JP2010195911A - Polyhalogenated phthalocyanine pigment composition and coloring composition using the same - Google Patents
Polyhalogenated phthalocyanine pigment composition and coloring composition using the same Download PDFInfo
- Publication number
- JP2010195911A JP2010195911A JP2009041629A JP2009041629A JP2010195911A JP 2010195911 A JP2010195911 A JP 2010195911A JP 2009041629 A JP2009041629 A JP 2009041629A JP 2009041629 A JP2009041629 A JP 2009041629A JP 2010195911 A JP2010195911 A JP 2010195911A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- polyhalogenated
- polyhalogenated phthalocyanine
- general formula
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 87
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Polymers N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 238000004040 coloring Methods 0.000 title claims description 17
- 229920005792 styrene-acrylic resin Polymers 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 11
- 238000010298 pulverizing process Methods 0.000 claims description 19
- 239000000987 azo dye Substances 0.000 claims description 14
- 239000001052 yellow pigment Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- 238000001238 wet grinding Methods 0.000 abstract description 10
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- -1 maleic acid ester Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 229920001577 copolymer Polymers 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000001056 green pigment Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000011362 coarse particle Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- 238000003384 imaging method Methods 0.000 description 2
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Landscapes
- Optical Filters (AREA)
Abstract
Description
本発明は、ポリハロゲン化フタロシアニン顔料組成物に関し、更に詳細には、微細でかつ均一な粒子径に整粒され、分散性が極めて良好で優れた粘度特性を有し、カラー液晶表示装置および固体撮像素子に用いられるカラーフィルターに使用すると、さらにコントラストや明度の高い均一な着色膜を形成し、表示品位の優れたカラーフィルターを提供することのできる上記顔料に関する。 The present invention relates to a polyhalogenated phthalocyanine pigment composition, and more specifically, it is finely sized to a uniform particle size, has a very good dispersibility, has excellent viscosity characteristics, a color liquid crystal display device and a solid When used in a color filter used in an image sensor, the present invention relates to the above pigment that can form a uniform colored film with higher contrast and brightness and provide a color filter with excellent display quality.
ハロゲン化フタロシアニン顔料は、ハロゲン基数により色相が青色から緑色までの色相を有し、特に、ポリハロゲン化銅フタロシアニン顔料は、緑色顔料として塗料、印刷インキ、プラスチック用着色剤として使用されてきた。また、近年は、液晶ディスプレイ用のカラーフィルター用着色剤やインクジェットインク記録用インキ着色剤などにも使用されている。ポリハロゲン化銅フタロシアニン顔料であるＣ．Ｉ．ピグメントグリーン７、同３６は、カラーフィルターの着色画素部のうち、緑色画素部を形成するための緑色顔料として使用されており、調色のために必要に応じて、黄色顔料が併用されている。
そして、液晶ディスプレイがモニター用途から大型カラーテレビ用途に拡大するに従って、液晶ディスプレイ用のカラーフィルターの高いコントラスト比や高明度化が求められるようになっている。その結果、カラーフィルターの高いコントラスト比を実現するために顔料は印刷インキ、グラビアインキ、着色剤で通常使用されているレベルよりさらに微細化、整粒化が行われている。
Halogenated phthalocyanine pigments have hues ranging from blue to green depending on the number of halogen groups. In particular, polyhalogenated copper phthalocyanine pigments have been used as paints, printing inks, and colorants for plastics as green pigments. In recent years, it has also been used as a color filter colorant for liquid crystal displays and an ink colorant for inkjet ink recording. C. a polyhalogenated copper phthalocyanine pigment. I. Pigment Green 7 and 36 are used as green pigments for forming the green pixel portion of the colored pixel portions of the color filter, and a yellow pigment is used in combination for color matching as necessary. .
As the liquid crystal display expands from a monitor application to a large color television application, a high contrast ratio and a high brightness of the color filter for the liquid crystal display are required. As a result, in order to realize a high contrast ratio of the color filter, the pigment is further refined and sized so as to be higher than the level normally used in printing ink, gravure ink and colorant.
緑色顔料の製造方法は、フタロシアニンのハロゲン化による粗製ポリハロゲン化フタロシアニン顔料の製造と、粗製顔料を鮮明で着色力の大きい製品顔料にする顔料化よりなる。粗製ポリハロゲン化フタロシアニン顔料の製造方法としては、塩化アルミニウムと食塩の共溶融塩、四塩化チタンを溶媒としてハロゲン化する方法、無機塩の粉末を担体としてハロゲン化する固相法、ハロゲン化フタルイミドなどの環化縮合反応による方法等が知られている。 The method for producing a green pigment comprises the production of a crude polyhalogenated phthalocyanine pigment by halogenation of phthalocyanine, and the pigmentation to make the crude pigment a product pigment having a clear and high coloring power. Crude polyhalogenated phthalocyanine pigments can be produced by co-molten salts of aluminum chloride and sodium chloride, halogenated with titanium tetrachloride as a solvent, solid phase method with inorganic salt powder as a carrier, halogenated phthalimide, etc. A method using a cyclocondensation reaction is known.
いずれの方法で合成された粗製ポリハロゲン化フタロシアニン顔料は、結晶形は無定形であり、粒子径は極めて微細で凝集状態である。従って、このままでは、ワニス中で十分に分散できず、色材としては適さない。そこで、結晶化を行うと同時に、最適な粒子径、粒度分布をもつ顔料に顔料化を行う必要がある。 The crude polyhalogenated phthalocyanine pigment synthesized by any method has an amorphous crystal form, an extremely fine particle size, and an agglomerated state. Therefore, as it is, it cannot be sufficiently dispersed in the varnish and is not suitable as a coloring material. Therefore, it is necessary to perform crystallization and pigmentization to a pigment having an optimum particle size and particle size distribution.
例えば、特許文献１は、粗製ポリハロゲン化フタロシアニンを有機溶剤で結晶成長させて顔料化する方法、湿式粉砕でシェアを加えながら加熱して結晶成長させ顔料化する方法が開示されている。しかし、これらの方法は粒子を成長させて顔料化しているため、微細な粒子を得るためには、粒子成長を防止させるためより低温で、しかも短時間で顔料化を終了させるしかない。しかし、ポリハロゲン化フタロシアニン顔料は、他の顔料と異なり結晶化しにくいため、微細な粒子を得ようとすると、一部顔料が顔料化せず残存し、結果として分散不良となりコントラストなどが低下するという問題点があった。 For example, Patent Document 1 discloses a method in which crude polyhalogenated phthalocyanine is crystallized with an organic solvent to form a pigment, and a method in which crystal is grown by heating while adding a share by wet grinding to form a pigment. However, since these methods grow the particles to form pigments, the only way to obtain fine particles is to complete the pigmentation at a lower temperature and in a shorter time in order to prevent particle growth. However, since polyhalogenated phthalocyanine pigments are difficult to crystallize unlike other pigments, when trying to obtain fine particles, some pigments remain without being pigmented, resulting in poor dispersion and reduced contrast and the like. There was a problem.
そのため、特許文献２には、最初に、溶剤処理や湿式粉砕で粒子成長させ、粒子を大きくして顔料化を行い、その後、低温で湿式粉砕を行って微細な顔料を得る方法が開示されている。しかし、この方法は顔料化を２回行わなければならず、非常に効率が悪い。しかも、この方法で微細化は不完全で、カラーフィルターでの市場が要求している高いコントラストや明度を得ることはできなかった。
顔料の微細化については、一般的に特許文献３に示されるように、色素誘導体が微細化する顔料の母体骨格または同様の類似骨格を有している方が顔料との吸着も強く、結晶成長を抑制する効果が高い。また、湿式粉砕する際の混錬状態も良好で微細化に効果があることが知られている。しかし、ポリハロゲン化フタロシアニンには特許文献４に示されるような顔料の母体骨格を有する色素誘導体があるが、微細化に大きな効果は見られず、今回使用する母体骨格を有しないアゾ色素誘導体の方が微細化に効果を示すことが明らかとなった。
Therefore, Patent Document 2 discloses a method in which particles are first grown by solvent treatment or wet pulverization, the particles are enlarged to form a pigment, and then wet pulverization is performed at a low temperature to obtain a fine pigment. Yes. However, this method has to be pigmented twice and is very inefficient. Moreover, miniaturization is incomplete by this method, and the high contrast and brightness required by the market for color filters could not be obtained.
Regarding the refinement of pigments, generally, as shown in Patent Document 3, if the pigment derivative has the base skeleton of the pigment to be refined or a similar skeleton, the adsorption to the pigment is stronger and the crystal growth The effect which suppresses is high. In addition, it is known that the kneading state at the time of wet pulverization is good and is effective in miniaturization. However, although polyhalogenated phthalocyanine has a pigment derivative having a base skeleton of a pigment as shown in Patent Document 4, no significant effect is seen in miniaturization, and the azo dye derivative having no host skeleton used this time It became clear that the method has an effect on miniaturization.
カラー液晶表示装置および固体撮像素子に用いられるカラーフィルターに使用すると、表示品位の優れた特に高いコントラストと明度を有するカラーフィルターを得ることのできるポリハロゲン化フタロシアニン顔料組成物を提供することを目的とする。 An object of the present invention is to provide a polyhalogenated phthalocyanine pigment composition capable of obtaining a color filter having a particularly high contrast and brightness with excellent display quality when used in a color filter used in a color liquid crystal display device and a solid-state imaging device. To do.
本発明者らは、上述の目的を達成すべく鋭意研究の結果、湿式粉砕時にアゾ系色素誘導体とスチレンアクリル樹脂を使用することで、顔料の微細化と易分散化が図れ、本発明を完成させるに至った。
すなわち本発明は、ポリハロゲン化フタロシアニンと一般式（１）に示すアゾ系色素誘導体とを無機塩類と有機溶剤の存在下で湿式粉砕することを特徴とする、ポリハロゲン化フタロシアニン顔料組成物に関する。
一般式（１）
That is, the present invention relates to a polyhalogenated phthalocyanine pigment composition characterized by wet pulverizing a polyhalogenated phthalocyanine and an azo dye derivative represented by the general formula (1) in the presence of an inorganic salt and an organic solvent.
General formula (1)
一般式（１）において、
Ａ、Ｂは、水酸基、あるいは下記一般式（２）〜（３）で示される塩基性置換基を表す。
In general formula (1),
A and B represent a hydroxyl group or a basic substituent represented by the following general formulas (2) to (3).
一般式（２）
一般式（３）
一般式（２）、（３）において、
Ｒ１、Ｒ２は、それぞれ独立に、置換されてもよい飽和もしくは不飽和のアルキル基、またはＲ１、Ｒ２で、窒素、酸素もしくは硫黄原子を含む、置換されてもよい複素環を示す。ただし、nは１〜１０の整数を表す。
In general formulas (2) and (3),
R 1 and R 2 each independently represents a saturated or unsaturated alkyl group which may be substituted, or a heterocyclic ring which may be substituted containing a nitrogen, oxygen or sulfur atom in R 1 or R 2. . However, n represents the integer of 1-10.
さらに本発明は、ポリハロゲン化フタロシアニンと上記一般式（１）に示すアゾ系色素誘導体とスチレンアクリル樹脂とを無機塩類と有機溶剤の存在下で湿式粉砕することを特徴とする、ポリハロゲン化フタロシアニン顔料組成物に関する。
さらに本発明は、ポリハロゲン化フタロシアニンがＣ．Ｉ．ピグメントグリーン７、Ｃ．Ｉ．ピグメントグリーン３６である上記顔料組成物に関する。
Furthermore, the present invention is a polyhalogenated phthalocyanine characterized by wet-pulverizing a polyhalogenated phthalocyanine, an azo dye derivative represented by the above general formula (1), and a styrene acrylic resin in the presence of an inorganic salt and an organic solvent. The present invention relates to a pigment composition.
Furthermore, the present invention provides that the polyhalogenated phthalocyanine is C.I. I. Pigment green 7, C.I. I. The present invention relates to the pigment composition which is CI Pigment Green 36.
さらに本発明は、上記顔料組成物と顔料担体とを含むことを特徴とする着色組成物に関する。 Furthermore, this invention relates to the coloring composition characterized by including the said pigment composition and a pigment carrier.
さらに本発明は、上記顔料と黄色顔料を含むことを特徴とする着色組成物に関する。
さらに本発明は、上記顔料組成物を緑色画素部に含有してなるカラーフィルターに関する。
Furthermore, this invention relates to the coloring composition characterized by including the said pigment and a yellow pigment.
Furthermore, this invention relates to the color filter formed by containing the said pigment composition in a green pixel part.
本発明で得られたポリハロゲン化フタロシアニン顔料組成物は、カラー液晶表示装置や固体撮像素子に用いられるカラーフィルターに使用されるのに好ましい吸収波長特性を有しており、カラーフィルターに使用した場合、その特性として重要な特にコントラスト、明度の高い着色皮膜が得られる。 The polyhalogenated phthalocyanine pigment composition obtained in the present invention has preferable absorption wavelength characteristics for use in color filters used in color liquid crystal display devices and solid-state imaging devices, and when used in color filters. A colored film having particularly high contrast and brightness, which is important as its characteristics, can be obtained.
次に発明の実施の形態を挙げて、本発明を更に詳細に説明する。 Next, the present invention will be described in more detail with reference to embodiments of the invention.
本発明で使用するポリハロゲン化フタロシアニンは、少なくとも４つ以上のハロゲン原子を有し、ハロゲン原子としては、フッ素、塩素、臭素、ヨウ素が挙げられる。ポリハロゲン化フタロシアニンの中心金属は、Ｍｇ、Ａｌ、Ｓｉ、Ｔｉ、Ｖ、Ｍｎ、Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ、Ｚｎ、Ｇｅ、Ｓｎであり、より好ましくは、Ｃｕである。中心金属の価数によては軸にハロゲン原子、水酸基が結合する。また、フタロシアニンのポリハロゲン化方法としては、従来公知の方法から選択でき、特に限定されない。ポリハロゲン化フタロシアニンとしては、Ｃ．Ｉ．ピグメントグリーン７、Ｃ．Ｉ．ピグメントグリーン３６がより好ましい。 The polyhalogenated phthalocyanine used in the present invention has at least four or more halogen atoms, and examples of the halogen atom include fluorine, chlorine, bromine and iodine. The central metal of the polyhalogenated phthalocyanine is Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Cu, Zn, Ge, or Sn, and more preferably Cu. Depending on the valence of the central metal, a halogen atom or a hydroxyl group is bonded to the axis. Further, the polyhalogenation method of phthalocyanine can be selected from conventionally known methods and is not particularly limited. Examples of the polyhalogenated phthalocyanine include C.I. I. Pigment green 7, C.I. I. Pigment Green 36 is more preferable.
本発明で使用するアゾ色素誘導体としては、下記一般式（１）で表される化合物が挙げられる。
一般式（１）
General formula (1)
一般式（１）において、
Ａ、Ｂは、水酸基、あるいは下記一般式（２）〜（３）で示される塩基性置換基を表す。
In general formula (1),
A and B represent a hydroxyl group or a basic substituent represented by the following general formulas (2) to (3).
一般式（２）
一般式（３）
一般式（２）、（３）において、
Ｒ１、Ｒ２は、それぞれ独立に、置換されてもよい飽和もしくは不飽和のアルキル基、またはＲ１、Ｒ２で、窒素、酸素もしくは硫黄原子を含む、置換されてもよい複素環を示す。ただし、nは１〜１０の整数を表す。
本発明で使用するアゾ色素誘導体としては、以下の化合物を用いることができるが、これらに限定されるものではない。
In general formulas (2) and (3),
R 1, R 2 are, each independently represent a optionally substituted saturated or unsaturated alkyl group, or R 1, R 2, nitrogen, oxygen or sulfur atom, the heterocyclic ring which may be substituted . However, n represents the integer of 1-10.
As the azo dye derivative used in the present invention, the following compounds can be used, but are not limited thereto.
本発明で使用するスチレンアクリル樹脂は、スチレン基を有するモノマーAと不飽和カルボン酸であるモノマーBとの共重合体である。モノマーAとしては、具体的には、スチレン、α−メチルスチレン、スチレンのオルト、メタ、パラ−アルキル誘導体等が挙げられ、単独で使用しても、２種類以上を混合して使用しもよい。モノマーBとしては、具体的にアクリル酸、アクリル酸エステル、マレイン酸、マレイン酸エステル、フマル酸、フマル酸エステル、イタコン酸、イタコン酸エステル等が挙げられ、単独で使用しても、２種類以上を混合して使用しもよい。モノマーAとモノマーBの重合方法は、従来公知の方法から選択でき、特に限定されない。 The styrene acrylic resin used in the present invention is a copolymer of a monomer A having a styrene group and a monomer B which is an unsaturated carboxylic acid. Specific examples of the monomer A include styrene, α-methylstyrene, ortho, meta, and para-alkyl derivatives of styrene. These may be used alone or in combination of two or more. . Specific examples of the monomer B include acrylic acid, acrylic acid ester, maleic acid, maleic acid ester, fumaric acid, fumaric acid ester, itaconic acid, itaconic acid ester, etc. May be used in combination. The polymerization method of monomer A and monomer B can be selected from conventionally known methods and is not particularly limited.
本発明におけるモノマーAとモノマーBを共重合させて得られる共重合体において、各モノマーの総量を１００重量％とした時の共重合重量分率が以下の範囲にあることが好ましい。 In the copolymer obtained by copolymerizing the monomer A and the monomer B in the present invention, the copolymer weight fraction when the total amount of each monomer is 100% by weight is preferably in the following range.
モノマーA；１０〜９５重量％、より好ましくは２０〜８５重量％
モノマーB；５〜９０重量％、より好ましくは１５〜８０重量％
本発明に使用するスチレンアクリル樹脂は、ガラス転移点（Ｔｇ）が２００℃以下が好ましく、より好ましくは、湿式粉砕をする時の温度と同じ５０〜１５０℃が好ましい。
Monomer A; 10 to 95% by weight, more preferably 20 to 85% by weight
Monomer B; 5-90% by weight, more preferably 15-80% by weight
The glass transition point (Tg) of the styrene acrylic resin used in the present invention is preferably 200 ° C. or less, and more preferably 50 to 150 ° C., which is the same as the temperature at which wet pulverization is performed.
本発明における湿式粉砕でポリハロゲン化フタロシアニンとアゾ系色素誘導体とスチレンアクリル樹脂の混合比は、各々の添加量の総量を１００重量％とした時の添加重量分立が以下の範囲にあることが好ましい。 The mixing ratio of the polyhalogenated phthalocyanine, the azo dye derivative, and the styrene acrylic resin in the wet pulverization according to the present invention is preferably such that the added weight separation when the total amount of each added amount is 100% by weight is in the following range. .
ポリハロゲン化フタロシアニン；６０〜９９重量％、より好ましくは７０〜９６重量％
アゾ色素誘導体；１〜２０重量％、より好ましくは２〜１５重量％
スチレンアクリル樹脂；０〜２０重量％、より好ましくは２〜１５重量％
本発明の湿式粉砕は、粗製ポリハロゲン化フタロシアニンを磨砕剤である水溶性無機塩類と湿潤剤である有機溶剤と共に粘長な液状組成物として粉砕する工程である。
Polyhalogenated phthalocyanine; 60-99 wt%, more preferably 70-96 wt%
Azo dye derivative; 1 to 20% by weight, more preferably 2 to 15% by weight
Styrene acrylic resin; 0 to 20% by weight, more preferably 2 to 15% by weight
The wet pulverization of the present invention is a step of pulverizing crude polyhalogenated phthalocyanine as a viscous liquid composition together with a water-soluble inorganic salt as a grinding agent and an organic solvent as a wetting agent.
本発明において用いられる磨砕剤である水溶性無機塩としては塩化ナトリウム、塩化カリウム、塩化カルシウム、塩化バリウム、硫酸ナトリウム等が挙げられる。
水溶性無機塩の使用量は、多い方が顔料の摩砕効果は高いが、粗製ポリハロゲン化フタロシアニンに対して１〜５０倍重量であることが好ましく、生産性の点で１〜２０倍重量であることがより好ましい。さらに、水溶性無機塩に含まれる水分は１％以下であることが好ましい。
Examples of the water-soluble inorganic salt that is a grinding agent used in the present invention include sodium chloride, potassium chloride, calcium chloride, barium chloride, sodium sulfate and the like.
The higher the amount of water-soluble inorganic salt used, the higher the pigment grinding effect, but it is preferably 1 to 50 times the weight of the crude polyhalogenated phthalocyanine, and 1 to 20 times the weight in terms of productivity. It is more preferable that Furthermore, the water content in the water-soluble inorganic salt is preferably 1% or less.
また、水溶性有機溶剤の使用量は、粗製ポリハロゲン化フタロシアニンに対して０．５〜３倍重量であることが好ましく、１〜２倍重量であることがより好ましい。 The amount of the water-soluble organic solvent used is preferably 0.5 to 3 times the weight, more preferably 1 to 2 times the weight of the crude polyhalogenated phthalocyanine.
本発明において用いられる湿潤剤としては、粗製ポリハロゲン化フタロシアニンと接触させることで、粗製ポリハロゲン化フタロシアニンが湿潤して摩砕効果が増大し微細化が促進するものであれば特に制限はないが、水溶性有機溶剤が好ましい。 The wetting agent used in the present invention is not particularly limited as long as it is brought into contact with the crude polyhalogenated phthalocyanine so that the crude polyhalogenated phthalocyanine is moistened to increase the grinding effect and promote miniaturization. A water-soluble organic solvent is preferred.
水溶性有機溶剤としては、メタノール、エタノール、イソプロパノール、ｎ−プロパノール、イソブタノール、ｎ−ブタノール、エチレングリコール、ジエチレングリコール、ジエチレングリコールモノメチルエーテール、ジエチレングリコールモノエチルエーテール、ジエチレングリコールモノブチルエーテール、プロピレングリコール、プロピレンゴリコールモノメチルエーテルアセテート、アセトン、ジメチルホルムアミド、ジメチルスルホキシド、Ｎ−メチルピロリドン等を挙げることができる。これらは、必要に応じて２種類以上を混合して使用してもよい。 Water-soluble organic solvents include methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol, propylene Examples include goricol monomethyl ether acetate, acetone, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and the like. These may be used as a mixture of two or more if necessary.
また、水溶性有機溶剤の使用量は、粗製ポリハロゲン化フタロシアニンに対して０．１〜１０倍重量であることが好ましく、１〜４倍重量であることがより好ましい。 Further, the amount of the water-soluble organic solvent used is preferably 0.1 to 10 times the weight, more preferably 1 to 4 times the weight of the crude polyhalogenated phthalocyanine.
湿式粉砕には、少量用いることで粗製ポリハロゲン化フタロシアニンに吸着して廃水中に流失しないならば、ベンゼン、トルエン、キシレン、エチルベンゼン、クロロベンゼン、ニトロベンゼン、アニリン、ピリジン、キノリン、テトラヒドロフラン、ジオキサン、酢酸エチル、酢酸イソプロピル、酢酸ブチル、ヘキサン、ヘプタン、オクタン、ノナン、デカン、ウンデカン、ドデカン、シクロヘキサン、メチルシクロヘササン、ハロゲン化炭化水素、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等を上記水溶性有機溶剤と併用しても良い。これらは、必要に応じて２種類以上を混合して使用してもよい。 For wet milling, if it is used in a small amount and adsorbs to the crude polyhalogenated phthalocyanine and does not run away in the wastewater, benzene, toluene, xylene, ethylbenzene, chlorobenzene, nitrobenzene, aniline, pyridine, quinoline, tetrahydrofuran, dioxane, ethyl acetate , Isopropyl acetate, butyl acetate, hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, methylcyclohesasan, halogenated hydrocarbon, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. in combination with the above water-soluble organic solvent May be. These may be used as a mixture of two or more if necessary.
本発明において使用する湿式粉砕装置については特に制限はないが、トリミックス（井上製作所製）、スーパーミックス（新栄機械製）や摩砕効果が高いニーダー（井上製作所製）等の装置を用いることができる。
本発明における湿式粉砕装置の運転条件については特に制限はないが、粉砕メディアによる磨砕を効果的に進行させるため、装置がニーダーの場合は、以下の運転条件が好ましい。すなわち、装置内のブレードの回転数は１０〜２００ｒｐｍが好ましく、２軸の回転比が相対的に大きいほうが、摩砕効果が大きく好ましい。また、運転時間は１〜２４時間が好ましく、装置の内温は５０〜１５０℃が好ましい。また、粉砕メディアである水溶性無機塩は、粉砕粒度が５〜５０μｍで、粒子径の分布がシャープで、かつ球形が好ましい。
Although there is no restriction | limiting in particular about the wet crushing apparatus used in this invention, It is using apparatus, such as a trimix (made by Inoue Seisakusho), a supermix (made by Shinei Machine), and a kneader (made by Inoue Seisakusho) with a high grinding effect. it can.
Although there is no restriction | limiting in particular about the operating conditions of the wet grinding apparatus in this invention, In order to advance grinding | pulverization by a grinding | pulverization media effectively, the following operating conditions are preferable when an apparatus is a kneader. That is, the rotation speed of the blade in the apparatus is preferably 10 to 200 rpm, and a relatively large biaxial rotation ratio is preferable because the grinding effect is large. The operation time is preferably 1 to 24 hours, and the internal temperature of the apparatus is preferably 50 to 150 ° C. The water-soluble inorganic salt that is a pulverizing medium preferably has a pulverized particle size of 5 to 50 μm, a sharp particle size distribution, and a spherical shape.
本発明においては、湿式粉砕時に必要に応じて、界面活性剤、高級脂肪酸を添加してもよい。界面活性剤としては特に制限はなく、アニオン性、中性、カチオン性のいずれの界面活性剤を用いても良い。 In the present invention, a surfactant and a higher fatty acid may be added as necessary during wet pulverization. The surfactant is not particularly limited, and any anionic, neutral or cationic surfactant may be used.
高級脂肪酸としては、炭素数が多い酸でグリセリンとの反応で油脂を構成し、広く動物脂肪や植物油の成分として含まれる、親油性の強い水に難溶の酸であり、パルミチン酸、リノール酸、ステアリン酸、リノレン酸、オレイン酸等がある。高級脂肪酸としては、炭素数１０以上の脂肪酸が好ましく、さらに２０℃〜３０℃で液体である不飽和高級脂肪酸が好ましい。これに対して、炭素数の少ない脂肪酸には酢酸、吉草酸、ラク酸があり、遊離酸の状態になり親水性である。顔料を湿潤させて摩砕効果を増大させ、微細化を促進する脂肪酸としては、親油性の強い高級脂肪酸が適している。また、湿式粉砕で使用する水溶性無機塩類および水溶性有機溶剤は、水で洗浄することにより顔料から分離するが、炭素数の少ない親水性の脂肪酸は水中に溶解してしまい、BOD、CODの増加の要因になるので好ましくない。高級脂肪酸は、必要に応じて２種類以上を混合して使用してもよい。
本発明のポリハロゲン化フタロシアニン顔料は、顔料担体中にすることにより、オフセット用印刷インキ、グラビア用印刷インキ、水無しオフセット印刷インキ、シルクスクリーン印刷用インキ、溶剤現像型あるいはアルカリ現像型着色レジスト剤等の着色組成物とすることができる。
Higher fatty acids are fatty acids that react with glycerin and react with glycerin, and are widely soluble in animal fats and vegetable oils. They are sparingly soluble in highly lipophilic water, such as palmitic acid and linoleic acid. , Stearic acid, linolenic acid, oleic acid and the like. As the higher fatty acid, a fatty acid having 10 or more carbon atoms is preferable, and an unsaturated higher fatty acid which is liquid at 20 ° C. to 30 ° C. is more preferable. In contrast, fatty acids with a small number of carbons include acetic acid, valeric acid, and lactic acid, which are free acid and hydrophilic. Higher fatty acids with strong lipophilicity are suitable as the fatty acid that wets the pigment to increase the grinding effect and promotes refinement. In addition, water-soluble inorganic salts and water-soluble organic solvents used in wet grinding are separated from the pigment by washing with water, but hydrophilic fatty acids with a small number of carbons are dissolved in water, resulting in BOD and COD. This is not preferable because it causes an increase. Two or more types of higher fatty acids may be used as needed.
When the polyhalogenated phthalocyanine pigment of the present invention is contained in a pigment carrier, the offset printing ink, gravure printing ink, waterless offset printing ink, silk screen printing ink, solvent development type or alkali development type coloring resist agent It can be set as a coloring composition.
本発明のポリハロゲン化フタロシアニン顔料を均一に顔料担体中に分散させてなる着色組成物は、安定した粘度特性を示し、該着色組成物を用いることにより、高いコントラスト、明度、鮮明性を有するカラーフィルターを製造することができる。
顔料担体は、樹脂、その前駆体、またはそれらの混合物から構成される。樹脂には、熱硬化性樹脂、熱可塑性樹脂、活性エネルギー線硬化性樹脂があり、樹脂の前駆体には、活性エネルギー線照射により硬化して樹脂と同様の塗膜を形成するモノマー、オリゴマー等があり、これらを単独で、または２種類以上混合して用いることができる。顔料担体は、ポリハロゲン化フタロシアニン顔料１００重量部に対して、好ましくは５０〜７００重量部、より好ましくは１００〜４００重量部の量で用いることができる。
The colored composition obtained by uniformly dispersing the polyhalogenated phthalocyanine pigment of the present invention in a pigment carrier exhibits stable viscosity characteristics, and by using the colored composition, a color having high contrast, brightness, and sharpness. A filter can be manufactured.
The pigment carrier is composed of a resin, its precursor, or a mixture thereof. Resins include thermosetting resins, thermoplastic resins, and active energy ray curable resins, and precursors of resins include monomers and oligomers that form a coating film similar to the resin by being cured by irradiation with active energy rays. These can be used alone or in combination of two or more. The pigment carrier can be used in an amount of preferably 50 to 700 parts by weight, more preferably 100 to 400 parts by weight with respect to 100 parts by weight of the polyhalogenated phthalocyanine pigment.
樹脂は、着色組成物を用いてカラーフィルターを製造する場合には、可視光領域の４００〜７００ｎｍの全波長領域において透過率が８０％以上、好ましくは９５％以上の透明樹脂であることが好ましい。また、カラーフィルターの製造における後の工程において高温加熱の処理が行われるため、耐熱性のよい樹脂を用いることが必要である。 In the case of producing a color filter using a colored composition, the resin is preferably a transparent resin having a transmittance of 80% or more, preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. . In addition, since a high-temperature heating process is performed in a later process in manufacturing the color filter, it is necessary to use a resin having good heat resistance.
熱可塑性樹脂としては、例えば、ブチラール樹脂、スチレンーマレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、ポリスチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリエチレン（ＨＤＰＥ、ＬＤＰＥ）、ポリブタジエン、ポリイミド樹脂等が挙げられる。また、熱硬化性樹脂としては、例えば、エポキシ樹脂、ベンゾグアナミン樹脂、ロジン変性マレイン酸樹脂、ロジン変性フマル酸樹脂、メラミン樹脂、尿素樹脂、フェノール樹脂等が挙げられる。 Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. Acrylic resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.
活性エネルギー線硬化性樹脂としては、水酸基、カルボキシル基、アミノ基等の反応性の置換基を有する高分子に、イソシアネート基、アルデヒド基、エポキシ基等を介して、（メタ）アクリル化合物、ケイヒ酸等の光架橋性基を導入した樹脂が用いられる。また、スチレン−無水マレイン酸共重合物やα−オレフィン−無水マレイン酸共重合物等の酸無水物を含む線状高分子をヒドロキシアルキル（メタ）アクリレート等の水酸基を有する（メタ）アクリル化合物によりハーフエステル化した重合物も用いられる。 Active energy ray curable resins include polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, (meth) acrylic compounds, cinnamic acid via isocyanate groups, aldehyde groups, epoxy groups, etc. A resin having a photocrosslinkable group introduced therein is used. Further, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified polymers can also be used.
樹脂の前駆体モノマー、オリゴマーとしては、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、トリシクロデカニル（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレートのカプロラクトン付加物のヘキサ（メタ）アクリレート等の各種アクリル酸エステルおよびメタクリル酸エステル、アクリル酸、メタクリル酸、（メタ）アクリルアミド、Ｎ-ヒドロキシメチル（メタ）アクリルアミド、スチレン、酢酸ビニル、アクリロニトリル、メラミン（メタ）アクリレート、エポキシ（メタ）アクリレートプレポリマー等が挙げられる。 Resin precursor monomers and oligomers include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, Various acrylic and methacrylic acid esters such as dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, hexa (meth) acrylate of caprolactone adduct of dipentaerythritol hexa (meth) acrylate, acrylic acid, Methacrylic acid, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, styrene, vinyl acetate, acrylonitrile, melamine (meth) acrylate, epoxy Examples include cis (meth) acrylate prepolymers.
着色組成物には、該組成物を紫外線照射により硬化するときには、光重合開始剤等が添加される。光重合開始剤としては、４−フェノキシジクロロアセトフェノン、４−ｔ−ブチル−ジクロロアセトフェノン、ジエトキシアセトフェノン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、１−ヒドロキシシクロヘキシルフェニルケトン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン、２−メチル−１−［４−（メチルチオ）フェニル］−２−モルフォリノプロパン−１−オン等のアセトフェノン系光重合開始剤、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール等のベンゾイン系光重合開始剤、ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、４−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、４−ベンゾイル−４’−メチルジフェニルサルファイド等のベンゾフェノン系光重合開始剤、チオキサンソン、２−クロルチオキサンソン、２−メチルチオキサンソン、イソプロピルチオキサンソン、２，４−ジイソプロピルチオキサンソン等のチオキサンソン系光重合開始剤、２，４，６−トリクロロ−ｓ−トリアジン、２−フェニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−メトキシフェニル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−トリル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−ピペロニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−スチリル−ｓ−トリアジン、２−（ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（４−メトキシ−ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−トリクロロメチル−（ピペロニル）−６−トリアジン、２，４−トリクロロメチル（４’−メトキシスチリル）−６−トリアジン等のトリアジン系光重合開始剤、ボレート系光重合開始剤、カルバゾール系光重合開始剤、イミダゾール系光重合開始剤等が用いられる。光重合開始剤は、ポリハロゲン化フタロシアニン顔料１００重量部に対して、５〜１５０重量部の量で用いることができる。 When the composition is cured by ultraviolet irradiation, a photopolymerization initiator or the like is added to the colored composition. Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane Acetophenone photopolymerization initiators such as -1-one, benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4 Benzophenone photopolymerization initiators such as phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2 Thioxanthone photopolymerization initiators such as 2,4-diisopropylthioxanthone, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p -Methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (Trichloromethyl) -s-triazine, 2,4-bis (tri (Loromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4 , 6-Bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, etc. A polymerization initiator, a borate photopolymerization initiator, a carbazole photopolymerization initiator, an imidazole photopolymerization initiator, or the like is used. A photoinitiator can be used in the quantity of 5-150 weight part with respect to 100 weight part of polyhalogenated phthalocyanine pigments.
上記光重合開始剤は、単独で、あるいは２種以上混合して用いるが、増感剤として、α−アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、９，１０−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、４，４’−ジエチルイソフタロフェノン、３，３’，４，４’−テトラ（ｔ−ブチルパーオキシカルボニル）ベンゾフェノン、４，４’−ジエチルアミノベンゾフェノン等の化合物を併用することもできる。増感剤は、光重合開始剤１００重量部に対して、０．１〜１５０重量部の量で用いることができる。 The above photopolymerization initiators are used alone or in combination of two or more. As sensitizers, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenance are used. Such as lenquinone, camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone, etc. A compound can also be used in combination. The sensitizer can be used in an amount of 0.1 to 150 parts by weight with respect to 100 parts by weight of the photopolymerization initiator.
着色組成物には、顔料を顔料担体中に充分に分散させ、基材に均一に塗布するために、溶剤を用いることができる。溶剤としては、例えばシクロヘキサノン、エチルセロソルブアセテート、ブチルセロソルブアセテート、１−メトキシ−２−プロピルアセテート、ジエチレングリコールジメチルエーテル、エチルベンゼン、エチレングリコールジエチルエーテル、キシレン、エチルセロソルブ、メチル−ｎアミルケトン、プロピレングリコールモノメチルエーテルトルエン、メチルエチルケトン、酢酸エチル、メタノール、エタノール、イソプロピルアルコール、ブタノール、イソブチルケトン、石油系溶剤等が挙げられ、これらを単独で、もしくは混合して用いる。溶剤は、ポリハロゲン化フタロシアニン顔料１００重量部に対して、５００〜４０００重量部の量で用いることができる。 In the coloring composition, a solvent can be used in order to sufficiently disperse the pigment in the pigment carrier and uniformly apply it to the substrate. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether toluene, methyl ethyl ketone. , Ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent and the like, and these are used alone or in combination. The solvent can be used in an amount of 500 to 4000 parts by weight with respect to 100 parts by weight of the polyhalogenated phthalocyanine pigment.
本発明のポリハロゲン化フタロシアニン顔料組成物の顔料担体中への分散には、三本ロールミル、二本ロールミル、サンドミル、ニーダー等の各種分散手段を使用できる。また、これらの分散を良好とするために適宜、各種界面活性剤、色素誘導体等の分散助剤を添加できる。分散助剤は、顔料の分散に優れ、分散後の顔料の再凝集を防止する効果が大きい。これらの印刷インキ、着色レジスト剤等の着色組成物は、遠心分離、焼結フィルタ、メンブレンフィルタ等の手段にて、５μｍ以上の粗大粒子、好ましくは１μｍ以上の粗大粒子、さらに好ましくは０．５μｍ以上の粗大粒子、および混入した塵を除去することが好ましい。 Various dispersion means such as a three-roll mill, a two-roll mill, a sand mill, and a kneader can be used for dispersing the polyhalogenated phthalocyanine pigment composition of the present invention in a pigment carrier. Moreover, in order to make these dispersion | distribution favorable, dispersion | distribution adjuvants, such as various surfactant and a pigment derivative, can be added suitably. The dispersion aid is excellent in dispersing the pigment and has a great effect of preventing reaggregation of the pigment after dispersion. These coloring compositions such as printing ink and coloring resist agent are coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove the coarse particles and the mixed dust.
本発明の着色組成物は、所望の色度に調色するため、必要に応じて、黄色顔料を併用することができる。これらの黄色顔料は、色特性を損なわない範囲で添加することが好ましい。また、これらの黄色顔料は、必要に応じて、公知慣用の顔料誘導体、分散剤、界面活性剤および樹脂等の表面処理剤によって顔料粒子の表面が被覆された表面処理顔料を使用してもよい。黄色顔料の添加方法としては、湿式粉砕時に添加する方法、分散時に添加する方法、それぞれの分散液を混合して添加する方法がある。 Since the coloring composition of this invention adjusts to desired chromaticity, a yellow pigment can be used together as needed. These yellow pigments are preferably added in a range that does not impair the color characteristics. In addition, these yellow pigments may use surface-treated pigments in which the surface of pigment particles is coated with surface treatment agents such as known and commonly used pigment derivatives, dispersants, surfactants and resins, if necessary. . As a method for adding the yellow pigment, there are a method of adding at the time of wet pulverization, a method of adding at the time of dispersion, and a method of adding the respective dispersions by mixing.
本発明で併用できる黄色顔料は、カラーフィルターに使用される場合、分光透過スペクトルの透過率が最大となる波長（Ｔｍａｘ）がバックライト光源の望ましい輝線を拾うために使用することができる。
本発明で併用できる調色用黄色顔料としては、例えば、Ｃ．Ｉ．ピグメントイエロー ８３、同１２８、同１３８、同１３９、同１５０、同１５４、同１８０、同１８５等の黄色顔料が挙げられる。
When used in a color filter, the yellow pigment that can be used in combination with the present invention can be used for picking up a desired emission line of a backlight light source having a wavelength (Tmax) that maximizes the transmittance of the spectral transmission spectrum.
Examples of toning yellow pigments that can be used in the present invention include C.I. I. Pigment yellow 83, 128, 138, 139, 150, 154, 180, 185 and the like.
これらの黄色顔料は、１種単独で用いることもでき、２種以上を併用することもできる。上記黄色顔料のなかでも、Ｃ．Ｉ．ピグメントイエロー１３８、同１３９、同１５０が色純度と透明性に優れる点でより好ましい。
黄色顔料の混合比率は、用途に応じて適宜選択することができるが、一般にカラーフィターに使用する場合は、質量基準で、本発明の緑色顔料組成物と黄色顔料の合計量に対して、１０〜６０％の範囲とするのが好ましく、なかでも、３０〜５０％の範囲とするのがより好ましい。
These yellow pigments can be used alone or in combination of two or more. Among the yellow pigments, C.I. I. Pigment Yellow 138, 139, and 150 are more preferable in terms of excellent color purity and transparency.
The mixing ratio of the yellow pigment can be appropriately selected according to the use.Generally, when used in a color filter, the total amount of the green pigment composition of the present invention and the yellow pigment is based on the mass, It is preferable to set it as 10 to 60% of range, and it is more preferable to set it as 30 to 50% of range especially.
次に本発明を、実施例および比較例により具体的に説明するが、本発明は以下の実施例に限定されるものではない。例中、「部」及び「％」は特に断らないかぎり重量によるものである。 EXAMPLES Next, although an Example and a comparative example demonstrate this invention concretely, this invention is not limited to a following example. In the examples, “parts” and “%” are by weight unless otherwise specified.
［実施例１］
粗製ポリハロゲン化銅フタロシアニン（臭素個数１３．１個、塩素個数２．２個）１５０部とアゾ色素誘導体（化合物１）５部とスチレンアクリル樹脂（ジョンクリル６１１：ＢＡＳＦジャパン株式会社製）５部を平均粒子径２０μｍの粉砕、乾燥した塩化ナトリウム１５００部と共にニーダーに加えた。温度を７０℃にコントロールして、ジエチレングリコール２２０部を加え、良好なドウ状態を形成後、６時間湿式粉砕を行った。湿式粉砕後、内容物の１０倍の水中に加えて攪拌し、塩化ナトリウムおよびジエチレングリコールを溶解させた後、濾過、精製を行って顔料と分離した。このウェットケーキを、乾燥機で水分１％未満になるまで乾燥した後、ハンマーミル型粉砕機で粉砕し、５ｍｍのスクリーンを通して、ポリハロゲン化銅フタロシアニン顔料を得た。
（化合物１）
Crude polyhalogenated copper phthalocyanine (bromine number: 13.1, chlorine number: 2.2) 150 parts, azo dye derivative (compound 1) 5 parts, and styrene acrylic resin (Johncrill 611: manufactured by BASF Japan Ltd.) 5 parts Was added to a kneader together with 1500 parts of crushed and dried sodium chloride having an average particle size of 20 μm. The temperature was controlled at 70 ° C., 220 parts of diethylene glycol was added, and after forming a good dough state, wet grinding was performed for 6 hours. After wet pulverization, the mixture was added to 10 times the content of water and stirred to dissolve sodium chloride and diethylene glycol, followed by filtration and purification to separate the pigment. The wet cake was dried with a dryer until the water content was less than 1%, and then pulverized with a hammer mill type pulverizer to obtain a polyhalogenated copper phthalocyanine pigment through a 5 mm screen.
(Compound 1)
[実施例２]
実施例１の化合物１を化合物２に変えた以外は、実施例１と同様の操作を行った。
（化合物２）
The same operation as in Example 1 was carried out except that Compound 1 in Example 1 was changed to Compound 2.
(Compound 2)
[実施例３]
実施例１の化合物１を化合物３に変えた以外は、実施例１と同様の操作を行った。
（化合物３）
The same operation as in Example 1 was carried out except that Compound 1 in Example 1 was changed to Compound 3.
(Compound 3)
[実施例４]
実施例１の化合物１を化合物４に変えた以外は、実施例１と同様の操作を行った。
（化合物４）
The same operation as in Example 1 was carried out except that Compound 1 in Example 1 was changed to Compound 4.
(Compound 4)
[実施例５]
実施例１のスチレンアクリル樹脂をジョンクリル５８６（ＢＡＳＦジャパン株式会社製）に変えた以外は、実施例１と同様の操作を行った。
[実施例６]
実施例１のスチレンアクリル樹脂をジョンクリル８１９（ＢＡＳＦジャパン株式会社製）に変えた以外は、実施例１と同様の操作を行った。
[実施例７]
実施例１のスチレンアクリル樹脂をジョンクリル６１Ｊ（ＢＡＳＦジャパン株式会社製）に変えた以外は、実施例１と同様の操作を行った。ジョンクリル６１Jは固形分計算で５部添加した。
[実施例８]
実施例１の粗製ポリハロゲン化銅フタロシアニン１５０部とアゾ色素誘導体（化合物１）５部を平均粒子径２０μｍの粉砕、乾燥した塩化ナトリウム１５００部と共にニーダーに加えた。実施例１と同様の方法で湿式粉砕を行い、ポリハロゲン化銅フタロシアニン顔料を得た。
（化合物１）
The same operation as in Example 1 was performed except that the styrene acrylic resin of Example 1 was changed to Joncrill 586 (BASF Japan Ltd.).
[Example 6]
The same operation as in Example 1 was performed except that the styrene acrylic resin of Example 1 was changed to Joncrill 819 (manufactured by BASF Japan Ltd.).
[Example 7]
The same operation as in Example 1 was performed except that the styrene acrylic resin in Example 1 was changed to Joncrill 61J (manufactured by BASF Japan Ltd.). Joncrill 61J was added in an amount of 5 parts by solid content calculation.
[Example 8]
150 parts of the crude polyhalogenated copper phthalocyanine of Example 1 and 5 parts of an azo dye derivative (Compound 1) were added to a kneader together with 1500 parts of pulverized and dried sodium chloride having an average particle diameter of 20 μm. Wet grinding was performed in the same manner as in Example 1 to obtain a polyhalogenated copper phthalocyanine pigment.
(Compound 1)
[比較例１]
実施例１の粗製ポリハロゲン化銅フタロシアニン１５０部を平均粒子径２０μｍの粉砕、乾燥した塩化ナトリウム１５００部と共にニーダーに加えた。実施例１と同様の方法で湿式粉砕を行い、ポリハロゲン化銅フタロシアニン顔料を得た。
[比較例２]
実施例１の粗製ポリハロゲン化銅フタロシアニン１５０部とスチレンアクリル樹脂（ジョンクリル６１１：ＢＡＳＦジャパン株式会社製）５部を平均粒子径２０μｍの粉砕、乾燥した塩化ナトリウム１５００部と共にニーダーに加えた。実施例１と同様の方法で湿式粉砕を行い、ポリハロゲン化銅フタロシアニン顔料を得た。
[比較例３]
実施例１の粗製ポリハロゲン化銅フタロシアニン１５０部とポリハロゲン化銅フタロシアニン色素誘導体（化合物５）５部を平均粒子径２０μｍの粉砕、乾燥した塩化ナトリウム１５００部と共にニーダーに加えた。実施例１と同様の方法で湿式粉砕を行い、ポリハロゲン化銅フタロシアニン顔料を得た。
（化合物５）
150 parts of the crude polyhalogenated copper phthalocyanine of Example 1 was added to a kneader together with 1500 parts of crushed and dried sodium chloride having an average particle size of 20 μm. Wet grinding was performed in the same manner as in Example 1 to obtain a polyhalogenated copper phthalocyanine pigment.
[Comparative Example 2]
150 parts of crude polyhalogenated copper phthalocyanine of Example 1 and 5 parts of styrene acrylic resin (Johncrill 611: manufactured by BASF Japan Ltd.) were added to a kneader together with 1500 parts of crushed and dried sodium chloride having an average particle diameter of 20 μm. Wet grinding was performed in the same manner as in Example 1 to obtain a polyhalogenated copper phthalocyanine pigment.
[Comparative Example 3]
150 parts of the crude polyhalogenated copper phthalocyanine of Example 1 and 5 parts of a polyhalogenated copper phthalocyanine dye derivative (Compound 5) were added to a kneader together with 1500 parts of pulverized and dried sodium chloride having an average particle size of 20 μm. Wet grinding was performed in the same manner as in Example 1 to obtain a polyhalogenated copper phthalocyanine pigment.
(Compound 5)
（実施例、比較例で得た顔料のカラーフィルター特性評価）
実施例、比較例で得た顔料について、色度、明度を測定した。これらの評価は、感光性着色組成物を作製し、感光性着色組成物をスピンコーターを用いてガラス基板に塗布し、露光、加熱後の塗布基板について、色度、明度、コントラストを測定した。以下、評価方法について詳細に記述する。
(Evaluation of color filter characteristics of pigments obtained in Examples and Comparative Examples)
The chromaticity and lightness of the pigments obtained in Examples and Comparative Examples were measured. In these evaluations, a photosensitive coloring composition was prepared, the photosensitive coloring composition was applied to a glass substrate using a spin coater, and the chromaticity, brightness, and contrast of the coated substrate after exposure and heating were measured. The evaluation method will be described in detail below.
（アクリル樹脂溶液の調製）
反応容器にシクロヘキサノン８００部を入れ、容器に窒素ガスを注入しながら１００℃に加熱して、同温度で下記モノマーおよび熱重合開始剤の混合物を１時間かけて滴下して重合反応を行った。
スチレン ６０．０部
メタクリル酸 ６０．０部
メタクリル酸メチル ６５．０部
メタクリル酸ブチル ６５．０部
アゾビスイソブチロニトリル １０．０部
(Preparation of acrylic resin solution)
A reaction vessel was charged with 800 parts of cyclohexanone, heated to 100 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Styrene 60.0 parts Methacrylic acid 60.0 parts Methyl methacrylate 65.0 parts Butyl methacrylate 65.0 parts Azobisisobutyronitrile 10.0 parts
滴下後さらに１００℃で３時間反応させた後、アゾビスイソブチロニトリル２．０部をシクロヘキサノン５０部で溶解させたものを添加し、さらに１００℃で１時間反応を続けて、重量平均分子量が約４００００のアクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約２ｇをサンプリングして１８０℃、２０分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が２０％となるようにシクロヘキサノンを添加してアクリル樹脂溶液を調製した。 After the dropwise addition, the mixture was further reacted at 100 ° C. for 3 hours, and then 2.0 parts of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour to obtain a weight average molecular weight. A solution of about 40,000 acrylic resin was obtained. After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20%. An acrylic resin solution was prepared.
（感光性着色組成物の作製）
下記組成の混合物を均一に分散撹拌混合した後、１μｍのフィルタで濾過して感光性着色組成物を作製した。
ポリハロゲン化フタロシアニン顔料 ４．５部
（実施例１〜８および比較例１〜３）
アクリル樹脂溶液 ２４．０部
トリメチロールプロパントリアクリレート ５．４部
（新中村化学社製「ＮＫエステルＡＴＭＰＴ」）
光開始剤（チバガイギー社製「イルガキュアー９０７」） ０．３部
増感剤（保土ヶ谷化学社製「ＥＡＢ−Ｆ」） ０．２部
シクロヘキサノン ６５．１部
(Preparation of photosensitive coloring composition)
A mixture having the following composition was uniformly dispersed, stirred and mixed, and then filtered through a 1 μm filter to prepare a photosensitive coloring composition.
Polyhalogenated phthalocyanine pigment 4.5 parts
(Examples 1-8 and Comparative Examples 1-3)
Acrylic resin solution 24.0 parts
5.4 parts of trimethylolpropane triacrylate
(Shin Nakamura Chemical "NK Ester ATMPT")
Photoinitiator ("Irgacure 907" manufactured by Ciba Geigy) 0.3 parts
Sensitizer (Hoabaya Chemical "EAB-F") 0.2 parts
65.1 parts cyclohexanone
実施例１〜８および比較例１〜３で得られた顔料を用いて作製した感光性着色組成物を、１００ｍｍ×１００ｍｍ、１．１ｍｍ厚のガラス基板上に、スピンコーターを用いて５００ｒｐｍ、１０００ｒｐｍ、２０００ｒｐｍの回転数で塗布し、膜厚が異なる３種の塗布基板を得た。次に、７０℃で２０分乾燥後、超高圧水銀ランプを用いて、積算光量１５０ｍＪで紫外線露光を行った。塗布基板を２２０℃で２０分間加熱後、放冷し着色膜を作製した。そして、得られた着色膜の分光を分光光度計（日立製作所製「Ｕ―３５００」）で測定し、Ｃ光源でのそれぞれの色度（Ｙ，ｘ，ｙ）を算出し、ｙ＝０．５００の時のそれぞれのＹ，ｘをさらに算出した。また、コントラストは、得られた着色膜をコントラストテスター（壺坂電機製「ＣＴ−１ＢＦ」）で測定しｙ＝０．５００の時のコントラストを算出した。粘度は、EL型粘度計（東機産業製ＴＶ−２０、５０ｒｐｍ、単位はｍＰａ・Ｓ）で測定した。その結果を表1に示す。 The photosensitive coloring composition produced using the pigments obtained in Examples 1 to 8 and Comparative Examples 1 to 3 was placed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm using a spin coater at 500 rpm and 1000 rpm. The coating was performed at a rotational speed of 2000 rpm to obtain three types of coated substrates having different film thicknesses. Next, after drying at 70 ° C. for 20 minutes, ultraviolet exposure was performed with an integrated light amount of 150 mJ using an ultrahigh pressure mercury lamp. The coated substrate was heated at 220 ° C. for 20 minutes and then allowed to cool to produce a colored film. Then, the spectrum of the obtained colored film was measured with a spectrophotometer (“U-3500” manufactured by Hitachi, Ltd.), and each chromaticity (Y, x, y) with a C light source was calculated, and y = 0. Each Y and x at 500 was further calculated. Further, the contrast was measured by measuring the obtained colored film with a contrast tester (“CT-1BF” manufactured by Aisaka Electric Co., Ltd.) and calculating the contrast when y = 0.500. The viscosity was measured with an EL type viscometer (TV-20, manufactured by Toki Sangyo, 50 rpm, the unit being mPa · S). The results are shown in Table 1.
表１の実施例１と比較例１、２を比較すると、粗製ポリハロゲン化フタロシアニンとアゾ系色素誘導体、スチレンアクリル樹脂とを同時に湿式粉砕することで、それぞれを添加なしに、またはスチレンアクリル樹脂のみで湿式粉砕するよりもコントラストや明度の高い着色皮膜と粘度の低い分散液を得る事が可能となった。また、他の実施例２〜７も同様の結果であった。実施例８と比較例３を比較するとアゾ色素誘導体の方が、ポリハロゲン化銅フタロシアニン色素誘導体を用いるよりもコントラストや粘度に効果があることが明らかである。 When Example 1 of Table 1 and Comparative Examples 1 and 2 are compared, the crude polyhalogenated phthalocyanine, the azo dye derivative, and the styrene acrylic resin are simultaneously wet pulverized without adding each of them, or only the styrene acrylic resin It became possible to obtain a colored film having a higher contrast and brightness and a dispersion having a lower viscosity than by wet pulverization. Moreover, the other Examples 2-7 were the same results. Comparing Example 8 and Comparative Example 3, it is clear that the azo dye derivative is more effective in contrast and viscosity than the polyhalogenated copper phthalocyanine dye derivative.
Claims (6)
一般式（１）
Ａ、Ｂは、水酸基、あるいは下記一般式（２）〜（３）で示される塩基性置換基を表す。
一般式（２）
Ｒ１、Ｒ２は、それぞれ独立に、置換されてもよい飽和もしくは不飽和のアルキル基、またはＲ１、Ｒ２で、窒素、酸素もしくは硫黄原子を含む、置換されてもよい複素環を示す。ただし、nは１〜１０の整数を表す。
A polyhalogenated phthalocyanine pigment composition characterized by wet-pulverizing a polyhalogenated phthalocyanine and an azo dye derivative represented by the general formula (1) in the presence of an inorganic salt and an organic solvent.
General formula (1)
A and B represent a hydroxyl group or a basic substituent represented by the following general formulas (2) to (3).
General formula (2)
R 1 and R 2 each independently represents a saturated or unsaturated alkyl group which may be substituted, or a heterocyclic ring which may be substituted containing a nitrogen, oxygen or sulfur atom in R 1 or R 2. . However, n represents the integer of 1-10.
A color filter comprising the polyhalogenated phthalocyanine pigment composition according to claim 1 in a green pixel portion.
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