CN104345552B - Colored photosensitive resin composition, colour filter and the liquid crystal display device with the colour filter - Google Patents
Colored photosensitive resin composition, colour filter and the liquid crystal display device with the colour filter Download PDFInfo
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- CN104345552B CN104345552B CN201410317429.3A CN201410317429A CN104345552B CN 104345552 B CN104345552 B CN 104345552B CN 201410317429 A CN201410317429 A CN 201410317429A CN 104345552 B CN104345552 B CN 104345552B
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- resin composition
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- colour filter
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G—PHYSICS
- 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
-
- 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
- G02F1/1303—Apparatus specially adapted to the manufacture of LCDs
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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
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- General Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The present invention relates to a kind of colored photosensitive resin composition, colour filter and with the liquid crystal display device of the colour filter.The colored photosensitive resin composition of the present invention includes colorant (A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), the colorant (A) includes one or more dyestuffs, and the antioxidant (E) includes the mixture of phenol antioxidant and sulphur class antioxidant；The colour filter is formed using the colored photosensitive resin composition.The colored photosensitive resin composition of the present invention has excellent heat resistance and provides high brightness.
Description
Technical field
The present invention relates to a kind of colored photosensitive resin composition, colour filter and with the liquid crystal display device of the colour filter.
Specifically, the present invention provides a kind of colored photosensitive resin composition, using the composition formed colour filter and with should
The liquid crystal display device of colour filter, the colored photosensitive resin composition has excellent heat resistance, after making pyroprocess
Color change is smaller and provides high brightness.
Background technology
Colour filter is widely used in imaging device and liquid crystal display (LCD), and its application range constantly extends.
Colour filter is prepared conventionally by following manner：Colored photosensitive resin composition comprising red, green or blue pigment is equal
It is coated on evenly on the black matrix substrate for being formed with black pattern, subsequent heat drying makes obtained coated film expose
Light simultaneously develops, and further heating and hardening when necessary, the pixel of each color is consequently formed, and repeat the above work to each color
Sequence.
Colored photosensitive resin composition generally comprises pigment, adhesive resin, photopolymerization monomer and Photoepolymerizationinitiater initiater.
In order to form black matrix", Photosensitve resin composition includes black pigment.
South Korea patent application bulletin 2009-0066076 discloses a kind of colour filter Photosensitve resin composition, described group
Object is closed comprising acryl adhesive resin, the acrylic compounds carboxylate resin containing double bond, photopolymerization monomer, photopolymerization to draw
Send out agent, pigment, antioxidant and solvent.The composition uses the mixture of the first antioxidant and the second antioxidant as anti-
Oxidant, first antioxidant are selected from the group that is made of chinol class, amine, phenolic compound and its mixture, and described the
Two antioxidants include phosphite (ester) class compound, thus prevent Photosensitve resin composition from aoxidizing and enhance its thermostabilization
Property.
But the brightness due to the use of the colour filter of the Photosensitve resin composition preparation only containing pigment is relatively low, therefore be
It highlights, the Photosensitve resin composition containing dyestuff is studied.But, the composition containing dyestuff is because heat-resisting
Property is relatively low and is difficult to obtain desired brightness.
Invention content
Technical problem
It is an object of the present invention to provide a kind of colored photosensitive resin composition, the composition has excellent heat-resisting
Property, to make, color change is smaller after pyroprocess and provides high brightness.
It is a further object of the present invention to provide a kind of colour filters formed by using the colored photosensitive resin composition.
It is yet another object of the invention to provide a kind of liquid crystal display devices with the colour filter.
Technical solution
According to an aspect of the invention, there is provided a kind of colored photosensitive resin composition, the composition includes coloring
Agent (A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), it is described
Colorant (A) includes one or more dyestuffs, and the antioxidant (E) includes phenol antioxidant and sulphur class antioxidant
Mixture.
According to another aspect of the present invention, a kind of colour filter formed by using the colored photosensitive resin composition is provided
Piece.
According to another aspect of the invention, a kind of liquid crystal display device with the colour filter is provided.
Advantageous effects
The colored photosensitive resin composition of the present invention uses the mixture conduct of phenol antioxidant and sulphur class antioxidant
Antioxidant, and be used together the lower one or more dyestuffs of heat resistance as colorant, thus improve heat resistance and provide
Colour filter with high brightness.
Specific implementation mode
The present invention is described in more detail below.
One embodiment of the present invention relates to a kind of colored photosensitive resin composition, the composition includes colorant
(A), adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), described
Toner (A) includes one or more dyestuffs, and the antioxidant (E) includes phenol antioxidant and sulphur class antioxidant
Mixture.
Colorant (A)
In an embodiment of the invention, colorant (A) is characterized in that including one or more dyestuffs, especially
Orchil.
Dyestuff can be commonly used in the art any, for example, cyanogen class, oxa anthracenes, azo, Anthraquinones, metal network
Close species, quinolines and pyrazoline ketone dyestuff.
Colorant (A) can also include the one or more pigment being used together with dyestuff.
Pigment may include being divided into Color Index (The Society of Dyers and Colourists)
The inorganic pigment (such as metal oxide, metal complex and the inorganic salts comprising barium sulfate) and organic pigment of pigment.With regard to heat-resisting
For property and colour rendering, preferably organic pigment.
As example, pigment is divided into Color Index (The Society of Dyers and Colourists)
Compound can be but not limited to the compound of following color index (C.I.) number.
C.I. pigment yellow 1,3,12,13,14,15,16,17,20,24,31,53,83,86,93,94,109,110,117,
125,128,137,138,139,147,148,150,153,154,166,173,180,185,194 and 214；
C.I. pigment orange 13,31,38,40,42,43,51,55,59,61,64,65,71 and 73；
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215,
216,224,242,254,255,264 and 265.
In with paint, preferably use selected from by C.I. pigment yellow 13s 8, C.I. pigment yellow 13s 9, C.I. pigment
In the group that Huang 150, C.I. pigment yellows 185, C.I. paratoneres 177, C.I. paratoneres 242 and C.I. paratoneres 254 form extremely
Few one kind.
Above-mentioned pigment can be used alone, or be used in combination.Such as it is preferable to use C.I. paratoneres
The mixture of 254 and C.I. paratoneres 177 forms red pixel.
Preferably, the total solids content of the colored photosensitive resin composition based on the present invention, with 5 weights of weight %~70
The amount for measuring %, more preferably 10 weight of weight %~50 % includes colorant (A).
Preferably, it is based on the total solids content of colorant (A), with 0.5 weight of weight %~100 %, more preferably 1 weight
The amount for measuring the weight of %~60 % includes dyestuff.When the amount of dyestuff is the 1 weight % of weight %~60, high brightness can be obtained, from
And pattern can be adequately formed and form the color filter pattern with high-quality.
Adhesive resin (B)
In an embodiment of the invention, adhesive resin (B) can be carboxyl group-containing monomer and can be with the monomer
The copolymer of the other monomers of copolymerization.
As example, other copolymerizable monomers can be the monomer containing carbon-to-carbon unsaturated bond, and the monomer includes fragrance
Race's vinyl compound, such as styrene, α-methylstyrene, vinyltoluene；
Unsaturated carboxylic ester compound, such as methyl acrylate, methyl methacrylate, ethyl acrylate, methacrylic acid
Ethyl ester, butyl acrylate, butyl methacrylate, acrylic acid 2- hydroxy methacrylates, 2-hydroxyethyl methacrylate, acrylic acid benzyl
Ester, benzyl methacrylate etc.；
Undersaturated carboxylic acid amide's alkyl ester compound, such as acrylate；
Undersaturated carboxylic acid epihydric alcohol ester compound, such as glycidyl methacrylate；
Vinyl esters of carboxylic acids compound, such as vinyl acetate, vinyl propionate；
Vinyl cyanide compound, such as acrylonitrile, methacrylonitrile, α-chloro-acrylonitrile；
Undersaturated oxetanes carboxylate compound, such as 3- methyl-acryloyloxies methy oxetane, 3- first
Base -3- methacryloxymethyls oxetanes, 3- ethyl -3- acryloyloxymethyls oxetanes, 3- ethyls -3-
Methacryloxymethyl oxetanes, 3- methyl -3- acryloyl-oxyethyls oxetanes, 3- methyl -3- methyl
Acryloyl-oxyethyl oxetanes, 3- methyl -3- acryloyl-oxyethyls oxetanes, 3- methyl -3- metering systems
Trimethylammonium oxetanes etc..
Above-mentioned monomer may be used singly or two or more in combination.
The molecular weight distribution [weight average molecular weight (Mw)/number-average molecular weight (Mn)] of adhesive resin (B) can be 1.5~
6.0, it is preferably 1.8~4.0.When the molecular weight distribution of adhesive resin is 1.5~6.0, developability can be improved.
Preferably, the total solids content based on colored photosensitive resin composition, with 5 weight of weight %~90 %, more excellent
The amount for being selected as 10 weight of weight %~70 % includes adhesive resin (B).When the amount of adhesive resin (B) is 5 weight %~90
When weight %, the dissolubility in developing solution will become enough to raw to make it be difficult on the substrate of non-pixellated part
At development residues, and it can prevent the film of pixelation part in exposure area from reducing in developing process, so as to obtain
Obtain the good leakage of non-pixellated part.
Photopolymerization monomer (C)
In an embodiment of the invention, photopolymerization monomer (C) is to be generated through irradiation by Photoepolymerizationinitiater initiater
Living radical or acid and polymerizable monomer.
The example of photopolymerization monomer may include ethylene glycol diacrylate, diacrylate triglycol ester, two propylene
Sour 1,4- butanediol esters, diacrylate 1,6-HD ester, diacrylic acid pentyl diol ester, acrylate, pentaerythritol, dipropyl
Olefin(e) acid pentaerythritol ester, pentaerythritol triacrylate, diacrylate dipentaerythritol ester, three acrylic acid dipentaerythritol esters,
Five acrylic acid dipentaerythritol esters, six acrylic acid dipentaerythritol esters, bisphenol a diacrylate, trimethylolpropane tris propylene
Acid esters, nobolak type epoxy base acrylate, ethylene glycol dimethacrylate, diethyleneglycol dimethacrylate, two
Methacrylic acid triglycol ester, dimethyl allene acid propylene glycol ester, dimethacrylate 1,4- butanediol esters, dimethyl allene
Sour 1,6-HD ester etc..
Preferably, the total solids content based on colored photosensitive resin composition, with 5 weight of weight %~45 %, more excellent
The amount for being selected as 10 weight of weight %~35 % includes photopolymerization monomer (C).When the amount of photopolymerization monomer (C) is 5 weight %
When~45 weight %, the intensity and smoothness of pixel can be improved.
Photoepolymerizationinitiater initiater (D)
In an embodiment of the invention, Photoepolymerizationinitiater initiater (D) is unrestricted, as long as it, which can be played, makes bonding
The effect of agent resin (B) and photopolymerization monomer (C) polymerization.In particular, with regard to polymerization property, efficiency of initiation, absorbing wavelength,
For availability and price etc., Photoepolymerizationinitiater initiater can be selected from by triazines, acetophenones, bisglyoxaline class compound, oxime
The group of compound and its mixture composition.
The example of compound in triazine class may include bis- (trichloromethyl) -6- (4- the methoxyphenyls) -1,3,5- three of 2,4-
Piperazine, 2,4- bis- (trichloromethyl) -6- (4- methoxyl groups naphthalene) -1,3,5- triazines, bis- piperonyl -1 (trichloromethyl) -6- 2,4-,
Bis- (trichloromethyl) -6- (4- the methoxyl-styrenes) -1,3,5- triazines of 3,5- triazines, 2,4-, bis- (the trichloromethyl) -6- of 2,4-
[2- (5- methylfuran -2- bases) vinyl] -1,3,5- triazines, bis- (the trichloromethyl) -6- of 2,4- [2- (furans -2- bases) ethylene
Base] -1,3,5- triazines, bis- (the trichloromethyl) -6- of 2,4- [2- (4- diethylamino -2- aminomethyl phenyls) vinyl] -1,3,5-
Triazine and bis- (the trichloromethyl) -6- of 2,4- [2- (3,4- Dimethoxyphenyls) vinyl] -1,3,5- triazines.
The example of acetophenone compounds may include diethoxy acetophenone, 2- hydroxy-2-methyl -1- phenyl propyl-s 1-
Ketone, benzyl dimethyl ketal, 2- hydroxyls -1- [4- (2- hydroxyl-oxethyls) phenyl] -2- methyl propyl- 1- ketone, 1- hydroxy-cyclohexyls
Phenyl ketone, 2- methyl-1s-(4- methyl thio phenyls) -2- morpholinyl propyl- 1- ketone, 2- benzyl -2- dimethylaminos -1- (4- morpholines
Base phenyl) butyl- 1- ketone, 2- hydroxy-2-methyls -1- [4- (1- methyl ethylenes) phenyl] propyl- 1- ketone and 2- (4- methylbenzyls) -
2- (dimethylamino) -1- (4- morpholino phenyls) butyl- 1- ketone.
The example of bisglyoxaline class compound may include bis- (2- the chlorphenyls) -4,4' of 2,2'-, 5,5'- tetraphenyls bisglyoxaline,
2,2'- bis- (2,3- dichlorophenyls) -4,4', 5,5'- tetraphenyls bisglyoxaline, 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetra-
(alkoxyl phenyl) bisglyoxaline, 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetra- (tri-alkoxy phenyl) bisglyoxaline, 2,2- are bis-
(2,6- dichlorophenyl) -4,4 ' 5,5 '-tetraphenyl -1,2 '-bisglyoxalines, and wherein 4,4', 5,5' phenyl substitution have alkane
The imidazoles of oxygen carbonyl.These, it is preferred to 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetraphenyl bisglyoxaline, 2,2'- it is bis- (2,
3- dichlorophenyls) -4,4', 5,5'- tetraphenyls bisglyoxaline and 2,2- bis- (2,6- dichlorophenyls) -4,4 ' 5,5 '-tetraphenyl -1,
2 '-bisglyoxalines.
The example of oxime compound may include adjacent ethoxy carbonyl-α-oxyimino group -1- phenyl propyl- 1- ketone and formula (I)~
(III) compound：
In addition, in the case where not damaging the effect of the present invention, it is poly- that other light known in the art can also be used together
Close initiator.Other Photoepolymerizationinitiater initiaters can be such as benzoin class, benzophenone, thioxanthene ketone class, anthracene compound,
It may be used singly or two or more in combination.
The example of benzoin class compound may include that benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin are different
Propyl ether and benzoin isobutyl ether.
The example of benzophenone compound may include benzophenone, o-benzoyl yl benzoic acid methyl esters, 4- phenyl two
Benzophenone, 4- benzoyl -4'- methyldiphenyls thioether, 3,3', 4,4'- tetra- (t-butyl peroxy carbonyl) benzophenone and 2,4,
6- tri-methyl benzophenones.
The example of thioxanthene ketone class compound may include 2-isopropylthioxanthone, 2,4- diethyl thioxanthones, 2,4- dichloros
Thioxanthones and the chloro- 4- propoxythioxanthones of 1-.
The example of anthracene compound may include 9,10- dimethoxys anthracene, 2- ethyl -9,10- dimethoxys anthracene, 9,10-
Diethoxy anthracene, 2- ethyl -9,10- diethoxy anthracenes.
In addition, the example of other Photoepolymerizationinitiater initiaters may include 2,4,6-trimethylbenzoyldiphenylphosphine oxide,
10- butyl -2- chloro-acridines ketone, 2- ethyl hydrazine, 9,10- phenanthrenequione, camphorquinone, phenylglyoxalates methyl esters and titanocenes compound.
In addition, Photoepolymerizationinitiater initiater (D) can be used together with light-initiated auxiliary agent (D-1).When Photoepolymerizationinitiater initiater (D) with
When light-initiated auxiliary agent (D-1) is used together, colored photosensitive resin composition can have the sensibility of enhancing, so as to improve
Productivity.
Specifically, light-initiated auxiliary agent (D-1) can be selected from by amine, carboxylic acid, organic compounds containing sulfur with mercapto
And its group of mixture composition.
The example of amine may include：Aliphatic amine, such as triethanolamine, methyl diethanolamine and triisopropanolamine；And fragrance
Race's amine, such as 4- dimethylaminobenzoic acids methyl esters, ethyl 4-dimethylaminobenzoate, 4- dimethylaminobenzoic acid isoamyls
Ester, 4- dimethylaminobenzoic acid 2- ethylhexyls, benzoic acid 2- dimethylamino ethyl esters, N, N- dimethyl-p-toluidines, 4,
Bis- (dimethylamino) benzophenone (michaelis ketone) of 4'- and bis- (diethylamino) benzophenone of 4,4'-.Preferably aromatic series
Amine.
Carboxylic acid may include the miscellaneous acetic acid of aromatic series, for example, phenyl acetic acid, aminomethyl phenyl thioacetic acid, ethylphenyl
Thioacetic acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenylthio acetic acid, dimethoxy
Phenyl acetic acid, chlorophenylthio acetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthio
Acetic acid, N- naphthalenes glycine and naphthoxy acetic acid.
The example of organic compounds containing sulfur with mercapto may include 2-mercaptobenzothiazole, bis- (the 3- sulfydryls of 1,4-
Butyryl acyloxy) butane, 1,3,5- tri- (3- sulfydryls butoxyethyl group) -1,3,5- triazines -2,4,6 (1H, 3H, 5H)-triketone, three
(3- mercaptopropionic acids) trihydroxy methyl propyl ester, four (3- mercaptobutyric acids) pentaerythritol esters, four (3- mercaptopropionic acids) pentaerythritol esters, six
(3- mercaptopropionic acids) dipentaerythritol ester and bis- (3- mercaptopropionic acids) tetraethylene glycol esters.
Preferably, be based on adhesive resin (B) and photopolymerization monomer (C) total solids content, with 0.1 weight %~
The amount of 40 weight %, more preferably 1 weight of weight %~30 % include Photoepolymerizationinitiater initiater (D).When Photoepolymerizationinitiater initiater (D)
Amount be the 0.1 weight % of weight %~40 when, colored photosensitive resin composition of the invention can have hypersensitivity so as to shorten
Thus time for exposure improves productivity, and keeps high-resolution.In addition, the composition be capable of providing enough image pixel intensities and
Good Pixel surface flatness.
In addition, when using light-initiated auxiliary agent (D-1), it is preferred that be based on adhesive resin (B) and photopolymerization monomer
(C) total solids content, the amount with 0.1 weight of weight %~50 %, more preferably 1 weight of weight %~40 % include light-initiated
Auxiliary agent (D-1).When the amount of light-initiated auxiliary agent is the 0.1 weight % of weight %~50, colored photosensitive resin composition of the invention
There can be the sensibility further improved, and improve the productivity of the colour filter formed using the composition.
Antioxidant (E)
In an embodiment of the invention, antioxidant (E) includes phenol antioxidant and sulphur class antioxidant
Mixture.Compared with using a kind of individually antioxidant, it can be shown using the mixture of phenol antioxidant and sulphur class antioxidant
Improved effect is shown.
The example of phenol antioxidant may include the bis- [2- [3- (3- tertiary butyl-4-hydroxy -5- aminomethyl phenyls) third of 3,9-
Acyloxy] -1,1- dimethyl ethyls] -2,4,8,10- four oxaspiro [5.5] hendecane (ADEKASTAB AO-80 of ADEKA,
The Sumilizer GA-80 of Sumitomo Chemical), four [3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid Ji Wusi
Alcohol ester (the ADEKASTAB AO-60 of IRGANOX1010, ADEKA of BASF, the Sumilizer of Sumitomo Chemical
BP-101), 1,3,5- trimethyls -2,4,6- three (3 ' 5 '-di-tert-butyl-4-hydroxyl benzyl) benzene (IRGANOX1330 of BASF,
The ADEKASTAB AO-330 of ADEKA), triethylene glycol-it is bis- [3- (3- tertiary butyl -5- methyl -4- hydroxy phenyls) propionic ester]
(the ADEKASTAB AO-70 of the IRGANOX245 and ADEKA of BASF), 4,4 '-thiobis (6- tertiary butyl -3- methylphenols)
(the Sumilizer WX of Sumitomo Chemical), three-(3,5- di-tert-butyl-4-hydroxyl benzyls)-isocyanuric acid esters
Bis- [3- (3,5- di-t-butyl -4- the hydroxyls of (the ADEKASTAB AO-20 of IRGANOX3114, ADEKA of BASF), 1,6-HD -
Base phenyl) propionic ester] (IRGANOX259 of BASF), the bis- [3- (3,5- di-t-butyl -4- hydroxy benzenes of 2,2- thiodiethylenes
Base) propionic ester] (IRGANOX1035 of BASF), N, N '-hexamethylene bis (3,5- di-t-butyls -4- hydroxyls-hydrocinnamamide
Amine) (IRGANOX1098 of BASF), bis- [(octylsulfo) the methyl]-o-cresols (IRGANOX1520L of BASF) of 2,4-, 18
Alkyl-[3- (3,5- di-tert-butyl-hydroxy phenyls) propionic esters (ADEKASTAB of IRGANOX1076, ADEKA of BASF
The Sumilizer BP-76 of AO-50, Sumitomo Chemical), 4,4 '-butylidenes-bis- (3 methy 6 tert butyl phenol)
(the ADEKASTAB AO-40 of ADEKA, the Sumilizer BBM of Sumitomo Chemical), (2- methyl -4- of 1,1,3- tri-
Hydroxyl -5- tert-butyl-phenyls) butane (the ADEKASTAB AO-30 of ADEKA), bis- (n-octylthio) -6- (the 4- hydroxyls-of 2,4-
3,5- di-tert-butyl anilines) -1,3,5- triazines (IRGANOX565 of BASF), the adjacent first of 4,6- bis- (dodecylthiomethyls) -
Phenol (IRGANOX1726 of BASF), 2- tertiary butyls -6- (3- tertiary butyl -2- hydroxy-5-methyl bases benzyl) -4- aminomethyl phenyl propylene
Acid esters (the Sumilizer GM of Sumitomo Chemical), 2- [1- (2- hydroxyl -3,5- di-tert-pentyl-phenyls) ethyl] -4,
6- di-tert-pentyl-phenyls acrylate (the Sumilizer GS of Sumitomo Chemical), mixed type 6- [3- (3- tertiary butyls-
4- hydroxy-5-methyl bases phenyl) propoxyl group] -2,4,8,10- tetra-terts dibenzo [d, f] [1,3,2] dioxa hydrogen phosphide
(dioxaphosphephine) (the Sumilizer GP of Sumitomo Chemical).
The example of sulphur class antioxidant may include 3,3 '-thio-2 acid two (dodecyl) ester (IRGANOX of BASF
PS800FD), 3,3 '-thio-2 acid two (octadecyl) esters (the IRGANOX PS802FD of BASF), thio-2 acid two (ten
Trialkyl) ester (the ADEKASTAB AO-503 of ADEKA), pentaerythrite four (β-lauryl thiopropionate) (ADEKA's
ADEKASTAB AO-412S), the 3,3 '-thiodipropionate dilauryls (Sumilizer of Sumitomo Chemical
TPL-R), 3,3 '-thio-2 acid, two myristin (the Sumilizer TPM of Sumitomo Chemical), 3,3 '-thio
Dipropionic acid distearyl base ester (the Sumilizer TPS of Sumitomo Chemical), (the 3- lauryls thio third of pentaerythrite four
Acid esters) (the Sumilizer TPD of Sumitomo Chemical), 3,3 '-thio-2 acid two (tridecyl) esters
(the Sumilizer TL of Sumitomo Chemical), the 2-mercaptobenzimidazole (Sumilizer of Sumitomo Chemical
MB)。
The colored photosensitive resin composition of the present invention uses the mixture of phenol antioxidant and sulphur class antioxidant, to
Improve heat resistance and high brightness is provided.
Preferably, it is based on the solid content of 100 parts by weight Photoepolymerizationinitiater initiaters (D), with the parts by weight of 5 parts by weight~75
Amount includes antioxidant (E).When the amount of antioxidant is 5 parts by weight~75 parts by weight, heat resistance can be improved and can
Obtain high brightness.
Solvent (F)
In an embodiment of the invention, solvent (F) can be the colored photosensitive that can disperse or dissolve the present invention
Any solvent for the other components for including in resin combination.Specifically, it is preferable that be ether, aromatic hydrocarbon, ketone, alcohol, ester and acyl
Amine.
As example, solvent (F) may include ethylene glycol monoalkyl ether, such as ethylene glycol single methyl ether, ethylene glycol list ethyl
Ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether；
Diethylene glycol dialkyl ether, such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether
And diethylene glycol dibutyl ether；
Ethylene glycol alkyl ether acetic acid esters, such as methylcellosolve acetate and ethyl cellosolve acetate；
Alkylene glycol alkyl ether acetic acid esters, such as propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, the third two
Alcohol list propyl ether acetic acid esters, methoxybutyl acetic acid esters and methoxyphenyl acetate；
Aromatic hydrocarbon, such as benzene,toluene,xylene and trimethylbenzene；
Ketone, such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl iso-butyl ketone (MIBK) and cyclohexanone；
Alcohol, such as ethyl alcohol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerine；With
Ester, such as 3- ethoxyl ethyl propionates, 3- methoxy methyl propionates and cyclic ester, such as gamma-butyrolacton.
For coating and drying, solvent (F) is preferably the organic solvent that boiling point is 100 DEG C~200 DEG C, more preferably
Alkylene glycol alkyl ether acetic acid esters, ketone and ester, such as 3- ethoxyl ethyl propionates and 3- methoxy methyl propionates, and then more preferably
Propylene glycol methyl ether acetate, propylene glycol monoethyl acetic acid esters, cyclohexanone, 3- ethoxyl ethyl propionates and 3- methoxypropionic acids
Methyl esters.Above-mentioned solvent can be used alone, or be used in combination.
Preferably, the gross weight of the colored photosensitive resin composition based on the present invention, with 60 weight of weight %~90 %, more
Preferably the amount of 70 weight of weight %~85 % includes solvent (F).When the amount of solvent (F) is the 60 weight % of weight %~90,
It can be obtained using coating machines such as such as roll coater, spin coater, slit spin coater, narrow slot-coating machines (also referred to as " die coating machine ") and ink jet printers
Obtain good coating.
When necessary, the colored photosensitive resin composition of an embodiment of the invention can also include other polymers, it is hard
Agent, surfactant, adhesion promotor, UV absorbents, anti-coalescent etc..
The example of other polymers may include：Curable resin, such as epoxy resin and maleimide resin；And thermoplastic
Property resin, such as polyvinyl alcohol, polyacrylic acid, polyalkylene glycol monoalkyl ether, polyacrylic acid fluothane base ester, polyester and polyurethane.
Curing agent is for enhancing depth-hardened and mechanical strength.The example of curing agent may include epoxide
(epoxies), multi-functional isocyanates, melamine and oxetanes.
The example of epoxide includes bisphenol A type epoxy resin, bisphenol-A epoxy resin, bisphenol F type epoxy tree
Fat, A Hydrogenated Bisphenol A F types epoxy resin, phenolic resin varnish type epoxy resin, other aromatic epoxy resins, acrylic compounds asphalt mixtures modified by epoxy resin
The brominated derivative of fat, glycidyl ester resin, glycidyl amine resins, these epoxy resin；Different from these asphalt mixtures modified by epoxy resin
The aliphatic of fat and brominated derivative, alicyclic or aromatic epoxy compound；Epoxy butadiene (co) polymer；Epoxy isoamyl
Diene (co) polymer；(methyl) glycidyl alcohol ester (co) polymer；With isocyanuric acid three-glycidyl alcohol ester.
The example of oxetanes may include carbonic acid dioxygen azetidine, dimethylbenzene dioxygen azetidine, adipic acid pair
Oxetanes, terephthalic acid (TPA) dioxygen azetidine and cyclohexane dicarboxylic acid dioxygen azetidine.
Curing agent can be used together with the stiffening aids for the ring-opening polymerisation that can induce epoxide or oxetanes.
The example of stiffening aids may include polybasic carboxylic acid, polybasic acid anhydride and acid agent.
Polybasic acid anhydride can be epoxy resin hardener commercial product, for example, ADEKAHADONA EH-700 (ADK
Industries), RIKACID HH (NJC) and MH-700 (NJC).
Above-mentioned curing agent can be used alone, or be used in combination.
Surfactant is used to enhance the coating forming properties of the colored photosensitive resin composition of the present invention, and can include
Fluorine and silicon class surfactant.
The example of silicon class surfactant may include commercial product, such as DC3PA, DC7PA, SH11PA, SH21PA and
SH8400 (Dow Corning Toray Silicone) and TSF-4440, TSF-4300, TSF-4445, TSF-4446,
TSF-4460 and TSF-4452 (GE Toshiba Silicones).The example of fluorine class surfactant may include commercially available production
Product, such as MEGAFACE F-470, F-471, F-475, F-482 and F-489 (Dainippon Ink and Chemical
Industry)。
Above-mentioned surfactant can be used alone, or be used in combination.
The example of adhesion promotor may include vinyltrimethoxysilane, vinyltriethoxysilane, vinyl
Three (2- methoxy ethoxies) silane, N- (2- amino-ethyls) -3- aminopropylmethyldimethoxysilanes, N- (2- amino second
Base) -3- TSL 8330s, 3-aminopropyltriethoxysilane, 3- glycidoxypropyl trimethoxies
Silane, 3- glycidoxypropyls dimethoxysilane, 2- (3,4- epoxycyclohexyls) ethyl trimethoxy silane, 3-
Chloropropylmethyldimethoxysilane, 3- r-chloropropyl trimethoxyl silanes, 3- methacryloxypropyl trimethoxy silanes,
3-mercaptopropyi trimethoxy silane, 3- isocyanate propyl trimethoxysilanes and 3- isocyanates propyl-triethoxysilicanes
Alkane.
Above-mentioned adhesion promotor can be used alone, or be used in combination.Preferably, based on the present invention's
The total solids content of Photosensitve resin composition, with 0.01 weight of weight %~10 %, more preferably 0.05 weight of weight %~2 %
Amount include adhesion promotor.
The example of UV absorbents may include 2- (3- tertiary butyl -2- hydroxy-5-methyl bases phenyl) -5- chlorobenzotriazoles and alkane
Oxygroup benzophenone.
The example of anti-coalescent may include Sodium Polyacrylate.
The colored photosensitive resin composition of one embodiment of the present invention can be prepared by the following method.For example, incite somebody to action
Toner (A) is mixed with solvent (F), and is disperseed the mixture using ball mill, until the average diameter of colorant reaches about 0.2
μm or less.When necessary, hybrid pigment dispersant or part or all of adhesive resin (B).(also referred to as to mixed dispersion
" powder base (mill base) ") in add remaining adhesive resin (B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D) and
Other components can further add solvent to obtain desired concentration, to prepare colored photosensitive resin combination when necessary
Object.
The colour filter that one embodiment of the present invention relates to be formed by using above-mentioned colored photosensitive resin composition.This
The colour filter of one embodiment of invention includes the dyed layer formed in the following manner：Colored photosensitive resin composition is coated
On substrate, with post-exposure and develop, to form pattern.
The method for forming pattern using the colored photosensitive resin composition of the present invention is described more fully below.
Using the present invention colored photosensitive resin composition formed pattern method can by means known in the art into
Row, and generally include coating, exposure and removal step.The colored photosensitive resin composition of the present invention is coated to substrate,
It then carries out photocuring and develops, to form the pattern as black matrix" or colour element (coloured image).
In coating step, the colored photosensitive resin composition of the present invention is coated in substrate (commonly used in the art, example
Such as, glass or silicon wafer, unrestricted) on or the pre-formed layer of colored photosensitive resin composition on, then carry out predrying with
Such as solvent volatile component is removed, to provide smooth coated film.Coated film is preferably with 1 μm~3 μm of thickness.
In step of exposure, in order to obtain desired pattern, the specific region of mask is used using UV irradiation coated films.
For using parallel rays uniform irradiation whole region and mask being made to be precisely directed to substrate, it is preferred to use mask aligner or
Stepper.
In removal step, cured coated film will be irradiated by UV and will be contacted with aqueous alkali so that unexposed area dissolves
Development, thus to obtain desired pattern.After development, it may be necessary to be dried 10 minutes~60 points at 150 DEG C~230 DEG C
Clock.
It can be developed using any developing solution known in the art.It is closed containing alkalization specifically, can use
The aqueous solution of object and surfactant.
Alkali compounds can be inorganic or organic basic compound.The example of inorganic alkaline compound may include hydrogen-oxygen
Change sodium, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium metasilicate,
Potassium silicate, sodium carbonate, potassium carbonate, sodium bicarbonate, saleratus, Boratex, potassium borate and ammonium hydroxide.The reality of organic basic compound
Example may include tetramethylammonium hydroxide, 2- hydroxyethyls trimethylammonium hydroxide, monomethyl amine, dimethyl amine, Trimethylamine,
Monoethylamine, diethylamide, triethylamine, single isopropylamine, diisopropylamine and ethanol amine.These inorganic and organic basics
It closes object can be used alone, or is used in combination.Gross weight based on developing solution, can be with the weight of 0.01 parts by weight~10
Measure part, the amount of the preferably parts by weight of 0.03 parts by weight~5 includes alkali compounds.
Surfactant can be nonionic, anionic or cationic surface active agent.Non-ionic surface is lived
The example of property agent may include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkylaryl ether and other polyoxies
Ethene derivatives, ethylene oxide-propylene oxide block copolymer, sorbitan aliphatic ester, Polyoxyethylene Sorbitan
Acid esters, polyoxyethylene sorbitol aliphatic ester, fatty acid glyceride, polyoxyethylene fatty acid ester and polyoxyethylene alkyl amine.
The example of anionic surfactant may include：Higher alcohol sulfate, such as sldium lauryl sulfate and oleyl alcohol sodium sulphate；Alkane
Base sulfate, such as NaLS and Texapon Special；Alkylaryl sulfonates, such as neopelex and 12
Negel.The example of cationic surface active agent may include amine and quaternary ammonium salt, such as stearic amine hydrochloride and the moon
Osmanthus base trimethyl ammonium chloride.These surfactants can be used alone, and can also be used in combination.It is molten based on developing
The gross weight of liquid, can be to be preferably the parts by weight of 0.01 parts by weight~10, the parts by weight of more preferably 0.05 parts by weight~8, Jin Ergeng
The amount of the parts by weight of preferably 0.1 parts by weight~5 includes surfactant.
As described above, colored photosensitive resin composition is coated, is dried, exposing patterns and development, thus provide with
The corresponding pixel of each color or black matrix" of coloured material in Photosensitve resin composition, and the color needed for colour filter
Quantity repeats these processes, thus to obtain colour filter.The composition of colour filter and preparation are well known in the art, thus herein
It omits the detailed description.
One embodiment of the present invention relates to a kind of liquid crystal display devices with above-mentioned colour filter.
The liquid crystal display device of the present invention has above-mentioned colour filter, and includes other assemblies as known in the art.Also
It is that present invention encompasses any liquid crystal display devices for capableing of colour filter using the present invention.Such as transmission-type liquid crystal display dress
It sets, wherein the comparative electrode substrate with thin film transistor (TFT) (TFT), pixel electrode and both alignment layers is facing with each other at a predetermined interval,
And liquid crystal material is introduced into the interval to form liquid crystal layer.Furthermore, it is possible to reflection-type liquid-crystal display device is mentioned, described device
There is reflecting layer between colour filtering chip basic board and dyed layer.Furthermore it is also possible to following liquid crystal display devices are mentioned, described device packet
Containing thin film transistor (TFT) (TFT) substrate being incorporated in the transparent electrode of colour filter and to be fixed on TFT substrate Chong Die with colour filter
Backlight on position.
It is further illustrated the present invention by following embodiment, comparative example and experimental example, and it is not considered that they limit this
The range of invention.
Examples 1 to 2 and comparative example 1~4：The preparation of colored photosensitive resin composition
Each component (unit is mixed by ratio listed in following table：Weight %) it is combined to prepare colored photosensitive resin
Object.
【Table 1】
The each component of upper table 1 is as follows.
Colorant (A)
A-1：C.I. paratonere 254
A-2：Red 94 (TCI) of acid
Adhesive resin (B)
B-1：Copolymerization (methacrylic acid unit and the benzyl methacrylate list of methacrylic acid and benzyl methacrylate
The molar ratio of member：31:69；Acid value：105；Weight average molecular weight：30,000)
Photopolymerization monomer (C)
C-1：Six acrylic acid dipentaerythritol esters (KAYARAD DPHA, Nippon Kayaku)
Photoepolymerizationinitiater initiater (D)
D-1：OXE-01(Ciba)
Antioxidant (E)
E-1：Phenol antioxidant AO-60 (ADEKA)
E-2：Sulphur class antioxidant AO-412S (ADEKA)
E-3：Sulphur class antioxidant AO-503 (ADAKA)
E-4：Mixed type inhibitors Sumilizer GP (Sumitomo Chemical)
Solvent (F)
F-1：Propylene glycol monomethyl ether
F-2：3- ethoxyl ethyl propionates
Additive (G)
G-1：Silicon class surfactant (SH-8400)
G-2：Pigment dispersing agent
G-3：Adhesion promotor (3- methacryloxypropyl trimethoxy silanes)
Experimental example 1：The evaluation of brightness and heat resistance
Colour filter is prepared using the colored photosensitive resin composition prepared in Examples 1 and 2 and comparative example 1~4.Specifically
For, each colored photosensitive resin composition is coated on the glass substrate by spin coating, and glass substrate is placed on heating plate
The temperature of upper 100 DEG C of holding 3 minutes, to form film on the glass substrate.It then, will be with 1 μm~50 μm of line/chart spacing
Case and light transmittance test photomask of the pattern of change in ladder shape in 1%~100% range is made to be placed on film, and not had
Have under any special optical filter using 1KW high-pressure sodium lamps with 100mJ/cm2100 μm are divided between film and photomask
Lower progress UV irradiations, the mercury lamp contain whole g, h and i rays.The film irradiated through UV is immersed into the KOH as developing solution
(pH10.5) 2 minutes in aqueous solution.After development, film is washed with distilled water and is dried with nitrogen, is then being set as 220 DEG C
Baking oven in heat 1 hour, to provide colour filter.The confirmed thickness of colour filter obtained is 2.0 μm.
Colour filter produced above evaluates its brightness and heat resistance using following methods.As a result it is shown in table 2.
(1) brightness (Y)
Brightness and the chromaticity coordinates of dyed layer are measured using microspectrophotometer OSP-SP2000.
O：More than 17.8, △：17.6~17.8, X：Less than 17.6
(2) heat resistance
After heating colour filter 2 hours in the baking oven for being set as 230 DEG C, color change (△ Eab) is measured, and really
Recognize brightness change (△ Y).
△Eab
O：Less than 3, △：3~4, X：More than 4
△Y
O：Less than 0.3, △：0.3~0.5, X：More than 0.5
【Table 2】
(standard Rx=0.656, Ry=0.323)
As shown in table 2, with the colored photosensitive tree that uses the comparative example 1~4 of phenol antioxidant or sulphur class antioxidant
Oil/fat composition is compared, and is combined using the colored photosensitive resin of the present invention of the mixture of phenol antioxidant and sulphur class antioxidant
Object has excellent heat resistance, and shows smaller brightness change and higher brightness after other heating.
Although only certain exemplary embodiments of this invention has been shown and described, it will be understood by those skilled in the art that it is not
It is intended to that the present invention is made to be limited to these preferred embodiments, and it will be apparent to one skilled in the art that can carries out
Various changes and modifications, without departing from the spirit and scope of the invention.
Therefore, the scope of the present invention will be defined by the appended claims and the equivalents thereof.
Claims (6)
1. a kind of colored photosensitive resin composition, the colored photosensitive resin composition includes colorant (A), adhesive resin
(B), photopolymerization monomer (C), Photoepolymerizationinitiater initiater (D), antioxidant (E) and solvent (F), the colorant (A) include one
Kind or a variety of dyestuffs, and the antioxidant (E) includes the mixture of phenol antioxidant and sulphur class antioxidant, and do not wrap
Being contained in has the antioxidant of functional group and the functional group based on sulphur based on phenol in a molecule,
Wherein, it is based on the total solids content of the colorant (A), the dyestuff is contained with the amount of 1 weight of weight %~60 %, and
And based on the solid content of Photoepolymerizationinitiater initiater (D) described in 100 parts by weight, contained with the amount of the parts by weight of 5 parts by weight~75 described
Antioxidant (E).
2. colored photosensitive resin composition as described in claim 1, wherein the colorant (A) includes one or more red
Color dyestuff.
3. colored photosensitive resin composition as described in claim 1, wherein the colorant (A) also includes pigment.
4. colored photosensitive resin composition as described in claim 1, wherein based on the total of the colored photosensitive resin composition
Solid content contains the colorant (A) with the amount of 5 weight of weight %~70 %.
5. a kind of colour filter, the colour filter is combined by using colored photosensitive resin according to any one of claims 1 to 4
Object is formed.
6. a kind of liquid crystal display device, described device has the colour filter described in claim 5.
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| KR1020130090640A KR102047371B1 (en) | 2013-07-31 | 2013-07-31 | Colored Photosensitive Resin Composition, Color Filter, and Liquid Crystal Display Device Having the Same |
| KR10-2013-0090640 | 2013-07-31 |
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| KR102288719B1 (en) * | 2015-03-27 | 2021-08-11 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102186496B1 (en) * | 2015-03-27 | 2020-12-03 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102299970B1 (en) * | 2015-03-27 | 2021-09-08 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102361511B1 (en) * | 2015-12-18 | 2022-02-10 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device using the same |
| JPWO2018163702A1 (en) * | 2017-03-07 | 2019-12-26 | 富士フイルム株式会社 | Laminate, optical filter, solid-state imaging device, image display device, infrared sensor and kit |
| JP6917950B2 (en) * | 2017-08-23 | 2021-08-11 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Color curable resin composition, color filter, and display device |
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| KR20150015098A (en) | 2015-02-10 |
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| KR102047371B1 (en) | 2019-11-21 |
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