JP2014026136A - 保護膜の製造方法 - Google Patents
保護膜の製造方法 Download PDFInfo
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- JP2014026136A JP2014026136A JP2012166677A JP2012166677A JP2014026136A JP 2014026136 A JP2014026136 A JP 2014026136A JP 2012166677 A JP2012166677 A JP 2012166677A JP 2012166677 A JP2012166677 A JP 2012166677A JP 2014026136 A JP2014026136 A JP 2014026136A
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- copolymer
- acrylic acid
- acrylate
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
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- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
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- 239000007864 aqueous solution Substances 0.000 description 4
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 4
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 3
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
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- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
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- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 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
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates 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
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QGOKIEUFWNCGFO-UHFFFAOYSA-N propanoic acid;pyrrole-2,5-dione Chemical compound CCC(O)=O.O=C1NC(=O)C=C1 QGOKIEUFWNCGFO-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 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
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Filters (AREA)
- Preparing Plates And Mask In Photomechanical Process (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Abstract
【解決手段】重合体(A)、(メタ)アクリル化合物(B)、重合開始剤(C)及び溶剤(E)を含む感光性樹脂組成物を凹凸基板上に塗布して塗膜を形成する工程と、凹凸基板の凹部および凸部に形成された塗膜に、凹部の位置の透過率が凸部の位置の透過率より大きい多階調マスクを介して露光する工程を含む保護膜の製造方法。
凹部の位置の透過率が60〜100%であり、かつ凸部の位置の透過率が10〜50%である多階調マスクを介して露光する前記の保護膜の製造方法。
【選択図】なし
Description
D)において、カラーフィルタ(color filter)は、ガラス、プラスチック又は
シリコンウェハー(silicon wafer)等の基板上に、ブラックマトリックス(B
lack matrix)をパターニング(patterning)した後、赤色(Red)、
緑色(Green)および青色(Blue)のピクセル着色層を形成し、その上に保護膜を形成することにより製造されている。
近年、カラーフィルタのさらなる平坦化が求められており、基板に凹凸があってもカラーフィルタを平坦化し得る保護膜の製造方法の開発が求められていた。
[2] 凹部の位置の透過率が60〜100%であり、かつ凸部の位置の透過率が10〜50%である多階調マスクを介して露光する[1]に記載の保護膜の製造方法。
[3] さらに、現像工程を有する[1]または[2]に記載の保護膜の製造方法。
[4] 重合体(A)が不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも一種に由来する構造単位と、炭素数2〜4の環状エーテル構造及びエチレン性不飽和結合を有する単量体に由来する構造単位とを有する[1]〜[3]のいずれかに記載の製造方法。
[5] [1]〜[4]のいずれかに記載の製造方法で得られた保護膜。
[6] [5]記載の保護膜を含む表示装置。
本発明の製造方法に使用される感光性樹脂組成物は、重合体(A)を含む。重合体(A)は、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種に由来する構造単位と、オキシラニル基を有する不飽和化合物に由来する構造単位とを含む付加重合体を含むことが好ましい。
重合体[A1]:不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種(a)(以下、「(a)」という場合がある)と、オキシラニル基を有する不飽和化合物(b)(以下、「(b)」という場合がある)とを重合してなる共重合体、
重合体[A2]:(a)と(b)と、(a)と(b)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる単量体)(以下、「(c)」という場合がある)とを重合してなる共重合体、
等が挙げられる。
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3‐ビニルフタル酸、4−ビニルフタル酸、3,4,5,6−テトラヒドロフタル酸、1,2,3,6−テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸、1、4−シクロヘキセンジカルボン酸等の不飽和ジカルボン酸類;
メチル−5−ノルボルネン−2,3−ジカルボン酸、5−カルボキシビシクロ[2.2.1]ヘプト−2−エン、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−5−エチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−メチルビシクロ[2.2.1]ヘプト−2−エン、5−カルボキシ−6−エチルビシクロ[2.2.1]ヘプト−2−エン等のカルボキシ基を含有するビシクロ不飽和化合物類;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3−ビニルフタル酸無水物、4−ビニルフタル酸無水物、3,4,5,6−テトラヒドロフタル酸無水物、1,2,3,6−テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6−ジカルボキシビシクロ[2.2.1]ヘプト−2−エン無水物等の不飽和ジカルボン酸類無水物;
α−(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和アクリレート類等が挙げられる。
これらのうち、アクリル酸、メタクリル酸、無水マレイン酸等が共重合反応性の点やアルカリ溶解性の点から好ましく用いられる。
本明細書において、「(メタ)アクリル酸」とは、アクリル酸及びメタクリル酸からなる群から選ばれる少なくとも1種を表す。「(メタ)アクリロイル」及び「(メタ)アクリレート」等の表記も同様の意味を有する。
本発明において、(b)は、オキシラニル基とエチレン性不飽和結合とを有する単量体であることが好ましく、オキシラニル基と(メタ)アクリロイルオキシ基とを有する単量体であることがより好ましい。また、(b)は(b2)であることが好ましい。
X1及びX2は、互いに独立に、単結合、−R3−、*−R3−O−、*−R3−S−、*−R3−NH−を表す。
R3は、炭素数1〜6のアルカンジイル基を表す。
*は、Oとの結合手を表す。
ヒドロキシアルキル基としては、ヒドロキシメチル基、1−ヒドロキシエチル基、2−ヒドロキシエチル基、1−ヒドロキシプロピル基、2−ヒドロキシプロピル基、3−ヒドロキシプロピル基、1−ヒドロキシ−1−メチルエチル基、2−ヒドロキシ−1−メチルエチル基、1−ヒドロキシブチル基、2−ヒドロキシブチル基、3−ヒドロキシブチル基、4−ヒドロキシブチル基等が挙げられる。
R1及びR2としては、好ましくは水素原子、メチル基、ヒドロキシメチル基、1−ヒドロキシエチル基、2−ヒドロキシエチル基が挙げられ、より好ましくは水素原子、メチル基が挙げられる。
X1及びX2としては、好ましくは単結合、メチレン基、エチレン基、*−CH2−O−基、*−CH2CH2−O−基が挙げられ、より好ましくは単結合、*−CH2CH2−O−基が挙げられる。*はOとの結合手を表す。
より好ましくは式(II−1)、式(II−7)、式(II−9)、式(II−15)が挙げられる。
シクロヘキシル(メタ)アクリレート、2−メチルシクロヘキシル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−8−イル(メタ)アクリレート(当該技術分野では、慣用名として、ジシクロペンタニル(メタ)アクリレートといわれている。
)、ジシクロペンタニルオキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート等の(メタ)アクリル酸シクロアルキルエステル類;
マレイン酸ジエチル、フマル酸ジエチル、イタコン酸ジエチル等のジカルボン酸ジエステル;
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート等の(メタ)アクリル酸ヒドロキシアルキルエステル類;
アクリロニトリル、メタクリロニトリル等のアクリロニトリル類;塩化ビニル、塩化ビニリデン、酢酸ビニル等のビニル化合物類;アクリルアミド、メタクリルアミド等のアクリルアミド類;1,3−ブタジエン、イソプレン、2,3−ジメチル−1,3−ブタジエン等のジエン化合物類;
3−メチル−3−メタクリルロイルオキシメチルオキセタン、3−メチル−3−アクリロイルオキシメチルオキセタン、3−エチル−3−メタクリロイルオキシメチルオキセタン、3−エチル−3−アクリロイルオキシメチルオキセタン、3−メチル−3−メタクリロイルオキシエチルオキセタン、3−メチル−3−アクリロイルオキシエチルオキセタン、3−エチル−3−メタクリロイルオキシエチルオキセタン、3−エチル−3−アクリロイルオキシエチルオキセタン等のオキセタニル基含有(メタ)アクリル酸エステル類;
テトラヒドロフルフリルアクリレート(例えば、ビスコートV#150、大阪有機化学工業(株)製)、テトラヒドロフルフリルメタクリレート等のテトラヒドロフリル基含有(メタ)アクリル酸エステル類等が挙げられる。
(a)に由来する構造単位;5〜60モル%より好ましくは10〜50モル%。
(b)に由来する構造単位;40〜95モル%、より好ましくは50〜90モル%。
重合体[A1]の構造単位の比率が、上記の範囲にあると、保存安定性、得られる塗膜の耐薬品性、耐熱性及び機械強度に優れる傾向がある。
(a)に由来する構造単位;2〜40モル%より好ましくは5〜35モル%。
(b)に由来する構造単位;2〜95モル%、より好ましくは5〜80モル%。
(c)に由来する構造単位;1〜65モル%、より好ましくは1〜60モル%。
また、(a)に由来する構造単位と(b)に由来する構造単位との合計は、重合体[A2]を構成する全構造単位の合計モル数に対して、70〜99モル%が好ましく、90〜99モル%がより好ましい。
重合体[A2]の構造単位の比率が、上記の範囲にあると、保存安定性、得られる塗膜の耐薬品性、耐熱性及び機械強度に優れる傾向がある。
重合体[A2]は、重合体[A1]と同様の方法により製造することができる。
(メタ)アクリル化合物(B)としては、(メタ)アクリルロイル基を3つ以上有する(メタ)アクリル化合物(B)が好ましく、ジペンタエリスリトールヘキサ(メタ)アクリレートがより好ましい。
また、特表2002−544205号公報に記載される、連鎖移動を起こしうる基を有する重合開始剤を使用してもよい。
溶剤(E)は、特に限定されず、当該分野で通常使用される溶剤を用いることができる。例えば、エステル溶剤(分子内に−COO−を含み、−O−を含まない溶剤)、エーテル溶剤(分子内に−O−を含み、−COO−を含まない溶剤)、エーテルエステル溶剤(分子内に−COO−と−O−とを含む溶剤)、ケトン溶剤(分子内に−CO−を含み、−COO−を含まない溶剤)、アルコール溶剤(分子内にOHを含み、−O−、−CO−及び−COO−を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等の中から選択して用いることができる。
これらの溶剤は、単独でも2種類以上を組み合わせて用いてもよい。
酸化防止剤(D)としては、例えば、2−tert−ブチル−6−(3−tert−ブチル−2−ヒドロキシ−5−メチルベンジル)−4−メチルフェニルアクリレート、2−[1−(2−ヒドロキシ−3,5−ジ−tert−ペンチルフェニル)エチル]−4,6−ジ−tert−ペンチルフェニルアクリレート、6−[3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロポキシ]−2,4,8,10−テトラ−tert−ブチルジベンズ[d、f][1,3,2]ジオキサホスフェピン、3,9−ビス[2−{3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ}−1,1−ジメチルエチル]−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン、2,2’−メチレンビス(6−tert−ブチル−4−メチルフェノール)、4,4’−ブチリデンビス(6−tert−ブチル−3−メチルフェノール)、4,4’−チオビス(2−tert−ブチル−5−メチルフェノール)、2,2’−チオビス(6−tert−ブチル−4−メチルフェノール)、ジラウリル3,3’−チオジプロピオネート、ジミリスチル3,3’−チオジプロピオネート、ジステアリル3,3’−チオジプロピオネート、ペンタエリスリチルテトラキス(3−ラウリルチオプロピオネート)、1,3,5−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、3,3’,3”,5,5’,5”−ヘキサ−tert−ブチル−a,a’,a”−(メシチレン−2,4,6−トリイル)トリ−p−クレゾール、ペンタエリスリトールテトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、2,6−ジ−tert−ブチル−4−メチルフェノール等が挙げられ、IRGANOX(登録商標)3114(BASFジャパン社製)等の市販品を用いてもよい。
酸化防止剤(F)の含有量が5質量部を超えると、鉛筆硬度が低下するおそれがある。
その他の高分子化合物として、マレイミド樹脂などの熱硬化性樹脂やポリビニルアルコール、ポリアクリル酸、ポリエチレングリコールモノアルキルエーテル、ポリフルオロアルキルアクリレート、ポリエステル、ポリウレタン等の熱可塑性樹脂などが挙げられる。
紫外線吸収剤として具体的には、2−(3−tert−ブチル−2−ヒドロキシ−5−メチルフェニル)−5−クロロベンゾトリアゾール、アルコキシベンゾフェノンなどが挙げられる。
連鎖移動剤としては、ドデシルメルカプタン、2,4−ジフェニル−4−メチル−1−ペンテンなどが挙げられる。
密着促進剤としては、例えば、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリス(2−メトキシエトキシ)シラン、3−グリシジルオキシキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、3-グリシドキシプロピルメチルジメトキシシラン、3-グリシドキシプロピルメチルジエトキシシラン、2−(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、3−クロロプロピルメチルジメトキシシラン、3−クロロプロピルトリメトキシシラン、3−メタクリロイルオキシプロピルトリメトキシシラン、3-メルカプトプロピルトリメトキシシラン、3−スルファニルプロピルトリメトキシシラン、3-イソシアネートプロピルトリエトキシシラン、N−2−(アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−2−(アミノエチル)−3−アミノプロピルメチルジエトキシシラン、N−2−(アミノエチル)−3−アミノプロピルトリメトキシシラン、N−2−(アミノエチル)−3−アミノプロピルメチルジエトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、N−フェニル−3−アミノプロピルトリメトキシシラン、N−フェニル−3−アミノプロピルトリエトキシシラン等が挙げられる。
硬化促進剤としては、例えば、1−メチルイミダゾール、2−メチルイミダゾール、2−ヒドロキシメチルイミダゾール、2−メチル−4−ヒドロキシメチルイミダゾール、5−ヒドロキシメチル−4−メチルイミダゾール、2−エチルイミダゾール、2−ウンデシルイミダゾール、2−ヘプタデシルイミダゾール、1,2−ジメチルイミダゾール、2−エチル−4−メチルイミダゾール、4−ヒドロキシメチル−2−フェニルイミダゾール、2−フェニルイミダゾール、2−フェニル2−ヒドロキシメチルイミダゾール、1−ベンジル−4−メチルイミダゾール、1−ベンジル−4−メチルイミダゾール、1−ベンジル−4−フェニルイミダゾール、1−ベンジル−5−ヒドロキシメチルイミダゾール、2−(p−ヒドロキシフェニル)イミダゾール、1−シアノメチル−2−メチルイミダゾール、1−(2−シアノエチル)−2−ヒドロキシメチルイミダゾール、2,4−ジフェニルイミダゾール、1−シアノメチル−2−ウンデシルイミダゾール、1−シアノメチル−2−エチル−4−メチルイミダゾール、1−シアノメチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾールなどが挙げられる。
この場合の塗膜の膜厚は、特に限定されず、用いる材料、用途等によって適宜調整することができ、例えば、1〜6μm程度が例示される。
露光は、水銀灯、発光ダイオードから発生する紫外線等の光を照射することにより通常、実施する。また凹凸基板の膜厚及び形状により、多階調マスクのパターンサイズやマスク透光部の透過率等は適宜調整することができる。
透明部には、フォトマスクに一般的に使用される、透明なリジット材またはフレキシブル材を用いることができ、熱膨張率が小さい石英ガラスが好ましく使用される。
遮光部には、実質的に露光光を透過しない金属膜、金属酸化物膜、金属窒化物膜を用いることができる。
半透過部には、使用する露光機の解像限界以下の微細パターンが形成されている構造で、遮光部に用いられる金属膜、金属酸化物膜、金属窒化物膜を使用して、例えばライン・アンド・スペースタイプ、ドット(網点)タイプ、或いはその他のパターンで透過率調整機能を有するものを用いることができ、特に限定されない。
ハーフトーンマスクもグレイトーンマスクと同様に透過部、遮光部、半透過部から構成されるが、半透過部がグレイトーンマスクと異なる。
半透過部には、半透過膜が形成されている構造で、その半透過膜は、通常金属膜であり、透過率調整機能を有するものを用いることができ、特に限定されない。該金属膜としては、例えば、クロム、モリブデンシリサイト、タンタル、アルミニウム、ケイ素、ニッケルの膜が挙げられるが、クロムの膜であることが好ましい。
現像方法は、液盛り法、ディッピング法、スプレー法等のいずれでもよい。さらに現像時に基板を任意の角度に傾けてもよい。
アルカリ性化合物は、無機及び有機のアルカリ性化合物のいずれでもよい。
無機アルカリ性化合物の具体例としては、水酸化ナトリウム、水酸化カリウム、燐酸水素二ナトリウム、燐酸二水素ナトリウム、燐酸水素二アンモニウム、燐酸二水素アンモニウム、燐酸二水素カリウム、ケイ酸ナトリウム、ケイ酸カリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、ホウ酸ナトリウム、ホウ酸カリウム、アンモニア等が挙げられる。
これらの無機及び有機アルカリ性化合物の水溶液中の濃度は、好ましくは0.01〜10質量%であり、より好ましくは0.03〜5質量%である。
界面活性剤は、ノニオン系界面活性剤、アニオン系界面活性剤又はカチオン系界面活性剤のいずれでもよい。
ノニオン系界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアリールエーテル、ポリオキシエチレンアルキルアリールエーテル、その他のポリオキシエチレン誘導体、オキシエチレン/オキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビトール脂肪酸エステル、グリセリン脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンアルキルアミン等が挙げられる。
アルカリ現像液中の界面活性剤の濃度は、好ましくは0.01〜10質量%、より好ましくは0.05〜8質量%、より好ましくは0.1〜5質量%である。
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を0.02L/分で流して窒素雰囲気とし、ジエチレングリコールエチルメチルエーテル140部を入れ、撹拌しながら70℃まで加熱した。次いでメタクリル酸40部;並びに単量体(I−1)及び単量体(II−1)の混合物{混合物中の単量体(I−1):単量体(II−1)のモル比=50:50}360部を、ジエチレングリコールエチルメチルエーテル190部に溶解させた溶液を調製し、この溶液を、滴下ロートを用いて4時間かけて、70℃に保温したフラスコ内に滴下した。
装置;K2479((株)島津製作所製)
カラム;SHIMADZU Shim−pack GPC−80M
カラム温度;40℃
溶媒;THF(テトラヒドロフラン)
流速;1.0mL/min
検出器;RI
校正用標準物質 ;TSK STANDARD POLYSTYRENE F−40、F−4、F−288、A−2500、A−500(東ソー(株)製)
上記で得られたポリスチレン換算の重量平均分子量及び数平均分子量の比(Mw/Mn)を分子量分布とした。
表1に示す各成分を、表1に示す割合で混合して、着色感光性樹脂組成物を得た。
形成された着色パターンの膜厚を測定したところ、2.3μmであることを確認した。
評価用基板に、感光性樹脂組成物を、スピンコーターを用いてポストベーク後の膜厚が2.0μmになるようにスピンコートし、次にホットプレート中、120℃で2分間プリベークし、次に露光機(TME−150RSK;トプコン(株)製、光源;超高圧水銀灯)を用いて、大気雰囲気下、100mJ/cm2の露光量(365nm基準)で、プリベーク後の塗膜を露光した。なおこの露光では、超高圧水銀灯からの放射光は、光学フィルタ(UV−31;旭テクノグラス(株)製)を通過させて行った。またフォトマスクは平坦性評価基板の凸部に対応するラインは光を25%通過させて、かつ平坦性評価基板の凹に対応するラインは光を100%透過する階調マスクを用いた。露光後、230℃で20分加熱して塗膜を得た。評価用基板上の塗膜のうち、塗膜の下に着色パターンが形成されていない部分で膜厚を測定し、2.0μmであることを確認した。
着色パターン上に形成された硬化膜表面の起伏の高低差を、膜厚測定と同様の操作で測定し、該高低差が0.4μmであった。
該高低差が0.4μm以内であれば塗膜の平坦性は良好であり、特にカラーフィルタ用保護膜として有用であるといえる。
評価用基板に、感光性樹脂組成物を、スピンコーターを用いてポストベーク後の膜厚が2.0μmになるようにスピンコートし、次にホットプレート中、120℃で2分間プリベークし、次に露光機(TME−150RSK;トプコン(株)製、光源;超高圧水銀灯)を用いて、大気雰囲気下、100mJ/cm2の露光量(365nm基準)で、プリベーク後の塗膜を露光した。なおこの露光では、超高圧水銀灯からの放射光は、光学フィルタ(UV−31;旭テクノグラス(株)製)を通過させて行った。またフォトマスクは平坦性評価基板の凸部に対応するラインは光を25%通過させて、かつ平坦性評価基板の凹に対応するラインは光を100%透過する階調マスクを用いた。露光後、非イオン系界面活性剤0.12%と水酸化カリウム0.04%を含む水系現像液に上記塗膜を25℃で60秒間浸漬して現像し、水洗後、230℃で20分加熱して塗膜を得た。評価用基板上の塗膜のうち、塗膜の下に着色パターンが形成されていない部分で膜厚を測定し、2.0μmであることを確認した。着色パターン上に形成された硬化膜表面の起伏の高低差を、膜厚測定と同様の操作で測定し、該高低差が0.1μmであった。
評価用基板に、感光性樹脂組成物を、スピンコーターを用いてポストベーク後の膜厚が2.0μmになるようにスピンコートし、次にホットプレート中、120℃で2分間プリベークし、次に露光機(TME−150RSK;トプコン(株)製、光源;超高圧水銀灯)を用いて、大気雰囲気下、180mJ/cm2の露光量(365nm基準)で、プリベーク後の塗膜を露光した。なおこの露光では、超高圧水銀灯からの放射光は、光学フィルタ(UV−31;旭テクノグラス(株)製)を通過させて行った。またフォトマスクは平坦性評価基板の凸部に対応するラインは光を25%通過させて、かつ平坦性評価基板の凹に対応するラインは光を100%透過する階調マスクを用いた。露光後、非イオン系界面活性剤0.12%と水酸化カリウム0.04%を含む水系現像液に上記塗膜を25℃で60秒間浸漬して現像し、水洗後、230℃で20分加熱して塗膜を得た。評価用基板上の塗膜のうち、塗膜の下に着色パターンが形成されていない部分で膜厚を測定し、2.0μmであることを確認した。着色パターン上に形成された硬化膜表面の起伏の高低差を、膜厚測定と同様の操作で測定し、該高低差が0.2μmであった。
評価用基板に、感光性樹脂組成物を、スピンコーターを用いてポストベーク後の膜厚が2.0μmになるようにスピンコートし、次にホットプレート中、120℃で2分間プリベークし、次に露光機(TME−150RSK;トプコン(株)製、光源;超高圧水銀灯)を用いて、大気雰囲気下、100mJ/cm2の露光量(365nm基準)で、プリベーク後の塗膜を露光した。なおこの露光では、超高圧水銀灯からの放射光は、光学フィルタ(UV−31;旭テクノグラス(株)製)を通過させて行った。またフォトマスクは使用せずに全面露光した。露光後、非イオン系界面活性剤0.12%と水酸化カリウム0.04%を含む水系現像液に上記塗膜を25℃で60秒間浸漬して現像し、水洗後、230℃で20分加熱して塗膜を得た。評価用基板上の塗膜のうち、塗膜の下に着色パターンが形成されていない部分で膜厚を測定し、2.0μmであることを確認した。着色パターン上に形成された硬化膜表面の起伏の高低差を、膜厚測定と同様の操作で測定し、該高低差が0.6μmであった。
Claims (6)
- 重合体(A)、(メタ)アクリル化合物(B)、重合開始剤(C)及び溶剤(E)を含む感光性樹脂組成物を凹凸基板上に塗布して塗膜を形成する工程と、凹凸基板の凹部および凸部に形成された塗膜に、凹部の位置の透過率が凸部の位置の透過率より大きい多階調マスクを介して露光する工程を含む保護膜の製造方法。
- 凹部の位置の透過率が60〜100%であり、かつ凸部の位置の透過率が10〜50%である多階調マスクを介して露光する請求項1に記載の保護膜の製造方法。
- さらに、現像工程を有する請求項1または2に記載の保護膜の製造方法。
- 重合体(A)が不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも一種に由来する構造単位と、炭素数2〜4の環状エーテル構造及びエチレン性不飽和結合を有する単量体に由来する構造単位とを有する請求項1〜3のいずれかに記載の製造方法。
- 請求項1〜4のいずれかに記載の製造方法で得られた保護膜。
- 請求項5記載の保護膜を含む表示装置。
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