JP7032457B2 - 量子ドット、これを含む硬化性組成物、前記組成物を用いて製造された硬化膜、前記硬化膜を含むカラーフィルタ、ディスプレイ装置、および前記硬化膜の製造方法 - Google Patents
量子ドット、これを含む硬化性組成物、前記組成物を用いて製造された硬化膜、前記硬化膜を含むカラーフィルタ、ディスプレイ装置、および前記硬化膜の製造方法 Download PDFInfo
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- JP7032457B2 JP7032457B2 JP2020006250A JP2020006250A JP7032457B2 JP 7032457 B2 JP7032457 B2 JP 7032457B2 JP 2020006250 A JP2020006250 A JP 2020006250A JP 2020006250 A JP2020006250 A JP 2020006250A JP 7032457 B2 JP7032457 B2 JP 7032457B2
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
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- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2014—Contact or film exposure of light sensitive plates such as lithographic plates or circuit boards, e.g. in a vacuum frame
- G03F7/2016—Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing
- G03F7/2018—Masking pattern obtained by selective application of an ink or a toner, e.g. ink jet printing
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B2207/00—Coding scheme for general features or characteristics of optical elements and systems of subclass G02B, but not including elements and systems which would be classified in G02B6/00 and subgroups
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Description
R1~R7はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基または置換もしくは非置換の炭素数6~20のアリール基であり、
L1~L16はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n1~n7はそれぞれ独立して、0~10の整数である。
R8およびR9はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基であり、
L17~L23はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n8~n10はそれぞれ独立して、0~10の整数である。
R10~R15はそれぞれ独立して、水素原子または置換もしくは非置換の炭素数1~10のアルキル基であり、
L24~L29はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n11~n16はそれぞれ独立して、0~10の整数である。
R16~R18はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基であり、
L30~L32はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n17~n19はそれぞれ独立して、0~10の整数である。
R19およびR20はそれぞれ独立して、水素原子または置換もしくは非置換の炭素数1~10のアルキル基であり、
L33およびL35はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
L34は、置換もしくは非置換の炭素数1~10のアルキレン基またはエーテル基である。
R1~R7はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基または置換もしくは非置換の炭素数6~20のアリール基であり、
L1~L16はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n1~n7はそれぞれ独立して、0~10の整数である。
R8およびR9はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基であり、
L17~L23はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n8~n10はそれぞれ独立して、0~10の整数である。
R10~R15はそれぞれ独立して、水素原子または置換もしくは非置換の炭素数1~10のアルキル基であり、
L24~L29はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n11~n16はそれぞれ独立して、0~10の整数である。
R16~R18はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基であり、
L30~L32はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n17~n19はそれぞれ独立して、0~10の整数である。
前記無溶媒型硬化性組成物に含まれる量子ドットとして前記化学式1~化学式14で表される化合物のうちのいずれか一つまたはこれらの組み合わせで表面改質された量子ドットを使用することができるが、必ずしもこれに限定されるのではない。
前記末端に炭素-炭素二重結合を有する単量体は、前記無溶媒型硬化性組成物総量に対して40重量%~80重量%で含まれなければならない。例えば、前記末端に炭素-炭素二重結合を有する単量体は、前記無溶媒型硬化性組成物総量に対して50重量%~80重量%で含まれ得る。前記末端に炭素-炭素二重結合を有する単量体の含量が前記範囲内であってこそ、インクジェッティングが可能な粘度を有する無溶媒型硬化性組成物の製造が可能であり、また製造された無溶媒型硬化性組成物内量子ドットが優れた分散性を有することができ、光特性も向上できる。
R19およびR20はそれぞれ独立して、水素原子または置換もしくは非置換の炭素数1~10のアルキル基であり、
L33およびL35はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
L34は、置換もしくは非置換の炭素数1~10のアルキレン基またはエーテル基(*-O-*)である。
一実施形態による無溶媒型硬化性組成物は重合開始剤をさらに含むことができ、例えば、光重合開始剤、熱重合開始剤またはこれらの組み合わせを含むことができる。
一実施形態による無溶媒型硬化性組成物は、光拡散剤をさらに含むことができる。
前記量子ドットの安定性および分散性向上のために、一実施形態による無溶媒型硬化性組成物は重合禁止剤をさらに含むことができる。
前記バインダー樹脂は、アクリル系樹脂(アクリル系バインダー樹脂ともいう)、カルド系樹脂、エポキシ樹脂またはこれらの組み合わせを含むことができる。
R31およびR32はそれぞれ独立して、水素原子または置換もしくは非置換の(メタ)アクリロイルオキシアルキル基であり、
R33およびR34はそれぞれ独立して、水素原子、ハロゲン原子または置換もしくは非置換の炭素数1~20のアルキル基であり、
Z1は、単一結合、O、CO、SO2、CR35R36、SiR37R38(ここで、R35~R38はそれぞれ独立して、水素原子または置換もしくは非置換の炭素数1~20のアルキル基である)または下記化学式16-1~化学式16-11で表される連結基のうちのいずれか一つであり、
Raは、水素原子、エチル基、C2H4Cl、C2H4OH、CH2CH=CH2またはフェニル基である。
t1およびt2はそれぞれ独立して、0~4の整数である。
Z3は、下記化学式17-1~化学式17-7で表され得る。
前記溶媒は、例えば、メタノール、エタノールなどのアルコール類;エチレングリコールメチルエーテル、エチレングリコールエチルエーテル、プロピレングリコールメチルエーテルなどのグリコールエーテル類;メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチルセロソルブアセテートなどのセロソルブアセテート類;メチルエチルカルビトール、ジエチルカルビトール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジエチルエーテルなどのカルビトール類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールプロピルエーテルアセテートなどのプロピレングリコールアルキルエーテルアセテート類;メチルエチルケトン、シクロヘキサノン、4-ヒドロキシ-4-メチル-2-ペンタノン、メチル-n-プロピルケトン、メチル-n-ブチルケトン、メチル-n-アミルケトン、2-ヘプタノンなどのケトン類;酢酸エチル、酢酸-n-ブチル、酢酸イソブチルなどの飽和脂肪族モノカルボン酸アルキルエステル類;メチルラクテート、エチルラクテートなどの乳酸アルキルエステル類;メチルヒドロキシアセテート、エチルヒドロキシアセテート、ブチルヒドロキシアセテートなどのヒドロキシ酢酸アルキルエステル類;メトキシメチルアセテート、メトキシエチルアセテート、メトキシブチルアセテート、エトキシメチルアセテート、エトキシエチルアセテートなどの酢酸アルコキシアルキルエステル類;メチル3-ヒドロキシプロピオネート、エチル3-ヒドロキシプロピオネートなどの3-ヒドロキシプロピオン酸アルキルエステル類;メチル3-メトキシプロピオネート、エチル3-メトキシプロピオネート、エチル3-エトキシプロピオネート、メチル3-エトキシプロピオネートなどの3-アルコキシプロピオン酸アルキルエステル類;メチル2-ヒドロキシプロピオネート、エチル2-ヒドロキシプロピオネート、プロピル2-ヒドロキシプロピオネートなどの2-ヒドロキシプロピオン酸アルキルエステル類;メチル2-メトキシプロピオネート、エチル2-メトキシプロピオネート、エチル2-エトキシプロピオネート、メチル2-エトキシプロピオネートなどの2-アルコキシプロピオン酸アルキルエステル類;メチル2-ヒドロキシ-2-メチルプロピオネート、エチル2-ヒドロキシ-2-メチルプロピオネートなどの2-ヒドロキシ-2-メチルプロピオン酸アルキルエステル類;メチル2-メトキシ-2-メチルプロピオネート、エチル2-エトキシ-2-メチルプロピオネートなどの2-アルコキシ-2-メチルプロピオン酸アルキルエステル類;2-ヒドロキシエチルプロピオネート、2-ヒドロキシ-2-メチルエチルプロピオネート、ヒドロキシエチルアセテート、メチル2-ヒドロキシ-3-メチルブタノエートなどのエステル類;またはピルビン酸エチルなどのケトン酸エステル類の化合物があり、またN-メチルホルムアミド、N,N-ジメチルホルムアミド、N-メチルホルムアニリド、N-メチルアセトアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、ジメチルスルホキシド、ベンジルエチルエーテル、ジヘキシルエーテル、アセチルアセトン、イソホロン、カプロン酸、カプリル酸、1-オクタノール、1-ノナノール、ベンジルアルコール、酢酸ベンジル、安息香酸エチル、シュウ酸ジエチル、マレイン酸ジエチル、γ-ブチロラクトン、エチレンカーボネート、プロピレンカーボネート、フェニルセロソルブアセテートなどが挙げられるが、これに限定されるのではない。
前記無溶媒型硬化性組成物は、インクジェット噴射方式で0.5~20μmの厚さで基板上に塗布するのが好ましい。前記インクジェット噴射は、各ノズル当り単一カラーのみ噴射して必要な色の数によって反復的に噴射することによってパターンを形成することができ、工程を減らすために必要な色の数を各インクジェットノズルを通じて同時に噴射する方式でパターンを形成することもできる。
前記得られたパターンを硬化させて画素を得ることができる。この時、硬化させる方法としては、熱硬化工程または光硬化工程を全て適用することができる。前記熱硬化工程は100℃以上の温度で加熱して硬化させるのが好ましく、さらに好ましくは100℃~300℃で加熱して硬化させることができ、より一層好ましくは160℃~250℃で加熱して硬化させることができる。前記光硬化工程は、190nm~450nm、例えば200nm~500nmのUV光線などの化学線を照射する。照射に使用される光源としては低圧水銀灯、高圧水銀灯、超高圧水銀灯、金属ハロゲン化物ランプ、アルゴンガスレーザなどを使用することができ、場合によってX線、電子線なども用いることができる。
前述の硬化性組成物を所定の前処理を行った基板上にスピンまたはスリットコート法、ロールコート法、スクリーン印刷法、アプリケータ法などの方法を使用して所望の厚さ、例えば2μm~10μmの厚さで塗布した後、70℃~90℃の温度で1分~10分間加熱して溶媒を除去することによって塗膜を形成する。
前記得られた塗膜に必要なパターン形成のために所定形態のマスクを介した後、190nm~450nm、例えば200nm~500nmのUV光線などの化学線を照射する。照射に使用される光源としては、低圧水銀灯、高圧水銀灯、超高圧水銀灯、金属ハロゲン化物ランプ、アルゴンガスレーザなどを使用することができ、場合によってX線、電子線なども用いることができる。
前記露光段階に続き、アルカリ性水溶液を現像液として用いて不必要な部分を溶解、除去することによって露光部分のみを残存させて画像パターンを形成させる。即ち、アルカリ現像液で現像する場合、非露光部は溶解され、イメージカラーフィルタパターンが形成される。
前記現像によって得られた画像パターンを耐熱性、耐光性、密着性、耐クラック性、耐化学性、高強度、保存安定性などの面で優れたパターンを得るために、再び加熱するか化学線照射などを行って硬化させることができる。
(製造例1)
3口丸底フラスコにマグネチックバーを入れて、量子ドット-CHA(cyclohexyl acetate:酢酸シクロヘキシル)溶液(固形分26wt%~27wt%)を計量投入した。ここに下記化学式Aで表されるリガンドを投入した。
化学式Aで表されるリガンドの代わりに下記化学式Eで表されるリガンドを使用したことを除いては製造例1と同様に行った。
化学式Aで表されるリガンドの代わりに下記化学式Kで表されるリガンドを使用したことを除いては製造例1と同様に行った。
化学式15-1で表される単量体の代わりに下記化学式15-3で表される単量体(ブチルジメタクリレート(Butyl dimethacrylate)、韓農化成社)を使用したことを除いては製造例1と同様に行った。
化学式15-1で表される単量体の代わりに末端に炭素-炭素二重結合を有していない単量体のOXT221(3-エチル-3{[(3-エチルオキセタン-3-イル)メトキシ]メチル}オキセタン;東亞合成株式会社製)を使用したことを除いては製造例1と同様に行った。
粒径分析器(Particle size analyzer)を用いて製造例1~製造例4および比較製造例1から製造された量子ドット分散液上の粒度をマイクロ粒度分析器(Micro Particle Size Analyzer)でそれぞれ3回ずつ測定して平均を求め、その結果を下記表1に示した。
(実施例1)
前記製造例1で得られた分散液を計量した後、前記化学式15-1で表される単量体と混合して希釈し、重合禁止剤(メチルヒドロキノン、東京化成工業株式会社(TOKYO CHEMICAL社)製;5wt% in 化学式2-1で表される単量体)を入れて5分間攪拌した。その次に光開始剤(TPO-L、ポリネトロン社製)を投入した後、光拡散剤(TiO2;SDT89、イリドス社製)を入れた。全体分散液を1時間攪拌して無溶媒型硬化性組成物を製造した。無溶媒型硬化性組成物総量に対して量子ドットは8重量%、化学式15-1で表される単量体は80重量%、重合禁止剤は1重量%、光開始剤は3重量%および光拡散剤は8重量%で含まれていた。
製造例1で得られた分散液の代わりに前記製造例2で得られた分散液を使用したことを除いては実施例1と同様に行って、無溶媒型硬化性組成物を製造した。
製造例1で得られた分散液の代わりに前記製造例3で得られた分散液を使用したことを除いては実施例1と同様に行って、無溶媒型硬化性組成物を製造した。
製造例1で得られた分散液の代わりに前記製造例4で得られた分散液を使用し、化学式15-1で表される単量体の代わりに前記化学式15-3で表される単量体を使用したことを除いては実施例1と同様に行って、無溶媒型硬化性組成物を製造した。
無溶媒型硬化性組成物総量に対して量子ドットは48重量%、化学式15-1で表される単量体は40重量%、重合禁止剤は1重量%、光開始剤は3重量%および光拡散剤は8重量%で含まれるようにしたことを除いては実施例2と同様に行って、無溶媒型硬化性組成物を製造した。
製造例1で得られた分散液の代わりに前記比較製造例1で得られた分散液を使用し、化学式15-1で表される単量体の代わりに前記末端に炭素-炭素二重結合を有していない単量体OXT221(3-エチル-3{[(3-エチルオキセタン-3-イル)メトキシ]メチル}オキセタン;東亞合成株式会社製)を使用したことを除いては実施例1と同様に行って、無溶媒型硬化性組成物を製造した。
無溶媒型硬化性組成物総量に対して量子ドットは50重量%、化学式15-1で表される単量体は38重量%、重合禁止剤は1重量%、光開始剤は3重量%および光拡散剤は8重量%で含まれるようにしたことを除いては実施例2と同様に行って、無溶媒型硬化性組成物を製造した。
無溶媒型硬化性組成物総量に対して量子ドットは6重量%、化学式15-1で表される単量体は82重量%、重合禁止剤は1重量%、光開始剤は3重量%および光拡散剤は8重量%で含まれるようにしたことを除いては実施例2と同様に行って、無溶媒型硬化性組成物を製造した。
実施例1~実施例5および比較例1~比較例3で製造された無溶媒型硬化性組成物をそれぞれガラス基板(G-1、G-2)またはイエローフォトレジスト(YPR)(Y-1、Y-2)の上にスピンコーティング機(Mikasa社製、Opticoat MS-A150、800rpm、5秒)を使用して約15μmの厚さで塗布し、窒素雰囲気下395nm UV露光器で5000mJ(83℃、10秒)で露光した。その後、積分球装備(QE-2100、otsuka electronics)に2cm×2cm単膜試片をローディングして、光吸収率および光効率を測定し、測定結果を下記表2~表9に示した。
実施例1~実施例5および比較例1~比較例3で製造された無溶媒型硬化性組成物に対する待機時間による吐出率を下記のような方法で評価して、その結果を下記表10に示した。
実施例1~実施例5および比較例1~比較例3で製造された無溶媒型硬化性組成物に対する待機時間による常温保存安定性を初期粘度値に対する時間経過後の粘度値の差で評価して、その結果を下記表11に示した。
(実施例6)
前記製造例1で得られた分散液を計量して量子ドット(23重量%)をジメチルアジペート(dimethyl adipate)(45重量%)に分散させた後、カルド系バインダー樹脂(TSR-TA01、TAKOMA社製)(8重量%)と混合して量子ドット分散液を製造した。その後、熱硬化性単量体としてOXT-221(3-エチル-3{[(3-エチルオキセタン-3-イル)メトキシ]メチル}オキセタン;東亞合成株式会社製)(1重量%)およびPFM-02(SMS社製)(16.5重量%)、光拡散剤(TiO2;SDT89、イリドス社製)(2重量%)、グリコールジ-3-メルカプトプロピオネート(BRUNO BOCK(ブルーノボック)社製)(4.2重量%)、重合禁止剤としてメチルヒドロキノン(東京化成工業株式会社(TCI)製)(0.3重量%)を混合し、ここに前記で製造した量子ドット分散液を投入、攪拌して溶媒型硬化性組成物を製造した。
下記に言及された構成成分を該当含量にして溶媒型硬化性組成物(感光性樹脂組成物)を製造した。
2)バインダー樹脂:カルド系バインダー樹脂(TSR-TA01、TAKOMA社製)25重量%
3)重合性単量体:ペンタエリトリトールヘキサメタクリレート(DPHA、日本化薬株式会社(Nippon Kayaku社)製)5.4重量%
4)光重合開始剤:ジフェニル(2,4,6-トリメチルベンゾイル)ホスフィンオキシド(TPO、Sigma-Aldrich社製)0.7重量%
5)溶媒:ジメチルアジペート(dimethyl adipate)39重量%
6)拡散剤:二酸化チタン分散液(TiO2固形分20重量%、平均粒径:200nm、ディットーテクノロジー株式会社製)15重量%
7)チオール添加剤:グリコールジ-3-メルカプトプロピオネート(BRUNO BOCK(ブルーノボック)社製)2重量%
8)その他の添加剤:フッ素系界面活性剤(F-554、DIC株式会社製)0.9重量%。
前記実施例6および実施例7で製造された溶媒型硬化性組成物をそれぞれガラス基板上にスピンコーティング機(Mikasa社製、Opticoat MS-A150、150rpm)を使用して2μmの厚さで単膜コーティングした後、熱板(hot-plate)を用いて80℃で1分間乾燥して塗膜を収得した後、初期青色光変換率を測定(第1段階)した。
Claims (16)
- 前記量子ドットは、500nm~680nmで最大蛍光発光波長を有する、請求項1に記載の量子ドット。
- 下記化学式3および化学式Kで表される化合物のうちのいずれか一つまたはこれらの組み合わせで表面改質された量子ドット、または請求項2に記載の量子ドット、および
末端に炭素-炭素二重結合を有する重合性単量体
を含み、
前記重合性単量体は、無溶媒型硬化性組成物総量に対して40重量%~80重量%で含まれる無溶媒型硬化性組成物;
上記化学式3中、
R 3 はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキル基または置換もしくは非置換の炭素数6~20のアリール基であり、
L 5 およびL 6 はそれぞれ独立して、置換もしくは非置換の炭素数1~10のアルキレン基であり、
n3はそれぞれ独立して、0~10の整数である。
- 前記重合性単量体は、220~1,000g/molの分子量を有する、請求項3に記載の無溶媒型硬化性組成物。
- 前記無溶媒型硬化性組成物は、重合開始剤、光拡散剤またはこれらの組み合わせをさらに含む、請求項3~5のいずれか1項に記載の無溶媒型硬化性組成物。
- 前記光拡散剤は、硫酸バリウム、炭酸カルシウム、二酸化チタン、ジルコニアまたはこれらの組み合わせを含む、請求項6に記載の無溶媒型硬化性組成物。
- 前記無溶媒型硬化性組成物は、重合禁止剤;マロン酸;3-アミノ-1,2-プロパンジオール;シラン系カップリング剤;レべリング剤;フッ素系界面活性剤;またはこれらの組み合わせをさらに含む、請求項6または7に記載の無溶媒型硬化性組成物。
- 前記溶媒型硬化性組成物は、重合性単量体、重合開始剤、光拡散剤またはこれらの組み合わせをさらに含む、請求項9に記載の溶媒型硬化性組成物。
- 前記溶媒型硬化性組成物は、感光性樹脂組成物である、請求項9または10に記載の溶媒型硬化性組成物。
- 請求項3~8のいずれか1項または請求項9~11のいずれか1項による組成物を用いて製造された硬化膜。
- 請求項12の硬化膜を含むカラーフィルタ。
- 請求項13のカラーフィルタを含むディスプレイ装置。
- 請求項3~8のいずれか1項または請求項9~11のいずれか1項による組成物を基板上にインクジェット噴射方法で塗布してパターンを形成する段階、および
前記パターンを硬化する段階
を含む硬化膜製造方法。 - 請求項3~8のいずれか1項または請求項9~11のいずれか1項による組成物を基板上に塗布後露光してパターンを形成する段階と、
前記パターンを現像する段階と、
前記現像後熱処理する段階と、
を含む硬化膜製造方法。
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