermal degradation temperature of perylene class dyestuff can be more than or equal to 250 DEG C, and specifically 250 DEG C to 500 DEG C.
Perylene class dyestuff can have about the solvent (that is, the solvent (E) hereinafter described) for the preparation of the photosensitive resin composition for color filter and is more than or equal to 2, and specifically 2 to 10 solubleness.Solubleness can be obtained by the amount of dye (gram) be dissolved in 100 grams of solvents.The when solubleness ， perylene class dyestuff had in described scope Dang perylene class dyestuff can guarantee with for the photosensitive resin composition of color filter in the compatibility of other component and dyeing property, and precipitation can be prevented.
Solvent can be specifically cyclohexanone, propylene glycol methyl ether acetate (propylene glycolmonomethylether acetate, PGMEA), ethyl lactate (ethyl lactate, EL), ethylene glycol ethyl ethers acetoacetic ester (ethylene glycol ethyl acetate, EGA), cyclohexanone (cyclohexanone) or its combination.
There is the color filter that described feature perylene class dyestuff can be effectively applied to for LCD, LED etc., in required hue coordinate, realize high brightness and high contrast ratio.
Perylene class dyestuff can with from the azo base class dyestuff for dyeing with select in oxa anthracenes dyestuff at least one together with use.
Colorant can comprise pigment Yi Ji perylene class dyestuff.
Pigment can comprise at least one that select from organic pigment and inorganic pigment.
Pigment can be two pyrrolopyrroles (dipyrrolopyrrole) pigment specifically, such as C.I. red pigment 254, C.I. red pigment 255, C.I. red pigment 264, C.I. red pigment 270 or C.I. red pigment 272; Pigment, such as C.I. red pigment 177 or C.I. red pigment 89; Isoindoline class pigment, such as C.I. yellow uitramarine 139; Quinoline yellow class pigment, such as C.I. yellow uitramarine 138; Nickel complex pigment, such as C.I. yellow uitramarine 150, and these pigment can for independent or be two kinds or be greater than the form of mixtures of two kinds.
Pigment can have the primary particle diameter of reduction.Specifically, this can comprise: hybrid pigment and water-soluble inorganic salt and wetting agent, and mediates in high pressure kneader (kneader) and pulverize described pigment composition primary particle diameter to be reduced to the method being less than 70 nanometers; Acid gelatinization method (acidpasting method), dissolve pigment in as the acid of sulfuric acid and by as described in pigment solution be added into poor solvent and pigment as described in deposition to reduce the primary diameter of pigment; Or dry grind pigment for a long time to reduce the method for the primary diameter of pigment by high speed sand mill, but be not limited to this.In addition, commercially available pigment is used can be good, as long as reduce primary particle diameter.
Pigment can have 30 nanometers to 70 nanometer primary particle diameter (D50).When pigment has the primary particle diameter in described scope, thermotolerance, chemical resistance, permanance etc. can be improved after formation pixel.
Pigment can be included in the photosensitive resin composition for color filter as dispersion liquid.Dispersible pigment dispersion can comprise pigment and solvent, spreading agent, adhesive resin etc.
Solvent can be Ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyglycol, cyclohexanone, propylene glycol monomethyl ether etc., and wherein preferably can use propylene glycol methyl ether acetate.
Spreading agent helps dispersed pigment, and can comprise nonionic, negative ion or cation dispersing agent.Specifically, spreading agent can be poly alkylene glycol or its ester, polyoxy alkene, polyol ester oxirane additive product, alcohol oxirane additive product, sulphonic acid ester, sulfonate, carboxylate, carboxylate, alkylamide oxirane additive product, alkyl amine etc., and they can separately in two kinds or be greater than two kinds form of mixtures use.
Adhesive resin can comprise acryl resin (comprising carboxyl), and the pattern improveing pixel is formed and the stability of dispersible pigment dispersion.
Pigment can have 10 nanometers to the primary particle diameter in 70 nanometer range.When pigment has the primary particle diameter in described scope, the stability in dispersible pigment dispersion and the resolution of pixel can be splendid.
The secondary particle diameter of pigment not by specific restriction, but can have the offspring diameter being less than or equal to 200 nanometers, and specifically when considering pixel resolution in 70 nanometers in 100 nanometer range.
Pigment can by the photosensitive resin composition total amount 0.1 % by weight to 30 % by weight for color filter, and specifically the amount of 1 % by weight to 20 % by weight is included.When comprising the pigment in described scope, dyeing property and developability are improved.
Perylene class dyestuff can mix with 1: 10 to 10: 1 weight ratio with pigment.When weight ratio is in described ratio ranges, high brightness and high contrast ratio can be obtained, and required color character can be realized.
Colorant can by the photosensitive resin composition total amount 0.01 % by weight to 60 % by weight for color filter, and specifically the amount of 0.1 % by weight to 40 % by weight is included.When comprising the colorant in described scope, high-dissolvability and splendid chemical resistance and high brightness and contrast ratio can be obtained.
(B) acryl based binder resin
Acryloyl class adhesive resin is the first ethene system unsaturated monomer and can the multipolymer of the second ethene system unsaturated monomer of copolymerization with it, and is the resin comprising at least one acryloyl class repetitive.
First ethene system unsaturated monomer is the ethene system unsaturated monomer comprising at least one carboxyl, and the example of described monomer comprises acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid or its combination.
First ethene system unsaturated monomer can by acryl based binder resin total amount 5 % by weight to 50 % by weight, and the amount specifically in 10 % by weight to 40 % by weight scopes is included.
Second ethene system unsaturated monomer can be aromatic ethenyl compound, as styrene, α-methyl styrene, vinyltoluene, vinyl benzene dimethyl cellosolve etc.; Unsaturated carboxylic ester compound, as (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) butyl acrylate, (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) acrylic acid 2-hydroxy butyl ester, (methyl) benzyl acrylate, (methyl) cyclohexyl acrylate, (methyl) phenyl acrylate etc.; Unsaturated carboxylic acid aminoalkyl ester compounds, as (methyl) acrylic acid 2-amino ethyl ester, (methyl) acrylic acid 2-dimethylamino ethyl ester etc.; Vinyl esters of carboxylic acids compound, as vinyl acetate, vinyl benzoate etc.; Unsaturated carboxylic acid epihydric alcohol ester compound, as (methyl) glycidyl acrylate etc.; Vinyl cyanide compound, as (methyl) vinyl cyanide etc.; Unsaturated acyl amines, as (methyl) acrylamide etc.; Deng, and can separately or in two kinds or be greater than two kinds form of mixtures use.
The particular instance of acryl based binder resin can be methacrylic acid/benzyl methacrylate multipolymer, methacrylic acid/benzyl methacrylate/styrol copolymer, methacrylic acid/benzyl methacrylate/HEMA multipolymer, methacrylic acid/benzyl methacrylate/styrene/methacrylic acid 2-hydroxyl methacrylate copolymers etc.; and be not limited to this, and these can separately in two kinds or be greater than two kinds of potpourris form use.
Acryl based binder resin can have 3,000 to 150, and 000, especially 5,000 to 50,000, and the weight average molecular weight more particularly in 20,000 to 30,000 scope.When acryl based binder resin has the weight average molecular weight in described scope, constituent can have and the splendid closed contact performance of substrate, good physical and chemical characteristic and suitable viscosity.
Acryl based binder resin can have 15 milligrams of KOH/ gram to 60 milligrams KOH/ gram, and the acid number specifically within the scope of 20 milligrams KOH/ gram to 50 milligrams KOH/ gram.When acryl based binder resin has the acid number in described scope, it can produce splendid pixel resolution.
Acryl based binder resin can by the photosensitive resin composition total amount 0.5 % by weight to 20 % by weight for color filter, and the amount specifically in 1 % by weight to 15 % by weight scope is included.When adhesive resin is included in the stable dispersion for pigment in dispersible pigment dispersion, the content of acryl based binder resin can reduce as much.When comprising the acryl based binder resin in described scope, constituent can have the crosslinked of splendid developing property and improvement, and therefore has excellent surface flatness when manufacturing color filter.
(C) photopolymerization initiator
Photopolymerization initiator can be any photopolymerization initiator of the photosensitive resin composition be such as generally used for for color filter, and can be acetophenone compounds, benzophenone compound, thioxanthones compounds, styrax compounds, compound in triazine class, oxime compound or its combination.
Acetophenone compounds can be 2,2 '-diethoxy acetophenone, 2,2 '-dibutoxy acetophenone, 2-hydroxy-2-methyl propiophenone, to tert-butyl group trichloroacetophenone, to tert-butyl group dichloroacetophenone, 4-chloro-acetophenone, 2,2 '-two chloro-4-metaphenoxy acetophenone, 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholinyl third-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-Ding-1-ketone etc.
Benzophenone compound can be benzophenone, benzoilbenzoate, benzoilbenzoate methyl esters, 4-phenyl benzophenone, dihydroxy benaophenonel, acrylated benzophenone, 4,4 '-bis-(dimethylamino) Benzophenone, 4,4 '-bis-(lignocaine) benzophenone, 4,4 '-dimethylamino benzopheone, 4,4 '-dichloro benzophenone, 3,3 '-dimethyl-2-methoxy benzophenone etc.
Thioxanthones compounds can be thioxanthones, 2-methyl thioxanthones, isopropyl thioxanthone, 2,4-diethyl thioxanthones, 2,4-diisopropylthioxanthone, CTX etc.
Styrax compounds can be styrax, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl Ketene dimethyl etc.
Compound in triazine class can be 2, 4, 6-trichloto-s-triazine, 2-phenyl 4, two (the trichloromethyl)-s-triazine of 6-, 2-(3 ', 4 '-dimethoxy-styryl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4 '-methoxyl naphthyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(p-methoxyphenyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(p-methylphenyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-xenyl 4, two (the trichloromethyl)-s-triazine of 6-, two (trichloromethyl)-6-styryl-s-triazine, 2-(naphthols-Ji)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-methoxynaphthol-Ji)-4, two (the trichloromethyl)-s-triazine of 6-, 2-4-trichloromethyl (piperonyl)-6-triazine, 2-4-trichloromethyl (4 '-methoxyl-styrene)-6-triazine etc.
Oxime compound can be O-acyl oxime compound, 2-(O-benzoyl oximes)-1-[4-(thiophenyl) phenyl]-1,2-acetyl caproyl, 1-(O-acetyl oxime)-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-base] ethyl ketone, O-carbethoxyl group-α-hydroxylamino-1-phenyl third-1-ketone etc.The particular instance of O-acyl oxime compound can be 1,2-acetyl caproyl, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholine-4-base-phenyl)-Ding-1-ketone, 1-(4-Phenylsulfanylphenyl)-butane-1,2-diketone 2-oxime-O-benzoic ether, 1-(4-Phenylsulfanylphenyl)-octane-1,2-diketone 2-oxime-O-benzoic ether, 1-(4-Phenylsulfanylphenyl)-Xin-1-ketoxime-O-acetic acid esters and 1-(4-Phenylsulfanylphenyl)-Ding-1-ketoxime-O-acetic acid esters etc.
Photopolymerization initiator can comprise carbazole compound, cyclohexadione compounds, boric acid sulfonium compounds, diazonium compounds, bisglyoxaline compounds etc. except foregoing photo-polymerization initiator.
Photopolymerization initiator can by the photosensitive resin composition total amount 0.1 % by weight to 20 % by weight for color filter, and the amount specifically in 1 % by weight to 10 % by weight scope is included.When comprising the photopolymerization initiator in described scope, by exposing and fully photopolymerization in for the Patternized technique of color filter, therefore susceptibility is strengthened, strengthen pattern linearity, strengthen the solubleness to solvent and storage stability, and unreacted initiator does not remain after photopolymerization, to prevent transmissivity deterioration.
(D) photopolymerizable monomer
Photopolymerizable monomer can be the multi-functional monomer having two or be greater than two hydroxyls.The particular instance of photopolymerizable monomer can be glycerine acrylate, dipentaerythritol acrylate, glycol diacrylate, triethylene glycol diacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediyl ester, neopentylglycol diacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol acrylate, pentaerythrite six acrylate, bisphenol a diacrylate, trimethylolpropane triacrylate, Epoxy Phenolic Acrylates, ethylene glycol dimethacrylate, dimethacrylate, TEGDMA, dimethacrylate, 1, 4-butanediol dimethylacrylate, 1, 6-hexanediol dimethacrylate etc.
Photopolymerizable monomer can by the photosensitive resin composition total amount 0.5 % by weight to 20 % by weight for color filter, and specifically the amount of 1 % by weight to 10 % by weight is included.When comprising the photopolymerizable monomer in described scope, for example, the clear formation during manufacture color filter of pattern flex point, therefore strengthens pattern characteristics and strengthens the developability to alkaline metal developing solution.
(E) solvent
The example of solvent can be alcohol, as methyl alcohol, ethanol etc.; Ether, as dichloroethyl ether, n-butyl ether, isoamyl ether, methyl phenylate, tetrahydrofuran etc.; Glycol ethers, as ethylene glycol monomethyl ether, ethylene glycol ethyl ether, propylene glycol monomethyl ether etc.; Cellosolve acetate, as methylcellosolve acetate, ethyl cellosolve acetate, ethylene glycol diethyl ether acetic acid esters etc.; Carbitol, as Methylethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol MEE, diethylene glycol diethyl ether etc.; Propylene glycol alkyl ether acetic acid ester, as propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid esters etc.; Aromatic series carbon hydrocarbon, as toluene, dimethylbenzene etc.; Ketone, as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-positive acetone, methyl-positive butanone, methyl-positive pentanone, 2-HEPTANONE etc.; Saturated aliphatic mono Arrcostab, as ethyl acetate, n-butyl acetate, isobutyl acetate etc.; Lactic acid alkyl ester, as methyl lactate, ethyl lactate etc.; Glycolic acid Arrcostab, as hydroxy methyl acetate, hydroxyl ethyl acetate, Butyl Glycolate etc.; Alkoxy alkyl acetates, as acetic acid methoxyl methyl esters, methoxy ethyl acetate, methoxy butyl acetate, acetic acid ethoxy methyl esters, ethoxyethyl acetate(EA) etc.; 3-hydroxyalkyl propionate, as 3-hydroxy methyl propionate, 3-hydroxypropionate etc.; 3-alkoxypropan acid alkyl ester, as 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxyl ethyl propionate, 3-ethoxypropanoate etc.; 2 hydroxy propanoic acid Arrcostab, as 2 hydroxy propanoic acid methyl esters, 2 hydroxy propanoic acid ethyl ester, 2 hydroxy propanoic acid propyl ester etc.; Alkyl 2-alkoxypropan acid alkyl ester, as 2-methoxy methyl propionate, 2-methoxypropionate, 2-ethoxyl ethyl propionate, 2-ethoxypropanoate etc.; 2-hydroxy-2-methyl alkyl propionates, as 2-hydroxy-2-methyl methyl propionate, 2-hydroxy-2-methyl ethyl propionate; 2-alkoxy-2 Methylpropionic acid Arrcostab, as 2-methoxyl-2 Methylpropionic acid methyl esters, 2-ethoxy-2 Methylpropionic acid ethyl ester etc.; Ester, as propionic acid 2-hydroxyl ethyl ester, propionic acid 2-hydroxy-2-methyl ethyl ester, acetic acid hydroxyl ethyl ester, 2-hydroxy-3-methyl methyl butyrate etc.; Or keto ester, as ethyl pyruvate.In addition, solvent can be N-METHYLFORMAMIDE, N, dinethylformamide, N-methyl formyl aniline, N-methylacetamide, DMA, 1-METHYLPYRROLIDONE, dimethyl sulfoxide, benzyl ether, two hexyl ethers, diacetone, isophorone, caproic acid, sad, 1-octanol, 1 nonyl alcohol, phenmethylol, phenylmethyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, gamma-butyrolacton, ethylene carbonate, propylene carbonate, ethylene glycol monophenyl ether acetic acid esters etc.These solvents can separately or in two kinds or be greater than two kinds form of mixtures use.
Consider miscibility (miscibility), reactivity etc., solvent can comprise glycol ethers, as ethylene glycol monoethyl ether etc.; Ethylene glycol alkylether acetates, as ethyl cellosolve acetate etc.; Ester, as propionic acid 2-hydroxy methacrylate etc.; Diethylene glycol, as diethylene glycol monomethyl ether etc.; Or propylene glycol alkyl ether acetic acid ester, as propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid esters etc.
Solvent by the surplus of the photosensitive resin composition total amount for color filter, and specifically can be included with the amount in 20 % by weight to 90 % by weight scopes.When comprising the solvent in described scope, the photosensitive resin composition for color filter can have splendid coating characteristics and be more than or equal to the flatness maintaining improvement in the layer of 2 microns at thickness.
(F) other adjuvant
In order to the spot during preventing from being coated with or spot, regulate planarization, or prevent because of the pattern residue caused by non-development, the photosensitive resin composition for color filter can comprise other adjuvant, further as malonic acid; 3-amino-1,2-PD; Silane coupling agent, comprises vinyl or (methyl) acryloxy; Leveling agent; Fluorine class surfactant; Free radical polymerization initiator.
Fluorine class surfactant can have 4,000 gram/mol to 10,000 gram/mol, and the specifically low weight mean molecular weight of 6,000 gram/mol to 10,000 gram/mol.In addition, fluorine class surfactant can have the surface tension (in 0.1% methoxypolyethylene glycol acrylate (polyethyleneglycol methylether acrylate, PEGMEA) solution measure) of 18 milli Newton/meter to 23 milli Newton/meter.When fluorine class surfactant has weight average molecular weight in described scope and surface tension, it provides splendid feature to slot coated (slit coating), described narrow painting is a kind of high-speed coating (high speedcoating) method, because leveling performance can be improved, and strengthen blob features under high-speed coating, and less formation bubble and reduce film defect.
The example of fluorine class surfactant can comprise F-482, F-484, F-478 etc. that Dainippon Ink. & Chemicals Inc (DIC Co., Ltd.) manufactures, but is not limited thereto.
Fluorine class surfactant can use together with organosilicone surfactants.
The example of silicone surfactant can comprise TSF400, TSF401, TSF410, TSF4440 etc. that organosilicon Co., Ltd. of Toshiba (Toshiba siliconeCo., Ltd.) manufactures, but is not limited thereto.
In addition, the photosensitive resin composition for color filter can comprise epoxy compound further to improve closed contact performance and further feature (if desired).
Epoxy compound can be epoxy novolac acryloyl carboxylate resin, Study On O-cresol Epoxy Resin, novalac epoxy, tetramethyl biphenyl base epoxy, bisphenol A epoxide resin, alicyclic ring epoxide resin or its combination.
When comprising epoxy compound further, the free radical polymerization initiator as superoxide initiator or azo two class initiator can be comprised further.
Photosensitive resin composition 0.01 weight portion that epoxy compound can be used for color filter by 100 weight portions is included to the amount of 5 weight portions.When comprising the epoxy compound in described scope, can modified storage characteristic and economic contact performance and further feature.
For the preparation of the method for the photosensitive resin composition of color filter not by specific restriction, but the described photosensitive resin composition for color filter can pass through mixed colorant, acryl based binder resin, photopolymerization initiator, photopolymerizable monomer, solvent and and optional adjuvant prepare.
According to another embodiment of the present invention, the color filter that a kind of use manufactures for the photosensitive resin composition of color filter is provided.
This color filter can use conventional method manufacture, but exactly, uses the method such as spin coating, roller coat, narrow painting of the photosensitive resin composition being used for color filter, make it have 2 microns to the thickness in 4 micrometer ranges.After coating, with layer described in UV ray, electron beam or X-radiation to form the pattern needed for color filter.UV ray can have 190 nanometers to 450 nanometers, and specifically 200 nanometers to the wavelength region may in 400 nanometer range.Subsequently, when by alkaline metal developing solution process coating, its non-radiation areas can be dissolved, thus form the pattern being used for image color filter.Depending on required R, G and B number of colours, repeat this process, thus manufacture the color filter with required pattern.In addition, by the solidification such as thermal treatment, actinic ray radiation by the image pattern obtained that develops, thus improved cracking, solvent resistance etc.
Use gained color filter pattern to measure the photosensitive resin composition being used for color filter, and its contrast ratio can be more than or equal to 9000.Use high-peaker test's device CT-1 (Contrast tester CT-1) that kettle slope motor (Tsubosaka) manufactures, measure contrast ratio by light intensity when measuring Polarizer open and close, and calculate contrast ratio according to following equation 1.
[equation 1]
Contrast ratio (contrast ratio)=L open/ L closed
L open: light intensity when Polarizer is opened
L closed: light intensity when Polarizer closes
Embodiment
Hereinafter, reference example is described in more detail the present invention.But these examples limit the scope of the invention going up in all senses to be all not interpreted as.
(Bei perylene class dyestuff)
Prepare example 1
3.0 grams of (0.0038 mole) N are added in 40 milliliters of 1-METHYLPYRROLIDONEs, N '-bis-(2,6-diisopropyl phenyl) 1-Xiu perylene 3,4,9, the sub-acid amides of 10-tetracarboxylic acid two and 1.26 grams of (0.0076 mole) 4-tert-butyl group thiophenols, add 2.1 grams of (0.0152 mole) K wherein 2cO 3, and add hot mixt under a nitrogen and reach to 120 DEG C and reflux 6 hours.When the reactions are completed, make products therefrom cool to room temperature, and to obtain precipitation in its slow impouring 400 milliliters of 10%HCl aqueous solution.Under reduced pressure filter described precipitation, with distilled water washing several times until its pH becomes 7, and in vacuum drying oven dry one day, obtain the compound represented by following chemical formula 4.
[chemical formula 4]
Prepare example 2
Except use 2.52 grams (0.0152 mole) 4-tert-butyl group thiophenol, obtain the compound represented by following chemical formula 5 according to the method identical with preparing example 1.
[chemical formula 5]
Relatively prepare example 1
Slowly be heated by 0.98 gram of (0.0025 mole of) perylene-3 under a nitrogen, 4,9,10-tetracarboxylic acid dianhydride (perylene-3,4,9,10-tetracarboxylic dianhydride) and 0.766 gram of (0.00575 mole, 2.3 equivalents) aminoacetal add the reactant that 60 milliliters of metacresols and 10 milliliters of isoquinoline (isoquinoline) obtain.Subsequently, reactant is refluxed 4 hours at 100 DEG C, at 120 DEG C 6 hours, at 150 DEG C 5 hours, and at 200 DEG C 2 hours, cool to room temperature subsequently.Subsequently, add 100 ml methanol (existing to be dissolved in solution form in methyl alcohol) to reactant, and use rotary distillation equipment make methyl alcohol and metacresol all evaporate after dry described solution in an oven.Desciccate is made to be dissolved in methylene chloride (CH 2cl 2) in, with water and 5% sodium hydrate aqueous solution repeated washing solution, use rotary distillation equipment to make it by magnesium sulfate (MgSO subsequently 4), remove methylene chloride.Dry described products therefrom one day in an oven, stirs 2 hours subsequently for precipitation after adding methyl alcohol wherein.Under reduced pressure filter the precipitation produced, and dry one day in an oven, obtain the compound represented by following chemical formula 6.
[chemical formula 6]
Relatively prepare example 2
Not using except aminoacetal except in the reactant preparing example 1, preparing the compound represented by following chemical formula 7 according to the method identical with preparing example 1.
[chemical formula 7]
(photosensitive resin composition for the preparation of color filter)
Component for the preparation of photosensitive resin composition is as follows.
(A) colorant
(A-1) perylene class dyestuff
(A-1-1) compound preparing preparation in example 1 is used.
(A-1-2) compound preparing preparation in example 2 is used.
(A-1-3) compound comparing and prepare preparation in example 1 is used.
(A-1-4) compound comparing and prepare preparation in example 2 is used.
(B) acryl based binder resin
Operating weight mean molecular weight is the methacrylic acid/benzyl methacrylate multipolymer (mixed weight is than 15/85) of 22,000 gram/mol.
(C) photopolymerizable monomer
Use dipentaerythritol acrylate.
(D) photopolymerization initiator
(D-1) 1,2-acetyl caproyl is used.
(D-2) 2-dimethylamino-2-(4-Metfayl-benzyl)-1-(4-morpholine-4-base-phenyl)-Ding-1-ketone is used.
(E) solvent
(E-1) cyclohexanone is used.
(E-2) propylene glycol methyl ether acetate is used.
Example 1 and example 2 and comparative example 1 and comparative example 2
According to the composition mixing often kind of component shown in following table 1, be provided for the photosensitive resin composition of color filter.Specifically, photopolymerization initiator is made to be dissolved in solvent, at room temperature agitating solution 2 hours; add colorant wherein; stir the mixture 30 minutes, add acryl based binder resin and photopolymerizable monomer wherein, and at room temperature stir gained potpourri 2 hours.Filter described solution three times, and from its removal of impurity, obtain the photosensitive resin composition being used for color filter.
(table 1) (% by weight)
Assess the solubleness of 1: perylene class dyestuff
Heat respectively to measure before and after 30 minutes in 200 DEG C of strong convection drying ovens and be used for example 1 and example 2 and comparative example 1 and the comparative example 2 perylene class dyestuff solubleness about solvent, and provide result in following table 2.
Herein, solubleness is by being dissolved in 100 grams of cyclohexanone and propylene glycol methyl ether acetate general assembly (TW) Zhong perylene class amount of dye (gram) acquisition.
Assessment 2: for the chemical resistance of the photosensitive resin composition of color filter
Often kind of photosensitive resin composition is applied to 2 microns to 3 micron thickness on 0.63 millimeters thick degreasing/cleaning glass substrate, and on 90 DEG C of hot plates dry 2 minutes, obtain film.Subsequently, described film is made to be exposed to the high-pressure sodium lamp of wavelength 365 nanometer, and in 230 DEG C of strong convection drying ovens dry 60 minutes, obtain sample.Sample to heat at 60 DEG C in the 1-METHYLPYRROLIDONE of 10 minutes and by using spectrophotometer (MCPD3000 be impregnated in, Ao Tesuka Electronics Co., Ltd. (Otsuka electronicsInc.)) taken out before and after again measure the color character (L* of sample, a*, b*), calculate the aberration (Δ Eab*) before and after dipping, and provide result in following table 2.
(table 2)
Reference table 2, uses and shows before heating than comparative example 1 and the higher solubleness of comparative example 2 according to the example 1 of the perylene class dyestuff of an embodiment and example 2, but about the solubleness step-down of solvent.Therefore, example 1 and example 2 dissolve display about the high-dissolvability of solvent and splendid chemical resistance because of the deterioration during heat curing.In addition, example 1 and example 2 show the hue feature difference with comparative example 1 and comparative example 2, and therefore show splendid chemical resistance.
Although combined be considered as practical exemplary embodiments at present content to describe the present invention, but should understand and the invention is not restricted to disclosed embodiment, but contrary, the present invention is intended to contain and is included in various amendment in the spirit and scope of claims and equivalent arrangements.Therefore, previous embodiment is interpreted as exemplary but does not limit the present invention in any way.

Claims (7)

1., for a photosensitive resin composition for color filter, comprise
(A) colorant, comprises by following chemical formula 1 Biao Shi perylene class dyestuff;
(B) acryl based binder resin;
(C) photopolymerization initiator
(D) photopolymerizable monomer; And
(E) solvent:
[chemical formula 1]
(wherein, in chemical formula 1,
R 1to R 10be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylene oxide group, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C2 to C20 alkenylene, substituted or unsubstituted C2 to C20 alkynylene, substituted or unsubstituted C3 to C20 cycloalkylidene, the sub-cycloalkenyl group of substituted or unsubstituted C3 to C20, the sub-cycloalkynyl radical of substituted or unsubstituted C3 to C20, the sub-Heterocyclylalkyl of substituted or unsubstituted C2 to C20, the sub-heterocycloalkenyl of substituted or unsubstituted C2 to C20, the sub-heterocycle alkynyl of substituted or unsubstituted C2 to C20, substituted or unsubstituted C6 to C30 arlydene, the sub-aryloxy group of substituted or unsubstituted C6 to C30,-S-or-S-S-, its restrictive condition is R 1to R 10in at least one be-S-or-S-S-, and
R 11to R 20be same to each other or different to each other, and be hydrogen atom, halogen atom, cyano group, hydroxyl, ether, amido or amine deriveding group, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 thiazolinyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C3 to C20 naphthenic base, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl radical, substituted or unsubstituted C2 to C20 Heterocyclylalkyl, substituted or unsubstituted C2 to C20 heterocycloalkenyl, substituted or unsubstituted C2 to C20 heterocycle alkynyl, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C6 to C30 aryloxy group.)
2. the photosensitive resin composition for color filter according to claim 1, Qi Zhong Suo Shu perylene class dyestuff comprises at least one that select from the compound represented by following chemical formula 2 and chemical formula 3:
[chemical formula 2]
[chemical formula 3]
(wherein, in chemical formula 2 and chemical formula 3,
R 21and R 25be same to each other or different to each other, and be singly-bound, substituted or unsubstituted C1 to C20 alkylidene, substituted or unsubstituted C6 to C30 arlydene ,-S-or-S-S-, its restrictive condition is R 21and R 25in at least one be-S-or-S-S-,
R 22and R 26substituted or unsubstituted C1 to C20 alkylidene independently of one another,
R 23, R 24, R 27, R 28, R 29, R 30and R 32substituted or unsubstituted C1 to C20 alkyl independently of one another,
R 31-S-or-S-S-, and
N 1to n 3the integer in 0 to 5 scopes independently of one another.)
3. the photosensitive resin composition for color filter according to claim 1, wherein said colorant also comprises pigment.
4. the photosensitive resin composition for color filter according to claim 3, wherein said pigment comprises C.I. red pigment 254, C.I. red pigment 255, C.I. red pigment 264, C.I. red pigment 270, C.I. red pigment 272, C.I. red pigment 177, C.I. red pigment 89, C.I. yellow uitramarine 139, C.I. yellow uitramarine 138, C.I. yellow uitramarine 150 or its combination.
5. the photosensitive resin composition for color filter according to claim 3, wherein said colorant comprises the Suo Shu perylene class dyestuff and described pigment that weight ratio is 1: 10 to 10: 1.
6. the photosensitive resin composition for color filter according to claim 1, the wherein said photosensitive resin composition for color filter comprises
Colorant (A) described in 0.01 % by weight to 60 % by weight;
Acryl based binder resin (B) described in 0.5 % by weight to 20 % by weight;
Photopolymerization initiator (C) described in 0.1 % by weight to 20 % by weight;
Photopolymerizable monomer (D) described in 0.5 % by weight to 20 % by weight; And
Solvent described in surplus (E).
7. a color filter, it uses the photosensitive resin composition according to any one of claim 1 to 6 to manufacture.
CN201380060623.1A 2012-12-13 2013-04-29 Photosensitive resin composition for color filter and color filter using same Pending CN104813233A (en)

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