WO2024143353A1 - Produit durci issu d'une composition photodurcissable, composant optique, dispositif électroluminescent et module - Google Patents
Produit durci issu d'une composition photodurcissable, composant optique, dispositif électroluminescent et module Download PDFInfo
- Publication number
- WO2024143353A1 WO2024143353A1 PCT/JP2023/046635 JP2023046635W WO2024143353A1 WO 2024143353 A1 WO2024143353 A1 WO 2024143353A1 JP 2023046635 W JP2023046635 W JP 2023046635W WO 2024143353 A1 WO2024143353 A1 WO 2024143353A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- light
- resin
- cured product
- photocurable composition
- optical component
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 230000003287 optical effect Effects 0.000 title claims description 31
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 30
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 30
- 238000002835 absorbance Methods 0.000 claims abstract description 29
- 239000002105 nanoparticle Substances 0.000 claims abstract description 29
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004566 IR spectroscopy Methods 0.000 claims abstract description 10
- 238000009826 distribution Methods 0.000 claims abstract description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005977 Ethylene Chemical group 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims description 19
- 239000011521 glass Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 description 64
- 229920005989 resin Polymers 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 238000002156 mixing Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K17/00—Electronic switching or gating, i.e. not by contact-making and –breaking
- H03K17/51—Electronic switching or gating, i.e. not by contact-making and –breaking characterised by the components used
- H03K17/78—Electronic switching or gating, i.e. not by contact-making and –breaking characterised by the components used using opto-electronic devices, i.e. light-emitting and photoelectric devices electrically- or optically-coupled
Definitions
- the metal oxide nanoparticles may contain, for example, a UV-polymerizable functional group. This allows the metal oxide nanoparticles to be properly bonded in the acrylate resin when the resin is cured by UV irradiation.
- the metal oxide nanoparticles may also be surface-modified (coated) with an oleophilic dispersant or the like.
- the surface-modified metal oxide nanoparticles may be, for example, a dispersion liquid (resin A) that is blended and dispersed in a liquid acrylate resin (organic solvent) separate from the acrylate resin containing the fluorene skeleton described below.
- the acrylate resin (resin B; first acrylate resin) has a fluorene skeleton.
- the fluorene skeleton has an aromatic ring with a three-ring structure.
- the fluorene skeleton has a large number of C-C bonds derived from the aromatic ring, and therefore has high thermal stability.
- acrylate resins with a fluorene skeleton have a slightly high refractive index (e.g., 1.58).
- this resin B has ether (or C-O-C) bonds. If there are many ether (or C-O-C) bonds in the polymer resin, the flexibility of the resin improves according to the interactions between molecules.
- the ratio of each component in the cured product obtained from the photocurable composition containing these components can be obtained using infrared spectroscopy.
- Infrared spectroscopy is a technique that uses the fact that infrared light irradiated to an object is absorbed in a wavenumber band (wavelength, frequency) corresponding to the components and structural parts (functional groups, etc.) of the object to identify the components and their amounts from the characteristics of the absorbed wavelength and the intensity of the absorption (absorbance).
- an offset may occur in each measured value (absolute value) (especially in the microscopic ATR method described below).
- a line located on both sides of the range including the wavenumber band of the object for which absorbance is detected and connecting the absorbance at wavenumbers where absorption is expected to be low is used as a reference line, and the area occupied by the reference line and the distribution of absorbance measured in the wavenumber band of the object for which absorbance is detected is obtained as a value corresponding to the amount of the component.
- the metal oxide nanoparticles (resin A) contain O-H bonds as described above, infrared light is absorbed in a wide range of 3100-3700 cm -1 according to the O-H bonds. On both sides of this region, 1790 cm -1 and 3720 cm -1 are assumed to be the minimum points of absorption (in actual measurements, the minimum points may be shifted slightly, and the above two minimum points may be fixed regardless of the shift).
- the light-emitting device 1 of the present disclosure also includes the optical component 10. Such a light-emitting device 1 can widely diffuse and radiate the emitted light. Therefore, the light-emitting device 1 can be used more reliably and widely in applications that require illumination over a wide area.
- the UV curing agent is added in addition to the resins A to C, but other components may be further included.
- the other components may include acrylate resins other than the resins A to C.
- the specific materials, components, structures, amounts and ratios shown in the above embodiments can be appropriately changed without departing from the spirit of the present invention.
- the scope of the present invention includes the scope of the invention described in the claims and its equivalents.
- This disclosure can be used in optical components, light emitting devices and modules.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Un produit durci issu d'une composition photodurcissable comprend des nanoparticules d'oxyde métallique, une résine acrylate ayant un squelette fluorène, ainsi qu'une résine acrylate ayant un squelette tétrahydrofurane et éthylène. Dans une distribution de l'absorbance obtenue à chaque nombre d'onde à l'aide d'une spectroscopie infrarouge, le rapport Io/Ie de la surface Io pour des nombres d'onde dans la plage de 3100 à 3700 cm-1 à la surface Ie pour des nombres d'onde dans la plage de 1075 à 1130 cm-1 est de 2 à 5.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022-211551 | 2022-12-28 | ||
JP2022211551 | 2022-12-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2024143353A1 true WO2024143353A1 (fr) | 2024-07-04 |
Family
ID=91718012
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2023/046635 WO2024143353A1 (fr) | 2022-12-28 | 2023-12-26 | Produit durci issu d'une composition photodurcissable, composant optique, dispositif électroluminescent et module |
Country Status (1)
Country | Link |
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WO (1) | WO2024143353A1 (fr) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006073755A1 (fr) * | 2004-12-30 | 2006-07-13 | 3M Innovative Properties Company | Monomères à indice de réfraction élevé pour applications optiques |
WO2011162293A1 (fr) * | 2010-06-23 | 2011-12-29 | 日本化成株式会社 | Matériau hybride inorganique-organique, matériau optique utilisant celui-ci, et composition de composite inorganique-organique |
CN109799552A (zh) * | 2017-11-16 | 2019-05-24 | 宁波长阳科技股份有限公司 | 一种防反射膜及其制备方法 |
WO2021261469A1 (fr) * | 2020-06-26 | 2021-12-30 | 富士フイルム株式会社 | Composition, film de transfert, procédé de production de stratifié, procédé de production de câblage de circuit et procédé de production de dispositif électronique |
WO2022044598A1 (fr) * | 2020-08-31 | 2022-03-03 | 株式会社巴川製紙所 | Composition de film optique anisotrope et film optique anisotrope |
-
2023
- 2023-12-26 WO PCT/JP2023/046635 patent/WO2024143353A1/fr unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006073755A1 (fr) * | 2004-12-30 | 2006-07-13 | 3M Innovative Properties Company | Monomères à indice de réfraction élevé pour applications optiques |
WO2011162293A1 (fr) * | 2010-06-23 | 2011-12-29 | 日本化成株式会社 | Matériau hybride inorganique-organique, matériau optique utilisant celui-ci, et composition de composite inorganique-organique |
CN109799552A (zh) * | 2017-11-16 | 2019-05-24 | 宁波长阳科技股份有限公司 | 一种防反射膜及其制备方法 |
WO2021261469A1 (fr) * | 2020-06-26 | 2021-12-30 | 富士フイルム株式会社 | Composition, film de transfert, procédé de production de stratifié, procédé de production de câblage de circuit et procédé de production de dispositif électronique |
WO2022044598A1 (fr) * | 2020-08-31 | 2022-03-03 | 株式会社巴川製紙所 | Composition de film optique anisotrope et film optique anisotrope |
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