JP2022092559A - Photosensitive coloring composition, cured film, and optical filter - Google Patents
Photosensitive coloring composition, cured film, and optical filter Download PDFInfo
- Publication number
- JP2022092559A JP2022092559A JP2021041958A JP2021041958A JP2022092559A JP 2022092559 A JP2022092559 A JP 2022092559A JP 2021041958 A JP2021041958 A JP 2021041958A JP 2021041958 A JP2021041958 A JP 2021041958A JP 2022092559 A JP2022092559 A JP 2022092559A
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- JP
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- Prior art keywords
- coloring composition
- parts
- photosensitive coloring
- mass
- meth
- 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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- 238000004040 coloring Methods 0.000 title claims abstract description 109
- 230000003287 optical effect Effects 0.000 title claims description 16
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- 239000011347 resin Substances 0.000 claims abstract description 107
- 239000000049 pigment Substances 0.000 claims abstract description 94
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- 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 abstract description 25
- 239000003999 initiator Substances 0.000 claims abstract description 20
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- 239000000178 monomer Substances 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
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- 150000005309 metal halides Chemical class 0.000 claims description 17
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- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 2
- 230000036211 photosensitivity Effects 0.000 claims description 2
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
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- 238000006116 polymerization reaction Methods 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 7
- 230000008034 disappearance Effects 0.000 description 7
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- KXEMQEGRZWUKJS-QIYNHLNTSA-N tetraphylline Chemical class COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-QIYNHLNTSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- GAMLUOSQYHLFCT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-3-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1(CC)COC1 GAMLUOSQYHLFCT-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QHCNTMCHBZHBDY-UHFFFAOYSA-N trihydroxy-(6-methylheptyl)-phenyl-lambda5-phosphane Chemical compound CC(C)CCCCCP(O)(O)(O)C1=CC=CC=C1 QHCNTMCHBZHBDY-UHFFFAOYSA-N 0.000 description 1
- SFESXIFARCRODZ-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-phenyl-$l^{5}-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C1=CC=CC=C1 SFESXIFARCRODZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Description
本発明は、感光性着色組成物、硬化膜、及び光学フィルタに関する。 The present invention relates to a photosensitive coloring composition, a cured film, and an optical filter.
光学フィルタは、画像の明るさの調整や像コントラストの改善、特定波長の透過や反射、また一つの画像を2つ独立した画像に特定比率で分割するといった様々な目的で使用され、カメラ、液晶や有機エレクトロルミネッセンス等の画像表示装置、C-MOS(Complementray Metal Oxide Semiconductor)イメージセンサ、CCD(Charge Coupled Device)イメージセンサ等の固体撮像素子、赤外線センサ、生体認証センサなどの機器・装置に使用されている。 Optical filters are used for various purposes such as adjusting the brightness of an image, improving image contrast, transmitting and reflecting a specific wavelength, and dividing one image into two independent images at a specific ratio. Used in image display devices such as organic electroluminescence, C-MOS (Complementary Metal Oxide Contrast) image sensors, solid-state image sensors such as CCD (Change Coupled Device) image sensors, infrared sensors, biometric authentication sensors, and other devices and devices. ing.
近年、光学フィルタは、高い色分離性や高精細化を要求されている。これらの要求を満たすために、光学フィルタを形成する組成物に含まれる着色剤の高濃度化や、高膜厚化などが検討されている。しかし、着色剤の高濃度化や高膜厚化した場合、硬化時に膜の表面にシワが発生する問題や、現像性やパターン形成性が悪化するといった問題があった。特に、着色剤に、紫外線領域における吸光度が高く、紫外線光を透過し難いハロゲン化金属フタロシアニン顔料を用いた場合に、これらの問題はより顕著になり、改善が求められていた。 In recent years, optical filters are required to have high color separation and high definition. In order to satisfy these requirements, it has been studied to increase the concentration of the colorant contained in the composition forming the optical filter and to increase the film thickness. However, when the concentration and the film thickness of the colorant are increased, there are problems that wrinkles are generated on the surface of the film at the time of curing and that the developability and the pattern forming property are deteriorated. In particular, when a metal halide phthalocyanine pigment having high absorbance in the ultraviolet region and difficult to transmit ultraviolet light is used as the colorant, these problems become more prominent and improvement is required.
上記の問題を解決するために、様々な取り組みがなされている。特許文献1には、アクリロイル基又はエポキシ基を有するアルカリ可溶性樹脂、アルキレンオキサイド構造を有する光重合性化合物、及び光重合開始剤としてオキシムエステル化合物を含む感光性樹脂組成物が開示さている。また、特許文献2には、二重結合当量が400g/mol以下であり、かつ、ビスフェノール骨格を有する光重合性モノマーを含有する着色樹脂組成物が開示されている。 Various efforts have been made to solve the above problems. Patent Document 1 discloses a photosensitive resin composition containing an alkali-soluble resin having an acryloyl group or an epoxy group, a photopolymerizable compound having an alkylene oxide structure, and an oxime ester compound as a photopolymerization initiator. Further, Patent Document 2 discloses a colored resin composition having a double bond equivalent of 400 g / mol or less and containing a photopolymerizable monomer having a bisphenol skeleton.
しかし、特許文献1、2に記載の組成物では、特に高膜厚化した場合の硬化時のシワ、現像性、及びパターン形成性は十分ではない。また、色分離性に関しては考慮されていない。 However, the compositions described in Patent Documents 1 and 2 do not have sufficient wrinkles, developability, and pattern-forming property at the time of curing, especially when the film thickness is increased. Also, no consideration is given to color separability.
本発明は、高膜厚化した場合であっても、硬化時のシワの発生が少なく、現像性、パターン形成性に優れ、かつ色分離性に優れた感光性着色組成物を提供することを課題とする。 INDUSTRIAL APPLICABILITY The present invention provides a photosensitive coloring composition which is less likely to cause wrinkles during curing even when the film thickness is increased, is excellent in developability and pattern formation, and is excellent in color separation. Make it an issue.
本発明は、有機顔料(A)、アルカリ可溶性樹脂(B)、重合性化合物(C)、光重合開始剤(D)、及びシリカ粒子(E)を含む、感光性着色組成物であって、
前記有機顔料(A)が、ハロゲン化金属フタロシアニン顔料(A-1)、及びイソインドリン顔料(A-2)を含み、
前記重合性化合物(C)が、ウレタン結合を有する重合性化合物(C-1)を含み、
前記有機顔料(A)の含有量が、感光性着色組成物の不揮発分100質量%中、25質量%以上である、感光性着色組成物に関する。
The present invention is a photosensitive coloring composition containing an organic pigment (A), an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and silica particles (E).
The organic pigment (A) contains a metal halide phthalocyanine pigment (A-1) and an isoindoline pigment (A-2).
The polymerizable compound (C) contains a polymerizable compound (C-1) having a urethane bond, and contains
The present invention relates to a photosensitive coloring composition in which the content of the organic pigment (A) is 25% by mass or more in 100% by mass of the non-volatile content of the photosensitive coloring composition.
また、本発明は、前記重合性化合物(C)が、さらに前記ウレタン結合を有する重合性化合物(C-1)以外の重合性化合物(C-2)を含む、上記感光性着色組成物に関する。 The present invention also relates to the above-mentioned photosensitive coloring composition, wherein the polymerizable compound (C) further contains a polymerizable compound (C-2) other than the polymerizable compound (C-1) having a urethane bond.
また、本発明は、前記ウレタン結合を有する重合性化合物(C-1)と前記重合性化合物(C-2)の質量比が、80:20~20:80である上記感光性着色組成物に関する。 The present invention also relates to the photosensitive coloring composition in which the mass ratio of the polymerizable compound (C-1) having a urethane bond to the polymerizable compound (C-2) is 80:20 to 20:80. ..
また、本発明は、前記ウレタン結合を有する重合性化合物(C-1)は、酸基を有する、上記感光性着色組成物に関する。 The present invention also relates to the above-mentioned photosensitive coloring composition in which the polymerizable compound (C-1) having a urethane bond has an acid group.
また、本発明は、前記アルカリ可溶性樹脂(B)が、脂環式炭化水素構造含有単量体単位(b1)、及びカルボキシル基含有単量体単位(b2)とを含有するアルカリ可溶性樹脂(B-1)を含む、上記感光性着色組成物に関する。 Further, in the present invention, the alkali-soluble resin (B) contains an alicyclic hydrocarbon structure-containing monomer unit (b1) and a carboxyl group-containing monomer unit (b2) (B). -1), the above-mentioned photosensitive coloring composition.
また、本発明は、前記アルカリ可溶性樹脂(B-1)が、前記脂環式炭化水素構造含有単量体単位(b1)を、前記アルカリ可溶性樹脂(B-1)の全構成単位100質量%中、5~60質量%含む、上記感光性着色組成物に関する。 Further, in the present invention, the alkali-soluble resin (B-1) contains the alicyclic hydrocarbon structure-containing monomer unit (b1) in an amount of 100% by mass of all the constituent units of the alkali-soluble resin (B-1). The present invention relates to the above-mentioned photosensitive coloring composition containing 5 to 60% by mass.
また、本発明は、前記ハロゲン化金属フタロシアニン顔料(A-1)とイソインドリン顔料(A-2)との質量比が、97:3~40:60である、上記感光性着色組成物に関する。 The present invention also relates to the above-mentioned photosensitive coloring composition in which the mass ratio of the metal halide phthalocyanine pigment (A-1) to the isoindoline pigment (A-2) is 97: 3 to 40:60.
また、本発明は、前記シリカ粒子(E)の含有量が、感光性着色組成物の不揮発分100質量%中、5~30質量%である、上記感光性着色組成物に関する。 The present invention also relates to the above-mentioned photosensitive coloring composition in which the content of the silica particles (E) is 5 to 30% by mass in 100% by mass of the non-volatile content of the photosensitive coloring composition.
また、本発明は、さらに、近赤外線吸収剤(H)を含む、上記感光性着色組成物に関する。 The present invention further relates to the above-mentioned photosensitive coloring composition containing a near-infrared absorber (H).
また、本発明は、上記感光性着色組成物を硬化して得られる、硬化膜に関する。 The present invention also relates to a cured film obtained by curing the photosensitive coloring composition.
また、本発明は、上記硬化膜を有する光学フィルタであって、前記硬化膜の膜厚が4.0μm以上である、光学フィルタに関する。 The present invention also relates to an optical filter having the cured film having a film thickness of 4.0 μm or more.
上記の本発明によれば、高膜厚化した場合であっても、硬化時のシワの発生が少なく、現像性、パターン形成性に優れ、かつ色分離性に優れた感光性着色組成物を提供できる。 According to the above invention, even when the film thickness is increased, a photosensitive coloring composition having less wrinkles during curing, excellent developability and pattern forming property, and excellent color separation property can be obtained. Can be provided.
以下に、本発明の感光性着色組成物を実施するための形態について詳細に説明する。なお、本発明は、以下の実施形態に制限されるものではなく、課題を解決可能な範囲内で変形して実施できる。 Hereinafter, embodiments for carrying out the photosensitive coloring composition of the present invention will be described in detail. The present invention is not limited to the following embodiments, and can be modified and implemented within a range in which the problem can be solved.
本明細書では、「(メタ)アクリロイル」、「(メタ)アクリル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、又は「(メタ)アクリルアミド」とは、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタアクリロイル」、「アクリル及び/又はメタアクリル」、「アクリル酸及び/又はメタアクリル酸」、「アクリレート及び/
又はメタクリレート」、又は「アクリルアミド及び/又はメタアクリルアミド」を意味する。また、「C.I.」は、カラーインデックス(C.I.;The Society of Dyers and Colourists発行)を意味する。重合性不飽和基は、エチレン性不飽和二重結合である。
In the present specification, "(meth) acryloyl", "(meth) acrylic", "(meth) acrylic acid", "(meth) acrylate", or "(meth) acrylamide" are referred to as "(meth) acrylamide" unless otherwise specified. "Acryloyl and / or metaacryloyl", "acrylic and / or methacrylic acid", "acrylic acid and / or methacrylic acid", "acrylate and /", respectively.
Or methacrylate ", or" acrylamide and / or metaacrylamide ". Further, "CI" means a color index (CI; The Society of Dyers and Colorists). The polymerizable unsaturated group is an ethylenically unsaturated double bond.
<感光性着色組成物>
本発明は、有機顔料(A)、アルカリ可溶性樹脂(B)、重合性化合物(C)、光重合開始剤(D)、及びシリカ粒子(E)を含む、感光性着色組成物であって、
前記有機顔料(A)が、ハロゲン化金属フタロシアニン顔料(A-1)、及びイソインドリン顔料(A-2)を含み、
前記重合性化合物(C)が、ウレタン結合を有する重合性化合物(C-1)を含み、
前記有機顔料(A)の含有量が、感光性着色組成物の不揮発分100質量%中、25質量%以上である、感光性着色組成物である。
<Photosensitive coloring composition>
The present invention is a photosensitive coloring composition containing an organic pigment (A), an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and silica particles (E).
The organic pigment (A) contains a metal halide phthalocyanine pigment (A-1) and an isoindoline pigment (A-2).
The polymerizable compound (C) contains a polymerizable compound (C-1) having a urethane bond, and contains
The photosensitive coloring composition has a content of the organic pigment (A) of 25% by mass or more in 100% by mass of the non-volatile content of the photosensitive coloring composition.
上記のような構成をとる感光性着色組成物で、本発明の課題を解決できるメカニズムは明らかではないが、本発明者らは、以下のように推測している。 Although the mechanism by which the problem of the present invention can be solved by the photosensitive coloring composition having the above-mentioned structure is not clear, the present inventors speculate as follows.
着色剤の高濃度化や高膜厚化すると、紫外線領域の光で感光性着色組成物を露光し硬化させる際、光が感光性着色組成物層の内部まで届かないため、表面と内部で硬化収縮度合いに差ができることで表面にシワが発生する。
しかし、シリカ粒子(E)は、透過性が高いため組成物層に光を通す道ができ、硬化性が改善すると考えられる。さらに、ウレタン結合を有する重合性化合物(C-1)のウレタン結合部分が硬化時の収縮を吸収、又は抑制し、シワの発生を抑えると考えられる。
そして、特定の有機顔料と含有量を組み合わせることで、各波長領域の透過率を制御し、優れた色分離性が得られたと考えられる。
When the concentration and film thickness of the colorant are increased, when the photosensitive coloring composition is exposed to light in the ultraviolet region and cured, the light does not reach the inside of the photosensitive coloring composition layer, so that the light does not reach the inside of the photosensitive coloring composition layer and is cured on the surface and inside. Wrinkles occur on the surface due to the difference in the degree of shrinkage.
However, since the silica particles (E) have high transparency, it is considered that a path for light to pass through the composition layer is formed and the curability is improved. Further, it is considered that the urethane-bonded portion of the polymerizable compound (C-1) having a urethane bond absorbs or suppresses shrinkage during curing and suppresses the generation of wrinkles.
Then, it is considered that the transmittance in each wavelength region was controlled by combining the content with a specific organic pigment, and excellent color separation was obtained.
[有機顔料(A)]
本発明の感光性着色組成物は、有機顔料(A)として、ハロゲン化金属フタロシアニン顔料(A-1)、及びイソインドリン顔料(A-2)を含み、有機顔料(A)の含有量が、感光性着色組成物の不揮発分100質量%中、25質量%以上である。
[Organic pigment (A)]
The photosensitive coloring composition of the present invention contains the halogenated metal phthalocyanine pigment (A-1) and the isoindoline pigment (A-2) as the organic pigment (A), and the content of the organic pigment (A) is high. It is 25% by mass or more in 100% by mass of the non-volatile content of the photosensitive coloring composition.
本発明の感光性着色組成物は、色分離性、シワの抑制の観点から、有機顔料(A)の含有量は、感光性着色組成物の不揮発分100質量%中、25~40質量%がより好ましく、25~35質量%が特に好ましい。 From the viewpoint of color separation and suppression of wrinkles, the photosensitive coloring composition of the present invention contains 25 to 40% by mass of the organic pigment (A) in 100% by mass of the non-volatile content of the photosensitive coloring composition. More preferably, 25 to 35% by mass is particularly preferable.
(ハロゲン化金属フタロシアニン顔料(A-1))
ハロゲン化金属フタロシアニン顔料(A-1)は、特に制限がなく、公知のものを用いることができる。具体的には、C.I.ピグメントグリーン7,10,36,37,58,59,62,63、特開2008-19383号公報、特開2007-320986号公報、特開2004-70342号公報、特許第4893859号公報、特開2016-57635号公報、特開2016-153481号公報、特開2017-197685号公報等に記載の顔料が挙げられる。なかでも、青色領域(波長400~500nmに高い透過率を有する領域)との色分離性の観点から、中心金属が、亜鉛、又はアルミニウムであるハロゲン化金属フタロシアニン顔料が好ましく、亜鉛であるハロゲン化金属フタロシアニン顔料がより好ましい。中心金属が亜鉛であるハロゲン化金属フタロシアニン顔料としては、C.I.ピグメントグリーン58,59が挙げられる。
(Metal halide phthalocyanine pigment (A-1))
The metal halide phthalocyanine pigment (A-1) is not particularly limited, and known ones can be used. Specifically, C.I. I. Pigment Green 7,10,36,37,58,59,62,63, JP-A-2008-19383, JP-A-2007-320986, JP-A-2004-70342, Patent No. 4893859, JP-A. Examples thereof include pigments described in JP-A-2016-57635, JP-A-2016-153481, JP-A-2017-197685, and the like. Among them, a halogenated metal phthalocyanine pigment in which the central metal is zinc or aluminum is preferable, and halogenation in which zinc is used, from the viewpoint of color separation from the blue region (region having a high transmittance at a wavelength of 400 to 500 nm). Metallic phthalocyanine pigments are more preferred. Examples of the metal halide phthalocyanine pigment in which the central metal is zinc include C.I. I. Pigment greens 58 and 59 can be mentioned.
ハロゲン化金属フタロシアニン顔料(A-1)は、単独または2種類以上を併用して使用できる。 The metal halide phthalocyanine pigment (A-1) can be used alone or in combination of two or more.
(イソインドリン顔料(A-2))
イソインドリン顔料(A-2)は、特に制限がなく、公知のものを用いることができる。具体的には、C.I.ピグメントイエロー139,185が挙げられ、青色領域の色分離性の観点から、C.I.ピグメントイエロー139がより好ましい。
(Isoindoline pigment (A-2))
The isoindoline pigment (A-2) is not particularly limited, and known ones can be used. Specifically, C.I. I. Pigment Yellow 139,185, and C.I. I. Pigment Yellow 139 is more preferred.
イソインドリン顔料(A-2)は、単独または2種類以上を併用して使用できる。 The isoindoline pigment (A-2) can be used alone or in combination of two or more.
本発明の感光性着色組成物は、青色領域、及び赤色領域(波長580nmより長波長側に高い透過率を有する領域)との色分離性の観点から、ハロゲン化金属フタロシアニン顔料(A-1)とイソインドリン顔料(A-2)の質量比は、97:3~40:60が好ましく、95:5~50:50がより好ましい。 The photosensitive coloring composition of the present invention has a halogenated metal phthalocyanine pigment (A-1) from the viewpoint of color separation from a blue region and a red region (a region having a high transmittance on the wavelength side longer than the wavelength of 580 nm). The mass ratio of the isoindoline pigment (A-2) to the isoindoline pigment (A-2) is preferably 97: 3 to 40:60, more preferably 95: 5 to 50:50.
(その他有機顔料(A-3))
本発明の感光性着色組成物は、ハロゲン化金属フタロシアニン顔料(A-1)、及びイソインドリン顔料(A-2)以外のその他有機顔料(A-3)を含有することができる。
(Other organic pigments (A-3))
The photosensitive coloring composition of the present invention can contain a metal halide phthalocyanine pigment (A-1) and other organic pigments (A-3) other than the isoindoline pigment (A-2).
その他有機顔料(A-3)としては、例えば、C.I.ピグメントレッド1,2,3,4,5,6,7,8,9,12,14,15,16,17,21,22,23,31,32,37,38,41,47,48,48:1,48:2,48:3,48:4,49,49:1,49:2,50:1,52:1,52:2,53,53:1,53:2,53:3,57,57:1,57:2,58:4,60,63,63:1,63:2,64,64:1,68,69,81,81:1,81:2,81:3,81:4,83,88,90:1,101,101:1,104,108,108:1,109,112,113,114,122,123,144,146,147,149,151,166,168,169,170,172,173,174,175,176,177,178,179,181,184,185,187,188,190,193,194,200,202,206,207,208,209,210,214,216,220,221,224,230,231,232,233,235,236,237,238,239,242,243,245,247,249,250,251,253,254,255,256,257,258,259,260,262,263,264,265,266,267,268,269,270,271,272,273,274,275,276,277,278,279,280,281,282,283,284,285,286,287,291,295,296、特開2014-134712号公報に記載された顔料、特許第6368844号公報に記載された顔料等の赤色有機顔料、
C.I.ピグメントオレンジ36,38,43,62,64,71,73等の橙色有機顔料、
C.I.ピグメントイエロー1,2,3,4,5,6,10,12,13,14,15,16,17,18,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,126,127,128,129,138,139,147,150,151,152、153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,192,193,194,196,198,199,213,214,231,233、特開2012-226110号公報に記載された顔料等の黄色有機顔料、
C.I.ピグメントグリーン1,2,4,7,8,10,13,14,15,17,18,19,26,36,37,45,48,50,51,54,55等の緑色有機顔料、
C.I.ピグメントブルー1,1:2,9,14,15,15:1,15:2,15:
3,15:4,15:6,16,17,19,25,27,28,29,33,35,36,56,56:1,60,61,61:1,62,63,66,67,68,71,72,73,74,75,76,78,79等の青色有機顔料、
C.I.ピグメントバイオレット1,1:1,2,2:2,3,3:1,3:3,5,5:1,14,15,16,19,23,25,27,29,31,32,37,39,42,44,47,49,50等の紫色有機顔料等が挙げられる。
Other organic pigments (A-3) include, for example, C.I. I. Pigment Red 1,2,3,4,5,6,7,8,9,12,14,15,16,17,21,22,23,31,32,37,38,41,47,48, 48: 1,48: 2,48: 3,48: 4,49,49: 1,49: 2,50: 1,52: 1,52: 2,53,53: 1,53: 2,53: 3,57,57: 1,57: 2,58: 4,60,63,63: 1,63: 2,64,64: 1,68,69,81,81: 1,81: 2,81: 3,81: 4,83,88,90: 1,101,101: 1,104,108,108: 1,109,112,113,114,122,123,144,146,147,149,1511 166,168,169,170,172,173,174,175,176,177,178,179,181,184,185,187,188,190,193,194,200,202,206,207,208, 209,210,214,216,220,221,224,230,231,232,233,235,236,237,238,239,242,243,245,247,249,250,251,253,254 255,256,257,258,259,260,262,263,264,265,266,267,268,269,270,271,272,273,274,275,276,277,278,279,280, 281,282,283,284,285,286,287,291,295,296, red organic pigments such as pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844.
C. I. Pigment Orange 36, 38, 43, 62, 64, 71, 73 and other orange organic pigments,
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, 104,106,108,109,110,113,114,115,116,117,118,119,120,123,126,127,128,129,138,139,147,150,151,152,153 154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188, 192,193,194,196,198,199,213,214,231,233, Yellow organic pigments such as the pigments described in JP2012-226110A.
C. I. Pigment Green 1,2,4,7,8,10,13,14,15,17,18,19,26,36,37,45,48,50,51,54,55 and other green organic pigments,
C. I. Pigment Blue 1,1: 2,9,14,15,15: 1,15: 2,15:
3,15: 4,15: 6,16,17,19,25,27,28,29,33,35,36,56,56:1,60,61,61:1,62,63,66, Blue organic pigments such as 67,68,71,72,73,74,75,76,78,79,
C. I. Pigment Violet 1,1: 1,2,2: 2,3,3: 1,3: 3,5,5: 1,14,15,16,19,23,25,27,29,31,32, Examples thereof include purple organic pigments such as 37, 39, 42, 44, 47, 49, 50 and the like.
本発明の感光性着色組成物は、色分離性の観点から、ハロゲン化金属フタロシアニン顔料(A-1)とイソインドリン顔料(A-2)の合計含有量が、有機顔料(A)100質量%中、95質量%以上であることが好ましく、99質量%以上であることがより好ましい。 From the viewpoint of color separability, the photosensitive coloring composition of the present invention has a total content of the halogenated metal phthalocyanine pigment (A-1) and the isoindoline pigment (A-2) of 100% by mass of the organic pigment (A). Of these, 95% by mass or more is preferable, and 99% by mass or more is more preferable.
[無機顔料]
本発明の感光性着色組成物は、無機顔料を含有できる。
[Inorganic pigment]
The photosensitive coloring composition of the present invention may contain an inorganic pigment.
無機顔料としては、特に限定されず、公知の無機顔料を用いることができる。例えば、亜鉛華、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(III))、カドミウム赤、群青
、紺青、酸化クロム緑、コバルト緑、アンバー等が挙げられる。また、黒色の無機顔料としては、チタン、及びジルコニウム等の第4族の金属元素、バナジウム及びニオブ等の第5族の金属元素、コバルト、クロム、銅、マンガン、ルテニウム、鉄、ニッケル、錫、並びに銀からなる群より選ばれた1種、又は2種以上の金属元素を含有する金属酸化物、金属窒化物、及び金属酸窒化物、カーボンブラック等が挙げられる。
The inorganic pigment is not particularly limited, and known inorganic pigments can be used. For example, zinc flower, lead sulfate, yellow lead, zinc yellow, red iron oxide (III), cadmium red, ultramarine blue, dark blue, chromium oxide green, cobalt green, amber and the like can be mentioned. Examples of the black inorganic pigment include group 4 metal elements such as titanium and zirconium, group 5 metal elements such as vanadium and niobium, cobalt, chromium, copper, manganese, ruthenium, iron, nickel and tin. Examples thereof include metal oxides, metal nitrides, metal oxynitrides, carbon blacks and the like containing one kind or two or more kinds of metal elements selected from the group consisting of silver.
[染料]
本発明の感光性着色組成物は、染料を含有できる。
[dye]
The photosensitive coloring composition of the present invention can contain a dye.
染料としては、特に限定されず、公知の染料を用いることができる。例えば、酸性染料、直接染料、塩基性染料、造塩染料、油溶性染料、分散染料、反応染料、媒染染料、建染染料、硫化染料等が挙げられる。また、これらの誘導体や、染料をレーキ化した形態であってもかまわない。 The dye is not particularly limited, and known dyes can be used. For example, acidic dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, medium dyes, building dyes, sulfide dyes and the like can be mentioned. Further, these derivatives or dyes may be in a laked form.
さらに、スルホン酸やカルボン酸等の酸性基を有する酸性染料、直接染料の形態の場合は、酸性染料の無機塩や、酸性染料と四級アンモニウム塩化合物、三級アミン化合物、二級アミン化合物、もしくは一級アミン化合物等の含窒素化合物との造塩化合物、又はこれらの官能基を有する樹脂成分を用いて造塩化して造塩化合物として用いること、あるいはスルホンアミド化してスルホン酸アミド化合物として用いることで耐性に優れたものとなるために、堅牢性に優れた着色組成物とすることができ、好ましい。
また、酸性染料とオニウム塩基を有する化合物との造塩化合物も、堅牢性に優れるため好ましく、より好ましくは、オニウム塩基を有する化合物が、側鎖にカチオン性基を有する樹脂である場合である。
Further, an acidic dye having an acidic group such as sulfonic acid or carboxylic acid, or in the case of a direct dye form, an inorganic salt of the acidic dye, an acidic dye and a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, Alternatively, a salt-forming compound with a nitrogen-containing compound such as a primary amine compound, or chloride-forming using a resin component having these functional groups to be used as a salt-forming compound, or sulfonamide formation and use as a sulfonic acid amide compound. It is preferable that the coloring composition has excellent toughness because it has excellent resistance.
Further, a salt-forming compound of an acid dye and a compound having an onium base is also preferable because it has excellent fastness, and more preferably, the compound having an onium base is a resin having a cationic group in the side chain.
塩基性染料の形態の場合は、有機酸や過塩素酸もしくはその金属塩を用いて造塩化して用いることができる。中でも、塩基性染料の造塩化合物が耐性、顔料との併用性に優れているために好ましく、さらに塩基性染料と、カウンタイオンとしてはたらくカウンタ成分である有機スルホン酸、有機硫酸、フッ素基含有リンアニオン化合物、フッ素基含有ホウ素アニオン化合物、シアノ基含有窒素アニオン化合物、ハロゲン化炭化水素基を有する有機酸の共役塩基を有するアニオン化合物、又は酸性染料とを造塩した、造塩化合物を用いることがより好ましいものである。 In the case of the basic dye form, it can be used by chlorinating with an organic acid, perchloric acid or a metal salt thereof. Among them, the salt-forming compound of the basic dye is preferable because it has excellent resistance and compatibility with the pigment, and further, the basic dye and the counter components that act as counter ions, such as organic sulfonic acid, organic sulfuric acid, and fluorine group-containing phosphorus, are preferable. It is possible to use a salt-forming compound obtained by salting an anionic compound, a fluorine group-containing boron anionic compound, a cyano group-containing nitrogen anion compound, an anion compound having a conjugated base of an organic acid having a halogenated hydrocarbon group, or an acidic dye. It is more preferable.
また、色素骨格に重合性不飽和基を有する場合、耐性に優れた染料とすることができ、
好ましい。
Further, when the dye skeleton has a polymerizable unsaturated group, the dye can be made into a dye having excellent resistance.
preferable.
染料の化学構造としては、例えば、アゾ系染料、ジスアゾ系染料、アゾメチン系染料(インドアニリン系染料、インドフェノール系染料など)、ジピロメテン系染料、キノン系染料(ベンゾキノン系染料、ナフトキノン系染料、アントラキノン系染料、アントラピリドン系染料など)、カルボニウム系染料(ジフェニルメタン系染料、トリフェニルメタン系染料、キサンテン系染料、アクリジン系染料など)、キノンイミン系染料(オキサジン系染料、チアジン系染料など)、アジン系染料、ポリメチン系染料(オキソノール系染料、メロシアニン系染料、アリーリデン系染料、スチリル系染料、シアニン系染料、スクアリリウム系染料、クロコニウム系染料など)、キノフタロン系染料、フタロシアニン系染料、サブフタロシアニン系染料、ペリノン系染料、インジゴ系染料、チオインジゴ系染料、キノリン系染料、ニトロ系染料、ニトロソ系染料、ローダミン系染料、及びそれらの金属錯体系染料等から選ばれる染料に由来する色素構造を挙げることができるが、特にこれらに限定されない。 The chemical structure of the dye includes, for example, azo dye, disazo dye, azomethin dye (Indoaniline dye, Indophenol dye, etc.), Dipyrromethene dye, Kinon dye (benzoquinone dye, naphthoquinone dye, anthraquinone). Dyes, anthrapyridone dyes, carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acrydin dyes, etc.), quinoneimine dyes (oxazine dyes, thiadine dyes, etc.), azine dyes. Dyes, polymethine dyes (oxonol dyes, merocyanine dyes, allylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone Examples of dye structures are derived from dyes selected from dyes such as dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and their metal complex dyes. , Especially not limited to these.
(顔料の微細化)
顔料は、微細化して用いることが好ましい。微細化方法は、特に限定されるものではなく、例えば、湿式磨砕、乾式磨砕、溶解析出法いずれも使用できる。これらの中でも、湿式磨砕の1種であるニーダー法によるソルトミリング処理が好ましい。微細化顔料のTEM(透過型電子顕微鏡)により求められる平均一次粒子径は、5~90nmが好ましい。なお、分散性、コントラスト比の観点から、平均一次粒子径は10~70nmがより好ましい。
(Pigment miniaturization)
The pigment is preferably used in a finely divided form. The miniaturization method is not particularly limited, and for example, wet grinding, dry grinding, and dissolution precipitation method can be used. Among these, the salt milling treatment by the kneader method, which is one of the wet grinding methods, is preferable. The average primary particle size determined by the TEM (transmission electron microscope) of the finely divided pigment is preferably 5 to 90 nm. From the viewpoint of dispersibility and contrast ratio, the average primary particle size is more preferably 10 to 70 nm.
ソルトミリング処理とは、顔料と水溶性無機塩と水溶性有機溶剤との混合物を、ニーダー、2本ロールミル、3本ロールミル、ボールミル、アトライター、サンドミル等の混練機を用いて、加熱しながら機械的に混練した後、水洗により水溶性無機塩と水溶性有機溶剤を除去する処理である。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顔料が破砕される。顔料をソルトミリング処理する際の条件を最適化することにより、一次粒子径が非常に微細であり、また、分布の幅がせまく、シャープな粒度分布をもつ顔料を得ることができる。 Salt milling treatment is a machine that heats a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent while heating it using a kneader such as a kneader, a 2-roll mill, a 3-roll mill, a ball mill, an attritor, or a sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the pigment is crushed by utilizing the high hardness of the inorganic salt during salt milling. By optimizing the conditions for the salt milling treatment of the pigment, it is possible to obtain a pigment having a very fine primary particle size, a narrow distribution width, and a sharp particle size distribution.
水溶性無機塩は、塩化ナトリウム、塩化カリウム、硫酸ナトリウム等が挙げられ、価格の点から塩化ナトリウム(食塩)が好ましい。水溶性無機塩の使用量は、処理効率と生産効率の両面から、顔料(A)100質量部に対して、50~2,000質量部が好ましく、300~1,000質量部がより好ましい。 Examples of the water-soluble inorganic salt include sodium chloride, potassium chloride, sodium sulfate and the like, and sodium chloride (salt) is preferable from the viewpoint of price. The amount of the water-soluble inorganic salt used is preferably 50 to 2,000 parts by mass, more preferably 300 to 1,000 parts by mass with respect to 100 parts by mass of the pigment (A) from the viewpoint of both treatment efficiency and production efficiency.
水溶性有機溶剤は、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。ただし、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。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。水溶性有機溶剤の使用量は、顔料100質量部に対して、5~1,000質量部が好ましく、50~500質量部がより好ましい。 The water-soluble organic solvent has a function of wetting the 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 used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety. For example, 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 and the like are used. The amount of the water-soluble organic solvent used is preferably 5 to 1,000 parts by mass, more preferably 50 to 500 parts by mass with respect to 100 parts by mass of the pigment.
ソルトミリング処理には、必要に応じて樹脂を添加してもよい。前記樹脂の種類は特に
限定されず、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挙げられる。これらの中でも、室温で固体であり、水不溶性であることが好ましく、かつ上記有機溶剤に一部可溶であることが好ましい。樹脂の添加量は、顔料100質量部に対して、2~200質量部が好ましい。
If necessary, a resin may be added to the salt milling treatment. The type of the resin is not particularly limited, and examples thereof include a natural resin, a modified natural resin, a synthetic resin, and a synthetic resin modified with a natural resin. Among these, it is preferable that it is solid at room temperature, is insoluble in water, and is partially soluble in the above organic solvent. The amount of the resin added is preferably 2 to 200 parts by mass with respect to 100 parts by mass of the pigment.
[色素誘導体(F)]
本発明の感光性着色組成物は、色素誘導体(F)を含有できる。
[Dye derivative (F)]
The photosensitive coloring composition of the present invention can contain a dye derivative (F).
色素誘導体(F)は、特に制限はなく、有機色素残基に酸性基、塩基性基、中性基などを有する色素誘導体が挙げられる。色素誘導体(F)は、例えば、スルホ基、カルボキシ基、リン酸基などの酸性置換基を有する化合物、およびこれらのアミン塩や、スルホンアミド基や末端に3級アミノ基などの塩基性置換基を有する化合物、フェニル基やフタルイミドアルキル基などの中性置換基を有する化合物が挙げられる。
有機色素は、例えばジケトピロロピロール系顔料、アントラキノン系顔料、キナクリドン系顔料、ジオキサジン系顔料、ペリノン系顔料、ペリレン系顔料、チアジンインジゴ系顔料、トリアジン系顔料、ベンズイミダゾロン系顔料、ベンゾイソインドール等のインドール系顔料、イソインドリン系顔料、イソインドリノン系顔料、キノフタロン系顔料、ナフトール系顔料、スレン系顔料、金属錯体系顔料、アゾ、ジスアゾ、ポリアゾ等のアゾ系顔料等が挙げられる。
The dye derivative (F) is not particularly limited, and examples thereof include a dye derivative having an acidic group, a basic group, a neutral group, or the like as an organic dye residue. The dye derivative (F) is, for example, a compound having an acidic substituent such as a sulfo group, a carboxy group or a phosphate group, an amine salt thereof, or a basic substituent such as a sulfonamide group or a tertiary amino group at the terminal. Examples thereof include compounds having a neutral substituent such as a phenyl group and a phthalimidealkyl group.
Organic pigments include, for example, diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazineindigo pigments, triazine pigments, benzimidazolone pigments, and benzoiso. Examples thereof include indol pigments such as indole, isoindolin pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, slene pigments, metal complex pigments, and azo pigments such as azo, disazo and polyazo.
具体的には、ジケトピロロピロール系色素誘導体としては、特開2001-220520号公報、国際公開第2009/081930号、国際公開第2011/052617号、国際公開第2012/102399号、特開2017-156397号公報、フタロシアニン系色素誘導体としては、特開2007-226161号公報、国際公開第2016/163351号、特開2017-165820号公報、特許第5753266号公報、アントラキノン系色素誘導体としては、特開昭63-264674号公報、特開平09-272812号公報、特開平10-245501号公報、特開平10-265697号公報、特開2007-079094号公報、国際公開第2009/025325号、キナクリドン系色素誘導体としては、特開昭48-54128号公報、特開平03-9961号公報、特開2000-273383号公報、ジオキサジン系色素誘導体としては、特開2011-162662号公報、チアジンインジゴ系色素誘導体としては、特開2007-314785号公報、トリアジン系色素誘導体としては、特開昭61-246261号公報、特開平11-199796号公報、特開2003-165922号公報、特開2003-168208号公報、特開2004-217842号公報、特開2007-314681号公報、ベンゾイソインドール系色素誘導体としては、特開2009-57478号公報、キノフタロン系色素誘導体としては、特開2003-167112号公報、特開2006-291194号公報、特開2008-31281号公報、特開2012-226110号公報、ナフトール系色素誘導体としては、特開2012-208329号公報、特開2014-5439号公報、アゾ系色素誘導体としては、特開2001-172520号公報、特開2012-172092号公報、酸性置換基としては、特開2004-307854号公報、塩基性置換基としては、特開2002-201377号公報、特開2003-171594号公報、特開2005-181383号公報、特開2005-213404号公報等に記載の公知の色素誘導体が挙げられる。なお、これらの文献には、色素誘導体を誘導体、顔料誘導体、分散剤、顔料分散剤若しくは単に化合物などと記載している場合があるが、前記した有機色素残基に酸性基、塩基性基、中性基などの置換基を有する化合物は、色素誘導体と同義である。 Specifically, as the diketopyrrolopyrrole dye derivative, JP-A-2001-22520, International Publication No. 2009/081930, International Publication No. 2011/0526117, International Publication No. 2012/102399, JP-A-2017 156397, as phthalocyanine dye derivatives, JP-A-2007-226161, International Publication No. 2016/163351, JP-A-2017-165820, Patent No. 5735266, as anthraquinone-based dye derivatives, special Kaisho 63-264674, JP-A-09-272812, JP-A-10-245501, JP-A-10-265697, JP-A-2007-079094, International Publication No. 2009/025325, Kinacridone-based As the dye derivative, JP-A-48-54128, JP-A-03-9961 and JP-A-2000-273383, and as the dioxazine-based dye derivative, JP-A-2011-162662, JP-A-2011-162662, the thiazine-indigo dye. As the derivative, JP-A-2007-314785, and as the triazine-based dye derivative, JP-A-61-246261, JP-A-11-19976, JP-A-2003-165922, JP-A-2003-168208. JP-A-2004-217842, JP-A-2007-314681, JP-A-2009-57478 as a benzoisoindole-based dye derivative, JP-A-2003-167112 as a quinophthalone-based dye derivative, JP. JP-A-2006-291194, JP-A-2008-31281, JP-A-2012-226110, and as naphthol-based dye derivatives, JP-A-2012-208329, JP-A-2014-5439, azo-based dyes. Derivatives are JP-A-2001-172520, JP-A-2012-1722092, acidic substituents are JP-A-2004-307854, and basic substituents are JP-A-2002-201377. Examples thereof include known dye derivatives described in JP-A-2003-171594, JP-A-2005-181383, JP-A-2005-213404 and the like. In these documents, the dye derivative may be described as a derivative, a pigment derivative, a dispersant, a pigment dispersant, or simply a compound, but the above-mentioned organic dye residue includes an acidic group, a basic group, and the like. A compound having a substituent such as a neutral group is synonymous with a dye derivative.
色素誘導体(F)は、単独または2種類以上を併用して使用できる。 The dye derivative (F) can be used alone or in combination of two or more.
色素誘導体(F)の含有量は、有機顔料(A)100質量部に対して、1~20質量部
が好ましく、2~10質量部がより好ましい。
The content of the dye derivative (F) is preferably 1 to 20 parts by mass, more preferably 2 to 10 parts by mass with respect to 100 parts by mass of the organic pigment (A).
[分散樹脂(G)]
本発明の感光性着色組成物は、分散樹脂(G)を含有できる。
[Dispersed resin (G)]
The photosensitive coloring composition of the present invention can contain a dispersion resin (G).
分散樹脂(G)は、顔料に親和性が高い吸着基を有している。吸着基は、カチオン性基、およびアニオン性基のうち1種以上が好ましい。 The dispersed resin (G) has an adsorbing group having a high affinity for the pigment. The adsorbing group is preferably one or more of a cationic group and an anionic group.
カチオン性基を有する樹脂は、例えば、カチオン性基として、1級アミノ基、2級アミノ基、3級アミノ基、4級アンモニア塩基、および含窒素複素環など窒素原子を含有する基等が挙げられる。 Examples of the resin having a cationic group include a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonia base, and a group containing a nitrogen atom such as a nitrogen-containing heterocycle as the cationic group. Be done.
アニオン性基を有する樹脂は、例えば、アニオン性基として、カルボキシル基、リン酸基、スルホン酸基等が挙げられる。なかでも、顔料への吸着性の観点からカルボキシル基、リン酸基であることが好ましい。 Examples of the resin having an anionic group include a carboxyl group, a phosphoric acid group, a sulfonic acid group and the like as anionic groups. Of these, a carboxyl group and a phosphoric acid group are preferable from the viewpoint of adsorptivity to pigments.
分散樹脂(G)の樹脂種は、例えば、ウレタン樹脂、ポリアクリレート等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等、(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-ル、ポリビニルピロリドン等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、リン酸エステル系等が挙げられる。 The resin type of the dispersed resin (G) is, for example, a urethane resin, a polycarboxylic acid ester such as polyacrylate, an unsaturated polyamide, a polycarboxylic acid, a polycarboxylic acid (partial) amine salt, a polycarboxylic acid ammonium salt, or a polycarboxylic acid. Alkylamine salts, polysiloxanes, long-chain polyaminoamidophosphates, hydroxyl group-containing polycarboxylic acid esters and modified products thereof, amides formed by the reaction of poly (lower alkyleneimine) with polyesters having free carboxyl groups. Water-soluble such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Examples thereof include sex resins, water-soluble polymer compounds, polyester-based materials, modified polyacrylate-based compounds, ethylene oxide / propylene oxide-added compounds, and phosphoric acid ester-based compounds.
分散樹脂(G)の構造は、例えば、ランダム構造、ブロック構造、グラフト構造、くし型構造、及び星型構造等が挙げられる。これらの中でも、分散安定性の観点から、ブロック構造、グラフト構造、及びくし型構造が好ましい。 Examples of the structure of the dispersed resin (G) include a random structure, a block structure, a graft structure, a comb-shaped structure, and a star-shaped structure. Among these, a block structure, a graft structure, and a comb-shaped structure are preferable from the viewpoint of dispersion stability.
分散樹脂(G)の市販品は、例えば、ビックケミー・ジャパン社製のDisperbyk-101, 103, 107, 108, 110,111,116,130,140,154,161,162,163,164,165,166,167,168,170,171,174,180,181,182,183,184,185,190,2000,2001,2009,2010,2020,2025,2050,2070,2095,2150,2155,2163,2164、またはAnti-Terra-U203,204、またはBYK-P104,P104S,220S、またはLactimon、Lactimon-WS、またはBykumen等、日本ルーブリゾール社製のSOLSPERSE-3000,9000,13000,13240,13650,13940,16000,17000,18000,20000,21000,24000,26000,27000,28000,31845,32000,32500,32550,33500,32600,34750,35100,36600,38500,41000,41090,53095,55000,56000,76500等、BASF社製のEFKA-46,47,48,452,4008,4009,4010,4015,4020,4047,4050,4055,4060,4080,4400,4401,4402,4403,4406,4408,4300,4310,4320,4330,4340,450,451,453,4540,4550,4560,4800,5010,5065,5066,5070,7500,7554,1101,120,150,1501,1502,1503等、味の素ファインテクノ社製のアジスーパーPA111,PB711,
PB821,PB822,PB824等、特開2008-029901号公報、特開2009-155406号公報、特開2010-185934号公報、特開2011-157416号公報等に記載の樹脂が挙げられる。
Commercially available products of the dispersed resin (G) include, for example, Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, manufactured by Big Chemie Japan. 166, 167, 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163 2164, or Anti-Terra-U203,204, or BYK-P104, P104S, 220S, or Lactimon, Lactimon-WS, or Bykuman, etc. , 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500 Etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, manufactured by BASF, etc. 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc. Aji Super PA111, PB711, manufactured by the company
Examples thereof include the resins described in JPB8211, PB822, PB824 and the like, JP-A-2008-029901, JP-A-2009-155406, JP-A-2010-185934, JP-A-2011-157416 and the like.
分散樹脂(G)は、単独または2種類以上を併用して使用できる。 The dispersed resin (G) can be used alone or in combination of two or more.
分散樹脂(G)の含有量は、分散安定性の観点から、有機顔料(A)100質量部に対して、3~200質量部が好ましく、5~100質量部がより好ましい。 The content of the dispersed resin (G) is preferably 3 to 200 parts by mass, more preferably 5 to 100 parts by mass with respect to 100 parts by mass of the organic pigment (A) from the viewpoint of dispersion stability.
[アルカリ可溶性樹脂(B)]
本発明の感光性着色組成物は、アルカリ可溶性樹脂(B)を含む。
[Alkali-soluble resin (B)]
The photosensitive coloring composition of the present invention contains an alkali-soluble resin (B).
アルカリ可溶性樹脂(B)は、アルカリ現像液に溶解する樹脂であればよく、公知の樹脂を用いることができる。アルカリ可溶性樹脂(B)は、非感光性アルカリ可溶性樹脂、感光性アルカリ可溶性樹脂に分類できる。アルカリ可溶性樹脂(B)は、例えば、カルボキシル基、リン酸基、スルホン酸基、ヒドロキシル基、フェノール性ヒドロキシル基などのアルカリ可溶性基を有する。これらの中でも、カルボキシル基が好ましい。
非感光性アルカリ可溶性樹脂は、例えば、酸性基を有するアクリル樹脂、α-オレフィン/(無水)マレイン酸共重合体、スチレン/スチレンスルホン酸共重合体、エチレン/(メタ)アクリル酸共重合体、又はイソブチレン/(無水)マレイン酸共重合体等が挙げられる。感光性アルカリ可溶性樹脂は、重合性不飽和基を有するアルカリ可溶性樹脂である。また、アルカリ可溶性樹脂(B)は、エポキシ基やオキセタニル基等の熱硬化性基を含有できる。
The alkali-soluble resin (B) may be any resin as long as it is soluble in an alkaline developer, and known resins can be used. The alkali-soluble resin (B) can be classified into a non-photosensitive alkali-soluble resin and a photosensitive alkali-soluble resin. The alkali-soluble resin (B) has, for example, an alkali-soluble group such as a carboxyl group, a phosphoric acid group, a sulfonic acid group, a hydroxyl group, and a phenolic hydroxyl group. Among these, a carboxyl group is preferable.
The non-photosensitive alkali-soluble resin is, for example, an acrylic resin having an acidic group, an α-olefin / (maleic) maleic anhydride copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, and the like. Alternatively, isobutylene / (maleic anhydride) maleic acid copolymer and the like can be mentioned. The photosensitive alkali-soluble resin is an alkali-soluble resin having a polymerizable unsaturated group. Further, the alkali-soluble resin (B) can contain a thermosetting group such as an epoxy group or an oxetanyl group.
アルカリ可溶性樹脂(B)の重量平均分子量(Mw)は、現像性の観点から、2,000~40,000が好ましく、3,000~300,00がより好ましく、4,000~20,000が特に好ましい。また、Mw/Mnの値は10以下が好ましい。適度な重量平均分子量(Mw)により基板に対する密着性、及び現像溶解性が向上する。 The weight average molecular weight (Mw) of the alkali-soluble resin (B) is preferably 2,000 to 40,000, more preferably 3,000 to 3,000, and 4,000 to 20,000 from the viewpoint of developability. Especially preferable. Further, the value of Mw / Mn is preferably 10 or less. Adhesion to the substrate and development solubility are improved by an appropriate weight average molecular weight (Mw).
アルカリ可溶性樹脂(B)の酸価は、50~200mgKOH/gが好ましく、70~180mgKOH/gがより好ましく、90~170mgKOH/gがさらに好ましい。適度な酸価により基板に対する密着性、及び現像溶解性が向上する。 The acid value of the alkali-soluble resin (B) is preferably 50 to 200 mgKOH / g, more preferably 70 to 180 mgKOH / g, and even more preferably 90 to 170 mgKOH / g. Adhesion to the substrate and development solubility are improved by an appropriate acid value.
アルカリ可溶性樹脂(B)の含有量は、有機顔料(A)100質量部に対して、20~400質量部が好ましく、50~250質量部がより好ましい。 The content of the alkali-soluble resin (B) is preferably 20 to 400 parts by mass, more preferably 50 to 250 parts by mass with respect to 100 parts by mass of the organic pigment (A).
アルカリ可溶性樹脂(B)は、単独または2種類以上を併用して使用できる。 The alkali-soluble resin (B) can be used alone or in combination of two or more.
アルカリ可溶性樹脂(B)は、パターン形成性の観点から、感光性アルカリ可溶性樹脂を含むことが好ましい。 The alkali-soluble resin (B) preferably contains a photosensitive alkali-soluble resin from the viewpoint of pattern formation.
(アルカリ可溶性樹脂(B-1))
本発明の感光性着色組成物は、アルカリ可溶性樹脂(B)として、パターン形成性の観点から、脂環式炭化水素構造含有単量体単位(b1)、及びカルボキシル基含有単量体単位(b2)とを含有するアルカリ可溶性樹脂(B-1)を含むことが好ましい。
(Alkali-soluble resin (B-1))
The photosensitive coloring composition of the present invention contains an alicyclic hydrocarbon structure-containing monomer unit (b1) and a carboxyl group-containing monomer unit (b2) as the alkali-soluble resin (B) from the viewpoint of pattern formation. ) And an alkali-soluble resin (B-1).
〔脂環式炭化水素構造含有単量体単位(b1)〕
脂環式炭化水素構造含有単量体単位(b1)を形成する脂環式炭化水素構造含有単量体としては、例えば、イソボロニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリ
レート、ジシクロペンタニルオキシエチル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、アダマンチル(メタ)アクリレート等が挙げられる。これらの中でも、パターン形成性の観点から、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンタニルオキシエチル(メタ)アクリレートが好ましい。
[Alicyclic hydrocarbon structure-containing monomer unit (b1)]
Examples of the alicyclic hydrocarbon structure-containing monomer forming the alicyclic hydrocarbon structure-containing monomer unit (b1) include isobolonyl (meth) acrylate, cyclohexyl (meth) acrylate, and dicyclopentanyl (meth). ) Acrylate, dicyclopentenyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, adamantyl (meth) acrylate and the like. Among these, dicyclopentenyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and dicyclopentenyloxyethyl (meth) acrylate are preferable from the viewpoint of pattern formation.
〔カルボキシル基含有単量体単位(b2)〕
カルボキシル基含有単量体単位(b2)を形成するカルボキシル基含有単量体としては、アクリル酸、メタクリル酸、クロトン酸、イタコン酸、マレイン酸、フマル酸等が挙げられる。また、α-(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基およびカルボキシル基を含有する単量体を併用することもできる。これらの中でも、アクリル酸、メタクリル酸が好ましい。
[Carboxyl group-containing monomer unit (b2)]
Examples of the carboxyl group-containing monomer forming the carboxyl group-containing monomer unit (b2) include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid and the like. Further, a monomer containing a hydroxy group and a carboxyl group in the same molecule, such as α- (hydroxymethyl) acrylic acid, can also be used in combination. Of these, acrylic acid and methacrylic acid are preferable.
〔その他単量体単位(b3)〕
アルカリ可溶性樹脂(B-1)は、脂環式炭化水素構造含有単量体(b1)、及びカルボキシル基含有単量体単位(b2)以外にその他単量体単位(b3)を含有できる。
[Other monomer unit (b3)]
The alkali-soluble resin (B-1) can contain other monomer units (b3) in addition to the alicyclic hydrocarbon structure-containing monomer (b1) and the carboxyl group-containing monomer unit (b2).
その他単量体単位(b3)を形成するその他単量体は、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、n-プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、t-ブチル(メタ)アクリレート、2-エチルヘキシル(メタ)アクリレート、ステアリル(メタ)アクリレート、ラウリル(メタ)アクリレート、フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、メトキシポリプロピレングリコール(メタ)アクリレート、エトキシポリエチレングリコール(メタ)アクリレート等の(メタ)アクリレート類;
2-ヒドロキシエチル(メタ)アクリレート、2-若しくは3-ヒドロキシプロピル(メタ)アクリレート、2-若しくは3-若しくは4-ヒドロキシブチル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート、又はシクロヘキサンジメタノールモノ(メタ)アクリレート等の水酸基含有(メタ)アクリレート類;
ヒドロキシアルキル(メタ)アクリレートに、エチレンオキシド、プロピレンオキシド、及び/又はブチレンオキシド等を付加重合させたポリエーテルモノ(メタ)アクリレートや、ポリγ-バレロラクトン、ポリε-カプロラクトン、及び/又はポリ12-ヒドロキシステアリン酸等を付加したポリエステルモノ(メタ)アクリレート類;
グリシジル(メタ)アクリレート、メチルグリシジル(メタ)アクリレート、2-グリシドキシエチル(メタ)アクリレート、3,4-エポキシブチル(メタ)アクリレート、及び3,4-エポキシシクロヘキシル(メタ)アクリレート等のエポキシ基含有(メタ)アクリレート類;
(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、ダイアセトン(メタ)アクリルアミド、又はアクリロイルモルホリン等の(メタ)アクリルアミド類;
スチレン、又はα-メチルスチレン等のスチレン類;
エチルビニルエーテル、n-プロピルビニルエーテル、イソプロピルビニルエーテル、n-ブチルビニルエーテル、又はイソブチルビニルエーテル等のビニルエーテル類;
酢酸ビニル、又はプロピオン酸ビニル等の脂肪酸ビニル類;
フェニルマレイミド、メチルマレイミド、エチルマレイミド、1,2-ビスマレイミドエタン1,6-ビスマレイミドヘキサン、3-マレイミドプロピオン酸、6,7-メチレンジオキシ-4-メチル-3-マレイミドクマリン、4,4’-ビスマレイミドジフェニルメタン、ビス(3-エチル-5-メチル-4-マレイミドフェニル)メタン、N,N’-1,3-フェニレンジマレイミド、N,N’-1,4-フェニレンジマレイミド、N-(
1-ピレニル)マレイミド、N-(2,4,6-トリクロロフェニル)マレイミド、N-(4-アミノフェニル)マレイミド、N-(4-ニトロフェニル)マレイミド、N-ベンジルマレイミド、N-ブロモメチル-2,3-ジクロロマレイミド、N-スクシンイミジル-3-マレイミドベンゾエ-ト、N-スクシンイミジル-3-マレイミドプロピオナ-ト、N-スクシンイミジル-4-マレイミドブチラ-ト、N-スクシンイミジル-6-マレイミドヘキサノア-ト、N-[4-(2-ベンゾイミダゾリル)フェニル]マレイミド、9-マレイミドアクリジン等のN-置換マレイミド類;
2-(メタ)アクリロイルオキシエチルアシッドフォスフェート、上述した水酸基含有(メタ)アクリレートの水酸基に、たとえば5酸化リンやポリリン酸等のリン酸エステル化剤を反応させた化合物等のリン酸エステル基含有(メタ)アクリレート類等が挙げられる。
Other monomers forming the monomer unit (b3) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, and n-butyl (meth). ) Acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, phenoxy (Meta) acrylates such as ethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate;
2-Hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol mono (meth) acrylate, or cyclohexanedimethanol mono (meth) ) Hydroxyl-containing (meth) acrylates such as acrylate;
Polyester mono (meth) acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide to hydroxyalkyl (meth) acrylate, poly γ-valerolactone, poly ε-caprolactone, and / or poly 12-. Polyester mono (meth) acrylates to which hydroxystearic acid etc. are added;
Epoxy groups such as glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, and 3,4-epoxycyclohexyl (meth) acrylate. Contains (meth) acrylates;
(Meta) acrylamides such as (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, or acryloyl morpholine. ;
Styrene, or styrenes such as α-methylstyrene;
Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether;
Vinyl acetate, or fatty acid vinyls such as vinyl propionate;
Phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimideethane 1,6-bismaleimidehexane, 3-maleimidepropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimidecoumarin, 4,4 '-Bismaleimide diphenylmethane, bis (3-ethyl-5-methyl-4-maleimidephenyl) methane, N, N'-1,3-phenylenedi maleimide, N, N'-1,4-phenylenedi maleimide, N -((
1-pyrenyl) maleimide, N- (2,4,6-trichlorophenyl) maleimide, N- (4-aminophenyl) maleimide, N- (4-nitrophenyl) maleimide, N-benzylmaleimide, N-bromomethyl-2 , 3-Dichloromaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-3-maleimidepropionate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimidehexa N-substituted maleimides such as Noato, N- [4- (2-benzoimidazolyl) phenyl] maleimide, 9-maleimide acrydin;
2- (meth) acryloyloxyethyl acid phosphate, containing a phosphate ester group such as a compound obtained by reacting the hydroxyl group of the above-mentioned hydroxyl group-containing (meth) acrylate with a phosphate esterifying agent such as phosphorus pentoxide or polyphosphoric acid. Examples thereof include (meth) acrylates.
アルカリ可溶性樹脂(B-1)は、脂環式炭化水素構造含有単量体単位(b1)、及びカルボキシル基含有単量体単位(b2)を含有すれば良く、その合成方法は特に限定されず、公知の方法を用いることができる。例えば、下記の方法(i)、又は方法(ii)で合成することができる。 The alkali-soluble resin (B-1) may contain an alicyclic hydrocarbon structure-containing monomer unit (b1) and a carboxyl group-containing monomer unit (b2), and the synthesis method thereof is not particularly limited. , A known method can be used. For example, it can be synthesized by the following method (i) or method (ii).
<方法(i)>
方法(i)は、例えば、脂環式炭化水素構造含有単量体、及びカルボキシル基含有単量体の共重合体を合成することで、アルカリ可溶性樹脂(B-1)を合成できる。
<Method (i)>
In method (i), for example, an alkali-soluble resin (B-1) can be synthesized by synthesizing a copolymer of an alicyclic hydrocarbon structure-containing monomer and a carboxyl group-containing monomer.
<方法(ii)>
方法(ii)は、例えば、脂環式炭化水素構造含有単量体、及びエポキシ基含有単量体の共重合体を合成する。次いで、前記共重合体のエポキシ基に、カルボキシル基含有単量体を付加し、生成した水酸基と脂肪酸無水物とをエステル化反応させることで、アルカリ可溶性樹脂(B-1)を合成できる。
<Method (ii)>
The method (ii) synthesizes, for example, a copolymer of an alicyclic hydrocarbon structure-containing monomer and an epoxy group-containing monomer. Next, an alkali-soluble resin (B-1) can be synthesized by adding a carboxyl group-containing monomer to the epoxy group of the copolymer and subjecting the generated hydroxyl group to an esterification reaction with the fatty acid anhydride.
エポキシ基含有単量体としては、その他単量体単位(b3)を形成するその他単量体で記載したものに含まれ、例えば、グリシジル(メタ)アクリレート、メチルグリシジル(メタ)アクリレート、2-グリシドキシエチル(メタ)アクリレート、3,4-エポキシブチル(メタ)アクリレート、及び3,4-エポキシシクロヘキシル(メタ)アクリレートが挙げられる。これらの中でも、反応性の観点で、グリシジル(メタ)アクリレートが好ましい。 The epoxy group-containing monomer is contained in those described in other monomers forming the monomer unit (b3), and is, for example, glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, and 2-glyce. Sidoxyethyl (meth) acrylates, 3,4-epoxybutyl (meth) acrylates, and 3,4-epoxycyclohexyl (meth) acrylates can be mentioned. Among these, glycidyl (meth) acrylate is preferable from the viewpoint of reactivity.
脂肪酸無水物は、例えば、テトラヒドロ無水フタル酸、無水フタル酸、ヘキサヒドロ無水フタル酸、無水コハク酸、無水マレイン酸等が挙げられ、単独又は2種以上併用して使用できる。 Examples of the fatty acid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride and the like, and can be used alone or in combination of two or more.
脂環式炭化水素構造含有単量体単位(b1)の含有量は、パターン形成性の観点から、アルカリ可溶性樹脂(B-1)の全構成単位100質量%中、5~60質量%であることが好ましく、10~50質量%であることがより好ましい。 The content of the alicyclic hydrocarbon structure-containing monomer unit (b1) is 5 to 60% by mass in 100% by mass of all the constituent units of the alkali-soluble resin (B-1) from the viewpoint of pattern forming property. It is preferably 10 to 50% by mass, and more preferably 10 to 50% by mass.
アルカリ可溶性樹脂(B-1)の含有量は、パターン形成性の観点から、アルカリ可溶性樹脂(B)100質量%中、50質量%以上が好ましく、70質量%以上がより好ましい。 From the viewpoint of pattern formation, the content of the alkali-soluble resin (B-1) is preferably 50% by mass or more, more preferably 70% by mass or more, based on 100% by mass of the alkali-soluble resin (B).
(アルカリ可溶性樹脂(B-2))
本発明の感光性着色組成物は、アルカリ可溶性樹脂(B)として、アルカリ可溶性樹脂(B-1)以外のアルカリ可溶性樹脂(B-2)を含有することができる。
(Alkali-soluble resin (B-2))
The photosensitive coloring composition of the present invention can contain an alkali-soluble resin (B-2) other than the alkali-soluble resin (B-1) as the alkali-soluble resin (B).
[重合性化合物(C)]
(ウレタン結合を有する重合性化合物(C-1))
本発明の感光性着色組成物は、重合性化合物(C)として、ウレタン結合を有する重合性化合物(C-1)を含む。ウレタン結合を有する重合性化合物(C-1)のウレタン結合部分が、硬化時の膜表面と内部での硬化度合いの違いによる硬化収縮を緩和、抑制し、表面のシワの発生をより効果的に改善できる。
重合性化合物(C)は、重合性不飽和基を含有する単量体(モノマーともいう)、2量体、3量体、およびオリゴマーである。重合性不飽和基は、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、(メタ)アクリロイルオキシ基等が挙げられる。
[Polymerizable compound (C)]
(Polymerizable compound having urethane bond (C-1))
The photosensitive coloring composition of the present invention contains a polymerizable compound (C-1) having a urethane bond as the polymerizable compound (C). The urethane-bonded portion of the polymerizable compound (C-1) having a urethane bond alleviates and suppresses curing shrinkage due to the difference in the degree of curing between the film surface and the inside during curing, and more effectively causes wrinkles on the surface. Can be improved.
The polymerizable compound (C) is a monomer (also referred to as a monomer) containing a polymerizable unsaturated group, a dimer, a trimer, and an oligomer. Examples of the polymerizable unsaturated group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a (meth) acryloyloxy group and the like.
ウレタン結合を有する重合性化合物(C-1)は、特に限定されず、公知のものを用いることができる。例えば、水酸基を有する(メタ)アクリレートに多官能イソシアネートを反応させて得られるウレタン(メタ)アクリレートや、多価アルコールに多官能イソシアネートを反応させ、さらに水酸基を有する(メタ)アクリレートを反応させて得られるウレタン(メタ)アクリレート等が挙げられる。 The polymerizable compound (C-1) having a urethane bond is not particularly limited, and known compounds can be used. For example, a urethane (meth) acrylate obtained by reacting a (meth) acrylate having a hydroxyl group with a polyfunctional isocyanate, or a polyhydric alcohol obtained by reacting a polyfunctional isocyanate and further reacting with a (meth) acrylate having a hydroxyl group. Urethane (meth) acrylate and the like can be mentioned.
上記水酸基を有する(メタ)アクリレートは、例えば、2-ヒドロキシエチル(メタ)
アクリレート、4-ヒドロキシブチル(メタ)アクリレート、トリメチロールプロパンジ
(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、ジトリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールエチレンオキサイド変性ペンタ(メタ)アクリレート、ジペンタエリスリトールプロピレンオキサイド変性ペンタ(メタ)アクリレート、ジペンタエリスリトールカプロラクトン変性ペンタ(メタ)アクリレート、グリセロールアクリレートメタクリレート、グリセロールジメタクリレート、2-ヒドロキシ-3-アクリロイルプロピルメタクリレート、エポキシ基含有化合物とカルボキシ(メタ)アクリレートの反応物、水酸基含有ポリオールポリアクリレート等が挙げられる。
The (meth) acrylate having a hydroxyl group is, for example, 2-hydroxyethyl (meth).
Acrylate, 4-Hydroxybutyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, ditrimethylol propanetri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol ethylene Oxide-modified penta (meth) acrylate, dipentaerythritol propylene oxide-modified penta (meth) acrylate, dipentaerythritol caprolactone-modified penta (meth) acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropylmethacrylate, epoxy Examples thereof include a reaction product of a group-containing compound and a carboxy (meth) acrylate, and a hydroxyl group-containing polyol polyacrylate.
上記多官能イソシアネートは、例えば、芳香族ジイソシアネートである1,5-ナフチレンジイソシアネート、4,4’-ジフェニルメタンジイソシアネート、4,4’-ジフェニルジメチルメタンジイソシアネート、4,4’-ジベンジルイソシアネート、ジアルキルジフェニルメタンジイソシアネート、テトラアルキルジフェニルメタンジイソシアネート、1,3-フェニレンジイソシアネート、1,4-フェニレンジイソシアネート、2,4-トルエンジイソシアネート、2,6-トルエンジイソシアネート、キシリレンジイソシアネート、m-テトラメチルキシリレンジイソシアネート、4,4-ジフェニルメタンジイソシアネート、トリレンジイソシアネート、ビス-クロロメチル-ジフェニルメタン-ジイソシアネート、2,6-ジイソシアネート-ベンジルクロライド、ビス(イソシアネートメチル)ベンゼン等;
脂肪族ジイソシアネートであるブタン-1,4-ジイソシアネート、ヘキサメチレンジイソシアネート、イソプロピレンジイソシアネート、メチレンジイソシアネート、2,2,4-トリメチルヘキサメチレンジイソシアネート等;
脂環式ジイソシアネートであるシクロヘキサン-1,4-ジイソシアネート、イソホロンジイソシアネート、ジメチルシクロヘキシルジイソシアネート、メチルシクロヘキシルジイソシアネート、ジシクロヘキシルメタン-4,4’-ジイソシアネート、1,3-ビス(イソシアネートメチル)シクロヘキサン、メチルシクロヘキサンジイソシアネート、ノルボルナンジイソシアネート、ビス(イソシアネートメチル)シクロヘキサン等が挙げられる。また、これらのビュレット体、イソシアネートヌレート体、トリメチロールプロパンアダクト体等が挙げられる。
The polyfunctional isocyanate is, for example, an aromatic diisocyanate such as 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzylisocyanide, or dialkyldiphenylmethane. Diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylenediocyanide, 1,4-phenylenediocyanide, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, xylylene diisocyanate, m-tetramethylxylylene diisocyanate, 4,4 -Diphenylmethane diisocyanate, toluene diisocyanate, bis-chloromethyl-diphenylmethane-diisocyanate, 2,6-diisocyanine-benzyl chloride, bis (isocyanisocyanide) benzene, etc .;
Butane-1,4-diisocyanate, hexamethylene diisocyanate, isopropylene diisocyanate, methylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, etc., which are aliphatic diisocyanates;
Cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dimethylcyclohexyldiisocyanate, methylcyclohexyldiisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, methylcyclohexanediisocyanate, which are alicyclic diisocyanates, Examples thereof include norbornane diisocyanate and bis (isocyanate methyl) cyclohexane. Further, these burette bodies, isocyanate nurate bodies, trimethylolpropane adduct bodies and the like can be mentioned.
ウレタン結合を有する重合性化合物(C-1)は、現像性の観点から、酸基を有することが好ましい。酸基は、例えば、スルホン酸基、カルボキシル基、リン酸基等を挙げられ
る。なかでも、カルボキシル基が好ましい。酸基及びウレタン結合を有する重合性化合物(C-1)は、下記一般式(1)で表される化合物が好ましい。
一般式(1)(H2C=C(R1)COO)m-X-(OCOCH(R1)CH2S(R2)COOH)n
一般式(1)中、R1は、水素原子又はメチル基、R2は、炭素数1~12の炭化水素基、Xは、(m+n)価の炭素数3~60のウレタン結合を有する有機基、mは2~18の整数、nは1~3の整数を示す。
The polymerizable compound (C-1) having a urethane bond preferably has an acid group from the viewpoint of developability. Examples of the acid group include a sulfonic acid group, a carboxyl group, a phosphoric acid group and the like. Of these, a carboxyl group is preferable. The polymerizable compound (C-1) having an acid group and a urethane bond is preferably a compound represented by the following general formula (1).
General formula (1) (H 2 C = C (R 1 ) COO) m -X- (OCOCH (R 1 ) CH 2 S (R 2 ) COOH) n
In the general formula (1), R 1 is a hydrogen atom or a methyl group, R 2 is a hydrocarbon group having 1 to 12 carbon atoms, and X is an organic having a (m + n) -valent urethane bond having 3 to 60 carbon atoms. The group, m is an integer of 2 to 18, and n is an integer of 1 to 3.
一般式(1)で表される化合物は、例えば、まず、上記多官能イソシアネート化合物と上記水酸基を有する(メタ)アクリレートとを反応させる。次いで、生成物にカルボキシル基を有するメルカプト化合物を付加させる方法で合成できる。 For the compound represented by the general formula (1), for example, first, the polyfunctional isocyanate compound is first reacted with the (meth) acrylate having a hydroxyl group. Then, it can be synthesized by a method of adding a mercapto compound having a carboxyl group to the product.
上記カルボキシル基を有するメルカプト化合物は、例えば、メルカプト酢酸、2-メルカプトプロピオン酸、3-メルカプトプロピオン酸、o-メルカプト安息香酸、2-メルカプトニコチン酸、メルカプトコハク酸等が挙げられる。 Examples of the mercapto compound having a carboxyl group include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, o-mercaptobenzoic acid, 2-mercaptonicotinic acid, and mercaptosuccinic acid.
ウレタン結合を有する重合性化合物(C-1)の重合性不飽和基数は、パターン形成性、シワの抑制の観点から、3~15個が好ましく、5~12個がより好ましい。 The number of polymerizable unsaturated groups of the polymerizable compound (C-1) having a urethane bond is preferably 3 to 15 and more preferably 5 to 12 from the viewpoint of pattern formation and suppression of wrinkles.
ウレタン結合を有する重合性化合物(C-1)は、シワの抑制の観点から、水酸基を有する(メタ)アクリレートと脂環式ジイソシアネート、又は芳香族ジイソシアネートとの反応物である脂環式、又は芳香族ウレタン(メタ)アクリレートを含有することが好ましく、芳香族ウレタン(メタ)アクリレートを含有することがより好ましい。剛直な構造を有する脂環式、又は芳香族ジイソシアネートを使用することで、硬化収縮が起こりにくくなり、シワを抑制する。 The polymerizable compound (C-1) having a urethane bond is an alicyclic or aromatic reaction product of a (meth) acrylate having a hydroxyl group and an alicyclic diisocyanate or an aromatic diisocyanate from the viewpoint of suppressing wrinkles. It is preferable to contain a group urethane (meth) acrylate, and more preferably to contain an aromatic urethane (meth) acrylate. By using an alicyclic or aromatic diisocyanate having a rigid structure, curing shrinkage is less likely to occur and wrinkles are suppressed.
ウレタン結合を有する重合性化合物(C-1)の市販品は、共栄社化学社製のAH-600、AT-600、UA-306H、UA-306T、UA-306I、UA-510H、UF-8001G、DAUA-167、新中村化学工業社製のU-15HA、UA-160TM,1100H、大阪有機化学工業社製のUV-4108F、UV-4117F、ダイセル・オルネクス社製のEBECRY220,1290,4513,5129等が挙げられる。 Commercially available products of the polymerizable compound (C-1) having a urethane bond are AH-600, AT-600, UA-306H, UA-306T, UA-306I, UA-510H, UF-8001G, manufactured by Kyoeisha Chemical Co., Ltd. DAUA-167, U-15HA, UA-160TM, 1100H manufactured by Shin-Nakamura Chemical Industry Co., Ltd., UV-4108F, UV-4117F manufactured by Osaka Organic Chemical Industry Co., Ltd., EBECRY 220, 1290, 4513, 5129 manufactured by Daicel Ornex, etc. Can be mentioned.
(その他重合性化合物(C-2))
本発明の感光性着色組成物は、パターン形成性の観点から、ウレタン結合を有する重合性化合物(C-1)以外にその他重合性化合物(C-2)を含むことが好ましい。
(Other polymerizable compounds (C-2))
From the viewpoint of pattern formation, the photosensitive coloring composition of the present invention preferably contains a polymerizable compound (C-2) in addition to the polymerizable compound (C-1) having a urethane bond.
その他重合性化合物(C-2)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-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、ポリプロピレングリコールジ(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、エトキシ化ビスフェノールAジ(メタ)アクリレート、トリメチロ-ルプロパントリ(メタ)アクリレート、フェノキシテトラエチレングリコール(メタ)アクリレート、フェノキシヘキサエチレングリコール(メタ)アクリレート、トリメチロ-ルプロパンPO変性トリ(メタ)アクリレート、トリメチロ-ルプロパンEO変性トリ(メタ)アクリレート、イソシアヌル酸EO変性ジ(メタ)アクリレート、イソシアヌル酸EO変性トリ(メタ)アクリレート、ジトリメチロ-ルプロパンテトラ(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、ペンタエリスリトールテトラ(メタ)アクリレート、1,6-ヘキサンジオ-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、ジペンタエリスリトールペンタ(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、メチロ-ル化メラミンの(メタ)アクリル酸エステル、エポキシ(メタ)アクリレート等の各種アクリル酸エステル及びメタクリル酸エステル、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。これらの中でも、パターン形成性の観点から、重合性不飽和基数が5以上のものが好ましい。 Examples of the other polymerizable compound (C-2) include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, and the like. β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanedioldi (meth) acrylate, triethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, tricyclodecandy Methanoldi (meth) acrylate, ethoxylated bisphenol A di (meth) acrylate, trimethylol propanetri (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, phenoxyhexaethylene glycol (meth) acrylate, trimethylol propane PO-modified tri (meth) Meta) Acrylate, Trimethylol Propane EO Modified Tri (Meta) Acrylate, Isocyanuric Acid EO Modified Di (Meta) Acrylate, Isocyanuric Acid EO Modified Tri (Meta) Acrylate, Ditrimethylol Propanetetra (Meta) Acrylate, Pentaerythritol Tri (Meta) ) Acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanedio-lurdiglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, di Various acrylic acid esters such as pentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodecanyl (meth) acrylate, methylolated melamine (meth) acrylic acid ester, and epoxy (meth) acrylate. And methacrylic acid ester, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinylformamide, acrylonitrile and the like. Among these, those having 5 or more polymerizable unsaturated groups are preferable from the viewpoint of pattern formation.
その他重合性化合物(C-2)の市販品は、例えば、日本化薬社製のKAYARAD R-128H,R526,PEG400DA,MAND,NPGDA,R-167,HX-220,R-551,R712,R-604,R-684,GPO-303,TMPTA,DPHA,DPEA-12,DPHA-2C,D-310,D-330,DPCA-20,DPCA-30,DPCA-60,DPCA-120、東亜合成社製のアロニックスM-303,M-305,M-306,M-309,M-310,M-321,M-325,M-350,M-360,M-313,M-315,M-400,M-402,M-403,M-404,M-405,M-406,M-450,M-452,M-408,M-211B,M-101A,M-5300,M-5400,M-5700,M-510,M-520,M-521、大阪有機社製のビスコート#2500P、新中村化学工業社製のNKエステルABE-300,A-DOG,A-DCP,A-BPE-4、ダイセル・オルネクス社製のEBECRY40,130,140,145等が挙げられる。 Other commercially available products of the polymerizable compound (C-2) include, for example, KAYARAD R-128H, R526, PEG400DA, MAND, NPGDA, R-167, HX-220, R-551, R712, R manufactured by Nippon Kayaku Co., Ltd. -604, R-684, GPO-303, TMPTA, DPHA, DPEA-12, DPHA-2C, D-310, D-330, DPCA-20, DPCA-30, DPCA-60, DPCA-120, Toagosei Co., Ltd. Aronix M-303, M-305, M-306, M-309, M-310, M-321, M-325, M-350, M-360, M-313, M-315, M-400 , M-402, M-403, M-404, M-405, M-406, M-450, M-452, M-408, M-211B, M-101A, M-5300, M-5400, M -5700, M-510, M-520, M-521, Viscoat # 2500P manufactured by Osaka Organic Co., Ltd., NK Ester ABE-300, A-DOG, A-DCP, A-BPE-4 manufactured by Shin-Nakamura Chemical Industry Co., Ltd. , EBECRY 40, 130, 140, 145 manufactured by Daicel Ornex Co., Ltd. and the like.
パターン形成性、表面のシワの抑制の観点から、ウレタン結合を有する重合性化合物(C-1)とその他重合性化合物(C-2)の質量比が、80:20~20:80であることが好ましく、70:30~30:70であることがより好ましい。 From the viewpoint of pattern formation and suppression of surface wrinkles, the mass ratio of the polymerizable compound (C-1) having a urethane bond to the other polymerizable compound (C-2) is 80:20 to 20:80. Is preferable, and 70:30 to 30:70 is more preferable.
重合性化合物(C)の含有量は、感光性着色組成物の不揮発分100質量%中、5~50質量%が好ましく、5~30質量%がより好ましい。 The content of the polymerizable compound (C) is preferably 5 to 50% by mass, more preferably 5 to 30% by mass, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.
[光重合開始剤(D)]
本発明の感光性着色組成物は、光重合開始剤(D)を含む。光重合開始剤(D)を含むことで、感光性着色組成物を紫外線照射により硬化させ、硬化膜を形成することができる。
[Photopolymerization Initiator (D)]
The photosensitive coloring composition of the present invention contains a photopolymerization initiator (D). By containing the photopolymerization initiator (D), the photosensitive coloring composition can be cured by irradiation with ultraviolet rays to form a cured film.
光重合開始剤(D)は、例えば、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-(ジメチルアミノ)-1-[4-(4-モルホリノ)フェニル]-2-(フェニルメチル)-1-ブタノン、又は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;
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、又は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;
1,2-オクタンジオン,1-〔4-(フェニルチオ)フェニル-,2-(O-ベンゾイルオキシム)〕、又はエタノーン,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〕-,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、又はジフェニル-2,4,6-トリメチルベンゾイルホスフィンオキサイド等のアシル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;あるいは、チタノセン系化合物等が挙げられる。
The photopolymerization initiator (D) is, for example, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-. On, 1-hydroxycyclohexylphenylketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, 2- (dimethylamino) -1- [4- (4-morpholino) ) Phenyl] -2- (phenylmethyl) -1-butanone, or 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1- Acetphenone compounds such as butanone;
2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s -Triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s-triazine,
2,4-bis (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, or 2,4-trichloromethyl- (4'-methoxystyryl) -6-Triazine compounds such as triazine;
1,2-octanedione, 1- [4- (phenylthio) phenyl-, 2- (O-benzoyloxime)], or esterone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole 3-Il]-, 1- (O-acetyloxime) and other oxime ester compounds;
Acylphosphine compounds such as bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide or diphenyl-2,4,6-trimethylbenzoylphosphine oxide;
Examples thereof include quinone-based compounds such as 9,10-phenanthrene quinone, camphorquinone, and ethylanthraquinone; borate-based compounds; carbazole-based compounds; imidazole-based compounds; and titanocene-based compounds.
市販品では、アセトフェノン系化合物として、IGM Resins社製の「Omnirad 907」(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)、「Omnirad 369E」(2-(ジメチルアミノ)-1-[4-(4-モルホリノ)フェニル]-2-(フェニルメチル)-1-ブタノン)、「Omnirad 379EG」(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)、アシルホスフィン系化合物として、IGM Resins社製の「Omnirad 819」(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)、「Omnirad TPO」(ジフェニル-2,4,6-トリメチルベンゾイルホスフィンオキサイド)、オキシム系化合物として、BASF社製の1,2-オクタンジオン,1-[4-(フェニルチオ)フェニル-,2-(O-ベンゾイルオキシム)](IRGACURE OXE-01)、エタノーン,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]-,1-(O-アセチルオキシム)(IRGACURE OXE-02)、IRGACURE OXE-03、IRGACURE OXE-04、ADEKA社製のN-1919、NCI-730、NCI-831、NCI-930、常州強力新材料社製のTRONLY TR-PBG-304、TRONLY TR-PBG-305、TRONLY TR-PBG-309、TRONLY TR-PBG-345、TRONLY TR-PBG-3054等が挙げられる。また、特開2007-210991号公報、特開2009-179619号公報、特開2010-037223号公報、特開2010-215575号公報、特開2011-020998号公報、国際公開WO2015/036910号等に記載のオキシム系化合物も挙げられる。これらの中でも、パターン形成性の観点から、オキシム系化合物が好ましく、下記化学式(2)の化合物がより好ましい。 Commercially available products include "Omnirad 907" (2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one) and "Omnirad 369E" (2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one) manufactured by IGM Resins as acetophenone compounds. 2- (dimethylamino) -1- [4- (4-morpholino) phenyl] -2- (phenylmethyl) -1-butanone), "Omnirad 379EG" (2- (dimethylamino) -2-[(4-4-) Methylphenyl) Methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone), as an acylphosphine-based compound, "Omnirad 819" (bis (2,4,6-trimethylbenzoyl)) manufactured by IGM Resins. )-Phenylphosphinoxide), "Omnirad TPO" (diphenyl-2,4,6-trimethylbenzoylphosphinoxide), as an oxime compound, 1,2-octanedione, 1- [4- (phenylthio), manufactured by BASF. Phenyl-, 2- (O-benzoyl oxime)] (IRGACURE OXE-01), Etanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole 3-yl]-, 1- (O) -Acetyl Oxime) (IRGACURE OXE-02), IRGACURE OXE-03, IRGACURE OXE-04, N-1919 manufactured by ADEKA, NCI-730, NCI-831, NCI-930, TRONLY TR manufactured by Joshu Strong New Materials Co., Ltd. -PBG-304, TRONLY TR-PBG-305, TRONLY TR-PBG-309, TRONLY TR-PBG-345, TRONLY TR-PBG-3054 and the like. Further, in JP-A-2007-210991, JP-A-2009-179619, JP-A-2010-037223, JP-A-2010-215575, JP-A-2011-029988, International Publication No. WO2015 / 036910, etc. The described oxime compounds are also mentioned. Among these, an oxime-based compound is preferable from the viewpoint of pattern-forming property, and a compound of the following chemical formula (2) is more preferable.
化学式(2)
化学式(2)の化合物の製造方法は、特に限定されるものではなく、公知の方法を用いることができる。例えば、国際公開WO2015/036910号に記載の方法を用いることができる。 The method for producing the compound of the chemical formula (2) is not particularly limited, and a known method can be used. For example, the method described in International Publication WO2015 / 036910 can be used.
光重合開始剤(D)は、単独または2種類以上を併用して使用できる。 The photopolymerization initiator (D) can be used alone or in combination of two or more.
光重合開始剤(D)の含有量は、有機顔料(A)100質量部に対して、光硬化性、現像性の観点から、2~50質量部が好ましく、2~30質量部がより好ましい。 The content of the photopolymerization initiator (D) is preferably 2 to 50 parts by mass and more preferably 2 to 30 parts by mass with respect to 100 parts by mass of the organic pigment (A) from the viewpoint of photocurability and developability. ..
[シリカ粒子(E)]
本発明の感光性着色組成物は、シリカ粒子(E)を含む。
[Silica particles (E)]
The photosensitive coloring composition of the present invention contains silica particles (E).
シリカ粒子(E)は、特に限定されず、公知のシリカ粒子を用いることができる。 The silica particles (E) are not particularly limited, and known silica particles can be used.
シリカ粒子(E)は、例えば、乾式シリカや、コロイダルシリカなどの湿式シリカが挙げられ、粒径形状や粒子径を制御しやすいコロイダルシリカが好ましい。 Examples of the silica particles (E) include dry silica and wet silica such as colloidal silica, and colloidal silica whose particle size shape and particle diameter can be easily controlled is preferable.
シリカ粒子(E)の形状は、硬化膜の表面平滑性の観点から、球状が好ましい。 The shape of the silica particles (E) is preferably spherical from the viewpoint of surface smoothness of the cured film.
シリカ粒子(E)の平均一次粒子径は、シワの抑制の観点から、1~100nmであることが好ましく、5~50nmであることがより好ましく、10~30nmであることが特に好ましい。 The average primary particle size of the silica particles (E) is preferably 1 to 100 nm, more preferably 5 to 50 nm, and particularly preferably 10 to 30 nm from the viewpoint of suppressing wrinkles.
シリカ粒子(E)の市販品は、例えば、扶桑化学工業製のPL-1-IPA、PL-1-TOL、PL-2L-PGME、PL-2L-MEK、アドマテックス社製のYA010C-LDI、YA050C-LHI、日産化学工業社製のMA-ST-M、MA-ST-L、IPA-ST、IPA-ST-L、IPA-ST-UP、EG-ST、NPC-ST-30、PGM-ST、MEK-ST-40、MEK-ST-UP、MIBK-ST、MIBK-ST-L、CHO-ST-M、EAC-ST、PMA-ST、TOL-ST、DMAC-ST、MEK-AC-2140Y、MEK-AC-4130Y、MEK-AC-5140Z、PGM-AC-2140Z、PEM-AC-4130Y、MIBK-AC-4130Y、MIBK-AC-2140Y、MIBK-SD-L、MEK-EC-2130Y、MEK-EC-6150P、MEK-EC-7150P、EP-F2130Y、EP-F6140P、EP-F7150P等が挙げられる。 Commercially available silica particles (E) include, for example, PL-1-IPA, PL-1-TOR, PL-2L-PGME, PL-2L-MEK manufactured by Fuso Chemical Industry, and YA010C-LDI manufactured by Admatex. YA050C-LHI, MA-ST-M, MA-ST-L, IPA-ST, IPA-ST-L, IPA-ST-UP, EG-ST, NPC-ST-30, PGM-manufactured by Nissan Chemical Industry Co., Ltd. ST, MEK-ST-40, MEK-ST-UP, MIBK-ST, MIBK-ST-L, CHO-ST-M, EAC-ST, PMA-ST, TOR-ST, DMAC-ST, MEK-AC- 2140Y, MEK-AC-4130Y, MEK-AC-5140Z, PGM-AC-2140Z, PEM-AC-4130Y, MIBK-AC-4130Y, MIBK-AC-2140Y, MIBK-SD-L, MEK-EC-2130Y, Examples thereof include MEK-EC-6150P, MEK-EC-7150P, EP-F2130Y, EP-F6140P, EP-F7150P and the like.
シリカ粒子(E)の含有量は、パターン形成性、シワの抑制の観点から、感光性着色組
成物の不揮発分100質量%中、5質量%以上、30質量%以下であることが好ましく、10質量%を超え、25質量%未満であることがより好ましい。
The content of the silica particles (E) is preferably 5% by mass or more and 30% by mass or less in 100% by mass of the non-volatile content of the photosensitive coloring composition from the viewpoint of pattern formability and suppression of wrinkles. More preferably, it exceeds% by mass and is less than 25% by mass.
[近赤外線吸収剤(H)]
本発明の感光性着色組成物は、固体撮像素子に用いる場合、近赤外線吸収剤(H)を含有することが好ましい。これにより、特定波長の近赤外線の透過を制御することができ、近赤外線領域との分離性が向上する。
近赤外線吸収剤(H)は、波長750~1,200nmの光を吸収する化合物である。
[Near infrared absorber (H)]
When the photosensitive coloring composition of the present invention is used for a solid-state image sensor, it preferably contains a near-infrared absorber (H). As a result, the transmission of near-infrared rays having a specific wavelength can be controlled, and the separability from the near-infrared rays region is improved.
The near-infrared absorber (H) is a compound that absorbs light having a wavelength of 750 to 1,200 nm.
近赤外線吸収剤(H)は、例えば、シアニン化合物、フタロシアニン化合物、ナフタロシアニン化合物、インモニウム化合物、ピロロピロ-ル化合物、スクアリリウム化合物、クロコニウム化合物等が挙げられる。これらの中でも、シアニン化合物、ピロロピロ-ル化合物、スクアリリウム化合物が好ましい。 Examples of the near-infrared absorber (H) include a cyanine compound, a phthalocyanine compound, a naphthalocyanine compound, an immonium compound, a pyrolopyrrole compound, a squarylium compound, a croconium compound and the like. Among these, a cyanine compound, a pyrolopyrrole compound, and a squarylium compound are preferable.
近赤外線吸収剤(H)の中でシアニン化合物は、国際公開第WO2006/006573号、国際公開第WO2010/073857号、特開2013-241598号公報、特開2016-113501号公報、特開2016-113504号公報;フタロシアニン化合物は、特開平4-23868号公報、特開平06-192584号公報、特開2000-63691号公報、国際公開第WO2014/208514号;ナフタロシアニン化合物は、特開平11-152414号公報、特開2000-86919号公報、特開2009-29955号公報、国際公開第WO2018/186490号;インモニウム化合物は、特開2005-336150号公報、特開2007-197492号公報、特開2008-88426号公報;ピロロピロ-ル化合物は、特開2009-263614号公報、特開2010-90313号公報、特開2011-068731号公報;スクアリリウム化合物は、特開2011-132361号公報、特開2016-142891号公報、国際公開第WO2017/135359号、国際公開第WO2018/225837号、特開2019-001987号公報、国際公開第WO2020/054718号;クロコニウム化合物は、国際公開第WO2019/021767号などに記載の化合物が挙げられる。 Among the near-infrared absorbers (H), the cyanine compounds are International Publication No. WO2006 / 006573, International Publication No. WO2010 / 073857, Japanese Patent Application Laid-Open No. 2013-241598, Japanese Patent Application Laid-Open No. 2016-11351, Japanese Patent Application Laid-Open No. 2016- No. 113504; The phthalocyanine compound is JP-A-4-23868, JP-A-06-192584, JP-A-2000-63691, International Publication No. WO2014 / 208514; The phthalocyanine compound is JP-A-11-152414. Japanese Patent Laid-Open No. 2000-86919, Japanese Patent Application Laid-Open No. 2009-29955, International Publication No. WO2018 / 18649; For immonium compounds, JP-A-2005-336150, JP-A-2007-197492, JP-A. 2008-88426; Pyrrolopyrrole compound is JP-A-2009-263614, JP-A-2010-90313, JP-A-2011-068731; Squarylium compound is JP-A-2011-132361, JP-A. 2016-142891, International Publication No. WO2017 / 135359, International Publication No. WO2018 / 225837, Japanese Patent Application Laid-Open No. 2019-001987, International Publication No. WO2020 / 054718; Examples of the compound described in.
近赤外線吸収剤(H)は、単独または2種類以上を併用して使用できる。 The near-infrared absorber (H) can be used alone or in combination of two or more.
近赤外線吸収剤(H)の含有量は、有機顔料(A)100質量部に対して、10~200質量部であることが好ましく、15~150質量部があることがより好ましく、20~100質量部であることが特に好ましい。 The content of the near-infrared absorber (H) is preferably 10 to 200 parts by mass, more preferably 15 to 150 parts by mass, and 20 to 100 parts by mass with respect to 100 parts by mass of the organic pigment (A). It is particularly preferable that it is by mass.
[増感剤(I)]
本発明の感光性着色組成物は、増感剤(I)を含有できる。
[Sensitizer (I)]
The photosensitive coloring composition of the present invention can contain a sensitizer (I).
増感剤(I)は、例えば、カルコン誘導体、ジベンザルアセトン等に代表される不飽和ケトン類、ベンジルやカンファーキノン等に代表される1,2-ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノール誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリ-ルメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピ
リリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレ-ン錯体、有機ルテニウム錯体、又はミヒラ-ケトン誘導体、α-アシロキシエステル、アシルオキサイド、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ーン、3,3’又は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’-ビス(ジエチルアミノ)ベンゾフェノン等が挙げられる。
The sensitizer (I) is, for example, a chalcone derivative, unsaturated ketones represented by dibenzalacetone, 1,2-diketone derivative represented by benzyl, camphorquinone, etc., benzoin derivative, fluorene derivative, naphthoquinone. Polymethine dyes such as derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, aclysine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indolin. Derivatives, azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triallylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphy Radin derivative, naphthalocyanine derivative, subphthalocyanine derivative, pyrylium derivative, thiopyrilium derivative, tetraphyllin derivative, anurene derivative, spiropyrane derivative, spiroxazine derivative, thiospiropyrane derivative, metal allene complex, organic ruthenium complex, or Mihira-ketone derivative. , Α-Acyloxyester, acyloxide, methylphenylglycilate, benzyl, 9,10-phenanthrene quinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalofenone, 3,3'or Examples thereof include 4,4'-tetra (t-butylperoxycarbonyl) benzophenone and 4,4'-bis (diethylamino) benzophenone.
増感剤(I)の中で、チオキサントン誘導体、ミヒラ-ケトン誘導体、カルバゾール誘導体が好ましい。具体的な化合物は、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2,4-ジクロロチオキサントン、2-イソプロピルチオキサントン、4-イソプロピルチオキサントン、1-クロロ-4-プロポキシチオキサントン、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、N-エチルカルバゾール、3-ベンゾイル-N-エチルカルバゾール、3,6-ジベンゾイル-N-エチルカルバゾール等が好ましい。 Among the sensitizers (I), thioxanthone derivatives, Mihira-ketone derivatives, and carbazole derivatives are preferable. Specific compounds include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis. (Dimethylamino) Benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'-bis (ethylmethylamino) benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl- N-ethylcarbazole and the like are preferable.
増感剤(I)は、単独または2種類以上を併用して使用できる。 The sensitizer (I) can be used alone or in combination of two or more.
増感剤(I)の含有量は、光重合開始剤(D)100質量部に対して、3~60質量部が好ましく、5~50質量部がより好ましい。適量含有すると光硬化性、現像性が向上する。 The content of the sensitizer (I) is preferably 3 to 60 parts by mass, more preferably 5 to 50 parts by mass with respect to 100 parts by mass of the photopolymerization initiator (D). When an appropriate amount is contained, photocurability and developability are improved.
[熱硬化性化合物(J)]
本発明の感光性着色組成物は、熱硬化性化合物(J)を含有できる。これにより、加熱工程で熱硬化性化合物(J)が反応し、架橋密度が高まるため耐熱性が向上する。
[Thermosetting compound (J)]
The photosensitive coloring composition of the present invention can contain a thermosetting compound (J). As a result, the thermosetting compound (J) reacts in the heating step, and the crosslink density is increased, so that the heat resistance is improved.
熱硬化性化合物(J)は、低分子化合物や、樹脂のような高分子量化合物でもよい。熱硬化性化合物(J)は、例えば、エポキシ化合物、オキセタン化合物、ベンゾグアナミン化合物、ロジン変性マレイン酸化合物、ロジン変性フマル酸化合物、メラミン化合物、尿素化合物、及びフェノール化合物が挙げられる。これらの中でもエポキシ化合物およびオキセタン化合物が好ましい。 The thermosetting compound (J) may be a low molecular weight compound or a high molecular weight compound such as a resin. Examples of the thermosetting compound (J) include an epoxy compound, an oxetane compound, a benzoguanamine compound, a rosin-modified maleic acid compound, a rosin-modified fumaric acid compound, a melamine compound, a urea compound, and a phenol compound. Among these, epoxy compounds and oxetane compounds are preferable.
(エポキシ化合物(J-1))
エポキシ化合物(J-1)は、例えば、ビスフェノール類(ビスフェノールA、ビスフェノールF、ビスフェノールS、ビフェノール、ビスフェノールAD等)、フェノール類(フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等)と各種アルデヒド(ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等)との重縮合物、フェノール類と各種ジエン化合物(ジシクロペンタジエン、テルペン類、ビニルシクロヘキセン、ノールボルナジエン、ビニルノールボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等)との重合物、フェノール類とケトン類(アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等)との重縮合物、フェノール類と芳香族ジメタノール類(ベンゼンジメタノール、α,α,α’,α’-ベンゼンジメタノール、ビフェニルジメタノール、α,α,α’,α’-ビフェニルジメタノール等)との重縮合物、フェノール類と芳香族ジクロロメチル類(α,α’-ジクロロキシレン、ビスクロロメチルビフェニル等)との重縮合物、ビスフェノール類と各種アルデヒドの重縮合物、アルコール類等をグリシジル化したグリシジルエーテル系エポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキシ樹脂、脂肪族エポキシ樹脂、グリシジルアミン系エポキシ樹脂、グリシジルエステル系エポキシ樹脂等が挙げられる。
(Epoxy compound (J-1))
The epoxy compound (J-1) includes, for example, bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, etc.). Dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthoaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.) With polycondensates, phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, nourbornadiene, vinylnolbornene, tetrahydroinden, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.) Polymers, phenols and ketones (acetone, methylethylketone, methylisobutylketone, acetophenone, benzophenone, etc.) and polycondensates, phenols and aromatic dimethanols (benzenedimethanol, α, α, α', α', α Polycondensate with'-benzenedimethanol, biphenyldimethanol, α, α, α', α'-biphenyldimethanol, etc.), phenols and aromatic dichloromethyls (α, α'-dichloroxylene, bischloro Polycondensate with (methylbiphenyl, etc.), polycondensate of bisphenols and various aldehydes, glycidyl ether-based epoxy resin obtained by glycidylizing alcohols, etc., alicyclic epoxy resin, heterocyclic epoxy resin, aliphatic epoxy resin, Examples thereof include a glycidylamine-based epoxy resin and a glycidyl ester-based epoxy resin.
市販品は、例えば、油化シェルエポキシ社製のエピコート807,815,825,827,828,190P,191P、三井化学社製のTECHMORE VG3101L、日本化薬社製のEPPN-201,501H,502H、EOCN-102S,103S,104S,1020ジャパンエポキシレジン社製のエピコート1004,1256、JER1032H60,157S65,157S70,152,154、ダイセル化学工業社製のセロキサイド2021、EHPE-3150、ナガセケムテックス社製のデナコールEX-211,212,252,313,314,321,411,421,512,521,611,612,614,614B,622,711,721、日産化学工業社製のTEPIC-L,H,S等が挙げられる。 Commercially available products include, for example, Epicoat 807,815,825,827,828,190P,191P manufactured by Yuka Shell Epoxy, TECHMORE VG3101L manufactured by Mitsui Chemicals, EPPN-201, 501H, 502H manufactured by Nippon Kayaku Co., Ltd. EOCN-102S, 103S, 104S, 1020 Epicoat 1004, 1256 manufactured by Japan Epoxy Resin, JER1032H60, 157S65, 157S70, 152, 154, Serokiside 2021 manufactured by Daicel Chemical Industries, Ltd. EX-21,212,252,313,314,321,411,421,512,521,611,612,614,614B,622,711,721, TEPIC-L, H, S, etc. manufactured by Nissan Chemical Industries, Ltd. Can be mentioned.
エポキシ化合物(J-1)の含有量は、硬化膜の耐熱性の観点から、有機顔料(A)100質量部に対して、0.5~300質量部が好ましく、1.0~50質量部がより好ましい。 The content of the epoxy compound (J-1) is preferably 0.5 to 300 parts by mass, preferably 1.0 to 50 parts by mass with respect to 100 parts by mass of the organic pigment (A) from the viewpoint of heat resistance of the cured film. Is more preferable.
(オキセタン化合物(J-2))
オキセタン化合物(J-2)は、オキセタン基を有する公知の化合物である。オキセタン化合物は、1官能オキセタン化合物、2官能オキセタン化合物、3官能以上のオキセタン化合物が挙げられる。
(Oxetane compound (J-2))
The oxetane compound (J-2) is a known compound having an oxetane group. Examples of the oxetane compound include a monofunctional oxetane compound, a bifunctional oxetane compound, and a trifunctional or higher functional oxetane compound.
1官能オキセタン化合物は、例えば、(3-エチルオキセタン-3-イル)メチルアクリレート、 (3-エチルオキセタン-3-イル)メチルメタクリレート、3-エチル-3-
ヒドロキシメチルオキセタン、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、3-エチル-3-(フェノキシメチル)オキセタン、3-エチル-3-(2-メタクリロキシメチル)オキセタン、3-エチル-3-{[3-(トリエトキシシリル)プロポキシ]メチル}オキセタン等が挙げられる。
The monofunctional oxetane compound is, for example, (3-ethyloxetane-3-yl) methyl acrylate, (3-ethyloxetane-3-yl) methyl methacrylate, 3-ethyl-3-yl.
Hydroxymethyl oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3- (2-methacryloxymethyl) oxetane, 3-ethyl -3-{[3- (triethoxysilyl) propoxy] methyl} oxetane and the like can be mentioned.
市販品は、例えば、大阪有機化学工業社製のOXE-10,30、東亞合成社製のOXT-101,212等が挙げられる。 Examples of commercially available products include OXE-10,30 manufactured by Osaka Organic Chemical Industry Co., Ltd., OXT-101,212 manufactured by Toagosei Co., Ltd., and the like.
2官能オキセタン化合物は、例えば、4,4’-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニル)、1,4-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ベンゼン、1,4-ビス{[(3-エチル-3-オキセタニル)メトキシ]メチル}ベンゼン、ジ[1-エチル(3-オキセタニル)]メチルエーテル、ジ[1-エチル(3-オキセタニル)]メチルエーテル3-エチル-3-ヒドロキシメチルオキセタン、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、3-エチル-3-(2-フェノキシメチル)オキセタン、3,7-ビス(3-オキセタニル)-5-オキサ-ノナン、1,2-ビス[(3-エチル-3-オキセタニルメトキシ)メチル]エタン、1,3-ビス[(3-エチル-3-オキセタニルメトキシ)メチル]プロパン、エチレングリコ-スビス(3-エチル-3-オキセタニルメチル)エーテル、ジシクロペンテニルビス(3-エチル-3-オキセタニルメチル)エーテル、トリエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、テトラエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、1,4-ビス(3-エチル-3-オキセタニルメトキシ)ブタン、1,6-ビス(3-エチル-3-オキセタニルメトキシ)ヘキサン、ポリエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、エチレンオキシド(EO)変性ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、プロピレンオキシド(PO)変性ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、EO変性水添ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、PO変性水添ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、EO変性ビスフェノールF(3-エチル-3-オキセタニルメチル)エーテル等が挙げられる。 Bifunctional oxetane compounds include, for example, 4,4'-bis [(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl), 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene, 1,4-Bis {[(3-ethyl-3-oxetanyl) methoxy] methyl} benzene, di [1-ethyl (3-oxetanyl)] methyl ether, di [1-ethyl (3-oxetanyl)] methyl ether 3 -Ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (2-phenoxymethyl) oxetane, 3,7-bis (3-oxetanyl)- 5-oxa-nonane, 1,2-bis [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl-3-oxetanylmethoxy) methyl] propane, ethylene glyco-subis (3-Ethyl-3-oxetanylmethyl) ether, dicyclopentenylbis (3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tetraethyleneglycolbis (3) -Ethyl-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, 1,6-bis (3-ethyl-3-oxetanylmethoxy) hexane, polyethylene glycol bis (3-) Ethyl-3-oxetanylmethyl) ether, ethylene oxide (EO) modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, propylene oxide (PO) modified bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, EO-modified hydrogenated bisphenol A bis (3-ethyl-3-oxetanylmethyl) ether, PO-modified hydrogenated bisphenol A-bis (3-ethyl-3-oxetanylmethyl) ether, EO-modified bisphenol F (3-ethyl-3-oxetanyl) Methyl) ether and the like can be mentioned.
市販品は、例えば、宇部興産社製のOXBP、OXTP、東亞合成社製のOXT-121,221等が挙げられる。 Examples of commercially available products include OXBP and OXTP manufactured by Ube Kosan Co., Ltd., and OXT-121,221 manufactured by Toagosei Co., Ltd.
3官能以上のオキセタン化合物は、例えば、ペンタエリスリトールトリス(3-エチル-3-オキセタニルメチル)エーテル、ペンタエリスリトールテトラキス(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールヘキサ(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールペンタキス(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールテトラキス(3-エチル-3-オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールヘキサ(3-エチル-3-オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールペンタキス(3-エチル-3-オキセタニルメチル)エーテル、ジトリメチロ-ルプロパンテトラキス(3-エチル-3-オキセタニルメチル)エーテル、オキセタン基を含有する樹脂(例えば、特許第3783462号記載のオキセタン変性フェノールノボラック樹脂等)や前述のOXE-30のような(メタ)アクリルモノマーをラジカル重合させて得られる重合体が挙げられる。 Examples of the trifunctional or higher functional oxetane compound include pentaerythritol tris (3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, and dipentaerythritol hexa (3-ethyl-3). -Oxetanylmethyl) ether, dipentaerythritol pentax (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol hexa (3-ethyl-) 3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol pentaxe (3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropanetetrakis (3-ethyl-3-oxetanylmethyl) ether, resin containing oxetane radical (3-ethyl-3-oxetanylmethyl) ether For example, a polymer obtained by radically polymerizing a (meth) acrylic monomer such as the oxetane-modified phenol novolak resin described in Patent No. 3783462 and the above-mentioned OXE-30 can be mentioned.
オキセタン化合物(J-2)の含有量は、感光性着色組成物の不揮発分100質量%中、0.5~50質量%が好ましく、1~40質量%がより好ましい。 The content of the oxetane compound (J-2) is preferably 0.5 to 50% by mass, more preferably 1 to 40% by mass, based on 100% by mass of the non-volatile content of the photosensitive coloring composition.
メラミン化合物は、メラミン環構造を有する化合物である。メラミン化合物は、メチロ-ル型やエーテル型の化合物が好ましく、メラミン環1個当たりのメチロ-ル基および/またはエーテル基数が平均5.0以上のメラミン化合物がより好ましい。適度にメチロ-ル基やエーテル基数を有すると過不足ない耐熱性が得やすい。 The melamine compound is a compound having a melamine ring structure. The melamine compound is preferably a methylol-type or ether-type compound, and more preferably a melamine compound having an average number of methylol groups and / or ether groups of 5.0 or more per melamine ring. If it has an appropriate number of methylol groups and ether groups, it is easy to obtain heat resistance that is not excessive or insufficient.
市販品は、例えば、三和ケミカル社製の二カラックMW-30HM,MW-390,MW-100LM,MX-750LM,MW-30M,MW-30,MW-22,MS-21,MS-11,MW-24X,MS-001,MX-002,MX-730,MX-750,MX-708,MX-706,MX-042,MX-45,MX-500,MX-520,MX-43,MX-417,MX-410、日本サイテックインダストリーズ社製のサイメル232,235,236,238,285,300,301,303,350,370等が挙げられる。 Commercially available products include, for example, Nikarak MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, manufactured by Sanwa Chemical Co., Ltd. MW-24X, MS-001, MX-002, MX-730, MX-750, MX-708, MX-706, MX-042, MX-45, MX-500, MX-520, MX-43, MX- Examples thereof include 417, MX-410, and Cymel 232,235,236,238,285,300,301,303,350,370 manufactured by Cytec Industries, Japan.
これらの中でもメラミン環1個当たりのメチロ-ル基、及び/又は、エーテル基数が平均5.0以上である、三和ケミカル社製のニカラックMW-30HM、MW-390、MW-100LM、MX-750LM、MW-30M、MW-30、MW-22、MS-21、MS-11、MW-24X、MX-45、日本サイテックインダストリ-ズ社製のサイメル232,235,236,238,300,301,303,350等は、架橋密度を高められる面で好ましい。 Among these, Nicarac MW-30HM, MW-390, MW-100LM, MX- of Sanwa Chemical Co., Ltd., which has an average number of methylol groups and / or ether groups of 5.0 or more per melamine ring. 750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, MX-45, Cymel 232,235,236,238,300, manufactured by Nippon Cytec Industries, Inc. 301, 303, 350 and the like are preferable in terms of increasing the crosslink density.
熱硬化性化合物(J)は、単独または2種類以上を併用して使用できる。 The thermosetting compound (J) can be used alone or in combination of two or more.
[硬化剤(硬化促進剤)]
本発明の感光性着色組成物は、熱硬化性化合物(J)の硬化を補助するため、硬化剤(硬化促進剤)を併用できる。硬化剤は、例えば、アミン系化合物、酸無水物、活性エステル、カルボン酸系化合物、スルホン酸系化合物等が挙げられる。硬化剤は、例えば、アミン化合物(例えば、ジシアンジアミド、ベンジルジメチルアミン、4-(ジメチルアミノ)-N,N-ジメチルベンジルアミン、4-メトキシ-N,N-ジメチルベンジルアミン、4-メチル-N,N-ジメチルベンジルアミン等)、4級アンモニウム塩化合物(例えば、トリエチルベンジルアンモニウムクロリド等)、ブロックイソシアネート化合物(例えば、ジメチルアミン等)、イミダゾール誘導体二環式アミジン化合物及びその塩(例えば、イミダゾール、2-メチルイミダゾール、2-エチルイミダゾール、2-エチル-4-メチルイミダゾール、2-フェニルイミダゾール、4-フェニルイミダゾール、1-シアノエチル-2-フェニルイミダゾール、1-(2-シアノエチル)-2-エチル-4-メチルイミダゾール等)、リン化合物(例えば、トリフェニルホスフィン等)、S-トリアジン誘導体(例えば、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン、2-ビニル-2,4-ジアミノ-S-トリアジン、2-ビニル-4,6-ジアミノ-S-トリアジン・イソシアヌル酸付加物、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン・イソシアヌル酸付加物等)等が挙げられる。
[Curing agent (curing accelerator)]
In the photosensitive coloring composition of the present invention, a curing agent (curing accelerator) can be used in combination in order to assist the curing of the thermosetting compound (J). Examples of the curing agent include amine-based compounds, acid anhydrides, active esters, carboxylic acid-based compounds, and sulfonic acid-based compounds. The curing agent is, for example, an amine compound (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl-N, N-Dimethylbenzylamine, etc.), quaternary ammonium salt compounds (eg, triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (eg, dimethylamine, etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg, imidazole, 2). -Methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2-ethyl-4 -Methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), S-triazine derivatives (eg, 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino- Examples thereof include S-triazine, 2-vinyl-4,6-diamino-S-triazine / isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine / isocyanuric acid adduct, etc.).
硬化剤は、単独または2種類以上を併用して使用できる。 The curing agent can be used alone or in combination of two or more.
硬化剤の含有量は、熱硬化性化合物(J)100質量部に対して、0.01~15質量部が好ましい。 The content of the curing agent is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting compound (J).
[チオール系連鎖移動剤(K)]
本発明の感光性着色組成物は、チオール系連鎖移動剤(K)を含有できる。チオール系連鎖移動剤(K)は、光重合開始剤(D)と併用すると光照射後のラジカル重合の際、酸素による重合阻害を受けにくいチイルラジカルが発生し、感光性着色組成物の光感度が向上する。
[Thiol chain transfer agent (K)]
The photosensitive coloring composition of the present invention can contain a thiol-based chain transfer agent (K). When the thiol-based chain transfer agent (K) is used in combination with the photopolymerization initiator (D), a chile radical that is less susceptible to polymerization inhibition by oxygen is generated during radical polymerization after light irradiation, and the photosensitivity of the photosensitive coloring composition is increased. improves.
チオール系連鎖移動剤(K)は、チオール基(SH基)2以上有る多官能チオールが好ましい。なお、チオール系連鎖移動剤は、SH基を4以上有することがより好ましい。官能基数が増えると膜の表面から最深部まで光硬化し易くなる。 The thiol-based chain transfer agent (K) is preferably a polyfunctional thiol having two or more thiol groups (SH groups). It is more preferable that the thiol-based chain transfer agent has 4 or more SH groups. As the number of functional groups increases, photocuring from the surface of the film to the deepest part becomes easier.
多官能チオールは、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-ルビスチオプロピオネート、1,4-ブタンジオ-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-ルプロパントリスチオグリコレート、トリメチロ-ルプロパントリスチオプロピオネート、トリメチロ-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-トリアジンなどが挙げられ、好ましくは、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-ルプロパントリスチオプロピオネート、ペンタエリスリトールテトラキスチオプロピオネート等が挙げられる。 Polyfunctional thiols include, for example, hexanedithiol, decandithiol, 1,4-butandio-rubistiopropionate, 1,4-butandio-rubistioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate. , Trimethylol Propane Tristhioglycolate, Trimethylol Propane Tristhiopropionate, Trimethylol Propanetris (3-Mercaptobutyrate), Pentaerythritol Tetrakissthioglycolate, Pentaerythritol Tetrakissthiopropionate, Trimercapto Tris (2-hydroxyethyl) propionate isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2- (N, N-dibutylamino) -4,6-dimercapto- Examples thereof include s-triazine, and preferred examples include ethylene glycol bisthiopropionate, trimethylolpropanetristhiopropionate, and pentaerythritol tetrakisthiopropionate.
チオール系連鎖移動剤(K)は、単独または2種類以上を併用して使用できる。 The thiol-based chain transfer agent (K) can be used alone or in combination of two or more.
チオール系連鎖移動剤(K)の含有量は、感光性着色組成物の不揮発分100質量部に対して、1~10質量部が好ましく、2~8質量部がより好ましい。適量含有すると光感度が向上し、硬化膜の表面にシワが発生し難くなる。 The content of the thiol-based chain transfer agent (K) is preferably 1 to 10 parts by mass, more preferably 2 to 8 parts by mass, based on 100 parts by mass of the non-volatile content of the photosensitive coloring composition. When an appropriate amount is contained, the light sensitivity is improved and wrinkles are less likely to occur on the surface of the cured film.
[重合禁止剤(L)]
本発明の感光性着色組成物は、重合禁止剤(L)を含有できる。
[Polymerization inhibitor (L)]
The photosensitive coloring composition of the present invention can contain a polymerization inhibitor (L).
重合禁止剤(L)は、例えば、カテコール、レゾールシノール、1,4-ヒドロキノーン、2-メチルカテコール、3-メチルカテコール、4-メチルカテコール、2-エチルカテコール、3-エチルカテコール、4-エチルカテコール、2-プロピルカテコール、3-プロピルカテコール、4-プロピルカテコール、2-n-ブチルカテコール、3-n-ブチルカテコール、4-n-ブチルカテコール、2-t-ブチルカテコール、3-t-ブチルカテコール、4-t-ブチルカテコール、3,5-ジ-t-ブチルカテコール等のアルキルカテコール系化合物、2-メチルレゾールシノール、4-メチルレゾールシノール、2-エチルレゾールシノール、4-エチルレゾールシノール、2-プロピルレゾールシノール、4-プロピルレゾールシノール、2-n-ブチルレゾールシノール、4-n-ブチルレゾールシノール、2-t-ブチルレゾールシノール、4-t-ブチルレゾールシノール等のアルキルレゾールシノール系化合物、メチルヒドロキノン、エチルヒドロキノーン、プロピルヒドロキノーン、t-ブチルヒドロキノン、2,5-ジ-t-ブチルヒドロキノン等のアルキルヒドロキノーン系化合物、トリブチルホスフィン、トリオクチルホスフィン、トリシクロヘキシルホスフィン、トリフェニルホスフィン、トリベンジルホスフィン等のホスフィン化合物、トリオクチルホスフィンオキサイド、トリフェニルホスフィンオキサイドなどのホスフィンオキサイド化合物、トリフェニルホスファイト、トリスノニルフェニルホスファイト等のホスファイト化合物、ピロガロ-ル、フロログルシン等が挙げられる。 The polymerization inhibitor (L) is, for example, catechol, resorcinol, 1,4-hydroquinone, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatecol, 3-ethylcatechol, 4-ethylcatechol. , 2-propyl catechol, 3-propyl catechol, 4-propyl catechol, 2-n-butyl catechol, 3-n-butyl catechol, 4-n-butyl catechol, 2-t-butyl catechol, 3-t-butyl catechol , 4-t-butylcatechol, alkylcatechol compounds such as 3,5-di-t-butylcatechol, 2-methylresorcinol, 4-methylresorcinol, 2-ethylresorsinol, 4-ethylresorsinol, 2 -Alkylresolsinol compounds such as propylresorsinol, 4-propylresorsinol, 2-n-butylresorsinol, 4-n-butylresorsinol, 2-t-butylresorsinol, 4-t-butylresorsinol, etc. Alkylhydroquinone compounds such as methylhydroquinone, ethylhydroquinone, propylhydroquinone, t-butylhydroquinone, 2,5-di-t-butylhydroquinone, tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, tri Examples thereof include phosphinic compounds such as benzylphosphin, phosphinoxide compounds such as trioctylphosphinoxide and triphenylphosphine oxide, phosphite compounds such as triphenylphosphite and trisnonylphenylphosphite, pyrogallol and fluoroglucin.
重合禁止剤(L)の含有量は、感光性着色組成物の不揮発分100質量%中、0.01~0.4質量%が好ましい。 The content of the polymerization inhibitor (L) is preferably 0.01 to 0.4% by mass based on 100% by mass of the non-volatile content of the photosensitive coloring composition.
[紫外線吸収剤(M)]
本発明の感光性着色組成物は、紫外線吸収剤(M)を含有できる。
[Ultraviolet absorber (M)]
The photosensitive coloring composition of the present invention can contain an ultraviolet absorber (M).
紫外線吸収剤(M)は、紫外線吸収機能を有する有機化合物であり、ベンゾトリアゾール系有機化合物、トリアジン系有機化合物、ベンゾフェノン系有機化合物、サリチル酸エステル系有機化合物、シアノアクリレート系有機化合物、及びサリシレート系有機化合物等が挙げられる。 The ultraviolet absorber (M) is an organic compound having an ultraviolet absorbing function, and is a benzotriazole-based organic compound, a triazine-based organic compound, a benzophenone-based organic compound, a salicylic acid ester-based organic compound, a cyanoacrylate-based organic compound, and a salicylate-based organic compound. Examples include compounds.
ベンゾトリアゾール系化合物は、例えば、2-(5メチル-2-ヒドロキシフェニル)ベンゾトリアゾール、2-(2-ヒドロキシ-5-t-ブチルフェニル)-2H-ベンゾトリアゾール、2-[2-ヒドロキシ-3,5-ビス(α, α-ジメチルベンジル)フェニル]-2H-ベンゾトリアゾール、2-(3-tブチル-5-メチル-2-ヒドロキシフェニル)-5-クロロベンゾトリアゾール、2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール、5%の2-メトキシ-1-メチルエチルアセテートと95%のベンゼンプロパン酸,3-(2H-ベンゾトリアゾール2-イル)-(1,1-ジメチルエチル)-4-ヒドロキシ,C7-9側鎖及び直鎖アルキルエステルの混合物、2-(2H-ベンゾトリアゾール2-イル)-4,6-ビス(1-メチル-1-フェニルエチル)フェノール、2-(2H-ベンゾトリアゾール2-イル)-6-(1-メチル-1-フェニルエチル)-4-(1,1,3,3-テトラメチルブチル)フェノール、メチル 3-(3-(2H-ベンゾトリアゾール2-イル)-5-t-ブチル-4-ヒドロキシフェニル)プロピオネート/ポリエチレングリコール300の反応生成物、2-(2H-ベンゾトリアゾール2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール、2,2’-メチレンビス[6-(2H-ベンゾトリアゾール2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール]、2-(2H-ベンゾトリアゾール2-イル)-p-クレゾール、2-(5-クロロ-2H-ベンゾトリアゾール2-イル)-6-t-ブチル-4-メチルフェノール、2-(3,5-ジ-t-アミル-2-ヒドロキシフェニル)ベンゾトリアゾール、2-[2-ヒドロキシ-5-[2-(メタクリロイルオキシ)エチル]フェニル]-2H-ベンゾトリアゾール、オクチル-3-[3-tert-ブチル-4-ヒドロキシ-5-(5-クロロ-2H-ベンゾトリアゾール2-イル)フェニル]プロピオネート、2-エチルヘキシル-3-[3-tert-ブチル-4-ヒドロキシ-5-(5-クロロ-2H-ベンゾトリアゾール2-イル)フェニル]プロピオネートが挙げられる。 Examples of the benzotriazole-based compound include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (2-hydroxy-5-t-butylphenyl) -2H-benzotriazole, 2- [2-hydroxy-3. , 5-Bis (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole, 2- (3-tbutyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (2'- Hydroxy-5'-t-octylphenyl) benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3- (2H-benzotriazole 2-yl)-(1,1- Dimethylethyl) -4-hydroxy, C7-9 side chain and linear alkyl ester mixture, 2- (2H-benzotriazole2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol, 2- (2H-benzotriazole2-yl) -6- (1-methyl-1-phenylethyl) -4- (1,1,3,3-tetramethylbutyl) phenol, methyl 3- (3- (2H) -Reaction product of -benzotriazole 2-yl) -5-t-butyl-4-hydroxyphenyl) propionate / polyethylene glycol 300, 2- (2H-benzotriazole 2-yl) -4- (1,1,3) 3-Tetramethylbutyl) phenol, 2,2'-methylenebis [6- (2H-benzotriazole2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol], 2- (2H-) Bentriazole 2-yl) -p-cresol, 2- (5-chloro-2H-benzotriazole 2-yl) -6-t-butyl-4-methylphenol, 2- (3,5-di-t-amyl) -2-Hydroxyphenyl) benzotriazole, 2- [2-hydroxy-5- [2- (methacryloyloxy) ethyl] phenyl] -2H-benzotriazole, octyl-3- [3-tert-butyl-4-hydroxy- 5- (5-Chloro-2H-benzotriazole2-yl) phenyl] propionate, 2-ethylhexyl-3- [3-tert-butyl-4-hydroxy-5- (5-chloro-2H-benzotriazole2-yl) ) Phenyl] propionate can be mentioned.
市販品は、例えば、BASFジャパン社製のTINUVIN P,PS,234,32
6,329,384-2,900,928,99-2,1130、ADEKA社製のアデカスタブLA-29,LA-31RG,LA-32,LA-36、ケミプロ化成社製のKEMISORB71,73,74,79,279、大塚化学社製のRUVA-93等が挙げられる。
Commercially available products include, for example, TINUVIN P, PS, 234, 32 manufactured by BASF Japan.
6,329,384-2,900,928,99-2,1130, ADEKA's ADEKA STAB LA-29, LA-31RG, LA-32, LA-36, KEMISORB71, 73, 74, manufactured by Chemipro Kasei. 79,279, RUVA-93 manufactured by Otsuka Chemical Co., Ltd. and the like can be mentioned.
トリアジン系化合物は、例えば、2,4-ビス(2,4-ジメチルフェニル)-6-(2-ヒドロキシ-4-n-オクチルオキシフェニル)-1,3,5-トリアジン、2-[4,6-ビス(2,4-ジメチルフェニル)-1,3,5-トリアジン-2-イル]-5-[3-(ドデシルオキシ)-2-ヒドロキシプロポキシ]フェノール、2-(2,4-ジヒドロキシフェニル)-4,6-ビス(2,4-ジメチルフェニル)-1,3,5-トリアジンと(2-エチルヘキシル)-グリシド酸エステルの反応生成物、2,4-ビス「2-ヒドロキシ-4-ブトキシフェニル」-6-(2,4-ジブトキシフェニル)-1,3,5-トリアジン、2-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)-5-(ヘキシルオキシ)フェノール、2-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)-5-[2-(2-エチルヘキサノイルオキシ)エトキシ]フェノール、2,4,6-トリス(2-ヒドロキシ-4-ヘキシルオキシ-3-メチルフェニル)-1,3,5-トリアジン等が挙げられる。 The triazine compound is, for example, 2,4-bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-n-octyloxyphenyl) -1,3,5-triazine, 2- [4. 6-bis (2,4-dimethylphenyl) -1,3,5-triazine-2-yl] -5- [3- (dodecyloxy) -2-hydroxypropoxy] phenol, 2- (2,4-dihydroxy) Phenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine and (2-ethylhexyl) -glycidate ester reaction product, 2,4-bis "2-hydroxy-4 -Butoxyphenyl "-6- (2,4-dibutoxyphenyl) -1,3,5-triazine, 2- (4,6-diphenyl-1,3,5-triazine-2-yl) -5-( Hexyloxy) Phenol, 2- (4,6-diphenyl-1,3,5-triazine-2-yl) -5- [2- (2-ethylhexanoyloxy) ethoxy] phenol, 2,4,6- Examples thereof include tris (2-hydroxy-4-hexyloxy-3-methylphenyl) -1,3,5-triazine.
市販品は、例えば、ケミプロ化成社製のKEMISORB 102、BASFジャパン
社製のTINUVIN 400,405,460,477,479,1577ED、AD
EKA社のアデカスタブLA-46,LA-F70、サンケミカル社製のCYASORB
UV-1164等が挙げられる。
Commercially available products include, for example, KEMISORB 102 manufactured by Chemipro Kasei Co., Ltd., TINUVIN 400, 405, 460, 477, 479, 1577ED manufactured by BASF Japan, and AD.
EKA's Adecaster LA-46, LA-F70, Sun Chemical's CYASORB
UV-1164 and the like can be mentioned.
ベンゾフェノン系化合物は、例えば、2,4-ジ-ヒドロキシベンゾフェノン、2-ヒドロキシ-4-メトキシベンゾフェノン、2-ヒドロキシ-4-メトキシベンゾフェノン5-スルホン酸-3水温、2-ヒドロキシ-4-n-オクトキシベンゾフェノーン、2,2’-ジ-ヒドロキシ-4-メトキシベンゾフェノン、2,2’-ジヒドロキシ-4,4’-ジメトキシベンゾフェノン、4-ドデシロキシ-2-ヒドロキシベンゾフェノン、2-ヒドロキシ-4-オクタデシロキシベンゾフェノン、2,2’ジヒドロキシ-4,4’-ジメトキシベンゾフェノン、2,2’,4,4’-テトラヒドロキシベンゾフェノン、2-ヒドロキシ-4-メトキシ-2’-カルボキシベンゾフェノン等が挙げられる。 Benzophenone compounds include, for example, 2,4-di-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone 5-sulfonic acid-3 water temperature, 2-hydroxy-4-n-oct. Xybenzophenone, 2,2'-di-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octa Examples thereof include decyloxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone and the like.
市販品は、例えば、ケミプロ化成社製のKEMISORB 10,11,11S,12
,111、シプロ化成社製のSEESORB 101,107、ADEKA社製のアデカ
スタブ1413、サンケミカル社製のUV-12等が挙げられる。
Commercially available products include, for example, KEMIPROB 10, 11, 11S, 12 manufactured by Chemipro Kasei Co., Ltd.
, 111, SEESORB 101, 107 manufactured by Sipro Kasei Co., Ltd., ADEKA STAB 1413 manufactured by ADEKA Co., Ltd., UV-12 manufactured by Sun Chemical Co., Ltd. and the like.
サリチル酸エステル系化合物は、例えば、サリチル酸フェニル、サリチル酸p-オクチルフェニル、サリチル酸p-tertブチルフェニル等が挙げられる。 Examples of the salicylic acid ester-based compound include phenyl salicylate, p-octylphenyl salicylate, and p-tert-butyl phenyl salicylate.
紫外線吸収剤(M)の含有量は、光重合開始剤(D)と紫外線吸収剤(M)との合計100質量%中、5~70質量%が好ましい。 The content of the ultraviolet absorber (M) is preferably 5 to 70% by mass based on 100% by mass of the total of the photopolymerization initiator (D) and the ultraviolet absorber (M).
[酸化防止剤(N)]
本発明の感光性着色組成物は、酸化防止剤(N)を含有できる。酸化防止剤(N)は、感光性着色組成物に含まれる光重合開始剤(D)や熱硬化性化合物(J)が、熱硬化やITOアニ-ル時の熱工程によって酸化による黄変を防ぐ。特に、感光性着色組成物の有機顔料(A)濃度が高い場合、相対的に重合性化合物(C)の含有量が減少するため、光重合開始剤(D)の増量や、熱硬化性化合物の配合で対応すると硬化膜が黄変し易い。そのため、酸化防止剤を含むことで、加熱工程時の酸化による硬化膜の黄変を防止する。
[Antioxidant (N)]
The photosensitive coloring composition of the present invention may contain an antioxidant (N). As the antioxidant (N), the photopolymerization initiator (D) and the thermosetting compound (J) contained in the photosensitive coloring composition undergo yellowing due to oxidation due to heat curing or a thermal process during ITO annealing. prevent. In particular, when the concentration of the organic pigment (A) in the photosensitive coloring composition is high, the content of the polymerizable compound (C) is relatively reduced, so that the amount of the photopolymerization initiator (D) is increased or the thermosetting compound is used. The cured film tends to turn yellow when it is mixed with. Therefore, by containing an antioxidant, yellowing of the cured film due to oxidation during the heating step is prevented.
酸化防止剤(N)は、例えば、ヒンダ-ドフェノール系、ヒンダ-ドアミン系、リン系、イオウ系、およびヒドロキシルアミン系の化合物が挙げられる。なお、本明細書で酸化防止剤は、ハロゲン原子を含有しない化合物が好ましい。 Examples of the antioxidant (N) include hydride-based phenol-based, hydride-based amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds. In the present specification, the antioxidant is preferably a compound containing no halogen atom.
これらの中でも、ヒンダ-ドフェノール系酸化防止剤、ヒンダ-ドアミン系酸化防止剤、リン系酸化防止剤、イオウ系酸化防止剤が好ましい。 Among these, a hydride-based phenol-based antioxidant, a hydride-based amine-based antioxidant, a phosphorus-based antioxidant, and a sulfur-based antioxidant are preferable.
ヒンダ-ドフェノール系酸化防止剤は、例えば、1,3,5-トリス(3,5-ジ-t-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、1,1,3-トリス-(2’-メチル-4’-ヒドロキシ-5’-t-ブチルフェニル)-ブタン、4,4’-ブチリデン-ビス-(2-t-ブチル-5-メチルフェノール)、3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオン酸ステアリル、ペンタエリスリトールテトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、3,9-ビス[2-[3-(3-t-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニルオキシ]-1,1-ジメチルエチル]-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン、1,3,5-トリス(3,5-ジ-t-ブチル-4-ヒドロキシフェニルメチル)-2,4,6-トリメチルベンゼン、1,3,5-トリス(3-ヒドロキシ-4-t-ブチル-2,6-ジメチルベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、2,2’-メチレンビス(6-t-ブチル-4-エチルフェノール)、2,2’-チオジエチルビス-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)-プロピオネート、N,N-ヘキサメチレンビス(3,5-ジ-t-ブチル-4-ヒドロキシ-ヒドロシンナムアミド)、i-オクチル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、4,6-ビス(ドデシルチオメチル)-o-クレゾール、3,5-ジ-t-ブチル-4-ヒドロキシベンジルホスホン酸モノエチルエステルのカルシウム塩、4,6-ビス(オクチルチオメチル)-o-クレゾール、ビス[3-(3-メチル-4-ヒドロキシ-5-t-ブチルフェニル)プロピオン酸]エチレンビスオキシビスエチレン、1,6-ヘキサンジオ-ルビス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、2,4-ビス-(n-オクチルチオ)-6-(4-ヒドロキシ-3,5-ジ-t-ブチルアニリノ)-1,3,5-トリアジン、2,2’-チオ-ビス-(6-t-ブチル-4-メチルフェノール)、2,5-ジ-t-アミル-ヒドロキノーン、2,6-ジ-t-ブチル-4-ノニルフェノール、2,2’-イソブチリデン-ビス-(4,6-ジメチル-フェノール)、2,2’-メチレン-ビス-(6-(1-メチル-シクロヘキシル)-p-クレゾール)、2,4-ジメチル-6-(1-メチル-シクロヘキシル)-フェノール等が挙げられる。 The hydride phenolic antioxidant is, for example, 1,3,5-tris (3,5-di-t-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 ( 1H, 3H, 5H) -trion, 1,1,3-tris- (2'-methyl-4'-hydroxy-5'-t-butylphenyl) -butane, 4,4'-butylidene-bis- (2) -T-butyl-5-methylphenol), 3- (3,5-di-t-butyl-4-hydroxyphenyl) stearyl propionate, pentaerythritol tetrakis [3- (3,5-di-t-butyl-) 4-Hydroxyphenyl) propionate, 3,9-bis [2- [3- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy] -1,1-dimethylethyl] -2,4 8,10-Tetraoxaspiro [5.5] undecane, 1,3,5-tris (3,5-di-t-butyl-4-hydroxyphenylmethyl) -2,4,6-trimethylbenzene, 1, 3,5-Tris (3-hydroxy-4-t-butyl-2,6-dimethylbenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, 2,2 '-Methylenebis (6-t-butyl-4-ethylphenol), 2,2'-thiodiethylbis- (3,5-di-t-butyl-4-hydroxyphenyl) -propionate, N, N-hexamethylene Bis (3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), i-octyl-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, 4,6- Bis (dodecylthiomethyl) -o-cresol, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoethyl ester, 4,6-bis (octylthiomethyl) -o-cresol, bis [3- (3-Methyl-4-hydroxy-5-t-butylphenyl) propionic acid] ethylenebisoxybisethylene, 1,6-hexanediolbis [3- (3,5-di-t-butyl-4) -Hydroxyphenyl) propionate, 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t-butylanilino) -1,3,5-triazine, 2,2'-thio -Bis- (6-t-butyl-4-methylphenol), 2,5-di-t-amyl-hydroquinone, 2,6-di-t-butyl-4-nonylphenol, 2,2'-isobutylidene-bis -(4) , 6-dimethyl-phenol), 2,2'-methylene-bis- (6- (1-methyl-cyclohexyl) -p-cresol), 2,4-dimethyl-6- (1-methyl-cyclohexyl) -phenol And so on.
市販品は、例えば、ADEKA社製のアデカスタブAO-20,AO-30,AO-40,AO-50,AO-60,AO-80,AO-330、ケミプロ社製のKEMINOX101,179,76,9425、BASFジャパン社製のIRGANOX1010,1035,1076,1098,1135,1330,1726,1425WL,1520L,245,259,3114,5057,565、サンケミカル社製のサイアノックスCY-1790,CY-2777等が挙げられる。 Commercially available products include, for example, ADEKA tabs AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, AO-330 manufactured by ADEKA, and KEMINOX 101, 179, 76, 9425 manufactured by Chemipro. , BASF Japan's IRGANOX 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 245, 259, 3114, 5057, 565, Sun Chemical's Sianox CY-1790, CY-2777, etc. Can be mentioned.
ヒンダ-ドアミン系酸化防止剤は、例えば、テトラキス(1,2,2,6,6-ペンタメチル-4-ピペリジル)-1,2,3,4-ブタンテトラカルボキシレート、テトラキス(2,2,6,6-テトラメチル-4-ピペリジル)1,2,3,4-ブタンテトラカルボキシレート、ビス(1,2,2,6,6-ペンタメチル-4-ピペリジル)セバケート、ビス(2,2,6,6-テトラメチル-4-ピペリジル)セバケート、ビス(1-ウンデカノキシ-2,2,6,6-テトラメチルピペリジン-4-イル)カルボネート、1,2,2,6,6-ペンタメチル-4-ピペリジルメタクリレート、2,2,6,6-テトラメチル-4-ピペリジルメタクリレート、コハク酸ジメチルと1-(2-ヒドロキシエチル)-4-ヒドロキシ-2,2,6,6-テトラメチルピペリジンとの重縮合物、ポリ[[6-[(1,1,3,3-テトラメチルブチル)アミノ]-s-トリアジン-2,4-ジイル]-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]-ヘキサメチレン-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]]、4-ヒドロキシ-2,2,6,6-テトラメチル-1-ピペリジンエタノールと3,5,5-トリメチルヘキサン酸のエステル、N,N’-4,7-テトラキス〔4,6-ビス{N-ブチル-N-(1,2,2,6,6-ペンタメチル-4-ピペリジル)アミノ}-1,3,5-トリアジン-2-イル〕-4,7-ジアザデカン-1,10-ジアミン、デカン二酸ビス(2,2,6,6-テトラメチル-1-(オクチルオキシ)-4-ピペリジニル)エステル,1,1-ジメチルエチルヒドロペルオキシドとオクタンの反応生成物、ビス(1,2,2,6,6-ペンタメチル-4-ピリペリジル)[[3,5-ビス(1,1ジメチルエチル)-4-ヒドロキシフェニル]メチル]ブチルマロネートメチル1,2,2,6,6-ペンタメチル-4-ピリペリジルセバケート、ポリ[[6-モルホリノ-s-トリアジン-2,4-ジイル]-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]-ヘキサメチレン-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]]、2,2,6,6-テトラメチル-4-ピペリジル-C12-21およびC18不飽和脂肪酸エステル、N,N’-ビス(2,2,6,6-テトラメチル-4-ピペリジル)-1,6-ヘキサメチレンジアミン、2-メチル-2-(2,2,6,6-テトラメチル-4-ピペリジル)アミノ-N-(2,2,6,6-テトラメチル-4-ピペリジル)プロピオンアミド等が挙げられる。 Examples of the hindered amine antioxidants include tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate and tetrakis (2,2,6). , 6-Tetramethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (2,2,6) , 6-Tetramethyl-4-piperidyl) sebacate, bis (1-undecanoxy-2,2,6,6-tetramethylpiperidine-4-yl) carbonate, 1,2,2,6,6-pentamethyl-4-yl Weights of piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidylmethacrylate, dimethyl succinate and 1- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine Condensate, poly [[6-[(1,1,3,3-tetramethylbutyl) amino] -s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4) -Piperidyl) imino] -hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl) imino]], 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinethanol Ester of 3,5,5-trimethylhexanoic acid, N, N'-4,7-tetrakis [4,6-bis {N-butyl-N- (1,2,2,6,6-pentamethyl-4-) Piperidine) amino} -1,3,5-triazine-2-yl] -4,7-diazadecan-1,10-diamine, bisdecanediate (2,2,6,6-tetramethyl-1- (octyl) Oxy) -4-piperidinyl) ester, reaction product of 1,1-dimethylethylhydroperoxide and octane, bis (1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis (3,5-bis (3,5-bis) 1,1 dimethylethyl) -4-hydroxyphenyl] methyl] butyl malonate methyl 1,2,2,6,6-pentamethyl-4-piperidylsevakate, poly [[6-morpholino-s-triazine-2 , 4-Diyl]-[(2,2,6,6-tetramethyl-4-piperidyl) imino] -hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl) imino]], 2,2,6,6-tetramethyl-4-piperidyl-C12-21 and C18 unsaturated fatty acid ester, N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) -1, 6-Hexamethylenediamine, 2-methyl-2- (2,2,6,6-tetramethyl-4-piperidyl) amino-N- (2,2,6,6-tetramethyl-4-piperidyl) propionamide And so on.
市販品は、例えば、ADEKA社製のアデカスタブLA-52,LA-57,LA-63P,LA-68,LA-72,LA-77Y,LA-77G,LA-81,LA-82,LA-87,LA-402F,LA-502XP、ケミプロ化成社製のKAMISTAB29,62,77,94、BASFジャパン社製のTinuvin111FDL,123,144,249,292,5100、サンケミカル社製のサイアソ-ブUV-3346,UV-3529,UV-3853等が挙げられる。 Commercially available products include, for example, ADEKA Tab LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, LA-77G, LA-81, LA-82, LA-87 manufactured by ADEKA. , LA-402F, LA-502XP, KAMISTAB29, 62, 77, 94 manufactured by Chemipro Kasei, Tinuvin111FDL, 123, 144, 249, 292, 5100 manufactured by BASF Japan, Siasorb UV-3346 manufactured by Sun Chemical Co., Ltd. , UV-3259, UV-3853 and the like.
リン系酸化防止剤は、例えば、ジ(2,6-ジ-t-ブチル-4-メチルフェニル)ペンタエリスリトールジホスファイト、ジステアリルペンタエリスリトールジホスファイト、2,2’-メチレンビス(4,6-ジ-t-ブチルフェニル)2-エチルヘキシルホスファイト、トリス(2,4-ジ-t-ブチルフェニル)ホスファイト、トリス(ノニルフェニル)ホスファイト、テトラ(C12~C15アルキル)-4,4’-イソプロピリデンジフェニルジホスファイト、ジフェニルモノ(2-エチルヘキシル)ホスファイト、ジフェニルイソデシルホスファイト、トリス(イソデシル)ホスファイト、トリフェニルホスファイト、テトラキス(2,4-ジ-t-ブチルフェニル)-4,4-ビフェニルジフォスホニト、トリス(トリデシル)ホスファイト、フェニルイソオクチルホスファイト、フェニルイソデシルホスファイト、フェニルジ(トリデシル)ホスファイト、ジフェニルイソオクチルホスファイト、ジフェニルトリデシルホスファイト、4,4’-イソプロピリデンジフェノールアルキルホスファイト、トリスノニルフェニルホスファイト、トリスジノニルフェニルホスファイト、トリス(ビフェニル)ホスファイト、ジ(2,4-ジ-t-ブチルフェニル)ペンタエリスリトールジホスファイト、ジ(ノニルフェニル)ペンタエリスリトールジホスファイト、フェニルビスフェノールAペンタエリスリトールジホスファイト、テトラトリデシル4,4’-ブチリデンビス(3-メチル-6-t-ブチルフェノール)ジホスファイト、ヘキサトリデシル1,1,3-トリス(2-メチル-4-ヒドロキシ-5-t-ブチルフェニル)ブタントリホスファイト、3,5-ジ-t-ブチル-4-ヒドロキシベンジルホスファイトジエチルエステル、ソジウムビス(4-t-ブチルフェニル)ホスファイト、ソジウム-2,2-メチレン-ビス(4,6-ジ-t-ブチルフェニル)-ホスファイト、1,3-ビス(ジフェノキシフォスフォニロキシ)-ベンゼン、亜リン酸エチルビス(2,4-ジt-ブチル-6-メチルフェニル)等が挙げられる。 Phylline antioxidants include, for example, di (2,6-di-t-butyl-4-methylphenyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, 2,2'-methylenebis (4,6). -Di-t-butylphenyl) 2-ethylhexyl phosphite, tris (2,4-di-t-butylphenyl) phosphite, tris (nonylphenyl) phosphite, tetra (C12-C15 alkyl) -4,4' -Isopropyridene diphenyl diphosphite, diphenylmono (2-ethylhexyl) phosphite, diphenylisodecylphosphite, tris (isodecyl) phosphite, triphenylphosphite, tetrakis (2,4-di-t-butylphenyl)- 4,4-Biphenyldiphoshonito, Tris (tridecyl) phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi (tridecyl) phosphite, diphenylisooctylphosphite, diphenyltridecylphosphite, 4,4 '-Isopropyridene diphenol alkyl phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris (biphenyl) phosphite, di (2,4-di-t-butylphenyl) pentaerythritol diphosphite, di (Nonylphenyl) Pentaerythritol diphosphite, Phenylbisphenol A Pentaerythritol diphosphite, tetratridecyl 4,4'-butylidenebis (3-methyl-6-t-butylphenol) diphosphite, hexatridecyl 1,1,3- Tris (2-methyl-4-hydroxy-5-t-butylphenyl) butanetriphosphite, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, sodiumbis (4-t-butylphenyl) phos Fight, Sodium-2,2-Methylene-bis (4,6-di-t-butylphenyl) -phosphite, 1,3-bis (diphenoxyphosphonyloxy) -benzene, ethylbis phosphite (2,4) -Dit-butyl-6-methylphenyl) and the like.
市販品は、例えば、ADEKA社製のアデカスタブPEP-36,PEP-8,HP-10,2112,1178,1500,C,135A,3010,TPP、BASFジャパン社製のIRGAFOS168、クラリアントケミカルズ社製のHostanoxP-EPQ等が挙げられる。 Commercially available products include, for example, ADEKA tab PEP-36, PEP-8, HP-10, 211, 1178, 1500, C, 135A, 3010, TPP, IRGAFOS168 manufactured by BASF Japan, and HostanoxP manufactured by Clariant Chemicals. -EPQ and the like can be mentioned.
イオウ系酸化防止剤は、例えば、2,2-ビス{〔3-(ドデシルチオ)-1-オキソプロポキシ〕メチル}プロパン-1,3-ジイルビス〔3-(ドデシルチオ)プロピオネート〕、3,3’-チオビスプロピオン酸ジトリデシル、2,2-チオ-ジエチレンビス〔3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート〕、2,4-ビス〔(オクチルチオ)メチル〕-o-クレゾール、2,4-ビス〔(ラウリルチオ)メチル〕-o-クレゾール等が挙げられる。 Sulfur-based antioxidants include, for example, 2,2-bis {[3- (dodecylthio) -1-oxopropoxy] methyl} propane-1,3-diylbis [3- (dodecylthio) propionate], 3,3'-. Ditridecyl thiobispropionate, 2,2-thio-diethylenebis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], 2,4-bis [(octylthio) methyl] -o- Cresol, 2,4-bis [(laurylthio) methyl] -o-cresol and the like can be mentioned.
市販品は、例えば、ADEKA社製のアデカスタブAO-412S,AO-503、ケミプロ化成社製のKEMINOXPLS等が挙げられる。 Examples of commercially available products include ADEKA STAB AO-412S and AO-503 manufactured by ADEKA, and KEMINOXPLS manufactured by Chemipro Kasei Co., Ltd.
酸化防止剤(N)は、単独または2種類以上を併用して使用できる。 The antioxidant (N) can be used alone or in combination of two or more.
酸化防止剤(N)の含有量は、感光性着色組成物の不揮発分100質量%中、0.5~5.0質量%が好ましい。適量含有すると透過率、分光特性、及び感度が向上する。 The content of the antioxidant (N) is preferably 0.5 to 5.0% by mass based on 100% by mass of the non-volatile content of the photosensitive coloring composition. When an appropriate amount is contained, the transmittance, spectral characteristics, and sensitivity are improved.
[レベリング剤(O)]
本発明の感光性着色組成物は、レベリング剤(O)を含有できる。これにより、塗工時の基板に対する濡れ性、及び乾燥性がより向上する。レベリング剤(O)は、例えば、シリコ-ン系界面活性剤、フッ素系界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、アニオン性界面活性剤、両性界面活性剤等が挙げられる。
[Leveling agent (O)]
The photosensitive coloring composition of the present invention can contain a leveling agent (O). As a result, the wettability and dryness to the substrate at the time of coating are further improved. Examples of the leveling agent (O) include a silicone-based surfactant, a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and an amphoteric surfactant.
シリコ-ン系界面活性剤は、例えば、シロキサン結合からなる直鎖状ポリマーや、側鎖や末端に有機基を導入した変性シロキサンポリマーが挙げられる。 Examples of the silicone-based surfactant include a linear polymer composed of a siloxane bond and a modified siloxane polymer having an organic group introduced into a side chain or a terminal.
市販品は、例えば、ビックケミー社製のBYK-300,306,310,313,315N,320,322,323,330,331,333,342,345,346,347,348,349,370,377,378,3455,UV3510,3570、東レ・ダウコ-ニング社製のFZ-7002,2110,2122,2123,2191,5609、信越化学工業社製のX-22-4952、X-22-4272、X-22-6266、KF-351A、KF-354L、KF-355A、KF-945、KF-640、KF-642、KF-643、X-22-4515、KF-6004、KP-341等が挙げられる。 Commercially available products include, for example, BYK-300, 306, 310, 313,315N, 320,322,323,330,331,333,342,345,346,347,348,349,370,377, manufactured by Big Chemie. 378,3455, UV3510,3570, FZ-7002,2110,2122,212,2191,5609, manufactured by Toray Industries, Inc., X-22-4952, X-22-4272, X-, manufactured by Shin-Etsu Chemical Co., Ltd. Examples thereof include 22-6266, KF-351A, KF-354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-4515, KF-6004, KP-341 and the like.
フッ素系界面活性剤は、例えば、フルオロカーボン鎖を有する界面活性剤又はレベリン
グ剤が挙げられる。
Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain or a leveling agent.
市販品は、例えば、AGCセイミケミカル社製のサーフロンS-242,243,420,611,651,386、DIC社製のメガファックF-253,477,551,552,555,558,560,570,575,576、R-40-LM、R-41、RS-72-K、DS-21、住友スリーエム社製のFC-4430,4432、三菱マテリアル電子化成社製のEF-PP31N09、EF-PP33G1、EF-PP32C1、ネオス社製フタージェントの602A等が挙げられる。 Commercially available products include, for example, AGC Seimi Chemical's Surflon S-242,243,420,611,651,386 and DIC's Megafuck F-253,477,551,552,555,558,560,570. , 575,576, R-40-LM, R-41, RS-72-K, DS-21, FC-4430, 4432 manufactured by Sumitomo 3M, EF-PP31N09, EF-PP33G1 manufactured by Mitsubishi Materials Electronics. , EF-PP32C1, Neos Co., Ltd. Futergent 602A and the like.
ノニオン性界面活性剤は、例えば、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セチルエーテル、ポリオキシエチレンステアリルエーテル、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アルキルエーテル、ポリオキシエチレンミリステルエーテル、ポリオキシエチレンオクチルドデシルエーテル、ポリオキシアルキレンアルキルエーテル、ポリオキシフェニレンジスチレン化フェニルエーテル、ポリオキシエチレントリベンジルフェニルエーテル、ポリオキシエチレンポリオキシプロピレングリコール、ポリオキシアルキレンアルケニルエーテル、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、ソルビタンモノラウレート、ソルビタンモノパルミテ-ト、ソルビタンモノステアレート、ソルビタンジステアレート、ソルビタントリステアレート、ソルビタンモノオレート、ソルビタントリオレート、ソルビタンセスキオレート、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテ-ト、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリステアレート、ポリオキシエチレンソルビタンモノオレート、ポリオキシエチレンソルビタントリイソステアレート、テトラオレイン酸ポリオキシエチレンソルビット、グリセロ-ルモノステアレート、グリセロ-ルモノオレート、ポリエチレングリコールモノラウレート、ポリエチレングリコールモノステアレート、ポリエチレングリコールジステアレート、ポリエチレングリコールモノオレート、ポリオキシエチレン硬化ヒマシ油、ポリオキシエチレンアルキルアミン、アルキルアルカノールアミド、アルキルイミダゾリン等が挙げられる。 Nonionic surfactants include, for example, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristel ether, and polyoxyethylene octyl. Dodecyl ether, polyoxyalkylene alkyl ether, polyoxyphenylenedistyrene phenyl ether, polyoxyethylene tribenzylphenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyalkylene alkenyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Alkyl ether phosphate ester, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, sorbitan monoolate, sorbitan triolate, sorbitan sesquiolate, polyoxyethylene sorbitan mono Laurate, Polyoxyethylene sorbitan monopalmitate, Polyoxyethylene sorbitan monostearate, Polyoxyethylene sorbitan tristearate, Polyoxyethylene sorbitan monoolate, Polyoxyethylene sorbitan triisostearate, Polyoxytetraoleate Ethylene sorbit, glycerol monostearate, glycerol monooleate, polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene glycol monostearate, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, alkyl Examples thereof include alkanolamide and alkylimidazolin.
市販品は、例えば、花王社製のエマルゲン103,104P,106,108,109P,120,123P,130K,147,150,210P,220,306P,320P,350,404,408,409PV,420,430,705,707,709,1108,1118S-70,1135S-70,1150S-60,2020G-HA,2025G,LS-106,LS-110,LS-114,MS-110,A-60,A-90,B-66,PP-290、ラテムルPD-420,PD-430,PD-430S,PD-450、レオドールSP-L10,SP-P10,SP-S10V,SP-S20,SP-S30V,SP-O10V,SP-O30V、スーパーSP-L10,AS-10V,AO-10V,AO-15V,TW-L120,TW-L106,TW-P120,TW-S120V,TW-S320V,TW-O120V,TW-O106V,TW-IS399C、スーパーTW-L120,430V,440V,460V,MS-50,MS-60,MO-60,MS-165V、エマノーン1112,3199V,3299V,3299RV,4110,CH-25,CH-40,CH-60(K),アミ-ト102,105,105A,302,320、アミノーンPK-02S、L-02、ホモゲノールL-95、ADEKA社製のアデカプルロニック(登録商標)L-23,31,44,61,62,64,71,72,101,121、TR-701,702,704,913R、共栄社化学社製の(メタ)アクリル酸系(共)重合体ポリフロ-No.75,No.90,No.95等が挙げられる。 Commercially available products include, for example, Emargen 103, 104P, 106, 108, 109P, 120, 123P, 130K, 147, 150, 210P, 220, 306P, 320P, 350, 404, 408, 409PV, 420, 430 manufactured by Kao Corporation. , 705,707,709,1108,1118S-70,1135S-70,1150S-60,2020G-HA, 2025G, LS-106, LS-110, LS-114, MS-110, A-60, A-90 , B-66, PP-290, Latemul PD-420, PD-430, PD-430S, PD-450, Leodor SP-L10, SP-P10, SP-S10V, SP-S20, SP-S30V, SP-O10V , SP-O30V, Super SP-L10, AS-10V, AO-10V, AO-15V, TW-L120, TW-L106, TW-P120, TW-S120V, TW-S320V, TW-O120V, TW-O106V, TW-IS399C, Super TW-L120, 430V, 440V, 460V, MS-50, MS-60, MO-60, MS-165V, Emanon 1112, 3199V, 3299V, 3299RV, 4110, CH-25, CH-40, CH-60 (K), Polymer 102, 105, 105A, 302, 320, Aminone PK-02S, L-02, Homogenol L-95, ADEKA Adecapluronic® L-23, 31, 44,61,62,64,71,72,101,121, TR-701,702,704,913R, (meth) acrylic acid-based (co) polymer polyflo-No. manufactured by Kyoeisha Chemical Co., Ltd. 75, No. 90, No. 95 and the like can be mentioned.
カチオン性界面活性剤は、例えばアルキルアミン塩やラウリルトリメチルアンモニウムクロライド、ステアリルトリメチルアンモニウムクロライド、セチルトリメチルアンモニ
ウムクロライドなどのアルキル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が挙げられる。
Examples of the cationic surfactant include alkylquaternary ammonium salts such as alkylamine salts, lauryltrimethylammonium chlorides, stearyltrimethylammonium chlorides, and cetyltrimethylammonium chlorides, and ethylene oxide adducts thereof.
市販品は、例えば、花王社製のアセタミン24、コータミン24P、60W、86Pコンク等が挙げられる。 Examples of commercially available products include acetamine 24, coatamine 24P, 60W, 86P conch piercing manufactured by Kao Corporation.
アニオン性界面活性剤は、例えば、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ナトリウム、スチレン-アクリル酸共重合体のアルカリ塩、アルキルナフタレ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等が挙げられる。 Anionic surfactants include, for example, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalene sulfonate, sodium alkyldiphenyl ether disulfonate, monoethanol lauryl sulfate. Examples thereof include amine, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate and the like.
市販品は、例えば、ネオス社製のフタージェント100,150、ADEKA社製のアデカホープYES-25、アデカコールTS-230E,PS-440E,EC-8600等が挙げられる。 Examples of commercially available products include Futergent 100 and 150 manufactured by Neos, Adeka Hope YES-25 manufactured by ADEKA, and Adecacol TS-230E, PS-440E, and EC-8600.
両性界面活性剤は、例えば、ラウリン酸アミドプロピルベタイン、ラウリルベタイン、コカミドプロピルベタイン、ステアリルベタイン、アルキルジメチルアミノ酢酸ベタイン等のアルキルベタイン、ラウリルジメチルアミンオキサイド等のアルキルアミンオキサイド等が挙げられる。 Examples of the amphoteric surfactant include alkyl betaines such as lauric acid amidopropyl betaine, lauryl betaine, cocamidopropyl betaine, stearyl betaine and alkyldimethylaminoacetic acid betaine, and alkylamine oxides such as lauryldimethylamine oxide.
市販品は、花王社製のアンヒトール20AB,20BS,24B,55AB,86B,20Y-B,20N等が挙げられる。 Examples of commercially available products include Anhitor 20AB, 20BS, 24B, 55AB, 86B, 20Y-B, 20N manufactured by Kao Corporation.
レベリング剤(O)は、単独または2種類以上を併用して使用できる。 The leveling agent (O) can be used alone or in combination of two or more.
レベリング剤(O)の含有量は、感光性着色組成物の不揮発分100質量%中、0.001~2.0質量%が好ましく、0.005~1.0質量%がより好ましい。この範囲内であることで、感光性着色組成物の塗布性と密着性のバランスがより向上する。 The content of the leveling agent (O) is preferably 0.001 to 2.0% by mass, more preferably 0.005 to 1.0% by mass, based on 100% by mass of the non-volatile content of the photosensitive coloring composition. Within this range, the balance between the coatability and the adhesiveness of the photosensitive coloring composition is further improved.
[貯蔵安定剤(P)]
本発明の感光性着色組成物は、貯蔵安定剤(P)を含有できる。これにより、感光性着色組成物の経時粘度が安定化する。貯蔵安定剤(P)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、テトラフェニルなどの有機ホスフィン、亜リン酸塩等が挙げられる。
[Storage stabilizer (P)]
The photosensitive coloring composition of the present invention can contain a storage stabilizer (P). This stabilizes the viscosity of the photosensitive coloring composition over time. The storage stabilizer (P) includes, for example, quaternary ammonium chloride such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and phosphoric acid and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, tetraphenyl and the like. Examples thereof include organic phosphine and phosphite.
貯蔵安定剤(P)の含有量は、有機顔料(A)100質量部に対して、0.1~10質量部が好ましい。 The content of the storage stabilizer (P) is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the organic pigment (A).
[密着向上剤(Q)]
本発明の感光性着色組成物は、密着向上剤(Q)を含有できる。これにより、硬化膜と基材の密着性が向上する。また、フォトリソグラフィー法で幅が狭いパターンを形成し易くなる。
[Adhesion improver (Q)]
The photosensitive coloring composition of the present invention can contain an adhesion improver (Q). This improves the adhesion between the cured film and the base material. In addition, the photolithography method facilitates the formation of narrow patterns.
密着向上剤(Q)は、例えば、シランカップリング剤等が挙げられる。シランカップリング剤は、例えば、ビニルトリメトキシシラン、ビニルトリエトキシシラン等のビニルシラン類、3-メタクリロキシプロピルメチルジメトキシシラン、3-メタクリロキシプロ
ピルトリメトキシシラン、3-メタクリロキシプロピルメチルジエトキシシラン、3-メタクリロキシプロピルトリエトキシシラン、3-ア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、2-(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、3-グリシドキシプロピルメチルジメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルメチルジエトキシシラン、3-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-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、3-トリエトキシシリル-N-(1,3-ジメチル-ブチリデン)プロピルアミン、N-フェニル-3-アミノプロピルトリメトキシシラン、N-(ビニルベンジル)-2-アミノエチル-3-アミノプロピルトリメトキシシランの塩酸塩等のアミノシラン類、3-メルカプトプロピルメチルジメトキシシラン、3-メルカプトプロピルトリメトキシシラン等のメルカプト類、p-スチリルトリメトキシシラン等のスチリル類、3-ウレイドプロピルトリエトキシシラン等のウレイド類、ビス(トリエトキシシリルプロピル)テトラスルフィド等のスルフィド類、3-イソシアネートプロピルトリエトキシシラン等のイソシアネート類などのシランカップリング剤が挙げられる。
Examples of the adhesion improver (Q) include a silane coupling agent and the like. Examples of the silane coupling agent include vinylsilanes such as vinyltrimethoxysilane and vinyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane. (Meta) acrylic silanes such as 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane , 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane and other epoxysilanes, N-2- (aminoethyl) -3-aminopropyl Methyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1,3-) Aminosilanes such as dimethyl-butylidene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane hydrochloride, 3-mercaptopropyl Melcaptos such as methyldimethoxysilane and 3-mercaptopropyltrimethoxysilane, styryls such as p-styryltrimethoxysilane, ureids such as 3-ureidopropyltriethoxysilane, bis (triethoxysilylpropyl) tetrasulfide and the like. Examples thereof include silane coupling agents such as sulfides and isocyanates such as 3-isocyanuspropyltriethoxysilane.
密着向上剤(Q)は、単独または2種類以上を併用して使用できる。 The adhesion improver (Q) can be used alone or in combination of two or more.
密着向上剤(Q)の含有量は、有機顔料(A)100質量部に対して、0.01~10質量部が好ましく、0.05~5質量部がより好ましい。 The content of the adhesion improver (Q) is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass with respect to 100 parts by mass of the organic pigment (A).
[有機溶剤(R)]
本発明の感光性組成物は、有機溶剤(R)を含有できる。
[Organic solvent (R)]
The photosensitive composition of the present invention can contain an organic solvent (R).
有機溶剤(R)は、例えば、1,2,3-トリクロロプロパン、1-メトキシ-2-プロパノール、乳酸エチル、1,3-ブタンジオ-ル、1,3-ブチレングリコール、1,3-ブチレングリコールジアセテート、1,4-ジオキサン、2-ヘプタノーン、2-メチル-1,3-プロパンジオ-ル、3,5,5-トリメチル-2-シクロヘキセン-1-オン、3,3,5-トリメチルシクロヘキサノン、3-エトキシプロピオン酸エチル、3-メチル-1,3-ブタンジオ-ル、3-メトキシ-3-メチル-1-ブタノール、3-メトキシ-3-メチルブチルアセテート、3-メトキシブタノール、3-メトキシブチルアセテート、4-ヘプタノーン、m-キシレン、m-ジエチルベンゼン、m-ジクロロベンゼン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、n-ブチルアルコール、n-ブチルベンゼン、n-プロピルアセテート、N-メチルピロリドン、o-キシレン、o-クロロトールエン、o-ジエチルベンゼン、o-ジクロロベンゼン、p-クロロトールエン、p-ジエチルベンゼン、sec-ブチルベンゼン、tert-ブチルベンゼン、γ-ブチロラクトン、イソブチルアルコール、イソホロン、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、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノターシャリーブチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノプロピルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、ジイソブチルケトン、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテル、シクロヘキサノール、シクロヘキサノールアセテート、シクロヘキサノン、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノメチルエーテル、ダイアセトンアルコール、トリアセチン、トリプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル、プロピレングリコールジアセテート、プロピレングリコールフェニルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、ベンジルアルコール、メチルイソブチルケトン、メチルシクロヘキサノール、酢酸n-アミル、酢酸n-ブチル、酢酸イソアミル、酢酸イソブチル、酢酸プロピル、二塩基酸エステル等が挙げられる。これらの中でも、顔料の分散性、アルカリ可溶樹脂の溶解性の観点から、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート等のグリコールアセテート類、ベンジルアルコール、ダイアセトンアルコール等のアルコール類やシクロヘキサノン等のケトン類が好ましい。 The organic solvent (R) is, for example, 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanjiol, 1,3-butylene glycol, 1,3-butylene glycol. Diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexene-1-one, 3,3,5-trimethylcyclohexanone , 3-ethoxypropionate ethyl, 3-methyl-1,3-butanjiol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutylacetate, 3-methoxybutanol, 3-methoxy Butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propylacetate, N -Methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, Isophoron, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monoterriary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene Glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether Acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acethe G, Dipropylene Glycol Monoethyl Ether, Dipropylene Glycol Monobutyl Ether, Dipropylene Glycol Monopropyl Ether, Dipropylene Glycol Monomethyl Ether, Diacetone Alcohol, Triacetin, Tripropylene Glycol Monobutyl Ether, Tripropylene Glycol Monomethyl Ether, Propylene Glycol Diacetate , Propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl Examples thereof include alcohol, methylisobutylketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid ester and the like. Among these, from the viewpoint of dispersibility of pigments and solubility of alkali-soluble resins, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate and the like Alcohols such as glycol acetates, benzyl alcohols and diacetone alcohols and ketones such as cyclohexanone are preferable.
有機溶剤(R)は、単独または2種類以上を併用して使用できる。 The organic solvent (R) can be used alone or in combination of two or more.
[感光性着色組成物の製造方法]
本発明の感光性着色組成物は、例えば、有機顔料(A)、分散樹脂(G)、及び有機溶剤(R)等を加えて分散処理を行うことで、分散体を製造する。その後、前記分散体に、アルカリ可溶性樹脂(B)、重合性化合物(C)、光重合開始剤(D)、シリカ粒子(E)を配合し混合することで製造できる。なお、各材料を配合するタイミングは、任意である。また、分散工程を複数回行うこともできる。
[Manufacturing method of photosensitive coloring composition]
The photosensitive coloring composition of the present invention is subjected to a dispersion treatment by adding, for example, an organic pigment (A), a dispersion resin (G), an organic solvent (R) and the like to produce a dispersion. Then, the dispersion can be produced by blending an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and silica particles (E) and mixing them. The timing of blending each material is arbitrary. Further, the dispersion step can be performed a plurality of times.
分散処理を行う分散機は、例えば、2本ロ-ルミル、3本ロールミル、ボ-ルミル、横型サンドミル、縦型サンドミル、アニュラー型ビ-ズミル、又はアトライター等が挙げられる。 Examples of the disperser for performing the dispersion treatment include a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annual bead mill, and an attritor.
分散体中の有機顔料(A)の平均分散粒子径(二次粒子径)は、30~200nmが好ましく、40~200nmがより好ましい。適度な粒子径を有すると分散安定性が高い感光性着色組成物が得やすい。 The average dispersed particle size (secondary particle size) of the organic pigment (A) in the dispersion is preferably 30 to 200 nm, more preferably 40 to 200 nm. When the particle size is appropriate, it is easy to obtain a photosensitive coloring composition having high dispersion stability.
平均分散粒子径(二次粒子径)の測定方法は、例えば、動的光散乱法(FFTパワ-スペクトール法)を採用した日機装社のマイクロトラックUPA-EX150を用い、粒子透過性を吸収モ-ド、粒子形状を非球形とし、D50粒子径を平均径とする。測定用の希釈溶剤は分散に使用した有機溶剤をそれぞれ用い、超音波で処理したサンプルについてサンプル調整直後に測定するとバラツキが少ない結果が得られやすく好ましい。 As a method for measuring the average dispersed particle size (secondary particle size), for example, Nikkiso's Microtrack UPA-EX150, which employs a dynamic light scattering method (FFT power-spector method), is used to absorb particle permeability. The particle shape is non-spherical, and the D50 particle diameter is the average diameter. As the diluting solvent for measurement, the organic solvent used for dispersion is used, and it is preferable to measure the sample treated by ultrasonic waves immediately after sample preparation because it is easy to obtain results with little variation.
感光性着色組成物は、遠心分離、焼結フィルタやメンブレンフィルタによる濾過等の手段にて、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。本発明の感光性着色組成物は、実質的に0.5μm以上の粒子を含まないことが好ましく、0.3μm以下の粒子を含まないことがより好ましい。 The photosensitive coloring composition is prepared by means such as centrifugation, filtration with a sintering filter or a membrane filter, and coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more, and coarse particles of 0.5 μm or more. It is preferable to remove the mixed dust. The photosensitive coloring composition of the present invention preferably contains substantially no particles of 0.5 μm or more, and more preferably does not contain particles of 0.3 μm or less.
<硬化膜>
本発明の硬化膜は、本発明の感光性着色組成物を用いて形成された膜を硬化して得られる。硬化膜は、パターン状の硬化膜も含む。
<Hardened film>
The cured film of the present invention is obtained by curing a film formed by using the photosensitive coloring composition of the present invention. The cured film also includes a patterned cured film.
[硬化膜の製造方法]
硬化膜の製造方法は、特に限定されず、例えば、基板上に感光性着色組成物を塗布し組成物の層を形成する工程(1)、前記層に、マスクを介してパターン状に露光する工程(2)、未露光部分をアルカリ現像しパターン状の硬化膜を形成する工程(3)、前記パターンを加熱処理(ポストベーク)する工程(4)を行い作製できる。
[Manufacturing method of cured film]
The method for producing the cured film is not particularly limited, and for example, in the step (1) of applying a photosensitive coloring composition on a substrate to form a layer of the composition, the layer is exposed in a pattern through a mask. It can be produced by performing a step (2), an alkaline development of an unexposed portion to form a patterned cured film (3), and a step (4) of heat-treating (post-baking) the pattern.
以下、硬化膜の製造方法を詳細に説明する。
(工程(1))
組成物の層を形成する工程(1)は、感光性着色組成物を基板上に、例えば、回転塗布、ロ-ル塗布、スリット塗布、流延塗布、またはインクジェット塗布等の方法で塗布し、必要に応じてオーブン、ホットプレート等を用いて、50~120℃の温度で10~120秒乾燥(プリベーク)する。
前記基板は、例えば、ガラス基板、シリコン基板等が挙げられる。シリコン基板は、例えば、表面にCCD、CMOS等の撮像素子が形成されていてもよい。また、基板上には、必要に応じて、上部との層との密着改良、物質の拡散防止、基板表面の平坦化のために下塗り層を設けてもよい。
層の膜厚は、色分離性の観点から、乾燥後4.0μm以上となるように塗布することが好ましく、6.0μm以上となるように塗布することがより好ましい。
Hereinafter, a method for producing a cured film will be described in detail.
(Step (1))
In the step (1) of forming the layer of the composition, the photosensitive coloring composition is applied onto the substrate by, for example, rotary coating, roll coating, slit coating, cast coating, or inkjet coating. If necessary, dry (pre-bake) at a temperature of 50 to 120 ° C. for 10 to 120 seconds using an oven, a hot plate, or the like.
Examples of the substrate include a glass substrate and a silicon substrate. For example, an image pickup element such as a CCD or CMOS may be formed on the surface of the silicon substrate. Further, if necessary, an undercoat layer may be provided on the substrate for improving the adhesion with the layer from the upper part, preventing the diffusion of substances, and flattening the surface of the substrate.
From the viewpoint of color separation, the film thickness of the layer is preferably 4.0 μm or more after drying, and more preferably 6.0 μm or more.
(工程(2))
露光工程は、工程(1)で得られた層を、例えば、ステッパ-等の露光装置を用い、マスクを介して特定のパターンを露光する。これにより硬化膜が得られる。
露光に用いる放射線は、例えば、g線、h線、i線等の紫外線が挙げられる。
(Step (2))
In the exposure step, the layer obtained in the step (1) is exposed to a specific pattern via a mask using, for example, an exposure device such as a stepper. This gives a cured film.
Examples of the radiation used for exposure include ultraviolet rays such as g-line, h-line, and i-line.
(工程(3))
工程(2)で得られた硬化膜は、アルカリ現像処理を行うことで、未露光部分の組成物の層がアルカリ水溶液に溶出し、硬化部分のみが残りパターン状の硬化膜が得られる。
現像液は、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム,硅酸ナトリウム、メタ硅酸ナトリウム、アンモニア水、エチルアミン、ジエチルアミン、ジメチルエタノールアミン、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、コリン、ピロ-ル、ピペリジン、1,8-ジアザビシクロ-〔5.4.0〕-7-ウンデセン等のアルカリ性化合物が挙げられる。
現像液の濃度は、0.001~10質量%が好ましく、0.01~1質量%がより好ましい。
アルカリ現像液のpHは、11~13が好ましく、11.5~12.5がより好ましい。適度なpHで使用するとパターンの荒れや剥離を抑制し、現像後の残膜率が向上する。
(Step (3))
The cured film obtained in the step (2) is subjected to an alkaline development treatment, so that the layer of the composition in the unexposed portion is eluted in the alkaline aqueous solution, and only the cured portion remains to obtain a patterned cured film.
The developing solution is, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, etc. Alkaline compounds such as pyrrol, piperidine, 1,8-diazabicyclo- [5.4.0] -7-undecene and the like can be mentioned.
The concentration of the developer is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
The pH of the alkaline developer is preferably 11 to 13, more preferably 11.5 to 12.5. When used at an appropriate pH, roughening and peeling of the pattern are suppressed, and the residual film ratio after development is improved.
現像方法は、例えば、ディップ法、スプレー法、パドール法等が挙げられる。現像温度は15~40℃ が好ましい。なお、アルカリ現像後は、純水で洗浄することが好ましい
。
Examples of the developing method include a dip method, a spray method, a paddle method and the like. The development temperature is preferably 15 to 40 ° C. After alkaline development, it is preferable to wash with pure water.
(工程(4))
加熱処理(ポストベーク)は、工程(3)で得られたパターン状の硬化膜を加熱により十分に硬化させる。ポストベークの加熱温度は、100~300℃が好ましく、150~250℃がより好ましい。また、加熱時間は、2分間~1時間程度が好ましく、3分間~30分間程度がより好ましい。
(Step (4))
In the heat treatment (post-baking), the patterned cured film obtained in the step (3) is sufficiently cured by heating. The heating temperature of the post bake is preferably 100 to 300 ° C, more preferably 150 to 250 ° C. The heating time is preferably about 2 minutes to 1 hour, more preferably about 3 minutes to 30 minutes.
本発明の感光性着色組成物を硬化して得られる硬化膜は、色分離性の観点から、膜厚4.0μm以上が好ましく、6.0μm以上がより好ましい。なお、上限は特に限定されないが、10.0μm以下が好ましい。 The cured film obtained by curing the photosensitive coloring composition of the present invention preferably has a film thickness of 4.0 μm or more, more preferably 6.0 μm or more, from the viewpoint of color separation. The upper limit is not particularly limited, but is preferably 10.0 μm or less.
前記硬化膜の膜厚の測定方法を以下に示す。 The method for measuring the film thickness of the cured film is shown below.
(膜厚の測定)
本発明の感光性着色組成物をスピンコート法により、乾燥後の膜厚が6.0μmとなるようにガラス基板上に塗布し、70℃1分間ホットプレートで乾燥後、超高圧水銀ランプを用い、250mJ/cm2で全面露光した。その後、この基板を23℃の0.2質量%
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、風乾し、クリーンオーブン中230℃で30分間加熱(ポストベーク)して硬化膜を得た。
得られた硬化膜を、Dektak 3030(日本真空技術社製)を用いて、任意の場所5点を測定しその平均値を膜厚とした。
なお、上記膜厚6.0μmとは、本発明が属する技術分野において許容される誤差の範囲を含むものとする。具体的には、膜厚6.0μm±0.2μmの範囲であることを意味する。
(Measurement of film thickness)
The photosensitive coloring composition of the present invention is applied onto a glass substrate by a spin coating method so that the film thickness after drying is 6.0 μm, dried on a hot plate at 70 ° C. for 1 minute, and then used with an ultra-high pressure mercury lamp. , 250 mJ / cm 2 for full exposure. Then, this substrate was subjected to 0.2% by mass at 23 ° C.
After spray-developing with an aqueous sodium carbonate solution, the cells were washed with ion-exchanged water, air-dried, and heated (post-baked) at 230 ° C. in a clean oven for 30 minutes to obtain a cured film.
The obtained cured film was measured at 5 points at arbitrary locations using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.), and the average value was taken as the film thickness.
The film thickness of 6.0 μm includes a range of errors allowed in the technical field to which the present invention belongs. Specifically, it means that the film thickness is in the range of 6.0 μm ± 0.2 μm.
<光学フィルタ>
本発明の硬化膜は、光学フィルタに用いることができる。本発明の感光性着色組成物を用いて作成された硬化膜は、膜表面にシワがなく、色分離性に優れる。本発明の光学フィルタの製造は、上述の硬化膜と同様の方法で製造できる。
<Optical filter>
The cured film of the present invention can be used for an optical filter. The cured film produced by using the photosensitive coloring composition of the present invention has no wrinkles on the film surface and is excellent in color separation. The optical filter of the present invention can be manufactured by the same method as the above-mentioned cured film.
本発明の光学フィルタは、例えば、カメラ、液晶や有機エレクトロルミネッセンス等の画像表示装置、C-MOSイメージセンサ、CCDイメージセンサ等の固体撮像素子、赤外線センサ、生体認証センサなどに使用できる。 The optical filter of the present invention can be used, for example, in a camera, an image display device such as a liquid crystal or an organic electroluminescence, a solid-state image sensor such as a C-MOS image sensor or a CCD image sensor, an infrared sensor, a biometric authentication sensor and the like.
以下、実施例で本発明をより具体的に説明する。ただし、本発明はこれらに限定されない。なお、「部」は「質量部」、「%」は「質量%」である。 Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not limited to these. In addition, "part" is "mass part", and "%" is "mass%".
実施例に先立ち、各測定方法について説明する。 Prior to the embodiment, each measurement method will be described.
樹脂の重量平均分子量(Mw)、数平均分子量(Mn)、酸価(mgKOH/g)は、以下の通りである。 The weight average molecular weight (Mw), number average molecular weight (Mn), and acid value (mgKOH / g) of the resin are as follows.
(アルカリ可溶性樹脂、及び分散樹脂の平均分子量)
アルカリ可溶性樹脂、及び分散樹脂の数平均分子量(Mn)、重量平均分子量(Mw)は、RI検出器を装備したゲルパーミエーションクロマトグラフィー(GPC)で測定した。装置としてHLC-8220GPC(東ソー社製)を用い、分離カラムを2本直列に繋ぎ、両方の充填剤には「TSK-GEL SUPER HZM-N」を2連でつなげて使用し、オーブン温度40℃、溶離液としてテトラヒドロフラン(THF)溶液を用い、流速0.35ml/minで測定した。サンプルは1wt%の上記溶離液からなる溶剤に溶解し、20マイクロリットール注入した。分子量は、ポリスチレン換算値である。
(Average molecular weight of alkali-soluble resin and dispersed resin)
The number average molecular weight (Mn) and weight average molecular weight (Mw) of the alkali-soluble resin and the dispersed resin were measured by gel permeation chromatography (GPC) equipped with an RI detector. Using HLC-8220GPC (manufactured by Tosoh Co., Ltd.) as an apparatus, two separation columns are connected in series, and "TSK-GEL SUPER HZM-N" is connected in two for both fillers, and the oven temperature is 40 ° C. , Tetrahydrofuran (THF) solution was used as an eluent, and the measurement was performed at a flow rate of 0.35 ml / min. The sample was dissolved in a solvent consisting of 1 wt% of the above eluent and injected with 20 microliters. The molecular weight is a polystyrene-equivalent value.
(アルカリ可溶性樹脂、及び分散樹脂の酸価)
アルカリ可溶性樹脂、及び分散樹脂溶液0.5~1gに、アセトン80ml及び水10mlを加えて攪拌して均一に溶解させ、0.1mol/LのKOH水溶液を滴定液として、自動滴定装置(「COM-555」平沼産業社製)を用いて滴定し、酸価(mgKOH/g)を測定した。そして、樹脂溶液の酸価と樹脂溶液の不揮発分濃度から、樹脂の不揮発分あたりの酸価を算出した。
(Acid value of alkali-soluble resin and dispersed resin)
80 ml of acetone and 10 ml of water are added to 0.5 to 1 g of an alkali-soluble resin and a dispersed resin solution, and the mixture is stirred to uniformly dissolve the solution. -555 ”manufactured by Hiranuma Sangyo Co., Ltd.) was used for titration, and the acid value (mgKOH / g) was measured. Then, the acid value per non-volatile component of the resin was calculated from the acid value of the resin solution and the non-volatile content concentration of the resin solution.
(分散樹脂のアミン価)
分散樹脂のアミン価は、ASTM D 2074の方法に準拠し、測定した全アミン価(mgKOH/g)を固形分換算した値である。
(Amine value of dispersed resin)
The amine value of the dispersed resin is a value obtained by converting the measured total amine value (mgKOH / g) into a solid content according to the method of ASTM D 2074.
<有機顔料(A)の製造>
(微細化したハロゲン化金属フタロシアニン顔料(A-1-1))
中心金属が亜鉛であるC.I.Pigment Green58(DIC社製「FASTGEN GREEN A110」)100部、粉砕した塩化ナトリウム1,200部、
およびジエチレングリコール120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、70℃で6時間混練した。この混練物を3,000部の温水に投入し、70℃に加熱しながら1時間撹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およびジエチレングリコールを除いた後、80℃で一昼夜乾燥し、微細化したハロゲン化金属フタロシアニン顔料(A-1-1)を得た。
<Manufacturing of organic pigment (A)>
(Miniaturized metal halide phthalocyanine pigment (A-1-1))
C. The central metal is zinc. I. Pigment Green 58 ("FASTGEN GREEN A110" manufactured by DIC Corporation) 100 parts, crushed sodium chloride 1,200 parts,
And 120 parts of diethylene glycol were charged in a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 6 hours. This kneaded product is put into 3,000 parts of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours. , A finely divided metal halide phthalocyanine pigment (A-1-1) was obtained.
(微細化したハロゲン化金属フタロシアニン顔料(A-1-2))
反応容器中で、濃硫酸1,500部にクロロアルミニウムフタロシアニン100部を氷浴下にて加えた。その後、1,3-ジブロモ-5,5-ジメチルヒダントイン296部を徐々に加え、20℃で8時間撹拌を行った。続けて、この硫酸溶液を3℃の冷水9,000部に注入し、生成した析出物をろ過、水洗、1%水酸化ナトリウム水溶液洗浄、水洗の順で処理を行い、乾燥して、159部の化合物(a)を得た。
次に、反応容器に、1-メチル-2-ピロリジノン1,000部、化合物(a)100部、リン酸ジフェニル32部を加えた。85℃で、3時間反応させた後、水8,000部中にこの溶液を注入した。反応生成物をろ過し、水16,000部で洗浄後、減圧下60℃にて一昼夜乾燥させて、112部の生成物を得た。次いで、プロピレングリコールモノメチルエーテルアセテート600部に得られた生成物を加え、120℃で2時間加熱した。生成物をろ過し、減圧下にて60℃で一昼夜乾燥させて、中心金属がアルミニウムであるハロゲン化金属フタロシアニン顔料(A-1-2)を得た。
その後、ハロゲン化金属フタロシアニン顔料(A-1-2)100部、粉砕した塩化ナトリウム1,000部、およびジエチレングリコール100部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、50℃で12時間混練した。この混合物を温水3,000部に投入し、約70℃に加熱しながらハイスピードミキサーで約1時間攪拌してスラリー状とし、濾過、水洗をくりかえして塩化ナトリウムおよび溶剤を除いた後、80℃で24時間乾燥し、微細化したハロゲン化金属フタロシアニン顔料(A-1-2)を得た。
(Miniaturized metal halide phthalocyanine pigment (A-1-2))
In the reaction vessel, 100 parts of chloroaluminum phthalocyanine was added to 1,500 parts of concentrated sulfuric acid under an ice bath. Then, 296 parts of 1,3-dibromo-5,5-dimethylhydantoin was gradually added, and the mixture was stirred at 20 ° C. for 8 hours. Subsequently, this sulfuric acid solution was poured into 9,000 parts of cold water at 3 ° C., and the generated precipitate was treated in the order of filtration, washing with water, washing with 1% sodium hydroxide aqueous solution, and washing with water, and dried to 159 parts. Compound (a) was obtained.
Next, 1,000 parts of 1-methyl-2-pyrrolidinone, 100 parts of compound (a), and 32 parts of diphenyl phosphate were added to the reaction vessel. After reacting at 85 ° C. for 3 hours, this solution was poured into 8,000 parts of water. The reaction product was filtered, washed with 16,000 parts of water, and dried under reduced pressure at 60 ° C. for 24 hours to obtain 112 parts of the product. Then, the obtained product was added to 600 parts of propylene glycol monomethyl ether acetate, and the mixture was heated at 120 ° C. for 2 hours. The product was filtered and dried under reduced pressure at 60 ° C. for 24 hours to obtain a metal halide phthalocyanine pigment (A-1-2) having an aluminum central metal.
Then, 100 parts of the metal halide phthalocyanine pigment (A-1-2), 1,000 parts of crushed sodium chloride, and 100 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) for 12 hours at 50 ° C. Kneaded. This mixture is poured into 3,000 parts of warm water, stirred with a high speed mixer for about 1 hour while heating at about 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and solvent, and then 80 ° C. The mixture was dried for 24 hours to obtain a finely divided metal halide phthalocyanine pigment (A-1-2).
(微細化したイソインドリン顔料(A-2-1))
C.I.ピグメントイエロー139(クラリアント社製「Novoperm Yellow P-M3R」)100部、粉砕した塩化ナトリウム800部、およびジエチレングリコール100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、70℃で12時間混練した。この混合物を温水3000部に投入し、約70℃に加熱しながらハイスピードミキサーで約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およびジエチレングリコールを除いた後、80℃で一昼夜乾燥し、微細化したイソインドリン顔料(A-2-1)を得た。
(Miniaturized isoindoline pigment (A-2-1))
C. I. Pigment Yellow 139 (Clariant's "Novoperm Yellow P-M3R"), 800 parts of crushed sodium chloride, and 100 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 12 hours. .. This mixture is put into 3000 parts of warm water, stirred with a high speed mixer for about 1 hour while heating at about 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then at 80 ° C. for a whole day and night. The dried and finely divided isoindoline pigment (A-2-1) was obtained.
(微細化したイソインドリン顔料(A-2-2))
C.I.ピグメントイエロー185(BASFジャパン社製「Palitol Yellow D1155」)100部、粉砕した塩化ナトリウム700部、及びジエチレングリコール180部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8リットルの温水に投入し、80℃に加熱しながら2 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、85℃で一昼夜乾燥し、微細化したイソインドリン顔料(A-
2-2)を得た。
(Miniaturized isoindoline pigment (A-2-2))
C. I. 100 parts of Pigment Yellow 185 (BASF Japan's "Palitol Yellow D1155"), 700 parts of crushed sodium chloride, and 180 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. .. Next, this kneaded product was put into 8 liters of warm water, stirred for 2 hours while heating at 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. for 24 hours. , Finely divided isoindoline pigment (A-
2-2) was obtained.
(微細化した有機顔料(A-3-1))
C.I.ピグメントイエロー138(BASF社製「パリオトールイエローK0960-HD」)100部、粉砕した塩化ナトリウム700部、及びジエチレングリコール180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、80℃で6時間混練した。この混合物を温水2,000部に投入し、80℃に加熱しながら1時間攪拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で一昼夜乾燥し、微細化した有機顔料(A-3-1)を得た。
(Miniaturized organic pigment (A-3-1))
C. I. Add 100 parts of Pigment Yellow 138 (BASF's "Pariotor Yellow K0960-HD"), 700 parts of crushed sodium chloride, and 180 parts of diethylene glycol to a 1-gallon stainless kneader (manufactured by Inoue Seisakusho) and knead at 80 ° C for 6 hours. did. This mixture is poured into 2,000 parts of warm water and stirred for 1 hour while heating at 80 ° C. to form a slurry, which is repeatedly filtered and washed with water to remove salt and solvent, and then dried at 80 ° C. for 24 hours to make it finer. The organic pigment (A-3-1) was obtained.
(微細化した有機顔料(A-3-2))
C.I.ピグメントイエロー150(ランクセス社製「E4GN」)100部、粉砕した塩化ナトリウム700部、及びジエチレングリコール180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、80℃で6時間混練した。この混合物を温水2,000部に投入し、80℃に加熱しながら1時間攪拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で一昼夜乾燥し、微細化した有機顔料(A-3-2)を得た。
(Miniaturized organic pigment (A-3-2))
C. I. Pigment Yellow 150 (“E4GN” manufactured by LANXESS), 700 parts of crushed sodium chloride, and 180 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80 ° C. for 6 hours. This mixture is poured into 2,000 parts of warm water and stirred for 1 hour while heating at 80 ° C. to form a slurry, which is repeatedly filtered and washed with water to remove salt and solvent, and then dried at 80 ° C. for 24 hours to make it finer. The organic pigment (A-3-2) was obtained.
<アルカリ可溶性樹脂(B)の製造>
(アルカリ可溶性樹脂(B-1-1)溶液)
撹拌機、温度計、還流冷却管、滴下ロ-トおよび窒素導入管を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート(以下、PGMAc)333部を導入し、フラスコ内雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5部(0.40モル)、グリシジルメタクリレート71.1部(0.50モル)、ジシクロペンタニルメタクリレート22.0部(0.10モル)および、PGMAc164部からなる混合物にアゾビスイソブチロニトリル3.6部を添加した溶液を滴下ロ-トから2時間かけてフラスコに滴下し、さらに100℃で5時間撹拌し続けた。次に、フラスコ内雰囲気を窒素から空気にし、メタクリル酸43.0部[0.5モル、(本反応に用いたグリシジルメタクリレートのグリシジル基に対して100モル%)]、トリスジメチルアミノメチルフェノール0.9部およびハイドロキノン0.145部をフラスコ内に投入し、110℃で6時間反応を続け不揮発分酸価が1mgKOH/gとなったところで反応を終了した。次に、テトラヒドロフタル無水フタル酸60.9部(0.40モル)、トリエチルアミン0.8部を加え、120℃で3.5時間反応させ酸価80mgKOH/gの感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2部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、先に合成した感光性透明樹脂溶液に不揮発分が40質量%になるようにPGMAcを添加して、感光性のアルカリ可溶性樹脂(B-1-1)溶液を調製した。質量平均分子量(Mw)は12,000であった。
<Manufacturing of alkali-soluble resin (B)>
(Alkali-soluble resin (B-1-1) solution)
After introducing 333 parts of propylene glycol monomethyl ether acetate (hereinafter, PGMAc) into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping rotor and a nitrogen introduction tube, the atmosphere inside the flask is changed from air to nitrogen. After heating to 100 ° C., 70.5 parts (0.40 mol) of benzyl methacrylate, 71.1 parts (0.50 mol) of glycidyl methacrylate, 22.0 parts (0.10 mol) of dicyclopentanyl methacrylate and A solution prepared by adding 3.6 parts of azobisisobutyronitrile to a mixture consisting of 164 parts of PGMAc was added dropwise to the flask over 2 hours from the dropping rotor, and stirring was continued at 100 ° C. for 5 hours. Next, the atmosphere in the flask was changed from nitrogen to air, and 43.0 parts of methacrylic acid [0.5 mol, (100 mol% with respect to the glycidyl group of glycidyl methacrylate used in this reaction)], trisdimethylaminomethylphenol 0. 9. 9 parts and 0.145 parts of hydroquinone were put into the flask, and the reaction was continued at 110 ° C. for 6 hours, and the reaction was terminated when the non-volatile acid value reached 1 mgKOH / g. Next, 60.9 parts (0.40 mol) of tetrahydrophthalic anhydride and 0.8 parts of triethylamine were added and reacted at 120 ° C. for 3.5 hours to obtain a photosensitive transparent resin solution having an acid value of 80 mgKOH / g. .. After cooling to room temperature, about 2 parts of the photosensitive transparent resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content. PGMAc was added so as to prepare a photosensitive alkali-soluble resin (B-1-1) solution. The mass average molecular weight (Mw) was 12,000.
(アルカリ可溶性樹脂(B-1-2)溶液)
撹拌機、温度計、還流冷却管、滴下ロ-トおよび窒素導入管を備えたフラスコに、PGMAc182部を導入し、フラスコ内雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5部(0.40モル)、メタクリル酸43.0部(0.5モル)、ジシクロペンタニルメタクリレート22.0部(0.10モル)およびPGMAc136部からなる混合物にアゾビスイソブチロニトリル3.6部を添加した溶液を滴下ロ-トから2時間かけてフラスコに滴下し、さらに100℃で5時間撹拌し続けた。次に、フラスコ内雰囲気を窒素から空気にし、グリシジルメタクリレート35.5部[0.25モル、(本反応に用いたメタクリル酸のカルボキシル基に対して50モル%)]、トリスジメチルアミノメチルフェノール0.9部およびハイドロキノン0.145部をフラスコ内に投入し、110℃で6時間反応を続け、酸価が79mgKOH/gの感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2部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、先に合成した感光性透明樹脂溶液に不揮発分が40質量%になるようにPGMAcを添加して、感光性のアルカリ可溶性樹脂(B-1-2)溶液を調製した。質量平均分子量(Mw)は13,000であった。
(Alkali-soluble resin (B-1-2) solution)
Introduce 182 parts of PGMAc into a flask equipped with a stirrer, thermometer, reflux cooling tube, dropping rotor and nitrogen introduction tube, change the atmosphere inside the flask from air to nitrogen, raise the temperature to 100 ° C, and then benzyl methacrylate. Azobisisobuty in a mixture consisting of 70.5 parts (0.40 mol), 43.0 parts (0.5 mol) of methacrylic acid, 22.0 parts (0.10 mol) of dicyclopentanyl methacrylate and 136 parts of PGMAc. The solution to which 3.6 parts of nitrogen was added was added dropwise from the dropping rotor to the flask over 2 hours, and the mixture was further stirred at 100 ° C. for 5 hours. Next, the atmosphere in the flask was changed from nitrogen to air, and 35.5 parts of glycidyl methacrylate [0.25 mol, (50 mol% with respect to the carboxyl group of methacrylic acid used in this reaction)], trisdimethylaminomethylphenol 0. 9. 9 parts and 0.145 parts of hydroquinone were put into a flask, and the reaction was continued at 110 ° C. for 6 hours to obtain a photosensitive transparent resin solution having an acid value of 79 mgKOH / g. After cooling to room temperature, about 2 parts of the photosensitive transparent resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content. PGMAc was added so as to prepare a photosensitive alkali-soluble resin (B-1-2) solution. The mass average molecular weight (Mw) was 13,000.
(アルカリ可溶性樹脂(B-2-1)溶液)
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、滴下管および撹拌装置を取り付けた反応容器にシクロヘキサノン196部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管より、n-ブチルメタクリレート37.2部、2-ヒドロキシエチルメタクリレート12.9部、メタクリル酸12.0部、パラクミルフェノールエチレンオキサイド変性アクリレート(東亞合成社製「アロニックスM110」)20.7部、2,2’-アゾビスイソブチロニトリル1.1部の混合物を2時間かけて滴下した。滴下終了後、更に3時間反応を継続し、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2部をサンプリングして180℃、20分間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40%になるようにPGMAcを添加して、非感光性のアルカリ可溶性樹脂(B-2-1)溶液を調製した。重量平均分子量(Mw)は26,000であった。
(Alkali-soluble resin (B-2-1) solution)
196 parts of cyclohexanone was charged in a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer in a separable 4-neck flask, the temperature was raised to 80 ° C., the inside of the reaction vessel was replaced with nitrogen, and then dropped. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, 20.7 parts of paracumylphenol ethylene oxide-modified acrylate (“Aronix M110” manufactured by Toa Synthetic Co., Ltd.) , 2,2'-Azobisisobutyronitrile 1.1 parts mixture was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for another 3 hours to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content, and PGMAc was added to the previously synthesized resin solution so that the non-volatile content was 40%. A non-photosensitive alkali-soluble resin (B-2-1) solution was prepared. The weight average molecular weight (Mw) was 26,000.
<ウレタン結合を有する重合性化合物(C-1)の製造>
(ウレタン結合を有する重合性化合物(C-1-1))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ペンタエリスリトールトリアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からヘキサメチレンジイソシアネート112部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。不揮発分が50質量%となるようにPGMAcを添加し、重合性不飽和基数6の脂肪族ウレタンアクリレート溶液を得た。
<Manufacturing of polymerizable compound (C-1) having urethane bond>
(Polymerizable compound having urethane bond (C-1-1))
400 parts of pentaerythritol triacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were placed in a 5-port flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube at 70 ° C. A mixture of 112 parts of hexamethylene diisocyanate and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aliphatic urethane acrylate solution having 6 polymerizable unsaturated groups.
(ウレタン結合を有する重合性化合物(C-1-2))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ペンタエリスリトールトリアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からイソホロンジイソシアネート148部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。不揮発分が50質量%となるようにPGMAcを添加し、重合性不飽和基数6の脂環式ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-2))
400 parts of pentaerythritol triacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were placed in a 5-port flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube at 70 ° C. A mixture of 148 parts of isophorone diisocyanate and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. PGMAc was added so that the non-volatile content was 50% by mass to obtain an alicyclic urethane acrylate solution having 6 polymerizable unsaturated groups.
(ウレタン結合を有する重合性化合物(C-1-3))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ペンタエリスリトールトリアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管から1,3-フェニレンジイソシアネート107部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。不揮発分が50質量%となるようにPGMAcを添加し、重合性不飽和基数6の芳香族ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-3))
400 parts of pentaerythritol triacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were placed in a 5-port flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube at 70 ° C. A mixture of 107 parts of 1,3-phenylenedi isocyanate and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aromatic urethane acrylate solution having 6 polymerizable unsaturated groups.
(ウレタン結合を有する重合性化合物(C-1-4))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ジペンタエリスリトールペンタアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からトルエンジイソシアネート
(2,4体と2,6体の混合物)66部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。不揮発分が50質量%となるようにPGMAcを添加し、重合性不飽和基数10の芳香族ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-4))
In a 5-necked flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube, 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were charged, and 70 parts were charged. The temperature was raised to ° C., and a mixture of 66 parts of toluene diisocyanate (a mixture of 2,4 and 2,6 bodies) and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aromatic urethane acrylate solution having 10 polymerizable unsaturated groups.
(ウレタン結合を有する重合性化合物(C-1-5))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ペンタエリスリトールトリアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からヘキサメチレンジイソシアネート112部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。ついで、メルカプトプロピオン酸13部、4-メトキシフェノール0.4部を仕込み、50~60℃の温度で6時間反応させた。不揮発分が50質量%となるようにPGMAcを添加し、一般式(1)で表される化合物として、酸基を有する平均重合性不飽和基数5の脂肪族ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-5))
400 parts of pentaerythritol triacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were placed in a 5-port flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube at 70 ° C. A mixture of 112 parts of hexamethylene diisocyanate and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. Then, 13 parts of mercaptopropionic acid and 0.4 parts of 4-methoxyphenol were charged and reacted at a temperature of 50 to 60 ° C. for 6 hours. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aliphatic urethane acrylate solution having an acid group and having an average polymerizable unsaturated group number of 5 as the compound represented by the general formula (1).
(ウレタン結合を有する重合性化合物(C-1-6))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ペンタエリスリトールトリアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からトルエンジイソシアネート(2,4体と2,6体の混合物)116部とPGMAc100部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。ついで、メルカプトプロピオン酸13部、4-メトキシフェノール0.4部を仕込み、50~60℃の温度で6時間反応させた。不揮発分が50質量%となるようにPGMAcを添加し、一般式(1)で表される化合物として、酸基を有する平均重合性不飽和基数5の芳香族ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-6))
400 parts of pentaerythritol triacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were placed in a 5-port flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube at 70 ° C. A mixture of 116 parts of toluene diisocyanate (a mixture of 2,4 and 2,6 bodies) and 100 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. Then, 13 parts of mercaptopropionic acid and 0.4 parts of 4-methoxyphenol were charged and reacted at a temperature of 50 to 60 ° C. for 6 hours. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aromatic urethane acrylate solution having an acid group and having an average polymerizable unsaturated group number of 5 as the compound represented by the general formula (1).
(ウレタン結合を有する重合性化合物(C-1-7))
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ジペンタエリスリトールペンタアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管から1,3-フェニレンジイソシアネート61部とPGMAc61部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認した。ついで、メルカプトプロピオン酸20部、4-メトキシフェノール0.6部を仕込み、50~60℃の温度で6時間反応させた。不揮発分が50質量%となるようにPGMAcを添加し、一般式(1)で表される化合物として、酸基を有する平均重合性不飽和基数9の芳香族ウレタンアクリレート溶液を得た。
(Polymerizable compound having urethane bond (C-1-7))
In a 5-necked flask equipped with a stirrer, a reflux condenser, a nitrogen introduction tube, a thermometer, and a dropping tube, 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 part of N, N-dimethylbenzylamine were charged, and 70 parts were charged. The temperature was raised to ° C., and a mixture of 61 parts of 1,3-phenylenedi isocyanate and 61 parts of PGMAc was added dropwise from the dropping tube over 2 hours. After the dropping, the reaction was carried out at a temperature of 50 to 70 ° C. for 8 hours, and the disappearance of the absorption of isocyanate of 2180 cm -1 was confirmed by IR. Then, 20 parts of mercaptopropionic acid and 0.6 part of 4-methoxyphenol were charged and reacted at a temperature of 50 to 60 ° C. for 6 hours. PGMAc was added so that the non-volatile content was 50% by mass to obtain an aromatic urethane acrylate solution having an acid group and having an average polymerizable unsaturated group number of 9 as the compound represented by the general formula (1).
<分散樹脂(G)の製造>
(分散樹脂(G-1)溶液)
ガス導入管、温度、コンデンサー、攪拌機を備えた反応容器に、メタクリル酸10部、メチルメタクリレート100部、i-ブチルメタクリレート70部、ベンジルメタクリレート20部、PGMAc50部を仕込み、窒素ガスで置換した。反応容器内を50℃に加熱撹拌し、3-メルカプト-1,2-プロパンジオール12部を添加した。90℃に昇温し、2,2’-アゾビスイソブチロニトリル0.1部をPGMAc90部に加えた溶液を添加しながら7時間反応した。不揮発分測定により95%が反応したことを確認した。ピロメリット酸無水物19部、PGMAc50部、シクロヘキサノン50部、触媒として1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン0.4部を追加し、100℃で7時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認し反応を終了し、不揮発分測定で不揮発分30%となるようPGMAcを加えて希釈し、酸価70mgKOH/g、重量平均分子量8,500の分散樹脂(G-1)溶液を得た。
<Manufacturing of dispersed resin (G)>
(Dispersed resin (G-1) solution)
In a reaction vessel equipped with a gas introduction tube, temperature, condenser, and stirrer, 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, 20 parts of benzyl methacrylate, and 50 parts of PGMAc were charged and replaced with nitrogen gas. The inside of the reaction vessel was heated and stirred at 50 ° C., and 12 parts of 3-mercapto-1,2-propanediol was added. The temperature was raised to 90 ° C., and the reaction was carried out for 7 hours while adding a solution in which 0.1 part of 2,2'-azobisisobutyronitrile was added to 90 parts of PGMAc. It was confirmed that 95% of the reaction occurred by measuring the non-volatile content. 19 parts of pyromellitic anhydride, 50 parts of PGMAc, 50 parts of cyclohexanone, and 0.4 part of 1,8-diazabicyclo- [5.4.0] -7-undecene were added as a catalyst, and the mixture was reacted at 100 ° C. for 7 hours. .. After confirming that 98% or more of the acid anhydride was half-esterified by measuring the acid value, the reaction was terminated, and PGMAc was added and diluted so that the non-volatile content was 30% by measuring the non-volatile content, and the acid value was 70 mgKOH / g. , A dispersion resin (G-1) solution having a weight average molecular weight of 8,500 was obtained.
(分散樹脂(G-2)溶液)
冷却管、添加用ロート、窒素用インレット、機械的攪拌機、デジタル温度計を備えた500mL丸底4口セパラブルフラスコに、テトラヒドロフラン(THF)250質量部及び開始剤のジメチルケテンメチルトリメチルシリルアセタール5.81質量部を、添加用ロートを介して加え、充分に窒素置換を行った。触媒のテトラブチルアンモニウムm-クロロベンゾエートの1モル/Lアセトニトリル溶液0.5質量部を、シリンジを用いて注入し、親溶剤性を有するブロック用モノマーのメタクリル酸2-ヒドロキシエチル19.7質量部、メタクリル酸2-エチルヘキシル7.5質量部、メタクリル酸n-ブチル12.9質量部、メタクリル酸ベンジル10.7質量部、メタクリル酸メチル30.9質量部を、添加用ロートを用いて60分かけて滴下した。反応フラスコを氷浴で冷却することにより、温度を40℃未満に保った。1時間後、色材吸着機能ブロック用モノマーであるジメチルアミノプロピルメタクリルアミド18.3質量部を20分かけて滴下した。1時間反応させた後、メタノール1質量部を加えて反応を停止させた。得られたブロック共重合体THF溶液はヘキサン中で再沈殿させ、濾過、真空乾燥により精製を行った。
続いて、100mL丸底フラスコ中でPGMAc35質量部に、得られたブロック共重合体15.0質量部を溶解させ、塩形成成分であるフェニルホスフィン酸1.1質量部(ジメチルアミノプロピルメタクリルアミドに対し、0.5モル等量)加え、反応温度30℃で20時間攪拌し、PGMAcを添加して調整し、不揮発分30%の分散樹脂(G-2)溶液を得た。
(Dispersed resin (G-2) solution)
In a 500 mL round bottom 4-port separable flask equipped with a condenser, an addition funnel, an inlet for nitrogen, a mechanical stirrer, and a digital thermometer, 250 parts by mass of tetrahydrofuran (THF) and the initiator dimethylketenemethyltrimethylsilylacetal 5.81 A mass portion was added via the addition funnel and sufficient nitrogen substitution was performed. 0.5 part by mass of 1 mol / L acetonitrile solution of tetrabutylammonium m-chlorobenzoate as a catalyst is injected using a syringe, and 19.7 parts by mass of 2-hydroxyethyl methacrylate, which is a solvent-friendly blocking monomer, is injected. , 7.5 parts by mass of 2-ethylhexyl methacrylate, 12.9 parts by mass of n-butyl methacrylate, 10.7 parts by mass of benzyl methacrylate, 30.9 parts by mass of methyl methacrylate for 60 minutes using an addition funnel. Dropped over. The temperature was kept below 40 ° C. by cooling the reaction flask in an ice bath. After 1 hour, 18.3 parts by mass of dimethylaminopropylmethacrylamide, which is a monomer for blocking the colorant adsorption function, was added dropwise over 20 minutes. After reacting for 1 hour, 1 part by mass of methanol was added to stop the reaction. The obtained block copolymer THF solution was reprecipitated in hexane, and purified by filtration and vacuum drying.
Subsequently, 15.0 parts by mass of the obtained block copolymer was dissolved in 35 parts by mass of PGMAc in a 100 mL round bottom flask, and 1.1 parts by mass of phenylphosphinic acid (dimethylaminopropylmethacrylamide), which is a salt-forming component, was dissolved. On the other hand, 0.5 mol equal amount) was added, and the mixture was stirred at a reaction temperature of 30 ° C. for 20 hours and adjusted by adding PGMAc to obtain a dispersed resin (G-2) solution having a non-volatile content of 30%.
<近赤外線吸収剤(H)の製造>
(近赤外線吸収剤(H-1))
トルエン400部に、1,8-ジアミノナフタレン40.0部、3,5-ジメチルシクロヘキサノン32.2部、p-トルエンスルホン酸一水和物0.087部を混合し、窒素ガスの雰囲気中で加熱攪拌し、3時間還流させた。反応中に生成した水は共沸蒸留により反応系中から除去した。反応終了後、トルエンを蒸留して得られた暗茶色固体をアセトンで抽出し、アセトンとエタノールの混合溶媒から再結晶することにより精製した。得られた茶色固体を、トルエン240部とn-ブタノール160部の混合溶媒に溶解させ、3,4-ジヒドロキシ-3-シクロブテン-1,2-ジオン13.8部を加えて、窒素ガスの
雰囲気中で加熱撹拌し、8時間還流反応させた。反応中に生成した水は共沸蒸留により反応系中から除去した。
反応終了後、溶媒を蒸留し、得られた反応混合物を攪拌しながら、ヘキサン200部を加えた。得られた黒茶色沈殿物を濾別した後、順次ヘキサン、エタノールおよびアセトンで洗浄を行い、減圧下で乾燥させ、下記化学式(3)で表される近赤外線吸収剤(H-1)を得た。得られた近赤外線吸収剤(H-1)50部、塩化ナトリウム500部、ジエチレングリコール60部をステンレス製ガロンニーダー(井上製作所製)中に仕込み、60℃ で12時間混練した。次に、混練した混合物を温水に投入し、約80℃ に加熱しながら1時間攪拌してスラリー状として、濾過および水洗をして塩化ナトリウムおよびジエチレングリコールを除いた後、80℃で一昼夜乾燥させ粉砕することにより、微細化した近赤外線吸収剤(H-1)を得た。
<Manufacturing of near-infrared absorber (H)>
(Near infrared absorber (H-1))
400 parts of toluene is mixed with 40.0 parts of 1,8-diaminonaphthalene, 32.2 parts of 3,5-dimethylcyclohexanone, and 0.087 parts of p-toluenesulfonic acid monohydrate in an atmosphere of nitrogen gas. The mixture was heated and stirred and refluxed for 3 hours. The water produced during the reaction was removed from the reaction system by azeotropic distillation. After completion of the reaction, the dark brown solid obtained by distilling toluene was extracted with acetone and purified by recrystallization from a mixed solvent of acetone and ethanol. The obtained brown solid was dissolved in a mixed solvent of 240 parts of toluene and 160 parts of n-butanol, and 13.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione was added to create an atmosphere of nitrogen gas. The mixture was heated and stirred inside, and the mixture was refluxed for 8 hours. The water produced during the reaction was removed from the reaction system by azeotropic distillation.
After completion of the reaction, the solvent was distilled and 200 parts of hexane was added while stirring the obtained reaction mixture. The obtained black-brown precipitate was filtered off, washed successively with hexane, ethanol and acetone, and dried under reduced pressure to obtain a near-infrared absorber (H-1) represented by the following chemical formula (3). rice field. 50 parts of the obtained near-infrared absorber (H-1), 500 parts of sodium chloride, and 60 parts of diethylene glycol were placed in a stainless steel gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 12 hours. Next, the kneaded mixture was put into warm water, stirred for 1 hour while heating at about 80 ° C. to form a slurry, filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours and crushed. By doing so, a finely divided near-infrared absorber (H-1) was obtained.
化学式(3)
<分散体の製造>
(分散体1)
下記の原料を均一になるように攪拌混合した後、直径0.5mmのジルコニアビ-ズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、孔径1.0μmのフィルタで濾過し、分散体1を作製した。有機溶剤(Q-1)は、PGMAcである。
微細化したハロゲン化フタロシアニン顔料(A-1-1) :20.0部
分散樹脂(G-1)溶液 : 9.3部
分散樹脂(G-2)溶液 : 9.2部
有機溶剤(R-1) :61.5部
<Manufacturing of dispersion>
(Dispersion 1)
The following raw materials are stirred and mixed so as to be uniform, and then dispersed for 3 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan Co., Ltd.) using a zirconia bead having a diameter of 0.5 mm, and then the pore diameter. The dispersion 1 was prepared by filtering with a 1.0 μm filter. The organic solvent (Q-1) is PGMAc.
Finely divided halogenated phthalocyanine pigment (A-1-1): 20.0 parts Dispersed resin (G-1) solution: 9.3 parts Dispersed resin (G-2) solution: 9.2 parts Organic solvent (R-) 1): 61.5 copies
(分散体2~7)
表1に記載した原料、量を変えた以外は、分散体1と同様にして分散体2~7を作製した。
(Dispersion 2-7)
Dispersions 2 to 7 were prepared in the same manner as in Dispersion 1 except that the raw materials and amounts shown in Table 1 were changed.
<感光性着色組成物の製造>
[実施例1]
(感光性着色組成物1)
以下の原料を混合、攪拌し、孔径1.0μmのフィルタで濾過して感光性着色組成物1を得た。
分散体1 :37.5部
分散体3 : 3.25部
アルカリ可溶性樹脂(B-1-1)溶液 :20.75部
アルカリ可溶性樹脂(B-1-2)溶液 : 3.0部
重合性化合物(C-1-1) : 8.0部
光重合開始剤(D-1) : 0.4部
シリカ粒子(E) : 9.7部
重合禁止剤(L) : 0.01部
酸化防止剤(N) : 0.1部
レベリング剤(O) : 1.0部
貯蔵安定剤(P) : 0.2部
有機溶剤(R) :16.09部
<Manufacturing of photosensitive coloring composition>
[Example 1]
(Photosensitive coloring composition 1)
The following raw materials were mixed and stirred, and filtered through a filter having a pore size of 1.0 μm to obtain a photosensitive coloring composition 1.
Dispersion 1: 37.5 parts Dispersion 3: 3.25 parts Alkaline-soluble resin (B-1-1) solution: 20.75 parts Alkaline-soluble resin (B-1-2) solution: 3.0 parts Polymerizable Compound (C-1-1): 8.0 parts Photopolymerization initiator (D-1): 0.4 parts Silica particles (E): 9.7 parts Polymerization inhibitor (L): 0.01 parts Antioxidation Agent (N): 0.1 part Leveling agent (O): 1.0 part Storage stabilizer (P): 0.2 part Organic solvent (R): 16.09 parts
[実施例2~31、比較例1~7]
(感光性着色組成物2~38)
実施例1の感光性着色組成物1を、表2-1~表2-3に記載した原料、量に変えた以外は、実施例1と同様にして感光性着色組成物2~38を作製した。
[Examples 2 to 31, Comparative Examples 1 to 7]
(Photosensitive coloring compositions 2-38)
Photosensitive coloring compositions 2 to 38 were prepared in the same manner as in Example 1 except that the photosensitive coloring composition 1 of Example 1 was changed to the raw materials and amounts shown in Tables 2-1 to 2-3. did.
表2-1~表2-3に記載したそれぞれの原料については、以下の通りである。 The raw materials listed in Tables 2-1 to 2-3 are as follows.
[重合性化合物(C)]
(その他重合性化合物(C-2))
C-2-1:KAYARAD DPHA(日本化薬社製、ジペンタエリスリトールヘキサアクリレートとジペンタエリスリトールペンタアクリレートの混合物、不揮発分100%)
C-2-1:アロニックスM-521(東亞合成社製、重合性不飽和基数5、不揮発分100%)
C-2-3:アロニックスM-309(東亞合成社製、重合性不飽和基数3、不揮発分100%)
[Polymerizable compound (C)]
(Other polymerizable compounds (C-2))
C-2-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, 100% non-volatile content)
C-2-1: Aronix M-521 (manufactured by Toagosei Co., Ltd., polymerizable unsaturated group number 5, non-volatile content 100%)
C-2-3: Aronix M-309 (manufactured by Toagosei Co., Ltd., polymerizable unsaturated group number 3, non-volatile content 100%)
[光重合開始剤(D)]
D-1:上記化学式(2)で表される化合物
D-2:イルガキュア907(BASF社製)
[Photopolymerization Initiator (D)]
D-1: Compound represented by the above chemical formula (2) D-2: Irgacure 907 (manufactured by BASF)
[シリカ粒子(E)]
PMA-ST(日産化学社製、一次粒子径12nm、不揮発分30%)
[Silica particles (E)]
PMA-ST (manufactured by Nissan Chemical Industries, Ltd., primary particle size 12 nm, non-volatile content 30%)
[増感剤(I)]
I-1:カヤキュアDETX-S(日本化薬社製)
I-2:CHEMARK DEABP(Chemark Chemical社製)
以上、(I-1)、(I-2)をそれぞれ同量にて混合し、増感剤(I)とした。
[Sensitizer (I)]
I-1: Kayacure DETX-S (manufactured by Nippon Kayaku Co., Ltd.)
I-2: CHEMARK DEABP (manufactured by Chemark Chemical)
As described above, (I-1) and (I-2) were mixed in the same amount to obtain a sensitizer (I).
[チオール系連鎖移動剤(K)]
ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)
[Thiol chain transfer agent (K)]
Pentaerythritol tetrakis (3-mercaptopropionate)
[重合禁止剤(L)]
L-1:4-メチルカテコール
L-2:メチルヒドロキノン
L-3:t-ブチルヒドロキノン
以上、(L-1)~(L-3)をそれぞれ同量にて混合し、重合禁止剤(L)とした。
[Polymerization inhibitor (L)]
L-1: 4-Methylcatechol L-2: Methylhydroquinone L-3: t-butylhydroquinone Above, (L-1) to (L-3) are mixed in the same amount, and the polymerization inhibitor (L) is used. And said.
[酸化防止剤(N)]
N-1:ペンタエリスリトールテトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート
N-2:3,3'-チオジプロパン酸ジオクタデシル
N-3:トリス[2,4-ジ-(t)-ブチルフェニル]ホスフィン
N-4:ビス(2,2,6,6-テトラメチル-4-ピペリジル)セバケート
N-5:サリチル酸p-オクチルフェニル
以上、(N-1)~(N-5)をそれぞれ同量にて混合し、酸化防止剤(N)とした。
[Antioxidant (N)]
N-1: Pentaerythritol tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate N-2: 3,3'-dioctadecylthiodipropanoate N-3: Tris [2,4- Di- (t) -Butylphenyl] Phenyl N-4: Bis (2,2,6,6-tetramethyl-4-piperidyl) Sevacate N-5: p-octylphenyl salicylate Above, (N-1) to ( N-5) were mixed in the same amount to prepare an antioxidant (N).
[レベリング剤(O)]
O-1:BYK-330(ビックケミー社製)
O-2:メガファックF-551(DIC社製)
以上、(O-1)、(O-2)をそれぞれ1部混合し、PGMAc98部に溶解させた
混合溶液をレベリング剤(O)とした。
[Leveling agent (O)]
O-1: BYK-330 (manufactured by Big Chemie)
O-2: Megafuck F-551 (manufactured by DIC Corporation)
As described above, 1 part each of (O-1) and (O-2) was mixed, and the mixed solution dissolved in 98 parts of PGMAc was used as the leveling agent (O).
[貯蔵安定剤(P)]
P-1:2,6-ビス(1,1-ジメチルエチル)-4-メチルフェノール
P-2:トリフェニルホスフィン
以上、(P-1)、(P-2)をそれぞれ同量にて混合し、貯蔵安定剤(P)とした。
[Storage stabilizer (P)]
P-1: 2,6-bis (1,1-dimethylethyl) -4-methylphenol P-2: triphenylphosphine The above (P-1) and (P-2) are mixed in the same amount. , Storage stabilizer (P).
[有機溶剤(R)]
R-1:プロピレングリコールモノメチルエーテルアセテート 30部
R-2:シクロヘキサノン 30部
R-3:3-エトキシプロピオン酸エチル 10部
R-4:プロピレングリコールモノメチルエーテル 10部
R-5:シクロヘキサノールアセテート 10部
R-6:ジプロプレングリコールメチルエーテルアセテート 10部
以上、(R-1)~(R-6)をそれぞれ上記質量部にて混合し、有機溶剤(R)とした。
[Organic solvent (R)]
R-1: Propylene glycol monomethyl ether acetate 30 parts R-2: Cyclohexanol 30 parts R-3: Ethyl 3-ethoxypropionate 10 parts R-4: Propylene glycol monomethyl ether 10 parts R-5: Cyclohexanol acetate 10 parts R -6: 10 parts or more of diproprene glycol methyl ether acetate and (R-1) to (R-6) were mixed in the above parts by mass to prepare an organic solvent (R).
<感光性着色組成物の評価>
得られた感光性着色組成物1~38について、現像性、パターン形成性、表面シワ、及び色分離性の評価を下記の方法で行った。評価結果を表3に示す。
<Evaluation of photosensitive coloring composition>
The obtained photosensitive coloring compositions 1 to 38 were evaluated for developability, pattern forming property, surface wrinkles, and color separability by the following methods. The evaluation results are shown in Table 3.
[現像性評価]
得られた感光性着色組成物1~38を、縦100mm×横100mm、0.7mm厚のガラス基板(コーニング社製イーグル2000)に、スピンコータを用いて乾燥膜厚が6.0μmとなるように塗工し、70℃1分間ホットプレートで乾燥した。次いで、超高圧水銀ランプを用い、照度30mW/cm2、250mJ/cm2で、100μm幅ストライプパターンのフォトマスクを介して紫外線を露光した。さらに、この基板を室温に冷却後、0.2質量%の炭酸ナトリウム水溶液を用いて、現像時間2水準(50秒、100秒)でスプレー現像し、イオン交換水で洗浄して風乾した。得られた基板をクリーンオーブン中で、230℃で30分間ポストベークを行い、基板上にストライプ状のパターンを形成した。パターンを光学顕微鏡にて観察し、未露光部の現像残渣、および欠けの有無を評価した。以下の通りであり、2以上が実用可能である。
3:現像時間100秒において、未露光部の現像残渣が無く、パターン欠けがなかった。
2:現像時間100秒において、未露光部に現像残渣が発生またはパターン欠けが発生した。
1:現像時間50秒において、未露光部に現像残渣が発生またはパターン欠けが発生した。
[Developability evaluation]
The obtained photosensitive coloring compositions 1 to 38 were applied to a glass substrate (Eagle 2000 manufactured by Corning Inc.) having a length of 100 mm, a width of 100 mm, and a thickness of 0.7 mm so that the dry film thickness was 6.0 μm using a spin coater. It was coated and dried on a hot plate at 70 ° C. for 1 minute. Then, using an ultra-high pressure mercury lamp, ultraviolet rays were exposed through a photomask having a 100 μm wide stripe pattern at an illuminance of 30 mW / cm 2 and 250 mJ / cm 2 . Further, after cooling the substrate to room temperature, the substrate was spray-developed with a 0.2 mass% sodium carbonate aqueous solution for a development time of 2 levels (50 seconds, 100 seconds), washed with ion-exchanged water, and air-dried. The obtained substrate was post-baked at 230 ° C. for 30 minutes in a clean oven to form a striped pattern on the substrate. The pattern was observed with an optical microscope, and the presence or absence of development residue and chipping in the unexposed portion was evaluated. It is as follows, and two or more are practical.
3: At a development time of 100 seconds, there was no development residue in the unexposed portion, and there was no pattern chipping.
2: At the development time of 100 seconds, a development residue was generated or a pattern was chipped in the unexposed portion.
1: At the development time of 50 seconds, development residue was generated or pattern chipping occurred in the unexposed area.
[パターン形成性評価(1):密着性]
得られた感光性着色組成物1~38を、スピンコート法により縦100mm×横100mm、0.7mm厚のガラス基板(コーニング社製イーグル2000)に、乾燥後の膜厚が6.0μmとなるように塗工し、70℃1分間ホットプレートで乾燥した。次いで、この基板を室温に冷却後、高圧水銀灯ランプを用い、100μm幅(ピッチ200μm)および10μm幅(ピッチ20μm)ストライプパターンのフォトマスクを介して照度30mW/cm2、250mJ/cm2で露光した。その後、この基板を0.2質量%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、風乾し、クリーンオーブン中230℃で30分間加熱し密着性評価用基板を得た。スプレー現像は、それぞれの感光性着色組成物での被膜について、現像残りなくパターン形成可能な最短時間で行い、これを適正現像時間とした。
密着性評価用基板のパターンのうち幅6~25μmの細線パターンについて、光学顕微鏡で観察し、残存した細線パターンの最小線幅を確認した。
5:10μm以下の細線が残存している。
4:15μm以下の細線が残存している。
3:20μm以下の細線が残存している。
2:25μm以下の細線が残存している。
1:細線が残存していない。
[Evaluation of pattern formation (1): Adhesion]
The obtained photosensitive coloring compositions 1 to 38 are applied to a glass substrate (Eagle 2000 manufactured by Corning Inc.) having a length of 100 mm, a width of 100 mm, and a thickness of 0.7 mm by a spin coating method, and the film thickness after drying is 6.0 μm. And dried on a hot plate at 70 ° C. for 1 minute. Next, after cooling this substrate to room temperature, it was exposed to illuminances of 30 mW / cm 2 and 250 mJ / cm 2 using a high-pressure mercury lamp with a photomask having a 100 μm width (pitch 200 μm) and 10 μm width (pitch 20 μm) stripe pattern. .. Then, this substrate was spray-developed with a 0.2 mass% sodium carbonate aqueous solution, washed with ion-exchanged water, air-dried, and heated in a clean oven at 230 ° C. for 30 minutes to obtain a substrate for adhesion evaluation. The spray development was performed for the coating film with each photosensitive coloring composition in the shortest time during which a pattern could be formed without any development residue, and this was set as the appropriate development time.
Among the patterns of the substrate for adhesion evaluation, the thin line pattern having a width of 6 to 25 μm was observed with an optical microscope, and the minimum line width of the remaining fine line pattern was confirmed.
Fine lines of 5:10 μm or less remain.
Thin lines of 4: 15 μm or less remain.
3: Fine lines of 20 μm or less remain.
Fine lines of 2: 25 μm or less remain.
1: No thin lines remain.
[パターン形成評価(2):直線性]
パターン形成性評価(1)で作成した基板を、Nikon社製ECLIPSE LV100POL Model光学顕微鏡を用いて、10箇所のストライプパターンの線幅の最大と最小部分を測定しその平均を求めることで評価を行った。評価基準は、以下の通りであり、3以上が実用可能である。
5:線幅の最大値と最小値の差が0.5μm未満
4:線幅の最大値と最小値の差が0.5μm以上、1.0μm未満
3:線幅の最大値と最小値の差が1.0μm以上、1.5μm未満
2:線幅の最大値と最小値の差が1.5μm以上、2.0μm未満
1:線幅の最大値と最小値の差が2.0μm以上
[Pattern formation evaluation (2): linearity]
Evaluation of pattern formability The substrate created in (1) is evaluated by measuring the maximum and minimum parts of the line width of 10 stripe patterns using an ECLIPSE LV100POL Model optical microscope manufactured by Nikon Corporation and calculating the average. rice field. The evaluation criteria are as follows, and 3 or more are practical.
5: The difference between the maximum and minimum values of the line width is less than 0.5 μm 4: The difference between the maximum and minimum values of the line width is 0.5 μm or more and less than 1.0 μm 3: The maximum and minimum values of the line width Difference is 1.0 μm or more and less than 1.5 μm 2: Difference between maximum and minimum line width is 1.5 μm or more and less than 2.0 μm 1: Difference between maximum and minimum line width is 2.0 μm or more
[表面シワ評価]
密着性評価で作成した基板を、光学顕微鏡(オリンパス光学社製「BX-51」、倍率:200倍)を用いて、パターン表面を観察した。評価基準は、以下の通りであり、3以上が実用可能である。
5:パターンの表面にシワが全く観察されない
4:パターンの表面にごく僅かにシワが観察される
3:パターンの表面に僅かにシワが観察される
2:パターンの表面にシワが観察される
1:パターンの表面に酷くシワが観察される
[Evaluation of surface wrinkles]
The surface of the pattern of the substrate prepared by the adhesion evaluation was observed using an optical microscope (“BX-51” manufactured by Olympus Optical Co., Ltd., magnification: 200 times). The evaluation criteria are as follows, and 3 or more are practical.
5: No wrinkles are observed on the surface of the pattern 4: Very slight wrinkles are observed on the surface of the pattern 3: Wrinkles are slightly observed on the surface of the pattern 2: Wrinkles are observed on the surface of the pattern 1 : Severe wrinkles are observed on the surface of the pattern
[色分離性評価]
得られた感光性着色組成物1~38を、縦100mm×横100mm、0.7mm厚のガラス基板(コ-ニング社製イ-グル2000)上に、スピンコート法により、乾燥後の膜厚が6.0μmとなるように塗工し、70℃1分間ホットプレートで乾燥した。次に、超高圧水銀ランプを用い、50mJ/cm2の露光量で全面露光後、クリーンオーブン中で、230℃で30分間ポストベークし色分離性評価用基板を得た。得られた色分離性評価用基板を、OSP-SP100(オリンパス社製)を用いて、被膜の厚み方向で、波長450~510nm、及び波長580~700nmの最大透過率を測定した。評価基準は、以下の通りであり、2以上が実用可能である。
4:波長450~510nmの最大透過率が30%未満、かつ波長580~700nmの最大透過率が30%未満
3:波長450~510nmの最大透過率が40%未満、かつ波長580~700nmの最大透過率が40%未満
2:波長450~510nmの最大透過率が50%未満、かつ波長580~700nmの最大透過率が50%未満
1:波長450~510nmの最大透過率50%以上、又は波長580~700nmの最大透過率が50%以上
[Evaluation of color separation]
The obtained photosensitive coloring compositions 1 to 38 are placed on a glass substrate (Eagle 2000 manufactured by Corning Co., Ltd.) having a length of 100 mm, a width of 100 mm, and a thickness of 0.7 mm by a spin coating method to obtain a film thickness after drying. The coating was applied so as to have a thickness of 6.0 μm, and the mixture was dried on a hot plate at 70 ° C. for 1 minute. Next, using an ultra-high pressure mercury lamp, the entire surface was exposed at an exposure amount of 50 mJ / cm 2 , and then post-baked at 230 ° C. for 30 minutes in a clean oven to obtain a substrate for color separability evaluation. The obtained substrate for color separability evaluation was measured for maximum transmittance at a wavelength of 450 to 510 nm and a wavelength of 580 to 700 nm in the thickness direction of the coating film using OSP-SP100 (manufactured by Olympus Corporation). The evaluation criteria are as follows, and 2 or more are practical.
4: Maximum transmittance of wavelength 450 to 510 nm is less than 30%, maximum transmittance of wavelength 580 to 700 nm is less than 30% 3: Maximum transmittance of wavelength 450 to 510 nm is less than 40%, and maximum transmittance of wavelength 580 to 700 nm Transmittance is less than 40% 2: Maximum transmittance of wavelength 450 to 510 nm is less than 50%, and maximum transmittance of wavelength 580 to 700 nm is less than 50% 1: Maximum transmittance of wavelength 450 to 510 nm is 50% or more, or wavelength Maximum transmittance of 580 to 700 nm is 50% or more
また、感光性着色組成物10、18、及び35を、乾燥後の膜厚が4.0μmとなるように塗工し、上述の各評価用基板を作製し、実施例32、33、及び比較例8として、現像性、パターン形成性、表面シワ、及び色分離性を評価した。 Further, the photosensitive coloring compositions 10, 18 and 35 were coated so that the film thickness after drying was 4.0 μm to prepare each of the above-mentioned evaluation substrates, and the above-mentioned Examples 32 and 33 and comparison were made. As Example 8, developability, pattern formability, surface wrinkles, and color separability were evaluated.
Claims (11)
前記有機顔料(A)が、ハロゲン化金属フタロシアニン顔料(A-1)、及びイソインドリン顔料(A-2)を含み、
前記重合性化合物(C)が、ウレタン結合を有する重合性化合物(C-1)を含み、
前記有機顔料(A)の含有量が、感光性着色組成物の不揮発分100質量%中、25質量%以上である、感光性着色組成物。 A photosensitive coloring composition comprising an organic pigment (A), an alkali-soluble resin (B), a polymerizable compound (C), a photopolymerization initiator (D), and silica particles (E).
The organic pigment (A) contains a metal halide phthalocyanine pigment (A-1) and an isoindoline pigment (A-2).
The polymerizable compound (C) contains a polymerizable compound (C-1) having a urethane bond, and contains
A photosensitive coloring composition in which the content of the organic pigment (A) is 25% by mass or more in 100% by mass of the non-volatile content of the photosensitive coloring composition.
The optical filter having the cured film according to claim 10, wherein the film thickness of the cured film is 4.0 μm or more.
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