JP6476660B2 - Photocurable resin composition, photocurable light-shielding coating material using the same, liquid crystal display panel, and liquid crystal display device - Google Patents
Photocurable resin composition, photocurable light-shielding coating material using the same, liquid crystal display panel, and liquid crystal display device Download PDFInfo
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- JP6476660B2 JP6476660B2 JP2014175152A JP2014175152A JP6476660B2 JP 6476660 B2 JP6476660 B2 JP 6476660B2 JP 2014175152 A JP2014175152 A JP 2014175152A JP 2014175152 A JP2014175152 A JP 2014175152A JP 6476660 B2 JP6476660 B2 JP 6476660B2
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- Prior art keywords
- liquid crystal
- crystal display
- light
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- mass
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- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
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- MGXHYQAQEKLYFL-UHFFFAOYSA-N C=CC(OC(COCCOCCOCCO)O)=O.N=C=O Chemical compound C=CC(OC(COCCOCCOCCO)O)=O.N=C=O MGXHYQAQEKLYFL-UHFFFAOYSA-N 0.000 description 1
- FZCMFHPUKKCQDK-UHFFFAOYSA-N CC(C(OC(COCCOCCOCCO)O)=O)=C.N=C=O Chemical compound CC(C(OC(COCCOCCOCCO)O)=O)=C.N=C=O FZCMFHPUKKCQDK-UHFFFAOYSA-N 0.000 description 1
- SRORDPCXIPXEAX-UHFFFAOYSA-N CCCCCCCCCCCCCP(CCCCCCCCCCCCC)(O)(OCCCCCCCC)OCCCCCCCC.CCCCCCCCCCCCCP(CCCCCCCCCCCCC)(O)(OCCCCCCCC)OCCCCCCCC Chemical compound CCCCCCCCCCCCCP(CCCCCCCCCCCCC)(O)(OCCCCCCCC)OCCCCCCCC.CCCCCCCCCCCCCP(CCCCCCCCCCCCC)(O)(OCCCCCCCC)OCCCCCCCC SRORDPCXIPXEAX-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
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- HLGYYLSEQXUWKC-UHFFFAOYSA-N OCCCCOC(C(=C)C)=O.OCCCOC(C(=C)C)=O Chemical compound OCCCCOC(C(=C)C)=O.OCCCOC(C(=C)C)=O HLGYYLSEQXUWKC-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- VTIXMGZYGRZMAW-UHFFFAOYSA-N ditridecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)OCCCCCCCCCCCCC VTIXMGZYGRZMAW-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- SAMYCKUDTNLASP-UHFFFAOYSA-N hexane-2,2-diol Chemical compound CCCCC(C)(O)O SAMYCKUDTNLASP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- FRCAGVUKJQCWBD-UHFFFAOYSA-L iodine green Chemical compound [Cl-].[Cl-].C1=CC(N(C)C)=CC=C1C(\C=1C=CC(=CC=1)[N+](C)(C)C)=C/1C=C(C)C(=[N+](C)C)C=C\1 FRCAGVUKJQCWBD-UHFFFAOYSA-L 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Description
本発明は、光硬化性樹脂組成物およびそれを用いた光硬化性遮光塗料、液晶表示パネル、液晶表示装置に関する。 The present invention relates to a photocurable resin composition, a photocurable light-shielding coating material using the same, a liquid crystal display panel, and a liquid crystal display device.
液晶表示装置は、液晶表示パネルと該液晶表示パネルを裏面から照明するバックライトで構成されている。そして、これらを筐体内に組み込む際には、バックライトの照明光が、液晶表示パネルの画像表示領域のみから透過し、例えば、液晶表示パネルと筐体との隙間などから漏出するのを抑制することが必要である。 The liquid crystal display device includes a liquid crystal display panel and a backlight that illuminates the liquid crystal display panel from the back side. When these are incorporated into the housing, the illumination light of the backlight is transmitted only from the image display area of the liquid crystal display panel, and is prevented from leaking from, for example, a gap between the liquid crystal display panel and the housing. It is necessary.
しかも、液晶表示装置においては、液晶表示装置の画面枠に対する狭額縁の要求があるため、額縁部分における筐体と液晶表示パネルとの隙間からの光漏れが発生し易くなる。 In addition, in the liquid crystal display device, since there is a demand for a narrow frame for the screen frame of the liquid crystal display device, light leakage from the gap between the casing and the liquid crystal display panel at the frame portion is likely to occur.
光漏れ対策としては、特許文献１のように、遮光性両面接着シートをバックライトと液晶表示パネルとの間の周辺部に配置する方法、特許文献２のように、光反射防止膜または光反射防止テープやスプレーなどで吹き付ける黒色の塗料などの光漏洩防止材をバックライトを収納するためのケースと液晶表示パネルとの間に配置する方法等が提案されている。 As a countermeasure against light leakage, a method of disposing a light-shielding double-sided adhesive sheet in the peripheral portion between the backlight and the liquid crystal display panel as in Patent Document 1, and a light reflection preventing film or light reflection as in Patent Document 2. A method of arranging a light leakage prevention material such as a black paint sprayed with a prevention tape or a spray between a case for storing a backlight and a liquid crystal display panel has been proposed.
しかしながら、これらの方法では遮光シートの幅が狭くなると配置する作業が煩雑になり、寸法精度や作業に時間がかかるという問題が生じ、また、遮光性塗料を塗布する方法の場合、溶剤乾燥型や加熱硬化型は、塗料を完全に乾燥硬化させる為に、高温度処理、また長時間処理が必要である。一方、短時間処理、例えば数秒〜数分での硬化が可能な光硬化性遮光塗料が開発されているが、遮光に必要な膜厚、数百μｍ程度を硬化させる光硬化性遮光塗料は得られていない。また、塗膜表面にタック性があるとごみや誇りが付着し、それを解決するために他官能の単量体を多く配合するという方法があるが、膜がもろくなり、被着体への密着性が低下するという問題が発生する。 However, in these methods, when the width of the light-shielding sheet becomes narrow, the work of arranging becomes complicated, and there arises a problem that it takes time for dimensional accuracy and work. In the case of a method of applying a light-shielding paint, a solvent drying type or The heat-curing type requires high-temperature treatment and long-time treatment in order to completely dry and cure the paint. On the other hand, photocurable light-shielding paints that can be cured in a short time, for example, several seconds to several minutes, have been developed. It is not done. In addition, if there is tackiness on the surface of the coating film, dust or pride adheres to it, and there is a method of adding many other functional monomers to solve it, but the film becomes brittle and it adheres to the adherend The problem that adhesiveness falls occurs.
本発明の解決しようとする課題は、上述のような従来技術の問題点を解決し、遮光に必要な膜厚を硬化させることができる光硬化性樹脂組成物若しくは光硬化性遮光塗料を提供することを目的とする。また、この光硬化性樹脂組成物若しくは光硬化性遮光塗料を用いた液晶表示パネル及びこれを用いた液晶表示装置を提供するものである。 The problem to be solved by the present invention is to provide a photocurable resin composition or a photocurable light-shielding paint capable of solving the above-mentioned problems of the prior art and curing the film thickness necessary for light shielding. For the purpose. Moreover, the liquid crystal display panel using this photocurable resin composition or a photocurable light-shielding coating material, and a liquid crystal display device using the same are provided.
本発明は、次に関する。
１． （Ａ）重量平均分子量が５００〜１０，０００の重合性不飽和基を有する樹脂、（Ｂ）重合性不飽和基を有する単量体および（Ｃ）分子中に二重結合を有するリン酸化合物である単量体を含有し、（Ｄ）光重合開始剤を（Ａ）成分と（Ｂ）成分の総計１００質量部に対して、１〜１０質量部を含有してなる光硬化性樹脂組成物。
２． さらに、平均粒子径が１μｍ以下のものである（Ｅ）有機顔料を含み、（Ｅ）成分が前記（Ａ）成分と（Ｂ）成分の総計１００質量部に対して０．１〜５質量部を含有する項１に記載の光硬化性樹脂組成物。
３． 項１又は項２のいずれかに記載の光硬化性樹脂組成物を含む光硬化性遮光塗料。
４． 項３に記載の光硬化性遮光塗料をパネル外周に塗布し、遮光した液晶表示パネル。
５． 項４に記載された液晶表示パネルを用いた液晶表示装置。
The present invention relates to the following.
1. (A) Resin having a polymerizable unsaturated group having a weight average molecular weight of 500 to 10,000, (B) a monomer having a polymerizable unsaturated group, and (C) a phosphoric acid compound having a double bond in the molecule A photocurable resin composition comprising 1 to 10 parts by mass of (D) a photopolymerization initiator with respect to a total of 100 parts by mass of the component (A) and the component (B). object.
2. Furthermore, (E) an organic pigment whose average particle diameter is 1 micrometer or less is included, and (E) component is 0.1-5 mass parts with respect to a total of 100 mass parts of said (A) component and (B) component. Item 2. The photocurable resin composition according to Item 1, comprising
3. Item 3. A photocurable light-shielding coating material comprising the photocurable resin composition according to any one of Items 1 and 2.
4). Item 4. A liquid crystal display panel in which the photocurable light-shielding coating material according to Item 3 is applied to the outer periphery of the panel to shield the light.
5. Item 5. A liquid crystal display device using the liquid crystal display panel according to item 4.
本発明によれば、短時間処理で遮光に必要な膜厚を硬化させることが可能である光硬化性遮光塗料であり、この塗料をパネル側面部へ塗布することで光漏れを抑制した液晶表示装置の製造法を提供することができる。 According to the present invention, a light-curable light-shielding paint capable of curing a film thickness necessary for light shielding in a short time treatment, and a liquid crystal display in which light leakage is suppressed by applying this paint to a side surface of the panel A method of manufacturing the device can be provided.
本発明に係る光硬化性樹脂組成物は、短時間処理が可能で、塗膜深部まで硬化でき、光硬化性遮光塗料として好適である。また、この塗料をパネル端面部へ塗布することで光漏れを抑制した液晶表示装置の製造法を提供することができる。 The photocurable resin composition according to the present invention can be processed for a short time, can be cured to the deep part of the coating film, and is suitable as a photocurable light-shielding coating material. Moreover, the manufacturing method of the liquid crystal display device which suppressed light leakage by apply | coating this coating material to a panel end surface part can be provided.
以下に本発明をその好適な実施形態に即して詳細に説明する。 Hereinafter, the present invention will be described in detail with reference to preferred embodiments thereof.
（Ａ）重量平均分子量が５００〜１０，０００の重合性不飽和基を有する樹脂の具体例としては、例えば、ウレタン（メタ）アクリレート、ポリエステル（メタ）アクリレート、トリス（アクリロキシテトラエチレングリコールイソシアネート）ヘキサメチレンイソシアヌレート、トリス（メタクリロキシテトラエチレングリコールイソシアネート）ヘキサメチレンイソシアヌレートなどがある。これらは１種を単独で又は２種以上を組み合わせて用いることができる。
重量平均分子量が小さすぎると成膜性が劣るようになり、大きすぎると樹脂組成物の粘度が高くなり塗装性に劣る傾向がある。上記の重量平均分子量は、１，０００〜８，０００の範囲にあることがより好ましい。
重量平均分子量は、例えば、ゲルパーミエーションクロマトグラフィーにより、標準物質（例えば、標準ポリスチレン）の検量線を用いて、測定することができる。
(A) Specific examples of the resin having a polymerizable unsaturated group having a weight average molecular weight of 500 to 10,000 include, for example, urethane (meth) acrylate, polyester (meth) acrylate, and tris (acryloxytetraethylene glycol isocyanate). Examples include hexamethylene isocyanurate and tris (methacryloxytetraethylene glycol isocyanate) hexamethylene isocyanurate. These can be used individually by 1 type or in combination of 2 or more types.
If the weight average molecular weight is too small, the film formability becomes poor, and if it is too large, the viscosity of the resin composition tends to be high and the paintability tends to be poor. The weight average molecular weight is more preferably in the range of 1,000 to 8,000.
The weight average molecular weight can be measured, for example, by gel permeation chromatography using a calibration curve of a standard substance (for example, standard polystyrene).
ウレタン（メタ）アクリレートは、多価イソシアネート化合物又はイソシアネート基を有するポリウレタンとヒドロキシル基含有（メタ）アクリレート化合物又はアクリル酸、メタクリル酸若しくはカルボキシル基を有する（メタ）アクリレートとを反応させて得ることができる。
多価イソシアネート化合物としては、トリレンジイソシアネート、キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、テトラメチルキシリレンジイソシアネート、イソフォロンジイソシアネート、水素添加されたトリレンジイソシアネート、水素添加されたキシリレンジイソシアネート、水素添加されたジフェニルメタンジイソシアネート、ノルボルネンジイソシアネート等のジイソシアネート、さらには上記したジイソシアネートの重合体、又は、ジイソシアネートの尿素変性体、ビュレット変性体等がある。
上記したイソシアネート基を有するポリウレタンは、多価アルコール化合物と上記のような多価イソシアネート化合物とを多価イソシアネート化合物過剰で反応させて得られ、通常、両末端にイソシアネート基を有する。多価アルコールとしては、プロピレングリコール、テトラメチレングリコール、１，４−ブタンジオール、１，５−ペンタンジオール、１，６−ヘキサンジオール、ネオペンチルグリコール、１，４−シクロヘキサンジメタノール、２−メチル−１，８−オクタンジオール、１，９−ノナンジオール、３−メチル−１，５−ペンタンジオール、ポリ１，２−ブチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、エチレングリコール−プロピレングリコール・ブロックコポリマー、エチレングリコール−テトラメチレングリコールコポリマー、メチルペンタンジオール変性ポリテトラメチレングリコール、プロピレングリコール変性ポリテトラメチレングリコール、ビスフェノールＡのプロピレンオキシド付加体、水添ビスフェノールＡのプロピレンオキシド付加体、ビスフェノールＦのプロピレンオキシド付加体、水添ビスフェノールＦのプロピレンオキシド付加体等がある。
水酸基を有する（メタ）アクリレートとしては、２−ヒドロキエチルアクリレート、２−ヒドロキシプロピルアクリレート、３−ヒドロキシプロピルアクリレート、４−ヒドロキシブチルアクリレート、ポリエチレングリコールモノアクリレート、ポリプロピレングリコールモノアクリレート、エチレングリコール−プロピレングリコール・ブロックコポリマーモノアクリレート、エチレングリコール−テトラメチレングリコールコポリマーモノアクリレート、カプロラクトン変性モノアクリレート（商品名プラクセルＦＡシリーズ、ダイセル化学（株）製）、ペンタエリスリトールトリアクリレート等のアクリル酸誘導体、２−ヒドロキエチルメタクリレート、２−ヒドロキシプロピルメタクリレート、３−ヒドロキシプロピルメタクリレート、４−ヒドロキシブチルメタクリレート、ポリエチレングリコールモノメタクリレート、ポリプロピレングリコールモノメタクリレート、エチレングリコール−プロピレングリコール・ブロックコポリマーモノメタクリレート、エチレングリコール−テトラメチレングリコールコポリマーモノメタクリレート、カプロラクトン変性モノメタクリレート（商品名プラクセルＦＭシリーズ：ダイセル化学（株）製）、ペンタエリスリトールトリメタクリレート等のメタクリル酸誘導体等がある。
また、上記と同様のポリウレタンであるが、多価アルコール過剰で反応させて得られる末端に水酸基を有するポリウレタンを、アクリル酸又はメタクリル酸、カルボキシル基を有する（メタ）アクリレート又はグリシシジル（メタ）アクリレート等のグリシジル基を有する（メタ）アクリレート又はイソシアネート基を有する（メタ）アクリレートと反応させることによりを得ることもできる
The urethane (meth) acrylate can be obtained by reacting a polyvalent isocyanate compound or polyurethane having an isocyanate group with a hydroxyl group-containing (meth) acrylate compound or acrylic acid, methacrylic acid or a (meth) acrylate having a carboxyl group. .
Polyisocyanate compounds include tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylylene. Examples thereof include diisocyanates such as diisocyanate, hydrogenated diphenylmethane diisocyanate, norbornene diisocyanate, and polymers of the diisocyanates described above, or urea-modified products and burette-modified products of diisocyanates.
The above-mentioned polyurethane having an isocyanate group is obtained by reacting a polyhydric alcohol compound with the above polyvalent isocyanate compound in excess of the polyvalent isocyanate compound, and usually has an isocyanate group at both ends. Examples of polyhydric alcohols include propylene glycol, tetramethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, 2-methyl- 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, poly1,2-butylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene glycol-propylene glycol block copolymer, Ethylene glycol-tetramethylene glycol copolymer, methylpentanediol modified polytetramethylene glycol, propylene glycol modified polytetramethylene glycol, propylene oxide adduct of bisphenol A Propylene oxide adduct of hydrogenated bisphenol A, propylene oxide adduct of bisphenol F, there is a propylene oxide adduct of hydrogenated bisphenol F.
As the (meth) acrylate having a hydroxyl group, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, polyethylene glycol monoacrylate, polypropylene glycol monoacrylate, ethylene glycol-propylene glycol, Block copolymer monoacrylate, ethylene glycol-tetramethylene glycol copolymer monoacrylate, caprolactone-modified monoacrylate (trade name Plaxel FA series, manufactured by Daicel Chemical Industries), acrylic acid derivatives such as pentaerythritol triacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate 4-hydroxybutyl methacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monomethacrylate, ethylene glycol-propylene glycol block copolymer monomethacrylate, ethylene glycol-tetramethylene glycol copolymer monomethacrylate, caprolactone-modified monomethacrylate (trade name Plaxel FM series: Daicel Chemical Co., Ltd.) and methacrylic acid derivatives such as pentaerythritol trimethacrylate.
Moreover, although it is the same polyurethane as the above, the polyurethane which has a hydroxyl group at the terminal obtained by making it react with polyhydric alcohol excess, acrylic acid or methacrylic acid, (meth) acrylate or glycidyl (meth) acrylate which has a carboxyl group, etc. It can also be obtained by reacting with (meth) acrylate having a glycidyl group or (meth) acrylate having an isocyanate group.
ポリエステル（メタ）アクリレートは、例えば、末端が水酸基であるポリエステルの（メタ）アクリレートである。詳しくは、ポリエステルポリオールとアクリル酸又はメタクリル酸、カルボキシル基を有する（メタ）アクリレート又はグリシジル基を有する（メタ）アクリレート又はイソシアネート基を有する（メタ）アクリレートを反応させることによりポリエステル（メタ）アクリレートを得ることができる。両末端が水酸基であるポリエステルのジ（メタ）アクリレートが特に好ましい。ポリエステルポリオールは、飽和酸と多価アルコールを反応させて製造することができる。飽和酸としては、アゼライン酸、アジピン酸、セバチン酸等の脂肪族ジカルボン酸があり、多価アルコールとしては、エチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、ブチレングリコール、ポリエチレングリコール、ポリプロピレングリコール等がある。
また、飽和酸と多価アルコールを反応させてポリエステルポリカルボン酸を作製し、水酸基を有する（メタ）アクリレート又はイソシアネート基を有する（メタ）アクリレート又はグリシシジル（メタ）アクリレートを反応させることによりポリエステル（メタ）アクリレートを得ることができる。この場合、特に、ポリエステルポリカルボン酸と水酸基を有する（メタ）アクリレートの反応物が好ましい。
The polyester (meth) acrylate is, for example, a polyester (meth) acrylate having a hydroxyl group at the end. Specifically, polyester (meth) acrylate is obtained by reacting polyester polyol with acrylic acid or methacrylic acid, (meth) acrylate having a carboxyl group, (meth) acrylate having a glycidyl group, or (meth) acrylate having an isocyanate group. be able to. Particularly preferred is a polyester di (meth) acrylate having hydroxyl groups at both ends. The polyester polyol can be produced by reacting a saturated acid and a polyhydric alcohol. Examples of saturated acids include aliphatic dicarboxylic acids such as azelaic acid, adipic acid, and sebacic acid. Examples of polyhydric alcohols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, butylene glycol, polyethylene glycol, and polypropylene glycol. is there.
Further, a polyester polycarboxylic acid is prepared by reacting a saturated acid and a polyhydric alcohol, and a polyester (meta) is obtained by reacting a (meth) acrylate having a hydroxyl group, a (meth) acrylate having an isocyanate group or a glycidyl (meth) acrylate. ) Acrylate can be obtained. In this case, a reaction product of polyester polycarboxylic acid and (meth) acrylate having a hydroxyl group is particularly preferable.
本発明に用いられる（Ｂ）重合性不飽和基を有する単量体としては、スチレン、ビニルトルエン、α−メチルスチレン、ｐ−ターシャリーブチルスチレン、クロルスチレン、ジビニルベンゼン、ジアリルフタレート、２−ヒドロオキシエチルメタクリレート、２−ヒドロオキシプロピルメタクリレート、メチルメタクリレート、エチルメタクリレート、ラウリルメタクリレート、メタクリル酸とカージュラＥ−１０（シェル化学社製、高級脂肪酸のグリシジルエステルの商品名）の反応物などの１官能性のメタクリル酸エステル、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、１，６−ヘキサンジオールジメタクリレートなどの２官能性のメタクリル酸エステル、トリメチロールプロパントリメタクリレートなどの３官能性のメタクリル酸エステル、メチルアクリレート、エチルアクリレート、ラウリルアクリレート、２−ヒドロオキシエチルアクリレート、２−ヒドロオキシプロピルアクリレート、アクリル酸とカージュラＥ−１０の反応物などの１官能性のアクリル酸エステル、エチレングリコールジアクリレート、ジエチレングリコールジアクリレート、１，６−ヘキサンジオールジアクリレートなどの２官能のアクリル酸エステル、トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレートなどの３官能性のアクリル酸エステル、ペンタエリスリトールテトラアクリレートなどの４官能性のアクリル酸エステル、ペンタエリスリトールヘキサアクリレートなどの６官能性のアクリル酸エステルなどが用いられる。 Examples of the monomer (B) having a polymerizable unsaturated group used in the present invention include styrene, vinyl toluene, α-methyl styrene, p-tertiary butyl styrene, chlorostyrene, divinylbenzene, diallyl phthalate, 2-hydro Monofunctionality such as reaction product of oxyethyl methacrylate, 2-hydroxypropyl methacrylate, methyl methacrylate, ethyl methacrylate, lauryl methacrylate, methacrylic acid and Cardura E-10 (trade name of glycidyl ester of higher fatty acid, manufactured by Shell Chemical Co., Ltd.) Methacrylic acid ester, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, bifunctional methacrylate such as 1,6-hexanediol dimethacrylate, trimethylolpropane trimethacrylate Monofunctional acrylics such as trifunctional methacrylates such as methyl acrylate, ethyl acrylate, lauryl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and a reaction product of acrylic acid and Cardura E-10 Bifunctional acrylic ester such as acid ester, ethylene glycol diacrylate, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, trifunctional acrylic ester such as trimethylolpropane triacrylate, pentaerythritol triacrylate, penta A tetrafunctional acrylic ester such as erythritol tetraacrylate and a hexafunctional acrylic ester such as pentaerythritol hexaacrylate are used.
これら（Ｂ）重合性不飽和基を有する単量体の配合割合は、硬化速度と塗料の粘度、および塗膜の可とう性の点から前記の（Ａ）成分５０質量部に対して、１〜５０質量部の範囲が好ましく、１０〜５０質量部の範囲がより好ましい。 The blending ratio of the monomer (B) having a polymerizable unsaturated group is 1 with respect to 50 parts by mass of the component (A) from the viewpoints of the curing speed, the viscosity of the coating material, and the flexibility of the coating film. The range of -50 mass parts is preferable, and the range of 10-50 mass parts is more preferable.
（Ｃ）分子中に二重結合を有するリン酸化合物である単量体の具体例としては、２−メタクリロイロキシエチルアシッドホスフェート（商品名ライトエステルＰ−１Ｍ、ライトエステルＰ−２Ｍ 共栄社化学（株）製）、エチレンオキサイド変性リン酸ジメタクリレート（商品名ＰＭ−２１日本化薬（株）製）、燐酸含有エポキシメタクリレート（商品名ニューフロンティアＳ−２３Ａ 第一工業製薬（株）製）等のリン酸（メタ）アクリレート化合物；ビニルホスホン酸（商品名ＶＰＡ−９０，ＶＰＡ−１００ ＢＡＳＦ社製）等が挙げられる。
これら（Ｃ）分子中に二重結合を有するリン酸化合物である単量体は、密着性向上の観点から前記の（Ａ）成分と（Ｂ）成分の総量１００質量部に対して０．０１〜１０質量部が好ましく、０．１〜８質量部の範囲がより好ましい。
(C) As a specific example of the monomer which is a phosphoric acid compound having a double bond in the molecule, 2-methacryloyloxyethyl acid phosphate (trade name: light ester P-1M, light ester P-2M Kyoeisha Chemical ( Co., Ltd.), ethylene oxide-modified phosphoric dimethacrylate (trade name PM-21 Nippon Kayaku Co., Ltd.), phosphoric acid-containing epoxy methacrylate (trade name New Frontier S-23A, Daiichi Kogyo Seiyaku Co., Ltd.), etc. Examples include phosphoric acid (meth) acrylate compounds; vinylphosphonic acid (trade names VPA-90, VPA-100 manufactured by BASF).
The monomer which is a phosphoric acid compound having a double bond in the molecule (C) is 0.01% with respect to 100 parts by mass of the total amount of the component (A) and the component (B) from the viewpoint of improving adhesion. -10 mass parts is preferable, and the range of 0.1-8 mass parts is more preferable.
（Ｄ）光重合開始剤は、増感剤と呼ばれるものも包含される。かかる光重合開始剤の具体例としては、アクリジン又は分子内に少なくとも１つのアクリジニル基を有するアクリジン系化合物、ベンゾフェノン、Ｎ，Ｎ’−テトラメチル−４，４’−ジアミノベンゾフェノン（ミヒラーケトン）等のＮ，Ｎ’−テトラアルキル−４，４’−ジアミノベンゾフェノン、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノン−１、２−メチル−１−［４−（メチルチオ）フェニル］−２−モルフォリノ−プロパノン−１等の芳香族ケトン、アルキルアントラキノン等のキノン類、ベンゾインアルキルエーテル等のベンゾインエーテル化合物、ベンゾイン、アルキルベンゾイン等のベンゾイン化合物、ベンジルジメチルケタール等のベンジル誘導体、２−（ｏ−クロロフェニル）−４，５−ジフェニルイミダゾール二量体、２−（ｏ−クロロフェニル）−４，５−ジ（メトキシフェニル）イミダゾール二量体、２−（ｏ−フルオロフェニル）−４，５−ジフェニルイミダゾール二量体、２−（ｏ−メトキシフェニル）−４，５−ジフェニルイミダゾール二量体、２−（ｐ−メトキシフェニル）−４，５−ジフェニルイミダゾール二量体等の２，４，５−トリアリールイミダゾール二量体、Ｎ−フェニルグリシン、Ｎ−フェニルグリシン誘導体、クマリン系化合物、オニウム塩などが挙げられる。これらは１種類を単独で又は２種類以上を組み合わせて使用できる。 (D) What is called a sensitizer is also contained in a photoinitiator. Specific examples of such a photopolymerization initiator include acridine or an acridine compound having at least one acridinyl group in the molecule, benzophenone, N, such as N, N′-tetramethyl-4,4′-diaminobenzophenone (Michler ketone), and the like. , N′-tetraalkyl-4,4′-diaminobenzophenone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2-methyl-1- [4- (methylthio) phenyl ] Aromatic ketones such as 2-morpholino-propanone-1, quinones such as alkylanthraquinones, benzoin ether compounds such as benzoin alkyl ether, benzoin compounds such as benzoin and alkylbenzoin, benzyl derivatives such as benzyldimethyl ketal, 2- (O-chlorophenyl) -4 5-diphenylimidazole dimer, 2- (o-chlorophenyl) -4,5-di (methoxyphenyl) imidazole dimer, 2- (o-fluorophenyl) -4,5-diphenylimidazole dimer, 2 2,4,5-triarylimidazole dimers such as-(o-methoxyphenyl) -4,5-diphenylimidazole dimer, 2- (p-methoxyphenyl) -4,5-diphenylimidazole dimer N-phenylglycine, N-phenylglycine derivatives, coumarin compounds, onium salts and the like. These can be used alone or in combination of two or more.
（Ｄ）光重合開始剤の配合割合は、硬化速度と造膜性、および塗膜の可とう性の点から前記の（Ａ）成分と（Ｂ）成分の総量１００質量部に対して０．１〜１５質量部が好ましく、０．１〜１０質量部の範囲がより好ましい。この配合割合が０．１質量部未満であると、光硬化が不十分となる傾向にあり、１５質量部を超えると、得られる硬化物の特性（深部硬化性、可とう性及び密着性等）が全般的に低下する傾向にある。 (D) The blending ratio of the photopolymerization initiator is 0. 0 with respect to 100 parts by mass of the total amount of the component (A) and the component (B) from the viewpoint of curing speed, film-forming property, and flexibility of the coating film. 1-15 mass parts is preferable and the range of 0.1-10 mass parts is more preferable. If the blending ratio is less than 0.1 parts by mass, photocuring tends to be insufficient, and if it exceeds 15 parts by mass, the properties of the resulting cured product (deep part curability, flexibility, adhesion, etc.) ) Generally tends to decrease.
（Ｅ）有機顔料の具体例としては、フタロシアニン・ブルー、フタロシアニン・グリーン、アイオディン・グリーン、ジアゾイエロー、アニリンブラック、ペリレンブラック等が挙げられる。これらは１種を単独で又は２種以上を組み合わせて用いることができる。 Specific examples of (E) organic pigments include phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, aniline black, and perylene black. These can be used individually by 1 type or in combination of 2 or more types.
（Ｅ）成分の配合割合は（Ａ）成分と（Ｂ）成分の総量１００質量部に対して０．１〜１０質量部、好ましくは０．１〜５質量部配合することが好ましい。該配合割合が０．１質量部未満では遮光の効果が小さくなる傾向があり、１０質量部を越えると深部硬化性が低下する傾向がある。遮光性の観点から、本発明に使用される（Ｅ）成分としては平均粒子径が２０μｍ以下のものが好ましく、さらに平均粒子径が１μｍ以下のものがより好ましい。また、遮光性の観点から０．０１μｍ以上であることが好ましい。なお、本明細書で記載する「平均粒子径」は、光散乱法による測定によって得られる値とする The blending ratio of the component (E) is 0.1 to 10 parts by weight, preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the total amount of the components (A) and (B). If the blending ratio is less than 0.1 parts by mass, the light shielding effect tends to be small, and if it exceeds 10 parts by mass, the deep curability tends to decrease. From the viewpoint of light shielding properties, the component (E) used in the present invention preferably has an average particle diameter of 20 μm or less, and more preferably has an average particle diameter of 1 μm or less. Moreover, it is preferable that it is 0.01 micrometer or more from a light-shielding viewpoint. The “average particle size” described in the present specification is a value obtained by measurement by a light scattering method.
本発明の光硬化性遮光塗料は、前記の（Ａ）、（Ｂ）、（Ｃ）、（Ｄ）および（Ｅ）の各成分を配合することによって得られる。また、本発明になる光硬化性遮光塗料には、必要に応じて、レベリング剤、フィラー、カップリング剤、重合禁止剤、着色剤などを添加することができる。 The photocurable light-shielding coating material of the present invention is obtained by blending the components (A), (B), (C), (D) and (E). Moreover, a leveling agent, a filler, a coupling agent, a polymerization inhibitor, a coloring agent, etc. can be added to the photocurable light-shielding coating material according to the present invention as necessary.
レベリング剤としては、一般に知られたものが使用でき、例えば、ＵＶ−３５７０（ビックケミー・ジャパン株式会社製、アクリル基を有するポリエーテル変性ポリジメチルシロキサン）などが好ましい。レベリング剤は、（Ａ）成分と（Ｂ）成分の総量１００質量部に対して０．０１〜１０質量部配合することが好ましい。 As the leveling agent, generally known agents can be used, and for example, UV-3570 (manufactured by Big Chemie Japan Co., Ltd., polyether-modified polydimethylsiloxane having an acrylic group) and the like are preferable. The leveling agent is preferably blended in an amount of 0.01 to 10 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B).
フィラーの具体例としては、シリコーンレジンパウダー、シリコーンゴムパウダー、シリコーンゴムパウダーの表面をシリコーンレジンで被覆した複合パウダー、アルミナ、ジルコニア、セラミック微粉、タルク、マイカ、窒化ホウ素、カオリン、又は硫酸バリウム等を使用することができる。 Specific examples of fillers include silicone resin powder, silicone rubber powder, composite powder in which the surface of silicone rubber powder is coated with silicone resin, alumina, zirconia, ceramic fine powder, talc, mica, boron nitride, kaolin, or barium sulfate. Can be used.
カップリング剤としては、チタネート系カップリング剤およびシラン系カップリング剤があり、チタネート系カップリング剤は、少なくとも炭素数１〜６０のアルキレート基を有するチタネート系カップリング剤、アルキルホスファイト基を有するチタネート系カップリング剤、アルキルホスフェート基を有するチタネート系カップリング剤もしくはアルキルパイロホスフェート基を有するチタネート系カップリング剤等が挙げられる。具体的にはイソプロピルトリイソステアロイルチタネート、イソプロピルトリオクタノイルチタネート、イソプロピルジメタクリルイソステアロイルチタネート、イソプロピルイソステアロイルジアクリルチタネート、イソプロピルトリス（ジオクチルパイロホスフェート）チタネート、テトラオクチルビス（ジトリデシルホスファイト）チタネート、テトラ（２，２−ジアリルオキシメチル−１−ブチル）ビス（ジトリデシル）ホスファイトチタネート、ビス（ジオクチルパイロホスフェート）オキシアセテートチタネート、ビス（ジオクチルパイロホスフェート）エチレンチタネートなどが挙げられる。 The coupling agent includes a titanate coupling agent and a silane coupling agent. The titanate coupling agent includes a titanate coupling agent having an alkylate group having at least 1 to 60 carbon atoms and an alkyl phosphite group. And titanate coupling agents having an alkyl phosphate group, titanate coupling agents having an alkyl phosphate group, and titanate coupling agents having an alkyl phosphate group. Specifically, isopropyl triisostearoyl titanate, isopropyl trioctanoyl titanate, isopropyl dimethacryl isostearoyl titanate, isopropyl isostearoyl diacryl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, tetraoctyl bis (ditridecyl phosphite) titanate, Examples include tetra (2,2-diallyloxymethyl-1-butyl) bis (ditridecyl) phosphite titanate, bis (dioctylpyrophosphate) oxyacetate titanate, bis (dioctylpyrophosphate) ethylene titanate, and the like.
またシラン系カップリング剤は、アミノ系シランカップリング剤、ウレイド系シランカップリング剤、ビニル系シランカップリング剤、メタクリル系シランカップリング剤、エポキシ系シランカップリング剤、メルカプト系シランカップリング剤及びイソシアネート系シランカップリング剤等が挙げられる。具体的には、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、Ｎ−β−（アミノエチル）−γ−アミノプロピルトリメトキシシラン、γ−フェニルアミノプロピルトリメトキシシラン、ウレイドプロピルトリエトキシシラン、ビニルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリス（β−メトキシエトキシ）シラン、γ−メタクリロキシプロピルトリメトキシシラン、γ−メタクリロキシプロピルメチルジメトキシシラン、β−（３，４−エポキシシクロヘキシル）エチルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−メルカプトプロピルトリメトキシシラン、γ−イソシアネートプロピルトリメトキシシランなどが挙げられ、これらは単独でまたは２種以上を組み合わせて使用できる。 Silane coupling agents include amino silane coupling agents, ureido silane coupling agents, vinyl silane coupling agents, methacrylic silane coupling agents, epoxy silane coupling agents, mercapto silane coupling agents and An isocyanate silane coupling agent etc. are mentioned. Specifically, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-β- (aminoethyl) -γ-aminopropyltrimethoxysilane, γ-phenylaminopropyltrimethoxysilane, ureidopropyltri Ethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, vinyltris (β-methoxyethoxy) silane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, β- (3,4-epoxycyclohexyl) Examples include ethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, and γ-isocyanatopropyltrimethoxysilane, which are used alone or in combination of two or more. It can be used Te.
重合禁止剤としては、ハイドロキノン、ハイドロキノンモノメチルエーテル、ベンゾキノン、ｐ−ｔｅｒｔ−ブチルカテコール、２，６−ジ−ｔｅｒｔ−ブチル−４−メチルフェノール、ピロガロール等のキノン類、その他一般に使用されているものが用いられる。 Polymerization inhibitors include hydroquinone, hydroquinone monomethyl ether, benzoquinone, p-tert-butylcatechol, quinones such as 2,6-di-tert-butyl-4-methylphenol, pyrogallol, and other commonly used ones. Used.
消泡剤としては例えば、シリコーン系オイル、フッ素系オイル、ポリカルボン酸系ポリマーなど一般に使用されているものが挙げられる。 Examples of the antifoaming agent include those commonly used such as silicone oil, fluorine oil, and polycarboxylic acid polymer.
本発明の光硬化性遮光塗料は、液晶表示パネル側面部にディスペンサー装置等で塗布され、高圧水銀灯、メタルハライドランプ等を光源としたランプ方式のＵＶ照射装置を用い、必要量の紫外線を照射し硬化させて用いる。 The photocurable light-shielding paint of the present invention is applied to a side surface of a liquid crystal display panel by a dispenser device or the like, and is cured by irradiating a necessary amount of ultraviolet rays using a lamp type UV irradiation device using a high pressure mercury lamp, a metal halide lamp or the like as a light source. Use it.
以下、本発明を実施例により詳細に説明する。以下に示す実施例は、本発明を好適に説明する例示であって、なんら本発明を限定するものではない。 Hereinafter, the present invention will be described in detail with reference to examples. The following examples are illustrations for suitably explaining the present invention, and do not limit the present invention.
（Ａ）成分としてＵＸ−０９３７（日本化薬株式会社製、ウレタンアクリレート樹脂）５０質量部、（Ｂ）成分としてイソボルニルアクリレート４５質量部及びジペンタエリスリトールヘキサアクリレート１０質量部、（Ｃ）成分としてエチレンオキサイド変性リン酸ジメタクリレート０．５質量部、（Ｄ）成分としてビス（２，４，６−トリメチルベンゾイル）−フェニルフォスフィンオキサイド３質量部、（Ｅ）成分としてペリレンブラック（平均粒子径０．０８μｍ）０．７５質量部、その他添加剤としてＵＶ−３５７０（ビックケミー・ジャパン株式会社製、アクリル基を有するポリエーテル変性ポリジメチルシロキサン）０．５質量部を６０℃で加熱攪拌して光硬化性遮光塗料を得た。 (A) component UX-0937 (manufactured by Nippon Kayaku Co., Ltd., urethane acrylate resin) 50 parts by mass, (B) component 45 parts by mass of isobornyl acrylate and 10 parts by mass of dipentaerythritol hexaacrylate, component (C) As ethylene oxide-modified dimethacrylate phosphate 0.5 parts by mass, (D) component bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide 3 parts by mass, component (E) perylene black (average particle size) 0.08 μm) 0.75 parts by mass, as an additive, UV-3570 (manufactured by Big Chemie Japan Co., Ltd., polyether-modified polydimethylsiloxane having an acrylic group) 0.5 parts by mass is heated and stirred at 60 ° C. A curable shading paint was obtained.
（Ａ）成分をＵＸ−０９３７（日本化薬株式会社製、ウレタンアクリレート樹脂）３０質量部及びＭ−６２５０（東亞合成株式会社製、ポリエステルアクリレート樹脂）６０質量部とし、（Ｂ）成分をジペンタエリスリトールヘキサアクリレート１０質量部としたこと以外は実施例１と同様にした。 Component (A) is 30 parts by mass of UX-0937 (manufactured by Nippon Kayaku Co., Ltd., urethane acrylate resin) and 60 parts by mass of M-6250 (manufactured by Toagosei Co., Ltd., polyester acrylate resin), and component (B) is dipenta The procedure was the same as Example 1 except that 10 parts by mass of erythritol hexaacrylate was used.
（Ａ）成分をＵＸ−０９３７（日本化薬株式会社製、ウレタンアクリレート樹脂）５０質量部とし、（Ｂ）成分をイソボルニルアクリレート２０質量部、１，１０−デカンジオールジアクリレート１５質量部及びジペンタエリスリトールヘキサアクリレート１５質量部としたこと以外は実施例１と同様にした。 Component (A) is 50 parts by mass of UX-0937 (manufactured by Nippon Kayaku Co., Ltd., urethane acrylate resin), and component (B) is 20 parts by mass of isobornyl acrylate, 15 parts by mass of 1,10-decanediol diacrylate, and Example 1 was repeated except that 15 parts by mass of dipentaerythritol hexaacrylate was used.
比較例１
実施例１のエチレンオキサイド変性リン酸ジメタクリレート０．５質量部を加えないこと以外は実施例１と同様にした。
Comparative Example 1
The same procedure as in Example 1 was conducted except that 0.5 part by mass of ethylene oxide-modified phosphoric dimethacrylate in Example 1 was not added.
比較例２
実施例１のエチレンオキサイド変性リン酸ジメタクリレート０．５質量部をγ−メタクリロキシプロピルトリエトキシシランに変えたこと以外は実施例１と同様にした。
Comparative Example 2
The procedure was the same as in Example 1 except that 0.5 part by mass of ethylene oxide-modified phosphoric dimethacrylate in Example 1 was changed to γ-methacryloxypropyltriethoxysilane.
比較例３
実施例１のエチレンオキサイド変性リン酸ジメタクリレート０．５質量部をγ−イソシアネートプロピルトリメトキシシランに変えたこと以外は実施例１と同様にした。
Comparative Example 3
The same procedure as in Example 1 was conducted except that 0.5 part by mass of ethylene oxide-modified phosphoric dimethacrylate in Example 1 was changed to γ-isocyanatopropyltrimethoxysilane.
以上で得た塗料について、深部硬化性、表面硬化性、色変化、および透過率について下記のようにして評価した。
〔深部硬化性〕
実施例１、２、３および比較例１、２、３で得られた塗料を深さが５ｍｍの鋳型へ流し込み、これに紫外線照射装置（日本電池株式会社製、ＵＶ−０３０８）で３６５ｎｍの波長において照射出力４００ｍＷ／ｃｍ２で総照射量が６００ｍＪ／ｃｍ２になるように照射して、硬化物の厚みをマイクロメータ（（株）ミツトヨ製、ＭＤＣ−ＭＪ）で測定した。
About the coating material obtained above, deep part curability, surface curability, color change, and transmittance were evaluated as follows.
[Deep part curability]
The paints obtained in Examples 1, 2, and 3 and Comparative Examples 1, 2, and 3 were poured into a mold having a depth of 5 mm, and a wavelength of 365 nm was applied to the mold by an ultraviolet irradiation device (manufactured by Nippon Battery Co., Ltd., UV-0308). Was irradiated so that the total irradiation amount was 600 mJ / cm 2 at an irradiation output of 400 mW / cm 2 , and the thickness of the cured product was measured with a micrometer (MDC-MJ, manufactured by Mitutoyo Corporation).
〔表面硬化性〕
実施例１、２、３および比較例１、２、３で得られた塗料をガラス板に３００μｍ厚みになるように塗布し紫外線照射装置（日本電池株式会社製、ＵＶ−０３０８）で３６５ｎｍの波長において照射出力４００ｍＷ／ｃｍ２で総照射量が６００ｍＪ／ｃｍ２になるように照射して試験片を作製し、塗膜表面のべたつきについて指触評価した。べたつきがないものを「○」」、べとつきがあり塗料が指につくものを「×」として評価した。
[Surface curing]
The coating materials obtained in Examples 1, 2, and 3 and Comparative Examples 1, 2, and 3 were applied to a glass plate so as to have a thickness of 300 μm, and a wavelength of 365 nm was obtained using an ultraviolet irradiation device (manufactured by Nippon Battery Co., Ltd., UV-0308) A test piece was prepared by irradiation so that the total irradiation amount was 600 mJ / cm 2 at an irradiation output of 400 mW / cm 2 , and the touch of the coating film surface was evaluated. Evaluations were made as “O” for those without stickiness, and “X” for those with stickiness and paint on fingers.
〔透過率〕
表面硬化性の評価と同様に、実施例１、２、３および比較例１、２、３で得られた塗料をガラス板に３００μｍ厚みになるように塗布し、紫外線照射装置（日本電池株式会社製、ＵＶ−０３０８）で３６５ｎｍの波長において照射出力４００ｍＷ／ｃｍ２で総照射量が６００ｍＪ／ｃｍ２になるように照射して試験片を作製し、分光光度計（日立ハイテクノロジーズ社製、商品名「Ｕ―３３１０」）を用いて、４００〜７００ｎｍにおける平均光透過率を測定した。
[Transmissivity]
Similarly to the evaluation of surface curability, the paints obtained in Examples 1, 2, and 3 and Comparative Examples 1, 2, and 3 were applied to a glass plate to a thickness of 300 μm, and an ultraviolet irradiation device (Nippon Battery Co., Ltd.). Manufactured by UV-0308) at a wavelength of 365 nm with an irradiation output of 400 mW / cm 2 and a total irradiation amount of 600 mJ / cm 2 to produce a test piece, a spectrophotometer (manufactured by Hitachi High-Technologies Corporation, product) The average light transmittance at 400 to 700 nm was measured using the name “U-3310”).
〔ガラス密着性〕
表面硬化性の評価と同様に、実施例１、２、３および比較例１、２、３で得られた塗料をガラス板に３００μｍ厚みになるように塗布し、紫外線照射装置（日本電池株式会社製、ＵＶ−０３０８）で３６５ｎｍの波長において照射出力４００ｍＷ／ｃｍ２で総照射量が６００ｍＪ／ｃｍ２になるように照射して塗膜を作製、その上に半径４ｍｍの平頭リベットの頭部分を接着し、バー部分をオートグラフで引っ張り、遮光材のガラス密着性を測定した。
[Glass adhesion]
Similarly to the evaluation of surface curability, the paints obtained in Examples 1, 2, and 3 and Comparative Examples 1, 2, and 3 were applied to a glass plate to a thickness of 300 μm, and an ultraviolet irradiation device (Nippon Battery Co., Ltd.). Manufactured by UV-0308) at a wavelength of 365 nm and an irradiation power of 400 mW / cm 2 and a total irradiation amount of 600 mJ / cm 2 to produce a coating film, on which a head portion of a flat head rivet with a radius of 4 mm is formed. The bar part was pulled with an autograph and the glass adhesion of the light shielding material was measured.
Claims (5)
前記（Ｂ）成分がイソボルニルアクリレートを含有する、光硬化性樹脂組成物。 (A) Resin having a polymerizable unsaturated group having a weight average molecular weight of 1,000 to 10,000, (B) a monomer having a polymerizable unsaturated group, and (C) phosphorus having a double bond in the molecule It contains a monomer that is an acid compound, and (D) a photopolymerization initiator is contained in an amount of 1 to 10 parts by mass with respect to a total of 100 parts by mass of the component (A) and the component (B).
The photocurable resin composition in which the component (B) contains isobornyl acrylate.
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| JP2002098945A (en) * | 2000-09-21 | 2002-04-05 | Seiko Epson Corp | Liquid crystal device, light-shielding sheet for liquid crystal device and manufacturing method of the liquid crystal device |
| JP2006154870A (en) * | 2006-03-09 | 2006-06-15 | Mitsubishi Electric Corp | Liquid crystal display device |
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| JP2011039404A (en) * | 2009-08-17 | 2011-02-24 | Asahi Glass Co Ltd | Photosensitive composition for forming barrier rib of optical element, black matrix using the same and manufacturing method of the same, as well as, method of manufacturing color filter |
| JP5665613B2 (en) * | 2011-03-09 | 2015-02-04 | 日本合成化学工業株式会社 | Method for coating metal substrate |
| JP2013184997A (en) * | 2012-03-06 | 2013-09-19 | Hitachi Chemical Co Ltd | Liquid photocurable resin composition, image display device using the same, and method of manufacturing the same |
| CN104169331A (en) * | 2012-03-12 | 2014-11-26 | 日立化成株式会社 | Photocurable resin composition, image display device, and method for producing image display device |
| JP2013195681A (en) * | 2012-03-19 | 2013-09-30 | Mitsubishi Chemicals Corp | Photosensitive resin composition, color filter, liquid crystal display device, and organic el display |
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