KR102146622B1 - 블랙 칼럼 스페이서 형성용 감광성 수지 조성물, 블랙 칼럼 스페이서 및 화상 표시 장치 - Google Patents

블랙 칼럼 스페이서 형성용 감광성 수지 조성물, 블랙 칼럼 스페이서 및 화상 표시 장치 Download PDF

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Publication number: KR102146622B1
Authority: KR; South Korea
Prior art keywords: meth; resin; group; acrylate; black column
Prior art date: 2016-05-27

Application number

KR1020187036136A

Other languages

English (en)

Korean (ko)

Other versions

KR20190008555A (ko

Inventor

마사요시 야나기

야스아키 가와구치

다케히로 기노시타

츠카사 하라

히로키 구라모토

Original Assignee

쇼와 덴코 가부시키가이샤

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2016-05-27

Filing date

2017-05-18

Publication date

2020-08-20

2017-05-18 Application filed by 쇼와 덴코 가부시키가이샤 filed Critical 쇼와 덴코 가부시키가이샤

2019-01-24 Publication of KR20190008555A publication Critical patent/KR20190008555A/ko

2020-08-20 Application granted granted Critical

2020-08-20 Publication of KR102146622B1 publication Critical patent/KR102146622B1/ko

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125000006850 spacer group Chemical group 0.000 title claims abstract description 84
239000011342 resin composition Substances 0.000 title claims abstract description 58
239000011347 resin Substances 0.000 claims abstract description 169
229920005989 resin Polymers 0.000 claims abstract description 169
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 62
239000002904 solvent Substances 0.000 claims abstract description 59
239000003086 colorant Substances 0.000 claims abstract description 26
125000003118 aryl group Chemical group 0.000 claims abstract description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 115
238000000034 method Methods 0.000 claims description 34
239000000049 pigment Substances 0.000 claims description 23
239000003085 diluting agent Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000002723 alicyclic group Chemical group 0.000 claims description 12
150000007519 polyprotic acids Polymers 0.000 claims description 12
150000008065 acid anhydrides Chemical class 0.000 claims description 7
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
125000005577 anthracene group Chemical group 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000000524 functional group Chemical group 0.000 abstract description 18
239000000178 monomer Substances 0.000 description 70
-1 acryloyloxy group Chemical group 0.000 description 48
239000000243 solution Substances 0.000 description 47
230000015572 biosynthetic process Effects 0.000 description 33
239000000203 mixture Substances 0.000 description 32
238000003786 synthesis reaction Methods 0.000 description 32
239000002253 acid Substances 0.000 description 28
239000000758 substrate Substances 0.000 description 26
238000007334 copolymerization reaction Methods 0.000 description 24
125000003700 epoxy group Chemical group 0.000 description 21
239000003505 polymerization initiator Substances 0.000 description 21
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 21
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 20
238000011084 recovery Methods 0.000 description 19
238000011161 development Methods 0.000 description 18
239000002243 precursor Substances 0.000 description 18
238000002156 mixing Methods 0.000 description 17
238000000576 coating method Methods 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
150000001875 compounds Chemical class 0.000 description 12
239000002270 dispersing agent Substances 0.000 description 12
238000007259 addition reaction Methods 0.000 description 11
239000011248 coating agent Substances 0.000 description 11
239000007787 solid Substances 0.000 description 10
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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230000000052 comparative effect Effects 0.000 description 9
238000006116 polymerization reaction Methods 0.000 description 9
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
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238000006243 chemical reaction Methods 0.000 description 8
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239000003112 inhibitor Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
230000003287 optical effect Effects 0.000 description 8
239000004593 Epoxy Substances 0.000 description 7
238000011156 evaluation Methods 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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238000001723 curing Methods 0.000 description 6
238000002845 discoloration Methods 0.000 description 6
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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239000007864 aqueous solution Substances 0.000 description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
239000007809 chemical reaction catalyst Substances 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
230000000694 effects Effects 0.000 description 5
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229920000642 polymer Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 4
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
WLTSXAIICPDFKI-UHFFFAOYSA-N 3-dodecene Chemical compound CCCCCCCCC=CCC WLTSXAIICPDFKI-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
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239000006229 carbon black Substances 0.000 description 4
238000013329 compounding Methods 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000003951 lactams Chemical class 0.000 description 4
239000004973 liquid crystal related substance Substances 0.000 description 4
125000003566 oxetanyl group Chemical group 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
239000000376 reactant Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
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125000004122 cyclic group Chemical group 0.000 description 3
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238000004519 manufacturing process Methods 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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229920001223 polyethylene glycol Polymers 0.000 description 3
238000003825 pressing Methods 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 2
NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
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150000008064 anhydrides Chemical class 0.000 description 2
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AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
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238000006735 epoxidation reaction Methods 0.000 description 2
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238000009472 formulation Methods 0.000 description 2
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238000001879 gelation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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238000004811 liquid chromatography Methods 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- 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
- G02F1/1339—Gaskets; Spacers; Sealing of cells
- 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
- 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
- H01L51/50—

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Physics & Mathematics (AREA)
Chemical & Material Sciences (AREA)
General Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nonlinear Science (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Optics & Photonics (AREA)
Mathematical Physics (AREA)
Spectroscopy & Molecular Physics (AREA)
Materials For Photolithography (AREA)
Liquid Crystal (AREA)
Macromonomer-Based Addition Polymer (AREA)

KR1020187036136A 2016-05-27 2017-05-18 블랙 칼럼 스페이서 형성용 감광성 수지 조성물, 블랙 칼럼 스페이서 및 화상 표시 장치 KR102146622B1 (ko)

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