WO2012091379A2 - 디이모늄계 화합물 및 이를 이용한 근적외선 흡수 필터 - Google Patents
디이모늄계 화합물 및 이를 이용한 근적외선 흡수 필터 Download PDFInfo
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- WO2012091379A2 WO2012091379A2 PCT/KR2011/010082 KR2011010082W WO2012091379A2 WO 2012091379 A2 WO2012091379 A2 WO 2012091379A2 KR 2011010082 W KR2011010082 W KR 2011010082W WO 2012091379 A2 WO2012091379 A2 WO 2012091379A2
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- WIPO (PCT)
- Prior art keywords
- dimonium
- compound
- near infrared
- absorption
- infrared absorption
- Prior art date
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- 238000010521 absorption reaction Methods 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000031700 light absorption Effects 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 239000000463 material Substances 0.000 description 21
- -1 tetrafluoroborate ions Chemical class 0.000 description 21
- 239000011358 absorbing material Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- INGVZLYSYVSTRR-UHFFFAOYSA-N 4-n-[4-[4-[bis(2-methylpropyl)amino]-n-[4-[bis(2-methylpropyl)amino]phenyl]anilino]phenyl]-4-n-[4-[bis(2-methylpropyl)amino]phenyl]-1-n,1-n-bis(2-methylpropyl)benzene-1,4-diamine Chemical compound C1=CC(N(CC(C)C)CC(C)C)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(CC(C)C)CC(C)C)C=1C=CC(=CC=1)N(CC(C)C)CC(C)C)C1=CC=C(N(CC(C)C)CC(C)C)C=C1 INGVZLYSYVSTRR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000032900 absorption of visible light Effects 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000005677 organic carbonates Chemical class 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- LVPYYSKDNVAARK-UHFFFAOYSA-N 4-n-[4-(4-amino-n-(4-aminophenyl)anilino)phenyl]-4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(N)=CC=1)C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 LVPYYSKDNVAARK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001692 polycarbonate urethane Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
Definitions
- the present invention relates to a dimonium-based compound and a near-infrared absorption filter using the same, and more particularly, a new dimonium-based compound exhibiting low light absorption in the visible light region and excellent absorption efficiency in the near-infrared light region and having excellent durability and weather resistance. And a near infrared absorption filter using the same.
- near-infrared absorbing material pigment
- a film including the same when attached to a window, it absorbs a part of sunlight and heats the inside and outside of the room. By reducing the exchange, it is possible to prevent excessive rise and fall of room temperature. Therefore, the near-infrared absorbing material can be used as a representative energy-saving material, has been actively applied in the building and automotive industry.
- Near-infrared absorbing materials used in films attached to windows of automobiles and buildings should have good near-infrared absorption performance and minimize absorption in the visible region.
- the driver's vision may be blurred or the view of the house may be deteriorated, and additional energy may be required for internal lighting. This is because the color may not be natural.
- Representative near-infrared absorbing materials include dimonium-based materials (compounds), phthalocyanine-based materials, cyanine-based materials, metal dithiolene-based materials, and the like.
- dimonium-based materials compounds
- phthalocyanine-based materials cyanine-based materials
- metal dithiolene-based materials metal dithiolene-based materials
- Pigments include dimonium-based materials (compounds), phthalocyanine-based materials, cyanine-based materials, metal dithiolene-based materials, and the like.
- Phthalocyanine-based materials which are representative near-infrared absorbing materials, have been actively applied for electronic devices including displays due to chemical stability, but have a disadvantage in that they cannot be applied alone due to high absorption of visible light range for application to automobile window films.
- Cyanine-based materials have a low chemical stability and have a narrow width of the near-infrared region that can be absorbed by a single substance, and thus, for practical applications, cyanine-based materials have to be mixed to expand the absorption region.
- the metal dithiol-based material has a high near-infrared absorption, but low solubility requires a dispersing facility for the film application, there is a disadvantage that it is difficult to apply to applications requiring high permeability.
- the dimonium-based material has a high and wide NIR absorption region and a very low absorption of the entire visible light region, so that the dimonium-based material can absorb the entire NIR region even with a single material.
- the main composition of the dimonium-based near infrared absorbing material is composed of a cation of the dimonium structure and various anions.
- Representative anions include ions containing an inorganic element such as fluorine (fluorine), chlorine, bromine, hexafluoro antimonate ions, perchlorate ions, tetrafluoroborate ions, etc.
- Organic carbonate ions, and the like, and bis (trifluoromethanesulfonyl) imide ions, bis (pentafluoroethanesulfonyl) imide ions and the like have been frequently used in recent years.
- the dimonium-based compound using the halogen ion as an anion is difficult to apply to a process for use as a near infrared absorbing material due to solubility problems, and the organic carbonate acid ion has high solubility in water, so that the yield of the dimonium-based compound is high. Difficult to manage, and weather resistance problem occurs in the product, it is difficult to actually use.
- anionic materials such as the antimony fluoride ions, which are widely used in recent years, may be used as a near-infrared absorbing material with appropriate physical properties, but toxic substances such as hydrofluoric acid may be emitted due to fluorine atoms present in the material. It is not suitable for use in places close to the human living environment such as cars and automobiles, and the durability of the product (film, etc.) may be degraded by the hydrofluoric acid.
- an object of the present invention is to provide a wide and even absorption of light in the near infrared region (particularly, wavelengths of 750 to 1100 nm), excellent transmission characteristics in the visible region (wavelengths of 400 to 750 nm), and excellent durability and weather resistance. It is to provide an immonium compound.
- Another object of the present invention is to provide an eco-friendly dimonium compound by not including a fluorine atom in the compound structure.
- Still another object of the present invention is to provide a near infrared absorption filter containing one or two dimonium compounds as a near infrared absorbing dye.
- the present invention provides a dimonium-based compound represented by the following formula (1).
- R 1 to R 8 are each independently a hydrogen atom (H), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, n is 0 or 1.
- the present invention provides a near-infrared absorption filter including the dimonium-based compound.
- the dimonium compound according to the present invention exhibits an optical characteristic inherent to the dimonium-based near infrared absorbing material, that is, a wide and even absorption efficiency in the near infrared region (particularly, a wavelength of 750 to 1100 nm) and a visible light region (wavelength of 400 to 750 nm). Shows excellent permeability and is useful as environment-friendly near-infrared absorbing material for homes and automobiles because it has excellent durability and weather resistance and does not contain fluorine atoms in the compound structure.
- Example 1 is a UV / VIS absorption spectrum of the dimonium compound prepared according to Example 1 and Comparative Examples 1 to 2 of the present invention.
- the dimonium compound according to the present invention is represented by the structure of the following formula (1).
- R 1 to R 8 are each independently a hydrogen atom (H), a substituted or unsubstituted C1 to 10, preferably a C1-6 alkyl group, a substituted or unsubstituted C6 to 14 , Preferably it is 6-10 aryl groups, for example, a substituted or unsubstituted phenyl group, n is 0 or 1.
- substituent of R 1 to R 8 may include an alkyl group having 1 to 5 carbon atoms, a halogen group other than fluorine, and the like.
- the dimonium-based compound according to the present invention can be prepared according to a known dimonium-based compound production method, for example, can be prepared by applying the production method shown in the following examples.
- the dimonium-based compound according to the present invention exhibits a wide and even light absorption efficiency in the near infrared region (particularly, a wavelength of 750 to 1100 nm), and has a low absorption of light in the visible region (wavelength of 400 to 750 nm), thereby showing excellent transmission characteristics.
- the thermal stability of the anionic material is very high and does not contain fluorine atoms in the compound, so that environmental problems and durability problems due to the generation of hydrofluoric acid do not occur.
- the dimonium-based compound since the dimonium-based compound has a wide absorption in the near infrared region even with a single material, sufficient near-infrared absorption can be obtained with a mixture of one or two compounds in the preparation of the near-infrared absorption filter, so that each dimonium-based compound and the binder material The compatibility between and the degradation of compatibility between dimonium-based compounds is improved.
- the dimonium compound according to the present invention can be used in the preparation of the near infrared absorption filter as a dye of the near infrared absorption filter, according to a conventional method.
- a polymer resin (binder material) suitable for a near-infrared absorption filter most transparent polymer resins such as polymethyl methacrylate, polyester, polycarbonate, and polyurethane can be used, but heat resistance and environmental resistance required for each application
- Use materials suitable for the conditions of The near-infrared absorbing filter may be prepared by dissolving the near-infrared absorbing dye in a solvent and coating the same on the polymer resin, and various solvents such as methyl ethyl ketone, tetrahydrofuran, chloroform, and toluene may be used.
- the layered dichloromethane layer was distilled by vacuum distillation to obtain 30 g of N, N, N ', N'-tetrakis (p-diisobutylaminophenyl) -p-phenylenediamine (crude reactant). .
- N, N, N ', N'-tetrakis (p-diisobutylaminophenyl) -p-phenylenediamine obtained in the same manner as in Example 1, 15 g of lithium bistrifluoromethanesulfonylimide and dichloro 150 g of methane and 60 g of ethanol were added and refluxed for 2 hours. Then, 10 g of sodium persulfate and 200 g of water were added and refluxed for 2 hours.
- VOPc vanadium oxide phthalocyanine
- VOPc (PhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 (C 6 H 11 NH) 4 (Ph) phenyl, A 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14 and A 15 in Formula 2 are PhS, and A 1 , A 5 , A 9 and A 13 are ⁇ 2,6 -(CH 3 ) 2 PhO ⁇ , A 4 , A 8 , A 12 and A 16 are C 6 H 11 NH).
- the dimonium compounds and vanadil phthalocyanine compounds prepared in Examples 1 and 2 and Comparative Examples 1 and 2 were respectively diluted in toluene, and UV / VIS spectra were measured.
- the maximum absorption wavelength of the dimonium compound of Examples 1 to 2 and Comparative Example 1 was 1000 nm or more, and the maximum absorption wavelength of the vanadil phthalocyanine compound of Comparative Example 2 was 932 nm.
- UV / VIS absorption spectrum of the dimonium-based compound and vanadil phthalocyanine compound prepared in Example 1 and Comparative Examples 1 to 2 are shown in FIG.
- the dimonium-based compound according to the present invention does not contain a fluorine atom (F) in the compound, it can be seen that the environmental problems and durability problems due to the generation of hydrofluoric acid (HF) does not occur Compared to the vanadil phthalocyanine compound prepared in Comparative Example 2, it exhibits broad and even absorption efficiency in the near infrared region (particularly, wavelength of 750 to 1100 nm) and excellent transmission characteristics in the visible region (wavelength of 400 to 700 nm). Able to know.
- F fluorine atom
- HF hydrofluoric acid
- the dimonium compound according to the present invention is useful as an environment-friendly near-infrared absorbing material for homes and automobiles.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Optical Filters (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (2)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013547321A JP5785623B2 (ja) | 2010-12-28 | 2011-12-26 | ジイモニウム系化合物およびこれを利用した近赤外線吸収フィルター |
US13/976,600 US9158048B2 (en) | 2010-12-28 | 2011-12-26 | Diimmonium-based component and near infrared absorption filter using same |
CN201180062964.3A CN103270019B (zh) | 2010-12-28 | 2011-12-26 | 基于二亚胺的化合物以及使用该化合物的近红外吸收滤光片 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2010-0136942 | 2010-12-28 | ||
KR20100136942A KR101251898B1 (ko) | 2010-12-28 | 2010-12-28 | 디이모늄계 화합물 및 이를 이용한 근적외선 흡수 필터 |
Publications (2)
Publication Number | Publication Date |
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WO2012091379A2 true WO2012091379A2 (ko) | 2012-07-05 |
WO2012091379A3 WO2012091379A3 (ko) | 2012-09-27 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/KR2011/010082 WO2012091379A2 (ko) | 2010-12-28 | 2011-12-26 | 디이모늄계 화합물 및 이를 이용한 근적외선 흡수 필터 |
Country Status (5)
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US (1) | US9158048B2 (ko) |
JP (1) | JP5785623B2 (ko) |
KR (1) | KR101251898B1 (ko) |
CN (1) | CN103270019B (ko) |
WO (1) | WO2012091379A2 (ko) |
Families Citing this family (7)
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KR101653865B1 (ko) * | 2013-06-18 | 2016-09-02 | 주식회사 엘지화학 | 염료 및 이를 포함하는 컬러필터 |
WO2016148518A1 (ko) * | 2015-03-17 | 2016-09-22 | 주식회사 엘엠에스 | 광학 필터 및 이를 포함하는 촬상 장치 |
US10969526B2 (en) * | 2017-09-08 | 2021-04-06 | Apple Inc. | Coatings for transparent substrates in electronic devices |
CN112004620B (zh) | 2018-10-31 | 2021-12-21 | 竹内忍 | 进行板材加工的加工装置及加工方法 |
KR102449992B1 (ko) * | 2018-12-10 | 2022-10-05 | 연세대학교 산학협력단 | 퀴노이드계 이온화합물, 이의 제조방법, 상기 퀴노이드계 이온화합물을 포함하는 투명한 근적외선 차단막 및 이의 제조방법 |
CN114616291B (zh) | 2019-11-01 | 2023-07-04 | Jsr株式会社 | 树脂组合物、化合物、光学滤波器、及光学传感装置 |
KR102575190B1 (ko) * | 2022-11-21 | 2023-09-06 | 한국화학연구원 | 근적외선 흡수제 및 이를 포함하는 근적외선 차단 필터 |
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US20070123614A1 (en) * | 2003-10-20 | 2007-05-31 | Tetsuya Nakabeppu | Near-infrared ray-shielding paint, near-infrared ray-shielding laminate obtained therefrom and production method thereof |
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KR20100036245A (ko) * | 2007-06-27 | 2010-04-07 | 니폰 가야꾸 가부시끼가이샤 | 근적외선 흡수 필름 및 이것을 이용한 플라즈마 디스플레이 패널용 광학 필터 |
DE102008021271A1 (de) * | 2008-04-29 | 2010-01-28 | Merck Patent Gmbh | Reaktive ionische Flüssigkeiten |
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- 2011-12-26 US US13/976,600 patent/US9158048B2/en not_active Expired - Fee Related
- 2011-12-26 WO PCT/KR2011/010082 patent/WO2012091379A2/ko active Application Filing
- 2011-12-26 JP JP2013547321A patent/JP5785623B2/ja not_active Expired - Fee Related
- 2011-12-26 CN CN201180062964.3A patent/CN103270019B/zh not_active Expired - Fee Related
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US20070123614A1 (en) * | 2003-10-20 | 2007-05-31 | Tetsuya Nakabeppu | Near-infrared ray-shielding paint, near-infrared ray-shielding laminate obtained therefrom and production method thereof |
KR20070053740A (ko) * | 2004-09-06 | 2007-05-25 | 니폰 가야꾸 가부시끼가이샤 | 디이모늄 화합물 및 그의 용도 |
KR20080007333A (ko) * | 2005-05-13 | 2008-01-18 | 니폰 가야꾸 가부시끼가이샤 | 디이모늄 화합물 및 그의 용도 |
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KR20120074947A (ko) | 2012-07-06 |
CN103270019A (zh) | 2013-08-28 |
JP2014506252A (ja) | 2014-03-13 |
WO2012091379A3 (ko) | 2012-09-27 |
JP5785623B2 (ja) | 2015-09-30 |
US20130331608A1 (en) | 2013-12-12 |
KR101251898B1 (ko) | 2013-04-08 |
CN103270019B (zh) | 2016-02-03 |
US9158048B2 (en) | 2015-10-13 |
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