CN110563737A - Metal phthalocyanine compound, printing ink and electrowetting display - Google Patents
Metal phthalocyanine compound, printing ink and electrowetting display Download PDFInfo
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- CN110563737A CN110563737A CN201910778317.0A CN201910778317A CN110563737A CN 110563737 A CN110563737 A CN 110563737A CN 201910778317 A CN201910778317 A CN 201910778317A CN 110563737 A CN110563737 A CN 110563737A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/063—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having oxygen or sulfur atom(s) linked directly to the skeleton
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B26/00—Optical devices or arrangements for the control of light using movable or deformable optical elements
- G02B26/004—Optical devices or arrangements for the control of light using movable or deformable optical elements based on a displacement or a deformation of a fluid
- G02B26/005—Optical devices or arrangements for the control of light using movable or deformable optical elements based on a displacement or a deformation of a fluid based on electrowetting
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Abstract
The invention discloses a metal phthalocyanine compound, printing ink and an electrowetting display, wherein the structural general formula of the metal phthalocyanine compound is shown as (I):wherein M is a metal ion, R1、R2、R3、R4Each independently selected from any one of alkoxy and alkyl phenoxy. The formed metal phthalocyanine compound is not in a metal phthalocyanine structure by introducing alkoxy and/or alkyl phenoxyThe metal phthalocyanine compound has high solubility in a polar solvent, the ink formed by the metal phthalocyanine compound has bright color, high saturation and ultrahigh color development intensity, an electrowetting display device formed by the ink has low switching response time and low reflux speed under constant voltage, and the metal phthalocyanine compound provided by the invention is very suitable for electrowetting display.
Description
Technical Field
the invention relates to the technical field of electrowetting, in particular to a metal phthalocyanine compound, printing ink and an electrowetting display.
Background
The electrowetting display technology (EFD), also called electrowetting display technology, is a display prototype based on electrowetting display, which was first developed by philips, netherlands in 2003. The display principle is that the surface performance of the hydrophobic layer is controlled by changing voltage, and the contact angle of an ink layer on the hydrophobic layer is changed: when no voltage is applied, the ink uniformly wets the insulating layer to form a colored pixel point; when voltage is applied, the surface performance of the hydrophobic layer is changed under the action of the electric field, so that the interfacial tension between the three phases of the ink, the polar liquid and the hydrophobic layer is changed, the ink is compressed, and transparent or substrate ground color pixel points are formed, thereby obtaining the image display effect.
The electrowetting display ink material is a proprietary material for electrowetting display colors, so that high requirements are provided for the solubility of dyes in non-polar solvents, color saturation, color development intensity and the like. In WO 2003/071346, WO 2010/031860, US 2011/0226998 and US 20130241815, ink materials mainly having an anthraquinone structure are patented, and the ink materials having an anthraquinone structure are used for electrowetting display, which have the advantages of low polarity and excellent light resistance of most dyes, but the anthraquinone organic dye has the defects of low color development intensity, low molar absorption coefficient and difficulty in covering color to cyan. Phthalocyanine dyes have the advantages of bright color, high molar absorptivity, and excellent light stability, and are commonly used cyan and green dyes. However, phthalocyanine dye molecules have poor solubility due to the strong pi-overlap effect, and are difficult to be applied to electrowetting display.
Disclosure of Invention
In view of the drawbacks of the prior art, an object of the present invention is to provide a metal phthalocyanine-based compound having excellent solubility, which can be applied as a cyan dye in an electrowetting display, an ink, and an electrowetting display.
The technical scheme adopted by the invention is as follows:
The invention provides a metal phthalocyanine compound, which has a structural general formula shown in (I):
Wherein M is a metal ion, R1、R2、R3、R4Each independently selected from any one of alkoxy and alkyl phenoxy.
preferably, R1、R2、R3、R4Not simultaneously alkyl phenoxy.
more preferably, the alkoxy is an alkoxy having 8 to 20 carbon atoms; the number of carbon atoms of an alkyl chain in the alkyl phenoxy group is 8-20.
further, R1、R2、R3、R4Each independently selected from the group consisting of octyloxy, isooctyloxy, nonyloxy, n-decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, n-octylphenoxy, isooctylphenoxy, nonylphenoxy, n-decylphenoxy, undecylphenoxy, dodecylphenoxy, tridecyloxy, tetradecylphenoxy, pentadecyloxy, hexadecylphenoxy, heptadecylphenoxy, octadecylphenoxy, nonadecylphenoxy, and eicosylphenoxy.
Preferably M is a transition metal ion, M includes but is not limited to Cu2+、Zn2+、Ni2+、Co2+At least one of (1).
The application of the metal phthalocyanine compound in electrowetting display dyes. The metal phthalocyanine compound can be used as a dye to be applied to electrowetting display.
The invention also provides ink which comprises the metal phthalocyanine compound.
Further, the ink comprises 1-30 parts by mass of the metal phthalocyanine compound and 5-100 parts by mass of a nonpolar solvent.
Still further, the non-polar solvent includes at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorine-containing alkane, and silane.
The invention also provides an electrowetting display comprising the ink.
The invention has the beneficial effects that:
the invention provides a metal phthalocyanine compound, which improves the solvability of parent metal phthalocyanine in a non-polar medium by introducing alkoxy and/or alkyl phenoxy in a metal phthalocyanine structure, taking heteroatom oxygen as a bridging group and long-chain alkyl/long-chain alkylphenyl as a solubilizing group, reduces the pi-pi interaction of a metal phthalocyanine nucleus by utilizing the steric hindrance effect of the long-chain alkyl, improves the higher solubility of the metal phthalocyanine compound in a non-polar solvent, has the advantages of high molar absorption coefficient, bright color, good light stability and high solubility, can be used as a cyan dye to be applied to electrowetting display, and meets the defect that the existing organic dye for electrowetting display lacks cyan with excellent performance. The ink formed by the metal phthalocyanine compound has bright color, high saturation and ultrahigh color development intensity, and is filled into an electrowetting display device, so that the formed electrowetting display device has lower switching response time and does not have a backflow phenomenon under constant voltage.
drawings
FIG. 1 is a graph showing a visible absorption spectrum of a metal phthalocyanine compound (I) in n-decane in example 1;
FIG. 2 is a graph showing a visible absorption spectrum of a metal phthalocyanine compound (II) in n-decane in example 2;
FIG. 3 is a graph showing a visible absorption spectrum of a metal phthalocyanine compound (III) in n-decane in example 3;
FIG. 4 is a graph showing a visible absorption spectrum of a metal phthalocyanine compound (IV) in n-decane in example 4;
FIG. 5 is a pictorial representation of an ink 1 filled electrowetting display of effect example 1;
FIG. 6 is a graph of response time for an ink 1 filled electrowetting display panel of effect example 1;
FIG. 7 is a graph of the reflow time for an ink 1 filled electrowetting display panel of effect example 1;
Fig. 8 is a graph of photostability testing of ink 1 filled electrowetting display panel in effect example 1.
Detailed Description
the concept and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments to fully understand the objects, features and effects of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
EXAMPLE 1 Synthesis of Metal Phthalocyanine-based Compound (I)
The metal phthalocyanine compound (I) is synthesized according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 2.58g (298g/mol, 0.00865mol) of 2-octyldodecanol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of an eicosoxyalkynedionitrile-based benzene intermediate with the yield of 73.3%.
Weighing 1.25g (424g/mol, 0.00295mol) of an eicosoxy dinitrile intermediate, adding 2 drops of organic base DBU, 0.125g (170g/mol, 0.000737mol) of CuCl2, adding 4ml of n-amyl alcohol, introducing nitrogen for protection, heating to 160 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction liquid, carrying out suction filtration to obtain a dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (I) with the yield of 60%.
The visible absorption spectra of solutions of metal phthalocyanine compound (I) dissolved in n-decane with different concentrations are shown in figure 1, and it can be seen from the figure that the prepared metal phthalocyanine compound (I) has better solubility in n-decane.
EXAMPLE 2 Synthesis of Metal Phthalocyanine-based Compound (II)
Synthesizing a metal phthalocyanine compound (II) according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 2.58g (298g/mol, 0.00865mol) of 2-octyldodecanol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of an eicosoxyalkynedionitrile-based benzene intermediate with the yield of 73.3%.
7.88g (424g/mol, 0.0186mol) of the eicosanoyloxydinitrileintermediate are weighed out and 4 drops of organic base DBU, 0.63g (136g/mol, 0.00465mol) of ZnCl are added2Adding 10ml of n-amyl alcohol, introducing nitrogen for protection, heating to 150 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (II) with the yield of 50%.
The visible absorption spectrogram of the prepared metal phthalocyanine compound (II) in n-decane is shown in figure 2, and experiments also verify that the metal phthalocyanine compound (II) has better solubility in n-decane.
Example 3 Synthesis of Metal Phthalocyanine-based Compound (III)
Synthesizing a metal phthalocyanine compound (III) according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 2.58g (298g/mol, 0.00865mol) of 2-octyldodecanol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of an eicosoxyalkynedionitrile-based benzene intermediate with the yield of 73.3%.
4.24g (424g/mol, 0.01mol) of the eicosoxyalkanedinitrile intermediate are weighed out and 3 drops of DBU, 0.32g (129.8g/mol, 0.0025mol) CoCl are added2Adding 10ml of n-amyl alcohol, introducing nitrogen for protection, heating to 150 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (III) with the yield of 55%.
The visible absorption spectrogram of the metal phthalocyanine compound (III) prepared by different concentrations in n-decane is shown in figure 3, and experiments also verify that the metal phthalocyanine compound (III) has better solubility in n-decane.
Example 4 Synthesis of Metal Phthalocyanine-based Compound (IV)
Synthesizing the metal phthalocyanine compound (IV) according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 2.58g (298g/mol, 0.00865mol) of 2-octyldodecanol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of an eicosoxyalkynedionitrile-based benzene intermediate with the yield of 73.3%.
4.24g (424g/mol, 0.01mol) of the eicosoxyalkenylbenzene intermediate are weighed out and 3 drops of DBU, 0.31g (125.8g/mol, 0.0025mol) MnCl are added2adding 10ml of n-amyl alcohol, introducing nitrogen for protection, heating to 150 ℃, reacting for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (IV) with the yield of 58%.
the absorption spectrogram of the prepared metal phthalocyanine compound (IV) in n-decane is shown in figure 4.
EXAMPLE 5 Synthesis of Metal Phthalocyanine-based Compound (V)
Synthesizing the metal phthalocyanine compound (V) according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 1.12g (130g/mol, 0.00865mol) of 2-ethylhexyl alcohol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of 2-ethylhexoxydinitrile benzene intermediate with the yield of 80.3%.
0.755g (256g/mol, 0.00295mol) of the 2-ethylhexyloxydianonitrilylbenzene intermediate was weighed out and 2 drops of organic base DBU, 0.125g (170g/mol, 0.000737mol) of CuCl were added2Adding 4ml of n-amyl alcohol, introducing nitrogen for protection, heating to 160 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (V) with the yield of 70%.
EXAMPLE 6 Synthesis of Metal Phthalocyanine Compound (VI)
The metal phthalocyanine compound (VI) is synthesized according to the following reaction formula:
the specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 1.78g (206g/mol, 0.00865mol) of 2-tert-octylphenol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of 2-ethylhexoxydinitrile benzene intermediate with the yield of 83.2%.
0.98g (332g/mol, 0.00295mol) of the tert-octylphenoxydinitrile intermediate are weighed out and 2 drops of DBU, 0.125g (170g/mol, 0.000737mol) of CuCl are added2Adding 4ml of n-amyl alcohol, introducing nitrogen for protection, heating to 160 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (VI) with the yield of 50%.
EXAMPLE 7 Synthesis of Metal phthalocyanine-based Compound (VII)
Synthesizing the metal phthalocyanine compound (VII) according to the following reaction formula:
The specific synthetic process is as follows: weighing 1.25g (173g/mol, 0.00722mol) of 4-nitrophthalonitrile, 2.62g (304g/mol, 0.00865mol) of 3-pentadecylphenol and 1.2g (138g/mol, 0.00865mol) of anhydrous potassium carbonate, dissolving in 10ml of DMSO, heating to 50 ℃ for reaction for 20 hours, adding 30ml of water after the reaction is finished, extracting by using petroleum ether, separating out an oil phase, and purifying by using column chromatography to obtain 2.2g of 2-ethylhexoxydinitrile intermediate with the yield of 83.2%.
1.27g (430g/mol, 0.00295mol) of 3-pentadecane phenoxy dinitrile intermediate is weighed and 2 drops of organic base DBU, 0.125g (170g/mol, 0.000737mol) of CuCl are added24ml of n-pentanol was added,Introducing nitrogen for protection, heating to 160 ℃ for reaction for 8h, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain a dark green solid dye, and purifying by column chromatography to obtain the metal phthalocyanine compound (VII) with the yield of 55%.
Example 8 Synthesis of Metal Phthalocyanine Compound (VIII)
the metal phthalocyanine compound (VIII) is synthesized according to the following reaction formula:
The specific synthetic process is as follows: regulating the ratio of two dicyan monomers to be 1: 1, obtaining a copper phthalocyanine dye having a mixed substitution structure: 1.27g (430g/mol, 0.00295mol) of 3-pentadecane phenoxydinitrile intermediate, 1.25g (424g/mol, 0.00295mol) of eicosoxy dinitrile intermediate, 4 drops of organic base DBU, 0.25g (170g/mol, 0.00147mol) of CuCl2Adding 8ml of n-amyl alcohol, introducing nitrogen for protection, heating to 160 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, performing suction filtration to obtain dark green solid dye, and purifying by adopting column chromatography to obtain the metal phthalocyanine compound (VIII) with the yield of 45%.
Example 9 Synthesis of Metal Phthalocyanine Compound (IX)
The metal phthalocyanine compound (IX) is synthesized according to the reaction formula shown below:
The specific synthetic process is as follows: regulating the ratio of two dicyan monomers to be 3: 1, obtaining a copper phthalocyanine dye having a mixed substitution structure: 0.63g (430g/mol, 0.00147mol) of 3-pentadecane phenoxydinitrile intermediate, 1.87g (424g/mol, 0.00442 mol) of eicosyloxydinitrile intermediate, 4 drops of organic base DBU, 0.25g (170g/mol, 0.00147mol) of CuCl were added2Adding 8ml of n-amyl alcohol, introducing nitrogen for protection, heating to 160 ℃ for reaction for 8 hours, cooling, adding 10ml of absolute ethyl alcohol into the reaction solution, and performing suction filtration to obtain the dark green solid dyeAnd purifying by column chromatography to obtain the metal phthalocyanine compound (IX), wherein the yield is 48%.
Effect example 1
0.1g of each of the metal phthalocyanine compounds prepared in examples 1 to 9 was weighed and dissolved in 10mL of n-decane to prepare electrowetting inks 1 to 9, respectively. The color, the maximum absorption wavelength (lambda max) and the solubility C in n-decane at 25 ℃ of the prepared electrowetting ink are shown in Table 1, and the result shows that the metal phthalocyanine compound prepared by the method has good solubility in a nonpolar solvent.
TABLE 1 Performance results for electrowetting ink materials
| sample (I) | numbering | Colour(s) | λmax(nm) | Solubility C |
| Example 1 | Ink 1 | Cyan color | 618，676 | >20％ |
| Example 2 | Ink 2 | Cyan color | 674 | >20％ |
| Example 3 | Ink 3 | Cyan color | 666 | >20％ |
| Example 4 | Ink 4 | Green colour | 728 | >20％ |
| Example 5 | ink 5 | Cyan color | 618，676 | 8％ |
| Example 6 | Ink 6 | Cyan color | 628，686 | 12％ |
| Example 7 | Ink 7 | Cyan color | 628，686 | 15％ |
| Example 8 | Ink 8 | Cyan color | 625，680 | 20％ |
| Example 9 | Ink 9 | Cyan color | 625，680 | >20％ |
A physical diagram of an electrowetting display panel prepared by filling the ink 1 is shown in fig. 5, the electrowetting display panel is a conventional electrowetting display, and the basic structure of the electrowetting display panel can be referred to in patent document CN 106054371A. The performance of the electrowetting display screen filled with the ink 1 is tested, and the results are shown in fig. 6-8, where fig. 6 is a response time curve of the electrowetting display screen, fig. 7 is a reflow time curve of the electrowetting display screen, fig. 8 is a light stability test chart of the electrowetting display screen, and the test conditions are as follows: irradiation intensity of 0.55W/m2(340nm), 40 ℃ and curves tested at 0h, 20h, 40h, 60h, 80h and 100h in the sequence indicated by the arrow in FIG. 8. Experimental results show that the electrowetting ink formed by the metal phthalocyanine compound has bright cyan light and high color saturation, and an electrowetting display device filled with the electrowetting ink has the advantages of high response time, low reflux speed under constant voltage and high light stability, so that the metal phthalocyanine compound provided by the invention is an excellent cyan electrowetting display dye and is very suitable for electrowetting display.
Claims (10)
1. The metal phthalocyanine compound is characterized in that the structural general formula of the metal phthalocyanine compound is shown as (I):
Wherein M is a metal ion, R1、R2、R3、R4Each independently selected from any one of alkoxy and alkyl phenoxy.
2. The metal phthalocyanine-based compound according to claim 1, wherein R is1、R2、R3、R4Not simultaneously alkyl phenoxy.
3. The metal phthalocyanine compound according to claim 1 or 2, wherein the alkoxy group is an alkoxy group having 8 to 20 carbon atoms; the number of carbon atoms of an alkyl chain in the alkyl phenoxy group is 8-20.
4. the metal phthalocyanine-based compound according to claim 3, wherein R is1、R2、R3、R4each independently selected from the group consisting of octyloxy, isooctyloxy, nonyloxy, n-decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, n-octylphenoxy, isooctylphenoxy, nonylphenoxy, n-decylphenoxy, undecylphenoxy, dodecylphenoxy, tridecyloxy, tetradecylphenoxy, pentadecyloxy, hexadecylphenoxy, heptadecylphenoxy, octadecylphenoxy, nonadecylphenoxy, and eicosylphenoxy.
5. The metal phthalocyanine-based compound according to any one of claims 1 to 4, wherein M comprises Cu2+、Zn2+、Ni2 +、Co2+At least one of (1).
6. use of a metal phthalocyanine-based compound according to any one of claims 1 to 5 in an electrowetting display dye.
7. An ink comprising the metal phthalocyanine-based compound according to any one of claims 1 to 5.
8. The ink according to claim 7, comprising 1 to 30 parts by mass of the metal phthalocyanine-based compound and 5 to 100 parts by mass of a nonpolar solvent.
9. The ink of claim 8, wherein the non-polar solvent comprises at least one of n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorine-containing alkanes, and silanes.
10. an electrowetting display comprising the ink according to any one of claims 7 to 9.
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| CN113136112A (en) * | 2021-04-16 | 2021-07-20 | 上海昀通电子科技有限公司 | Near infrared absorbing dye with wide spectral band |
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