KR101677574B1 - Phthalocyanine compound and near infrared ray absorption filter using the same - Google Patents
Phthalocyanine compound and near infrared ray absorption filter using the same Download PDFInfo
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- KR101677574B1 KR101677574B1 KR1020090126787A KR20090126787A KR101677574B1 KR 101677574 B1 KR101677574 B1 KR 101677574B1 KR 1020090126787 A KR1020090126787 A KR 1020090126787A KR 20090126787 A KR20090126787 A KR 20090126787A KR 101677574 B1 KR101677574 B1 KR 101677574B1
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- phthalocyanine compound
- near infrared
- phthalocyanine
- absorption
- metal
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- -1 Phthalocyanine compound Chemical class 0.000 title claims abstract description 43
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 5
- 150000005309 metal halides Chemical class 0.000 claims abstract description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 5
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 5
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 241000282472 Canis lupus familiaris Species 0.000 claims abstract description 3
- 229910001935 vanadium oxide Chemical group 0.000 claims description 10
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical group [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 150000001875 compounds Chemical group 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000975 dye Substances 0.000 description 18
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 16
- 238000010992 reflux Methods 0.000 description 13
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 235000003270 potassium fluoride Nutrition 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 2
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical class C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 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
- 238000002360 preparation method Methods 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
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- 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
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
A novel phthalocyanine compound and a near-infrared absorption filter using the same, which exhibit a low absorption rate of light in the visible light region but exhibit excellent absorption efficiency in the near-infrared region (wavelength of 750 to 1100 nm) are disclosed. The phthalocyanine compound is represented by the following general formula (1).
[Chemical Formula 1]
In Formula 1, A 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14 and A 15 are each independently OR 1 , SR 2 or a halogen atom; Wherein A 1 , A 4 , A 5 , A 8 , A 9 , A 12 , A 13 and A 16 are each independently OR 1 , SR 2 , NR 3 R 4 , NHR 5 or a halogen atom, dogs NR 3 R 4 or NHR 5, and, at least one of which is NR 3 R 4, and; Each of R 1 , R 2 , R 3 , R 4 and R 5 independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, To 20; R 3 and R 4 may be connected to each other to form a cyclic structure; M is a non-metal, metal, metal oxide or metal halide.
Phthalocyanine compound, near infrared absorption filter, maximum absorption wavelength, half width, absorption region
Description
The present invention relates to a phthalocyanine compound and a near infrared absorbing filter using the same and more particularly to a novel phthalocyanine compound exhibiting an excellent absorption efficiency in a near infrared region (wavelength of 750 to 1100 nm) The present invention relates to a near-infrared absorption filter used.
The phthalocyanine compound has excellent thermal and chemical stability due to its structural characteristics and its absorption characteristics change depending on the metal element introduced at the center of the compound structure or the characteristic group substituted in the structure outline, A dye for absorbing near infrared rays of a near infrared ray absorbing filter for a display such as an organophotoreceptor applied dye and a PDP (plasma display), a sensitizer for a solar cell, a near infrared ray absorbing filter for a heat shield used for a home or automobile, Has been widely applied. Among the above applications, the recent expansion of the display industry and eco-friendly business (energy conservation through the heat conduction) has led to the development of a near infrared absorbing dye of a near infrared absorbing filter used for PDP, The usage is increasing rapidly.
The near infrared absorbing dye for PDP exhibits high light absorption characteristics in the region of 750 to 1100 nm but has a low light absorbing property in the visible light region, that is, a high transmittance, so that the light in the near infrared region, which may cause malfunction of the remote control, , Color reproducibility of the display device can be improved. In addition, since the near infrared absorbing dye used for the purpose of heat shielding is mainly used for buildings and automobile exterior, it should have excellent thermal and chemical stability and have broad and high light absorption characteristics in the range of 750 to 1100 nm. As such a near-infrared absorbing dye, various compounds such as a cyanine compound, a nickel-dithionyl compound, and a diimonium compound are used in addition to a phthalocyanine compound. However, the cyanine-based compound has insufficient heat resistance and narrow absorption region, and therefore, it is difficult to apply the diimonium compound. Diimonium-based compounds have limited applications because of their durability to the surrounding environment such as moisture and compatibility with high molecular materials, It is not suitable for the coating type near infrared ray filter method which is being used recently. Further, the nickel-dithionyl compound has an advantage of low absorption property in the visible light region, but its application is limited because of its low solubility.
On the other hand, the phthalocyanine compound is excellent in durability and environmental resistance as compared with other compounds, and solubility problem can be solved by controlling substituents on the structure outer side, and absorption at a maximum absorption wavelength is also large. Type near-infrared absorption filter. However, the conventional phthalocyanine compound for near infrared absorption has a narrow wavelength region having absorption, so that the full width at half maximum (FWHM) is merely 70 to 90 nm. Therefore, in order to use a conventional phthalocyanine compound as a dye for a PDP or a near infrared ray absorption filter applied to a heat shield, three or more pigments (phthalocyanine compounds having different maximum absorption wavelengths) are mixed as a near infrared absorbing dye, (Phthalocyanine compound), compatibility between the near-infrared absorbing dye (phthalocyanine compound) and the binder material, compatibility between the near infrared absorbing dye (phthalocyanine compound) itself and the like may occur.
Accordingly, an object of the present invention is to provide a phthalocyanine compound exhibiting a wide and uniform absorption efficiency in a near-infrared region (wavelength of 750 to 1100 nm) and exhibiting excellent transmission characteristics in a visible light region (wavelength of 400 to 700 nm).
Another object of the present invention is to provide a near infrared absorbing filter comprising one or two phthalocyanine compounds as a near infrared absorbing dye.
In order to achieve the above object, the present invention provides a phthalocyanine compound represented by the following general formula (1).
[Chemical Formula 1]
In
Further, the present invention provides a near infrared absorbing filter comprising the phthalocyanine compound.
The phthalocyanine compound according to the present invention has a maximum absorption wavelength in the range of 750 to 1100 nm and a half width of 130 nm or more, and the half width is 2 to 3 times wider as compared with the conventional phthalocyanine compound. Therefore, in the production of the near infrared absorbing filter, only one or two kinds of phthalocyanine compounds can be used as the near infrared absorbing coloring matter. In addition, when the near infrared absorbing coloring matter (phthalocyanine compound) Problems of compatibility between the near-infrared absorbing dye itself and the like can be prevented.
Hereinafter, the present invention will be described in detail.
The phthalocyanine compound according to the present invention is a near-infrared absorbing compound exhibiting an excellent absorption efficiency in a near-infrared region (wavelength of 750 to 1100 nm), while having a low light absorption rate in a visible light region.
In Formula 1, A 2, A 3, A 6, A 7, A 10, A 11, A 14 and A 15 are, each independently, is OR 1, SR 2 or a halogen atom, A 1, A 4, A 5, a 8, a 9, a 12, a 13 and a 16 are each independently, oR 1, SR 2, NR 3 R 4, and NHR 5, or a halogen atom, at least five of which NR 3 R 4, or and NHR 5, at least one of which is NR 3 R 4. R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, a substituted or unsubstituted group having 6 to 14 carbon atoms, Is an aryl group having 6 to 10 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, preferably 7 to 16 carbon atoms, and R 3 and R 4 are connected to each other to form a cyclic structure In this case, NR 3 R 4 forms a heterocyclic compound having 4 to 20 carbon atoms, preferably 4 to 8 carbon atoms, such as a pyrrolidine or piperidine structure. can do. M is at least one selected from the group consisting of a nonmetal, a metal, a metal oxide or a metal halide, preferably a nonmetal such as hydrogen, a metal such as copper, zinc or nickel, a metal oxide such as titanium oxide or vanadium oxide, a metal halide such as indium chloride or gallium chloride , More preferably copper or vanadium oxide.
The phthalocyanine compound according to the present invention can be prepared by a known method for preparing a phthalocyanine compound, for example, a substituted dicyanobenzene or a substituted diiminoisoindoline can be produced through a high temperature reaction together with a suitable catalyst , Preferably prepared using substituted dicyanobenzene as described in various articles (e.g., Inorg. Chem. 1995, 34, 1636-1637) and in patents (e.g. Japanese Patent No. 1997-316049) can do.
The phthalocyanine compound according to the present invention has a maximum absorption wavelength in the range of 750 to 1100 nm, preferably 900 to 1100 nm, and has a full width at half maximum (FWHM) of 100 to 300 nm, preferably 130 to 300 nm . When the half-width of the phthalocyanine compound is less than 100 nm, at least three kinds of phthalocyanine compounds should be used as the near infrared absorbing dye in the production of the near-infrared absorbing filter, so that compatibility between the phthalocyanine compound and the binder material and compatibility of the phthalocyanine compound may be deteriorated , There is a possibility that the near-infrared absorption effect is lowered.
The phthalocyanine compound according to the present invention can be used in the production of a near infrared absorbing filter as a dye of a near infrared absorbing filter according to a conventional method. Most of transparent polymer resins such as polymethylmethacrylate, polyester, polycarbonate and polyurethane can be used as the polymer resin suitable for the near-infrared absorbing filter. However, in view of heat resistance and environmental resistance required for each application Use suitable materials. The near infrared absorbing filter may be prepared by dissolving the near infrared absorbing dye in a solvent and coating the solution with the polymer resin. As the solvent, various solvents such as methyl ethyl ketone, tetrahydrofuran, chloroform, and toluene may be used.
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. The following examples illustrate the present invention, and the scope of the present invention is not limited by the following examples.
[Example 1] Production of vanadium oxide phthalocyanine compound (VOPc (PhS) 8 (C 4 H 8 N) 8 )
10 g of 3,4,5,6-tetrafluoro phthalonitrile, 10 g of thiophenol and 7 g of potassium fluoride were placed in a three-necked flask equipped with a reflux condenser, and 30 ml of acetonitrile was added as a solvent, followed by stirring at room temperature for 12 hours . After completion of the reaction, the reaction solution was filtered and vacuum distilled. 20 g of the thus obtained crude reaction product was placed in a three-necked flask equipped with a reflux condenser and subjected to a reflux reaction for 8 hours together with 2 g of vanadium trichloride, 2 g of 1-octanol and 30 g of benzonitrile. After completion of the reaction, a precursor compound VOPc (PhS) 8 F 8 (where Ph = phenyl) was obtained through vacuum distillation. 10 g of the crude vanadium oxide phthalocyanine precursor compound and 50 ml of pyrrolidine were placed in a three-necked flask equipped with a reflux condenser and reacted at 60 ° C for 8 hours. After completion of the reaction, the reaction solution was concentrated in vacuo to obtain a vanadium phthalocyanine oxide compound VOPc (PhS) 8 (C 4 H 8 N) 8 . The vanadium oxide phthalocyanine compound thus prepared had a maximum absorption wavelength of 1052 nm and a half width of 200 nm or more.
[Example 2] Production of vanadium oxide phthalocyanine compound (VOPc (PhS) 8 {(C 4 H 9 ) 2 N} 8 )
(VOPc: Oxo-Vanadium Phthalocyanine) precursor compound VOPc (PhS) 8 F 8 (where Ph = phenyl) was obtained in the same manner as in Example 1 above. 10 g of the crude vanadium phthalocyanine precursor compound and 50 ml of dibutylamine were placed in a three-necked flask equipped with a reflux condenser and reacted at 160 ° C for 20 hours. Concentrated in vacuo and the reaction solution after the completion of the reaction by, vanadium phthalocyanine compound VOPc (PhS) 8 {(C 4 H 9) 2 N} to obtain a 8. The vanadium oxide phthalocyanine compound thus prepared had a maximum absorption wavelength of 1040 nm and a half width of 200 nm or more.
[Example 3] Preparation of copper phthalocyanine compound (CuPc (2,5-Cl 2 PhO) 8 (C 4 H 8 N) 8 )
10 g of 3,4,5,6-tetrafluoro phthalonitrile, 15 g of 2,5-dichlorophenol and 7 g of potassium fluoride were placed in a three-necked flask equipped with a reflux condenser, 30 ml of acetonitrile as a solvent was added, Stir for 12 hours. After completion of the reaction, the reaction solution was filtered and vacuum distilled. 20 g of the thus obtained crude reaction product was placed in a three-necked flask equipped with a reflux condenser and subjected to a reflux reaction together with 2 g of cupric chloride and 30 g of dimethylformamide for 8 hours. After completion of the reaction, a copper phthalocyanine (CuPc) precursor compound CuPc (2,5-Cl 2 PhO) 8 F 8 (where Ph = phenyl) was obtained through vacuum distillation. 10 g of the crude copper phthalocyanine-based precursor compound and 50 ml of pyrrolidine were placed in a three-necked flask equipped with a reflux condenser and reacted at 60 ° C for 8 hours. After completion of the reaction, the reaction solution was concentrated in vacuo to obtain a copper phthalocyanine compound CuPc (2,5-Cl 2 PhO) 8 (C 4 H 8 N) 8 . The maximum absorption wavelength of the produced copper phthalocyanine compound was 940 nm, and the half width was 137 nm.
COMPARATIVE EXAMPLE Production of vanadium oxide phthalocyanine compound (VOPc ( PhS ) 8 {2,6- (CH 3 ) 2 PhO} 4 ( C 6 H 11 NH ) 4 )
10 g of 3,4,5,6-tetrafluoro phthalonitrile, 10 g of thiophenol and 7 g of potassium fluoride were placed in a three-necked flask equipped with a reflux condenser and 30 ml of acetonitrile was added as a solvent. Then, Lt; / RTI > After completion of the reaction, 7 g of 2,6-dimethylphenol and 4 g of potassium fluoride were added to the reaction mixture, and the mixture was refluxed for 8 hours. When the reaction was completed, the reaction mixture was vacuum distilled. 20 g of the crude reaction product thus obtained was placed in a three-necked flask equipped with a reflux condenser and subjected to a reflux reaction for 8 hours together with 2 g of vanadium trichloride, 2 g of 1-octanol and 30 g of benzonitrile. After completion of the reaction, the vanadium phthalocyanine precursor compound VOPc (PhS) 8 {2,6- (CH 3 ) 2 PhO} 4 F 4 was obtained through vacuum distillation. 10 g of the crude vanadium phthalocyanine-based precursor compound and 50 ml of cyclohexylamine were placed in a three-necked flask equipped with a reflux condenser and reacted at 60 ° C for 8 hours. After the reaction was completed, the reaction solution was concentrated in vacuo to obtain a vanadium phthalocyanine oxide compound VOPc (PhS) 8 {2,6- (CH 3 ) 2 PhO} 4 (C 6 H 11 NH) 4 . The vanadium oxide phthalocyanine compound thus prepared had a maximum absorption wavelength of 932 nm and a half width of 77 nm.
[Experimental Example] UV / VIS spectrum analysis
The phthalocyanine compounds prepared in Examples 1 to 3 and Comparative Examples were each diluted to a concentration of 10 ppm in toluene, and UV / VIS spectra were measured. The UV / VIS absorption spectra of the phthalocyanine compounds prepared in Examples 1 to 3 and Comparative Examples are shown in Fig. 1, from which the maximum absorption wavelength was calculated. The difference between the wavelengths representing half of the extinction coefficient at the maximum absorption wavelength is represented by the half width (nm).
From the above Table 1, it can be seen that the phthalocyanine compounds (Examples 1 to 3) according to the present invention have a broader half-width than the phthalocyanine compound represented by the above-mentioned formula (4) prepared in the comparative example, and are broad in the entire near infrared region (750 to 1100 nm) Infrared absorption absorptive filter, it is possible to use only one or two kinds of phthalocyanine compounds as near-infrared absorbing dyes in the production of the near-infrared absorbing filter, and to obtain each of the near-infrared absorbing dyes (phthalocyanine compounds) Compatibility problems between the binder material and the binder material, compatibility problems between the near infrared absorbing dye itself and the like can be prevented.
1 is a UV / VIS absorption spectrum of the phthalocyanine compound prepared in Examples 1 to 3 and Comparative Example of the present invention.
Claims (3)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020090126787A KR101677574B1 (en) | 2009-12-18 | 2009-12-18 | Phthalocyanine compound and near infrared ray absorption filter using the same |
| PCT/KR2010/009009 WO2011074886A2 (en) | 2009-12-18 | 2010-12-16 | Phthalocyanine compounds and near infrared-absorbing filters using same |
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| KR1020090126787A KR101677574B1 (en) | 2009-12-18 | 2009-12-18 | Phthalocyanine compound and near infrared ray absorption filter using the same |
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| KR101677574B1 true KR101677574B1 (en) | 2016-11-18 |
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| JP6007428B2 (en) * | 2011-10-26 | 2016-10-12 | 山田化学工業株式会社 | Phthalocyanine compound and synthesis method thereof, near-infrared absorbing dye and near-infrared absorbing material |
| JP6024048B2 (en) * | 2012-07-23 | 2016-11-09 | 山田化学工業株式会社 | Heat ray shielding material |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2000026748A (en) * | 1998-02-03 | 2000-01-25 | Nippon Shokubai Co Ltd | Phthalocyanine compound, and its production and application thereof |
| JP2000281927A (en) * | 1999-03-31 | 2000-10-10 | Nippon Shokubai Co Ltd | Pigment dispersing agent and its use |
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| JP4011766B2 (en) * | 1998-10-20 | 2007-11-21 | 富士フイルム株式会社 | Anti-reflection coating |
| US20060051586A1 (en) * | 2004-08-28 | 2006-03-09 | Park Sang H | Film for PDP filter, PDP filter comprising the same and plasma display panel produced by using the PDP filter |
| JP4639803B2 (en) * | 2004-12-28 | 2011-02-23 | 東洋紡績株式会社 | Near infrared absorbing filter and method for producing wave near infrared absorbing film for plasma display |
| KR100764589B1 (en) * | 2006-08-07 | 2007-10-08 | 재단법인서울대학교산학협력재단 | Dyes for pdp filter absorbable neon and near ir radiation at the same time |
| KR100953556B1 (en) * | 2007-02-08 | 2010-04-21 | 주식회사 엘지화학 | Pdp filter for absorbing near infrared ray |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2000026748A (en) * | 1998-02-03 | 2000-01-25 | Nippon Shokubai Co Ltd | Phthalocyanine compound, and its production and application thereof |
| JP2000281927A (en) * | 1999-03-31 | 2000-10-10 | Nippon Shokubai Co Ltd | Pigment dispersing agent and its use |
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| Publication number | Publication date |
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| WO2011074886A2 (en) | 2011-06-23 |
| WO2011074886A3 (en) | 2011-11-24 |
| KR20110070099A (en) | 2011-06-24 |
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