CN103576455A - A colored photosensitive resin composition, color filter and liquid crystal display device having the same - Google Patents
A colored photosensitive resin composition, color filter and liquid crystal display device having the same Download PDFInfo
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- CN103576455A CN103576455A CN201310325754.XA CN201310325754A CN103576455A CN 103576455 A CN103576455 A CN 103576455A CN 201310325754 A CN201310325754 A CN 201310325754A CN 103576455 A CN103576455 A CN 103576455A
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- 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
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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
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a colored photosensitive resin composition,a color filter and a liquid crystal display device having the same. The colored photosensitive resin composition comprises colorant (A), alkali-soluble resin (B), photopolymerizable polymer (C), photopolymerizable initiator (D), cross-linking agent (E), and solvent (F). The hydroxyl value of the alkali-soluble resin (B) is in a range from 30-180mgKOH/g, and the cross-linking agent (E) can be expressed by the formula 1.
Description
Technical field
The present invention relates to photosensitive composition, the photosensitive composition for color filter using while more specifically, relating to the color filter of use in manufacturing color liquid crystal display arrangement etc., the liquid crystal indicator that uses the color filter of its manufacture and comprise this color filter.
Background technology
Color filter (color filter) is built in the color image pickup apparatus of imageing sensor of complementary metal oxide semiconductor (CMOS) (complementary metal oxide semiconductor, CMOS) or charge coupled cell (charge coupled device, CCD), be actually and obtained coloured image and use, in addition, be widely used in imaging apparatus, plasma display panel (PDP), liquid crystal indicator (LCD), Field Emission Display (FEL) and active display (LED) etc. its range of application rapid growth.Particularly more increased recently the purposes to LCD, thus, on the basis of toning that reappears LCD, color filter is familiar with as one of most important member.
The photosensitive composition that this color filter can comprise colorant by use forms the method for desirable colored pattern and manufactures.Particularly, by repeatedly carrying out following a series of process, manufacture: on substrate, form the coat being formed by photosensitive composition, at formed coat, form pattern and expose and develop, heat and make its heat curing.
With the photosensitive composition that colorant comprises dyestuff, manufacture in the situation of color filter, because the compatibility with used material is not enough, when the formation of dyed layer, produce foreign matter.In addition, while manufacturing color filter, developing powder is slow, and sensitivity is not enough, the problem that when generation utilizes alkaline developer to carry out developing procedure continually, the pattern of formation is peeled off.Therefore, require exploitation can solve the photosensitive composition that is suitable for photo-mask process of the problem when containing dyestuff as colorant or using separately dyestuff as colorant.
In order to address this is that, in No. 10-2010-0063571st, Korea S's publication, a kind of photosensitive composition is disclosed, it is by applicable multi-functional huge monomer, even in the situation that containing high concentration pigment, also can improve developability, surperficial illumination etc., but still need to carry out problem for solving developing powder and sensitivity, the problem such as the pattern while utilizing alkaline developer to carry out developing procedure is peeled off, reliability.
Patent documentation
Patent documentation 1: Korea S publication 10-2010-0063571 instructions
Summary of the invention
In order to address the above problem, the object of the invention is to, a kind of color filter photosensitive composition that can access the color filter of permeability excellence is provided.
In addition, the object of the invention is to, provide that a kind of developing powder is fast, sensitivity and adhesiveness is excellent, there is no that pattern is peeled off, bin stability excellent in developing procedure, also can not produce sensitivity during long preservation, photosensitive composition that viscosity increases.
The invention provides a kind of photosensitive composition, comprise colorant (A), alkali soluble resins (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D), crosslinking chemical (E) and solvent (F), it is characterized in that
The hydroxyl value of aforementioned bases soluble resin (B) is 30～180mgKOH/g, and aforementioned crosslinking chemical (E) represents by following Chemical formula 1,
[Chemical formula 1]
In aforementioned Chemical formula 1,
Aforementioned R
1and R
2alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently,
Aforementioned A is hydrocarbon ring or replacement or the unsubstituted heterocycle that replacement or unsubstituted carbon number are 2～6,
Substituting group is alkyl, amino, ether, ketone group or ester group,
Two aforementioned substituting groups can connect and form condensed ring,
The heteroatoms containing in heterocycle is O, N or S.
Aforementioned crosslinking chemical (E) is more preferably represented by following Chemical formula 2, chemical formula 3, chemical formula 4 or chemical formula 5.
[Chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
In aforementioned chemical formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9and R
10alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently.
In addition, the invention provides a kind of color filter, its top that is included in substrate is coated with photosensitive composition of the present invention, with the pattern of stipulating, exposes and develops and the color layer that forms.
And the present invention also provides a kind of liquid crystal indicator, it is characterized in that, comprise aforementioned color filter.
Photosensitive composition of the present invention provides following characteristic: developing powder is fast and adhesiveness is excellent, is difficult for producing the pattern short circuit in developing procedure, and the throughput rate of color filter is excellent.In addition, use the reliability excellence of the color filter of this photosensitive composition manufacture, what in the time of can being reduced in rear operation, produce is bad.
Embodiment
Below the present invention is described in more detail.
The present invention relates to a kind of photosensitive composition, comprise colorant (A), alkali soluble resins (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D), crosslinking chemical (E) and solvent (F), it is characterized in that
The hydroxyl value of aforementioned bases soluble resin (B) is 30～180mgKOH/g, and aforementioned crosslinking chemical (E) is represented by following Chemical formula 1.
[Chemical formula 1]
In aforementioned Chemical formula 1,
Aforementioned R
1and R
2alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently,
Aforementioned A is hydrocarbon ring or replacement or the unsubstituted heterocycle that replacement or unsubstituted carbon number are 2～6,
Substituting group is alkyl, amino, ether, ketone group or ester group,
Two aforementioned substituting groups can connect and form condensed ring,
The heteroatoms containing in heterocycle is O, N or S.
Aforementioned crosslinking chemical (E) is more preferably represented by following Chemical formula 2, chemical formula 3, chemical formula 4 or chemical formula 5.
[Chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
In aforementioned chemical formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9and R
10alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently.
Below, each formation is described in more detail.
(A) colorant
The pigment (a1) that aforementioned colorant (A) comprises more than one, as essential composition, can also comprise more than one dyestuff (a2).
pigment (a1)
Aforementioned pigment can be used normally used organic pigment or inorganic pigment in this field.Aforementioned pigment can be used the various pigment that use in printer's ink, ink jet ink etc., particularly, can list water-soluble azo pigment, insoluble azo colour, phthalocyanine color, quinacridone pigment, isoindoline ketone pigment, isoindoline pigment, perylene dye, pyrene ketone pigment, triazine dioxin pigment, anthraquinone pigment, DIANTHRAQUINONE pigment, anthracene pyrimidine pigment, anthracene buttress anthraquinone (anthanthrone) pigment, indanthrone pigment, flavanthrone pigment, pyranthrone pigments and diketopyrrolo-pyrrole pigment etc.As aforementioned inorganic pigment, can list the metallic compounds such as metal oxide, metal complex, particularly, can enumerate tap a blast furnace, the oxide of the metal such as cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black or composite metal oxide etc.Especially, as aforementioned organic pigment and inorganic pigment, particularly, can list the compound that is categorized as pigment under colour rendering index (The society of Dyers and Colourists publication), more specifically, the pigment of numbering as colour rendering index (C.I.) below can be listed, but this might not be defined in.
C.I. pigment yellow 13,20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173,180 and 185
C.I. pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,224,242,254,255 and 264
C.I. pigment violet 14,19,23,29,32,33,36,37 and 38
C.I. pigment blue 15 (15:3,15:4,15:6 etc.), 21,28,60,64 and 76
C.I. pigment Green 7,10,15,25,36,47 and 58
C.I. pigment brown 28
C.I. pigment black 1 and 7 etc.
Aforementioned pigment (a1) can be used separately respectively or combine two or more use.
In aforementioned illustrative C.I. pigment, also can more suitably use the pigment that is selected from following pigment: C.I. pigment orange 38, C.I. pigment red 122, C.I. paratonere 166, C.I. paratonere 177, C.I. paratonere 208, C.I. paratonere 242, C.I. paratonere 254, C.I. paratonere 255, C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150, C.I. pigment yellow 185, C.I. pigment Green 7, C.I. pigment green 36, C.I. naphthol green 58, C.I. pigment Violet 23, C.I. pigment blue 15: 3, C.I. pigment blue 15: 6.
The content of aforementioned pigment (a1) for all solids composition of pigment dispensing composition by weight mark count 20～90 % by weight, preferably in the scope of 30～70 % by weight.As long as the content of aforementioned pigment is by aforementioned benchmark in the scope of 20～90 % by weight, viscosity is low, bin stability is excellent, dispersion efficiency is high, effectively improved contrast, therefore preferably.
pigment dispersing agent (a3)
Aforementioned pigment is preferably used the homodisperse dispersible pigment dispersion of its particle diameter.As carrying out method of dispersion treatment etc. for making an example of the homodisperse method of particle diameter of pigment, can list to contain pigment dispersing agent (a3), according to described method, can access the dispersible pigment dispersion that pigment is dispersed in the state in solution.
As the concrete example of aforementioned pigment dispersing agent, can list the surfactants such as kation system, negative ion system, nonionic system, both sexes, polyester system, polyamine system etc., these pigment dispersing agents can be used separately respectively or combine two or more use.
Aforementioned pigment dispersing agent (a3), except aforementioned acrylic acid dispersant, also can be used other resene pigment dispersing agents.As aforementioned other resene pigment dispersing agents, can list: known resene pigment dispersing agent, particularly take (part) amine salt, the ammonium salt of poly carboxylic acid, the alkylamine salt of poly carboxylic acid, polysiloxane, long-chain polyaminoamide phosphate, hydroxyl of polycarboxylate that polyurethane, polyacrylate is representative, unsaturated polyester acid amides, poly carboxylic acid, poly carboxylic acid-containing the acid esters of poly carboxylic acid and their modification product or by the oily spreading agent such with gathering acid amides that reacting of (low-grade alkylidene imines) form or these salt of the polyester with freedom (free) carboxyl; (methyl) acrylic acid-styrol copolymer, (methyl) acrylic acid-(methyl) acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol (PVA) or such water soluble resin or the water-soluble polymeric compounds of polyvinylpyrrolidone; Polyester; Modified polyacrylate; The addition product of ethylene oxide/propylene oxide and phosphate etc.In the commercially available product of aforementioned resin type spreading agent, as kation, be pitch dispersant, for example, can list: the trade name of BYK (Bi Ke) chemical company: DISPER BYK-160, DISPERBYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPERBYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184, DISPERBYK-2001; The trade name of BASF AG: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; The trade name of Lubirzol company: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; The trade name of Chuan Yan fine chemicals company: ヒ ノ ア Network ト (HINOACT) T-6000, HINOACTT-7000, HINOACTT-8000; The trade name of aginomoto company: ア ジ ス パ ー (AJISPUR) PB-821, AJISPURPB-822, AJISPURPB-823; Trade name: フ ロ ー レ Application (FLORENE) DOPA-17HF of chemical company of common prosperity society, FLORENEDOPA-15BHF, FLORENEDOPA-33, FLORENEDOPA-44 etc.Except aforementioned acrylic acid dispersant, other resene pigment dispersing agents also can be used separately respectively or combine two or more use, also can use with acrylic acid dispersant simultaneously.
The consumption of aforementioned pigment dispersing agent (a3) with respect to solid constituent 100 weight portions of used pigment (a1) in the scope of 5～60 weight portions, more preferably in the scope of 15～50 weight portions.When the content of aforementioned pigment dispersing agent (a3) surpasses 60 weight portion by aforementioned benchmark, viscosity raises, and during containing quantity not sufficient 5 weight portion, causes and is difficult to carry out the micronize of pigment or disperses the problems such as rear gelation.
dyestuff (a2)
Aforementioned dyestuff (a2) just can unrestrictedly be used as long as have for the dissolubility of organic solvent.Preferably, preferably use and there is the dissolubility for organic solvent, and can guarantee the dyestuff of the reliability of dissolubility for alkaline developer, thermotolerance, solvent resistance etc.
As aforementioned dyestuff (a2), can use the salt of the acid dyes, acid dyes and the nitrogen-containing compound that are selected from acidic-groups such as thering is sulfonic acid or carboxylic acid, the dyestuff of the sulfonamide compound of acid dyes etc. and their derivant, in addition, also can select azo system, xanthene system, phthalocyanine is acid dyes and their derivant.Preferably, aforementioned dyestuff can list: in colour rendering index (The Society of Dyers and Colourists publication), be categorized as the compound of dyestuff, or the known dyestuff of recording in dyeing notes (dyeing and weaving company).
In the concrete example of aforementioned dyestuff, as C.I. solvent dye, there are C.I. solvent red 8,45,49,89,111,122,125,130,132,146, the orchils such as 179;
C.I. the blue dyes such as solvent blue 5,35,36,37,44,59,67,70;
C.I. solvent purple 8,9,13,14,36,37,47, the cudbears such as 49;
C.I. the weld such as solvent yellow 4,14,15,23,24,38,62,63,68,82,94,98,99,162;
C.I. solvent orange 2,7,11,15,26, the oranges such as 56;
C.I. green colouring material such as solvent green 1,3,4,5,7,28,29,32,33,34,35 etc.
C.I. in solvent dye preferably for the C.I. solvent red 8,49,89,111,122,132,146,179 of the dissolubility excellence of organic solvent; C.I. solvent blue 35,36,44,45,70; C.I. solvent violet 13; Wherein, more preferably C.I. solvent red 8,122,132.
In addition, as C.I. acid dyes, can list: C.I. azogeramine, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426 orchils such as grade,
C.I. Indian yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251 welds such as grade,
C.I. the orange such as acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,169,173;
C.I. Blue VRS, 7,9,15,18,23,25,27,29,40,42,45,51,62,70,74,80,83,86,87,90,92,96,103,112,113,120,129,138,147,150,158,171,182,192,210,242,243,256,259,267,278,280,285,290,296,315,324:1,335, the blue dyess such as 340;
C.I. acid violet 6B, 7,9,17,19, the cudbears such as 66;
C.I. green colouring material such as acid green 1,3,5,9,16,25,27,50,58,63,65,80,104,105,106,109 etc.
The C.I. acid red 92 of the preferred solubleness excellence for organic solvent in acid dyes; C.I. acid blue 80,90; C.I. acid violet 66.
In addition, as C.I. direct dyes, can list: the orchils such as C.I. direct red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177,179,181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250;
C.I. direct welds such as yellow 2,33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98,102,108,109,129,136,138,141;
C.I. the orange such as direct orange 34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107;
C.I. directly blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293 blue dyess such as grade,
C.I. direct cudbears such as purple 47,52,54,59,60,65,66,79,80,81,82,84,89,90,93,95,96,103,104;
C.I. green colouring material such as direct green 25,27,31,32,34,37,63,65,66,67,68,69,72,77,79,82 etc.
Can list: the welds such as C.I. mordant Huang 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65;
C.I. the orchil such as mordant red 1,2,3,4,9,11,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,41,43,45,46,48,53,56,63,71,74,85,86,88,90,94,95;
C.I. the orange such as mordant orange 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47,48;
C.I. the blue dyes such as mordant indigo plant 1,2,3,7,8,9,12,13,15,16,19,20,21,22,23,24,26,30,31,32,39,40,41,43,44,48,49,53,61,74,77,83,84;
C.I. the cudbear such as mordant purple 1,2,4,5,7,14,22,24,30,31,32,37,40,41,44,45,47,48,53,58;
C.I. green colouring material such as mordant green 1,3,4,5,10,15,19,26,29,33,34,35,41,43,53 etc.
These dyestuffs can be used separately respectively or combine two or more use.
The content of the dyestuff in aforementioned colorant (A) preferably contains 0.5～90 % by weight with respect to the general assembly (TW) of the solid constituent of colorant (A), and more preferably 0.5～60 % by weight, is particularly preferably 1～50 % by weight.The content of the dyestuff in aforementioned colorant (A) in the situation in aforementioned range, after forming pattern, can prevent that organic solvent from making the problem of the reliability decrease of dyestuff stripping in aforementioned benchmark, and sensitivity is excellent and preferred.
The content of aforementioned colorant (A) preferably contains 5～60 % by weight with respect to the general assembly (TW) of the solid constituent of photosensitive composition, more preferably contains 10～45 % by weight.In the situation that aforementioned colorant (A) contains 5～60 % by weight in aforementioned benchmark, even if form film, the colour saturation of pixel is also abundant, and during development, the damaged property of non-pixel portion does not decline yet, and therefore can suppress the generation of residue, therefore preferably.
In the present invention, the content of the total solid composition in photosensitive composition refers to the total content of composition residual from photosensitive composition is removed solvent.
(B) alkali soluble resins
For the alkaline-based developer using in the development treatment operation when forming pattern has solubility, the ethylenically unsaturated monomer (b1) with carboxyl of usining is manufactured as must composition carrying out copolymerization.
Aforementioned bases soluble resin (B) comprises hydroxyl.By comprising hydroxyl, there is the improved effect of developing powder.More than the hydroxyl value of alkali soluble resins (B) is restricted to 30mgKOH/g and below 180mgKOH/g.In the situation of the not enough 30mgKOH/g of hydroxyl value, can not guarantee sufficient developing powder, surpass in the situation of 180mgKOH/g, the dimensional stability of the pattern that forms reduces, it is bad that the craspedodrome of pattern easily becomes, and reduces with the compatibility of dyestuff, easily produces the problem of bin stability.
In addition, the contained alkali soluble resins of the present invention is characterised in that the active unsaturated group that contains 50 % by mole to 70 % by mole.When alkali soluble resins contains active unsaturated group, produce hydroxyl, show in the present invention heat curing characteristic, can there is aforementioned hydroxyl value.
As the aforementioned concrete example with the ethylenically unsaturated monomer (b1) of carboxyl, can list: the monocarboxylic acid classes such as acrylic acid, methacrylic acid, crotonic acid; The omega-dicarboxylic acids such as fumaric acid, mesaconic acid, itaconic acid; And the acid anhydrides of these omega-dicarboxylic acids; ω-carboxyl polycaprolactone list (methyl) acrylate etc. have list (methyl) esters of acrylic acid of the polymkeric substance of carboxyl and hydroxyl etc. at two ends, be preferably acrylic acid, methacrylic acid.
In order to provide hydroxyl to alkali soluble resins (B), can manufacture as follows: will there is the ethylenically unsaturated monomer (b1) and ethylenically unsaturated monomer (b2) copolymerization with hydroxyl of carboxyl; The multipolymer that makes to have the ethylenically unsaturated monomer (b1) of carboxyl appends and reacts with the compound (b3) with glycidyl.In addition, can also append with the multipolymer with the ethylenically unsaturated monomer (b2) of hydroxyl and react to manufacture with the compound (b3) with glycidyl by making to have the ethylenically unsaturated monomer (b1) of carboxyl.
As the aforementioned concrete example with the compound (b3) of glycidyl, there is butyl glycidyl base ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyric ester, glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, tert-butyl group glycidyl ether, benzyl glycidyl ether, glycidyl-4-p t butylbenzoic acid ester, glycidyl stearate, arylolycidyl base ether, glycidyl methacrylate etc., be preferably butyl glycidyl base ether, arylolycidyl base ether, glycidyl methacrylate, can combine two or more use.
Unsaturated monomer (b4) that can copolymerization during the manufacture of aforementioned bases soluble resin (B) is illustration as follows, but must not be defined in this.
As the concrete example with the polymerizable monomer (b4) of unsaturated link that can copolymerization, there are styrene, vinyltoluene, α-methyl styrene, to chlorostyrene, O-methoxy styrene, meta-methoxy styrene, to methoxy styrene, adjacent vinyl benzyl methyl ether, a vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinyl benzyl glycidol ether, a vinyl benzyl glycidol ether, to aromatic ethylene compounds such as vinyl benzyl glycidol ethers;
N-N-cyclohexylmaleimide, N-benzyl maleimide, N-phenylmaleimide, N-o-hydroxy-phenyl maleimide, hydroxy phenyl maleimide between N-, N-p-hydroxybenzene maleimide, N-o-methyl-phenyl-maleimide, aminomethyl phenyl maleimide between N-, N-p-methylphenyl maleimide, N-o-methoxyphenyl maleimide, N-m-methoxyphenyl maleimide, the N-substituted maleimide amine compounds such as N-p-methoxyphenyl maleimide,
(methyl) alkyl-acrylates such as (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) acrylic acid n-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate; Alicyclic (methyl) esters of acrylic acids such as (methyl) acrylic acid ring pentyl ester, (methyl) cyclohexyl acrylate, (methyl) acrylic acid-2-methyl cyclohexyl, (methyl) acrylic acid three ring [5.2.1.02,6] decane-8-base esters, (methyl) acrylic acid-2-bis-cyclopentyloxy ethyl esters, (methyl) isobornyl acrylate;
(methyl) hydroxy-ethyl acrylate classes such as (methyl) acrylic acid-2-hydroxyl ethyl ester, (methyl) 2-hydroxypropyl acrylate, (methyl) acrylic acid 4-hydroxy butyl ester, (methyl) acrylic acid-2-hydroxyl-3-phenoxy group propyl ester, N-hydroxyethyl acrylamide;
(methyl) acrylic acid aryl ester classes such as (methyl) phenyl acrylate, (methyl) benzyl acrylate;
3-(methacryloxy methyl) oxetanes, 3-(methacryloxypropyl methyl)-3-Ethyloxetane, 3-(methacryloxy methyl)-2-trifluoromethyl oxetanes, 3-(methacryloxy methyl)-2-phenyl oxetanes, 2-(methacryloxy methyl) oxetanes, 2-(methacryloxy methyl)-unsaturated oxetane compounds such as 4-trifluoromethyl oxetanes etc.
As the aforementioned illustrated monomer of unsaturated monomer (b4) that can copolymerization, can use separately respectively or combine two or more use.
The content of aforementioned bases soluble resin (B) with respect to the general assembly (TW) of the solid constituent in photosensitive composition preferably contain 10～80 % by weight, more preferably in the scope of 10～70 % by weight.As long as the content of aforementioned bases soluble resin (B) is counted 10～80 % by weight by aforementioned benchmark, in developer, dissolubility is abundant, easily forms pattern, prevents that the film of the pixel portion of exposure portion from reducing during development, the damaged property of non-pixel portion becomes well, therefore preferably.
(C) optical polymerism compound
Aforementioned optical polymerism compound (C) be can polymerization under the effect of following Photoepolymerizationinitiater initiater (D) compound, can use monofunctional monomer, bifunctional monomer or polyfunctional monomer, preferably, can use polyfunctional monomer more than difunctionality.
Concrete example as aforementioned monofunctional monomer, there are nonyl phenyl carbitol acrylate, 2-hydroxyl-3-phenoxy propyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxy ethyl methacrylate or NVP etc., but are not limited thereto.
Concrete example as aforementioned bifunctional monomer, have 1, two (acrylyl oxy-ethyl) ether of 6-hexanediol two (methyl) acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, bisphenol-A or 3-methyl pentanediol two (methyl) acrylate etc., but be not limited thereto.
Concrete example as aforementioned polyfunctional monomer, there are trimethylolpropane tris (methyl) acrylate, propenoxylated trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate of trimethylolpropane tris (methyl) acrylate, ethoxylation, dipentaerythritol six (methyl) acrylate, propenoxylated dipentaerythritol six (methyl) acrylate or dipentaerythritol six (methyl) acrylate etc. of ethoxylation, but are not limited thereto.
Aforementioned optical polymerism compound (C) preferably contains 5～45 % by weight with respect to the general assembly (TW) of the solid constituent in photosensitive composition, more preferably contains 7～45 % by weight.In the situation that aforementioned optical polymerism compound (C) contains 5～45 % by weight in aforementioned benchmark, intensity, the flatness of pixel portion are good, therefore preferably.
(D) Photoepolymerizationinitiater initiater
Aforementioned Photoepolymerizationinitiater initiater (D), as long as can make optical polymerism compound (C) polymerization, does not limit especially its kind and uses.Particularly, aforementioned Photoepolymerizationinitiater initiater (D) considers from viewpoints such as polymerization property, efficiency of initiation, absorbing wavelength, acquired, prices, preferably uses more than one the compound selecting in the group that free acetophenone based compound, benzophenone based compound, triazine based compound, bisglyoxaline based compound, oxime compound and thioxanthones based compound form.
Concrete example as aforementioned acetophenone based compound, can list: diethoxy acetophenone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, benzil dimethyl ketal, 2-hydroxyl-1-[4-(2-hydroxyl-oxethyl) phenyl]-2-methylpropane-1-ketone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-(4-methyl thio phenyl)-2-morpholinyl propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone, 2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] propane-1-ketone, 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morpholino phenyl) butane-1-ketone etc.
As aforementioned benzophenone based compound, for example, there are benzophenone, o-benzoyl yl benzoic acid methyl esters, 4-phenyl benzophenone, 4-benzoyl-4 '-methyldiphenyl thioether, 3,3 '; 4; 4 '-tetra-(t-butyl peroxy carbonyl) benzophenone, 2,4,6-tri-methyl benzophenone etc.
Concrete example as aforementioned triazine based compound, can list: 2, two (the trichloromethyl)-6-(4-methoxyphenyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl naphthyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-of 4-piperonyl-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1 of 4-, 3, 5-triazine, 2, two (trichloromethyl)-6-[2-(5-methylfuran-2-yl) vinyl of 4-]-1, 3, 5-triazine, 2, two (trichloromethyl)-6-[2-(furans-2-yl) vinyl of 4-]-1, 3, 5-triazine, 2, two (trichloromethyl)-6-[2-(4-diethylamino-2-aminomethyl phenyl) vinyl of 4-]-1, 3, 5-triazine, 2, two (the trichloromethyl)-6-[2-(3 of 4-, 4-Dimethoxyphenyl) vinyl]-1, 3, 5-triazine etc.
Concrete example as aforementioned united imidazole, can list: 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2, 3-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(alkoxyl phenyl) bisglyoxaline, 2, 2 '-bis-(2-chlorphenyls)-4, 4 ', 5, 5 '-tetra-(tri-alkoxy phenyl) bisglyoxaline, 2, 2-two (2, 6-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl-1, 2 '-bisglyoxaline or 4, 4 ', 5, imidazolium compounds after the phenyl of 5 ' position is replaced by alkoxy carbonyl group etc.Among these, preferably use 2,2 '-bis-(2-chlorphenyls)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis-(2,3-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2-two (2,6-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl-1,2 '-bisglyoxaline.
As the concrete example of aforementioned oxime compound, can list adjacent ethoxy carbonyl-α-oxyimino group-1-phenyl-propane-1-ketone etc., as commercially available prod, be typically OXE01, the OXE02 of BASF AG.
As aforementioned thioxanthones based compound, for example, have: ITX, 2,4-diethyl thioxanthone, 2,4-bis-clopenthixal ketones, the chloro-4-propoxyl group of 1-thioxanthones etc.
In addition, in order to improve the sensitivity of photosensitive composition of the present invention, aforementioned (D) Photoepolymerizationinitiater initiater can also further comprise photopolymerization and cause assistant (d1).The photosensitive composition the present invention relates to causes assistant (d1) owing to comprising photopolymerization, makes sensitivity higher, thereby can boost productivity.
Aforementioned photopolymerization causes assistant (d1) and for example can preferably use and select free amines, carboxylic acid compound, have more than one the compound in the group that the organosulfur compound of mercapto forms.
As aforementioned amines, preferably use aromatic amine compound, particularly, can use fatty amine compound, 4-dimethylaminobenzoic acid methyl esters, EDMAB, 4-dimethylaminobenzoic acid isopentyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, benzoic acid 2-dimethylamino ethyl ester, the N such as triethanolamine, methyldiethanolamine, triisopropanolamine, N-dimethyl-p-toluidine, 4, Michler's keton), 4,4 '-bis-(lignocaine) benzophenone etc. 4 '-bis-(dimethylamino) benzophenone (is commonly called as:.
Aforementioned carboxylic acid compound is preferably the assorted acetic acid class of aromatic series, particularly, can list: thiophenyl acetic acid, methylbenzene ethyl thioglycollic acid, ethylbenzene ethyl thioglycollic acid, ethyl methyl benzene ethyl thioglycollic acid, dimethyl benzene ethyl thioglycollic acid, methoxybenzene ethyl thioglycollic acid, dimethoxy-benzene ethyl thioglycollic acid, chlorobenzene ethyl thioglycollic acid, dichloro-benzenes ethyl thioglycollic acid, N-phenylglycine, phenoxy acetic acid, naphthalene ethyl thioglycollic acid, N-naphthyl glycocoll, BNOA etc.
As the aforementioned concrete example with the organosulfur compound of mercapto, can list: 2-mercaptobenzothiazole, 1, two (the 3-sulfydryl butyryl acyloxy) butane, 1 of 4-, 3,5-tri-(3-sulfydryl butoxyethyl group)-1,3,5-triazine-2,4,6 (1H, 3H, 5H)-triketone, trimethylolpropane tris (3-mercaptopropionic acid ester), pentaerythrite four (3-sulfydryl butyric ester), pentaerythrite four (3-mercaptopropionic acid ester), dipentaerythritol six (3-mercaptopropionic acid ester), TEG two (3-mercaptopropionic acid ester) etc.
Aforementioned (D) Photoepolymerizationinitiater initiater take photosensitive composition of the present invention solid constituent general assembly (TW) as benchmark, with respect to (B) alkali soluble resins and (C) total content of optical polymerism compound can contain 0.1～40 % by weight, can preferably contain 1～30 % by weight.In the situation that aforementioned (D) Photoepolymerizationinitiater initiater is within the scope of aforementioned 0.1～40 % by weight, photosensitive composition high-sensitivity, the time shutter shortens, and throughput rate is improved, and can keep high resolving power, therefore preferably.And, use the intensity of the pixel portion that the composition of aforementioned condition forms and the surperficial flatness of aforementioned pixel portion to become good.
In addition, further use aforementioned photopolymerization to cause in the situation of assistant (d1), aforementioned photopolymerization cause assistant (d1) take photosensitive composition of the present invention solid constituent general assembly (TW) as benchmark, with respect to (B) alkali soluble resins and (C) total content of optical polymerism compound can contain 10～40 % by weight, can preferably contain 1～30 % by weight.The consumption that causes assistant (d1) in aforementioned photopolymerization is within the scope of aforementioned 0.1～40 % by weight in the situation that, and the sensitivity of photosensitive composition further improves, and the effect of using the throughput rate of the color filter that foregoing forms to improve is provided.
(E) crosslinking chemical
Aforementioned crosslinking chemical (E) is preferably represented by following Chemical formula 1.
[Chemical formula 1]
In aforementioned Chemical formula 1,
Aforementioned R
1and R
2the alkyl of the straight or branched of C1～C8 independently, or naphthenic base,
Aforementioned A is the hydrocarbon ring that replacement or unsubstituted carbon number are 2～6, or replacement or unsubstituted heterocycle,
Substituting group is alkyl, amino, ether, ketone group or ester group,
Two aforementioned substituting groups can connect and form condensed ring,
The heteroatoms containing in heterocycle is O, N or S.
Aforementioned crosslinking chemical is more preferably represented by following Chemical formula 2, chemical formula 3, chemical formula 4 or chemical formula 5.
[Chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
In aforementioned chemical formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9and R
10straight or branched alkyl or the naphthenic base of H, C1～C8 independently.
Aforementioned crosslinking chemical more preferably selects one or more in the group that freely following compound forms: 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (1, 3, 4, 6-tetrakis (methoxymethyl) tetrahydroimidazo[4, 5-d] imidazole-2, 5 (1h, 3h)-dion e), 1, two (the methoxy)-imidazolidinones (1 of 3-, 3-Bis (methoxymethyl)-2-imidazolidone), two (methoxies) (oxo dimethylene) urea (Bis (methoxymethyl) is urea (oxydimethylene)), 3, two (butoxymethyl) tetrahydrochysene-4H-1 of 5-, 3, 5-oxadiazine-4-ketone (3, 5-Bis (butoxymethyl) tetrahydro-4H-1, 3, 5-oxadiazin-4-one), 1, 3, 4, 6-tetra-(butoxymethyl) imidazolidine also (4, 5-d)-2, 5 (1H, 3H) diketone (1, 3, 4, 6-Tetrakis (butoxymethyl) tetrahydroimidazo (4, 5-d) imidazole-2, 5 (1H, 3H)-dion e), 1, two (methoxy) 2-ketone benzimidaozoles (1 of 3-, 3-bis (methoxymethyl) benzimidazol-2-one), 1, two (methoxy)-1 of 3-, 3-basudin-2-ketone (1, 3-bis (methoxymethyl)-1, 3-diazinan-2-one), 1, two (ethoxyl methyl) imidazolidin-2-ones (1 of 3-, 3-bis (ethoxymethyl) imidazolidin-2-one), 1, two (the 2-methyl-prop oxygen ylmethyl) imidazolidin-2-ones (1 of 3-, 3-bis (2-methylpropoxymethyl) imidazolidin-2-one) and 1, 3, 4, 6-tetra-(2-methyl-prop oxygen ylmethyl)-3a, 6a-glyoxalidine also [4, 5-d] imidazoles-2, 5-diketone (1, 3, 4, 6-tetrakis (2-methylpropoxymethyl)-3a, 6a-dihydroimidazo[4, 5-d] imidazole-2, 5-dione).
Aforementioned crosslinking chemical take the general assembly (TW) of solid constituent of photosensitive composition as benchmark, can preferably contain 0.1～15 % by weight, can more preferably contain 0.5～10 % by weight.In the situation that aforementioned crosslinking chemical contains 0.1～15 % by weight with respect to the general assembly (TW) of the solid constituent of photosensitive composition, for manufacturing the color filter that developing powder and adhesiveness are excellent, reliability is excellent, be effective.
(F) solvent
Aforementioned (F) solvent is as long as effectively dissolve other compositions that comprise in photosensitive composition, the solvent using in common photosensitive composition be can use with no particular limitation, ethers, aromatic hydrocarbon based, ketone, alcohols, ester class or amide-type etc. particularly preferably used.
Aforementioned (F) solvent particularly can list: the ethylene glycol monoalkyl ether classes such as glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether;
The diethylene glycol dialkyl ether classes such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, dipropylene glycol dipropyl ether, dibutyl ethylene glycol ether; The ethylene glycol such as methylcellosolve acetate, ethyl cellosolve acetate alkyl ether acetate esters;
The aklylene glycol alkyl ether acetate esters such as propylene glycol monomethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol list propyl ether acetic acid esters, methoxyacetic acid butyl ester, methoxyacetic acid pentyl ester;
Benzene,toluene,xylene, trimethylbenzene etc. are aromatic hydrocarbon based;
The ketones such as MEK, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone;
The alcohols such as ethanol, propyl alcohol, butanols, hexanol, cyclohexanol, ethylene glycol, glycerine;
The ester classes such as 3-ethoxyl ethyl propionate, 3-methoxy methyl propionate; The cyclic ester classes such as gamma-butyrolacton etc.
Aforementioned solvents (F) is from the viewpoint of coating and drying property, be preferably the organic solvent of 100 ℃～200 ℃ of boiling points, more preferably can use propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, cyclohexanone, ethyl lactate, butyl lactate, 3-ethoxyl ethyl propionate, 3-methoxy methyl propionate etc.
The solvent of foregoing example (F) can be used separately respectively or mix two or more use, take the general assembly (TW) of photosensitive composition of the present invention as benchmark can contain 60～90 % by weight, can preferably contain 70～85 % by weight.As long as in the scope of aforementioned solvents (F) in aforementioned 60～90 % by weight, while using the apparatus for coating coating of roll coater, rotary coating machine, slit rotary coating machine, slit type coater (sometimes also referred to as groove film coating machine), ink jet type etc., the effect that provides coating to improve.
(G) adjuvant
Photosensitive composition of the present invention can also comprise adjuvant.
Aforementioned additive (G) is optionally added as required, such as listing: other macromolecular compounds, surfactant, adhesion promoter, antioxidant, ultraviolet light absorber, deflocculant etc.
Concrete example as aforementioned other macromolecular compounds, can list: the thermoplastic resins such as the curable resins such as epoxy resin, maleimide resin, polyvinyl alcohol (PVA), polyacrylic acid, polyalkylene glycol monoalkyl ether, poly-fluoroalkyl acrylate, polyester, polyurethane etc.
Aforementioned surfactants can be used in the film forming of further raising photosensitive polymer combination, and can preferably use fluorine is surfactant or silicon-type surfactant etc.
Aforementioned silicon-type surfactant is such as have DC3PA, DC7PA, SH11PA, the SH21PA of eastern beautiful DOW CORNING organosilicon company limited, TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, the TSF-4452 etc. of organosilicon company limited of SH8400 Deng， GE Toshiba as commercially available product.Aforementioned fluorine is that surfactant is such as メ ガ ピ ス F-470, F-471, F-475, F-482, F-489 etc. as commercially available product You great Japanese ink chemical industrial company.The surfactant of foregoing example can be used separately respectively or combine two or more use.
Concrete example as aforementioned adhesion promoter, can list: vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-aminopropyl trimethoxysilane, APTES, 3-glycidoxypropyltrime,hoxysilane, 3-epoxypropoxy methyl dimethoxysilane, 2-(3, 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-methacryloxypropyl trimethoxy silane, 3-sulfydryl propyl trimethoxy silicane, 3-isocyanates propyl trimethoxy silicane, 3-isocyanate group propyl-triethoxysilicane etc.The adhesion promoter of foregoing example can be used separately respectively or combine two or more use.Aforementioned adhesion promoter can preferably contain 0.01～10 % by weight with respect to the general assembly (TW) of the solid constituent of photosensitive composition, can more preferably contain 0.05～2 % by weight.
The concrete example of aforementioned antioxidant, can list: 2, and 2 '-thiobis (4-methyl-6-tert-butylphenol), 2,6-di-tert-butyl-4-methy phenol etc.
Concrete example as aforementioned ultraviolet light absorber, can list: 2-(the 3-tert-butyl group-2-hydroxy-5-methyl base phenyl)-5-chlorobenzotriazole, alkoxy benzophenone etc.
Concrete example as aforementioned deflocculant, can list sodium polyacrylate etc.
the manufacture method of photosensitive composition
Below, for example the manufacture method of photosensitive composition of the present invention is described.
First, the pigment (a1) in aforementioned colorant (A) is mixed with solvent (F), use ball mill etc. disperses until the mean grain size of pigment is left and right below 0.2 μ m.Now, can make as required part or all of pigment dispersing agent (a3), alkali soluble resins (B), or (a2) dyestuff is mixed together, dissolves or disperse with (F) solvent.
To further add in the aforementioned dispersion liquid having mixed surplus (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D), crosslinking chemical (E) and (G) adjuvant as required of dyestuff (a2), alkali soluble resins and (F) solvent to form the concentration of regulation, can manufacture photosensitive composition of the present invention.
In addition, the invention provides a kind of color filter, this color filter is formed by aforementioned photosensitive composition manufacture.
Color filter of the present invention can obtain as follows: be coated with aforementioned photosensitive composition solution, carry out preliminary drying and obtain dry coating, this dry coating is implemented to develop after patterned exposure, and through above-mentioned operation, can access the constituent that is equivalent to photosensitive composition is pixel or the black matrix" of the color of colorant; In addition, by only repeatedly carrying out the above-mentioned operation that color filter needs number of color, can access color filter thus.
The formation of color filter and manufacture method are extensively known in this technical field, therefore can use it to manufacture color filter.
The present invention relates to the liquid crystal indicator that comprises aforementioned color filter
Foregoing liquid crystal display device, except comprising aforementioned color filter, also comprises structure well known by persons skilled in the art.That is the liquid crystal indicator that, can be suitable for color filter of the present invention includes in the present invention.As an example, can enumerate sends as an envoy to comprises the relative with the interval of regulation to electrode base board of thin film transistor (TFT) (TFT element), pixel electrode and oriented layer, and gap portion injects liquid crystal material and forms the transmission liquid crystal display device of liquid crystal layer betwixt.In addition, also has the reflective LCD device that is provided with reflection horizon between the substrate of color filter and dyed layer.
As another example, can list the TFT that matches on the transparency carrier that is included in color filter (thin film transistor (TFT): Thin Film Transistor) substrate and TFT substrate are fixed in the liquid crystal indicator backlight with color filter overlapping position.Aforementioned TFT substrate can comprise: the external frame being formed by the anti-photopolymer resin (light-proof resin) that surrounds the periphery surface of color filter; The liquid crystal layer being formed by the nematic liquid crystal being additional in external frame; A plurality of pixel electrodes that each region of liquid crystal layer is provided; Be formed with the transparent glass substrate of pixel electrode; With the polaroid forming on the exposing surface of transparent glass substrate.
Below, based on embodiment, the present invention will be described in more detail, yet following disclosed embodiments of the present invention are only example, and scope of the present invention is not limited by these embodiments.Scope of the present invention as shown in claims, and then comprise and the impartial meaning of the record of claims and scope in whole changes.In addition, in following embodiment, comparative example, represent that " % " and " part " of content refers to weight basis as long as no mentioning especially.
the manufacture of Production Example 1. pigment dispensing compositions
< pigment dispensing composition M1>
Using the pigment C.I. paratonere 254 of 12 weight portions, pigment dispersing agent DISPERBYK-2001 (manufacture of BYK company) 4.0 weight portions, mix 12 hours by ball mill as propylene glycol monomethyl ether 44 weight portions and propylene glycol monomethyl ether 40 weight portions of solvent, thereby its dispersion is produced to dispersible pigment dispersion M1.
the manufacture of embodiment 1 to 4 and comparative example 1 to 6. photosensitive composition
< embodiment 1>
By the < pigment dispensing composition M1>22.5 weight portion of aforementioned manufacture, the acid glycidyl methacrylate of modification and the copolymer resin of benzyl methacrylate (hydroxyl value 30mgKOH/g) 14 weight portions, KAYARAD DPHA (dipentaerythritol acrylate) (Nippon Kayaku K. K's manufacture) 4.5 weight portions, crosslinking chemical 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (1, 3, 4, 6-tetrakis (methoxymethyl) tetrahydroimidazo[4, 5-d] imidazole-2, 5 (1h, 3h)-dion e) (Powderlink1174, CYTEC company) 4.5 weight portions, Irgacure907 (BASF AG's manufacture) 0.3 weight portion, OXE-01 (BASF AG's manufacture) 0.7 weight portion, propylene glycol monomethyl ether 20.5 weight portions, propylene glycol monomethyl ether 34.0 weight portions mix, manufacture photosensitive composition.
< embodiment 2>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 80mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), crosslinking chemical 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< embodiment 3>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 180mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), crosslinking chemical 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< embodiment 4>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 40mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< comparative example 1>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 10mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< comparative example 2>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 20mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< comparative example 3>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 190mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< comparative example 4>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 200mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone (Powderlink1174, CYTEC company) 4.5 parts, 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
< comparative example 5>
34.0 parts of aforementioned < pigment dispensing composition M1>22.5 part, the glycidyl methacrylate of sour modification and 14 parts of the copolymer resins of benzyl methacrylate (hydroxyl value 80mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, propylene glycol monomethyl ethers are mixed, manufacture photosensitive composition.
< comparative example 6>
By aforementioned < pigment dispensing composition M1>22.5 part, 14 parts of the acid glycidyl methacrylate of modification and the copolymer resins of benzyl methacrylate (hydroxyl value 80mgKOH/g), 4.5 parts of KAYARAD DPHA (Nippon Kayaku K. K's manufacture), 4.5 parts of crosslinking chemical YDCN-500-80P (KUKDO chemistry is manufactured), 0.3 part of Irgacure907 (BASF AG's manufacture), 0.7 part of OXE-01 (BASF AG's manufacture), 20.5 parts of propylene glycol monomethyl ether, 34.0 parts of mixing of propylene glycol monomethyl ether, manufacture photosensitive composition.
experimental example 1: developing powder and adhering mensuration
With the photosensitive composition of manufacturing in previous embodiment 1 to 4 and comparative example 1 to 6, manufacture color filter.
Particularly, with method of spin coating, aforementioned photosensitive composition is coated on respectively to glass substrate (Corning Incorporated's manufacture of 2 square inches, " EAGLE XG ") upper after, be positioned on heating plate, at the temperature of 100 ℃ and kept 3 minutes, form film.Then, on aforementioned film, mounting has the pattern of transmittance stepped variation in 1～100% scope and a test photomask of 1 μ m～50 μ m live width/intermittent pattern, by and the interval of testing between photomask be made as 100 μ m, irradiation ultraviolet radiation.Now, ultraviolet light source uses and to comprise that the whole 1KW high-pressure sodium lamp of g, h, i ray is with 100mJ/cm
2illumination irradiate, do not use special light filter.By having irradiated aforementioned ultraviolet thin film dipped in the KOH of pH10.5 aqueous solution developing solution 2 minutes, make its development.Use distilled water washing to be coated with after the glass plate of aforementioned film, be blown into nitrogen and be dried, in the heating furnace of 200 ℃, heat 25 minutes, produce color filter.The film thickness of the aforementioned color filter producing is 2.0 μ m.
< adhesiveness >
By optical microscope evaluation, generate pattern time, the degree with peeling on pattern as described below is evaluated, and is shown in following < table 1>.
Zero: on pattern, do not peel off
△: have 1～3 to peel off on pattern
*: on pattern, there are 4 to peel off above
< developing powder >
While measure developing, non-exposure portion is dissolved in the required time of developer solution completely.
the mensuration of experimental example 2. solvent resistances
Solvent resistance is used the color filter of similarly manufacturing with aforementioned < experimental example 1> to measure.
< solvent resistance >
Solvent resistance is measured as follows: the color filter of similarly manufacturing with aforementioned < experimental example 1> is cut into after the size of 1 square inch, in the 1-METHYLPYRROLIDONE of 23 ℃, flood 30 minutes, use colorimeter (Olympus Co., Ltd's manufacture, OSP-200) to measure aberration △ E*ab value before dipping and afterwards.
The results are shown in < table 1> of previous experiments example 1,2.
[table 1]
| ? | Adhesiveness | Developing powder | Solvent resistance |
| Embodiment 1 | ○ | 11 | 6.3 |
| Embodiment 2 | ○ | 15 | 4.5 |
| Embodiment 3 | ○ | 23 | 2.7 |
| Embodiment 4 | ○ | 12 | 5.2 |
| Comparative example 1 | × | 9 | 14.2 |
| Comparative example 2 | × | 12 | 13.5 |
| Comparative example 3 | ○ | 57 | 3.2 |
| Comparative example 4 | ○ | 72 | 4.6 |
| Comparative example 5 | × | 35 | 14.2 |
| Comparative example 6 | ○ | 87 | 4.3 |
Shown in aforementioned table 1, use the color filter of the photosensitive composition of embodiments of the invention 1 to 4 all to express excellent result in adhesiveness, developing powder and solvent resistance.On the contrary, the not enough comparative example 1 of 30mgKOH/g of hydroxyl value sum of alkali soluble resins and optical polymerism compound is, in the situation of comparative example 2, adhesiveness reduces, solvent resistance is bad, surpasses the comparative example 3 of 180mgKOH/g, in the situation of comparative example 4, developing powder is significantly low.Containing the comparative example 5 of crosslinking chemical have that adhesiveness reduces, also low problem of developing powder.Use in the situation of comparative example 6 of other crosslinking chemicals, developing powder is significantly low.
Therefore, confirmed the high-quality color filter that reliability, throughput rate and yield improve, developing powder fast, sensitivity excellent of photosensitive composition of the present invention on can manufacturing process.
Claims (8)
1. a photosensitive composition, comprises colorant (A), alkali soluble resins (B), optical polymerism compound (C), Photoepolymerizationinitiater initiater (D), crosslinking chemical (E) and solvent (F), it is characterized in that,
The hydroxyl value of described alkali soluble resins (B) is 30～180mgKOH/g, and described crosslinking chemical (E) represents by following Chemical formula 1,
[Chemical formula 1]
In described Chemical formula 1,
Described R
1and R
2alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently,
Described A is hydrocarbon ring or replacement or the unsubstituted heterocycle that replacement or unsubstituted carbon number are 2～6,
Substituting group is alkyl, amino, ether, ketone group or ester group,
Two described substituting groups can connect and form condensed ring,
The heteroatoms containing in heterocycle is O, N or S.
2. photosensitive composition according to claim 1, is characterized in that, described photosensitive composition comprises with respect to the general assembly (TW) of solid constituent:
The described colorant (A) of 5～60 % by weight;
The described alkali soluble resins (B) of 10～80 % by weight;
The described optical polymerism compound (C) of 5～45 % by weight;
Total content with respect to alkali soluble resins (B) and optical polymerism compound (C) is the described Photoepolymerizationinitiater initiater (D) of 0.1～40 % by weight,
General assembly (TW) with respect to solid constituent is the described crosslinking chemical (E) of 0.1～15 % by weight,
General assembly (TW) with respect to photosensitive composition is the described solvent (F) of 60～90 % by weight.
3. photosensitive composition according to claim 1, is characterized in that, described crosslinking chemical (E) represents by following Chemical formula 2, chemical formula 3, chemical formula 4 or chemical formula 5,
[Chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
In described chemical formula, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9and R
10alkyl or the naphthenic base of the straight or branched of H, C1～C8 independently.
4. photosensitive composition according to claim 1, it is characterized in that, described crosslinking chemical is one or more in the choosing group that freely following compound forms: 1, 3, 4, 6-tetra-(methoxy) imidazolidine also [4, 5-d] imidazoles-2, 5 (1h, 3h)-diketone, 1, two (the methoxy)-imidazolidinones of 3-, two (methoxies) (oxo dimethylene) urea, 3, two (butoxymethyl) tetrahydrochysene-4H-1 of 5-, 3, 5-oxadiazine-4-ketone, 1, 3, 4, 6-tetra-(butoxymethyl) imidazolidine also (4, 5-d) imidazoles-2, 5 (1H, 3H) diketone, 1, two (methoxy) 2-ketone benzimidaozoles of 3-, 1, two (methoxy)-1 of 3-, 3-basudin-2-ketone, 1, two (ethoxyl methyl) imidazolidin-2-ones of 3-, 1, two (the 2-methyl-prop oxygen ylmethyl) imidazolidin-2-ones and 1 of 3-, 3, 4, 6-tetra-(2-methyl-prop oxygen ylmethyl)-3a, 6a-glyoxalidine also [4, 5-d] imidazoles-2, 5-diketone.
5. photosensitive composition according to claim 1, is characterized in that, described photosensitive composition also comprises adjuvant.
6. photosensitive composition according to claim 5, it is characterized in that, described adjuvant is to select one or more in the group that free macromolecular compound, surfactant, adhesion promoter, antioxidant, ultraviolet light absorber and deflocculant form.
7. a color filter, is characterized in that, described color filter is manufactured by the photosensitive composition described in any one in claim 1～6.
8. a liquid crystal indicator, is characterized in that, described liquid crystal indicator comprises color filter claimed in claim 7.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020120086968A KR20140020495A (en) | 2012-08-08 | 2012-08-08 | A colored photosensitive resin composition, color filter and liquid crystal display device having the same |
| KR10-2012-0086968 | 2012-08-08 |
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| CN103576455A true CN103576455A (en) | 2014-02-12 |
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| JP (1) | JP2014035547A (en) |
| KR (1) | KR20140020495A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110308617A (en) * | 2018-03-20 | 2019-10-08 | 东友精细化工有限公司 | Photosensitive composition, colour filter and image display device comprising it |
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| KR101656000B1 (en) * | 2014-02-24 | 2016-09-08 | 제일모직 주식회사 | Photosensitive resin composition, light blocking layer using the same and color filter |
| KR101982080B1 (en) * | 2015-03-23 | 2019-05-24 | 동우 화인켐 주식회사 | A colored photo sensitive resin composition, color filter and liquid crystal display device having the same |
| WO2018043215A1 (en) * | 2016-09-02 | 2018-03-08 | 日産化学工業株式会社 | Thioglycoluril compound, and method for producing same |
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| CN101390017A (en) * | 2006-05-31 | 2009-03-18 | 三菱化学株式会社 | Heat curable composition for protective film, cured product, and liquid crystal display device |
| JP2010128011A (en) * | 2008-11-25 | 2010-06-10 | Hitachi Chemical Dupont Microsystems Ltd | Positive photosensitive resin composition, method for producing patterned cured film using the same, and electronic component |
| CN101937172A (en) * | 2009-06-29 | 2011-01-05 | Jsr株式会社 | Positive radiation line sensitive compositions, cured film, interlayer dielectric and forming method thereof, display element and siloxane polymer |
| CN102540729A (en) * | 2010-12-30 | 2012-07-04 | 第一毛织株式会社 | Hard mask composition, method of forming pattern, and semiconductor integrated circuit device including pattern |
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|---|---|---|---|---|
| JP2000298339A (en) * | 1999-04-14 | 2000-10-24 | Dainippon Printing Co Ltd | Photosensitive resin composition |
| JP4569759B2 (en) * | 2004-02-23 | 2010-10-27 | 日産化学工業株式会社 | Dye-containing resist composition and color filter using the same |
| JP5573724B2 (en) * | 2011-02-18 | 2014-08-20 | Ｊｓｒ株式会社 | Coloring composition, color filter and display element |
-
2012
- 2012-08-08 KR KR1020120086968A patent/KR20140020495A/en not_active Application Discontinuation
-
2013
- 2013-07-30 CN CN201310325754.XA patent/CN103576455A/en active Pending
- 2013-08-06 JP JP2013163253A patent/JP2014035547A/en active Pending
- 2013-08-07 TW TW102128262A patent/TW201407282A/en unknown
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| US4031057A (en) * | 1975-04-28 | 1977-06-21 | Monsanto Company | Liquid aminoplast polyfunctional resin compositions |
| CN101390017A (en) * | 2006-05-31 | 2009-03-18 | 三菱化学株式会社 | Heat curable composition for protective film, cured product, and liquid crystal display device |
| JP2010128011A (en) * | 2008-11-25 | 2010-06-10 | Hitachi Chemical Dupont Microsystems Ltd | Positive photosensitive resin composition, method for producing patterned cured film using the same, and electronic component |
| CN101937172A (en) * | 2009-06-29 | 2011-01-05 | Jsr株式会社 | Positive radiation line sensitive compositions, cured film, interlayer dielectric and forming method thereof, display element and siloxane polymer |
| CN102540729A (en) * | 2010-12-30 | 2012-07-04 | 第一毛织株式会社 | Hard mask composition, method of forming pattern, and semiconductor integrated circuit device including pattern |
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| CN110308617A (en) * | 2018-03-20 | 2019-10-08 | 东友精细化工有限公司 | Photosensitive composition, colour filter and image display device comprising it |
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| KR20140020495A (en) | 2014-02-19 |
| TW201407282A (en) | 2014-02-16 |
| JP2014035547A (en) | 2014-02-24 |
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