WO2010050720A4 - Absorbant de proche infrarouge constitué de complexe métallique de dithiol, procédé de préparation dudit complexe métallique de dithiol, et filtre optique et filtre de protection contre l'infrarouge thermique contenant un tel absorbant - Google Patents
Absorbant de proche infrarouge constitué de complexe métallique de dithiol, procédé de préparation dudit complexe métallique de dithiol, et filtre optique et filtre de protection contre l'infrarouge thermique contenant un tel absorbant Download PDFInfo
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- WO2010050720A4 WO2010050720A4 PCT/KR2009/006216 KR2009006216W WO2010050720A4 WO 2010050720 A4 WO2010050720 A4 WO 2010050720A4 KR 2009006216 W KR2009006216 W KR 2009006216W WO 2010050720 A4 WO2010050720 A4 WO 2010050720A4
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- WO
- WIPO (PCT)
- Prior art keywords
- dithiol
- metal complex
- near infrared
- based metal
- formula
- Prior art date
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- 239000002250 absorbent Substances 0.000 title claims abstract description 26
- 230000002745 absorbent Effects 0.000 title claims abstract description 26
- -1 dithiol metal complex Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000003287 optical effect Effects 0.000 title abstract description 22
- 239000002952 polymeric resin Substances 0.000 claims abstract description 20
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 150000004662 dithiols Chemical class 0.000 claims description 74
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 58
- 150000004696 coordination complex Chemical class 0.000 claims description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 239000006096 absorbing agent Substances 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 31
- 229910052759 nickel Inorganic materials 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000001033 ether group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 150000002815 nickel Chemical class 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000004925 Acrylic resin Substances 0.000 claims description 8
- 229920000178 Acrylic resin Polymers 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 229910052736 halogen Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 229920001225 polyester resin Polymers 0.000 claims description 8
- 239000004645 polyester resin Substances 0.000 claims description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012461 cellulose resin Substances 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 238000005805 hydroxylation reaction Methods 0.000 claims description 6
- 229920001230 polyarylate Polymers 0.000 claims description 6
- 229920005668 polycarbonate resin Polymers 0.000 claims description 6
- 239000004431 polycarbonate resin Substances 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 229910001510 metal chloride Inorganic materials 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
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- 238000010521 absorption reaction Methods 0.000 abstract description 14
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- 238000002156 mixing Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000012153 distilled water Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- 0 CCC**c1c(*)c(*)cc(C2=N*N=C2c2cc(*)c(**CCC)c(*)c2)c1 Chemical compound CCC**c1c(*)c(*)cc(C2=N*N=C2c2cc(*)c(**CCC)c(*)c2)c1 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LRRQSCPPOIUNGX-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(O)C(=O)C1=CC=C(OC)C=C1 LRRQSCPPOIUNGX-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OIFKAYYDTOHLSS-UHFFFAOYSA-N 1,2-bis(3,4,5-trimethoxyphenyl)ethane-1,2-dione Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 OIFKAYYDTOHLSS-UHFFFAOYSA-N 0.000 description 1
- JIDNYUKRPUJZAL-UHFFFAOYSA-N 2-hydroxy-1,2-bis(3,4,5-trimethoxyphenyl)ethanone Chemical compound COC1=C(OC)C(OC)=CC(C(O)C(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 JIDNYUKRPUJZAL-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- DMHBUEWIMWWGIH-YJSPFGELSA-N CC/C(/I)=C/C=C(\C=C)/C(S1)=C(C2=CC=C=CC=C2)S[N]11SC(c2ccccc2)=C(/C(/C=C\C)=C/C=C)S1 Chemical compound CC/C(/I)=C/C=C(\C=C)/C(S1)=C(C2=CC=C=CC=C2)S[N]11SC(c2ccccc2)=C(/C(/C=C\C)=C/C=C)S1 DMHBUEWIMWWGIH-YJSPFGELSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- FWQHRZXEQNUCSY-UHFFFAOYSA-N tert-butyl N-[2-(ethoxycarbonylamino)-5-[(4-fluorophenyl)methyl-prop-2-ynylamino]phenyl]carbamate Chemical compound CCOC(=O)NC1=C(C=C(C=C1)N(CC#C)CC2=CC=C(C=C2)F)NC(=O)OC(C)(C)C FWQHRZXEQNUCSY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/10—Thiols having mercapto groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- 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
Definitions
- the present invention relates to a near infrared absorber made of a dithiol-based metal complex, a method for producing the dithiol-based metal complex, an optical filter containing the same and an infrared ray shielding filter. More particularly, By providing a near infrared ray absorbent made of a novel ditol-based nickel complex, it is possible to efficiently mix with an organic material such as a polymer resin mixed in the production of an optical filter, thereby exhibiting excellent near infrared absorption performance of the ditol- Which does not deteriorate the near infrared absorbing ability.
- These image display devices display a color image by a combination of three primary colors of red, blue, and green light.
- light of unnecessary wavelength is emitted from the display device, and there is a problem in malfunction of the peripheral electronic device and high quality of the display image.
- the plasma display also emits near-infrared rays or electromagnetic waves in the 800 to 1000 nm range. Since the wavelength range of the near-infrared rays overlaps with the wavelength range used in near-infrared communication or remote controllers of other electronic apparatuses, do.
- An optical filter containing a specific light absorbing agent is used for the above problem.
- an optical filter for absorbing near infrared rays is disclosed in Japanese Patent Application Laid-Open Nos. 9-230134 and 11-73115
- An optical filter using an aromatic dithiol nickel compound as a light absorber has been reported in JP-A-11-12425, JP-A 2000-206322, and JP-A 2000-212546.
- the near infrared absorber for optical filters it is required to selectively absorb wavelength light in the near infrared region and transmit light in the visible light region.
- the conventional light absorbing agent absorbs the visible light region and is not suitable as the light absorbing agent for the optical filter.
- dithiol-based nickel complexes represented by the following formula (13) are typical examples of those having excellent performance as a near-infrared absorbing agent by effectively absorbing near-infrared rays in a wavelength region of 800 to 900 nm.
- the dithiol-based nickel complex is useful as an antioxidant such as polyolefins, an anti-discoloration agent such as an anti-fouling agent or a color photograph since it has a good inactivating action against singlet oxygen in addition to its use as a near infrared absorber. Furthermore, the dithiol-based nickel complexes have excellent properties applicable to various fields such that they can be usefully utilized as catalysts or liquid crystal materials for photodecomposition and dehydration of water.
- the organic material such as a binder resin, a plastic, an ionic coating or an organic solvent should be dissolved or contained in an optimal amount uniformly.
- the dithiol-based nickel complex has a low solubility with respect to an organic material, so that it can not contain a sufficient amount in an organic material, so that the performance can not be sufficiently exhibited.
- the present inventors have made efforts to solve the problems of the conventional light absorbents for optical filters. As a result, they have found that a novel dithiol-based nickel complex compound having improved solubility in an organic material and absorbing only near- The present inventors have completed the present invention by producing a novel near infrared absorbing dye in which the performance of the dithiol-based nickel complex is sufficiently exhibited and the near infrared absorbing ability is not deteriorated for a long time, and an optical filter and a thermal infrared ray shielding filter using the same.
- Another object of the present invention is to provide a novel method for preparing a dithiol-based nickel complex.
- Still another object of the present invention is to provide an optical filter, a thermal infrared ray shielding filter, and a plasma display panel employing the infrared filter, which contain a near infrared absorbent composed of the dithiol-based nickel complex.
- the present invention provides a near infrared ray absorbent made of a dithiol-based nickel complex having improved solubility in an organic material.
- the present invention provides a near infrared ray absorbent comprising a dithiol-based metal complex represented by the following formula (1).
- M is a nickel, palladium or platinum
- R is an ether group of hydrogen
- X is hydrogen or halogen
- m 1 ⁇ 3
- o q-r ', p', q 'and r' are 0 to 3
- [o-o '], [p- ] Are 0 to 3, respectively, and are positive integers.
- the dithiol-based metal complex of the present invention provides a near infrared absorber characterized in that the benzene ring is substituted with 1 to 5 hydroxy groups to improve solubility.
- the metal element is preferably nickel.
- the dithiol-based metal complexes of the present invention can be obtained by reacting a compound represented by the general formula (1) in a group consisting of dichloromethane, dichloroethane, methyl ethyl ketone, methyl isobutyl ketone, toluene, ethylene glycol monoethyl ether, ethanol, xylene, tetrahydrofuran and 1,4- And exhibit solubility-improving effects on any one of the selected organic solvents.
- the present invention also provides a process for preparing a dithiol-based metal complex having improved solubility.
- M is a nickel, palladium or platinum
- R is an ether group of hydrogen
- X is hydrogen or halogen
- m 1 ⁇ 3
- o q-r ', p', q 'and r' are 0 to 3
- [o-o '], [p- ] Are 0 to 3, respectively, and are positive integers.
- At least one Lewis acid selected from the group consisting of AlCl 3 , ZnCl 2 and BF 3 is used in an amount of 2 to 15 mol%, more preferably 2 to 10 mol %
- a partial hydroxylation reaction to prepare a symmetrical or asymmetric dithiol-based metal complex.
- the dithiol-based metal complex preferably has 2 to 5 hydroxyl group substituents, and the central metal is preferably nickel.
- the present invention also relates to an optical filter manufactured in the form of a film or a panel by applying a composition containing a near infrared absorber and a polymer resin composed of a dithiol-based metal complex represented by Chemical Formula 1 on a glass or transparent base film, Filter.
- the central metal is preferably nickel
- the polymer resin may be at least one selected from the group consisting of an acrylic resin, a polyester resin, a polycarbonate resin, a urethane resin, a cellulose resin, a polyisocyanate, a polyarylate, May be used.
- the composition further comprises a near infrared absorbing agent and a polymer resin, and the polymer resin contains 1 to 3% by weight of a near infrared absorbing agent.
- the present invention is characterized in that the optical filter or the thermal infrared ray shielding filter is used for an image display device, and in particular, 1 to 3% by weight of a near infrared absorbent composed of a dithiol-based metal complex and an acrylic resin, a polyester resin, a polycarbonate resin, , 98 to 99% by weight of a polymeric resin selected from the group consisting of an acrylic resin, a polyester resin, a cellulose resin, a polyisocyanate, a polyarylate, and an epoxy resin is applied on a glass or transparent base film, A plasma display panel employing an infrared shielding filter is provided.
- a near infrared ray absorbent made of a dithiol-based metal complex having a small absorption in the visible ray region, selectively absorbing the wavelength light in the near infrared ray region and improving the solubility in an organic material
- an optical filter, a thermal infrared ray shielding filter and a plasma display panel employing the same that do not deteriorate the near infrared ray absorption ability for a long time by containing a near infrared ray absorbent.
- 1 is an absorption spectrum of a dithiol-based nickel complex of the present invention using an ultraviolet spectrometer.
- the present invention provides a near infrared ray absorbent comprising a dithiol-based metal complex represented by Chemical Formula (1), which is a conventional dithiol-based metal complex compound known as a near infrared absorber to solve the problem of low solubility in an organic solvent.
- a dithiol-based metal complex represented by Chemical Formula (1) which is a conventional dithiol-based metal complex compound known as a near infrared absorber to solve the problem of low solubility in an organic solvent.
- M is a nickel, palladium or platinum
- R is an ether group of hydrogen
- X is hydrogen or halogen
- m 1 ⁇ 3
- o q-r ', p', q 'and r' are 0 to 3
- [o-o '], [p- ] Are 0 to 3, respectively, and are positive integers.
- the alkyl group of R is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group and an n-hexyl group, and more preferably the alkyl group of R is a methyl group or an ethyl group .
- the solubility improvement in the present invention means that the dithiol-based metal complexes of the present invention are improved in solubility not only in ketone-based solvents and halogen-based solvents but also in alcohols such as ethylene glycol monoethyl ether and ethanol. More specifically, it is preferable to use a solvent selected from the group consisting of dichloromethane, dichloroethane, methyl ethyl ketone, methyl isobutyl ketone, toluene, ethylene glycol monoethyl ether, ethanol, xylene, tetrahydrofuran and 1,4- And has a solubility in one organic solvent.
- the dithiol-based metal complex of the present invention selectively absorbs near-infrared rays in the wavelength region of 930 to 960 nm.
- R is an ether group of hydrogen, C 1 ⁇ C 6 alkyl group or a C 1 ⁇ C 6 in.
- R is an ether group of hydrogen, C 1 ⁇ C 6 alkyl group or a C 1 ⁇ C 6 in.
- the near infrared absorber according to the third preferred embodiment of the present invention contains a dithiol-based nickel complex selected from the asymmetric dithiol-based nickel complexes represented by the following general formulas (7) to (9) will be.
- R is an ether group of hydrogen, C 1 ⁇ C 6 alkyl group or a C 1 ⁇ C 6 in.
- the present invention provides a method for preparing a dithiol-based metal complex contained in the near infrared absorber and having improved solubility.
- the production method of the present invention is characterized in that at least one Lewis acid selected from the group consisting of AlCl 3 , ZnCl 2 and BF 3 is added to the dithiol-based metal complex in an amount of 2 to 15 mol%, more preferably 2 to 10 mol % ≪ / RTI > to effect a partial hydroxylation reaction.
- at least one Lewis acid selected from the group consisting of AlCl 3 , ZnCl 2 and BF 3 is added to the dithiol-based metal complex in an amount of 2 to 15 mol%, more preferably 2 to 10 mol % ≪ / RTI > to effect a partial hydroxylation reaction.
- AlCl 3 it is preferably 2 to 10 mol%
- ZnCl 2 when ZnCl 2 is used, a change in the desired absorption wavelength, a change in solubility and yield can be obtained by 2 to 15 mol%.
- the dithiol-based metal complex of the present invention exhibits excellent solubility in an organic solvent when 1 to 5, more preferably 2 to 5, hydroxyl group substituents are present.
- the solubility is excellent, but the long-wavelength shift is remarkable, which is outside the desired wavelength range, and it is difficult to separate and purify the desired nickel complex.
- the organic solvent may be any one selected from the group consisting of chloromethane, dichloroethane, methyl ethyl ketone, methyl isobutyl ketone, toluene, ethylene glycol monoethyl ether, ethanol, xylene, tetrahydrofuran and 1,4- And exhibits excellent solubility in insoluble which is hardly dissolved in the prior art.
- the present invention relates to an optical filter and a thermal infrared ray shielding filter manufactured in the form of a film or a panel by applying a composition containing a near infrared absorber made of a dithiol-based metal complex represented by the above formula (1) and a polymer resin on a glass or transparent base film to provide.
- the central metal is preferably nickel
- the polymer resin may be at least one selected from the group consisting of an acrylic resin, a polyester resin, a polycarbonate resin, a urethane resin, a cellulose resin, a polyisocyanate, a polyarylate, May be used.
- the transparent substrate film used in the present invention is preferably polyester or polycarbonate.
- the composition of the near infrared absorber and the polymer resin of the present invention can control the near infrared absorption ratio according to the content of the composition.
- the polymer resin contains 1 to 3% by weight of a near infrared ray absorbent composed of a dithiol-based metal complex compound. If the content of the near infrared absorbing agent is less than 1% by weight, the near infrared ray absorbing ability is insufficient. If the content is more than 3% by weight, the transmittance of the visible ray decreases.
- the composition of the present invention is applied to a glass or transparent base film by a wet process to produce a film or a panel.
- the coating solution prepared by dissolving or dispersing the near infrared absorber and the polymer resin in an organic solvent
- a roll coating method, a spin coating method, a casting method, or a melt extrusion method is used, though not limited to the present invention.
- the organic solvent is selected from the group consisting of dichloromethane, dichloroethane (DME), methyl ethyl ketone, methyl isobutyl ketone, toluene, ethylene glycol monoethyl ether, ethanol, xylene, tetrahydrofuran and 1,4-
- the dithiol-based metal complex of the present invention can be easily dissolved in the organic solvent.
- the dithiol-metal complex compound of the present invention is remarkably improved in solubility, as well as ketones and halogenated solvents, ethylene glycol monoethyl ether alcohols such as ethanol and the flow table 2.
- the near infrared ray absorbent of the present invention is dissolved or kneaded in the polymer resin, and then molded into a film or a panel by extrusion molding.
- the present invention can provide an optical filter and a thermal infrared ray shielding filter as a method for producing a film by mixing a master batch produced by mixing a near infrared absorber and a polymer resin.
- additives such as an antioxidant, a heat stabilizer, a viscosity adjuster, a plasticizer, a color improving agent, a lubricant, a nucleating agent, an ultraviolet stabilizer, an antistatic agent, an antioxidant, a binder and a catalyst may be further used in the masterbatch composition And the content of the additive can be adjusted within a range of 1 to 3% by weight of the near infrared absorber.
- the heat shielding film is excellent in the dispersibility of the near infrared absorber, so that unevenness of dyeing does not occur and heat shielding efficiency can be improved. Therefore, it is possible to provide a uniform quality heat shielding film, and it is possible to realize an economical effect by simplifying the process than the conventional dyeing process.
- the present invention is characterized in that the optical filter or the thermal infrared ray shielding filter is used for an image display device, and in particular, 1 to 3% by weight of a near infrared absorbent composed of a dithiol-based metal complex and an acrylic resin, a polyester resin, a polycarbonate resin, , 98 to 99% by weight of a polymeric resin selected from the group consisting of an acrylic resin, a polyester resin, a cellulose resin, a polyisocyanate, a polyarylate, and an epoxy resin is applied on a glass or transparent base film, A plasma display panel employing an infrared shielding filter is provided.
- Step 1 After dissolving 13.5 g of 3,4,5-trimethoxybenzaldehyde in 50 ml of ethanol, 20 ml of distilled water containing 4.5 g of potassium cyanide was slowly added. After refluxing for 1 hour and cooling, 150 ml of distilled water was added to form a precipitate, which was then filtered under reduced pressure, washed several times with distilled water, and dried to obtain 8.2 g of yellow object.
- Step 2 48 g of 2-hydroxy-1,2-bis (3,4,5-trimethoxyphenyl) ethanone was dissolved in 150 g of pyridine and 100 ml of distilled water containing 50 g of CuSO 4 .5H 2 O Slowly added. After cooling to reflux for 10 hours, 500 ml of distilled water was added to form a precipitate, which was then filtered under reduced pressure, washed several times with distilled water, and then dried to obtain 40 g of a pale yellow object.
- Step 3 32 g of 1,2-bis (3,4,5-trimethoxyphenyl) ethane-1,2-dione and 18 g of P 2 S 5 were placed in 150 ml of 1,4-dioxane and stirred. The solution was refluxed for 5 hours, cooled and filtered. The filtrate was transferred to a 500 ml reactor, and a solution of 11 g of NiCl 2 .H 2 O dissolved in 100 ml of distilled water was slowly added over 1 hour. After completion of the addition, the mixture was refluxed for 30 hours and cooled. 100 ml of ethanol was added to the cooled reactant, and the mixture was filtered under reduced pressure, washed several times with acetone, and then dried to obtain 14 g of a dark green object.
- Step 4 After stirring the AlCl 3 of 14.7g (0.11 mol) in dichloromethane 30ml for 30 minutes, diluted with 12-methoxy -Ni- complex compound 10g (0.011 mol) prepared in Step 3 in dichloromethane 50ml Lt; / RTI > After reacting for 1 hour and 30 minutes at room temperature, 600 ml of distilled water was slowly added while stirring in an ice chamber. The precipitate formed was filtered under reduced pressure, washed several times with distilled water, and then purified.
- Example 1 The target compounds prepared in Example 1 were analyzed by HPLC and mass spectrometer (LC-Mass spectrometer, VG BIO TECH, model name: VG BIO TECH), and the results are shown in Tables 1 and 2 below.
- thermogravimetric analyzer TGA
- mp 258.71, 320.59 and 342.82 ° C peaks were confirmed.
- DSC differential pressure calorimeter
- the search observe the compound as a result, the maximum absorption wavelength ( ⁇ max) is 960nm ( ⁇ 2.9 ⁇ 10 4 L / cm and g) was measured by a UV spectrometer was dissolved in methyl ethyl ketone [1] Accordingly, it can be used as a near-infrared absorbing agent suitable for use in a plasma display panel (PDP).
- ⁇ max the maximum absorption wavelength
- solubilities (g / g) of the dithiol-based nickel complexes of Example 1 were measured for each of 100 g of ethanol, methyl ethyl ketone, ethyl acetate and toluene solvent. The results are shown in Table 5 .
- the dithiol-based nickel complexes prepared in Example 1 were significantly improved in solubility not only in ketone-based and halogen-based solvents but also in alcohols such as ethanol, compared with dithiol-based nickel complexes substituted with methoxy groups.
- Step 1 After 40 g of p-anisaldehyde was dissolved in 40 ml of ethanol, 20 ml of distilled water containing 22 g of potassium cyanide was slowly added. The mixture was refluxed for 1 hour, cooled, and then 350 ml of distilled water was added to form a precipitate. The precipitate was filtered under reduced pressure, and the precipitate was stirred with 40 ml of ethanol for 20 minutes. After filtration, washed several times with ethanol and dried, ≪ / RTI >
- Step 2 19 g of 2-hydroxy-1,2-bis (4-methoxyphenyl) ethanone and 14 g of P 2 S 5 were placed in 100 ml of 1,4-dioxane and stirred. The solution was refluxed for 28 hours, cooled and filtered. The filtrate was transferred to a 500 ml reactor. A solution of 9 g of NiCl 2 .H 2 O dissolved in 30 ml of distilled water was slowly added over 2 hours. After completion of the addition, the mixture was refluxed for 30 hours and cooled. 200 ml of acetone was added to the cooled reaction product, which was then filtered under reduced pressure, washed several times with acetone, and then dried to obtain 12 g of a dark green object.
- Step 3 A stirring 22g of AlCl 3 in dichloromethane 50ml for 30 minutes and then diluted 12-methoxy -Ni- complex 21g 60ml in dichloromethane was added slowly. After reacting for 30 minutes at room temperature, 200 ml of distilled water was added slowly under ice chamber. The precipitate formed was filtered under reduced pressure, washed several times with distilled water, and washed with a small amount of methanol. And dried to obtain 19 g of a dark green object.
- Step 1 After 50 g of benzaldehyde was dissolved in 80 ml of ethanol, 70 ml of distilled water containing 8 g of sodium cyanide was slowly added. The mixture was refluxed for 3 hours and then cooled. The precipitate thus formed was filtered under reduced pressure. The precipitate was washed several times with ethanol and then dried to obtain 35 g of a pale yellow object.
- Step 2 8.6 g of 2-hydroxy-1,2-diphenylethanone and 11.8 g of 2-hydroxy-1,2-bis (4-methoxyphenyl) ethanone were mixed with 18 g of P 2 S 5 , Was added to 100 ml of 4-dioxane and stirred. After refluxing for 4 hours, the reaction solution was cooled and filtered. The filtrate was transferred to a 500 ml reactor, and then cooled to 0 ° C using an ice bath. A solution of 10 g of NiCl 2 .H 2 O dissolved in distilled water Lt; / RTI > After the addition was complete, the mixture was refluxed for 28 hours and cooled. 50 ml of acetone was added to the cooled reactant, the mixture was filtered under reduced pressure, washed several times with acetone, and then dried to obtain 16 g of a dark green object.
- Step 3 After stirring the 20g of AlCl 3 in dichloromethane 60ml for 30 minutes by diluting the 12-methoxy -Ni- complex 30g 50ml in dichloromethane was added slowly. After reacting at room temperature for 30 minutes, 200 ml of distilled water was added slowly under ice bath. The precipitate formed was filtered under reduced pressure, washed several times with distilled water, and washed with a small amount of methanol. And dried to obtain 17 g of a dark green object.
- Example 6 The procedure of Example 6 was repeated, except that 24.12 g (0.165 mol, 15 eq) of ZnCl 2 was used.
- a near infrared ray absorbent comprising a novel dithiol-based metal complex having improved solubility in an organic solvent of alcohols as well as ketone-based and halogen-based solvents.
- the near infrared absorber with improved solubility can realize efficient mixing with an organic material such as a polymer resin, the excellent near infrared absorbing property of the dithiol-based metal complex compound is sufficiently exhibited, and the near- Or a thermal infrared shielding filter.
- an optical filter using the near infrared ray absorbent excellent in the selective near infrared ray shielding effect and excellent in high-temperature stability can be obtained by providing the near infrared ray absorbent of the present invention in a manufacturing process step or in a separate master batch form, It can be usefully used for a thermal infrared shielding filter.
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Abstract
La présente invention concerne un absorbant de proche infrarouge constitué de complexe métallique de dithiol, un procédé de préparation dudit complexe métallique de dithiol, et un filtre optique et filtre de protection contre l'infrarouge thermique contenant ledit absorbant de proche infrarouge. L'absorbant de proche infrarouge est constitué d'un complexe métallique de dithiol qui réalise une absorption sélective du seul proche infrarouge, et étant donné que ledit complexe métallique de dithiol présente une solubilité améliorée par rapport aux solvants organiques, un mélange efficace est obtenu avec des matériaux organiques comprenant de la résine polymérique et analogue, qui sont mélangés lors de la fabrication d'un filtre optique, de sorte qu'une performance suffisamment supérieure d'absorption de proche infrarouge dudit complexe métallique de dithiol est assurée, et permet la préparation d'un nouvel absorbant de proche infrarouge dont la capacité d'absorption de proche infrarouge ne se détériore pas sur une longue période. En outre, l'absorbant de proche infrarouge selon la présente invention est préparé et obtenu soit par une étape de procédé de fabrication soit sous une forme de mélange maître; ainsi il peut être utilisé avantageusement pour un filtre optique, particulièrement un filtre de protection contre l'infrarouge thermique par l'utilisation d'un colorant d'absorption de proche infrarouge et présentant à la fois des effets de protection sélective contre le proche infrarouge qui sont supérieurs aux films de revêtement existants, et également une excellente stabilité à des températures élevées.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020080105189A KR20100046373A (ko) | 2008-10-27 | 2008-10-27 | 디티올계 금속 착화합물로 이루어진 근적외선 흡수제, 상기디티올계 금속 착화합물의 제조방법, 그를 함유한 광학 필터 및 열적외선 차폐 필터 |
| KR10-2008-0105189 | 2008-10-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2010050720A2 WO2010050720A2 (fr) | 2010-05-06 |
| WO2010050720A3 WO2010050720A3 (fr) | 2010-08-05 |
| WO2010050720A4 true WO2010050720A4 (fr) | 2010-09-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2009/006216 WO2010050720A2 (fr) | 2008-10-27 | 2009-10-27 | Absorbant de proche infrarouge constitué de complexe métallique de dithiol, procédé de préparation dudit complexe métallique de dithiol, et filtre optique et filtre de protection contre l’infrarouge thermique contenant un tel absorbant |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20100046373A (fr) |
| WO (1) | WO2010050720A2 (fr) |
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| WO2012152584A1 (fr) * | 2011-05-06 | 2012-11-15 | Basf Se | Chromophores comprenant des substituants perfluoroalkyle |
| CN104177238B (zh) * | 2014-07-25 | 2016-05-25 | 山东大学 | 合成3,4-二(3,4,5-三甲氧基苯基)-2,5-二苯基环戊二烯酮的方法 |
| CN118005543A (zh) * | 2024-04-10 | 2024-05-10 | 蜂巢能源科技股份有限公司 | 一种电解液添加剂及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1112425A (ja) * | 1997-06-23 | 1999-01-19 | Mitsubishi Rayon Co Ltd | プラズマディスプレイ用光学フィルタ |
| US6217796B1 (en) * | 1998-11-17 | 2001-04-17 | Nisshinbo Industries, Inc. | Near infrared absorption composition |
| JP2001138623A (ja) * | 1999-11-12 | 2001-05-22 | Canon Inc | 被記録媒体 |
-
2008
- 2008-10-27 KR KR1020080105189A patent/KR20100046373A/ko not_active Application Discontinuation
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- 2009-10-27 WO PCT/KR2009/006216 patent/WO2010050720A2/fr active Application Filing
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| Publication number | Publication date |
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| WO2010050720A3 (fr) | 2010-08-05 |
| WO2010050720A2 (fr) | 2010-05-06 |
| KR20100046373A (ko) | 2010-05-07 |
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