CN110275392A - Light converts resin combination, light conversion layer folds substrate and image display device - Google Patents

Light converts resin combination, light conversion layer folds substrate and image display device Download PDF

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Publication number
CN110275392A
CN110275392A CN201910199943.4A CN201910199943A CN110275392A CN 110275392 A CN110275392 A CN 110275392A CN 201910199943 A CN201910199943 A CN 201910199943A CN 110275392 A CN110275392 A CN 110275392A
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Prior art keywords
ethyoxyl
chemical formula
mentioned
quantum dot
acid
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CN201910199943.4A
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CN110275392B (en
Inventor
金亨柱
金正植
申奎澈
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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    • 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
    • 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 present invention provides light conversion resin combination, light conversion layer folds substrate and image display device.Above-mentioned light conversion resin combination includes the two or more quantum dots and adhesive resin that centre of luminescence wavelength differs 50nm or more each other, above-mentioned adhesive resin includes Cardo system adhesive resin and acrylic adhesive resin containing epoxy group, above-mentioned quantum dot includes the polyethylene glycol system ligand for being configured at surface, above-mentioned polyethylene glycol system ligand includes compound represented by chemical formula 1-A, so that brightness and long-term reliability are excellent.

Description

Light converts resin combination, light conversion layer folds substrate and image display device
Technical field
Substrate is folded the present invention relates to light conversion resin combination, light conversion layer and folds substrate using above-mentioned light conversion layer Image display device.
Background technique
By light-emitting component (Light Emitting Diode, LED) for back light unit (BackLight Unit, BLU in liquid crystal display (Liquid Crystal Display, LCD) TV), LED BLU is the part for being actually sent out light, It is one of most important part in LCD TV.
As the method for the LED BLU for forming white, usually by red (Red, R), green (Green, G) and blue The LED chip of (Blue, B) combines and is formed the LED BLU of white, or using blue LED die and has wide half breadth Emission wavelength yellow (Yellow, Y) fluorophor combination and white is presented.
However, in the case where combining the LED chip of red, green, blue, have due to LED chip number and Complicated process and the high such problems of manufacturing expense can not in the case where combining yellow fluorophor with blue LED die Green and red wavelength are distinguished, therefore excitation purity is poor, leads to the problem of colorrendering quality decline therewith, thus recently, it is intended to The color of image display device is improved by applying the optical film comprising quantum dot in the backlight for having used blue LED die Reproducibility and brightness.
However, inevitably being made in the manufacture of application composition using the ligand of the low-down compound of polarity With the solvent of toluene, hexane, chloroform etc, thus there are operators to have in the environment for being exposed to the solvent being harmful to the human body Middle implementation operation is such inconvenient.
In addition, in the case where above-mentioned optical film, other than the luminescent layer comprising quantum dot, barrier layer, substrate layer Etc. structures become complicated, it may occur that the decline of the light emission luminance of quantum dot caused by thus.In addition, with very in manufacturing process When high temperature makes film, it may occur that the problem of quantum dot delustring, and in order to be processed into the form of optical film, in low process It is carried out in temperature, therewith, there are problems in terms of long-term reliability, therefore it is required that the improvement to this.
Patent document 1 provides a kind of quantum dot composition, it includes: quantum dot；Include TiO2Core portion and covering are above-mentioned At least part of of core portion surface contains SiO2Shell portion core-shell structure scattering particles；And curable resin, it is above On the basis of the total weight for stating the solid component of quantum dot composition, above-mentioned scattering particles is 5 weight % or more, 50 weight % or less.
Patent document 2 provides a kind of optical sheet, it includes: multiple non-cadmium system quantum are dispersed in macromolecule resin Point, and the patterned polymer resin layer of one or both sides；Be formed in the one side of above-mentioned polymer resin layer first stops Film；And it is formed in the second barrier film of the another side of above-mentioned polymer resin layer, the bottom surfaces warp of above-mentioned polymer resin layer Prism pattern or lens pattern, in the case where the bottom surfaces of above-mentioned polymer resin layer are through prism pattern, above-mentioned rib The spacing of mirror pattern is 20~70 μm, and apex angle is 95~120 °, and the section of above-mentioned pattern is triangle；In above-mentioned macromolecule resin In the case that the bottom surfaces of layer are through lens pattern, the spacing of said lens pattern is 20~70 μm, the ratio of spacing and height For 4:1~10:1, the section of above-mentioned pattern is semicircle.
In addition, structure becomes complicated in the case where above-mentioned optical sheet, the light emission luminance of quantum dot is thus caused to decline, And firing temperature is low, therefore the problem of long-term reliability difference occurs.
Existing technical literature
Patent document
Patent document 1: Korean Patent Registration 10-1718592 bulletin
Patent document 2: Korean Patent Registration 10-1690624 bulletin
Summary of the invention
Problems to be solved by the invention
The present invention is used for problem as described above, it is intended that providing by the inclusion of Cardo system adhesive resin and containing There is the acrylic adhesive resin of epoxy group to brightness and the excellent light conversion resin combination of long-term reliability, light conversion Laminated substrate and the image display device that substrate is folded using above-mentioned light conversion layer.
In addition, another object of the present invention is to provide differ each other by the inclusion of two or more centre of luminescence wavelength 50nm or more and the quantum dot of new ligand has been imported so as to the light transition tree with excellent dispersibility and optical characteristics Oil/fat composition, light conversion layer are folded substrate and are folded the image display device of substrate using above-mentioned light conversion layer.
The method used for solving the problem
Light conversion resin combination of the invention for achieving the above object is characterized in that, includes centre of luminescence wavelength The two or more quantum dots and adhesive resin of 50nm or more are differed each other, and above-mentioned adhesive resin is viscous comprising Cardo system Mixture resin and acrylic adhesive resin containing epoxy group, above-mentioned quantum dot are matched comprising being configured at the polyethylene glycol system on surface Body, above-mentioned polyethylene glycol system ligand include compound represented by following chemical formula 1-A.
[chemical formula 1-A]
(in above-mentioned chemical formula 1-A,
R ' indicates by chemical formula 1-1,
[chemical formula 1-1]
*-R1-O-R2
In above-mentioned chemical formula 1-1,
R1 is to be directly connected to or the alkylidene of carbon atom number 1~10,
R2 indicates by chemical formula 1-2,
[chemical formula 1-2]
In above-mentioned chemical formula 1-2,
A be oxygen atom or sulphur atom,
R3 is to be directly connected to or the alkylidene of carbon atom number 1~10,
B is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateOr amido (- NH2),
R " is hydrogen atom, sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphoric acid BaseAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that k is 1~100,
The integer that l is 0~1,
The integer that m is 0~10).
Invention effect
Light conversion resin combination of the invention by the inclusion of Cardo system adhesive resin and contains the acrylic acid of epoxy group Be adhesive resin, thus have can be effectively performed with 100~250 degree of coating formation temperature processing, light characteristic and The excellent such effect of long-term reliability.
In addition, light conversion resin combination of the invention differs 50nm by the inclusion of two or more centre of luminescence wavelength each other Above and the quantum dot of new ligand is imported, to have dispersibility and the excellent such effect of optical characteristics.
Substrate is folded by the light conversion layer of above-mentioned light conversion resin combination manufacture and folds substrate using the light conversion layer Image display device has such effect excellent in reliability.
Specific embodiment
Hereinafter, the present invention is described in more detail.
It not only include a certain component and another structure when pointing out that a certain component is located at another component "upper" in the present invention The case where part contacts, include thes case where that there are other components between two components.
In the present invention, when pointing out a certain constituent element of certain a part of "comprising", mean, as long as no especially opposite Record, then can further include other constituent elements, rather than other constituent elements are excluded.
< light converts resin combination >
Light conversion resin combination of the invention is characterized in that, differs 50nm's or more each other comprising centre of luminescence wavelength Two or more quantum dots and adhesive resin, above-mentioned adhesive resin is comprising Cardo system adhesive resin and contains epoxy group Acrylic adhesive resin, above-mentioned quantum dot include the polyethylene glycol system ligand for being configured at surface, and above-mentioned polyethylene glycol system matches Body includes compound represented by following chemical formula 1-A.
[chemical formula 1-A]
(in above-mentioned chemical formula 1-A,
R ' indicates by chemical formula 1-1,
[chemical formula 1-1]
*-R1-O-R2
In above-mentioned chemical formula 1-1,
R1 is to be directly connected to or the alkylidene of carbon atom number 1~10,
R2 indicates by chemical formula 1-2,
[chemical formula 1-2]
In above-mentioned chemical formula 1-2,
A be oxygen atom or sulphur atom,
R3 is to be directly connected to or the alkylidene of carbon atom number 1~10,
B is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateOr amine (- NH2),
R " is hydrogen atom, sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphoric acid BaseAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that k is 1~100,
The integer that l is 0~1,
The integer that m is 0~10).
Quantum dot
Light conversion resin combination of the invention includes that centre of luminescence wavelength differs the two or more of 50nm or more each other Quantum dot, above-mentioned quantum dot include the polyethylene glycol system ligand for being configured at surface, and above-mentioned polyethylene glycol system ligand includes following Compound represented by chemical formula 1-A.
[chemical formula 1-A]
(in above-mentioned chemical formula 1-A,
R ' indicates by chemical formula 1-1,
[chemical formula 1-1]
*-R1-O-R2
In above-mentioned chemical formula 1-1,
R1 is to be directly connected to or the alkylidene of carbon atom number 1~10,
R2 indicates by chemical formula 1-2,
[chemical formula 1-2]
In above-mentioned chemical formula 1-2,
A be oxygen atom or sulphur atom,
R3 is to be directly connected to or the alkylidene of carbon atom number 1~10,
B is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateOr amido (- NH2),
R " is hydrogen atom, sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphoric acid BaseAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that k is 1~100,
The integer that l is 0~1,
The integer that m is 0~10).
Light of the invention converts quantum dot contained in resin combination as the semiconductor substance of nano-scale.Atomic building Molecule, molecule constitute cluster as small molecule aggregate and form nanoparticle, but when such nanoparticle particular with When the characteristic of semiconductor, it is referred to as quantum dot.If such quantum dot receives energy from outside and becomes excited state, There can be spontaneously release to be equivalent to the characteristic of the energy of band gap.To sum up, light conversion resin combination of the invention is logical It crosses comprising such quantum dot, so as to convert to the light of green light and red light by incident blue-light source.
As long as above-mentioned quantum dot can be shone by stimulating caused by light, there is no particular limitation, but preferably non-cadmium System, it is, for example, possible to use be selected from II-VI race's semiconducting compound, III-V semiconductor compound, group IV-VI semiconductor chemical combination Object and IV race element or one or more of compound comprising IV race element.
Above-mentioned II-VI race's semiconducting compound can be for selected from by Was Used compound, three element compounds and four elements One or more of the group of compound composition, above-mentioned Was Used compound be selected from by CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, The group of ZnO, HgS, HgSe, HgTe and their mixture composition；Above-mentioned three element compound be selected from by CdSeS, CdSeTe, CdSTe、ZnSeS、ZnSeTe、ZnSTe、HgSeS、HgSeTe、HgSTe、CdZnS、CdZnSe、CdZnTe、CdHgS、CdHgSe、 The group of CdHgTe, HgZnS, HgZnSe, HgZnTe and their mixture composition；Above-mentioned four element compound be selected from by CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe with And the group of their mixture composition.
Above-mentioned III-V race semiconducting compound can be for selected from by Was Used compound, three element compounds and four elements Close one or more of the group of object composition, above-mentioned Was Used compound be selected from by GaN, GaP, GaAs, GaSb, AlN, AlP, The group of AlAs, AlSb, InN, InP, InAs, InSb and their mixture composition；Above-mentioned three element compound be selected from by GaNP、GaNAs、GaNSb、GaPAs、GaPSb、AlNP、AlNAs、AlNSb、AlPAs、AlPSb、InNP、InNAs、InNSb、 The group of InPAs, InPSb, GaAlNP and their mixture composition；Above-mentioned four element compound be selected from by GaAlNAs, GaAlNSb、GaAlPAs、GaAlPSb、GaInNP、GaInNAs、GaInNSb、GaInPAs、GaInPSb、InAlNP、 The group of InAlNAs, InAlNSb, InAlPAs, InAlPSb and their mixture composition.
Above-mentioned IV-VI race's semiconducting compound can be for selected from by Was Used compound, three element compounds and four elements One or more of the group of compound composition, above-mentioned Was Used compound are selected from by SnS, SnSe, SnTe, PbS, PbSe, PbTe And the group of their mixture composition；Above-mentioned three element compound be selected from by SnSeS, SnSeTe, SnSTe, PbSeS, The group of PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and their mixture composition；Above-mentioned four element compound is selected from The group being made of SnPbSSe, SnPbSeTe, SnPbSTe and their mixture.
Above-mentioned IV race element or compound comprising IV race's element can be for selected from by single element compound and Was Useds One or more of the group of object composition is closed, said units element compound is selected from the group being made of Si, Ge and their mixture； Above-mentioned Was Used compound is selected from the group being made of SiC, SiGe and their mixture, and but not limited thereto.
Above-mentioned quantum dot can be (homogeneous) single structure of homogeneous；Core-shell structure copolymer (core-shell) structure, ladder Spend the dual structure of (gradient) structure or the like；Or their mixed structure.Such as at above-mentioned core-shell structure copolymer (core-shell) Dual structure in, the substance for constituting each core and shell can be formed by the above-mentioned semiconducting compound different from each other referred to.More Specifically, above-mentioned core may include selected from the group being made of Was Used compound, three element compounds and four element compounds One or more of substance, however, not limited to this, above-mentioned Was Used compound be selected from by GaN, GaP, GaAs, GaSb, AlN, The group of AlP, AlAs, AlSb, InN, InP, InAs, InSb and their mixture composition；Above-mentioned three element compound is selected from By GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, The group of InPAs, InPSb, GaAlNP and their mixture composition；Above-mentioned four element compound be selected from by GaAlNAs, GaAlNSb、GaAlPAs、GaAlPSb、GaInNP、GaInNAs、GaInNSb、GaInPAs、GaInPSb、InAlNP、 The group of InAlNAs, InAlNSb, InAlPAs, InAlPSb and their mixture composition.Above-mentioned shell, which may include, to be selected from The substance of one or more of ZnSe, ZnS and ZnTe, but not limited thereto.
For example, the quantum dot of nucleocapsid structure can enumerate InP/ZnS, InP/ZnSe, InP/GaP/ZnS, InP/ZnSe/ ZnS, InP/ZnSeTe/ZnS and InP/MnSe/ZnS etc..
Above-mentioned quantum dot can pass through wet chemistry process (wet chemical process), Metal Organic Chemical Vapor Deposition procedures (MOCVD, metalorganic chemical vapor deposition) or process of molecular beam epitaxy (MBE, Molecular beam epitaxy) and synthesize, but not limited thereto.
In the present invention, above-mentioned quantum dot can be non-cadmium system quantum dot.Specifically, above-mentioned quantum dot may include non-cadmium It is quantum dot.
In the present invention, in the case where above-mentioned quantum dot is non-cadmium system quantum dot, it is able to suppress the danger of environmental pollution, it is right Human body is harmless, therefore having the advantages that can be thus preferred comprising the health of the operator of operation quantum dot.
Convert to the light of green light and red light, above-mentioned non-cadmium system quantum dot to use incident blue-light source It may include two kinds or the quantum dot more than it of centre of luminescence wavelength difference 50nm or more different from each other, specific.Preferably, Above-mentioned non-cadmium system quantum dot may include the two or more quantum dots that centre of luminescence wavelength differs 70nm or more each other.
In the case where the difference of the centre of luminescence wavelength of the above two above non-cadmium system quantum dot is above range, tool There is the advantage that being capable of providing the display of excellent image quality because of wide colorrendering quality.
In above-mentioned non-cadmium system quantum dot, above-mentioned quantum dot is the green of 510nm~540nm using the range of centre of luminescence wavelength The range of color quantum dot and centre of luminescence wavelength is the red quantum dot of 610nm~630nm, this is for excellent color reproduction The realization of property is effective.Preferably, above-mentioned quantum dot may include the range of centre of luminescence wavelength within the above range Above-mentioned green quantum dot and above-mentioned red quantum dot have the advantages that meet above-mentioned shine respectively by application in this case The quantum dot of wavelength can be realized the white light source that blue by blue-light source is formed through light, green emitting, emitting red light The use of colour filter, therefore it is capable of providing the display equipment with wide colorrendering quality.
Above-mentioned polyethylene glycol system ligand is configured at the surface of quantum dot by being chemically combined.
Specifically, quantum dot of the invention include be configured at surface containing chemical combination represented by following chemical formula 1-A The polyethylene glycol system ligand of object.Specifically, above-mentioned polyethylene glycol system ligand is configured at the table of quantum dot by being chemically combined Face.
[chemical formula 1-A]
(in above-mentioned chemical formula 1-A,
R ' indicates by chemical formula 1-1,
[chemical formula 1-1]
*-R1-O-R2
In above-mentioned chemical formula 1-1,
R1 is to be directly connected to or the alkylidene of carbon atom number 1~10,
R2 indicates by chemical formula 1-2,
[chemical formula 1-2]
In above-mentioned chemical formula 1-2,
A be oxygen atom or sulphur atom,
R3 is to be directly connected to or the alkylidene of carbon atom number 1~10,
B is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateOr amido (- NH2),
R " is hydrogen atom, sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that k is 1~100,
The integer that l is 0~1,
The integer that m is 0~10).
In the present invention, abovementioned alkyl can be linear chain or branched chain, such as have methyl, ethyl, n-propyl, isopropyl, positive fourth Base, isobutyl group, tert-butyl, sec-butyl, 1- methyl-butvl, 1- Ethyl-butyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, N-hexyl, 1- methyl amyl, 2- methyl amyl, 4- methyl -2- amyl, 3,3- dimethylbutyl, 2- ethyl-butyl, n-heptyl, 1- methylhexyl, n-octyl, t-octyl, 1- methylheptyl, 2- ethylhexyl, 2- propylpentyl, n-nonyl, 2,2- dimethyl-g Base, 1- Ethyl-propyl, 1,1- Dimethyl-propyl, isohesyl, 2- methyl amyl, 4- methylhexyl, 5- methylhexyl etc., but not It is defined in this.
In the present invention, above-mentioned alkylidene can be applicable in explanation related with alkyl other than it is divalent.
In the present invention, above-mentioned * indicates linking group.
Compound represented by above-mentioned chemical formula 1-A can be indicated by following chemical formula 1-3.
[chemical formula 1-3]
(in above-mentioned chemical formula 1-3,
R " is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that o is 0~5,
The integer that p is 0~1,
The integer that q is 1~50).
In the case where the quantum dot of ligand as comprising oleic acid (oleic acid), oleyl amine (oleylamine), though It is so well dispersed within the volatilization nonpolar solvent of height as hexane (n-hexane) and chloroform, but is usually existed against corrosion in manufacture Point when agent or production display device in propylene glycol series solvent as used methyl proxitol acetate (PGMEA) Dissipate the very weak problem of property.However, quantum dot of the invention is well dispersed within PGMEA due to using polyethylene glycol system ligand Such solvent, therefore become easy with operability, and the advantage that can more protect the health of operator, make Use compound represented by above-mentioned chemical formula 1-3 as in the case where compound represented by above-mentioned chemical formula 1-A, it is especially above-mentioned The advantages of maximize, therefore preferably.
As the concrete example of above-mentioned polyethylene glycol system ligand, 2- (2- methoxy ethoxy) acetic acid (He Guanggong can be enumerated Department), 2- [2- (2- methoxy ethoxy) ethyoxyl] acetic acid (2- [2- (2- methoxy ethoxy) ethyoxyl] acetic acid (He Guanggong Department), mono succinate-[2- (2- Mehtoxy-ethoxy)-ethyl] ester, malonic acid it is mono- [2- (2- Mehtoxy-ethoxy)-ethyl] Ester, glutaric acid mono- { 2- [2- (2- ethoxy-ethoxy)-ethyoxyl]-ethyl } ester, { 2- [2- (2- ethyl-hexyloxy)-second Oxygroup]-ethyoxyl }-acetic acid, mono succinate-[2- (2- { 2- [2- (2- { 2- [2- (2- ethoxy-ethoxy)-ethyoxyl]-second Oxygroup }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] ester, mono succinate-[2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- Mehtoxy-ethoxy)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-second Oxygroup]-ethyoxyl }-ethyoxyl)-ethyl] ester, mono- [2- (2- { 2- [2- (2- { 2- [2- (the 2- isobutoxy-ethoxy of malonic acid Base)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] ester, the mono- [2- (2- of adipic acid { 2- [2- (2- Mehtoxy-ethoxy)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] ester, 2- oxo-adipic acid 6- (2- { 2- [2- (2- ethoxy-ethoxy)-ethyoxyl]-ethyoxyl }-ethyl) ester, mono succinate-[2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- Mehtoxy-ethoxy)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]- Ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethoxy Base }-ethyoxyl)-ethyl] ester, O- (succinyl)-O '-methyl polyethylene glycol 2 ' 000 (aldrich company), (2- butoxy- Ethyoxyl)-acetic acid ((2- butoxy-ethyoxyl)-acetic acid (and light company), { 2- [2- (Carboxvmethoxv) ethyoxyl] ethoxy Base } acetic acid (and light company), 2- [2- (benzyloxy) ethyoxyl] acetic acid, (2- Carboxvmethoxv-ethyoxyl)-acetic acid (He Guanggong Department), ((2- butoxy-ethyoxyl)-acetic acid (and light company) etc., but not limited thereto for (2- butoxy-ethyoxyl)-acetic acid.
Above-mentioned non-cadmium system quantum dot by using polyethylene glycol system ligand, thus even if using colour filter production line of batch Used in solvent as propylene glycol monomethyl ether without the use of the volatility as toluene, hexane, chloroform big Solvent can also assign the dispersing characteristic of good quantum dot.
Relative to quantum dot entirety, the content of the above-mentioned non-cadmium system quantum dot comprising polyethylene glycol system ligand for 5%~ 150%, more preferably 10%~100%.It is less than in the content of the above-mentioned non-cadmium system quantum dot comprising polyethylene glycol system ligand upper In the case where stating range, the dispersing characteristic of quantum dot may be bad, in the case where being greater than above range, although point of quantum dot Excellent is dissipated, but the curing characteristics of film may decline, therefore preferred content is met the above range.
Relative to 100 parts by weight of solid component of light conversion resin combination, the content of above-mentioned quantum dot can be 1~40 Parts by weight preferably can be 2~20 parts by weight.The content of above-mentioned quantum dot within the above range in the case where, have hair Light efficiency is excellent, coating it is excellent in reliability the advantage that.In the case where the content of above-mentioned quantum dot is less than above range, The light conversion efficiency of green light and red light is insufficient, in the case where being greater than above range, the release relative drop of blue light, Colorrendering quality variation can be led to the problem of.
Adhesive resin
Light conversion resin combination of the invention includes adhesive resin, and above-mentioned adhesive resin may include thermosetting property tree Rouge or alkali soluble resins.Specifically, above-mentioned adhesive resin may include acrylic adhesive resin containing epoxy group and Cardo system adhesive resin is as thermosetting resin or alkali soluble resins.
Above-mentioned acrylic adhesive resin containing epoxy group may include at least one in 2~chemical formula of following chemical formula 4 Kind repetitive unit.
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
(in above-mentioned chemical formula 2~4,
R4, R5 and R6 are each independently hydrogen or methyl).
Including the acrylic acid series containing epoxy group at least one of above-mentioned 2~chemical formula of chemical formula 4 repetitive unit In the case where adhesive resin, the excellent light conversion ratio of resin combination and excellent is converted by excellent mechanical property and light Different light sustainment rate, colorrendering quality and reliability can become good.
Above-mentioned Cardo system adhesive resin has the function of the reactivity by means of light, heat, and the dispersion as quantum dot is situated between Matter and play a role.As long as the Cardo system adhesive resin conduct contained in light conversion resin combination of the invention For quantum dot binder resin and play a role and can be used as the resin of the supporter of light conversion coating, just do not limit System.
Above-mentioned Cardo system adhesive resin may include at least one of 5~chemical formula of following chemical formula 10 and repeat list Member.
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
In above-mentioned chemical formula 5~8,
X and X ' is each independently singly-bound ,-CO- ,-SO2-、-C(CF3)2-、-Si(CH3)2-、-CH2-、-C(CH3)2-、- O-、
Y is anhydride residue,
Z is acid dianhydride residue,
R " ' is hydrogen atom, ethyl, phenyl ,-C2H4Cl、-C2H4OH or-CH2CH=CH2,
R7, R7 ', R8, R8 ', R9, R9 ', R10, R10 ', R11, R11 ', R12 and R12 ' be each independently hydrogen atom or Methyl,
R13, R13 ', R14 and R14 ' are each independently the straight-chain alkyl-sub or carbon atom number 3~6 of carbon atom number 1~6 Branched alkylidene, above-mentioned alkylidene can be by the Asia of ester bond, the cycloalkylidene of carbon atom number 6~14 and carbon atom number 6~14 At least one of aryl interrupts,
It is former that R15, R15 ', R16, R16 ', R17, R17 ', R18 and R18 ' are each independently hydrogen atom, halogen atom or carbon The straight chained alkyl of subnumber 1~6 or the branched alkyl of carbon atom number 3~6,
R and s is respectively the integer for meeting 0≤m≤30,0≤n≤30,
Wherein, r and s is not 0 simultaneously.
[chemical formula 9]
[chemical formula 10]
In above-mentioned chemical formula 9 and 10,
P is each independently
R19 and R20 is each independently hydrogen, hydroxyl, mercapto, amino, nitro or halogen atom,
Ar1 is each independently C6~C15 aryl,
Y ' is anhydride residue,
Z ' is acid dianhydride residue,
A ' be O, S, N, Si or Se,
A and b is each independently 1~6 integer,
C and d is each independently 0~30 integer,
Wherein, c and d is not 0 simultaneously.
It include in the repetitive unit with above-mentioned 5~chemical formula of chemical formula 10 in light conversion resin combination of the invention In the case where the Cardo system adhesive resin of at least one repetitive unit, there is reliability between process to become excellent, the production of outgassing Raw minimize and panel do not generate ghost when starting, and the image quality, excellent of high-quality can be assigned because of excellent reflection preventing effect The advantages of different heat resistance, chemical resistance, durability and reliability.
The Y of above-mentioned chemical formula 5 and 7 is the residue of acid anhydrides, can make the conjunction as Cardo system adhesive resin of the invention It reacts and obtains with anhydride compound at the bisphenol epoxies base acrylate compounds of intermediate.The acid anhydrides of residue Y can be imported Compound is not particularly limited, for example, maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydro can be enumerated Phthalic anhydride, hexahydrophthalic anhydride, methylendomethylenetetrahydrophthalic tetrabydrophthalic anhydride, chlorendic anhydride, methyl tetrahydro Phthalic anhydride etc..
The Z of above-mentioned chemical formula 6 and 8 is the residue of acid dianhydride, can be made as Cardo system adhesive resin of the invention The bisphenol epoxies base acrylate compounds of synthetic intermediate are reacted with acid dianhydride compounds to be obtained.It can import residue Z's Acid dianhydride compounds are not particularly limited, for example, pyromellitic acid anhydride, benzophenone tetracarboxylic dianhydride, biphenyl can be enumerated The aromatic polycarboxylic acids acid anhydride such as tetracarboxylic acid dianhydride, bibenzene tetracarboxylic dianhydride.
Above-mentioned " acid dianhydride " means that intramolecular has the compound of 2 anhydride groups.
In the present invention, the manufacturing method of above-mentioned Cardo system adhesive resin is not particularly limited.For example, bis-phenol can be made Compound is reacted with epoxide, after bisphenol synthesis epoxide, makes the bisphenol epoxy compound and acrylate of synthesis Compound reacts, and after bisphenol synthesis epoxy acrylic ester compounds, makes bisphenol epoxy acrylate compound and acid anhydrides, acid dianhydride Or their mixture is reacted and is manufactured, but not limited thereto.
The weight ratio of above-mentioned Cardo system adhesive resin and the acrylic adhesive resin containing epoxy group can be 10:90 ~90:10.It is above range in the ratio of above-mentioned Cardo system adhesive resin and the acrylic adhesive resin containing epoxy group In the case of, the physical characteristic with the heat curable properties for warming film in treatment process after after coating film due to excellent is excellent The advantage that, in the case where being detached from above range, the curing degree of film is insufficient and reliability may decline.
Relative to whole 100 parts by weight of above-mentioned light conversion resin combination, the content of above-mentioned adhesive resin can be 1 ~40 parts by weight preferably can be 1~30 parts by weight, more preferably can be 2~10 parts by weight.In containing for above-mentioned adhesive resin Amount within the above range in the case where, heat cure is easy, and when heat cure prevents film from reducing, and coating characteristic becomes well, thus It is preferred that.In the case where above-mentioned adhesive resin content is less than above range, film-strength be may be decreased due to curing degree deficiency, In the case that the content of above-mentioned adhesive resin is greater than above range, coating reduces and is likely difficult to form uniform film.
Scattering particles
Light conversion resin combination of the invention may include scattering particles.
Common inorganic material can be used in above-mentioned scattering particles, and preferably may include average grain diameter is 50~1,000nm Metal oxide.
Specifically, above-mentioned metal oxide can be for selected from by Al2O3、SiO2、ZnO、ZrO2、BaTiO3、TiO2、 Ta2O5、Ti3O5、ITO、IZO、ATO、ZnO-Al、Nb2O3, SnO, MgO and their combination composition one of group.It is necessary When, the material that by acrylate etc. there is the compound of unsaturated bond to be surface-treated also can be used.
In addition, passing through above-mentioned scattering particles in the case where light conversion resin combination of the invention includes scattering particles The path of the light issued from quantum dot can be made to increase, improve the overall optical efficiency on light conversion coating, therefore preferably.
Above-mentioned scattering particles can have the average grain diameter of 50~1,000nm, and the model of 100~500nm preferably can be used The scattering particles enclosed.At this point, can not expect the sufficient scattering effect of the light issued from quantum dot if particle size is too small Fruit in the case where excessive, is precipitated in composition in contrast, or can not obtain the light emitting layer surface of uniform quality, Therefore use can be suitably adjusted within the above range.
Relative to 100 parts by weight of all solids ingredient of above-mentioned light conversion resin combination, the content of above-mentioned scattering particles It can be 0.5~20 parts by weight, preferably can be 1~15 parts by weight.Above-mentioned scattering particles content within the above range In the case where, the increase effect of luminous intensity can be made to maximize, therefore preferably.It is less than in the content of above-mentioned scattering particles above-mentioned In the case where range, it may be difficult to the luminous intensity for ensuring to go for, in the case where being greater than above range, blue irradiation light Permeability decline, there may be problems in terms of luminous efficiency, therefore preferably appropriate within the above range use.
Heat-curable compounds
Light conversion resin combination of the invention may include heat-curable compounds.
The average molecular weight of above-mentioned heat-curable compounds is preferably 20,000 hereinafter, being especially more preferably 1,000~20, 000.In the case where the average molecular weight of above-mentioned heat-curable compounds meets above-mentioned condition, membrane left rate and excellent heat resistance.
Above-mentioned heat-curable compounds are preferably by converting whole 100 parts by weight of resin combination relative to light as 10~80 weight The epoxide of part is constituted.It, may be strong because of film in the case where the content of above-mentioned heat-curable compounds is less than above range Degree is insufficient and leads to reliability decrease.
As the concrete example for the heat-curable compounds for meeting above-mentioned condition, 2- [4- (2,3- glycidoxy) can be enumerated Phenyl] -2- [4- [bis- [4- ([2,3- glycidoxy] the phenyl)] ethyls of 1,1-] phenyl] propane and the bis- [4- [1- [4- of 1,3- (2,3- glycidoxy) phenyl] -1- [4- [1- [4- (2,3- glycidoxy phenyl) -1- Methylethyl] phenyl] ethyl] benzene Oxygroup] -2- propyl alcohol mixture, 2- [4- (2,3- glycidoxy) phenyl] -2- [4- [bis- [4- ([the third oxygen of 2,3- epoxy of 1,1- Base] phenyl)] ethyl] phenyl] propane etc..As commercially available commodity, JER157S65,157S70 (trade name can be enumerated；JER Company's product) etc..They can respectively individually or be used in combination of two or more.
Heat-curable compounds of the invention can further include other than above-mentioned bisphenol A novolac type ring oxygen compound Epoxy resin.As the epoxy resin that can include together with above-mentioned phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin and use simultaneously Bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, diphenyl ether type ring oxygen can be used in preference Resin, hydroquinone type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, fluorenes epoxy resin, phenol novolak type ring Oxygen resin, o-cresol phenolic epoxy varnish, trihydroxy benzene methylmethane type epoxy resin, trifunctional type epoxy resin, four Phenolic group ethane type epoxy resin, dicyclopentadiene phenol epoxy resin, bisphenol-A epoxy resin, bisphenol-A are polynary containing core Alcohol type epoxy resin, polypropylene glycol type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, second Dialdehyde type epoxy resin, ester ring type polyfunctional epoxy resin, heterocyclic-type epoxy resin etc..These epoxy resin can respectively individually Or two or more combinations are further included into use with above-mentioned phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin.
As above-mentioned epoxy resin, following commercially available product can be used.More specifically, it can enumerate as Bisphenol F YDF-175S (Dongdu be melted into company's product) of type epoxy resin etc., as (Dongdu YDB-715 of bisphenol A type epoxy resin Cheng company product) etc., as EPICLON EXA1514 (the big Japanese ink chemical industrial company system of bisphenol-s epoxy resin Product) etc., as YDC-1312 (Dongdu be melted into company's product) of hydroquinone type epoxy resin etc., as naphthalene type epoxy resin EPICLON EXA4032 (big Japanese ink chemical industrial company product) etc., as the EPIKOTE of biphenyl type epoxy resin YX4000H (JER company product) etc., as JER157S65 or 157S70 (the JER company of phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin Product) etc., as EPPN-201 (Japanese chemical drug corporation product), the JER152,154 (JER of phenol novolak type epoxy resin Company's product) etc., as EOCN-102S, 103S, 104S of cresol novolak type epoxy resin or 1020 (Japanese chemical drug is public Take charge of product), as EPIKOTE 1032H60 (JER company product) of trihydroxy benzene methylmethane type epoxy resin etc., as three officials Can type epoxy resin VG3101M80 (Mitsui Chemicals, Inc.'s system product) etc., as the EPIKOTE of four phenolic group ethane type epoxy resin 10315 (JER company products) etc., as ST-3000 (Dongdu be melted into company's product) of bisphenol-A epoxy resin etc., make EPIKOTE 190P (JER company product) for glycidyl ester type epoxy resin etc., as glycidyl amine type epoxy resin YH-434 (Dongdu be melted into company's product) etc., as the YDG-414 of glyoxal type epoxy resin (Dongdu is melted into company's product) Deng, as EPOLEAD GT-401 (Daicel chemical company product) of ester ring type polyfunctional epoxy resin etc..Above-mentioned asphalt mixtures modified by epoxy resin Rouge can respectively individually or be used in combination of two or more.
Relative to the 100 weight % of solid component of light conversion resin combination, the content of above-mentioned heat-curable compounds is preferred For 10~80 weight %, more preferably 15~70 weight %.It is within above range in the content of above-mentioned heat-curable compounds In the case where, membrane left rate and flatness are good.
Curing accelerator
Light conversion resin combination of the invention may include curing accelerator.
Above-mentioned curing accelerator can it is preferable to use selected from by such as carboxylic acid compound, organic sulfur chemical combination with mercapto The compound of one or more of the group of object, acid agent composition, but not limited thereto.
Above-mentioned carboxylic acid compound is preferably the miscellaneous acetic acid class of aromatic series, can specifically enumerate phenyl acetic acid, aminomethyl phenyl Thioacetic acid, ethylphenyl thioacetic acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenyl Thioacetic acid, dimethoxyphenylthio acetic acid, chlorophenylthio acetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, benzene Ethoxyacetic acid, naphthylthio acetic acid, N- naphthalene glycine, naphthoxy acetic acid, 1,2,4- benzenetricarboxylic acid acid anhydrides etc., but be not limited to This.
As the concrete example of above-mentioned organosulfur compound with mercapto, 2-mercaptobenzothiazole, Isosorbide-5-Nitrae-can be enumerated Bis- (3- sulfydryl butyryl acyloxy) butane, 1,3,5- tri- (3- sulfydryl butoxyethyl group) -1,3,5- triazine -2,4,6 (1H, 3H, 5H) - Triketone, trimethylolpropane tris (3-thiopropionate), pentaerythrite four (3- mercaptobutylate), (the 3- sulfydryl of pentaerythrite four Propionic ester), dipentaerythritol six (3-thiopropionate), tetraethylene glycol bis- (3-thiopropionates) etc., but not limited thereto.
As the concrete example of above-mentioned acid agent, 4- hydroxy phenyl dimethyl sulfonium tosilate, 4- hydroxyl can be enumerated Pheiiyldimetliyl sulfonium hexafluoro antimonate, 4- acetoxyl group phenyl dimethyl sulfonium tosilate, 4- acetoxyl group phenyl methyl Benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, diphenyl iodineTo toluene sulphur Hydrochlorate, diphenyl iodineHexafluoro antimonate etc.Salt, nitrobenzyl tosylate class, benzoin toluenesulfonic acid salt etc..
On the basis of 100 parts by weight of solid component of above-mentioned light conversion resin combination, relative to above-mentioned adhesive resin With above-mentioned 100 parts by weight of heat-curable compounds, the content of above-mentioned curing accelerator can be 0.1~40 parts by weight, preferably can be with For 1~30 parts by weight.In the case where the content of above-mentioned curing accelerator is met the above range, the light comprising it converts resin group Object high-sensitivity is closed, the curing time of film shortens, therefore there is productivity to improve, and can be realized excellent as high reliability Point, and there is the surface smoothness in the painting film strength formed using it and above-mentioned film portion can become the advantage that good.Phase Instead, in the case where the content of above-mentioned curing accelerator is less than above range, the decline of curing degree can not be solved, in subsequent handling There may be gauffers, and in the case where being greater than above range, there are the characteristics of luminescence declines of light conversion resin combination, and brightness is not Abundant such problems.
Solvent
Light conversion resin combination of the invention may include solvent.
Solvent contained by light conversion resin combination of the invention usually may include one or more, especially In the case where include 50% or more boiling point relative to whole solvents being 100~180 DEG C of solvent, flow behavior is excellent, no The uneven and dry foreign matter of coating can occur, therefore be capable of providing the folded substrate of good light conversion layer for not coating foreign matter.
As concrete example, may include selected from being made of ethers, aromatic hydrocarbon, ketone, alcohols, esters and amides etc. One or more of group, specifically, can be for selected from by propylene glycol monomethyl ether, ethylene glycol single methyl ether, second Glycol list ethylether, methylcellosolve acetate, ethyl cellosolve acetate, mesitylene, methyl amyl ketone, methyl-isobutyl Ketone, 3- ethoxyl ethyl propionate, 1,3 butylene glycol diacetate esters, ethyl -3- ethoxy-c acid esters, propylene-glycol diacetate, second Glycol list propyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, methoxybutyl acetic acid esters, ethylene glycol and γ-Ding Nei One or more of groups of compositions such as ester.
In the case where solvent of the above-mentioned boiling point less than 100 DEG C is 50% or more of whole solvents, rate of drying is fast, therefore When being dried in vacuo (Vacuum Dry) process the surface of film occur it is uneven and may cause it is bad, in boiling point greater than 180 DEG C In the case that solvent is 50% or more of whole solvents, required time (Tack-time) becomes when may cause Vacuum Drying Step Long problem.Therefore, the solvent that it is 100~180 DEG C using boiling point that 50% or more solvent of whole solvents, which is suitble to,.
100 weight % of resin combination is converted relative to above-mentioned light, the content of above-mentioned solvent can be 50~90 weight %, It is preferred that can be 60~85 weight %.The content of above-mentioned solvent within the above range in the case where, utilize roll coater, spin coating When the apparatus for coating such as machine, slit spin coater, slit coater (otherwise referred to as die applicator), ink jet printer are coated, Coating can become good.
Additive
Light conversion resin combination of the invention can further include well known additive according to diversified purpose. As such additive, such as filler also can be used together, auxiliary curing agent, other high-molecular compounds, closely sealed promotor, resist The additives such as oxidant, ultraviolet absorbing agent, anticoagulant.One or more can be used in these additives, it is contemplated that light Efficiency etc., it is preferably used below with 1 weight % in entire combination object.
As above-mentioned filler, it can be glass, silica, aluminium oxide etc., polyvinyl alcohol, polypropylene can be enumerated Thermoplastic resins such as acid, polyalkylene glycol monoalkyl ether, poly- fluoroalkyl, polyester, polyurethane etc..
As other above-mentioned high-molecular compounds, the curable resins such as maleimide resin, poly- second can be specifically enumerated Thermoplastic resins such as enol, polyacrylic acid, polyalkylene glycol monoalkyl ether, poly- fluoroalkyl, polyester, polyurethane etc..
As above-mentioned closely sealed promotor, it can be cited for example that vinyltrimethoxysilane, vinyltriethoxysilane, Vinyl three (2- methoxy ethoxy) silane, N- (2- amino-ethyl) -3- aminopropylmethyldimethoxysilane, N- (2- Amino-ethyl) -3- TSL 8330,3-aminopropyltriethoxysilane, 3- epoxypropoxy trimethoxy Base silane, 3- glycidoxypropyl dimethoxysilane, 2- (3,4- epoxycyclohexyl) ethyl trimethoxy silane, 3- chlorine Hydroxypropyl methyl dimethoxysilane, 3- r-chloropropyl trimethoxyl silane, 3- methacryloxypropyl trimethoxy silane, 3- Mercaptopropyi trimethoxy silane etc..
As above-mentioned antioxidant, 2,2 '-thiobis (4- methyl-6-tert-butylphenol), 2,6- bis--can be specifically enumerated Tert-butyl-4-methyl-Phenol etc..
As above-mentioned ultraviolet absorbing agent, it is specifically as follows 2- (3- tert-butyl -2- hydroxy-5-methyl base phenyl) -5- chlorobenzene And triazole, alkoxy benzophenone etc..
As above-mentioned anticoagulant, Sodium Polyacrylate etc. can be specifically enumerated.
Those skilled in the art suitably additional within the scope of the effect of the invention can use above-mentioned additive. Such as whole 100 parts by weight relative to above-mentioned light conversion resin combination, above-mentioned additive can with 0.05~10 parts by weight, It is preferred that 0.1~10 parts by weight, more preferable 0.1~5 parts by weight use, but not limited thereto.
< light conversion layer folds substrate >
Light conversion layer of the invention folds the solidfied material that substrate includes the light conversion resin combination being formed on substrate.It is above-mentioned Light conversion layer folds substrate by the inclusion of the solidfied material of light conversion resin combination, so as on the glass substrate with 100~250 DEG C coating formation temperature be more effectively carried out processing, compared with previous labyrinth, brightness and long-term reliability are excellent.
Above-mentioned light conversion layer, which folds substrate, to be silicon (Si), Si oxide (SiOx) or polymeric substrate, above-mentioned macromolecule Substrate can be polyether sulfone (PES) or polycarbonate (PC) etc..
Above-mentioned light conversion layer, which folds substrate, can convert resin combination by being coated with above-mentioned light, and carry out heat cure and shape At.
< image display device >
Image display device of the invention includes that light conversion layer above-mentioned folds substrate.Above-mentioned image display device specifically can be with Enumerate liquid crystal display (liquid crystal display device；LCD), organic el display (organic EL display device), liquid crystal projection apparatus, game The portable terminals such as machine display device, portable phone display device, digital camera display device, automobile navigation display dress It the display devices etc. such as sets, is especially suitable for colour display device.
Above-mentioned image display device can also include technology of the invention other than having above-mentioned light conversion layer and folding substrate Those skilled in the art are known in field is constituted, that is, the present invention includes the figure that substrate can be folded using light conversion layer of the invention As display device.
Hereinafter, being described in detail to illustrate this specification using embodiment.However, the implementation in this specification Example can be deformed into various other modes, and the range of this specification will not be interpreted by the reality being described below in detail Apply the restriction of example.Embodiment in this specification be in order to more completely illustrate this specification to those of ordinary skill in the art and It provides.In addition, then " % " and " part " of following presentation content is weight basis as long as no specifically mentioned.
The manufacture of scattering particles dispersion liquid
Production Example 1: the manufacture of scattering particles dispersion liquid S1
By the TiO as the partial size 220nm of scattering particles2(Huntsman Corporation TR-88) 70.0 parts by weight, as dispersing agent DISPERBYK-2001 (manufacture of Bi Ke company) 4.0 parts by weight, 26 parts by weight of methyl proxitol acetate as solvent Mixing/dispersion in 12 hours is carried out using ball mill, manufactures scattering particles dispersion liquid S1.
Synthesis example 1: the synthesis (Q-1) of green quantum dot
Reactor is added in indium acetate 0.4mmol (0.058g), palmitinic acid 0.6mmol (0.15g) and 1- octadecylene 20mL In, it is heated to 120 DEG C under vacuum.After 1 hour, the atmosphere in reactor is converted into nitrogen.After being heated to 280 DEG C, quickly Inject three (trimethyl silyl) phosphine (TMS3P) the mixed solution of 0.2mmol (58 μ L) and tri octyl phosphine 1.0mL, and carry out It reacts within 0.5 minute.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, selenium (Se/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally mixed Object is closed react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, will be precipitated obtained by centrifuge separation into Row is filtered under diminished pressure, and is then dried under reduced pressure, and InP/ZnSe core-shell structure copolymer is formed.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, sulphur (S/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally to mix Object react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, is carried out being precipitated obtained by centrifuge separation It is filtered under diminished pressure, is then dried under reduced pressure, obtain the quantum dot of InP/ZnSe/ZnS nucleocapsid structure, so that it is scattered in chlorine later In imitative.
The maximum glow peak of the luminescent spectrum of resulting nano-quantum point is 515nm, and quantum dot solution 5mL is added and is centrifuged In separating pipe, ethyl alcohol 20mL, which is added, makes its precipitating.Supernatant is removed by being centrifugated, the chlorine of 2mL is added in sediment It is imitative to disperse quantum dot, (2- butoxy-ethyoxyl)-acetic acid of 0.50g is then added, is heated in a nitrogen atmosphere with 60 DEG C, It carries out reacting for 1 hour simultaneously.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 516nm.
Synthesis example 2: the synthesis (Q-2) of green quantum dot
The quantum dot solution 5mL being scattered in chloroform synthesized in synthesis example 1 is added in centrifugal separating tube, ethyl alcohol is added 20mL makes its precipitating.Supernatant is removed by being centrifugated, the chloroform that 2mL is added in sediment disperses quantum dot, so O- (succinyl)-the O '-methyl polyethylene glycol 2 ' 000 (aldrich company) of 0.5g is added afterwards, in a nitrogen atmosphere with 60 DEG C Heating, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 515nm.
Synthesis example 3: the synthesis (Q-3) of green quantum dot
Reactor is added in indium acetate 0.4mmol (0.058g), palmitinic acid 0.6mmol (0.15g) and 1- octadecylene 20mL In, it is heated to 120 DEG C under vacuum.After 1 hour, the atmosphere in reactor is converted into nitrogen.After being heated to 280 DEG C, quickly Inject three (trimethyl silyl) phosphine (TMS3P) the mixed solution of 0.2mmol (58 μ L) and tri octyl phosphine 1.0mL, and carry out 1 Minute reaction.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, selenium (Se/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally mixed Object is closed react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, will be precipitated obtained by centrifuge separation into Row is filtered under diminished pressure, and is then dried under reduced pressure, and InP/ZnSe core-shell structure copolymer is formed.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, sulphur (S/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally to mix Object react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, is carried out being precipitated obtained by centrifuge separation It is filtered under diminished pressure, is then dried under reduced pressure, obtain the quantum dot of InP/ZnSe/ZnS nucleocapsid structure, so that it is scattered in chlorine later In imitative.
The maximum glow peak of the luminescent spectrum of resulting nano-quantum point is 526nm, and quantum dot solution 5mL is added and is centrifuged In separating pipe, ethyl alcohol 20mL, which is added, makes its precipitating.Supernatant is removed by centrifuge separation, is added 2mL's in sediment Chloroform disperses quantum dot, and (2- butoxy-ethyoxyl)-acetic acid of 0.50g is then added, and is added in a nitrogen atmosphere with 60 DEG C Heat, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 526nm.
Synthesis example 4: the synthesis (Q-4) of green quantum dot
The quantum dot solution 5mL being scattered in chloroform synthesized in synthesis example 3 is added in centrifugal separating tube, ethyl alcohol is added 20mL makes its precipitating.Supernatant is removed by being centrifugated, the chloroform that 2mL is added in sediment disperses quantum dot, so O- (succinyl)-the O '-methyl polyethylene glycol 2 ' 000 (aldrich company) of 0.5g is added afterwards, in a nitrogen atmosphere with 60 DEG C Heating, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 525nm.
Synthesis example 5: the synthesis (Q-5) of green quantum dot
Reactor is added in indium acetate 0.4mmol (0.058g), palmitinic acid 0.6mmol (0.15g) and 1- octadecylene 20mL In, it is heated to 120 DEG C under vacuum.After 1 hour, the atmosphere in reactor is converted into nitrogen.After being heated to 280 DEG C, quickly Inject three (trimethyl silyl) phosphine (TMS3P) the mixed solution of 0.2mmol (58 μ L) and tri octyl phosphine 1.0mL, and carry out It reacts within 1.5 minutes.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, selenium (Se/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally mixed Object is closed react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, will be precipitated obtained by centrifuge separation into Row is filtered under diminished pressure, and is then dried under reduced pressure, and InP/ZnSe core-shell structure copolymer is formed.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, sulphur (S/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally to mix Object react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, is carried out being precipitated obtained by centrifuge separation It is filtered under diminished pressure, is then dried under reduced pressure, obtain the quantum dot of InP/ZnSe/ZnS nucleocapsid structure, so that it is scattered in chlorine later In imitative.
The maximum glow peak of the luminescent spectrum of resulting nano-quantum point is 526nm, and quantum dot solution 5mL is added and is centrifuged In separating pipe, ethyl alcohol 20mL, which is added, makes its precipitating.Supernatant is removed by centrifuge separation, is added 2mL's in sediment Chloroform disperses quantum dot, the carboxyl-EG6- undecane thiol (aldrich company) of 0.65g is then added, in nitrogen atmosphere Under with 60 DEG C heat, while carry out 1 hour react.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 536nm.
Synthesis example 6: the synthesis (Q-6) of green quantum dot
The quantum dot solution 5mL being scattered in chloroform synthesized in synthesis example 5 is added in centrifugal separating tube, ethyl alcohol is added 20mL makes its precipitating.Supernatant is removed by being centrifugated, the chloroform that 2mL is added in sediment disperses quantum dot, so O- (succinyl)-the O '-methyl polyethylene glycol 2 ' 000 (aldrich company) of 0.5g is added afterwards, in a nitrogen atmosphere with 60 DEG C Heating, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, will precipitate After object separation, propylene glycol monomethyl ether 4mL is put into, is heated with 80 DEG C, while being dispersed.Using PGMEA by solid Composition adjustment is to 25%.Maximum luminous wavelength is 534nm.
Synthesis example 7: the synthesis (Q-7) of red quantum dot
Reactor is added in indium acetate 0.4mmol (0.058g), palmitinic acid 0.6mmol (0.15g) and 1- octadecylene 20mL In, it is heated to 120 DEG C under vacuum.After 1 hour, the atmosphere in reactor is converted into nitrogen.After being heated to 280 DEG C, quickly Inject three (trimethyl silyl) phosphine (TMS3P) the mixed solution of 0.2mmol (58 μ L) and tri octyl phosphine 1.0mL, and carry out 5 Minute reaction, is then quickly cooled to room temperature for reaction solution.It shows and absorbs 560~590nm of maximum wavelength.
Zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, under vacuum It is heated to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is made to be warming up to 280 DEG C.It is added previous The InP core solution 2mL of synthesis, then, be added tri octyl phosphine in selenium (Se/TOP) 4.8mmol, then make final mixture into It reacts within row 2 hours, is down to room temperature later, form InP/ZnSe core-shell structure copolymer.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, sulphur (S/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally to mix Object react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, is carried out being precipitated obtained by centrifuge separation It is filtered under diminished pressure, is then dried under reduced pressure, obtain the quantum dot of InP/ZnSe/ZnS nucleocapsid structure, so that it is scattered in chlorine later In imitative.
The maximum glow peak of the luminescent spectrum of resulting nano-quantum point is 628nm, and the quantum dot solution 5mL of synthesis is added Enter in centrifugal separating tube, ethyl alcohol 20mL, which is added, makes its precipitating.Supernatant is removed by centrifuge separation, is added in sediment The chloroform of 2mL disperses quantum dot, and 2- [2- (2- methoxy ethoxy) ethyoxyl] acetic acid (He Guanggong of 0.65g is then added Department), it is heated in a nitrogen atmosphere with 60 DEG C, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, by supernatant Liquid removes after separating sediment, puts into propylene glycol monomethyl ether 4mL, is heated with 80 DEG C, while being dispersed.Benefit Solid component is adjusted to 25% with PGMEA.Maximum luminous wavelength is 628nm.
Synthesis example 8: the synthesis (Q-8) of red quantum dot
Reactor is added in indium acetate 0.4mmol (0.058g), palmitinic acid 0.6mmol (0.15g) and 1- octadecylene 20mL In, it is heated to 120 DEG C under vacuum.After 1 hour, the atmosphere in reactor is converted into nitrogen.After being heated to 280 DEG C, quickly Inject three (trimethyl silyl) phosphine (TMS3P) the mixed solution of 0.2mmol (58 μ L) and tri octyl phosphine 1.0mL, and carry out It reacts within 4.5 minutes, reaction solution is then quickly cooled to room temperature.It shows and absorbs 550~585nm of maximum wavelength.
Zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, under vacuum It is heated to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is made to be warming up to 280 DEG C.It is added previous The InP core solution 2mL of synthesis, then, be added tri octyl phosphine in selenium (Se/TOP) 4.8mmol, then make final mixture into It reacts within row 2 hours, is down to room temperature later, form InP/ZnSe core-shell structure copolymer.
Next, zinc acetate 2.4mmol (0.448g), oleic acid 4.8mmol and trioctylamine 20mL are added in reactor, Heating under vacuum is to 120 DEG C.After 1 hour, the atmosphere in reactor is converted into nitrogen, and reactor is warming up to 280 DEG C.Add Enter previously synthesized InP core solution 2mL, then, sulphur (S/TOP) 4.8mmol in tri octyl phosphine is added, then makes finally to mix Object react within 2 hours.Ethyl alcohol is added in the reaction solution for being quickly cooled to room temperature, is carried out being precipitated obtained by centrifuge separation It is filtered under diminished pressure, is then dried under reduced pressure, obtain the quantum dot of InP/ZnSe/ZnS nucleocapsid structure, so that it is scattered in chlorine later In imitative.
The maximum glow peak of the luminescent spectrum of resulting nano-quantum point is 616nm, and the quantum dot solution 5mL of synthesis is added Enter in centrifugal separating tube, ethyl alcohol 20mL, which is added, makes its precipitating.Supernatant is removed by centrifuge separation, is added in sediment The chloroform of 2mL disperses quantum dot, and 2- [2- (2- methoxy ethoxy) ethyoxyl] acetic acid (He Guanggong of 0.65g is then added Department), it is heated in a nitrogen atmosphere with 60 DEG C, while react within 1 hour.
Quantum dot is precipitated next, the n-hexane of 25mL is added in reactant, then implements centrifuge separation, by supernatant Liquid removes after separating sediment, puts into propylene glycol monomethyl ether 4mL, is heated with 80 DEG C, while being dispersed.Benefit Solid component is adjusted to 25% with PGMEA.Maximum luminous wavelength is 616nm.
Synthesis example 9: the adhesive resin (E-1) comprising Cardo system adhesive resin
(1) in the reactor, 9,9 '-bis- (4- glycidoxypropyl phenyl) fluorenes as bisphenol epoxy compound are added (Hear chem company) 138g, acrylic acid 54g, benzyltriethylammoinium chloride (great Jing Hua King Company) 1.4g, triphenylphosphine are (difficult to understand Delhi surprise company) 1g, methyl proxitol acetate (Daicel chemical company) 128g and quinhydrones 0.5g, it is warming up to 120 DEG C Afterwards, it maintains 12 hours, synthesizes compound represented by following chemical formula 11.
(2) in the reactor, compound 60g, bibenzene tetracarboxylic dianhydride (Mitsubishi watt represented by following chemical formula 11 is added This company) 11g, tetrabydrophthalic anhydride (aldrich company) 3g, methyl proxitol acetate (Daicel chemistry public affairs Department) 20g and N, N '-tetramethyl ammonium chloride 0.1g, it after being warming up to 120 DEG C, maintains 2 hours, synthesizes 12 tables of following chemical formula The compound shown.The weight average molecular weight of compound represented by resulting following chemical formula 12 is 5,400g/mol.Acid value is 95mgKOH/g。
[chemical formula 11]
[chemical formula 12]
Synthesis example 10: the adhesive resin (E-2) comprising Cardo system adhesive resin
(1) in order to synthesize the compound of following chemical formula 13, by 4,4 "-(9H- Xanthones in the three neck round bottom flask of 3000ml Ton -9,9- diyl) diphenol 364.4g and tert-butyl ammonium bromide 0.4159g mixing, be added epichlorohydrin 2359g, be heated to 90 DEG C into Row reaction.It is analyzed using liquid chromatogram, if 4,4 "-(9H- xanthene -9,9- diyl) diphenol are totally consumed, then cool down To 30 DEG C, it is slowly added 50%NaOH aqueous solution (3 equivalent).It is analyzed using liquid chromatogram, if epichlorohydrin is disappeared completely Consumption after then being extracted with methylene chloride, carries out 3 washings, then by after organic layer magnesium sulfate drying, methylene chloride is depressurized and is steamed It evaporates, is recrystallized using the methylene chloride and methanol of mixing ratio 50:50.
By 1 equivalent of epoxide synthesized in this way and 0.004 equivalent of tert-butyl ammonium bromide, 2,6- diisobutyl phenol After 0.001 equivalent, the mixing of 2.2 equivalent of acrylic acid, solvent propylene glycol monomethyl ether acetate 24.89g is added and mixes.It is anti-at this It answers in solution and air is blown into 25ml/min on one side, temperature is heated to 95 DEG C on one side and is dissolved.Become gonorrhoea in reaction solution In the state of temperature be heated to 120 DEG C make it completely dissolved.If solution went clear, viscosity are got higher, acid value is measured, is stirred It is less than 1.0mgKOH/g to acid value.Acid value needs 11 hours until reaching target (0.8).After reaction, by the temperature of reactor Degree is down to room temperature, obtains colorless and transparent compound.
[chemical formula 13]
(2) propylene glycol monomethyl ether 600g is added in the compound 307.0g of above-mentioned chemical formula 13 and is dissolved Afterwards, bibenzene tetracarboxylic dianhydride 78g and tetraethylammonium bromide 1g is mixed, is slowly heated up, carries out reacting for 4 hours at 110 DEG C.Confirmation acid After anhydride group disappears, 1,2,3,6- tetrabydrophthalic anhydride 38.0g are mixed, carry out reacting for 6 hours at 90 DEG C, aggregate into Cardo It is adhesive resin.The disappearance of acid anhydrides is confirmed by IR spectrum.Acid value is 120mgKOH/g.
Synthesis example 11: the adhesive resin (E-3) comprising Cardo system adhesive resin
(1) after reflux condenser and thermometer being set to three-necked flask, it is added 9,9- bisphenol fluorene 42.5g, and by 2- (chloromethane Base) it injects after ethylene oxide 220mL is quantitative.After tetrabutylammonium bromide 100mg is added, start to stir, while temperature being warming up to 90℃.After the content of confirmation unreacted reactant is less than 0.3%, it is evaporated under reduced pressure.
After cooling the temperature to 30 DEG C, methylene chloride is injected, and slowly put into NaOH.Utilize high performance liquid chromatography (HPLC) side After method confirms that product is 96% or more, 5%HCl, which is added dropwise, terminates reaction.After reactant is extracted and carries out layer separation, will have Machine layer is washed, and washing is to as neutrality.Organic layer MgSO4After drying, it is evaporated under reduced pressure and is concentrated using rotary evaporator. Methylene chloride is added in the product of concentration, temperature is risen to 40 DEG C, while putting into methanol while stirring, it then will be molten Liquid temperature is reduced and is stirred.After solid generated filtering, it is dried in vacuo in room temperature, obtains white solid powder 52.7g (yield 94%).Confirmed about its structure by 1H NMR.
[reaction equation 1]
1H NMR (CDCl3): 7.75 (2H), 7.35-7.254 (6H), 7.08 (4H), 6.74 (4H), 4.13 (2H), 3.89 (2H), 3.30 (2H), 2.87 (2H), 2.71 (2H).
(2) 3,3 '-(((9H- fluorenes -9,9- diyl) bis- (4,1- phenylenes)) bis- (oxygen)) bis- (1- thiophenyl) propane -2- Alcohol) synthesis
After reflux condenser and thermometer are set to three-necked flask, reactant (1000g), the benzenethiol in (1) stage is added 524g, ethyl alcohol 617g are simultaneously stirred.Triethylamine 328g is slowly added dropwise in reaction solution.Pass through high performance liquid chromatography (HPLC) method After confirming that initial substance disappears, reaction was completed.After reaction, ethyl alcohol is evaporated under reduced pressure and is removed.Organic matter is dissolved in two It after chloromethanes, is washed with water, methylene chloride is then passed through into vacuum distillation removal.The organic matter of concentration is dissolved in ethyl acetate Afterwards, ether solvent is added dropwise, and stir within 30 minutes.Compound is evaporated under reduced pressure, faint yellow oil 945g (yield 64%) is obtained, Its structure is confirmed by 1H NMR.
[reaction equation 2]
1H NMR (CDCl3): 7.82 (2H), 7.38-6.72 (20H), 6.51 (4H), 4.00 (2H), 3.97 (2H), 3.89 (2H), 3.20 (2H), 3.01 (2H), 2.64 (2H).
(3) synthesis of adhesive resin
After reflux condenser and thermometer is arranged to three-necked flask, addition was dissolved in (2) stage of 50%PGMEA solvent 3,3 '-(((9H- fluorenes -9,9- diyl) bis- (4,1- phenylenes)) bis- (oxygen)) bis- (1- thiophenyl) propane -2- alcohol of synthesis) monomer 200g is warming up to 115 DEG C.After 115 DEG C of 3,3 ', 4,4 '-bibenzene tetracarboxylic dianhydride 31.1g of dropwise addition, 115 DEG C, 6 hours are maintained, It is stirred simultaneously.Phthalic anhydride 7.35g, which is added, terminates reaction after futher stirring 2 hours.After cooling, weight is obtained Average molecular weight is the adhesive resin of 3,500g/mol.Acid value is 150mgKOH/g.
Synthesis example 12: the adhesive resin (E-4) comprising the acrylic adhesive resin containing epoxy group
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 2g, acrylic acid 18g, to vinyl Toluene 37.9g, methyl methacrylate 10g, glycidyl methacrylate 34.1g, n-dodecane mercaptan 3g, and carry out nitrogen Gas displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 140mgKOH/g, is about 13,110 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 13: the adhesive resin (E-5) comprising the acrylic adhesive resin containing epoxy group
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 2g, acrylic acid 15g, to vinyl Toluene 15.0g, methyl methacrylate 20g, glycidyl methacrylate 50.0g, n-dodecane mercaptan 3g, and carry out nitrogen Gas displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 115mgKOH/g, is about 13,110 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 14: the adhesive resin (E-6) comprising the acrylic adhesive resin containing epoxy group
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 2g, acrylic acid 16g, to vinyl Toluene 14.0g, methyl methacrylate 20g, 7- oxabicyclo [4.1.0] heptane -3- methyl acrylate 50.0g, positive ten Two alkanethiol 3g, and carry out nitrogen displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 125mgKOH/g, is about 11,110 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 15: the adhesive resin (E-7) comprising the acrylic adhesive resin containing epoxy group
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 3.5g, acrylic acid 16g, to ethylene Base toluene 14.0g, methyl methacrylate 20g, glycidyl methacrylate 20.0g, 7- oxabicyclo [4.1.0] heptan Alkane -3- methyl acrylate 20.0g, n-dodecane mercaptan 3g, and carry out nitrogen displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 98mgKOH/g, is about 8,090 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 16: the synthesis of the adhesive resin (E-8) comprising the acrylic adhesive resin containing epoxy group
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 1.2g, acrylic acid 16g, to ethylene Base toluene 14.0g, methyl methacrylate 20g, 3- vinyl -7- oxa--bicyclic [4.1.0] heptane 50.0g, n-dodecane sulphur Alcohol 1.5g, and carry out nitrogen displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 98mgKOH/g, is about 18,090 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 17: adhesive resin (E-9)
Propylene glycol is put into the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe Monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 2g, acrylic acid 5g, methacrylic acid Benzyl ester 35.0g, methyl methacrylate 60g, n-dodecane mercaptan 3g, and carry out nitrogen displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 40mgKOH/g, is about 12,370 by the weight average molecular weight Mw that GPC is measured.
Synthesis example 18: adhesive resin (E-10)
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, investment the third two Alcohol monomethyl ether acetate 120g, propylene glycol monomethyl ether 80g, 2,2 '-azodiisobutyronitrile 2g, acrylic acid 20g, metering system Acid benzyl ester 30.0g, methyl methacrylate 50g, n-dodecane mercaptan 3g, and carry out nitrogen displacement.
Later, so that the temperature of reaction solution is risen to 80 DEG C while stirring, and react within 8 hours.So synthesize The acid value of the solid component of adhesive resin is 160mgKOH/g, is about 11,874 by the weight average molecular weight Mw that GPC is measured.
The manufacture of light conversion resin combination: Examples 1 to 24 and comparative example 1~7
Using the ingredient and content (weight %) of following table 1~table 3, the light for manufacturing embodiment and comparative example converts resin Composition.
[table 1]
[table 2]
[table 3]
Experimental example
Light conversion coating is manufactured as follows using the light conversion resin combination manufactured in above-described embodiment and comparative example, and logical Cross brightness, light sustainment rate, colorrendering quality, heat resistance and the hardness of film of method measurement as described below at this time, evaluation As a result it is recorded in following table 4.
(1) manufacture of light conversion coating
Use the light conversion resin combination manufacture film manufactured in embodiment and comparative example.That is, will be upper by spin-coating method It states after each light conversion resin combination is coated on the glass substrate of 5cm × 5cm, is placed in heating plate, in 100 DEG C of temperature Degree maintains 10 minutes after forming film, carries out heating for 30 minutes in 180 DEG C of heated oven, manufacture light conversion coating.It closes In the thickness of the light conversion resin film of above-mentioned manufacture, 10 μ 0 of thickness is made according to the content of quantum dot.
(2) evaluation of brightness
The film manufactured in above-mentioned (1) is placed in blue-light source, and (XLamp XR-E LED, Royal blue 450, section is sharp Company) top after, use brightness tester (CAS140CT Spectrometer, Instrument systems company) survey Determine brightness, evaluation result is recorded in following table 4.
(3) light sustainment rate
The coated substrate made by the manufacturing method of above-mentioned smooth conversion coating is carried out to hard baking in 60 minutes at 230 DEG C (Hard bake), luminous efficiency and the luminous efficiency after hard dry, confirmation before measuring hard dry maintain the level of luminous efficiency, by Its evaluation result is recorded in following table 4.
(4) evaluation of heat resistance
After forming film by above-mentioned (1), the variation of the thickness after thermal shock is confirmed using following numerical expressions 1.Specifically, 1 hour 230 DEG C of heat is applied to the film being finally completed, front/rear thickness is heated in measurement, calculates and becomes by following mathematical expressions 1 Rate.At this point, be bad (×) when less than 90% for good (zero) if the change rate of thickness is 90% or more, Evaluation result is recorded in following table 4.
[mathematical expression 1]
The shrinking percentage of film={ (film thickness after heat treatment)/(film thickness before heat treatment) } × 100 (%)
(5) hardness of film
Use hardometer (HM500；Fei Xier company product) in the middle film manufactured of 150 DEG C of pyrometries above-mentioned (1) Curing degree, surface hardness evaluated based on following benchmark.The results are shown in following table 2.
< evaluation criteria >
Zero: surface hardness is 50 or more
△: surface hardness is 30 more than and less than 50
×: surface hardness is less than 30
(6) colorrendering quality
The film manufactured in above-mentioned (1) is placed in blue-light source, and (XLamp XR-E LED, Royal blue 450, section is sharp Company) top, place on it be formed with red, green, blue color patterns filter substrate (using UN65, Samsung The TV colour filter of company) after, using determination of colority device (OSP-200, Olympus Corp), red, green, blue the color of measurement Coordinate, calculates area ratio of the color reproduction region shown at this time relative to NTSC color region, and evaluation result is recorded in down It states in table 4.
[table 4]
Referring to above-mentioned table 4, include Cardo system adhesive resin and the tree of acrylic adhesive containing epoxy group in of the invention In the case where the embodiment of rouge, hardness of film and heat resistance are observed that very excellent performance relative to comparative example, from this The result of sample is it is found that the rupture of the evaporation film occurred in the heat treatment procedure imported when making display can be greatly reduced It is bad.
In addition, the difference of the centre of luminescence wavelength of the quantum dot of the embodiment of the present invention is 50nm or more, in application with green Color emission wavelength is 510nm~540nm, emitting red light central wavelength is two or more quantum that 610nm~630nm is characterized It in the case where point, is able to confirm that colorrendering quality is very excellent, but using a kind of quantum dot, and is applying In the case where quantum dot of the difference of centre of luminescence wavelength less than 50nm, it can be confirmed due to the performance of colorrendering quality deficiency It is difficult to use in the light source of colour filter.Moreover, additionally it is possible to confirm the enhanced strength with film, the brightness of embodiment and light Sustainment rate is obvious excellent compared with comparative example.

Claims (13)

1. a kind of light converts resin combination, which is characterized in that differ two kinds of 50nm or more each other comprising centre of luminescence wavelength Above quantum dot and adhesive resin,
Described adhesive resin includes Cardo system adhesive resin and acrylic adhesive resin containing epoxy group,
The quantum dot includes the polyethylene glycol system ligand for being configured at surface,
Polyethylene glycol system ligand includes compound represented by following chemical formula 1-A,
Chemical formula 1-A
In the chemical formula 1-A,
R ' indicates by chemical formula 1-1,
Chemical formula 1-1
*-R1-O-R2
In the chemical formula 1-1,
R1 is to be directly connected to or the alkylidene of carbon atom number 1~10,
R2 indicates by chemical formula 1-2,
Chemical formula 1-2
In the chemical formula 1-2,
A be oxygen atom or sulphur atom,
R3 is to be directly connected to or the alkylidene of carbon atom number 1~10,
B is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphate Or amido (- NH2),
R " is hydrogen atom, sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that k is 1~100,
The integer that l is 0~1,
The integer that m is 0~10.
2. light according to claim 1 converts resin combination, which is characterized in that change represented by the chemical formula 1-A Close object is indicated by following chemical formula 1-3,
Chemical formula 1-3
In the chemical formula 1-3,
R " is sulfydryl (*-SH), carboxylic acid groupMethyl-carbithionic acid basePhosphateAmido (- NH2), the branched alkyl of the straight chained alkyl of carbon atom number 1~20 or carbon atom number 3~20,
The integer that o is 0~5,
The integer that p is 0~1,
The integer that q is 1~50.
3. light according to claim 1 converts resin combination, which is characterized in that the quantum dot is non-cadmium system quantum Point.
4. light according to claim 1 converts resin combination, which is characterized in that the quantum dot includes core and shell,
The core include selected from one of group for being made of Was Used compound, three element compounds and four element compounds with On substance, the Was Used compound be selected from by GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, The group of InAs, InSb and their mixture composition；Three element compound be selected from by GaNP, GaNAs, GaNSb, GaPAs、GaPSb、AlNP、AlNAs、AlNSb、AlPAs、AlPSb、InNP、InNAs、InNSb、InPAs、InPSb、GaAlNP And the group of their mixture composition；Four element compound be selected from by GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb、GaInNP、GaInNAs、GaInNSb、GaInPAs、GaInPSb、InAlNP、InAlNAs、InAlNSb、 The group of InAlPAs, InAlPSb and their mixture composition,
The shell includes the substance selected from one or more of ZnSe, ZnS and ZnTe.
5. light according to claim 1 converts resin combination, which is characterized in that the quantum dot includes centre of luminescence wave The long two or more quantum dots for differing 70nm or more each other.
6. light according to claim 5 converts resin combination, which is characterized in that the quantum dot includes selected from by shining The range of green quantum dot and centre of luminescence wavelength that the range of central wavelength is 510nm~540nm is 610nm~630nm's It is two or more in the group of red quantum dot composition.
7. light according to claim 1 converts resin combination, which is characterized in that polyethylene glycol system ligand includes choosing Free 2- (2- methoxy ethoxy) acetic acid, 2- [2- (2- methoxy ethoxy) ethyoxyl] acetic acid, mono succinate-[2- (2- first Oxygroup-ethyoxyl)-ethyl] ester, mono- [2- (the 2- Mehtoxy-ethoxy)-ethyl] ester of malonic acid, the mono- { 2- [2- (2- of glutaric acid Ethoxy-ethoxy)-ethyoxyl]-ethyl } ester, { 2- [2- (2- ethyl-hexyloxy)-ethyoxyl]-ethyoxyl }-acetic acid, amber Mono- [2- (2- { 2- [2- (2- { 2- [2- (2- ethoxy-ethoxy)-ethyoxyl]-ethyoxyl }-the ethyoxyl)-ethoxy of amber acid Base]-ethyoxyl }-ethyoxyl)-ethyl] ester, mono succinate-[2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- methoxyl group- Ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethoxy Base)-ethyl] ester, mono- [2- (2- { 2- [2- (2- { 2- [2- (2- isobutoxy-ethyoxyl)-the ethyoxyl]-ethoxy of malonic acid Base }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] ester, mono- [2- (2- { 2- [2- (the 2- methoxyl group-second of adipic acid Oxygroup)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] ester, 2- oxo-adipic acid 6- (2- { 2- [2- (2- ethyoxyl-ethoxy Base)-ethyoxyl]-ethyoxyl }-ethyl) ester, mono succinate-[2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- { 2- [2- (2- Mehtoxy-ethoxy)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-second Oxygroup]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyoxyl]-ethyoxyl }-ethyoxyl)-ethyl] Ester, (2- butoxy-ethyoxyl)-acetic acid, carboxyl-EG6- undecane thiol and (2- Carboxvmethoxv-ethyoxyl)-acetic acid composition One or more of group.
8. light according to claim 1 converts resin combination, which is characterized in that the bonding of acrylic acid series containing epoxy group Agent resin includes at least one of 2~chemical formula of following chemical formula 4 repetitive unit,
Chemical formula 2
Chemical formula 3
Chemical formula 4
In the chemical formula 2~4,
R4, R5 and R6 are each independently hydrogen or methyl.
9. light according to claim 1 converts resin combination, which is characterized in that the Cardo system adhesive resin packet Containing at least one of 5~chemical formula of following chemical formula 10 repetitive unit,
Chemical formula 5
Chemical formula 6
Chemical formula 7
Chemical formula 8
In the chemical formula 5~8,
X and X ' is each independently singly-bound ,-CO- ,-SO2-、-C(CF3)2-、-Si(CH3)2-、-CH2-、-C(CH3)2-、-O-、
Y is anhydride residue,
Z is acid dianhydride residue,
R " ' is hydrogen atom, ethyl, phenyl ,-C2H4Cl、-C2H4OH or-CH2CH=CH2,
R7, R7 ', R8, R8 ', R9, R9 ', R10, R10 ', R11, R11 ', R12 and R12 ' are each independently hydrogen atom or methyl,
R13, R13 ', R14 and R14 ' are each independently the straight-chain alkyl-sub of carbon atom number 1~6 or the branch of carbon atom number 3~6 Chain alkylidene, the alkylidene can be by ester bonds, the arlydene of the cycloalkylidene of carbon atom number 6~14 and carbon atom number 6~14 At least one of interrupt,
R15, R15 ', R16, R16 ', R17, R17 ', R18 and R18 ' are each independently hydrogen atom, halogen atom or carbon atom number 1~6 straight chained alkyl or the branched alkyl of carbon atom number 3~6,
R and s is respectively the integer for meeting 0≤m≤30,0≤n≤30,
Wherein, r and s is not 0 simultaneously,
Chemical formula 9
Chemical formula 10
In the chemical formula 9 and 10,
P is each independently
R19 and R20 is each independently hydrogen, hydroxyl, mercapto, amino, nitro or halogen atom,
Ar1 is each independently the aryl of C6~C15,
Y ' is anhydride residue,
Z ' is acid dianhydride residue,
A ' be O, S, N, Si or Se,
A and b is each independently 1~6 integer,
C and d is each independently 0~30 integer,
Wherein, c and d is not 0 simultaneously.
10. light according to claim 1 converts resin combination, which is characterized in that the light convert resin combination into One step include selected from one of group for being made of scattering particles, heat-curable compounds, curing accelerator, additive and solvent with On.
11. a kind of light conversion layer folds substrate, it includes light according to any one of claims 1 to 10 conversion resin combinations Solidfied material.
12. light conversion layer according to claim 11 folds substrate, which is characterized in that the light conversion layer folds the material of substrate For glass.
13. a kind of image display device, it includes the light conversion layers described in claim 11 to fold substrate.
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