JP4437651B2 - 感光性樹脂組成物及びそれを用いたカラーフィルター - Google Patents
感光性樹脂組成物及びそれを用いたカラーフィルター Download PDFInfo
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- JP4437651B2 JP4437651B2 JP2003304248A JP2003304248A JP4437651B2 JP 4437651 B2 JP4437651 B2 JP 4437651B2 JP 2003304248 A JP2003304248 A JP 2003304248A JP 2003304248 A JP2003304248 A JP 2003304248A JP 4437651 B2 JP4437651 B2 JP 4437651B2
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- 239000006229 carbon black Substances 0.000 description 3
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- 150000005215 alkyl ethers Chemical class 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- CNASVLXXMGAQGK-UHFFFAOYSA-N bis(3,5-dichloro-4-hydroxyphenyl)methanone Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C(=O)C1=CC(Cl)=C(O)C(Cl)=C1 CNASVLXXMGAQGK-UHFFFAOYSA-N 0.000 description 1
- JWAPUVVSOVJCJB-UHFFFAOYSA-N bis(4-hydroxy-3,5-dimethylphenyl)methanone Chemical compound CC1=C(O)C(C)=CC(C(=O)C=2C=C(C)C(O)=C(C)C=2)=C1 JWAPUVVSOVJCJB-UHFFFAOYSA-N 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Liquid Crystal (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
ここ数年、液晶テレビ、液晶モニター、カラー液晶携帯電話などあらゆる分野でカラー液晶表示装置が用いられてきた。カラーフィルターはカラー液晶表示装置の視認性を左右する重要な部材の一つであり、視認性の向上、すなわち、鮮明な画像を得るためには、カラーフィルターを構成する赤、緑、青などの画素を今まで以上に高色純度化、及び、ブラックマトリックスでは高遮光化を達成する必要があり、感光性樹脂組成物に着色剤を従来より多量に添加しなければならない。
このように、着色剤の含有割合が多く光硬化が困難なカラーフィルター用感光性樹脂組成物を低露光量でパターン寸法安定性、パターン密着性、パターンのエッジ形状のシャープ性が良好なパターンを広い現像マージンで得ることが求められており、そのためには感光性樹脂組成物の高感度化が不可欠である。
(A)ビスフェノール類から誘導される2個のグリシジルエーテル基を有するエポキシ化合物と(メタ)アクリル酸との反応物を更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有アルカリ可溶性樹脂化合物、
(B)少なくとも1個以上のエチレン性不飽和結合を有する光重合性モノマー、
(C)光重合開始剤、
(D)着色剤、
を必須成分として含むカラーフィルター用感光性樹脂組成物において、(A)成分と(B)成分との重量割合(A/B)が、20/80〜90/10であり、(A)成分と(B)成分の合計100重量部に対して(C)成分を2〜30重量部含有し、且つ、(C)成分の光重合開始剤として下記一般式(I)で表される化合物を含有することを特徴とするカラーフィルター用感光性樹脂組成物である。
R1は、フェニル基(炭素数1〜6のアルキル基、フェニル基若しくはハロゲン原子で置換されていてもよい)、炭素数1〜20のアルキル基(1個以上の水酸基で置換されていてもよく、アルキル鎖の中間に1個以上の酸素原子を有していてもよい)、炭素数5〜8のシクロアルキル基、炭素数2〜20のアルカノイル基又はベンゾイル基(炭素数が1〜6のアルキル基若しくはフェニル基で置換されてもよい)を示し;
R2は、炭素数2〜12のアルカノイル基(1以上のハロゲン原子若しくはシアノ基で置換されていてもよい)、その二重結合がカルボニル基と共役していない炭素数4〜6のアルケノイル基、ベンゾイル基(炭素数1〜6のアルキル基、ハロゲン原子若しくはシアノ基で置換されていてもよい)、炭素数2〜6のアルコキシカルボニル基又はフェノキシカルボニル基(1以上の炭素数1〜6のアルキル基若しくはハロゲン原子で置換されていてもよい)を示し;
R3、R4、R5、R6、R7、R8、R9及びR10は、相互に独立に、水素原子、ハロゲン原子、炭素数1〜12のアルキル基、シクロペンチル基、シクロヘキシル基、フェニル基、ベンジル基、ベンゾイル基、炭素数2〜12のアルカノイル基、炭素数2〜12のアルコキシカルボニル基(アルコキシル基の炭素数が2〜11の場合、主鎖炭素原子間に1以上の酸素原子を有してもよく、1以上の水酸基で置換されていてもよい)又はフェノキシカルボニル基を示す。
R11及びR12は、独立に水素原子、炭素数1〜5のアルキル基又はハロゲン原子を示し、
Xは、‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は不存在を示し、nは0〜10の整数である。
本発明のカラーフィルター用感光性樹脂組成物(以下、単に組成物ともいう)は、(A)〜(D)成分を必須成分として含有する。ここで、(B)成分及び(D)成分並びに必要に応じて加えられる溶剤やその他の成分については、特許文献1〜6等に記載されており、これらから選択して使用することができる。したがって、(A)及び(C)成分以外の成分については簡潔に説明し、(A)及び(C)成分について詳細に説明する。
また、ブラックマトリックスは、遮光感光性樹脂組成物を用い、前記画素アレイの場合と同様にして形成することができる。
(A)-2:Mw8800、酸価130のN−フェニルマレイミド/メタクリル酸/ベンジルメタク リレート共重合体のプロピレングリコールモノメチルエーテルアセテート溶液(樹脂固 形分濃度=37.9重量%)(N−フェニルマレイミド:メタクリル酸:ベンジルメタクリ レート=26:34:40mol%)
(A)-3:Mw160000、酸価95のN−フェニルマレイミド/メタクリル酸/ベンジルメタク リレート共重合体のプロピレングリコールモノメチルエーテルアセテート溶液(樹脂固 形分濃度=38.1重量%)(N−フェニルマレイミド:メタクリル酸:ベンジルメタクリ レート=36:25:39mol%)
(C)−2:p,p-ジエチルアミノベンゾフェノン
(C)−3:2-(4-メトキシスチリル)-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン
(C)−4:2‐ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1
(C)−5:2-メチル-1-[4-(メチルチオ)フェニル]-2-モノフォリノプロパン-1-オン
(C)−6:1,2-オクタンジオン,1-[4-(フェニルチオ)フェニル]-,2-(O-ベンゾイルオキシム)、(化学式:下記)
(D)−2:臭塩素化フタロシアニングリーン顔料(C.I.ピグメントグリーン36)濃度15 .1重量%、高分子分散剤濃度4.0重量%のプロピレングリコールモノメチルエーテルア セテート分散液(固形分19.1%)
(D)−3:ジケトピロロピロールレッド顔料( C.I.ピグメントレッド254)濃度15.0 重量%、高分子分散剤濃度5.3重量%のプロピレングリコールモノメチルエーテルアセ テート分散液(固形分18.3%)
(D)−4:ニッケルアゾイエロー顔料( C.I.ピグメントイエロー150)濃度13.3重量 %、高分子分散剤濃度4.4重量%のプロピレングリコールモノメチルエーテルアセテー ト分散液(固形分17.7%)
(D)−5:カーボンブラック濃度20重量%、高分子分散剤濃度5重量%のプロピレングリ コールモノメチルエーテルアセテート分散液(固形分25.0%)
(E)−2:乳酸エチル
(F):エポキシ樹脂(ジャパンエポキシレジン社製 商品名YX4000H)
(G):シランカップリング剤
(H):界面活性剤
実施例、比較例におけるパターン画素パターンの評価項目と方法は以下の通りである。
パターン線幅:測長顕微鏡((株)ニコン製 商品名XD-20)を用い、赤、緑、青色感光性樹脂組成物については、マスク幅100μm、黒色感光性樹脂組成物についてはマスク幅20μmに対して線太り率が±10%未満のときを○<良好>、それ以上のときを×<不良>と判定した。
パターン直線性:現像後の画素パターンを顕微鏡観察し、基板に対する剥離やパターンエッジ部分のギザツキが認められないものを○<良好>、認められるものを×<不良>と評価した。
塗膜表面粗度:現像、熱焼成後の塗膜の表面粗度(Ra)の値が、150Å未満を○<良好>、150Å以上を×<不良>と評価した。
パターン密着性:ピーリングテストで20μmパターンの剥がれが認められないものを○<良好>、認められるものを×<不良>と評価した。
(C)成分として、(C)-4を0.3重量部、及び、(C)-6を1.5重量部とした以外は、実施例1と同様の条件で画素パターンを形成して評価を行ったが、パターンにぎざつきが認められ、パターン直線性が不良(×)であった。
(A)成分を、(A)-2に変更した以外は、実施例3と同様の条件で画素パターンを製造して評価を行ったが、90秒現像で、線幅に10%以上の線細りが認められ、線幅判定は不良(×)であった。更に、パターン直線性、密着性判定も不良(×)であった。
(C)成分を、(C)-3を2.0重量部に変更した以外は、実施例4と同様の条件で画素パターンを製造して評価を行ったが、パターン直線性が不良(×)で、更に、(C)-3の不溶物と思われる異物が塗膜表面に点在した。
(A)成分の種類を(A)-2に変更した以外は、実施例5と同様の条件で画素パターンを製造して評価を行ったが、現像時間80秒で感度不足のためパターンが欠落したため不良とした。
(C)成分を、(C)−6を18重量部に変更した以外は、実施例5と同様の条件で画素パターンを製造して評価を行ったが、90秒現像で、線幅に10%以上の線細りが認められ、線幅判定は不良(×)であった。更に、パターン直線性も不良(×)であった。
(C)成分の添加量を0.1重量部にした以外は、実施例5と同様の条件で画素パターンを製造して評価を行ったが、50秒現像で、線幅に10%以上の線細りが認められ、線幅判定は不良(×)であった。更に、パターン直線性、密着性判定も不良(×)、表面粗度が250Åとなり、不良(×)であった。
(A)成分の種類を、(A)-3に変更した以外は、実施例8と同様の条件で画素パターンを製造して評価を行ったが、パターン直線性、密着性判定ともに不良(×)であった。
Claims (5)
- 下記(A)〜(D)成分、
(A)ビスフェノール類から誘導される2個のグリシジルエーテル基を有するエポキシ化合物と(メタ)アクリル酸との反応物を更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有アルカリ可溶性樹脂化合物、
(B)少なくとも1個以上のエチレン性不飽和結合を有する光重合性モノマー、
(C)光重合開始剤、
(D)着色剤(黒色色材を除く)、
を必須成分として含むカラーフィルター用感光性樹脂組成物において、(A)成分と(B)成分との重量割合(A)/(B)が、20/80〜90/10であり、(A)成分と(B)成分の合計100重量部に対して(C)成分を2〜30重量部含有し、且つ、(C)成分の光重合開始剤として下記一般式(I)で表される化合物を含有し、該カラーフィルター用感光性樹脂組成物がR、G、B用のインクであることを特徴とするカラーフィルター用感光性樹脂組成物。
R1は、フェニル基(炭素数1〜6のアルキル基、フェニル基若しくはハロゲン原子で置換されていてもよい)、炭素数1〜20のアルキル基(1個以上の水酸基で置換されていてもよく、アルキル鎖の中間に1個以上の酸素原子を有していてもよい)、炭素数5〜8のシクロアルキル基、炭素数2〜20のアルカノイル基又はベンゾイル基(炭素数が1〜6のアルキル基若しくはフェニル基で置換されてもよい)を示し;
R2は、炭素数2〜12のアルカノイル基(1以上のハロゲン原子若しくはシアノ基で置換されていてもよい)、その二重結合がカルボニル基と共役していない炭素数4〜6のアルケノイル基、ベンゾイル基(炭素数1〜6のアルキル基、ハロゲン原子若しくはシアノ基で置換されていてもよい)、炭素数2〜6のアルコキシカルボニル基又はフェノキシカルボニル基(1以上の炭素数1〜6のアルキル基若しくはハロゲン原子で置換されていてもよい)を示し;
R3、R4、R5、R6、R7、R8、R9及びR10は、相互に独立に、水素原子、ハロゲン原子、炭素数1〜12のアルキル基、シクロペンチル基、シクロヘキシル基、フェニル基、ベンジル基、ベンゾイル基、炭素数2〜12のアルカノイル基、炭素数2〜12のアルコキシカルボニル基(アルコキシル基を構成するアルキル基の炭素数が2以上の場合、アルキル基は1個以上の水酸基で置換されていてもよく、アルキル鎖の中間に1個以上の酸素原子を有していてもよい)又はフェノキシカルボニル基を示す。 - 請求項1〜3のいずれかに記載のカラーフィルター用感光性樹脂組成物を硬化させて形成したことを特徴とする塗膜。
- 請求項1〜3のいずれかに記載のカラーフィルター用感光性樹脂組成物を透明基板上に塗布、プリベークした後、紫外線露光装置による露光、アルカリ水溶液による現像、ポストベークして作製された画素を備えたことを特徴とするカラーフィルター。
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CN111095044B (zh) | 2017-09-25 | 2022-08-12 | 东丽株式会社 | 着色树脂组合物、着色膜、滤色器及液晶显示装置 |
US20220121113A1 (en) | 2019-01-23 | 2022-04-21 | Basf Se | Oxime ester photoinitiators having a special aroyl chromophore |
JP2023517304A (ja) | 2020-03-04 | 2023-04-25 | ベーアーエスエフ・エスエー | オキシムエステル光開始剤 |
CN113189842B (zh) * | 2020-12-20 | 2024-05-17 | 江苏穿越光电科技有限公司 | 一种彩色滤光片的制备方法 |
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JP3986406B2 (ja) | 2002-09-25 | 2007-10-03 | 株式会社ニデック | 非接触式眼圧計 |
TWI289577B (en) * | 2002-10-28 | 2007-11-11 | Mitsubishi Chem Corp | Photopolymerization composition and color filter using the same |
JP2005062494A (ja) | 2003-08-13 | 2005-03-10 | Fujifilm Arch Co Ltd | 光硬化性組成物及びそれを用いたカラーフィルタ |
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TWI351581B (en) | 2011-11-01 |
TWI447523B (zh) | 2014-08-01 |
JP2005077451A (ja) | 2005-03-24 |
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