CN106959583A - Self-emission type Photosensitve resin composition, color conversion layer prepared therefrom and the image display device containing color conversion layer - Google Patents

Self-emission type Photosensitve resin composition, color conversion layer prepared therefrom and the image display device containing color conversion layer Download PDF

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Publication number
CN106959583A
CN106959583A CN201611223467.8A CN201611223467A CN106959583A CN 106959583 A CN106959583 A CN 106959583A CN 201611223467 A CN201611223467 A CN 201611223467A CN 106959583 A CN106959583 A CN 106959583A
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China
Prior art keywords
weight
self
emission type
resin composition
conversion layer
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CN201611223467.8A
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Chinese (zh)
Inventor
吴龙虎
朴廷烋
李宗洙
张虎振
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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Publication of CN106959583A publication Critical patent/CN106959583A/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • G02F1/1336—Illuminating 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • G02F1/1336—Illuminating devices
    • G02F1/133614—Illuminating devices using photoluminescence, e.g. phosphors illuminated by UV or blue light

Abstract

The fluorescent dye for including being represented by following formula 1 according to a kind of self-emission type Photosensitve resin composition of the present invention：[formula 1]Wherein, substituent is as defined in description.

Description

Self-emission type Photosensitve resin composition, color conversion layer prepared therefrom and containing color The image display device of conversion layer
Technical field
The present invention relates to a kind of self-emission type Photosensitve resin composition, color conversion layer prepared therefrom and including color The image display device of conversion layer.
Background technology
In recent years, display industry is significantly from cathode-ray tube (CRT) to by Plasmia indicating panel (PDP), flat-panel monitor (FPD) transformation of the representative such as Organic Light Emitting Diode (OLED), liquid crystal display (LCD).At these Central, LCD has been widely used as the image display device almost used in all industrial circles, and their application still exists Lasting extension.
In an lcd, when the white light produced from back light unit pass through liquid crystal cell when transmissivity is adjusted, and by it is red, The three primary colors that green and blue (RGB) colour filter is launched are mixed panchromatic to realize.
Cold-cathode fluorescence lamp (CCFL) is used as the light source of back light unit.In this case, CCFL is always needed because of back light unit The problem of power being provided to CCFL and there is high power consumption.In addition, it is also existed only has about 70% compared to tradition CRT The shortcoming of low color reprodubility, and cause due to the addition of mercury environmental pollution.
As the alternative solution for solving the above problems, actively deploy to the back of the body using light emitting diode (LED) The research of light unit.When LED is used as into back light unit, national television system committee (NTSC) color reprodubility is exceeded 100% as defined in scope, hence in so that more lively picture quality can be provided to consumer.
Therefore, proposed in same industry field using material and the side of structure for changing colour filter and LCD Method, with the efficiency for the light source for improving back light unit.
In colour filter, using including the dispersible composition of pigment or dyestuff, and make it by patterning process with shape Into the pixel of each color.Here, the pigment and dyestuff have problems in that, the efficiency of transmission of the light source of back light unit may Reduction.Efficiency of transmission reduction causes the color reproduction of display device to deteriorate, and therefore, it is difficult to realize high-quality image.
The problem of for example color reproduction is low can be solved by increasing the light efficiency of colour filter.Accordingly, it has been suggested that The method of increase filter thickness or on colour filter stacked color conversion layer (or light conversion layer) or the vicinity in colour filter The method for introducing color conversion layer (or light conversion layer).
Fig. 1 is the schematic diagram of the effect of color conversion layer in display device.As shown in figure 1, the light produced from back light unit 1 Source can directly improve light efficiency by color conversion layer 3 and colour filter 5.In the composition of color conversion layer, dyestuff or color Element has been used to the field of correlation.However, when the dyestuff and pigment are used alone, it may be difficult to improve light efficiency, and brightness It may also deteriorate.It is therefore proposed that being used as the material of color conversion layer 3 using fluorescent material.
The blue photoactivation that fluorescent material is launched from back light unit 1, and the wavelength of blue light is converted with along just Launch light in face direction.In such a case, it is possible to launch with red white light, with viridescent white light etc. so that light efficiency Improve.
Many patents on the color conversion layer including fluorescent material are applied for.Among these, Korean Patent Unexamined Publication No.2012-0048218 discloses a kind of display device, and it includes optical conversion element, and the optical conversion element is set Between back light unit and substrate or it is arranged in shutter unit, and is configured in blue light or ultraviolet (UV) wavelength model Incident light in enclosing is converted to the light in predetermined wavelength range, wherein, optical conversion element has at least one fluorescent material.
Korean patent unexamined discloses No.2013-0083807 and discloses a kind of liquid crystal display device, and it includes carrying The back light unit of bloom efficiency, wherein, introduce color conversion material (such as phosphor, quantum dot, white scattering material, electroluminescent Luminescent material and embedded photoluminescent material) to improve light efficiency.
Japanese patent publication discloses No.2013-077825 and discloses a kind of face for introducing and being made up of green light emitting phosphor Method of the color converting layer to improve the brightness of white light LEDs.
In these patents, various trials, which are intended to introduce, includes the color conversion layer of phosphor etc., to improve display dress The quality put.Here, these patents are only proposed including color is changed without the method for directly proposing to form color conversion layer The simple method being dispersed in solvent with wet coating color conversion layer of layer.
Color conversion layer, which can have, is formed as red (R) corresponding with colour filter and the corresponding figure of green (G) pixel cell Case.In this case, due to the size with hundreds of microns with formed the phosphor interspersion of color conversion layer in a solvent and It will not dissolve, so being difficult to form micro- pattern, and physical property can not be easily adjusted such as thickness.
Because micro- pattern can be formed by using the photoetching process of Photosensitve resin composition, it is possible to excluded these and asked Topic.
In the case of common Photosensitve resin composition, the use of light trigger is required to polymerization.However, photosensitive Resin combination exist new problem be：Because the free radical produced in light trigger is so that the fluorescence efficiency of phosphor may Reduction, and color conversion layer may be by light trigger yellow in the rear baking process carried out during photoetching process.
Korean patent unexamined discloses No.2009-0066076 and discloses a kind of Photosensitve resin composition, and it can pass through Using double bond containing acrylic carboxylate's resin and the Photoinitiated reactions of Acrylic Binder Resin, heat is improved to increase crosslinking Characteristic, wherein, the anti-oxidant of the oxidation for being prevented from Photosensitve resin composition is used during the preparation of Photosensitve resin composition Agent, to improve heat endurance.However, Photosensitve resin composition remains the not enough shortcoming of heat resistance.
Korean patent unexamined discloses No.2015-0039691 and discloses a kind of dye dispersion, wherein using dispersant Dyestuff is scattered in solvent, wherein, the dyestuff includes coumarine dye, and the gross weight based on dyestuff, coumarine dye Content in the range of 40 mass %-100 mass %, but do not confirm that heat resistance, light resistance, fluorescence efficiency whether can It is improved.
【Prior art literature】
【Patent document】
Patent document 1：Korean patent unexamined discloses No.2012-0048218
Patent document 2：Korean patent unexamined discloses No.2013-0083807
Patent document 3：Japanese patent publication discloses No.2013-077825
Patent document 4：Korean patent unexamined discloses No.2009-0066076
Patent document 5：Korean patent unexamined discloses No.2015-0039691
The content of the invention
Therefore, present invention seek to address that problem of the prior art, and use it is an object of the invention to provide one kind special Determine the self-emission type Photosensitve resin composition that can improve heat resistance, light resistance and fluorescence efficiency of fluorescent dye, by its preparation Color conversion layer and image display device including color conversion layer.
In order to solve the above problems, according to a kind of self-emission type photosensitive composition of illustrative embodiments of the present invention Thing includes fluorescent dye, adhesive resin, photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent, wherein, the fluorescent dye Including the dyestuff represented by following formula 1.
[formula 1]
In formula 1, substituent is as defined in description.
Brief description of the drawings
Fig. 1 is the schematic diagram for showing the effect of color conversion layer in display device.
Embodiment
According to the present invention, self-emission type Photosensitve resin composition includes the dyestuff represented by following formula 1.
Fluorescent dye
The fluorescent dye that the self-emission type Photosensitve resin composition of the present invention includes can include the dye represented by following formula 1 Material.
[formula 1]
In formula 1, L represents the divalent fluorinated alkyl with 1-20 carbon numbers, the divalent hydrocarbon with 1-20 carbon numbers Base or sulfonyl,
X represents oxygen atom or sulphur atom,
R7-R13Independently of one another represent hydrogen atom, halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,- SO3M、-CO2M, hydroxyl, formoxyl, amino or the univalence hydrocarbyl with 1-20 carbon numbers.
Constitute the methylene bridge-CH of alkyl2- can be by oxygen atom, sulphur atom ,-N (R14)-, sulfonyl or carbonyl substitution, And the hydrogen atom included in alkyl can be by halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,-SO3M、- CO2M, hydroxyl, formoxyl or amino substitution.
R14Hydrogen atom or the univalence hydrocarbyl with 1-20 carbon numbers are represented, if R14In the presence of plural number, it can phase It is same or different.
M represents hydrogen atom or alkali metal atom, if in the presence of M is with plural number, its can with identical or different, and
Z represents the compound represented by following formula 2 or formula 3.
[formula 2]
In formula 2, R1The alkyl with 1-20 carbon numbers is represented, and constitutes the methylene bridge-CH of alkyl2- can be by oxygen Atom replaces.
R2-R6Independently of one another represent hydrogen atom, halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,- SO3M、-CO2M, hydroxyl, formoxyl, amino or the univalence hydrocarbyl with 1-20 carbon numbers, constitute alkyl methylene bridge- CH2- can be by oxygen atom, sulphur atom ,-N (R30)-, amino or carbonyl substitution, and the hydrogen atom included in alkyl can be by halogen Plain atom, cyano group, nitro, carbamoyl, sulfamoyl ,-SO3M、-CO2M, hydroxyl, formoxyl or amino substitution,
R30Hydrogen atom or the univalence hydrocarbyl with 1-20 carbon numbers are represented, if R30In the presence of plural number, it can phase It is same or different, and
* bonded portion is represented.
[formula 3]
In formula 3, Ar1 and Ar2 represent to include the alkane with 1-8 carbon numbers at ortho position and/or meta independently of one another The phenyl of base, and
* bonded portion is represented.
Adhesive resin
The adhesive resin that includes of self-emission type Photosensitve resin composition of the present invention be typically due to light or heat effect and With reactivity and alkali solubility, and the decentralized medium as coloured material.In the self-emission type Photosensitve resin composition of the present invention Including all types of adhesive resins can use, if they can act as the adhesive resin of fluorescent dye, and Can be dissolved in for prepare color conversion layer developing process in used alkaline-based developer.
Adhesive resin can include such as carboxylic monomer and copolymerization that can be with another monomer of the monomer copolymerization Thing etc..Carboxylic monomer can for example include unsaturated monocarboxylic acid；Or unsaturated carboxylic acid for example has one in the molecule Or the unsaturated polyvalent carboxylic acid of multiple carboxyls, for example, unsaturated dicarboxylic, unsaturated tricarboxylic acids etc..Here, unsaturated unitary carboxylic Acid can be such as including acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid.Unsaturated dicarboxylic can be wrapped Include such as maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid.Unsaturated polyvalent carboxylic acid can be acid anhydrides, its specific example Maleic anhydride, itaconic anhydride, citraconic anhydride etc. can be included.In addition, unsaturated polyvalent carboxylic acid can be its list (2- methyl-props Alkene acyloxyallcyl) ester, its example can be for example including list (2- acryloyl-oxyethyls) succinate, list (2- metering systems Trimethylammonium) succinate, list (2- acryloyl-oxyethyls) phthalic acid ester, list (2- methacryloxyethyls) Phthalic acid ester etc..Unsaturated polyvalent carboxylic acid can be list (methyl) acrylic acid in the dicarboxyl based polyalcohol of two end Ester, its example can be for example including ω-carboxy-polycaprolactone mono acrylic ester or ω-carboxy-polycaprolactone monomethacrylates Deng.The carboxylic monomer may be used singly or in combination of two or more.Other monomers that can be with carboxyl group-containing monomer copolymerization Can for example include aromatic vinyl compound (such as styrene, α-methylstyrene, adjacent vinyltoluene, a vinyltoluene, To vinyltoluene, p-chlorostyrene, o-methoxystyrene, meta-methoxy styrene, to methoxy styrene, adjacent vinyl Benzyl methyl ether, a vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinylbenzyl glycidyl base ether, Vinylbenzyl glycidyl base ether, to vinylbenzyl glycidyl base ether, indenes etc.), esters of unsaturated carboxylic acids (such as acrylic acid first Ester, methyl methacrylate, ethyl acrylate, EMA, n-propyl, n propyl methacrylate, third Isopropyl gadoleate, isopropyl methacrylate, n-butyl acrylate, n-BMA, isobutyl acrylate, methyl-prop The secondary butyl ester of olefin(e) acid isobutyl ester, sec-butyl acrylate, methacrylic acid, tert-butyl acrylate, Tert-butyl Methacrylate, propylene Acid -2- hydroxy methacrylates, methacrylic acid -2- hydroxy methacrylates, 2-hydroxypropyl acrylate, methacrylic acid -2- hydroxy propyl esters, Acrylic acid -3- hydroxy propyl esters, methacrylic acid -3- hydroxy propyl esters, acrylic acid -4- hydroxybutyls, methacrylic acid -4- hydroxyl fourths Ester, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, methyl Cyclohexyl acrylate, phenyl acrylate, phenyl methacrylate, acrylic acid -2- methoxy acrylates, methacrylic acid -2- methoxies Base ethyl ester, acrylic acid -2- phenoxy ethyls, methacrylic acid -2- phenoxy ethyls, methoxyl group diethylene glycol (DEG) acrylate, methoxy Base diethylene glycol (DEG) methacrylate, methoxy triglycol acrylate, methoxy triglycol methacrylate, methoxy propyl two Alcohol acrylate, MPEG methacrylate, methoxyl group DPG acrylate, methoxyl group dipropylene glycol methyl Acrylate, isobornyl acrylate, isobornyl methacrylate, acrylic acid bicyclopentadiene ester, the ring of methacrylic acid two Pentadiene ester, (methyl) acrylic acid Buddha's warrior attendant alkyl ester, (methyl) acrylic acid norborneol ester, acrylic acid -2- hydroxyl -3- phenoxy groups third Ester, methacrylic acid -2- hydroxyl -3- phenoxy-propyls, glycerol mono-acrylate, glycerin monomethyl acrylic ester etc.)；It is unsaturated Carboxylic acid amide's Arrcostab (such as acrylic acid -2- amino ethyl esters, methacrylic acid -2- amino ethyl esters, acrylic acid -2- dimethylaminos Ethyl ester, methacrylic acid -2- dimethylamino ethyl esters, acrylic acid -2- amino propyl ester, methacrylic acid -2- amino propyl ester, propylene Acid -2- dimethylaminos propyl ester, methacrylic acid -2- dimethylaminos propyl ester, acrylic acid -3- amino propyl ester, methacrylic acid - 3- amino propyl ester, acrylic acid -3- dimethylaminos propyl ester, methacrylic acid -3- dimethylamino propyl ester etc.)；Unsaturated carboxylic acid Ethylene oxidic ester (such as glycidyl acrylate, GMA)；Vinyl carboxylates (such as vinyl acetate Ester, propionate, vinyl butyrate, vinyl benzoate etc.)；Unsaturated ethers (such as vinyl methyl ether, vinyl ethyl Ether, allyl glycidyl ether etc.)；Vinyl cyanide compound (such as acrylonitrile, methacrylonitrile, α-chloro-acrylonitrile, inclined dicyan Ethene etc.)；Unsaturated amides (such as acrylamide, Methacrylamide, α-chloroacrylamide, N-2- hydroxyethyl acrylamides, N-2- hydroxyethyl methacrylamides etc.)；Unsaturated acyl imines (such as maleimide, benzyl maleimide, N- phenyl horses Come acid imide, N- N-cyclohexylmaleimides etc.), aliphatic conjugated dienes (such as 1,3- butadiene, isoprene, chlorobutadiene Deng)；With polymer molecular chain (such as polystyrene, PMA, polymethyl methacrylate, polyacrylic acid N-butyl, Vinalac 5920, polysiloxanes etc.) end there is the macromolecular list of single acryloyl group or monomethacrylate acyl group Body.These monomers may be used singly or in combination of two or more.Especially it is preferable to use for example with norborny The large volume monomer such as the monomer of skeleton, the monomer with adamantane framework, monomer with rosin skeleton as can with containing carboxyl Other monomers of monomer copolymerization, because large volume monomer is easy to reduce dielectric constant values.
Preferably there is 20-200 (mg KOH/g) acid number according to the adhesive resin of the present invention.When acid number falls in the scope When interior, the dissolubility in developer solution can be improved, so as to dissolving easily unexposed area and cause the raising of sensitivity. Therefore, because pattern is maintained on exposure area during developing, therefore it can preferably improve film residual rate.Here, term " acid Value " refers to the measured value of the amount (mg) as the potassium hydroxide needed for neutralization 1g acrylic polymers, and can generally make Calculated with potassium hydroxide aqueous solution by titrating.In addition, such as passing through gel permeation chromatography (GPC；Using tetrahydrofuran as Eluting solvent) determined, the weight average molecular weight (hereinafter referred to as " weight average molecular weight ") converted relative to polystyrene standards, Adhesive resin in the range of 3000-200000 is preferred, and the adhesive resin in the range of 5000-100000 is more excellent Choosing.When molecular weight within the range when, film can have improved hardness and high film residual rate, and unexposed area can be with There is excellent dissolubility in developer solution, and be easy to improve resolution ratio.
The molecular weight distribution [weight average molecular weight (Mw)/number-average molecular weight (Mn)] of adhesive resin is preferably 1.5-6.0's In the range of, more preferably in the range of 1.8-4.0.When molecular weight distribution [weight average molecular weight (Mw)/number-average molecular weight (Mn)] exists When in the range of 1.5-6.0, developing property can be excellent.
According to the present invention, based on the overall weight percent of the solid in self-emission type Photosensitve resin composition, comprising it is viscous The content of mixture resin is preferably 1 weight %-60 weight %.When adhesive resin content within the range when, due to aobvious Enough dissolubilities in shadow liquid, development residues will not can be readily formed on the substrate with non-pixel region, and Because the film thickness of the pixel region in exposure area is not easy to reduce during developing, tend to remove non-pixel region.
Photopolymerizable compound
Photopolymerizable compound according to being included in the self-emission type Photosensitve resin composition of the present invention is by following The effect of light and Photoepolymerizationinitiater initiater and the compound that can polymerize, can include monofunctional monomer, bifunctional monomer, Qi Taduo Functional monomer etc..
The specific example of monofunctional monomer can include nonyl phenyl carbitol acrylate, acrylic acid 2- hydroxyl -3- benzene Epoxide propyl ester, 2- ethylhexyl carbitols acrylate, acrylic acid 2- hydroxy methacrylates, NVP etc..
The specific example of bifunctional monomer can include 1,6-HD two (methyl) acrylate, ethylene glycol two (methyl) Acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, double (acryloxies of bisphenol-A Ethyl) ether, 3- methyl pentanediols two (methyl) acrylate etc..
The specific example of other polyfunctional monomers can include trimethylolpropane tris (methyl) acrylate, pentaerythrite Three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, two seasons penta 4 Alcohol six (methyl) acrylate etc..Among these, bifunctional monomer is preferably used or higher polyfunctional monomer.
Based on the overall weight percent of solid in self-emission type Photosensitve resin composition, the content of photopolymerizable compound is excellent Elect 5 weight %-50 weight %, more preferably 7 weight %-45 weight % as.When the content of photopolymerizable compound is in the scope When interior, pixel cell can have enhanced intensity or good smoothness properties.
Photoepolymerizationinitiater initiater
The Photoepolymerizationinitiater initiater used in the present invention preferably comprises acetophenone compounds.Acetophenone compounds can example Such as include diethoxy acetophenone, 2- hydroxy-2-methyl -1- phenyl propyl- 1- ketone, benzyl dimethyl ketal, 2- hydroxyl -1- [4- (2- hydroxyl-oxethyls) phenyl] -2- methyl propyl- 1- ketone, 1- hydroxycyclohexylphenylketones, 2- methyl isophthalic acids-(4- methyl mercaptos phenyl) - 2- morpholino propyl- 1- ketone, 2- benzyl -2- dimethylaminos -1- (4- morphlinophenyls) butyl- 1- ketone, 2- hydroxyl 2- methyl [4- (1- methyl ethylenes) phenyl] propyl- 1- ketone etc. oligomer, and preferably 2- benzyls -2- dimethylaminos -1- (4- morpholinoes Phenyl) butyl- 1- ketone.Furthermore, it is possible to which the Photoepolymerizationinitiater initiater in addition to acetophenone compounds is applied in combination.Except acetophenones Free-radical generating agent that Photoepolymerizationinitiater initiater beyond compound can include being used for producing free radical in light irradiation, sensitizer, Acid producing agent etc..Free-radical generating agent can be for example including benzoin class compound, benzophenone compound, thioxanthene ketone class Compound, compound in triazine class etc..Benzoin class compound can be for example including benzoin, benzoin methylether, benzoin ethyl ether, benzene Anisoin isopropyl ether, benzoin isobutyl ether etc..Benzophenone compound can be for example including benzophenone, o-benzoyl Ji Benjia Sour methyl esters, 4- phenyl benzophenones, 4- benzoyl -4'- methyldiphenyls thioether, 3,3', 4,4'- tetra- (t-butyl peroxy carbonyl) Benzophenone, 2,4,6- tri-methyl benzophenones etc..Thioxanthene ketone class compound can be for example different including ITX, 4- Propyl group thioxanthones, 2,4- diethyl thioxanthones, the clopenthixal ketones of 2,4- bis-, the chloro- 4- propoxythioxanthones of 1- etc..Compound in triazine class Can be for example including double (trichloromethyl) -6- (4- the methoxyphenyls) -1,3,5- triazines of 2,4-, double (the trichloromethyl) -6- of 2,4- (4- methoxyl groups naphthyl) -1,3,5- triazines, 2,4- double (trichloromethyl) -6- (4- methoxyl-styrenes) -1,3,5- triazines, 2, Double (trichloromethyl) -6- [2- (5- methylfuran -2- bases) the vinyl] -1,3,5- triazines of 4-, double (the trichloromethyl) -6- of 2,4- Double (trichloromethyl) -6- [2- (4- diethylamino -2- methylbenzenes of [2- (furans -2- bases) vinyl] -1,3,5- triazines, 2,4- Base) vinyl] -1,3,5- triazines, double (trichloromethyl) -6- [2- (3,4- Dimethoxyphenyls) the vinyl] -1,3,5- of 2,4- Triazine etc..The double benzene of (Chloro-O-Phenyl) -4,4', 5,5'- tetra- of such as 2,4,6- trimethyl benzoyl diphenyls base phosphine oxide, 2,2'- Base -1,2'- bisglyoxalines, 10- butyl -2- chloro-acridines ketone, 2- EAQs, benzil, 9,10- phenanthrenequione, camphorquinone, ethylalbenzene Sour methyl esters, titanocenes compound etc., may be used as free-radical generating agent.Acid producing agent can be for example including salt such as 4- hydroxyls Pheiiyldimetliyl sulfonium tosilate, 4- hydroxy phenyl dimethyl sulfoniums hexafluoro antimonate, 4- acetoxyl group phenyl dimethyl sulfoniums Tosilate, 4- acetoxyl group phenyl methyl benzyl sulfoniums hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium Hexafluoro antimonate, Er Ben Ji Iodonium tosilate, Er Ben Ji Iodonium hexafluoro antimonates etc., or nitrobenzyl tosylat, Benzoin tosylate etc..Among these compounds, the compound for producing acid and free radical can be used as freedom Base producing agent.For example, triazines Photoepolymerizationinitiater initiater is also used as acid producing agent.
Overall weight percent based on adhesive resin and photopolymerizable compound, photosensitive according to self-emission type of the present invention The content of the Photoepolymerizationinitiater initiater used in resin combination can be 0.1 weight %-40 weight %, preferably 1 weight %-30 Weight %.When comprising Photoepolymerizationinitiater initiater within the range when, self-emission type Photosensitve resin composition can be height be sensitized So that the pixel cell formed using said composition is had good intensity or had at the surface of pixel cell good Smoothness properties.
In addition, photopolymerization initiator auxiliary agent can be used in the present invention.Photopolymerization initiator auxiliary agent generally triggers with photopolymerization Agent is applied in combination, and is to be used to promote the change that photopolymerizable compound (its polymerization is triggered by Photoepolymerizationinitiater initiater) is polymerize Compound.Photopolymerization initiator auxiliary agent can include aminated compounds, alkoxy anthracene compound, thioxanthene ketone class compound etc..
Aminated compounds can be for example including triethanolamine, methyl diethanolamine, triisopropanolamine, 4- dimethylamino benzene Methyl formate, EDMAB, 4- dimethylaminobenzoic acids isopentyl ester, benzoic acid -2- dimethylaminos Ethyl ester, 4- dimethylaminobenzoic acid -2- Octyl Nitrites, N, double (dimethylamino) hexichol of N- dimethyl-p-toluidines, 4,4'- Ketone (commonly referred to as michaelis ketone), double (diethylamino) benzophenone of 4,4'-, double (ethylmethylamino) the hexichol first of 4,4'- Ketone etc..In addition, among these, double (diethylamino) benzophenone of preferably 4,4'-.Alkoxy anthracene compound can be such as Including 9,10- dimethoxys anthracene, 2- ethyl -9,10- dimethoxys anthracene, 9,10- diethoxies anthracene, 2- ethyl -9,10- diethoxies Base anthracene etc..Thioxanthene ketone class compound can be for example including ITX, ITX, 2,4- diethyl thioxanthenes Ketone, the clopenthixal ketones of 2,4- bis-, the chloro- 4- propoxythioxanthones of 1- etc..
These Photoepolymerizationinitiater initiaters be can be used alone or multiple combinations are used.In addition it is possible to use commercially available photopolymerization Auxiliary agent is triggered to be used as photopolymerization initiator auxiliary agent.For example, commercially available photopolymerization initiator auxiliary agent can include trade name " EAB-F " (by Hodogaya Chemical Co.Ltd. are manufactured) etc..
When using these photopolymerization initiator auxiliary agents, photopolymerization initiator auxiliary agent can be preferably with every mole of Photoepolymerizationinitiater initiater Amount for below 10mol (more preferably 0.01-5mol) is used.When comprising photopolymerization initiator auxiliary agent within the range when, can Further to improve the sensitivity of self-emission type Photosensitve resin composition, and it is easy to improve the color turn using said composition formation Change the making of layer.
Solvent
Solvent included in self-emission type Photosensitve resin composition according to the present invention is not particularly limited.For example, The various organic solvents used in self-emission type Photosensitve resin composition field can be used.
The specific example of solvent can include ethylene glycol monoalkyl ether (such as glycol monoethyl ether, ethylene glycol monoethyl ether, second two Alcohol list propyl ether, ethylene glycol monobutyl ether etc.)；Diethylene glycol dialkyl ether (such as diethylene glycol dimethyl ether, diethylene glycol diethyl Ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether etc.)；Ethylene glycol alkyl ether acetic acid esters (such as methylcellosolve acetate, Ethyl cellosolve acetate etc.)；Aklylene glycol alkylether acetates (such as propylene glycol methyl ether acetate, dihydroxypropane single-ether Acetic acid esters, propylene glycol monopropyl ether acetic acid esters, methoxy butyl acetate, acetic acid methoxyl group pentyl ester etc.), aromatic hydrocarbons (such as benzene, toluene, two Toluene, mesitylene etc.)；Ketone (such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl iso-butyl ketone (MIBK), cyclohexanone)；Alcohol is (such as Ethanol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerine etc.)；Ester (such as 3- ethoxyl ethyl propionates, 3- methoxypropionic acids Methyl esters etc.)；Cyclic ethers (such as gamma-butyrolacton).Among these, above-mentioned solvent preferably includes boiling point to be had for 100 DEG C -200 DEG C Machine solvent, more preferably aklylene glycol alkylether acetates, ketone or ester (such as 3- ethoxyl ethyl propionates or 3- methoxypropionic acids Methyl esters) etc., and from coating and the angle of drying property, most preferably propylene glycol methyl ether acetate, dihydroxypropane single-ether Acetic acid esters, cyclohexanone, 3- ethoxyl ethyl propionates, 3- methoxy methyl propionates etc..These solvents can be used alone or two kinds Combination of the above is used.
Based on the overall weight percent of self-emission type Photosensitve resin composition, according to the self-emission type photosensitive resin of the present invention The content of solvent is preferably 60 weight %-90 weight % in composition, more preferably 70 weight %-85 weight %.When solvent Content within the range when, self-emission type Photosensitve resin composition use coating system such as roll coater, spin coater, slit and rotation When turning the coating such as coating machine, slit coater (being commonly referred to as molded coating machine), ink jet printer, good coating can be shown Property.
Antioxidant
Antioxidant can also be included according to the self-emission type Photosensitve resin composition of the present invention.The species of antioxidant can To be used alone or be used in combination.It is anti-oxidant based on the overall weight percent of self-emission type Photosensitve resin composition Agent can be used with 0.1 weight %-10 weight % content, preferably be used with 0.2 weight %-7 weight % content.The content Refer to prevent scope that the light efficiency of Photoepolymerizationinitiater initiater declines and selected, and especially, for Photoepolymerizationinitiater initiater with A range of weight ratio is used.
Preferably, light stabilizer is made up of Photoepolymerizationinitiater initiater and antioxidant so that Photoepolymerizationinitiater initiater and anti-oxidant Agent is with 1:0.1-1:3 weight ratio is used, or more preferably with 1:0.2-1:0.5 weight ratio is used.When antioxidant and light are poly- When the weight ratio for closing initiator is less than the scope, it may not be possible to ensure light efficiency, this makes it difficult to ensure that sufficient color conversion Characteristic.On the other hand, when the weight ratio of antioxidant and Photoepolymerizationinitiater initiater is more than the scope, brightness may be reduced.
Can use selected from by benzotriazole light stabilizer, triazines as light stabilizer, benzophenone light stabilizer, It is at least one as antioxidant in the group that HALS classes light stabilizer and combinations thereof are constituted, but the invention is not restricted to This.
Known BTA analog derivative can be used as benzotriazole light stabilizer or commercially available product. Specifically, the example of BTA analog derivative can include 2- (2'- hydroxyl -5'- aminomethyl phenyls) BTA, 2- (2'- hydroxyls Base -5'- tert-butyl-phenyls) BTA, 2- (2'- hydroxyls -3', 5- di-tert-butyl-phenyl) BTA, 2- (2'- hydroxyls - 5'- t-octyls phenyl) BTA, 2- (the t-octyl phenyl of 2'- hydroxyls -3', 5'- bis-) BTA, or commercially available TINUVIN PS、TINUVIN 99-2、TINUVIN 109、TINUVIN384-2、TINUVIN 571、TINUVIN 900、TINUVIN 928 Or TINUVIN 1130 (trade name of Ciba Specialty Chemicals Inc. manufactures) etc..
In addition, triazines as light stabilizer is preferably hydroxyphenyltriazinuv class UV absorbents.Triazines as light stabilizer can be Commercially available product, can include such as TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN 479 or TINUVIN 1577 (trade names of Ciba Specialty Chemicals Inc. manufactures) etc..
Furthermore it is known that benzophenone light stabilizer is may be used as the benzophenone analog derivative of light stabilizer, It can be commercially available product.Specifically, the example of benzophenone analog derivative can include 2,4-DihydroxyBenzophenone, 2- hydroxyls- 4- methoxy benzophenones, BP-4,2-hydroxy-4-n-octoxybenzophenone, 2- Hydroxyl -4- positive 12-alkoxy benzophenones, 2- hydroxyl -4- behzyloxybenzophenones, double (5- benzoyl -4- hydroxyl -2- first Phenyl) methane, 2,2'- dihydroxy -4- methoxy benzophenones or 2,2'- dihydroxy -4,4'- dimethoxy hexichol first Ketone, or commercially available CHIMASSORB 81 (trade name of Ciba Specialty Chemicals Inc. manufactures).
Light stabilizer may be used singly or in combination of two or more, preferably can be with having wide inhale in below 350nm Benzotriazole, triazines or the benzophenone light stabilizer for receiving region are applied in combination.Preferably, TINUVIN 5050, TINUVIN 5060 or TINUVIN 5151 can be commercially available.
Additive
As necessary, it can be used together additive according in the present invention self-emission type Photosensitve resin composition and (such as fill out Material), other polymer compounds, pigment dispersing agent, adhesion promoter, antioxidant, UV absorbents or anti-coagulants etc..
Filler can be such as including glass, silica, aluminum oxide.
Specifically, other polymer compounds can include curable resin (such as epoxy resin or maleimide resin Deng) and thermoplastic resin (such as polyvinyl alcohol, polyacrylic acid, polyalkylene glycol monoalkyl ether, acrylic acid Polyfluoroalkyl ester, polyester, poly- Urethane etc.).
Commercially available surfactant can be used as pigment dispersing agent, can be for example including silicon class surfactant, fluorine Class surfactant, esters surface active agent, cationic surface active agent, anionic surfactant, nonionic table Face activating agent, bipolarity surfactant etc..These surfactants may be used singly or in combination of two or more.Surface Activating agent can be for example including polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyethylene glycol di, sorbitan fatty Acid esters, fatty acid modified polyester, tertiary-amine modified polyurethane, polyethyleneimine etc..Except above-mentioned surfactant, surface-active Agent can include trade name KP (Shin-Etsu Chemical Co.Ltd. manufactures), POLYFLOW (Kyoeisha Chemical Co.Ltd. manufacture), EFTOP (Tochem Products Co.Ltd. manufactures), MEGAFAC (Dainippon Ink Chemical Industry Co. manufacture), Flourad (Sumitomo 3M Ltd. manufactures), Asahi guard, Surflon (Asahi Glass Co.Ltd. manufactures), SOLSPERSE (Zeneca Ltd. manufactures), EFKA (EFKA Chemicals B.V. Manufacture), PB 821 (Ajinomoto Co.Inc. manufactures) etc..
Adhesion promoter can include such as vinyltrimethoxy silane, VTES, (the 2- methoxies of vinyl three Base oxethyl) silane, N- (2- amino-ethyls) -3- amino propyl methyls dimethoxysilane, N- (2- amino-ethyls) -3- amino Propyl trimethoxy silicane, APTES, 3- glycidoxypropyltrime,hoxysilanes, 3- epoxies third Epoxide hydroxypropyl methyl dimethoxysilane, 2- (3,4- epoxycyclohexyls) ethyl trimethoxy silane, 3- chloropropyl diformazans TMOS, 3- r-chloropropyl trimethoxyl silanes, 3- methacryloxypropyl trimethoxy silanes, 3- mercaptopropyi front threes TMOS etc..
Specifically, antioxidant can include 2,2'- thiobis (4- methyl-6-tert-butylphenols), 2,6- di-t-butyls- 4- methylphenols etc..
Specifically, UV absorbents can include 2- (the 3- tert-butyl group -2- hydroxy-5-methyl bases phenyl) -5- chlorobenzotriazoles, alkane Epoxide benzophenone etc..
Specifically, anti-coagulants can be including Sodium Polyacrylate etc..
For example, according to the self-emission type Photosensitve resin composition of the present invention method as described below can be used to prepare.In advance First dyestuff is mixed to be dissolved in wherein with solvent.In this case, alternatively using pigment dispersing agent, and can also be by Some or all adhesive resins are blended.Can by remaining adhesive resin, photopolymerizable compound, Photoepolymerizationinitiater initiater, Antioxidant and the other components alternatively used and optional other solvent are further added to dispersions obtained (following Commonly referred to as base-material starches (mill base)) in, to obtain required self-emission type Photosensitve resin composition.
Color conversion layer
In addition, the invention provides the color conversion layer prepared by self-emission type Photosensitve resin composition.
When by image display device is applied to according to the color conversion layer of the present invention, with the light from image display device Color conversion layer can light when the light of source transmitting is irradiated, and this makes it possible to achieve excellent light efficiency.Further, since tool Coloured light is launched, so color reproduction can become excellent, and because light is launched forward because of luminescence generated by light, Visual angle can also be increased.
More specifically, in the normal image display device including color conversion layer, white light is by color conversion layer with reality Existing colour.In this process, because some light are absorbed into color conversion layer, light efficiency may be reduced.However, when bag Include by according to the present invention self-emission type Photosensitve resin composition prepare color conversion layer when, color conversion layer can by from The light of light source transmitting spontaneously lights, and this makes it possible to achieve excellent light efficiency.
Color conversion layer includes substrate and the patterned layer formed on substrate.
Substrate can be the substrate of color conversion layer itself, or can also be for setting color turns thereon in a display device Region of layer etc. is changed, but the present invention is not particularly limited to this.Substrate can be glass, silicon (Si), silica (SiOx) or polymerization Thing substrate.Here, polymeric substrates can be polyether sulfone (PES) or makrolon (PC) substrate.
Patterned layer is the layer of the self-emission type photonasty oil/fat composition comprising the present invention.In such a case, it is possible to pass through Self-emission type Photosensitve resin composition is coated with, by resin combination exposure to form predetermined pattern, and is developed and heat reactive resin Composition is with forming layer.
The patterned layer formed by self-emission type Photosensitve resin composition can include the red containing red quantum dot particle Patterned layer, the green pattern layer containing green quantum dot particles and the blue color patterns layer containing blue quantum dot particles.Work as illumination When penetrating, red pattern layer, green pattern layer and blue color patterns layer launch feux rouges, green glow and blue light respectively.
In this case, when being applied to image display device, the light launched from light source is had no particular limits.So And, it is contemplated that excellent color reproduction, the light source of transmitting blue light can be used.
According to the another exemplary embodiment of the present invention, patterned layer can also only include red pattern layer, green pattern Two in layer and blue color patterns layer.In this case, patterned layer can also include the transparent pattern without quantum dot particles Layer.
When only including two color pattern layers, it can use transmitting that there is representative not to be included in two color pattern layers Other colors wavelength light light source.For example, when including red pattern layer with green pattern layer, transmitting can be used blue The light source of coloured light.In this case, red quantum dot particle and green quantum dot particles launch feux rouges and green glow respectively, and Complete blue light passes through transparent pattern layer to produce blueness.
As described above, the color conversion layer of the color conversion layer including substrate and patterned layer is additionally may included between pattern The barrier layer of formation, and black matrix" can also be included.In addition, color conversion layer is additionally may included in what is formed in patterned layer Diaphragm.
Image display device
In addition, present invention also offers a kind of image display device including color conversion layer.
Conventional liquid crystal display device can be applied not only to according to the color conversion layer of the present invention, various figures are applied also for As display device, such as el display device, plasm display device or field emission type display unit.
Color conversion layer can be included according to the image display device of the present invention, the color conversion layer includes containing amount of red Red pattern layer, the green pattern layer containing green quantum dot particles and the blueness containing blue quantum dot particles of son point particle Patterned layer.In this case, when being applied to image display device, the light launched from light source is not particularly limited.However, In view of excellent color reproduction, it is preferable to use the light source of transmitting blue light.
According to the another exemplary embodiment of the present invention, image display device of the invention can also be included only including red The color conversion layer of two in chromatic graph pattern layer, green pattern layer and blue color patterns layer.In this case, color conversion layer is also Including the transparent pattern layer without quantum dot particles.
When only including two color pattern layers, it can use transmitting that there is representative not to be included in two color patterns The light source of the light of the wavelength of other colors in layer.For example, when including red pattern layer with green pattern layer, hair can be used Penetrate the light source of blue light.In this case, red quantum dot particle and green quantum dot particles launch feux rouges and green glow respectively, And complete blue light passes through transparent pattern layer to produce blueness.
High brightness can be shown due to excellent light efficiency according to the image display device of the present invention, and can be had There are excellent color reproduction and wide visual angle.
Hereinafter, the preferred embodiment of the present invention will be described, to help to understand the present invention.However, for this area It is obvious to the skilled person that set forth herein the preferred embodiment that is for illustrative purposes only of description, and be not intended to Limitation limits the scope of the present invention.It will thus be appreciated that without departing from the scope of the invention, can be to this hair Bright illustrative embodiments make various changes and modifications so that as long as they are in appended claims and its equivalence In the range of, the present invention will cover all such changes and modifications.Hereinafter, unless otherwise indicated, all of content are represented " part " and " percentage " is by weight.
Compare synthesis example 1
By double (3- amino-4-hydroxylphenyls) sulfones (Tokyo Kasei Kogyo Co., Ltd. manufacture) of 4.98 parts by weight Mixed with the methanol of 28.1 parts by weight, be then slowly added to the 3- second of 8.18 parts by weight thereto while 10 DEG C stirred below Epoxide -3- imino group propionate hydrochlorides.Then, 24h is stirred at room temperature in 10 DEG C of 7h stirred below in reactant mixture, And stir 24h at 60 DEG C.Reactant mixture is cooled to room temperature, the crystal of precipitation is then obtained by suction filtration.By precipitation Crystal is washed with methanol, then at 60 DEG C be dried in vacuo, obtain 6.77 parts by weight by following formula (pt1- 1b) represent chemical combination Thing.
(analysis) ESI+：M/z=[M+H]+473.1
Exact Mass：472.1
Synthesis example 1
By double (3- amino-4-hydroxylphenyls) sulfone (Tokyo Kasei Kogyo Co., Ltd. systems of 10.6 parts by weight Make), 4- (diethylamino) salicylide of 14.6 parts by weight (Tokyo Kasei Kogyo Co., Ltd. manufacture), 3.17 weight The benzoic acid (Tokyo Kasei Kogyo Co., Ltd. manufacture) of part, 1- amylalcohols (the Tokyo Kasei of 183 parts by weight Kogyo Co., Ltd. manufacture) and 8.61 parts by weight acetic acid cyanaoethyl methacrylate (Tokyo Kasei Kogyo Co., Ltd. manufacture) Mixing, and the stirring 3h (hour) at 120 DEG C.By 4- (diethylamino) salicylide (the Tokyo Kasei of 14.6 parts by weight Kogyo Co., Ltd. manufacture), the benzoic acid (Tokyo Kasei Kogyo Co., Ltd. manufacture) and 8.61 of 3.17 parts by weight The acetic acid cyanaoethyl methacrylate (manufacture of Tokyo Kasei Kogyo Co., Ltd.s) of parts by weight is added in gained reaction solution, and 12h is stirred at 120 DEG C.Reaction solution is cooled to room temperature, the crystal then precipitated by filtered off with suction.After filtering, 236 are added The acetonitrile of parts by weight and the isopropanol of 234 parts by weight and stirring, then pass through filtered off with suction insoluble solid.
After filtering, the acetonitrile of 236 parts by weight and isopropanol and the stirring of 234 parts by weight are added, then passes through filtered off with suction Insoluble solid.Hereafter, the chloroform of 2220 parts by weight is added, stirs and filters.530 parts by weight are added into gained filtrate 5% sodium hydrate aqueous solution, stirring, extraction chloroformic solution layer.18% sodium-chloride water solution of 610 parts by weight is added to chloroform In solution, and stir, and extract chloroformic solution layer.The magnesium sulfate of 10 parts by weight is added in chloroformic solution, stirred, then mistake Filter.By evaporator distillation filtrate to remove solvent, and be dried under reduced pressure at 60 DEG C, obtain 19.5 parts by weight under (IB-1) The compound that formula is represented.
The structure is to be confirmed by H-NMR.
H-NMR(500MHz,DMSO-d6):1.14(12H,t),3.50(8H,q),6.61(2H,d),6.82(2H,dd), 7.71(2H,d),7.95(2H,d),8.04(2H,dd),8.43(2H,d),8.83(2H,s)。
Synthesis example 2
By the m-anisidine of 24.0 parts by weight, the iodo- meta-xylenes of 4- of 99.7 parts by weight, the potassium carbonate of 117 parts by weight, The copper powder of 27.3 parts by weight, the o-dichlorohenzene of the parts by weight of 18- crown ethers -6 and 511 of 4.64 parts by weight are mixed in a nitrogen atmosphere, And stir 19h at 175 DEG C.Then, the potassium carbonate, the copper powder of 8.19 parts by weight, 1.39 weights of 35.1 parts by weight are added thereto The o-dichlorohenzene of the parts by weight of 18- crown ethers -6 and 22.0 of part is measured, and 17h is stirred at 175 DEG C.Gained mixture is cooled to room Temperature, is then filtered.Obtained filtrate is washed three times with the 2N hydrochloric acid of 450 parts by weight and the ethyl acetate of 450 parts by weight, then Washed three times with the aqueous solution of the sodium chloride comprising 18 weight % of 470 parts by weight.By obtained ethyl acetate solution sulfuric acid Magnesium is dried, filtering.Removed from filtrate after solvent, by column chromatography eluting filtrate, obtain 64.1 parts by weight by following formula (pt2- 1b) represent compound.
(analysis) ESI+:M/z=[M+H]+332.2
Accurate mass：331.2
By 31.7 parts by weight by formula (pt2- 1b) represent compound and 190 parts by weight dehydration dichloromethane in nitrogen Mixed under atmosphere below 0 DEG C.Then, the dichloromethane that the boron bromide comprising 17 weight % of 199 parts by weight is added thereto is molten Liquid, and stir 1h.Then, 12h is stirred at room temperature in gained mixture.Add mixture to the frozen water of 1100 parts by weight In, then extract chloroform layer with the chloroform of 740 parts by weight.The chloroformic solution of gained is included into 18 weight % with 470 parts by weight The aqueous solution of sodium chloride is washed twice, and is dried with magnesium sulfate, is then filtered.Removed from filtrate after solvent, pass through column chromatography Purify filtrate, obtain 30.0 parts by weight by following formula (pt3- 1b) represent compound.
(analysis) ionization mode=ESI+:M/z=[M+H]+318.2
Accurate mass：317.2
By 7.46 parts by weight by formula (pt3- 1b) represent compound and 14.4 parts by weight N,N-dimethylformamide Mixed in a nitrogen atmosphere at 5-10 DEG C.7.21 parts by weight phosphoryl chloride phosphorus oxychlorides are further added into gained mixture, while will be mixed Compound is maintained at 5-10 DEG C of temperature.Then, by mixture in 10 DEG C of 1h stirred below, be stirred at room temperature 1h, and 80 DEG C with Lower stirring 1h.Reactant mixture is naturally cooled into room temperature, then with 48% sodium hydrate aqueous solution and the ice of 100 parts by weight Water is neutralized.The ethyl acetate of 180 parts by weight is added into mixture, diatomite is continuously added to and stirs.Mixture is filtered, so After extract ethyl acetate layer.Ethyl acetate layer is dried with magnesium sulfate, and filtered.Removed from filtrate after solvent, pass through post color Spectrometry purify filtrate, obtain 6.26 parts by weight by following formula (pt4- 1b) represent compound.
(analysis) ionization mode=ESI+:M/z=[M+H]+346.2
Accurate mass：345.2
By 6.01 parts by weight by formula (pt4- 1b) represent compound, 4.04 parts by weight by formula (pt1- 1b) represent The toluene mixing of compound, the piperidines of 0.357 parts by weight and 33.4 parts by weight, in 105 DEG C of 6h stirred below.Mixture is cooled down To room temperature, the methanol of 153 parts by weight is then added into mixture.By precipitation filtering, then by column chromatography eluting, obtain The compound represented by following formula (IB-2) of 7.76 parts by weight.
1H-NMR(CDCl3,270MHz)δ2.13(12H),2.34(12H),6.38(2H),6.52(2H),6.92-7.02 (8H),7.10(4H),7.37(2H),7.67(2H),7.98(2H),8.40(2H),8.64(2H)。
Preparation example 1：Adhesive resin A
By 23.3g methyl -2- (bromomethyl)-acrylate (available commercially from Sigma-Aldrich Co.), 15.8g Triethylamine (commercially available from Sigma-Aldrich Co.) and 115.0g propylene glycol monomethyl ethers are (available commercially from Tokyo Chemical Industry (TCI) Co.Ltd.) add equipped with the four-neck flask of dropping funel, thermometer, condenser and agitator, and And the inside of four-neck flask is purged with nitrogen.Next, flask is heated to after 90 DEG C, and dropwise addition includes 15.1g methyl -2- (hydroxymethyl)-acrylate (available commercially from Sigma-Aldrich Co.), 3.2g 2,2'- azodiisobutyronitriles it is (commercially available From Wako Co.Ltd.) and 110.0g propylene glycol monomethyl ethers (available commercially from TCI Co.Ltd.) mixed solution 1h, make polymerisation 0.5h is carried out, to generate the polymer containing pyrans.Then, it is slowly added dropwise including 37.5g methacrylic acids, 19.0g metering systems The mixing of sour methyl esters, 225.0g propylene glycol monomethyl ethers and 3.2g 2,2'- azodiisobutyronitriles (available commercially from Wako Co.Ltd.) is molten Liquid 1h, polymerize 8h, is subsequently cooled to room temperature.After four-neck flask inside is purged with nitrogen, by the metering system of 61.5 parts by weight Acid glycidyl ester (available commercially from Mitsubishi Rayon Co.Ltd.), 3.6g tetra-n-butyl ammonium bromide (available commercially from TCI Co.Ltd.) and 0.15g methyl quinone (methoquinone) (available commercially from Junsei Chemical Co.Ltd.) addition 12h is reacted so that GMA is added in the carboxyl of copolymer into flask, and at 80 DEG C, so as to obtain adhesive resin A.It is logical Gpc measurement is crossed, adhesive resin A weight average molecular weight is 23000.
Preparation example 2：Adhesive resin B
182g propylene glycol methyl ether acetates are added to equipped with agitator, thermometer, reflux condenser, dropping funel In the flask of nitrogen inlet duct, flask interior is changed into nitrogen from air, 100 DEG C are then heated to.Then, will be by inciting somebody to action 3.6g azodiisobutyronitriles are added to including 70.5g (0.40mol) benzyl methacrylate, 45.0g (0.50mol) metering system Acid, 44.5g (0.10mol) have the monomethacrylates of homoatomic ring skeleton and the mixing of 136g propylene glycol methyl ether acetates In thing obtained solution from dropping funel be added drop-wise to flask in 2h, and continue at 100 DEG C to stir other 5h.Then, by flask Internal atmosphere be changed into air from nitrogen, and by 30g (0.2mol) GMA (relative to making in the reaction The carboxyl of methacrylic acid is 40mol%), (dimethylaminomethyl) phenol of 0.9g tri- and 0.145g quinhydrones are added to burning In bottle, and the successive reaction 6h at 110 DEG C, obtain the adhesive resin B that solid acid value is 99mgKOH/g.Determined by GPC, The resin glue B converted relative to polystyrene standards weight average molecular weight is 28000, and molecular weight distribution (Mw/Mn) is 2.2。
Equipment：HLC-8120GPC (Tosoh Co. manufactures)
Post：TSK-GELG4000HXL+TSK-GELG2000HXL (is connected in series)
Column temperature：40℃
Mobile phase solvent：Tetrahydrofuran
Flow velocity：1.0mL/min (minute)
Injection volume：50μL
Detector：RI
The sample concentration of measure：0.6 mass % (solvent=tetrahydrofuran)
Standard material for calibration：TSK polystyrene standards F-40, F-4, F-1, A-2500, A-500 (Tosoh Co. Manufacture)
The ratio of the weight average molecular weight of resulting sample and number-average molecular weight is set as molecular weight distribution (Mw/Mn).
Examples 1 and 2 and comparative example 1 and 2
Table 1
1st, (color changes pixel to color conversion layer；Glass substrate) preparation embodiment
Color is prepared using the self-emission type Photosensitve resin composition prepared in Examples 1 and 2 and comparative example 1 and 2 to turn Change layer.That is, each self-emission type Photosensitve resin composition is applied on glass substrate using spin-coating method, glass substrate is placed on In heating plate, 3min is then kept to form film at a temperature of 100 DEG C.Then, the film is irradiated with ultraviolet.This In the case of, use ultrahigh pressure mercury lamp (trade name：USH-250D, available commercially from Ushio Denki Co.Ltd.) as UV light sources, In air atmosphere with 40mJ/cm2The exposure film of (365nm), and without using specific filter.It is aobvious using spraying Shadow machine development 60 seconds in KOH reagent solutions (pH 12.5) by the film being irradiated with ultraviolet, then add at 220 DEG C 20min is heated in oven heat to form pattern.The film thickness of thus prepared self-emission type color conversion layer pattern is 3.0 μm. The thickness of color conversion layer can be controlled differently to 500 μm.
The measurement of luminous intensity
For each coated substrate, quantum efficiency measurement system (QE-1000, available commercially from Otsuka is used Pharmaceutical Co.Ltd.) to using the photosensitive tree of self-emission type prepared in Examples 1 and 2 and comparative example 1 and 2 Thickness prepared by oil/fat composition measures for the luminescence generated by light (PL) of 3.0 μm of self-emission type multicolour pattern.As a result, hair Luminous intensity is listed in the table below in 2.
In this case, with the luminous intensity increase of measurement, color conversion layer has excellent light characteristic.
Table 2
λmax Luminous intensity
Embodiment 1 500 13050
Embodiment 2 500 12800
Comparative example 1 500 9800
Comparative example 2 500 9900
Reference table 2 is as can be seen that because the Photosensitve resin composition of Examples 1 and 2 is with higher than comparative example 1 and 2 Luminous intensity, so the Photosensitve resin composition of Examples 1 and 2 shows the Photosensitve resin composition better than comparative example 1 and 2 Fluorescence efficiency.
2nd, Evaluation of Heat Tolerance
Color conversion layer is prepared using the Photosensitve resin composition prepared in Examples 1 and 2 and comparative example 1 and 2.Specifically Ground, 2 inches × 2 inches of glass substrate is coated on (available commercially from Corning using spin-coating method by each Photosensitve resin composition Inc. " EAGLE XG "), and glass substrate is put on hot plate, and keep 3min thin to be formed at a temperature of 100 DEG C Film.Then, by with transmissivity in a stepwise manner from 1-100% change pattern and 1 μm -50 μm of size line/spacing figure The test photomask of the pattern of case is placed on film, is irradiated with ultraviolet at test photomask at intervals of 100 μm.At this In the case of kind, using the 1kW high-pressure sodium lamps including whole g, h and i rays as UV light sources, with 100mJ/cm2Exposure intensity Film is irradiated, and without using specific filter.By the film being irradiated through UV in KOH reagent solutions (pH 10.5) Develop 2min.The glass substrate distillation water washing of film will be coated with thereon, dried by nitrogen blowing, and in 200 DEG C of heating 25min is heated in baking oven to prepare color conversion layer.Thus the film thickness of the color conversion layer prepared is 2.0 μm.
Heat resistance
It is at 230 DEG C that the color change value (Δ Eab) after color conversion layer heating 120min is resistance to evaluate by measuring It is hot.△ Eab refer to using the value needed for the following saturation equation of the coordinate of CIE 1976 (L*, a*, b*) color space. (color science handbook：New edition.(1985) are worked out by Japanese color science association, page 266).
△ E*ab={ (△ L) 2+ (△ a) 2+ (△ b) 2 } 1/2
[evaluation criterion of heat resistance]
○：△ E*ab values：Less than 3
△：△ E*ab values：3-10
×：△ E*ab values：More than 10
3rd, the evaluation of developing powder and residue
Using spin-coating method by each self-emission type photoresist group prepared in Examples 1 and 2 and comparative example 1 and 2 Compound be coated with the glass substrate, then by the glass substrate place on hot plate, at a temperature of 100 DEG C keep 3min with Form film.Hereafter, it is exposed by the whole surface to film in the case of without using photomask, uses 50mJ/cm2's Ultraviolet irradiates film.Then, using film thickness measuring system (DEKTAK 6M, available commercially from Veeco Instruments, Inc. the film thickness of pattern) is measured.By the development 80 in KOH reagent solutions (pH 10.5) again of the substrate of thickness measure Second, and confirm whether self-emission type photosensitive polymer combination is remained in unexposed area.
[evaluation criterion of developing powder]
The time needed for unexposed area is completely dissolved during measurement development in developer solution.When no develop, Represented by " X ".
[evaluation criterion of residue]
O：There is no residue
△：Residue surplus is more than 0% and less than 20%
×：Residue surplus is more than 20%.
Table 3
Film coated surface characteristic Developing powder (second) Residue Heat resistance
Embodiment 1 O 16 O O
Embodiment 2 O 17 O O
Comparative example 1 × 17 O ×
Comparative example 2 △ 24 × △
With reference to table 3 as can be seen that the self-emission type sense of the Examples 1 and 2 including the specific fluorescent dyestuff according to the present invention Photosensitive resin composition has excellent film coated surface characteristic and quick developing powder.In addition, it could be seen that Examples 1 and 2 Self-emission type Photosensitve resin composition due to produced without residue and excellent heat resistance and with excellent quality.
On the other hand, it can be seen that the self-emission type Photosensitve resin composition of comparative example 1 and 2 does not both have good painting Film surface characteristic, also without good physical property, such as developing powder, residue are produced and heat resistance.
[brief description of part in accompanying drawing]
1：Back light unit
3：Color conversion layer
5：Colour filter

Claims (8)

1. a kind of self-emission type Photosensitve resin composition, the self-emission type Photosensitve resin composition includes what is represented by following formula 1 Fluorescent dye：
[formula 1]
Wherein, L represents the divalent fluorinated alkyl with 1-20 carbon numbers, bivalent hydrocarbon radical or sulphur with 1-20 carbon numbers Acyl group；
X represents oxygen atom or sulphur atom；
R7-R13Hydrogen atom, halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,-SO are represented independently of one another3M、- CO2M, hydroxyl, formoxyl, amino or the univalence hydrocarbyl with 1-20 carbon numbers；
Constitute the methylene bridge-CH of the alkyl2- can be by oxygen atom, sulphur atom ,-N (R14)-, sulfonyl or carbonyl substitution, And the hydrogen atom included in the alkyl can by halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,- SO3M、-CO2M, hydroxyl, formoxyl or amino substitution；
R14Represent hydrogen atom or the univalence hydrocarbyl with 1-20 carbon numbers, R14To be identical or different in the presence of plural number；
M represents hydrogen atom or alkali metal atom, M to be identical or different in the presence of plural number, and
Z represents the compound represented by following formula 2 or formula 3：
[formula 2]
Wherein, R1The alkyl with 1-20 carbon numbers is represented, and constitutes the methylene bridge-CH of the alkyl2- can be former by oxygen Son substitution；
R2-R6Hydrogen atom, halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,-SO are represented independently of one another3M、- CO2M, hydroxyl, formoxyl, amino or the univalence hydrocarbyl with 1-20 carbon numbers；
Constitute the methylene bridge-CH of the alkyl2- can be by oxygen atom, sulphur atom ,-N (R30)-, amino or carbonyl substitution, and Hydrogen atom included in the alkyl can be by halogen atom, cyano group, nitro, carbamoyl, sulfamoyl ,-SO3M、- CO2M, hydroxyl, formoxyl or amino substitution；
R30Represent hydrogen atom or the univalence hydrocarbyl with 1-20 carbon numbers, R30To be identical or different in the presence of plural number, and
* bonded portion is represented, and
[formula 3]
Wherein, Ar1 and Ar2 represent the benzene for including the alkyl with 1-8 carbon numbers at ortho position and/or meta independently of one another Base, and
* bonded portion is represented.
2. self-emission type Photosensitve resin composition according to claim 1, wherein, the self-emission type photosensitive composition Thing is used to form color conversion layer.
3. self-emission type Photosensitve resin composition according to claim 1, also including adhesive resin, optical polymerism chemical combination Thing, Photoepolymerizationinitiater initiater and solvent.
4. self-emission type Photosensitve resin composition according to claim 3, wherein, based in the photosensitive tree of the self-emission type The content of the overall weight percent of solid in oil/fat composition, described adhesive resin and the photopolymerizable compound is respectively 1 weight %-60 weight % and 5 weight %-50 weight %,
Overall weight percent based on described adhesive resin and the photopolymerizable compound, the Photoepolymerizationinitiater initiater contains Measure as 0.1 weight %-40 weight %,
Based on the overall weight percent of the self-emission type Photosensitve resin composition, the content of the solvent is 60 weight %-90 Weight %, and
The content of the fluorescent dye is surplus.
5. self-emission type Photosensitve resin composition according to claim 3, also including antioxidant.
6. self-emission type Photosensitve resin composition according to claim 5, wherein, based on the self-emission type photosensitive resin The overall weight percent of composition, the content of the antioxidant is 0.1 weight %-10 weight %.
7. a kind of color conversion layer, the color conversion layer is as the self-emission type sense according to any one of claim 1-6 It is prepared by photopolymer resin composition.
8. a kind of image display device, described image display device includes color conversion layer according to claim 7.
CN201611223467.8A 2016-01-12 2016-12-27 Self-emission type Photosensitve resin composition, color conversion layer prepared therefrom and the image display device containing color conversion layer Pending CN106959583A (en)

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