CN101743514A - Color composition and color filter using the same - Google Patents
Color composition and color filter using the same Download PDFInfo
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- CN101743514A CN101743514A CN200880024876A CN200880024876A CN101743514A CN 101743514 A CN101743514 A CN 101743514A CN 200880024876 A CN200880024876 A CN 200880024876A CN 200880024876 A CN200880024876 A CN 200880024876A CN 101743514 A CN101743514 A CN 101743514A
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- Prior art keywords
- transparent resin
- polymerizable monomer
- photo
- curable transparent
- coloured composition
- Prior art date
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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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Disclosed is a color composition containing a polymerizable monomer having an ethylenically unsaturated double bond, a transparent resin having an ethylenically unsaturated double bond, a coloring agent and an organic solvent. The ratio of the solubility parameter MSP of the polymerizable monomer relative to the double-bond equivalent weight MDC of the polymerizable monomer, namely MSP/MDC is not more than 0.10, and the ratio of the solubility parameter PSP of the transparent resin relative to the double-bond equivalent weight PDC of the transparent resin, namely PSP/PDC is not less than 0.012. The polymerizable monomer is contained in an amount of 30-150% by weight relative to the transparent resin. Also disclosed is a color filter which comprises, on a substrate, a filter segment made of the color composition.
Description
Technical field
The present invention relates to be adapted to constitute the coloured composition and the color filter that use in the manufacturing of color filter of color liquid crystal display arrangement, colour pick-up tube element etc.
Background technology
In recent years, liquid crystal indicator is applied in television monitor purposes, individual computer monitor purposes, the mobile device purposes etc.For employed color filter in the liquid crystal indicator,, require level more and more higher to brightness, excitation etc. in order to improve colorrendering quality.In addition, because liquid crystal indicator used for a long time,, also very strong to the requirement of the quality aspect relevant such as thermotolerance and photostability with patience therefore for color filter.And then, employed coloured composition in the manufacturing for color filter, the coating homogeneity when forming filter section of all kinds, sensitivity, development, pattern form require level also more and more higher.Improve the concentration of the colouring matters such as pigment in the coloured composition in order to tackle these requirements, and reduce the constituent concentration of light-cured resin and monomer accordingly.
In addition, the demand for the sustainable growth of tackling liquid crystal indicator in the manufacturing of color filter, can also shorten the production time by simplifying working process.
But, increase the concentration of the colouring matter in the coloured composition and reduce the photo-curable composition, perhaps shorten ultraviolet irradiation time for the manufacturing process of simplifying color filter, can cause solidifying bad painted filming.Here, solidify bad painted filming and be meant, the part of fully solidifying in the position that should solidify is filmed with curing the painted of inadequate partially mixed existence.By carrying out the alkali development to solidifying bad painted filming, can the generation aberration between part of fully solidifying and the inadequate part of curing.
People of the present invention attempt solving the problem that produces above-mentioned aberration by prior art.
At first, studied disclosed method in the TOHKEMY 2005-099488 communique, promptly: use the photosensitive coloring composition of the Photoepolymerizationinitiater initiater that contains high sensitivity, even it is bad whether also can to solve the curing of filming with seldom photocuring composition and ultraviolet irradiation amount seldom.But, use the Photoepolymerizationinitiater initiater of high sensitivity, even increase its content,, thereby become and solidify saturatedly because the amount of the photocuring composition that solidifies is limited, do not resulted from the cured coating film that solidifies bad aberration yet.
Secondly, studied disclosed photosensitive composite in TOHKEMY 2002-318453 communique, this photosensitive composite in specific ratio comprise the A composition that constitutes by multifunctional (methyl) acrylic monomers, the B composition that constitutes by polymkeric substance, the C composition that constitutes by monofunctional monomer and by at least a D composition that constitutes in Photoepolymerizationinitiater initiater and the light sensitizer with the structural unit that comprises specific cyclic hydrocarbon, have alkali patience.But because the contained B composition that is made of polymkeric substance can't solidify by the ultraviolet ray irradiation in this photosensitive composite, so alkali produces to film when developing and peels off, and produces very big aberration on the contrary.
Summary of the invention
Therefore, the object of the present invention is to provide by the high coloured composition of UV-induced curable and possess and do not see and result from the color filter of the filter section that solidifies bad aberration.
According to 1 aspect of the present invention, a kind of coloured composition is provided, it is characterized in that, it is the coloured composition that contains the polymerizable monomer with ethylenic unsaturated double-bond, the transparent resin with ethylenic unsaturated double-bond, colouring matter and organic solvent, the solubility parameter M of described polymerizable monomer
SPTwo key equivalent M with respect to described polymerizable monomer
DCRatio M
SP/ M
DCBe below 0.10, the solubility parameter P of described transparent resin
SPTwo key equivalent P with respect to described transparent resin
DCRatio P
SP/ P
DCBe more than 0.012, the content of described polymerizable monomer be described transparent resin weight 30～150%.
In addition, according to another aspect of the present invention, provide the color filter that on substrate, possesses the filter section that forms by coloured composition of the present invention.
Embodiment
At first, coloured composition of the present invention is specifically described.
Coloured composition of the present invention contains polymerizable monomer with ethylenic unsaturated double-bond (below, be called polymerizable monomer), has transparent resin, colouring matter and the organic solvent of ethylenic unsaturated double-bond.
And, in the coloured composition of the present invention, the solubility parameter M of polymerizable monomer
SPTwo key equivalent M with respect to polymerizable monomer
DCRatio M
SP/ M
DCBe below 0.10, the solubility parameter P of transparent resin
SPTwo key equivalent P with respect to transparent resin
DCRatio P
SP/ P
DCBe more than 0.012, and polymerizable monomer exist with 30～150% ratio of transparent resin weight.
The solubility parameter M of the polymerizable monomer among the present invention
SPAccording to " Port リ マ one エ Application ジ ニ ア リ Application グ ア Application De サ イ エ Application ス (Polymer Eng.﹠amp; Sci.) " the 14th the volume, No. 2 (1974), P.148～P.154 in the record the Fedors formula, be that following formula (1) is calculated.
Formula (1): M
SP=(∑ Δ e
i/ ∑ Δ v
i)
1/2
In the formula (1), Δ e
iFor belonging to the evaporation energy under atom or group 25 ℃, Δ v
iBe the molar volume under atom or group 25 ℃.
Δ e in the formula (1)
iWith Δ v
iFor giving i atom in the molecule and certain numerical value of group.The typical example of Δ e that table 1 expression is given atom or group and the numerical value of Δ v.
Table 1
Annotate: Ph represents phenyl ring
The following calculating of solubility parameter of the acrylic acid 2-hydroxy methacrylate shown in the following structural formula (2) for example.
Formula (2):
That is, because acrylic acid 2-hydroxy methacrylate comprises 1=CH
2, 1-CH=, 1-COO-, 2-CH
2-, 1-OH (C is adjacent), so its ∑ Δ e
iBe 1030+1030+4300+1180 * 2+5220=13940 (cal/mol).In addition, ∑ Δ v
iBe 28.5+13.5+18+16.1 * 2+13=105.2 (cm
3/ mol).Therefore, the solubility parameter M of acrylic acid 2-hydroxy methacrylate
SPBe (∑ Δ e
i/ ∑ Δ v
i)
1/2=11.5 (cal/cm
3).
In addition, the solubility parameter of the potpourri of the polymerizable monomer more than 2 kinds is calculated according to following formula:
M
SPmix＝a
M1M
SPM1+a
M2M
SPM2+a
M3M
SPM3+…+a
MnM
SPMn
Wherein,
M
SPmixBe the solubility parameter of the potpourri of polymerizable monomer,
M
SPM1Be the solubility parameter of polymerizable monomer 1,
M
SPM2Be the solubility parameter of polymerizable monomer 2,
M
SPM3Be the solubility parameter of polymerizable monomer 3,
…
M
SPMnBe the solubility parameter of polymerizable monomer n,
a
M1Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 1,
a
M2Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 2,
a
M3Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 3,
…
a
MnWeight fraction for the polymerizable monomer n in the potpourri of polymerizable monomer.
In addition, two key equivalents of polymerizable monomer calculate according to following formula, and it becomes the yardstick of two key amounts contained in polymerizable monomer 1 molecule.If be the compound of same molecular amount, then the numerical value of two key equivalents is more little, and the amount of two keys is many more.
Two key equivalents of＜polymerizable monomer 〉=＜molecular weight of polymerizable monomer 〉/＜double key number in polymerizable monomer 1 molecule 〉
In addition, two key equivalents of polymerizable monomer potpourri calculate according to following formula more than 2 kinds:
M
DCmix＝a
M1M
DCM1+a
M2M
DCM2+a
M3M
DCM3+…+a
MnM
DCMn
Wherein,
M
DCmixBe two key equivalents of the potpourri of polymerizable monomer,
M
DCM1Be two key equivalents of polymerizable monomer 1,
M
DCM2Be two key equivalents of polymerizable monomer 2,
M
DCM3Be two key equivalents of polymerizable monomer 3,
…
M
DCMnBe two key equivalents of polymerizable monomer n,
a
M1Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 1,
a
M2Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 2,
a
M3Be the weight fraction of the polymerizable monomer in the potpourri of polymerizable monomer 3,
…
a
MnWeight fraction for the polymerizable monomer n in the potpourri of polymerizable monomer.
The solubility parameter M of polymerizable monomer
SPTwo key equivalent M with respect to polymerizable monomer
DCRatio M
SP/ M
DCGreater than 0.1 o'clock, carry out the curing of film coated surface by the ultraviolet ray irradiation, can crack in the cured coating film etc.M
SP/ M
DCBe preferably more than 0.03, more preferably more than 0.05 and less than 0.07.
Two key equivalents of contained polymerizable monomer are preferably 120～350 in the coloured composition of the present invention, and more preferably 150～300.Two key equivalents of polymerizable monomer carried out the curing of film coated surface less than 120 o'clock by the ultraviolet ray irradiation, can crack in the cured coating film sometimes etc.In addition, two key equivalents of polymerizable monomer were greater than 350 o'clock, and the sensitivity of coloured composition is insufficient, even irradiation ultraviolet radiation is filmed and also can not solidified sometimes.
As polymerizable monomer, can illustration acrylic acid 2-hydroxy methacrylate (solubility parameter (hereinafter referred to as SP): 11.5, two key equivalents (hereinafter referred to as DC): 116), 2-hydroxyethyl methacrylate (SP:13.2, DC:130), acrylic acid 2-hydroxy propyl ester (SP:11.7, DC:130), methacrylic acid 2-hydroxy propyl ester (SP:10.7, DC:143), cyclohexyl methacrylate (SP:9.3, DC:154), cyclohexyl methacrylate (SP:9.2, DC:168), polyethyleneglycol diacrylate (SP:9.9, DC:151), polyethylene glycol dimethacrylate (SP:9.8, DC:165), pentaerythritol triacrylate (SP:12.2, DC:99), pentaerythritol acrylate trimethyl (SP:11.6, DC:113), trimethylolpropane triacrylate (SP:9.9, DC:100), trimethylol-propane trimethacrylate (SP:11.4, DC:113), dipentaerythritol acrylate (SP:10.8, DC:97), dipentaerythritol hexamethyl acrylate (SP:10.4, DC:111), acrylic acid three ring ester (SP:11.6 in the last of the ten Heavenly stems, DC:84), methacrylic acid three ring ester (SP:11.0 in the last of the ten Heavenly stems, DC:98), melamine acrylate (SP:11.3, DC:149), melamine methacrylate (SP:10.9, DC:163), epoxy acrylate (SP:8.7, DC:295), epoxy methacrylates (SP:8.6, DC:309) various acrylate and methacrylate such as, acrylic acid (SP:11.1, DC:72), methacrylic acid (SP:10.7, DC:86), styrene (SP:7.9, DC:104), vinyl acetate (SP:8.9, DC:86), Methacrylamide (SP:14.2, DC:71), Methacrylamide (SP:13.3, DC:85), N hydroxymethyl acrylamide (SP:15.4, DC:101), N-methylol methacrylamide (SP:14.5, DC:115), vinyl cyanide (SP:11.1, DC:53) etc.Can also use a part of carbochain caprolactone, oxirane, the resulting material of epoxy pronane modification with described polymerizable monomer.
Polymerizable monomer can use a kind separately, also can mix use more than 2 kinds.
Transparent resin among the present invention (hereinafter referred to as the photo-curable transparent resin) with ethylenic unsaturated double-bond, be have the ethylenic unsaturated double-bond and be preferably more than 80% in total wavelength region may internal transmission factor of 400～700nm of visible region, the resin more than 95% more preferably.The solubility parameter of photo-curable transparent resin and polymerizable monomer similarly calculate according to the formula of Fedors.But, under the situation of photo-curable transparent resin, form (mol ratio) according to theoretical monomer shown in the following formula, that constitute this resin and calculate.
The solubility parameter P of photo-curable transparent resin
SP=Wta * SPa+Wtb * SPb+Wtc * SPc
Wherein,
Wta: the mole fraction of monomer A,
Wtb: the mole fraction of monomers B,
Wtc: the mole fraction of monomer C,
…
SPa: the solubility parameter of monomer A,
SPb: the solubility parameter of monomers B,
SPc: the solubility parameter of monomers B,
…
For example, if the formation monomer of photo-curable transparent resin is a methacrylic acid (molecular weight: 86, solubility parameter: 10.7) 70 weight %, methyl methacrylate (molecular weight: 100, solubility parameter: 9.3) during 30 weight %, then this dissolving resin degree parameter is (mole fraction of methacrylic acid) * (solubility parameter of methacrylic acid)+(mole fraction of methyl methacrylate) * (solubility parameter of methyl methacrylate)=(70/86)/(70/86+30/100) * 10.7+ (30/100)/(70/86+30/100) * 9.3=10.32.
In addition, the solubility parameter of the potpourri of photo-curable transparent resin is calculated according to following formula more than 2 kinds:
P
SPmix＝a
P1M
SPM1+a
P2M
SPM2+a
P3M
SPM3+…+a
PnM
SPMn
Wherein,
P
SPmixBe the solubility parameter of the potpourri of photo-curable transparent resin,
P
SPS1Be the solubility parameter of photo-curable transparent resin 1,
P
SPS2Be the solubility parameter of photo-curable transparent resin 2,
P
SPS3Be the solubility parameter of photo-curable transparent resin 3,
…
M
SPSnBe the solubility parameter of photo-curable transparent resin n,
a
P1Be the weight fraction of the photo-curable transparent resin 1 in the potpourri of photo-curable transparent resin,
a
P2Be the weight fraction of the photo-curable transparent resin 2 in the potpourri of photo-curable transparent resin,
a
P3Be the weight fraction of the photo-curable transparent resin 3 in the potpourri of photo-curable transparent resin,
…
a
PnWeight fraction for the photo-curable transparent resin n in the potpourri of photo-curable transparent resin.
In addition, two key equivalents of photo-curable transparent resin calculate according to following formula, and it is the yardstick of two key amounts contained in the 1 molecule photo-curable transparent resin.If the photo-curable transparent resin of same molecular amount, then the numerical value of two key equivalents is more little, and the amount of two keys is many more.
Two key equivalents of＜photo-curable transparent resin 〉=＜weight-average molecular weight of photo-curable transparent resin 〉/double key number in＜1 molecule photo-curable transparent resin 〉
Two key equivalents of the potpourri of photo-curable transparent resin calculate according to following formula more than 2 kinds:
P
DCmix＝a
P1P
DCP1+a
P2P
DCP2+a
P3P
DCP3+…+a
PnP
DCPn
Wherein,
P
DCmixBe two key equivalents of the potpourri of photo-curable transparent resin,
P
DCP1Be two key equivalents of photo-curable transparent resin 1,
P
DCP2Be two key equivalents of photo-curable transparent resin 2,
P
DCP3Be two key equivalents of photo-curable transparent resin 3,
…
P
DCPnBe two key equivalents of photo-curable transparent resin n,
a
P1Be the weight fraction of the photo-curable transparent resin 1 in the potpourri of photo-curable transparent resin,
a
P2Be the weight fraction of the photo-curable transparent resin 2 in the potpourri of photo-curable transparent resin,
a
P3Be the weight fraction of the photo-curable transparent resin 3 in the potpourri of photo-curable transparent resin,
…
a
PnWeight fraction for the photo-curable transparent resin n in the potpourri of photo-curable transparent resin.
The solubility parameter P of photo-curable transparent resin
SPTwo key equivalent P with respect to the photo-curable transparent resin
DCRatio P
SP/ P
DCBe 0.012 when following, the photo-curable of coloured composition reduces, and also can fully not solidify even irradiation ultraviolet radiation is filmed.P
SP/ P
DCBe preferably below 0.05, more preferably more than 0.015 and below 0.045.
Two key equivalents of contained photo-curable transparent resin are preferably 200～800 in the coloured composition of the present invention, and more preferably 300～700.Two key equivalents of photo-curable transparent resin carried out the curing of film coated surface less than 200 o'clock by the ultraviolet ray irradiation, can crack in the cured coating film sometimes etc.In addition, two key equivalents of photo-curable transparent resin can not get the sensitivity of sufficient coloured composition greater than 800 o'clock, also can fully not solidify even irradiation ultraviolet radiation is filmed.
As the photo-curable transparent resin, can use have hydroxyl, carboxyl, the substituent wire macromolecule of amino isoreactivity imported the resulting resins of photocrosslinking reaction group such as (methyl) acryloyl group, styryl with having isocyanate group, aldehyde radical, substituent (methyl) acyclic compound of epoxy radicals isoreactivity or cinnamic acid reaction in this wire macromolecule.In addition, can also use (methyl) acyclic compound that has a hydroxyl by hydroxy alkyl (methyl) acrylate etc. that the wire macromolecule that styrene-maleic anhydride copolymer or alpha-olefin-copolymer-maleic anhydride etc. contains acid anhydrides is carried out the material that half esterization obtains.
The photo-curable transparent resin can use a kind separately, also can mix use more than 2 kinds.
In the coloured composition of the present invention, the content of described polymerizable monomer be the photo-curable transparent resin weight 30～150%, and be preferably 50～100%.In the coloured composition of the present invention, the effect of main body is solidified in the polymerizable monomer performance, and auxiliary effect is solidified in the performance of photo-curable transparent resin.Compare with polymerizable monomer, photo-curable transparent resin itself is less for the influence of photocuring, on the other hand, because polymerizable monomer himself solidifies because of light, therefore stipulates its amount as mentioned above.Preferred balance contains photo-curable transparent resin and polymerizable monomer well.
If to using the formed irradiation ultraviolet radiation of filming of coloured composition of the present invention, then the ethylenic unsaturated double-bond that is had with the photo-curable transparent resin is a starting point, promote the polymerization of polymerizable monomer, shone filming of ultraviolet part and totally can not produce and solidify badly, fully solidify.Surpass in the amount of polymerizable monomer under 150% the situation of weight of described photo-curable transparent resin, then the photo-curable transparent resin as the starting point of the polymerization of polymerizable monomer is few, and polymerizable monomer can fully not solidify, and is therefore not preferred.In addition, the amount of polymerizable monomer less than 30% situation under, polymerizable monomer fully solidifies, but the absolute magnitude of polymerizable monomer reduces, it is insufficient that the curing of filming can become, therefore not preferred.
The photo-curable transparent resin can use by the amount that is 30～700 weight portions with respect to colouring matter 100 weight portions, is preferably 60～450 weight portions.
As colouring matter contained in the coloured composition of the present invention, organic pigment or inorganic pigment can be carried out mixing separately or more than 2 kinds use.In the middle of the pigment, preferred color emissivity height and high pigment, the particularly high pigment of heat-resisting decomposability of thermotolerance use organic pigment usually.
Below, number represent the object lesson of the organic pigment that can preferably use in the coloured composition of the present invention with pigment index (C.I.).
As the red colored composition that is used to form red filter joint, for example can use C.I. paratonere 7,9,14,41,48:1,48:2,48:3,48:4,81:1,81:2,81:3,97,122,123,146,149,168,177,178,180,184,185,187,192,200,202,208,210,215,216,217,220,223,224,226,227,228,240,246,254,255,264, red pigments such as 272.In red colored composition, can and use yellow uitramarine, orange pigment.
Yellow coloring composition as being used to form the yellow filter joint can use for example C.I. pigment yellow 1,2,3,4,5,6,10,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199 yellow uitramarines such as grade.
As the orange coloured composition that is used to form orange filter section, for example can use C.I. pigment orange 36,43,51,55,59, orange pigments such as 61.
As the green coloring composition that is used to form green filter joint, for example can use C.I. pigment Green 7,10,36, viridine greens such as 37.In green coloring composition, can and use yellow uitramarine.
As the blue colored composition that is used to form blue electric-wave filter joint, for example can use C.I. pigment blue 15,15:1,15:2,15:3,15:4,15:6,16,22,60, blue pigments such as 64.In blue colored composition can and with C.I. pigment violet 1, violet pigments such as 19,23,27,29,30,32,37,40,42,50.
As the cyan coloured composition that is used to form the cyan filter section, can use for example C.I. pigment blue 15: 1,15:2,15:4,15:3,15:6,16, blue pigments such as 81.
As the magenta coloured composition that is used to form the magenta filter section, can use for example violet pigment and red pigment such as C.I. pigment violet 1,19, C.I. paratonere 144,146,177,169,81.In the magenta coloured composition, can and use yellow uitramarine.
In addition, as inorganic pigment, can list metal oxide powder or metal sulfide powder or metal powders etc. such as barium sulphate, the flowers of zinc, lead sulfate, chrome yellow, zinc yellow, colcother (red iron oxide (III)), cadmium red, ultramarine, Prussian blue, chrome oxide green, cobalt green, umber, black, the synthetic iron oxide black of titanium, titanium dioxide, tri-iron tetroxide.In order in the balance that obtains chroma and brightness, to guarantee inorganic pigment and organic pigment to be used in combination good coating, sensitivity, development etc.
In order to mix colours, can contain dyestuff not reducing stable on heating scope in the coloured composition of the present invention.
As organic solvent contained in the coloured composition of the present invention, can list the 2-heptanone, the 4-heptanone, cyclohexanone, n-butyl acetate, isobutyl acetate, isoamyl acetate, n-Amyl acetate, methyl isobutyl ketone, normal butyl alcohol, ethylene glycol monomethyl ether, the ethylene glycol bisthioglycolate ethylether, the glycol monomethyl methyl ether, the glycol monomethyl propyl ether, the glycol monomethyl isopropyl ether, the ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol list ethylether, propylene glycol list propyl ether, propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters, N, dinethylformamide, 1,2, the 3-trichloropropane, ortho-chlorotolu'ene, o-xylene, m-xylene, 3-methoxyl-3-methyl isophthalic acid-butanols, 1, the 3-butylene glycol, the 3-methyl isophthalic acid, the 3-butylene glycol, the 2-methyl isophthalic acid, the 3-propane diol, diisobutyl ketone, ethylene glycol monobutyl ether, ethylene glycol mono hexyl ether, the ethylene glycol monobutyl ether acetic acid esters, the ethylene glycol bisthioglycolate butyl ether, the diglycol monotertiary methyl ether, carbiphene, diethylene glycol diethyl ether, the diglycol monotertiary isopropyl ether, the propylene glycol single-butyl ether, propylene-glycol diacetate, DPGME, dihydroxypropane single-ethyl ether, the single propyl ether of dipropylene glycol, the dipropylene glycol dimethyl ether, the tripropylene glycol monomethyl ether, the 3-ethoxyl ethyl propionate, 3-methoxyl butylacetic acid ester, 3-methoxyl-3-methyl butyl acetic acid esters, gamma-butyrolacton, N,N-dimethylacetamide, N-Methyl pyrrolidone, parachlorotoluene, adjacent diethylbenzene, between diethylbenzene, p-diethylbenzene, o-dichlorobenzene, m-dichlorobenzene, n-butylbenzene, sec-butylbenzene, tert-butyl benzene, cyclohexanol, methyl cyclohexanol etc.They can use separately or mix more than 2 kinds and use.Organic solvent can use by the amount that is 800～4000 weight portions with respect to 100 weight portions of the colouring matter in the coloured composition, is preferably 1000～2500 weight portions.
Can add Photoepolymerizationinitiater initiater in the coloured composition of the present invention.
As Photoepolymerizationinitiater initiater, can use 4-phenoxy group dichloroacetophenone, the 4-tert-butyl group-dichloroacetophenone, diethoxy acetophenone, 1-(4-isopropyl phenyl)-2-hydroxy-2-methyl propane-1-ketone, 1-hydroxycyclohexylphenylketone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-butane-acetophenones Photoepolymerizationinitiater initiaters such as 1-ketone; Benzoin class Photoepolymerizationinitiater initiaters such as benzoin, benzoin methylether, benzoin ethyl ether, benzoin iso-propylether, benzil dimethyl ketal; Benzophenone, benzoylbenzoic acid, benzoylbenzoic acid methyl esters, 4-phenyl benzophenone, dihydroxy benaophenonel, propylene acidylate benzophenone, 4-benzoyl-4 '-benzophenone Photoepolymerizationinitiater initiaters such as methyldiphenyl base sulfide; Thioxanthones, 2-clopenthixal ketone, 2-methyl thioxanthones, isopropyl thioxanthone, 2, thioxanthene ketone Photoepolymerizationinitiater initiaters such as 4-diisopropyl thioxanthones; 2,4,6-three chloro-s-triazines, 2-phenyl-4,6-two (trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-two (trichloromethyl)-s-triazine, 2-(p-methylphenyl)-4,6-two (trichloromethyl)-s-triazine, 2-piperonyl-4,6-two (trichloromethyl)-s-triazine, 2,4-two (trichloromethyl)-6-styryl-s-triazine, 2-(naphthalene-1-yl)-4,6-two (trichloromethyl)-s-triazine, 2-(4-methoxyl-naphthalene-1-yl)-4,6-two (trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, 2,4-trichloromethyl (4 '-methoxyl-styrene)-triazines Photoepolymerizationinitiater initiaters such as 6-triazine; Borate family Photoepolymerizationinitiater initiater, carbazoles Photoepolymerizationinitiater initiater, imidazoles Photoepolymerizationinitiater initiater etc.Photoepolymerizationinitiater initiater can use by the amount that is 5～200 weight portions with respect to 100 weight portions of the colouring matter in the coloured composition, is preferably 10～150 weight portions.
Above-mentioned Photoepolymerizationinitiater initiater can be used singly or two or more kinds mixed; as sensitizer; can also and use α-acyl oxime ester (α-acyloxime ester), acylphosphine oxide, aminomethyl phenyl glyoxylic ester, benzil, 9; 10-phenanthrenequione, camphorquinone, EAQ, 4; 4 '-diethyl between phthalophenone (4; 4 '-diethyl isophthalophenone), 3; 3 '; 4; 4 '-four (t-butyl peroxy carbonyl) benzophenone, 4, compounds such as 4 '-diethylamino benzophenone.Sensitizer can use by the amount that with respect to 100 weight portions of the Photoepolymerizationinitiater initiater in the coloured composition is 0.1～60 weight portion.
Coloured composition of the present invention can be distributed to the colouring matter more than a kind or 2 kinds in described photo-curable transparent resin and the organic solvent with described polymerizable monomer and Photoepolymerizationinitiater initiater and make imperceptibly by using various diverting devices such as triple-roller mill, two roller mill, sand milling, kneader, masher.In addition, the coloured composition that contains colouring matter more than 2 kinds can also mix and makes by being dispersed in the material that obtains in described photo-curable transparent resin and the organic solvent respectively imperceptibly by each colouring matter.When being distributed in described photo-curable transparent resin and organic solvent as colouring matter pigment, can suitably containing resin type pigment dispersing agent, surfactant, pigment derivative etc. and disperse auxiliary agent.Dispersing aid is because the effect that the pigment to the dispersing of pigments excellence, after preventing to disperse condenses again is big, therefore when adopting when using dispersing aid obtains pigment dispersing in described photo-curable transparent resin and organic solvent coloured composition, can obtain the color filter of transparency excellence.
As the resin type pigment dispersing agent, be to comprise pigment compatibility position and have the position of compatibility and play to be adsorbed in the material that pigment makes pigment effect of stable dispersion in pigment carrier with pigment carrier with the character that is adsorbed in pigment.As the resin type pigment dispersing agent, specifically can adopt polyurethane, polycarboxylates such as polyacrylate, the unsaturated polyester acid amides, poly carboxylic acid, poly carboxylic acid (part) amine salt, the poly carboxylic acid ammonium salt, the poly carboxylic acid alkylamine salt, polysiloxane, the long-chain polyaminoamide phosphate, the polycarboxylate of hydroxyl or their modifier, oiliness spreading agents such as the acid amides that forms by poly-(rudimentary alkylene imines) and pet reaction or its salt with free carboxyl, (methyl) acrylic acid-styrol copolymer, (methyl) acrylic acid-(methyl) acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol (PVA), water soluble resin or water-soluble high-molecular compounds such as polyvinylpyrrolidone, polyesters, the modified polyacrylate class, the ethylene oxide/propylene oxide additive compound, phosphoric acid esters etc., they can use separately or mix more than 2 kinds and use.
As surfactant, can list the anionic surface active agent such as monoethanolamine, polyoxyethylene alkyl ether phosphate of alkali salt, sodium alkyl naphthalene sulfonate, alkyl diphenyl base ether sodium disulfonate, lauryl sulfate monoethanolamine, triethanolamine lauryl sulfate, Texapon Special, stearic acid monoethanolamine, odium stearate, NaLS, the styrene-propene acid copolymer of polyoxyethylene alkyl ether sulfate salt, neopelex, styrene-propene acid copolymer; Non-ionics such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylplenyl ether, polyoxyethylene alkyl ether phosphate, Tween-60, polyethylene glycol monolaurate; Alkyl quaternary ammonium salts or their cationic surfactants such as ethylene oxide adduct; Amphoteric surfactantes such as alkyl betaine, alkyl imidazoline such as alkyl dimethyl aminoacetic acid betaine, they can be used singly or two or more kinds mixed.
Pigment derivative is to import substituting group and the compound that obtains in organic pigment, as organic pigment, generally also comprises flaxen aromatic series polycyclic compunds such as the naphthalene class that is not called as pigment, anthraquinone class.As pigment derivative, can use the compound of record in Japanese kokai publication sho 63-305173 communique, Japanese Patent Publication 57-15620 communique, Japanese Patent Publication 59-40172 communique, Japanese Patent Publication 63-17102 communique, the special fair 5-9469 communique of Japan etc., they can use separately or mix more than 2 kinds and use.
Above-mentioned dispersing aid can use by the amount that is 0.1～40 weight portion with respect to colouring matter 100 weight portions, is preferably 0.1～30 weight portion.
Can contain the non-photosensitive transparent resin in the coloured composition of the present invention, with dissolubility or the tolerance of control for developer solution.The non-photosensitive transparent resin be do not have the ethylenic unsaturated double-bond and in total wavelength region may of 400～700nm of visible region transmissivity be preferably more than 80%, the transparent resin more than 95% more preferably.Non-photosensitive transparent resin as such comprises thermoplastic resin and heat-curing resin, and they can use separately or mix more than 2 kinds and use.
As the non-photosensitive thermoplastic resin, for example can list butyral resin, styrene-maleic acid copolymer, haloflex, chlorinated polypropylene, Polyvinylchloride, vinyl chloride-vinyl-acetic ester multipolymer, polyvinyl acetate base ester, polyurethanes resin, vibrin, acrylic resin, alkyd resin, styrene resin, polyamide, rubber resin, thermoprene resinoid, cellulose family, polybutadiene, polyimide resin etc.In addition, as the non-photosensitive heat-curing resin, for example can list epoxy resin, benzoguanamine resin, Abietyl modified maleic acid resin, Abietyl modified fumaric resin, melamine resin, urea resin, phenolics etc.
The non-photosensitive thermoplastic resin can use by the amount that is 10～1000 weight portions with respect to colouring matter 100 weight portions, is preferably 50～800 weight portions.
In addition, can contain the storage-stable agent in the coloured composition of the present invention so that composition through the time viscosity stabilization.As the storage-stable agent, for example can list quinhydrones, methylnaphthohydroquinone, 2,5-di-tert-butyl hydroquinone, tertiary butylated hydroquinone, the tert-butyl group-β-benzoquinones, tertiary butylated hydroquinone, 2, phosphine oxide compounds such as phosphine compound, tri octyl phosphine oxide, triphenylphosphine oxidation thing such as organic acid such as aliquat, lactic acid, oxalic acid such as quinhydrones based compounds such as 5-diphenyl-1,4-benzoquinone, benzyl trimethyl chloride, diethyl hydramine and methyl ether thereof, tributylphosphine, tri octyl phosphine, tricyclohexyl phosphine, triphenylphosphine, tribenzyl phosphine; Phosphate compound, tert-butyl catechols etc. such as triphenyl, three nonyl phenyl phosphate ester.The storage-stable agent can be used by the amount that with respect to 100 weight portions of the colouring matter in the coloured composition is 0.1～10 weight portion.
In addition, in order to improve the adaptation with substrate, can also contain driving fit improving agents such as silane coupling agent.
As silane coupling agent; can list vinyl three ('beta '-methoxy ethoxy) silane; the vinyl Ethoxysilane; vinyl silanes classes such as vinyltrimethoxy silane; γ-methacryloxypropyl trimethoxy silane etc. (methyl) acryloyl group silanes; β-(3; 4-epoxy radicals cyclohexyl) ethyl trimethoxy silane; β-(3; 4-epoxy radicals cyclohexyl) methyltrimethoxy silane; β-(3; 4-epoxy radicals cyclohexyl) ethyl triethoxysilane; β-(3,4-epoxy radicals cyclohexyl) methyl triethoxysilane; γ-glycidoxypropyltrime,hoxysilane; γ-epoxy radicals silicone hydride classes such as glycidoxy propyl-triethoxysilicane; N-β (aminoethyl) γ-An Bingjisanjiayangjiguiwan; N-β (aminoethyl) gamma-aminopropyl-triethoxy-silane; N-β (aminoethyl) γ-aminopropyl methyldiethoxysilane; gamma-aminopropyl-triethoxy-silane; γ-An Bingjisanjiayangjiguiwan; N-phenyl-γ-An Bingjisanjiayangjiguiwan; amino silane classes such as N-phenyl-gamma-aminopropyl-triethoxy-silane; γ-Qiu Jibingjisanjiayangjiguiwan; Thiosilicane classes such as γ-sulfydryl propyl-triethoxysilicane etc.Silane coupling agent can use by the amount that is 0.01～10 weight portion with respect to 100 weight portions of the colouring matter in the color composition for color filter, is preferably 0.05～5 weight portion.
For coloured composition of the present invention, the preferred devices such as centrifuging, sintered filter, membrane filter that use are removed the above oversize grain of 5 μ m, are preferably the above oversize grain of 1 μ m, the more preferably above oversize grain of 0.5 μ m and the dust of sneaking into.
In addition, do not filmed uniformly in order not produce crawling, coloured composition of the present invention preferably will be adjusted into below the 10mPas 25 ℃ of viscosity of using E type viscosity meter to record with rotating speed 20rpm down, more preferably be adjusted into more than the 1mPas and below the 8mPas.
Coloured composition of the present invention can be made the form of solvent develop type or the painted erosion resistant of alkali developable.
Then, the color filter that possesses the filter section that is formed by coloured composition of the present invention is described.
Color filter is to form the filter section that is selected from least 2 looks among R (red), G (green), B (indigo plant), Y (Huang), M (magenta), the C (green grass or young crops) to form on transparent or reflection substrate.Filter section of all kinds can use coloured composition of the present invention to form by photoetching process.
As transparency carrier, can adopt resin plates such as glass plate or polycarbonate, polymethylmethacrylate, polyethylene terephthalate.
As reflection substrate, can adopt silicon or on described transparency carrier, be formed with aluminium, silver, substrate that silver/copper/palldium alloy film etc. forms.
When forming filter section of all kinds by photoetching process, by coating processes such as spraying process or spin-coating method, slot coated method, rolling methods, will be as above-mentioned solvent develop type or the painted resist of alkali developable and the coloured composition that makes is that the mode of 0.2～5 μ m is applied on the substrate by dry film thickness.As required, by contact with this film or contactless state under the mask of the pattern that is provided with regulation, to drying film carry out ultraviolet exposure., be impregnated in solvent or alkaline developer or by spraying etc. developer solution sprayed remove uncured portion form desired pattern after, other colors are repeated same operation, can make color filter thereafter.And then, in order to promote the polymerization of painted resist, can also implement heating as required.By photoetching process, can make the color filter higher than print process precision.
As developing method, can adopt spray development method, spray development method, dipping (dipping) development method, soak and put (puddle contains liquid) development method etc.
In addition, in order to improve the ultraviolet exposure sensitivity, after above-mentioned painted erosion resistant coating drying, also can be will coatings such as water-soluble or alkali soluble resin, for example polyvinyl alcohol (PVA) or water soluble acrylic resin drying and after formation prevents to hinder the film of polymerization because of oxygen, carry out ultraviolet exposure.
Below, illustrate in greater detail the present invention with embodiment, following embodiment to interest field of the present invention without any restriction.In addition, " part " expression " weight portion " among the embodiment.
Synthesis example 1
In reaction vessel, pack into 560 parts of cyclohexanone, nitrogen injection is heated to 80 ℃ on one side in container on one side, under same temperature, with 47.0 parts of 34.0 parts of methacrylic acids, 23.0 parts of methyl methacrylates, 45.0 parts of n-BMAs, glycerin monomethyl acrylic ester and 2, the potpourri that 2 '-azoisobutyronitrile is 4.0 parts dripped with 1 hour, carried out polyreaction.
After drip finishing,, be added on 1.0 parts of azoisobutyronitriles of dissolving in 55 parts of the cyclohexanone then and the solution that obtains, continue reaction 1 hour down at 80 ℃ again, obtain copolymer solution again 80 ℃ of reactions 3 hours down.
Then, with respect to 338 parts of the copolymer solutions that obtains, the potpourri with 120.0 parts of 32.0 parts of 2-methacryl ethyl isocyanates, 0.4 part of dibutyl tin laurate and cyclohexanone under 70 ℃ dripped with 3 hours.
After being cooled to room temperature, with the about 2g of photo-curable transparent resin solution that obtains as sample, 180 ℃ of following heat dryings 20 minutes, measure nonvolatile component, based on this measured value, in synthetic photo-curable transparent resin solution, add cyclohexanone so that nonvolatile component is 20 weight %, preparation photo-curable transparent resin solution A.The weight-average molecular weight of the photo-curable transparent resin that obtains is 20000, and two key equivalents are 470, and solubility parameter is 11.0.
Synthesis example 2
In reaction vessel, pack into 520 parts of cyclohexanone, nitrogen injection is heated to 80 ℃ on one side in container on one side, under same temperature, with 66.0 parts of 7.0 parts of methacrylic acids, 7.0 parts of methyl methacrylates, 63.0 parts of methacrylic acid 2-hydroxyl ethyl esters, glycerin monomethyl acrylic ester and 2, the potpourri that 2 '-azoisobutyronitrile is 4.0 parts dripped with 1 hour, carried out polyreaction.
After drip finishing,, be added on 1.0 parts of azoisobutyronitriles of dissolving in 70 parts of the cyclohexanone then and the solution that obtains, continue reaction 1 hour down at 80 ℃ again, obtain copolymer solution again 80 ℃ of reactions 3 hours down.
Then, with respect to 220 parts of the copolymer solutions that obtains, the potpourri with 220.0 parts of 56.0 parts of 2-methacryl ethyl isocyanates, 0.4 part of dibutyl tin laurate and cyclohexanone under 70 ℃ dripped with 3 hours.
After being cooled to room temperature, similarly add cyclohexanone so that nonvolatile component is 20 weight %, preparation photo-curable transparent resin solution B with synthesis example 1.The weight-average molecular weight of the photo-curable transparent resin that obtains is 20000, and two key equivalents are 270, and solubility parameter is 11.0.
Synthesis example 3
In reaction vessel, pack into 480 parts of cyclohexanone, nitrogen injection is heated to 80 ℃ on one side in container on one side, under same temperature, with 15.0 parts of 32.0 parts of methacrylic acids, 24.0 parts of methyl methacrylates, 16.0 parts of methacrylic acid n-butyl, 48.0 parts of benzyl methacrylates, glycerin monomethyl acrylic ester and 2, the potpourri that 2 '-azoisobutyronitrile is 4.0 parts dripped with 1 hour, carried out polyreaction.
After drip finishing,, be added on 1.0 parts of azoisobutyronitriles of dissolving in 80 parts of the cyclohexanone then and the solution that obtains, continue reaction 1 hour down at 80 ℃ again, obtain copolymer solution again 80 ℃ of reactions 3 hours down.
Then, with respect to 445 parts of the copolymer solutions that obtains, the potpourri with 55.0 parts of 14.0 parts of 2-methacryl ethyl isocyanates, 0.4 part of dibutyl tin laurate and cyclohexanone under 70 ℃ dripped with 3 hours.
After being cooled to room temperature, similarly add cyclohexanone so that nonvolatile component is 20 weight %, preparation photo-curable transparent resin solution C with synthesis example 1.The weight-average molecular weight of the photo-curable transparent resin that obtains is 20000, and two key equivalents are 1000, and solubility parameter is 10.8.
Embodiment 1
After the potpourri of following composition mixed equably, use the beaded glass of diameter 1mm, disperse 5 hours with sand mill after, filter with the filtrator of 5 μ m, prepare the copper phthalocyanine dispersion.
The composition of potpourri (copper phthalocyanine dispersion):
Epsilon-copper phthalocyanine (C.I. pigment blue 15: 6) 12.00 parts
(BASF system " Heliogen Blue L-6700F ")
2.40 parts of spreading agents (Japanese Lubrizol corporate system " Solsperse20000 ")
28.10 parts of the photo-curable transparent resin solution A that obtains in the synthesis example 1
57.50 parts of cyclohexanone
Then, the potpourri of following composition is mixed after evenly, the filtrator filtration with 1 μ m obtains the coloured composition that forms as blue erosion resistant adjustment.The composition of coloured composition (be with the coloured composition total amount 100 weight ratio) is as shown in table 2.
The composition of potpourri (coloured composition):
45.05 parts of copper phthalocyanine dispersions
18.05 parts of the photo-curable transparent resin solution A that obtains in the synthesis example 1
4.80 parts of caprolactone modification trimethylolpropane triacrylates
2.50 parts of Photoepolymerizationinitiater initiaters
(Ciba Specialty Chemicals corporate system " IRGACURE907 ")
0.20 part of sensitizer (hodogaya chemical Co., Ltd. system " EAB-F ")
0.01 part of levelling agent
(BYK-Chemie Japan Co., Ltd. system " BYK-323 ")
29.40 parts of cyclohexanone
Embodiment 2～9 and comparative example 1～7
The composition of pigment, spreading agent, photo-curable transparent resin solution, solvent is changed to the ratio shown in the table 2 (be with the pigment dispersion total amount 100 weight ratio), obtain pigment dispersion of all kinds similarly to Example 1.
Then, except the composition with pigment dispersion, photo-curable transparent resin solution, polymerizable monomer, Photoepolymerizationinitiater initiater, sensitizer, organic solvent, levelling agent changes to the ratio of table shown in 3-1, the 3-2 (be with the coloured composition total amount 100 weight ratio), obtain the coloured composition that forms as erosion resistant adjustment of all kinds similarly to Example 1.
Table 2
| Blue 1 | Blue 2 | Blue 3 | Red 1 | Red 2 | Green 1 | Green 2 | |
| ??PB15:6 | ??12.00 | ??12.00 | ??12.00 | ||||
| ??PR254 | ??11.29 | ??11.29 | |||||
| ??PR177 | ??1.82 | ??1.82 | |||||
| ??PY199 | ??0.44 | ??0.44 | |||||
| ??PG36 | ??7.22 | ??7.22 | |||||
| ??PY150 | ??5.22 | ??5.22 | |||||
| Spreading agent | ??2.40 | ??2.40 | ??2.40 | ??2.40 | ??2.40 | ??2.40 | ??2.40 |
| Resin A | ??28.10 | ??20.20 | ??25.80 | ||||
| Resin B | ??28.10 | ||||||
| Resin C | ??28.10 | ??20.20 | ??25.80 | ||||
| Cyclohexanone | ??57.50 | ??57.50 | ??57.50 | ??63.84 | ??63.84 | ??59.36 | ??59.36 |
| Add up to | ??100.00 | ??100.00 | ??100.00 | ??100.00 | ??100.00 | ??100.00 | ??100.00 |
In the table 2,
PB15:6=epsilon-copper phthalocyanine (C.I. pigment blue 15: 6) (BASF system " Heliogen BlueL-6700F ");
PR254=diketopyrrolopyrroles pigment (C.I. paratonere 254) (Ciba SpecialtyChemicals corporate system " Irgaphor Red B-CF ");
PR177=anthraquinone class pigment (C.I. paratonere 177) (Ciba Specialty Chemicals corporate system " Cromophtal Red A2B ");
PY199=anthraquinone class pigment (C.I. pigment yellow 199) (Ciba Specialty Chemicals corporate system " Cromophtal Yellow GT-AD ");
PG36=copper halide phthalocyanine pigment (C.I. pigment green 36) (Toyo Ink manufacturing company system " LionolGreen 6YK ");
PY150=monoazo class pigment (C.I. pigment yellow 150) (Lanxess corporate system " Fanchon FastYellow Y-5688 ")
Spreading agent=Japanese Lubrizol corporate system " Solsperse20000 ";
The photo-curable transparent resin solution A that obtains in Resin A=synthesis example 1;
The photo-curable transparent resin solution B that obtains in resin B=synthesis example 2;
The photo-curable transparent resin solution C that obtains in the resin C=synthesis example 3.
Among table 3-1, the 3-2,
Monomer A=caprolactone modification trimethylolpropane triacrylate (DAICEL-CYTEC corporate system " Ebecryl 2047 ", solubility parameter: 10.6, two key equivalents: 201);
Monomers B=oxirane modification trimethylolpropane triacrylate
(East Asia Synesis Company system " ARONIX M-350 ", solubility parameter: 10.1, two key equivalents: 143);
Monomer C=trimethylolpropane triacrylate (Xin Zhong village chemical company system " NK ester A-TMPT, " solubility parameter: 10.5, two key equivalents: 99);
The photo-curable transparent resin solution A that obtains in Resin A=synthesis example 1;
The photo-curable transparent resin solution B that obtains in resin B=synthesis example 2;
The photo-curable transparent resin solution C that obtains in the resin C=synthesis example 3;
Photoepolymerizationinitiater initiater=Ciba Specialty Chemicals corporate system " IRGACURE 907 ";
Sensitizer=hodogaya chemical Co., Ltd. system " EAB-F ";
Levelling agent=BYK-Chemie Japan corporate system " BYK-323 ".
Use spinner, the erosion resistant of all kinds that obtains in embodiment 1～9 and the comparative example 1～7 is coated on the thick glass substrate of 100mm * 100mm, 0.7mm, forming thickness is filming of 2.0 μ m.Then, after carrying out 20 minutes prebake under 70 ℃, carry out 100mJ/cm
2Ultraviolet exposure.After using microspectrophotometer (Olympus Optical Co Ltd.'s system " OSP-SP100 ") to measure the spectral transmission of the photocuring film that obtains, impregnated in 0.25% sodium hydrate aqueous solution.Flood after 2 minutes, reuse microspectrophotometer and measure spectral transmission, calculate aberration Δ Eab.In addition, dipping is after 2 minutes in 0.25% sodium hydrate aqueous solution, use the develop observation of spot of optical microscope, by 4 grades (◎: do not observe development spot, zero: observe less and light development spot, △: observe on the whole light development spot, *: observe dense development spot on the whole) estimate.The result is as shown in table 4.
Table 4
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | Embodiment 8 | |
| Color | Blue | Blue | Blue | Blue | Red | Green | Blue | Blue |
| Aberration Δ Eab | ??0.69 | ?1.10 | ??1.21 | ??2.58 | ?0.68 | ?0.91 | ??2.55 | ??2.66 |
| The development spot | ??◎ | ?○ | ??○ | ??○ | ?◎ | ?◎ | ??○ | ??○ |
| Embodiment 9 | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | |
| Color | Blue | Blue | Blue | Blue | Blue | Blue | Red | Green |
| Aberration Δ Eab | ??0.65 | ?7.14 | ??8.12 | ??9.01 | ?5.57 | ?8.11 | ??10.25 | ??11.41 |
| The development spot | ??◎ | ?△ | ??× | ??× | ?△ | ?× | ??× | ??× |
The cured coating film that the coloured composition that obtains in using cured coating film that the coloured composition that obtains among the embodiment 1～6 forms and using comparative example 1～7 forms is compared, aberration Δ Eab before and after the dipping of sodium hydrate aqueous solution is less, do not observe the generation of development spot, the result is good.
And, the cured coating film that uses the coloured composition that obtains among the embodiment 7～9 to make, with the approaching use level of preferred range under, aberration Δ Eab compares greatly with most preferred embodiment 9, the generation of development spot is compared also with embodiment 9 and is observed.
As mentioned above, because coloured composition of the present invention fully solidifies by the ultraviolet ray irradiation, therefore the cured coating film that uses coloured composition of the present invention to form is brought into play sufficient tolerance for alkaline developer.Consequently, aberration disappears in the face of the filter section that color filter possessed, and can obtain good liquid crystal indicator.Stably obtain the effect that good liquid crystal indicator can produce following excellence: the fraction defective of manufacturing line reduces, and deals with the liquid crystal indicator market of the demand sustainable growth that causes because of growing up fast by the raising of cost reduction and growing amount.
Claims (4)
1. a coloured composition is characterized in that, contains the polymerizable monomer with ethylenic unsaturated double-bond, the transparent resin with ethylenic unsaturated double-bond, colouring matter and organic solvent; The solubility parameter M of described polymerizable monomer
SPTwo key equivalent M with respect to described polymerizable monomer
DCRatio M
SP/ M
DCBe below 0.10, the solubility parameter P of described transparent resin
SPTwo key equivalent P with respect to described transparent resin
DCRatio P
SP/ P
DCBe more than 0.012, the content of described polymerizable monomer be described transparent resin weight 30～150%.
2. coloured composition according to claim 1 is characterized in that, two key equivalent M of polymerizable monomer
DCBe 120～350.
3. coloured composition according to claim 1 and 2 is characterized in that, two key equivalent P of transparent resin
DCBe 200～800.
4. color filter, it possesses on substrate by any filter section that described coloured composition forms in the claim 1～3.
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| JP189736/2007 | 2007-07-20 | ||
| JP2007189736A JP5075510B2 (en) | 2007-07-20 | 2007-07-20 | Coloring composition and color filter using the same |
| PCT/JP2008/062836 WO2009014044A1 (en) | 2007-07-20 | 2008-07-16 | Color composition and color filter using the same |
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| CN104423149A (en) * | 2013-09-06 | 2015-03-18 | 三星Sdi株式会社 | Photosensitive Resin Composition and Color Filter Using the Same |
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| JP5266958B2 (en) * | 2008-08-22 | 2013-08-21 | 凸版印刷株式会社 | Color filter for liquid crystal display |
| TW201031713A (en) * | 2009-02-13 | 2010-09-01 | Toyo Ink Mfg Co | The coloring composition for color filters and color filters |
| JP5663878B2 (en) * | 2009-02-18 | 2015-02-04 | Jsr株式会社 | Colored radiation-sensitive composition, color filter, and color liquid crystal display element |
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| JP2002107930A (en) * | 2000-09-28 | 2002-04-10 | Toppan Printing Co Ltd | Photosensitive resin composition |
| JP4195329B2 (en) * | 2003-03-24 | 2008-12-10 | 大日本印刷株式会社 | Pigment dispersion for coloring resist, photosensitive coloring composition, and color filter |
| JP4597693B2 (en) * | 2004-12-24 | 2010-12-15 | 東洋インキ製造株式会社 | Blue coloring composition for color filter and color filter |
| CN100543585C (en) * | 2004-12-24 | 2009-09-23 | 东洋油墨制造株式会社 | Color composition for color filter and color filter |
| JP4597692B2 (en) * | 2005-02-07 | 2010-12-15 | 東洋インキ製造株式会社 | Coloring composition for color filter and color filter |
| JP5246994B2 (en) * | 2005-08-01 | 2013-07-24 | 東洋インキＳｃホールディングス株式会社 | Photosensitive composition and color filter |
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2007
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- 2008-07-16 WO PCT/JP2008/062836 patent/WO2009014044A1/en active Application Filing
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104423149A (en) * | 2013-09-06 | 2015-03-18 | 三星Sdi株式会社 | Photosensitive Resin Composition and Color Filter Using the Same |
| CN104423149B (en) * | 2013-09-06 | 2019-10-15 | 三星Sdi株式会社 | Photosensitive resin composition and the colour filter for using it |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101431502B1 (en) | 2014-08-20 |
| TWI432797B (en) | 2014-04-01 |
| CN101743514B (en) | 2013-09-11 |
| JP2009025634A (en) | 2009-02-05 |
| TW200912396A (en) | 2009-03-16 |
| KR20100039279A (en) | 2010-04-15 |
| JP5075510B2 (en) | 2012-11-21 |
| WO2009014044A1 (en) | 2009-01-29 |
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