TWI606296B - 著色光敏樹脂組成物 - Google Patents
著色光敏樹脂組成物 Download PDFInfo
- Publication number
- TWI606296B TWI606296B TW104104802A TW104104802A TWI606296B TW I606296 B TWI606296 B TW I606296B TW 104104802 A TW104104802 A TW 104104802A TW 104104802 A TW104104802 A TW 104104802A TW I606296 B TWI606296 B TW I606296B
- Authority
- TW
- Taiwan
- Prior art keywords
- anhydride
- alkali
- soluble resin
- acid
- colored photosensitive
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 42
- 239000000049 pigment Substances 0.000 claims description 81
- 229920005989 resin Polymers 0.000 claims description 70
- 239000011347 resin Substances 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000003086 colorant Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- 229940014800 succinic anhydride Drugs 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 claims description 3
- HDFKMLFDDYWABF-UHFFFAOYSA-N 3-phenyloxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1=CC=CC=C1 HDFKMLFDDYWABF-UHFFFAOYSA-N 0.000 claims description 3
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 claims description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UYCICMIUKYEYEU-ZHACJKMWSA-N 3-[(e)-dodec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCC\C=C\CC1CC(=O)OC1=O UYCICMIUKYEYEU-ZHACJKMWSA-N 0.000 claims description 2
- HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- -1 o-vinyl phenyl Chemical group 0.000 description 51
- 239000000975 dye Substances 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000011161 development Methods 0.000 description 20
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- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000002253 acid Substances 0.000 description 17
- 239000002270 dispersing agent Substances 0.000 description 17
- 230000009477 glass transition Effects 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
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- 230000035945 sensitivity Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
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- 239000004094 surface-active agent Substances 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
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- 230000000052 comparative effect Effects 0.000 description 7
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- 238000004519 manufacturing process Methods 0.000 description 6
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- 238000002834 transmittance Methods 0.000 description 6
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- 239000006185 dispersion Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- WROUWQQRXUBECT-UHFFFAOYSA-M 2-ethylacrylate Chemical compound CCC(=C)C([O-])=O WROUWQQRXUBECT-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- 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 4
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- 239000001045 blue dye Substances 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 2
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- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
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- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nonlinear Science (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
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KR1020140030510A KR20150107491A (ko) | 2014-03-14 | 2014-03-14 | 착색 감광성 수지 조성물 |
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TW201539125A TW201539125A (zh) | 2015-10-16 |
TWI606296B true TWI606296B (zh) | 2017-11-21 |
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TW104104802A TWI606296B (zh) | 2014-03-14 | 2015-02-12 | 著色光敏樹脂組成物 |
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JP (1) | JP2015176152A (ja) |
KR (1) | KR20150107491A (ja) |
CN (1) | CN104914674B (ja) |
TW (1) | TWI606296B (ja) |
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WO2017110893A1 (ja) * | 2015-12-24 | 2017-06-29 | 三菱化学株式会社 | 感光性着色組成物、硬化物、着色スペーサー、画像表示装置 |
KR102529779B1 (ko) * | 2016-08-19 | 2023-05-08 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러 필터 및 이를 구비한 화상 표시 장치 |
TWI603149B (zh) * | 2016-10-28 | 2017-10-21 | 聯致科技股份有限公司 | 光聚合性樹脂及感光型樹脂組成物 |
KR102371945B1 (ko) * | 2017-11-03 | 2022-03-08 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러필터 및 화상표시장치 |
KR102349145B1 (ko) * | 2018-03-02 | 2022-01-10 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 사용하여 제조된 컬러필터, 및 상기 컬러필터를 포함하는 표시장치 |
KR102335614B1 (ko) * | 2018-03-21 | 2021-12-03 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 포함하는 컬러필터 및 화상표시장치 |
KR102420536B1 (ko) * | 2019-03-27 | 2022-07-13 | 주식회사 엘지화학 | 알칼리 가용성, 광경화성 및 열경화성을 갖는 공중합체, 이를 이용한 감광성 수지 조성물, 감광성 수지 필름, 및 컬러필터 |
KR102094372B1 (ko) * | 2019-04-23 | 2020-03-27 | 주식회사 신아티앤씨 | 알칼리 가용성 수지, 이를 포함하는 감광성 수지 조성물 및 컬러필터 |
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US8507569B2 (en) * | 2009-03-23 | 2013-08-13 | Basf Se | Photoresist compositions |
TWI444441B (zh) * | 2009-09-25 | 2014-07-11 | Toyo Ink Mfg Co | 著色組成物及彩色濾光片 |
JP5835014B2 (ja) * | 2011-03-31 | 2015-12-24 | Jsr株式会社 | 画素パターンの形成方法及びカラーフィルタの製造方法 |
JP5998546B2 (ja) * | 2012-03-13 | 2016-09-28 | 三菱化学株式会社 | カラーフィルタ用着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機el表示装置 |
KR20130135077A (ko) * | 2012-05-31 | 2013-12-10 | 주식회사 엘지화학 | 신규한 고분자 및 이를 포함하는 감광성 수지 조성물 |
JP6157193B2 (ja) * | 2013-04-22 | 2017-07-05 | 昭和電工株式会社 | (メタ)アクリレート系ポリマー、該ポリマーを含む組成物及びその用途 |
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- 2015-03-13 JP JP2015051441A patent/JP2015176152A/ja active Pending
- 2015-03-16 CN CN201510113092.9A patent/CN104914674B/zh active Active
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TW201539125A (zh) | 2015-10-16 |
CN104914674B (zh) | 2020-04-21 |
JP2015176152A (ja) | 2015-10-05 |
CN104914674A (zh) | 2015-09-16 |
KR20150107491A (ko) | 2015-09-23 |
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