CN107844029A - Photosensitive composition, colour filter and image display device - Google Patents

Photosensitive composition, colour filter and image display device Download PDF

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Publication number
CN107844029A
CN107844029A CN201710796753.1A CN201710796753A CN107844029A CN 107844029 A CN107844029 A CN 107844029A CN 201710796753 A CN201710796753 A CN 201710796753A CN 107844029 A CN107844029 A CN 107844029A
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mentioned
chemical formula
photosensitive composition
alkyl
colour filter
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CN107844029B (en
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金荣圣
吴相旼
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

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

Abstract

The present invention provides a kind of photosensitive composition, colour filter and image display device, the photosensitive composition is characterised by, comprising the alkali soluble resins containing the repeat unit represented by chemical formula 1 with containing selected from the compound group represented by chemical formula 2 into one or more of group compound Photoepolymerizationinitiater initiater.In the chemical formula 1, R1And R2It is each independently hydrogen atom or methyl, R3For the residue containing carboxylic acid obtained by being derived as acid anhydrides, in the chemical formula 2, R4~R13It is each independently hydrogen, halogen, C1~C20Alkyl, C6~C20Aryl, C1~C20Alkoxy, C7~C40Aryl alkyl, C1~C20Hydroxy alkyl, C2~C40Hydroxy alkoxy alkyl or C3~C20Cycloalkyl.

Description

Photosensitive composition, colour filter and image display device
Technical field
The present invention relates to a kind of photosensitive composition, utilize the colour filter and image display device of its manufacture.
Background technology
In general, in image display device, in order to realize that coloured image is shown, using with correspondence image display member The colour filter for multiple dyed layers that the mode of multiple pixels of part configures.
Such colour filter can't be formed at thin film transistor (TFT) (the Thin Film with switch element Transistor:Hereinafter referred to as TFT) substrate (hereinafter referred to as TFT substrate) side for being formed, and be formed in and TFT substrate phase Pair and configure opposing substrate side.
However, by color filter arrangement in the case of opposing substrate side, arranged with the position of each pixel electrode in TFT substrate Arrange and remarkable, and aperture opening ratio diminishes.Further, since colour filter and the distance between liquid crystal layer are larger, therefore occur because from inclining The problem of display quality caused by the incident light of tilted direction reduces.It is such in order to solve the problems, such as, Japanese Unexamined Patent Publication 09-73078 COA (Color Filter on Array (colour filter on the array)) mode for forming colour filter on the tft substrate is utilized in number It is such to solve the problems, such as.
When forming colour filter in above-mentioned TFT substrate, need to form contact hole (Contact hole, conducting in process Road), therefore actual conditions are, it is necessary to develop the technology for adjusting above-mentioned contact hole.
In addition, in the case of forming colour filter in above-mentioned TFT substrate, may be sent out in etching work procedure and agent treatment Show bad caused by the raw unstability by pixel film, thus actual conditions are, it is necessary to which developing improves above-mentioned display not Good technology.
Ebrean Registered Patent the 1st, 541,542 is related to a kind of photosensitive composition, it is characterised in that in order to Overlapping (Overlap) difference of height (Ra) of the dyed layer formed by photosensitive composition is adjusted, comprising specific heavy The adhesive resin of molecular weight.
However, for above-mentioned document, although solving the problems, such as development residue, but in addition to that, Wu Fati For for showing bad solution, and it is basic without cognition to for should when forming colour filter in above-mentioned TFT substrate The problem of contact hole of regulation.
It is therefore desirable to develop improve comprehensively various pictures show it is bad, and can adjust above-mentioned contact hole size and The photosensitive composition of shape.
Prior art literature
Patent document
Ebrean Registered Patent the 1,541,542nd (2015.07.28)
The content of the invention
Problem to be solved
It is an object of the invention to provide a kind of photosensitive composition, and it improves the colour filter of manufacture COA modes The display for the picture that may occur during device is bad, and the excellent contact hole of alignment precision can be formed on R, G, B-tree adipose membrane.
In addition, the present invention provides colour filter and image the display dress manufactured using above-mentioned photosensitive composition Put.
The method for solving problem
Photosensitive composition of the invention for reaching above-mentioned purpose is characterised by, comprising containing following The alkali soluble resins of repeat unit represented by chemical formula 1 with containing selected from the compound group represented by following chemical formula 2 into One or more of group compound Photoepolymerizationinitiater initiater：
[chemical formula 1]
(in above-mentioned chemical formula 1,
R1And R2Hydrogen atom or methyl are each independently,
R3For the residue containing carboxylic acid obtained by being derived as acid anhydrides)
[chemical formula 2]
(in above-mentioned chemical formula 2,
R4~R13It is each independently hydrogen, halogen, C1~C20Alkyl, C6~C20Aryl, C1~C20Alkoxy, C7 ~C40Aryl alkyl, C1~C20Hydroxy alkyl, C2~C40Hydroxy alkoxy alkyl or C3~C20Cycloalkyl).
In addition, the present invention provides the colour filter of the solidfied material comprising above-mentioned photosensitive composition and includes the filter The image display device of color device.
Invention effect
Photosensitive composition of the invention for reaching above-mentioned purpose passes through comprising containing specific structure Photoepolymerizationinitiater initiater represented by the alkali soluble resins and specified chemical formula of repeat unit, so as to improvement manufacture COA modes Colour filter when the display of picture that may occur it is bad and can form the excellent contact of alignment precision on R, G, B-tree adipose membrane The advantages of hole.
In addition, utilize the colour filter of the photosensitive composition manufacture of the present invention and the image comprising the colour filter Display device has the bad effect of the display for improving picture.
Brief description of the drawings
Fig. 1 is the process chart for forming colour filter by COA modes using the photosensitive composition of the present invention.
Symbol description
1：TFT substrate
2：Pattern of pixels
3：TFT elements
4：Nitride film (SiNx)
Embodiment
Hereinafter, the present invention is illustrated in more detail.
In the present invention, when point out a certain component positioned at it is another form " on " when, it not only includes a certain component and another structure Into other components between the situation of contact, in addition to two components being present.
In the present invention, when pointing out a certain inscape of certain a part of "comprising", it means, as long as no especially opposite Record, then can further include other inscapes, rather than other inscapes are excluded.
<Photosensitive composition>
The mode of the present invention is related to a kind of photosensitive composition, comprising containing 1 table of following chemical formula The alkali soluble resins of the repeat unit shown with containing selected from the compound group represented by following chemical formula 2 into group in one The Photoepolymerizationinitiater initiater of kind above compound.
[chemical formula 1]
(in above-mentioned chemical formula 1,
R1And R2Hydrogen atom or methyl are each independently,
R3For the residue containing carboxylic acid obtained by being derived as acid anhydrides)
[chemical formula 2]
(in above-mentioned chemical formula 2,
R4~R13It is each independently hydrogen, halogen, C1~C20Alkyl, C6~C20Aryl, C1~C20Alkoxy, C7 ~C40Aryl alkyl, C1~C20Hydroxy alkyl, C2~C40Hydroxy alkoxy alkyl or C3~C20Cycloalkyl).
Alkali soluble resins
The alkali soluble resins of the present invention is characterised by, contains the repeat unit represented by following chemical formula 1.
Above-mentioned alkali soluble resins typically has the function that the reactivity and alkali-solubility because of light or heat, can be used as with coloring Agent plays a role for the decentralized medium of the solid constituent of representative and performs the function of binder resin.
[chemical formula 1]
(in above-mentioned chemical formula 1,
R1And R2Hydrogen atom or methyl are each independently,
R3For the residue containing carboxylic acid obtained by being derived as acid anhydrides.)
The alkali soluble resins of the present invention contains the repeat unit of above-mentioned chemical formula 1, has the following advantages that：By comprising above-mentioned In the case that the photosensitive composition of alkali soluble resins forms multicolour pattern, it can make by above-mentioned coloring phototonus tree The difference of height of pattern caused by colouring agent included in oil/fat composition minimizes and significantly improves flatness, can manufacture transmission Rate also excellent colour filter.
In addition, the glass transition temperature (Tg) of the alkali soluble resins containing the repeat unit represented by above-mentioned chemical formula 1 0 DEG C can be less than, in this case, the development of the photosensitive composition comprising the alkali soluble resins can be significantly improved Speed, and closing force is improved, so as to the effect with the difference of height problem that can suppress the pattern as caused by increasing developing powder Fruit.
Relative to alkali soluble resins entirety molar percentage, the content of the repeat unit represented by above-mentioned chemical formula 1 can be with For 50~90 moles of %, specially 55~85 moles of %, more specifically 60~75 moles of %.
The repeat unit represented by above-mentioned chemical formula 1 content in above range in the case of, having easily makes bag The advantages of glass transition temperature of alkali soluble resins containing the repeat unit is less than 0 DEG C.
According to an embodiment of the present invention, alkali soluble resins of the invention can be by that will contain the above-mentioned institute of chemical formula 1 The monomer (a1) of the repeat unit of expression and the copolymerizable monomer (a2) with unsaturated double-bond are copolymerized and manufactured.
The species of the above-mentioned copolymerizable monomer (a2) with unsaturated double-bond is not particularly limited.Concrete example can enumerate benzene Ethene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, meta-methoxy styrene, to methoxy Base styrene, adjacent vinyl benzyl methyl ether, a vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinyl benzyl Base glycidol ether, a vinylbenzyl glycidyl ether close to aromatic vinyls such as vinylbenzyl glycidyl ethers Thing；N- N-cyclohexylmaleimides, N- benzyl maleimides, N-phenylmaleimide, N- o-hydroxy-phenyl maleimides Between amine, N- between hydroxyphenyl-maleimides, N- p-hydroxybenzenes maleimide, N- o-methyl-phenyls maleimide, N- Methylphenylmaleimide, N- p-methylphenyls maleimide, N- o-methoxyphenyls maleimide, N- meta-methoxies The N- substituted maleimide amine compounds such as phenyl maleimide or N- p-methoxyphenyl maleimides；(methyl) propylene Sour methyl esters, (methyl) ethyl acrylate, (methyl) n-propyl, (methyl) isopropyl acrylate, (methyl) acrylic acid are just (methyl) alkyl acrylates such as butyl ester, (methyl) isobutyl acrylate, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate Base ester class；(methyl) acrylic acid ring pentyl ester, (methyl) cyclohexyl acrylate, the own ester of (methyl) acrylic acid 2- methyl, (methyl) third Olefin(e) acid 2- methyl cyclohexyls, three rings [5.2.1.0 2,6] decane -8- bases (methyl) acrylate, the rings of (methyl) acrylic acid 2- bis- Alicyclic (methyl) esters of acrylic acid such as amoxy ethyl ester or (methyl) isobornyl acrylate；(methyl) acrylic acid 2- hydroxyl second Ester, (methyl) acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 4- hydroxybutyls, (methyl) acrylic acid 2- hydroxyl -3- phenoxy groups Propyl ester or N- hydroxyethyl acrylamides etc. (methyl) Hydroxyethyl Acrylate class；(methyl) phenyl acrylate or (methyl) propylene Acid benzyl ester etc. (methyl) benzyl acrylate class；3- (methacryloxymethyl) oxetanes, 3- (methacryloxypropyl first Base) -3- Ethyloxetanes, 3- (methacryloxymethyl) -2- trifluoromethyls oxetanes, 3- (methacryls Oxygen methyl) -2- phenyl oxetanes, 2- (methacryloxymethyl) oxetanes or 2- (methacryloxypropyl first Base) the unsaturated oxetane compound such as -4- trifluoromethyl oxetanes etc..Above-mentioned monomer can be each individually or by two Kind combination of the above uses.
The content of the above-mentioned copolymerizable monomer (a2) with unsaturated double-bond is not particularly limited, for example, relative to In the monomer total moles percentage of polymerization alkali soluble resins, the content of the copolymerizable monomer with unsaturated double-bond can be 10 ~50 moles of %, preferably can be 25~40 moles of %.In the case where meeting above range, there is the glass transition of resin The advantages of temperature shows to be less than 0 DEG C and can minimize difference of height.
The manufacture method of the alkali soluble resins of another embodiment of the present invention is as follows.
In the past, the alkali soluble resins of photosensitive composition was in order to for forming development treatment process during pattern Used in alkaline developer have solubility, the ethylene unsaturated monomer with carboxyl is copolymerized as neccessary composition And manufacture.But there is main chain and include carboxyl to be difficult to manufacture glass in the alkali soluble resins formed by such manufacture method Change the problem of transition temperature is less than 0 DEG C of resin.
But alkali soluble resins of the invention can be present in side chain with carboxyl rather than participate in the main chain of polymerisation Mode is manufactured, it is thus possible to the alkali solubility tree that glass transition temperature is less than 0 DEG C is manufactured while suitable developability is assigned Fat.
On the other hand, in an embodiment of the manufacture method of above-mentioned alkali soluble resins, can include：(S1) by (methyl) The step of glycidyl acrylate (a1) polymerize with the monomer (a2) with unsaturated double-bond；(S2) copolymerization of above-mentioned manufacture is made The step of thing reacts with the ethylene unsaturated monomer with carboxyl；And (S3) make it is anti-via the copolymer and acid anhydrides of above-mentioned reaction The step of answering.
Above-mentioned (S2) step is the step of assigning photo-curable to the alkali soluble resins of the present invention, in above-mentioned (S2) step, On the species of the ethylene unsaturated monomer with carboxyl, as long as the scope for playing its function is just not particularly limited, example Such as, (methyl) acrylic acid, ethyl acrylate and/or butyl acrylate etc. can be enumerated, is specifically as follows methacrylic acid.
Above-mentioned (S3) step is the step of assigning suitable acid number to the alkali soluble resins of the present invention, if more specifically It is bright, then it is that side chain of the hydroxyl for making to derive from the glycidyl of alkali soluble resins with anhydride reaction and in alkali soluble resins imports The step of carboxyl.
On the species of the acid anhydrides used in above-mentioned (S3) step, just it is not particularly limited as long as it plays function, example Such as, phthalic anhydride (Phthalic anhydride), (2- laurylene -1- bases) succinic anhydride ((2- can be enumerated Dodecen-1-yl) succinic anhydride), maleic anhydride (Maleic anhydride), succinic anhydride (Succinic Anhydride), citraconic anhydride (Citraconic anhydride), glutaric anhydride (Glutaric anhydride), methyl amber Amber acid anhydrides (Methylsuccinic anhydride), 3,3- dimethylated pentanedioic acid acid anhydrides (3,3-Dimethylglutaric Anhydride), phenylsuccinic acid acid anhydride (Phenylsuccinic anhydride), itaconic anhydride (Itaconic Anhydride), 3,4,5,6- tetrabydrophthalic anhydrides (3,4,5,6-Tetrahydrophthalic anhydride), partially Benzenetricarboxylic anhydride (Trimellitic anhydride) and hexahydrophthalic anhydride (Hexahydrophthalic Anhydride) etc., specifically, from the aspect of price and the easiness of reaction, maleic anhydride (Maleic can be used Anhydride), phthalic anhydride (Phthalic anhydride), trimellitic anhydride (Trimellitic Anhydride), succinic anhydride (Succinic anhydride), hexahydrophthalic anhydride (Hexahydrophthalic Anhydride), carbic anhydride (Carbic anhydride), more specifically, trimellitic anhydride can be used (Trimellitic anhydride), succinic anhydride (Succinic anhydride) and hexahydrophthalic anhydride (Hexahydrophthalic anhydride)。
In order to ensure the storage stability of compatibility and composition with the dyestuff included in composition, according to above-mentioned system The acid number for making the alkali soluble resins of the invention of method manufacture can be 30~150mgKOH/g.In the acid of above-mentioned alkali soluble resins Value be less than 30mgKOH/g in the case of, photosensitive composition is likely difficult to ensure sufficient developing powder, more than In the case of 150mgKOH/g, reduced with the adaptation of substrate, the short circuit of pattern easily occurs, and occur with the compatibility of dyestuff Problem, it may occur however that the dyestuff in photosensitive composition separates out or the preservation of photosensitive composition is stable Property reduce and viscosity rise the problem of.
The content of alkali soluble resins containing the repeat unit represented by above-mentioned chemical formula 1 is for example with coloring phototonus resin It can be 1~80 weight % on the basis of feline amount in composition, be specifically as follows 5~75 weight %, more specifically Can be 10~70 weight %.In the case where above-mentioned alkali soluble resins content is in above range, the dissolubility in developer solution Fully and the formation of pattern is easy, and prevent the pixel portion of exposure portion film reduce and coming off for non-pixel portion can be expected Property become good effect.
Photoepolymerizationinitiater initiater
The present invention Photoepolymerizationinitiater initiater be characterised by, be selected from represented by following chemical formula 2 compound group into One or more of group.
[chemical formula 2]
(in above-mentioned chemical formula 2,
R4~R13It is each independently hydrogen, halogen, C1~C20Alkyl, C6~C20Aryl, C1~C20Alkoxy, C7 ~C40Aryl alkyl, C1~C20Hydroxy alkyl, C2~C40Hydroxy alkoxy alkyl or C3~C20Cycloalkyl).
Specifically, above-mentioned R4~R13Can be hydrogen, bromine, chlorine, iodine, methyl, ethyl, n-propyl, isopropyl independently of one another Base, normal-butyl, isobutyl group, the tert-butyl group, n-pentyl, isopentyl, n-hexyl, isohesyl, phenyl, naphthyl, xenyl, terphenyl Base, anthryl, indenyl, phenanthryl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, Hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxy-n-butyl, hydroxyisobutyl, hydroxyl n-pentyl, hydroxyl isopentyl, hydroxyl N-hexyl, hydroxyl isohesyl, hydroxymethoxy methyl, hydroxymethoxy ethyl, hydroxymethoxy propyl group, hydroxymethoxy fourth Base, hydroxyethoxymethyl, hydroxyl ethoxy ethyl, hydroxyethoxypropyl, hydroxyl-oxethyl butyl, hydroxyethoxypentyl Or hydroxyl-oxethyl hexyl, more specifically, above-mentioned R4Can be hydrogen, methyl, ethyl, propyl group or butyl；R5Can be methyl, Ethyl or propyl group；R6Can be methyl, ethyl, propyl group or butyl；R7~R13Can be hydrogen.
The Photoepolymerizationinitiater initiater of the present invention be selected from compound group represented by above-mentioned chemical formula 2 into group, so as to have Make the effect of sensitivity and curing degree raising.
In addition, the Photoepolymerizationinitiater initiater of the present invention is with the alkali soluble resins of the present invention by being used together, so as to such as Lower advantage：In the image display device of COA structures, the excellent contact hole of alignment precision can be formed on R, G, B-tree adipose membrane, And when to form above-mentioned resin film be the electric pathway of pixel electrode and active component (TFT), it can be ensured that utilize dry etching method R, G, B-tree fat when contact hole is formed and the indium zinc oxide (Indium Zinc Oxide, IZO) as pixel electrode is deposited The pattern stability of film, improve as bad for pixel caused by ensuring R, G, B broken string of high aperture.
Abovementioned alkyl refers to, is only made up of carbon and hydrogen atom, without degree of unsaturation, passes through singly-bound and the remainder of molecule With reference to straight or branched hydrocarbon free radical.Specifically, abovementioned alkyl can be the straight-chain or branch of carbon number 1~20 Chain-like alkyl, can be the straight-chain or branched-chain alkyl of carbon number 1~10, more specifically, Ke Yiwei more specifically The straight-chain or branched-chain alkyl of carbon number 1~6.As the example of such non-substituted alkyl, methyl, second can be enumerated Base, n-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group, amyl group, isopentyl, hexyl etc..Institute in abovementioned alkyl The more than one hydrogen atom contained can be by halogen atom, hydroxyl, mercapto (- SH), nitro, cyano group, substituted or non-substituted Amino, amidino groups, diazanyl or hydrazone group, carboxyl, sulfonic group, phosphate, C1~C20Alkyl, C1~C20Haloalkyl, C2~C20 Alkenyl, C2~C20Alkynyl, C1~C20Miscellaneous alkyl, C6~C20Aryl, C6~C20Aryl alkyl, C6~C20Heteroaryl Base or C6~C20Heteroaryl alkyl substitution.
Above-mentioned aryl refers to, the aromatic monocyclic or polycyclic hydrocarbon ring system being only made up of hydrogen and carbon, now, ring system can part or It is fully saturated.At least more than one hydrogen atom in above-mentioned aryl can be taken by the substituent same with the situation of abovementioned alkyl Generation.Above-mentioned aryl be remove a hydrogen and derived from aromatic hydrocarbon organic free radical, can include each ring in comprising 4 to 7, The specific monocyclic or condensed ring system for including 5 or 6 annular atoms, multiple aryl can also be included by singly linked form.Above-mentioned virtue Base can include 6~20 carbon atoms, can specifically include 6~18 carbon atoms.
Above-mentioned alkoxy can be oxygen-containing straight-chain or the branched alkane of each moieties with carbon number 1~20 Epoxide.Specifically, it can be the alkoxy with 1~10 carbon atom, can be with 1~4 carbon original more specifically The alkoxy of son.Above-mentioned Alkoxy can such as enumerate methoxyl group, ethyoxyl, propoxyl group, butoxy and tert-butoxy.It is above-mentioned Alkoxy can also be further substituted with by the more than one halogen atom of fluorine, chlorine or bromine etc and provide halogenated alkoxy.Make For such example, fluorine methoxyl group, chloromethane epoxide, trifluoromethoxy, trifluoro ethoxy, fluorine ethyoxyl, the oxygen of fluorine third can be enumerated Base etc..More than one hydrogen atom in above-mentioned alkoxy can be substituted by the substituent same with the situation of abovementioned alkyl.
Above-mentioned aryl alkyl refers to that the more than one hydrogen atom of abovementioned alkyl is substituted by above-mentioned aryl.Above-mentioned aryl alkane The carbon number of base can be 7~40, specifically, carbon number can be 7~28, more specifically, can be 7~ 24.
Above-mentioned hydroxy alkyl refers to, the OH- alkyl that hydroxyl is combined into alkyl defined above, above-mentioned hydroxy alkoxy base Alkyl refers to, the hydroxy alkyl-O- alkyl that above-mentioned hydroxy alkyl is linked with alkyl by oxygen.The carbon of above-mentioned hydroxy alkyl is former Subnumber can be 1~20, specifically, carbon number can be 1~10, more specifically, carbon number can be 1~ 6.Above-mentioned hydroxy alkoxy alkyl can be carbon number 2~40, and specifically, carbon number can be 2~20, more For body, carbon number can be 2~9.
It is also to include polycyclic system hydrocarbon that above-mentioned cycloalkyl, which not only includes monocyclic, the hydrogen of at least more than one in above-mentioned cycloalkyl Atom can be substituted by the substituent same with the situation of abovementioned alkyl.The carbon number of above-mentioned cycloalkyl can be 3~20, Specifically, carbon number can be 3~10, and more specifically, carbon number can be 3~8.
On the basis of the feline amount in photosensitive composition, above-mentioned optical polymerism initiator contains Amount can be 0.1~40 weight % relative to the content of alkali soluble resins and photopolymerizable compound, be specifically as follows 0.5~35 Weight %, more specifically can be 1~30 weight %.It is the situation in above range in the content of above-mentioned optical polymerism initiator Under, there is advantages below：Photosensitive composition comprising the optical polymerism initiator is by high-sensitivity, during exposure Between shorten, productivity ratio improves, and can maintain high-resolution, and the intensity of pixel portion and the flatness on pixel portion surface become good.
The photosensitive composition of one embodiment of the present invention can be with addition to above-mentioned Photoepolymerizationinitiater initiater The common optical polymerism initiator further polymerizeing comprising the photopolymerizable compound that can further include the present invention, Photopolymerization initiator can also be further included further according to needs.
Now, on the basis of photosensitive composition total solid content, the content of above-mentioned photopolymerization initiator It can be 0.1~40 weight % relative to the content of alkali soluble resins and photopolymerizable compound, be specifically as follows 0.5~35 weight % is measured, more specifically can be 1~30 weight %.Above-mentioned photopolymerization initiator content in above range in the case of, Sensitivity with the photosensitive composition comprising the photopolymerization initiator improves, and includes the coloring phototonus tree The advantages of productivity ratio of the colour filter of oil/fat composition manufacture improves.
The photosensitive composition of another embodiment of the present invention can further be included and is selected from by photopolymerization Property compound, colouring agent, one or more of the group of solvent and additive composition.
Photopolymerizable compound
The photosensitive composition of one embodiment of the present invention can further include photopolymerizable compound.
Above-mentioned photopolymerizable compound is compound that can be by the effect of above-mentioned Photoepolymerizationinitiater initiater to polymerize, can be with Enumerate monofunctional monomer, two functional monomers and polyfunctional monomer etc..
The species of above-mentioned monofunctional monomer is not particularly limited, for example, can enumerate nonyl phenyl carbitol acrylate, Acrylic acid 2- hydroxyl -3- phenoxy-propyls, 2- ethylhexyl carbitols acrylate, acrylic acid 2- hydroxy methacrylates, N- vinyl Pyrrolidones etc..
The species of above-mentioned two functional monomer is not particularly limited, for example, 1,6- hexylene glycols two (methyl) propylene can be enumerated Acid esters, ethylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylic acid Double (acrylyl oxy-ethyl) ether, 3- methyl pentanediols two (methyl) acrylate etc. of ester, bisphenol-A.
The species of above-mentioned polyfunctional monomer is not particularly limited, for example, trimethylolpropane tris (methyl) third can be enumerated Olefin(e) acid ester, ethoxylated trimethylolpropane three (methyl) acrylate, propoxylation trimethylolpropane tris (methyl) propylene Acid esters, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol three (methyl) propylene Acid esters, dipentaerythritol five (methyl) acrylate, ethoxylated dipentaerythritol six (methyl) acrylate, propoxylation two Pentaerythrite six (methyl) acrylate, dipentaerythritol six (methyl) acrylate etc..
On the basis of the feline amount in above-mentioned photosensitive composition, above-mentioned photopolymerizable compound Content can be 5~45 weight %, be specifically as follows 6~44 weight %, more specifically can be 7~43 weight %.Above-mentioned The content of photopolymerizable compound be above range in the case of, have the pixel portion comprising the photopolymerizable compound it is strong Degree or flatness become good effect.
Colouring agent
The photosensitive composition of one embodiment of the present invention can further include containing more than one The colouring agent of pigment or more than one dyestuff.
Pigment
Above-mentioned pigment can use the organic pigment or inorganic pigment used generally in the art.Above-mentioned pigment can use Various pigment used in printing-ink, jetted ink etc., specifically, water-soluble azo pigment, insoluble can be enumerated AZOpigments, phthalocyanine color, quinacridone pigment, isoindolenone pigments, isoindoline pigment, pigment, pyrene ketone pigment, twoPiperazine pigment, anthraquinone pigment, DIANTHRAQUINONE base pigment, anthracene pyrimidine pigment, anthracene form anthrone (anthanthrone) pigment, indanthrone (indanthrone) pigment, flavanthrone pigment, pyranthrone (pyranthrone) pigment, diketopyrrolo-pyrrole pigment etc.. As above-mentioned inorganic pigment, the metallic compounds such as metal oxide or metal complex can be enumerated, specifically, can be enumerated Metal oxide or metal composite oxide of iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black etc. etc..Particularly, As above-mentioned organic pigment and inorganic pigment, specifically, colour index (association of dyeing man will (The society can be enumerated Of Dyers and Colourists) publish) in be categorized as the compound of pigment, more specifically, following color can be enumerated and referred to The pigment of number (C.I.) numbering, but this is not necessarily limited to, they each individually or can be used in combination of two or more.
C.I. pigment yellow 13,20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147, 148th, 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 9,97,105,122,123,144,149,166,168,176,177,180,192,208,215, 216th, 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 7,10,15,25,36,47,59,62 and 63；
C.I pigment browns 28；
C.I pigment blacks 1 and 7；Deng
Above-mentioned pigment can use the organic pigment or inorganic pigment used generally in the art, and they can be each independent Or it is used in combination of two or more.
In foregoing illustrative C.I. pigment, specifically, it can use selected from C.I. pigment yellow 13s 8, C.I. pigment yellows 139th, C.I. pigment yellows 150, C.I. pigment yellows 185, C.I. pigment oranges 38, C.I. pigment red 122s, C.I. paratoneres 166, C.I. Paratonere 177, C.I. paratoneres 208, C.I. paratoneres 242, C.I. paratoneres 254, C.I. paratoneres 255, C.I. pigment violets 23rd, C.I. pigment blue 15s:3rd, pigment blue 15:6th, the pigment in C.I. pigment Green 7s, C.I. pigment green 36s, C.I. naphthol greens 58.
The dispersible pigment dispersion that above-mentioned pigment is preferably disperseed using its uniform particle sizes.As the uniform particle sizes point for making pigment One example of scattered method, can be enumerated by adding pigment dispersing agent to carry out method of decentralized processing etc., by above-mentioned Method can obtain the dispersible pigment dispersion of pigment dispersed state in the solution.
As the concrete example of above-mentioned pigment dispersing agent, can enumerate cation system, anion system, nonionic system, both sexes from Surfactants such as subsystem, Polyester, polyamine system etc., they each individually or can be used in combination of two or more.
Pigment dispersing agent
Above-mentioned pigment dispersing agent is in order to which the solution of pigment is solidifying and maintains stability and adds, and can unrestrictedly use ability The pigment dispersing agent typically used in domain.Specifically, it can contain and include butyl methacrylate (BMA) or methacrylic acid The acrylic ester dispersant (hereinafter referred to as dispersant containing acrylic) of N, N- dimethylamino ethyl ester (DMAEMA).Now, on Dispersant containing acrylic is stated preferably using the active controlling party legal system by being provided in KR published patent 2004-0014311 The material made, as the commercially available product of the acrylic ester dispersant manufactured by above-mentioned active control method, it can enumerate DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 etc..
Foregoing illustrative dispersant containing acrylic each individually or can be used in combination of two or more.
Above-mentioned pigment dispersing agent can also use other resin-bonded pigment dispersants beyond aforesaid propylene acid system dispersant. As other above-mentioned resin-bonded pigment dispersants, known resin-bonded pigment dispersant, particularly polyurethane can be enumerated, with poly- Acrylate is the polycarboxylate of representative, the ammonium salt of unsaturated polyamide, polycarboxylic acids, (part) amine salt of polycarboxylic acids, polycarboxylic acids, Alkylamine salt, polysiloxanes, long-chain polyaminoamide phosphate, the ester of hydroxyl polycarboxylic acids and their the modified life of polycarboxylic acids The acid amides that is formed into thing or with the freely polyester of (free) carboxyl and the reaction of poly- (low-grade alkylidene imines) or they Oily dispersant as salt；(methyl) acrylic-styrene copolymer, (methyl) acrylic acid-(methyl) acrylic ester copolymer Thing, styrene-maleic acid copolymer, polyvinyl alcohol or water-soluble resin as polyvinylpyrrolidone or water-soluble polymer Compound；Polyester；Modified polyacrylate；The addition product of ethylene oxide/propylene oxide；With phosphate etc..As above-mentioned The commercially available product of resin-bonded pigment dispersant, for cation system pitch dispersant, such as BYK (Bi Ke) chemistry can be enumerated The trade name of company：DISPER BYK-160、DISPER BYK-161、DISPER BYK-162、DISPER BYK-163、 DISPER BYK-164、DISPER BYK-166、DISPER BYK-171、DISPER BYK-182、DISPER BYK-184； The trade name of BASF (BASF) company：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 (Lu Borun) company：SOLSPERS-24000、 SOLSPERS-32550、NBZ-4204/10；Grind the trade name for the company of refining in river：HINOACT T-6000、HINOACT T- 7000、HINOACT T-8000；The trade name of aginomoto company：AJISPUR PB-821、AJISPUR PB-822、AJISPUR PB-823；The trade name of chemical company of common prosperity society：FLORENE DOPA-17HF、FLORENE DOPA-15BHF、FLORENE DOPA-33, FLORENE DOPA-44 etc..Other resin-bonded pigment dispersants beyond aforesaid propylene acid system dispersant can be each From individually or be used in combination of two or more, can also with dispersant containing acrylic and use and use.
On the basis of the feline amount of used pigment, the content of above-mentioned pigment dispersing agent can be 5~60 Parts by weight, it is specifically as follows 10~55 parts by weight, more specifically can is 15~50 parts by weight.In the content of above-mentioned pigment dispersing agent In the case of above range, viscosity may uprise, and in the case of less than above range, the micronized of pigment is difficult, or The problems such as gelation may occur after scattered.
Dyestuff
As long as above-mentioned dyestuff for organic solvent there is dissolubility can unrestrictedly to use.Specifically, can make Dissolubility and heat resistance for alkaline developer, solvent resistance etc. are may insure with not only having the dissolubility for organic solvent The dyestuff of reliability.
As above-mentioned dyestuff, acid dyes, the acid dyes for being selected from the acidic-group with sulfonic acid, carboxylic acid etc. can be used Material in sulfonamide body of salt, acid dyes with nitrogen-containing compound etc. and their derivative, in addition, it can also select Choose spouse the acid dyes and their derivative of nitrogen system, xanthene system, phthalocyanine system.
Above-mentioned dyestuff can use compound or the dyeing for being classified as dyestuff in colour index (association of dyeing man will is published) Known dyestuff described in handbook (Se Ran societies).
As the concrete example of above-mentioned dyestuff, for C.I. solvent dyes, can enumerate：
C.I. solvent yellow 4,14,15,16,21,23,24,38,56,62,63,68,79,82,93,94,98,99,151, 162nd, the weld such as 163；
C.I. the orchil such as solvent red 8,45,49,89,111,122,125,130,132,146,179；
C.I. the orange such as solvent orange 2,7,11,15,26,41,45,56,62；
C.I. the blue dyes such as solvent blue 5,35,36,37,44,59,67,70；
C.I. the cudbear such as solvent purple 8,9,13,14,36,37,47,49；
C.I. green green colouring material such as 1,3,4,5,7,28,29,32,33,34,35 of solvent etc..
C.I. in solvent dye, specifically, can use for the excellent C.I. solvent yellows of the dissolubility of organic solvent 14、16、21、56、151、79、93；C.I. solvent red 8,49,89,111,122,132,146,179；C.I. solvent orange 41,45, 62；C.I. solvent blue 35,36,44,45,70；C.I. solvent violet 13, more specifically, C.I. solvent yellow 2s 1,79 can be used； C.I. solvent red 8,122,132.
In addition, for C.I. acid dyes, can enumerate：
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、 212nd, the weld such as 214,220,221,228,230,232,235,238,240,242,243,251；
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、 417th, the orchil such as 418,422,426；
C.I. acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108, 169th, the orange such as 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、324:1st, the blue dyes such as 335,340；
C.I. the cudbear such as acid violet 6B, 7,9,17,19,66；
C.I. the green colouring material such as acid green 1,3,5,9,16,25,27,50,58,63,65,80,104,105,106,109 Deng.
In above-mentioned acid dyes, specifically, it can use for the excellent C.I. Indian yellows of the solubility of organic solvent 42；C.I. acid red 92；C.I. acid blue 80,90；C.I. acid violet 66；C.I. acid green 27.
In addition, for C.I. direct dyess, can enumerate：
C.I. directly Huang 2,33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98, 102nd, the weld such as 108,109,129,136,138,141；
C.I. directly red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177, 179th, 181,182,184,204,207,211,213,218,220,221,222,232,233,234,241,243,246,250 etc. Orchil；
C.I. direct orange 34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107 etc. is orange Dyestuff；
C.I. directly indigo plant 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、 252nd, the blue dyes such as 256,257,259,260,268,274,275,293；
C.I. direct purple 47,52,54,59,60,65,66,79,80,81,82,84,89,90,93,95,96,103,104 Deng cudbear；
C.I. the green colouring material such as direct green 25,27,31,32,34,37,63,65,66,67,68,69,72,77,79,82 Deng.
In addition, for C.I. mordant dyes, can enumerate：
C.I. the weld such as medium Huang 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65；
C.I. medium red 1,2,3,4,9,11,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37, 38th, the orchil such as 39,41,43,45,46,48,53,56,63,71,74,85,86,88,90,94,95；
C.I. medium orange 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47, 48 grade oranges；
C.I. medium indigo plant 1,2,3,7,8,9,12,13,15,16,19,20,21,22,23,24,26,30,31,32,39, 40th, the blue dyes such as 41,43,44,48,49,53,61,74,77,83,84；
C.I. the purple such as medium purple 1,2,4,5,7,14,22,24,30,31,32,37,40,41,44,45,47,48,53,58 Color dyestuff；
C.I. green green colouring material such as 1,3,4,5,10,15,19,26,29,33,34,35,41,43,53 of medium etc..
Above-mentioned dyestuff each individually or can be used in combination of two or more.
On the basis of the feline amount in above-mentioned photosensitive composition, the content of above-mentioned colouring agent can Think 5~60 parts by weight, be specifically as follows 7~50 parts by weight, more specifically can be 10~45 parts by weight.In above-mentioned colouring agent In the case that content includes within the above range, following advantage be present, even with above-mentioned photosensitive composition shape Into film, the color depth of pixel is also abundant, and the deciduous of non-pixel portion will not reduce and can suppress to produce residue during development.
Solvent
Photosensitive composition according to an embodiment of the present invention can further include solvent.
As long as above-mentioned solvent is effective when dissolving the other compositions included in photosensitive composition, then may be used To use the solvent used in common photosensitive composition, specifically, Ke Yiju without particular limitation Go out ethers, aromatic hydrocarbon, ketone, alcohols, esters or amide-type etc..
Above-mentioned solvent can specifically enumerate ethylene glycol single methyl ether, ethylene glycol monomethyl ether, ethylene glycol monopropyl ether, The ethylene glycol monoalkyl ether class such as ethylene glycol monobutyl ether；Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol two The diethylene glycol dialkyl ether class such as propyl ether, diethylene glycol dibutyl ether；Methylcellosolve acetate, ethyl cellosolve acetate Deng ethylene glycol alkyl ether acetate esters；Propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propane diols list propyl group The aklylene glycol alkylether acetates class such as ether acetic acid ester, methoxybutyl acetic acid esters, methoxypentyl acetic acid esters；Benzene, toluene, Dimethylbenzene, mesitylene etc. are aromatic hydrocarbon；Methyl ethyl ketone, acetone, methyl amyl ketone, methyl iso-butyl ketone (MIBK), cyclohexanone etc. Ketone；The alcohols such as ethanol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerine；3- ethoxyl ethyl propionates, 3- methoxy propyls The esters such as sour methyl esters, ethyl lactate, butyl lactate；Ring-type esters such as gamma-butyrolacton etc..
In addition, from the aspect of coating and drying property, above-mentioned solvent can specifically use boiling point be 100 DEG C~ 200 DEG C of organic solvent, more specifically can use propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, Cyclohexanone, ethyl lactate, butyl lactate, 3- ethoxyl ethyl propionates, 3- methoxy methyl propionates etc..
Foregoing illustrative solvent each individually or can be use mixing two or more, with the coloring phototonus tree of the present invention On the basis of the gross weight of oil/fat composition, content can be 60~90 weight %, be specifically as follows 65~88 weight %, more specifically may be used Think 70~85 weight %.In the case where above-mentioned solvent includes within the above range, when utilization roll coater, spin coater, slit , can be to when the apparatus for coating such as formula spin coater, slit type coater (otherwise referred to as die coating machine), ink-jet printer are coated Property to be coated becomes good effect.In the case where the content of above-mentioned solvent is less than above range, coating may reduce and make work Sequence mutually strains difficulty, in the case larger than the above-mentioned range, it may occur that the colour filter formed by above-mentioned red sensitive resin combination The problem of performance of device may reduce.
Additive
Photosensitive composition according to an embodiment of the present invention can be included further as needed to be added Add agent.
Above-mentioned additive can be specifically used in dispersant, wetting agent, silane coupler and anticoagulant etc. It is at least one.
As above-mentioned dispersant, commercially available surfactant can be used, as above-mentioned surfactant, can have been enumerated Machine silicon systems surfactant, fluorine system surfactant, the silicone based surfactants and their mixture with fluorine atom Deng.As above-mentioned silicone based surfactants, surfactant with siloxanes key etc. can be enumerated as an example.As Commercially available product, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone can be enumerated DC11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone 29SHPA、 Toray Silicone SH30PA, polyether modified silicon oil SH8400 (east beautiful organosilicon (strain) manufacture), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (SHIN-ETSU HANTOTAI organosilicon manufacture), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (GE Toshiba organosilicon (strain) manufacture) etc..As above-mentioned fluorine system Surfactant, surfactant with fluorocarbon chain etc. can be enumerated as an example.Specifically, can enumerate Fluorinert (trade name) FC430, Fluorinert FC431 (Sumitomo 3M (strain) manufactures), Megafac (trade name) F142D、Megafac F171、Megafac F172、Megafac F173、Megafac F177、Megafac F183、 Megafac R30 (big Japanese ink chemical industry (strain) manufacture), F-Top (trade name) EF301, F-Top EF303, F-Top EF351, F-Top EF352 (new autumn fields chemical conversion (strain) manufacture), Surflon (trade name) S381, Surflon S382, Surflon SC101, Surflon SC105 (Asahi Glass glass (strain) manufacture), E5844 ((strain) great Jin fine chemistries research institutes Manufacture), BM-1000, BM-1100 (trade name：BMChemie companies manufacture) etc. as an example.As above-mentioned with fluorine atom Silicone based surfactants, surfactant with siloxanes key and fluorocarbon chain etc. can be enumerated as an example.It is specific and Speech, can enumerate Megafac (trade name) R08, Megafac BL20, Megafac F475, Megafac F477, Megafac F443 (big Japanese ink chemical industry (strain) manufacture) etc. is as an example.
As above-mentioned wetting agent, such as, glycerine, diethylene glycol and ethylene glycol etc. can be enumerated, can be included selected from wherein More than one.
As above-mentioned silane coupler, such as, aminopropyltriethoxywerene werene, γ-mercaptopropyi front three can be enumerated TMOS and γ-methacryloxypropyl trimethoxy silane etc., as commercially available product, having SH6062, SZ6030, (east is beautiful DOW CORNING organosilicon company (Toray-Dow Corning Silicon co., Ltd.) manufacture), KBE903, KBM803 (SHIN-ETSU HANTOTAI Organosilicon company (Shin-Etsu silicone co., Ltd.) manufactures) etc..
Above-mentioned anticoagulant can such as enumerate Sodium Polyacrylate..
<Colour filter>
The another way of the present invention is to provide the colour filter using the manufacture of above-mentioned photosensitive composition.
Above-mentioned colour filter includes substrate and is formed at the patterned layer on the top of aforesaid substrate.
For aforesaid substrate, above-mentioned colour filter can be substrate in itself, or can also be colour filter in display device etc. Position residing for device, is not particularly limited.Aforesaid substrate can be glass, silicon (Si), silica (SiOx) or polymeric substrate, Above-mentioned polymeric substrate can be polyether sulfone (polyethersulfone, PES) or makrolon (polycarbonate, PC) Deng.
Layer of the above-mentioned patterned layer as the photosensitive composition comprising the present invention, can be above-mentioned by being coated with Photosensitive composition and it is exposed, develops and heat cure and the layer that is formed in a predetermined pattern.Above-mentioned patterned layer It can be formed by implementing method commonly known in the art.
Colour filter comprising aforesaid substrate and patterned layer can also may be used further comprising the next door being formed between each pattern Further to include black matrix, but it is not limited to this.
Further, it is also possible to further include the diaphragm on the patterned layer top for being formed at above-mentioned colour filter.
<Image display device>
In addition, the another way of the present invention is related to the image display device for including above-mentioned colour filter.Now, above-mentioned image shows Showing device can be the image display device for the COA structures that colour filter is formed on the substrate formed with thin film transistor (TFT) (TFT). In the case of the photosensitive composition comprising the present invention, there is advantages below：The image of above-mentioned COA structures is shown In device, the excellent contact hole of alignment precision can be formed in R, G, B-tree adipose membrane, and above-mentioned resin film be pixel electrode with it is active When element (TFT) forms electric pathway, it can be ensured that utilize the contact hole formation of dry etching method and the IZO as pixel electrode R, G, the pattern stability of B-tree adipose membrane during evaporation, improve as ensure high aperture R, G, B break caused by pixel not It is good.
The colour filter of the present invention can be applied not only to common liquid crystal display device, can also show applied to electroluminescent The various image display devices such as showing device, plasm display device, field emission display device.
Hereinafter, in order to illustrate this specification, enumerate embodiment and be described in detail.But the implementation of this specification Example can be deformed into other various forms, should not be construed to the scope of this specification by implementation following detailed description of The restriction of example.The embodiment of this specification is provided to be described more fully this specification to those skilled in the art 's.In addition, as long as no specifically mentioned, " % " and " part " of following presentation content is weight basis.
Synthesis example：Alkali soluble resins (A-1)
Prepare the flask for possessing mixer, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe.In above-mentioned burning Propylene glycol monomethyl ether (PGMEA) 100g, propylene glycol monomethyl ether (PGME) 100g, azodiisobutyronitrile are put into bottle (AIBN) 8.2g, 2-EHA 73.6g, 4- methyl styrene 5.9g, GMA 78.1g, N-dodecane mercaptan 6.1g, and it is replaced as nitrogen.Afterwards, stir while the temperature of reaction solution is risen into 80 DEG C, Ran Houjin Row reacts for 4 hours.The temperature of above-mentioned reaction solution is down to normal temperature, by the atmosphere of flask from nitrogen displacement into air after, input three Ethylamine 0.2g, 4- metoxyphenol 0.1g, acrylic acid 39.6g, carry out reacting for 6 hours at 100 DEG C.Afterwards, by reaction solution Temperature is down to normal temperature, puts into succinic anhydride 6.0g, carries out reacting for 6 hours at 80 DEG C, synthesis alkali soluble resins (A-1).
The acid number of the alkali soluble resins of above-mentioned synthesis is 32.8mgKOH/g.
On the weight average molecular weight (Mw) of the alkali soluble resins of above-mentioned synthesis, the result determined by GPC method is 6,230, The glass transition temperature determined by differential scanning calorimetry (DSC) is -21.0 DEG C.
Production Example：The manufacture of pigment dispensing composition (D)
Using the C.I. pigment blue 15s as pigment of 30 parts by weight:6th, BYK-2001 (the BYK companies as pigment dispersing agent Manufacture) 4.0 parts by weight, as solvent the parts by weight of propylene glycol monomethyl ether 66 mix, fill pigment using ball mill It is scattered.
Embodiment 1~6 and comparative example 1~4：The manufacture of photosensitive composition
Embodiment 1.
Using the weight % of alkali soluble resins (A-1) 15.869 of above-mentioned synthesis example, two seasons as photopolymerizable compound (B) The acrylate of penta tetrol six (KAYARAD DPHA, Japanese chemical drug) 4.015 weight %, 0.964 weight % conduct photopolymerization are drawn Send out C-1, the weight % of pigment dispensing composition (D) 4.5, the 3- ethyoxyls as solvent of above-mentioned Production Example of the table 1 below of agent The weight % of ethyl propionate (E-1) 17, the weight % of propylene glycol monomethyl ether (E-2) 57.646 and the polyethers as additive Modified silicon oil (SH8400, the beautiful organosilicon (strain) in east) 0.006 weight % mixing, manufactures photosensitive composition.
Embodiment 2~6.
Using the composition described in table 1 below and content and by manufacturing color sensation with the identical method of above-described embodiment 1 Photosensitive resin composition.
Comparative example 1~4.
Using the composition described in table 1 below and content and by manufacturing color sensation with the identical method of above-described embodiment 1 Photosensitive resin composition.
[table 1]
Colour filter Production Example
The photosensitive composition of above-described embodiment 1~6 and comparative example 1~4 is coated on 5 by spin-coating method × On the glass substrate (Corning Incorporated) of 5cm sizes, it is then placed within heating plate, is maintained 3 minutes in 100 DEG C of temperature, is formed The film of 3.0 μ m thicks.Then, on the above-mentioned films place with make transmitance 1~100% scope with stepped change Pattern and 1 μm to 100 μm of line/space pattern experiment photomask, 100 μm will be set to testing the interval of photomask, shone Penetrate ultraviolet.Now, ultraviolet light source uses the high-pressure mercury-vapor lamp for including the whole 1kw of g, h, I line, with 100mJ/cm2Photograph Degree is irradiated, not using special optical filter.By it is above-mentioned by ultraviolet irradiation film pH 10.5 KOH water Impregnate 2 minutes and developed in solution development solution.After the glass plate washing of above-mentioned film being covered with using distilled water, nitrogen blowing It is dried, in 200 DEG C of heated oven, heats 30 minutes.Pattern form (film) thickness of thus obtained colour filter is 3 μm。
Experimental example 1：Developing powder, sensitivity, pattern stability, the experiment of conical surface line width
1) developing powder：Non-exposed portion is initial during measure development (spray development (Spray Developer) HPMJ modes) The time needed for developer solution is dissolved in, result is recorded in table 2 below.
2) sensitivity：Determine to form after development the minimum exposure amount for not having the film of figuratum peeling and needing, will As a result it is recorded in table 2 below.
3) pattern stability：Determine and the mistake (figure of pattern mask pattern after exposure is utilized under low light exposure (20~100mJ) Degree that case is peeled off, rectilinear propagation are bad etc.) degree.The benchmark of pattern stability is evaluated as follows, and result is recorded in into table 2 below In.Now, light microscope (ECLIPSE LV100POL Model, the Buddhist nun that the mistake on pattern passes through three-dimensional surface topography instrument Kanggong department manufactures) confirmed.
○：Without mistake or less than 3 on pattern
×：Mistake on pattern has more than 3
4) conical surface line width：It is exposed using pattern mask after forming the pattern of 100 μm of lateral length, passes through and scan electricity The cured film that sub- microscope (S-4600, (strain) Hitachi system) observation obtains, determines the line width of pattern, shows the result in down State in table 2.
[table 2]
With reference to above-mentioned table 2, (implement in the case of both alkali soluble resins and Photoepolymerizationinitiater initiater comprising the present invention Example 1~6), compared with the alkali soluble resins not comprising the present invention and the situation (comparative example 1~2) of Photoepolymerizationinitiater initiater, confirm Sensitivity and pattern stability are improved, and particularly, compared with above-mentioned comparative example 1, conical surface line width is also improved, with not wrapping The situation (comparative example 3) of Photoepolymerizationinitiater initiater containing the present invention is compared, and confirming sensitivity and pattern stability is improved, with The situation (comparative example 4) of alkali soluble resins not comprising the present invention is compared, and confirms developing powder, sensitivity, pattern stability Improved with conical surface line width.
Experimental example 2：Hardness, solvent resistance, heat resistance and heat resistance it is front/rear brightness change confirm experiment
1) pencil hardness：Pencil hardness test is implemented according to JIS K5600-5-4, and result is recorded in Table 3 below.
2) solvent resistance：After METHYLPYRROLIDONE (NMP) solvent is consistently maintained into 23 DEG C, impregnate 30 minutes And determine color change (△ E*ab).Now, measure device uses microspectrophotometer (Microscopic Spectrophotometer；Model No.OSP-SP2000, Olympus Corp), solvent resistance is determined respectively using the device The front and rear CIE chromaticity coordinates values of evaluation, confirm color change degree by following mathematical expressions 1, result is recorded in Table 3 below.
[mathematical expression 1]
△ E*ab=[(△ L*)2+(△a*)2+(△b*)2]1/2
○：△E*ab<1
△：1≤△E*ab≤3
×：△Eab>3
3) heat resistance and Evaluation of Heat Tolerance it is front/rear brightness (△ Y) change：The colour filter that will be manufactured in the Production Example of the present invention After device heats 2 hours in 230 DEG C of heated oven, calculated by above-mentioned mathematical expression 1 and heat front/rear color change, in addition Pass through microspectrophotometer (Microscopic Spectrophotometer；Model No.OSP-SP2000, Olympus are public Department) confirm the front/rear brightness change of Evaluation of Heat Tolerance, it is confirmed whether the luminance-reduction caused by hot xanthochromia be present.Heat resistance is commented Valency benchmark is identical with above-mentioned solvent resistance, and brightness change benchmark is described below.Experimental result is recorded in Table 3 below.
○：-0.04≤△Y≤0.00
×：- 0.04 ＞ △ Y
[table 3]
With reference to above-mentioned table 3, by the situation (embodiment of both alkali soluble resins and Photoepolymerizationinitiater initiater comprising the present invention 1~6) with the alkali soluble resins not comprising the present invention and the situation (comparative example 1~2) of Photoepolymerizationinitiater initiater, not comprising the present invention Situation (comparative example 3), the situation (comparative example 4) of alkali soluble resins not comprising the present invention of Photoepolymerizationinitiater initiater when comparing, Confirming hardness, solvent resistance, heat resistance and brightness change is improved.
Experimental example 3:The size/shape of contact hole, stripper, IZO etching solution tolerance tests
The minus PR of above-described embodiment 1~6 and comparative example 1~4 (photoresist (Photoresist)) is coated on R/ On G/B pattern coating films, it is then placed within heating plate, is maintained 1 minute in 90 DEG C of temperature and form film.Then, above-mentioned On film place with make transmitance 1~100% scope with the pattern of stepped change and 1 μm to 50 μm of line/gap The experiment photomask of pattern, 100 μm will be set to testing the interval of photomask, irradiate ultraviolet.Now, ultraviolet light source uses The whole 1kw of g, h, i line high-pressure mercury-vapor lamp is included, with 100mJ/cm2Illumination be irradiated, not using special optics Filter.By it is above-mentioned by ultraviolet irradiation film be again placed in heating plate, 110 DEG C temperature maintain 1 minute and incite somebody to action Film further solidifies.The above-mentioned film by ultraviolet irradiation is dipped in the aqueous development solution of TMAH 2.38% to enter for 30 seconds Row development.The glass plate of the film is covered with using distilled water cleaning, then nitrogen blowing is dried, in 130 DEG C of heated oven Middle heating 2 minutes.Thus obtained minus PR pattern forms (film) thickness is 3 μm.On the evaporation condition of IZO films, utilize Sputter (Sputter),It is suitable, is more preferablyDegree.For the research of each experiment Benchmark is as follows, and result is recorded in table 4 below.
1) size of contact hole：Contact after the exposure of 40 μm of patterns of contact hole mask (Contact Hole Mask) The diameter in hole
2) shape of contact hole：After the exposure of 40 μm of square patterns of contact hole mask, SEM (S-4300, (strain) Hitachi system Make made) the performance degree of 40 μm of mask patterns on image
Now, on showing degree, by the diameter of contact hole after exposure and the consistent degree of the diameter of contact hole mask Represented with %, it is about higher close to 100% consistent degree.
3) stripper, IZO etching solution tolerances：By stripper (PRS-2000, the friendly fine chemistry industry in east), IZO etching solutions (MA-S03/MASZ02, the friendly fine chemistry industry in east) is same with used Spray Developer (HPMJ modes) during above-mentioned development Ground is carried out.On IZO etching conditions, washed after being impregnated 2 minutes at 35 DEG C, confirm the stabilization of the film as caused by IZO etching solutions Property, for the condition of stripper, implement 4 minutes or so to evaluate in the case where being adjusted to the temperature conditionss of 70~80 DEG C of scopes.For stripping The evaluation of chaotropic, also confirm the stability of film.Specifically, evaluated for the tolerance of above-mentioned stripper and IZO etching solutions In, the WRONG PATTERN degree after the exposure of 100 μm of patterns of evaluation pattern generating mask, pass through the optical microphotograph of three-dimensional surface topography instrument Mirror confirms the mistake of above-mentioned pattern, and is evaluated by following benchmark, and result is recorded in table 4 below.
○：Mistake on pattern 1~3
×：Dislocation on pattern is more than 3 and pattern is peeled off
[table 4]
With reference to above-mentioned table 4, by the situation (embodiment of both alkali soluble resins and Photoepolymerizationinitiater initiater comprising the present invention 1~6) with the alkali soluble resins not comprising the present invention and the situation (comparative example 1~2) of Photoepolymerizationinitiater initiater and not comprising this hair When the situation (comparative example 3) of bright Photoepolymerizationinitiater initiater compares, contact hole size, shape, stripper tolerance and IZO are confirmed Etching solution tolerance is improved, and when compared with the situation (comparative example 4) of the alkali soluble resins not comprising the present invention, is confirmed It is improved to contact hole shape, stripper tolerance and IZO etching solution tolerances.
Experimental example 4：Deaerate determination experiment
The colour filter manufactured in above-mentioned Production Example at 230 DEG C thermally decompose within 30 minutes by Py-GC/FID, analysis is caught The compound of collection, metewand are as follows.
The degassing value of comparative example 1 is set to 100% benchmark, is indicated with percentage, the value is smaller more excellent.By result It is recorded in table 5 below.
[table 5]
With reference to above-mentioned table 5, by the situation (embodiment of both alkali soluble resins and Photoepolymerizationinitiater initiater comprising the present invention 1~6) with the alkali soluble resins not comprising the present invention and the situation (comparative example 1~2) of Photoepolymerizationinitiater initiater, not comprising the present invention The situation (comparative example 3) of Photoepolymerizationinitiater initiater and the situation (comparative example 4) of alkali soluble resins not comprising the present invention compare When, confirming degassing (%) phenomenon is improved.

Claims (8)

1. a kind of photosensitive composition, it includes the alkali solubility containing the repeat unit represented by following chemical formula 1 Resin with containing selected from the compound group represented by following chemical formula 2 into one or more of group compound photopolymerization Initiator：
Chemical formula 1
In the chemical formula 1,
R1And R2Hydrogen atom or methyl are each independently,
R3For the residue containing carboxylic acid obtained by being derived as acid anhydrides,
Chemical formula 2
In the chemical formula 2,
R4~R13It is each independently hydrogen, halogen, C1~C20Alkyl, C6~C20Aryl, C1~C20Alkoxy, C7~C40 Aryl alkyl, C1~C20Hydroxy alkyl, C2~C40Hydroxy alkoxy alkyl or C3~C20Cycloalkyl.
2. photosensitive composition according to claim 1, it is characterised in that always rubbed relative to alkali soluble resins That percentage, the content of the repeat unit represented by the chemical formula 1 is 50~90 moles of %.
3. photosensitive composition according to claim 1, it is characterised in that with coloring phototonus resin combination On the basis of feline amount in thing, the content of the Photoepolymerizationinitiater initiater is 0.1~40 weight %.
4. photosensitive composition according to claim 1, it is characterised in that the coloring phototonus resin group Compound is further included selected from one or more of group being made up of photopolymerizable compound, colouring agent, solvent and additive.
5. a kind of colour filter, include the solidfied material of photosensitive composition according to any one of claims 1 to 4.
6. colour filter according to claim 5, it is characterised in that the diameter of the contact hole included in the colour filter with The consistent degree of the diameter of used contact hole mask is more than 90% when contact hole exposes.
7. a kind of image display device, include the colour filter described in claim 5.
8. image display device according to claim 7, it is characterised in that with array in described image display device Colour filter is COA mode application colour filters.
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