TWI579271B - A color photosensitive resin composition, color filter and display device comprising the same - Google Patents
A color photosensitive resin composition, color filter and display device comprising the same Download PDFInfo
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- TWI579271B TWI579271B TW103128128A TW103128128A TWI579271B TW I579271 B TWI579271 B TW I579271B TW 103128128 A TW103128128 A TW 103128128A TW 103128128 A TW103128128 A TW 103128128A TW I579271 B TWI579271 B TW I579271B
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- Prior art keywords
- weight
- photosensitive resin
- resin composition
- colored photosensitive
- compound
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- 239000011342 resin composition Substances 0.000 title claims description 77
- 239000000049 pigment Substances 0.000 claims description 94
- -1 oxime ester compound Chemical class 0.000 claims description 86
- 239000003999 initiator Substances 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000002904 solvent Substances 0.000 claims description 51
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- 239000011347 resin Substances 0.000 claims description 43
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 38
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 22
- 238000002835 absorbance Methods 0.000 claims description 18
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- 239000002253 acid Substances 0.000 claims description 16
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- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
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- 239000012965 benzophenone Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
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- 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 14
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- 239000012299 nitrogen atmosphere Substances 0.000 description 4
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- HRMOLDWRTCFZRP-UHFFFAOYSA-L disodium 5-acetamido-3-[(4-acetamidophenyl)diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].OC1=C(C(=CC2=CC(=CC(=C12)NC(C)=O)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC=C(C=C1)NC(C)=O.[Na+] HRMOLDWRTCFZRP-UHFFFAOYSA-L 0.000 description 1
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
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- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
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- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- KRGGVEDZUSPSAC-UHFFFAOYSA-N oxetan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCO1 KRGGVEDZUSPSAC-UHFFFAOYSA-N 0.000 description 1
- AMUUFLNQHMIHRP-UHFFFAOYSA-N oxetan-3-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1 AMUUFLNQHMIHRP-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000001935 peptisation Methods 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000010452 phosphate Substances 0.000 description 1
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- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
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- 239000001508 potassium citrate Substances 0.000 description 1
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- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229960004599 sodium borate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- FJBHGWADYLMEJG-UHFFFAOYSA-M sodium;3-[[4-[[4-(diethylamino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC=1C=C(C=CC=1)S([O-])(=O)=O)=C(C=C1)C=CC1=[N+](CC)CC1=CC=CC(S([O-])(=O)=O)=C1 FJBHGWADYLMEJG-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 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
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920005992 thermoplastic resin Polymers 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
Description
本發明是關於著色感光性樹脂組合物、包含該著色感光性樹脂組合物的濾色器和顯示裝置。 The present invention relates to a colored photosensitive resin composition, a color filter including the colored photosensitive resin composition, and a display device.
濾色器由於廣泛用於攝像元件、液晶顯示裝置(LCD)等,其應用範圍正在急速擴大。用於彩色液晶顯示裝置或攝像元件等的濾色器通常通過旋塗,將包含相當於紅色、綠色以及藍色等各種顏色的顏料的著色感光性樹脂組合物均勻塗布在圖案形成為黑色矩陣的基板上之後,通過將加熱乾燥(以下,也稱為“預烘焙”)形成的塗膜進行曝光、顯影,並且根據需要進一步按照每種顏色反復進行加熱固化(以下,也稱為“後烘焙”)的操作,形成各種顏色的畫素而製造。此處,形成圖案的著色矩陣通常由黑色感光性樹脂組合物形成。 Color filters are widely used in imaging devices, liquid crystal display devices (LCDs), etc., and their applications are rapidly expanding. A color filter used for a color liquid crystal display device, an image pickup element, or the like is generally uniformly coated with a coloring photosensitive resin composition containing pigments of various colors such as red, green, and blue by spin coating to form a black matrix. After the substrate, the coating film formed by heat drying (hereinafter, also referred to as "prebaking") is exposed and developed, and further heat curing is repeated for each color as needed (hereinafter, also referred to as "post-baking"). The operation is made by forming pixels of various colors. Here, the patterned color matrix is usually formed of a black photosensitive resin composition.
這種著色感光性樹脂組合物大多使用包含顏料和黏合劑樹脂、光聚合性化合物以及光聚合引發劑的組合物。 A coloring resin composition containing a pigment and a binder resin, a photopolymerizable compound, and a photopolymerization initiator are often used.
最近,為了提高工程上的成品率,著色感光性樹脂組合物要求即使較少的曝光量也具有同等的靈敏度和黏附性 的著色感光性樹脂組合物。 Recently, in order to improve the yield on the engineering, the colored photosensitive resin composition requires the same sensitivity and adhesion even with a small amount of exposure. The colored photosensitive resin composition.
此外,最近著色感光性樹脂組合物的著色材料由於為了滿足高色純度和高亮度等性能要求而被微粒化。因此,使用其形成畫素時,形成於基底的著色層存在顯影時未除去的顯影殘渣的問題。為了解決其的現有技術通常是調節黏合劑樹脂的酸值和分子量或黏合劑樹脂與組合物的酸值的方法,但其應用範圍受限,酸值過高時,黏附性不夠,成為表面不良的原因,此外,甚至金屬氧化膜、矽氮化膜上殘留的殘渣也存在難以解決的限制。 Further, recently, the coloring material of the colored photosensitive resin composition is micronized in order to satisfy performance requirements such as high color purity and high brightness. Therefore, when a pixel is formed using the same, the coloring layer formed on the substrate has a problem of development residue which is not removed at the time of development. The prior art for solving the problem is generally a method for adjusting the acid value and molecular weight of the binder resin or the acid value of the binder resin and the composition, but the application range is limited, and when the acid value is too high, the adhesion is insufficient and the surface is poor. For this reason, in addition, even the residues remaining on the metal oxide film or the tantalum nitride film have limitations that are difficult to solve.
[專利文獻] [Patent Literature]
專利文獻1:韓國授權專利第10-1222390號說明書 Patent Document 1: Korean Patent No. 10-1222390
本發明的目的在於,藉由使用包含肟酯類化合物的光聚合引發劑和包含4-羥基-4-甲基-2-戊酮的溶劑來製造著色感光性樹脂組合物,從而製造貯存穩定性、靈敏度和黏附性優異的濾色器和顯示裝置。 An object of the present invention is to produce a storage stability by using a photopolymerization initiator containing an oxime ester compound and a solvent containing 4-hydroxy-4-methyl-2-pentanone to produce a colored photosensitive resin composition. Color filter and display device with excellent sensitivity and adhesion.
為了實現上述目的,提供一種著色感光性樹脂組合物,包含著色劑、鹼溶性樹脂、光聚合性化合物、光聚合引發劑和溶劑,其特徵在於,該光聚合引發劑包含以下化學式1的肟酯類化合物,該溶劑包含4-羥基-4-甲基-2-戊酮。 In order to achieve the above object, a coloring photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerization initiator comprises the oxime ester of the following Chemical Formula 1 is provided a compound of the type comprising 4-hydroxy-4-methyl-2-pentanone.
式中,R1為碳數1~8的烷基、OR3基、經鹵素基團取代的碳數6~10的芳基或經鹵素基團取代的碳數7~24的芳烷基,R2為碳數1~8的烷基、碳數6~10的芳基或碳數7~24的芳烷基,R3為碳數1~20的烷基或碳數1~20的烷氧基。 In the formula, R 1 is an alkyl group having 1 to 8 carbon atoms, an OR 3 group, an aryl group having 6 to 10 carbon atoms substituted by a halogen group, or an aralkyl group having 7 to 24 carbon atoms substituted by a halogen group. R 2 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 24 carbon atoms, and R 3 is an alkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms. Oxygen.
另外,本發明提供包含該著色感光性樹脂組合物的濾色器。 Further, the present invention provides a color filter comprising the colored photosensitive resin composition.
進而,本發明還提供包含該濾色器的顯示裝置。 Further, the present invention also provides a display device including the color filter.
本發明的著色感光性樹脂組合物藉由作為光聚合引發劑包含前述化學式1的肟酯類化合物且作為溶劑包含4-羥基-4-甲基-2-戊酮,能夠製造貯存穩定性、靈敏度和黏附性優異的濾色器。 The colored photosensitive resin composition of the present invention contains the oxime ester compound of the above Chemical Formula 1 as a photopolymerization initiator and contains 4-hydroxy-4-methyl-2-pentanone as a solvent, thereby enabling storage stability and sensitivity. And a color filter with excellent adhesion.
此外,該濾色器具有在顯影工序中難以發生圖案短路的優點,能夠提高濾色器的生產率。 Further, this color filter has an advantage that pattern short-circuiting is less likely to occur in the development process, and the productivity of the color filter can be improved.
以下對本發明進行更詳細說明。 The invention is described in more detail below.
本發明關於一種著色感光性樹脂組合物,包含著色劑、鹼溶性樹脂、光聚合性化合物、光聚合引發劑和溶劑,其特徵在於,前述光聚合引發劑包含以下化學式1的肟酯類化合物,前述溶劑包含4-羥基-4-甲基-2-戊酮。 The present invention relates to a coloring photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerization initiator contains an oxime ester compound of the following Chemical Formula 1, The aforementioned solvent contains 4-hydroxy-4-methyl-2-pentanone.
式中,R1為碳數1~8的烷基、OR3基、經鹵素基團取代的碳數6~10的芳基或經鹵素基團取代的碳數7~24的芳烷基,R2為碳數1~8的烷基、碳數6~10的芳基或碳數7~24的芳烷基,R3為碳數1~20的烷基或碳數1~20的烷氧基。 In the formula, R 1 is an alkyl group having 1 to 8 carbon atoms, an OR 3 group, an aryl group having 6 to 10 carbon atoms substituted by a halogen group, or an aralkyl group having 7 to 24 carbon atoms substituted by a halogen group. R 2 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 24 carbon atoms, and R 3 is an alkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms. Oxygen.
如果使用包含前述化學式1的光聚合引發劑,以0.01重量%以上的濃度包含前述光聚合引發劑的丙二醇甲醚乙酸酯溶液的吸光度在405nm處為0.5以上,用405nm的鐳射曝光器進行曝光而形成濾色器的圖案時,初始效率變高,即使不使用過多的光聚合引發劑,也能夠得到著色感光性樹脂組合物的高靈敏度和優異的可靠性。 When the photopolymerization initiator containing the above Chemical Formula 1 is used, the absorbance of the propylene glycol methyl ether acetate solution containing the photopolymerization initiator at a concentration of 0.01% by weight or more or more is 0.5 or more at 405 nm, and exposure is performed with a 405 nm laser exposure device. When the pattern of the color filter is formed, the initial efficiency is increased, and high sensitivity and excellent reliability of the colored photosensitive resin composition can be obtained without using too much photopolymerization initiator.
此外,藉由使用包含4-羥基-4-甲基-2-戊酮的溶劑,能夠增加前述光聚合引發劑的溶解度。 Further, by using a solvent containing 4-hydroxy-4-methyl-2-pentanone, the solubility of the aforementioned photopolymerization initiator can be increased.
用前述組合物製造的著色感光性樹脂組合物可發現高濃度和高透過率,分散穩定性好,隨時間變化的特性優異,可有效地用作形成構成濾色器的著色圖案的原料,著色感光性樹脂組合物根據需要可包含附加的添加劑。 The colored photosensitive resin composition produced by the above composition can be found to have high concentration and high transmittance, has good dispersion stability, and is excellent in characteristics over time, and can be effectively used as a raw material for forming a colored pattern constituting a color filter, and is colored. The photosensitive resin composition may contain an additional additive as needed.
以下,分別進行詳細說明本發明著色感光性樹脂組合物的各成分。 Hereinafter, each component of the colored photosensitive resin composition of the present invention will be described in detail.
(A)著色劑 (A) colorant
前述著色劑的特徵在於包含一種以上的顏料、一種以上的染料或它們的混合物。 The aforementioned colorants are characterized by comprising more than one pigment, more than one dye, or a mixture thereof.
(a1)顏料 (a1) pigment
前述顏料可以使用在該領域中通常使用的有機顏料或無機顏料。此外,必要時,該顏料可以進行樹脂處理、採用了引入酸性或鹼性基團的顏料衍生物等的表面處理、高分子化合物等接枝到顏料表面的接枝處理、硫酸微粒化法等進行的微粒化處理、或藉由有機溶劑或水等除去雜質的清洗處理、用離子交換法等除去離子性雜質的除去處理等。 As the aforementioned pigment, an organic pigment or an inorganic pigment which is generally used in the field can be used. Further, if necessary, the pigment may be subjected to a resin treatment, a surface treatment such as a pigment derivative in which an acidic or basic group is introduced, a graft treatment in which a polymer compound or the like is grafted onto a pigment surface, a sulfuric acid micronization method, or the like. The micronization treatment, the cleaning treatment for removing impurities by an organic solvent or water, or the removal treatment of removing ionic impurities by an ion exchange method or the like.
前述有機顏料可以使用在印刷墨、噴墨墨等中使用的各種顏料,具體而言,可列舉出水溶性偶氮顏料、不溶性偶氮顏料、酞菁顏料、喹吖啶酮顏料、異吲哚滿酮顏料、異二氫吲哚顏料、苝顏料、芘酮顏 料、二噁嗪顏料、蒽醌顏料、二蒽醌顏料、蒽嘧啶顏料、蒽垛蒽醌(anthanthrone)顏料、陰丹酮顏料、黃烷士酮顏料、皮蒽酮顏料及二酮吡咯并吡咯顏料等。 As the organic pigment, various pigments used in printing inks, inkjet inks, and the like can be used, and specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, and isoindoles. Ketone pigment, isoindoline pigment, anthraquinone pigment, anthrone Materials, dioxazine pigments, anthraquinone pigments, diterpene pigments, pyrimidine pigments, anthrone (thantithrone) pigments, indanthrone pigments, flavanone pigments, dermatanone pigments and diketopyrrolopyrrole Pigments, etc.
此外,作為前述無機顏料,可列舉出金屬氧化物、金屬配位元化合物等金屬化合物,具體而言,可列舉出鐵、鈷、鋁、鎘、鉛、銅、鈦、鎂、鉻、鋅、銻、炭黑、有機黑色顏料、鈦黑以及混合紅色、綠色和藍色而呈黑色的顏料等金屬的氧化物或複合金屬氧化物等。 In addition, examples of the inorganic pigment include metal compounds such as metal oxides and metal complex compounds, and specific examples thereof include iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, and zinc. An oxide of a metal such as ruthenium, carbon black, an organic black pigment, titanium black, or a mixture of red, green, and blue pigments, or a composite metal oxide.
尤其是,作為前述有機顏料及無機顏料,具體而言,可列舉出在顯色指數(The society of Dyers and Colourists出版)下分類為顏料的化合物,更具體而言,可列舉出如下面的顯色指數(C.I.)編號的顏料,但並不一定限定於此。 In particular, specific examples of the organic pigment and the inorganic pigment include compounds classified as pigments under the color rendering index (published by The Society of Dyers and Colourists), and more specifically, the following are exemplified. The color index (CI) number of pigments, but is not necessarily limited to this.
C.I.顏料黃13、20、24、31、53、83、86、93、94、109、110、117、125、137、138、139、147、148、150、153、154、166、173、180及185;C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65及71;C.I.顏料紅9、97、105、122、123、144、149、166、168、176、177、180、192、215、216、224、242、254、255及264;C.I.顏料紫14、19、23、29、32、33、36、37及38;C.I.顏料藍15(15:3、15:4、15:6等)、21、28、60、64及76;C.I.顏料綠7、10、15、25、36、47及58; C.I.顏料棕28;C.I.顏料黑1及7等顏料。 CI Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 And 185; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71; CI Pigment Red 9, 97, 105, 122, 123, 144, 149 , 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264; CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 21, 28, 60, 64 and 76; CI Pigment Green 7, 10, 15, 25, 36, 47 and 58; C.I. Pigment Brown 28; C.I. Pigment Black 1 and 7 and other pigments.
較佳地,使用從C.I.顏料黃138、139、150以及185、C.I.顏料橙38、C.I.顏料紅255、C.I.顏料紫23、C.I.顏料藍15:3、15:6、C.I.顏料綠7、36以及58組成的群組中選擇的一種以上。 Preferably, from CI Pigment Yellow 138, 139, 150 and 185, CI Pigment Orange 38, CI Pigment Red 255, CI Pigment Violet 23, CI Pigment Blue 15:3, 15:6, CI Pigment Green 7, 36 and One or more selected from the group consisting of 58.
前述顏料較佳使用其粒徑均勻分散的顏料分散液。作為用於使顏料的粒徑均勻分散的方法的一例,可列舉出含有顏料分散劑(a2)進行分散處理的方法等,根據所述方法,能夠得到顏料均勻分散於溶液中的狀態的顏料分散液。 The pigment is preferably a pigment dispersion liquid whose particle diameter is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment is a method in which a pigment dispersant (a2) is dispersed and treated, and according to the method, pigment dispersion in a state in which the pigment is uniformly dispersed in a solution can be obtained. liquid.
(a2)顏料分散劑 (a2) pigment dispersant
所述顏料分散劑是為了維持顏料的反絮凝以及穩定性而添加的,作為前述顏料分散劑的具體示例,可列舉出陽離子類、陰離子類、非離子類、兩性、聚酯類、聚胺類等表面活性劑等,這些顏料分散劑可以分別單獨使用或組合兩種以上進行使用。 The pigment dispersant is added to maintain deflocculation and stability of the pigment. Specific examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, and polyamine. These pigment dispersants may be used singly or in combination of two or more kinds, such as a surfactant.
前述陽離子類表面活性劑的具體示例可列舉出十八烷基胺鹽酸鹽和月桂基三甲基氯化銨等胺鹽或季銨鹽等。 Specific examples of the cationic surfactant include an amine salt such as octadecylamine hydrochloride and lauryl trimethylammonium chloride, or a quaternary ammonium salt.
前述陰離子類表面活性劑的具體示例可列舉出月桂醇硫酸酯鈉和油酸醇硫酸酯鈉等高級醇硫酸酯鹽類、月桂基硫酸鈉和月桂基硫酸銨等烷基硫酸鹽類、十二烷基苯磺酸鈉和十二烷基萘磺酸鈉等的烷基芳基磺酸鹽類等。 Specific examples of the anionic surfactant include higher alcohol sulfate salts such as sodium lauryl sulfate and sodium oleate sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, and twelve. An alkylarylsulfonate such as sodium alkylbenzenesulfonate or sodium dodecylnaphthalenesulfonate.
前述非離子類表面活性劑的具體示例可列舉出聚氧乙烯烷基 醚、聚氧乙烯芳基醚、聚氧乙烯烷基芳基醚、其他的聚氧乙烯衍生物、氧乙烯/氧丙烯嵌段共聚物、山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇脂肪酸酯、丙三醇脂肪酸酯、聚氧乙烯脂肪酸酯和聚氧乙烯烷基胺等。 Specific examples of the aforementioned nonionic surfactants include polyoxyethylene alkyl groups. Ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene/oxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitol Anhydride fatty acid ester, polyoxyethylene sorbitan fatty acid ester, glycerin fatty acid ester, polyoxyethylene fatty acid ester, and polyoxyethylene alkylamine.
其他,可列舉出聚氧乙烯烷基醚類、聚氧乙烯烷基苯醚類、聚乙二醇二酯類、山梨糖醇酐脂肪酸酯類、脂肪酸改質的聚酯類、例如叔胺改質的聚氨酯類、聚乙烯亞胺類等。 Other examples include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, for example, tertiary amines. Polyurethanes, polyethyleneimine, etc.
此外,前述顏料分散劑較佳包含丙烯酸酯類分散劑(以下,丙烯酸酯類分散劑),該丙烯酸酯類分散劑包含甲基丙烯酸丁酯(BMA)或甲基丙烯酸-N,N-二甲基氨基乙酯(DMAEMA)。前述丙烯酸酯類分散劑的市售品可列舉出DISPER BYK-2000、DISPER BYK-2001、DISPER BYK-2070或DISPER BYK-2150等,該丙烯酸酯類分散劑可以分別單獨或組合兩種以上使用。 Further, the pigment dispersant preferably contains an acrylate dispersant (hereinafter, an acrylate dispersant) containing butyl methacrylate (BMA) or methacrylic acid-N, N-dimethyl methacrylate Aminoethyl ester (DMAEMA). The commercially available product of the acrylate-based dispersant may, for example, be DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070 or DISPER BYK-2150, and the acrylate-based dispersant may be used alone or in combination of two or more.
前述顏料分散劑除了前述丙烯酸分散劑之外,也能夠使用其他樹脂類顏料分散劑。作為前述其他樹脂類顏料分散劑,可列舉出:公知的樹脂類顏料分散劑,特別是以聚氨酯、聚丙烯酸酯為代表的聚羧酸酯、不飽和聚醯胺、聚羧酸、聚羧酸的(部分)胺鹽、聚羧酸的銨鹽、聚羧酸的烷基胺鹽、聚矽氧烷、長鏈聚氨基醯胺磷酸鹽、羥基-含聚羧酸的酸酯以及它們的改質生成物、或由具有自由(free)羧基的聚酯與聚(低級亞烷基亞胺)的反應形成的醯胺或這些鹽那樣的油質的分散劑;(甲基)丙烯酸-苯乙烯共聚物、(甲基)丙烯酸-(甲基)丙 烯酸酯共聚物、苯乙烯-馬來酸共聚物、聚乙烯醇或聚乙烯吡咯烷酮那樣的水溶性樹脂或水溶性聚合物化合物;聚酯;改質聚丙烯酸酯;環氧乙烷/環氧丙烷的加成生成物及磷酸酯等。 In addition to the aforementioned acrylic dispersant, the above-mentioned pigment dispersant can also use other resin-based pigment dispersants. Examples of the other resin-based pigment dispersant include a known resin-based pigment dispersant, particularly a polycarboxylate represented by polyurethane or polyacrylate, an unsaturated polyamine, a polycarboxylic acid, and a polycarboxylic acid. (partial) amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polyoxyalkylene oxides, long chain polyaminoguanamine phosphates, hydroxyl-containing polycarboxylic acid esters, and their modifications a product, or a decylamine formed by the reaction of a polyester having a free carboxyl group with a poly(lower alkyleneimine) or an oily dispersant such as these salts; (meth)acrylic acid-styrene Copolymer, (meth)acrylic acid-(meth)acrylic acid Water-soluble resin or water-soluble polymer compound such as olefin copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; polyester; modified polyacrylate; ethylene oxide/epoxy An addition product of propane, a phosphate ester, or the like.
前述其他樹脂型顏料分散劑的市售品中,作為陽離子類樹脂分散劑,例如可列舉出:BYK(畢克)化學公司的商品名:DISPER BYK-160、DISPER BYK-161、DISPER BYK-162、DISPER BYK-163、DISPER BYK-164、DISPER BYK-166、DISPER BYK-171、DISPER BYK-182、DISPER BYK-184;BASF公司的商品名:EFKA-44、EFKA-46、EFKA-47、EFKA-48、EFKA-4010、EFKA-4050、EFKA-4055、EFKA-4020、EFKA-4015、EFKA-4060、EFKA-4300、EFKA-4330、EFKA-4400、EFKA-4406、EFKA-4510、EFKA-4800;Lubirzol公司的商品名:SOLSPERS-24000、SOLSPERS-32550、NBZ-4204/10;川研精細化學品公司的商品名:(HINOACT)T-6000、HINOACTT-7000、HINOACTT-8000;味之素公司的商品名: (AJISPUR)PB-821、AJISPURPB-822、AJISPURPB-823;共榮社化學公司的商品名:(FLORENE)DOPA-17HF、FLORENEDOPA-15BHF、FLORENEDOPA-33、FLORENEDOPA-44等。 In the commercially available product of the above-mentioned other resin-type pigment dispersant, examples of the cationic resin-dispersing agent include: BYK (Chemical Co., Ltd.): DISPER BYK-160, DISPER BYK-161, DISPER BYK-162 DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; trade names of BASF: EFKA-44, EFKA-46, EFKA-47, EFKA -48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800 Lubirzol's trade name: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Chuanyan Fine Chemicals Co., Ltd. (HINOACT) T-6000, HINOACTT-7000, HINOACTT-8000; Ajinomoto company's trade name: (AJISPUR) PB-821, AJISPURPB-822, AJISPURPB-823; Gongrongshe Chemical Company's trade name: (FLORENE) DOPA-17HF, FLORENEDOPA-15BHF, FLORENEDOPA-33, FLORENEDOPA-44, etc.
除了前述丙烯酸酯類分散劑之外,其他樹脂類顏料分散劑也能夠分別單獨使用或組合兩種以上進行使用,也能夠與丙烯酸酯類分散劑同時使用。 In addition to the acrylate-based dispersant, other resin-based pigment dispersants may be used singly or in combination of two or more kinds, or may be used together with an acrylate-based dispersant.
前述顏料分散劑相對於顏料中的固體成分100重量份在5~60重量份的範圍內,較佳在15~50重量份的範圍內。前述顏料分散劑的含量超過60重量份時,黏度升高,含量不足5重量份時,引起難以進行顏料的微粒化或者分散後凝膠化等問題。 The pigment dispersant is in the range of 5 to 60 parts by weight, preferably 15 to 50 parts by weight, based on 100 parts by weight of the solid content of the pigment. When the content of the pigment dispersant exceeds 60 parts by weight, the viscosity is increased, and when the content is less than 5 parts by weight, problems such as microparticulation of the pigment or gelation after dispersion are difficult to occur.
(a3)染料 (a3) dye
前述染料只要具有對於有機溶劑的溶解性就能無限制地使用。較佳地,較佳使用具有對於有機溶劑的溶解性,且能夠確保對於鹼性顯影劑的溶解性、耐熱性、耐溶劑性等的可靠性的染料。 The dye can be used without limitation as long as it has solubility in an organic solvent. Preferably, a dye having solubility in an organic solvent and ensuring reliability against solubility, heat resistance, solvent resistance, and the like of an alkali developer is preferably used.
作為前述染料,能夠使用選自具有磺酸或羧酸等酸性基團的酸性染料、酸性染料與含氮化合物的鹽、酸性染料的磺醯胺化物等和它們的衍生物的染料,除此以外,也能夠選擇偶氮類、呫噸類、酞菁類酸性染料及它們的衍生物。較佳地,前述染料可列舉出:在顯色指數(The Society of Dyers and Colourists出版)內分類為染料的化合物,或染色筆記(染織公司)中記載的公知染料。 As the dye, a dye selected from an acid dye having an acidic group such as a sulfonic acid or a carboxylic acid, a salt of an acid dye and a nitrogen-containing compound, a sulfonamide of an acid dye, or the like, and a derivative thereof can be used. It is also possible to select azo, xanthene, phthalocyanine acid dyes and their derivatives. Preferably, the dye is a compound classified as a dye in a color rendering index (published by The Society of Dyers and Colourists), or a known dye described in a dyeing note (dyeing company).
在前述染料的具體示例中,作為C.I.溶劑染料可列舉出,C.I.溶劑紅8、45、49、89、111、122、125、130、132、146和179;C.I.溶劑藍5、35、36、37、44、59、67和70;C.I.溶劑紫8、9、13、14、36、37、47和49;C.I.溶劑黃4、14、15、23、24、38、62、63、68、82、94、98、99和162; C.I.溶劑橙2、7、11、15、26和56;C.I.溶劑綠1、3、4、5、7、28、29、32、33、34和35。 In the specific examples of the aforementioned dye, as the CI solvent dye, CI solvent red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146 and 179; CI solvent blue 5, 35, 36, 37, 44, 59, 67 and 70; CI solvent violet 8, 9, 13, 14, 36, 37, 47 and 49; CI solvent yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 and 162; C.I. Solvent Oranges 2, 7, 11, 15, 26 and 56; C.I. Solvent Greens 1, 3, 4, 5, 7, 28, 29, 32, 33, 34 and 35.
C.I.溶劑染料中,C.I.溶劑紅8、49、89、111、122、132、146、179;C.I.溶劑藍35、36、44、45、70;C.I.溶劑紫13對有機溶劑的溶解性優異,較佳C.I.溶劑紅8、122、132。 CI solvent dyes, CI solvent red 8, 49, 89, 111, 122, 132, 146, 179; CI solvent blue 35, 36, 44, 45, 70; CI solvent violet 13 is excellent in solubility in organic solvents, Good CI solvent red 8, 122, 132.
另外,作為C.I.酸性染料,可列舉出:C.I.酸性紅1、4、8、14、17、18、26、27、29、31、34、35、37、42、44、50、51、52、57、66、73、80、87、88、91、92、94、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、195、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、418、422和426;C.I.酸性黃1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243和251;C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169和173; C.I.酸性藍1、7、9、15、18、23、25、27、29、40、42、45、51、62、70、74、80、83、86、87、90、92、96、103、112、113、120、129、138、147、150、158、171、182、192、210、242、243、256、259、267、278、280、285、290、296、315、324:1、335和340;C.I.酸性紫6B、7、9、17、19和66;C.I.酸性綠1、3、5、9、16、25、27、50、58、63、65、80、104、105、106和109。 Further, examples of the CI acid dye include: CI acid red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, and 426; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29 , 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139 , 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207 , 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, and 251; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52 , 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169 and 173; CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103 , 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324:1 , 335 and 340; CI Acid Violet 6B, 7, 9, 17, 19 and 66; CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105 , 106 and 109.
酸性染料中,C.I.酸性紅92;C.I.酸性藍80、90;C.I.酸性紫60對有機溶劑的溶解度優異。 Among the acid dyes, C.I. Acid Red 92; C.I. Acid Blue 80, 90; C.I. Acid Violet 60 is excellent in solubility in an organic solvent.
另外,作為C.I.直接染料,可列舉出:C.I.直接紅79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246和250;C.I.直接黃2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138和141;C.I.直接橙34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106和107;C.I.直接藍38、44、57、70、77、80、81、84、85、86、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、137、149、150、153、155、156、158、159、160、 161、162、163、164、166、167、170、171、172、173、188、189、190、192、193、194、196、198、199、200、207、209、210、212、213、214、222、228、229、237、238、242、243、244、245、247、248、250、251、252、256、257、259、260、268、274、275和293;C.I.直接紫47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103和104;C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79和82。 Further, as the CI direct dye, CI direct red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, and 250; CI Direct Yellow 2, 33, 34, 35, 38, 39 , 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138 and 141; CI Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106 and 107; CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85 , 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, and 293; CI Direct Violet 47 , 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103 and 104; CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79 and 82.
此外,作為C.I.媒染劑染料,可列舉出:C.I.媒染劑黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62和65;C.I.媒染劑紅1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、30、32、33、36、37、38、39、41、43、45、46、48、53、56、63、71、74、85、86、88、90、94和95;C.I.媒染劑橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47和48;C.I.媒染劑藍1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83和84;C.I.媒染劑紫1、2、4、5、7、14、22、24、30、31、32、37、40、41、44、45、47、48、53和58;C.I.媒染劑綠1、3、4、5、10、15、19、26、29、33、34、35、 41、43和53。 Further, as the CI mordant dye, CI mordant yellows 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, and 65; Red, 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94 and 95; CI mordant oranges 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47 and 48; CI mordant blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83 and 84; CI mord Agent violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53 and 58; CI mordant green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43 and 53.
前述染料能夠分別單獨使用或組合兩種以上進行使用。 These dyes can be used individually or in combination of 2 or more types, respectively.
前述著色劑中的染料的含量相對於著色劑的固體成分的總重量為0.5~80重量%,較佳為0.5~60重量%,更佳為1~50重量%。前述著色劑中的染料的含量為0.5~80重量%時,在形成圖案後,能夠防止有機溶劑使染料溶出的可靠性下降的問題,靈敏度變高。 The content of the dye in the colorant is from 0.5 to 80% by weight, preferably from 0.5 to 60% by weight, more preferably from 1 to 50% by weight, based on the total weight of the solid content of the colorant. When the content of the dye in the coloring agent is from 0.5 to 80% by weight, the pattern can be prevented from deteriorating the reliability of elution of the dye by the organic solvent, and the sensitivity is increased.
前述著色劑的含量相對於著色感光性樹脂組合物中的固體成分的總重量為5~60重量%,較佳為10~45重量%。在前述著色劑為5~60重量%的情況下,即使形成薄膜,畫素的色濃度也充分,顯影時非畫素部的缺損性也不下降,難以產生殘渣。 The content of the colorant is 5 to 60% by weight, preferably 10 to 45% by weight based on the total weight of the solid content in the colored photosensitive resin composition. When the coloring agent is 5 to 60% by weight, even if a film is formed, the color density of the pixel is sufficient, and the defect of the non-pixel portion at the time of development does not decrease, and it is difficult to generate a residue.
本發明中,著色感光性樹脂組合物中的固體成分的重量是指從著色感光性樹脂組合物中去除溶劑後剩餘成分的總含量。 In the present invention, the weight of the solid component in the colored photosensitive resin composition means the total content of the remaining components after the solvent is removed from the colored photosensitive resin composition.
(B)鹼溶性樹脂 (B) alkali soluble resin
為了對形成圖案時的顯影處理工序中使用的鹼性顯影液具有可溶性,以具有羧基的烯屬不飽和單體作為必需成分進行共聚來製造。 It is produced by copolymerizing an ethylenically unsaturated monomer having a carboxyl group as an essential component in order to be soluble in the alkaline developing solution used in the developing treatment step at the time of pattern formation.
作為前述具有羧基的烯屬不飽和單體的具體示例,可列舉出:丙烯酸、甲基丙烯酸、巴豆酸等單羧酸類;富馬酸、中康酸、衣康酸等二羧酸類;二羧酸類的酸酐;ω-羧基聚己內酯單(甲基)丙烯酸酯等在兩末端具有羧基和羥基的聚合物的單(甲基)丙烯酸酯類等,較佳為丙烯酸、甲基丙烯酸。 Specific examples of the ethylenically unsaturated monomer having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; and dicarboxylic acid; An acid anhydride or a mono(meth)acrylate such as a ω-carboxypolycaprolactone mono(meth)acrylate having a carboxyl group and a hydroxyl group at both terminals, preferably acrylic acid or methacrylic acid.
為了確保對鹼溶性樹脂附加的顯影性,可提供羥基。用於提供羥 基的方法有如下方法:將具有羧基的烯屬不飽和單體與具有羥基的烯屬不飽和單體共聚而進行製造的方法;使具有羧基的烯屬不飽和單體的共聚物與具有縮水甘油基的化合物追加反應而進行製造的方法;以及藉由使具有羧基的烯屬不飽和單體與具有羥基的烯屬不飽和單體的共聚物追加地與具有縮水甘油基的化合物反應而進行製造的方法。 In order to ensure additional developability to the alkali-soluble resin, a hydroxyl group can be provided. For the supply of hydroxyl The method of the base has a method of producing a copolymer of an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group; and a copolymer of an ethylenically unsaturated monomer having a carboxyl group and having a shrinkage a method of producing a glycerol-based compound by additional reaction; and further reacting a copolymer of an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group with a compound having a glycidyl group The method of manufacture.
作為前述具有羥基的烯屬不飽和單體的具體示例,有(甲基)丙烯酸-2-羥乙酯、(甲基)丙烯酸-2-羥丙酯、(甲基)丙烯酸-4-羥丁酯、(甲基)丙烯酸-2-羥基-3-苯氧基丙酯、N-羥基以及丙烯醯胺等,其中,較佳為(甲基)丙烯酸-2-羥乙酯。前述具有羥基的烯屬不飽和單體可組合兩種以上使用。 Specific examples of the above ethylenically unsaturated monomer having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate. The ester, 2-hydroxy-3-phenoxypropyl (meth)acrylate, N-hydroxyl and acrylamide, etc., among them, 2-hydroxyethyl (meth)acrylate is preferred. The above ethylenically unsaturated monomer having a hydroxyl group may be used in combination of two or more kinds.
作為前述具有縮水甘油基的化合物的具體示例,有丁基縮水甘油基醚、縮水甘油基丙基醚、縮水甘油基苯基醚、2-乙基己基縮水甘油基醚、縮水甘油基丁酸酯、縮水甘油基甲基醚、乙基縮水甘油基醚、縮水甘油基異丙基醚、叔丁基縮水甘油基醚、苄基縮水甘油基醚、縮水甘油基-4-叔丁基苯甲酸酯、縮水甘油基硬脂酸酯、芳基縮水甘油基醚和甲基丙烯酸縮水甘油酯等,較佳地,可列舉出丁基縮水甘油基醚、芳基縮水甘油基醚、甲基丙烯酸縮水甘油酯,前述具有縮水甘油基的化合物能夠組合兩種以上使用。 Specific examples of the compound having a glycidyl group include butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, and glycidyl butyrate. , glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, tert-butyl glycidyl ether, benzyl glycidyl ether, glycidyl-4-tert-butylbenzoic acid Ester, glycidyl stearate, aryl glycidyl ether, glycidyl methacrylate, etc., preferably, butyl glycidyl ether, aryl glycidyl ether, methacrylic acid shrinkage The glyceride and the above compound having a glycidyl group can be used in combination of two or more.
前述鹼溶性樹脂的製造時能夠共聚的不飽和單體可如下例示,但不必須限定於此。 The unsaturated monomer copolymerizable in the production of the alkali-soluble resin can be exemplified as follows, but is not necessarily limited thereto.
作為具有能夠共聚的不飽和鍵的聚合性單體的具體示例,有苯乙 烯、乙烯基甲苯、α-甲基苯乙烯、對氯苯乙烯、鄰甲氧基苯乙烯、間甲氧基苯乙烯、對甲氧基苯乙烯、鄰乙烯基苄基甲基醚、間乙烯基苄基甲基醚、對乙烯基苄基甲基醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚等芳香族乙烯化合物;N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-苯基馬來醯亞胺、N-鄰羥基苯基馬來醯亞胺、N-間羥基苯基馬來醯亞胺、N-對羥基苯基馬來醯亞胺、N-鄰甲基苯基馬來醯亞胺、N-間甲基苯基馬來醯亞胺、N-對甲基苯基馬來醯亞胺、N-鄰甲氧基苯基馬來醯亞胺、N-間甲氧基苯基馬來醯亞胺、N-對甲氧基苯基馬來醯亞胺等N-取代馬來醯亞胺類化合物;(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸仲丁酯、(甲基)丙烯酸叔丁酯等(甲基)丙烯酸烷基酯類;(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸-2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸-2-二環戊氧基乙酯、(甲基)丙烯酸異冰片酯等脂環族(甲基)丙烯酸酯類;(甲基)丙烯酸-2-羥乙酯、(甲基)丙烯酸-2-羥丙酯、(甲基)丙烯酸4-羥丁酯、(甲基)丙烯酸-2-羥基-3-苯氧基丙酯、N-羥乙基丙烯醯胺等(甲基)丙烯酸羥乙酯類; (甲基)丙烯酸苯酯、(甲基)丙烯酸苄酯等(甲基)丙烯酸芳基酯類;3-(甲基丙烯醯氧基甲基)氧雜環丁烷、3-(甲基丙烯醯氧甲基)-3-乙基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-三氟甲基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-苯基氧雜環丁烷、2-(甲基丙烯醯氧基甲基)氧雜環丁烷、2-(甲基丙烯醯氧基甲基)-4-三氟甲基氧雜環丁烷等不飽和氧雜環丁烷化合物等。 As a specific example of a polymerizable monomer having a copolymerizable unsaturated bond, there is phenylethyl Alkene, vinyl toluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, methylene Aromatic vinyl compounds such as benzylbenzyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether; N- Cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenyl malayan Amine, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m-methylphenylmaleimide, N-p-methylphenylmale N-substituted Malay such as imine, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, N-p-methoxyphenylmaleimide a quinone imine compound; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, ( Isobutyl methacrylate, sec-butyl (meth) acrylate, (meth)acrylic acid alkyl esters such as t-butyl (meth)acrylate; cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate , (meth)acrylic acid tricyclo [5.2.1.02,6]decane-8-yl ester, (meth)acrylic acid-2-dicyclopentyloxyethyl ester, (meth)acrylic acid isobornyl ester and other alicyclic Group (meth) acrylates; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, (meth) acrylate - Hydroxyethyl (meth)acrylate such as 2-hydroxy-3-phenoxypropyl ester or N-hydroxyethyl acrylamide; (A) aryl (meth) acrylate such as phenyl (meth) acrylate or benzyl (meth) acrylate; 3-(methacryloxymethyl) oxetane, 3-(methacryl)醯Oxymethyl)-3-ethyloxetane, 3-(methacryloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloxyloxy) Methyl)-2-phenyloxetane, 2-(methacryloxymethyl)oxetane, 2-(methacryloxymethyl)-4-trifluoromethyl An unsaturated oxetane compound such as a oxetane or the like.
前述例示的單體能夠分別單獨使用或者組合兩種以上進行使用。 The monomers exemplified above can be used singly or in combination of two or more.
為了確保與鹼溶性樹脂的染料的相溶性和著色感光性樹脂組合物的貯存穩定性,酸值較佳為30~150mgKOH/g。鹼溶性樹脂的酸值不足30mgKOH/g的情況下,著色感光性樹脂組合物的顯影速度慢,超過150mgKOH/g的情況下,與基板的附著性降低且容易發生圖案短路,產生與染料的相溶性問題,著色感光性樹脂組合物內的染料析出,貯存穩定性降低,黏度上升。 The acid value is preferably from 30 to 150 mgKOH/g in order to ensure compatibility with the dye of the alkali-soluble resin and storage stability of the colored photosensitive resin composition. When the acid value of the alkali-soluble resin is less than 30 mgKOH/g, the development speed of the colored photosensitive resin composition is slow, and when it exceeds 150 mgKOH/g, the adhesion to the substrate is lowered, and pattern short-circuiting is likely to occur, and a phase with the dye is generated. The solubility problem causes the dye in the colored photosensitive resin composition to precipitate, the storage stability is lowered, and the viscosity is increased.
此外,前述鹼溶性樹脂的含量相對於著色感光性樹脂組合物中的固體成分的總重量為10~80重量%,較佳為10~70重量%。只要前述鹼溶性樹脂的含量為10~80重量%,則在顯影液中溶解性優異,容易形成圖案,顯影時防止曝光部的畫素部分的膜減少,非畫素部分的缺損性變得良好。 Further, the content of the alkali-soluble resin is from 10 to 80% by weight, preferably from 10 to 70% by weight, based on the total weight of the solid content in the colored photosensitive resin composition. When the content of the alkali-soluble resin is from 10 to 80% by weight, the solubility in the developer is excellent, the pattern is easily formed, and the film of the pixel portion of the exposed portion is prevented from being reduced during development, and the defect of the non-pixel portion is improved. .
(C)光聚合性化合物 (C) Photopolymerizable compound
前述光聚合性化合物(C)只要是在下述光聚合引發劑(D)的作用 下能夠聚合的化合物即可。 The photopolymerizable compound (C) is used as long as it is in the following photopolymerization initiator (D) The compound which can be polymerized can be used.
官能團數量沒有特別限定,但較佳使用雙官能以上的多官能光聚合性化合物,更佳聚合性優異且固化充分進行的三官能以上的多官能光聚合性化合物。 The number of the functional groups is not particularly limited, and a difunctional or higher polyfunctional photopolymerizable compound is preferably used, and a trifunctional or higher polyfunctional photopolymerizable compound which is excellent in polymerizability and sufficiently cured is preferably used.
作為前述雙官能光聚合性化合物的具體示例,有2-羥基-1,3-二甲基丙烯醯氧基丙烷、2-羥基-1-丙烯醯氧基-3-甲基丙烯醯氧基丙烷等。 Specific examples of the aforementioned difunctional photopolymerizable compound include 2-hydroxy-1,3-dimethylpropenyloxypropane, 2-hydroxy-1-propenyloxy-3-methylpropenyloxypropane Wait.
作為前述三官能以上的多官能光聚合性化合物的具體示例,有季戊四醇三丙烯酸酯、二季戊四醇五丙烯酸酯等,可組合兩種以上使用。市售品有商品名701(NK ESTER)、701A(NK ESTER)、A-TMM-3L(NK ESTER)、KAYARAD DPHA(日本化藥)等。 Specific examples of the trifunctional or higher polyfunctional photopolymerizable compound include pentaerythritol triacrylate and dipentaerythritol pentaacrylate, and two or more kinds thereof may be used in combination. Commercially available products include trade name 701 (NK ESTER), 701A (NK ESTER), A-TMM-3L (NK ESTER), KAYARAD DPHA (Japan Chemical).
前述光聚合性化合物(C)相對於著色感光性樹脂組合物中的固體成分的總重量為5~45重量%,較佳為7~45重量%。在前述光聚合性化合物(C)為5~45重量%的情況下,畫素部的強度、平滑性良好。 The total amount of the photopolymerizable compound (C) relative to the solid content in the colored photosensitive resin composition is 5 to 45% by weight, preferably 7 to 45% by weight. When the photopolymerizable compound (C) is 5 to 45% by weight, the strength and smoothness of the pixel portion are good.
(D)光聚合引發劑 (D) Photopolymerization initiator
光聚合引發劑(D)的特徵在於包含由下述化學式1表示的乙基咔唑結構中取代有NO2的肟酯類化合物(d1)。以0.01重量%以上的濃度包含前述光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度必須為0.5以上。 The photopolymerization initiator (D) is characterized by comprising an oxime ester compound (d1) in which an ethyl carbazole structure represented by the following Chemical Formula 1 is substituted with NO 2 . The propylene glycol methyl ether acetate solution containing the photopolymerization initiator at a concentration of 0.01% by weight or more must have an absorbance at 405 nm of 0.5 or more.
[化學式1]
式中,R1為碳數1~8的烷基、OR3基、經鹵素基團取代的碳數6~10的芳基或經鹵素基團取代的碳數7~24的芳烷基,R2為碳數1~8的烷基、碳數6~10的芳基或碳數7~24的芳烷基,R3為碳數1~20的烷基或碳數1~20的烷氧基。 In the formula, R 1 is an alkyl group having 1 to 8 carbon atoms, an OR 3 group, an aryl group having 6 to 10 carbon atoms substituted by a halogen group, or an aralkyl group having 7 to 24 carbon atoms substituted by a halogen group. R 2 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 24 carbon atoms, and R 3 is an alkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms. Oxygen.
在以0.01重量%以上的濃度包含前述化學式1的肟酯類化合物的光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.5以上的情況下,用405nm的鐳射曝光器進行曝光而形成圖案時,初始效率變高,即使不使用過多的光聚合引發劑,也能夠得到著色感光性樹脂組合物的高靈敏度和優異的可靠性。 When the propylene glycol methyl ether acetate solution containing the photopolymerization initiator of the oxime ester compound of the above Chemical Formula 1 at a concentration of 0.01% by weight or more or more has an absorbance at 405 nm of 0.5 or more, exposure is performed with a 405 nm laser exposure device. On the other hand, when the pattern is formed, the initial efficiency is high, and high sensitivity and excellent reliability of the colored photosensitive resin composition can be obtained without using too much photopolymerization initiator.
此外,在不損害本發明效果的範圍內,可附加使用前述以外的光聚合引發劑(d2)。前述光聚合引發劑(d2)的示例較佳使用選自由苯乙酮類化合物、二苯甲酮類化合物、三嗪類化合物、聯咪唑類化合物及噻噸酮類化合物組成的群組中的一種以上的化合物。 Further, the photopolymerization initiator (d2) other than the above may be additionally used insofar as the effects of the present invention are not impaired. The above photopolymerization initiator (d2) is preferably one selected from the group consisting of an acetophenone compound, a benzophenone compound, a triazine compound, a biimidazole compound, and a thioxanthone compound. The above compounds.
作為前述苯乙酮類化合物的具體示例,可列舉出:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、苯偶醯二甲基縮酮、2-羥基-1-[4- (2-羥基乙氧基)苯基]-2-甲基丙烷-1-酮、1-羥基環己基苯基酮、2-甲基-1-(4-甲基硫苯基)-2-嗎啉基丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-嗎啉代苯基)丁烷-1-酮、2-羥基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙烷-1-酮和2-(4-甲基苄基)-2-(二甲基氨基)-1-(4-嗎啉代苯基)丁烷-1-酮等。 Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and benzoin dimethyl ketal. 2-hydroxy-1-[4- (2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylthiophenyl)-2- Morpholinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1- [4-(1-Methylvinyl)phenyl]propan-1-one and 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl) Butane-1-one and the like.
作為前述二苯甲酮類化合物,例如有二苯甲酮、鄰苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4′-甲基二苯硫醚、3,3′,4,4′-四(叔丁基過氧羰基)二苯甲酮和2,4,6-三甲基二苯甲酮等。 As the benzophenone compound, for example, benzophenone, methyl orthobenzoylbenzoate, 4-phenylbenzophenone, 4-benzylidene-4'-methyldiphenylsulfide Ether, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone and 2,4,6-trimethylbenzophenone.
作為前述三嗪類化合物的具體示例,可列舉出:2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(4-二乙基氨基-2-甲基苯基)乙烯基]-1,3,5-三嗪和2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三嗪等。 Specific examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4. - bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-1,3 ,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl) - 6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan) -2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl) Vinyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3, 5-triazine and the like.
作為前述聯咪唑化合物的具體示例,可列舉出:2,2′-雙(2-氯苯基)-4,4′,5,5′-四苯基聯咪唑、2,2′-雙(2,3-二氯苯基)-4,4′,5,5′-四苯基聯咪唑、2,2′-雙(2-氯苯基)-4,4′,5,5′-四(烷氧基苯基)聯咪唑、2,2′-雙(2-氯苯基)-4,4′,5,5′-四(三烷氧基苯基)聯咪唑、2,2-雙(2,6-二氯苯基)-4,4′,5,5′-四苯基-1,2′-聯咪唑和 4,4′,5,5′位置的苯基由烷氧羰基置換後的咪唑化合物等。這些之中,較佳為2,2′-雙(2-氯苯基)-4,4′,5,5′-四苯基聯咪唑、2,2′-雙(2,3-二氯苯基)-4,4′,5,5′-四苯基聯咪唑和2,2-雙(2,6-二氯苯基)-4,4′,5,5′-四苯基-1,2′-聯咪唑。 Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis ( 2,3-Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'- Tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole, 2,2 -bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole and An imidazole compound or the like in which a phenyl group at the 4, 4', 5, 5' position is substituted with an alkoxycarbonyl group. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichloro) is preferred. Phenyl)-4,4',5,5'-tetraphenylbiimidazole and 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl- 1,2'-biimidazole.
作為前述噻噸酮類化合物,例如有:2-異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-二氯噻噸酮和1-氯-4-丙氧基噻噸酮等。 As the aforementioned thioxanthone compound, for example, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxy group Thioxanthone and the like.
另外,為了提高本發明的著色感光性樹脂組合物的靈敏度,前述光聚合引發劑還能夠進一步包含光聚合引發輔助劑(d3)。本發明涉及的著色感光性樹脂組合物由於包含光聚合引發輔助劑(d3),使得靈敏度更高,從而能夠提高生產率。 In addition, the photopolymerization initiator may further contain a photopolymerization initiation aid (d3) in order to increase the sensitivity of the coloring photosensitive resin composition of the present invention. The colored photosensitive resin composition according to the present invention contains a photopolymerization initiation aid (d3), so that sensitivity is higher, and productivity can be improved.
前述光聚合引發輔助劑(d3)例如能夠較佳使用選自由胺化合物、羧酸化合物、具有硫醇基的有機硫化合物組成的群組中的一種以上的化合物。 The photopolymerization initiation aid (d3) can preferably be, for example, one or more compounds selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group.
作為前述胺化合物,較佳使用芳香胺化合物,具體而言,能夠使用三乙醇胺、甲基二乙醇胺、三異丙醇胺等脂肪族胺化合物、4-二甲基氨基苯甲酸甲酯、4-二甲基氨基苯甲酸乙酯、4-二甲基氨基苯甲酸異戊酯、4-二甲基氨基苯甲酸2-乙基己酯、苯甲酸2-二甲基氨基乙酯、N,N-二甲基對甲苯胺、4,4′-雙(二甲氨基)二苯甲酮(俗稱:米蚩酮)和4,4′-雙(二乙氨基)二苯甲酮等。 As the amine compound, an aromatic amine compound is preferably used. Specifically, an aliphatic amine compound such as triethanolamine, methyldiethanolamine or triisopropanolamine, methyl 4-dimethylaminobenzoate or the like can be used. Ethyl dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N - dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as: Michler's ketone) and 4,4'-bis(diethylamino)benzophenone.
前述羧酸化合物較佳為芳香族雜乙酸類,具體而言,可列舉出:苯硫基乙酸、甲基苯硫基乙酸、乙基苯硫基乙酸、甲基乙基苯硫基乙 酸、二甲基苯硫基乙酸、甲氧基苯硫基乙酸、二甲氧苯硫基乙酸、氯苯硫基乙酸、二氯苯硫基乙酸、N-苯基甘氨酸、苯氧乙酸、萘硫基乙酸、N-萘基甘氨酸和萘氧乙酸等。 The carboxylic acid compound is preferably an aromatic heteroacetic acid, and specific examples thereof include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, and methylethylphenylthioethyl. Acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthalene Thioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.
作為前述具有硫醇基的有機硫化合物的具體示例,可列舉出:2-巰基苯并噻唑、1,4-雙(3-巰基丁醯氧基)丁烷、1,3,5-三(3-巰基丁氧基乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丁酸酯)、季戊四醇四(3-巰基丙酸酯)、二季戊四醇六(3-巰基丙酸酯)和四乙二醇雙(3-巰基丙酸酯)等。 Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1,4-bis(3-mercaptobutyloxy)butane, and 1,3,5-tri ( 3-mercaptobutoxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropane tris(3-mercaptopropionate), Pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), and tetraethylene glycol bis(3-mercaptopropionate).
前述光聚合引發劑相對於本發明著色感光性樹脂組合物中的固體成分的總重量為0.1~30重量%,較佳可為1~20重量%。在前述光聚合引發劑在前述0.1~30重量%範圍內的情況下,著色感光性樹脂組合物的靈敏度變高,曝光時間縮短,使得生產率得以提高,能夠保持高解析度。並且,使用前述組合物形成的畫素部的強度與前述畫素部的表面的平滑性變得良好。 The total amount of the photopolymerization initiator relative to the solid content in the colored photosensitive resin composition of the present invention is 0.1 to 30% by weight, preferably 1 to 20% by weight. When the photopolymerization initiator is in the range of 0.1 to 30% by weight, the sensitivity of the colored photosensitive resin composition is increased, the exposure time is shortened, productivity is improved, and high resolution can be maintained. Further, the strength of the pixel portion formed using the composition and the smoothness of the surface of the pixel portion are good.
前述化學式1的肟酯類化合物(d1)相對於全部光聚合引發劑的總重量為10~100重量%,較佳為20~100重量%。化學式1的肟酯類化合物(d1)在全部光聚合引發劑中的比例不到10重量%時,不能克服由染料造成的靈敏度降低,在顯影工序中容易發生圖案短路。 The total weight of the oxime ester compound (d1) of the above Chemical Formula 1 is from 10 to 100% by weight, preferably from 20 to 100% by weight, based on the total weight of all the photopolymerization initiators. When the proportion of the oxime ester compound (d1) of Chemical Formula 1 in all the photopolymerization initiators is less than 10% by weight, the decrease in sensitivity due to the dye cannot be overcome, and pattern short-circuiting easily occurs in the development step.
在附加使用前述光聚合引發輔助劑(d3)的情況下,光聚合引發輔助劑(d3)相對於本發明的著色感光性樹脂組合物中的固體成分的總重 量為0.1~30重量%,較佳可為1~20重量%。在前述光聚合引發輔助劑(d3)的含量在前述0.1~30重量%範圍內的情況下,著色感光性樹脂組合物的靈敏度進一步提高,提供使用前述組合物形成的濾色器的生產率提高的效果。 In the case where the photopolymerization initiating auxiliary (d3) is additionally used, the total weight of the photopolymerization initiating auxiliary (d3) relative to the solid content in the colored photosensitive resin composition of the present invention The amount is 0.1 to 30% by weight, preferably 1 to 20% by weight. When the content of the photopolymerization initiation aid (d3) is in the range of 0.1 to 30% by weight, the sensitivity of the colored photosensitive resin composition is further improved, and the productivity of the color filter formed using the composition is improved. effect.
(E)溶劑 (E) solvent
在本發明中,溶劑的特徵在於必需包含4-羥基-4-甲基-2-戊酮。 In the present invention, the solvent is characterized in that it is necessary to contain 4-hydroxy-4-methyl-2-pentanone.
此外,前述溶劑只要有效溶解著色感光性樹脂組合物中包含的其他成分,即可無特別限制地使用通常著色感光性樹脂組合物中使用的溶劑,特別佳為醚類、芳香族烴類、酮類、醇類、酯類或醯胺類等。 In addition, the solvent to be used in the coloring photosensitive resin composition can be used without particular limitation, and it is particularly preferable that it is an ether, an aromatic hydrocarbon, or a ketone, as long as it is effective to dissolve other components contained in the coloring photosensitive resin composition. Classes, alcohols, esters or guanamines.
前述醚類例如可列舉出:乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、二乙二醇二甲醚、二乙二醇二乙醚、二丙二醇二丙醚和二乙二醇二丁醚等。 Examples of the ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether. Dipropylene glycol dipropyl ether and diethylene glycol dibutyl ether.
前述芳香族烴類例如可列舉出:苯、甲苯、二甲苯和三甲苯等。 Examples of the aromatic hydrocarbons include benzene, toluene, xylene, and trimethylbenzene.
前述酮類例如可列舉出:甲乙酮、丙酮、甲基戊基酮、甲基異丁基酮和環己酮等。 Examples of the ketones include methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone.
前述醇類例如可列舉出:乙醇、丙醇、丁醇、己醇、環己醇、乙二醇和丙三醇等。 Examples of the alcohols include ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.
前述酯類例如可列舉出:3-乙氧基丙酸乙酯、3-甲氧基丙酸甲酯、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、乙酸乙酯、乙酸丁酯、乙酸戊酯、乳酸甲酯、乳酸乙酯、乳酸丁酯、乙酸-3-甲氧基丁酯、乙酸-3-甲基-3-甲氧基-1-丁酯、乙酸甲氧基戊酯、乙二醇單乙酸酯、乙二醇 二乙酸酯、丙酸-3-甲氧基甲酯、丙二醇甲醚乙酸酯、2-氨基-2-甲基-1,3-丙二醇、2-氨基-2-乙基-1,3-丙二醇、乳酸乙酯、丙二醇、正丙醚、丙酸-3-乙氧基乙酯、丙二醇單丁醚、乙酸-3-甲氧基-1-丁酯、乙二醇單丁醚、二乙二醇甲基乙基醚、1,2-丙二醇二乙酸酯、二丙二醇單甲醚、乙二醇單丁醚乙酸酯、二丙二醇單乙醚、γ-丁內酯、二乙二醇單乙醚乙酸酯、二丙二醇甲醚乙酸酯、二乙二醇單丁醚、1,3-丁二醇二乙酸酯、二乙二醇單丁醚乙酸酯、乙二醇單甲醚乙酸酯、二乙二醇單乙酸酯、二乙二醇二乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇乙二醇單乙酸酯、丙二醇二乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、碳酸亞乙酯、碳酸亞丙酯、γ-丁內酯等。 Examples of the esters include ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellosolve acetate, ethyl cellosolve acetate, and ethyl acetate. Butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, acetic acid Oxyvalyl ester, ethylene glycol monoacetate, ethylene glycol Diacetate, 3-methoxymethyl propionate, propylene glycol methyl ether acetate, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3 -propylene glycol, ethyl lactate, propylene glycol, n-propyl ether, 3-ethoxyethyl propionate, propylene glycol monobutyl ether, acetic acid-3-methoxy-1-butyl ester, ethylene glycol monobutyl ether, two Ethylene glycol methyl ethyl ether, 1,2-propylene glycol diacetate, dipropylene glycol monomethyl ether, ethylene glycol monobutyl ether acetate, dipropylene glycol monoethyl ether, γ-butyrolactone, diethylene glycol Monoethyl ether acetate, dipropylene glycol methyl ether acetate, diethylene glycol monobutyl ether, 1,3-butylene glycol diacetate, diethylene glycol monobutyl ether acetate, ethylene glycol monomethyl Ether acetate, diethylene glycol monoacetate, diethylene glycol diacetate, diethylene glycol monobutyl ether acetate, propylene glycol ethylene glycol monoacetate, propylene glycol diacetate, propylene glycol Monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene carbonate, propylene carbonate, γ-butyrolactone, and the like.
前述示例的溶劑中,從塗布性及乾燥性方面考慮,較佳為沸點100℃~200℃的有機溶劑,例如能夠使用丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、環己酮、乳酸乙酯、乳酸丁酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸甲酯等。 In the solvent of the above-mentioned example, from the viewpoint of coatability and drying property, an organic solvent having a boiling point of 100 ° C to 200 ° C is preferable, and for example, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, or a ring can be used. Hexanone, ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like.
前述示例的溶劑能夠分別單獨使用或混合兩種以上進行使用,以本發明的著色感光性樹脂組合物的總重量為基準可含有60~90重量%,較佳可含有70~85重量%。只要前述溶劑處於前述60~90重量%的範圍內,則使用輥式塗布機、旋轉塗布機、狹縫旋轉塗布機、狹縫式塗布機(也稱為槽膜塗布機)、噴墨式等的塗布裝置塗布時,提供塗布性良好的效果。 The solvent of the above-mentioned example can be used singly or in combination of two or more kinds, and may be contained in an amount of 60 to 90% by weight, preferably 70 to 85% by weight based on the total weight of the colored photosensitive resin composition of the present invention. When a solvent is in the range of 60 to 90% by weight, a roll coater, a spin coater, a slit spin coater, a slit coater (also referred to as a slot coater), an ink jet type, or the like is used. When the coating device is applied, the coating property is excellent.
此外,前述4-羥基-4-甲基-2-戊酮相對於本發明的著色感光性樹 脂組合物中的溶劑總重量較佳為5~20重量%。前述4-羥基-4-甲基-2-戊酮的含量不到5重量%時,著色感光性樹脂組合物中的染料析出並產生異物,對比度降低。此外,超出20重量%時,產生著色感光性樹脂組合物的分散性降低、黏度上升的問題。 Further, the aforementioned 4-hydroxy-4-methyl-2-pentanone is colored relative to the colorimetric tree of the present invention. The total weight of the solvent in the fat composition is preferably from 5 to 20% by weight. When the content of the 4-hydroxy-4-methyl-2-pentanone is less than 5% by weight, the dye in the colored photosensitive resin composition is precipitated to generate foreign matter, and the contrast is lowered. In addition, when it exceeds 20% by weight, the dispersibility of the colored photosensitive resin composition is lowered and the viscosity is increased.
(F)添加劑 (F) additive
前述添加劑根據需要可選擇性地添加,例如可包含從其他高分子化合物、固化劑、表面活性劑、黏附促進劑、紫外線吸收劑和抗絮凝劑組成的組中選擇的一種以上。 The above-mentioned additives may be optionally added as needed, and for example, may be one or more selected from the group consisting of other polymer compounds, curing agents, surfactants, adhesion promoters, ultraviolet absorbers, and deflocculants.
作為前述其他高分子化合物的具體示例,可列舉出:環氧樹脂、馬來醯亞胺樹脂等固化性樹脂、聚乙烯醇、聚丙烯酸、聚乙二醇單烷基醚、聚氟烷基丙烯酸酯、聚酯、聚氨酯等熱塑性樹脂等。 Specific examples of the other polymer compound include curable resins such as epoxy resins and maleic imine resins, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, and polyfluoroalkyl acrylic acid. Thermoplastic resins such as esters, polyesters, and polyurethanes.
前述固化劑為了提高深部固化和機械強度而使用,固化劑的具體示例可列舉出環氧化合物、多官能異氰酸酯化合物、三聚氰胺化合物、氧雜環丁烷化合物等。 The curing agent is used to improve deep curing and mechanical strength, and specific examples of the curing agent include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, and the like.
在前述固化劑中,環氧化合物可列舉出例如雙酚A型環氧樹脂、氫化雙酚A型環氧樹脂、雙酚F型環氧樹脂、氫化雙酚F型環氧樹脂、酚醛清漆型環氧樹脂、其他芳香族類環氧樹脂、脂環族類環氧樹脂、縮水甘油酯類樹脂、縮水甘油胺類樹脂或前述環氧樹脂溴化衍生物、環氧樹脂及其溴化衍生物以外的脂肪族脂環族或芳香族環氧化合物、丁二烯(共)聚合物的環氧化物、異戊二烯(共)聚合物的環氧化物、(甲基)丙烯酸縮水甘油酯(共)聚合物、異氰脲酸三縮水甘 油酯等。 In the above curing agent, examples of the epoxy compound include bisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol F type epoxy resin, hydrogenated bisphenol F type epoxy resin, and novolak type. Epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin, glycidyl ester resin, glycidylamine resin or the above-mentioned epoxy resin brominated derivative, epoxy resin and brominated derivative thereof Aliphatic alicyclic or aromatic epoxy compounds, epoxides of butadiene (co)polymers, epoxides of isoprene (co)polymers, glycidyl (meth)acrylates ( Common) polymer, isocyanuric acid triglycoside Oil esters, etc.
在前述固化劑中,氧雜環丁烷化合物可列舉出例如碳酸酯雙氧雜環丁烷、二甲苯雙氧雜環丁烷、己二酸雙氧雜環丁烷、對苯二甲酸雙氧雜環丁烷、環己烷二羧酸二-氧雜環丁烷等。 Among the above curing agents, the oxetane compound may, for example, be a carbonate dioxetane, xylene dioxetane, adipic acid dioxetane or dioxyethylene terephthalate. Heterocyclobutane, cyclohexanedicarboxylic acid di-oxetane, and the like.
前述固化劑可與固化劑一起合用使環氧化合物的環氧基、氧雜環丁烷化合物的氧雜環丁烷骨架開環聚合的固化輔助化合物。前述固化輔助化合物例如有多元羧酸類、多元羧酸酐類、酸產生劑等。前述羧酸酐類可以使用作為環氧樹脂固化劑的市售品。前述環氧樹脂固化劑的具體示例可列舉出EH-700(旭電業公司製造)、HH(新日本化工公司製造)、MH-700(新日本化工公司製造)等。前述示例的固化劑可以單獨使用或混合兩種以上使用。 The curing agent may be used in combination with a curing agent to form a curing auxiliary compound for ring-opening polymerization of an epoxy group of an epoxy compound or an oxetane skeleton of an oxetane compound. Examples of the curing auxiliary compound include polycarboxylic acids, polycarboxylic anhydrides, acid generators and the like. As the carboxylic acid anhydride, a commercially available product as an epoxy resin curing agent can be used. Specific examples of the aforementioned epoxy resin curing agent can be exemplified EH-700 (made by Asahi Electric Co., Ltd.), HH (manufactured by Nippon Chemical Co., Ltd.), MH-700 (manufactured by Nippon Chemical Co., Ltd.), etc. The curing agents of the foregoing examples may be used singly or in combination of two or more.
前述表面活性劑能夠用於進一步提高感光性樹脂組合物的成膜性,較佳可使用有機矽類、氟類、酯類、陽離子類、陰離子類、非離子類、兩性表面活性劑等。具體地,可列舉出聚氧乙烯烷基醚類、聚氧乙烯烷基苯醚類、聚乙二醇二酯類、山梨糖醇酐脂肪酸酯類、脂肪酸改質的聚酯類、叔胺改質的聚氨酯類、聚乙烯亞胺類等。此外,前述有機矽類表面活性劑例如作為市售品有東麗道康寧有機矽有限公司的DC3PA、DC7PA、SH11PA、SH21PA、SH8400等,GE東芝有機矽有限公司的TSF-4440、TSF-4300、TSF-4445、TSF-4446、TSF-4460、TSF-4452等。前述氟類表面活性劑例如作為市售品有大日本油墨化學工業公司的F-470、F-471、F-475、F-482、F-489 等。此外,其它可使用的市售品可列舉出KP(信越化學工業公司製造)、POLYFLOW(共榮社化學公司製造)、EFTOP(Tochem Products公司製造)、MEGAFAC(大日本油墨化學工業公司製造)、Flourad(住友3M公司製造)、Asahi guard、Surflon(以上,旭硝子公司製造)、SOLSPERSE(捷利康公司製造)、EFKA(EFKA化學公司製造)、PB821(味之素公司製造)、Disperbyk-series(BYK-chemi)等。前述示例的表面活性劑能夠分別單獨使用或組合兩種以上進行使用。 The surfactant can be used to further improve the film formability of the photosensitive resin composition, and organic hydrazines, fluorines, esters, cations, anions, nonionics, amphoteric surfactants, and the like are preferably used. Specific examples thereof include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, and tertiary amines. Polyurethanes, polyethyleneimine, etc. Further, the above-mentioned organic terpene surfactants are, for example, DC3PA, DC7PA, SH11PA, SH21PA, SH8400, etc. of Toray Dow Corning Organic Co., Ltd., and TSF-4440, TSF-4300, TSF of GE Toshiba Organic Co., Ltd. -4445, TSF-4446, TSF-4460, TSF-4452, etc. The fluorosurfactant is, for example, a commercially available product of Dainippon Ink Chemical Industry Co., Ltd. F-470, F-471, F-475, F-482, F-489, etc. In addition, other commercially available products which can be used include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products Co., Ltd.), MEGAFAC (manufactured by Dainippon Ink Chemical Industry Co., Ltd.), Flourad (manufactured by Sumitomo 3M), Asahi guard, Surflon (above, manufactured by Asahi Glass Co., Ltd.), SOLSPERSE (manufactured by Jielikon), EFKA (manufactured by EFKA Chemical Co., Ltd.), PB821 (manufactured by Ajinomoto Co., Ltd.), Disperbyk-series (BYK) -chemi) and so on. The surfactants of the foregoing examples can be used singly or in combination of two or more.
前述黏附促進劑的種類沒有特別限定,可使用的黏附促進劑的具體示例可列舉出:乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、N-(2-氨基乙基)-3-氨丙基甲基二甲氧基矽烷、N-(2-氨基乙基)-3-氨丙基三甲氧基矽烷、3-氨基丙基三乙氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧丙基甲基二甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷、3-異氰酸酯丙基三甲氧基矽烷、3-異氰酸酯基丙基三乙氧基矽烷等。前述示例的黏附促進劑能夠分別單獨使用或組合兩種以上進行使用。前述黏附促進劑相對於著色感光性樹脂組合物中的固體成分的總重量通常為0.01~10重量%,較佳可為0.05~2重量%。 The type of the adhesion promoter is not particularly limited, and specific examples of the adhesion promoter which can be used include vinyl trimethoxy decane, vinyl triethoxy decane, and vinyl tris(2-methoxyethoxy). ) decane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropane Triethoxy decane, 3-glycidoxypropyltrimethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)B Trimethoxy decane, 3-chloropropylmethyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethyl Oxydecane, 3-isocyanate propyl trimethoxy decane, 3-isocyanate propyl triethoxy decane, and the like. The adhesion promoters of the foregoing examples can be used singly or in combination of two or more. The total weight of the adhesion promoter to the solid content in the colored photosensitive resin composition is usually 0.01 to 10% by weight, preferably 0.05 to 2% by weight.
作為前述紫外線吸收劑的種類沒有特別限定,可使用的具體示例可列舉出:2-(3-叔丁基-2-羥基-5-甲基苯基)-5-氯苯并三唑、烷氧基 二苯甲酮等。 The type of the ultraviolet absorber is not particularly limited, and specific examples thereof which can be used include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole and an alkane. Oxyl Benzophenone and the like.
作為前述抗絮凝劑的種類沒有特別限定,可使用的的具體示例可列舉出聚丙烯酸鈉等。 The type of the deflocculant is not particularly limited, and specific examples of usable may be sodium polyacrylate or the like.
若舉例說明本發明的著色感光性樹脂組合物的製造方法,則如下所述。 The method for producing the colored photosensitive resin composition of the present invention will be described below by way of example.
首先,將前述著色劑(A)中的顏料(a1)與溶劑(E)混合,使用珠磨機等進行分散直至顏料的平均粒徑為0.2μm以下左右。此時,根據需要可以使顏料分散劑(a2)、鹼溶性樹脂(B)的一部分或全部,或者染料(a3)與溶劑(E)一起混合、溶解或分散。 First, the pigment (a1) in the coloring agent (A) is mixed with the solvent (E), and dispersed by using a bead mill or the like until the average particle diameter of the pigment is about 0.2 μm or less. At this time, a part or all of the pigment dispersant (a2) or the alkali-soluble resin (B) or the dye (a3) may be mixed, dissolved or dispersed together with the solvent (E) as needed.
向前述混合了的分散液中進一步添加染料(a3)、鹼溶性樹脂的餘量(B)、光聚合性化合物(C)、光聚合引發劑(D)以及根據需要的添加劑(F)和溶劑(E)以形成規定的濃度,能夠製造本發明的著色感光性樹脂組合物。 Further, the dye (a3), the balance of the alkali-soluble resin (B), the photopolymerizable compound (C), the photopolymerization initiator (D), and the additive (F) and the solvent as needed are further added to the above-mentioned mixed dispersion liquid. (E) The colored photosensitive resin composition of the present invention can be produced by forming a predetermined concentration.
此外,本發明提供了由前述著色感光性樹脂組合物製造的濾色器以及包含該濾色器的顯示裝置。 Further, the present invention provides a color filter manufactured from the above-described colored photosensitive resin composition and a display device including the color filter.
顯示裝置可以藉由如下述將前述著色感光性樹脂組合物塗布在基材上並進行光固化及顯影,從而形成圖案來製造。 The display device can be produced by applying the coloring photosensitive resin composition onto a substrate as described below, and performing photocuring and development to form a pattern.
首先,在將著色感光性樹脂組合物塗布在基板(通常是玻璃)或事先形成的由著色感光性樹脂組合物的固體成分構成的層上之後,藉由加熱乾燥除去溶劑等的揮發成分而得到光滑的塗膜。 First, after the colored photosensitive resin composition is applied onto a substrate (usually glass) or a layer formed of a solid component of a colored photosensitive resin composition which is formed in advance, a volatile component such as a solvent is removed by heating and drying. Smooth coating.
塗布方法例如可藉由旋塗法、柔性塗布法、輥塗法、狹縫旋塗法 或狹縫塗布法等實施。塗布後的加熱乾燥(預烘焙)、或減壓乾燥後進行加熱而使溶劑等的揮發成分揮發。此處,加熱溫度通常為70至200℃,較佳為80至130℃。加熱乾燥後的塗膜厚度通常為1至8μm左右。對如此得到的塗膜藉由用於形成目標圖案的掩膜進行紫外線照射。此時,對曝光部整體均勻地照射平行光線,另外,較佳使用掩膜對準器或步進器等裝置,以使得掩膜和基板對齊至正確位置。如果照射紫外線,則被紫外線照射的部位固化。 The coating method can be, for example, a spin coating method, a flexible coating method, a roll coating method, or a slit spin coating method. Or a slit coating method or the like. After heating and drying (prebaking) after application, or drying under reduced pressure, heating is performed to volatilize volatile components such as a solvent. Here, the heating temperature is usually from 70 to 200 ° C, preferably from 80 to 130 ° C. The thickness of the coating film after heat drying is usually about 1 to 8 μm. The coating film thus obtained was irradiated with ultraviolet rays by a mask for forming a target pattern. At this time, the entire exposed portion is uniformly irradiated with parallel rays, and a device such as a mask aligner or a stepper is preferably used to align the mask and the substrate to the correct position. When ultraviolet rays are irradiated, the portion irradiated with ultraviolet rays is solidified.
紫外線可以使用g-線(波長:436nm)、h-線、i-線(波長:365nm)等。紫外線的照射量根據需要可以恰當選擇,本發明對此沒有限定。使固化後的塗膜接觸顯影液並溶解非曝光部而顯影,則可以形成目標圖案形狀。 As the ultraviolet light, a g-line (wavelength: 436 nm), an h-line, an i-line (wavelength: 365 nm), or the like can be used. The amount of ultraviolet rays to be irradiated can be appropriately selected as needed, and the present invention is not limited thereto. When the cured coating film is brought into contact with the developing solution and the non-exposed portion is dissolved and developed, a target pattern shape can be formed.
顯影方法採用液體添加法、浸漬法、噴塗等任意一種都可以。另外,顯影時可將基板傾斜任意角度。該顯影液通常為包含鹼性化合物和表面活性劑的水溶液。該鹼性化合物可以是無機以及有機鹼性化合物的任一種。無機鹼性化合物具體例可列舉出氫氧化鈉、氫氧化鉀、磷酸氫二鈉、磷酸二氫鈉、磷酸氫二銨、磷酸二氫銨、磷酸二氫鉀、矽酸鈉、矽酸鉀、碳酸鈉、碳酸鉀、碳酸氫鈉、碳酸氫鉀、硼酸鈉、硼酸鉀、硼酸銨等。另外,有機鹼性化合物具體例可列舉出四甲基氫氧化銨、2-羥乙基三甲基氫氧化銨、單甲胺、二甲胺、三甲胺、單乙胺、二乙胺、三乙胺、單異丙胺、二異丙胺、乙醇胺等。 The development method may be any one of a liquid addition method, a dipping method, and a spray coating. In addition, the substrate can be tilted at any angle during development. The developer is usually an aqueous solution containing a basic compound and a surfactant. The basic compound may be any of an inorganic as well as an organic basic compound. Specific examples of the inorganic basic compound include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium citrate, potassium citrate, Sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium borate, potassium borate, ammonium borate, and the like. Further, specific examples of the organic basic compound include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, and trisole. Ethylamine, monoisopropylamine, diisopropylamine, ethanolamine, and the like.
這些無機以及有機鹼性化合物可以分別單獨使用或組合兩種以 上使用。鹼顯影液中的鹼性化合物的濃度較佳為0.01~10重量%,進一步較佳為0.03~5重量%。 These inorganic and organic basic compounds may be used alone or in combination of two. Used on. The concentration of the basic compound in the alkali developing solution is preferably 0.01 to 10% by weight, and more preferably 0.03 to 5% by weight.
鹼顯影液中的表面活性劑可以從由非離子類表面活性劑、陰離子類表面活性劑或陽離子類表面活性劑組成的群組選擇至少一種使用。 The surfactant in the alkali developer may be at least one selected from the group consisting of a nonionic surfactant, an anionic surfactant, or a cationic surfactant.
非離子類表面活性劑的具體例可列舉出聚氧乙烯烷基醚、聚氧乙烯芳基醚、聚氧乙烯烷基芳基醚、其他的聚氧乙烯衍生物、氧乙烯/氧丙烯嵌段共聚物、山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇脂肪酸酯、丙三醇脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯烷基胺等。 Specific examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, and oxyethylene/oxypropylene blocks. Copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, glycerol fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene oxide Alkylamine and the like.
陰離子類表面活性劑的具體例可列舉出月桂醇硫酸酯鈉和油酸醇硫酸酯鈉等高級醇硫酸酯鹽類、月桂基硫酸鈉和月桂基硫酸銨等烷基硫酸鹽類、十二烷基苯磺酸鈉和十二烷基萘磺酸鈉等的烷基芳基磺酸鹽類等。 Specific examples of the anionic surfactant include higher alcohol sulfate salts such as sodium lauryl sulfate and sodium oleate sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, and dodecane. An alkylarylsulfonate such as sodium benzenesulfonate or sodium dodecylnaphthalenesulfonate.
陽離子類表面活性劑的具體例可列舉出十八烷基胺鹽酸鹽和月桂基三甲基氯化銨等胺鹽或季銨鹽等。這些表面活性劑可以單獨使用或組合使用兩種以上。 Specific examples of the cationic surfactant include an amine salt such as octadecylamine hydrochloride and lauryltrimethylammonium chloride, or a quaternary ammonium salt. These surfactants may be used alone or in combination of two or more.
顯影液中的表面活性劑的濃度通常為0.01~10重量%,較佳為0.05~8重量%,進一步較佳為0.1~5重量%。顯影後進行水洗,另外,必要時,可在150~230℃下後烘焙10~60分鐘。 The concentration of the surfactant in the developer is usually 0.01 to 10% by weight, preferably 0.05 to 8% by weight, and more preferably 0.1 to 5% by weight. After the development, the water is washed, and if necessary, it may be post-baked at 150 to 230 ° C for 10 to 60 minutes.
使用本發明的著色感光性樹脂組合物,經過以上各程序,可以在基板上形成特定的圖案。 Using the colored photosensitive resin composition of the present invention, a specific pattern can be formed on the substrate by the above respective procedures.
以下,為了具體說明本發明,例舉實施例進行詳細說明。但本發明涉及的實施例可以進行各種不同形式改變,本發明的範圍不應解釋為受限於下述實施例。本發明的實施例是為了向本領域技術人員更完整地說明本發明而提供。 Hereinafter, in order to specifically describe the present invention, an exemplary embodiment will be described in detail. However, the embodiments of the present invention are susceptible to various modifications and the scope of the present invention should not be construed as being limited to the embodiments described below. The embodiments of the present invention are provided to more fully illustrate the present invention by those skilled in the art.
製造例1、顏料分散組合物(M1)的製造 Production Example 1, Production of Pigment Dispersion Composition (M1)
將13.5重量份的顏料C.I.顏料紅254、顏料分散劑DISPERBYK-2001(BYK公司製造)5.0重量份、作為溶劑的丙二醇單甲基醚乙酸酯61.5重量份以及4-羥基-4-甲基-2-戊酮20重量份藉由珠磨機混合12小時,將其分散從而製造出顏料分散組合物M1。 15.5 parts by weight of pigment CI Pigment Red 254, pigment dispersant DISPERBYK-2001 (manufactured by BYK) 5.0 parts by weight, propylene glycol monomethyl ether acetate as solvent 61.5 parts by weight, and 4-hydroxy-4-methyl- 20 parts by weight of 2-pentanone was mixed by a bead mill for 12 hours, and it was dispersed to produce a pigment dispersion composition M1.
製造例2、顏料分散組合物(M2)的製造 Production Example 2, Production of Pigment Dispersion Composition (M2)
將13.5重量份的顏料C.I.顏料綠58、顏料分散劑DISPERBYK-2001(BYK公司製造)5.0重量份、作為溶劑的丙二醇單甲基醚乙酸酯61.5重量份以及4-羥基-4-甲基-2-戊酮20重量份藉由珠磨機混合12小時,將其分散從而製造出顏料分散組合物M2。 15.5 parts by weight of pigment CI Pigment Green 58, 5.0 parts by weight of pigment dispersant DISPERBYK-2001 (manufactured by BYK Corporation), 61.5 parts by weight of propylene glycol monomethyl ether acetate as a solvent, and 4-hydroxy-4-methyl- 20 parts by weight of 2-pentanone was mixed by a bead mill for 12 hours, and dispersed to prepare a pigment dispersion composition M2.
製造例3、顏料分散組合物(M3)的製造 Production Example 3, Production of Pigment Dispersion Composition (M3)
將13.5重量份的顏料C.I.顏料紅254、顏料分散劑DISPERBYK-2001(BYK公司製造)5.0重量份、作為溶劑的丙二醇單甲基醚乙酸酯81.5重量份通過珠磨機混合12小時,將其分散從而製造出顏料分散組合物M3。 5.0 parts by weight of pigment CI Pigment Red 254, a pigment dispersant DISPERBYK-2001 (manufactured by BYK), 5.0 parts by weight, and 81.5 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed by a bead mill for 12 hours. Dispersion to produce a pigment dispersion composition M3.
合成例1、鹼溶性樹脂的合成 Synthesis Example 1, Synthesis of alkali soluble resin
將丙二醇單甲醚乙酸酯120重量份、丙二醇單甲醚80重量份、AIBN2重量份、丙烯酸13重量份、甲基丙烯酸苄酯10重量份、4-甲基苯乙烯57重量份、甲基丙烯酸甲酯20重量份、正十二烷硫醇3重量份加入到包括攪拌機、溫度計、回流冷卻管、滴液漏斗和氮氣導入管的燒瓶,替換為氮氣氣氛。之後,進行攪拌,使反應液的溫度升至110℃並反應6小時。用前述方法製造的鹼溶性樹脂的固體成分酸值為100.2mgKOH/g,藉由GPC測定的重均分子量Mw為15110。 120 parts by weight of propylene glycol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN, 13 parts by weight of acrylic acid, 10 parts by weight of benzyl methacrylate, 57 parts by weight of 4-methylstyrene, methyl group 20 parts by weight of methyl acrylate and 3 parts by weight of n-dodecyl mercaptan were placed in a flask including a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube, and replaced with a nitrogen atmosphere. Thereafter, stirring was carried out to raise the temperature of the reaction liquid to 110 ° C and react for 6 hours. The alkali-soluble resin produced by the above method had a solid content acid value of 100.2 mgKOH/g, and the weight average molecular weight Mw measured by GPC was 15,110.
合成例2、光聚合引發劑(d1)的合成 Synthesis Example 2 Synthesis of Photopolymerization Initiator (d1)
步驟1 step 1
將37.3g的AlCl3和112.0g的二氯乙烷加入到氮氣氣氛的反應器中,保持5℃的溫度進行攪拌,在17.27g的乙醯氯溶液中溶解240.3g的二氯乙烷和48.1g的硝基咔唑,將前述溶解後的溶液以1小時滴入反應器中。之後,將溫度升至15℃並進一步攪拌2小時。將蒸餾水放入前述反應器中,洗淨並分離後,對溶劑進行乾燥,得到純度94%的反應物1。 37.3 g of AlCl 3 and 112.0 g of dichloroethane were placed in a reactor under a nitrogen atmosphere, stirred at a temperature of 5 ° C, and 240.3 g of dichloroethane and 48.1 were dissolved in 17.27 g of an acetonitrile chloride solution. The nitrocarbazole of g was dropped into the reactor in 1 hour. Thereafter, the temperature was raised to 15 ° C and further stirred for 2 hours. Distilled water was placed in the reactor, washed and separated, and the solvent was dried to obtain a reactant 1 having a purity of 94%.
步驟2 Step 2
將35.0g的前述反應物1、11.1g的鹽酸羥胺、15.1g的乙酸鈉、90g的乙醇和30g的蒸餾水加入到氮氣氣氛的反應器中,保持80℃的溫度並攪拌5小時。之後,放入蒸餾水,分離並乾燥析出物,得到純度92%的反應物2。 35.0 g of the aforementioned reactant 1, 11.1 g of hydroxylamine hydrochloride, 15.1 g of sodium acetate, 90 g of ethanol and 30 g of distilled water were placed in a reactor under a nitrogen atmosphere, and the temperature was maintained at 80 ° C and stirred for 5 hours. Thereafter, distilled water was placed, and the precipitate was separated and dried to obtain a reactant 2 having a purity of 92%.
步驟3 Step 3
將26.0g的反應物2和78g的二氯甲烷加入到氮氣氣氛的反應器中,在常溫下攪拌。之後,將用15.0g的二氯乙烷稀釋15.0g的乙酸酐的混合溶液以1小時滴入反應器後,攪拌1小時。攪拌後,放入蒸餾水進行數次洗淨之後,將二氯甲烷蒸發,得到純度90%的化學式2。此外,化學式2是化學式1的R1和R2為甲基的結構,可表示如下。此外,下述化學式2的化合物用0.01重量%濃度的丙二醇甲醚乙酸酯溶液在405nm處的吸光度測定為0.523。 26.0 g of the reactant 2 and 78 g of dichloromethane were added to a reactor under a nitrogen atmosphere, and stirred at normal temperature. Thereafter, a mixed solution of 15.0 g of acetic anhydride diluted with 15.0 g of dichloroethane was added dropwise to the reactor over 1 hour, followed by stirring for 1 hour. After stirring, the mixture was washed with distilled water for several times, and then dichloromethane was evaporated to obtain a chemical formula 2 having a purity of 90%. Further, Chemical Formula 2 is a structure in which R 1 and R 2 of Chemical Formula 1 are a methyl group, and can be represented as follows. Further, the compound of the following Chemical Formula 2 was determined to have an absorbance at 405 nm of 0.523 with a 0.01% by weight concentration of a propylene glycol methyl ether acetate solution.
實施例1 Example 1
將38.89重量份的前述製造例1製造的顏料分散組合物M1、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、合成例2製造的光聚合引發劑(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.52)0.71重量份、作為溶劑的4-羥基-4-甲基-2- 戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造實施例1的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, and light produced in Synthesis Example 2 a polymerization initiator (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.52) of 0.71 part by weight, 4-hydroxy-4-methyl-2- as a solvent 0.72 parts by weight of pentanone and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Example 1.
實施例2 Example 2
將38.89重量份的前述製造例2製造的顏料分散組合物M2、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、合成例2製造的光聚合引發劑(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.52)0.71重量份、作為溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造實施例2的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M2 produced in the above Production Example 2, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, and light produced in Synthesis Example 2 a polymerization initiator (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.52) of 0.71 part by weight, 4-hydroxy-4-methyl-2- as a solvent 0.72 parts by weight of pentanone and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Example 2.
實施例3 Example 3
將36.94重量份的前述製造例1製造的顏料分散組合物M1、0.26重量份的作為染料的C.I.溶劑黃21、合成例1製造的樹脂10.79重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.59重量份、合成例2製造的光聚合引發劑(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.52)0.72重量份、作為溶劑的4-羥基-4-甲基-2-戊酮1.11重量份、丙二醇單甲醚乙酸酯46.59重量份進行混合,製造實施例3的著色感光性樹脂組合物。 36.94 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 0.26 parts by weight of CI Solvent Yellow 21 as a dye, 10.79 parts by weight of a resin produced in Synthesis Example 1, and KAYARAD DPHA as a photopolymerizable compound (Japanese) 3.59 parts by weight of a photopolymerization initiator produced in Synthesis Example 2 (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.52) of 0.72 parts by weight as a solvent 1.11 parts by weight of 4-hydroxy-4-methyl-2-pentanone and 46.59 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Example 3.
實施例4 Example 4
將36.94重量份的前述製造例2製造的顏料分散組合物M2、0.26 重量份的作為染料的C.I.溶劑黃21、合成例1製造的樹脂10.79重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.59重量份、合成例2製造的光聚合引發劑(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.52)0.72重量份、作為溶劑的4-羥基-4-甲基-2-戊酮1.11重量份、丙二醇單甲醚乙酸酯46.59重量份進行混合,製造實施例4的著色感光性樹脂組合物。 36.94 parts by weight of the pigment dispersion composition M2, 0.26 produced in the above Production Example 2 a part by weight of CI solvent yellow 21 as a dye, 10.79 parts by weight of a resin produced in Synthesis Example 1, 3.59 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, and a photopolymerization initiator produced in Synthesis Example 2 (at 0.01) The absorbance at 405 nm of the propylene glycol methyl ether acetate solution containing the photopolymerization initiator at a concentration of more than % by weight or more is 0.52), 0.72 parts by weight, and 1.11 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent. 46.59 parts by weight of propylene glycol monomethyl ether acetate was mixed to prepare a colored photosensitive resin composition of Example 4.
比較例1 Comparative example 1
將38.89重量份的前述製造例1製造的顏料分散組合物M1、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的Irgacure OXE-01(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.013,BASF公司)0.71重量份、作為溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造比較例1的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, as a photopolymerization initiator Irgacure OXE-01 (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.013, BASF Corporation) 0.71 part by weight, 4-hydroxy-4-methyl as a solvent 0.72 parts by weight of keto-2-pentanone and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Comparative Example 1.
比較例2 Comparative example 2
將38.89重量份的前述製造例1製造的顏料分散組合物M1、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的Irgacure OXE-02(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.004,BASF公司)0.71重量份、作為 溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造比較例2的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, as a photopolymerization initiator Irgacure OXE-02 (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.004, BASF Corporation) of 0.71 part by weight 0.72 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Comparative Example 2.
比較例3 Comparative example 3
將38.89重量份的前述製造例1製造的顏料分散組合物M1、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的N-1919(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.015,旭電業公司)0.71重量份、作為溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造比較例3的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, as a photopolymerization initiator N-1919 (absorbance of propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.015, Asahi Electric Co., Ltd.) 0.71 part by weight, 4-hydroxy-4-methyl as a solvent 0.72 parts by weight of 2-pentanone and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Comparative Example 3.
比較例4 Comparative example 4
將38.89重量份的前述製造例2製造的顏料分散組合物M2、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的Irgacure OXE-01(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.013,BASF公司)0.71重量份、作為溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造比較例4的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M2 produced in the above Production Example 2, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, as a photopolymerization initiator Irgacure OXE-01 (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.013, BASF Corporation) 0.71 part by weight, 4-hydroxy-4-methyl as a solvent 0.72 parts by weight of keto-2-pentanone and 45.48 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Comparative Example 4.
比較例5 Comparative Example 5
將38.89重量份的前述製造例2製造的顏料分散組合物M2、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的Irgacure OXE-02(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.004,BASF公司)0.71重量份、作為溶劑的4-羥基-4-甲基-2-戊酮0.72重量份、丙二醇單甲醚乙酸酯45.48重量份進行混合,製造比較例5的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M2 produced in the above Production Example 2, 10.65 parts by weight of the resin produced in Synthesis Example 1, and KAYARAD as a photopolymerizable compound 3.55 parts by weight of DPHA (Nippon Chemical), Irgacure OXE-02 as a photopolymerization initiator (absorbance of propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at 405 nm is 0.004, BASF 0.71 parts by weight, 0.72 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, and 45.48 parts by weight of propylene glycol monomethyl ether acetate, and the colored photosensitive resin composition of Comparative Example 5 was produced. .
比較例6 Comparative Example 6
將36.94重量份的前述製造例1製造的顏料分散組合物M1、0.26重量份的作為染料的C.I.溶劑黃21、合成例1製造的樹脂10.79重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.59重量份、作為光聚合引發劑的Irgacure OXE-02(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.004,BASF公司)0.72重量份、作為溶劑的4-羥基-4-甲基-2-戊酮1.11重量份、丙二醇單甲醚乙酸酯46.59重量份進行混合,製造比較例6的著色感光性樹脂組合物。 36.94 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 0.26 parts by weight of CI Solvent Yellow 21 as a dye, 10.79 parts by weight of a resin produced in Synthesis Example 1, and KAYARAD DPHA as a photopolymerizable compound (Japanese) Medicine: 3.59 parts by weight of Irgacure OXE-02 as a photopolymerization initiator (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.004, BASF) 0.72 by weight The mixture was mixed with 1.11 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent and 46.59 parts by weight of propylene glycol monomethyl ether acetate to prepare a colored photosensitive resin composition of Comparative Example 6.
比較例7 Comparative Example 7
將36.94重量份的前述製造例1製造的顏料分散組合物M1、0.26重量份的作為染料的C.I.溶劑黃21、合成例1製造的樹脂10.79重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.59重量份、作為光聚合引發劑的N-1919(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.015,旭電業公司)0.72重量份、作為溶劑的4-羥基-4-甲基-2-戊酮1.11重 量份、丙二醇單甲醚乙酸酯46.59重量份進行混合,製造比較例7的著色感光性樹脂組合物。 36.94 parts by weight of the pigment dispersion composition M1 produced in the above-mentioned Production Example 1, 0.26 parts by weight of CI Solvent Yellow 21 as a dye, 10.79 parts by weight of a resin produced in Synthesis Example 1, and KAYARAD DPHA as a photopolymerizable compound (Japanese) Medicine: 3.59 parts by weight of N-1919 as a photopolymerization initiator (absorbance of propylene glycol methyl ether acetate solution containing photopolymerization initiator at a concentration of 0.01% by weight or more at 405 nm of 0.015, Asahi Electric Co., Ltd.) 0.72 parts by weight , as a solvent, 4-hydroxy-4-methyl-2-pentanone 1.11 The amount of the mixture and 46.59 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition of Comparative Example 7.
比較例8 Comparative Example 8
將38.89重量份的前述製造例3製造的顏料分散組合物M3、合成例1製造的樹脂10.65重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.55重量份、作為光聚合引發劑的N-1919(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.015,旭電業公司)0.71重量份、作為溶劑的丙二醇單甲醚乙酸酯46.2重量份進行混合,製造比較例8的著色感光性樹脂組合物。 38.89 parts by weight of the pigment dispersion composition M3 produced in the above Production Example 3, 10.65 parts by weight of the resin produced in Synthesis Example 1, and 3.55 parts by weight of KAYARAD DPHA (Nippon Chemical Co., Ltd.) as a photopolymerizable compound, as a photopolymerization initiator N-1919 (absorbance of propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.015, Asahi Electric Co., Ltd.) 0.71 part by weight, propylene glycol monomethyl ether acetate as a solvent 46.2 The colored photosensitive resin composition of Comparative Example 8 was produced by mixing in parts by weight.
比較例9 Comparative Example 9
將36.94重量份的前述製造例3製造的顏料分散組合物M3、0.26重量份的作為染料的C.I.溶劑黃21、合成例1製造的樹脂10.79重量份、作為光聚合性化合物的KAYARAD DPHA(日本化藥)3.59重量份、合成例2製造的光聚合引發劑(以0.01重量%以上的濃度包含光聚合引發劑的丙二醇甲醚乙酸酯溶液在405nm處的吸光度為0.52)0.72重量份、作為溶劑的丙二醇單甲醚乙酸酯47.7重量份進行混合,製造比較例9的著色感光性樹脂組合物。 36.94 parts by weight of the pigment dispersion composition M3 produced in the above Production Example 3, 0.26 parts by weight of CI Solvent Yellow 21 as a dye, 10.79 parts by weight of a resin produced in Synthesis Example 1, and KAYARAD DPHA as a photopolymerizable compound (Japanese) 3.59 parts by weight of a photopolymerization initiator produced in Synthesis Example 2 (absorbance of a propylene glycol methyl ether acetate solution containing a photopolymerization initiator at a concentration of 0.01% by weight or more at a 405 nm of 0.52) of 0.72 parts by weight as a solvent 47.7 parts by weight of propylene glycol monomethyl ether acetate was mixed to prepare a colored photosensitive resin composition of Comparative Example 9.
實驗例1、濾色器的製造 Experimental Example 1, Manufacturing of Color Filters
用旋轉塗布法將前述實施例1至4和比較例1至9的著色感光性樹脂組合物塗布在2平方英寸的玻璃基板(康寧公司製造,“EAGLE XG”)上後,將其放置於加熱板上、在100℃的溫度下保持3分鐘,形成薄膜。接著,在前述薄膜上載置具有透光率在1~100%的範圍內呈階梯狀變化的圖案與1μm~50μm線寬/間隔圖案的試驗光掩模,將與試驗光掩模之間的間隔設為300μm,照射紫外線。此時,紫外線光源使用包括g、h、i射線全部的1KW高壓汞燈以40mJ/cm2的照度進行照射,沒有使用特殊的濾光器。將照射了前述紫外線的薄膜浸漬於pH 10.5的KOH水溶液顯影溶液中2分鐘,使其顯影。使用蒸餾水洗淨塗覆有前述薄膜的玻璃板後,吹入氮氣進行乾燥,在230℃的加熱爐中加熱25分鐘,製造出濾色器。前述製造出的濾色器的薄膜厚度為2.3μm。 The colored photosensitive resin compositions of the above Examples 1 to 4 and Comparative Examples 1 to 9 were applied onto a 2 square inch glass substrate ("EAGLE XG" manufactured by Corning Incorporated) by spin coating, and then placed in a heating. The sheet was held at a temperature of 100 ° C for 3 minutes to form a film. Next, a test photomask having a pattern in which the light transmittance is changed in a range of 1 to 100% and a line width/space pattern of 1 μm to 50 μm is placed on the film, and the interval from the test photomask is placed. It was set to 300 μm and irradiated with ultraviolet rays. At this time, the ultraviolet light source was irradiated with a illuminance of 40 mJ/cm 2 using a 1 KW high-pressure mercury lamp including all of g, h, and i rays, and no special filter was used. The film irradiated with the above ultraviolet rays was immersed in a KOH aqueous solution developing solution having a pH of 10.5 for 2 minutes to be developed. The glass plate coated with the above-mentioned film was washed with distilled water, dried with nitrogen gas, and heated in a heating furnace at 230 ° C for 25 minutes to produce a color filter. The film thickness of the above-described color filter was 2.3 μm.
實驗例2、濾色器的製造 Experimental Example 2, Manufacturing of Color Filters
除了未使用試驗光掩模之外,用與實驗例1相同的方法分別製造濾色器。 A color filter was separately manufactured in the same manner as in Experimental Example 1, except that the test photomask was not used.
實驗例3、實驗例1和實驗例2的濾色器的物性測定 Physical properties of color filters of Experimental Example 3, Experimental Example 1 and Experimental Example 2
對實驗例1中製造的各濾色器測定黏附性和圖案線寬,對實驗例2中製造的各濾色器測定耐溶劑性。物性測定結果示於以下表1中。 The adhesion and the line width of the pattern were measured for each of the color filters manufactured in Experimental Example 1, and the solvent resistance of each of the color filters manufactured in Experimental Example 2 was measured. The physical property measurement results are shown in Table 1 below.
(1)黏附性 (1) Adhesion
通過光學顯微鏡觀察生成的圖案時,評價圖案上的剝裂現象程度。 When the generated pattern was observed by an optical microscope, the degree of peeling phenomenon on the pattern was evaluated.
○:圖案上沒有剝裂 ○: no peeling on the pattern
△:圖案上有1~3個剝裂 △: 1~3 peelings on the pattern
×:圖案上有4個以上剝裂 ×: There are more than 4 strips on the pattern.
(2)圖案線寬 (2) pattern line width
用掃描型電子顯微鏡測定生成的圖案的線寬。圖案的線寬測定為光掩膜的線寬以上的情況下,著色感光性樹脂組合物的靈敏度充分,線寬擴大。 The line width of the resulting pattern was measured by a scanning electron microscope. When the line width of the pattern is measured to be equal to or greater than the line width of the photomask, the sensitivity of the colored photosensitive resin composition is sufficient, and the line width is enlarged.
(3)耐溶劑性 (3) Solvent resistance
將濾色器在常溫的NMP溶液中浸漬30分鐘後,用超純水洗淨並在加熱至120℃的熱板上乾燥2分鐘後,測定浸漬前後的色度。此時使用的公式通過表示以L*、a*、b*定義的三維色度計下的顏色變化的下述數學式1來計算,顏色變化值越小,越能夠製造出可靠性高的濾色器。 The color filter was immersed in a normal temperature NMP solution for 30 minutes, washed with ultrapure water, and dried on a hot plate heated to 120 ° C for 2 minutes, and then the chromaticity before and after the immersion was measured. The formula used at this time is calculated by the following mathematical expression 1 indicating the color change under the three-dimensional colorimeter defined by L*, a*, b*, and the smaller the color change value, the more reliable the filter can be manufactured. Color.
[數學式1]△Eab*=〔(△L*)2+(△a*)2+(△b*)2〕^0.5 [Math 1] △Eab*=[(△L*)2+(△a*)2+(△b*)2]^0.5
藉由前述結果,使用了包含作為光聚合引發劑的前述合成例2製造的化學式2的化合物以及作為溶劑的4-羥基-4-甲基-2-戊酮的本發明著色感光性樹脂組合物的實施例1至4的濾色器,與比較例1至9的濾色器相比,表現出黏附性、圖案線寬和耐溶劑性的任一性能均優異的結果。 By the above results, the coloring photosensitive resin composition of the present invention containing the compound of Chemical Formula 2 produced as the photopolymerization initiator and the 4-hydroxy-4-methyl-2-pentanone as a solvent is used. The color filters of Examples 1 to 4 exhibited excellent results in any of the properties of adhesion, pattern line width, and solvent resistance as compared with the color filters of Comparative Examples 1 to 9.
因此可知,本發明的著色感光性樹脂組合物在貯存穩定性、靈敏度和黏附性上具有更優異的效果。 Therefore, it is understood that the colored photosensitive resin composition of the present invention has more excellent effects in storage stability, sensitivity, and adhesion.
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