JP2010039060A

JP2010039060A - インクジェット法カラーフィルタ用着色硬化性樹脂組成物、カラーフィルタ、液晶表示装置および有機ｅｌディスプレイ

インクジェット法カラーフィルタ用着色硬化性樹脂組成物、カラーフィルタ、液晶表示装置および有機ｅｌディスプレイ Download PDF

Info

Publication number: JP2010039060A
Authority: JP; Japan
Prior art keywords: meth; acid; acrylate; resin composition; curable resin
Prior art date: 2008-08-01
Legal status : Withdrawn

Application number

JP2008199717A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010039060A5 (OSRAM

Inventor

Hiroshi Ishihara

啓石原

Yukiya Haraguchi

幸也原口

Current Assignee

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Corp

Priority date

2008-08-01

Filing date

2008-08-01

Publication date

2010-02-18

2008-08-01 Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp

2008-08-01 Priority to JP2008199717A priority Critical patent/JP2010039060A/ja

2010-02-18 Publication of JP2010039060A publication Critical patent/JP2010039060A/ja

2011-09-08 Publication of JP2010039060A5 publication Critical patent/JP2010039060A5/ja

Status Withdrawn legal-status Critical Current

Links

239000011342 resin composition Substances 0.000 title claims abstract description 104
239000004973 liquid crystal related substance Substances 0.000 title claims description 40
238000000034 method Methods 0.000 title abstract description 68
239000011347 resin Substances 0.000 claims abstract description 102
229920005989 resin Polymers 0.000 claims abstract description 102
239000000049 pigment Substances 0.000 claims abstract description 93
239000002253 acid Substances 0.000 claims abstract description 69
239000002270 dispersing agent Substances 0.000 claims abstract description 52
239000011230 binding agent Substances 0.000 claims abstract description 31
229920001400 block copolymer Polymers 0.000 claims abstract description 26
239000003960 organic solvent Substances 0.000 claims abstract description 24
125000003277 amino group Chemical group 0.000 claims abstract description 23
239000007787 solid Substances 0.000 claims abstract description 23
150000001412 amines Chemical class 0.000 claims abstract description 22
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 119
239000000178 monomer Substances 0.000 claims description 99
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 48
229920001577 copolymer Polymers 0.000 claims description 45
239000002904 solvent Substances 0.000 claims description 44
125000003700 epoxy group Chemical group 0.000 claims description 40
239000000758 substrate Substances 0.000 claims description 29
238000009835 boiling Methods 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 21
229920006243 acrylic copolymer Polymers 0.000 claims description 18
239000003505 polymerization initiator Substances 0.000 claims description 18
229920000642 polymer Polymers 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
150000008064 anhydrides Chemical class 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
150000007519 polyprotic acids Polymers 0.000 claims description 10
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
230000000379 polymerizing effect Effects 0.000 claims description 8
239000005977 Ethylene Substances 0.000 claims description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
238000003763 carbonization Methods 0.000 claims 1
239000011248 coating agent Substances 0.000 abstract description 35
238000000576 coating method Methods 0.000 abstract description 35
230000002829 reductive effect Effects 0.000 abstract description 12
230000007547 defect Effects 0.000 abstract description 9
239000004793 Polystyrene Substances 0.000 abstract description 7
229920002223 polystyrene Polymers 0.000 abstract description 7
230000009467 reduction Effects 0.000 abstract description 4
-1 acryl Chemical group 0.000 description 83
239000010408 film Substances 0.000 description 52
239000006185 dispersion Substances 0.000 description 40
239000000976 ink Substances 0.000 description 36
150000001875 compounds Chemical class 0.000 description 34
239000004094 surface-active agent Substances 0.000 description 29
125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 22
230000036961 partial effect Effects 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
239000000975 dye Substances 0.000 description 19
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238000009736 wetting Methods 0.000 description 18
238000001035 drying Methods 0.000 description 17
238000006116 polymerization reaction Methods 0.000 description 17
150000003458 sulfonic acid derivatives Chemical class 0.000 description 16
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LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 14
230000000694 effects Effects 0.000 description 13
229920001296 polysiloxane Polymers 0.000 description 13
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239000002585 base Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
239000010410 layer Substances 0.000 description 12
239000011159 matrix material Substances 0.000 description 12
238000012719 thermal polymerization Methods 0.000 description 12
VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 11
238000005227 gel permeation chromatography Methods 0.000 description 11
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
125000001931 aliphatic group Chemical group 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
238000003756 stirring Methods 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 9
210000002858 crystal cell Anatomy 0.000 description 9
229920001187 thermosetting polymer Polymers 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
150000002170 ethers Chemical class 0.000 description 8
239000003999 initiator Substances 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
230000008569 process Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
238000004448 titration Methods 0.000 description 8
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
238000007334 copolymerization reaction Methods 0.000 description 7
238000001723 curing Methods 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
230000000977 initiatory effect Effects 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
238000010550 living polymerization reaction Methods 0.000 description 7
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DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
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 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
239000002245 particle Substances 0.000 description 6
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
239000007870 radical polymerization initiator Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
230000001235 sensitizing effect Effects 0.000 description 6
238000003860 storage Methods 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 5
MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
239000003086 colorant Substances 0.000 description 5
238000004040 coloring Methods 0.000 description 5
230000000052 comparative effect Effects 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
230000007423 decrease Effects 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
150000002440 hydroxy compounds Chemical class 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
238000000879 optical micrograph Methods 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
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238000010926 purge Methods 0.000 description 5
125000006850 spacer group Chemical group 0.000 description 5
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
230000037303 wrinkles Effects 0.000 description 5
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 4
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
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
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125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 4
239000003822 epoxy resin Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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239000000463 material Substances 0.000 description 4
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VOTNBIJNPNEGJA-UHFFFAOYSA-N methyl 2-(2-methoxycarbonylprop-2-enoxymethyl)prop-2-enoate Chemical compound COC(=O)C(=C)COCC(=C)C(=O)OC VOTNBIJNPNEGJA-UHFFFAOYSA-N 0.000 description 4
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OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 3
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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