JP7312107B2 - 重合性組成物、ブラックマトリクス用感光性組成物及びブラックカラムスペーサ用感光性組成物 - Google Patents
重合性組成物、ブラックマトリクス用感光性組成物及びブラックカラムスペーサ用感光性組成物 Download PDFInfo
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- JP7312107B2 JP7312107B2 JP2019525422A JP2019525422A JP7312107B2 JP 7312107 B2 JP7312107 B2 JP 7312107B2 JP 2019525422 A JP2019525422 A JP 2019525422A JP 2019525422 A JP2019525422 A JP 2019525422A JP 7312107 B2 JP7312107 B2 JP 7312107B2
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- VVNRQZDDMYBBJY-UHFFFAOYSA-M sodium 1-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 VVNRQZDDMYBBJY-UHFFFAOYSA-M 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 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
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
- G02F1/1362—Active matrix addressed cells
- G02F1/136209—Light shielding layers, e.g. black matrix, incorporated in the active matrix substrate, e.g. structurally associated with the switching element
-
- 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
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
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- 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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
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- Structural Engineering (AREA)
- Architecture (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Electroluminescent Light Sources (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
R2、R4及びR6は、それぞれ独立に炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
R3及びR4が、複数存在する場合、同一の場合も異なる場合もあり、
Y1、Y2及びY3は、直接結合、炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
Y2が、複数存在する場合、同一の場合も異なる場合もあり、
Z1、Z2及びZ3は、それぞれ独立して炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
Z2が、複数存在する場合、同一の場合も異なる場合もあり、
R2、R4、R6、Y1、Y2、Y3、Z1、Z2及びZ3で表される基中の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、メルカプト基、イソシアネート基又は複素環を含有する炭素原子数2~20の基で置換される場合があり、
R2、R4、R6、Y1、Y2、Y3、Z1、Z2及びZ3で表される基中のメチレン基は-O-、-CO-、-COO-、-OCO-、-S-、-SO2-、-SCO-又は-COS-で置換される場合もあり、
mは0又は10以下の正の数を表し、aは、0又は4以下の正の数を表し、bは、0又は3以下の正の数を表し、cは、0又は4以下の正の数を表し、
mが2以上の場合、bは同一の場合も異なる場合もある。)
R13は、水素原子、炭素原子数1~20の炭化水素基を表し、
nは0又は1を表し、
式中の*は、結合手を表す。)
本発明の重合性組成物に用いられる着色剤(A)は、有機着色剤(A1)及び無機着色剤(A2)を含有し、既知の顔料や染料を混合して用いることができる。ここで、顔料とは、後述する溶剤に不溶の着色剤を意味し、無機又は有機着色剤の中でも溶剤に不溶であるもの、或いは無機又は有機染料をレーキ化したものも含まれる。
例えば厚さ1~3μmの硬化物を形成する場合には、着色剤(A)の含有量は、特に限定されるものではないが、アルカリ現像性化合物(B)100質量部に対して、好ましくは5~10質量部、より好ましくは10~80質量部、更に好ましくは20~60質量部である。
また780nmの透過率が高いことから、重合組成物中、有機着色剤(A1)100質量部に対し、無機着色剤(A2)が30質量部以下であることが好ましく、20質量部以下がより好ましい。一方、遮光性が高いことから、有機着色剤(A1)100質量部に対し、無機着色剤(A2)が2質量部以上であることが好ましく、5質量部以上であることがより好ましい。
本発明に係るアルカリ現像性化合物(B)は、親水性基を有し、且つ、アルカリ現像性を示す化合物である。本発明においては、アルカリ現像性化合物(B)として、上記の条件を満たしている限り、従来用いられている化合物を用いることができる。
上記親水性基としては、水酸基、チオール基、カルボキシル基、スルホ基、アミノ基、アミド基又はその塩等が挙げられ、水酸基及びカルボキシル基が、アルカリ現像性化合物(B)のアルカリ現像性が高いため好ましい。
親水性基の官能基当量が上記の範囲である場合、アルカリ現像性に優れるため好ましい。
Mで表される炭素原子数1~20の炭化水素基中の水素原子はハロゲン原子で置換される場合があり、R21、R22、R23、R24、R25、R26、R27及びR28(以下、R21~R28とも記載)は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基、又はハロゲン原子を表し、kは0~10の数であり、k≧1の場合、複数存在するR21~R28及びMは、それぞれ、同一である場合も、異なる場合もある。)
R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56、R57及びR58(以下、R30~R58とも記載)は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基、複素環を含有する炭素原子数2~20の基、又はハロゲン原子を表し、
R31~R38及びR40~R68で表される基中のメチレン基は、不飽和結合、-O-又は-S-で置換される場合があり、
R30とR31、R31とR32、R32とR33、R33とR34、R35とR36、R36とR37、R37とR38、R43とR44、R44とR45、R45とR46、R51とR52、R52とR53、R53とR54、R55とR56、R56とR57及びR57とR58は結合して環を形成する場合があり、
(a)、(b)、(c)及び(d)で表される基中の*は、結合手を表す。)
上記式中のZで表される炭素原子数1~6のアルキレン基としては、メチレン、エチレン、プロピレン、メチルエチレン、ブチレン、1-メチルプロピレン、2-メチルプロピレン、1,2-ジメチルプロピレン、1,3-ジメチルプロピレン、1-メチルブチレン、2-メチルブチレン、3-メチルブチレン、4-メチルブチレン、2,4-ジメチルブチレン、1,3-ジメチルブチレン、ペンチレン、へキシレン等の直鎖又は分岐のアルキレン基を挙げることができる。
上記不飽和一塩基酸としては、例えば、アクリル酸、メタクリル酸、クロトン酸、桂皮酸、ソルビン酸及びヒドロキシエチルメタクリレート・マレート、ヒドロキシプロピルメタクリレート・マレート、ヒドロキシプロピルアクリレート・マレート及びジシクロペンタジエン・マレート等が挙げられる。
即ち、上記エポキシ付加化合物は、上記エポキシ化合物のエポキシ基1個に対し、上記不飽和一塩基酸のカルボキシル基が0.1~1.0個の比率となるように付加させるのが好ましく、また上記エチレン性不飽和化合物は、上記エポキシ付加物の水酸基1個に対し、上記多塩基酸無水物の酸無水物構造が0.1~1.0個となる比率となるようにするのが好ましい。
上記一般式(III)で表されるエポキシ化合物、上記不飽和一塩基酸及び上記多塩基酸無水物の反応は、常法に従って行なうことができる。
上記ビスフェノール型エポキシ化合物としては、上記一般式(III)で表されるエポキシ化合物を用いることができる他、例えば、水添ビスフェノール型エポキシ化合物等のビスフェノール型エポキシ化合物も用いることができる。
また上記グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4-ブタンジオールジグリシジルエーテル、1,6-ヘキサンジオールジグリシジルエーテル、1,8-オクタンジオールジグリシジルエーテル、1,10-デカンジオールジグリシジルエーテル、2,2-ジメチル-1,3-プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、1,4-シクロヘキサンジメタノールジグリシジルエーテル、1,1,1-トリ(グリシジルオキシメチル)プロパン、1,1,1-トリ(グリシジルオキシメチル)エタン、1,1,1-トリ(グリシジルオキシメチル)メタン、1,1,1,1-テトラ(グリシジルオキシメチル)メタン等を用いることができる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4-エポキシ-6-メチルシクロヘキシルメチル-3,4-エポキシ-6-メチルシクロヘキサンカルボキシレート、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、1-エポキシエチル-3,4-エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジルp-アミノフェノール、N,N-ジグリシジルアニリン等のグリシジルアミン類;1,3-ジグリシジル-5,5-ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物;トリフェニルメタン型エポキシ化合物;ジシクロペンタジエン型エポキシ化合物等を用いることもできる。
該市販品としては、例えば、SPC1000、SPC-2000、SPC-3000、SPRR-1X、SPRR-2X、SPRR-3X、SPRR-5X、SPRR-6X、SPRR-7X、SPRR-8X、SPRR-9X、SPRR-10X、SPRR-11X、SPRR-12X、SPRR-13X、SPRR-14X、SPRR-15X、SPRR-16X、SPRR-17X、SPRR-18X、SPRR-19X、SPRR-20X、SPRR-21X(以上、昭和電工社製)、JET2000、AGOR1060、AGOR3060、ORGA1060、ORGA2060(以上、大阪有機化学社製)、CCR-1171H(日本化薬社製)等が挙げられる。
例えば厚さ2~5μmの硬化膜を形成する場合には、アルカリ現像性化合物(B)の含有量は、特に限定されるものではないが、着色剤(A)、アルカリ現像性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは、10~95質量部、より好ましくは、30~90質量部であり、更に好ましくは、30~80質量部である。
またアルカリ現像性化合物(B)が、一般式(I)で表される化合物を含有する場合、一般式(I)で表される化合物の含有量は、着色剤(A)、アルカリ現像性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは、10~60質量部、より好ましくは、20~50質量部である。また、上記一般式(III)で表される化合物に不飽和一塩基酸を付加させた構造を有するエポキシ付加化合物又は該エポキシ付加化合物と、多塩基酸無水物とのエステル化反応により得られる反応生成物であるアルカリ現像性化合物を含有する場合、該エポキシ付加化合物及び該エポキシ付加化合物と多塩基酸無水物とのエステル化反応により得られる反応生成物の含有量は、着色剤(A)、アルカリ現像性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは、5~80質量部、より好ましくは、5~40質量部である。上記のエポキシ付加化合物及び該エポキシ付加化合物と多塩基酸無水物とのエステル化反応により得られる反応生成物の含有量とは、該エポキシ付加化合物及び該反応生成物の一方のみを含有する場合はその量であり、両方を含有する場合はその合計量である。
本発明の重合性組成物に用いられる重合開始剤(C)としては、従来既知のラジカル重合開始剤を用いることが可能である。
R61及びR62は、それぞれ独立に、水素原子、ニトロ基、シアノ基、炭素原子数1~20のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は複素環を含有する炭素原子数2~20の基を表し、
X1は、酸素原子、硫黄原子、セレン原子、CR63R64、CO、NR65又はPR66を表し、
X2は、無結合、直接結合、炭素原子数1~20の炭化水素基、COを表し、R63~R66は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、R61~R66で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアン基、水酸基、カルボキシル基又は複素環基で置換される場合もあり、
R61~R66で表される基中のメチレン基は、酸素が隣り合わない条件で-O-に置換される場合もあり、
R61~R66は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成する場合もあり、
gは、0~4の数を表し、
hは、0~3の数を表す。)
Xsは、硫黄原子又はNR100を表し、
R100、R101、R102、R103及びR104は、それぞれ独立に、水素原子、炭素原子数1~12のアルキル基、フェニル基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~12のアルケニル基を表し、該アルキル基は水酸基、カルボキシル基、ハロゲン原子、シアノ基又はニトロ基で置換されている場合があり、該フェニル基及び該アリールアルキル基は炭素原子数1~4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基又はニトロ基で置換されている場合があり、
R101とR102は、連結して3~6員環の複素環を形成している場合があり、該複素環中の窒素原子にはR99が結合している場合があり
R103とR104は、連結して3~6員環を形成していてもよく、
R105、R106、R107及びR108はそれぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基、カルボキシル基又は炭素原子数1~12のアルキル基を表し、該アルキル基は、ハロゲン原子、カルボキシル基、シアノ基、ニトロ基又は水酸基で置換されている場合があり、
R99は水素原子、炭素原子数1~12のアルキル基、フェニル基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~12のアルケニル基を表し、該アルキル基は水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている場合があり、該フェニル基及び該アリールアルキル基は炭素原子数1~4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている場合がある。
上記で挙げた各アルキル基及び上記各アリールアルキル基中のメチレン基は、-O-、-S-、-NR117-、-CO-、-CO-O-、-O-CO-又は-O-CO-O-で置換されている場合がある。
R117は、水素原子、炭素原子数1~12のアルキル基、フェニル基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~12のアルケニル基を表し、該アルキル基は水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている場合があり、該フェニル基及び該アリールアルキル基は炭素原子数1~4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている場合がある。
ただし、式(V)で表される化合物は、分子中に少なくとも一つの水酸基を有している。)
式中の下記(i-1)
R111は、水素原子、ハロゲン原子、水酸基、カルボキシル基、シアノ基、アミノ基又はフェニル基を表し、該フェニル基は炭素原子数1~4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている場合があり、pは、1~12の数を表す。)
R106又はR107は、R112又はR116と結合して環を形成している場合がある。)
V)と同じであり、R109、R110及びpは、上記一般式(i)と同じである。)
例えば厚さ2~5μmの硬化膜を形成する場合には、重合開始剤(C)の含有量は、特に限定されるものではないが、着色剤(A)、アルカリ現像性化合物(B)及び重合開始剤(C)の合計100質量部に対して、好ましくは0.1~20質量部、より好ましくは0.3~10質量部、より好ましくは0.3~5質量部である。
上記エチレン性不飽和化合物は、単独で又は2種以上を混合して使用することができる。
例えば厚さ1~3μmの硬化膜を形成する場合には、エチレン性不飽和化合物の含有量は、特に限定されるものではないが、重合開始剤(C)、着色剤(A)、アルカリ現像性化合物(B)及びエチレン性不飽和化合物の合計100質量部に対して、エチレン性不飽和化合物は好ましくは、1~50質量部、より好ましくは、1~30質量部であり、更に好ましくは、5~20質量部である。
溶剤の含有量が上記範囲の場合、ハンドリング性(重合性組成物の粘度や濡れ性)、乾燥時のムラの低減及び液安定性(組成物に含まれる成分の析出や沈降を伴わない)に優れる重合性組成物となり、硬化物を得る際に硬化物の厚さを適切にコントロールできることから好ましい。
また縮合反応終了後に、前記親水性溶媒に反応混合物を溶解し、水、n-ヘキサン及びn-ヘプタン等の沈殿剤に添加することにより、ノボラック樹脂を析出させ、析出物を分離し、加熱乾燥することにより回収することもできる。
上記潜在性添加剤としてはWO2014/021023号パンフレットに記載されているものを好ましく使うことができる。
上記アルカリ現像性化合物(B)と共に、上記有機重合体を用いることによって、硬化物の特性を改善することもできる。
有機重合体を使用する場合、その使用量は、上記アルカリ現像性化合物(B)100質量部に対して、好ましくは10~500質量部である。
また、これら無機化合物は、例えば、充填剤、反射防止剤、導電剤、安定剤、難燃剤、機械的強度向上剤、特殊波長吸収剤及び撥インク剤等としても好適に用いられる。
カップリング剤を添加することにより、硬化物と基材間(特にガラス)の密着性を向上するので好ましい。
上記マスクとしては、ハーフトーンマスク又はグレースケールマスク等の多階調マスクを用いることもできる。
有機系の黒色顔料(ラクタムブラックとしてブラック582;BASF社製)、分散剤(BYK-167)および分散物のためのポリマー(後述するアルカリ現像性化合物PGMEA溶液B-2)を、それぞれ、16質量部、3.2質量部および3.6 質量部で混合した後で、この混合物にプロピレングリコールモノメチルエーテルアセタート(PGMEA)を固形分濃度25質量%となるよう秤量して添加し、混合物を作成した。
上記混合物をスターラーにより予備混合した後、直径0.3mmのジルコニアビーズを分散物(混合物から溶剤であるPGMEAを除いたもの)と同じ重量で添加し、25~60℃の温度で6時間にわたってペイントシェーカーによる分散物処理にかけたのち、フィルタを用いてジルコニアビーズを取り除き、分散液を得た。得られた分散液にPGMEAを追加し、分散物濃度が20質量%となるように調整し、スターラーにより均一にした後、ラクタムブラック分散液A-1を得た。
有機系の黒色顔料[ペリレンブラックとしてC.I.ピグメントブラック31(PalIogenBlackS0084;BASF社製)]、分散剤(BYK-167)及び分散物のためのポリマー(後述するアルカリ現像性化合物PGMEA溶液B-2)を、それぞれ、12質量部、3.6質量部および8質量部で混合した後で、この混合物にプロピレングリコールモノメチルエーテルアセタート(PGMEA)を固形分濃度25質量%となるよう秤量して添加し、混合物を作成した。
上記混合物をスターラーにより予備混合した後、直径0.3mmのジルコニアビーズを分散物(混合物から溶剤であるPGMEAを除いたもの)と同じ重量で添加し、25~60℃の温度で6時間にわたってペイントシェーカーによる分散物処理にかけたのち、フィルタを用いてジルコニアビーズを取り除き、分散液を得た。得られた分散液にPGMEAを追加し、分散物濃度が20質量%となるように調整し、スターラーにより均一にした後、ペリレンブラック分散液A-2を得た。
カーボンブラックとしてMA100(三菱化学社製)を20質量部、分散剤としてBYK161(ビックケミー(BYK)社製)12.5質量部(固形分濃度40質量%)、溶媒としてプロピレングリコールモノメチルエーテルアセテート67.5質量部を混合し、ビーズミルにより処理して、カーボンブラック分散液A-3を調製した。
1,1-ビス〔4-(2,3-エポキシプロピルオキシ)フェニル〕インダンの184g、アクリル酸58g、2,6-ジ-tert-ブチル-p-クレゾール0.26g、テトラ-n-ブチルアンモニウムブロミド0.11g及びPGMEA105gを仕込み、120℃で16時間撹拌した。反応液を室温まで冷却し、PGMEA160g、ビフタル酸無水物59g及びテトラ-n-ブチルアンモニウムブロミド0.24gを加えて、120℃で4時間撹拌した。更に、テトラヒドロ無水フタル酸20gを加え、120℃で4時間、100℃で3時間、80℃で4時間、60℃で6時間、40℃で11時間撹拌した後、PGMEA128gを加えて、PGMEA溶液としてアルカリ現像性化合物B-2を得た(Mw=5000、Mn=2100、酸価(固形分)92.7mgKOH/g)。アルカリ現像性化合物PGMEA溶液B-2におけるアルカリ現像性化合物の含有率は45質量%であった。
9,9-ビス(4-グリシジルオキシフェニル)フルオレン75.0g、アクリル酸23.8g、2,6-ジ-t-ブチル-p-クレゾール0.273g、テトラブチルアンモニウムクロリド0.585g、及びPGMEA65.9gを仕込み、90℃で1時間、100℃で1時間、110℃で1時間及び120℃で14時間撹拌した。室温まで冷却し、無水コハク酸25.9g、テトラブチルアンモニウムクロリド0.427g、及びPGMEA1.37gを加えて、100℃で5時間撹拌した。さらに、9,9-ビス(4-グリシジルオキシフェニル)フルオレン30.0g、2,6-ジ-t-ブチル-p-クレゾール0.269g、及びPGMEA1.50gを加えて、90℃で90分、120℃で4時間撹拌後、PGMEA122.2gを加えて、PGMEA溶液として目的物であるアルカリ現像性化合物B-3を得た(Mw=4190、Mn=2170,酸価(固形分)52mg・KOH/g)。アルカリ現像性化合物PGMEA溶液B-3におけるアルカリ現像性化合物の含有率は45質量%であった。
[表1]~[表4]の配合に従って各成分を混合し、重合性組成物(実施例1~15及び比較例1~4)を得た。尚、表中の配合の数値は質量部を表す。
また、表中の各成分の符号は、下記の成分を表す。
A1-1 ラクタムブラック分散液A-1
A1-2 ペリレンブラック分散液A-2
A2-1 カーボンブラック分散液A-3
B-1 CCR-1171H
[一般式(I)で表されるアルカリ現像性化合物PGMEA溶液 固形分69.5%; 日本化薬社製]
B-2 アルカリ現像性化合物PGMEA溶液B-2
B-3 アルカリ現像性化合物PGMEA溶液B-3
C-1 化合物No.C1-1
C-2 化合物No.C1-8
C-3 化合物No.C2-1
D-1 カヤラッドDPHA(エチレン性不飽和化合物;日本化薬社製)
D-2 UA-306H(ウレタンアクリレート、共栄社化学社製)
D-3 M-450(エチレン性不飽和化合物;東亞合成社製)
E-1 γ-グリシドキシプロピルトリメトキシシラン(カップリング剤)
E-2 カレンズPE-1(チオール化合物 ;昭和電工社製)
F-1 PGMEA
F-2 3-メトキシブチルアセテート
F-3 コハク酸ジメチル
実施例1~15及び比較例1~4の比較重合性組成物から得られる硬化物について、弾性回復率、遮光性(OD値)、比誘電率、低液晶汚染性(VHR)、耐薬品性及び780nm透過率の評価を、下記の手順で行った。結果を[表1]~[表4]に併記する。
ガラス基板上に実施例1~15の重合性組成物及び比較例1~3の比較重合性組成物をスピンコート(3μm厚,300rpm×7秒)により塗布し、乾燥した後90℃において100秒間プリベークを行い、溶剤を除去した。次いで、フォトマスクを使用して高圧水銀ランプにて100mJ/cm2露光後、0.04wt%KOH水溶液を用いて現像を行った。その後、230℃にて30分加熱し、パターンを作成した。得られたパターンの20μm部分で、島津社ダイナミック微小硬度計DUH-211を用いて、40mNにて荷重を負荷-除荷試験をおこなった。弾性回復率(%)を下記の計算式によって算出した。
弾性回復率(%)=[(回復距離/圧縮変位)×100]
弾性回復率(%)が、60%以上の硬化物はBCSとして使用することができ、弾性回復率(%)が、70%以上の硬化物はBCSとして好ましく使用することができ、弾性回復率(%)が、80%以上の硬化物はBCSとして特に好ましく使用することができる。
ガラス基板上に実施例1~15の重合性組成物及び比較例1~3の比較重合性組成物をスピンコート(300rpm、7秒間)し乾燥させた後、90℃で100秒間プリベークを行った。光源として超高圧水銀ランプを用いて露光後した後、230℃で30分間ベークして硬化物を作成した。得られた膜のOD値を、マクベス透過濃度計を用いて測定し、該OD値をポストベーク後の膜厚で割って、膜厚あたりのOD値を算出した。
膜厚あたりのOD値が1.0以上の硬化物は、汎用BCSとして使用することができ、1.5以上の硬化物は、遮光性が高いため、高遮光性BCSとして使用することができ、膜厚あたりのOD値が1.75以上の硬化物は高遮光性BCSとして好ましく使用することができ、膜厚あたりのOD値が2.0以上の硬化物はBCSとして特に好ましく使用できる。膜厚あたりのOD値が1.0未満の硬化物はBCSとして使用できない。
ガラス基板上に実施例1~15の重合性組成物及び比較例1~3の比較重合性組成物をスピンコート(3μm厚,300rpm×7秒間)し、乾燥させた後、90℃で100秒間プリベークを行ない、マスクを使用せず高圧水銀ランプにて100mJ/cm2露光した後、230℃×180分間加熱し、上記評価サンプルを作成した。(評価法)上記評価サンプルについて、LCRメーター、アジレント社4284Aを用いて、AC1V、1kHz印加し測定を行った。
比誘電率が5.0未満の硬化物はBCSとして使用することができ、比誘電率が4.5以下の硬化物はBCSとして好まし使用でき、比誘電率が4.0以下の硬化物はBCSとして特に好ましく使用できる。比誘電率が5.0以上の硬化物はBCSとして使用できない。
実施例1~15で得られた重合性組成物及び比較例1~3で得られた比較重合性組成物を、ガラス基板(100mm×100mm)上にスピンコーターを用いて塗布し、90℃で100秒間プリベークを行い、膜厚3.0μmの塗膜を形成した。次いで、ミラープロジェクションアライナー(製品名:TME-150RTO、株式会社トプコン製)を使用し、マスクを介さず塗膜に紫外線を照射量200mJ/cm2で照射した。その後、230℃で30分間、ポストベークを行った。
ポストベーク後の塗膜の1質量部を40質量部のADEKA社製の液晶「RS-182」と混合し、120℃で1時間保存した。これを室温に取り出し静置後、上澄み液を採取した。採取した液晶組成物のVHR(電圧保持率)を測定した。詳細な評価方法は、下記の通りである。液晶組成物を液晶評価用TNセル(セル厚5μm、電極面積8mm×8mm配向膜JALS2096)に注入し、VHRをVHR-1A(東陽テクニカ社製)を用い測定した。(測定条件:パルス電圧幅60μs、フレーム周期16.7ms、波高±5V、測定温度60℃)
VHRが、90%以上の硬化物は、低液晶汚染性であり、BCSとして使用することができ、VHRが、95%以上の硬化物は、BCSとして好ましく使用することができ、VHRが、98%以上の硬化物は、BCSとして特に好ましく使用することができる。VHRが90%未満の硬化物は、BCSとして使用できない。
N-メチルピロリドン(NMP)溶出試験は以下の手順にて行った。
まず、調製した実施例1~15で得られた重合性組成物及び比較例1~3で得られた比較重合性組成物を最終的な膜厚が3μmとなるようにスピンコーターにてガラス基板に塗布し、1分間減圧乾燥した後にホットプレート90℃で120秒間乾燥した。高圧水銀ランプにて50mJ/cm2露光後に現像工程を経てからオーブン230℃で40分間加熱してレジスト塗工基板を得た。作製したレジスト塗工基板から測定用基板(25mm×35mm角)2枚を切り出してN-メチルピロリドン(NMP)8mL入りの10mL用バイアル瓶に浸漬した。そして、その測定用基板入りのバイアル瓶を90℃のクリーンオーブンに、60分間静置した状態でNMP溶出試験を実施した。40分静置後に熱浴からバイアル瓶を取り出して、そのNMP溶出溶液を分光光度計(島津製作所社製「UV-3100PC」)により300~800nmの波長範囲で1nmおきに吸光度を測定した。光源には、ハロゲンランプ及び重水素ランプ(切り替え波長360nm)を使用して、検出器には、フォトマルを使用しており、スリット幅2nmを測定条件としている。試料溶液を1cm角の石英セルに入れて測定した。吸光度とは、分光法において、ある物体を光が通過した際に光強度がどの程度減衰するかを示す無次元量であり、以下の式で定義される。
測定した吸光度のスペクトル面積(nm)を算出して、下記の基準によりNMP耐薬品性を評価した。
NMP溶出溶液の吸収スペクトルの面積値による判定(波長300~800nm)
○: 20(nm)未満
△: 20(nm)以上60(nm)未満
×: 60(nm)以上
NMP耐薬品性評価が〇であるものは、BCSとして特に好ましく使用でき、△であるものは、BCSとして使用でき、×のものは、BCSとして使用できない。
実施例1~15で得られた重合性組成物及び比較例1~3で得られた比較重合性組成物を、ガラス基板(100mm×100mm)上にスピンコーターを用いて塗布し、90℃で100秒間プリベークを行い、膜厚3.0μmの塗膜を形成した。次いで、ミラープロジェクションアライナー(製品名:TME-150RTO、株式会社トプコン製)を使用し、マスクを介さず塗膜に紫外線を照射量200mJ/cm2で照射した。その後、230℃で30分間、ポストベークを行ない、サンプルを作成した。得られたサンプルの780nm透過率を吸光光度計によって測定した。780nm透過率が80%以上を○、60%超80%未満を△、60%以下を×とした。
上記評価が〇、△のものは、BCSとして使用でき、〇のものは、特に好ましく使用できる。上記評価が×のものはBCSとして使用できない。
Claims (8)
- 着色剤(A)、アルカリ現像性化合物(B)及び重合開始剤(C)を含有する重合性組成物であって、上記着色剤(A)が有機着色剤(A1)及び無機着色剤(A2)を含有する着色剤であり、有機着色剤(A1)及び無機着色剤(A2)がそれぞれ有機黒色顔料及び無機黒色顔料であり、着色剤(A)の含有量が、前記アルカリ現像性化合物(B)100質量部に対して10~80質量部であり、アルカリ現像性化合物(B)が、下記一般式(I)で表されるアルカリ現像性化合物を含有する重合性組成物。
(式中、R1、R3及びR5は、それぞれ独立に水素原子又はメチル基を表し、
R2、R4及びR6は、それぞれ独立に炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
R3及びR4が、複数存在する場合、同一の場合も異なる場合もあり、
Y1、Y2及びY3は、直接結合、炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
Y2が、複数存在する場合、同一の場合も異なる場合もあり、
Z1、Z2及びZ3は、それぞれ独立して炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、
Z2が、複数存在する場合、同一の場合も異なる場合もあり、
R2、R4、R6、Y1、Y2、Y3、Z1、Z2及びZ3で表される基中の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、メルカプト基、イソシアネート基又は複素環を含有する炭素原子数2~20の基で置換される場合があり、
R2、R4、R6、Y1、Y2、Y3、Z1、Z2及びZ3で表される基中のメチレン基は-O-、-CO-、-COO-、-OCO-、-S-、-SO2-、-SCO-又は-COS-で置換される場合もあり、
mは0又は10以下の正の数を表し、aは、0又は4以下の正の数を表し、bは、0又は3以下の正の数を表し、cは、0又は4以下の正の数を表し、
mが2以上の場合、bは同一の場合も異なる場合もある。) - アルカリ現像性化合物(B)が、下記一般式(III)で表されるエポキシ化合物に不飽和一塩基酸を付加させた構造を有するエポキシ付加化合物、又は下記一般式(III)で表されるエポキシ化合物に不飽和一塩基酸を付加させた構造を有するエポキシ付加化合物と、多塩基酸無水物とのエステル化反応により得られる構造を有する樹脂を含有する請求項1に記載の重合性化合物。
(式中、Mは直接結合、炭素原子数1~20の炭化水素基、-O-、-S-、-SO2-、-SS-、-SO-、-CO-、-OCO-又は下記式(a)、(b)、(c)又は(d)で表される群から選ばれる置換基を表し、
Mで表される炭素原子数1~20の炭化水素基中の水素原子はハロゲン原子で置換される場合があり、R21、R22、R23、R24、R25、R26、R27及びR28(以下、R21~R28とも記載)は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基、又はハロゲン原子を表し、kは0~10の数であり、k≧1の場合、複数存在するR21~R28及びMは、それぞれ、同一である場合も、異なる場合もある。)
(式中、R29は、炭素原子数1~20の炭化水素基を表し、
R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49、R50、R51、R52、R53、R54、R55、R56、R57及びR58(以下、R30~R58とも記載)は、それぞれ独立に、水素原子、炭素原子数1~20の炭化水素基、複素環を含有する炭素原子数2~20の基、又はハロゲン原子を表し、
R31~R38及びR40~R68で表される基中のメチレン基は、不飽和結合、-O-又は-S-で置換される場合があり、
R30とR31、R31とR32、R32とR33、R33とR34、R35とR36、R36とR37、R37とR38、R43とR44、R44とR45、R45とR46、R51とR52、R52とR53、R53とR54、R55とR56、R56とR57及びR57とR58は結合して環を形成する場合があり、
(a)、(b)、(c)及び(d)で表される基中の*は、結合手を表す。) - 重合開始剤(C)が、下記一般式(II)で表される基を有する重合開始剤である請求項1又は2に記載の重合性組成物。
(式中、R11及びR12は、それぞれ独立に水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基又は複素環を含有する炭素原子数2~20の基を表し、R11及びR12で表される基中の水素原子はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環を含有する炭素原子数2~20の基で置換される場合があり、R11及びR12で表される基中のメチレン基は-O-、-CO-、-COO-、-OCO-、-NR13-、-NR13CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合もあり、
R13は、水素原子又は炭素原子数1~20の炭化水素基を表し、
nは0又は1を表し、
式中の*は、結合手を表す。) - 請求項1~3の何れか一項に記載の重合性組成物を含有するブラックマトリクス用感光性組成物。
- 請求項1~3の何れか一項に記載の重合性組成物を含有するブラックカラムスペーサ用感光性組成物。
- 請求項1~3の何れか一項に記載の重合性組成物、請求項4に記載のブラックマトリクス用感光性組成物又は請求項5に記載のブラックカラムスペーサ用感光性組成物に対し、光照射又は加熱することにより、硬化物を製造する方法。
- 請求項1~3の何れか一項に記載の重合性組成物、請求項4に記載のブラックマトリクス用感光性組成物又は請求項5に記載のブラックカラムスペーサ用感光性組成物の硬化物。
- 請求項7に記載の硬化物を含有する表示装置。
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JP2014529652A (ja) | 2011-08-26 | 2014-11-13 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 光重合性不飽和樹脂、これを含む感光性樹脂組成物、並びにそれから形成された光遮蔽スペーサーおよび液晶ディスプレイデバイス |
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JP2014529652A (ja) | 2011-08-26 | 2014-11-13 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 光重合性不飽和樹脂、これを含む感光性樹脂組成物、並びにそれから形成された光遮蔽スペーサーおよび液晶ディスプレイデバイス |
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