KR20140087701A - Novel bis-dipyrrinato based copper complex derivatives, pigment dispersion composition comprising the same, and color filter using the same - Google Patents
Novel bis-dipyrrinato based copper complex derivatives, pigment dispersion composition comprising the same, and color filter using the same Download PDFInfo
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- KR20140087701A KR20140087701A KR1020120158275A KR20120158275A KR20140087701A KR 20140087701 A KR20140087701 A KR 20140087701A KR 1020120158275 A KR1020120158275 A KR 1020120158275A KR 20120158275 A KR20120158275 A KR 20120158275A KR 20140087701 A KR20140087701 A KR 20140087701A
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- South Korea
- Prior art keywords
- pigment
- compound
- formula
- color filter
- dispersion composition
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 92
- 239000006185 dispersion Substances 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 150000004699 copper complex Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 239000011230 binding agent Substances 0.000 claims description 23
- 239000011342 resin composition Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 15
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- 239000000126 substance Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ODOQKWUKLACHRO-UHFFFAOYSA-N 2-[phenyl(1h-pyrrol-2-yl)methyl]-1h-pyrrole Chemical class C1=CNC(C(C=2NC=CC=2)C=2C=CC=CC=2)=C1 ODOQKWUKLACHRO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/02—Diffusing elements; Afocal elements
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/02—Diffusing elements; Afocal elements
- G02B5/0205—Diffusing elements; Afocal elements characterised by the diffusing properties
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optical Filters (AREA)
Abstract
Description
The present invention relates to a novel bis-dipyrinato based copper complex derivative, a pigment dispersion composition containing the same, and a color filter using the same.
Liquid crystal displays (LCDs) are thin and light, have superior resolution and low power consumption, and are expanding their application range not only for notebook PCs but also for mobile phones, video cameras, and large televisions. Color filters, which are optical materials that realize colorization in LCDs, have been studied as a representative fine chemical products that have a great influence on the technological competitiveness of the LCD manufacturing industry. Conventional color filter manufacturing methods include pigment dispersion method (photolithography method using photo-polymer), electrodeposition method, printing method, dyeing method (dyeing of photopolymer pattern) and actively researching transfer method and ink jet method . Among them, the pigment dispersion method has excellent pattern accuracy and chemical properties and is used as a mainstream in recent color filter manufacturing.
In the past, dyes and pigments were mainly used in paints, inks, plastics, and textiles. However, due to the rapid development of the display industry in contemporary society with the development of the information technology industry, these materials have expanded their applicability as a core material for color filters (CF). Also recently, these dye and pigment materials have been widely applied to charge-coupled device (CCD) cameras and image sensors used in web-cameras. The way in which the dyes and pigments work in the color filter is that when white-backlight is injected into the CF, red, green and blue pigments, they reflect or absorb light of a particular wavelength, Spectrum. Thus, the desired optical properties of the pigments used in the CF should have a high molar extinction coefficient at the wavelengths required for absorption, since the light of the desired wavelength must be transmitted in large quantities and the remaining wavelengths must be filtered in the maximum amount. Another characteristic is that an improvement in thermal stability is required because thermal stability of 250 DEG C or higher is required during the CF manufacturing process. Molecular design for new dye materials has been considered primarily through this concept.
Bis (dipyrinetto) metal complexes were first reported by Fischer in 1924 [Treibs, A., & Kreuzer, FH (1968). Liebigs Ann . Chem . , 718 , 208.]. A number of derivatives of bis (dipyrrinethene) metal complexes have been synthesized in a number of research groups and their optical properties have been studied. However, there has been no meaningful report on the fundamental study of the possibility of bis (dipyrinetto) metal complex derivatives for use as materials of color filters through electro-optical properties.
One embodiment of the present invention is to provide a novel compound as a red pigment for a color filter having a high molar extinction coefficient and thermal stability.
Another embodiment of the present invention is to provide a pigment dispersion composition comprising the novel compound as a pigment derivative.
Another embodiment of the present invention is to provide a photosensitive resin composition for a color filter comprising the pigment dispersion composition.
Another embodiment of the present invention is to provide a color filter manufactured from the photosensitive resin composition for a color filter.
It is to be understood, however, that the technical scope of the present invention is not limited to the above-described problems, and other technical problems will be apparent to those skilled in the art from the following description.
An embodiment of the present invention provides a compound represented by the following formula (1).
≪ Formula 1 >
In the above formula (1), R is C 5 -8 aryl which is unsubstituted or substituted by halogen.
Another embodiment of the present invention provides a process for preparing the compound represented by the general formula (1).
Another embodiment of the present invention is a pigment composition comprising (A) a pigment derivative comprising a compound represented by Formula 1 above; (B) a pigment; (C) a dispersing agent; (D) a binder resin; And (E) a solvent.
Another embodiment of the present invention provides a photosensitive resin composition for a color filter comprising the pigment dispersion composition.
Another embodiment of the present invention provides a color filter produced from the photosensitive resin composition for a color filter.
Other details of the embodiments of the present invention are included in the following detailed description.
According to the present invention, the pigment dispersion composition comprising the novel compound as a pigment derivative has a high molar extinction coefficient at a red wavelength and has a thermal stability of 250 DEG C or higher, so that it can be advantageously applied to the manufacture of a color filter.
1 is a UV-Vis spectrum (Cu (PPN) 2 : Cu (4-ClPN) 2 : Cu (PPN) 2 ) spectrum in a THF solution of a novel compound according to an embodiment of the present invention. 4-FPN) 2 : O, and Cu (PFPPN) 2 : DELTA).
Figure 2 is a UV-Vis spectrum (Cu (PPN) 2 : □, Cu (4-ClPN) in a spin-coated film on a glass substrate of a novel compound according to one embodiment of the present invention ) 2 : Cu (4-FPN) 2 : O, and Cu (PFPPN) 2 : DELTA).
FIG. 3 is a scanning electron microscope (SEM) photograph of a novel compound and a commercial pigment (Red 254) according to an embodiment of the present invention ((a) Red 254, (b) Cu (PPN) 2 , 4-ClPN) 2 , (d) Cu (4-FPN) 2 , and (e) Cu (PFPPN) 2 .
Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).
[Chemical Formula 1]
(Wherein R is C 5-8 aryl which is unsubstituted or substituted by halogen).
Preferably, R is phenyl which is unsubstituted or substituted by one or more F or Cl.
More preferably, the compound of formula 1 may be selected from the group consisting of:
According to another embodiment of the present invention, there is provided a process for preparing the compound of Chemical Formula 1.
The process for the preparation of the compound of formula (1) according to the present invention comprises reacting a compound of formula (2) with a compound of formula (3) as shown in Scheme 1 below to give a 2,2- (Step 1); And
The 2,2- (phenylmethylene) bis (1H-pyrrole) derivative of Formula 4 prepared in Step 1 above was reacted with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone DDQ) and copper acetate to produce a compound of Formula 1 (Step 2).
[Reaction Scheme 1]
(In the above Reaction Scheme 1, R is as defined in Formula 1.)
First, Step 1 is a step of reacting a compound of Formula 2 with a compound of Formula 3 to prepare a 2,2- (phenylmethylene) bis (1H-pyrrole) derivative of Formula 4.
Specifically, the substituted aromatic aldehyde of formula (2) and the pyrrole of formula (3) are reacted at room temperature in the presence of trifluoroacetic acid (TFA) to give the 2,2- (phenylmethylene) bis .
In the present step, the starting materials, the compounds of the general formulas (2) and (3), may be commercially available or synthesized using conventional methods used in organic chemistry. In the synthesis of the compound of general formula (4) Can be, but not limited to, conventional reaction conditions used in organic chemistry.
Next, Step 2 is a step of reacting the 2,2- (phenylmethylene) bis (1H-pyrrole) derivative of Formula 4 prepared in Step 1 above with 2,3-dichloro-5,6-dicyano- Is reacted with 4-benzoquinone (DDQ) and copper acetate to prepare a compound of formula (1).
Specifically, in this step, the four compounds synthesized are oxidized to DDQ and then reduced with copper acetate, and the resulting copper complex is synthesized through the combination of Cu metal and ligand, preferably, bis (dipyrinato) copper complex core In which the substituent is substituted at the 5-position of the dipyrrinate moiety.
At this time, the organic solvent may be acetonitrile, and the base may be triethanolamine, but is not limited thereto.
As a result of measuring the optical properties and thermal stability of the compound of formula (1) prepared by the above-mentioned method, it was found that the compound of formula (1) in the THF solution is a compound of a diketopyrrolopyrrole (DPP) derivative which is a main red pigment widely known as a commercially available substance Exhibited a very high molar extinction coefficient of log size of 4.78 or more, which exceeded the average value (log?: 4.24), and exhibited thermal stability higher than the maximum temperature of 250 占 폚 applied during LCD manufacturing process, thereby being useful as a pigment for LCD color filters Lt; / RTI >
According to another embodiment of the present invention, there is provided a pigment dispersion composition comprising the novel compound as a pigment derivative. Hereinafter, each component constituting the pigment dispersion composition will be described in detail.
(A) Pigment derivatives
As the above-mentioned pigment derivative, the compound represented by the above-mentioned Formula 1 can be used.
The pigment derivative is contained in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 3 parts by weight based on the total amount of the pigment dispersion composition. When the pigment derivative is included in the above range, the color expression can be effectively performed and an appropriate viscosity can be maintained, and when the pigment dispersion composition containing the pigment derivative is applied to a product, excellent optical, physical and chemical quality can be secured.
(B) Pigment
The pigment dispersion composition of the present invention can be appropriately selected from various conventionally known inorganic pigments or organic pigments.
Examples of the inorganic pigments include metal compounds represented by metal oxides and metal complex salts. Specific examples thereof include metal oxides such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, , Complex oxides of the above metals, and the like.
Examples of the organic pigments include
These organic pigments may be used alone or in combination of several to improve the color purity. Specific examples of combinations are shown below.
As the red pigment, for example, an anthraquinone pigment, a perylene pigment, a diketopyrrolopyrrole pigment or at least one of them, a bisazo yellow pigment, an isoindoline yellow pigment, a quinophthalone yellow pigment A pigment or a mixture of a perylene red pigment may be used. Examples of the anthraquinone pigments include CI Pigment Red 177, the perylene pigments include CI Pigment Red 155 and CI Pigment Red 224, and the diketopyrrolopyrrole pigments include CI Pigment Red 254 And is preferably mixed with CI Pigment Yellow 139 in terms of color reproducibility. The mass ratio of the red pigment to the yellow pigment is preferably 100: 5-100: 50. When the ratio is less than 100: 5, it becomes difficult to suppress the light transmittance of 400 nm-500 nm, and the color purity may not be improved. On the other hand, when the ratio exceeds 100: 50, the main wavelength becomes near the short wavelength and the deviation from the NTSC target color may become large. Particularly, the mass ratio is most preferably in the range of 100: 10-100: 30. In the case of a combination of red pigments, it can be adjusted in accordance with the chromaticity.
As the green pigment, a halogenated phthalocyanine pigment may be used singly or in combination with a bisazo yellow pigment, a quinophthalone yellow pigment, an azomethine yellow pigment or an isoindoline yellow pigment. For example, these examples include C.I. Pigment Green 7, 36, 37 and C.I. Pigment Yellow 83, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 180 or C.I. Pigment Yellow 185 is preferable. The mass ratio of the green pigment to the yellow pigment is preferably 100: 5-100: 150. When the mass ratio is less than 100: 5, it is difficult to suppress the light transmittance of 400 nm-450 nm, and the color purity may not be improved. On the other hand, when the ratio exceeds 100: 150, the dominant wavelength becomes near the long wavelength and the deviation from the NTSC target color may become large. The mass ratio is particularly preferably in the range of 100: 30-100: 120.
As the blue pigment, a phthalocyanine-based pigment may be used singly or a mixture of the phthalocyanine-based pigment and a dioxazine-based purple pigment may be used. For example, a mixture of C. I. Pigment Blue 15: 6 and C. I. Pigment Violet 23 is preferred. The mass ratio of the blue pigment to the purple pigment is preferably 100: 0-100: 50, more preferably 100: 5-100: 30.
As the pigment for the black matrix, carbon, titanium black, iron oxide, titanium oxide alone or a mixture thereof may be listed, and a combination of carbon and titanium black is preferable. The mass ratio of carbon to titanium black is preferably in the range of 100: 0-100: 60. If it exceeds 100: 60, dispersion stability may be lowered.
The content of the pigment in the pigment dispersion composition is preferably 40-90 parts by weight, more preferably 50-80 parts by weight, based on the total solid content (weight) of the composition. When the content of the pigment is within the above range, it is also effective in ensuring a color characteristic excellent in color density.
(C) Dispersant
The dispersing agent is used for uniformly dispersing the pigment in a solvent. The dispersing agent may be a polyester compound, a polycarboxylic acid ester compound, an unsaturated polyamide compound, a polycarboxylic acid compound, a polycarboxylic acid alkyl salt compound, a polyacrylic compound , A polyethylene imine compound, a polyurethane compound, and a combination thereof.
Specific examples of the dispersant include DISPERBYK 161, DISPERBYK 163, DISPERBYK 164, DISPERBYK 2000, DISPERBYK 2001, BYK 21116, BYK 130 and BYK 109 of VW Kaya and EFKA-4046, EFKA-4047 of FFP, SOLSPERSE 32550 , SOLSPERSE 32500, and SOLSPERSE 33500.
The dispersant preferably has an amine value of 10-200 mgKOH / g, more preferably 40-200 mgKOH / g, and most preferably 50-150 mgKOH / g. When the amine value of the dispersant is 10-200 mgKOH / g, the dispersibility and developability are improved.
The dispersing agent may be contained in an amount of 1-20 parts by weight, preferably 2-15 parts by weight, based on the total amount of the pigment dispersion composition. When the dispersant is contained in the above range, effective dispersion is achieved, dispersion stability is improved, and the optical, physical, and chemical quality are improved when the product is applied while maintaining an appropriate viscosity, which is preferable in view of excellent balance of dispersion stability and viscosity.
(D) binder resin
As the binder resin, an acrylic copolymer resin is used. The acrylic copolymer may be at least one selected from the group consisting of styrene, N-benzyl phthalic imide, (meth) acrylic acid, alkyl (meth) acrylate, aryl (meth) acrylate, (Meth) acrylate, and the like, and they may be used alone or in combination of two or more.
More specifically, it is possible to use acrylic acid, methacrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, ethylhexyl (meth) Acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, o-silyl (meth) acrylate, glycerol (meth) acrylate, alkylaryl (meth) acrylate, succinic And monomers. These may be used singly or in combination of two or more.
The binder resin may be preferably an acrylic copolymer having at least one acidic group. Examples of the acidic group include a carboxyl group, a sulfonic acid group and a phosphoric acid group.
The binder resin preferably has an acid value of 70 to 150 mgKOH / g. The acid value of the binder resin is determined by the amine value of the dispersant used, usually the dispersant used has an amine value of 10-200 mgKOH / g. The acid value of the binder resin serves to enhance the stability of the pigment dispersion composition by offsetting the amine value of the dispersant to be used and to facilitate development of the non-exposed portion when the pigment dispersion composition is color photoresisted. Of course, in order to improve the developability of the unexposed portion, the acid value of the binder resin to be added when preparing the photoresist is primarily important, but also the acid value of the binder resin used when preparing the pigment dispersion composition is of course important. Since the amine value of the dispersant is very high, the higher the acid value of the binder resin used to offset it, the better. Particularly, the acid value of the binder resin is more preferably 80 to 130 mgKOH / g.
The binder resin preferably has a weight average molecular weight of 3,000 to 30,000, more preferably 5,000 to 30,000. When the weight average molecular weight of the binder resin is 3,000 to 30,000, excellent balance of dispersibility and viscosity can be obtained.
The binder resin is contained in an amount of 1 to 20 parts by weight, preferably 2 to 15 parts by weight, based on the total amount of the pigment dispersion composition. When the binder resin is contained in the above range, the dispersion is effectively dispersed to improve the dispersion stability, and the optical, physical and chemical quality is improved when the product is applied while maintaining an appropriate viscosity, which is preferable in view of excellent balance of dispersion stability and viscosity.
(E) Solvent
The solvent is not particularly limited, but specific examples thereof include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide Benzyl alcohol, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, Ethyl benzoate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.
Given the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate can be preferably used.
The solvent is included as a remainder with respect to the total amount of the pigment dispersion composition, preferably 30 to 90 parts by weight.
When the solvent is included in the above-mentioned range, the viscosity of the pigment dispersion composition is appropriately maintained, so that it has an excellent physical and optical property when applied to a product
According to another embodiment of the present invention, there is provided a photosensitive resin composition for a color filter comprising the above-described pigment dispersion composition, a binder resin, a photopolymerization initiator, a photopolymerizable monomer and a solvent.
Hereinafter, each component of the photosensitive resin composition for a color filter according to another embodiment of the present invention will be described in detail.
(I) Pigment dispersion composition
The pigment dispersion composition according to one embodiment of the present invention is contained in an amount of 10-70 parts by weight, preferably 30-60 parts by weight, based on the total amount of the photosensitive resin composition for a color filter. When the pigment dispersion composition is in the above range, the color filter has excellent pattern characteristics and excellent developing properties.
(Ii) binder resin
The binder resin used in the photosensitive resin composition for a color filter according to one embodiment of the present invention may be the same as the binder resin (D) constituting the above-mentioned pigment dispersion composition.
The binder resin is contained in an amount of 1-50 parts by weight, preferably 3-30 parts by weight, based on the total amount of the photosensitive resin composition for a color filter. When the binder resin is contained in the above-mentioned range, there is an advantage in that the color filter is excellent in developability and chemical resistance.
(Iii) Light curing Initiator
The photopolymerization initiator is a photopolymerization initiator generally used in a photosensitive resin composition. Examples of the photopolymerization initiator include an acetophenone compound, a benzophenone compound, a thioazane compound, a benzoin compound, a triazine compound, a oxime compound, And combinations thereof.
Examples of the acetophenone compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one can be used.
Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
As the thiozantone-based compound, thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone and the like can be used .
Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
Examples of the triazine type compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s- triazine, 2- (3 ', 4'-dimethoxy (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho 1-yl) (Trichloromethyl) -s-triazine, 2- (4-methoxynaphtho 1-yl) -4,6-bis (trichloromethyl) 6-triazine, 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine and the like can be used.
Examples of the oxime compounds include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (o- 6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone.
In addition to the photopolymerization initiator, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, a nonimidazole compound or the like can also be used as a photopolymerization initiator.
The photopolymerization initiator may be contained in an amount of 0.01-5 parts by weight, preferably 0.05-3 parts by weight, based on the total amount of the photosensitive resin composition for a color filter. When the photopolymerization initiator is contained in the above range, there is an advantage that the composition has excellent sensitivity and physical and optical properties.
(Iv) Photopolymerization Monomer
As the photopolymerizable monomer, a polyfunctional monomer having two or more hydroxyl groups may be used. Specific examples of the photopolymerizable monomer include glycerol acrylate, pentaerythritol hexaacrylate, ethylene glycol diacrylate, triethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate , Neopentyl glycol diacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol acrylate, pentaerythritol hexaacrylate , Bisphenol A diacrylate, trimethylolpropane triacrylate, novolak epoxy acrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate There is a rate like.
The photopolymerizable monomer may be contained in an amount of 1-80 parts by weight, preferably 5-50 parts by weight, based on the total amount of the photosensitive resin composition for a color filter. When the photopolymerizable monomer is contained in the above-mentioned range, proper viscosity can be maintained while maintaining the pattern well after exposure, and a pattern of a desired size can be obtained since there is no residue after exposure, so that physical and optical characteristics There is an excellent advantage.
(V) Solvent
The solvent used in the photosensitive resin composition for a color filter according to one embodiment of the present invention may be the same as the solvent (E) constituting the pigment dispersion composition.
The solvent is included as a remainder with respect to the total amount of the photosensitive resin composition for a color filter, and preferably 20 to 60 parts by weight. When the solvent is included in the above range, the viscosity of the resin composition is appropriately maintained, so that it is advantageous in physical and optical properties when applied to a product.
(Vi) Other additives
The photosensitive resin composition for a color filter according to an embodiment of the present invention may include at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid to prevent stains, spots, leveling, 3-amino-1,2-propanediol; A vinyl group or a silane coupling agent having a (meth) acryloxy group, and the like. The amount of these additives to be used can be easily controlled depending on the desired physical properties.
In addition, the photosensitive resin composition for a color filter according to an embodiment of the present invention may further include an epoxy compound as needed to improve adhesion and other characteristics.
Examples of the epoxy compound include epoxy novolac acrylate carboxylate resin, orthocresol novolak epoxy resin, phenol novolac epoxy resin, tetramethyl biphenyl epoxy resin, bisphenol A type epoxy resin, alicyclic epoxy resin, May be used.
The content of the epoxy compound is preferably 0.01 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition for a color filter.
When the epoxy compound is included in the above range, adhesion and economical adhesion and other properties can be improved.
When the epoxy compound is further included, it may further include a radical polymerization initiator such as a peroxide initiator or an azobis-based initiator.
According to another embodiment of the present invention, there is provided a color filter made from the photosensitive resin composition for a color filter. Since such a color filter can be manufactured by a conventional method, a detailed description will be omitted.
EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited by the following Examples.
< Example 1>
Bis [5- ( Phenyl ) - Dipyrine ]Copper Complex ( Cu ( PPN ) 2 ) Synthesis of
(1 g, 4.5 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.123 g, 4.95 mmol ) Were stirred in acetonitrile (AN) (20 ml) at room temperature for 4 hours. This was then quenched with triethylamine (TEA) (0.06 ml, 0.45 mmol). A saturated methanol solution of copper acetate (0.413 g, 2.25 mmol) was added to the reaction mixture and stirred for 5 hours. After completion of the reaction, the product was extracted and the solvent evaporated in vacuo with dichloromethane (CH 2 Cl 2). Wash the solution with water, and CH2Cl 2 and dried over anhydrous magnesium sulfate (MgSO 4). The solvent was evaporated to give Cu (PPN) 2 as a green solid which was recrystallized from dichloromethane (CH 2 Cl 2 ) and methanol. (Yield 22%), C 30 H 22 CuN 4, measured C, 71.79; H, 4.41; N, 11.11 Calcd. C, 71.77; H, 4.42; N, 11.16, FAB-Mass: 501 m / z
< Example 2>
Bis [5- (4- Fluorophenyl ) - Dipyrine ]Copper Complex ( Cu (4- FPN ) 2 ) Synthesis of
The title compound was obtained by applying the method of Example 1 (yield: 48%). C 30 H 20 CuF 2 N 4 , measurement C, 66.89; H, 3.79; N, 10.40, calculated as C, 66.97; H, 3.75; N, 10.41, FAB-Mass: 537 m / z.
< Example 3>
Bis [5- ( Pentafluorophenyl ) - Dipyrine ]Copper Complex ( Cu ( PFPPN ) 2 ) Synthesis of
The title compound was obtained by applying the method of Example 1 (yield: 48%). C 30 H 12 CuF 10 N 4 , measurement C, 53.24; H, 1.75; N, 8.24, Calcd. C, 52.84; H, 1.77; N, 8.22, FAB-Mass: 681 m / z.
< Example 4>
Bis [5- (4- Chlorophenyl ) - Dipyrine ]Copper Complex ( Cu (4- ClPN ) 2 ) Synthesis of
The title compound was obtained by applying the method of Example 1 (yield: 18%). C 30 H 20 Cl 2 CuN 4 , found C, 63.17; H, 3.57; N, 9.75, calculated C, 63.11; H, 3.53; N, 9.81, FAB-Mass: 569 m / z.
<Measurement>
1 H-NMR spectra were recorded on Bruker,
(1) Optical property measurement
The optical properties of the compounds synthesized according to Examples 1-4 of the present invention were evaluated by ultraviolet-visible (UV-Vis) absorption spectra, and the results are shown in Figs. 1-2 and Table 1.
UVmax (nm)
UVmax (nm)
(L / mol.cm)
(eV)
(eV)
(eV)
Cu (PPN) 2 , Cu (4ClPN) 2 in which phenyl, 4-chloro-phenyl and 4-fluoro-phenyl groups are substituted, respectively, in the ultraviolet-visible light spectrum in THF solution, 2 , and Cu (4FPN) 2 exhibited a maximum absorption wavelength between 463 and 467 nm and a shoulder peak of about 500 nm. On the other hand, Cu (PFPPN) 2 substituted with a pentafluorophenyl group exhibits a maximum absorption wavelength of 477 nm and a shoulder peak of 513 nm, indicating that the maximum peak and shoulder peak are red-shifted to about 10 nm or more, respectively. This may be due to the strong electron-attracting effect of the five fluorine atoms attached to the phenyl ring.
In addition, as shown in FIG. 2 and Table 1, Cu (PPN) 2 , Cu (4 ClPN), and Cu (Cu) were measured in an ultraviolet-visible light spectrum measured from a solution prepared by a solution of chloroform ) 2, and Cu (4FPN) maximum absorption wavelength of 2 was approximately 513 ± 1 nm, the case of Cu (PFPPN) 2, had the maximum absorption wavelength is appeared at 530 nm, which approximately 18 compared to the Cu (PPN) 2 nm red-shifted.
However, all of the synthesized pigments prepared in the Examples showed an appearance of red color.
As a result of measurement of the extinction coefficient of the synthesized material in the THF solution, all the pigments showed a very high logarithmic value of 4.78 or more (see Table 1), which is a major red pigment, diketopyrrolopyrrole DPP) derivatives (log ε: 4.24). Such a molar extinction coefficient means that the compound of formula (1) of the present invention can be applied as a pigment for an LCD color filter.
(2) Electrical characteristics measurement
HOMO and LUMO levels were calculated using the cyclic voltammetry (CV) of the compound synthesized according to Example 1-4 of the present invention and the band gap calculated through ultraviolet-visible light absorption spectra See Table 1). For the HOMO levels of the synthesized compounds, all compounds in the examples showed similar values of 5.4-5.5 eV. However, at the LUMO level, the LUMO levels of Cu (PPN) 2 , Cu (4ClPN) 2 and Cu (4FPN) 2 have a similar value of about 3.2 eV, but they have a large value of the pentafluorophenyl group Substituted Cu (PFPPN) 2 showed a LUMO level of 3.35 eV, which showed a decrease of about 0.15 eV.
(3) Measurement of thermal properties
The melting point temperature (Tm) and the decomposition temperature (Td) of the compound synthesized according to Example 1-4 of the present invention were measured, and the results are shown in Table 2 below.
As shown in Table 2, the decomposition temperatures (Td) values of Cu (PPN) 2 , Cu (4ClPN) 2 , Cu (4FPN) 2 and Cu (PFPPN) 2 were 270, 262, 234, and 277 ° C, respectively.
As to the melting point temperature (Tm), Cu (4FPN) 2 and Cu (PFPPN) 2 did not show definite Tm values and Tm of Cu (PPN) 2 and Cu (4ClPN) 2 had 276 and 262 ° C, respectively. As a result, Cu (4FPN) 2 and Cu (PPN) 2, Cu ( 4ClPN) 2 and Cu (PFPPN) except 2 it can be seen that having a relatively high thermal stability.
This is equivalent to a level of thermal stability higher than the highest temperature applied during the LCD manufacturing process of 250 ° C. These materials have a high possibility for application as a pigment for LCD.
(4) Measurement of thin film properties
In order to evaluate the characteristics of the thin film of the synthetic compound, the compound was spin-coated on a glass, and then a scanning electron microscope (SEM) was measured and shown in FIG.
As a result, a commercial product called Red 254 exhibits a rough surface as shown in Fig. 3 (a), but as shown in Fig. 3 (b) - (e) Showed a generally smooth surface.
The present invention has been described with reference to the preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is defined by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.
Claims (8)
[Chemical Formula 1]
In the above formula (1), R is C 5 -8 aryl which is unsubstituted or substituted by halogen.
Wherein R is phenyl which is unsubstituted or substituted with one or more F or Cl.
Wherein the compound of Formula 1 is selected from the group consisting of the following compounds:
Wherein the compound of formula 1 is selected from the group consisting of:
The 2,2- (phenylmethylene) bis (1H-pyrrole) derivative of Formula 4 prepared in Step 1 above was reacted with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (Step 2) of reacting a compound of formula (I) with a compound of formula
[Reaction Scheme 1]
In the above scheme 1, R is a C 5 -8 aryl unsubstituted or substituted by halogen.
The pigment dispersion composition may contain,
0.1 to 10% by weight of the pigment derivative represented by the formula (1);
5 to 30% by weight of pigment;
1 to 20% by weight of a dispersant;
1 to 20% by weight of a binder resin; And
And a solvent residue.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105732593A (en) * | 2016-04-20 | 2016-07-06 | 江苏大学 | Carbazole dipyrrylmethanes metal complex and preparing method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105732593A (en) * | 2016-04-20 | 2016-07-06 | 江苏大学 | Carbazole dipyrrylmethanes metal complex and preparing method thereof |
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