TWI529478B - Colored radiation-sensitive composition, color filter and color liquid crystal display element - Google Patents
Colored radiation-sensitive composition, color filter and color liquid crystal display element Download PDFInfo
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- TWI529478B TWI529478B TW099103882A TW99103882A TWI529478B TW I529478 B TWI529478 B TW I529478B TW 099103882 A TW099103882 A TW 099103882A TW 99103882 A TW99103882 A TW 99103882A TW I529478 B TWI529478 B TW I529478B
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- DQIPXGFHRRCVHY-UHFFFAOYSA-N chromium zinc Chemical compound [Cr].[Zn] DQIPXGFHRRCVHY-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- 238000011109 contamination Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- FPSFKBGHBCHTOE-UHFFFAOYSA-M sodium 1-[(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)diazenyl]-4-sulfonaphthalen-2-olate Chemical compound [Na+].O=C1C(N=NC=2C3=CC=CC=C3C(=CC=2O)S([O-])(=O)=O)C(C)=NN1C1=CC=CC=C1 FPSFKBGHBCHTOE-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- 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
- G02F1/133514—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
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Description
本發明係關於著色感放射線性組成物、彩色濾光片及彩色液晶顯示元件,更詳而言之,係關於在對於使用於穿透型或是反射型的彩色液晶顯示裝置、彩色攝影管元件、有機EL顯示元件、電子紙等的彩色濾光片為有用的著色層之形成中所使用的感放射線性組成物、具有由該感放射線性組成物所形成之著色層的彩色濾光片、以及具備該彩色濾光片之彩色液晶顯示元件。The present invention relates to a color-sensitive radiation composition, a color filter, and a color liquid crystal display element, and more particularly to a color liquid crystal display device or a color photographic tube device for use in a transmissive or reflective type. A color filter such as an organic EL display element or an electronic paper is a radiation-sensitive composition used for forming a useful coloring layer, a color filter having a coloring layer formed of the radiation-sensitive composition, and a color filter. And a color liquid crystal display element having the color filter.
至今,已知有當使用著色感放射線性組成物以製造彩色濾光片的時候,在基板上或是在預先形成所期望圖案的遮光層之基板上,塗布並乾燥著色感放射線性組成物之後,藉由對乾燥塗膜照射放射線成所期望的圖案形狀且顯像(以下,稱為「曝光」),以得到各色畫素的方法(例如,參照專利文獻1及2)。Heretofore, it has been known that when a coloring sensitizing radioactive composition is used to manufacture a color filter, after coating and drying the coloring sensitizing radioactive composition on a substrate or on a substrate on which a light-shielding layer of a desired pattern is formed in advance A method in which the dried coating film is irradiated with a desired pattern shape and developed (hereinafter referred to as "exposure") to obtain each color pixel (for example, refer to Patent Documents 1 and 2).
而且,在近年的彩色濾光片的技術領域中,除了曝光量降低且縮短生產間隔時間為主流之外,為了對應於對於彩色液晶顯示元件之高色純度化的要求,有逐漸地提高在著色感放射線性組成物中所佔有之顔料的含有比例的傾向。這樣的狀況下,係顯然存在有畫素圖案的剖面形狀形成倒錐形(懸垂物)且使得在畫素圖案上形成之ITO等的透明電極斷線了,且畫素的耐溶劑性降低等各式各樣的問題。然而,尚未發現到解決這些問題的有效手段。Further, in the technical field of color filters in recent years, in addition to the reduction in the amount of exposure and the shortening of the production interval, the coloring is gradually increased in order to correspond to the requirement for high color purity of color liquid crystal display elements. There is a tendency for the proportion of the pigment contained in the radiation-sensitive composition to be contained. In such a case, it is apparent that the cross-sectional shape of the pixel pattern forms an inverted taper (overhang), and the transparent electrode of ITO or the like formed on the pixel pattern is broken, and the solvent resistance of the pixel is lowered. A variety of problems. However, no effective means of solving these problems have been found.
專利文獻1 特開平2-144502號公報Patent Document 1 JP-A-2-144502
專利文獻2 特開平3-53201號公報Patent Document 2 Japanese Patent Publication No. 3-53201
本發明係基於以上的情形而完成者,其課題係提供即使在低曝光量亦可形成正錐形形狀且耐溶劑性優異之畫素的新穎的著色感放射線性組成物。The present invention has been made in view of the above circumstances, and a problem is to provide a novel color-sensing radiation composition which can form a forward-conical shape and has excellent solvent resistance even at a low exposure amount.
本發明人等專心一意檢討的結果,發現藉由在著色感放射線性組成物中含有具有己內酯構造之分散劑或是多官能性單體、與特定的光聚合引發劑,可解決上述課題,而完成本發明。As a result of intensive review, the present inventors have found that the above problem can be solved by including a dispersing agent having a caprolactone structure or a polyfunctional monomer in a coloring sensitizing radiation composition and a specific photopolymerization initiator. The present invention has been completed.
換言之,本發明係提供一種著色感放射線性組成物,其特徵係含有(A)著色劑、(C)鹼可溶性樹脂、(D)多官能性單體、及(E)光聚合引發劑之著色感放射線性組成物,其中(D)多官能性單體係具有己內酯構造者,且(E)光聚合引發劑係具有2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮者。In other words, the present invention provides a color-sensing radiation linear composition characterized by (A) a colorant, (C) an alkali-soluble resin, (D) a polyfunctional monomer, and (E) a photopolymerization initiator. a radiation sensitive composition in which (D) a polyfunctional single system has a caprolactone structure, and (E) a photopolymerization initiator has a 2-(4-methylbenzyl)-2-(dimethyl group) Amino)-1-(4- Olostinophenyl)butan-1-one.
另外,本發明係提供一種著色感放射線性組成物,其特徵係含有(A)著色劑、(B)分散劑、(C)鹼可溶性樹脂、(D)多官能性單體、及(E)光聚合引發劑之著色感放射線性組成物,其中(B)分散劑係具有己內酯構造者,且(E)光聚合引發劑係具有2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮者。Further, the present invention provides a color-sensing radiation linear composition comprising (A) a colorant, (B) a dispersant, (C) an alkali-soluble resin, (D) a polyfunctional monomer, and (E) A color-sensing radioactive composition of a photopolymerization initiator, wherein (B) a dispersant has a caprolactone structure, and (E) a photopolymerization initiator has 2-(4-methylbenzyl)-2-( Dimethylamino)-1-(4- Olostinophenyl)butan-1-one.
另外,本發明亦提供一種具備使用該著色感放射線性組成物所形成之著色層而成的彩色濾光片、及具備該彩色濾光片所形成的彩色液晶顯示元件者。Moreover, the present invention also provides a color filter including a coloring layer formed using the coloring radiation composition, and a color liquid crystal display element including the color filter.
本發明中所謂的「放射線」係意味包含可見光線、紫外線、遠紫外線、電子束、X射線等者。The term "radiation" as used in the present invention means to include visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray, and the like.
本發明中所謂的「著色層」係意味由使用於彩色濾光片的畫素及/或黑色矩陣所構成之層。The "colored layer" in the present invention means a layer composed of a pixel and/or a black matrix used for a color filter.
使用本發明的著色感放射線性組成物,即使在低曝光量亦可形成正錐形形狀且耐溶劑性也優異的畫素。According to the color-sensing radiation composition of the present invention, a pixel having a forward tapered shape and excellent solvent resistance can be formed even at a low exposure amount.
因此,本發明的著色感放射線性組成物係非常適合使用於以彩色液晶顯示元件用彩色濾光片、固體攝影元件的色分解用彩色濾光片、有機EL顯示元件用彩色濾光片、電子紙用彩色濾光片為首的各種用途之彩色濾光片的製造。Therefore, the color-sensing radiation composition of the present invention is very suitable for use in color filters for color liquid crystal display elements, color filters for color separation of solid-state imaging elements, color filters for organic EL display elements, and electrons. The manufacture of color filters for various purposes, including paper color filters.
以下,針對本發明進行詳細地說明。Hereinafter, the present invention will be described in detail.
針對本發明的著色感放射線性組成物(以下,有時候會只稱為「感放射線性組成物」)的構成成分進行說明。The constituent components of the color-sensing radiation composition of the present invention (hereinafter sometimes referred to simply as "radiation-sensitive composition") will be described.
-(A)著色劑-- (A) colorant -
在本發明的著色劑係色調沒有特別地限定,按照所得之彩色濾光片的用途而適當選定,無論是顔料、染料或是天然色素那一者均可。由於彩色濾光片要求耐熱性,所以作為本發明的著色劑係較佳為有機顔料或是無機顔料。The color tone of the coloring agent of the present invention is not particularly limited, and may be appropriately selected depending on the use of the obtained color filter, regardless of whether it is a pigment, a dye or a natural pigment. Since the color filter requires heat resistance, the coloring agent of the present invention is preferably an organic pigment or an inorganic pigment.
前述有機顔料,可舉出例如在色指數(C.I.;The Society of Dyers and Colourists公司發行)中分類為顏料之化合物,具體而言,可舉出如下述的附上色指數(C.I.)名者。The organic pigment is, for example, a compound classified as a pigment in a color index (C.I.; issued by The Society of Dyers and Colourists), and specific examples thereof include the following color index (C.I.).
C.I.顏料黃12、C.I.顏料黃13、C.I.顏料黃14、C.I.顏料黃17、C.I.顏料黃20、C.I.顏料黃24、C.I.顏料黃31、C.I.顏料黃55、C.I.顏料黃83、C.I.顏料黃93、C.I.顏料黃109、C.I.顏料黃110、C.I.顏料黃138、C.I.顏料黃139、C.I.顏料黃150、C.I.顏料黃153、C.I.顏料黃154、C.I.顏料黃155、C.I.顏料黃166、C.I.顏料黃168、C.I.顏料黃180、C.I.顏料黃211;C.I.顏料橙5、C.I.顏料橙13、C.I.顏料橙14、C.I.顏料橙24、C.I.顏料橙34、C.I.顏料橙36、C.I.顏料橙38、C.I.顏料橙40、C.I.顏料橙43、C.I.顏料橙46、C.I.顏料橙49、C.I.顏料橙61、C.I.顏料橙64、C.I.顏料橙68、C.I.顏料橙70、C.I.顏料橙71、C.I.顏料橙72、C.I.顏料橙73、C.I.顏料橙74;C.I.顏料紅1、C.I.顏料紅2、C.I.顏料紅5、C.I.顏料紅17、C.I.顏料紅31、C.I.顏料紅32、C.I.顏料紅41、C.I.顏料紅122、C.I.顏料紅123、C.I.顏料紅144、C.I.顏料紅149、C.I.顏料紅166、C.I.顏料紅168、C.I.顏料紅170、C.I.顏料紅171、C.I.顏料紅175、C.I.顏料紅176、C.I.顏料紅177、C.I.顏料紅178、C.I.顏料紅179、C.I.顏料紅180、C.I.顏料紅185、C.I.顏料紅187、C.I.顏料紅202、C.I.顏料紅206、C.I.顏料紅207、C.I.顏料紅209、C.I.顏料紅214、C.I.顏料紅220、C.I.顏料紅221、C.I.顏料紅224、C.I.顏料紅242、C.I.顏料紅243、C.I.顏料紅254、C.I.顏料紅255、C.I.顏料紅262、C.I.顏料紅264、C.I.顏料紅272;C.I.顏料紫1、C.I.顏料紫19、C.I.顏料紫23、C.I.顏料紫29、C.I.顏料紫32、C.I.顏料紫36、C.I.顏料紫38;C.I.顏料藍15、C.I.顏料藍15:3、C.I.顏料藍15:4、C.I.顏料藍15:6、C.I.顏料藍60、C.I.顏料藍80;C.I.顏料綠7、C.I.顏料綠36、C.I.顏料綠58;C.I.顏料棕23、C.I.顏料棕25;C.I.顏料黑1、C.I.顏料黑7。CI Pigment Yellow 12, CI Pigment Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 55, CI Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 109, CI Pigment Yellow 110, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 153, CI Pigment Yellow 154, CI Pigment Yellow 155, CI Pigment Yellow 166, CI Pigment Yellow 168, CI Pigment Yellow 180, CI Pigment Yellow 211; CI Pigment Orange 5, CI Pigment Orange 13, CI Pigment Orange 14, CI Pigment Orange 24, CI Pigment Orange 34, CI Pigment Orange 36, CI Pigment Orange 38, CI Pigment Orange 40, CI Pigment Orange 43, CI Pigment Orange 46, CI Pigment Orange 49, CI Pigment Orange 61, CI Pigment Orange 64, CI Pigment Orange 68, CI Pigment Orange 70, CI Pigment Orange 71, CI Pigment Orange 72, CI Pigment Orange 73, CI Pigment Orange 74; CI Pigment Red 1, CI Pigment Red 2, CI Pigment Red 5, CI Pigment Red 17, CI Pigment Red 31, CI Pigment Red 32, CI Pigment Red 41, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 170 CI Pigment Red 171, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 178, CI Pigment Red 179, CI Pigment Red 180, CI Pigment Red 185, CI Pigment Red 187, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207, CI Pigment Red 209, CI Pigment Red 214, CI Pigment Red 220, CI Pigment Red 221, CI Pigment Red 224, CI Pigment Red 242, CI Pigment Red 243, CI Pigment Red 254, CI pigment red 255, CI pigment red 262, CI pigment red 264, CI pigment red 272; CI pigment violet 1, CI pigment violet 19, CI pigment violet 23, CI pigment violet 29, CI pigment violet 32, CI pigment violet 36, CI Pigment Violet 38; CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, CI Pigment Blue 80; CI Pigment Green 7, CI Pigment Green 36 , CI Pigment Green 58; CI Pigment Brown 23, CI Pigment Brown 25; CI Pigment Black 1, CI Pigment Black 7.
在本發明中,有機顔料係亦可藉由再結晶法、再沈殿法、溶劑洗淨法、昇華法、真空加熱法、與此等的組合來進行精製而使用。In the present invention, the organic pigment may be purified by a combination of a recrystallization method, a re-sinking method, a solvent washing method, a sublimation method, a vacuum heating method, or the like.
另外,上述無機顔料,可舉出例如氧化鈦、硫酸鋇、碳酸鈣、氧化鋅、硫酸鉛、黃色鉛、鋅鉻、三氧化二鐵(紅色氧化鐵(III))、鉻紅、群青、普魯士藍、氧化鉻綠、鈷綠、琥珀、鈦黑、合成鐵黑、碳黑等。Further, examples of the inorganic pigment include titanium oxide, barium sulfate, calcium carbonate, zinc oxide, lead sulfate, yellow lead, zinc chromium, ferric oxide (red iron oxide (III)), chrome red, ultramarine blue, and Prussian. Blue, chrome oxide green, cobalt green, amber, titanium black, synthetic iron black, carbon black, and the like.
這些著色劑可根據要求的,亦可以樹脂改質其粒子表面而使用。These colorants can be used as needed, or the resin can be modified to the surface of the particles.
作為改質顔料的粒子表面之樹脂,可舉出例如特開2001-108817號公報中記載的媒液樹脂、與市售的各種顔料分散用的樹脂。關於碳黑表面的樹脂被覆方法,例如特開平9-71733號公報、特開平9-95625號公報、特開平9-124969號公報等中所揭示的。The resin of the surface of the particle of the modified pigment is, for example, a vehicle liquid resin described in JP-A-2001-108817, and a resin for dispersing various commercially available pigments. The resin coating method of the surface of the carbon black is disclosed in, for example, JP-A-H09-71733, JP-A-9-95625, JP-A-9-124969, and the like.
前述著色劑係可單獨或混合2種以上使用。These coloring agents can be used singly or in combination of two or more.
使用本發明的感放射線性組成物形成畫素之情形中,由於對畫素要求高精細的發色,所以作為(A)著色劑較佳係發色性高的著色劑,具體而言較佳係使用有機顔料。In the case of forming a pixel using the radiation sensitive composition of the present invention, since a high-definition coloring is required for a pixel, a coloring agent having a high coloring property as a coloring agent (A) is preferable. Organic pigments are used.
另一方面,使用本發明的感放射線性組成物形成黑色矩陣之情形中,由於黑色矩陣要求遮光性,所以做為(A)著色劑較佳係使用有機顔料或碳黑。On the other hand, in the case of forming a black matrix using the radiation sensitive composition of the present invention, since the black matrix requires light blocking properties, it is preferred to use an organic pigment or carbon black as the (A) colorant.
本發明的感放射線性組成物,著色劑的含量係在感放射線性組成物的總固體含量中,即使為30重量%以上之情形,亦可形成正錐形形狀且耐溶劑性也優異的畫素。另外,在本發明中,著色劑含量的上限係基於確保顯像性之觀點,在感放射線性組成物的總固體含量中,較佳係70重量%以下,特佳係60重量%以下。這裡,所謂的固體含量係後述的溶媒以外的成分。In the radiation-sensitive composition of the present invention, the content of the colorant is such that, even in the case of 30% by weight or more of the total solid content of the radiation sensitive composition, a positively tapered shape and excellent solvent resistance can be formed. Prime. Further, in the present invention, the upper limit of the colorant content is preferably 70% by weight or less, and particularly preferably 60% by weight or less, based on the total solid content of the radiation sensitive composition, from the viewpoint of ensuring developability. Here, the solid content is a component other than the solvent described later.
-(B)分散劑-- (B) Dispersant -
本發明的感放射線性組成物係含有具有己內酯構造的(B)分散劑及具有後述之己內酯構造的(D)多官能性單體之至少一者。藉此,即使低曝光量亦可形成正錐形形狀的畫素。The radiation sensitive composition of the present invention contains at least one of (B) a dispersing agent having a caprolactone structure and a (D) polyfunctional monomer having a caprolactone structure described later. Thereby, even a low exposure amount can form a pixel having a forward tapered shape.
具有己內酯構造之分散劑只要是在其分子內具有己內酯構造的話,沒有特別地限制,較佳係在主鏈或側鏈上具有聚己內酯鏈之高分子分散劑。此時,聚己內酯鏈的分子量係在提高所期望的效果之點而言,為100以上為佳,200以上為較佳,200~5,000為特佳。The dispersing agent having a caprolactone structure is not particularly limited as long as it has a caprolactone structure in its molecule, and is preferably a polymer dispersing agent having a polycaprolactone chain in a main chain or a side chain. In this case, the molecular weight of the polycaprolactone chain is preferably 100 or more, and more preferably 200 or more, and particularly preferably 200 to 5,000.
具有聚己內酯鏈之高分子分散劑,可舉出例如使聚(伸烷基亞胺)或聚(烯丙基胺)與聚ε-己內酯反應而成之接枝聚合物、具有聚己內酯鏈之(甲基)丙烯酸系單體的共聚物、具有聚己內酯鏈之磷酸酯、具有聚己內酯鏈之分枝胺基甲酸酯樹脂等。更具體而言,可舉出特開昭61-174939號公報、特開平9-169821號公報、特開2000-95827號公報、特開2000-95992號公報、特開2000-104005號公報、特開2007-231106號公報、特開2007-269873號公報等中記載的分散劑。The polymer dispersing agent having a polycaprolactone chain may, for example, be a graft polymer obtained by reacting poly(alkyleneimine) or poly(allylamine) with poly(ε-caprolactone). A copolymer of a (meth)acrylic monomer having a polycaprolactone chain, a phosphate having a polycaprolactone chain, a branched urethane resin having a polycaprolactone chain, or the like. More specifically, JP-A-61-174939, JP-A-H09-169821, JP-A-2000-95827, JP-A-2000-95992, JP-A-2000-104005, and The dispersing agent described in JP-A-2007-269873, and the like.
具有聚己內酯鏈之高分子分散劑亦可為商業上可取得的,可舉出例如AJISPER PB821(味之素Fine-Techno股份有限公司製)等。在本發明中,具有己內酯構造之分散劑係可單獨或混合2種以上使用。The polymer dispersing agent having a polycaprolactone chain is also commercially available, and examples thereof include AJISPER PB821 (manufactured by Ajinomoto Fine-Techno Co., Ltd.). In the present invention, the dispersing agent having a caprolactone structure may be used alone or in combination of two or more.
本發明的感放射線性組成物中,在使用具有己內酯構造之(D)多官能性單體、而不使用具有己內酯構造之分散劑的情形下,可使用不具有己內酯構造的陽離子系、陰離子系、非離子系與兩性等適宜的分散劑。這樣的分散劑係可舉出例如變性丙烯酸系共聚物、丙烯酸系共聚物、聚胺基甲酸酯、高分子共聚物的烷基銨鹽或磷酸酯鹽等。在本發明中,不具有己內酯構造的分散劑係可單獨或混合2種以上使用。In the radiation sensitive composition of the present invention, in the case of using the (D) polyfunctional monomer having a caprolactone structure without using a dispersing agent having a caprolactone structure, a caprolactone structure can be used. Suitable dispersing agents such as cationic, anionic, nonionic and amphoteric. Examples of such a dispersing agent include a denatured acrylic copolymer, an acrylic copolymer, a polyurethane, an alkylammonium salt or a phosphate salt of a polymer copolymer. In the present invention, the dispersing agent having no caprolactone structure may be used alone or in combination of two or more.
當然也可以同時併用具有己內酯構造的分散劑,以及不具有己內酯構造的這些分散劑。It is of course also possible to use together a dispersing agent having a caprolactone structure and a dispersing agent having no caprolactone structure.
在本發明中,分散劑的含量係相對於(A)著色劑100質量份,通常為0.5~100質量份,較佳為1~70質量份、更佳為10~50質量份。此時,分散劑的含量過多時,恐有損失顯像性等之虞。In the present invention, the content of the dispersant is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, more preferably 10 to 50 parts by mass, per 100 parts by mass of the (A) colorant. At this time, when the content of the dispersant is too large, there is a fear of loss of developability and the like.
另外,不使用具有己內酯構造之(D)多官能性單體而使用具有己內酯構造之分散劑的情形,基於提高所期望的效果之點而言,其含有比例在全分散劑中,較佳為25質量%以上、更佳為50質量%以上。Further, in the case where a dispersing agent having a caprolactone structure is used without using the (D) polyfunctional monomer having a caprolactone structure, the content is contained in the total dispersing agent based on the point of improving the desired effect. It is preferably 25% by mass or more, and more preferably 50% by mass or more.
在本發明,可同時併用分散劑以及分散助劑。分散助劑,可舉出例如顔料衍生物,具體而言,可舉出銅酞菁、二酮基吡咯並吡咯、喹啉黃的磺酸衍生物等。In the present invention, a dispersing agent and a dispersing aid can be used in combination. The dispersing aid may, for example, be a pigment derivative, and specific examples thereof include a copper phthalocyanine, a diketopyrrolopyrrole, and a sulfonic acid derivative of quinoline yellow.
-(C)鹼可溶性樹脂--(C) alkali soluble resin -
本發明的感放射線性組成物中所含有的(C)鹼可溶性樹脂,係對於在形成著色層之際的顯像處理步驟中所使用的鹼顯像液具有可溶性者即可,沒有特別地限制,通常係具有羧基、酚性羥基等的酸性官能基之聚合物。其中,尤以含有具有羧基之聚合物(有時稱為「羧基含有聚合物」)為佳,該聚合物係可舉出例如具有1個以上羧基之乙烯性不飽和單體(以下,有時稱為「不飽和單體(c1)」)與其他可共聚合的乙烯性不飽和單體(以下,有時稱為「不飽和單體(c2)」)的共聚物。The (C) alkali-soluble resin contained in the radiation-sensitive composition of the present invention is not particularly limited as long as it is soluble in the alkali developing solution used in the development processing step in forming the colored layer. It is usually a polymer having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group. In particular, a polymer having a carboxyl group (may be referred to as a "carboxy group-containing polymer") is preferable, and the polymer may, for example, be an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter, sometimes A copolymer of an "unsaturated monomer (c1)") and another copolymerizable ethylenically unsaturated monomer (hereinafter sometimes referred to as "unsaturated monomer (c2)").
前述不飽和單體(c1),可舉出例如(甲基)丙烯酸、馬來酸、馬來酸酐、琥珀酸單[2-(甲基)丙烯醯氧基乙基]、ω-羧基聚己內酯單(甲基)丙烯酸酯等。這些不飽和單體(c1)係可單獨或混合2種以上使用。The unsaturated monomer (c1) may, for example, be (meth)acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2-(methyl)acryloxyethyl), ω-carboxypoly Lactone mono(meth)acrylate and the like. These unsaturated monomers (c1) can be used individually or in mixture of 2 or more types.
在不飽和單體(c1)與不飽和單體(c2)的共聚物中,不飽和單體(c1)的共聚合比例係較佳為5~50質量%、更佳為10~40質量%。藉由以這樣的範圍共聚合不飽和單體(c1),可得到鹼顯像性優異之感放射線性組成物。In the copolymer of the unsaturated monomer (c1) and the unsaturated monomer (c2), the copolymerization ratio of the unsaturated monomer (c1) is preferably from 5 to 50% by mass, more preferably from 10 to 40% by mass. . By copolymerizing the unsaturated monomer (c1) in such a range, a radiation-sensitive composition excellent in alkali developability can be obtained.
另外,前述不飽和單體(c2),可舉出例如:如N-苯基馬來醯亞胺、N-環己基馬來醯亞胺的N-位置換馬來醯亞胺;如苯乙烯、α-甲基苯乙烯、p-羥基-α-甲基苯乙烯的芳香族乙烯系化合物;如(甲基)丙烯酸甲酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異酯、(甲基)丙烯酸三環[5.2.1.02,6]癸-8-基酯、單(甲基)丙烯酸甘油酯、(甲基)丙烯酸4-羥基苯酯、對基酚之環氧乙烷變性(甲基)丙烯酸酯的不飽和羧酸酯;如聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚矽氧烷的在聚合物分子鏈的末端具有單(甲基)丙烯醯基之大分子單體等。Further, the unsaturated monomer (c2) may, for example, be an N-position-substituted maleimide such as N-phenylmaleimide or N-cyclohexylmaleimide; for example, styrene, An aromatic vinyl compound of α-methylstyrene or p-hydroxy-α-methylstyrene; such as methyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethyl (meth)acrylate Hexyl hexyl ester, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylate Ester, tricyclo[5.1.02 2,6 ]non-8-yl ester, glycerol mono(meth)acrylate, 4-hydroxyphenyl (meth)acrylate, pair An unsaturated carboxylic acid ester of an ethylene oxide-modified (meth) acrylate of a phenol; for example, polystyrene, poly(methyl) methacrylate, poly(methyl) methacrylate, polyoxyalkylene A macromonomer having a mono(meth)acrylonitrile group at the end of the polymer molecular chain or the like.
這些不飽和單體(c2)係可單獨或混合2種以上使用。These unsaturated monomers (c2) can be used individually or in mixture of 2 or more types.
不飽和單體(c1)與不飽和單體(c2)的共聚物的具體例,可舉出例如特開平7-140654號公報、特開平10-31308號公報、特開平10-300922號公報、特開平11-174224號公報、特開平11-258415號公報、特開2000-56118號公報、特開2004-101728等中所揭示的共聚物。Specific examples of the copolymer of the unsaturated monomer (c1) and the unsaturated monomer (c2), for example, JP-A-7-140654, JP-A-10-31308, JP-A-10-300922, The copolymer disclosed in JP-A-H11-174224, JP-A-H11-258415, JP-A-2000-56118, JP-A-2004-101728, and the like.
另外,在本發明,亦可將例如在特開平5-19467號公報、特開平6-230212號公報、特開平7-207211號公報、特開平11-140144號公報、特開2008-181095號公報等中所揭示的在側鏈具有(甲基)丙烯醯基等的聚合性不飽和鍵之羧基含有聚合物,作為鹼可溶性樹脂使用。In addition, the present invention is also disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. The carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acrylonitrile group in the side chain disclosed in the above is used as an alkali-soluble resin.
在本發明的鹼可溶性樹脂以凝膠滲透層析法(GPC、溶出溶媒:四氫呋喃)所測定之聚苯乙烯換算重量平均分子量(以下,稱為「Mw」),通常係1,000~100,000、較佳係3,000~50,000。此時,Mw過小時,所得之被膜的殘膜率等會下降,又圖案形狀、耐熱性等會受損,另外電氣特性恐有惡化之虞,另一方面如果過大時,解像度會下降,又圖案形狀會受損,另外在藉由狹縫噴嘴方式之塗布時恐有乾燥異物變得容易產生之虞。The polystyrene-equivalent weight average molecular weight (hereinafter referred to as "Mw") measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) of the alkali-soluble resin of the present invention is usually 1,000 to 100,000, preferably 1,000 to 100,000. It is 3,000~50,000. In this case, when the Mw is too small, the residual film ratio of the obtained film may be lowered, the pattern shape, heat resistance, and the like may be impaired, and the electrical characteristics may be deteriorated. On the other hand, if the film size is too large, the resolution may be lowered. The shape of the pattern is impaired, and in the case of coating by the slit nozzle method, it is feared that drying of foreign matter is likely to occur.
另外,在本發明的鹼可溶性樹脂的Mw與利用凝膠滲透層析法(GPC、溶出溶媒:四氫呋喃)所測定之聚苯乙烯換算數量平均分子量(以下,稱為「Mn」)的比(Mw/Mn),較佳為1.0~5.0、更佳為1.0~3.0。In addition, the ratio of the Mw of the alkali-soluble resin of the present invention to the polystyrene-equivalent number average molecular weight (hereinafter referred to as "Mn") measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) (Mw) /Mn), preferably 1.0 to 5.0, more preferably 1.0 to 3.0.
在本發明的鹼可溶性樹脂可利用眾所周知的方法而製造,亦可藉由例如特開2003-222717號公報、特開2006-259680號公報、國際公開第07/029871號手冊等中所揭示的方法,控制其構造與Mw、Mw/Mn。The alkali-soluble resin of the present invention can be produced by a known method, and the method disclosed in, for example, JP-A-2003-222717, JP-A-2006-259680, and International Publication No. 07/029871. , control its structure and Mw, Mw / Mn.
在本發明中,鹼可溶性樹脂係可單獨或混合2種以上使用。In the present invention, the alkali-soluble resin may be used singly or in combination of two or more.
在本發明中,鹼可溶性樹脂的含量係相對於(A)著色劑100質量份,通常為10~1,000質量份、較佳為20~500質量份。此時,鹼可溶性樹脂的含量過少時,例如會有鹼顯像性下降,又在未曝光部的基板上或是遮光層上恐有殘渣或質地污染產生之虞,另一方面如果過大時,相對地由於顔料濃度下降,所以恐有難以達成做為薄膜目的之色濃度之虞。In the present invention, the content of the alkali-soluble resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. In this case, when the content of the alkali-soluble resin is too small, for example, the alkali developability is lowered, and the residue or the texture is contaminated on the substrate of the unexposed portion or the light-shielding layer, and if it is too large, In contrast, since the concentration of the pigment is lowered, it is difficult to achieve the color density as a film target.
-(D)多官能性單體--(D) Polyfunctional monomer -
在本發明的多官能性單體係具有2個以上的聚合性不飽和鍵之單體。本發明的感放射線性組成物係含有具有己內酯構造之分散劑及具有己內酯構造之多官能性單體中的至少一者,惟較佳係含有具有己內酯構造之多官能性單體。The monomer having two or more polymerizable unsaturated bonds in the polyfunctional single system of the present invention. The radiation sensitive composition of the present invention contains at least one of a dispersing agent having a caprolactone structure and a polyfunctional monomer having a caprolactone structure, and preferably containing a polyfunctionality having a caprolactone structure. monomer.
作為具有己內酯構造之多官能性單體只要其分子內具有己內酯構造即可,沒有特別地限制,可舉出例如:藉由將三羥甲基乙烷、二-三羥甲基乙烷、三羥甲基丙烷、二-三羥甲基丙烷、新戊四醇、二新戊四醇、三新戊四醇、甘油、雙甘油、三羥甲基三聚氰胺等的多元醇,與(甲基)丙烯酸及ε-己內酯進行酯化所得的ε-己內酯變性多官能(甲基)丙烯酸酯。其中,較佳係下述式(1)所表示的具有己內酯構造之多官能性單體。The polyfunctional monomer having a caprolactone structure is not particularly limited as long as it has a caprolactone structure in the molecule, and examples thereof include trimethylolethane and di-trimethylol. Polyols such as ethane, trimethylolpropane, di-trimethylolpropane, neopentyltetraol, dipentaerythritol, tripentenol, glycerin, diglycerin, trimethylol melamine, etc. The ε-caprolactone denatured poly(meth)acrylate obtained by esterification of (meth)acrylic acid and ε-caprolactone. Among them, a polyfunctional monomer having a caprolactone structure represented by the following formula (1) is preferred.
(式中,6個R係全部為下述式(2)所表示之基、或6個R之中的1~5個為下述式(2)所表示之基,剩餘的為下述式(3)所表示之基)(In the formula, all of the six R systems are groups represented by the following formula (2), or one to five of the six R groups are groups represented by the following formula (2), and the rest are as follows: (3) the base expressed)
(式中,R1表示氫原子或甲基,m表示1或2的數,「*」表示連結鍵)(wherein R 1 represents a hydrogen atom or a methyl group, m represents a number of 1 or 2, and "*" represents a linkage bond)
(式中,R1表示氫原子或甲基,「*」表示連結鍵)(wherein R 1 represents a hydrogen atom or a methyl group, and "*" represents a linkage bond)
像這樣的具有己內酯構造之多官能性單體係可舉出例如:由日本化藥(股)作為KAYARAD DPCA系列所市售的,DPCA-20(在上述式(1)~(3)中,m=1、式(2)所表示之基的數=2、R1全部為氫原子之化合物)、DPCA-30(同式中,m=1、式(2)所表示之基的數=3、R1全部為氫原子之化合物)、DPCA-60(同式中,m=1、式(2)所表示之基的數=6、R1全部為氫原子之化合物)、DPCA-120(同式中,m=2、式(2)所表示之基的數=6、R1全部為氫原子之化合物)等。Such a polyfunctional single system having a caprolactone structure as described above may, for example, be commercially available as a KAYARAD DPCA series from Nippon Chemical Co., Ltd., DPCA-20 (in the above formulas (1) to (3) In the formula, m = 1, the number of the group represented by the formula (2) = 2, the compound in which all of R 1 are a hydrogen atom), DPCA-30 (in the same formula, m = 1, the group represented by the formula (2) a number = 3, a compound in which all R 1 are a hydrogen atom), DPCA-60 (in the formula, m = 1, a number of groups represented by the formula (2) = 6, a compound in which all of R 1 are a hydrogen atom), DPCA -120 (in the same formula, m = 2, the number of the groups represented by the formula (2) = 6, the compound in which all of R 1 are a hydrogen atom), and the like.
在本發明中,具有己內酯構造之多官能性單體係可單獨或混合2種以上使用。In the present invention, the polyfunctional single system having a caprolactone structure may be used singly or in combination of two or more.
在本發明的感放射線性組成物中,使用具有己內酯構造之分散劑、而不使用具有己內酯構造之多官能性單體的情形中,可使用不具有己內酯構造的適宜的多官能性單體。另外,同時併用具有己內酯構造之多官能性單體、以及不具有己內酯構造之多官能性單體的話,從提高殘膜率之點而言為佳。像這樣的多官能性單體,可舉出例如:乙二醇、丙二醇等的伸烷基醇的二(甲基)丙烯酸酯類;聚乙二醇、聚丙二醇等的聚伸烷基醇的二(甲基)丙烯酸酯類;甘油、三羥甲基丙烷、新戊四醇、二新戊四醇等的3價以上的多元醇之聚(甲基)丙烯酸酯類、與此等之二羧酸變性物;聚酯、環氧樹脂、胺基甲酸酯樹脂、醇酸樹脂、聚矽氧樹脂、螺環樹脂等的寡(甲基)丙烯酸酯類;兩末端羥基聚-1,3-丁二烯、兩末端羥基聚異戊二烯等的兩末端羥基化聚合物的二(甲基)丙烯酸酯類;參[2-(甲基)丙烯醯氧基乙基]磷酸酯,或異三聚氰酸環氧乙烷變性三丙烯酸酯;具有胺基甲酸酯構造之聚(甲基)丙烯酸酯等。In the radiation sensitive composition of the present invention, in the case of using a dispersant having a caprolactone structure without using a polyfunctional monomer having a caprolactone structure, a suitable one having no caprolactone structure can be used. Polyfunctional monomer. Further, when a polyfunctional monomer having a caprolactone structure and a polyfunctional monomer having no caprolactone structure are used in combination, it is preferred from the viewpoint of increasing the residual film ratio. Examples of such a polyfunctional monomer include di(meth)acrylates of alkylene alcohols such as ethylene glycol and propylene glycol; and polyalkylene glycols such as polyethylene glycol and polypropylene glycol. Di(meth)acrylates; poly(meth)acrylates of trivalent or higher polyhydric alcohols such as glycerin, trimethylolpropane, neopentyl alcohol, and dipentaerythritol, and the like Carboxylic acid denatured; oligo(meth)acrylates of polyester, epoxy resin, urethane resin, alkyd resin, polyoxyxylene resin, spiro resin, etc.; a di(meth)acrylate of a two-terminal hydroxylated polymer of butadiene, a terminal hydroxyl group, a polyisoprene, or the like; a [2-(methyl)propenyloxyethyl]phosphate, or Isocyanuric acid ethylene oxide denatured triacrylate; poly(meth)acrylate having a urethane structure, and the like.
這些不具有己內酯構造之多官能性單體之中,較佳係3價以上的多元醇之聚(甲基)丙烯酸酯類與此等之二羧酸變性物、以及具有胺基甲酸酯構造之聚(甲基)丙烯酸酯。作為3價以上的多元醇之聚(甲基)丙烯酸酯類與此等之二羧酸變性物,從著色層的強度高、著色層的表面平滑性優良、且在未曝光部的基板上及遮光層上難以產生質地污染、膜殘留等之點而言,較佳為三羥甲基丙烷三丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、新戊四醇三丙烯酸酯、新戊四醇三甲基丙烯酸酯、新戊四醇四丙烯酸酯、新戊四醇四甲基丙烯酸酯、二新戊四醇五丙烯酸酯、二新戊四醇五甲基丙烯酸酯、二新戊四醇六丙烯酸酯、二新戊四醇六甲基丙烯酸酯、新戊四醇三丙烯酸酯與琥珀酸的單酯化物、新戊四醇三甲基丙烯酸酯與琥珀酸的單酯化物、二新戊四醇五丙烯酸酯與琥珀酸的單酯化物、二新戊四醇五甲基丙烯酸酯與琥珀酸的單酯化物,特佳係三羥甲基丙烷三丙烯酸酯、新戊四醇三丙烯酸酯、二新戊四醇五丙烯酸酯、二新戊四醇六丙烯酸酯、新戊四醇三丙烯酸酯與琥珀酸的單酯化物、二新戊四醇五丙烯酸酯與琥珀酸的單酯化物。 Among these polyfunctional monomers having no caprolactone structure, poly(meth)acrylates of polyvalent alcohols having a valence of three or more, and dicarboxylic acid denatured products thereof, and having an aminocarboxylic acid are preferred. Poly(meth)acrylate of ester structure. The poly(meth)acrylates of the trivalent or higher polyhydric alcohols and the dicarboxylic acid denatured materials have high strength from the colored layer, excellent surface smoothness of the colored layer, and on the substrate of the unexposed portion. In terms of difficulty in causing texture contamination, film residue, and the like on the light-shielding layer, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, and neopentyl are preferable. Alcohol trimethacrylate, neopentyl alcohol tetraacrylate, neopentyl alcohol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethyl acrylate, dipentaerythritol Hexaacrylate, dipentaerythritol hexamethacrylate, monoester of pentaerythritol triacrylate and succinic acid, monoester of pentaerythritol trimethacrylate and succinic acid, dipentane Monoester of tetraol pentaacrylate and succinic acid, monoester of dipentaerythritol pentamethyl acrylate and succinic acid, especially trimethylolpropane triacrylate, neopentyl alcohol triacrylate , dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate New pentaerythritol triacrylate succinic acid monoester, succinic pentaacrylate and pentaerythritol di new monoester.
在本發明中,不具有己內酯構造之多官能性單體係可單獨或混合2種以上使用。 In the present invention, the polyfunctional single system having no caprolactone structure may be used singly or in combination of two or more.
在本發明的多官能性單體的含量係相對於(C)鹼可溶性樹脂100質量份,通常為20~400質量份、較佳為50~300質量份。藉由使多官能性單體的含量在像這樣的範圍,可形成強度與表面平滑性、耐溶劑性優異的著色層,而且可得到鹼顯像性也優異的感放射線性組成物。The content of the polyfunctional monomer in the present invention is usually 20 to 400 parts by mass, preferably 50 to 300 parts by mass, per 100 parts by mass of the (C) alkali-soluble resin. By setting the content of the polyfunctional monomer in such a range, a coloring layer excellent in strength, surface smoothness, and solvent resistance can be formed, and a radiation-sensitive composition excellent in alkali developability can be obtained.
另外,不使用具有己內酯構造之分散劑、而使用具有己內酯構造之多官能性單體的情形中,基於提高所期望的效果之點而言,其含有比例較佳係在全多官能性單體中為10質量%以上。Further, in the case where a dispersing agent having a caprolactone structure is not used and a polyfunctional monomer having a caprolactone structure is used, the content ratio is preferably based on the point of improving the desired effect. The functional monomer is 10% by mass or more.
-(E)光聚合引發劑--(E) Photopolymerization Initiator -
在本發明的光聚合引發劑係可為藉由曝光可見光線、紫外線、遠紫外線、電子束、X射線等的放射線,起始前述(D)多官能性單體的聚合而產生活性來源的化合物。The photopolymerization initiator of the present invention may be a compound which initiates polymerization of the above (D) polyfunctional monomer by exposing radiation of visible light, ultraviolet light, far ultraviolet ray, electron beam, X-ray or the like to produce an active source. .
在本發明中,光聚合引發劑係含有2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮者。該光聚合引發劑係藉由與前述具有己內酯構造之分散劑及/或具有己內酯構造之多官能性重量體組合而含有的話,可形成正錐形形狀且耐溶劑性優異的畫素。基於提高著色層的耐溶劑性之點而言,其含有比例較佳係在全光聚合引發劑中為25%質量以上。In the present invention, the photopolymerization initiator contains 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Olostinophenyl)butan-1-one. When the photopolymerization initiator is contained in combination with the above-described dispersant having a caprolactone structure and/or a polyfunctional weight having a caprolactone structure, a film having a forward tapered shape and excellent solvent resistance can be formed. Prime. The content of the colored layer is preferably 25% by mass or more in the total photopolymerization initiator, in view of improving the solvent resistance of the colored layer.
在本發明,藉由同時併用2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮、以及由氧硫系化合物及O-醯基肟系化合物所構成群組所選出之至少1種的話,可分外令人吃驚地進一步提高所期望的效果。氧硫 系化合物,可舉出例如下述式(4)所表示的化合物。In the present invention, by simultaneously using 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Olefinophenyl)butan-1-one, and by oxygen When at least one selected from the group consisting of a compound and an O-mercapto lanthanide compound can be surprisingly further improved the desired effect. Oxygen and sulfur The compound represented by the following formula (4) is mentioned, for example.
(式中,R2~R5係表示相互獨立的氫原子、鹵素原子、碳數1~18的烷基或碳數1~18的烷氧基)。(In the formula, R 2 to R 5 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms).
上述式(4)中,作為R2及R4較佳為氫原子,作為R3及R5較佳為氫原子、鹵素原子或碳數1~12的烷基。再者,作為R3及R5較佳為其兩者為碳數1~6的烷基。In the above formula (4), R 2 and R 4 are preferably a hydrogen atom, and R 3 and R 5 are preferably a hydrogen atom, a halogen atom or an alkyl group having 1 to 12 carbon atoms. Further, R 3 and R 5 are preferably an alkyl group having 1 to 6 carbon atoms.
作為上述式(4)所示之氧硫系化合物的具體例,可舉出氧硫、2-甲基氧硫、2-異丙基氧硫、4-異丙基氧硫、2-十二烷基氧硫、2,4-二甲基氧硫、2,4-二乙基氧硫、2,4-二異丙基氧硫、2-氯氧硫等。As the oxygen sulfur represented by the above formula (4) Specific examples of the compound, oxygen sulphur 2-methyloxosulfur 2-isopropyloxysulfur 4-isopropyloxysulfur 2-dodecyloxysulfur 2,4-dimethyloxosulfur 2,4-diethyloxysulfide 2,4-diisopropyloxysulfide 2-chlorooxosulfur Wait.
這些氧硫系化合物之中,較佳為2,4-二甲基氧硫、2,4-二乙基氧硫、2,4-二異丙基氧硫,特佳為2,4-二乙基氧硫。These oxygen and sulfur Among the compounds, 2,4-dimethyloxysulfide is preferred. 2,4-diethyloxysulfide 2,4-diisopropyloxysulfide , especially good for 2,4-diethyl oxysulfide .
在本發明中,氧硫系化合物係可單獨或混合2種以上使用。In the present invention, oxygen sulfur The compound can be used singly or in combination of two or more.
基於更提高所期望的效果之點而言,2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮與氧硫 系化合物的配合質量比,較佳為1:1~20:1,更佳為2:1~15:1。Based on the point that the desired effect is further improved, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Olefinophenyl)butan-1-one and oxysulfide The compounding mass ratio of the compound is preferably 1:1 to 20:1, more preferably 2:1 to 15:1.
另外,O-醯基肟系化合物係只要是具有醯基肟構造(>C=N-O-CO-)之光聚合引發劑即可,沒有特別地限制,可舉出例如:國際公開第2002/100903號手冊、國際公開第2006/018973號手冊、國際公開第2008/078678號手冊等中記載的化合物。作為O-醯基肟系化合物的較佳具體例,可舉出1,2-辛二酮,1-[4-(苯硫基)苯基]-,2-(O-苯甲醯)、乙酮,1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-,1-(O-乙醯肟)、乙酮,1-{9-乙基-6-(2-甲基-4-四氫呋喃基甲氧基苯甲醯基)-9H-咔唑-3-基]-,1-(O-乙醯肟)、乙酮,1-[9-乙基-6-{2-甲基-4-(2,2-二甲基-1,3-二氧雜環戊基)甲氧基苯甲醯基}-9H-咔唑-3-基]-,1-(O-乙醯肟)。In addition, the O-mercapto fluorene-based compound is not particularly limited as long as it is a photopolymerization initiator having a fluorenyl fluorene structure (>C=NO-CO-), and for example, International Publication No. 2002/100903 The compound described in the manual, International Publication No. 2006/018973, and International Publication No. 2008/078678. Preferred examples of the O-mercapto lanthanide compound include 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzamide). ), ethyl ketone, 1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-, 1-(O-acetamidine), ethyl ketone, 1-{9-ethyl-6-(2-methyl-4-tetrahydrofurylmethoxybenzylidene)-9H-indazol-3-yl]-, 1-(O-acetyl), Ethylketone, 1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzylidene}- 9H-carbazol-3-yl]-, 1-(O-acetamidine).
在本發明中,O-醯基肟系化合物係可單獨或混合2種以上使用。In the present invention, the O-mercapto fluorene-based compound may be used alone or in combination of two or more.
基於更提高所期望的效果之點而言,2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮與O-醯基肟系化合物的配合質量比,較佳為1:1~20:1,更佳為1:1~10:1。Based on the point that the desired effect is further improved, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- The mass ratio of the complex of the phenylphenyl)butan-1-one to the O-indenyl quinone compound is preferably from 1:1 to 20:1, more preferably from 1:1 to 10:1.
在本發明,亦可進一步使用2-甲基-1-[4-(甲硫基)苯基]-2-啉代丙-1-酮、2-苄基-2-二甲基胺基-1-(4-啉代苯基)丁烷-1-酮等的2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮以外的苯乙酮系化合物;2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基-1,2’-聯二咪唑、2,2’-雙(2,4-二氯苯基)-4,4’,5,5’-四苯基-1,2’-聯二咪唑、2,2’-雙(2,4,6-三氯苯基)-4,4’,5,5’-四苯基-1,2’-聯二咪唑等的聯二咪唑系化合物;2,4,6-參(三氯甲基)-s-三、2-甲基-4,6-雙(三氯甲基)-s-三、2-[2-(5-甲基呋喃-2-基)乙烯基]-4,6-雙(三氯甲基)-s-三、2-[2-(呋喃-2-基)乙烯基]-4,6-雙(三氯甲基)-s-三、2-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-4,6-雙(三氯甲基)-s-三、2-[2-(3,4-二甲氧基苯基)乙烯基]-4,6-雙(三氯甲基)-s-三、2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-s-三、2-(4-乙氧基苯乙烯基)-4,6-雙(三氯甲基)-s-三、2-(4-n-丁氧基苯基)-4,6-雙(三氯甲基)-s-三等的三系化合物等的眾所周知的光聚合引發劑。In the present invention, 2-methyl-1-[4-(methylthio)phenyl]-2- can also be further used. Phenylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4- 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-) of phenylphenyl)butan-1-one An acetophenone compound other than phenyl phenyl) butan-1-one; 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2 '-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2' - bibiimidazole compounds such as bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole; 2,4,6 - ginseng (trichloromethyl)-s-three 2-methyl-4,6-bis(trichloromethyl)-s-three ,2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl)-s-three ,2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-s-three 2-[2-(4-Diethylamino-2-methylphenyl)vinyl]-4,6-bis(trichloromethyl)-s-three ,2-[2-(3,4-dimethoxyphenyl)vinyl]-4,6-bis(trichloromethyl)-s-three , 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-three , 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-three , 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-three Three A well-known photopolymerization initiator of a compound or the like.
另外,亦可併用4,4’-雙(二甲基胺基)二苯基酮、4,4’-雙(二乙基胺基)二苯基酮、4-二乙基胺基苯乙酮、4-二甲基胺基苯丙酮、4-二甲基胺基安息香酸乙酯、4-二甲基胺基安息香酸2-乙基己酯、2,5-雙(4-二乙基胺基亞苄基)環己酮、7-二乙基胺基-3-(4-二乙基胺基苯甲醯基)香豆素、4-(二乙基胺基)查耳酮等的眾所周知的增感劑。In addition, 4,4'-bis(dimethylamino)diphenyl ketone, 4,4'-bis(diethylamino)diphenyl ketone, 4-diethylamino phenyl ketone may also be used in combination. Ketone, 4-dimethylaminopropiophenone, ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethyl) Aminobenzylidene)cyclohexanone, 7-diethylamino-3-(4-diethylaminobenzimidyl)coumarin, 4-(diethylamino)chalcone Well known sensitizers.
在本發明中,光聚合引發劑的含量係相對於(D)多官能性單體100質量份,通常為0.01~120質量份,較佳為1~100質量份、更佳為1~70質量份。此時,光聚合引發劑的含量過少時,因曝光所引起的硬化恐有變得不夠充分之虞,另一方面變得過多時,會有著色層在顯像時變得容易自基板上脫落下來的傾向。In the present invention, the content of the photopolymerization initiator is usually 0.01 to 120 parts by mass, preferably 1 to 100 parts by mass, more preferably 1 to 70% by mass based on 100 parts by mass of the (D) polyfunctional monomer. Share. In this case, when the content of the photopolymerization initiator is too small, the curing due to exposure may become insufficient, and when the amount is too large, the colored layer may easily fall off from the substrate during development. The tendency to come down.
-添加劑--additive-
本發明的感放射線性組成物係含有上述(A)~(E)成分者,亦可按照需要更含有其他的添加劑。The radiation sensitive composition of the present invention contains the above components (A) to (E), and may further contain other additives as needed.
前述其他的添加劑,可舉出例如:玻璃、氧化鋁等的充填劑;聚乙烯醇、聚(氟代烷基丙烯酸酯)類等的高分子化合物;非離子系界面活性劑、陽離子系界面活性劑、陰離子系界面活性劑等的界面活性劑;乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基參(2-甲氧基乙氧基)矽烷、N-(2-胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、N-(2-胺基乙基)-3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-氫硫基丙基三甲氧基矽烷等的黏附促進劑;2,2-硫代雙(4-甲基-6-第三丁基酚)、2,6-二-第三丁基酚等的氧化防止劑;2-(3-第三丁基-5-甲基-2-羥基苯基)-5-氯苯并三唑、烷氧基二苯基酮類等的紫外線吸收劑;聚丙烯酸鈉等的凝集防止劑;丙二酸、己二酸、衣康酸、檸康酸、富馬酸、中康酸等的殘渣改善劑;琥珀酸單[2-(甲基)丙烯醯氧基乙基]、苯二甲酸單[2-(甲基)丙烯醯氧基乙基]、ω-羧基聚己內酯單(甲基)丙烯酸酯等的顯像性改善劑等。Examples of the other additives include a filler such as glass or alumina, a polymer compound such as polyvinyl alcohol or poly(fluoroalkyl acrylate), a nonionic surfactant, and a cationic interface activity. Surfactant, agent such as anionic surfactant; vinyl trimethoxy decane, vinyl triethoxy decane, vinyl ginseng (2-methoxyethoxy) decane, N-(2-amino group Ethyl)-3-aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxylate Decane, 3-glycidoxypropyltrimethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxy Decane, 3-chloropropylmethyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-hydrothiopropyltrimethoxydecane Adhesion promoters such as 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-di-t-butylphenol, etc.; 2-(3- Third butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, alkoxy Ultraviolet absorber such as diphenyl ketone; anti-aggregation inhibitor such as sodium polyacrylate; residue improver of malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, etc.; Acid mono [2-(methyl) propylene oxiranyl ethyl], phthalic acid mono [2-(methyl) propylene oxiranyl ethyl], ω-carboxy polycaprolactone mono (meth) acrylate Imaging improver, etc.
-溶媒-- solvent -
本發明的感放射線性組成物係以前述(A)~(E)成分作為必要成分,可按照需要含有前述添加劑成分,通常係配合溶媒調製成液狀組成物。The radiation sensitive composition of the present invention contains the components (A) to (E) as essential components, and may contain the above-mentioned additive component as necessary, and usually is prepared by mixing a solvent to prepare a liquid composition.
作為前述溶媒,只要能構成感放射線性組成物的(A)~(E)成分與分散或溶解添加劑成分,且不與這些成分反應,並具有適度的揮發性者即可,可適宜地選擇使用。The solvent may be appropriately selected as long as it can constitute the components (A) to (E) of the radiation sensitive composition and disperse or dissolve the additive component, and does not react with these components, and has moderate volatility. .
像這樣的溶媒,可舉出例如:乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單正丙基醚、乙二醇單正丁基醚、二甘醇單甲基醚、二甘醇單乙基醚、二甘醇單正丙基醚、二甘醇單正丁基醚、三乙二醇單甲基醚、三乙二醇單乙基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單正丙基醚、丙二醇單正丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二丙二醇單正丙基醚、二丙二醇單正丁基醚、三丙二醇單甲基醚、三丙二醇單乙基醚等的(聚)伸烷基醇單烷基醚類;乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、二甘醇單甲基醚乙酸酯、二甘醇單乙基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯等的(聚)伸烷基醇單烷基醚乙酸酯類;二甘醇二甲基醚、二甘醇甲基乙基醚、二甘醇二乙基醚、四氫呋喃等的其他醚類;甲基乙基酮、環己酮、2-庚酮、3-庚酮等的酮類;丙二醇二乙酸酯、1,3-丁二醇二乙酸酯、1,6-己二醇二乙酸酯等的二乙酸酯類;乳酸甲酯、乳酸乙酯等的乳酸烷基酯類;2-羥基-2-甲基丙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲基-3-甲氧基丁基丙酸酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸異丁酯、甲酸正戊酯、乙酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸正丙酯、丁酸異丙酯、丁酸正丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸正丙酯、乙醯乙醯基甲酯、乙醯乙醯基乙酯、2-羥丁酸乙酯等的其他酯類;甲苯、二甲苯等的芳香族烴類;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等的醯胺或內醯胺類等。Examples of such a solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, and diethylene glycol monomethyl. Ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl Ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl (poly)alkyl alcohol monoalkyl ethers such as ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate Ester, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 3-methoxybutyl B (poly)alkyl alcohol monoalkyl ether acetates such as esters, 3-methyl-3-methoxybutyl acetate, etc.; diethylene glycol dimethyl ether, diethylene glycol methyl ethyl Ether, diethylene glycol diethyl ether, tetrahydrogen Other ethers such as ketone; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone; propylene glycol diacetate, 1,3-butanediol diacetate, 1 , diacetate such as 6-hexanediol diacetate; alkyl lactate such as methyl lactate or ethyl lactate; ethyl 2-hydroxy-2-methylpropionate, 3-methoxy Methyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, 2-hydroxyl Methyl 3-methylbutanoate, 3-methyl-3-methoxybutylpropionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, N-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, acetone Other esters such as n-propyl acrylate, acetamethylene methyl ester, ethyl acetonitrile ethyl ester, ethyl 2-hydroxybutyrate; aromatic hydrocarbons such as toluene and xylene; N, N-di A guanamine or an indoleamine such as methylformamide, N,N-dimethylacetamide or N-methylpyrrolidone.
這些溶媒之中,基於溶解性、顔料分散性、塗布性等之觀點而言,較佳為丙二醇單甲基醚、乙二醇單甲基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、3-甲氧基丁基乙酸酯、二甘醇二甲基醚、二甘醇甲基乙基醚、環己酮、2-庚酮、3-庚酮、丙二醇二乙酸酯、1,3-丁二醇二乙酸酯、乳酸乙酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲基-3-甲氧基丁基丙酸酯、乙酸正丁酯、乙酸異丁酯、甲酸正戊酯、乙酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸異丙酯、丁酸正丁酯、丙酮酸乙酯等。Among these solvents, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and the like are preferred from the viewpoints of solubility, pigment dispersibility, and coatability. Propylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone , propylene glycol diacetate, 1,3-butanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropionic acid Ethyl ester, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, Isopropyl butyrate, n-butyl butyrate, ethyl pyruvate, and the like.
前述溶媒係可單獨或混合2種以上使用。These solvents may be used singly or in combination of two or more.
另外,亦可同時併用前述溶媒以及苄基乙基醚、二正己基醚、丙酮基丙酮、異佛爾酮、己酸、辛酸、1-辛醇、1-壬醇、苄基醇、乙酸苄酯、安息香酸乙酯、乙二酸二乙酯、馬來酸二乙酯、γ-丁內酯、碳酸乙烯酯、碳酸丙烯酯、乙二醇單苯基醚乙酸酯等的高沸點溶媒。In addition, the above solvent may be used together with benzyl ethyl ether, di-n-hexyl ether, acetone acetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate. High-boiling solvent of ester, benzoic acid ethyl ester, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol monophenyl ether acetate .
這些高沸點溶媒係可單獨或混合2種以上使用。These high-boiling solvent systems can be used alone or in combination of two or more.
溶媒的含量係沒有特別地限制,基於所得之感放射線性組成物的塗布性、保存安定性等的觀點而言,該組成物去除溶媒之各成分的合計濃度為5~50質量%之量為佳,特佳為10~40質量%之量。The content of the solvent is not particularly limited, and the total concentration of each component of the composition-removing solvent is 5 to 50% by mass based on the coating property and storage stability of the obtained radiation-sensitive composition. Good, especially good for 10~40% by mass.
其次,針對使用本發明的感放射線性組成物,形成本發明的彩色濾光片之方法進行說明。Next, a method of forming the color filter of the present invention using the radiation sensitive composition of the present invention will be described.
形成彩色濾光片之方法通常係含有至少下述(1)~(4)的步驟。The method of forming a color filter generally includes at least the following steps (1) to (4).
(1)在基板上形成本發明感放射線性組成物的塗膜之步驟。(1) A step of forming a coating film of the radiation sensitive composition of the present invention on a substrate.
(2)曝光前述塗膜的至少一部份之步驟。(2) a step of exposing at least a part of the aforementioned coating film.
(3)顯像曝光後的塗膜之步驟。(3) The step of coating the film after exposure.
(4)後烘焙顯像後的塗膜之步驟。(4) A step of post-baking the film after development.
以下,針對這些步驟依序進行說明。Hereinafter, these steps will be described in order.
-(1)步驟-- (1) Step -
首先,可按照需要,在基板的表面上,區劃形成畫素之部分的方式形成遮光層(黑色矩陣),且將例如含有紅色的(A)著色劑之本發明的感放射線性組成物當作液狀組成物塗布至基板上之後,藉由進行預烘焙以去除溶媒,而形成塗膜。First, a light shielding layer (black matrix) may be formed on the surface of the substrate by dividing a portion of the pixel as needed, and the radiation sensitive composition of the present invention containing, for example, a red (A) coloring agent may be regarded as After the liquid composition is applied onto the substrate, the coating film is formed by performing prebaking to remove the solvent.
在該步驟所使用的基板,除了例如玻璃、矽、聚碳酸酯、聚酯、芳香族聚醯胺、聚醯胺醯亞胺、聚醯亞胺、聚醚碸之外,還可舉例如環狀烯烴的開環聚合物與其氫添加物等。The substrate used in this step may be, for example, a ring, in addition to, for example, glass, ruthenium, polycarbonate, polyester, aromatic polyamine, polyamidimide, polyimine, or polyether oxime. A ring-opening polymer of an olefin and a hydrogen additive thereof.
另外,可根據所要求的,預先對這些基板實施矽烷偶合劑等之藥品處理、電漿處理、離子鍍敷、噴濺、氣相反應法、真空蒸鍍等適宜的前處理。Further, an appropriate pretreatment such as a drug treatment such as a decane coupling agent, a plasma treatment, an ion plating, a sputtering, a gas phase reaction method, or a vacuum vapor deposition may be performed on these substrates in advance.
在將液狀組成物塗布至基板之際,可採用使用回轉塗布法、流延塗布法、輥塗法、縫模塗布法之塗布法等適宜的塗布法,較佳係使用回轉塗布法、縫模塗布法。When the liquid composition is applied to the substrate, an appropriate coating method such as a coating method using a spin coating method, a cast coating method, a roll coating method, or a slit die coating method may be employed, and a spin coating method or a slit is preferably used. Mold coating method.
預烘焙通常係組合減壓乾燥與加熱乾燥而進行的。減壓乾燥通常係進行至到達50~200Pa為止。另外,加熱乾燥的條件通常在70~110℃中實施1~10分左右。Prebaking is usually carried out by combining vacuum drying and heat drying. Drying under reduced pressure is usually carried out until it reaches 50 to 200 Pa. In addition, the conditions of heat drying are usually carried out at about 70 to 110 ° C for about 1 to 10 minutes.
塗布厚度係為預烘焙後的膜厚,通常為1.0~10μm,較佳為1.0~8.0μm,特佳為1.0~6.0μm。The coating thickness is a film thickness after prebaking, and is usually 1.0 to 10 μm, preferably 1.0 to 8.0 μm, and particularly preferably 1.0 to 6.0 μm.
-(2)步驟-- (2) Step -
然後,曝光所形成之塗膜的至少一部份。此時,在曝光塗膜的一部份之際,通常係透過具有規定的圖案之光罩進行曝光。Then, at least a portion of the formed coating film is exposed. At this time, when a part of the coating film is exposed, exposure is usually performed through a photomask having a predetermined pattern.
使用曝光之放射線的光源,可舉出例如氙氣燈、鹵素燈、鎢絲燈、高壓水銀燈、超高壓水銀燈、金屬鹵化物水銀燈、中壓水銀燈、低壓水銀燈等的燈光源與氬離子雷射、YAG雷射、XeCl準分子雷射、氮雷射等的雷射光源等,較佳係波長在190~450nm範圍之放射線。Examples of the light source using the exposed radiation include a lamp source such as a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide mercury lamp, a medium pressure mercury lamp, a low pressure mercury lamp, and the argon ion laser, YAG. A laser source such as a laser, a XeCl excimer laser, or a nitrogen laser is preferably a radiation having a wavelength in the range of 190 to 450 nm.
放射線的曝光量通常為10~10,000J/m2。根據本發明的感放射線性組成物,即使以800J/m2以下的曝光量、進而即使以600J/m2以下的曝光量,亦可形成正錐形形狀且耐溶劑性也優異的畫素。另外,曝光量的下限,基於使用照度高的光源之情形的控制性之觀點而言,較佳為100J/m2以上。The exposure amount of the radiation is usually 10 to 10,000 J/m 2 . According to the radiation sensitive composition of the present invention, even if the exposure amount is 800 J/m 2 or less, and even if the exposure amount is 600 J/m 2 or less, a pixel having a forward tapered shape and excellent solvent resistance can be formed. Further, the lower limit of the exposure amount is preferably 100 J/m 2 or more from the viewpoint of controllability in the case of using a light source having a high illuminance.
-(3)步驟-- (3) Step -
然後,使用顯像液、較佳係使用鹼顯像液進行顯像,以溶解去除塗膜的未曝光部。Then, development is carried out using a developing solution, preferably using an alkali developing solution, to dissolve and remove the unexposed portion of the coating film.
前述鹼顯像液,較佳係例如碳酸鈉、氫氧化鈉、氫氧化鉀、氫氧化四甲基銨、膽鹼、1,8-二氮雜二環-[5.4.0]-7-十一碳烯、1,5-二氮雜二環-[4.3.0]-5-壬烯等的水溶液。The alkali imaging solution is preferably, for example, sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5.4.0]-7-ten An aqueous solution of monocarbene, 1,5-diazabicyclo-[4.3.0]-5-nonene or the like.
亦可於前述鹼顯像液中,適量添加例如甲醇、乙醇等的水溶性有機溶劑與界面活性劑等。A water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like may be added to the alkali developing solution in an appropriate amount.
作為顯像處理法,可應用淋浴顯像法、噴霧顯像法、浸塗(浸漬)顯像法、攪煉(液盛)顯像法等。As the development processing method, a shower development method, a spray development method, a dip coating (immersion) development method, a pulverization (liquid suspension) development method, or the like can be applied.
顯像條件係在常溫下10~300秒左右為佳。The development condition is preferably about 10 to 300 seconds at normal temperature.
-(4)步驟-- (4) Step -
然後,經由後烘焙顯像後的塗膜,可得到以規定的配列方式配置由感放射線性組成物的硬化物所構成之紅色畫素圖案而成之基板。Then, the substrate obtained by post-baking development can be obtained by disposing a red pixel pattern composed of a cured product of the radiation-sensitive composition in a predetermined arrangement.
後烘焙的條件係在180~280℃中10~60分左右為佳。The post-baking conditions are preferably about 10 to 60 minutes at 180 to 280 °C.
像這樣所形成之畫素的膜厚通常為0.5~5.0μm,較佳為1.0~3.0μm。The film thickness of the pixel formed as described above is usually 0.5 to 5.0 μm, preferably 1.0 to 3.0 μm.
再者,藉由使用含有綠色的(A)著色劑之綠色感放射線性組成物,並重複前述(1)~(4)步驟,在同一基板上形成綠色的畫素圖案,然後藉由使用含有藍色的(A)著色劑之藍色感放射線性組成物,並重複前述(1)~(4)步驟,在同一基板上形成藍色的畫素圖案,可藉以在基板上形成以規定的配列方式配置紅色、綠色及藍色三原色的畫素圖案而成的畫素陣列。但是,各色畫素圖案的形成順序可任意地選擇。Further, by using the green radiation-sensitive linear composition containing the green (A) colorant and repeating the above steps (1) to (4), a green pixel pattern is formed on the same substrate, and then by using Blue (A) colorant blue luminosity linear composition, and repeating the above steps (1) to (4), forming a blue pixel pattern on the same substrate, which can be formed on the substrate by a predetermined A pixel array in which the pixel patterns of the three primary colors of red, green, and blue are arranged in a matching manner. However, the order in which the respective color pixel patterns are formed can be arbitrarily selected.
黑色矩陣係可藉由使用含有黑色的(A)著色劑之黑色感放射線性組成物,並進行前述(1)~(4)步驟而形成。The black matrix can be formed by using the black radiation-sensitive linear composition containing black (A) colorant and performing the above steps (1) to (4).
本發明的彩色濾光片係具有由本發明的感放射線性組成物以上述的方式所形成之畫素及/或黑色矩陣者。The color filter of the present invention has a pixel and/or a black matrix formed by the radiation sensitive composition of the present invention in the above-described manner.
本發明的彩色液晶顯示元件係具備本發明的彩色濾光片者。The color liquid crystal display element of the present invention includes the color filter of the present invention.
在如上述般所形成之彩色濾光片上,按照需要形成保護膜之後,藉由噴濺透明導電膜而形成。作為透明導電膜,可舉出例如由氧化銦-氧化錫所構成之ITO膜、由氧化銦-氧化鋅所構成之IZO膜等。使用本發明的感放射線性組成物所形成之畫素圖案的剖面形狀由於為正錐形,所以透明電極沒有斷線。因此,可製作電氣特性方面優良之高品質的彩色液晶顯示元件。On the color filter formed as described above, a protective film is formed as needed, and then formed by sputtering a transparent conductive film. Examples of the transparent conductive film include an ITO film composed of indium oxide-tin oxide, an IZO film composed of indium oxide-zinc oxide, and the like. Since the cross-sectional shape of the pixel pattern formed using the radiation sensitive composition of the present invention is a forward taper, the transparent electrode is not broken. Therefore, it is possible to produce a high-quality color liquid crystal display element excellent in electrical characteristics.
另外,作為本發明的彩色液晶顯示元件的形態之一,可藉由使用本發明的著色感放射線性組成物,在薄膜電晶體基板陣列上,以如前述的方式形成畫素及/或黑色矩陣,可製作具有特別優異特性之彩色液晶顯示元件。Further, as one of the forms of the color liquid crystal display element of the present invention, a pixel and/or a black matrix can be formed on the thin film transistor substrate array in the foregoing manner by using the color sensation radiation composition of the present invention. It is possible to produce a color liquid crystal display element having particularly excellent characteristics.
以下,列舉實施例以更具體地說明本發明。但是,本發明係不受限於下述實施例者。Hereinafter, the present invention will be described more specifically by way of examples. However, the present invention is not limited to the following embodiments.
在具備溫度計、攪拌機、氮導入口及回流管之反應燒瓶內,進料12-羥基硬脂酸(純正化學製)10.0質量份及ε-己內酯(純正化學製)190質量份,在氮氣流下歷經4小時昇溫至160℃,且在160℃中加熱2小時之後,加熱至ε-己內酯的殘量成為1%以下為止。接著,冷卻至室溫。該反應液中所含有的聚酯係具有數量平均分子量為2580且酸價為21.0mg KOH/g的特性。In a reaction flask equipped with a thermometer, a stirrer, a nitrogen inlet, and a reflux tube, 10.0 parts by mass of 12-hydroxystearic acid (manufactured by Junsei Chemical Co., Ltd.) and 190 parts by mass of ε-caprolactone (manufactured by Pure Chemical Co., Ltd.) were fed in nitrogen. The mixture was heated to 160 ° C over 4 hours, and heated at 160 ° C for 2 hours, and then heated until the residual amount of ε-caprolactone became 1% or less. Then, it was cooled to room temperature. The polyester contained in the reaction liquid had a property of having a number average molecular weight of 2,580 and an acid value of 21.0 mg KOH/g.
接著,在反應燒瓶內,於160℃中攪拌由二甲苯114.6質量份與聚(烯丙基胺)10%水溶液(日東紡績(股)製「PAA-1LV」、數量平均分子量約3000)70質量份所構成之混合物,使用分離裝置蒸餾去除水的同時,一邊使二甲苯回流至反應溶液中(確認蒸餾去除水的50重量%者),一邊於其中加入使含有前述聚酯之反應液69.59質量份昇溫至160℃者,並在160℃中進行反應2小時。藉由如此,以得到含有在側鏈具有聚己內酯鏈之聚(烯丙基胺)分散劑的溶液(固體含量濃度=40.1%)。將該分散劑當作「分散劑(B-1)」。分散劑(B-1)係具有胺價為10.5mg KOH/g、酸價為19.8mg KOH/g的特性。Next, in the reaction flask, 114.6 parts by mass of xylene and a 10% aqueous solution of poly(allylamine) ("PAA-1LV" manufactured by Nitto Bose Co., Ltd., number average molecular weight of about 3000) 70 mass were stirred at 160 °C. The mixture of the components was subjected to distillation to remove water, and the xylene was refluxed to the reaction solution (it is confirmed that 50% by weight of the distilled water was removed), and 69.59 mass of the reaction liquid containing the polyester was added thereto. The temperature was raised to 160 ° C, and the reaction was carried out at 160 ° C for 2 hours. Thus, a solution containing a poly(allylamine) dispersant having a polycaprolactone chain in a side chain (solid content concentration = 40.1%) was obtained. This dispersant was referred to as "dispersant (B-1)". The dispersant (B-1) has a property that the amine value is 10.5 mg KOH/g and the acid value is 19.8 mg KOH/g.
(A)使用作為著色劑之C.I.顏料紅254(Ciba Specialty Chemicals公司製、商品名BK-CF)/C.I.顏料紅 177(Ciba Specialty Chemicals公司製、商品名A3B)/C.I.顏料黃150=40/40/20(重量比)混合物20質量份、作為分散劑之分散劑(B-1)5質量份(固體含量換算)、作為溶媒之固體含量濃度為25%的丙二醇單甲基醚乙酸酯,並藉由砂磨機進行處理,以調製顔料分散液(R1)。(A) CI Pigment Red 254 (manufactured by Ciba Specialty Chemicals Co., Ltd., trade name BK-CF) / CI Pigment Red 177 (manufactured by Ciba Specialty Chemicals Co., Ltd., trade name A3B) / CI Pigment Yellow 150 = 40/40 was used as a coloring agent. 20 parts by mass of the mixture of 20 parts by weight, 5 parts by mass of the dispersing agent (B-1) as a dispersing agent (in terms of solid content), and propylene glycol monomethyl ether acetate having a solid content of 25% as a solvent. It is treated by a sand mill to prepare a pigment dispersion (R1).
(A)使用作為著色劑之C.I.顏料綠36/C.I.顏料黃150=50/50(重量比)混合物20質量份、作為分散劑之分散劑(B-1)5質量份(固體含量換算)、作為溶媒之固體含量濃度為25%的丙二醇單甲基醚乙酸酯,並藉由砂磨機進行處理,以調製顔料分散液(G1)。(A) 20 parts by mass of a mixture of CI Pigment Green 36/CI Pigment Yellow 150=50/50 (weight ratio) as a coloring agent, 5 parts by mass of a dispersing agent (B-1) as a dispersing agent (converted in terms of solid content), As a solvent, the propylene glycol monomethyl ether acetate having a solid content concentration of 25% was treated by a sand mill to prepare a pigment dispersion liquid (G1).
除了使用不具有聚己內酯鏈之變性丙烯酸系共聚物Disperbyk-2000(BYK Chemie(BYK)公司製)作為分散劑以外,與調製例1同樣地調製顔料分散液(R2)。A pigment dispersion liquid (R2) was prepared in the same manner as in Preparation Example 1, except that a distorted acrylic copolymer Disperbyk-2000 (manufactured by BYK Chemie (BYK) Co., Ltd.) having no polycaprolactone chain was used as a dispersing agent.
除了使用含有53質量%的由環氧乙烷及環氧丙烷所衍生之共聚合單位之胺價14mg KOH/g、重量平均分子量24,000的胺基甲酸酯樹脂作為分散劑以外,與調製例2同樣地調製顔料分散液(G2)。The preparation example 2 was prepared except that a urethane resin having an amine price of 14 mg KOH/g and a weight average molecular weight of 24,000 containing 53% by mass of a copolymerization unit derived from ethylene oxide and propylene oxide was used as a dispersant. The pigment dispersion (G2) was prepared in the same manner.
在具備冷却管、攪拌機之燒瓶中,進料2,2’-偶氮雙異丁腈3質量份、丙二醇單甲基醚乙酸酯200質量份,緊接著進料甲基丙烯酸15質量份、甲基丙烯酸苄酯35質量份、乙烯合萘30質量份、甲基丙烯酸2-羥基乙酯10質量份、ω-羧基聚己內酯單丙烯酸酯10質量份、及2,4-二苯基-4-甲基-1-戊烯(鏈轉移劑)5質量份,並進行氮置換。然後緩慢地攪拌,使反應溶液的溫度上升至80℃,保持該溫度3小時進行聚合,以得到共聚物溶液。所得之樹脂係Mw=11,000、Mn=5,000、固體含量濃度=31.0%。將該共聚物當作「鹼可溶性樹脂(C-1)」。In a flask equipped with a cooling tube and a stirrer, 3 parts by mass of 2,2'-azobisisobutyronitrile and 200 parts by mass of propylene glycol monomethyl ether acetate were fed, followed by feeding 15 parts by mass of methacrylic acid. 35 parts by mass of benzyl methacrylate, 30 parts by mass of ethylene naphthalene, 10 parts by mass of 2-hydroxyethyl methacrylate, 10 parts by mass of ω-carboxypolycaprolactone monoacrylate, and 2,4-diphenyl group 5 parts by mass of 4-methyl-1-pentene (chain transfer agent) and nitrogen substitution. Then, the mixture was slowly stirred, the temperature of the reaction solution was raised to 80 ° C, and the temperature was maintained for 3 hours to carry out polymerization to obtain a copolymer solution. The obtained resin was Mw = 11,000, Mn = 5,000, and solid content concentration = 31.0%. This copolymer was referred to as "alkali-soluble resin (C-1)".
在具備冷却管、攪拌機之燒瓶中,進料環己酮800質量份,一邊將氮氣注入至燒瓶中、一邊加熱至100℃,在相同溫度下,歷經1小時滴下苯乙烯60質量份、甲基丙烯酸60質量份、甲基丙烯酸甲酯65質量份、甲基丙烯酸丁酯65質量份、及偶氮雙異丁腈10質量份的混合物,進而在100℃使其反應3小時之後,添加以環己酮50質量份使偶氮雙異丁腈2質量份溶解而成者,再在100℃中繼續反應1小時以得到共聚物溶液。冷卻至室溫後,取樣約2g的共聚物溶液且180℃中加熱乾燥20分鐘以測定不揮發分,在先前所合成之共聚物溶液中添加環己酮以使得不揮發分成為20%,以調製共聚物溶液。所得之樹脂係Mw=40,000、Mn=15,000。將該共聚物當作「鹼可溶性樹脂(C-2)」。In a flask equipped with a cooling tube or a stirrer, 800 parts by mass of cyclohexanone was fed, and while nitrogen gas was injected into the flask, the mixture was heated to 100 ° C, and 60 parts by mass of styrene and methyl group were dropped at the same temperature for 1 hour. 60 parts by mass of acrylic acid, 65 parts by mass of methyl methacrylate, 65 parts by mass of butyl methacrylate, and 10 parts by mass of azobisisobutyronitrile were further reacted at 100 ° C for 3 hours, and then added in a ring. 50 parts by mass of hexanone was dissolved in 2 parts by mass of azobisisobutyronitrile, and the reaction was further continued at 100 ° C for 1 hour to obtain a copolymer solution. After cooling to room temperature, about 2 g of the copolymer solution was sampled and dried by heating at 180 ° C for 20 minutes to determine a nonvolatile matter, and cyclohexanone was added to the previously synthesized copolymer solution so that the nonvolatile content became 20%. The copolymer solution was prepared. The obtained resin was Mw = 40,000 and Mn = 15,000. This copolymer was referred to as "alkali-soluble resin (C-2)".
混合顔料分散液(R1)100質量份、作為(C)鹼可溶性樹脂之鹼可溶性樹脂(C-1)10質量份(固體含量換算)、作為(D)多官能性單體之二新戊四醇六丙烯酸酯15質量份、作為(E)光聚合引發劑之2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮(Ciba Specialty Chemicals公司製、商品名IRGACURE 379)5質量份、及作為溶媒之固體含量濃度為25重量%的丙二醇單甲基醚乙酸酯,以調製液狀組成物(S-1)。100 parts by mass of the mixed pigment dispersion (R1), 10 parts by mass of the alkali-soluble resin (C-1) as the (C) alkali-soluble resin (in terms of solid content), and (D) polyfunctional monomer 15 parts by mass of the alcohol hexaacrylate, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-) as the (E) photopolymerization initiator 5 parts by mass of phenylol phenyl)butan-1-one (manufactured by Ciba Specialty Chemicals, trade name IRGACURE 379), and propylene glycol monomethyl ether acetate as a solvent having a solid content concentration of 25% by weight to prepare Liquid composition (S-1).
針對液狀組成物(S-1),按照下述的順序進行評價。將評價結果表示於表2。The liquid composition (S-1) was evaluated in the following order. The evaluation results are shown in Table 2.
使用旋轉塗布機,塗布液狀組成物(S-1)至玻璃基板的表面上之後,以90℃的加熱板進行預烘焙4分鐘,以形成膜厚2.0μm的塗膜。接著,使該基板冷卻至室溫之後,使用高壓水銀燈且透過光罩,並以400J/m2的曝光量,對基板上的塗膜進行曝光。然後,藉由對基板上的塗膜,以1.5kgf/cm2的顯像壓力(噴嘴徑1mm)吐出60秒鐘的23℃的0.04重量%氫氧化鉀水溶液,以進行淋浴顯像。接著,在220℃中進行後烘焙30分鐘,以在基板上形成90μm的條紋狀畫素圖案。The liquid composition (S-1) was applied onto the surface of the glass substrate using a spin coater, and then prebaked on a hot plate at 90 ° C for 4 minutes to form a coating film having a film thickness of 2.0 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to light at a thickness of 400 J/m 2 using a high-pressure mercury lamp and passing through a photomask. Then, a shower development was carried out by discharging a 0.04% by weight aqueous solution of 0.04% by weight of 23° C. at 23° C. for 60 seconds at a development pressure of 1.5 kgf/cm 2 (nozzle diameter: 1 mm) on the coating film on the substrate. Next, post-baking was performed at 220 ° C for 30 minutes to form a 90 μm striped pixel pattern on the substrate.
接著,利用掃瞄型電子顯微鏡觀察所得之畫素圖案的剖面形狀,測定圖1所示之錐形角。該錐形角為80度以上時,透明電極膜恐有斷線之虞。理想的錐形角為30~70度。Next, the cross-sectional shape of the obtained pixel pattern was observed by a scanning electron microscope, and the taper angle shown in Fig. 1 was measured. When the taper angle is 80 degrees or more, the transparent electrode film may be broken. The ideal taper angle is 30 to 70 degrees.
使用旋轉塗布機,塗布液狀組成物(S-1)至玻璃基板的表面上之後,以90℃的加熱板進行預烘焙2分鐘,以形成膜厚2.0μm的塗膜。接著,使該基板冷卻至室溫之後,使用高壓水銀燈且透過光罩,並以400J/m2的曝光量,對基板上的塗膜進行曝光。然後,藉由對基板上的塗膜,以1.5kgf/cm2的顯像壓力(噴嘴徑1mm)吐出60秒鐘的23℃的0.04重量%氫氧化鉀水溶液,以進行淋浴顯像。接著,在220℃中進行後烘焙30分鐘,以在基板上形成200×200μm的點陣圖案。The liquid composition (S-1) was applied onto the surface of the glass substrate using a spin coater, and then prebaked on a hot plate at 90 ° C for 2 minutes to form a coating film having a film thickness of 2.0 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to light at a thickness of 400 J/m 2 using a high-pressure mercury lamp and passing through a photomask. Then, a shower development was carried out by discharging a 0.04% by weight aqueous solution of 0.04% by weight of 23° C. at 23° C. for 60 seconds at a development pressure of 1.5 kgf/cm 2 (nozzle diameter: 1 mm) on the coating film on the substrate. Next, post-baking was performed at 220 ° C for 30 minutes to form a dot pattern of 200 × 200 μm on the substrate.
接著,使所得之基板浸漬於60℃的N-甲基吡咯啶酮30分鐘。其結果,於浸漬後點陣圖案保持且浸漬後的N-甲基吡咯啶酮完全沒有著色之情形評價為◎,於浸漬後雖然點陣圖案保持、但是浸漬後的N-甲基吡咯啶酮有若干著色之情形評價為○,於浸漬後觀察到自基板剝離的點陣圖案的同時,浸漬後的N-甲基吡咯啶酮有著色之情形評價為×。Next, the obtained substrate was immersed in N-methylpyrrolidone at 60 ° C for 30 minutes. As a result, after the immersion lattice pattern was maintained and the immersed N-methylpyrrolidone was not colored at all, it was evaluated as ◎, and after the immersion, although the dot pattern was maintained, the immersed N-methylpyrrolidone was obtained. In the case of some coloring, it was evaluated as ○, and the dot pattern which was peeled off from the substrate was observed after immersion, and the case where the immersed N-methylpyrrolidone was colored was evaluated as ×.
使用旋轉塗布機,塗布液狀組成物(S-1)至玻璃基板的表面上之後,以90℃的加熱板進行預烘焙4分鐘,以形成膜厚2.0μm的塗膜。接著,使該基板冷卻至室溫之後,使用高壓水銀燈且透過光罩,並以400J/m2的曝光量,對基板上的塗膜進行曝光。然後,藉由對基板上的塗膜,以1kgf/cm2的顯像壓力(噴嘴徑1mm)吐出60秒鐘的23℃的0.04重量%氫氧化鉀水溶液,以進行淋浴顯像。接著,在220℃中進行後烘焙30分鐘,以形成200×200μm的點陣圖案。The liquid composition (S-1) was applied onto the surface of the glass substrate using a spin coater, and then prebaked on a hot plate at 90 ° C for 4 minutes to form a coating film having a film thickness of 2.0 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to light at a thickness of 400 J/m 2 using a high-pressure mercury lamp and passing through a photomask. Then, by applying a coating solution on the substrate to a developing pressure of 1 kgf/cm 2 (nozzle diameter: 1 mm), a 0.04% by weight aqueous solution of 0.04% by weight of potassium hydroxide at 23° C. was discharged for 60 seconds to perform shower development. Next, post-baking was performed at 220 ° C for 30 minutes to form a dot pattern of 200 × 200 μm.
接著,藉由利用掃瞄型電子顯微鏡觀察所得之基板上的點陣圖案並測定膜厚,以算出殘膜率(後烘焙後的膜厚×100/1.3)。可以說殘膜率越高的話,感度越良好。Next, the dot pattern on the obtained substrate was observed by a scanning electron microscope, and the film thickness was measured to calculate the residual film ratio (film thickness after post-baking × 100 / 1.3). It can be said that the higher the residual film rate, the better the sensitivity.
除了使液狀組成物之各成分的種類及量如表1所表示的以外,與實施例1同樣地,以調製液狀組成物(S-2)~(S-22)。The liquid compositions (S-2) to (S-22) were prepared in the same manner as in Example 1 except that the types and amounts of the respective components of the liquid composition were as shown in Table 1.
接著,除了取代液狀組成物(S-1)而改使用各液狀組成物(S-2)~(S-22)以外,與實施例1同樣地進行評價。將結果表示於表2。Then, the evaluation was carried out in the same manner as in Example 1 except that each of the liquid compositions (S-2) to (S-22) was used instead of the liquid composition (S-1). The results are shown in Table 2.
表1中,各成分係如下所述。In Table 1, each component is as follows.
D-1:二新戊四醇六丙烯酸酯D-1: dipentaerythritol hexaacrylate
D-2:在上述式(1)~(3)中,m=1、式(2)所表示之基的數=6、R1全部為氫原子之化合物(商品名KAYARAD DPCA-60、日本化藥公司製)D-2: In the above formulas (1) to (3), m = 1, the number of groups represented by the formula (2) = 6, and all of R 1 are hydrogen atoms (trade name KAYARAD DPCA-60, Japan) Chemical company)
D-3:在上述式(1)~(3)中,m=2、式(2)所表示之基的數=6、R1全部為氫原子之化合物(商品名KAYARAD DPCA-120、日本化藥公司製)D-3: In the above formulas (1) to (3), m = 2, the number of groups represented by the formula (2) = 6, and R 1 is a compound of a hydrogen atom (trade name KAYARAD DPCA-120, Japan) Chemical company)
E-1:2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮(Ciba Specialty Chemicals公司製、商品名IRGACURE 379)E-1: 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Olefinophenyl)butan-1-one (manufactured by Ciba Specialty Chemicals, trade name IRGACURE 379)
E-2:2,4-二乙基氧硫 E-2: 2,4-diethyloxysulfide
E-3:4,4’-雙(二乙基胺基)二苯基酮E-3: 4,4'-bis(diethylamino)diphenyl ketone
E-4:2-苄基-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮(商品名IRGACURE 369、Ciba Specialty Chemicals公司製)E-4: 2-benzyl-2-(dimethylamino)-1-(4- Olefinophenyl)butan-1-one (trade name: IRGACURE 369, manufactured by Ciba Specialty Chemicals)
E-5:2-甲基-1-[4-(甲硫基)苯基]-2-啉代丙-1-酮(商品名IRGACURE 907、Ciba Specialty Chemicals公司製)E-5: 2-methyl-1-[4-(methylthio)phenyl]-2- Olostino-1-one (trade name: IRGACURE 907, manufactured by Ciba Specialty Chemicals)
E-6:乙酮,1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-,1-(O-乙醯肟)(商品名IRGACURE OXE02、Ciba Specialty Chemicals公司製)E-6: ethyl ketone, 1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-, 1-(O-acetyl) (product IRGACURE OXE02, manufactured by Ciba Specialty Chemicals)
E-7:1,2-辛二酮,1-[4-(苯硫基)-,2-(O-苯甲醯肟)(商品名IRGACURE OXE01、Ciba Specialty Chemicals公司製)E-7: 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzamide) (trade name: IRGACURE OXE01, manufactured by Ciba Specialty Chemicals Co., Ltd.)
根據表2,可明顯得知(B)分散劑及(D)多官能性單體的至少一者為具有己內酯構造之成分(顔料分散液為R1或G1、(D)成分為D-2或D-3)、且光聚合引發劑為含有2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-啉代苯基)丁烷-1-酮之(E-1)的本發明著色感放射線性組成物,其所形成之畫素圖案為正錐形形狀、具有優異的耐溶劑性,同時殘膜率高、感度良好。According to Table 2, it is apparent that at least one of the (B) dispersant and the (D) polyfunctional monomer is a component having a caprolactone structure (the pigment dispersion is R1 or G1, and the component (D) is D- 2 or D-3), and the photopolymerization initiator contains 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- a coloring sensitizing radioactive composition of the present invention (O-1) of phenylphenyl)butan-1-one, which has a specular pattern formed into a forward tapered shape, excellent solvent resistance, and a residual film The rate is high and the sensitivity is good.
另一方面,在無論(B)分散劑及(D)多官能性單體中的哪一者均不含有具有己內酯構造之成分的情形、或是光聚合引發劑不含有前述(E-1)之情形中,所形成之畫素形成倒錐形,或是耐溶劑性惡化。 On the other hand, in either case, the (B) dispersant and the (D) polyfunctional monomer do not contain a component having a caprolactone structure, or the photopolymerization initiator does not contain the above (E- In the case of 1), the formed pixels form an inverted cone or the solvent resistance is deteriorated.
1‧‧‧畫素圖案 1‧‧‧ pixel pattern
2‧‧‧錐形角 2‧‧‧ cone angle
3‧‧‧基板 3‧‧‧Substrate
圖1係表示畫素圖案的剖面形狀之模式圖。 Fig. 1 is a schematic view showing a sectional shape of a pixel pattern.
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CN103329044A (en) * | 2011-01-18 | 2013-09-25 | 株式会社Lg化学 | Photosensitive resin composition, and photosensitive material comprising same |
TW201303489A (en) * | 2011-04-19 | 2013-01-16 | Sumitomo Chemical Co | Photosensitive resin composition |
JP5900203B2 (en) * | 2011-09-21 | 2016-04-06 | Jsr株式会社 | Coloring composition, color filter and display element |
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