JP6640436B2

JP6640436B2 - ブロック共重合体、分散剤、着色組成物およびカラーフィルタ

ブロック共重合体、分散剤、着色組成物およびカラーフィルタ Download PDF

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Publication number: JP6640436B2
Authority: JP; Japan
Prior art keywords: group; meth; mass; acrylate; block
Prior art date: 2017-11-29
Legal status : Active

Application number

JP2019541203A

Other languages

English (en)

Japanese (ja)

Other versions

JPWO2019107020A1 (ja

Inventor

宏幸石飛

達彦清水

Current Assignee

Otsuka Chemical Co Ltd

Original Assignee

Otsuka Chemical Co Ltd

Priority date

2017-11-29

Filing date

2018-10-24

Publication date

2020-02-05

2018-10-24 Application filed by Otsuka Chemical Co Ltd filed Critical Otsuka Chemical Co Ltd

2020-01-16 Publication of JPWO2019107020A1 publication Critical patent/JPWO2019107020A1/ja

2020-02-05 Application granted granted Critical

2020-02-05 Publication of JP6640436B2 publication Critical patent/JP6640436B2/ja

Status Active legal-status Critical Current

2038-10-24 Anticipated expiration legal-status Critical

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238000004040 coloring Methods 0.000 title claims description 112
239000000203 mixture Substances 0.000 title claims description 107
229920001400 block copolymer Polymers 0.000 title claims description 100
239000002270 dispersing agent Substances 0.000 title claims description 57
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 198
-1 halogen anion Chemical class 0.000 claims description 151
239000000178 monomer Substances 0.000 claims description 101
125000000217 alkyl group Chemical group 0.000 claims description 84
229920002554 vinyl polymer Polymers 0.000 claims description 76
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 50
125000003118 aryl group Chemical group 0.000 claims description 45
229920005989 resin Polymers 0.000 claims description 41
239000011347 resin Substances 0.000 claims description 41
230000002378 acidificating effect Effects 0.000 claims description 33
239000011230 binding agent Substances 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
239000002612 dispersion medium Substances 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 18
125000006165 cyclic alkyl group Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
239000003086 colorant Substances 0.000 claims description 15
238000009826 distribution Methods 0.000 claims description 15
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
125000004122 cyclic group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 10
150000002500 ions Chemical class 0.000 claims description 10
229920001515 polyalkylene glycol Polymers 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
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125000001183 hydrocarbyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 description 61
238000000034 method Methods 0.000 description 51
239000000049 pigment Substances 0.000 description 47
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239000000243 solution Substances 0.000 description 39
239000000463 material Substances 0.000 description 34
238000006116 polymerization reaction Methods 0.000 description 27
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
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150000001875 compounds Chemical class 0.000 description 20
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239000003513 alkali Substances 0.000 description 18
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239000000975 dye Substances 0.000 description 17
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238000009835 boiling Methods 0.000 description 15
238000000576 coating method Methods 0.000 description 15
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239000003431 cross linking reagent Substances 0.000 description 12
150000002430 hydrocarbons Chemical group 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
229910052786 argon Inorganic materials 0.000 description 11
239000000523 sample Substances 0.000 description 11
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
238000010526 radical polymerization reaction Methods 0.000 description 10
239000000758 substrate Substances 0.000 description 10
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235000014113 dietary fatty acids Nutrition 0.000 description 9
JPIIVHIVGGOMMV-UHFFFAOYSA-N ditellurium Chemical compound [Te]=[Te] JPIIVHIVGGOMMV-UHFFFAOYSA-N 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
239000003999 initiator Substances 0.000 description 9
239000003505 polymerization initiator Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000011161 development Methods 0.000 description 8
229920005604 random copolymer Polymers 0.000 description 8
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
125000006615 aromatic heterocyclic group Chemical group 0.000 description 7
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
238000005956 quaternization reaction Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
239000004973 liquid crystal related substance Substances 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
230000000704 physical effect Effects 0.000 description 6
125000001453 quaternary ammonium group Chemical group 0.000 description 6
150000003512 tertiary amines Chemical group 0.000 description 6
238000004448 titration Methods 0.000 description 6
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
150000008065 acid anhydrides Chemical class 0.000 description 5
239000000654 additive Substances 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
239000002585 base Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
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 5
238000001035 drying Methods 0.000 description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
238000002156 mixing Methods 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
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238000003756 stirring Methods 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 5
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 5
YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 description 4
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
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125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
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239000011324 bead Substances 0.000 description 4
238000011088 calibration curve Methods 0.000 description 4
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238000005227 gel permeation chromatography Methods 0.000 description 4
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 4
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 4
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
239000003586 protic polar solvent Substances 0.000 description 4
239000001054 red pigment Substances 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
125000000542 sulfonic acid group Chemical group 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
238000012360 testing method Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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230000015572 biosynthetic process Effects 0.000 description 3
239000001055 blue pigment Substances 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
238000002485 combustion reaction Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229920000359 diblock copolymer Polymers 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000011521 glass Substances 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
239000001056 green pigment Substances 0.000 description 3
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238000006386 neutralization reaction Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
238000010926 purge Methods 0.000 description 3
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