WO2011074890A2 - 바나딜 프탈로시아닌 화합물 및 이를 이용한 근적외선 흡수 필터 - Google Patents
바나딜 프탈로시아닌 화합물 및 이를 이용한 근적외선 흡수 필터 Download PDFInfo
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- WO2011074890A2 WO2011074890A2 PCT/KR2010/009015 KR2010009015W WO2011074890A2 WO 2011074890 A2 WO2011074890 A2 WO 2011074890A2 KR 2010009015 W KR2010009015 W KR 2010009015W WO 2011074890 A2 WO2011074890 A2 WO 2011074890A2
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- Prior art keywords
- absorption
- phthalocyanine compound
- region
- vanadil
- infrared
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- 238000010521 absorption reaction Methods 0.000 title claims abstract description 52
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical class [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 title abstract description 10
- -1 phthalocyanine compound Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims description 2
- 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 abstract description 17
- 230000031700 light absorption Effects 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000975 dye Substances 0.000 description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 238000002834 transmittance Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000008033 biological extinction Effects 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- 238000000411 transmission spectrum Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 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
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
-
- 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
Definitions
- the present invention relates to a vanadil phthalocyanine compound and a near infrared absorption filter using the same. More specifically, the absorption of light is low in the visible region, while the absorption efficiency is excellent in the long wavelength region (especially, a wavelength of 950 to 1100 nm) in the near infrared region. And a novel vanadil phthalocyanine compound and a near infrared absorption filter using the same.
- Phthalocyanine compounds were first developed as pigments and are not only thermally and chemically stable, but also when various substituents are introduced into the outer structure, solubility and light absorption properties change depending on the structural properties of each material. Therefore, the phthalocyanine compound is used for various applications requiring thermal and chemical stability, for example, dyes for near infrared absorption of near-infrared absorption filters for displays such as organophotoreceptor applied dyes for laser printers and plasma displays (PDPs), and sensitizers for solar cells. It is widely applied to pigments for absorbing near infrared rays of near-infrared absorption filters for heat shielding purposes used in homes or cars. In recent years, with the rapid expansion of the display industry and eco-friendly business (energy saving through heat shielding), the amount of the near-infrared absorbing dye for the PDP, in particular, is rapidly increasing.
- the near infrared absorbing dye for PDP exhibits high light absorption characteristics in the 800 to 1100 nm region, but has low light absorption characteristics in the visible region, that is, high transmittance, so as to block light in the near infrared region that may cause malfunction of the remote controller.
- the color reproducibility of the display device can be improved.
- a near-infrared absorbing dye not only a phthalocyanine compound but various compounds, such as a cyanine type compound, a nickel- dithionyl type compound, and a dimonium type compound, are used.
- cyanine-based compounds are poor in practical application due to lack of heat resistance and narrow absorption region, and dimonium-based compounds have insufficient durability to surrounding environments such as moisture and compatibility with high molecular materials, and thus their use is limited. In particular, it is not suitable for the coating type near infrared filter method currently used.
- the nickel-dithionyl compound has the advantage of low absorption in the visible light region, but the solubility is low, the use is limited.
- phthalocyanine compounds compared with other compounds, have excellent durability and environmental resistance, can solve the solubility problem by adjusting the substituents in the outer structure, and by changing the central metal, relatively in the near-infrared region of 800 to 950nm, Absorption efficiency can be increased freely, and it is known that it is suitable for the coating type near-infrared absorption filter system applied to PDP.
- the conventional phthalocyanine compound for near-infrared absorption use is mainly excellent in the photosensitivity in the 800-950 nm area
- an object of the present invention is to provide a vanadil phthalocyanine compound that exhibits a broad and high absorption efficiency in a long wavelength region (especially a wavelength of 950 to 1100 nm) in the near infrared region and exhibits excellent transmission characteristics in a visible region (wavelength of 400 to 700 nm). To provide.
- Another object of the present invention is to provide a near infrared absorption filter containing one or two vanadil phthalocyanine compounds as the near infrared absorbing dye.
- the present invention provides a vanadil phthalocyanine compound represented by the following formula (1).
- a 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14, and A 15 are SR 1 ;
- R 1 , R 2 , R 3 , R 4 and R 5 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms or a substituted or unsubstituted carbon number
- Aralkyl groups of 7 to 20, R 4 and R 5 may be connected to each other to form a cyclic structure.
- the present invention also provides a near-infrared absorption filter comprising the vanadil phthalocyanine compound.
- the vanadil phthalocyanine compound according to the present invention has a maximum absorption wavelength in the range of 950 to 1000 nm, excellent half width and absorbance at the maximum absorption wavelength, and transmittance (T%) at the maximum absorption wavelength is 10%. It has a transmittance of 75% or more in the visible light region (about 450nm). Therefore, since only one or two phthalocyanine compounds are used as the near-infrared absorbing dye in the preparation of the near-infrared absorbing filter, problems such as compatibility caused when mixing three or more dyes can be improved, and the manufacturing process is simple and economical. to be.
- Example 1 is a UV / VIS absorption spectrum of the vanadil phthalocyanine compound prepared in Examples 1 to 3 and Comparative Example 1 of the present invention.
- the vanadil phthalocyanine compound according to the present invention is a near-infrared absorbing compound that exhibits a wide and high absorption efficiency in a long wavelength region (especially, a wavelength of 950 to 1100 nm) in the near infrared region and an excellent transmission characteristic in the visible region (wavelength of 400 to 700 nm). As represented by the structure of the formula (1).
- a 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14, and A 15 are SR 1 , A 1 , A 4 , A 5 , A 8 , A 9 , A 12 , A 13 and A 16 are each independently SR 1 , OR 2 , NHR 3 , NR 4 R 5 or a halogen atom, at least 4 of which are OR 2 , and 1 to 4 are NR 4 R 5 .
- R 1 , R 2 , R 3 , R 4 and R 5 are each independently a substituted or unsubstituted C1-10 alkyl group, preferably a C1-6 alkyl group, a substituted or unsubstituted C6-14, preferably Preferably 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 4 and R 5 may be linked to each other to form a cyclic structure.
- the NR 4 R 5 is a heterocyclic compound having 4 to 20, preferably 4 to 8 carbon atoms, such as pyrrolidine, piperidine structure, etc. can do.
- the vanadil phthalocyanine compound according to the present invention may be prepared by a known method for preparing phthalocyanine compounds, and for example, substituted dicyanobenzene or substituted diiminoisoindolin may be prepared through high temperature reaction with a suitable catalyst. And substituted dicyanobenzene, preferably as described in various articles (e.g., Inorg. Chem. 1995, 34, 1636-1637) and patents (e.g., Japanese Patent Laid-Open No. 1997-316049). It can be prepared using.
- the vanadil phthalocyanine compound according to the present invention preferably has a maximum absorption wavelength in the range of 950 to 1000 nm, has a full width at half maximum (FWHM) of 50 to 150 nm, and an absorption coefficient ( ⁇ ). , Unit: ml / g ⁇ cm) is excellent, 50,000 to 70,000.
- T% at the maximum absorption wavelength is 10%, it has a transmittance of 75% or more in the visible light region (around 450 nm).
- the vanadil phthalocyanine compound which concerns on this invention can be used for manufacture of a near-infrared absorption filter as a pigment
- the polymer resin suitable for the near infrared absorption filter most transparent polymer resins such as polymethyl methacrylate, polyester, polycarbonate, and polyurethane can be used, but the conditions such as heat resistance and environmental resistance required for each application can be used. Use suitable materials.
- 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.
- Vanac (Vanadium Phthalocyanine) precursor compound VOPc (PhS) 8 ⁇ 2,6 -(CH 3 ) 2 PhO ⁇ 4 F 4 10 g (hereinafter, Ph phenyl, A 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14 and A 15 in Formula 1 is PhS); Into a three-necked flask equipped with a reflux device, it was reacted with 200 ml of pyrrolidine for 2 hours at 60 °C.
- vanadil phthalocyanine compound VOPc (PhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 (C 4 H 8 N) 4 The maximum absorption wavelength of the manufactured vanadil phthalocyanine compound was 962 nm, and the absorption coefficient was 61,400 ml / g ⁇ cm.
- Vanadic phthalocyanine precursor compound VOPc (4-CH 3 OPhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ having a UV / VIS maximum absorption wavelength of 803 nm and an absorption coefficient ( ⁇ ) of 96,400 ml / g ⁇ cm 10 g of 4 F 4 was charged to a three-necked flask equipped with a reflux device, and reacted with 200 ml of pyrrolidine at 60 ° C. for 2 hours.
- vanadil phthalocyanine compound VOPc (4-CH 3 OPhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 (C 4 H 8 N) 4 It was.
- the maximum absorption wavelength of the manufactured vanadil phthalocyanine compound was 972 nm, and the absorption coefficient was 59,200 ml / g ⁇ cm.
- VOPc (PhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 F 4 10 g was charged to a three-necked flask equipped with a reflux device and reacted with 200 ml of dibutylamine at 160 ° C. for 48 hours. After the reaction was completed, the reaction solution was filtered and concentrated in vacuo to give vanadil phthalocyanine compound VOPc (PhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 (C 8 H 18 N) 4 .
- the maximum absorption wavelength of the manufactured vanadil phthalocyanine compound was 954 nm, and the absorption coefficient was 58,300 ml / g ⁇ cm.
- VOPc (PhS) 8 ⁇ 2,6- (CH 3 ) 2 PhO ⁇ 4 (C 6 H 11 NH) 4 The maximum absorption wavelength of the manufactured vanadil phthalocyanine compound was 932 nm, and the absorption coefficient was 57,100 ml / g ⁇ cm.
- the vanadil phthalocyanine compounds prepared in Examples 1 to 3 and Comparative Example 1 were diluted in toluene at a concentration of 10 ppm, respectively, and UV / VIS spectra were measured.
- UV / VIS absorption spectra of the vanadil phthalocyanine compounds prepared in Examples 1 to 3 and Comparative Example 1 are shown in FIG. 1, from which the maximum absorption wavelength and extinction coefficient (ml / g ⁇ cm) were calculated.
- UV / VIS transmission spectra of the vanadil phthalocyanine compounds prepared in Examples 1 to 3 and Comparative Example 1 are shown in FIG. 2, from which the maximum absorption wavelength and the transmittance in the visible region, ie, 455 nm, are measured.
- the transmittance in the visible light region means transmittance when the transmittance at the maximum absorption wavelength is fixed at 10%.
- the difference between wavelengths representing the half value of the extinction coefficient at the maximum absorption wavelength is represented by half width (nm).
- the vanadil phthalocyanine compound (Examples 1 to 3) according to the present invention it can be seen that the maximum absorption wavelength is a longer wavelength than the vanadil phthalocyanine compound prepared in Comparative Example 1, the half-width is wide and the absorption coefficient Since it is large, it can be seen that it exhibits a wide and high absorption efficiency in the long wavelength region (wavelength of 950 to 1100 nm) of the near infrared region. In addition, it can be seen that the transmission of visible light is also excellent.
- the vanadil phthalocyanine compound which concerns on this invention is useful as a near-infrared absorption filter as a near-infrared absorption dye.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Optical Filters (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (2)
- 하기 화학식 1로 표시되는 바나딜 프탈로시아닌 화합물.[화학식 1]상기 화학식 1에서, A2, A3, A6, A7, A10, A11, A14 및 A15는 SR1이며; A1, A4, A5, A8, A9, A12, A13 및 A16은 각각 독립적으로, SR1, OR2, NHR3, NR4R5 또는 할로겐 원자이며, 이들 중 적어도 4개는 OR2이고, 1 내지 4개는 NR4R5이며; R1, R2, R3, R4 및 R5는 각각 독립적으로, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 탄소수 6 내지 14의 아릴기 또는 치환 또는 비치환된 탄소수 7 내지 20의 아랄킬기이며, R4 및 R5는 서로 연결되어 고리(cyclic) 구조를 형성할 수 있다.
- 제1항에 따른 바나딜 프탈로시아닌 화합물을 포함하는 근적외선 흡수 필터.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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US13/516,218 US20120271044A1 (en) | 2009-12-18 | 2010-12-16 | Vanadyl phthalocyanine compounds and near-infrared absorption filters using same |
CN201080064114.2A CN102762580B (zh) | 2009-12-18 | 2010-12-16 | 氧钒基酞菁化合物及使用其的近红外吸收滤光器 |
EP10837886.0A EP2514755A4 (en) | 2009-12-18 | 2010-12-16 | Vanadyl phthalocyanine compounds and near-infrared absorption filters using same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR10-2009-0126778 | 2009-12-18 | ||
KR1020090126778A KR101153787B1 (ko) | 2009-12-18 | 2009-12-18 | 바나딜 프탈로시아닌 화합물 및 이를 이용한 근적외선 흡수 필터 |
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WO2011074890A2 true WO2011074890A2 (ko) | 2011-06-23 |
WO2011074890A3 WO2011074890A3 (ko) | 2011-11-03 |
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PCT/KR2010/009015 WO2011074890A2 (ko) | 2009-12-18 | 2010-12-16 | 바나딜 프탈로시아닌 화합물 및 이를 이용한 근적외선 흡수 필터 |
Country Status (5)
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US (1) | US20120271044A1 (ko) |
EP (1) | EP2514755A4 (ko) |
KR (1) | KR101153787B1 (ko) |
CN (1) | CN102762580B (ko) |
WO (1) | WO2011074890A2 (ko) |
Cited By (1)
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JP2014031421A (ja) * | 2012-08-02 | 2014-02-20 | Nippon Shokubai Co Ltd | フタロシアニン化合物およびこれを含む赤外線カットフィルター |
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CN102637636A (zh) | 2011-08-24 | 2012-08-15 | 京东方科技集团股份有限公司 | 有机薄膜晶体管阵列基板及其制作方法和显示装置 |
JP6007428B2 (ja) * | 2011-10-26 | 2016-10-12 | 山田化学工業株式会社 | フタロシアニン化合物及びその合成方法、近赤外吸収色素並びに近赤外吸収材 |
CN110446974B (zh) * | 2017-03-29 | 2023-09-12 | 东丽株式会社 | 感光性组合物、固化膜和有机el显示装置 |
JP6922361B2 (ja) * | 2017-04-07 | 2021-08-18 | Jsr株式会社 | 固体撮像素子用組成物、赤外線遮蔽膜及び固体撮像素子 |
Citations (1)
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JPH09316049A (ja) | 1996-05-24 | 1997-12-09 | Yamamoto Chem Inc | フタロニトリル化合物、その製造方法、これより得られるフタロシアニン化合物及びその用途 |
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CA2005520A1 (en) * | 1988-12-15 | 1990-06-15 | Hisato Itoh | Near infrared absorbent and display/recording materials prepared by using same |
EP1375600B1 (en) * | 2002-06-12 | 2006-04-05 | Nippon Shokubai Co., Ltd. | Phthalocyanine compound, near infrared absorbing dye and heat ray shielding |
JP5046515B2 (ja) * | 2005-12-19 | 2012-10-10 | 株式会社日本触媒 | フタロシアニン化合物並びにその製造方法及び用途 |
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2009
- 2009-12-18 KR KR1020090126778A patent/KR101153787B1/ko active IP Right Grant
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2010
- 2010-12-16 WO PCT/KR2010/009015 patent/WO2011074890A2/ko active Application Filing
- 2010-12-16 CN CN201080064114.2A patent/CN102762580B/zh not_active Expired - Fee Related
- 2010-12-16 EP EP10837886.0A patent/EP2514755A4/en not_active Withdrawn
- 2010-12-16 US US13/516,218 patent/US20120271044A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09316049A (ja) | 1996-05-24 | 1997-12-09 | Yamamoto Chem Inc | フタロニトリル化合物、その製造方法、これより得られるフタロシアニン化合物及びその用途 |
Non-Patent Citations (2)
Title |
---|
INORG. CHEM., vol. 34, 1995, pages 1636 - 1637 |
See also references of EP2514755A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014031421A (ja) * | 2012-08-02 | 2014-02-20 | Nippon Shokubai Co Ltd | フタロシアニン化合物およびこれを含む赤外線カットフィルター |
Also Published As
Publication number | Publication date |
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KR101153787B1 (ko) | 2012-06-13 |
KR20110070092A (ko) | 2011-06-24 |
US20120271044A1 (en) | 2012-10-25 |
CN102762580A (zh) | 2012-10-31 |
EP2514755A2 (en) | 2012-10-24 |
EP2514755A4 (en) | 2017-04-26 |
CN102762580B (zh) | 2015-08-05 |
WO2011074890A3 (ko) | 2011-11-03 |
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