JP3945242B2 - Coloring composition for color filter and color filter - Google Patents
Coloring composition for color filter and color filter Download PDFInfo
- Publication number
- JP3945242B2 JP3945242B2 JP2001382455A JP2001382455A JP3945242B2 JP 3945242 B2 JP3945242 B2 JP 3945242B2 JP 2001382455 A JP2001382455 A JP 2001382455A JP 2001382455 A JP2001382455 A JP 2001382455A JP 3945242 B2 JP3945242 B2 JP 3945242B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- green
- parts
- crude
- color filter
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 77
- 238000004040 coloring Methods 0.000 title description 35
- 239000000049 pigment Substances 0.000 claims description 139
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 claims description 71
- 150000004820 halides Chemical class 0.000 claims description 38
- 229910052751 metal Inorganic materials 0.000 claims description 38
- 239000002184 metal Substances 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 229910052782 aluminium Inorganic materials 0.000 claims description 29
- 239000003086 colorant Substances 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 21
- 229910052802 copper Inorganic materials 0.000 claims description 21
- 239000010949 copper Substances 0.000 claims description 21
- 239000000040 green colorant Substances 0.000 claims description 19
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000001056 green pigment Substances 0.000 description 85
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
- 238000000034 method Methods 0.000 description 38
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 25
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- 239000000460 chlorine Substances 0.000 description 21
- 229910052801 chlorine Inorganic materials 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000576 coating method Methods 0.000 description 16
- -1 polypropylene Polymers 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- 239000001052 yellow pigment Substances 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
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- 230000005540 biological transmission Effects 0.000 description 11
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 125000001246 bromo group Chemical class Br* 0.000 description 10
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- 239000003513 alkali Substances 0.000 description 9
- 229910017053 inorganic salt Inorganic materials 0.000 description 9
- 208000012641 Pigmentation disease Diseases 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 230000019612 pigmentation Effects 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
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- 239000000975 dye Substances 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 239000000025 natural resin Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 238000002834 transmittance Methods 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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 4
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 239000002245 particle Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000001054 red pigment Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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Description
【０００１】
【発明の属する技術分野】
本発明は、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用着色組成物、およびこの着色組成物を用いたカラーフィルタに関する。
【０００２】
【従来の技術】
カラーフィルタは、ガラス等の透明な基板の表面に２種以上の異なる色相の微細な帯（ストライプ）状のフィルタセグメントを平行または交差して配置したもの、あるいは微細なフィルタセグメントを縦横一定の配列で配置したものからなっている。フィルタセグメントは、数ミクロン〜数１００ミクロンと微細であり、しかも色相毎に所定の配列で整然と配置されている。
カラー液晶表示装置に用いられているカラーフィルタの上には、一般に液晶を駆動させるための透明電極が蒸着あるいはスパッタリングにより形成され、さらにその上に液晶を一定方向に配向させるための配向膜が形成されている。これらの透明電極および配向膜の性能を充分に得るには、その形成工程を一般に２００℃以上好ましくは２３０℃以上の高温で行う必要がある。
【０００３】
このため、現在、カラーフィルタの製造方法としては、耐光性、耐熱性に優れる顔料を着色剤とする顔料分散法と呼ばれる方法が主流となっており、主に下記の２通りの方法でカラーフィルタが製造されている。
第１の方法では，感光性透明樹脂溶液中に顔料を分散したものをガラス等の透明基板に塗布し、乾燥により溶剤を除去した後、一つのフィルタ色のパターン露光を行い、次いで未露光部を現像工程で除去して１色目のパターンを形成、必要に応じて加熱等の処理を加えた後、同様の操作を全フィルタ色について順次繰り返すことによりカラーフィルタを製造することができる。
【０００４】
第２の方法では、透明樹脂溶液中に顔料を分散したものをガラス等の透明基板に塗布し、乾燥により溶剤を除去した後、その塗膜上にポジ型レジスト等のレジストを塗布し、一つのフィルタ色のパターン露光を行い、現像してレジストパターンを形成し、これをエッチングレジストとして、レジストパターンの付着していない顔料分散塗膜をエッチング液で除去し，レジスト塗膜を剥離して１色目のパターンを形成、必要により加熱等の処理を加えた後、同様の操作を全フィルタ色について順次繰り返すことによりカラーフィルタを製造することができる。なお、レジストの現像と顔料分散塗膜のエッチングを同時に行うこともできる。
【０００５】
【発明が解決しようとする課題】
上記方法において、緑色フィルタの製造には、従来よりハロゲン化銅フタロシアニングリーン顔料を含む着色組成物が用いられている。銅フタロシアニンには分子構造上１６個のハロゲンが導入でき、塩素のみが導入された C.I. Pigment Green 7 と，臭素と塩素が導入された C.I. Pigment Green 36が知られている。一般に、臭素導入量が多いほど可視光の透過波長領域が長波長側にシフトするが，カラーフィルタの緑色フィルタとしては透過波長領域がより長波長側にあるほうがＸＹＺ表色系の３刺激値の中の明度（Ｙ値）が高くなるため、一般に C.I. Pigment Green 36が用いられている。
【０００６】
しかし，臭素導入量には限界があり，更に明度を向上させるために、より長波長側に透過領域がシフトした緑色着色用組成物が求められていた。
そこで、本発明の目的は、より明度の高い緑色フィルタを与えるカラーフィルタ用着色組成物およびカラーフィルタを提供することにある。
【０００７】
【課題を解決するための手段】
本発明者らは、上記課題を解決するため鋭意検討を重ねた結果、ハロゲン化銅フタロシアニン顔料と、中心金属である銅を積極的に異種金属に置換したハロゲン化異種金属フタロシアニン顔料とを特定の比率で含む着色組成物を用いることにより、透過波長領域が長波長側にシフトし、より明度の高い緑色フィルターが得られることを見出し、本発明に至った。
【０００８】
すなわち、本発明は、透明樹脂、その前駆体またはそれらの混合物からなる着色料担体と、該着色料担体に分散された、１分子内に平均して１２〜１６個の臭素を含むハロゲン化銅フタロシアニン顔料および中心金属がMg,Al,Si,Ti,V,Mn,Fe,Co,Ni,Zn,Ge,Snからなる群から選ばれる少なくとも1 種のハロゲン化異種金属フタロシアニン顔料からなる緑色着色料を含み、かつ該ハロゲン化異種金属フタロシアニン顔料の含有量が、緑色着色料の全量を基準として１〜８０モル％であることを特徴とするカラーフィルタ用着色組成物を提供する。
【０００９】
本発明の着色組成物において、ハロゲン化異種金属フタロシアニン顔料は、１分子内に平均して８〜１６個の臭素を含むことが好ましい。また、本発明は、少なくとも１つの赤色フィルタセグメント、少なくとも１つの青色フィルタセグメント、および少なくとも１つの緑色フィルタセグメントを具備し、該少なくとも１つの緑色フィルタセグメントが上記本発明の着色組成物から形成されているカラーフィルタを提供する。
【００１０】
【発明の実施の形態】
本発明の着色組成物は、透明樹脂、その前駆体またはそれらの混合物からなる着色料担体と、この着色料担体に分散された緑色着色料を含有する。緑色着色料は、ハロゲン化銅フタロシアニン顔料およびハロゲン化異種金属フタロシアニン顔料からなる。着色料担体は、得られる緑色フィルタセグメントにおいて樹脂質バインダーを提供する。
【００１１】
本発明に使用されるハロゲン化銅フタロシアニン顔料として具体的には、臭素と塩素が導入されたC.I. Pigment Green 36 が挙げられる。
本発明に使用されるハロゲン化銅フタロシアニン顔料は、透過波長領域が長波長側になるため、１分子内に平均して１２〜１６個の臭素を含む。
【００１２】
ハロゲン化銅フタロシアニン顔料と共に緑色着色料を構成するハロゲン化異種金属フタロシアニン顔料は、緑色フィルタセグメントの透過波長領域をより長波長側にシフトさせる働きをするものである。ハロゲン化異種金属フタロシアニン顔料の中心金属は、Mg,Al,Si,Ti,V,Mn,Fe,Co,Ni,Zn,Ge,Snから選ばれる少なくとも１種の異種金属である。ハロゲン化異種金属フタロシアニン顔料は、中心金属が異なる２種類以上を混合して用いることもできる。また、中心金属がAl,Si,Ti,V,Mn,Fe,Ge,Snなどの３価または４価の金属の場合、軸置換基が存在する。軸置換基としては、-F, -Cl, -Br, -I等のハロゲン、アルコキシル基、フェノキシ基,=O 等が挙げられるがこれらに限定するものではない。
【００１３】
ハロゲン化異種金属フタロシアニン顔料のハロゲンは全て塩素でもよいが、透過波長領域がより長波長側にあるため、臭素が導入されたハロゲン化銅フタロシアニン顔料が好適に用いられる。ハロゲン化異種金属フタロシアニン顔料は、透過波長領域が長波長側になるため、１分子内に平均して８〜１６個の臭素を含むことが好ましく、平均して１２〜１６個のより臭素を含むことがより好ましい。
【００１４】
本発明において、ハロゲン化異種金属フタロシアニン顔料の含有量は、緑色着色料（ハロゲン化銅フタロシアニン＋ハロゲン化異種金属フタロシアニン顔料）の全量を基準として、１〜８０モル％、好ましくは５〜６０モル％、さらに好ましくは９〜４５モル％である。ハロゲン化異種金属フタロシアニン顔料の含有量が１モル％未満の場合は、透過波長領域が長波長側にならず、ハロゲン化異種金属フタロシアニン顔料の含有量が８０モル％を越えると、透過波長領域がより長波長側になるが緑色としては色が薄くなり彩度が低くなるため、本発明には不適当である。
【００１５】
本発明に使用される緑色着色料は、例えば、粗製異種金属フタロシアニン顔料を既知の方法でハロゲン化したものと粗製ハロゲン化銅フタロシアニン顔料を混合する方法や、異種金属化合物の存在下で粗製銅フタロシアニン顔料をハロゲン化することにより、銅の一部が異種金属で置換された粗製ハロゲン化（銅／異種金属）フタロシアニン顔料を合成する方法等により製造することができる。また、粗製ハロゲン化銅フタロシアニン顔料の銅の一部を異種金属で置換する方法によっても製造することができる。
【００１６】
上記方法で得られた粗製ハロゲン化（銅／異種金属）フタロシアニン顔料は粒子の形状が無定形に近く、このままでは分散が困難であるため、既知の方法で結晶成長させることが好ましい。結晶成長させる方法としては、無定形の上記粗製ハロゲン化（銅／異種金属）フタロシアニン顔料を有機溶剤中に分散し、加熱することにより結晶成長させる方法、および機械的なシェアを加えながら加熱して結晶成長させる方法などがある（以後これらの工程を顔料化処理と呼ぶ）。
【００１７】
具体的には、前者の顔料化処理方法の一例として、無定形の粗製ハロゲン化（銅／異種金属）フタロシアニン顔料を約５〜３０重量倍のキシレンと混合し、攪拌しながらキシレン還流下で煮沸することにより結晶成長させる方法が挙げられる。また、後者の顔料化処理方法の一例としては、無定形の粗製ハロゲン化（銅／異種金属）フタロシアニン顔料と水溶性無機塩と少量の水溶性有機溶剤の混合物を、ニーダーを用いて加熱しながら混練することにより結晶成長させる、ソルトミリングと呼ばれる方法が挙げられる。ただし、カラーフィルタには透明性が要求されるため、上記顔料化処理による結晶成長は、得られる顔料の一次粒子の平均粒径が０．１μｍ以下、特に０．０５μｍ以下になる程度にとどめることが好ましい。
【００１８】
顔料化処理に用いられる溶剤としては、上記キシレンの他に、トルエン、エチルベンゼン、ジエチルベンゼン、メチルシクロヘキサン、エチルシクロヘキサン等の炭化水素系溶剤、トリクロロエタン、テトラクロロエタン、トリクロロプロパン、モノクロロベンゼン、ジクロロベンゼン、トリクロロベンゼン、クロロトルエン等のハロゲン化炭化水素系溶剤、ブチルアルコール、イソペンチルアルコール、ヘキサノール、２−エチル−１−ヘキサノール、ベンジルアルコール、シクロヘキサノール、エチレングリコール、プロピレングリコール等のアルコール系溶剤、フェノール、クレゾール等のフェノール系溶剤、ジブチルエーテル、アニソール、ジオキサン、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル等のエーテル系溶剤、ブチルメチルケトン、イソブチルケトン、シクロヘキサノン、メチルシクロヘキサノン、アセトフェノン等のケトン系溶剤、酢酸プロピル、酢酸ブチル、酢酸イソブチル、酢酸イソペンチル、３−メトキシブチルアセタート、２−エチルブチルアセタート、２−エチルヘキシルアセタート、プロピオン酸ブチル、安息香酸エチル、マレイン酸ジエチル、エチレングリコールモノアセタート等のエステル系溶剤、ニトロベンゼン、Ｎ−メチルアニリン、ピペリジン、ピリジン、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチル−２−ピロリドン、エチルセロソルブ、ブチルセロソルブ、エチルカルビトール等の溶剤をあげることができる。これらの溶剤は単独でまたは混合して用いることができる。また、非水溶性の溶剤を活性剤で水に分散したエマルジョンを用いることもできる。
【００１９】
上記ソルトミリングは、粗製顔料と水溶性無機塩および水溶性有機溶剤を混合して、加熱しながら混練した後、水洗により無機塩と高沸点溶剤を除去することによって顔料化処理する方法である。水溶性無機塩は、破砕助剤として働くものであり、ソルトミリング時に無機塩の硬度の高さを利用して粗製顔料が破砕され、それにより活性面が生じて、結晶成長がおこると考えられている。従って、混練時は粗製顔料の破砕と結晶成長が同時に起こり、混練条件により得られる顔料の一次粒子径が異なる。ソルトミリングで顔料化処理を行う場合には、加熱により結晶成長を促進する必要があり、加熱温度は７０〜１５０℃が好ましい。加熱温度が７０℃未満の場合は、結晶成長が十分に起こらず、顔料粒子の形状が無定形に近くなるため好ましくない。一方、加熱温度が１５０℃を越える場合は、結晶成長が進みすぎ、顔料の一次粒子径が大きくなるため、カラーフィルタ用着色組成物の着色料としては好ましくない。
【００２０】
ソルトミリングにおいて水溶性無機塩としては、塩化ナトリウム、塩化バリウム、塩化カリウム、硫酸ナトリウム等を用いることができるが、価格の点から塩化ナトリウム（食塩）を用いるのが好ましい。ソルトミリングする際に用いる無機塩の量は、処理効率と生産効率の両面から、粗製顔料の０．５〜２０重量倍、特に１〜１０重量倍であることが好ましい。
【００２１】
水溶性有機溶剤は、粗製顔料および水溶性無機塩を湿潤する働きをするものであり、水に溶解（混和）し、かつ用いる無機塩を実質的に溶解しないものであれば特に限定されない。但し、ソルトミリング時に温度が上昇し、溶剤が蒸発し易い状態になるため、安全性の点から、沸点１２０℃以上の高沸点溶剤が好ましい。水溶性有機溶剤としては、例えば、２−メトキシエタノール、２−ブトキシエタノール、２−（イソペンチルオキシ）エタノール、２−（ヘキシルオキシ）エタノール、ジエチレングリコール、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液状のポリエチレングリコール、１−メトキシ−２−プロパノール、１−エトキシ−２−プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、液状のポリプロピレングリコール等が用いられる。
【００２２】
ソルトミリング時には、顔料化処理後に得られる顔料を乾燥する際の強い凝集を防止し、容易に透明樹脂に分散できるようにするため、樹脂を併用することができる。ソルトミリング時に樹脂を併用することにより、柔らかい粉体顔料を得ることができる。ソルトミリングに用いる樹脂としては、室温で固体で、水不溶性で、かつ上記有機溶剤に少なくとも一部可溶であるものが好ましく、天然樹脂、変性天然樹脂、合成樹脂、天然樹脂で変性された合成樹脂等が用いられる。天然樹脂としてはロジンが代表的で、変性天然樹脂としてはロジン誘導体、繊維素誘導体、ゴム誘導体、タンパク誘導体およびそれらのオリゴマーが用いられる。合成樹脂としては、エポキシ樹脂、アクリル樹脂、マレイン酸樹脂、ブチラール樹脂、ポリエステル樹脂、メラミン樹脂、フェノール樹脂、ポリウレタン樹脂、ポリアマイド樹脂等が挙げられる。天然樹脂で変性された合成樹脂としてはロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂等が挙げられる。樹脂の使用量は、粗製顔料に対して５〜１００重量％の範囲であることが好ましい。
【００２３】
ソルトミリング時には、上記樹脂の他に、顔料分散助剤、可塑剤等の添加剤、あるいは一般に体質顔料として知られている炭酸カルシウム、硫酸バリウム、シリカ等の無機顔料を併用してもよい。また、色相を調整するために他の顔料と混合して処理を行ってもよい。
【００２４】
本発明の緑色着色料を分散させる着色料担体は、上述したように、透明樹脂、その前駆体またはそれらの混合物により構成される。透明樹脂は、可視光領域の４００〜７００ｎｍの全波長領域において透過率が好ましくは８０％以上、より好ましくは９５％以上の樹脂である。透明樹脂には、熱可塑性樹脂、熱硬化性樹脂、および感光性樹脂が含まれ、その前駆体には、放射線照射により硬化して透明樹脂を生成するモノマーもしくはオリゴマーが含まれ、これらを単独または２種以上混合して用いることができる。
本発明のカラーフィルタ用着色組成物には、該組成物を紫外線照射により硬するときには、光開始剤等が添加される。
【００２５】
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、塩化ビニルー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、フェノール樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、スチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム、セルロース類、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、メラミン樹脂、尿素樹脂等が挙げられる。
【００２６】
感光性樹脂としては、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線状高分子にイソシアネート基、アルデヒド基、エポキシ基等の反応性置換基を有する（メタ）アクリル化合物やケイヒ酸を反応させて、（メタ）アクリロイル基、スチリル基等の光架橋性基を該線状高分子に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ものも用いられる。
【００２７】
モノマーおよび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、メラミン（メタ）アクリレート、エポキシ（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、（メタ）アクリル酸、スチレン、酢酸ビニル、（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、アクリロニトリル等が挙げられる。
【００２８】
光開始剤としては、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−オン等のアセトフェノン系光開始剤、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開始剤およびボレート系光開始剤、カルバゾール系光開始剤、イミダゾール系光開始剤等が用いられる。
【００２９】
上記光開始剤は、単独あるいは２種以上混合して用いるが、増感剤として、α−アシロキシムエステル、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。
【００３０】
本発明のカラーフィルタ用着色組成物は、ハロゲン化銅フタロシアニン顔料およびハロゲン化異種金属フタロシアニン顔料からなる緑色着色料を、必要に応じて上記光開始剤と共に、着色料担体中に、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用いて微細に分散して製造することができる。また、本発明のカラーフィルタ用着色組成物は、ハロゲン化銅フタロシアニン顔料とハロゲン化異種金属フタロシアニン顔料とを別々に着色料担体に分散したものを、ハロゲン化異種金属フタロシアニン顔料の含有量が上記比率となるよう混合して製造することもできる。
【００３１】
顔料を着色料担体中に分散する際には、適宜、樹脂型顔料分散剤、界面活性剤、色素誘導体等の分散助剤を含有させることができる。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ので、分散助剤を用いて顔料を着色料担体中に分散してなる着色組成物を用いた場合には、透明性に優れたカラーフィルタが得られる。
【００３２】
樹脂型顔料分散剤は、顔料に吸着する性質を有する顔料親和性部位と、着色料担体と相溶性のある部位とを有し、顔料に吸着して顔料の着色料担体への分散を安定化する働きをするものである。樹脂型顔料分散剤として具体的には、ポリウレタン、ポリアクリレートなどのポリカルボン酸エステル、不飽和ポリアミド、ポリカルボン酸、ポリカルボン酸（部分）アミン塩、ポリカルボン酸アンモニウム塩、ポリカルボン酸アルキルアミン塩、ポリシロキサン、長鎖ポリアミノアマイドリン酸塩、水酸基含有ポリカルボン酸エステルや、これらの変性物、ポリ（低級アルキレンイミン）と遊離のカルボキシル基を有するポリエステルとの反応により形成されたアミドやその塩などの油性分散剤；（メタ）アクリル酸−スチレン共重合体、（メタ）アクリル酸−（メタ）アクリル酸エステル共重合体、スチレン−マレイン酸共重合体、ポリビニルアルコール、ポリビニルピロリドンなどの水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート系、エチレンオキサイド／プロピレンオキサイド付加化合物、燐酸エステル系等が用いられ、これらは単独でまたは２種以上を混合して用いることができる。
【００３３】
界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ソーダ、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどのアニオン性界面活性剤；ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレートなどのノニオン性界面活性剤；アルキル４級アンモニウム塩やそれらのエチレンオキサイド付加物などのカオチン性界面活性剤；アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤が挙げられ、これらは単独でまたは２種以上を混合して用いることができる。
【００３４】
色素誘導体は、有機色素に置換基を導入した化合物であり、本発明に用いられる色素誘導体は色相の関係から緑色または黄色であることが好ましいが、添加量が少なければ青色のものを用いても良い。有機色素には、一般に色素とは呼ばれていないナフタレン系、アントラキノン系等の淡黄色の芳香族多環化合物も含まれる。色素誘導体としては、特開昭６３−３０５１７３号公報、特公昭５７−１５６２０号公報、特公昭５９−４０１７２号公報、特公昭６３−１７１０２号公報、特公平５−９４６９号公報等に記載されているものを使用でき、これらは単独でまたは２種類以上を混合して用いることができる。
【００３５】
また、本発明のカラーフィルタ用着色組成物には、緑色フィルタに要求されるスペクトルを実現するため黄色顔料を含有させることが好ましい。黄色顔料は特に限定されないが、要求スペクトルに合い、かつ緒耐性に優れた顔料を選択するのが好ましい。具体的には、C.I. Pigment Yellow １、２、３、４、５、６、１０、１２、１３、１４、１５、１６、１７、１８、２４、３１、３２、３４、３５、３５：１、３６、３６：１、３７、３７：１、４０、４２、４３、５３、５５、６０、６１、６２、６３、６５、７３、７４、７７、８１、８３、９３、９４、９５、９７、９８、１００、１０１、１０４、１０６、１０８、１０９、１１０、１１３、１１４、１１５、１１６、１１７、１１８、１１９、１２０、１２６、１２７、１２８、１２９、１３８、１３９、１５０、１５１、１５２、１５３、１５４、１５５、１５６、１６１、１６２、１６４、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７９、１８０、１８１、１８２、１８５、１８７、１９９などが挙げられる。
これらは、単独でまたは２種類以上を混合して用いることができる。黄色顔料は、単独で着色料担体中に分散して黄色の着色組成物とし、上記緑色着色料を着色料担体中に分散してなる緑色の着色組成物と配合して用いるか、上記緑色着色料と混合して着色料担体中に分散して用いる。
【００３６】
さらに、本発明のカラーフィルタ用着色組成物には、顔料を充分に着色料担体中に分散させ、ガラス基板等の透明基板上に乾燥膜厚が０．２〜５μｍとなるように塗布して緑色フィルタセグメントを形成することを容易にするために溶剤を含有させることができる。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。
【００３７】
また、本発明のカラーフィルタ用着色組成物には、組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。貯蔵安定剤としては、例えばベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの４級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、ｔ−ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。
【００３８】
本発明のカラーフィルタ用着色組成物は、グラビアオフセット用印刷インキ、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材の形態で調製することができる。着色レジスト材は、熱可塑性樹脂、熱硬化性樹脂または感光性樹脂とモノマー、光開始剤を含有する組成物中に本発明の緑色着色料を分散させたものである。
【００３９】
本発明の緑色着色料および必要に応じて用いられる黄色顔料は、好ましくは、緑色フィルタセグメントをフォトリソグラフ法により形成する場合には、緑色着色料と黄色顔料を合計して着色組成物中に１．５〜７重量％の割合で含有され、緑色フィルタセグメントを印刷法により形成する場合には、緑色着色料と黄色顔料を合計して着色組成物中に１．５〜４０重量％の割合で含有される。いずれにせよ、顔料（緑色着色料＋黄色顔料）は、最終緑色フィルタセグメント中に好ましくは１０〜５５重量％、より好ましくは２０〜５０重量％の割合で含有され、その残部は、着色料担体により提供される樹脂質バインダーから実質的になる。緑色着色料と黄色顔料の重量比は、１：１〜２．５：１であることが好ましい。従って、最終緑色フィルタセグメント中に含まれる緑色着色料の量は、５〜３９重量％であることが好ましい。
【００４０】
本発明のカラーフィルタ用着色組成物は、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の除去を行うことが好ましい。
【００４１】
記述のように、本発明のカラーフィルタは、少なくとも１つの赤色フィルタセグメント、少なくとも１つの青色フィルタセグメント、および少なくとも１つの緑色フィルタセグメントを具備し、ここで、緑色フィルタセグメントは本発明の着色組成物を用いて形成される。赤色フィルタセグメントおよび青色フィルタセグメントは、通常の赤色の着色組成物および通常の青色の着色組成物を用いてそれぞれ形成することができる。
【００４２】
赤色の着色組成物は、本発明の緑色着色料の代わりに、赤色顔料を用いて得られる組成物である。赤色顔料としては、C.I. Pigment Red ７、１４、４１、４８：１、４８：２、４８：３、４８：４、１４６、１７７、１７８、１８４、１８５、１８７、２００、２０２、２０８、２１０、２４６、２５４、２５５、２６４、２７２を使用することができる。
【００４３】
また、青色の着色組成物は、本発明の緑色着色料の代わりに、例えばC.I. Pigment Blue １５、１５：１、１５：２、１５：３、１５：４、１５：６、１６、６０等の青色顔料、および必要に応じ調色用として、C.I. Pigment Violet １９、２３、２７、３２、４２等の紫色顔料や上記黄色顔料を用いて得られる組成物である。
【００４４】
本発明のカラーフィルタは、印刷法またはフォトリソグラフィー法により、本発明の着色組成物を用いて透明基板上に各色のフィルタセグメントを形成することにより製造することができる。
透明基板としては、ガラス板や、ポリカーボネート、ポリメタクリル酸メチル、ポリエチレンテレフタレートなどの樹脂板が用いられる。
【００４５】
印刷法による各色フィルタセグメントの形成は、上記各種の印刷インキとして調製した着色組成物の印刷と乾燥を繰り返すだけでパターン化ができるため、カラーフィルタの製造法としては、低コストで量産性に優れている。さらに、印刷技術の発展により高い寸法精度および平滑度を有する微細パターンの印刷を行うことができる。印刷を行うためには、印刷の版上にて、あるいはブランケット上にてインキが乾燥、固化しないような組成とすることが好ましい。また、印刷機上でのインキの流動性の制御も重要であり、分散剤や体質顔料によるインキ粘度の調整を行うこともできる。
【００４６】
フォトリソグラフィー法により各色フィルタセグメントを形成する場合は、上記溶剤現像型あるいはアルカリ現像型着色レジスト材として調製した着色組成物を、透明基板上に、スプレーコートやスピンコート、スリットコート、ロールコート等の塗布方法により、乾燥膜厚が０．２〜５μｍとなるように塗布する。必要により乾燥された膜には、この膜と接触あるいは非接触状態で設けられた所定のパターンを有するマスクを通して紫外線露光を行う。その後、溶剤またはアルカリ現像液に浸漬するかもしくはスプレーなどにより現像液を噴霧して未硬化部を除去して所望のパターンを形成したのち、同様の操作を他色について繰り返してカラーフィルタを製造することができる。さらに、着色レジスト材の重合を促進するため、必要に応じて加熱を施すこともできる。フォトリソグラフィー法によれば、上記印刷法より精度の高いカラーフィルタが製造できる。
【００４７】
現像に際しては、アルカリ現像液として炭酸ナトリウム、水酸化ナトリウム等の水溶液が使用され、ジメチルベンジルアミン、トリエタノールアミン等の有機アルカリを用いることもできる。また、現像液には、消泡剤や界面活性剤を添加することもできる。
なお、紫外線露光感度を上げるために、上記着色レジスト材を塗布乾燥後、水溶性あるいはアルカリ水溶性樹脂、例えばポリビニルアルコールや水溶性アクリル樹脂等を塗布乾燥し酸素による重合阻害を防止する膜を形成した後、紫外線露光を行うこともできる。
【００４８】
本発明のカラーフィルタは、上記方法の他に電着法、転写法などにより製造することができるが、本発明の着色組成物は、いずれの方法にも用いることができる。なお、電着法は、透明基板上に形成した透明導電膜を利用して、コロイド粒子の電気泳動により各色フィルタセグメントを透明導電膜の上に電着形成することでカラーフィルタを製造する方法である。また、転写法は剥離性の転写ベースシートの表面に、あらかじめカラーフィルタ層を形成しておき、このカラーフィルタ層を所望の透明基板に転写させる方法である。
【００４９】
【実施例】
以下に、本発明を実施例に基づいて説明するが、本発明はこれによって限定されるものではない。なお、実施例および比較例中、「部」とは「重量部」を、「％」とは「モル％」をそれぞれ意味する。
まず、実施例および比較例に用いたアクリル樹脂溶液、粗製緑色顔料、緑色顔料について説明する。
【００５０】
（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
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。
【００５１】
以下に、粗製緑色顔料の合成法を記す。なお、合成した粗製顔料中の金属の測定は、以下の方法で行った。まず、１００ｍｌビーカーに粗製顔料０．５ｇ，硫酸１ｍｌ，および硝酸３ｍｌを入れ、ガスコンロで１時間３０分加熱して分解後、６００℃の電気炉で４時間加熱して分解した。分解物に、塩酸５ｍｌおよび純水２５ｍｌ入れて溶解し、溶解物を５０ｍｌに定容し、ＩＣＰ原子発光分光分析により金属原子量を測定した。また、粗製顔料中の塩素、臭素の数（１分子内に含まれる平均塩素数および平均臭素数）は、Ｎｏ．６の濾紙に粗製顔料０．０１ｇを包み、過酸化水素５滴を滴下して、酸素置換した燃焼フラスコ中で燃焼した。燃焼後１００ｍｌに定容し、イオンクロマトグラフ分析により測定した。
【００５２】
［粗製緑色顔料１］
塩化アルミニウム４２９部および塩化ナトリウム９６部の１４０℃の溶融塩に、銅フタロシアニン６４部およびアルミニウムフタロシアニン５部を溶解し、温度を保ったまま２時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり４８部で５時間滴下した。その後、塩素を１時間あたり３０部で２時間導入した。この反応液を水４０００部に徐々に注入したのち、濾過、水洗して１９７．２部の粗製緑色顔料１を得た。得られた粗製緑色顔料１は、粗製ハロゲン化銅フタロシアニン顔料９０．５％および粗製ハロゲン化アルミニウムフタロシアニン顔料９．５％からなり、粗製ハロゲン化銅フタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であり、粗製ハロゲン化アルミニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５３】
［粗製緑色顔料２］
塩化アルミニウム４２９部および塩化ナトリウム９６部の１６０℃の溶融塩に、銅フタロシアニン６９部を溶解し、温度を２００℃に昇温して２時間攪拌した。反応温度を１８０℃に下げ、臭素を１時間あたり４８部で５時間滴下した。その後、塩素を１時間あたり３０部で２時間導入した。この反応液を水４０００部に徐々に注入したのち、濾過、水洗して１９６．６部の粗製緑色顔料２を得た。得られた粗製緑色顔料２は、粗製ハロゲン化銅フタロシアニン顔料５８．０％および粗製ハロゲン化アルミニウムフタロシアニン顔料４２．０％からなり、粗製ハロゲン化銅フタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であり、粗製ハロゲン化アルミニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５４】
［粗製緑色顔料３］
塩化アルミニウム４２９部および塩化ナトリウム９６部の１４０℃の溶融塩に、アルミニウムフタロシアニン６５部を溶解し、温度を保ったまま２時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり４８部で５時間滴下した。その後、塩素を１時間あたり３０部で２時間導入した。この反応液を水４０００部に徐々に注入したのち、濾過、水洗して１９３．５部の粗製緑色顔料３を得た。得られた粗製緑色顔料３は、粗製ハロゲン化アルミニウムフタロシアニン顔料のみからなり、１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５５】
［粗製緑色顔料４］
塩化アルミニウム４２９部および塩化ナトリウム９６部の１３０℃の溶融塩に、銅フタロシアニン６５部を溶解し、温度を保ったまま２時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり４８部で５時間滴下した。その後、塩素を１時間あたり３０部で２時間導入した。この反応液を水４０００部に徐々に注入したのち、濾過、水洗して１９３．５部の粗製緑色顔料４を得た。得られた粗製緑色顔料４は、粗製ハロゲン化銅フタロシアニン顔料９７％および粗製ハロゲン化アルミニウムフタロシアニン顔料３％からなり、粗製ハロゲン化銅フタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であり、粗製ハロゲン化アルミニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５６】
［粗製緑色顔料５］
ビフェニル２５５部およびナフタリン４５部、 フタロジニトル１２８部、 四塩化チタン４８部、 ピリジン２部を混合して２００℃に加熱・ 反応後、 ろ過、 乾燥粉砕して粗製チタニウムフタロシアニンを得た。 次いで、塩化アルミニウム２００部および塩化ナトリウム４０部を加熱して１２０℃の共融塩とした後、 粗製チタニウムフタロシアニン４０部を添加し３０分撹拌した。 反応温度を１８０℃に上げ、臭素を１時間あたり３０部で５時間滴下した。その後、塩素を１時間あたり２０部で２時間導入した。この反応液を水２５００部に徐々に注入したのち、濾過、水洗して粗製緑色顔料５を得た。得られた粗製緑色顔料５は、粗製ハロゲン化チタニウムフタロシアニン顔料５８．０％および粗製ハロゲン化アルミニウムフタロシアニン顔料４２．０％からなり、粗製ハロゲン化チタニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であり、粗製ハロゲン化アルミニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５７】
［粗製緑色顔料６］
塩化アルミニウム８０部、塩化ナトリウム１０部および硫酸ナトリウム１０部の１５０℃の溶融塩に、銅フタロシアニン２０部を溶解し、反応温度を１６０℃に昇温し、臭素を１時間あたり７．４部で６時間滴下した。その後、反応液を１８０℃に昇温し、塩素を１時間あたり４部で５時間導入した。この反応液を水１０００部に徐々に注入したのち、濾過、水洗して４５．４部の粗製緑色顔料６を得た。得られた粗製緑色顔料６は、粗製ハロゲン化銅フタロシアニン顔料９９．９％および粗製ハロゲン化アルミニウムフタロシアニン顔料０．１％からなり、粗製ハロゲン化銅フタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であり、粗製ハロゲン化アルミニウムフタロシアニン顔料１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
【００５８】
次に、下記の方法で粗製緑色顔料を顔料化処理し、緑色顔料を製造した。
［緑色顔料１］
粗製緑色顔料４：５００部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダー（井上製作所製）に仕込み、１２０℃で４時間混練した。次にこの混練物を５リットルの温水に投入し、７０℃に加熱しながら１時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、８０℃で一昼夜乾燥し、４９０部の緑色顔料１を得た。なお、緑色顔料１は、ハロゲン化銅フタロシアニン顔料９７％およびハロゲン化アルミニウムフタロシアニン顔料３％からなるものであった。
【００５９】
［緑色顔料２］
粗製緑色顔料４：３４５部、粗製緑色顔料１：１５５部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダー（井上製作所製）に仕込み、１２０℃で４時間混練した。つぎにこの混練物を５リットルの温水に投入し、７０℃に加熱しながら１時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、８０℃で一昼夜乾燥、４９０部の緑色顔料２を得た。なお、緑色顔料２は、ハロゲン化銅フタロシアニン顔料９５％およびハロゲン化アルミニウムフタロシアニン顔料５％からなるものであった。
【００６０】
［緑色顔料３］
粗製緑色顔料１：５００部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料３を得た。なお、緑色顔料３は、ハロゲン化銅フタロシアニン顔料９０．５％およびハロゲン化アルミニウムフタロシアニン顔料９．５％からなるものであった。
【００６１】
［緑色顔料４］
粗製緑色顔料４：２８２部、粗製緑色顔料２：２１８部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料４を得た。なお、緑色顔料４は、ハロゲン化銅フタロシアニン顔料７９．０％およびハロゲン化アルミニウムフタロシアニン顔料２１．０％からなるものであった。
【００６２】
［緑色顔料５］
粗製緑色顔料４：１５４部、粗製緑色顔料２：３４６部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料５を得た。なお、緑色顔料５は、ハロゲン化銅フタロシアニン顔料７０．０％およびハロゲン化アルミニウムフタロシアニン顔料３０．０％からなるものであった。
【００６３】
［緑色顔料６］
粗製緑色顔料２：５００部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料６を得た。なお、緑色顔料６は、ハロゲン化銅フタロシアニン顔料５８．０％およびハロゲン化アルミニウムフタロシアニン顔料４２．０％からなるものであった。
【００６４】
［緑色顔料７］
粗製緑色顔料４：４１０部、粗製緑色顔料５：９０部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料７を得た。なお、緑色顔料７は、ハロゲン化銅フタロシアニン顔料７９．５％、ハロゲン化アルミニウムフタロシアニン顔料１０．０％およびハロゲン化チタニウムフタロシアニン顔料１０．５％からなるものであった。
【００６５】
［緑色顔料８］
粗製緑色顔料６：５００部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料８を得た。なお、緑色顔料８は、ハロゲン化銅フタロシアニン顔料９９．９％およびハロゲン化アルミニウムフタロシアニン顔料０．１％からなるものであった。
【００６６】
［緑色顔料９］
粗製緑色顔料３：４５０部、粗製緑色顔料６：５０部、塩化ナトリウム：５００部、およびジエチレングリコール：２５０部をステンレス製１ガロンニーダーに仕込み、緑色顔料１と同様の操作を行い、４９０部の緑色顔料９を得た。なお、緑色顔料９は、ハロゲン化銅フタロシアニン顔料９．９％およびハロゲン化アルミニウムフタロシアニン顔料９０．１％からなるものであった。
【００６７】
次に、これらの緑色顔料を用いて、ハロゲン化銅フタロシアニン顔料とハロゲン化異種金属フタロシアニン顔料の配合比を変えた緑色の感光性着色組成物（レジスト材）を作製した。
【００６８】
［実施例１］
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アルカリ現像型感光性着色組成物を作製した。
緑色顔料１ ４．５部
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
【００６９】
［実施例２〜７］
緑色顔料１を緑色顔料２〜７に変えた以外は、実施例１と同様にしてアルカリ現像型感光性着色組成物を作製した。
［比較例１］
緑色顔料１を緑色顔料８に変えた以外は、実施例１と同様にしてアルカリ現像型感光性着色組成物を作製した。
［比較例２］
緑色顔料１を緑色顔料９に変えた以外は、実施例１と同様にしてアルカリ現像型感光性着色組成物を作製した。
【００７０】
実施例１〜７および比較例１〜２で得られ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、１５００ｒｐｍ、２０００ｒｐｍの回転数で塗布し、膜厚が異なる４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２３０℃で１時間加熱、放冷後、得られた緑色塗膜のＣ光源での色度（Ｙ，ｘ，ｙ）を顕微分光光度計（オリンパス光学社製「ＯＳＰ−ＳＰ１００」）を用いて測定した。４組の色度・分光測定結果から、４００〜７００ｎｍ波長の分光透過率の最小値が１％になる時の最大透過率（Tmax) 、ｘおよびｙを求めた。さらに１０００ｒｐｍの塗布基板の表面状態を光学顕微鏡（オリンパス光学社製「ＢＸ６０」）で観察した。結果を表１に示す。
【００７１】
【表１】
表１に示すように、本発明の着色組成物を用いて得られた緑色塗膜は、いずれも色度ｘが０．２５〜０．３４の範囲および色度ｙが０．４３〜０．５８の範囲のときに、明度Ｙが大きく、また、ハロゲン化アルミニウムフタロシアニン顔料の含有量が８０モル％以下の範囲内では、ハロゲン化アルミニウムフタロシアニン顔料の含有量が多いほど明度が大きくなっている。これに対して、ハロゲン化アルミニウムフタロシアニン顔料の含有量が０．１％と本発明の範囲より少ない比較例１の緑色塗膜は明度が小さい。また、ハロゲン化アルミニウムフタロシアニン顔料の含有量が９０％と本発明の範囲より多い比較例２の緑色塗膜は、明度Ｙは６７と大きな値を示すが、y が０．４１７５と小さい値を示すので緑色としては色が薄く、緑色フィルターセグメントとしては適していない。
【００７３】
次に、調色するために、緑色顔料と黄色顔料（C.I. Pigment Yellow 150 ）を併用して、緑色の感光性着色組成物（レジスト材）を作製した。
［実施例８］
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アルカリ現像型感光性着色組成物を作製した。
緑色顔料１ ３．６部
黄色顔料（ＰＹ１５０） ０．９部
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
【００７４】
［実施例９〜１３］
緑色顔料の種類、および緑色顔料と黄色顔料の割合（重量比）を表２に記載したように変えた以外は、実施例８と同様にしてアルカリ現像型感光性着色組成物を作製した。
【００７５】
実施例８〜１３で得られ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、ｘ＝０．３１７２、ｙ＝０．４７０３になるような膜厚に塗布した。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２３０℃で１時間加熱して放冷後、顕微分光光度計（オリンパス光学社製「ＯＳＰ−ＳＰ１００」）を用いて、得られた緑色塗膜のＤ６５光源での明度（Ｙ）、最大透過率（Tmax) 、最小透過率(Tmin)、コントラストを求めた。さらに塗膜の表面状態を光学顕微鏡（オリンパス光学社製「ＢＸ６０」）で観察した。結果を表２に示す。
【００７６】
【表２】
表２に示すように、本発明の着色組成物を用いて得られた緑色塗膜は、ｘとｙ（色相）を黄色顔料によって合わせた場合においても、ハロゲン化アルミニウムフタロシアニン顔料の含有量が多いほど明度が大きくなる。また、ハロゲン化アルミニウムフタロシアニン顔料の含有量が８０モル％以下の範囲内では、ハロゲン化アルミニウムフタロシアニン顔料の含有量が多いほど、調色に用いる黄色顔料の量が少なくすみ、それとともにコントラストが向上している。
【００７８】
次に、緑色感光性着色組成物と同様にして、下記組成の青色感光性着色組成物および緑色感光性着色組成物を調製し、該２種の着色組成物および実施例１〜１３で得られた緑色感光性着色組成物を用いて、下記の方法でカラーフィルタを作製した。
［青色感光性着色組成物］
青色顔料：C.I. Pigment Blue １５：６ ４．５部
（東洋インキ製造社製「リオノールブルー ＥＳ」）
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
【００７９】
［赤色感光性着色組成物］
赤色顔料：C.I. Pigment Red 254 ４．０部
（チバガイギー社製「イルガフォーレッド Ｂ−ＣＦ」）
赤色顔料：C.I. Pigment Red 177 ０．５部
（チバガイギー社製「クロモフタールレッド Ａ２Ｂ」）
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
【００８０】
ガラス基板の一方の表面上に、上記感光性着色組成物をスピンコーターを用いて塗布し、７０℃、２０分熱風オーブンで乾燥した後、幅１００μｍのストライプ状の開口部を有するフォトマスクを介して紫外線露光し、５重量％炭酸ナトリウム水溶液で未露光部を洗い流し、２３０℃、３０分熱風オーブンでベークして、１００μｍ幅のストライプ状の赤色フィルタセグメント、青色フィルタセグメントおよび緑色フィルタセグメントを具備するカラーフィルタを作製した。
得られたカラーフィルタは、すべて白色の明度が高かった。
【００８１】
【発明の効果】
本発明の着色組成物は、ハロゲン化銅フタロシアニン顔料とハロゲン化異種金属フタロシアニン顔料とを特定の比率で含有することにより、透過波長領域が長波長側にシフトしているため、極めて明度の高い緑色フィルタセグメントを基板上に形成することができる。
本発明の着色組成物を用いて形成される緑色フィルタセグメントを具備するカラーフィルタは、カラー液晶表示装置に高明度と高彩度とを同時に付与することができ、透過型・反射型のカラー液晶表示装置ならびに固体撮像素子の色分解用カラーフィルターとして好適である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a colored composition for a color filter used for a color liquid crystal display device or a solid-state imaging device, and a color filter using the colored composition.
[0002]
[Prior art]
A color filter has two or more kinds of fine band (striped) filter segments arranged in parallel or intersecting with each other on the surface of a transparent substrate such as glass, or the fine filter segments are arranged vertically and horizontally. It is made up of those arranged in The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.
On the color filter used in the color liquid crystal display device, a transparent electrode for driving the liquid crystal is generally formed by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed thereon. Has been. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, it is necessary to perform the formation process at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher.
[0003]
Therefore, at present, as a method for producing a color filter, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used. The color filter is mainly produced by the following two methods. Is manufactured.
In the first method, a dispersion of a pigment in a photosensitive transparent resin solution is applied to a transparent substrate such as glass, the solvent is removed by drying, a pattern exposure of one filter color is performed, and then an unexposed portion is obtained. The color filter can be manufactured by repeating the same operation for all the filter colors in order after forming a first color pattern by applying a process such as heating if necessary.
[0004]
In the second method, a dispersion of a pigment in a transparent resin solution is applied to a transparent substrate such as glass, the solvent is removed by drying, and then a resist such as a positive resist is applied on the coating film. Two filter color patterns are exposed and developed to form a resist pattern. Using this as an etching resist, the pigment-dispersed coating film without the resist pattern is removed with an etching solution, and the resist coating film is peeled off. A color filter can be manufactured by forming a color pattern and, if necessary, applying a treatment such as heating, and then repeating the same operation for all filter colors. Note that the development of the resist and the etching of the pigment-dispersed coating film can be performed simultaneously.
[0005]
[Problems to be solved by the invention]
In the above method, a colored composition containing a copper halide phthalocyanine green pigment has been conventionally used for producing a green filter. Copper phthalocyanine is known to be CI Pigment Green 7 into which 16 halogens can be introduced due to its molecular structure and into which only chlorine is introduced, and CI Pigment Green 36 into which bromine and chlorine are introduced. In general, as the amount of bromine introduced increases, the transmission wavelength region of visible light shifts to the longer wavelength side. However, as the green filter of the color filter, the tristimulus value of the XYZ color system has a longer transmission wavelength region. CI Pigment Green 36 is generally used because of its high brightness (Y value).
[0006]
However, the amount of bromine introduced is limited, and in order to further improve the brightness, a green coloring composition having a transmission region shifted to a longer wavelength side has been demanded.
Then, the objective of this invention is providing the coloring composition for color filters and a color filter which give a green filter with higher brightness.
[0007]
[Means for Solving the Problems]
As a result of intensive studies in order to solve the above problems, the present inventors have identified a copper halide phthalocyanine pigment and a halogenated heterometallic phthalocyanine pigment in which copper as a central metal is positively substituted with a different metal. It has been found that by using a coloring composition contained in a ratio, the transmission wavelength region is shifted to the longer wavelength side, and a green filter with higher brightness can be obtained, and the present invention has been achieved.
[0008]
That is, the present invention relates to a colorant carrier composed of a transparent resin, a precursor thereof or a mixture thereof, and dispersed in the colorant carrier. Contains an average of 12 to 16 bromines in one molecule The copper halide phthalocyanine pigment and the central metal are composed of at least one halogenated heterometallic phthalocyanine pigment selected from the group consisting of Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge and Sn Provided is a coloring composition for a color filter, which contains a green colorant and the content of the halogenated dissimilar metal phthalocyanine pigment is 1 to 80 mol% based on the total amount of the green colorant.
[0009]
In the coloring composition of the present invention, the halogenated foreign metal phthalocyanine pigment is contained in one molecule. on average Preferably it contains 8 to 16 bromines. The present invention further includes at least one red filter segment, at least one blue filter segment, and at least one green filter segment, and the at least one green filter segment is formed from the colored composition of the present invention. Provide a color filter.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
The coloring composition of the present invention contains a colorant carrier composed of a transparent resin, a precursor thereof, or a mixture thereof, and a green colorant dispersed in the colorant carrier. The green colorant consists of a halogenated copper phthalocyanine pigment and a halogenated dissimilar metal phthalocyanine pigment. The colorant carrier provides a resinous binder in the resulting green filter segment.
[0011]
Specific examples of the copper halide phthalocyanine pigment used in the present invention include CI Pigment Green 36 into which bromine and chlorine are introduced.
The copper halide phthalocyanine pigment used in the present invention contains 12 to 16 bromines on average in one molecule because the transmission wavelength region is on the long wavelength side.
[0012]
The halogenated dissimilar metal phthalocyanine pigment constituting the green colorant together with the halogenated copper phthalocyanine pigment functions to shift the transmission wavelength region of the green filter segment to a longer wavelength side. The central metal of the halogenated dissimilar metal phthalocyanine pigment is at least one dissimilar metal selected from Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Zn, Ge, and Sn. Two or more kinds of halogenated different metal phthalocyanine pigments having different central metals can be mixed and used. In addition, when the central metal is a trivalent or tetravalent metal such as Al, Si, Ti, V, Mn, Fe, Ge, or Sn, an axial substituent exists. Axial substituents include, but are not limited to, halogens such as -F, -Cl, -Br, -I, alkoxyl groups, phenoxy groups, = O.
[0013]
All halogens of the halogenated dissimilar metal phthalocyanine pigment may be chlorine, but since the transmission wavelength region is on the longer wavelength side, a halogenated copper phthalocyanine pigment into which bromine is introduced is preferably used. The halogenated dissimilar metal phthalocyanine pigment has a transmission wavelength region on the long wavelength side, and therefore preferably contains 8 to 16 bromines on average in one molecule, and contains 12 to 16 more bromines on average. It is more preferable.
[0014]
In the present invention, the content of the halogenated different metal phthalocyanine pigment is 1 to 80 mol%, preferably 5 to 60 mol%, based on the total amount of the green colorant (halogenated copper phthalocyanine + halogenated different metal phthalocyanine pigment). More preferably, it is 9 to 45 mol%. When the content of the halogenated foreign metal phthalocyanine pigment is less than 1 mol%, the transmission wavelength region does not reach the long wavelength side. When the content of the halogenated foreign metal phthalocyanine pigment exceeds 80 mol%, the transmission wavelength region is Although it is on the longer wavelength side, green is unsuitable for the present invention because the color is light and the saturation is low.
[0015]
The green colorant used in the present invention is, for example, a method in which a crude different metal phthalocyanine pigment is halogenated by a known method and a crude copper halide phthalocyanine pigment, or a crude copper phthalocyanine in the presence of a different metal compound. By halogenating the pigment, it can be produced by a method of synthesizing a crude halogenated (copper / foreign metal) phthalocyanine pigment in which a part of copper is substituted with a different metal. It can also be produced by a method in which a part of copper in the crude copper halide phthalocyanine pigment is replaced with a different metal.
[0016]
The crude halogenated (copper / dissimilar metal) phthalocyanine pigment obtained by the above method has an almost amorphous particle shape and is difficult to disperse as it is. As a method for crystal growth, the above-mentioned amorphous crude halogenated (copper / foreign metal) phthalocyanine pigment is dispersed in an organic solvent and heated, and heated while adding a mechanical share. There are methods such as crystal growth (hereinafter, these steps are referred to as pigmentation treatment).
[0017]
Specifically, as an example of the former pigmentation treatment method, an amorphous crude halogenated (copper / foreign metal) phthalocyanine pigment is mixed with about 5 to 30 times by weight of xylene and boiled under reflux with xylene while stirring. There is a method of crystal growth by doing so. Also, as an example of the latter pigmentation treatment method, a mixture of an amorphous crude halogenated (copper / foreign metal) phthalocyanine pigment, a water-soluble inorganic salt, and a small amount of a water-soluble organic solvent is heated using a kneader. There is a method called salt milling in which crystals are grown by kneading. However, since the color filter is required to be transparent, crystal growth by the above pigmentation treatment should be limited to an average particle size of primary particles of 0.1 μm or less, particularly 0.05 μm or less. Is preferred.
[0018]
Solvents used for the pigmentation treatment include hydrocarbons such as toluene, ethylbenzene, diethylbenzene, methylcyclohexane, ethylcyclohexane, trichloroethane, tetrachloroethane, trichloropropane, monochlorobenzene, dichlorobenzene, trichlorobenzene in addition to the above xylene. , Halogenated hydrocarbon solvents such as chlorotoluene, butyl alcohol, isopentyl alcohol, hexanol, 2-ethyl-1-hexanol, benzyl alcohol, cyclohexanol, ethylene glycol, propylene glycol and other alcohol solvents, phenol, cresol, etc. Phenolic solvents, dibutyl ether, anisole, dioxane, ethylene glycol diethyl ether, ethylene glycol dibutyl ether Ether solvents, butyl methyl ketone, isobutyl ketone, cyclohexanone, methyl cyclohexanone, ketone solvents such as acetophenone, propyl acetate, butyl acetate, isobutyl acetate, isopentyl acetate, 3-methoxybutyl acetate, 2-ethylbutyl acetate, Esters such as 2-ethylhexyl acetate, butyl propionate, ethyl benzoate, diethyl maleate, ethylene glycol monoacetate, nitrobenzene, N-methylaniline, piperidine, pyridine, N, N-dimethylformamide, N-methyl Examples of the solvent include 2-pyrrolidone, ethyl cellosolve, butyl cellosolve, and ethyl carbitol. These solvents can be used alone or in combination. Also, an emulsion in which a water-insoluble solvent is dispersed in water with an activator can be used.
[0019]
The salt milling is a method in which a crude pigment is mixed with a water-soluble inorganic salt and a water-soluble organic solvent, kneaded while heating, and then subjected to a pigmentation treatment by removing the inorganic salt and the high-boiling solvent by washing with water. The water-soluble inorganic salt works as a crushing aid, and it is considered that the crude pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and crystal growth. ing. Accordingly, during kneading, crushing and crystal growth of the crude pigment occur simultaneously, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions. When the pigmentation treatment is performed by salt milling, it is necessary to promote crystal growth by heating, and the heating temperature is preferably 70 to 150 ° C. When the heating temperature is less than 70 ° C., crystal growth does not occur sufficiently, and the shape of the pigment particles becomes undesirably close to amorphous. On the other hand, when the heating temperature exceeds 150 ° C., crystal growth proceeds excessively and the primary particle diameter of the pigment becomes large, which is not preferable as a colorant for the color filter coloring composition.
[0020]
As the water-soluble inorganic salt in salt milling, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The amount of the inorganic salt used for salt milling is preferably 0.5 to 20 times, particularly 1 to 10 times the weight of the crude pigment, from the viewpoints of processing efficiency and production efficiency.
[0021]
The water-soluble organic solvent functions to wet the crude pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent easily evaporates. Examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used.
[0022]
At the time of salt milling, a resin can be used in combination in order to prevent strong agglomeration when the pigment obtained after the pigmentation treatment is dried and to easily disperse the pigment in the transparent resin. By using a resin together during salt milling, a soft powder pigment can be obtained. The resin used for salt milling is preferably a resin that is solid at room temperature, insoluble in water, and at least partially soluble in the above organic solvent. Natural resin, modified natural resin, synthetic resin, synthetic resin modified with natural resin Resin or the like is used. As the natural resin, rosin is representative, and as the modified natural resin, rosin derivatives, fiber derivatives, rubber derivatives, protein derivatives and oligomers thereof are used. Examples of the synthetic resin include epoxy resin, acrylic resin, maleic acid resin, butyral resin, polyester resin, melamine resin, phenol resin, polyurethane resin, and polyamide resin. Examples of synthetic resins modified with natural resins include rosin-modified maleic acid resins and rosin-modified phenolic resins. The amount of the resin used is preferably in the range of 5 to 100% by weight based on the crude pigment.
[0023]
At the time of salt milling, in addition to the above resins, additives such as pigment dispersion aids and plasticizers, or inorganic pigments such as calcium carbonate, barium sulfate, and silica, which are generally known as extender pigments, may be used in combination. Moreover, in order to adjust a hue, you may mix and process with another pigment.
[0024]
As described above, the colorant carrier in which the green colorant of the present invention is dispersed is composed of a transparent resin, a precursor thereof, or a mixture thereof. The transparent resin is a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. The transparent resin includes a thermoplastic resin, a thermosetting resin, and a photosensitive resin, and a precursor thereof includes a monomer or an oligomer that is cured by radiation irradiation to form a transparent resin, which are used alone or in combination. Two or more kinds can be mixed and used.
When the composition is hardened by ultraviolet irradiation, a photoinitiator or the like is added to the colored composition for a color filter of the present invention.
[0025]
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, phenol resin, Examples include polyester resins, acrylic resins, alkyd resins, styrene resins, polyamide resins, rubber resins, cyclized rubbers, celluloses, polybutadiene, and polyimide resins. Moreover, as a thermosetting resin, an epoxy resin, a benzoguanamine resin, a melamine resin, a urea resin etc. are mentioned, for example.
[0026]
Examples of the photosensitive resin include (meth) acrylic compounds having a reactive substituent such as an isocyanate group, an aldehyde group, and an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group, A resin obtained by reacting an acid and introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the linear polymer 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 products are also used.
[0027]
As monomers and oligomers, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa Various acrylic esters and methacrylic esters such as (meth) acrylate, tricyclodecanyl (meth) acrylate, melamine (meth) acrylate, epoxy (meth) acrylate, (meth) acrylic acid, styrene, vinyl acetate, (meth) Examples include acrylamide, N-hydroxymethyl (meth) acrylamide, and acrylonitrile.
[0028]
As photoinitiators, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1one, 1-hydroxycyclohexyl Acetophenone photoinitiators such as phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzyl Benzoin photoinitiators such as dimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'- Benzophenone photoinitiators such as methyldiphenyl sulfide, thioxanthone photoinitiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 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-pienyl-4,6-bis (trichloromethyl) -s-triazine, 2,4-bis (trichloromethyl)- 6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s- Riadin, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloro Triazine photoinitiators such as methyl (4′-methoxystyryl) -6-triazine, borate photoinitiators, carbazole photoinitiators, imidazole photoinitiators and the like are used.
[0029]
The photoinitiator may be used alone or in combination of two or more. As a sensitizer, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, Combined use of compounds such as camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 4,4'-diethylaminobenzophenone You can also
[0030]
The coloring composition for a color filter of the present invention comprises a green colorant composed of a halogenated copper phthalocyanine pigment and a halogenated dissimilar metal phthalocyanine pigment, if necessary, together with the photoinitiator, in a colorant carrier, a three roll mill, It can be produced by finely dispersing using various dispersing means such as a two-roll mill, a sand mill, and a kneader. The coloring composition for a color filter of the present invention is obtained by dispersing a halogenated copper phthalocyanine pigment and a halogenated foreign metal phthalocyanine pigment separately in a colorant carrier, and the content of the halogenated foreign metal phthalocyanine pigment is the above ratio. It can also be produced by mixing.
[0031]
When the pigment is dispersed in the colorant carrier, a dispersion aid such as a resin-type pigment dispersant, a surfactant, or a dye derivative can be appropriately contained. The dispersion aid is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, when a coloring composition is used in which the pigment is dispersed in the colorant carrier using the dispersion aid. In this case, a color filter having excellent transparency can be obtained.
[0032]
The resin-type pigment dispersant has a pigment affinity part that has the property of adsorbing to the pigment and a part that is compatible with the colorant carrier, and adsorbs to the pigment to stabilize the dispersion of the pigment into the colorant carrier. It works to do. Specific examples of resin-type pigment dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkyleneimines) with polyesters having free carboxyl groups, and the like Oil-based dispersants such as salts; water-soluble such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester Modified polyacrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more.
[0033]
Surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, lauryl sulfate monoethanolamine, lauryl Anionic surfactants such as triethanolamine sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene ether Nonionic surfactants such as kill ether phosphates, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more.
[0034]
The dye derivative is a compound in which a substituent is introduced into an organic dye, and the dye derivative used in the present invention is preferably green or yellow in terms of hue, but if the addition amount is small, a blue one may be used. good. Organic dyes also include light yellow aromatic polycyclic compounds such as naphthalene and anthraquinone that are not generally called dyes. Examples of the dye derivatives are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. These can be used alone or in combination of two or more.
[0035]
The color composition for color filter of the present invention preferably contains a yellow pigment in order to realize a spectrum required for a green filter. The yellow pigment is not particularly limited, but it is preferable to select a pigment that meets the required spectrum and has excellent cord resistance. Specifically, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 1 5,187,199 and the like.
These can be used alone or in admixture of two or more. The yellow pigment is used alone to form a yellow colored composition dispersed in a colorant carrier, and the green pigment is used in combination with a green colored composition obtained by dispersing the green colorant in the colorant carrier. It is mixed with the colorant and dispersed in the colorant carrier.
[0036]
Furthermore, in the coloring composition for a color filter of the present invention, a pigment is sufficiently dispersed in a colorant carrier, and applied to a transparent substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm. A solvent can be included to facilitate the formation of the green filter segment. 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, Examples include methyl ethyl ketone, ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent, and the like. These may be used alone or in combination.
[0037]
In addition, the colored composition for a color filter of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the composition. Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Examples thereof include phosphine and phosphite.
[0038]
The colored composition for color filter of the present invention can be prepared in the form of gravure offset printing ink, waterless offset printing ink, silk screen printing ink, solvent development type or alkali development type colored resist material. The colored resist material is obtained by dispersing the green colorant of the present invention in a composition containing a thermoplastic resin, a thermosetting resin or a photosensitive resin, a monomer, and a photoinitiator.
[0039]
The green colorant of the present invention and the yellow pigment used as necessary are preferably 1 in the colored composition by adding the green colorant and the yellow pigment together when the green filter segment is formed by photolithography. When the green filter segment is formed by a printing method, the green colorant and the yellow pigment are added together at a ratio of 1.5 to 40% by weight in the colored composition. Contained. In any case, the pigment (green colorant + yellow pigment) is preferably contained in the final green filter segment in a proportion of 10 to 55% by weight, more preferably 20 to 50% by weight, the balance being the colorant carrier. It substantially consists of the resinous binder provided by. The weight ratio of the green colorant to the yellow pigment is preferably 1: 1 to 2.5: 1. Accordingly, the amount of the green colorant contained in the final green filter segment is preferably 5 to 39% by weight.
[0040]
The colored composition for a color filter of the present invention is a coarse particle having a size of 5 μm or more, preferably a coarse particle having a size of 1 μm or more, more preferably a coarse particle having a size of 0.5 μm or more. It is preferable to remove the mixed dust.
[0041]
As described, the color filter of the present invention comprises at least one red filter segment, at least one blue filter segment, and at least one green filter segment, wherein the green filter segment is the colored composition of the present invention. It is formed using. The red filter segment and the blue filter segment can be formed using a normal red coloring composition and a normal blue coloring composition, respectively.
[0042]
The red coloring composition is a composition obtained by using a red pigment instead of the green coloring agent of the present invention. Red pigments include CI Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 146, 177, 178, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 272 can be used.
[0043]
Further, the blue coloring composition is replaced with, for example, CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60 or the like instead of the green coloring agent of the present invention. It is a composition obtained by using a blue pigment, and a purple pigment such as CI Pigment Violet 19, 23, 27, 32, 42, or the above-mentioned yellow pigment for toning as necessary.
[0044]
The color filter of this invention can be manufactured by forming the filter segment of each color on a transparent substrate using the coloring composition of this invention by the printing method or the photolithographic method.
As the transparent substrate, a glass plate or a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate is used.
[0045]
The formation of each color filter segment by the printing method can be patterned simply by repeating the printing and drying of the colored composition prepared as the above various printing inks. Therefore, the color filter manufacturing method is low-cost and excellent in mass productivity. ing. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.
[0046]
When forming each color filter segment by a photolithography method, the colored composition prepared as the solvent developing type or alkali developing type colored resist material is applied on a transparent substrate, such as spray coating, spin coating, slit coating, roll coating, etc. By a coating method, coating is performed so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the printing method can be manufactured.
[0047]
In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
In order to increase the UV exposure sensitivity, after coating and drying the colored resist material, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.
[0048]
The color filter of the present invention can be produced by an electrodeposition method, a transfer method, or the like in addition to the above method, but the colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a transparent substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. is there. The transfer method is a method in which a color filter layer is formed in advance on the surface of a peelable transfer base sheet, and this color filter layer is transferred to a desired transparent substrate.
[0049]
【Example】
Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In Examples and Comparative Examples, “part” means “part by weight” and “%” means “mol%”.
First, the acrylic resin solution, crude green pigment, and green pigment used in Examples and Comparative Examples will be described.
[0050]
(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.
60.0 parts of styrene
Methacrylic acid 60.0 parts
Methyl methacrylate 65.0 parts
65.0 parts butyl methacrylate
Azobisisobutyronitrile 10.0 parts
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.
[0051]
Below, the synthesis method of a crude green pigment is described. In addition, the measurement of the metal in the synthetic | combination crude pigment was performed with the following method. First, 0.5 g of crude pigment, 1 ml of sulfuric acid, and 3 ml of nitric acid were placed in a 100 ml beaker, decomposed by heating for 1 hour 30 minutes on a gas stove, and then heated for 4 hours in a 600 ° C. electric furnace for decomposition. The decomposed product was dissolved in 5 ml of hydrochloric acid and 25 ml of pure water, and the dissolved product was made up to a volume of 50 ml, and the amount of metal atoms was measured by ICP atomic emission spectrometry. The number of chlorine and bromine in the crude pigment (average number of chlorines and average number of bromines contained in one molecule) The filter paper of No. 6 was wrapped with 0.01 g of crude pigment, 5 drops of hydrogen peroxide were added dropwise, and burned in a combustion flask purged with oxygen. After combustion, the volume was fixed to 100 ml and measured by ion chromatography analysis.
[0052]
[Crude green pigment 1]
In a molten salt of 429 parts of aluminum chloride and 96 parts of sodium chloride at 140 ° C., 64 parts of copper phthalocyanine and 5 parts of aluminum phthalocyanine were dissolved and stirred for 2 hours while maintaining the temperature. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 48 parts per hour for 5 hours. Thereafter, chlorine was introduced at 30 parts per hour for 2 hours. The reaction solution was gradually poured into 4000 parts of water, then filtered and washed with water to obtain 197.2 parts of crude green pigment 1. The obtained crude green pigment 1 was composed of 90.5% crude copper halide phthalocyanine pigment and 9.5% crude aluminum halide phthalocyanine pigment. The average number of bromine contained in one molecule of crude copper halide phthalocyanine pigment was 13 The average number of chlorine was 2.5, the average number of bromine contained in one molecule of the crude aluminum halide phthalocyanine pigment was 13.5, and the average number of chlorine was 2.5.
[0053]
[Crude green pigment 2]
In a molten salt of 429 parts of aluminum chloride and 96 parts of sodium chloride at 160 ° C., 69 parts of copper phthalocyanine was dissolved, and the temperature was raised to 200 ° C. and stirred for 2 hours. The reaction temperature was lowered to 180 ° C., and bromine was added dropwise at 48 parts per hour for 5 hours. Thereafter, chlorine was introduced at 30 parts per hour for 2 hours. The reaction solution was gradually poured into 4000 parts of water, then filtered and washed with water to obtain 196.6 parts of crude green pigment 2. The obtained crude green pigment 2 comprises 58.0% of a crude halogenated copper phthalocyanine pigment and 42.0% of a crude aluminum halide phthalocyanine pigment, and the average number of bromines contained in one molecule of the crude copper halide phthalocyanine pigment is 13. The average number of chlorine was 2.5, the average number of bromine contained in one molecule of the crude aluminum halide phthalocyanine pigment was 13.5, and the average number of chlorine was 2.5.
[0054]
[Crude green pigment 3]
In a molten salt of 429 parts of aluminum chloride and 96 parts of sodium chloride at 140 ° C., 65 parts of aluminum phthalocyanine was dissolved and stirred for 2 hours while maintaining the temperature. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 48 parts per hour for 5 hours. Thereafter, chlorine was introduced at 30 parts per hour for 2 hours. The reaction solution was gradually poured into 4000 parts of water, then filtered and washed with water to obtain 193.5 parts of crude green pigment 3. The obtained crude green pigment 3 consisted of only a crude aluminum halide phthalocyanine pigment, and the average number of bromines contained in one molecule was 13.5 and the average number of chlorines was 2.5.
[0055]
[Crude green pigment 4]
In a molten salt of 130 ° C. of 429 parts of aluminum chloride and 96 parts of sodium chloride, 65 parts of copper phthalocyanine was dissolved and stirred for 2 hours while maintaining the temperature. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 48 parts per hour for 5 hours. Thereafter, chlorine was introduced at 30 parts per hour for 2 hours. The reaction solution was gradually poured into 4000 parts of water, then filtered and washed with water to obtain 193.5 parts of crude green pigment 4. The obtained crude green pigment 4 comprises 97% of a crude halogenated copper phthalocyanine pigment and 3% of a crude aluminum halide phthalocyanine pigment. The average number of bromine contained in one molecule of the crude copper halide phthalocyanine pigment is 13.5, The average chlorine number was 2.5, the average bromine number contained in one molecule of the crude aluminum halide phthalocyanine pigment was 13.5, and the average chlorine number was 2.5.
[0056]
[Crude green pigment 5]
255 parts of biphenyl, 45 parts of naphthalene, 128 parts of phthalodinitrol, 48 parts of titanium tetrachloride and 2 parts of pyridine were mixed, heated to 200 ° C., reacted, filtered, dried and ground to obtain crude titanium phthalocyanine. Next, 200 parts of aluminum chloride and 40 parts of sodium chloride were heated to form a eutectic salt at 120 ° C., and then 40 parts of crude titanium phthalocyanine was added and stirred for 30 minutes. The reaction temperature was raised to 180 ° C. and bromine was added dropwise at 30 parts per hour for 5 hours. Thereafter, chlorine was introduced at 20 parts per hour for 2 hours. The reaction solution was gradually poured into 2500 parts of water, then filtered and washed with water to obtain a crude green pigment 5. The obtained crude green pigment 5 comprises 58.0% of a crude halogenated titanium phthalocyanine pigment and 42.0% of a crude aluminum halide phthalocyanine pigment, and the average number of bromines contained in one molecule of the crude halogenated titanium phthalocyanine pigment is 13. The average number of chlorine was 2.5, the average number of bromine contained in one molecule of the crude aluminum halide phthalocyanine pigment was 13.5, and the average number of chlorine was 2.5.
[0057]
[Crude green pigment 6]
20 parts of copper phthalocyanine is dissolved in 80 parts of aluminum chloride, 10 parts of sodium chloride and 10 parts of sodium sulfate at 150 ° C., the reaction temperature is raised to 160 ° C., and bromine is added at 7.4 parts per hour. It was dripped for 6 hours. Thereafter, the reaction solution was heated to 180 ° C., and chlorine was introduced at 4 parts per hour for 5 hours. The reaction solution was gradually poured into 1000 parts of water, then filtered and washed with water to obtain 45.4 parts of crude green pigment 6. The obtained crude green pigment 6 comprises 99.9% of a crude halogenated copper phthalocyanine pigment and 0.1% of a crude aluminum halide phthalocyanine pigment, and the average number of bromine contained in one molecule of the crude copper halide phthalocyanine pigment is 13. The average number of chlorine was 2.5, the average number of bromine contained in one molecule of the crude aluminum halide phthalocyanine pigment was 13.5, and the average number of chlorine was 2.5.
[0058]
Next, the crude green pigment was pigmented by the following method to produce a green pigment.
[Green pigment 1]
Crude green pigment 4: 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 4 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 490 parts of green pigment 1 were obtained. Green pigment 1 was composed of 97% halogenated copper phthalocyanine pigment and 3% halogenated aluminum phthalocyanine pigment.
[0059]
[Green pigment 2]
Crude green pigment 4: 345 parts, crude green pigment 1: 155 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 4 hours. Next, the kneaded product is put into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered, washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 490 parts of green pigment 2 were obtained. Green pigment 2 was composed of 95% halogenated copper phthalocyanine pigment and 5% halogenated aluminum phthalocyanine pigment.
[0060]
[Green pigment 3]
Crude green pigment 1: 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader, and the same operation as in green pigment 1 was performed to obtain 490 parts of green pigment 3. The green pigment 3 was composed of 90.5% of a halogenated copper phthalocyanine pigment and 9.5% of an aluminum halide phthalocyanine pigment.
[0061]
[Green pigment 4]
Crude green pigment 4: 282 parts, crude green pigment 2: 218 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader, and the same operation as in green pigment 1 was performed, and 490 parts of green Pigment 4 was obtained. The green pigment 4 was composed of 79.0% halogenated copper phthalocyanine pigment and 21.0% aluminum halide phthalocyanine pigment.
[0062]
[Green pigment 5]
Crude green pigment 4: 154 parts, crude green pigment 2: 346 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader, and the same operation as for green pigment 1 was performed, and 490 parts of green Pigment 5 was obtained. The green pigment 5 was composed of 70.0% of a halogenated copper phthalocyanine pigment and 30.0% of an aluminum halide phthalocyanine pigment.
[0063]
[Green pigment 6]
Crude green pigment 2: 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader, and the same operation as in green pigment 1 was performed to obtain 490 parts of green pigment 6. The green pigment 6 was composed of 58.0% of a halogenated copper phthalocyanine pigment and 42.0% of an aluminum halide phthalocyanine pigment.
[0064]
[Green pigment 7]
Crude green pigment 4: 410 parts, crude green pigment 5: 90 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged into a stainless steel 1 gallon kneader, and the same operation as for green pigment 1 was performed, and 490 parts of green Pigment 7 was obtained. The green pigment 7 was composed of 79.5% halogenated copper phthalocyanine pigment, 10.0% aluminum halide phthalocyanine pigment and 10.5% halogenated titanium phthalocyanine pigment.
[0065]
[Green pigment 8]
Crude green pigment 6: 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged in a stainless steel 1 gallon kneader, and the same operation as in green pigment 1 was performed to obtain 490 parts of green pigment 8. The green pigment 8 was composed of 99.9% of a halogenated copper phthalocyanine pigment and 0.1% of an aluminum halide phthalocyanine pigment.
[0066]
[Green pigment 9]
Prepare 450 parts of crude green pigment, 6 parts of crude green pigment, 6 parts of green pigment, 500 parts of sodium chloride and 250 parts of diethylene glycol in a stainless steel 1 gallon kneader, and perform the same operation as for green pigment 1, 490 parts of green. Pigment 9 was obtained. The green pigment 9 was composed of 9.9% of a halogenated copper phthalocyanine pigment and 90.1% of an aluminum halide phthalocyanine pigment.
[0067]
Next, using these green pigments, green photosensitive coloring compositions (resist materials) were prepared in which the compounding ratio of the halogenated copper phthalocyanine pigment and the halogenated dissimilar metal phthalocyanine pigment was changed.
[0068]
[Example 1]
A mixture having the following composition was uniformly dispersed and stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali developing type photosensitive coloring composition.
4.5 parts of green pigment 1
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
[0069]
[Examples 2 to 7]
An alkali-developable photosensitive coloring composition was prepared in the same manner as in Example 1 except that the green pigment 1 was changed to the green pigments 2 to 7.
[Comparative Example 1]
An alkali developing photosensitive coloring composition was prepared in the same manner as in Example 1 except that the green pigment 1 was changed to the green pigment 8.
[Comparative Example 2]
An alkali developing photosensitive coloring composition was prepared in the same manner as in Example 1 except that the green pigment 1 was changed to the green pigment 9.
[0070]
The photosensitive coloring compositions obtained in Examples 1 to 7 and Comparative Examples 1 and 2 were rotated on a glass substrate of 100 mm × 100 mm and 1.1 mm thickness using a spin coater at 500 rpm, 1000 rpm, 1500 rpm, and 2000 rpm. Four types of coated substrates having different film thicknesses were obtained. 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 230 ° C. for 1 hour and allowed to cool, and then the chromaticity (Y, x, y) of the obtained green coating film with a C light source was measured with a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). It measured using. From the four sets of chromaticity / spectral measurement results, the maximum transmittance (Tmax), x, and y when the minimum value of the spectral transmittance at a wavelength of 400 to 700 nm was 1% were determined. Furthermore, the surface state of the coated substrate at 1000 rpm was observed with an optical microscope (“BX60” manufactured by Olympus Optical Co., Ltd.). The results are shown in Table 1.
[0071]
[Table 1]
As shown in Table 1, all the green coating films obtained using the colored composition of the present invention have a chromaticity x in the range of 0.25 to 0.34 and a chromaticity y of 0.43 to 0.00. In the range of 58, the brightness Y is large, and within the range where the content of the aluminum halide phthalocyanine pigment is 80 mol% or less, the lightness increases as the content of the aluminum halide phthalocyanine pigment increases. On the other hand, the green coating film of Comparative Example 1 having a content of aluminum halide phthalocyanine pigment of 0.1%, which is less than the range of the present invention, has low brightness. Further, the green coating film of Comparative Example 2 having a content of the aluminum halide phthalocyanine pigment of 90%, which is larger than the range of the present invention, has a brightness Y as large as 67 but y as small as 0.4175. Therefore, the color is light as green and is not suitable as a green filter segment.
[0073]
Next, a green photosensitive coloring composition (resist material) was prepared by using a green pigment and a yellow pigment (CI Pigment Yellow 150) in combination for color matching.
[Example 8]
A mixture having the following composition was uniformly dispersed and stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali developing type photosensitive coloring composition.
3.6 parts of green pigment 1
Yellow pigment (PY150) 0.9 part
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
[0074]
[Examples 9 to 13]
An alkali-developable photosensitive coloring composition was prepared in the same manner as in Example 8 except that the type of green pigment and the ratio (weight ratio) of the green pigment to the yellow pigment were changed as shown in Table 2.
[0075]
Using the spin coater, the photosensitive coloring compositions obtained in Examples 8 to 13 are formed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm so that x = 0.3172 and y = 0.4703. The film was applied to a proper film thickness. 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 230 ° C. for 1 hour and allowed to cool, and then the brightness (Y) of the obtained green coating film with a D65 light source using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) Maximum transmittance (Tmax), minimum transmittance (Tmin), and contrast were determined. Furthermore, the surface state of the coating film was observed with an optical microscope (Olympus Optical Co., Ltd. “BX60”). The results are shown in Table 2.
[0076]
[Table 2]
As shown in Table 2, the green coating film obtained using the colored composition of the present invention has a high content of aluminum halide phthalocyanine pigment even when x and y (hue) are combined with a yellow pigment. The lightness increases. In addition, when the content of the aluminum halide phthalocyanine pigment is within the range of 80 mol% or less, the higher the content of the aluminum halide phthalocyanine pigment, the smaller the amount of yellow pigment used for toning, and the contrast is improved. ing.
[0078]
Next, in the same manner as the green photosensitive coloring composition, a blue photosensitive coloring composition and a green photosensitive coloring composition having the following compositions were prepared, and the two kinds of coloring compositions and Examples 1 to 13 were obtained. Using the green photosensitive coloring composition, a color filter was prepared by the following method.
[Blue photosensitive coloring composition]
Blue pigment: CI Pigment Blue 15: 6 4.5 parts
("Rionol Blue ES" manufactured by Toyo Ink Co., Ltd.)
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
[0079]
[Red photosensitive coloring composition]
Red pigment: 4.0 parts CI Pigment Red 254
("Irga Four Red B-CF" manufactured by Ciba Geigy)
Red pigment: CI Pigment Red 177 0.5 part
(Ciba Geigy "Chromophthal Red A2B")
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
[0080]
The photosensitive coloring composition is applied on one surface of a glass substrate using a spin coater, dried in a hot air oven at 70 ° C. for 20 minutes, and then passed through a photomask having a stripe-shaped opening having a width of 100 μm. UV exposure, wash the unexposed area with 5% by weight sodium carbonate aqueous solution, and bake in a hot air oven at 230 ° C. for 30 minutes to provide 100 μm wide striped red filter segment, blue filter segment and green filter segment A color filter was prepared.
All of the obtained color filters had high whiteness.
[0081]
【The invention's effect】
The colored composition of the present invention contains a halogenated copper phthalocyanine pigment and a halogenated heterometallic phthalocyanine pigment in a specific ratio, so that the transmission wavelength region is shifted to the long wavelength side, so that the green color is extremely high in brightness. A filter segment can be formed on the substrate.
A color filter having a green filter segment formed using the colored composition of the present invention can simultaneously impart high brightness and high saturation to a color liquid crystal display device, and is a transmissive / reflective color liquid crystal display device Moreover, it is suitable as a color filter for color separation of a solid-state image sensor.
Claims (3)
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| JP2001382455A JP3945242B2 (en) | 2000-12-22 | 2001-12-17 | Coloring composition for color filter and color filter |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE330239T1 (en) | 2001-02-23 | 2006-07-15 | Dainippon Ink & Chemicals | COLOR FILTER |
| KR100708327B1 (en) | 2002-07-24 | 2007-04-17 | 다이니폰 인사츠 가부시키가이샤 | Green pigment for color filter, green pigment dispersion, photosensitive color composition, color filter, and liquid crystal panel |
| JP4525122B2 (en) * | 2004-03-19 | 2010-08-18 | 東洋インキ製造株式会社 | Green coloring composition for color filter and color filter |
| JP2007002076A (en) * | 2005-06-23 | 2007-01-11 | Sumika Color Kk | Yellow pigment |
| JP4983029B2 (en) * | 2006-02-03 | 2012-07-25 | 東洋インキＳｃホールディングス株式会社 | Coloring composition |
| JP5141939B2 (en) * | 2006-04-18 | 2013-02-13 | Ｄｉｃ株式会社 | Polyhalogenated zinc phthalocyanine pigment composition and color filter |
| JP4752590B2 (en) * | 2006-04-18 | 2011-08-17 | Ｄｉｃ株式会社 | Polyhalogenated zinc phthalocyanine pigment composition and color filter |
| JP5145649B2 (en) * | 2006-04-25 | 2013-02-20 | 東洋インキＳｃホールディングス株式会社 | Composition of chlorinated brominated phthalocyanine skeleton-containing compound, method for producing the composition, and pigment-dispersed ink and color filter using the composition |
| KR101024205B1 (en) * | 2007-11-05 | 2011-03-23 | 주식회사 엘지화학 | Ink composition for roll printing |
| JP5239385B2 (en) * | 2008-02-20 | 2013-07-17 | 東洋インキＳｃホールディングス株式会社 | Method for producing polyhalogenated copper phthalocyanine pigment, polyhalogenated copper phthalocyanine pigment produced by the method, and coloring composition using the same |
| KR20100033928A (en) * | 2008-09-22 | 2010-03-31 | 후지필름 가부시키가이샤 | Colored photosensitive composition, color filter and liquid crystal display device |
| JP5381533B2 (en) * | 2009-09-14 | 2014-01-08 | 東洋インキＳｃホールディングス株式会社 | Coloring composition, photosensitive coloring composition for color filter, and color filter |
| JP4893859B1 (en) * | 2011-01-28 | 2012-03-07 | 東洋インキＳｃホールディングス株式会社 | Coloring composition for color filter, and color filter |
| JP6402464B2 (en) * | 2014-03-24 | 2018-10-10 | 東洋インキＳｃホールディングス株式会社 | Method for producing halogenated organic pigment, halogenated organic pigment obtained by the production method, and coloring composition containing the same |
| KR20160039620A (en) | 2013-08-05 | 2016-04-11 | 토요잉크Sc홀딩스주식회사 | Method for producing halogenated organic pigment, halogenated organic pigment produced by said production method, and colored composition containing said halogenated organic pigment |
| JP6205288B2 (en) | 2014-02-14 | 2017-09-27 | 富士フイルム株式会社 | Coloring composition, cured film, color filter, pattern forming method, color filter manufacturing method, solid-state imaging device, and image display device |
| KR102029354B1 (en) | 2015-02-03 | 2019-10-07 | 토요잉크Sc홀딩스주식회사 | Phthalocyanine Pigment, Coloring Composition and Color Filter |
| JP2017197685A (en) | 2016-04-28 | 2017-11-02 | 東洋インキＳｃホールディングス株式会社 | Phthalocyanine pigment, colored composition and color filter |
| JP2021015169A (en) * | 2019-07-11 | 2021-02-12 | 東洋インキＳｃホールディングス株式会社 | Coloring composition, photosensitive coloring composition, color filter and liquid crystal display device |
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