CN112639537A - Composition for lens, method for producing lens, and display device - Google Patents
Composition for lens, method for producing lens, and display device Download PDFInfo
- Publication number
- CN112639537A CN112639537A CN201980055711.XA CN201980055711A CN112639537A CN 112639537 A CN112639537 A CN 112639537A CN 201980055711 A CN201980055711 A CN 201980055711A CN 112639537 A CN112639537 A CN 112639537A
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- lens
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- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
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- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/875—Arrangements for extracting light from the devices
- H10K59/879—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- G—PHYSICS
- 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
-
- 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
- G03F7/027—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
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- G03F7/075—Silicon-containing compounds
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Electroluminescent Light Sources (AREA)
- Optical Filters (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The invention provides a composition for a lens for forming a lens on an optical path of light transmitting a color filter of a display device having the color filter, a lens using the composition for the lens, a method for manufacturing the lens, and a display device. The lens composition comprises a polymerizable monomer M, a photopolymerization initiator A and a resin B. When a film having a thickness of 2 μm is produced using the lens composition, the maximum value of the absorbance of the film at a wavelength of 400 to 700nm is 0.05 or less, and the refractive index of the film at a wavelength of 550nm is 1.5 or more.
Description
Technical Field
The present invention relates to a composition for a lens. More particularly, the present invention relates to a lens composition for forming a lens on an optical path of light transmitted through a color filter in a display device having the color filter. The present invention also relates to a lens, a method of manufacturing the lens, and a display device.
Background
In various display devices, color filters are generally used for colorizing a display image. For example, patent document 1 describes the following: a color filter is formed using a photosensitive composition for a color filter, which contains a compound (A) containing a furyl group, a compound (B) containing a photopolymerizable functional group, a photopolymerization initiator (C), and a colorant, and an organic electroluminescent display device is manufactured.
Prior art documents
Patent document
Patent document 1: japanese patent laid-open publication No. 2017-194662
Disclosure of Invention
Technical problem to be solved by the invention
In recent years, further improvement in luminance of a display device has been desired. The present inventors have conducted various studies to further improve the luminance of a display device having a color filter, and have found that the luminance can be improved by providing a lens on the optical path of light transmitted through the color filter.
Accordingly, an object of the present invention is to provide a composition for a lens, a method for manufacturing a lens, and a display device, which can improve the luminance of a display device having a color filter.
Means for solving the technical problem
The present inventors provide the following.
< 1 > a composition for a lens for forming a lens on an optical path of light transmitted through a color filter of a display device having the color filter, wherein,
the composition for a lens comprises a polymerizable monomer M, a photopolymerization initiator A and a resin B,
when a film having a thickness of 2 μm is produced using the composition for a lens, the maximum value of the absorbance of the film at a wavelength of 400 to 700nm is 0.05 or less, and the refractive index of the film at a wavelength of 550nm is 1.5 or more.
< 2 > the composition for a lens as < 1 >, wherein the resin B contains a resin B1 comprising a repeating unit derived from a compound represented by the following formula (I),
[ chemical formula 1]
In the formula, X1Represents O or NH, and is selected from the group consisting of,
R1represents a hydrogen atom or a methyl group,
L1represents a linking group having a valence of 2,
R10represents a substituent group, and a pharmaceutically acceptable salt thereof,
m represents an integer of 0 to 2,
p represents an integer of 0 or more.
< 3 > the composition for a lens as < 2 >, wherein the resin b1 further comprises a repeating unit derived from an alkyl (meth) acrylate.
[ 4] the lens composition according to any one of [ 1] to [ 3], wherein the photopolymerization initiator A contains an oxime compound.
[ 5] the lens composition according to any one of [ 1] to [ 4], wherein the photopolymerization initiator A comprises:
an absorption coefficient of 1.0X 10 at a wavelength of 365nm in methanol3A photopolymerization initiator A1 of mL/gcm or more; and
an absorption coefficient of 1.0X 10 at a wavelength of 365nm in methanol2mL/gcm or less, and an absorption coefficient at a wavelength of 254nm of 1.0X 103A photopolymerization initiator A2 having a concentration of mL/gcm or more.
< 6 > the composition for a lens, wherein the photopolymerization initiator A1 is an oxime compound containing a fluorine atom, as < 5 >.
< 7 > such as < 5 > or < 6 > wherein the photopolymerization initiator A2 is a hydroxyalkylphenone compound.
The lens composition as defined in any one of < 8 > to < 5 > to < 7 >, wherein the photopolymerization initiator A2 is contained in an amount of 50 to 200 parts by mass based on 100 parts by mass of the photopolymerization initiator A1.
The lens composition as defined in any one of < 9 > to < 5 > to < 8 >, wherein the total content of the photopolymerization initiator A1 and the photopolymerization initiator A2 in the total solid content of the lens composition is 5 to 15% by mass.
[ 10] the lens composition according to any one of [ 1] to [ 9], wherein the polymerizable monomer M contains a compound containing 3 or more ethylenically unsaturated groups.
The composition for a lens described in any one of < 11 > to < 1 > to < 10 > which contains a silane coupling agent.
[ 12] the composition for a lens according to any one of [ 1] to [ 11], which comprises a compound containing a furyl group.
< 13 > the composition for a lens as < 12 >, wherein the compound containing a furyl group is at least 1 selected from the group consisting of a compound represented by the following formula (fur-1) and a resin containing a repeating unit derived from the compound represented by the following formula (fur-1),
[ chemical formula 2]
In the formula, Rf1Represents a hydrogen atom or a methyl group, Rf2Represents a 2-valent linking group.
< 14 > a lens obtained from the lens composition according to any one of < 1 > to < 13 >.
< 15 > a method for manufacturing a lens, comprising:
a step of applying the composition for a lens described in any one of < 1 > -to < 13 > to a support to form a composition layer; and
and a step of processing the composition layer into a lens shape.
< 16 > the method for producing a lens, wherein the entire process is carried out at a temperature of 150 ℃ or lower.
< 17 > such as < 15 > or < 16 >, wherein the step of shaping the lens comprises applying 1J/cm to the composition layer2And irradiating the light with an exposure amount of at least 350nm and at most 380 nm.
The method for manufacturing a lens, wherein the step of processing the lens into a lens shape includes a step of exposing the composition layer by irradiating light having a wavelength of more than 350nm and 380nm or less, and then further exposing the composition layer by irradiating light having a wavelength of 254 to 350 nm.
The method of manufacturing a lens according to any one of < 19 > to < 15 > to < 18 >, wherein the step of processing the composition layer into a lens shape includes a step of heating the composition layer at a temperature of 100 to 150 ℃ for 10 minutes or more.
< 20 > and < 19 > wherein the heating step is performed in an inert gas atmosphere.
< 21 > a display device having a color filter and a lens obtained from the composition for a lens described in any one of < 1 > -to < 13 > provided on an optical path of light transmitting the color filter.
< 22 > the display device as < 21 > which is an organic electroluminescent display device.
Effects of the invention
According to the present invention, a lens composition, a lens, and a method for manufacturing a lens, which can improve the luminance of a display device having a color filter, can be provided. Further, according to the present invention, a display device with high luminance can be provided.
Detailed Description
The present invention will be described in detail below.
In the labeling of the group (atomic group) in the present specification, the label not labeled with substitution and not substituted includes a group (atomic group) having no substituent and also includes a group (atomic group) having a substituent. For example, "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In the present specification, "exposure" includes not only exposure using light but also drawing using a particle beam such as an electron beam or an ion beam unless otherwise specified. The light used for exposure is generally an active light or radiation such as a bright line spectrum of a mercury lamp, a far ultraviolet ray typified by an excimer laser, an extreme ultraviolet ray (EUV light), an X-ray, and an electron beam.
In the present specification, the numerical range expressed by the term "to" means a range including the numerical values before and after the term "to" as the lower limit value and the upper limit value.
In the present specification, the total solid content means the total mass of all components of the composition excluding the solvent.
In the present specification, "(meth) acrylate" represents both or either of acrylate and methacrylate, "(meth) acrylic acid" represents both or either of acrylic acid and methacrylic acid, "(meth) allyl" represents both or either of allyl and methallyl, and "(meth) acryloyl" represents both or either of acryloyl and methacryloyl.
The term "step" in the present specification is not limited to an independent step, and is also included in the present term as long as a desired action of the step is achieved even when the term cannot be clearly distinguished from other steps.
In the present specification, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene equivalent values measured by Gel Permeation Chromatography (GPC).
< composition for lens >
The composition for a lens of the present invention is used for forming a lens on an optical path of light transmitted through a color filter in a display device having the color filter,
the lens composition comprises a polymerizable monomer M, a photopolymerization initiator A and a resin B,
when a film having a thickness of 2 μm is produced using the lens composition, the maximum value of the absorbance of the film at a wavelength of 400 to 700nm is 0.05 or less, and the refractive index of the film at a wavelength of 550nm is 1.5 or more.
By using the lens composition of the present invention, the luminance of a display device having a color filter can be further improved.
When the composition of the present invention is used for producing a film having a thickness of 2 μm, the maximum value of absorbance of the film at a wavelength of 400 to 700nm is 0.05 or less, preferably 0.04 or less, and more preferably 0.03 or less. In order to achieve such absorbance conditions, it is preferable to use a material having a small absorbance at a wavelength of 400 to 700nm, more preferably a material having a maximum value of absorbance at a wavelength of 400 to 700nm of 0.05 or less, and still more preferably a material having a maximum value of 0.03 or less as a material used in the lens composition. Further, when the composition of the present invention is used for producing a film having a thickness of 2 μm, the refractive index of the film at a wavelength of 550nm is 1.5 or more, preferably 1.52 or more, and more preferably 1.54 or more. The upper limit is preferably 2.0 or less, more preferably 1.85 or less. Such a condition of the refractive index can be achieved by including a material having a high refractive index at a wavelength of 550nm in the lens composition.
The composition of the present invention satisfies the above conditions of absorbance and refractive index, thereby reducing the loss of light amount and consequently further improving the luminance.
The composition for a lens of the present invention is preferably used for a color filter included in a display device, the color filter having a plurality of color pixels, and a lens being formed on an optical path of at least a part of the pixels.
The lens composition of the present invention will be described in detail below.
Polymerizable monomer
The lens composition of the present invention contains a polymerizable monomer. Examples of the polymerizable monomer include compounds having an ethylenically unsaturated group. Examples of the ethylenically unsaturated group include a vinyl group, (meth) allyl group, and (meth) acryloyl group. The polymerizable monomer is preferably a compound capable of radical polymerization (radical polymerizable monomer).
The molecular weight of the polymerizable monomer is preferably 100 to 2000. The upper limit is preferably 1500 or less, more preferably 1000 or less. The lower limit is more preferably 150 or more, and still more preferably 250 or more.
The ethylenically unsaturated group value (hereinafter referred to as C value) of the polymerizable monomer is preferably 2 to 14mmol/g from the viewpoint of the stability of the composition over time. The lower limit is preferably 3mmol/g or more, more preferably 4mmol/g or more, and still more preferably 5mmol/g or more. The upper limit is preferably 12mmol/g or less, more preferably 10mmol/g or less, and still more preferably 8mmol/g or less. The value of C ═ C of the polymerizable monomer was calculated by dividing the number of ethylenically unsaturated groups contained in 1 molecule of the polymerizable monomer by the molecular weight of the polymerizable monomer.
The polymerizable monomer is preferably a compound containing 3 or more ethylenically unsaturated groups, and more preferably a compound containing 4 or more ethylenically unsaturated groups. The upper limit of the number of ethylenically unsaturated groups is preferably 15 or less, more preferably 10 or less, and still more preferably 6 or less. The polymerizable monomer is preferably a (meth) acrylate compound having 3 or more functions.
The polymerizable monomer is also preferably a compound containing an ethylenically unsaturated group and an alkyleneoxy group. Such polymerizable monomers have high flexibility and are easy to move the ethylenically unsaturated group, and therefore the polymerizable monomers are easy to react with each other during exposure, and a lens having excellent adhesion to a support or the like can be formed. Further, when a hydroxyalkylphenone compound is used as a photopolymerization initiator, it is presumed that the polymerizable monomer can be more efficiently reacted by the polymerizable monomer being brought close to the photopolymerization initiator and generating radicals in the vicinity of the polymerizable monomer, and a lens having more excellent adhesiveness and solvent resistance can be easily formed.
The number of alkyleneoxy groups contained in 1 molecule of the polymerizable monomer is preferably 3 or more, and more preferably 4 or more. From the viewpoint of the stability of the composition over time, the upper limit is preferably 20 or less.
The SP value (Solubility Parameter) of the compound containing an ethylenically unsaturated group and an alkyleneoxy group is preferably 9.0 to 11.0 from the viewpoint of compatibility with other components in the composition. The upper limit is preferably 10.75 or less, more preferably 10.5 or less. The lower limit is preferably 9.25 or more, and more preferably 9.5 or more. In the present specification, the SP value is calculated by the Fedors method.
As the polymerizable monomer, dipentaerythritol triacrylate (KAYARAD D-330; NIPPON KAYAKU co., ltd., product), dipentaerythritol tetraacrylate (KAYARAD D-320; NIPPON KAYAKU co., product ltd., product D.), dipentaerythritol penta (meth) acrylate (KAYARAD D-310; NIPPON KAYAKU co., product D.), dipentaerythritol hexa (meth) acrylate (KAYARAD DPHA; NIPPON KAYAKU co., product D-DPH-12E; product f-NAKAMURA chemcal co., product D.), and a compound having a structure in which (meth) acryloyl groups thereof are bonded to each other via ethylene glycol and/or propylene glycol residues (e.g., SR454, SR499, product D., product c.). Further, as the polymerizable monomer, a 3-functional (meth) acrylate compound such as trimethylolpropane tri (meth) acrylate, trimethylolpropane-propylene oxide-modified tri (meth) acrylate, trimethylolpropane-ethylene oxide-modified tri (meth) acrylate, isocyanuric acid-ethylene oxide-modified tri (meth) acrylate, pentaerythritol tri (meth) acrylate, or the like can be used. Commercially available 3-functional (meth) acrylate compounds include ARONIX M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, M-450 (manufactured by TOAGOSEI CO., LTD.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, TMPT (Shin-Nakamura Chemical Co., manufactured by Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., manufactured by Ltd.) and THE like.
The polymerizable monomer may have an acid group. Examples of the acid group include a carboxyl group, a sulfo group, and a phosphate group, and a carboxyl group is preferable. Commercially available products of polymerizable monomers having an acid group include ARONIX M-510, M-520, and ARONIX TO-2349(TOAGOSEI CO., LTD., Ltd.).
The acid value of the polymerizable monomer having an acid group is preferably 0.1 to 40mgKOH/g, more preferably 5 to 30 mgKOH/g. The acid value of the polymerizable monomer is preferably not less than 0.1mgKOH/g, from the viewpoint of good solubility in a developer, and preferably not more than 40mgKOH/g, from the viewpoint of production or handling.
The polymerizable monomer is also preferably a compound having a caprolactone structure. Polymerizable compounds having a caprolactone structure are commercially available as KAYARAD DPCA series from, for example, NIPPON KAYAKU CO., Ltd., and examples thereof include DPCA-20, DPCA-30, DPCA-60 and DPCA-120.
As the polymerizable monomer, compounds described in Japanese patent laid-open Nos. 2017-048367, 6057891, 6031807, 2017-194662, 8UH-1006, 8UH-1012 (above, Taisei Fine Chemical Co., Ltd., manufactured by Ltd.), and Light-Acrylate POB-A0(KYOEISHA CHEMICAL Co., manufactured by LTD.) are also preferably used.
The content of the polymerizable monomer is preferably 10 to 60% by mass of the total solid content of the lens composition. The upper limit is preferably 55% by mass or less, more preferably 50% by mass or less. The lower limit is preferably 15% by mass or more, and more preferably 30% by mass or more.
Photopolymerization initiator
The lens composition of the present invention contains a photopolymerization initiator. Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds such as acylphosphine oxides, oxime compounds such as hexaarylbiimidazole compounds and oxime derivatives, organic peroxides, sulfur compounds, ketone compounds, aromatic onium salts, ketoxime ether compounds, aminoalkylphenone compounds, hydroxyalkylphenone compounds, and benzoylformate compounds. Specific examples of the photopolymerization initiator include those described in, for example, paragraphs 0265 to 0268 of Japanese patent laid-open publication No. 2013-029760 and Japanese patent laid-open publication No. 6301489, which are incorporated herein by reference.
Examples of the benzoylformate compound include methyl benzoylformate. The commercially available product may be DAROCUR-MBF (manufactured by BASF corporation).
Examples of the aminoalkyl phenone compound include the aminoalkyl phenone compounds described in Japanese patent application laid-open No. 10-291969. Also, IRGACURE-907, IRGACURE-369 and IRGACURE-379 (both manufactured by BASF) can be used as the aminoalkyl phenone compound.
The acylphosphine compound may be an acylphosphine compound described in japanese patent No. 4225898. Specific examples thereof include bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide and the like. As the acylphosphine compound, IRGACURE-819 or DAROCUR-TPO (both manufactured by BASF) can be used.
Examples of the hydroxyalkylphenone compound include compounds represented by the following formula (V).
Formula (V)
[ chemical formula 3]
In the formula Rv1Represents a substituent group, Rv2And Rv3Each independently represents a hydrogen atom or a substituent, Rv2And Rv3Or may be bonded to each other to form a ring, and m represents an integer of 0 to 5.
As Rv1Examples of the substituent include an alkyl group (preferably an alkyl group having 1 to 10 carbon atoms) and an alkoxy group (preferably an alkoxy group having 1 to 10 carbon atoms). The alkyl group and the alkoxy group are preferably straight-chain or branched, and more preferably straight-chain. Rv1The alkyl group and the alkoxy group may be unsubstituted or substituted. As a substitutionExamples of the group include a hydroxyl group and a group having a hydroxyalkylphenone structure. As the group having a hydroxyalkylphenone structure, there may be mentioned Rv in the formula (V)1Bound benzene ring or from Rv1Groups of structure which remove 1 hydrogen atom.
Rv2And Rv3Each independently represents a hydrogen atom or a substituent. The substituent is preferably an alkyl group (preferably an alkyl group having 1 to 10 carbon atoms). And, Rv2And Rv3The ring may be bonded to each other to form a ring (preferably a ring having 4 to 8 carbon atoms, more preferably an aliphatic ring having 4 to 8 carbon atoms). The alkyl group is preferably straight-chain or branched, more preferably straight-chain.
Specific examples of the compound represented by the formula (V) include the following compounds.
[ chemical formula 4]
As the hydroxyalkylphenone compounds, IRGACURE-184, DAROCUR-1173, IRGACURE-500, IRGACURE-2959, and IRGACURE-127 (product names: manufactured by BASF) can also be used.
Examples of oxime compounds include a compound described in Japanese patent laid-open No. 2001-233842, a compound described in Japanese patent laid-open No. 2000-080068, a compound described in Japanese patent laid-open No. 2006-342166, a compound described in J.C.S.Perkin II (1979, pp.1653-1660), a compound described in J.C.S.Perkin II (1979, pp.156-162), a compound described in Journal of Photopharmaceuticals Science and Technology (1995, pp.202-232), a compound described in Japanese patent laid-open No. 2000-066385, a compound described in Japanese patent laid-open No. 2004-534797, a compound described in Japanese patent laid-open No. 2006-342166, a compound described in Japanese patent laid-open No. 2017-019766, a compound described in Japanese patent laid-open No. 6065596, a compound described in Japanese patent laid-open No. 2015/152153, A compound described in International publication No. 2017/051680, a compound described in Japanese patent laid-open publication No. 2017-198865, a compound described in paragraphs 0025 to 0038 of International publication No. 2017/164127, and the like. Specific examples of the oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one. Commercially available products include IRGACURE-OXE01, IRGACURE-OXE02, IRGACURE-OXE03, IRGACURE-OXE04 (manufactured by BASF Co., Ltd.), TR-PBG-304(Changzhou Tronly Electronic Materials CO., manufactured by LTD.), Adeka Optomer N-1919 (photopolymerization initiator 2 described in ADEKA CORPORATION, Japanese patent application laid-open No. 2012 and 014052).
Further, as the oxime compound, a compound described in Japanese patent application laid-open No. 2009-519904 in which oxime is linked to the N-position of a carbazole ring, a compound described in U.S. Pat. No. 7626957 in which a hetero substituent is introduced into a benzophenone moiety, a compound described in Japanese patent application laid-open No. 2010-015025 and U.S. Pat. No. 2009-292039 in which a nitro group is introduced into a dye moiety, a ketoxime compound described in International publication No. 2009/131189, a compound described in U.S. Pat. No. 7556910 in which a triazine skeleton and an oxime skeleton are contained in the same molecule, a compound described in Japanese patent application laid-open No. 2009-221114 in which an absorption maximum is 405nm and which has excellent sensitivity to a g-line light source, and the like can be used. For example, reference can be made to paragraphs 0274 to 0306 of Japanese patent application laid-open No. 2013-029760, which is incorporated herein by reference.
The oxime compound is preferably an oxime compound containing a fluorine atom. The oxime compound containing a fluorine atom preferably has a group containing a fluorine atom. The group containing a fluorine atom is preferably an alkyl group having a fluorine atom (hereinafter, also referred to as a fluorine-containing alkyl group) or a group containing an alkyl group having a fluorine atom (hereinafter, also referred to as a fluorine-containing group). As fluorine-containing group, it is preferably selected from-ORF1、-SRF1、-CORF1、-COORF1、-OCORF1、-NRF1RF2、-NHCORF1、-CONRF1RF2、-NHCONRF1RF2、-NHCOORF1、-SO2RF1、-SO2ORF1and-NHSO2RF1At least 1 group. RF1Represents a fluorine-containing alkyl group, RF2Represents a hydrogen atom, an alkyl group, a fluoroalkyl group, an aryl group or a heterocyclic group. The fluorine-containing group is preferably-ORF1。
The alkyl group and the fluoroalkyl group preferably have 1 to 20, more preferably 1 to 15, further preferably 1 to 10, and particularly preferably 1 to 4 carbon atoms. The alkyl group and the fluorine-containing alkyl group may be any of linear, branched and cyclic, and are preferably linear or branched. In the fluoroalkyl group, the substitution rate of fluorine atoms is preferably 40 to 100%, more preferably 50 to 100%, and further preferably 60 to 100%. The substitution rate of fluorine atoms means a ratio (%) of the number of fluorine atoms substituted with fluorine atoms to the number of all hydrogen atoms of the alkyl group.
The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10.
The heterocyclic group is preferably a 5-membered ring or a 6-membered ring. The heterocyclic group may be a single ring or a condensed ring. The number of fusion is preferably 2 to 8, more preferably 2 to 6, further preferably 3 to 5, particularly preferably 3 to 4. The number of carbon atoms constituting the heterocyclic group is preferably 3 to 40, more preferably 3 to 30, and still more preferably 3 to 20. The number of hetero atoms constituting the heterocyclic group is preferably 1 to 3. The hetero atom constituting the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom, and more preferably a nitrogen atom.
The group containing a fluorine atom preferably has a terminal structure represented by formula (1) or (2). Wherein denotes a bond.
*-CHF2 (1)
*-CF3 (2)
The number of all fluorine atoms in the oxime compound containing a fluorine atom is preferably 3 or more, and more preferably 4 to 10.
The oxime compound containing a fluorine atom is preferably a compound represented by the formula (OX-1).
(OX-1)
[ chemical formula 5]
In the formula (OX-1), Ar1And Ar2Each independently represents an optionally substituted aromatic hydrocarbon ring, R1Represents an aryl group having a group containing a fluorine atom, R2And R3Each independently represents an alkyl group or an aryl group.
Ar1And Ar2Each independently represents an aromatic hydrocarbon ring which may have a substituent. The aromatic hydrocarbon ring may be a single ring or a condensed ring. The number of carbon atoms in the ring constituting the aromatic hydrocarbon ring is preferably 6 to 20, more preferably 6 to 15, and particularly preferably 6 to 10. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring. Wherein Ar is1And Ar2At least one of (A) is preferably a benzene ring, Ar1More preferably a benzene ring. Ar (Ar)2Preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring.
As Ar1And Ar2Examples of the substituent which may be present include an alkyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, a halogen atom, -ORX1、-SRX1、-CORX1、-COORX1、-OCORX1、-NRX1RX2、-NHCORX1、-CONRX1RX2、-NHCONRX1RX2、-NHCOORX1、-SO2RX1、-SO2ORX1and-NHSO2RX1And the like. RX1And RX2Each independently represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferable. Alkyl as a substituent and RX1And RX2The number of carbon atoms of the alkyl group is preferably 1 to 30. The alkyl group may be linear, branched or cyclic, and is preferably linear or branched. In the alkyl group, a part or all of the hydrogen atoms may be substituted with a halogen atom (preferably a fluorine atom). In the alkyl group, some or all of the hydrogen atoms may be substituted by the above-mentioned substituentsAnd (4) substituting. Aryl as a substituent and RX1And RX2The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10. The aryl group may be a single ring or a condensed ring. In the aryl group, a part or all of the hydrogen atoms may be substituted by the above-mentioned substituent. Heterocyclic group as substituent and RX1And RX2The heterocyclic group represented is preferably a 5-or 6-membered ring. The heterocyclic group may be a single ring or a condensed ring. The number of carbon atoms constituting the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and still more preferably 3 to 12. The number of hetero atoms constituting the heterocyclic group is preferably 1 to 3. The hetero atom constituting the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. In the heterocyclic group, a part or all of the hydrogen atoms may be substituted by the above-mentioned substituent.
Ar1The aromatic hydrocarbon rings represented are preferably unsubstituted. Ar (Ar)2The aromatic hydrocarbon ring may be unsubstituted or substituted. Preferably with substituents. As the substituent, preferred is-CORX1。RX1Preferably an alkyl, aryl or heterocyclic group, more preferably an aryl group. The aryl group may have a substituent or may be unsubstituted. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms.
R1Represents an aryl group having a group containing a fluorine atom. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10. The group containing a fluorine atom preferably includes an alkyl group having a fluorine atom (a fluorine-containing alkyl group) and a group containing an alkyl group having a fluorine atom (a fluorine-containing group). The group containing a fluorine atom has the same meaning as the above range, and the preferable range is also the same.
R2Represents an alkyl or aryl group, preferably an alkyl group. The alkyl group and the aryl group may be unsubstituted or substituted. As the substituent, the above-mentioned Ar is mentioned1And Ar2The substituents illustrated in the substituents which may be present. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, and particularly preferably 1 to 4. The alkyl group may be linear, branched or cyclic, and is preferably linear or branched. Number of carbon atoms of aryl groupPreferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10.
R3Represents an alkyl or aryl group, preferably an alkyl group. The alkyl group and the aryl group may be unsubstituted or substituted. As the substituent, the above-mentioned Ar is mentioned1And Ar2The substituents illustrated in the substituents which may be present. R3The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 10. The alkyl group may be linear, branched or cyclic, and is preferably linear or branched. R3The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10.
Specific examples of the oxime compound having a fluorine atom include compounds described in Japanese patent application laid-open No. 2010-262028, compounds 24, 36 to 40 described in Japanese patent application laid-open No. 2014-500852, and compounds (C-3) described in Japanese patent application laid-open No. 2013-164471.
As the oxime compound, an oxime compound having a fluorene ring can also be used. Specific examples of oxime compounds having a fluorene ring include those described in Japanese patent application laid-open No. 2014-137466. This matter is incorporated in the present specification.
Further, an oxime compound having a benzofuran skeleton can also be used as the oxime compound. Specific examples thereof include compounds OE-01 to OE-75 described in International publication No. 2015/036910.
Further, an oxime compound having a skeleton in which at least 1 benzene ring of a carbazole ring is a naphthalene ring can also be used. Specific examples of such oxime compounds include those described in international publication No. 2013/083505.
Further, an oxime compound having a nitro group can be used. The oxime compounds having a nitro group are also preferably dimers. Specific examples of the oxime compound having a nitro group include compounds described in paragraphs 0031 to 0047 of Japanese patent laid-open publication No. 2013-114249, paragraphs 0008 to 0012 and paragraphs 0070 to 0079 of Japanese patent laid-open publication No. 2014-137466, and compounds described in paragraphs 0007 to 0025 of Japanese patent laid-open publication No. 4223071.
Specific examples of oxime compounds are shown below, but the present invention is not limited thereto.
[ chemical formula 6]
[ chemical formula 7]
The photopolymerization initiator used in the present invention is preferably a material satisfying the following condition 1.
Condition 1: a composition prepared by mixing 1 part by mass of a photopolymerization initiator, 47.5 parts by mass of a resin P1 having the following structure, and 51.5 parts by mass of Propylene Glycol Monomethyl Ether Acetate (PGMEA) was applied onto a glass substrate by a spin coater so that the film thickness after prebaking became 2.0 μm, and a film was formed by heating (prebaking) with a hot plate at 100 ℃ for 120 seconds, and when the absorbance of the formed film in the wavelength range of 400 to 700nm was measured, the maximum value of the absorbance in the above range was 0.03 or less.
Resin P1: propylene glycol monomethyl ether acetate solution of benzyl methacrylate/methacrylic acid (70/30 [ molar ratio ]) copolymer (40 mass% solid content, weight average molecular weight 30000, FUJIKURA KASEI CO., LTD., Acrybase FF-187)
In the present invention, it is preferable to use a photopolymerization initiator having an absorption coefficient of 1.0X 10 at 365nm in methanol together3A photopolymerization initiator A1 having a concentration of mL/gcm or more and an absorption coefficient at a wavelength of 365nm in methanol of 1.0X 102mL/gcm or less and an absorption coefficient at a wavelength of 254nm of 1.0X 103A photopolymerization initiator A2 having a concentration of mL/gcm or more. According to this embodiment, the lens composition can be easily cured sufficiently by exposure, and a lens having excellent properties such as solvent resistance can be produced in a low-temperature process (for example, at a temperature of 150 ℃ or lower, preferably at a temperature of 120 ℃ or lower throughout all steps).Therefore, it is particularly effective in manufacturing a lens in a low temperature process. The photopolymerization initiator a1 and the photopolymerization initiator a2 are preferably used by selecting a compound having the above absorption coefficient from the above compounds.
In the present invention, the absorption coefficient at the above wavelength of the photopolymerization initiator is a value measured as follows. That is, a measurement solution was prepared by dissolving a photopolymerization initiator in methanol, and the absorbance of the measurement solution was measured and calculated. Specifically, the measurement solution was placed on a glass dish having a width of 1cm, and absorbance was measured by using a UV-Vis-NIR spectrometer (Cary5000) manufactured by Agilent Technologies, and the absorbance was substituted into the following formula to calculate the absorption coefficient (mL/gcm) at a wavelength of 365nm and a wavelength of 254 nm.
[ numerical formula 1]
In the above formula,. epsilon.represents an absorption coefficient (mL/gcm), A represents an absorbance, c represents a concentration (g/mL) of a photopolymerization initiator, and l represents an optical path length (cm).
The photopolymerization initiator A1 had an absorption coefficient of 1.0X 10 at a wavelength of 365nm in methanol3mL/gcm or more, preferably 1.0X 104mL/gcm or more, more preferably 1.1X 104mL/gcm or more, and more preferably 1.2X 104～1.0×105mL/gcm, more preferably 1.3X 104～5.0×104mL/gcm, particularly preferably 1.5X 104～3.0×104mL/gcm。
The photopolymerization initiator A1 preferably has an absorption coefficient of 1.0X 10 for light having a wavelength of 254nm in methanol4～1.0×105mL/gcm, more preferably 1.5X 104～9.5×104mL/gcm, more preferably 3.0X 104～8.0×104mL/gcm。
The photopolymerization initiator a1 is preferably an oxime compound, an aminoalkylphenone compound, or an acylphosphine compound, more preferably an oxime compound or an acylphosphine compound, still more preferably an oxime compound, and particularly preferably an oxime compound containing a fluorine atom, from the viewpoint of compatibility with other components contained in the composition. As the oxime compound containing a fluorine atom, a compound represented by the above formula (OX-1) is preferable. Specific examples of the photopolymerization initiator A1 include 1, 2-octanedione, 1- [4- (phenylthio) -,2- (o-benzoyloxime) ] (commercially available, for example, IRGACURE-OXE01, manufactured by BASF corporation), ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (o-acetyloxime) (commercially available, for example, IRGACURE-OXE02, manufactured by BASF corporation), bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (commercially available, for example, IRGACURE-819, manufactured by BASF corporation), and (C-13) and (C-14) shown in the specific examples of the oxime compound.
The photopolymerization initiator A2 has an absorption coefficient of 1.0X 10 for light having a wavelength of 365nm in methanol2mL/gcm or less, preferably 10 to 1.0X 102mL/gcm, more preferably 20 to 1.0X 102mL/gcm. The difference between the absorption coefficient of the photopolymerization initiator A1 for light having a wavelength of 365nm in methanol and the absorption coefficient of the photopolymerization initiator A2 for light having a wavelength of 365nm in methanol was 9.0X 102mL/gcm or more, preferably 1.0X 103mL/gcm or more, more preferably 5.0X 103～3.0×104mL/gcm, more preferably 1.0X 104～2.0×104mL/gcm. The photopolymerization initiator A2 had an absorption coefficient of 1.0X 10 for light having a wavelength of 254nm in methanol3mL/gcm or more, preferably 1.0X 103～1.0×106mL/gcm, more preferably 5.0X 103～1.0×105mL/gcm。
The photopolymerization initiator a2 is preferably a hydroxyalkyl phenone compound, a benzoyl formate compound, an aminoalkyl phenone compound, or an acylphosphine compound, more preferably a hydroxyalkyl phenone compound or a benzoyl formate compound, and still more preferably a hydroxyalkyl phenone compound. The hydroxyalkyl phenone compound is preferably a compound represented by the above formula (V). Specific examples of the photopolymerization initiator A2 include 1-hydroxy-cyclohexyl-phenyl-ketone (commercially available, for example, IRGACURE-184, manufactured by BASF corporation), 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (commercially available, for example, IRGACURE-2959, manufactured by BASF corporation), and the like.
As the combination of the photopolymerization initiator a1 and the photopolymerization initiator a2, a combination in which the photopolymerization initiator a1 is an oxime compound and the photopolymerization initiator a2 is a hydroxyalkylphenone compound is preferable, a combination in which the photopolymerization initiator a1 is an oxime compound and the photopolymerization initiator a2 is a compound represented by the above formula (V) is more preferable, and a combination in which the photopolymerization initiator a1 is an oxime compound containing a fluorine atom and the photopolymerization initiator a2 is a compound represented by the above formula (V) is particularly preferable. By adopting such a combination, a lens having excellent properties such as solvent resistance can be produced in a low-temperature process. Further, a lens with less wrinkles or voids can be manufactured.
The content of the photopolymerization initiator is preferably 1 to 20% by mass based on the total solid content of the lens composition. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 14% by mass or less, and still more preferably 13% by mass or less. The lens composition of the present invention preferably contains 5 to 50 parts by mass of a photopolymerization initiator per 100 parts by mass of the polymerizable monomer. The upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less. The lower limit is preferably 10 parts by mass or more, and more preferably 15 parts by mass or more. According to this embodiment, a pattern having excellent rectangularity can be formed.
In the lens composition of the present invention, when the photopolymerization initiator a1 is used as a photopolymerization initiator, the content of the photopolymerization initiator a1 is preferably 1 to 15% by mass based on the total solid content of the lens composition. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and further preferably 4% by mass or more. The upper limit is preferably 14% by mass or less, more preferably 12.5% by mass or less, and still more preferably 10% by mass or less.
In the lens composition of the present invention, when the photopolymerization initiator a2 is used as a photopolymerization initiator, the content of the photopolymerization initiator a2 is preferably 0.5 to 15% by mass based on the total solid content of the lens composition. The lower limit is preferably 1% by mass or more, more preferably 1.5% by mass or more, and further preferably 2% by mass or more. The upper limit is preferably 12.5% by mass or less, more preferably 10% by mass or less, and still more preferably 7.5% by mass or less.
When the photopolymerization initiator a1 and the photopolymerization initiator a2 are used as photopolymerization initiators in the lens composition of the present invention, the lens composition of the present invention preferably contains 50 to 200 parts by mass of the photopolymerization initiator a2 per 100 parts by mass of the photopolymerization initiator a 1. The upper limit is preferably 175 parts by mass or less, and more preferably 150 parts by mass or less. The lower limit is preferably 60 parts by mass or more, and more preferably 70 parts by mass or more. According to this embodiment, the lens composition can be easily cured sufficiently by exposure, and a lens can be produced in a low-temperature process (for example, at a temperature of 150 ℃ or lower, preferably 120 ℃ or lower throughout all steps). Further, a lens with less wrinkles or voids can be manufactured.
In the lens composition of the present invention, when the photopolymerization initiator a1 and the photopolymerization initiator a2 are used as photopolymerization initiators, the total content of the photopolymerization initiator a1 and the photopolymerization initiator a2 in the total solid content of the lens composition is preferably 5 to 15% by mass. The lower limit is preferably 6% by mass or more, more preferably 7% by mass or more, and further preferably 8% by mass or more. The upper limit is preferably 14.5% by mass or less, more preferably 14% by mass or less, and still more preferably 13% by mass or less. Within the above range, the lens composition can be easily sufficiently cured by exposure, and a lens can be produced in a low-temperature process (for example, at a temperature of 150 ℃ or less, preferably 120 ℃ or less throughout all steps). Further, a lens with less wrinkles or voids can be manufactured.
Resin (resin)
The lens composition of the present invention contains a resin. The resin is blended for use in dispersing particles such as a pigment in the composition or for use in a binder, for example. The resin mainly used for dispersing particles and the like in the composition is also referred to as a dispersant. However, such an application of the resin is an example, and the resin may be used for an application other than this application.
The weight average molecular weight (Mw) of the resin is preferably 2000 to 2000000. The upper limit is preferably 1000000 or less, more preferably 500000 or less. The lower limit is preferably 3000 or more, more preferably 4000 or more, and further preferably 5000 or more.
Examples of the resin include (meth) acrylic resins, (meth) acrylamide resins, epoxy resins, olefin thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenyl resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and silicone resins.
In the present invention, it is preferable to use a resin having a refractive index of 1.5 or more at a wavelength of 550nm (hereinafter, also referred to as a high refractive index resin). The refractive index of the resin at a wavelength of 550nm is preferably 1.6 or more, more preferably 1.7 or more, and still more preferably 1.8 or more. The upper limit is preferably 4.0 or less, more preferably 3.9 or less, still more preferably 3.5 or less, and particularly preferably 3.0 or less. The high refractive index resin can be used as a binder or a dispersant.
The refractive index of the resin can be measured in an uncured state by the following method. As for a specific measurement method, after a film composed only of a resin as a measurement object was made on a silicon wafer at a thickness of 300nm, the refractive index of the obtained film was measured using an ellipsometer (Lambda Ace RE-3300 (product name), Dainippon Screen mfg.
The resin used in the present invention may have an acid group. Examples of the acid group include a carboxyl group, a phosphoric group, a sulfo group, and a phenolic hydroxyl group. The number of such acid groups may be only 1, or may be 2 or more. A resin having an acid group can also be used as the alkali-soluble resin or the dispersant.
The acid value of the resin having an acid group is preferably 30 to 500 mgKOH/g. The lower limit is more preferably 50mgKOH/g or more, and still more preferably 70mgKOH/g or more. The upper limit is more preferably 400mgKOH/g or less, still more preferably 200mgKOH/g or less, particularly preferably 150mgKOH/g or less, most preferably 120mgKOH/g or less.
As the resin having an acid group, a polymer having a carboxyl group in a side chain is preferable. Examples thereof include copolymers having repeating units derived from monomers such as methacrylic acid, acrylic acid, itaconic acid, crotonic acid, maleic acid, 2-carboxyethyl (meth) acrylic acid, vinylbenzoic acid, and partial esterified maleic acid, alkali-soluble phenol resins such as novolak type resins, acidic cellulose derivatives having a carboxyl group in a side chain, and polymers obtained by adding a polymer having a hydroxyl group to an acid anhydride. In particular, a copolymer of (meth) acrylic acid and other monomer copolymerizable therewith is preferable. Examples of the other monomer copolymerizable with (meth) acrylic acid include alkyl (meth) acrylates, aryl (meth) acrylates, and vinyl compounds. Examples of the alkyl (meth) acrylate and aryl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl methacrylate, and tetrahydrofurfuryl methacrylate. Examples of the vinyl compound include styrene, α -methylstyrene, vinyltoluene, acrylonitrile, vinyl acetate, N-vinylpyrrolidone, a polystyrene macromonomer, and a polymethyl methacrylate macromonomer. The number of other monomers copolymerizable with these (meth) acrylic acids may be only 1, or may be 2 or more.
The resin having an acid group may also have a repeating unit derived from a maleimide compound. As the maleimide compound, N-alkyl maleimide, N-aryl maleimide and the like can be mentioned. As the repeating unit derived from the maleimide compound, a repeating unit represented by the formula (C-mi) can be mentioned.
[ chemical formula 8]
In formula (C-mi), Rmi represents an alkyl group or an aryl group. The number of carbon atoms in the alkyl group is preferably 1 to 20. The alkyl group may be any of linear, branched, and cyclic. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6 to 10. Rmi is preferably aryl.
The resin having an acid group is also preferably a resin containing a repeating unit derived from a compound represented by the following formula (ED1) and/or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer").
[ chemical formula 9]
In the formula (ED1), R1And R2Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
[ chemical formula 10]
In the formula (ED2), R represents a hydrogen atom or an organic group having 1-30 carbon atoms. As a specific example of the formula (ED2), reference can be made to the description of Japanese patent laid-open No. 2010-168539.
As for a specific example of the ether dimer, reference can be made to paragraph 0317 of Japanese patent application laid-open No. 2013-029760, which is incorporated herein by reference.
Examples of the resin containing a repeating unit derived from an ether dimer include resins having the following structures. In the following structural formula, Me represents a methyl group.
[ chemical formula 11]
The resin used in the present invention may have a polymerizable group. Examples of the polymerizable group include groups having an ethylenically unsaturated bond such as a vinyl group, (meth) allyl group, and (meth) acryloyl group. Commercially available products of resins having a polymerizable group include DIANAL NR series (LTD. manufactured), Photomer6173 (urethane acrylate oligomer containing a carboxyl group, Diamond Shamrock Co., Ltd.), VISCOAT R-264, KS RESIST 106 (manufactured by OSAKA ORGANIC CHEMICAL LTD., manufactured by CYCLOMER P series (for example, ACA230AA), PLACCEL CF200 series (manufactured by Daicel Corporation), Ebecryl3800(DAICEL UCB CO., LTD. manufactured by LTD., manufactured by ACRORE RD-F8(NIPPON SHOKUBA CO., manufactured by LTD., manufactured by FUFIJILM FIRECES Co., manufactured by Ltd.), and the like.
The resin used in the present invention preferably contains a resin b1 containing a repeating unit derived from a compound represented by the formula (I) (hereinafter, also referred to as a repeating unit b 1-1). By using a resin having the repeating unit b1-1, a lens having more excellent transparency can be easily formed.
[ chemical formula 12]
X1Represents O or NH, preferably O.
R1Represents a hydrogen atom or a methyl group.
L1Represents a 2-valent linking group. As the linking group having a valence of 2, there may be mentioned hydrocarbon groups, heterocyclic groups, -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and a combination of 2 or more thereof. Examples of the hydrocarbon group include an alkyl group and an aryl group. The heterocyclic group may be a non-aromatic heterocyclic group or an aromatic heterocyclic group. The heterocyclic group is preferably a 5-membered ring or a 6-membered ring. Examples of the hetero atom constituting the heterocyclic group include a nitrogen atom, an oxygen atom, a sulfur atom and the like. The number of hetero atoms constituting the heterocyclic group is preferably 1 to 3. The heterocyclic group may be a single ring or a condensed ring. The hydrocarbon group and the heterocyclic group may have a substituent. Examples of the substituent include an alkyl group, an aryl group, a hydroxyl group, and a halogen atom.
R10Represents a substituent. As R10The substituent represented by the formula (I) includes the substituent T shown below, preferably a hydrocarbon group, and more preferably a group which may have an aryl group as a substituentAn alkyl group.
m represents an integer of 0 to 2, preferably 0 or 1, more preferably 0.
p represents an integer of 0 or more, preferably 0 to 4, more preferably 0 to 3, further preferably 0 to 2, further preferably 0 or 1, and particularly preferably 1.
(substituent T)
Examples of the substituent T include a halogen atom, a cyano group, a nitro group, a hydrocarbon group, a heterocyclic group and-ORt1、-CORt1、-COORt1、-OCORt1、-NRt1Rt2、-NHCORt1、-CONRt1Rt2、-NHCONRt1Rt2、-NHCOORt1、-SRt1、-SO2Rt1、-SO2ORt1、-NHSO2Rt1or-SO2NRt1Rt2。Rt1And Rt2Each independently represents a hydrogen atom, a hydrocarbon group or a heterocyclic group. Rt1And Rt2May be bonded to form a ring.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group. The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and still more preferably 1 to 8. The alkyl group may be linear, branched or cyclic, and is preferably linear or branched, and more preferably branched.
The number of carbon atoms of the alkenyl group is preferably 2 to 30, more preferably 2 to 12, and particularly preferably 2 to 8. The alkenyl group may be linear, branched or cyclic, and is preferably linear or branched.
The number of carbon atoms of the alkynyl group is preferably 2 to 30, more preferably 2 to 25. The alkynyl group may be any of linear, branched and cyclic, and is preferably linear or branched.
The number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12.
The heterocyclic group may be a single ring or a condensed ring. The heterocyclic group is preferably a monocyclic ring or a condensed ring having a condensed number of 2 to 4. The number of hetero atoms constituting the ring of the heterocyclic group is preferably 1 to 3. The hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and still more preferably 3 to 12.
The hydrocarbon group and the heterocyclic group may have a substituent or may be unsubstituted. Examples of the substituent include the substituents described above for the substituent T.
The compound represented by the formula (I) is preferably a compound represented by the following formula (I-1).
[ chemical formula 13]
X1Represents O or NH, preferably O.
R1Represents a hydrogen atom or a methyl group.
R2、R3And R11Each independently represents a hydrocarbon group.
R2And R3The hydrocarbon group represented is preferably an alkylene group or an arylene group, and more preferably an alkylene group. The number of carbon atoms of the alkylene group is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 2 or 3. R11The hydrocarbon group represented may preferably be an alkyl group having an aryl group as a substituent, and more preferably an alkyl group having an aryl group as a substituent. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 10, and still more preferably 1 to 5. The number of carbon atoms of an alkyl group when the alkyl group has an aryl group as a substituent means the number of carbon atoms of the alkyl group site.
R12Represents a substituent. As R12The substituent represented by the formula (I) includes the substituent (T).
n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and further preferably an integer of 0 to 3.
m represents an integer of 0 to 2, preferably 0 or 1, more preferably 0.
p1 represents an integer of 0 or more, preferably 0 to 4, more preferably 0 to 3, further preferably 0 to 2, further preferably 0 to 1, and particularly preferably 0.
q1 represents an integer of 1 or more, preferably 1 to 4, more preferably 1 to 3, further preferably 1 to 2, and particularly preferably 1.
The compound represented by the formula (I) is preferably a compound represented by the following formula (III).
[ chemical formula 14]
In the formula, R1Represents a hydrogen atom or a methyl group, R21And R22Each independently represents an alkylene group, and n represents an integer of 0 to 15. R21And R22The number of carbon atoms of the alkylene group is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 2 or 3. n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and further preferably an integer of 0 to 3.
Examples of the compound represented by the formula (I) include ethylene oxide-or propylene oxide-modified (meth) acrylates of cumylphenol. As a commercially available product, ARONIX M-110 (manufactured by TOAGOSEI CO., LTD.) and the like can be mentioned.
Preferably, the resin b1 further contains a repeating unit derived from an alkyl (meth) acrylate (hereinafter, also referred to as a repeating unit b 1-2). The alkyl group of the alkyl (meth) acrylate preferably has 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms, and still more preferably 3 to 6 carbon atoms. Preferable specific examples of the alkyl (meth) acrylate include n-butyl (meth) acrylate and the like.
The resin b1 also preferably further contains a repeating unit having an acid group (hereinafter, also referred to as a repeating unit b 1-3).
The lens composition of the present invention may contain a resin as a dispersant. Examples of the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin). Here, the acidic dispersant (acidic resin) means a resin in which the amount of acid groups is larger than the amount of basic groups. The acidic dispersant (acidic resin) is preferably a resin in which the amount of the acid group is 70 mol% or more, and more preferably a resin substantially consisting of only the acid group, when the total amount of the acid group and the basic group is 100 mol%. The acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g. The basic dispersant (basic resin) is a resin having a larger amount of basic groups than that of acid groups. The basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the acid groups and the amount of basic groups is 100 mol%. The basic group of the basic dispersant is preferably an amino group.
Examples of the dispersant include polymeric dispersants [ e.g., polyamides and salts thereof, polycarboxylic acids and salts thereof, high molecular weight unsaturated acid esters, modified polyurethanes, modified polyesters, modified poly (meth) acrylates, (meth) acrylic copolymers, formalin naphthalene sulfonate thick compounds ], polyoxyethylene alkyl phosphate esters, polyoxyethylene alkylamines, alkanolamines, and the like. The polymer dispersants can be further classified into linear polymers, terminal-modified polymers, graft polymers, and block polymers according to their structures. The polymeric dispersant is adsorbed on the surface of particles such as pigments, and exerts a function of preventing reagglomeration. Therefore, a terminal-modified polymer, a graft polymer, or a block polymer having a site anchored to the surface of a particle such as a pigment can be given as a preferable structure. Further, the dispersants described in paragraphs 0028 to 0124 of Japanese patent application laid-open No. 2011-070156 and the dispersants described in Japanese patent application laid-open No. 2007-277514 are also preferably used.
In the present invention, a block copolymer can also be used as the dispersant. The details of the block copolymer can be found in paragraphs 0131 to 0160 of Japanese patent application laid-open Nos. 2012 and 137564, which are incorporated herein by reference. In the present invention, an oligoimine copolymer containing a nitrogen atom in at least one of the main chain and the side chain can also be used as the dispersant. Regarding the oligoimine-based copolymer, the contents of paragraphs 0102 to 0174 of Japanese patent application laid-open No. 2012 and 255128 can be referred to and incorporated herein.
The dispersant is also available as a commercially available product, and specific examples thereof include Disperbyk series (for example, Disperbyk-111, 2001 and the like) manufactured by BYK Chemie GmbH, SOLSPERSE series (for example, SOLSPERSE20000, 76500 and the like) manufactured by Lubrizol Japan Ltd, Ajinomoto Fine-Techno Co., manufactured by Inc., AJISPER series and the like. Further, the products described in paragraph 0129 of Japanese patent laid-open Nos. 2012 and 137564 and 0235 of Japanese patent laid-open Nos. 2017 and 194662 can also be used as the dispersing agent.
The content of the resin is preferably 15 to 75% by mass based on the total solid content of the lens composition. The upper limit is preferably 65% by mass or less, more preferably 55% by mass or less. The lower limit is preferably 25% by mass or more, and more preferably 35% by mass or more.
The content of the resin is preferably 25 to 200 parts by mass per 100 parts by mass of the polymerizable monomer. The upper limit is preferably 175 parts by mass or less, and more preferably 150 parts by mass or less. The lower limit is preferably 50 parts by mass or more, and more preferably 75 parts by mass or more.
The content of the resin b1 (including the repeating unit derived from the compound represented by the formula (III)) in the total amount of resins contained in the lens composition of the present invention is preferably 0.1 to 100% by mass, and more preferably 10 to 100% by mass. The upper limit may be 90 mass% or less, may be 80 mass% or less, and may be 70 mass% or less.
The content of the resin b1 is preferably 0.1 to 70% by mass based on the total solid content of the lens composition. The upper limit is preferably 60% by mass or less, more preferably 50% by mass or less. The lower limit is preferably 1% by mass or more, and more preferably 5% by mass or more.
Compounds containing furyl group
The lens composition of the present invention preferably contains a compound containing a furyl group (hereinafter, also referred to as a compound containing a furyl group). According to this embodiment, a lens composition having excellent low-temperature curability can be obtained.
The structure of the furyl group-containing compound is not particularly limited as long as it contains a furyl group (a group in which 1 hydrogen atom is removed from furan).
As the compound containing a furyl group, the compounds described in paragraphs 0049 to 0089 of Japanese patent laid-open publication No. 2017-194662 can be used. Further, compounds described in Japanese patent laid-open Nos. 2000-233581, 1994-271558, 1994-293830, 1996-239421, 1998-508655, 2000-001529, 2003-183348, 2006-193628, 2007-186684, 2010-265377, 2011-170170069, and the like can be used.
The compound containing a furyl group may be a monomer or a polymer. The polymer is preferable because a lens having excellent durability can be easily obtained. In the case of a polymer, the weight average molecular weight is preferably 2000 to 70000. The upper limit is preferably 60000 or less, more preferably 50000 or less. The lower limit is preferably 3000 or more, more preferably 4000 or more, and further preferably 5000 or more. In addition, the polymeric furanyl group containing compound is a component of a resin in the lens composition according to the invention as well.
As the monomeric furyl group-containing compound (hereinafter, also referred to as furyl group-containing monomer), a compound represented by the following formula (fur-1) can be mentioned.
[ chemical formula 15]
In the formula, Rf1Represents a hydrogen atom or a methyl group, Rf2Represents a 2-valent linking group.
As Rf2The 2-valent linking group may be an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, or a combination of 2 or more thereof. The number of carbon atoms of the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group may be any of linear, branched, and cyclic. The number of carbon atoms of the arylene group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxyl group.
The furyl group-containing monomer is preferably a compound represented by the following formula (fur-1-1).
[ chemical formula 16]
In the formula, Rf1Represents a hydrogen atom or a methyl group, Rf11represents-O-or-NH-, Rf12Represents a single bond or a 2-valent linking group. As Rf12The 2-valent linking group may be an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, or a combination of 2 or more thereof. The number of carbon atoms of the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group may be any of linear, branched, and cyclic. The number of carbon atoms of the arylene group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxyl group.
Specific examples of the furyl group-containing monomer include compounds having the following structures. In the following structural formula, Rf1Represents a hydrogen atom or a methyl group.
[ chemical formula 17]
As the polymeric furyl group-containing compound (hereinafter, also referred to as furyl group-containing polymer), a resin containing a repeating unit containing a furyl group is preferable, and a resin containing a repeating unit derived from the compound represented by the above formula (fur-1) is more preferable. The concentration of the furyl group in the furyl group-containing polymer is preferably 0.5 to 6.0mmol, more preferably 1.0 to 4.0mmol, per 1g of the furyl group-containing polymer. When the concentration of the furyl group is 0.5mmol or more, preferably 1.0mmol or more, a lens having excellent solvent resistance and the like can be easily formed. When the concentration of the furyl group is 6.0mmol or less, preferably 4.0mmol or less, the stability of the lens composition with time becomes good.
The polymer containing a furyl group may contain, in addition to the repeating unit having a furyl group, a repeating unit having an acid group and/or a repeating unit having a polymerizable group. Examples of the acid group include a carboxyl group, a phosphoric group, a sulfo group, and a phenolic hydroxyl group. Examples of the polymerizable group include groups having an ethylenically unsaturated bond such as a vinyl group, (meth) allyl group, and (meth) acryloyl group.
When the polymer containing a furyl group contains a repeating unit having an acid group, the solubility of the polymer containing a furyl group in the lens composition becomes high, and thus a lens having more excellent transparency is easily formed. Further, the reactivity with the polymerizable monomer is improved, and the curability at low temperature is further improved, and a lens having further excellent solvent resistance and the like is easily formed. When the polymer having a furyl group contains a repeating unit having an acid group, the acid value is preferably 10 to 200mgKOH/g, more preferably 40 to 130 mgKOH/g.
When the polymer containing a furyl group includes a repeating unit having a polymerizable group, a lens having more excellent solvent resistance and the like can be easily formed.
The furyl group-containing polymer can be produced by the method described in paragraphs 0052 to 0101 of Japanese patent application laid-open No. 2017-194662.
The content of the furyl group-containing compound is preferably 0.1 to 70% by mass based on the total solid content of the lens composition. The lower limit is preferably 2.5% by mass or more, more preferably 5.0% by mass or more, and further preferably 7.5% by mass or more. The upper limit is preferably 65% by mass or less, more preferably 60% by mass or less, and still more preferably 50% by mass or less.
When a polymer containing a furyl group is used as the compound containing a furyl group, the content of the polymer containing a furyl group in the resin contained in the lens composition is preferably 0.1 to 100% by mass. The lower limit is preferably 10% by mass or more, and more preferably 15% by mass or more. The upper limit is preferably 90% by mass or less, more preferably 80% by mass or less.
When the resin used in the lens composition of the present invention contains the resin b1 and a polymer containing a furyl group is used as the compound containing a furyl group, the content of the polymer containing a furyl group is preferably 10 to 200 parts by mass per 100 parts by mass of the resin b 1. The upper limit is preferably 175 parts by mass or less, and preferably 150 parts by mass or less. The lower limit is preferably 25 parts by mass or more, and preferably 50 parts by mass or more. By using the resin b1 and the polymer containing a furyl group together, effects such as excellent low-temperature curability and transparency can be expected. Further, when the ratio of the two is within the above range, a lens having excellent durability can be easily obtained.
Compound having epoxy group
The lens composition of the present invention preferably further contains a compound having an epoxy group. The compound having an epoxy group is preferably a compound having 2 or more epoxy groups in 1 molecule. Preferably, the epoxy group has 2 to 100 epoxy groups in 1 molecule. The upper limit may be set to, for example, 10 or less, or may be set to 5 or less. The epoxy equivalent of the compound having an epoxy group (the molecular weight of the compound having an epoxy group/the number of epoxy groups) is preferably 500g/eq or less, more preferably 100 to 400g/eq, and still more preferably 100 to 300 g/eq. The compound having an epoxy group may be a low molecular compound (for example, a molecular weight of less than 1000) or a high molecular compound (macromolecule) (for example, in the case of a polymer having a molecular weight of 1000 or more, the weight average molecular weight is 1000 or more). The molecular weight (weight average molecular weight in the case of a polymer) of the compound having an epoxy group is preferably 200 to 100000, more preferably 500 to 50000. The upper limit of the molecular weight (weight average molecular weight in the case of a polymer) is preferably 3000 or less, more preferably 2000 or less, and still more preferably 1500 or less.
As the compound having an epoxy group, compounds described in paragraphs 0034 to 0036 of Japanese patent application laid-open No. 2013-011869, paragraphs 0147 to 0156 of Japanese patent application laid-open No. 2014-043556, paragraphs 0085 to 0092 of Japanese patent application laid-open No. 2014-089408, and compounds described in Japanese patent application laid-open No. 2017-179172 can be used. These are incorporated into the present specification.
When the lens composition of the present invention contains a compound having an epoxy group, the content of the compound having an epoxy group is preferably 0.1 to 40% by mass in the total solid content of the lens composition. The lower limit is more preferably 0.5% by mass or more, and still more preferably 1% by mass or more. The upper limit is more preferably 30% by mass or less, and still more preferably 20% by mass or less. The epoxy group-containing compound may be used alone in 1 kind or in combination of 2 or more kinds. When 2 or more kinds are used simultaneously, the total amount is preferably within the above range.
White or colorless pigment (white pigment)
The lens composition of the present invention may contain a white or colorless pigment (hereinafter, also referred to as a white pigment). When the composition for a lens of the present invention contains a white pigment, a lens having a high refractive index can be easily formed.
Examples of the white pigment include particles containing an oxide of at least 1 element selected from Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P, and S, and preferably particles containing an oxide of at least 1 element selected from Ti, Zr, Sn, Al, and Si. The oxide is preferably titanium oxide or zirconium oxide, and more preferably titanium oxide. Further, as the titanium oxide, rutile type titanium oxide, Anatase (Anatase) type titanium oxide, and amorphous type titanium oxide are exemplified, and rutile type titanium oxide is preferable. The oxide is also preferably surface-treated with a surface treatment agent. The surface treatment agent includes inorganic compounds and organic compounds. Both inorganic compounds and organic compounds may be used. Specific examples of the surface treatment agent include polyhydric alcohols, alumina, aluminum hydroxide, amorphous silica, hydrous silica, alkanolamines, stearic acid, organosiloxanes, zirconia, hydrogenated polydimethylsiloxanes, silane coupling agents, titanate coupling agents, and the like.
The shape of the white pigment is not particularly limited. Examples of the shape include isotropic shapes (e.g., spherical, polyhedral, etc.), anisotropic shapes (e.g., needle-like, rod-like, plate-like, etc.), and irregular shapes.
The weight average particle diameter of 1 st particle of the white pigment is preferably 150nm or less, more preferably 100nm or less, and further preferably 80nm or less. The lower limit is not particularly limited, but is preferably 1nm or more. In addition, as for the weight average particle diameter of the white-based pigment, unless otherwise specified, it is obtained by diluting a mixed liquid or a dispersion liquid containing the white-based pigment by 80 times with propylene glycol monomethyl ether acetate, and measuring the obtained diluted liquid with a dynamic light scattering method. The weight average particle diameter obtained by using Microtrac (product name) UPA-EX150 manufactured by Nikkiso co.
The specific surface area of the white pigment is preferably 10 to 400m2(ii) g, more preferably 20 to 200m2(iv)/g, further preferably 30 to 150m2/g。
The refractive index of the white pigment is preferably 1.6 to 3.0. The lower limit is preferably 1.7 or more, more preferably 1.8 or more. The upper limit is preferably 2.9 or less, and more preferably 2.8 or less. The refractive index of the white pigment is measured in accordance with Japanese Industrial standards (JIS K0062: 1992).
Commercially available white pigments can be used. Examples of the titanium oxide include TTO series (TTO-51(A), TTO-51(C), TTO-55(C), etc.), TTO-S, V series (TTO-S-1, TTO-S-2, TTO-V-3, etc.) (above, product name, Ishihara Sangyo Kaisha, LTD. manufactured), MT series (MT-01, MT-POR05, etc.) (product name, manufactured by TAYCA CORATION), etc.
When the lens composition of the present invention contains a white pigment, the content of the white pigment is preferably 10 to 60% by mass based on the total solid content of the lens composition. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less. The lower limit is preferably 15% by mass or more, and more preferably 20% by mass or more. The lens composition of the present invention may contain only 1 kind of white pigment, or may contain 2 or more kinds. When 2 or more species are contained, the total amount of these is preferably within the above range.
Further, it is also preferable that the lens composition of the present invention contains substantially no white pigment. According to this embodiment, a lens with small surface roughness can be easily formed. The case where the lens composition of the present invention contains substantially no white pigment means that the content of the white pigment is 0.1% by mass or less, preferably 0.05% by mass or less, more preferably 0.01% by mass or less, and particularly preferably no white pigment in the total solid content of the lens composition.
Solvents
The lens composition of the present invention preferably contains a solvent. As the solvent, an organic solvent is exemplified. The solvent is not particularly limited as long as it satisfies the solubility of each component or the coatability of the lens composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For details of these, reference can be made to paragraph 0223 of international publication No. 2015/166779, which is incorporated in the present specification. Also, ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, methylene chloride, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethylcetearyl acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropionamide, and 3-butoxy-N, N-dimethylpropionamide. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, and the like) as a solvent may be reduced to be preferable for environmental reasons and the like (for example, the aromatic hydrocarbons may be set to 50 mass ppm (parts per million) or less, may be set to 10 mass ppm or less, and may be set to 1 mass ppm or less with respect to the total amount of the organic solvent).
In the present invention, a solvent having a small metal content is preferably used, and for example, the metal content of the solvent is preferably 10 parts per billion (ppb) or less by mass. Solvents of quality ppt (parts per trillion) grade, such as those provided by TOYO Gosei co., ltd. (journal of chemical industry, 11/13/2015), may also be used as desired.
Examples of a method for removing impurities such as metals from a solvent include distillation (molecular distillation, membrane distillation, etc.) and filtration using a filter. The filter pore diameter of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and still more preferably 3 μm or less. The material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
The solvent may contain isomers (compounds having the same atomic number but different structures). The isomer may include only 1 kind or a plurality of kinds.
In the present invention, the content of the peroxide in the organic solvent is preferably 0.8mmol/L or less, and more preferably, the organic solvent does not substantially contain a peroxide.
The content of the solvent in the lens composition is preferably 40 to 90% by mass. The lower limit is preferably 50% by mass or more, more preferably 55% by mass or more, and still more preferably 60% by mass or more. The upper limit is preferably 85% by mass or less, more preferably 80% by mass or less, and still more preferably 75% by mass or less.
In view of environmental regulations, it is preferable that the lens composition of the present invention contains substantially no environmental regulations. In the present invention, the substantial absence of the environmental regulation substance means that the content of the environmental regulation substance in the lens composition is 50 mass ppm or less, preferably 30 mass ppm or less, more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less. Examples of the environmental regulation substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are registered as environmental regulation substances based on the REACH (Registration Evaluation Authorization and Restriction of CHemicals) regulation, the PRTR (pollution Release and Transfer Register) method, the VOC (Volatile Organic Compounds) regulation and the like, and the amount of use and the treatment method are strictly regulated. These compounds may be used as a solvent in the production of each component used in the lens composition of the present invention, and may be mixed into the lens composition as a residual solvent. From the viewpoint of safety to humans and environmental considerations, it is preferable to reduce these substances as much as possible. As a method for reducing the environmental regulation substance, there is a method in which the inside of the system is heated and depressurized to a boiling point of the environmental regulation substance or higher, and the environmental regulation substance is distilled off from the system and reduced. In addition, when a small amount of environmental regulation substances is removed by distillation, it is also useful to azeotropically separate the solvent with a solvent having the same boiling point as the solvent in order to improve efficiency. Further, when a compound having radical polymerizability is contained, it is possible to add a polymerization inhibitor and then remove it by distillation under reduced pressure, so that crosslinking between molecules due to radical polymerization reaction in the process of removing it by distillation under reduced pressure can be suppressed. These distillation removal methods can be performed in any of the raw material stage, the stage of the product of reacting the raw materials (for example, the resin solution after polymerization and the polyfunctional monomer solution), or the stage of the lens composition produced by mixing these compounds.
Curing accelerators
The lens composition of the present invention may contain a curing accelerator for the purpose of accelerating the reaction of the polymerizable monomer or lowering the curing temperature. Examples of the curing accelerator include a polyfunctional thiol compound having 2 or more mercapto groups in the molecule. The polyfunctional thiol compound may be added for the purpose of improving stability, odor, resolution, developability, adhesion, and the like. The polyfunctional thiol compound is preferably a secondary alkyl thiol, and more preferably a compound represented by the formula (T1).
Formula (T1)
[ chemical formula 18]
(in the formula (T1), n represents an integer of 2-4, and L represents a 2-4 valent linking group.)
In the formula (T1), the linking group L is preferably an aliphatic group having 2 to 12 carbon atoms, n is 2, and L is particularly preferably an alkylene group having 2 to 12 carbon atoms.
Furthermore, as the curing accelerator, a methylol compound (e.g., a compound exemplified as a crosslinking agent in the 0246 paragraph of Japanese patent laid-open No. 2015-034963), an amine, a phosphonium salt, an amidine salt, and an amide compound (e.g., the curing agent described in the 0186 paragraph of Japanese patent laid-open No. 2013-041165) can be used, examples of the base generating agent include an alkali generating agent (for example, an ionic compound described in Japanese patent laid-open publication No. 2014-055114), a cyanate ester compound (for example, a compound described in paragraph 0071 of Japanese patent laid-open publication No. 2012-150180), an alkoxysilane compound (for example, an alkoxysilane compound having an epoxy group described in Japanese patent laid-open publication No. 2011-253054), an onium salt compound (for example, a compound described as an acid generating agent in paragraph 0216 of Japanese patent laid-open publication No. 2015-034963, and a compound described in Japanese patent laid-open publication No. 2009-180949).
When the lens composition of the present invention contains a curing accelerator, the content of the curing accelerator is preferably 0.3 to 8.9% by mass, and more preferably 0.8 to 6.4% by mass, based on the total solid content of the lens composition.
Silane coupling agent
The lens composition of the present invention preferably contains a silane coupling agent. By containing the silane coupling agent, a lens having excellent adhesion to the support can be easily obtained. As the silane coupling agent, a silane compound having at least 2 functional groups different in reactivity in one molecule is preferable. The silane coupling agent is preferably a silane compound having at least 1 group selected from a vinyl group, an epoxy group, a styryl group, a methacryloyl group, an amino group, an isocyanurate group, a urea group, a mercapto group, a thioether group and an isocyanate group, and an alkoxy group. Specific examples of the silane coupling agent include N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane (Shin-Etsu Chemical Co., Ltd., KBM-602, manufactured by Ltd.), N-2- (aminoethyl) -3-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., manufactured by Ltd., KBM-603), 3-aminopropyltrimethoxysilane (Shin-Etsu Chemical Co., manufactured by Ltd., KBM-903), 3-aminopropyltriethoxysilane (Shin-Etsu Chemical Co., manufactured by Ltd., KBE-903), 3-methacryloxypropyltrimethoxysilane (Shin-Etsu Chemical Co., manufactured by Ltd., KBM-503), and 3-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., manufactured by Shin-Etsu Co., Ltd., KBM-503, Co., manufactured by Shin-Etsu Chemical Co., Ltd., 3-glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Etsu Co., manufactured by Shin-Etsu, Co., Ltd., N-2-aminopropylmethyld, ltd. system, KBM-403), and the like. The details of the silane coupling agent can be found in paragraphs 0155 to 0158 of Japanese patent application laid-open No. 2013-254047, which is incorporated herein by reference. When the lens composition of the present invention contains a silane coupling agent, the content of the silane coupling agent is preferably 0.001 to 20% by mass, more preferably 0.01 to 10% by mass, and particularly preferably 0.1 to 5% by mass, based on the total solid content of the lens composition. The lens composition of the present invention may contain only 1 kind of silane coupling agent, or may contain 2 or more kinds. When 2 or more species are contained, the total amount of these is preferably within the above range.
Polymerization inhibitor
The lens composition of the present invention may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4 '-thiobis (3-methyl-6-t-butylphenol), 2' -methylenebis (4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxylamine salt (ammonium salt, cerium salt, etc.). When the lens composition of the present invention contains a polymerization inhibitor, the content of the polymerization inhibitor is preferably 0.0001 to 5% by mass based on the total solid content of the lens composition. The lens composition of the present invention may contain only 1 polymerization inhibitor, or may contain 2 or more polymerization inhibitors. When 2 or more species are contained, the total amount of these is preferably within the above range.
Ultraviolet absorbent
The lens composition of the present invention may contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound, and the like can be used. For details of these, the descriptions of paragraphs 0052 to 0072 of japanese patent application laid-open No. 2012-208374, paragraphs 0317 to 0334 of japanese patent application laid-open No. 2013-068814, and paragraphs 0061 to 0080 of japanese patent application laid-open No. 2016-162946 are referred to and incorporated herein. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by DAITO CHEMICAL CO., LTD.). Examples of the benzotriazole compound include MIYOSHI & FAT co, MYUA series manufactured by ltd (journal of chemical industry, 2016, 2 months and 1 day). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese patent No. 6268967 can be used. When the lens composition of the present invention contains an ultraviolet absorber, the content of the ultraviolet absorber is preferably 0.1 to 10% by mass, more preferably 0.1 to 5% by mass, and particularly preferably 0.1 to 3% by mass, based on the total solid content of the lens composition. The ultraviolet absorber may be used in only 1 kind, or may be used in 2 or more kinds. When 2 or more species are used, the total amount is preferably within the above range.
Surface active agent
The lens composition of the present invention may contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicon-based surfactant can be used. Regarding the surfactant, it is possible to refer to paragraphs 0238 to 0245 of International publication No. 2015/166779, which is incorporated herein by reference.
In the present invention, the surfactant is preferably a fluorine-based surfactant. By adding a fluorine-based surfactant to the lens composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid-saving property can be further improved. Further, a film with a small thickness variation can be formed.
The fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. The fluorine-containing surfactant having a fluorine content within the above range is effective in terms of uniformity of thickness of a coating film and liquid saving, and has good solubility in the lens composition.
Examples of the fluorine-based surfactant include surfactants described in paragraphs 0060 to 0064 of Japanese patent application laid-open No. 2014-041318 (paragraphs 0060 to 0064 of corresponding International publication No. 2014/017669), and surfactants described in paragraphs 0117 to 0132 of Japanese patent application laid-open No. 2011-132503, and these are incorporated herein. Commercially available fluorine-based surfactants include, for example, Magaface F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS-330 (see DIC CORPORATION), Fluorad FC430, FC431, FC171 (see Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (see ASAHI GLASS CO., LTD.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (see OMNOVA SOLUTION C., INC).
Further, the fluorine-based surfactant can also preferably use an acrylic compound having a molecular structure with a functional group containing a fluorine atom, and when heated, a part of the functional group containing a fluorine atom is cleaved and the fluorine atom is volatilized. Examples of the fluorine-containing surfactant include the Magaface DS series (chemical industry journal, 2016, 2, 22 days) (Nissan industry News, 2016, 2, 23 days), such as Magaface DS-21, manufactured by DIC CORPORATION.
Further, as the fluorine-based surfactant, a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound is also preferably used. Such a fluorine-based surfactant can be described in Japanese patent application laid-open No. 2016-216602, and the contents thereof are incorporated herein.
The fluorine-based surfactant may be a block polymer. Examples thereof include compounds described in Japanese patent application laid-open No. 2011-089090. The fluorine-containing surfactant can also preferably use a fluorine-containing polymer compound containing: a repeating unit derived from a (meth) acrylate compound having a fluorine atom; and a repeating unit derived from a (meth) acrylate compound having 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups). The following compounds are also exemplified as the fluorine-based surfactant used in the present invention.
[ chemical formula 19]
The weight average molecular weight of the above compound is preferably 3000 to 50000, for example 14000. In the above compound,% representing the proportion of the repeating unit is mol%.
Further, as the fluorine-containing surfactant, a fluoropolymer having an ethylenically unsaturated bond group in a side chain can be used. Specific examples thereof include compounds described in paragraphs 0050 to 0090 and paragraphs 0289 to 0295 of Japanese patent application laid-open No. 2010-164965, such as Magaface RS-101, RS-102 and RS-718K, RS-72-K manufactured by DIC CORPORATION. As the fluorine-based surfactant, the compounds described in paragraphs 0015 to 0158 of Japanese patent laid-open publication No. 2015-117327 can be used.
Examples of the nonionic surfactant include glycerol, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (e.g., glycerol propoxylate, glycerol ethoxylate), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, PLURONIC L10, L31, L61, L62, 10R5, 17R2, 25R2 (manufactured by BASF Co., Ltd.), TETRONIC 304, 701, 704, 901, 904, 150R1 (manufactured by BASF Co., Ltd.), SOLSPERSE20000 (manufactured by Lubrizol Japan Ltd.), NCW-101, NCW-1001, NCW-1002 (manufactured by Wako Pure), PIONIN D-6112, D-6112-W, D-6315(Takemoto Co., Ltd., Fakeo Co., Ltd., Japan, and the like, ltd), OLFIN E1010, Surfynol 104, 400, 440(Nissin Chemical co., ltd), and the like.
Examples of the silicon-based surfactant include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (manufactured by Dow Corning Toray Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials Inc.), KP-341, KF-6001, KF-6002 (manufactured by Shin-Etsu Chemical Co., Ltd.), BYK307, BYK323, and Chemie 330 (manufactured by BYK).
The content of the surfactant in the total solid content of the lens composition is preferably 0.001 to 5.0% by mass, and more preferably 0.005 to 3.0% by mass. The number of the surfactants may be only 1, or may be 2 or more. When the number of the compounds is 2 or more, the total amount of these compounds is preferably in the above range.
Other additives
The lens composition of the present invention may contain various additives such as fillers, adhesion promoters, antioxidants, and anti-agglomeration agents, as required. Examples of such additives include those described in paragraphs 0155 to 0156 of Japanese patent application laid-open No. 2004-295116, the contents of which are incorporated herein by reference. As the antioxidant, for example, a phenol compound, a phosphorus compound (e.g., the compound described in paragraph 0042 of jp 2011-an 090147), a thioether compound, or the like can be used. Examples of commercially available products include the Adekastab series (AO-20, AO-30, AO-40, AO-50F, AO-60, AO-60G, AO-80, AO-330, etc.) manufactured by ADEKA CORPORATION. Further, as the antioxidant, a polyfunctional hindered amine antioxidant described in international publication No. 2017/006600, an antioxidant described in international publication No. 2017/164024, and an antioxidant described in paragraphs 0023 to 0048 of japanese patent No. 6268967 can be used. The antioxidant may be used in 1 type or 2 or more types. The lens composition of the present invention may contain a latent antioxidant, if necessary. The latent antioxidant includes a compound in which a site functioning as an antioxidant is protected with a protecting group, and the protecting group is released by heating at 100 to 250 ℃ or heating at 80 to 200 ℃ in the presence of an acid/base catalyst to function as an antioxidant. Specific examples of latent antioxidants include compounds described in international publication nos. WO2014/021023, 2017/030005 and 2017-008219. Examples of commercially available products include ADEKAARKLS GPA-5001 (manufactured by ADEKA CORPORATION). The lens composition of the present invention may contain a sensitizer or photostabilizer described in paragraph 0078 of Japanese patent application laid-open No. 2004-295116 and a thermal polymerization inhibitor described in paragraph 0081 of Japanese patent application laid-open No. 2004-295116.
The lens composition of the present invention preferably contains substantially no color colorant or black colorant. The case where the lens composition of the present invention contains substantially no color colorant and no black colorant means that the total content of the color colorant and the black colorant is 0.1 mass% or less, preferably 0.05 mass% or less, more preferably 0.01 mass% or less, and particularly preferably contains no color colorant and no black colorant in the total solid content of the lens composition. The color colorant mentioned here does not contain the white pigment.
The viscosity (25 ℃) of the lens composition of the present invention is preferably 1.5 to 10 mPas. The lower limit is preferably 2.0 mPas or more, more preferably 2.5 mPas or more. The upper limit is preferably 9.5 mPas or less, more preferably 9.0 mPas or less. When the viscosity is within the above range, the coating property is excellent.
The solid content concentration of the lens composition of the present invention is preferably 15 to 50 mass%. The lower limit is preferably 20% by mass or more, and more preferably 25% by mass or more. The upper limit is preferably 45% by mass or less, more preferably 40% by mass or less. If the solid content concentration is within the above range, a lens in which wrinkles or voids are suppressed can be easily produced.
The content of free metal not bonded or coordinated to the pigment or the like in the lens composition of the present invention is preferably 100ppm or less, more preferably 50ppm or less, further preferably 10ppm or less, and particularly preferably substantially none. According to this embodiment, effects such as stabilization of pigment dispersibility (inhibition of aggregation), improvement of spectral characteristics associated with improvement of dispersibility, stabilization of curable components, inhibition of variation in conductivity associated with elution of metal atoms/metal ions, and improvement of display characteristics can be expected. Further, the effects described in Japanese patent laid-open Nos. 2012-153796, 2000-345085, 2005-200560, 08-043620, 2004-145078, 2014-119487, 2010-083997, 2017-090930, 2018-025612, 2018-025797, 2017-155228, 2018-036521 and the like can be obtained. Examples of the kind of the free metal include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, Cs, and Bi. In the lens composition of the present invention, the content of free halogen not bonded or coordinated to a pigment or the like is preferably 100ppm or less, more preferably 50ppm or less, further preferably 10ppm or less, and particularly preferably substantially none. Examples of the method for reducing the amount of free metal or halogen in the composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.
The lens composition of the present invention preferably does not contain terephthalate.
< storage Container >
The container for containing the lens composition of the present invention is not particularly limited, and a known container can be used. Further, as the storage container, it is also preferable to use a multilayer bottle made of 6 kinds of 6-layer resins or a bottle having a 7-layer structure of 6 kinds of resins for the inner wall of the container for the purpose of suppressing impurities from being mixed into the raw material or the lens composition. Examples of such a container include those described in Japanese patent laid-open publication No. 2015-123351.
< method for producing composition for lens >
The lens composition of the present invention can be produced by mixing the above components. When producing the composition for a lens, the composition for a lens may be produced by dissolving and/or dispersing all the components in a solvent at the same time, or may be produced by mixing the components at the time of use (at the time of coating) as a solution or dispersion liquid in which 2 or more components are appropriately contained as necessary.
Further, a process of dispersing particles such as a pigment may be included in the production of the composition for a lens. In the process of dispersing the pigment, the mechanical force used for dispersing the pigment may be compression, pressing, impact, shearing, cavitation, or the like. Specific examples of these processes include bead mills, sand mills (sand mills), roll mills, ball mills, paint mixers (paint shakers), microfluidizers (microfluidizers), high-speed impellers, sand mills, jet mixers (flowjet mixers), high-pressure wet atomization, ultrasonic dispersion, and the like. In addition, in the pulverization of the pigment in the sand mill (bead mill), it is preferable to perform the treatment under the conditions that the pulverization efficiency is improved by using beads having a small diameter, increasing the packing ratio of the beads, or the like. After the pulverization treatment, it is preferable to remove coarse particles by filtration, centrifugation, or the like. Further, the process and the dispersing machine for dispersing the pigment can be preferably used as described in "the general term of dispersion technology, johaokiko co., ltd. release, 7/15/2005" or "the actual data set on the dispersion technology and industrial application centered on suspension (solid/liquid dispersion system), published by the department of business development center, 10/1978" and paragraph 0022 of japanese patent application laid-open No. 2015-157893 ". In the process of dispersing the pigment, the particle size reduction treatment can be performed by a salt milling (salt milling) step. Materials, equipment, processing conditions, and the like used in the salt milling step can be described in, for example, japanese patent application laid-open nos. 2015-194521 and 2012-046629.
When the composition for a lens is produced, it is preferable to filter the composition for a lens by a filter for the purpose of removing foreign matter, reducing defects, and the like. The filter may be used without particular limitation as long as it is a filter that has been used for filtration purposes and the like. Examples of the filter include filters made of materials such as a fluororesin such as Polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (e.g., nylon-6, 6), and a polyolefin resin (including a high-density, ultrahigh-molecular-weight polyolefin resin) such as Polyethylene and Polypropylene (PP). Of these materials, polypropylene (including high density polypropylene) and nylon are preferred.
The pore diameter of the filter is preferably 0.01 to 7.0. mu.m, more preferably 0.01 to 3.0. mu.m, and still more preferably 0.05 to 0.5. mu.m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably. As regards the pore size value of the filter, reference can be made to the nominal value of the filter manufacturer. The filters can be any of the various filters provided by NIHON PALL LTD. (DFA4201NIEY, etc.), Advantec Toyo Kaisha, Ltd., Nihon Entegris K.K, (for merly Nippon micro liquid Co., Ltd.), and KITZMICORFITER CORPORATION, etc.
Further, a fibrous filter material is also preferably used as the filter. Examples of the fibrous filter material include polypropylene fibers, nylon fibers, and glass fibers. Commercially available products include ROKI TECHNO CO, SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by LTD.
When a filter is used, different filters (for example, the 1 st filter and the 2 nd filter) may be combined. In this case, the filtration by each filter may be performed only 1 time, or may be performed 2 times or more. Also, filters of different pore sizes may be combined within the above range. The filtration by the 1 st filter may be performed only on the dispersion, or the filtration may be performed by the 2 nd filter after mixing other components.
< lens >
The lens of the present invention is a lens obtained from the above-mentioned composition for a lens of the present invention. The maximum value of absorbance at a wavelength of 400 to 700nm of the lens of the present invention is preferably 0.05 or less, more preferably 0.04 or less, and still more preferably 0.03 or less. The transmittance of the lens of the present invention for light having a wavelength of 400 to 700nm is preferably 90% or more, more preferably 91.5% or more, and still more preferably 93% or more. The refractive index of the lens of the present invention for light having a wavelength of 550nm is preferably 1.5 or more, more preferably 1.52 or more, and still more preferably 1.54 or more. The upper limit is preferably 2.0 or less, more preferably 1.85 or less.
As the lens shape, various shapes derived by optical system design can be adopted, and examples thereof include a convex shape, a concave shape, and the like. For example, by forming the lens in a concave shape (concave lens), the light condensing property of light can be easily improved.
The radius of curvature of the lens is preferably within a range that exhibits a desired effect, and is not particularly limited.
The thickness of the lens is preferably 0.5 to 3.0 μm. The upper limit is preferably 2.5 μm or less, more preferably 2.0 μm or less. The lower limit is preferably 0.7 μm or more, more preferably 0.9 μm or more. Here, the thickness of the lens means the thickness of the thickest part of the lens. For example, in the case of a biconvex lens, the distance from the apex of one convex surface to the apex of the other convex surface is referred to.
The lens of the present invention is used in a display device having a color filter, and is disposed on an optical path of light transmitted through the color filter. The lens of the present invention may be provided on the incident light side to be incident on the color filter, or may be provided on the outgoing light side to be emitted from the color filter. When the light source is provided on the incident light side to the color filter, the amount of light condensed on the color filter can be increased. In addition, when the light source is provided on the light emission side of the color filter, the amount of light condensed on the display can be increased. The lens of the present invention may be in direct contact with the color filter, or another layer such as an adhesive layer or a planarization layer may be provided between the lens of the present invention and the color filter. The lens of the present invention can be arranged and used as described in international publication No. 2018/135189.
Examples of a display device using the lens of the present invention include an organic electroluminescence display device, a liquid crystal display device, and the like, and an organic electroluminescence display device is preferable.
< method for manufacturing lens >
Next, a method for manufacturing a lens of the present invention will be described. The method for producing a lens of the present invention includes a step of applying the composition for a lens of the present invention on a support to form a composition layer, and a step of processing the composition layer into a lens shape.
In the method for producing a lens of the present invention, the entire process is preferably performed at a temperature of 150 ℃ or lower, more preferably at a temperature of 120 ℃ or lower, and still more preferably at a temperature of 100 ℃ or lower. By manufacturing the lens in this manner, the lens with wrinkles or few voids is easily formed by suppressing the heat shrinkage of the film. Further, damage to the support body due to heat can be reduced. In particular, the organic light-emitting layer such as an organic electroluminescent element tends to have low heat resistance, and damage to the organic light-emitting layer due to heat can be reduced by performing a curing treatment at a low temperature of 150 ℃ or lower (preferably 120 ℃ or lower).
(Process for Forming composition layer)
Next, each step will be described. In the step of forming the composition layer, the composition layer is formed on the support using the composition for a lens of the present invention. Examples of the support include a glass substrate, a polycarbonate substrate, a polyester substrate, an aromatic polyamide substrate, a polyamideimide substrate, and a polyimide substrate. Organic light emitting layers may be formed on these substrates. Also, a color filter may be further formed on the organic light emitting layer. The substrate or the color filter may be provided with an undercoat layer for improving adhesion to an upper layer, preventing diffusion of a substance, or planarizing the surface.
As a method for applying the composition for a lens, a known method can be used. For example, a dropping method (drop casting: drop cast); slit coating method; spraying; a roll coating method; spin coating method (spin coating method); tape casting coating method; slit spin coating; a prewet method (for example, the method described in Japanese patent laid-open No. 2009-145395); various printing methods such as discharge printing such as ink jet (e.g., on-demand, piezoelectric, and thermal), nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing; a transfer method using a mold or the like; nanoimprint method, and the like. The application method by the ink jet is not particularly limited, and examples thereof include a method shown in "unlimited possibility in the expansion and usable ink jet-patent", release in 2.2005, s.b. reset co., ltd. "(especially from 115 to 133 pages), and a method described in japanese patent laid-open publication nos. 2003-262716, 2003-185831, 2003-261827, 2012-126830, and 2006-1699325. Further, as for the method for applying the curable composition, reference can be made to the descriptions of international publication No. 2017/030174 and international publication No. 2017/018419, and these contents are incorporated in the present specification.
The composition layer formed on the support may also be dried (prebaked). When the prebaking is performed, the prebaking temperature is preferably 100 ℃ or lower, more preferably 90 ℃ or lower, still more preferably 80 ℃ or lower, and particularly preferably 70 ℃ or lower. The lower limit can be set to 40 ℃ or higher, for example. The pre-baking time is preferably 10-3600 seconds. The prebaking can be performed using a hot plate, an oven, or the like.
(Process of shaping into lens shape)
As a method for processing the composition layer into a lens shape, a conventionally known processing method can be used. For example, the optical film can be manufactured by a transfer method, an imprint method, a heat sagging method (heat scattering), or the like. Among these, the transfer method is preferable for the reason of facilitating the control of the lens shape.
In the transfer method, the composition layer formed on the support is cured to form a cured product layer, a resist layer is formed on the cured product layer, the resist layer is patterned into a lens shape, and the cured product layer is dry-etched using the patterned resist layer as a mask to transfer the lens shape to the cured product layer. Further, as the method for producing a lens using the transfer method, the methods described in japanese patent laid-open nos. 2006-.
In the imprint method, the composition layer can be produced by pressing a mold having a pattern on the composition layer formed on the support to sandwich the composition layer between the mold and the support, exposing the composition layer to light in a state where the composition layer is sandwiched between the mold and the support and curing the exposed composition layer, and then peeling the mold from the support.
In the thermal sag method, a composition layer formed on a support is cured to form a cured material layer, and the surface of the cured material layer is thermally sagged by heating the cured material layer, whereby the cured material layer can be processed into a lens shape.
The step of processing into a lens shape preferably includes a step of exposing the composition layer. Thereby, the composition layer of the exposed portion can be cured. The exposure serves as a curing process for the composition layer. The exposure is preferably performed by irradiating the composition layer with radiation. Examples of the radiation include g-line and i-line. Light having a wavelength of 300nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300nm or less include KrF line (wavelength: 248nm) and ArF line (wavelength: 193nm), and KrF line (wavelength: 248nm) is preferable. Further, a long-wave light source of 300nm or more can be used.
In addition, during exposure, exposure may be performed by continuous irradiation or exposure may be performed by pulsed irradiation (pulse exposure). The pulse exposure is an exposure method in which exposure is performed by repeating irradiation and stop of light in a short time (for example, millisecond order or less) cycle. In the case of pulse exposure, the pulse width is preferably 100 nanoseconds (ns) or less, more preferably 50 nanoseconds or less, and still more preferably 30 nanoseconds or less. The lower limit of the pulse width is not particularly limited, and may be 1 femtosecond (fs) or more, or 10 femtoseconds or more. The frequency is preferably 1kHz or more, more preferably 2kHz or more, and further preferably 4kHz or more. The upper limit of the frequency is preferably 50kHz or less, more preferably 20kHz or less, and further preferably 10kHz or less. The maximum instantaneous illumination intensity is preferably 50000000W/m2Above, more preferably 100000000W/m2The above, more preferably 200000000W/m2The above. Further, the upper limit of the maximum instantaneous illuminance is preferably 1000000000W/m2Hereinafter, 800000000W/m is more preferable2Hereinafter, 500000000W/m is more preferable2The following. The pulse width is a time during which light is irradiated in a pulse period. And, the frequency refers to the number of pulse cycles per second. The maximum instantaneous illuminance is an average illuminance over the time period in which light is irradiated in the pulse period. The pulse period is a period in which irradiation and stop of light in pulse exposure are 1 cycle.
The dose (exposure) is preferably 0.03 to 2.5J/cm2More preferably 0.05 to 1.0J/cm2. The oxygen concentration at the time of exposure can be appropriately selected, and in addition to the atmospheric air, for example, exposure may be performed in a low oxygen atmosphere (for example, 15 vol%, 5 vol%, or substantially no oxygen) in which the oxygen concentration is 19 vol% or less, or exposure may be performed in a high oxygen atmosphere (for example, 22 vol%, 30 vol%, or 50 vol%) in which the oxygen concentration is more than 21 vol%. The exposure illuminance can be set appropriately, and can be usually setFrom 1000W/m2～100000W/m2(e.g., 5000W/m)2、15000W/m2、35000W/m2) Is selected. The oxygen concentration and the exposure illuminance may be combined under appropriate conditions, and for example, the oxygen concentration may be 10 vol% and the illuminance may be 10000W/m2An oxygen concentration of 35 vol% and an illuminance of 20000W/m2And the like.
The composition layer may be exposed in a pattern in the exposure treatment of the composition layer. For example, the composition layer can be exposed in a pattern form by exposing the composition layer through a mask having a predetermined mask pattern by using a stepper, a scanner, or the like. Thereby, the composition layer of the exposed portion can be selectively cured. Further, the unexposed portion of the composition layer is removed by development, whereby a pattern can be formed. The development removal of the unexposed portion of the composition layer can be performed using a developer. The temperature of the developing solution is preferably 20 to 30 ℃. The developing time is preferably 20 to 180 seconds. Further, in order to improve the residue removal property, a process of throwing off the developer every 60 seconds and further supplying the developer again may be repeated several times. Examples of the developer include an organic solvent and an alkali developer. The alkali developing solution is preferably an alkaline aqueous solution obtained by diluting an alkaline agent with pure water. Examples of the alkali agent include organic basic compounds such as ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, and 1, 8-diazabicyclo [5.4.0] -7-undecene, and inorganic basic compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate, and sodium metasilicate. As the alkaline agent, a compound having a large molecular weight is preferable in terms of environment and safety. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. Also, the developing solution may further include a surfactant. The surfactant includes the above-mentioned surfactants, and preferably a nonionic surfactant. From the viewpoint of easy transportation and storage, the developer may be once prepared as a concentrated solution and diluted to a desired concentration when used. The dilution ratio is not particularly limited, and can be set, for example, in the range of 1.5 to 100 times. Further, it is also preferable to perform cleaning (rinsing) with pure water after the development. In addition, it is preferable that the rinsing is performed by rotating the support on which the composition layer after development is formed and supplying the rinsing liquid to the composition layer after development. It is also preferable that the rinse liquid is discharged by moving a nozzle from the center of the support to the peripheral edge of the support. In this case, the nozzle may be moved while gradually decreasing the moving speed of the nozzle when moving from the center portion to the peripheral portion of the support body of the nozzle. By performing flushing in this way, in-plane variations in flushing can be suppressed. The same effect can be obtained by moving the nozzle from the central portion to the peripheral portion of the support body and gradually decreasing the rotation speed of the support body.
The heat treatment (post-baking) may be performed after the exposure (after the development, and after the drying). The heating temperature is preferably 100 to 150 ℃, and more preferably 100 to 120 ℃. The heating time is preferably 1 minute or more, more preferably 5 minutes or more, and further preferably 10 minutes or more. The upper limit is not particularly limited, and from the viewpoint of productivity, 300 minutes or less is preferable. The post-baking is also preferably performed under an atmosphere of an inert gas. According to this aspect, thermal polymerization can be performed with very high efficiency without being affected by oxygen, and even when a lens is produced at a temperature of 150 ℃ or lower (preferably 120 ℃ or lower) throughout all steps, a lens having excellent characteristics such as solvent resistance can be produced. The inert gas includes nitrogen, argon, helium, and the like, and nitrogen is preferable. The oxygen concentration at the time of post-baking is preferably 100ppm or less.
In the present invention, the step of processing into a lens shape preferably includes subjecting the composition layer to a treatment of 1J/cm2And irradiating the light with an exposure amount of at least 350nm and at most 380 nm. By performing exposure in this manner, the composition layer can be sufficiently cured, and even when a lens is produced at a temperature of 150 ℃ or lower throughout all steps, excellent properties such as solvent resistance can be producedA hetero lens.
In the present invention, the step of processing into a lens shape preferably includes a step of irradiating the composition layer with light having a wavelength of more than 350nm and 380nm or less to perform exposure (hereinafter, also referred to as exposure 1), and then further irradiating the composition layer with light having a wavelength of 254 to 350nm to perform exposure (hereinafter, also referred to as exposure 2). In this manner, the composition layer can be sufficiently cured, and even when a lens is produced at a temperature of 150 ℃ or lower throughout all steps, a lens having excellent properties such as solvent resistance can be produced.
In forming a pattern, it is preferable that the composition layer is exposed to light having a wavelength of more than 350nm and 380nm or less in a patterned state (exposure 1), the composition layer after the exposure 1 is developed, and the composition layer after the development is exposed to light having a wavelength of 254 to 350nm (exposure 2). By exposing the composition layer in two stages, i.e., before development and after development, the composition can be appropriately cured by the first exposure (exposure before development), and the entire composition can be almost completely cured by the next exposure (exposure after development). As a result, the composition can be sufficiently cured even under low temperature conditions, and a pattern excellent in solvent resistance, adhesiveness, and rectangularity can be formed.
The light used in the exposure 1 is light having a wavelength of more than 350nm and 380nm or less, preferably light having a wavelength of 355 to 370nm, and more preferably i-line. The dose (exposure dose) is preferably 30 to 1500mJ/cm2More preferably 50 to 1000mJ/cm2. The oxygen concentration at the time of exposure can be appropriately selected.
The light used in the exposure 2 has a wavelength of 254 to 350nm, and preferably 254 nm. The exposure 2 can be performed by, for example, an ultraviolet photoresist curing apparatus. The ultraviolet photoresist curing device may be irradiated with light having a wavelength of 254 to 350nm and other light (i-ray, for example). The difference between the wavelength of light used in the exposure 1 and the wavelength of light used in the exposure 2 is preferably 200nm or less, and more preferably 100 to 150 nm. The dose (exposure dose) of the exposure 2 is preferably 30 to 4000mJ/cm2More preferably 50 to 3500mJ/cm2. Regarding the oxygen concentration at the time of exposure, canCan be appropriately selected.
< display device >
The display device of the present invention has the lens and the color filter of the present invention described above. In the display device of the present invention, the lens is disposed on the optical path of the light transmitted through the color filter. Examples of the color filter include filters having colored pixels such as red pixels, blue pixels, green pixels, cyan pixels, magenta pixels, and yellow pixels of 1 color or more. Specific examples of the color filter include a filter having at least a red pixel, a blue pixel, and a green pixel, a filter having at least a cyan pixel, a magenta pixel, and a yellow pixel, and the like. The color filter can be manufactured using a coloring composition containing a color colorant.
In the display device of the present invention, the color filter included in the display device has pixels of a plurality of colors, and the lens of the present invention is preferably formed on the optical path of at least a part of the pixels.
The color filter may have a structure in which each colored pixel is filled in a space partitioned into, for example, a lattice shape by a partition wall. The partition walls in this case are preferably low in refractive index for each colored pixel. The partition walls may be formed in the structure described in US 2018/0040656.
Examples of the display device include a liquid crystal display device and an organic electroluminescence display device. The definition of the display device and the details of each image display device are described in, for example, "electronic display device (published by gazozu shoff, Kogyo Chosakai Publishing co., ltd.1990)", "display device (published by yibushu, Sangyo-Tosho Publishing co.ltd., 1989)", and the like. The liquid crystal display device is described in, for example, "next generation liquid crystal display technology (edited by infiniband man, Kogyo Chosakai Publishing co., ltd., 1994)". The liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, liquid crystal display devices of various types described in the "next generation liquid crystal display technology" described above.
The organic electroluminescent display device may have a light source composed of a white organic electroluminescent element. As the white organic electroluminescent element, a tandem structure is preferable. The tandem structure of organic electroluminescent elements is described in japanese patent application laid-open No. 2003-045676, the third best effort supervision, "the first line of organic EL technology development-high brightness, high precision, long lifetime, and know-how collection-", the association of technical information, page 328 of 326-045676, and 2008. The spectrum of white light emitted from the organic EL element preferably has strong maximum emission peaks in the blue region (430nm-485nm), green region (530nm-580nm), and yellow region (580nm-620 nm). In addition to these light emission peaks, it is more preferable to further have a maximum light emission peak in a red region (650nm to 700 nm).
Examples
The present invention will be specifically described below with reference to examples. The materials, the amounts used, the ratios, the processing contents, the processing steps, and the like shown in the following examples can be appropriately modified without departing from the spirit of the present invention. Accordingly, the scope of the present invention is not limited to the specific examples shown below.
< preparation of pigment Dispersion >
(pigment Dispersion liquid T1)
A mixed liquid having the following composition a was subjected to dispersion treatment as described below using an Ultra Apex Mill (product name) manufactured by Kotobuki Industries co., ltd., as a circulation type dispersing device (bead Mill) to prepare a pigment dispersion liquid T1.
(composition A)
White pigments (using aluminum hydroxide (Al (OH))3) Amorphous silicon dioxide (SiO)2) And stearic acid (C)17H35COOH) … … 22.8.8 parts by mass of particles (containing 75% by mass or more of titanium dioxide, less than 15% by mass of aluminum hydroxide, less than 5% by mass of amorphous silica, less than 10% by mass of stearic acid), the particle surfaces of which have been surface-treated with a surface-treating agent of COOH) … …
… … 6.1.1 parts by mass of a dispersant (resin having the following structure, acid value: 50mgKOH/g, weight average molecular weight: 10,000, numerical values attached to the main chain as a molar ratio, and numerical values attached to the side chains as the number of repeating units)
[ chemical formula 20]
… … 71.1.1 parts by mass of Propylene Glycol Monomethyl Ether Acetate (PGMEA)
The dispersion apparatus was operated under the following conditions.
Bead diameter: diameter of 0.05mm
Bead filling ratio: 75% by volume
Peripheral speed: 8m/sec
Pump supply amount: 10Kg/hour
Cooling water: tap water
Internal volume of annular passage of bead mill: 0.15L
Amount of mixed liquid for dispersion treatment: 0.44kg
< preparation of composition for lens >
(example 1)
The following raw materials were mixed and stirred, and then filtered through a nylon filter (manufactured by NIHON fill ltd.) having a pore size of 0.45 μm to prepare a composition for a lens.
Photopolymerization initiator A1 (initiator 1) … … 1.75.75 parts by mass
Photopolymerization initiator A2 (initiator 4) … … 1.41.41 parts by mass
… … 39.54.54 parts by mass of resin (40% by mass PGMEA solution of resin 1)
Polymerizable monomer M1 … … 28.84.84 parts by mass
… … 0.008.008 parts by mass of polymerization inhibitor 1 (p-methoxyphenol)
… … 0.021.021 parts by mass of surfactant 1(a compound having the following structure, Mw 14000, and the numerical value of% indicating the proportion of the repeating unit is mol%) (iii)
[ chemical formula 21]
… … 0.175.175 parts by mass of silane coupling agent 1(KBM-602, manufactured by Shin-Etsu Chemical Co., Ltd.)
PGMEA … … 28.25.25 parts by mass
(examples 2 to 15, 17 to 33, comparative example 1)
A lens composition was prepared in the same manner as in example 1, except that the kind and content of the photopolymerization initiator, the kind of the resin, the kind of the polymerizable monomer, the kind of the solvent, and the total solid content of the lens composition were changed as shown in the following table. In addition, the total solid content of the lens composition was adjusted by changing the blending amount of the solvent.
(example 16)
The following raw materials were mixed and stirred, and then filtered through a nylon filter (manufactured by NIHON fill ltd.) having a pore size of 0.45 μm to prepare a composition for a lens.
69.29 parts by mass of pigment Dispersion T1 … … 69.29
Photopolymerization initiator A1 (initiator 1) … … 1.75.75 parts by mass
Photopolymerization initiator A2 (initiator 4) … … 1.41.41 parts by mass
… … 9.29.29 parts by mass of resin (40% by mass PGMEA solution of resin 1)
14.52 parts by mass of a polymerizable monomer M1 … … 14.52
Polymerization inhibitor 1 … … 0.008.008 parts by mass
Surfactant 1 … … 0.021.021 parts by mass
Silane coupling agent 1 … … 17.5.5 parts by mass
PGMEA … … 3.57.57 parts by mass
[ Table 1]
The numerical values in the column of the content in the table are values of the content (% by mass) of the photopolymerization initiator a1 or the photopolymerization initiator a2 in the total solid content of the lens composition.
(photopolymerization initiator)
Initiator 1: IRGACURE-OXE01 (a compound having the following structure, manufactured by BASF corporation, and having an absorption coefficient of 69669 mL/gcm at 365nm in methanol. the maximum value of absorbance of an initiator coating film measured by the following method was 0.01.)
Initiator 2: IRGACURE-OXE02 (a compound having the following structure, manufactured by BASF corporation, and having an absorption coefficient of 7749mL/gcm at 365nm in methanol. the maximum value of absorbance of an initiator coating film measured by the following method was 0.01.)
Initiator 3: a compound having the following structure (absorption coefficient of light having a wavelength of 365nm in methanol: 18900 mL/gcm; maximum value of absorbance of an initiator-coated film measured by the following method: 0.02.)
Initiator 4: IRGACURE-2959 (a compound having the following structure, manufactured by BASF corporation, and having an absorption coefficient of 48.93mL/gcm at 365nm in methanol and an absorption coefficient of 3.0X 10 at 254nm4mL/gcm. The maximum value of absorbance of the initiator-coated film measured by the following method was 0.005. )
Initiator 5: IRGACURE-184 (a compound having the following structure, manufactured by BASF corporation, having an absorption coefficient of 88.64mL/gcm at 365nm in methanol and an absorption coefficient of 3.3X 10 at 254nm4mL/gcm. The maximum value of absorbance of the initiator-coated film measured by the following method was 0.004. )
Initiator 6: a compound having the following structure (absorption coefficient of light having a wavelength of 365nm in methanol: 13200 mL/gcm. maximum value of absorbance of an initiator-coated film measured by the following method: 0.13.)
[ chemical formula 22]
(polymerizable monomer)
M1: a compound of the structure
[ chemical formula 23]
M2: ARONIX M-309(TOAGOSEI CO., LTD. manufactured, trimethylolpropane triacrylate)
M3: ARONIX M-310(TOAGOSEI CO., LTD. manufactured, trimethylolpropane polyoxypropylene modified triacrylate)
M4: ARONIX M-350(TOAGOSEI CO., LTD. manufactured, trimethylolpropane polyoxyethylene modified triacrylate)
M5: ARONIX M-408(TOAGOSEI CO., LTD. manufactured, ditrimethylolpropane tetraacrylate)
(resin)
Resin 1: a resin having the following structure (Mw 11000, acid value 31.5mgKOH/g, and the number attached to the main chain is a molar ratio.)
[ chemical formula 24]
Resin 2: resin synthesized by the following method
70.0 parts by mass of cyclohexanone was added to a separable 4-neck flask equipped with a thermometer, a cooling tube, a nitrogen introduction tube, a dropping tube, and a stirring device, the flask was heated to 80 ℃ and the nitrogen in the flask was replaced, and then a mixture of 13.3 parts by mass of n-butyl methacrylate, 4.6 parts by mass of 2-hydroxyethyl methacrylate, 4.3 parts by mass of methacrylic acid, and 7.4 parts by mass of cumylphenol ethylene oxide-modified acrylate (toagaei osco., ltd., ARONIX M110) and 0.4 part by mass of 2, 2' -azobisisobutyronitrile was dropped through the dropping tube over 2 hours. After the completion of the dropwise addition, the reaction was continued for further 3 hours to obtain a 30 mass% solution of resin 2(Mw 26000).
Resin 3: resin synthesized by the following method
90.0 parts by mass of propylene glycol monomethyl ether acetate was charged into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser and a gas inlet tube, and heated to 60 ℃ while injecting nitrogen gas into the vessel, and a mixture of 50.0 parts by mass of furfuryl methacrylate, 26.7 parts by mass of 2-methacryloyloxyethylsuccinic acid, 23.3 parts by mass of 2-hydroxyethyl methacrylate and 2.5 parts by mass of 2, 2' -azobis (2, 4-dimethylvaleronitrile) was added dropwise at the same temperature over 2 hours to carry out polymerization reaction. After completion of the dropwise addition, the reaction mixture was further reacted at 60 ℃ for 1 hour, and then a solution prepared by dissolving 0.5 part by mass of 2, 2' -azobis (2, 4-dimethylvaleronitrile) in 10.0 parts by mass of propylene glycol monomethyl ether acetate was added, followed by continuous stirring at the same temperature for 3 hours to obtain a copolymer. After cooling to room temperature, a 20 mass% solution of resin 3(Mw 52000) was obtained by dilution with propylene glycol monomethyl ether acetate.
Resin 4: a resin having the following structure (Mw 30000, the number attached to the main chain being a molar ratio.)
[ chemical formula 25]
Resin 5: resin synthesized by the following method
90.0 parts by mass of propylene glycol monomethyl ether acetate was charged into a reaction vessel equipped with a stirrer, a thermometer, a dropping device, a reflux condenser and a gas inlet tube, and heated to 60 ℃ while injecting nitrogen gas into the vessel, and a mixture of 35.0 parts by mass of glycidyl methacrylate, 45.0 parts by mass of methyl methacrylate and 2.5 parts by mass of 2, 2' -azobisisobutyronitrile was added dropwise at the same temperature over 2 hours to carry out polymerization reaction. After completion of the dropwise addition, the reaction mixture was further reacted at 60 ℃ for 1 hour, and then a solution prepared by dissolving 0.5 part by mass of 2, 2' -azobisisobutyronitrile in 10.0 parts by mass of propylene glycol monomethyl ether acetate was added thereto, followed by continuous stirring at the same temperature for 3 hours to obtain a copolymer. Then, dry air was injected into the reaction vessel, 10.0 parts by mass of acrylic acid, 30.2 parts by mass of propylene glycol monomethyl ether acetate, 1.30 parts by mass of dimethylbenzylamine, and 0.26 parts by mass of methoquinone (methoquinone) were added, and the mixture was heated to 100 ℃ and stirred for 20 hours, and the acid value was measured, whereby it was confirmed that the target product was produced. Further, 10.0 parts by mass of tetrahydrophthalic anhydride and 27.7 parts by mass of propylene glycol monomethyl ether acetate were continuously added to the reaction vessel, and after stirring at 60 ℃ for 3 hours, the mixture was cooled to room temperature and then diluted with propylene glycol monomethyl ether acetate, thereby obtaining a 20 mass% solution of resin 5(Mw 12000).
(solvent)
PGMEA: propylene glycol monomethyl ether acetate
PGME: propylene glycol monomethyl ether
[ measurement of absorbance of initiator-coated film ]
Initiator composition 1 was prepared by mixing 1 part by mass of initiator 1, 47.5 parts by mass of resin, and 51.5 parts by mass of PGMEA.
Resin P1: propylene glycol monomethyl ether acetate solution of benzyl methacrylate/methacrylic acid (70/30 [ molar ratio ]) copolymer (40 mass% solid content, weight average molecular weight 30000, FUJIKURA KASEI co., ltd., Acrybase FF-187, manufactured by ltd.)
Initiator compositions 2 to 6 were prepared in the same manner as initiator composition 1 except that initiators 2 to 6 were used instead of initiator 1.
Each initiator composition was applied onto a glass substrate by a spin coater so that the film thickness after prebaking became 2.0 μm, and heat treatment (prebaking) was performed for 120 seconds by a hot plate at 100 ℃. The obtained coating film was measured for absorbance of light in the wavelength range of 400 to 700nm using a spectrophotometer (reference: glass substrate) of ultraviolet-visible near-infrared spectrophotometer UV3600 (manufactured by Shimadzu Corporation).
< evaluation >
(Absorbance and refractive index)
Each lens composition was coated on a glass substrate by a spin coater so that the thickness of the pre-baked composition became 2.0. mu.m, and the thickness was 100. mu.mThe hot plate was subjected to heat treatment (prebaking) at 120 ℃ for 120 seconds. Next, the film was exposed to light at 100mJ/cm by an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.)2The exposure dose of (2) irradiates the i-line. Next, using an ultraviolet photoresist curing apparatus (UMA-802-HC-552; manufactured by USHIO INC., Ltd.), at 3000mJ/cm2The cured film was produced by exposure to the above exposure amount.
The obtained cured film was measured for absorbance of light in the wavelength range of 400 to 700nm using a spectrophotometer (reference: glass substrate) of ultraviolet-visible near-infrared spectrophotometer UV3600 (manufactured by Shimadzu Corporation). The smaller the absorbance, the more excellent the transparency. The evaluation criteria of absorbance are as follows.
AA: the maximum value of absorbance in the whole range of the wavelength of 400-700 nm is less than 0.03.
A: the maximum value of absorbance in the whole range of wavelength 400-700 nm is more than 0.03 and less than 0.04.
B: the maximum value of absorbance in the whole range of wavelength 400-700 nm is more than 0.04 and less than 0.05.
C: the maximum value of absorbance in the whole range of wavelength 400-700 nm is 0.05 or more.
The refractive index of the obtained cured film was measured by an ellipsometer manufactured by j.a. woollam Japan co.
(solvent resistance)
The obtained cured film was subjected to solvent resistance test by dropping N-methylpyrrolidone (NMP), leaving it for 200 seconds, and rinsing it with running water for 10 seconds. The solvent resistance was evaluated by measuring the thickness of the film before and after the solvent resistance test and measuring the residual film ratio. The more the residual film ratio is close to 1, the more excellent the solvent resistance is.
Residual film ratio (thickness of cured film before and after solvent resistance test)/thickness of cured film before solvent resistance test
AA: the residual film ratio is 0.95 to 1.0.
A: the residual film ratio is 0.90 or more and less than 0.95.
B: the residual film ratio is 0.85 or more and less than 0.90.
C: the residual film rate is less than 0.85.
(rectangular)
Each lens composition was applied onto a glass substrate by a spin coating method so that the thickness of the composition after prebaking became 2.0 μm, and then heat treatment was performed for 120 seconds by a hot plate at 100 ℃. Next, the substrate was exposed by an i-line stepper through a mask formed with a 10 μm square island pattern at 100mJ/cm2The exposure amount of (a) exposes i-lines. Thereafter, the resultant was subjected to liquid-in-solution development at 23 ℃ for 60 seconds using a 0.3 mass% aqueous solution of tetramethylammonium hydroxide, followed by rinsing treatment. Then, at 3000mJ/cm2The exposure amount of (1) is used to expose light with a wavelength of 254-350 nm to form a pattern.
The width of the pattern formed on the glass substrate and the length of the diagonal line of the pattern were observed from directly above the glass substrate by a length measuring SEM (scanning electron microscope). The rectangularity was evaluated by the following criteria. Length of diagonal line of pattern/(width of pattern × 2)0.5) The closer to 1.0, the better the rectangularity.
AA: length of diagonal line of pattern/(width of pattern × 2)0.5) Is more than 0.95 and 1.0 or less.
A: length of diagonal line of pattern/(width of pattern × 2)0.5) Is more than 0.90 and 0.95 or less.
B: length of diagonal line of pattern/(width of pattern × 2)0.5) Is more than 0.80 and 0.90 or less.
C: length of diagonal line of pattern/(width of pattern × 2)0.5) Is 0.80 or less.
< wrinkling of the lens surface >
The composition for a lens was applied to an 8-inch (20.32cm) silicon wafer sprayed with hexamethyldisilazane by a spin coating method so that the film thickness after prebaking became 2.0 μm, and then heat treatment was performed for 120 seconds by a hot plate at 100 ℃. Next, an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) was used to expose a substrate having a thickness of 100 μmIsland pattern mask of square 100mJ/cm2The exposure dose of (2) irradiates the i-line. Thereafter, the silicon wafer on which the composition layer to be exposed was formed was placed on a horizontal rotary table of a rotary spray developing machine (DW-30 type; manufactured by Chemitronics co., ltd.) and subjected to liquid-coating development at 23 ℃ for 180 seconds using a 40% diluted solution of CD-2000 (manufactured by FUJIFILM Electronic Materials co., ltd.). Next, the silicon wafer was fixed to a horizontal rotary table by a vacuum chuck method, rotated at 50rpm by a rotation device, and subjected to rinsing treatment by supplying pure water in a shower form from a discharge nozzle from above the center of rotation, followed by spin drying. Next, the cured product was cured at 3000mJ/cm using an ultraviolet photoresist curing apparatus (UMA-802-HC-552; manufactured by USHIO INC., Ltd.)2The pattern is formed by performing exposure (post-exposure) with the exposure amount of (1).
Subsequently, a positive resist solution (HPR-204ESZ-9-5 mPas, manufactured by FUJIFILM Electronic Materials Co., Ltd.) was applied to the obtained pattern so that the dry film thickness became 0.5. mu.m, and heated at 90 ℃ for 1 minute by a hot plate. Then, the light transmittance of the central portion of each lens was 0%, and the light transmittance was adjusted to 300mJ/cm by using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon inc.) through a halftone mask in which the light transmittance was adjusted to increase as the light transmittance extended to the peripheral portion2The exposure dose of (2) irradiates the i-line. Subsequently, the substrate was subjected to liquid-in-solution development for 60 seconds at room temperature using an alkali developing solution (HPRD-429E, FUJIFILM Electronic Materials co., ltd.), and then further subjected to rinsing for 20 seconds using a spin shower using pure water. After that, the substrate was dried by high-speed rotation after being further washed with pure water, and further heated at 100 ℃ for 15 minutes by a hot plate to form a lens-shaped resist pattern.
The substrate obtained as above was subjected to dry etching treatment under the following conditions using a dry etching apparatus (manufactured by Hitachi High-Technologies corporation: U-621), and processed into a shape capable of being used as a microlens, to manufacture a lens.
(lens processing conditions)
RF (radio frequency) power: 800W
Antenna bias: 100W
Wafer bias: 500W
Internal pressure of the chamber: 0.5Pa
Substrate temperature: 50 deg.C
Type and flow rate of mixed gas: CF (compact flash)4/C4F6/O2175/25/50/200 ml/min
Photoresist etch rate: 140 nm/min
The obtained lens surface was observed with an optical microscope (500 times), and the surface was observed for wrinkling and evaluated according to the evaluation criteria shown below.
AA: no wrinkling was confirmed at all on the surface.
A: wrinkles were hardly confirmed on the surface.
B: wrinkling was slightly confirmed on the surface.
C: significant wrinkling was observed.
[ Table 2]
As shown in the above tables, examples 1 to 33 are excellent in the properties of absorbance and refractive index. In particular, the evaluation of the lens surface wrinkling was good for examples 1 to 16, 19, 20, 22 to 33. Further, both the solvent resistance and the rectangularity were evaluated to be B or more.
As a result of forming the lenses of examples 1 to 33 on the surface of the color filter of the display device having the color filter and mounting the lens on the display device, the luminance was better than that of the display device without the lenses of examples 1 to 33. In particular, the luminance of the display devices mounted with the lenses of examples 1 to 19, 20, 22 to 33 was particularly good.
On the other hand, the luminance of the display device with the lens of comparative example 1 was observed to be lower than that of the display device without the lens.
When evaluating the wrinkling of the lens surface, the lens was manufactured by the same method and the wrinkling result of the lens surface was observed, except that the post-exposure was performed instead of performing the post-exposure by performing the heat curing with the hot plate under the conditions of 230 ℃ for 15 minutes, and a larger amount of wrinkling was observed than when the post-exposure was performed to manufacture the lens.
The lens composition of example 12 or example 33 was coated on a glass substrate by a spin coater so that the thickness after prebaking became 2.0 μm, and was subjected to heat treatment (prebaking) for 120 seconds by a hot plate at 100 ℃. Next, the substrate was exposed by an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) at 3000mJ/cm2The cured film was produced by irradiating the i-line with the exposure of (1). The solvent resistance of the cured film obtained was evaluated in the same manner as described above, and the solvent resistance was evaluated as AA.
The lens composition of example 12 or example 33 was coated on a glass substrate by a spin coater so that the thickness after prebaking became 2.0 μm, and was subjected to heat treatment (prebaking) for 120 seconds by a hot plate at 100 ℃. Next, the film was exposed to light at 100mJ/cm by an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.)2The exposure dose of (2) irradiates the i-line. Subsequently, a cured film was produced by heating with a hot plate at 120 ℃ for 900 seconds. The solvent resistance of the cured film obtained was evaluated in the same manner as described above, and all the solvent resistances were evaluated as a.
The same effects as in each example can be obtained by forming a concave-shaped lens using the lens composition of each example.
Claims (22)
1. A composition for a lens for forming a lens on an optical path of light transmitted through a color filter in a display device having the color filter,
the composition for a lens comprises a polymerizable monomer M, a photopolymerization initiator A and a resin B,
when a film having a thickness of 2 μm is produced using the lens composition, the maximum value of the absorbance of the film at a wavelength of 400 to 700nm is 0.05 or less, and the refractive index of light having a wavelength of 550nm is 1.5 or more.
2. The composition for a lens according to claim 1, wherein,
the resin B contains a resin B1 containing a repeating unit derived from a compound represented by the following formula (I),
in the formula, X1Represents O or NH, and is selected from the group consisting of,
R1represents a hydrogen atom or a methyl group,
L1represents a linking group having a valence of 2,
R10represents a substituent group, and a pharmaceutically acceptable salt thereof,
m represents an integer of 0 to 2,
p represents an integer of 0 or more.
3. The composition for a lens according to claim 2, wherein,
the resin b1 further comprises repeating units derived from an alkyl (meth) acrylate.
4. The composition for a lens according to any one of claims 1 to 3,
the photopolymerization initiator a contains an oxime compound.
5. The composition for a lens according to any one of claims 1 to 4,
the photopolymerization initiator a includes:
an absorption coefficient of 1.0X 10 at a wavelength of 365nm in methanol3A photopolymerization initiator A1 of mL/gcm or more; and
an absorption coefficient of 1.0X 10 at a wavelength of 365nm in methanol2mL/gcm or less, and an absorption coefficient at a wavelength of 254nm of 1.0X 103A photopolymerization initiator A2 having a concentration of mL/gcm or more.
6. The composition for a lens according to claim 5, wherein,
the photopolymerization initiator a1 is an oxime compound containing a fluorine atom.
7. The composition for a lens according to claim 5 or 6, wherein,
the photopolymerization initiator A2 is a hydroxyalkyl benzophenone compound.
8. The composition for a lens according to any one of claims 5 to 7,
the photopolymerization initiator A2 is contained in an amount of 50 to 200 parts by mass based on 100 parts by mass of the photopolymerization initiator A1.
9. The composition for a lens according to any one of claims 5 to 8,
the total content of the photopolymerization initiator A1 and the photopolymerization initiator A2 in the total solid content of the lens composition is 5 to 15% by mass.
10. The composition for a lens according to any one of claims 1 to 9,
the polymerizable monomer M contains a compound containing 3 or more ethylenically unsaturated groups.
11. The composition for a lens according to any one of claims 1 to 10, comprising a silane coupling agent.
12. The composition for a lens according to any one of claims 1 to 11, which contains a compound containing a furyl group.
13. The composition for a lens according to claim 12, wherein,
the compound containing a furyl group is at least 1 selected from the group consisting of a compound represented by the following formula (fur-1) and a resin containing a repeating unit derived from a compound represented by the following formula (fur-1),
in the formula, Rf1Represents a hydrogen atom or a methyl group, Rf2Represents a 2-valent linking group.
14. A lens obtained from the composition for a lens of any one of claims 1 to 13.
15. A method of manufacturing a lens, the method comprising:
a step of forming a composition layer by applying the composition for a lens according to any one of claims 1 to 13 on a support; and
and a step of processing the composition layer into a lens shape.
16. The method for manufacturing a lens according to claim 15,
all the steps are carried out at a temperature of 150 ℃ or less.
17. The method for manufacturing a lens according to claim 15 or 16,
the step of processing into a lens shape comprises subjecting the composition layer to a temperature of 1J/cm2And irradiating the light with an exposure amount of at least 350nm and at most 380 nm.
18. The method for manufacturing a lens according to claim 15 or 16,
the step of processing into a lens shape includes a step of irradiating the composition layer with light having a wavelength of more than 350nm and 380nm or less to perform exposure, and then further irradiating the composition layer with light having a wavelength of 254nm to 350nm to perform exposure.
19. The method for manufacturing a lens according to any one of claims 15 to 18,
the step of processing into a lens shape includes a step of heating the composition layer at a temperature of 100 to 150 ℃ for 10 minutes or more.
20. The method for manufacturing a lens according to claim 19,
the heating step is performed in an inert gas atmosphere.
21. A display device having a color filter and a lens obtained from the composition for a lens described in any one of claims 1 to 13 provided on an optical path of light transmitting the color filter.
22. The display device according to claim 21, which is an organic electroluminescent display device.
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| JP2018159433 | 2018-08-28 | ||
| JP2018-159433 | 2018-08-28 | ||
| PCT/JP2019/032742 WO2020045208A1 (en) | 2018-08-28 | 2019-08-22 | Lens composition, lens, lens production method, and display device |
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| JP (1) | JP7241762B2 (en) |
| CN (1) | CN112639537A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110062476A1 (en) * | 2009-09-14 | 2011-03-17 | Manabu Tobise | Light-extraction member, organic el element, and method for producing the organic el element |
| JP2012251125A (en) * | 2011-05-06 | 2012-12-20 | Fujifilm Corp | Dispersion composition, curable composition using the same, transparent film, microlens and solid-state imaging element |
| JP2012255128A (en) * | 2011-05-18 | 2012-12-27 | Fujifilm Corp | Composition, and transparent film, microlens, solid-state image sensing device, method for manufacturing transparent film, method for manufacturing microlens and method for manufacturing solid-state image sensing device using the same |
| JP2013014740A (en) * | 2011-06-10 | 2013-01-24 | Jnc Corp | Photocurable inkjet ink |
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| US20070015847A1 (en) * | 2005-07-15 | 2007-01-18 | Applied Materials, Inc. | Red printing ink for color filter applications |
| JP5073542B2 (en) * | 2008-03-21 | 2012-11-14 | 富士フイルム株式会社 | Colored curable composition, color filter, method for producing the same, and solid-state imaging device |
| JP6726317B2 (en) * | 2017-02-09 | 2020-07-22 | 富士フイルム株式会社 | Photosensitive composition, cured film, optical filter, solid-state image sensor, image display device and infrared sensor |
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- 2019-08-22 TW TW108129931A patent/TW202012456A/en unknown
- 2019-08-22 JP JP2020539382A patent/JP7241762B2/en active Active
- 2019-08-22 WO PCT/JP2019/032742 patent/WO2020045208A1/en active Application Filing
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110062476A1 (en) * | 2009-09-14 | 2011-03-17 | Manabu Tobise | Light-extraction member, organic el element, and method for producing the organic el element |
| JP2012251125A (en) * | 2011-05-06 | 2012-12-20 | Fujifilm Corp | Dispersion composition, curable composition using the same, transparent film, microlens and solid-state imaging element |
| JP2012255128A (en) * | 2011-05-18 | 2012-12-27 | Fujifilm Corp | Composition, and transparent film, microlens, solid-state image sensing device, method for manufacturing transparent film, method for manufacturing microlens and method for manufacturing solid-state image sensing device using the same |
| JP2013014740A (en) * | 2011-06-10 | 2013-01-24 | Jnc Corp | Photocurable inkjet ink |
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| TW202012456A (en) | 2020-04-01 |
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