JP4677262B2 - Photocurable coloring composition and color filter formed using the same - Google Patents
Photocurable coloring composition and color filter formed using the same Download PDFInfo
- Publication number
- JP4677262B2 JP4677262B2 JP2005086767A JP2005086767A JP4677262B2 JP 4677262 B2 JP4677262 B2 JP 4677262B2 JP 2005086767 A JP2005086767 A JP 2005086767A JP 2005086767 A JP2005086767 A JP 2005086767A JP 4677262 B2 JP4677262 B2 JP 4677262B2
- Authority
- JP
- Japan
- Prior art keywords
- coloring composition
- photocurable coloring
- pigment
- weight
- red
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 62
- 238000004040 coloring Methods 0.000 title claims description 49
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- 239000011347 resin Substances 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000001062 red colorant Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 239000000040 green colorant Substances 0.000 claims description 12
- 239000012860 organic pigment Substances 0.000 claims description 6
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical group C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- -1 -1-one Chemical compound 0.000 description 26
- 239000000049 pigment Substances 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
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- 238000000576 coating method Methods 0.000 description 8
- 238000011161 development Methods 0.000 description 8
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- 239000003513 alkali Substances 0.000 description 5
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- 239000001054 red pigment Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000001052 yellow pigment Substances 0.000 description 5
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- 229910019142 PO4 Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 3
- 239000001055 blue pigment Substances 0.000 description 3
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- 238000001035 drying Methods 0.000 description 3
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- 238000000206 photolithography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
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- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
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- SYQKAWAEPBPOQD-UHFFFAOYSA-N 1-(4-benzyl-2,3-dimethylphenyl)-2-hydroxy-2-phenylethanone Chemical class C(C1=CC=CC=C1)C1=C(C(=C(C=C1)C(=O)C(O)C1=CC=CC=C1)C)C SYQKAWAEPBPOQD-UHFFFAOYSA-N 0.000 description 1
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
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Description
本発明は、カラー液晶表示装置、カラー撮像管素子等に用いられるカラーフィルタの製造に使用される光硬化性着色組成物、およびそれを用いて形成されるカラーフィルタに関する。 The present invention relates to a photocurable coloring composition used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter formed using the same.
近年、カラー液晶表示装置は、カーナビゲーション、液晶表示装置一体型のノートパソコン等に用いられて大きな市場を形成するに至っており、省エネ、省スペースという特徴を活かして、デスクトップパソコン用のモニターおよびカラーテレビとしても普及し始めており色再現性のよいディスプレイが求められている。
カラー液晶表示装置において、色再現を司る重要な部材がカラーフィルタであり、その構成は、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パターン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一定の配列で配置したものからなっている
In recent years, color liquid crystal display devices have been used in car navigation, liquid crystal display integrated laptops, etc. to form a large market. Taking advantage of energy saving and space saving features, monitors and color monitors for desktop personal computers. A display having good color reproducibility has been demanded as it has begun to spread as a television.
In a color liquid crystal display device, an important member for color reproduction is a color filter, and its structure is a fine band (striped) filter segment pattern of two or more different hues on the surface of a transparent substrate such as glass. Are arranged in parallel or intersecting with each other, or fine filter segments are arranged in a fixed arrangement.
カラーフィルタの色再現特性向上のためには、光硬化性着色組成物中の着色剤の含有量を多くするか、あるいはフィルタセグメントの膜厚を厚くする必要がある。しかし、いずれの方法を用いても、フィルタセグメントを形成する際の照射光が顔料に吸収され、膜底部まで照射光が届かず基板に近い部分が未硬化となり、フィルタセグメントの断面形状が逆テーパー形状となる等の問題が発生する。フィルタセグメントの断面形状が逆テーパー形状となると、カラーフィルタ上に蒸着等で形成される透明電極がカラーフィルタ周辺底部に回り込めず不連続となるので、断線が生じて液晶ディスプレイの表示性能に障害がでる。
本発明は、着色剤含有量が多くても高感度で、膜厚が厚くとも、パタ−ン形状が優れたフィルタセグメントを形成することができる光硬化性着色組成物、およびフィルタセグメントのパターン形状が良好で高品質なカラーフィルタの提供を目的とする。 The present invention relates to a photocurable coloring composition capable of forming a filter segment having an excellent pattern shape even when the colorant content is high and having a high sensitivity and a large film thickness, and a filter segment pattern shape The purpose is to provide a color filter with good quality.
本発明の光硬化性着色組成物は、エチレン性不飽和化合物、透明樹脂、赤色または緑色の有機顔料、および光重合開始剤を含有する光硬化性着色組成物であって、前記光重合開始剤の含有量が光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として１８．０〜３０重量％であることを特徴とする。
また、本発明のカラーフィルタは、本発明の光硬化性着色組成物から形成されるフィルタセグメントを備えることを特徴とする。
The photocurable coloring composition of the present invention is a photocurable coloring composition containing an ethylenically unsaturated compound, a transparent resin, a red or green organic pigment, and a photopolymerization initiator, and the photopolymerization initiator The content of is 18.0 to 30% by weight based on the weight (100% by weight) of the total solid content in the photocurable coloring composition.
Moreover, the color filter of this invention is equipped with the filter segment formed from the photocurable coloring composition of this invention, It is characterized by the above-mentioned.
本発明の光硬化性着色組成物は、光重合開始剤が、２−（ジメチルアミノ）−２−[（４−メチルフェニル）メチル]−１ −[４−（４−モルホリニル）フェニル]−１−ブタノン、または１，２-オクタンジオン−１−〔４−（フェニルチオ）−２−（Ｏ−ベンゾイルオキシム）〕を含み、かつ光重合開始剤の含有量が光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として１８．０〜３０重量％と、従来の光硬化性着色組成物と比べてかなり多いため着色剤含有量が多くても感度が高く、フィルタセグメントの膜厚が厚くとも、パターン形状が優れた各色フィルタセグメントを形成することができる。
In the photocurable coloring composition of the present invention, the photopolymerization initiator is 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1. -Butanone or 1,2-octanedione-1- [4- (phenylthio) -2- (O-benzoyloxime)], and the content of the photopolymerization initiator is all in the photocurable coloring composition Since the solid content is 18.0 to 30% by weight (100% by weight), which is considerably higher than the conventional photocurable coloring composition, the sensitivity is high even if the colorant content is large. Even if the film thickness is large, each color filter segment having an excellent pattern shape can be formed.
まず、本発明の光硬化性着色組成物について具体的に説明する。
本発明の光硬化性着色組成物は、エチレン性不飽和化合物、透明樹脂、赤色または緑色の有機顔料、および光重合開始剤を含有し、該光重合開始剤が、２−（ジメチルアミノ）−２−[（４−メチルフェニル）メチル]−１ −[４−（４−モルホリニル）フェニル]−１−ブタノン、または１，２-オクタンジオン−１−〔４−（フェニルチオ）−２−（Ｏ−ベ ンゾイルオキシム）〕を含む。
光重合開始剤は、１種類を単独で用いても、複数種を組み合わせて用いてもよい
First, the photocurable coloring composition of this invention is demonstrated concretely.
The photocurable coloring composition of the present invention contains an ethylenically unsaturated compound, a transparent resin, a red or green organic pigment , and a photopolymerization initiator, and the photopolymerization initiator is 2- (dimethylamino)- 2-[(4-Methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone or 1,2-octanedione-1- [4- (phenylthio) -2- (O -Benzoyloxime)] .
A photoinitiator may be used individually by 1 type, or may be used in combination of multiple types.
光重合開始剤としては、４−フェノキシジクロロアセトフェノン、４−ｔ−ブチル−ジクロロアセトフェノン、ジエトキシアセトフェノン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、１−ヒドロキシシクロヘキシルフェニルケトン、２−メチル−１−[４−（メチルチオ）フェニル]−２−モルフォリノプロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン、２−（ジメチルアミノ）−２−[（４−メチルフェニル）メチル]−１−[４−（４−モルホリニル）フェニル]−１−ブタノン等のアセトフェノン系化合物、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化合物、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、３，３’，４，４’−テトラ（ｔ−ブチルパーオキシカルボニル）ベンゾフェノン等のベンゾフェノン系化合物、チオキサントン、２−クロルチオキサントン、２−メチルチオキサントン、イソプロピルチオキサントン、２，４−ジイソプロピルチオキサントン、２，４−ジエチルチオキサントン等のチオキサントン系化合物、２，４，６−トリクロロ−ｓ−トリアジン、２−フェニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−メトキシフェニル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−トリル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−ピペロニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−スチリル−ｓ−トリアジン、２−（ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（４−メトキシ−ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−トリクロロメチル−（ピペロニル）−６−トリアジン、２，４−トリクロロメチル（４’−メトキシスチリル）−６−トリアジン等のトリアジン系化合物、１−［４−（フェニルチオ）フェニル］−オクタン−１，２−ジオン２−（Ｏ−ベンジルオキシム）、１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル］−エタノン１−（Ｏ−アセチルオキシム）等のオキシムエステル系化合物、ビス（２，４，６−トリメチルベンゾイル）フェニルホスフィンオキサイド、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキサイド等のホスフィン系化合物、９，１０−フェナンスレンキノン、カンファーキノン、エチルアントラキノン等のキノン系化合物、ボレート系化合物、カルバゾール系化合物、イミダゾール系化合物、チタノセン系化合物等が用いられる。 Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane Acetophenone compounds such as -1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, benzoin, benzoinmethyl Ether, benzoin ethyl ether, benzoin isopropyl ether, benzyldimethyl Benzoin compounds such as ketals, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4' Benzophenone compounds such as tetra (t-butylperoxycarbonyl) benzophenone, thioxanthone compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-diethylthioxanthone 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bi (Trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s-triazine, 2 , 4-Bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphtho-) 1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6 Triazine compounds such as triazine, 1- [4- (phenylthio) phenyl] -octane-1,2-dione 2- (O-benzyloxime), 1- [9-ethyl-6- Oxime ester compounds such as (2-methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4 Phosphine compounds such as 1,6-trimethylbenzoyldiphenylphosphine oxide, quinone compounds such as 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, borate compounds, carbazole compounds, imidazole compounds, titanocene compounds, etc. Is used.
本発明の光硬化性組成物には、増感剤として、トリエタノールアミン、メチルジエタノールアミン、トリイソプロパノールアミン、４−ジメチルアミノ安息香酸メチル、４−ジメチルアミノ安息香酸エチル、４−ジメチルアミノ安息香酸イソアミル、安息香酸２−ジメチルアミノエチル、４−ジメチルアミノ安息香酸２−エチルヘキシル、Ｎ，Ｎ−ジメチルパラトルイジン、４，４'−ビス（ジメチルアミノ）ベンゾフェノン、４，４'−ビス（ジエチルアミノ）ベンゾフェノン、４，４'−ビス（エチルメチルアミノ）ベンゾフェノン等のアミン系化合物を含有させることもできる。これらの増感剤は、１種を単独で、または２種以上を混合して用いることができる。
特に、光重合開始剤２−（ジメチルアミノ）−２−[（４−メチルフェニル）メチル]−１ −[４−（４−モルホリニル）フェニル]−１−ブタノン、または１，２-オクタンジオン−１−〔４−（フェニルチオ）−２−（Ｏ−ベ ンゾイルオキシム）〕と、２,４−ジエチルチオキサントン（光重合開始剤）または４，４'−ビス（ジエチルアミノ）ベンゾフェノン（増感剤）とを組み合わせて用いると、光重合開始剤が効率よく増感されるためより好ましい。
In the photocurable composition of the present invention, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate are used as sensitizers. 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, An amine compound such as 4,4′-bis (ethylmethylamino) benzophenone can also be contained. These sensitizers can be used individually by 1 type or in mixture of 2 or more types.
In particular, photoinitiator 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, or 1,2-octanedione- 1- [4- (phenylthio) -2- (O-benzoyloxime)] and 2,4-diethylthioxanthone (photopolymerization initiator) or 4,4′-bis (diethylamino) benzophenone (sensitizer) Is used in combination because the photopolymerization initiator is efficiently sensitized.
光重合開始剤の含有量は、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として１８．０〜３０重量％であり、１８．０〜２５重量％であることが好ましい。光重合開始剤の含有量が１８．０未満では、塗膜のパターン形状が不良となり、３０重量％を越えると塗膜の強度が弱くなってしまう。
また、増感剤の含有量は、増感剤が３６５ｎｍの光を吸収して塗膜底部に光が届かず硬化塗膜のパターン形状が不良となることを防止するため、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として０．1〜２重量％であることが好ましい。
The content of the photopolymerization initiator is 18.0 to 30 wt% of the weight of the total solids of the photocurable colored composition based (100 wt%), and 18.0 to 25 wt% Is preferred. If the content of the photopolymerization initiator is less than 18.0 , the pattern shape of the coating film becomes poor, and if it exceeds 30% by weight, the strength of the coating film becomes weak.
The content of the sensitizer is such that the sensitizer absorbs light at 365 nm so that the light does not reach the bottom of the coating film and the pattern shape of the cured coating film is not good. It is preferably 0.1 to 2% by weight based on the weight (100% by weight) of the total solid content in the product.
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。透明樹脂としては、熱可塑性樹脂および熱硬化性樹脂が挙げられ、これらを単独で、または２種以上混合して用いることができる。透明樹脂の含有量は、硬化物の強度の点から、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として ２０〜７０重量％であることが好ましい。
熱可塑性樹脂としては、例えば、ブチラール樹脂、スチレンーマレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、ポリスチレン、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリエチレン、ポリブタジエン、ポリイミド樹脂等が挙げられる。また、熱硬化性樹脂としては、例えば、エポキシ樹脂、ベンゾグアナミン樹脂、ロジン変性マレイン酸樹脂、ロジン変性フマル酸樹脂、メラミン樹脂、尿素樹脂、フェノール樹脂等が挙げられる。
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. Examples of the transparent resin include thermoplastic resins and thermosetting resins, and these can be used alone or in admixture of two or more. From the viewpoint of the strength of the cured product, the content of the transparent resin is preferably 20 to 70% by weight based on the weight of the total solid content in the photocurable coloring composition (100% by weight).
Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.
エチレン性不飽和化合物には、感光性樹脂、および光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ある。
エチレン性不飽和化合物の含有量は、光硬化性の点から、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として１０〜５０重量％であることが好ましい。
Ethylenically unsaturated compounds include photosensitive resins and monomers or oligomers that are cured by light irradiation to produce transparent resins.
The content of the ethylenically unsaturated compound is preferably 10 to 50% by weight based on the weight of the total solid content in the photocurable coloring composition (100% by weight) from the viewpoint of photocurability.
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。 As the photosensitive resin, a (meth) acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or 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 in which a photocrosslinkable group such as a (meth) acryloyl group or a styryl group is introduced by reacting cinnamic acid 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.
モノマーもしくはオリゴマーとしては、例えばメチル（メタ）アクリレート、エチル（メタ）アクリレート、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、β−カルボキシエチル（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、１，６−ヘキサンジオールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート、トリメチロールプロパントリ（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、１, ６−ヘキサンジオールジグリシジルエーテルジ（メタ）アクリレート、ビスフェノールＡジグリシジルエーテルジ（メタ）アクリレート、ネオペンチルグリコールジグリシジルエーテルジ（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、エステルアクリレート、メチロール化メラミンの（メタ）アクリル酸エステル、エポキシ（メタ）アクリレート、ウレタン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、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、（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、Ｎ−ビニルホルムアミド、アクリロニトリル等が挙げられる。これらは、単独でまたは２種類以上混合して用いることができる。 Examples of the monomer or oligomer include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, and β-carboxyethyl (meth). Acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, penta Erythritol tri (meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate , Neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, (meth) acrylic acid ester of methylolated melamine, epoxy (meth) Various acrylates and methacrylates such as acrylate and urethane acrylate, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl ( Examples include meth) acrylamide, N-vinylformamide, acrylonitrile and the like. These can be used alone or in admixture of two or more.
赤色または緑色の着色剤としては、有機または無機の顔料を、単独でまたは２種類以上混合して用いることができる。顔料のなかでは、発色性が高く、且つ耐熱性の高い顔料、特に耐熱分解性の高い顔料が好ましく、通常は有機顔料が用いられる。
本発明の光硬化性着色組成物においては、赤色または緑色の着色剤の含有量が光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として５〜７０重量％と多くても画素形状は順テーパー形状となる。しかし、赤色または緑色の着色剤の含有量は、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として２０〜５０重量％であることが好ましい。
As the red or green colorant, organic or inorganic pigments can be used alone or in admixture of two or more. Among the pigments, pigments having high color developability and high heat resistance, particularly pigments having high heat decomposition resistance are preferred, and organic pigments are usually used.
In the photocurable coloring composition of the present invention, the content of the red or green colorant is as high as 5 to 70% by weight based on the weight (100% by weight) of the total solid content in the photocurable coloring composition. However, the pixel shape is a forward tapered shape. However, the content of the red or green colorant is preferably 20 to 50% by weight based on the weight (100% by weight) of the total solid content in the photocurable coloring composition.
以下に、赤色着色剤または緑色着色剤として使用可能な有機顔料の具体例を、カラーインデックス番号で示す。
赤色着色剤としては、例えばC.I. Pigment Red ７、９、１４、４１、４８：１、４８：２、４８：３、４８：４、８１：１、８１：２、８１：３、９７、１２２、１２３、１４６、１４９、１６８、１７７、１７８、１７９、１８０、１８４、１８５、１８７、１９２、２００、２０２、２０８、２１０、２１５、２１６、２１７、２２０、２２３、２２４、２２６、２２７、２２８、２４０、２４６、２５４、２５５、２６４、２７２、２７９等の赤色顔料を用いることができる。赤色着色剤には、黄色顔料、オレンジ顔料を併用することができる。
緑色着色剤としては、例えばC.I. Pigment Green ７、１０、３６、３７等の緑色顔料を用いることができる。緑色着色剤には、黄色顔料を併用することができる。
Below, the specific example of the organic pigment which can be used as a red colorant or a green colorant is shown with a color index number.
Examples of the red colorant include CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 179, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, Red pigments such as 240, 246, 254, 255, 264, 272, and 279 can be used. A yellow pigment and an orange pigment can be used in combination with the red colorant.
As the green colorant, for example, a green pigment such as CI Pigment Green 7, 10, 36, 37 can be used. A yellow pigment can be used in combination with the green colorant.
赤色または緑色着色剤に併用できる黄色顔料としては、例えばC.I. Pigment Yellow １、２、３、４、５、６、１０、１２、１３、１４、１５、１６、１７、１８、２０、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、８６、９３、９４、９５、９７、９８、１００、１０１、１０４、１０６、１０８、１０９、１１０、１１３、１１４、１１５、１１６、１１７、１１８、１１９、１２０、１２３、１２５、１２６、１２７、１２８、１２９、１３７、１３８、１３９、１４７、１４８、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、１８８、１９３、１９４、１９９、２１３、２１４等が挙げられる。
また、赤色着色剤に併用できるオレンジ色顔料としては、例えばC.I. Pigment orange ３６、４３、５１、５５、５９、６１、７１、７３等が挙げられる。
Examples of yellow pigments that can be used in combination with red or green colorants include CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 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, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 1 0,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214, and the like.
Examples of the orange pigment that can be used in combination with the red colorant include CI Pigment orange 36, 43, 51, 55, 59, 61, 71, 73, and the like.
さらに、本発明の光硬化性着色組成物には、連鎖移動剤としての働きをする多官能チオールを含有させることができる。
多官能チオールは、チオール基を２個以上有する化合物であればよく、例えば、ヘキサンジチオール 、デカンジチオール 、１，４−ブタンジオールビスチオプロピオネート、１，４−ブタンジオールビスチオグリコレート、エチレングリコールビスチオグリコレート、エチレングリコールビスチオプロピオネート、トリメチロールプロパントリスチオグリコレート、トリメチロールプロパントリスチオプロピオネート、トリメチロールプロパントリス（３−メルカプトブチレート）、ペンタエリスリトールテトラキスチオグリコレート、ペンタエリスリトールテトラキスチオプロピオネート、トリメルカプトプロピオン酸トリス（２−ヒドロキシエチル）イソシアヌレート、１，４−ジメチルメルカプトベンゼン、２、４、６−トリメルカプト−ｓ−トリアジン、２−（Ｎ，Ｎ−ジブチルアミノ）−４，６−ジメルカプト−ｓ−トリアジン等が挙げられる。これらの多官能チオールは、１種または２種以上混合して用いることができる。
多官能チオールの含有量は、光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として好ましくは０．１〜３０重量％であり、より好ましくは１〜２０重量％である。多官能チオールの含有量が０．１重量％未満では多官能チオールの添加効果が不充分であり、３０重量％を越えると感度が高すぎて逆に解像度が低下する。
Furthermore, the photocurable coloring composition of the present invention can contain a polyfunctional thiol that functions as a chain transfer agent.
The polyfunctional thiol may be a compound having two or more thiol groups. For example, hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene Glycol bisthioglycolate, ethylene glycol bisthiopropionate, trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, Pentaerythritol tetrakisthiopropionate, trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimerca DOO -s- triazine, 2- (N, N- dibutylamino) -4,6-dimercapto -s- triazine. These polyfunctional thiols can be used alone or in combination.
The content of the polyfunctional thiol is preferably 0.1 to 30% by weight, more preferably 1 to 20% by weight, based on the weight of the total solid content in the photocurable coloring composition (100% by weight). is there. If the content of the polyfunctional thiol is less than 0.1% by weight, the effect of adding the polyfunctional thiol is insufficient, and if it exceeds 30% by weight, the sensitivity is too high and the resolution is lowered.
光硬化性着色組成物には、赤色または緑色の着色剤を充分にエチレン性不飽和化合物および透明樹脂中に分散させ、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赤色または緑色の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、プロピレングリコールモノメチルエーテルアセテート、ジエチレングリコールジメチルエーテル、エチルベンゼン、エチレングリコールジエチルエーテル、キシレン、エチルセロソルブ、メチル−ｎアミルケトン、プロピレングリコールモノメチルエーテル、トルエン、メチルエチルケトン、酢酸エチル、メタノール、エタノール、イソプロピルアルコール、ブタノール、イソブチルケトン、石油系溶剤等が挙げられ、これらを単独でもしくは混合して用いる。溶剤は、光硬化性着色組成物の全固形分の重量に対して、一般的に３〜１０重量倍、好ましくは４〜８重量倍の範囲で用いられる。 In the photocurable coloring composition, a red or green colorant is sufficiently dispersed in an ethylenically unsaturated compound and a transparent resin, and a dry film thickness is 0.2 to 5 μm on a transparent substrate such as a glass substrate. In order to make it easier to apply and form a red or green filter segment, a solvent can be included. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether, toluene, methyl ethyl ketone, acetic acid Examples thereof include ethyl, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent, and the like. These may be used alone or in combination. The solvent is generally used in a range of 3 to 10 times, preferably 4 to 8 times the weight of the total solid content of the photocurable coloring composition.
本発明の光硬化性着色組成物は、１種または２種以上の赤色着色剤または緑色着色剤を、上記光重合開始剤と共に、エチレン性不飽和化合物、透明樹脂および溶剤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、アトライタ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、２種以上の着色剤を含む光硬化性着色組成物は、各着色剤を別々にエチレン性不飽和化合物、透明樹脂および溶剤中に微細に分散したものを混合して製造することもできる。着色剤をエチレン性不飽和化合物、透明樹脂および溶剤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エチレン性不飽和化合物、透明樹脂および溶剤中に分散してなる光硬化性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。 The photocurable coloring composition of the present invention comprises one or two or more red colorants or green colorants, together with the photopolymerization initiator, in an ethylenically unsaturated compound, a transparent resin and a three-roll mill, It can be produced by finely dispersing using various dispersing means such as a two-roll mill, a sand mill, a kneader, and an attritor. Moreover, the photocurable coloring composition containing 2 or more types of colorants can also be produced by mixing each colorant separately with an ethylenically unsaturated compound, a transparent resin and a finely dispersed one in a solvent. . When dispersing the colorant in the ethylenically unsaturated compound, the transparent resin, and the solvent, a dispersion aid such as a resin-type pigment dispersant, a surfactant, and a dye derivative can be appropriately contained. The dispersion aid is excellent in dispersing the pigment and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, the dispersion aid is used to disperse the pigment in an ethylenically unsaturated compound, a transparent resin and a solvent. When a photocurable coloring composition is used, a color filter excellent in transparency can be obtained.
樹脂型顔料分散剤としては、顔料に吸着する性質を有する顔料親和性部位と、エチレン性不飽和化合物や透明樹脂と相溶性のある部位とを有し、顔料に吸着して顔料のエチレン性不飽和化合物や透明樹脂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。 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 ethylenically unsaturated compound or the transparent resin. It functions to stabilize dispersion in saturated compounds and transparent resins. 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 alkylene imines) with polyesters having free carboxyl groups, and the like Water-based dispersants such as oily dispersants such as salts, (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylic acid ester copolymers, styrene-maleic acid copolymers, 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.
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。 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.
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、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。 The dye derivative is a compound in which a substituent is introduced into an organic dye, and the organic dye includes a light yellow aromatic polycyclic compound such as a naphthalene-based or anthraquinone-based compound that is not generally called a dye. 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.
光硬化性着色組成物には、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、また、透明基板との密着性を高めるためにシランカップリング剤等の密着向上剤を含有させることもできる。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。 The photocurable coloring composition can contain a storage stabilizer in order to stabilize the viscosity of the composition with time, and in order to improve the adhesion to a transparent substrate, the adhesion improvement of a silane coupling agent or the like is improved. An agent can also be contained. 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.
シランカップリング剤としては、ビニルトリス（β−メトキシエトキシ）シラン、ビニルエトキシシラン、ビニルトリメトキシシラン等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の（メタ）アクリルシラン類、β−（３，４−エポキシシクロヘキシル）エチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）エチルトリエトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、Ｎ−β（アミノエチル）γ−アミノプロピルトリメトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルトリエトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリエトキシシラン等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン等のチオシラン類等が挙げられる。 Examples of the silane coupling agent include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3 , 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) ) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β ( Aminoethyl) γ-aminopro Lutriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N Examples include aminosilanes such as -phenyl-γ-aminopropyltriethoxysilane, thiosilanes such as γ-mercaptopropyltrimethoxysilane, and γ-mercaptopropyltriethoxysilane.
本発明の光硬化性着色組成物は、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。 The photocurable coloring composition 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.
次に、本発明のカラーフィルタについて説明する。
本発明のカラーフィルタは、本発明の光硬化性着色組成物から形成されるフィルタセグメントを備えるものである。一般的なカラーフィルタは、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つの緑色フィルタセグメント、および少なくとも１つの青色フィルタセグメントを具備するものであり、少なくとも１つの赤色フィルタセグメントおよび／または少なくとも１つの緑色フィルタセグメントが、本発明の光硬化性着色組成物から形成される。
青色フィルタセグメントは、本発明の光硬化性着色組成物中の赤色着色剤または緑色着色剤の代わりに青色顔料を含有する青色光硬化性性着色組成物を用いて形成することができる。青色顔料としては、例えばC.I. Pigment Blue １５、１５：１、１５：２、１５：３、１５：４、１５：６、１６、２２、６０、６４、８０等を用いることができる。青色顔料には、C.I. Pigment Violet １、１９、２３、２７、２９、３０、３２、３７、４０、４２、５０等の紫色顔料を併用することができる。
Next, the color filter of the present invention will be described.
The color filter of this invention is provided with the filter segment formed from the photocurable coloring composition of this invention. A typical color filter comprises at least one red filter segment, at least one green filter segment, and at least one blue filter segment, and has at least one red filter segment and / or at least one green filter segment. Is formed from the photocurable coloring composition of the present invention.
The blue filter segment can be formed using a blue light curable coloring composition containing a blue pigment in place of the red colorant or the green colorant in the photocurable coloring composition of the present invention. As a blue pigment, CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 80 etc. can be used, for example. Purple pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 can be used in combination with the blue pigment.
本発明のカラーフィルタは、フォリソグラフィー法により、本発明の赤色光硬化性着色組成物、緑色光硬化性着色組成物および前記青色光硬化性着色組成物を用いて、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。
基板としては、可視光に対して透過率の高い、ソーダ石灰ガラス、低アルカリ硼珪酸ガラス、無アルカリアルミノ硼珪酸ガラスなどのガラス板や、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。また、ガラス板や樹脂板の表面には、パネル化後の液晶駆動のために、酸化インジウム、酸化錫などからなる透明電極が形成されていてもよい。
フィルタセグメントの乾燥膜厚は、０．２〜１０μｍであることが好ましく、より好ましくは０．２〜５μｍである。塗布膜を乾燥させる際には、減圧乾燥機、コンベクションオーブン、ＩＲオーブン、ホットプレート等を使用してもよい。
The color filter of the present invention is prepared by using the red light curable coloring composition, the green light curable coloring composition, and the blue light curable coloring composition of the present invention on a substrate by a photolithography method. Can be manufactured.
Substrates include glass plates such as soda lime glass, low alkali borosilicate glass, and non-alkali aluminoborosilicate glass that have a high transmittance for visible light, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate. Used. In addition, a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
The dry film thickness of the filter segment is preferably 0.2 to 10 μm, more preferably 0.2 to 5 μm. When drying the coating film, a vacuum dryer, a convection oven, an IR oven, a hot plate, or the like may be used.
フォトリソグラフィー法による各色フィルタセグメントの形成は、下記の方法で行う。すなわち、溶剤現像型あるいはアルカリ現像型に調製した光硬化性着色組成物を、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０．２〜１０μｍ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所望のパターンを形成してフィルタセグメントを形成することができる。さらに、光硬化性着色組成物の硬化を促進するため、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、印刷法より精度の高いフィルタセグメントが形成できる。 The formation of each color filter segment by photolithography is performed by the following method. That is, the photocurable coloring composition prepared in a solvent development type or an alkali development type is dried on a substrate by a coating method such as spray coating, spin coating, slit coating, roll coating, etc. Apply so that 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. Thereafter, the filter segment can be formed by immersing in a solvent or an alkaline developer, or spraying the developer by spraying or the like to remove the uncured portion and forming a desired pattern. Furthermore, in order to accelerate | stimulate hardening of a photocurable coloring composition, it can also heat as needed. According to the photolithography method, a filter segment with higher accuracy than the printing method can be formed.
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。
現像処理方法としては、シャワー現像法、スプレー現像法、ディップ（浸漬）現像法、パドル（液盛り）現像法等を適用することができる。
なお、紫外線露光感度を上げるために、光硬化性着色組成物を塗布乾燥後、水溶性あるいはアルカリ可溶性樹脂、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、酸素による硬化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。
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.
As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
In order to increase the UV exposure sensitivity, a film that prevents the inhibition of curing by oxygen by applying and drying a water-soluble or alkali-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin after applying and drying the photocurable coloring composition. After forming, UV exposure can also be performed.
以下に、実施例により本発明をより具体的に説明するが、本発明はその要旨を超えない限り以下の実施例に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」を意味する。
まず、実施例および比較例で用いたアクリル樹脂溶液の調製について説明する。樹脂の分子量は、GPC（ゲルパーミエーションクロマトグラフィ）により測定したポリスチレン換算の重量平均分子量である。
Hereinafter, the present invention will be described more specifically by way of examples. However, the present invention is not limited to the following examples unless it exceeds the gist.
In the examples and comparative examples, “parts” means “parts by weight”.
First, preparation of acrylic resin solutions used in Examples and Comparative Examples will be described. The molecular weight of the resin is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography).
［アクリル樹脂溶液の調製］
反応容器にシクロヘキサノン４５０部を入れ、容器に窒素ガスを注入しながら８０℃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。
メタクリル酸 ２０．０部
メチルメタクリレート １０．０部
ブチルメタクリレート ５５．０部
ヒドロキシエチルメタクリレート １５．０部
アゾビスイソブチロニトリル ４．０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時間反応を続けてアクリル樹脂の溶液を得た。アクリル樹脂の重量平均分子量は、約４００００であった。
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重量％に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。
[Preparation of acrylic resin solution]
450 parts of cyclohexanone was placed in a reaction vessel, heated to 80 ° 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.
Methacrylic acid 20.0 parts
Methyl methacrylate 10.0 parts
Butyl methacrylate 55.0 parts
Hydroxyethyl methacrylate 15.0 parts
Azobisisobutyronitrile 4.0 parts After the 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 further at 100 ° C. The reaction was continued for 1 hour to obtain an acrylic resin solution. The weight average molecular weight of the acrylic resin was about 40,000.
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% by weight. To prepare an acrylic resin solution.
［赤色顔料分散体の調整］
下記の組成の混合物を均一に撹拌混合し、直径１ｍｍのジルコニアビーズを用いて、サンドミルで５時間分散した後、５μｍのフィルタで濾過し赤色顔料分散体を作製した。
ジケトピロロピロール系赤色顔料(C.I. Pigment Red 254) １０．０部
（チバガイギー社製「イルガフォーレッドＢ−ＣＦ」）
アントラキノン系赤色顔料(C.I. Pigment Red 177) １．６部
（チバガイギー社製「クロモフタールレッドＡ２Ｂ」）
メチン・アゾメチン系黄色顔料(C.I. Pigment Yellow 139) ０．４部
（チバガイギー社製「イルガフォアイエロー ２Ｒ−ＣＦ」）
分散剤（ゼネカ社製「ソルスパース２００００」） ２．４部
アクリル樹脂溶液 ２８．０部
シクロヘキサノン ５７．６部
[Adjustment of red pigment dispersion]
A mixture having the following composition was stirred and mixed uniformly, dispersed with a sand mill for 5 hours using zirconia beads having a diameter of 1 mm, and then filtered with a 5 μm filter to prepare a red pigment dispersion.
Diketopyrrolopyrrole red pigment (CI Pigment Red 254) 10.0 parts ("Irga Four Red B-CF" manufactured by Ciba Geigy)
1.6 parts of anthraquinone red pigment (CI Pigment Red 177) (Chromotal Red A2B manufactured by Ciba Geigy)
0.4 parts of methine / azomethine yellow pigment (CI Pigment Yellow 139) (“Irgafore Yellow 2R-CF” manufactured by Ciba Geigy)
Dispersant (“Solsperse 20000” manufactured by Zeneca) 2.4 parts Acrylic resin solution 28.0 parts Cyclohexanone 57.6 parts
［緑色顔料分散体の調整］
下記の組成の混合物を均一に撹拌混合し、直径１ｍｍのジルコニアビーズを用いて、サンドミルで５時間分散した後、５μｍのフィルタで濾過し緑色顔料分散体を作製した。
ハロゲン化銅フタロシアニン系緑色顔料(C.I. Pigment Green 36) ８．２部
（東洋インキ製造社製「リオノールグリーン６ＹＫ」）
モノアゾ系黄色顔料(C.I. Pigment Yellow 150) ５．８部
（バイエル社製「ファンチョンファーストエローＹ−５６８８」）
分散剤（ゼネカ社製「ソルスパース２００００」） ２．８部
アクリル樹脂溶液 １６．０部
シクロヘキサノン ６７．２部
[Adjustment of green pigment dispersion]
A mixture having the following composition was stirred and mixed uniformly, dispersed with a sand mill for 5 hours using zirconia beads having a diameter of 1 mm, and then filtered with a 5 μm filter to prepare a green pigment dispersion.
Halogenated copper phthalocyanine-based green pigment (CI Pigment Green 36) 8.2 parts ("Rionol Green 6YK" manufactured by Toyo Ink Co., Ltd.)
5.8 parts of monoazo yellow pigment (CI Pigment Yellow 150) (“Funchon First Yellow Y-5688” manufactured by Bayer)
Dispersant (“Solsperse 20000” manufactured by Zeneca) 2.8 parts Acrylic resin solution 16.0 parts Cyclohexanone 67.2 parts
［実施例１〜１６および比較例１〜４］（光硬化性着色組成物の調整）
表１〜２に示す配合組成で、混合物を均一になるように攪拌混合した後、１μｍのフィルタで濾過して、光硬化性着色組成物を得た。
ただし、実施例１、３、４、８、１２、１４、および１５は参考例である。
After the mixture was stirred and mixed with the composition shown in Tables 1 and 2 so as to be uniform, the mixture was filtered through a 1 μm filter to obtain a photocurable coloring composition.
However, Examples 1, 3, 4, 8, 12, 14, and 15 are reference examples.
光重合開始剤の含有量：光硬化性着色組成物中の全固形分を基準（１００重量％）とした 光重合開始剤の含有量
モノマー ：ジペンタエリスリトールペンタ及びヘキサアクリレート
（東亞合成社製「Ｍ４００」）
光重合開始剤Ａ：２−（ジメチルアミノ）−２−[（４−メチルフェニル）メチル]−１ −[４−（４−モルホリニル）フェニル]−１−ブタノン
（チバ・スペシャルティ・ケミカルズ社製「イルガキュア ３７９」、 365nmにおける吸光度：0.029）
光重合開始剤Ｂ：１，２-オクタンジオン−１−〔４−（フェニルチオ）−２−（Ｏ−ベ ンゾイルオキシム）〕（チバ・スペシャルティ・ケミカルズ社製「イル ガキュア ＯＸＥ０１」、365nmにおける吸光度：0.060）
光重合開始剤Ｃ：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)-ブタノン-１（チバ・スペシャルティ・ケミカルズ社製「イルガ キュア ３６９」、365nmにおける吸光度：0.032）
光重合開始剤Ｄ：２−メチル−１−[４−（メチルチオ）フェニル]−２−モルフォリノ プロパン−１−オン （チバ・スペシャルティ・ケミカルズ社製「イル ガキュア ９０７」）
光重合開始剤Ｅ：ビス（２，４，６−トリメチルベンゾイル）フェニルホスフィンオキサ イド（チバ・スペシャルティ・ケミカルズ社製「イルガキュア ８１９ 」、365における吸光度：0.023）
光重合開始剤Ｆ：２,４−ジエチルチオキサントン（365nmにおける吸光度：0.18）
増感剤 ：４，４'−ビス（ジエチルアミノ）ベンゾフェノン
（365nmにおける吸光度：1.2）
溶剤 ：プロピレングリコールモノメチルエーテルアセテート
Content of photopolymerization initiator: Content of photopolymerization initiator based on the total solid content in the photocurable coloring composition (100% by weight) Monomer: Dipentaerythritol penta and hexaacrylate (manufactured by Toagosei Co., Ltd. M400 ")
Photopolymerization initiator A: 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (manufactured by Ciba Specialty Chemicals) IRGACURE 379 ”, absorbance at 365 nm: 0.029)
Photopolymerization initiator B: 1,2-octanedione-1- [4- (phenylthio) -2- (O-benzoyloxime)] (“Irgacure OXE01” manufactured by Ciba Specialty Chemicals, Inc., absorbance at 365 nm : 0.060)
Photopolymerization initiator C: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (“Irgacure 369” manufactured by Ciba Specialty Chemicals, absorbance at 365 nm: 0.032)
Photopolymerization initiator D: 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one (“Irgacure 907” manufactured by Ciba Specialty Chemicals)
Photopolymerization initiator E: bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide (“Irgacure 819” manufactured by Ciba Specialty Chemicals, absorbance at 365: 0.023)
Photopolymerization initiator F: 2,4-diethylthioxanthone (absorbance at 365 nm: 0.18)
Sensitizer: 4,4′-bis (diethylamino) benzophenone (absorbance at 365 nm: 1.2)
Solvent: Propylene glycol monomethyl ether acetate
［フィルタセグメントの形成］
得られた光硬化性着色組成物をスピンコート法により１０cm×１０cmのガラス基板にポストベーク後の膜厚が、１．９μｍになるよう塗工した後、クリーンオーブン中で、７０℃で１５分間プリベークした。次いで、この基板を室温に冷却後、超高圧水銀ランプを用い、フォトマスクを介して紫外線を露光した。その後、この基板を２３℃の炭酸ナトリウム水溶液を用いてスプレー現像した後、イオン交換水で洗浄し、風乾した。その後、クリーンオーブン中で、２３０℃で２０分間ポストベークを行い、基板上にストライプ状のフィルタセグメントを形成した。
[Formation of filter segment]
The obtained photocurable coloring composition was applied to a 10 cm × 10 cm glass substrate by spin coating so that the film thickness after post-baking was 1.9 μm, and then in a clean oven at 70 ° C. for 15 minutes. Pre-baked. Next, after cooling the substrate to room temperature, ultraviolet rays were exposed through a photomask using an ultrahigh pressure mercury lamp. Thereafter, the substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, and air-dried. Thereafter, post-baking was performed at 230 ° C. for 20 minutes in a clean oven to form striped filter segments on the substrate.
［評価］
得られた光硬化性着色組成物を用いて形成されたフィルタセグメントのパタ−ン形状を下記の方法で評価した。結果を表３〜４に示す。
[Evaluation]
The pattern shape of the filter segment formed using the obtained photocurable coloring composition was evaluated by the following method. The results are shown in Tables 3-4.
（フィルタセグメントのパタ−ン形状）
（１）パタ−ンの直線性
光学顕微鏡によりパターンの直線性を観察して評価を行った。評価のランクは次の通りである。
○：直線性良好
△：部分的に直線性良好
×：直線性不良
（２）パタ−ンの断面形状
走査型電子顕微鏡（ＳＥＭ）によりパターンの断面形状を観察して評価を行った。評価のランクは次の通りである。
○：順テーパー形状。
△：垂直形状。
×：逆テーパー形状。
(Filter segment pattern shape)
(1) Pattern linearity The linearity of the pattern was observed and evaluated using an optical microscope. The rank of evaluation is as follows.
○: Good linearity Δ: Partially good linearity ×: Poor linearity (2) Cross-sectional shape of the pattern The cross-sectional shape of the pattern was observed and evaluated by a scanning electron microscope (SEM). The rank of evaluation is as follows.
○: Forward tapered shape.
Δ: Vertical shape.
X: Reverse taper shape.
表３〜４に示すように、光重合開始剤の含有量が光硬化性着色組成物中の全固形分の重量を基準（１００重量％）として１８．０〜３０重量％である実施例２、５〜７、９、１０、１１、１３および１６の光硬化性着色組成物を用いて形成されたフィルタセグメントは、パタ−ンの直線性および断面形状が良好であった。これに対し、光重合開始剤の含有量が１０重量％と少ない比較例１〜４の光硬化性着色組成物を用いて形成されたフィルタセグメントは、パタ−ンの断面形状が不良であった。
As shown in Tables 3 to 4, Example 2 in which the content of the photopolymerization initiator is 18.0 to 30% by weight based on the weight of the total solid content in the photocurable coloring composition (100% by weight) The filter segments formed using the photocurable coloring compositions of Nos. 5 to 7, 9, 10, 11, 13, and 16 had good pattern linearity and cross-sectional shape. On the other hand, the filter segment formed using the photocurable coloring composition of Comparative Examples 1 to 4 having a low content of the photopolymerization initiator of 10% by weight had a poor pattern cross-sectional shape. .
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