KR101986604B1 - Compound for green dye, optical article using the same and intermediate thereof - Google Patents
Compound for green dye, optical article using the same and intermediate thereof Download PDFInfo
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- KR101986604B1 KR101986604B1 KR1020120076555A KR20120076555A KR101986604B1 KR 101986604 B1 KR101986604 B1 KR 101986604B1 KR 1020120076555 A KR1020120076555 A KR 1020120076555A KR 20120076555 A KR20120076555 A KR 20120076555A KR 101986604 B1 KR101986604 B1 KR 101986604B1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
TECHNICAL FIELD The present invention relates to a compound for a green pigment, an optical use using the compound, and a synthetic intermediate of the compound.
The present invention can improve the solubility of a compound according to the intramolecular three-dimensional structure design and allow the compound to realize green while maintaining stable image characteristics in solution and on a film, . In addition, the green pigment compound of the present invention realizes an electrical characteristic having a low band gap of 2.0 eV or less, thereby providing a low-molecular-weight solar cell using the same. Further, it is possible to provide a synthetic intermediate of the compound for green pigment suitable for the three-dimensional structure design of the present invention.
Description
TECHNICAL FIELD The present invention relates to a compound for a green pigment, an optical use thereof, and a synthetic intermediate thereof, and more particularly, to a green pigment composition which improves solubility according to intramolecular structure design, And to realize an electrical characteristic having a low band gap of 2.0 eV or less, an optical use of a color filter or a low-molecular-weight solar cell for color image display using the same, and a synthetic intermediate of the compound.
Generally, a color filter has a plurality of colored layers arranged to correspond to a plurality of pixels in order to realize color image display. Such a color filter usually has a structure in which a pigment corresponding to each color of red, green, and blue is uniformly coated on a substrate, a colored photosensitive resin composition containing the coloring material is uniformly coated, then exposed and developed, And repeating the process according to each color to form a colored layer corresponding to each color.
At this time, the photosensitive resin composition of each color for forming the red, green, and blue coloring layers has been continuously studied to improve the high brightness and high contrast characteristics of the liquid crystal display device.
Among them, in the case of a photosensitive resin composition for forming a green coloring layer, many green colors having strong yellow color have been proposed in order to realize a high luminance of a liquid crystal display device. On the other hand, in the recent field of liquid crystal display devices, a sufficient color reproduction rate is required according to the NTSC standard. According to the NTSC standard, a pixel showing a dark green color rather than a strong yellow color is required to realize a sufficient color reproduction rate.
In such a case, it is difficult to realize a deep green as a combination of pigments using an excessive amount of conventional yellow pigment.
Further, in a liquid crystal display device using a WLED light source, it has been pointed out that the color purity of green is lowered due to the unnecessary wavelength of the light source depending on the type of the WLED light source. Accordingly, a pixel showing a dark green color is required as one method for preventing color purity due to unnecessary wavelength of a light source from being lowered.
In this case, however, there is a limit to realizing a dark green as a combination of pigments using an excessive amount of conventional yellow pigment.
Accordingly, the present inventors have made efforts to solve the problems for implementing green in the past, and as a result, they have found that a green pigment compound capable of stably implementing a green color according to the intramolecular three-dimensional structure design is synthesized, and the green pigment compound has a wide absorption wavelength region To maintain the stable optical properties in solution phase and on the film, and confirm the electrical properties, thus completing the present invention.
It is an object of the present invention to provide a compound for a pigment which realizes green.
It is another object of the present invention to provide a color filter for color image display or a low molecular weight solar cell to which the above green pigment compound is applied.
It is still another object of the present invention to provide a synthetic intermediate of the compound for green pigment.
In order to accomplish the above object, the present invention provides a green pigment compound represented by the following general formula (1).
Formula 1
(Wherein M is a divalent transition metal, R 1 is a substituted or unsubstituted C 3 to C 8 alicyclic or aromatic compound, and the substitution is substituted with a C 2 to C 10 linear or branched alkyl group .)
The preferred central metal in the green pigment compound is Ti or Ni.
In the green pigment compound, preferably, the C 3 to C 8 alicyclic or aromatic compound R 1 is substituted with a secondary alkyl group or a tertiary alkyl group.
The present invention further provides a compound represented by the following general formula (2) among the above green pigment compounds.
(2)
(Wherein M is a divalent transition metal, R 2 to R 5 are selected from hydrogen or a straight or branched alkyl group of C 2 to C 10 , and are not simultaneously substituted with hydrogen, and R 6 to R 9 are hydrogen or A straight or branched alkyl group having 2 to 10 carbon atoms, and is not substituted with hydrogen at the same time.)
More preferably, any one of the substituents R 2 to R 5 and any one of the substituents R 6 to R 9 are mutually stereoscopically symmetrical.
Accordingly, the present invention provides a color filter for color image display using a composition liquid containing a green pigment compound.
The present invention also provides a low-molecular-weight solar cell having a low band gap since the band gap of the green pigment compound is 2.0 eV or less.
Further, the present invention provides a synthetic intermediate of the compound for green pigment represented by the following general formula (3).
(3)
In the above, the synthetic intermediate is a red compound having an absorption wavelength band in the region of 450 to 550 nm, and the optical properties in the ultraviolet-visible region are maintained even in the solution phase and the film.
According to the present invention, it is possible to provide a compound for green pigment according to the intramolecular three-dimensional structure design, so that the physical property and structure of the compound can be controlled by the three-dimensional structure, and the physical property implementation suitable for the application field can be designed.
Accordingly, the green pigment compound of the present invention can be obtained by using PGMEA (Propylene Glycol Mnomethyl Ether Acetate ) Solvent, the solubility is improved to 11% or more and 30% or more, and it is applicable to the display field. Since stable optical and electrical properties are confirmed, the color pigment for color image display or the low- Battery can be provided.
Furthermore, the present invention can provide a synthetic intermediate which enables the three-dimensional structure design of the green pigment compound.
BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a graph of the spectroscopic characteristics in the ultraviolet-visible region of the synthetic intermediate of the green pigment compound of the present invention,
FIG. 2 is a graph of the spectroscopic characteristics in the ultraviolet-visible region on the solution containing the green pigment compound of the present invention,
FIG. 3 is a graph of the spectroscopic characteristics in the ultraviolet-visible region on the film made of the compound for green pigment of the present invention,
4 is a graph for evaluating the thermal stability of the green pigment compound of the present invention,
5 is a graph showing the electrical behavior of the green pigment compound prepared in Example 1 of the present invention,
6 is a graph showing the electrical behavior of the green pigment compound prepared in Example 2 of the present invention.
Hereinafter, the present invention will be described in detail.
The present invention provides a green pigment compound represented by the following general formula (1).
Formula 1
(Wherein M is a divalent transition metal, R 1 is a substituted or unsubstituted C 3 to C 8 alicyclic or aromatic ring compound, and the substitution is a C 2 to C 10 linear or branched alkyl group will be.)
In the green pigment compound of the present invention, the central metal may be a bivalent transition metal constituting a tetracoordinate, more preferably titanium (Ti), nickel (Ni) or copper (Cu) In the embodiment of the present invention, titanium (Ti) is used as the most preferable example, but the present invention is not limited thereto.
The compound for green pigment of the present invention controls the physical properties, optical and electrical properties according to the intramolecular three-dimensional structure design, and the compound represented by Formula 1 is [Zn (dmit) 2 ] 2- anion -dithiole-2-thione-4,5-dithiolate) may be placed in one side of the entire structure to be stereoscopically fixed, and the remaining two coordination complexes may be appropriately combined.
At this time, the remaining two coordination body substituent of R 1 is a substituted or unsubstituted C 3 to C 8 aliphatic or aromatic compound, in the exemplary embodiment of the present invention, but are described as to only the C 5 compound, it shall not be limited to .
More preferably,
At this time, it is possible to control the physical properties of the compound by substituting a secondary alkyl group or a tertiary alkyl group as a substituent on the periphery, thereby giving a steric hindrance.
Accordingly, the present invention provides a compound represented by the following general formula (2), among the above green pigment compounds.
(2)
(Wherein M is a divalent transition metal, R 2 to R 5 are selected from hydrogen or a straight or branched alkyl group of C 2 to C 10 , and are not simultaneously substituted with hydrogen, and R 6 to R 9 are hydrogen or A straight or branched alkyl group having 2 to 10 carbon atoms, and is not substituted with hydrogen at the same time.)
The center metal M is limited to titanium (Ti) in the examples. However, it is possible to use a bivalent transition metal constituting a tetrahedral coordination body. Examples thereof include nickel (Ni) or copper can do.
In the compound represented by the general formula (2), any one of the substituents R 2 to R 5 and the substituent group of any of R 6 to R 9 are mutually stereoscopically symmetrical.
FIG. 1 is a spectroscopic characteristic graph in an ultraviolet-visible region of a compound for the preparation of a green pigment according to the present invention, showing a wide absorption band in the region of 450 to 550 nm, and also shows the ultraviolet- And the red pigment compound having a maximum absorption wavelength of 507 nm can be confirmed.
FIG. 2 is a graph of spectroscopic characteristics in the ultraviolet-visible region on the solution containing the green pigment compound of the present invention, and FIG. 3 is a graph of the spectroscopic characteristics in the ultraviolet-visible region on the film made of the compound of green pigment of the present invention , A green pigment compound having a maximum absorption wavelength of 427 to 430 nm and 632 to 650 nm, and the optical characteristics in the ultraviolet-visible region are maintained even in the solution phase and on the film.
Thus, in the green pigment compound represented by the general formula (1) of the present invention, it is preferable that the substituent group around R 1 , which is a bidentate substituent which enables the intramolecular stereostructure design, to be substituted is a three- The physical properties can be controlled according to the disability.
At this time, in the embodiment of the present invention, the R 1 is limited to a C 5 -aromatic ring, but a C 6 -aromatic ring may be substituted, C 3 to C 8 alicyclic or aromatic ring compounds for the purpose of imparting a bulky property to the resin.
In addition, as a substituent around R 1 , preferably a secondary alkyl group or a tertiary alkyl group is substituted to give a steric hindrance to improve the solubility of the compound, and the bulkiness of the compound due to the steric structure serves as an electron transfer path Can be performed.
Specifically, the use of PGMEA (Propylene Glycol Mnomethyl Ether Acetate ) Solubility under solvent conditions must be at least 10% or more. The green pigment compound of the present invention is preferably a PGMEA (Propylene Glycol Mnomethyl Ether Acetate ) Solvent, the solubility can be improved from 11% to 30%, which is applicable to the display field.
4 is a result of evaluation of the thermal stability of the green pigment compound of the present invention, which is suitable for a display field requiring heat resistance. In the heat resistance evaluation, as the bulky property of the intramolecular structure increases, the TGA starting temperature tends to be lowered. However, since the temperature is at least 185 ° C, the heat resistance applicable to the display field is shown.
Accordingly, the present invention provides a color filter for color image display using a composition liquid containing a green pigment compound.
The field to which the color filter is applied includes fields such as a photographing element, a plasma display panel (PDP), a liquid crystal display (LCD), a field emission display (FEL), a light emitting display (LED)
FIG. 5 shows the electrical behavior of the green pigment compound prepared in Example 1 of the present invention, and FIG. 6 shows the electrical behavior of the green pigment compound prepared in Example 2 of the present invention.
From the above results, stable electrical characteristics can be confirmed as the bulky property of the intramolecular structure in the green pigment compound of the present invention increases, and the bulkiness of the compound due to the three-dimensional structure can serve as an electron transfer path.
In particular, the green pigment compound of the present invention meets a low band gap of 2.0 eV or less, thereby providing a low-molecular-weight solar cell using the same.
Further, the present invention provides a synthetic intermediate for the preparation of the green pigment compound represented by the following general formula (3).
(3)
The above synthetic intermediate is a red compound having a wide absorption band in the region of 450 to 550 nm, as shown in Fig. 1, and optical properties within the ultraviolet-visible region are maintained in the solution phase and also on the film.
The skeleton of the [Zn (dmit) 2 ] 2- anion (dmit = 1,3-dithiole-2-thione-4,5-dithiolate) is placed in one side of the entire structure of the compound of the present invention, , It is possible to provide stable optical and electrical properties to the target compound represented by the formula (1).
Hereinafter, the present invention will be described in more detail with reference to Examples.
The present invention is intended to more specifically illustrate the present invention, and the scope of the present invention is not limited to these embodiments.
≪ Example 1 >
Step 1: Synthesis of 5- (4-amyloxybenzyl) -dipyrromethane (C 3 S 5 Na)
2.3 g (0.1 mol) of Na were washed with ether in a nitrogen gas atmosphere, placed in a 3-necked flask, 18 ml (0.3 mol) of CS 2 was added under ice bath conditions and dropping funnel), 20 ml of DMF was added slowly for 40 minutes, and the mixture was stirred for 6 hours to synthesize the target compound (5- (4-amyloxybenzyl) -dipyrromethane).
Step 2: Synthesis of zinc-complex (Zn-complex)
In an ice bath condition, the C 3 S 5 Na compound prepared in
Step 3: Synthesis of NRTiR
1 g of bis (cyclopentadienyl) titanium dichloride and 1.18 g of the zinc complex [Zn (dmit) 2 ] (NET 4 ) 2 prepared in the
≪ Example 2 >
1 g of bis (ethylcyclopentadienyl) titanium dichloride and 1.18 g of the zinc-complex [Zn (dmit) 2 ] (NET 4 ) 2 prepared in the
≪ Example 3 >
[Zn (dmit) 2 ] (NET 4 ) prepared in
<Example 4>
1 g of bis (isopropylcyclopentadienyl) titanium dichloride and 1.18 g of the zinc-complex [Zn (dmit) 2 ] (NET 4 ) 2 prepared in the
<Experimental Example 1> Optical characteristics 1
Optical properties were observed using an ultraviolet spectrophotometer (HP 8453 UV-vis-NIR spectrometer) of the Zn-complex [Zn (dmit) 2 ] (NET 4 ) 2 prepared in
The results are shown in Fig. 1, in which the maximum absorption wavelength in the solution phase was observed to be 507 nm, and the maximum absorption wavelength on the film was observed to be red (red) observed at 502 nm.
From the above results, it can be seen that the zinc-complex [Zn (dmit) 2 ] (NET 4 ) 2 exhibits an absorption peak having a green absorption wavelength range in blue and that the optical characteristics in the ultraviolet- .
EXPERIMENTAL EXAMPLE 2
For the target compounds obtained in Examples 1 to 4 synthesized using the zinc-complex [Zn (dmit) 2 ] (NET 4 ) 2 prepared in
As a result, the optical properties in the ultraviolet-visible region on the solution containing the target compound 1 x 10 -4 M are shown in Fig. 2 , and the optical characteristics in the ultraviolet-visible region on the film containing 1 wt% of the target compound are shown in Fig .
Table 1 below shows the results of comparing the optical properties in the solution phase of the target compound and in the ultraviolet-visible region on the film.
From the results shown in Figs. 2 and 3 and Table 1, the target compounds prepared in Examples 1 to 4 exhibited two specific absorption peaks in the ultraviolet-visible region in the same pattern in the solution phase and film phase, ≪ / RTI >
<Experimental Example 3> Solubility test
The solubility test of the target compound prepared in the above Example was carried out using PGMEA (Propylene Glycol Mnomethyl Ether Acetate ) Solvent conditions.
Specifically, 0.01 g of the target compound prepared in Examples 1 to 4 was dissolved in 0.15 ml of PGMEA, and the mixture was ultrasonically vibrated for 1 minute and then stirred for 10 hours. Thereafter, the sample was filtered with a syringe filter (membrane material: Teflon), and the weight of the sample remaining on the membrane was measured by weight difference between before and after filtration. At this time, the PGMEA solvent was used as a solvent for manufacturing a color filter resist, and a commercial product was purchased and used.
Table 2 below shows the results of the solubility test.
From the results shown in Table 2, it was confirmed that the solubility of the target compound in the PGMEA solvent was improved as the steric hindrance of the substituent of the target compound became larger.
Generally, when the PGMEA solvent is used in a display application, the target compound of the present invention satisfies the desirable solubility requirement for the PGMEA solvent, so that the PGMEA solvent can be usefully used in a solution state when the PGMEA solvent is used in a display application of 10% or more, more preferably 15% A color filter for color image display or a low molecular weight solar cell.
<Experimental Example 4> Evaluation of heat resistance
The target compounds prepared in the above Examples were measured for thermal stability using a thermogravimetric analyzer.
The results are shown in Table 3 and FIG.
≪ Experimental Example 5 >
In order to confirm the electrical characteristics of the target compound prepared in the above example, a working electrode ITO, an auxiliary electrode Pt wire, a reference electrode Ag / AgNO 3 , and a methylene chloride solution containing 0.1 M TBAT were dissolved in an electrolyte solution Respectively. At this time, the compounds of Examples 1 and 2 were selected and utilized. The concentrations of the compounds of Examples 1 and 2 were prepared by dissolving 1 × 10 -4 M in methylene chloride. The experimental conditions were observed at a scanning speed of 100 mg / s and a range of -1.2 V to + 1.02 V.
Figure 5 shows the electrical test results of the compound of Example 1 and Figure 6 shows the results of the same conditions for the compound of Example 2.
From the results of FIG. 5 and FIG. 6, it can be seen from the result of FIG. 6 that the alkyl group of the substituent is increased, and the stable electrical characteristic is smaller than that of FIG. 5. Therefore, it is predicted that when the alkyl group of the substituent is increased, the skeleton of the parent compound is maintained, and the degree of steric hindrance becomes large, and thus it can be provided as an electron transfer path.
Table 4 below shows the band gaps calculated from the electrical test results of the compounds of Examples 1 and 2.
As shown in Table 4, since the target compound of the present invention has a band gap of 2.0 eV or less, it can be utilized as a low-band electron donor for low-molecular solar cells.
As described above, the present invention provides a green pigment compound having improved solubility and excellent optical and electrical properties according to the intramolecular three-dimensional structure design.
Particularly, when the green pigment compound is PGMEA (Propylene Glycol Mnomethyl Ether Acetate ) Solvent, the solubility is improved to 11% or more and 30% or more, so that a color filter for color image display can be applied.
In addition, since the green pigment compound realizes electrical characteristics having a low band gap of 2.0 eV or less, it can be effectively applied to optical applications, particularly, to low molecular weight solar cells.
Further, the present invention provides a synthetic intermediate which enables the three-dimensional structure design of the green pigment compound.
While the invention has been shown and described with reference to certain exemplary embodiments thereof, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (11)
A green pigment for display in which optical characteristics with a maximum absorption wavelength of 427 to 430 nm and 632 to 650 nm are maintained in a solution phase or a film containing the compound;
Formula 1
In the above, M is a divalent transition metal, R 1 is a substituted C 3 to C 8 alicyclic or aromatic compound, and the substituent is a C 2 to C 10 linear or branched alkyl group.
(2)
Wherein M is as defined in claim 1 and R 2 to R 5 are selected from hydrogen or a straight or branched alkyl group of C 2 to C 10 and are not simultaneously substituted by hydrogen and R 6 to R 9 are Is hydrogen or a straight or branched alkyl group of C 2 to C 10 , and is not substituted with hydrogen at the same time.
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| KR1020120076555A KR101986604B1 (en) | 2012-07-13 | 2012-07-13 | Compound for green dye, optical article using the same and intermediate thereof |
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| KR1020120076555A KR101986604B1 (en) | 2012-07-13 | 2012-07-13 | Compound for green dye, optical article using the same and intermediate thereof |
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| KR101986604B1 true KR101986604B1 (en) | 2019-06-07 |
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Non-Patent Citations (2)
| Title |
|---|
| Inorganica Chimica Acta, Vol. 239, pp. 117-124, 1995* |
| J. Am. Chem. Soc., Vol. 111, pp. 3465-3466, 1989* |
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