CN106338885A - Quantum dot dispersion, self-emission type photosensitive resin composition, color filter and image display device - Google Patents
Quantum dot dispersion, self-emission type photosensitive resin composition, color filter and image display device Download PDFInfo
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- CN106338885A CN106338885A CN201610133057.8A CN201610133057A CN106338885A CN 106338885 A CN106338885 A CN 106338885A CN 201610133057 A CN201610133057 A CN 201610133057A CN 106338885 A CN106338885 A CN 106338885A
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- quantum dot
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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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- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
- C09K11/881—Chalcogenides
- C09K11/883—Chalcogenides with zinc or cadmium
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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
Abstract
The invention relates to quantum dot dispersion, a self-emission type photosensitive resin composition, a color filter and an image display device. The self-emission type photosensitive resin composition contains the quantum dot dispersion. The color filter is manufactured by using the self-emission type photosensitive resin composition. Specifically, according to the invention, the quantum dot dispersion is characterized in that the quantum dot dispersion includes a photoluminescence quantum dot particle, a dispersion agent and a solvent. The dispersion agent is a compound having a carboxylic acid and an unsaturated double bond within 1 molecule. Also, according to the invention, the color filter is characterized in that the color filter is manufactured by the self-emission type photosensitive resin composition which contains the quantum dot dispersion, and the image display device is characterized by containing the color filter.
Description
Technical field
The present invention relates to quantum dot dispersion and the emissive type photoresist comprising this quantum dot dispersion
Compositionss and the color filter using the manufacture of this emissive type photosensitive polymer combination and image display dress
Put.
Background technology
Color filter be can, green, blue 3 kind colors red from white light extraction and form fine pixel
The thin film membranous type opticses of unit, the size of 1 pixel is tens of to hundreds of microns.Such filter
Color utensil has: in order to by the boundary member shading between each pixel on the transparent substrate by the pattern shape determining
The black matrix layer that becomes and in order to form each pixel and multiple colors are (usually red (r), green (g) and blue
Color (b) 3 primary colors) structure that stacks gradually of tactic pixel portion to determine.In general, color filter
By staining, electrodeposition process, print process, pigment dispersion method etc., more than 3 kinds colors can be coated on
To manufacture on bright substrate, recently, to make use of based on the pigment dispersion method one-tenth of photoresist of pigment-dispersing type
Stream.
As the pigment dispersion method realizing one of the method for color filter, it is to be provided with the saturating of black matrix"
On bright base material, coating comprises coloring agent and alkali soluble resins, photo polymerization monomer, Photoepolymerizationinitiater initiater, epoxy
Resin, solvent, the photosensitive polymer combination of other additive, the pattern of the form that will be formed is exposed
After light, non-exposed position is removed with solvent, carries out heat cure, this serial procedures is repeated, from
And the method forming coloured film, its actively be applied to manufacture portable phone, notebook computer, monitor,
The lcd of TV etc..In recent years, practical situation is for make use of the pigment dispersion method with various advantages
Color filter photosensitive polymer combination, do not require nothing more than excellent pattern properties, and have high demands color again
The performance that now rate and high brightness and high-contrast etc. further increase.
However, color reproduction is the light transmission color filter irradiating from light source and realizes, but in this process,
A part for light is colored device and absorbs, and therefore light efficiency reduces, and additionally, there are because of the pigment as color filter
Characteristic and make the not enough such basic restriction of perfect color reproduction.
As the scheme that can solve this problem, have and make use of the emissive type photonasty tree comprising quantum dot
The color filter manufacturing method of oil/fat composition.Luminescent waveform can be reduced using quantum dot, there is pigment and be unable to
The high color fulfillment capability realized, thus have excellent light characteristic.
However, quantum dot has the problem becoming prone to aoxidize because of the oxygen of in the air, in normal circumstances,
Make it be scattered in the non-polar solvens such as toluene, chloroform to be preserved and use.However, being so scattered in
In the case that the quantum dot of non-polar solven is used in photosensitive polymer combination, due to photoresist group
The problem of the compatibility of the polar solvent in compound and occur separate out foreign body, therefore, have the characteristics of luminescence reduce
Problem.Therefore, in order to improve the compatibility with the photosensitive polymer combination of polar solvent system, maintenance dose
The luminous efficiency of son point is it is necessary to add exploitation.
Korean Patent Publication No. 10-2013-0000506 publication discloses a skill being related to display device
Art, this display device comprises light source and from the incident display floater of the light of above-mentioned light source outgoing, above-mentioned aobvious
Show that panel comprises multiple colour switching portions, above-mentioned colour switching portion comprises to make the multiple of the wavelength conversion of above-mentioned light
Wavelength conversion particle and absorb in above-mentioned light predetermined wavelength band light multiple color filter particles.
Although however, above-mentioned prior art is similar at the aspect comprising quantum dot, to photoresist group
The content of compound does not illustrate, and only discloses the display device with high color reproduction rate and brightness, because
This needs photosensitive polymer combination to be carried out add exploitation.
Prior art literature
Patent documentation
Patent documentation 1: Korean Patent Publication No. 10-2013-0000506 publication
Content of the invention
Invent problem to be solved
The present invention proposes to solve problem as described above, it is intended that by comprising to be used as
1 intramolecular has the dispersant of the compound of carboxylic acid and unsaturated double-bond, thus providing the fall not having light efficiency
Generation that is low and separating out foreign body, can maintain the quantum dot dispersion of luminous efficiency.
Additionally, it is an object of the present invention to provide by the emissive type comprising quantum dot dispersion as described above
The color filter of photosensitive polymer combination manufacture and the image display device comprising this color filter.
Method for solving problem
Quantum dot dispersion according to the present invention for reaching above-mentioned purpose is characterised by, comprises photic
Light quanta point particle, dispersant and solvent, above-mentioned dispersant is to have carboxylic acid and unsaturation pair in 1 intramolecular
The compound of key.
Additionally, the present invention is with by the emissive type photosensitive polymer combination system comprising above-mentioned quantum dot dispersion
The color filter made and comprise this color filter image display device as feature.
The effect of invention
Quantum dot dispersion according to the present invention because comprise to have the dispersant of carboxylic acid and unsaturated double-bond and not
Produce the foreign body being caused by precipitation such that it is able to provide during the exposure process of color filter manufacturing process because based on not
Saturation double bond formed protecting film and make light maintain excellent high-quality photosensitive polymer combination.
Additionally, the present invention has the emissive type photonasty tree that can provide by comprising above-mentioned quantum dot dispersion
The color filter of oil/fat composition manufacture and comprise this color filter image display device effect.
Specific embodiment
Quantum dot dispersion according to the present invention is it is characterised in that comprising luminescence generated by light quantum dot particles, dividing
Powder and solvent, above-mentioned dispersant is the compound in 1 intramolecular with carboxylic acid and unsaturated double-bond.
Hereinafter, explain the present invention.
＜ quantum dot dispersion ＞
Luminescence generated by light quantum dot particles
The quantum dot dispersion of the present invention comprises luminescence generated by light quantum dot particles.
So-called quantum dot, is the semiconductor substance of nano-scale.Atom forms molecule, and molecule constitutes cluster so
Little molecular aggregate and form nanoparticle.Such nanoparticle is particularly with characteristic of semiconductor
When, it is referred to as quantum dot.Quantum dot, if accepting energy from outside and become excited state, voluntarily
Release meets the energy of corresponding energy bandgaps.
The quantum dot dispersion of the present invention comprises such luminescence generated by light quantum dot particles, the colour filter being produced from
Device can light (luminescence generated by light) by the irradiation of light.
As long as luminescence generated by light quantum dot particles according to the present invention can be by the stimulation of light and luminous amount
Son point particle, is just not particularly limited, can be selected from such as ii-vi race semiconducting compound；Iii-v race
Semiconducting compound；Iv-vi race semiconducting compound；Iv race element or the compound comprising iv race element；
The group being formed with combinations thereof.They can be used alone or are used in mixed way two or more.
Above-mentioned ii-vi race semiconducting compound can selected from following substances composition group: selected from cds,
Cdse, cdte, zns, znse, znte, zno, hgs, hgse, hgte and their mixing
Was Used compound in the group that thing is formed；Selected from cdses, cdsete, cdste, znses,
znsete、znste、hgses、hgsete、hgste、cdzns、cdznse、cdznte、cdhgs、
In the group that cdhgse, cdhgte, hgzns, hgznse, hgznte and their mixture are formed
Three element compounds；With selected from cdznses, cdznsete, cdznste, cdhgses,
Cdhgsete, cdhgste, hgznses, hgznsete, hgznste and their mixture institute
Four element compounds in the group of composition, above-mentioned iii-v race semiconducting compound can be selected from following substances
Composition group: selected from gan, gap, gaas, gasb, aln, alp, alas, alsb, inn,
Was Used compound in the group that inp, inas, insb and their mixture are formed；Selected from ganp,
ganas、gansb、gapas、gapsb、alnp、alnas、alnsb、alpas、alpsb、
The group that innp, innas, innsb, inpas, inpsb, gaalnp and their mixture are formed
In three element compounds；With selected from gaalnas, gaalnsb, gaalpas, gaalpsb,
gainnp、gainnas、gainnsb、gainpas、gainpsb、inalnp、inalnas、inalnsb、
Four element compounds in the group that inalpas, inalpsb and their mixture are formed, above-mentioned iv-vi
Race's semiconducting compound can selected from following substances composition group: selected from sns, snse, snte, pbs,
Was Used compound in the group that pbse, pbte and their mixture are formed；Selected from snses,
Snsete, snste, pbses, pbsete, pbste, snpbs, snpbse, snpbte and they
The group that formed of mixture in three element compounds；With selected from snpbsse, snpbsete,
Four element compounds in the group that snpbste and their mixture are formed, above-mentioned iv race element or
Comprise above-mentioned iv race element compound can selected from following substances composition group: selected from si, ge,
Element compound in the group being formed with their mixture；With selected from sic, sige and they
Was Used compound in the group that mixture is formed.
Quantum dot particles can be (homogeneous) single structure of homogenizing；Core-shell structure copolymer (core-shell), ladder
Such dual structure such as degree (gradient) structure；Or their mixed structure.
Form core (core) and the material of shell (shell), Ke Yiyou respectively in the dual structure of core-shell structure copolymer (core-shell)
The above-mentioned mutually different semiconducting compound mentioning is formed.For example, above-mentioned core can comprise selected from cdse,
Cds, zns, znse, cdte, cdsete, cdzns, pbse, aginzns and zno are formed
More than a kind material in group, but it is not limited to this.Above-mentioned shell can comprise selected from cdse, znse,
More than a kind material in the group that zns, znte, cdte, pbs, tio, srse and hgse are formed,
But it is not limited to this.
The photosensitive composition that the manufacture of common color filter is used, can wrap to embody color
Containing red, green, blue coloring agent, identical with this, luminescence generated by light quantum dot particles also can be categorized into
Red quantum point particle, green quantum dot particles and blue quantum dot particles, quantum dot grain according to the present invention
Son can be red quantum point particle, green quantum dot particles or blue quantum dot particles.
Quantum dot particles can pass through wet chemical processes (wet chemical process), organometallic chemistry
Evaporation process or molecular beam epitaxial process are synthesizing.Wet chemical processes are to add precursor in organic solvent
Matter and the method that makes particle growth.During crystalline growth, organic solvent is coordinated to the table of quantum dot crystallization naturally
Face, play dispersant effect, adjust crystallization growth, therefore with Metalorganic Chemical Vapor (mocvd,
Metal organic chemical vapor deposition), molecular beam epitaxy (mbe, molecular beam
Epitaxy as), vapor coating method is compared, can be by being more prone to and cheap technique controls and receives
The growth of rice corpuscles.
The content of luminescence generated by light quantum dot particles according to the present invention, is not particularly limited, such as in quantum dot
It is preferably 10～90 weight %, more preferably with 15～80 weight % in the gross weight of the solid constituent of dispersion
Comprise.If the content of luminescence generated by light quantum dot particles is less than 10 weight %, it is used in emissive type sense
During photosensitive resin composition, the content of dispersant is many compared with the content of quantum dot, and photobehavior produces problem,
If the content of luminescence generated by light quantum dot particles is more than 90 weight %, the content of the dispersant that can use
Deficiency, the dispersion of quantum dot can produce problem.
Dispersant
Above-mentioned dispersant is to give the de- coagulation effect of quantum dot and photosensitive being used in emissive type
Property resin combination when the precipitation phenomenon that caused by polarity difference of suppression, and assign in the manufacturing process of color filter
The effect of the protective layer of quantum dot is given to use.
According to the present invention, using the situation of the compound comprising carboxylic acid and unsaturated double-bond in above-mentioned dispersant
Under, the dispersion of quantum dot becomes easy, can manufacture the compatibility with emissive type photosensitive polymer combination
Excellent quantum dot dispersion.
Now, as the example of the above-mentioned compound comprising carboxylic acid and unsaturated double-bond, can enumerate acrylic acid,
(to-1382, East Asia is closed for the acrylic compounds such as methacrylic acid, Dipentaerythritol Pentaacrylate monomester succinate
Cheng company), pentaerythritol triacrylate monomester succinate (to-756, East Asia Synesis Company), two seasons penta
The succinate modified thing of tetrol five acrylate (dpe6a-ms, common prosperity company), pentaerythritol triacrylate
Succinate modified thing (pe3a-ms, common prosperity company), Dipentaerythritol Pentaacrylate are orthophthalic modified
Thing (dpe6a-mp, common prosperity company), the orthophthalic modified thing of pentaerythritol acrylate (pe3a-mp),
Use glycidyl metering system in order to unsaturated double-bond group is imported to the copolymer comprising acrylic compounds
Macromolecular compound obtained by the addition polymerizations such as acid esters.
Foregoing illustrative comprise carboxylic acid and the dispersant of unsaturated double-bond can each be used alone or by 2 kinds
Combination of the above uses.
Dispersant according to the present invention, in addition to the above-mentioned compound with carboxylic acid and unsaturated double-bond, also
The dispersant of pigment dispersion used resin type can be used together.As the pigment dispersing agent of above-mentioned resin type,
It is disper that the acryloyl system dispersant manufacturing using active (living) control method can be enumerated
Byk-2000, disper byk-2001, disper byk-2070, disper byk-2150 etc.,
Additionally, as the pigment dispersing agent of other resin types, the pigment dispersing agent of known resin type can be comprised,
Polycarboxylate particularly with polyurethane, polyacrylate as representative, unsaturated polyamide, polycarboxylic acids, poly-
(part) amine salt of carboxylic acid, the ammonium salt of polycarboxylic acids, the alkylamine salt of polycarboxylic acids, polysiloxanes, long-chain gather
Amino amides phosphate, hydroxyl-containing the ester of polycarboxylic acids and their modified product or by having freedom
(free) reaction of the polyester of carboxyl and poly- (low-grade alkylidene imines) and the amide being formed or their salt are such
Oily dispersant；(methyl) acrylic-styrene copolymer, (methyl) acrylic acid-(methyl) acrylate is common
Polymers, styrene-maleic acid copolymer, polyvinyl alcohol or water-soluble resin as Polyvinylpyrrolidone
Or water-soluble polymeric compounds；Polyester；Modified polyacrylate；The addition of ethylene oxide/propylene oxide
Product and phosphate ester.
As the commercially available product of the pigment dispersing agent of above-mentioned resin type, as cation system pitch dispersant, can
Enumerate for example, the trade name of byk (Bi Ke) chemie company: disper byk-160, disper
byk-161、disper byk-162、disper byk-163、disper byk-164、disper
byk-166、disper byk-171、disper byk-182、disper byk-184；BASF
(basf) trade name of company: efka-44, efka-46, efka-47, efka-48, efka-4010,
efka-4050、efka-4055、efka-4020、efka-4015、efka-4060、efka-4300、
efka-4330、efka-4400、efka-4406、efka-4510、efka-4800；Lu Borun
(lubrizol) trade name of company: solspers-24000, solspers-32550, nbz-4204/10；
The trade name of Chuan Yan fine chemistry industry company: hinoact t-6000, hinoact t-7000, hinoact
t-8000；The trade name of aginomoto company: ajisper pb-821, ajisper pb-822, ajisper
pb-823；The trade name of chemical company of common prosperity society: florene dopa-17hf, florene
Dopa-15bhf, florene dopa-33, florene dopa-44 etc..
The weight average molecular weight of above-mentioned dispersant is 200～6,000, more preferably 300～5,000 model
Enclose.If weight average molecular weight is less than above range, the light efficiency of quantum dot maintains becomes difficult, if weight
Average molecular weight exceedes above range, then there is a problem of being difficult to disperse quantum dot.
Solvent
Solvent according to the present invention, is not particularly limited, and can be usually used in the art organic molten
Agent.
As concrete example, the non-polar solven class such as benzene,toluene,xylene, chloroform, hexane and second can be enumerated
The ethylene glycol such as glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether
Monoalkyl ethers；Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol two
The diethylene glycol dialkyl ether such as butyl ether；The ethylene glycol such as methylcellosolve acetate, ethyl cellosolve acetate
Alkylether acetates class；The propylene glycol alkyl ethers such as propylene glycol monomethyl ether；Propylene glycol monomethyl ether,
Propylene glycol monoethyl acetass, propylene glycol monopropyl ether acetass, methoxybutyl acetass, methoxyl group
The aklylene glycol alkylether acetates class such as pentaacetic acid ester；The virtues such as benzene,toluene,xylene, sym-trimethylbenzene.
Fragrant race hydro carbons；Methyl ethyl ketone, acetone, methyl amyl ketone, methyl iso-butyl ketone (MIBK), Ketohexamethylene, Ketocyclopentane
Deng ketone；The alcohols such as ethanol, propanol, butanol, hexanol, Hexalin, ethylene glycol, glycerol；3- ethyoxyl
The esters such as ethyl propionate, 3- methoxy methyl propionate；The ring-type esters such as gamma-butyrolacton；Deng.They can be single
Solely use or two or more is used in mixed way.
As long as the content of solvent according to the present invention can disperse quantum dot, it is able to maintain that and photoresist
The scope of the compatibility of compositionss, is just not particularly limited, such as with respect to the solid constituent 100 of quantum dot
Mass parts are 5～600 mass parts, the scope of more preferably 10～500 mass parts.If dispersant
Usage amount in terms of said reference more than 600 mass parts, then viscosity uprises sometimes, less than 5 mass parts
In the case of, the difficulties in dispersion of quantum dot, or consistency problem can be caused.
＜ emissive type photosensitive polymer combination ＞
The emissive type photosensitive polymer combination of the present invention is by comprising above-mentioned quantum dot dispersion, photopolymerization
Monomer, Photoepolymerizationinitiater initiater, alkali soluble resins and solvent, can be formed the characteristics of luminescence and pattern properties excellent,
High brightness fine pattern.
The quantum dot dispersion contained by emissive type photosensitive polymer combination of the present invention and solvent are as said
Above-mentioned shown in bright book.
The photo polymerization monomer contained by emissive type photosensitive polymer combination of the present invention is to pass through light
Effect with Photoepolymerizationinitiater initiater described later and the compound that is polymerized, can enumerate monofunctional monomer, two sense lists
Body, other polyfunctional monomer etc..
As the concrete example of monofunctional monomer, nonyl phenyl carbitol acrylate, 2- hydroxyl -3- can be enumerated
Phenoxypropylacrylate, 2- ethylhexyl carbitol acrylate, acrylic acid 2- hydroxy methacrylate, n-
Vinyl pyrrolidone etc..
As the concrete example of two functional monomers, 1,6- hexanediol two (methyl) acrylate, ethylene glycol can be enumerated
Two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, 2,2'-ethylenedioxybis(ethanol). two (methyl) acrylate, double
Double (acryloyl-oxyethyl) ether, 3- methyl pentanediol two (methyl) acrylate etc. of phenol a.
As the concrete example of other polyfunctional monomers, trimethylolpropane tris (methyl) acrylic acid can be enumerated
Ester, tetramethylolmethane three (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, dipentaerythritol five (first
Base) acrylate, dipentaerythritol six (methyl) acrylate etc..Wherein preferably use the many of more than two senses
Functional monomer.
The Photoepolymerizationinitiater initiater contained by emissive type photosensitive polymer combination of the present invention, does not limit,
But it is selected from triazine based compound, 1-Phenylethanone. based compound, bisglyoxaline based compound and oxime compound institute group
More than a kind compound in the group becoming.Emissive type photoresist group containing above-mentioned Photoepolymerizationinitiater initiater
Compound is high sensitivity, and the pixel being formed using said composition can make the intensity of this pixel portion, pattern become
Obtain well.If additionally, and using photopolymerization initiator auxiliary agent in Photoepolymerizationinitiater initiater, containing they from
Light emitting-type photosensitive polymer combination is further changed to high sensitivity, when forming color filter using said composition
Productivity improve therefore preferred.
The alkali soluble resins contained by emissive type photosensitive polymer combination of the present invention is that had by comprising
The polymerization of the ethylene unsaturated monomer of carboxyl.It is to the development treatment work being formed during pattern
The alkaline-based developer utilizing in sequence gives the composition of solubility.
There is the ethylene unsaturated monomer of carboxyl, be not particularly limited, such as acrylic acid, methyl can be enumerated
The monocarboxylic acid class such as acrylic acid .beta.-methylacrylic acid；The omega-dicarboxylic acids such as fumaric acid, mesaconic acid, itaconic acid and their acid anhydride；
Two ends such as ω-carboxy-polycaprolactone list (methyl) acrylate have the list (first of the polymer of carboxyl and hydroxyl
Base) esters of acrylic acid etc. is it may be preferred to be acrylic acid and methacrylic acid.They can be used alone or by 2
Plant use mixed above.
＜ color filter ＞
The color filter of the present invention in the case of being applied to image display device, due to by display device light source
Light and light, therefore can realize more excellent light efficiency.Further, since release has coloured light,
Therefore colorrendering quality is more excellent, due to discharging light by luminescence generated by light in whole directions, therefore can also
Improve visual angle.
Color filter comprises substrate and the patterned layer being formed on the top of aforesaid substrate.
With regard to substrate, color filter itself can be substrate, or can be color filter institute in display equipment etc.
The position at place, is not particularly limited.Aforesaid substrate can be glass, silicon (si), Si oxide (siox) or high
Molecule substrate, above-mentioned polymeric substrate can be polyether sulfone (polyethersulfone, pes) or Merlon
(polycarbonate, pc) etc..
Patterned layer is the layer of the photosensitive polymer combination comprising the present invention, and can be above-mentioned photosensitive for coating
Property resin combination, the layer being formed with predetermined pattern exposure, development and heat cure.
The patterned layer being formed by above-mentioned photosensitive polymer combination can possess containing red quantum point particle
Red pattern layer, the green pattern layer containing green quantum dot particles and the indigo plant containing blue quantum dot particles
Chromatic graph pattern layer.In the irradiation of light, red pattern layer discharges red light, and green pattern layer discharges green light,
Blue color patterns layer discharges blue light.
In this case, when being applied to image display device, the release light of light source is not particularly limited,
But from the aspect of excellent colorrendering quality, can be using the light source of release blue light.
According to other embodiments of the present invention, above-mentioned patterned layer can only possess red pattern layer, green figure
The patterned layer of 2 kinds of colors in pattern layer and blue color patterns layer.In this case, above-mentioned patterned layer enters one
Step possesses the transparent pattern layer not containing quantum dot particles.
In the case of the patterned layer only possessing 2 kinds of colors, can show, using release, the remaining face that not comprise
The light source of the light of the wavelength of color.For example, in the case of comprising red pattern layer and green pattern layer, can
Light source using release blue light.In this case, red quantum point particle release red light, green
Quantum dot particles discharge green light, and transparent pattern layer is directed through blue light and shows blueness.
The color filter comprising substrate and patterned layer as described above, can be further contained in shape between each pattern
The dividing plate becoming, can comprise black matrix further.Furthermore, it is possible to the patterned layer further contained in color filter
Top formed protecting film.
＜ image display device ＞
Additionally, the present invention provides the image display device comprising above-mentioned color filter.
The color filter of the present invention can not only be applied to common liquid crystal indicator, and can be applied to electricity
The various image display device such as photoluminescence display device, plasm display device, field-emission display device.
The image display device of the present invention can possess comprise the red pattern layer containing red quantum point particle,
Green pattern layer containing green quantum dot particles and the filter of the blue color patterns layer containing blue quantum dot particles
Color device.In this case, when being applied to image display device, the release light of light source does not especially limit
Fixed, but from the aspect of more excellent colorrendering quality, it is preferably able to the light source using release blue light.
According to other embodiments of the present invention, the image display device of the present invention can possess and only comprises redness
The color filter of the patterned layer of 2 kinds of colors in patterned layer, green pattern layer and blue color patterns layer.Such
In the case of, above-mentioned color filter is further equipped with not containing the transparent pattern layer of quantum dot particles.
In the case of the patterned layer only possessing 2 kinds of colors, can show, using release, the remaining face that not comprise
The light source of the light of the wavelength of color.For example, in the case of comprising red pattern layer and green pattern layer, can
Light source using release blue light.In this case, red quantum point particle release red light, green
Quantum dot particles discharge green light, and transparent pattern layer is directed through blue light and shows blueness.
The image display device of the present invention, light efficiency is excellent, exhibit high brilliance, and colorrendering quality is excellent, tool
There is wide viewing angle.
Hereinafter, the present invention is illustrated in greater detail by embodiment.However, following embodiments is for entering
One step specifically describes the present invention, and the scope of the present invention is not limited by following embodiments.Following embodiments
Can suitably be revised by those skilled in the art within the scope of the invention or change.
The synthesis of the luminescence generated by light green quantum dot particles a of Production Example 1.cdse (core)/zns (shell) structure
By cdo (0.4mmol), zinc acetate (zinc acetate) (4mmol), Oleic acid (oleic acid) (5.5ml)
It is added in reactor together with 1- vaccenic acid (1-octadecene) (20ml), being heated to 150 DEG C makes it anti-
Should.Then, in order to remove the acetic acid (acetic acid) that zinc is replaced Oleic acid and generated, above-mentioned reactant is existed
Place 20 minutes under the vacuum of 100mtorr.Then, apply 310 DEG C of heat, obtain transparent mixing
After thing, after it is maintained 20 minutes at 310 DEG C, the se powder of 0.4mmol and the s of 2.3mmol will be made
Se the and s solution obtained by tri octyl phosphine (trioctylphosphine) that powder is dissolved in 3ml rapidly injects
To equipped with cd (oa)2With zn (oa)2In the reactor of solution.Make thus obtained mixture in 310 DEG C of lifes
After long 5 minutes, make growth interruption using ice-water bath (ice bath).Then, with ethanol precipitation, using centrifugation
Separating quantum dot, unnecessary impurity utilizes chloroform (chloroform) and ethanol to wash, with 80 DEG C to seperator
Drying oven be dried 6 hours, thus obtained with Oleic acid stabilisation, karyosome footpath is distributed with and thickness of the shell it
Quantum dot powder a with cdse (core)/zns (shell) structure of the particle for 3～5nm etc..
Production Example 2-1: the synthesis of dispersant (b1)
Possessing agitator, thermometer, throwing in the flask of reflux cooling pipe, Dropping funnel and nitrogen ingress pipe
Enter propylene glycol monomethyl ether 100 weight portion, propylene glycol monomethyl ether 100 weight portion, aibn8
Weight portion, 2- ethylhexyl acrylate 21.4 weight portion, 4- methyl styrene 1.5 weight portion, methyl-prop
Olefin(e) acid ethylene oxidic ester 46 weight portion, n-dodecyl mercaptan 3 weight portion, and carry out nitrogen displacement.So
Afterwards, stirring makes the temperature of reactant liquor rise to 80 DEG C, reacts 4 hours.
Then, the temperature of reactant liquor is reduced to room temperature, the atmosphere of flask is become after air from nitrogen displacement,
Put into triethylamine 0.2 weight portion, 4- methoxyphenol 0.1 weight portion, acrylic acid 23.3 weight portion, at 100 DEG C
Reaction 6 hours.Then, the temperature of reactant liquor is reduced to room temperature, puts into succinic anhydrides 12.5 weight portion,
React 6 hours at 80 DEG C.The acid number of so solid constituent of alkali soluble resins of synthesis is 69mgkoh/g,
Obtain the dispersant (b1) that the weight average molecular weight (mw) being measured by gpc is 2980.
Production Example 2-2～2-4: the synthesis of dispersant (b2～b4)
In above-mentioned Production Example 2-1, the content of comonomer and ratio are fixed, the content of aibn is altered to 1～
6 weight portions and make acid number identical, obtain weight average molecular weight be respectively 5,800 (dispersant b2), 7,400 (point
Powder b3), the dispersant (b2～b4) of 9,800 (dispersant b4).
Production Example 3: the synthesis of alkali soluble resins (d ')
Prepare possess agitator, thermometer, the flask of reflux cooling pipe, Dropping funnel and nitrogen ingress pipe,
On the other hand, n- benzyl maleimide 35 weight portion, tricyclodecyl methacrylate 10 weight are put into
Amount part, acrylic acid 55 weight portion, tert-butyl hydroperoxide -2-ethylhexanoate 4 weight portion, propylene glycol list
Methylether acetate (hereinafter referred to as " pgmea ") 20 weight portions, propylene glycol monomethyl ether 20 weight portion
Afterwards, stirring mixing, prepares monomer Dropping funnel, adds n-dodecane mercaptan 6 weight portion, pgmea24
Weight portion, stirring mixing, prepare chain-transferring agent Dropping funnel.
Then, import pgmea395 weight portion in flask, the atmosphere in flask is replaced as from air
After nitrogen, stir and the temperature of flask is warmed up to 90 DEG C.Then, by monomer and chain-transferring agent
Start Deca from Dropping funnel.During Deca, maintain 90 DEG C, carry out on one side 2 hours respectively, 1
After being warmed up to 110 DEG C and maintain 3 hours after hour, so that gas introduction tube is imported, start oxygen/nitrogen=5/95 (v/v)
Mixed gas bubbling.Then, in flask put into glycidyl methacrylate 50 weight portion,
2,2 '-di-2-ethylhexylphosphine oxide (4- methyl-6-tert-butylphenol) 0.4 weight portion, triethylamine 0.8 weight portion, at 110 DEG C
Continue reaction 8 hours, then, cooling, until room temperature, obtains solid constituent 30.0 weight %, weight simultaneously
Average molecular weight 15,000, acid number are 60mgkoh/g, acryloyl group equivalent is the alkali solubility tree of 435g/eq
Fat d '.
Now, the assay method of molecular weight, solid constituent and acid number is as follows.
Molecular weight is evaluated
With regard to the mensure of the weight average molecular weight (mw) of each alkali soluble resins of above-mentioned manufacture, existed using gpc method
Carry out under conditions of below.
Device: hlc-8120gpc (eastern Cao's (strain) manufactures)
Post: tsk-gelg4000hxl+tsk-gelg2000hxl (is connected in series)
Column temperature: 40 DEG C
Mobile phase solvent: oxolane
Flow velocity: 1.0ml/ minute
Sample size: 50 μ l
Detector: ri
Measure sample solution concentration: 0.6 weight % (solvent=oxolane)
Correction standard substance: tsk polystyrene standard (standard polystyrene) f-40,
F-4, f-1, a-2500, a-500 (eastern Cao's (strain) manufactures)
Solid constituent
Weigh about 1g polymer solution and put in aluminum cup, after interpolation about 3g acetone makes it dissolve, normal
Temperature spontaneously dries.And, using air drier (espec Co., Ltd. manufactures, trade name: phh-101),
Under vacuo after 160 DEG C of dryings 3 hours, let cool in exsiccator, gravimetry.Subtracting by this weight
A small amount of solid constituent calculating polymer solution.
Acid number
Precision weighing 3g resin solution so as to be dissolved in the mixed solvent of acetone 90g/ water 10g, by hundred li
Phenol is blue to be used as indicator, and the koh aqueous solution of 0.1n is used as volumetric solution, (flat by automatic titration device
Natural pond industry companies manufacture, trade name: com-555) measure polymer solution acid number, by the acid number of solution
Obtain the acid number of every 1g solid constituent with the solid constituent of solution.
Production Example 4: the manufacture of quantum dot dispersion
Each composition described in table 1 below～table 2 is quantum dot (a), dispersant (b), solvent (c) mixing,
After being mixed into the 1.0mm zirconium oxide bead of same volume, using paint shaker das-200 (lau hemmer
Company), dispersion in 3 hours is carried out with the speed of 600 circle/minutes, manufactures quantum dot dispersion 4-1～4-15,
With regard to non-dispersant Production Example 4-15, in order to identical with quantum dot weight % of Production Example 4-1～4-14,
Additional input chloroform is manufacturing.
[table 1]
[table 2]
Embodiment 1: the manufacture of emissive type photosensitive polymer combination
Using in each composition described in Table 3 below and 4 in addition to quantum dot dispersion (a ') as spontaneous
The Photoepolymerizationinitiater initiater (b ') of light type photoresist composition, photo polymerization monomer (c '), alkali soluble resins (d ')
After mixing first with solvent (e '), put into Production Example 4-1～4-15, to manufacture embodiment 1～8 and comparative example
1～7.
[table 3]
[table 4]
Experimental example 1: the dispersibility of quantum dot dispersion and compatible with emissive type photosensitive polymer combination
Property evaluate
(1) the dispersibility evaluation of quantum dot dispersion
The dispersibility of the quantum dot dispersion with regard to manufacturing, visually observes the transparent level of dispersion liquid, not
It can be determined that being that dispersion is bad in the case of transparent.
The dispersibility result of Production Example 4-1～15 is recorded in table 5.
(2) Compatibility Evaluation with emissive type photosensitive polymer combination
As embodiment 1～8 and comparative example 1～7, mix with photoresist composition in quantum dot dispersion
Visually observe precipitation foreign body during conjunction to have or not, be recorded in table 5.
Experimental example 2: color filter manufacture and evaluation
(1) manufacture of color filter
Using the emissive type photoresist group manufacturing in above-described embodiment 1～8 and comparative example 1 and 7
Compound is manufacturing color filter.
That is, each emissive type photosensitive polymer combination above-mentioned is coated on glass base by method of spin coating
After on plate, mounting on hot plate, maintains form thin film within 3 minutes in 100 DEG C of temperature.Then, upper
State and the transmission pattern with horizontal stroke × vertical 20mm × 20mm square and 1 μm～100 μm are loaded on thin film
Line/space pattern test photomask, make and test being spaced apart 100 μm and carrying out irradiation ultraviolet radiation of photomask.
Now, the extra-high-pressure mercury vapour lamp (trade name ush-250d) that ultraviolet light source is made using ushio motor (strain)
With 200mj/cm under the atmosphere of air2Light exposure (365nm) carry out light irradiation, do not use special light
Learn filter.By the above-mentioned thin film having irradiated ultraviolet in the koh aqueous development solution of ph 10.5
Impregnate 80 seconds to develop.After the glass plate being applied with this thin film is washed using distilled water, nitrogen blowing
It is dried, is heated 10 minutes with 150 DEG C of heated ovens, manufacture color filter pattern.
The thickness of the film of emissive type color filter pattern of above-mentioned middle manufacture is 5.0 μm.
(2) mensure of luminous intensity
To the pattern with 20mm × 20mm square in the color filter defining above-mentioned spontaneous light pixel
The drafting department being formed uses 365nm cast 4w uv irradiator (vl-4lc, vilber lourmat)
Measure the region having carried out light conversion, with regard to the luminous intensity of embodiment 1～8 and comparative example 1～7, utilize
Beam splitter (ocean optics company system) is measuring the luminous intensity in 550nm region.
May determine that the luminous intensity of mensure is higher, then more play excellent spontaneous light characteristic, by luminous intensity
Measurement result be shown in table 5 below.
Now, with regard to color filter, 230 DEG C carry out 60 minutes hard toast, before measuring hard baking and it
Luminous intensity afterwards, is confirmed to maintain the level of luminous efficiency, is shown with luminous intensity sustainment rate in table 5.
[table 5]
With reference to above-mentioned table 5 understand, using the present invention weight average molecular weight be 300～5,000 there is carboxylic acid
Manufacture in the embodiment 1～embodiment 8 of quantum dot dispersion with the dispersant of unsaturated double-bond, quantum dot
Dispersing characteristic and photosensitive polymer combination the compatibility, using this photosensitive polymer combination colour filter
The characteristics of luminescence of device and light sustainment rate etc. are excellent.
But, as comparative example 5 and 6, in the case that the molecular weight of dispersant is less than 300, though
So the dispersing characteristic of quantum dot is good, but the compatibility with photosensitive polymer combination and the characteristics of luminescence are poor, such as
Comparative example 1 and 2 like that, is 5 in the molecular weight of dispersant, in the case of more than 000, cannot be sufficiently
The dispersing characteristic of quantum dot.Additionally, in the comparative example 3 of the dispersant of application carbamate system, obtaining
The dispersibility of quantum dot and the excellent compatibility with photosensitive polymer combination, but the characteristics of luminescence is very fragile
Result.Additionally, in the comparative example 4 of the dispersant applying acryloyl system and the comparison not applying dispersant
In the case of example 7, when mixing with photosensitive polymer combination, there is precipitation phenomenon, therefore, it can confirm to send out
The result of light characteristic difference.
Claims (8)
1. a kind of quantum dot dispersion is it is characterised in that comprise luminescence generated by light quantum dot particles, dispersant
And solvent,
Described dispersant is the compound in 1 intramolecular with carboxylic acid and unsaturated double-bond.
2. quantum dot dispersion according to claim 1 is it is characterised in that the weight of described dispersant
Average molecular weight is 300～5,000.
3. quantum dot dispersion according to claim 1 is it is characterised in that described luminescence generated by light amount
Son point particle is red quantum point particle, green quantum dot particles or blue quantum dot particles.
4. quantum dot dispersion according to claim 1 is it is characterised in that with described luminescence generated by light
As benchmark, described dispersant is 10～500 mass parts to content 100 mass parts of quantum dot particles.
5. quantum dot dispersion according to claim 1 it is characterised in that described have carboxylic acid and
The group that the compound of unsaturated double-bond is formed selected from following compound: acrylic acid, methacrylic acid, two seasons
Penta tetrol five acrylate monomester succinate, pentaerythritol triacrylate monomester succinate, dipentaerythritol
The succinate modified thing of five acrylate, the succinate modified thing of pentaerythritol triacrylate, dipentaerythritol five
The orthophthalic modified thing of acrylate, the orthophthalic modified thing of pentaerythritol acrylate and in order to
The copolymer comprising acrylic or methacrylic acid is imported by unsaturated double-bond group and uses glycidyl first
Macromolecular compound obtained by base acrylate addition polymerization.
6. a kind of emissive type photosensitive polymer combination is it is characterised in that comprise in Claims 1 to 5
Quantum dot dispersion described in any one.
7. a kind of color filter is it is characterised in that be by the emissive type photonasty tree described in claim 6
Oil/fat composition manufactures.
8. a kind of image display device, it comprises the color filter described in claim 7.
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| KR10-2015-0096360 | 2015-07-07 | ||
| KR1020150096360A KR101878421B1 (en) | 2015-07-07 | 2015-07-07 | Quantum dot dispersion, self emission type photosensitive resin composition comprising the same, color filter and image display device manufactured using the same |
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| JP (1) | JP2017021322A (en) |
| KR (1) | KR101878421B1 (en) |
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| Publication number | Publication date |
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| TW201702353A (en) | 2017-01-16 |
| KR20170006024A (en) | 2017-01-17 |
| JP2017021322A (en) | 2017-01-26 |
| TWI679269B (en) | 2019-12-11 |
| KR101878421B1 (en) | 2018-07-13 |
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