JP2010204363A - ブラックレジスト用感光性樹脂組成物及びカラーフィルター遮光膜 - Google Patents
ブラックレジスト用感光性樹脂組成物及びカラーフィルター遮光膜 Download PDFInfo
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- JP2010204363A JP2010204363A JP2009049446A JP2009049446A JP2010204363A JP 2010204363 A JP2010204363 A JP 2010204363A JP 2009049446 A JP2009049446 A JP 2009049446A JP 2009049446 A JP2009049446 A JP 2009049446A JP 2010204363 A JP2010204363 A JP 2010204363A
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- -1 methacryloyl group Chemical group 0.000 claims abstract description 51
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000012860 organic pigment Substances 0.000 claims abstract description 12
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 9
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 8
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- 239000000463 material Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 238000011161 development Methods 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
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- 125000005843 halogen group Chemical group 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000006229 carbon black Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
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- 238000012360 testing method Methods 0.000 abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 4
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
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- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 1
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- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
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- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
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- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
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- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133512—Light shielding layers, e.g. black matrix
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
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Abstract
【解決手段】(a)アクリロイル基及びメタクリロイル基からなる群から選ばれる基のいずれか一方又は両方を合計2個有する二官能モノマー、(b)エポキシ基を2個以上有する化合物と(メタ)アクリル酸との反応物を、更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有樹脂、(c)光重合開始剤、及び(d)黒色有機顔料、混色有機顔料及び遮光材からなる群から選ばれた1以上の遮光成分を含有する遮光性分散液を含有することを特徴とするブラックレジスト用感光性樹脂組成物である。
【選択図】なし
Description
(a)アクリロイル基及びメタクリロイル基からなる群から選ばれる基のいずれか一方又は両方を合計2個有する二官能モノマー、
(b)エポキシ基を2個以上有する化合物と(メタ)アクリル酸との反応物を、更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有樹脂、
(c)光重合開始剤、及び
(d)黒色有機顔料、混色有機顔料及び遮光材からなる群から選ばれた1以上の遮光成分を含有する遮光性分散液
を含有することを特徴とするブラックレジスト用感光性樹脂組成物である。
(式中、R1及びR2は水素原子又はメチル基を表し、互いに同じか異なってもよく、AO及びBOは炭素数2〜4の互いに異なるオキシアルキレン基を表す。また、m及びnは0以上の整数であり、m+n=4〜30の範囲である。)
(式中、R1及びR2は水素原子又はメチル基を表し、互いに同じか異なってもよく、R3〜R10は、それぞれ独立に、水素原子、ハロゲン原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数1〜5のアルキニル基、炭素数5〜9のシクロアルキル基、炭素数6〜10のアリール基、又は炭素数1〜5のアルコキシ基を表し、Xは‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は単結合を示す。AO及びBOは炭素数2〜4の互いに異なるオキシアルキレン基を表す。また、m及びnは0以上の整数であり、m+n=4〜30の範囲である。)
(但し、式(3)中、R11及びR12は水素原子、炭素数1〜5のアルキル基又はハロゲン原子であり、互いに同じか異なってもよくXは‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は単結合を示し、nは0〜10の整数である)
(但し、式(4)中、nは1以上5以下の整数を表し、R13〜R16は、それぞれ独立に、水素原子、炭素数1〜5のアルキル基、炭素数5〜9のシクロアルキル基、又は炭素数6〜10のアリール基を表し、R17〜R27は、それぞれ独立に、水素原子、ハロゲン原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数1〜5のアルキニル基、炭素数5〜9のシクロアルキル基、炭素数6〜10のアリール基、又は炭素数1〜5のアルコキシ基を表す。)
(但し、式(3)中、R11及びR12は水素原子、炭素数1〜5のアルキル基又はハロゲン原子であり、互いに同じか異なってもよくXは‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は単結合を示し、nは0〜10の整数である)
(但し、式(4)中、nは1以上5以下の整数を表し、R13〜R16は、それぞれ独立に、水素原子、炭素数1〜5のアルキル基、炭素数5〜9のシクロアルキル基、又は炭素数6〜10のアリール基を表し、R17〜R27は、それぞれ独立に、水素原子、ハロゲン原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数1〜5のアルキニル基、炭素数5〜9のシクロアルキル基、炭素数6〜10のアリール基、又は炭素数1〜5のアルコキシ基を表す。)
(a)-1:アルコキシ化ネオペンチルグリコールジアクリレート(サートマー・ジャパン社製 商品名CD9043)
(a)-2:アルコキシ化ヘキサンジオールジアクリレート(サートマー・ジャパン社製 商品名CD564)
(a)-3:ポリエチレングリコールジアクリレート(日油(株)社製 商品名ブレンマーADE-600)
(a)-4:ポリエチレングリコールジアクリレート(日油(株)社製 商品名ブレンマーADE-400)
(a)-5:エトキシ化(10)ビスフェノールAジアクリレート(サートマー・ジャパン社製 商品名SR602)
(a)-6:ペンタエリスリトールテトラアクリレート(サートマー・ジャパン(株)製、商品名SR295)
(a)-7: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との混合物(日本化薬(株)製、商品名DPHA)
(b)-1:フルオレン骨格を有するエポキシアクリレートの酸無水物重縮合物のプロピレングリコールモノメチルエーテルアセテート溶液(樹脂固形分濃度=56.5質量%、新日鐵化学(株)製、商品名V259ME)
(b)-2:Mw(重量平均分子量)9000、酸価80のN-フェニルマレイミド/アクリル酸/スチレン供重合体のプロピレングリコールモノメチルエーテルアセテート溶液(樹脂固形分濃度=35.5質量%)、(N-フェニルマレイミド:アクリル酸:スチレン=19:22:59mol%)
(c)-1:エタノン,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−(0−アセチルオキシム)、(チバ・ジャパン社製、製品名イルガキュアOXE02)
(c)-2:2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1(チバ・ジャパン社製、製品名イルガキュア369)
(c)-3:2−(ピプロニル)−4,6−ビス(トリクロロメチル)−1,3,5−トリアジン(日本シーベルヘグナー社製、製品名トリアジンPP)
(d):カーボンブラック濃度25.0質量%、高分子分散剤濃度4.75質量%のプロピレングリコールモノメチルエーテルアセテート分散液(固形分29.75%)
(e):3−メタクリロキシプロピルトリメトキシシラン(商品名:KBM-503:信越化学(株)製)
(f)-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
(f)-2:シクロヘキサノン
(g):メガファックF475(大日本インキ化学工業(株)製)
上記の配合成分を表1に記載の割合で配合して、実施例1〜6及び比較例1〜5に係るブラックレジスト用感光性樹脂組成物を調製した。表1において(b)成分の( )内の数字は不飽和基含有樹脂中における固形分量(g)を示し、(d)成分の( )内の数字は遮光成分の固形分量(g)を示す。
測長顕微鏡((株)ニコン製 商品名XD-20)を用いてマスク幅20μmのパターン線幅を測定した。
現像後の20μmマスクパターンを顕微鏡観察し、基板に対する剥離やパターンエッジ部分のギザツキが認められないものを○、認められるものを×と評価した。
2μm、4μm、5μm、6μm、8μm、10μm、及び20μmマスクパターンのうち、基板上に残った最小パターンサイズを解像度とした。解像度が2、4、5、6又は8μmの場合を○とし、10μm以上の場合を×と評価した。
Claims (8)
- (a)アクリロイル基及びメタクリロイル基からなる群から選ばれる基のいずれか一方又は両方を合計2個有する二官能モノマー、
(b)エポキシ基を2個以上有する化合物と(メタ)アクリル酸との反応物を、更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有樹脂、
(c)光重合開始剤、及び
(d)黒色有機顔料、混色有機顔料及び遮光材からなる群から選ばれた1以上の遮光成分を含有する遮光性分散液
を含有することを特徴とするブラックレジスト用感光性樹脂組成物。 - 前記(a)アクリロイル基及びメタクリロイル基からなる群から選ばれる基のいずれか一方又は両方を合計2個有する二官能モノマーは、下記一般式(1)又は一般式(2)で表される請求項1に記載のブラックレジスト用感光性樹脂組成物。
(式中、R1及びR2は水素原子又はメチル基を表し、互いに同じか異なってもよく、AO及びBOは炭素数2〜4の互いに異なるオキシアルキレン基を表す。また、m及びnは0以上の整数であり、m+n=4〜30の範囲である。)
(式中、R1及びR2は水素原子又はメチル基を表し、互いに同じか異なってもよく、R3〜R10は、それぞれ独立に、水素原子、ハロゲン原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数1〜5のアルキニル基、炭素数5〜9のシクロアルキル基、炭素数6〜10のアリール基、又は炭素数1〜5のアルコキシ基を表し、Xは‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は単結合を示す。AO及びBOは炭素数2〜4の互いに異なるオキシアルキレン基を表す。また、m及びnは0以上の整数であり、m+n=4〜30の範囲である。) - (b)成分を得る際に用いるエポキシ基を2個以上有する化合物が、下記一般式(3)及び一般式(4)で表される化合物からなる群から選ばれた少なくとも1種の化合物である請求項1又は2に記載のブラックレジスト用感光性樹脂組成物。
(但し、式(3)中、R11及びR12は水素原子、炭素数1〜5のアルキル基又はハロゲン原子であり、互いに同じか異なってもよくXは‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は単結合を示し、nは0〜10の整数である)
(但し、式(4)中、nは1以上5以下の整数を表し、R13〜R16は、それぞれ独立に、水素原子、炭素数1〜5のアルキル基、炭素数5〜9のシクロアルキル基、又は炭素数6〜10のアリール基を表し、R17〜R27は、それぞれ独立に、水素原子、ハロゲン原子、炭素数1〜5のアルキル基、炭素数1〜5のアルケニル基、炭素数1〜5のアルキニル基、炭素数5〜9のシクロアルキル基、炭素数6〜10のアリール基、又は炭素数1〜5のアルコキシ基を表す。) - (d)成分における遮光成分が、カーボンブラックである請求項1〜3のいずれかに記載のブラックレジスト用感光性樹脂組成物。
- (d)成分における遮光成分の含有量が、ブラックレジスト用感光性樹脂組成物中の固形分に対して40〜60質量%である請求項1〜4のいずれかに記載のブラックレジスト用感光性樹脂組成物。
- (c)光重合開始剤が、アシルオキシム系光重合開始剤から選ばれた1種又は2種以上である請求項1〜5のいずれかに記載のブラックレジスト用感光性樹脂組成物。
- カラーフィルター遮光膜形成用である請求項1〜6のいずれかに記載のブラックレジスト用感光性樹脂組成物。
- 請求項7記載のブラックレジスト用感光性樹脂組成物を透明基板上に塗布し、乾燥した後、(i)紫外線露光装置による露光、(ii)アルカリ水溶液による現像、及び(iii)熱焼成の各工程を必須として得られることを特徴とするカラーフィルター遮光膜。
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JP2013114008A (ja) * | 2011-11-28 | 2013-06-10 | Nichigo Morton Co Ltd | 感光性樹脂組成物、及びこれを用いたフォトレジストフィルム |
WO2014041940A1 (ja) | 2012-09-14 | 2014-03-20 | 富士フイルム株式会社 | 硬化性組成物および画像形成方法 |
JP2016061939A (ja) * | 2014-09-18 | 2016-04-25 | 株式会社Adeka | 光硬化性組成物 |
KR20180063055A (ko) | 2015-09-30 | 2018-06-11 | 도레이 카부시키가이샤 | 네거티브형 착색 감광성 수지 조성물, 경화막, 소자 및 표시 장치 |
CN111435220A (zh) * | 2019-01-15 | 2020-07-21 | 新应材股份有限公司 | 感光性树脂组合物、光学膜及其制造方法 |
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