JP2020511559A - Photoinitiator and light-shielding photosensitive resin composition containing the same - Google Patents
Photoinitiator and light-shielding photosensitive resin composition containing the same Download PDFInfo
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- JP2020511559A JP2020511559A JP2019528044A JP2019528044A JP2020511559A JP 2020511559 A JP2020511559 A JP 2020511559A JP 2019528044 A JP2019528044 A JP 2019528044A JP 2019528044 A JP2019528044 A JP 2019528044A JP 2020511559 A JP2020511559 A JP 2020511559A
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- Prior art keywords
- group
- light
- resin composition
- photosensitive resin
- compound
- Prior art date
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- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- -1 hydroxyalkoxyalkyl Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000003949 imides Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 claims 1
- 229920000178 Acrylic resin Polymers 0.000 claims 1
- 229920002050 silicone resin Polymers 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 230000007261 regionalization Effects 0.000 abstract description 6
- 238000000206 photolithography Methods 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 70
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 14
- 239000000178 monomer Substances 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000002952 polymeric resin Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 229920006243 acrylic copolymer Polymers 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 3
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 3
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- DOVZUKKPYKRVIK-UHFFFAOYSA-N 1-methoxypropan-2-yl propanoate Chemical compound CCC(=O)OC(C)COC DOVZUKKPYKRVIK-UHFFFAOYSA-N 0.000 description 2
- LCSAOPVSVLGDLE-UHFFFAOYSA-N 2-[[4-[9-[4-(oxiran-2-ylmethoxy)phenyl]fluoren-9-yl]phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1C1(C2=CC=CC=C2C2=CC=CC=C21)C(C=C1)=CC=C1OCC1CO1 LCSAOPVSVLGDLE-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SGQHDGJJZODGHE-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;methyl acetate Chemical compound COC(C)=O.OCCOCCO SGQHDGJJZODGHE-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HAUVRGZOEXGUJS-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-yl)but-2-enoic acid Chemical compound OC(=O)C(C)=CCC1CO1 HAUVRGZOEXGUJS-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 1
- DGQOZCNCJKEVOA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1CC(=O)OC1=O DGQOZCNCJKEVOA-UHFFFAOYSA-N 0.000 description 1
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- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 1
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- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
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- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- FBNXYLDLGARYKQ-UHFFFAOYSA-N methoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(C)CCCOCC1CO1 FBNXYLDLGARYKQ-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- VHWQFHRWNWSMGM-UHFFFAOYSA-N tert-butyl(disilanyl)silane Chemical compound CC(C)(C)[SiH2][SiH2][SiH3] VHWQFHRWNWSMGM-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Polymerisation Methods In General (AREA)
Abstract
本発明は、光開始剤、及びそれを含む遮光用感光性樹脂組成物に関し、より具体的には、式（１）で示される群、式（２）で示される群、及び式（３）で示される群から選ばれる２以上の群の化合物を含有する光開始剤、並びにそれを含む遮光用感光性樹脂組成物に関する。上記遮光用感光性樹脂組成物は、遮光性が向上し、深部硬化性に優れ、フォトリソグラフィー法を用いたパターン形成、及び現象工程に有利であるため、有機発光表示ディスプレイパネル用遮光用感光性樹脂組成物として好適に用いることができる。The present invention relates to a photoinitiator and a light-shielding photosensitive resin composition containing the same, and more specifically, a group represented by formula (1), a group represented by formula (2), and a formula (3). The present invention relates to a photoinitiator containing two or more groups of compounds selected from the group represented by, and a light-shielding photosensitive resin composition containing the same. The light-shielding photosensitive resin composition is improved in light-shielding property, is excellent in deep-curing property, and is advantageous for pattern formation using a photolithography method and a phenomenon process, and therefore, it is used as a light-shielding photosensitive resin for an organic light emitting display panel. It can be suitably used as a resin composition.
Description
本発明は、光開始剤、及びそれを含む遮光用感光性樹脂組成物に関し、より具体的には、式（１）で示される群、式（２）で示される群、及び式（３）で示される群から選ばれる２以上の群の化合物を含有する光開始剤、並びにそれを含む遮光用感光性樹脂組成物に関する。上記遮光用感光性樹脂組成物は、遮光性が向上し、深部硬化性に優れ、フォトリソグラフィー法を用いたパターン形成、及び現象工程に有利であるため、有機発光表示ディスプレイパネル用遮光用感光性樹脂組成物として好適に用いることができる。 The present invention relates to a photoinitiator and a light-shielding photosensitive resin composition containing the same, and more specifically, a group represented by formula (1), a group represented by formula (2), and a formula (3). The present invention relates to a photoinitiator containing two or more groups of compounds selected from the group represented by, and a light-shielding photosensitive resin composition containing the same. The light-shielding photosensitive resin composition is improved in light-shielding property, excellent in deep-part curability, and advantageous for pattern formation using a photolithography method and a phenomenon process, and therefore, the light-shielding photosensitive resin composition for an organic light-emitting display panel. It can be suitably used as a resin composition.
ディスプレイ用装置においては、近年、ＵＤ（Ｕｌｔｒａ Ｄｅｆｉｎｉｔｉｏｎ）以上の高解像度用装置、及び２４０Ｈｚ以上の高速作動用として、ＬＴＰＳ（Ｌｏｗ Ｔｅｍｐｅｒａｔｕｒｅ Ｐｏｌｙ−Ｓｉｌｉｃｏｎ）及び酸化物薄膜トランジスタが盛んに研究されている。 In display devices, in recent years, LTPS (Low Temperature Poly-Silicon) and oxide thin film transistors have been actively studied for high resolution devices of UD (Ultra Definition) or higher and for high speed operation of 240 Hz or higher.
一般に、酸化物薄膜トランジスタは、光による半導体の特性変化を示すので、遮光層を導入して、上記問題を最小限に抑えている。遮光層の形成後、高温でＰＥ−ＣＶＤなどの後続工程を行うため、遮光層としては主に金属遮光層が用いられる。しかし、金属遮光層は反射率が高いため、ソース・ドレイン電極と遮光層との間に反射光を導入することによって、ソース・ドレイン電極間に寄生電圧を発生させ、素子の動作に抵抗を与える要因として作用する。その結果、データ線の負荷が増大するという問題がある。 In general, an oxide thin film transistor exhibits a change in semiconductor characteristics due to light, so a light shielding layer is introduced to minimize the above problems. Since the subsequent steps such as PE-CVD are performed at a high temperature after forming the light shielding layer, a metal light shielding layer is mainly used as the light shielding layer. However, since the metal light-shielding layer has a high reflectance, by introducing reflected light between the source / drain electrode and the light-shielding layer, a parasitic voltage is generated between the source / drain electrodes, which gives a resistance to the operation of the device. Act as a factor. As a result, there is a problem that the load on the data line increases.
特に、有機発光表示ディスプレイ及び透明ディスプレイでは、上下の金属配線の反射によるコントラスト比の著しい低下を解消するために遮光層を設けている。 Particularly, in the organic light emitting display and the transparent display, a light shielding layer is provided in order to prevent a remarkable decrease in contrast ratio due to reflection of upper and lower metal wirings.
感光性組成物に用いられる光開始剤の一般的な例としては、アセトフェノン誘導体、ベンゾフェノン誘導体、トリアジン誘導体、ビイミダゾール誘導体、アシルホスフィンオキシド誘導体、及びオキシムエステル誘導体などの幾つかの種類が知られている。この中でも、オキシムエステル誘導体は紫外線を吸収し、発色しにくく、ラジカル発生効率が高いこと、他の感光性組成物材料との相容性が良いこと、安定性が良いことなどのメリットがある。しかし、初期段階で開発されたオキシム誘導体化合物は光開始効率が低く、特にパターン露光過程での感度が低いため、露光量を増やさなければならず、生産量が低下した。このような短所を改善するために、光開始剤として様々なオキシムエステル誘導体化合物が提案されてきた（例えば、特許文献１、２）。 As general examples of the photoinitiator used in the photosensitive composition, several kinds such as acetophenone derivative, benzophenone derivative, triazine derivative, biimidazole derivative, acylphosphine oxide derivative, and oxime ester derivative are known. There is. Among them, the oxime ester derivative has advantages that it absorbs ultraviolet rays and hardly develops color, has high radical generation efficiency, has good compatibility with other photosensitive composition materials, and has good stability. However, since the oxime derivative compound developed in the initial stage has low photoinitiating efficiency and particularly low sensitivity in the pattern exposure process, the exposure amount has to be increased and the production amount has decreased. In order to improve such disadvantages, various oxime ester derivative compounds have been proposed as photoinitiators (for example, Patent Documents 1 and 2).
本発明の目的は、遮光性が向上し、深部硬化性に優れ、フォトリソグラフィー法を用いたパターン形成、及び現象工程に有利であることから、有機発光表示ディスプレイパネル用遮光用感光性樹脂組成物として好適に用いることができる感光性樹脂組成物、及び該感光性樹脂組成物に特に好適に用いられる光開始剤を提供することである。 The object of the present invention is to improve the light-shielding property, the deep-curing property is excellent, and it is advantageous for the pattern formation using the photolithography method and the phenomenon process. Therefore, the light-shielding photosensitive resin composition for an organic light-emitting display panel is used. The present invention provides a photosensitive resin composition that can be preferably used as the above, and a photoinitiator that is particularly preferably used for the photosensitive resin composition.
本発明の目的は、下記式（１） An object of the present invention is to provide the following formula (1)
で示される群、下記式（２）
Group represented by the following formula (2)
で示される群又は下記式（３）
Or a group represented by the following formula (3)
で示される群から選ばれる２以上の群の化合物を含有する光開始剤を提供する。
また、本発明の他の側面は、［Ａ］アルカリ可溶性樹脂、［Ｂ］不飽和結合を有する重合性化合物、［Ｃ］着色剤、及び［Ｄ］上記光開始剤を含む遮光用感光性樹脂組成物を提供する。
Provided is a photoinitiator containing two or more groups of compounds selected from the group represented by:
Further, another aspect of the present invention is a photosensitive resin for shading containing [A] an alkali-soluble resin, [B] a polymerizable compound having an unsaturated bond, [C] a colorant, and [D] the above photoinitiator. A composition is provided.
本発明のさらに他の側面は、上記遮光用感光性樹脂組成物から形成された硬化膜を提供する。 Yet another aspect of the present invention provides a cured film formed from the light-shielding photosensitive resin composition.
本発明のさらに他の側面は、上記硬化膜を含むディスプレイ素子（例えば、有機発光表示ディスプレイ（ＯＬＥＤ）素子）を提供する。 Yet another aspect of the present invention provides a display device (for example, an organic light emitting display (OLED) device) including the cured film.
本発明の光開始剤を含む遮光用感光性樹脂組成物は、遮光性が向上し、深部硬化性に優れ、フォトリソグラフィー法を用いたパターン形成、及び現象工程に有利であることから、有機発光表示ディスプレイパネル用遮光用感光性樹脂組成物として好適に用いることができる。 The light-shielding photosensitive resin composition containing the photoinitiator of the present invention has an improved light-shielding property, is excellent in deep-side curability, and is advantageous for pattern formation using a photolithography method, and a phenomenon process, and thus organic light emission. It can be preferably used as a light-shielding photosensitive resin composition for a display panel.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の光開始剤は、下記式（１） The photoinitiator of the present invention has the following formula (1)
で示される群、下記式（２）
Group represented by the following formula (2)
で示される群、又は下記式（３）
Or a group represented by the following formula (3)
で示される群から選ばれる２以上の群の化合物を含む。
The compound of 2 or more groups selected from the group shown by is included.
上記において、具体的には、アルキル及びアルコキシの炭素数は１〜１０、シクロアルキルの炭素数は３〜８、アリールの炭素数は６〜３０であってもよい。アルキル及びアルコキシの炭素数は１〜８、シクロアルキルの炭素数は３〜６、アリールの炭素数は６〜２０であってもよい。 In the above, specifically, the alkyl and alkoxy may have 1 to 10 carbon atoms, the cycloalkyl may have 3 to 8 carbon atoms, and the aryl may have 6 to 30 carbon atoms. Alkyl and alkoxy may have 1 to 8 carbon atoms, cycloalkyl may have 3 to 6 carbon atoms, and aryl may have 6 to 20 carbon atoms.
さらに具体的には、上記Ｒ１〜Ｒ６は、それぞれ独立して、水素、ブロモ、クロロ、ヨード、メチル、エチル、ｎ−プロピル、ｉ−プロピル、ｎ−ブチル、ｉ−ブチル、ｔ−ブチル、ｎ−ペンチル、ｉ−ペンチル、ｎ−ヘキシル、ｉ−ヘキシル、フェニル、ナフチル、ビフェニル、テルフェニル、アントリル、インデニル、フェナントリル、メトキシ、エトキシ、ｎ−プロピルオキシ、ｉ−プロピルオキシ、ｎ−ブトキシ、ｉ−ブトキシ、ｔ−ブトキシ、ヒドロキシメチル、ヒドロキシエチル、ヒドロキシｎ−プロピル、ヒドロキシｎ−ブチル、ヒドロキシｉ−ブチル、ヒドロキシｎ−ペンチル、ヒドロキシｉ−ペンチル、ヒドロキシｎ−ヘキシル、ヒドロキシｉ−ヘキシル、ヒドロキシメトキシメチル、ヒドロキシメトキシエチル、ヒドロキシメトキシプロピル、ヒドロキシメトキシブチル、ヒドロキシエトキシメチル、ヒドロキシエトキシエチル、ヒドロキシエトキシプロピル、ヒドロキシエトキシブチル、ヒドロキシエトキシペンチル、又はヒドロキシエトキシヘキシルであってもよく；
Ａは、水素、又はニトロであってもよい。
More specifically, R 1 to R 6 are each independently hydrogen, bromo, chloro, iodo, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl. , N-pentyl, i-pentyl, n-hexyl, i-hexyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethyl, hydroxyethyl, hydroxy n-propyl, hydroxy n-butyl, hydroxy i-butyl, hydroxy n-pentyl, hydroxy i-pentyl, hydroxy n-hexyl, hydroxy i-hexyl, hydroxy Methoxymethyl, hydroxymethoxyethyl, hydr Alkoxy methoxypropyl, hydroxy methoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxy butyl, hydroxyethoxy pentyl, or may be a hydroxyethoxy hexyl;
A may be hydrogen or nitro.
本発明による式（１）の化合物としては、代表的に、下記群から選ばれる１つ以上が挙げられるが、下記化合物は本発明を限定しない： The compound of formula (1) according to the present invention typically includes one or more selected from the following group, but the following compounds do not limit the present invention:
本発明による式（２）の化合物としては、代表的に、下記群から選ばれる１つ以上が挙げられるが、下記化合物は本発明を限定しない： The compound of formula (2) according to the present invention typically includes one or more selected from the following group, but the following compounds do not limit the present invention:
本発明による式（３）の化合物としては、代表的に、下記群から選ばれる１つ以上が挙げられるが、下記の化合物は本発明を限定しない： The compound of formula (3) according to the present invention typically includes one or more selected from the following group, but the following compounds do not limit the present invention:
本発明の光開始剤に含まれる式（１）〜（３）の化合物間の含量比には特別な制限がない。 There is no particular limitation on the content ratio between the compounds of formulas (1) to (3) contained in the photoinitiator of the present invention.
一具体例において、式（１）〜（３）の群の内、２つの群（即ち、第１群、及び第２群）の化合物を使用する場合、第１群化合物：第２群化合物が、例えば、１：０．１〜１：１０、より具体的には１：０．２〜１：５、さらに具体的には１：０．５〜１：２、さらに具体的には１：０．８〜１：１．３の重量比で使用するが、これに限定されない。ここで、第１群、及び第２群は、式（１）〜（３）の３つの群から選ばれる２つの群を意味し、それぞれは、式（１）及び（２）、又は式（１）及び（３）、又は式（２）及び（３）であってもよい。 In one embodiment, when compounds of two groups (that is, the first group and the second group) of the groups of formulas (1) to (3) are used, the first group compound: the second group compound is , For example, 1: 0.1 to 1:10, more specifically 1: 0.2 to 1: 5, more specifically 1: 0.5 to 1: 2, still more specifically 1: It is used in a weight ratio of 0.8 to 1: 1.3, but is not limited thereto. Here, the first group and the second group mean two groups selected from the three groups of the formulas (1) to (3), respectively, and the formulas (1) and (2) or the formula ( 1) and (3), or formulas (2) and (3).
他の具体例において、式（１）〜（３）の３つの群の化合物（即ち、第１群〜第３群）を全て使用する場合、第１群化合物：第２群化合物：第３群化合物が、例えば、１：０．１〜１０：０．１〜１０、より具体的には１：０．２〜５：０．２〜５、さらに具体的には１：０．５〜２：０．５〜２、さらに具体的には１：０．８〜１．３：０．８〜１．３の重量比で使用するが、これに限定されない。ここで、第１群、第２群、及び第３群のそれぞれは、式（１）〜（３）の３群のそれぞれを意味し、それらは、式（１）、（２）及び（３）、又は式（１）、（３）及び（２）、式（２）、（１）及び（３）、又は式（２）、（３）及び（１）、又は式（３）、（１）及び（２）、又は式（３）、（２）及び（１）であってもよい。 In another embodiment, when all the compounds of the three groups of formulas (1) to (3) (that is, the first to third groups) are used, the first group compound: the second group compound: the third group The compound is, for example, 1: 0.1-10: 0.1-10, more specifically 1: 0.2-5: 0.2-5, more specifically 1: 0.5-2. : 0.5 to 2, more specifically 1: 0.8 to 1.3: 0.8 to 1.3, but not limited thereto. Here, each of a 1st group, a 2nd group, and a 3rd group means each of 3 groups of Formula (1)-(3), and those are Formula (1), (2), and (3. ), Or the formulas (1), (3) and (2), the formulas (2), (1) and (3), or the formulas (2), (3) and (1), or the formulas (3), ( 1) and (2) or formulas (3), (2) and (1) may be used.
本発明の遮光用感光性樹脂組成物は、［Ａ］アルカリ可溶性樹脂、［Ｂ］不飽和結合を有する重合性化合物、［Ｃ］着色剤、及び［Ｄ］本発明の光開始剤を含む。 The light-shielding photosensitive resin composition of the present invention contains [A] an alkali-soluble resin, [B] an unsaturated bond-containing polymerizable compound, [C] a colorant, and [D] the photoinitiator of the present invention.
本発明の遮光用感光性樹脂組成物は、色差発生の阻害現象を抑制し、深部硬化性に優れ、パターン形成に有利であるなど薄膜物性に優れる。 INDUSTRIAL APPLICABILITY The light-shielding photosensitive resin composition of the present invention suppresses the phenomenon of inhibition of color difference generation, is excellent in deep-part curability, is advantageous in pattern formation, and is excellent in thin-film physical properties.
本発明の遮光用感光性樹脂組成物にバインダー樹脂として含まれるアルカリ可溶性樹脂［Ａ］としては、アクリル重合体、又は側鎖にアクリル不飽和結合を有するアクリル重合体であるアクリル系バインダー樹脂、シリコーン系バインダー樹脂、カルド系バインダー樹脂、及びイミド系バインダー樹脂を用いることができる。 As the alkali-soluble resin [A] contained as a binder resin in the light-shielding photosensitive resin composition of the present invention, an acrylic polymer or an acrylic binder resin which is an acrylic polymer having an acrylic unsaturated bond in a side chain, silicone A system binder resin, a cardo system binder resin, and an imide system binder resin can be used.
特に限定されないが、パターン特性の調節、耐熱性、及び耐化学性などの薄膜物性の観点から、本発明の感光性樹脂組成物１００重量％中に含まれる上記アルカリ可溶性樹脂の含量は、好ましくは３〜５０重量％であり、より好ましくは５〜４０重量％である。また、アルカリ可溶性樹脂の重量平均分子量は、２，０００〜３００，０００が好ましく、４，０００〜１００，０００がより好ましい。また、アルカリ可溶性樹脂の分散度は１．０〜１０．０が好ましい。 Although not particularly limited, the content of the alkali-soluble resin contained in 100% by weight of the photosensitive resin composition of the present invention is preferably from the viewpoint of thin film physical properties such as adjustment of pattern characteristics, heat resistance, and chemical resistance. It is 3 to 50% by weight, and more preferably 5 to 40% by weight. The weight average molecular weight of the alkali-soluble resin is preferably 2,000 to 300,000, more preferably 4,000 to 100,000. In addition, the dispersity of the alkali-soluble resin is preferably 1.0 to 10.0.
一具体例において、上記アクリル重合体は、アクリル系単量体を含む単量体の（共）重合体であってもよい。このようなアクリル系単量体の例として、メチル（メタ）アクリレート、エチル（メタ）アクリレート、プロピル（メタ）アクリレート、ブチル（メタ）アクリレート、ペンチル（メタ）アクリレート、ヘキシル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、ヘプチル（メタ）アクリレート、オクチル（メタ）アクリレート、ノニル（メタ）アクリルレート、デシル（メタ）アクリレート、ラウリル（メタ）アクリレート、トデシル（メタ）アクリレート、テトラデシル（メタ）アクリレート、ヘキサデシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、アダマンチル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ベンジル（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、（メタ）アクリル酸、イタコン酸、マレイン酸、マレイン酸無水物、マレイン酸モノアルキルエステル、イタコン酸モノアルキル、フマル酸モノアルキル、グリシジル（メタ）アクリレート、３，４−エポキシブチル（メタ）アクリレート、２，３−エポキシシクロヘキシル（メタ）アクリレート、３，４−エポキシシクロヘキシルメチル（メタ）アクリレート、３−メチルオキセタン−３−メチル（メタ）アクリレート、３−エチルオキセタン−３−メチル（メタ）アクリレート、（メタ）アクリルアミド、Ｎ−メチル（メタ）アクリルアミドなどが挙げられるが、これらは単独で用いてもよく、２種以上を併用してもよい。また、このようなアクリル系単量体と、スチレン、α−メチルスチレン、アセトキシスチレン、Ｎ−メチルマレイミド、Ｎ−エチルマレイミド、Ｎ−プロピルマレイミド、Ｎ−ブチルマレイミド、Ｎ−シクロヘキシルマレイミドなどの単量体を共重合して得られた共重合体も本発明では使用可能である。 In one embodiment, the acrylic polymer may be a (co) polymer of a monomer containing an acrylic monomer. Examples of such acrylic monomers include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl ( (Meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, todecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (meth) ) Acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acryl , 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, (meth) acrylic acid, itaconic acid, maleic acid, maleic anhydride, maleic acid monoalkyl ester, itaconic acid monoalkyl, fumaric acid Monoalkyl, glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, 3-methyloxetane-3- Examples thereof include methyl (meth) acrylate, 3-ethyloxetane-3-methyl (meth) acrylate, (meth) acrylamide, N-methyl (meth) acrylamide, etc. These may be used alone or in combination of two or more. You may use together. Further, such acrylic monomers and a single amount of styrene, α-methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, etc. A copolymer obtained by copolymerizing the polymer can also be used in the present invention.
一具体例において、上記側鎖にアクリル不飽和結合を有するアクリル重合体は、カルボン酸を含有するアクリル共重合体にエポキシ樹脂を付加反応して得られる共重合体であってもよい。例えば、アクリル酸、メタクリル酸、イタコン酸、マレイン酸、マルレイクサンモノアルキルエステルなどのカルボン酸を含有したアクリルモノマーとメチル（メタ）アクリレート、ヘキシル（メタ）アクリレートなどのアルキル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、アダマンチル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ベンジル（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、スチレン、α−メチルスチレン、アセトキシスチレン、Ｎ−メチルマレイミド、Ｎ−エチルマレイミド、Ｎ−プロピルマレイミド、Ｎ−ブチルマレイミド、Ｎ−シクロヘキシルマレイミド、（メタ）アクリルアミド、Ｎ−メチル（メタ）アクリルアミドなどを共重合して得られた、カルボン酸を含有するアクリル共重合体にグリシジルアクリレート、グリシジルメタクリルレート、３，４−エポキシブチル（メタ）アクリレート、２，３−エポキシシクロヘキシル（メタ）アクリレート、３，４−エポキシシクロヘキシルメチル（メタ）アクリレートなどのエポキシモノマーを４０〜１８０℃の温度で付加反応して得られたものをバインダー樹脂として用いることができる。 In one specific example, the acrylic polymer having an acrylic unsaturated bond in the side chain may be a copolymer obtained by addition reaction of an epoxy resin with an acrylic copolymer containing a carboxylic acid. For example, acrylic monomers containing carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, and mallaken monoalkyl ester, and methyl (meth) acrylates, hexyl (meth) acrylates and other alkyl (meth) acrylates, cyclohexyl (Meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2 -Ethoxyethyl (meth) acrylate, styrene, α-methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N- Acrylic copolymer containing carboxylic acid obtained by copolymerizing chlorhexylmaleimide, (meth) acrylamide, N-methyl (meth) acrylamide and the like with glycidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl ( A binder resin is obtained by addition reaction of epoxy monomers such as (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, and 3,4-epoxycyclohexylmethyl (meth) acrylate at a temperature of 40 to 180 ° C. Can be used.
側鎖にアクリル不飽和結合を有するアクリル重合体の他の例としては、エポキシ基を含有するアクリル共重合体にカルボン酸を付加反応して得られる共重合体を挙げられる。例えば、グリシジルアクリレート、グリシジルメタクリルレート、３，４−エポキシブチル（メタ）アクリレート、２，３−エポキシシクロヘキシル（メタ）アクリレート、３，４−エポキシシクロヘキシルメチル（メタ）アクリレートなどのエポキシ基を含有したアクリルモノマーとメチル（メタ）アクリレート、ヘキシル（メタ）アクリレートなどのアルキル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、アダマンチル（メタ）アクリルレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ベンジル（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、スチレン、α−メチルスチレン、アセトキシスチレン、Ｎ−メチルマレイミド、Ｎ−エチルマレイミド、Ｎ−プロピルマレイミド、Ｎ−ブチルマレイミド、Ｎ−シクロヘキシルマレイミド、（メタ）アクリルアミド、Ｎ−メチル（メタ）アクリルアミドなどのモノマーを共重合して得られた、エポキシ基を含有するアクリル共重合体にアクリル酸、メタクリル酸、イタコン酸、マレイン酸、マレイン酸モノアルキルエステルなどのカルボン酸を含有するアクリルモノマーを４０〜１８０℃の温度で付加反応して得られたものをバインダー樹脂として用いることができる。 Another example of the acrylic polymer having an acrylic unsaturated bond in its side chain is a copolymer obtained by addition-reacting a carboxylic acid with an acrylic copolymer containing an epoxy group. For example, acryl containing an epoxy group such as glycidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, and 3,4-epoxycyclohexylmethyl (meth) acrylate. Monomers and alkyl (meth) acrylates such as methyl (meth) acrylate and hexyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, di Cyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, styrene, α-methyls Copolymerization of monomers such as len, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, (meth) acrylamide, N-methyl (meth) acrylamide. The resulting acrylic copolymer containing an epoxy group is subjected to an addition reaction with an acrylic monomer containing a carboxylic acid such as acrylic acid, methacrylic acid, itaconic acid, maleic acid or maleic acid monoalkyl ester at a temperature of 40 to 180 ° C. The thus obtained product can be used as a binder resin.
一具体例において、上記シリコーンバインダー樹脂は、下記式（４） In one embodiment, the silicone binder resin has the following formula (4)
Ｘは、ヒドロキシ、カルボン酸基、カルボン酸無水物基、カルボン酸無水物誘導体基、イミド基、イミド誘導体基、アミド基、アミド誘導体基、アミン基、又はメルカプトであり；
ｎは、０〜３の整数であり；ｎ＝３の重合単位は、ｎが３ではない他の重合単位と併用することができる）で示される重合単位を含有する。
X is hydroxy, carboxylic acid group, carboxylic acid anhydride group, carboxylic acid anhydride derivative group, imide group, imide derivative group, amide group, amide derivative group, amine group, or mercapto;
n is an integer of 0 to 3; the polymerized unit of n = 3 can be used in combination with another polymerized unit in which n is not 3).
また、上記シリコーンバインダー樹脂として例えば、テトラアルコキシシラン、トリアルコキシシラン、メチルトリアルコキシシラン、エチルトリアルコキシシラン、ｎ−プロピルトリアルコキシシラン、イソプロピルトリアルコキシシラン、ｎ−ブチルトリアルコキシシラン、ｔｅｒｔ−ブチルトリアルコキシシラン、フェニルトリアルコキシシラン、ナフタトリアルコキシシラン、ビニルトリアルコキシシラン、メタクリルオキシメチルトリアルコキシシラン、２−メタクリルオキシエチルトリアルコキシシラン、３−メタクリルオキシプロピルトリアルコキシシラン、３−メタクリルオキシプロピルメチルジアルコキシシラン、３−メタクリルオキシプロピルエチルジアルコキシシラン、アクリルオキシメチルトリアルコキシシラン、２−アクリルオキシエチルトリアルコキシシラン、３−アクリルオキシプロピルトリアルコキシシラン、３−アクリルオキシプロピルメチルジアルコキシシラン、３−アクリルオキシプロピルエチルジアルコキシシラン、３−グリシジルオキシプロピルトリアルコキシシラン、２−エポキシシクロヘキシルエチルトリアルコキシシラン、３−エポキシシクロヘキシルプロピルトリアルコキシシラン、ジメチルアルコキシシラン、ジエチルジアルコキシシラン、ジプロピルジアルコキシシラン、ジフェニルジアルコキシシラン、ジフェニルシランジオール、及びフェニルメチルジアルコキシシランで構成される群から選ばれる１種、又は２種以上の単量体が挙げられる。ここで、アルコキシは、炭素数１〜７の直鎖状、分岐状、又は環状の脂肪族又は芳香族アルコキシであってもよい。また、加水分解可能なハロゲン化シリコーン化合物を単量体として用いることもできる。 Examples of the silicone binder resin include tetraalkoxysilane, trialkoxysilane, methyltrialkoxysilane, ethyltrialkoxysilane, n-propyltrialkoxysilane, isopropyltrialkoxysilane, n-butyltrialkoxysilane, and tert-butyltrisilane. Alkoxysilane, phenyltrialkoxysilane, naphthaletrialkoxysilane, vinyltrialkoxysilane, methacryloxymethyltrialkoxysilane, 2-methacryloxyethyltrialkoxysilane, 3-methacryloxypropyltrialkoxysilane, 3-methacryloxypropylmethyldi Alkoxysilane, 3-methacryloxypropylethyldialkoxysilane, acryloxymethyltrialkoxysilane, -Acryloyloxyethyltrialkoxysilane, 3-acryloxypropyltrialkoxysilane, 3-acryloxypropylmethyldialkoxysilane, 3-acryloxypropylethyldialkoxysilane, 3-glycidyloxypropyltrialkoxysilane, 2-epoxycyclohexyl From a group consisting of ethyltrialkoxysilane, 3-epoxycyclohexylpropyltrialkoxysilane, dimethylalkoxysilane, diethyldialkoxysilane, dipropyldialkoxysilane, diphenyldialkoxysilane, diphenylsilanediol, and phenylmethyldialkoxysilane. One kind or two or more kinds of selected monomers may be mentioned. Here, the alkoxy may be a linear, branched, or cyclic aliphatic or aromatic alkoxy having 1 to 7 carbon atoms. Further, a hydrolyzable halogenated silicone compound can also be used as a monomer.
一具体例において、上記カルド系バインダー樹脂は、下記式（５） In one specific example, the cardo binder resin has the following formula (5).
Ｒ１２は、水素、炭素数１〜２０の直鎖状、分岐状、又は環状のアルキル基、炭素数６〜１０のアリール基、炭素数２〜１０の不飽和炭化水素基、又は−Ｃ（＝Ｏ）−Ｒ１２’であり、ここで、Ｒ１２'は、水素、ヒドロキシ、炭素数１〜２０の直鎖状、分岐状、若しくは環状のアルキル基、又は炭素数６〜１０のアリール基である。｝であり、
Ｒ１０は、同一又は異なっており、それぞれ独立して、水素、ヒドロキシ、炭素数１〜２０の直鎖状、分岐状、若しくは環状のアルキル基、又は炭素数６〜１０のアリール基であり；
Ｙは、
R 12 is hydrogen, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an unsaturated hydrocarbon group having 2 to 10 carbon atoms, or -C (. = O) -R 12 ' , wherein R 12' is hydrogen, hydroxy, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 10 carbon atoms. Is. },
R 10 s are the same or different and each independently represent hydrogen, hydroxy, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 10 carbon atoms;
Y is
一具体例において、上記イミド系バインダー樹脂は、下記式（６） In one specific example, the imide-based binder resin has the following formula (6).
Ｒ１７は水素、炭素数１〜２０の直鎖状、分岐状、若しくは環状のアルキル基、炭素数６〜１０のアリール基、炭素数２〜１０の不飽和炭化水素基、又は
R 17 is hydrogen, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an unsaturated hydrocarbon group having 2 to 10 carbon atoms, or
である］で示される化合物から由来した重合単位を含有する。
The polymerized unit derived from the compound represented by
本発明の遮光用感光性樹脂組成物に含まれる不飽和結合を有する重合性化合物［Ｂ］は、パターン形成時、光反応によって架橋して、パターンを形成する役割を果たし、高温加熱時に架橋して、耐化学性及び耐熱性を与える。 The polymerizable compound [B] having an unsaturated bond contained in the light-shielding photosensitive resin composition of the present invention crosslinks by a photoreaction during pattern formation, plays a role of forming a pattern, and crosslinks at high temperature heating. To provide chemical resistance and heat resistance.
本発明の感光性樹脂組成物１００重量％に含まれる上記不飽和結合を有する重合性化合物の含量は、特に限定されないが、例えば、０．００１〜４０重量％、より具体的に０．０１〜３０重量％であってもよい。感光性樹脂組成物に不飽和結合を有する重合性化合物を添加し過ぎると、架橋度が高くなり過ぎ、パターンの軟性が低下する場合がある。 The content of the polymerizable compound having an unsaturated bond contained in 100% by weight of the photosensitive resin composition of the present invention is not particularly limited, but is, for example, 0.001 to 40% by weight, more specifically 0.01 to 40% by weight. It may be 30% by weight. If the polymerizable compound having an unsaturated bond is added too much to the photosensitive resin composition, the degree of cross-linking becomes too high, and the softness of the pattern may decrease.
一具体例において、上記不飽和結合を有する重合性化合物は、ヒドロキシル基、又はカルボキシル基を有する重合性不飽和化合物であってもよい。 In one specific example, the polymerizable compound having an unsaturated bond may be a polymerizable unsaturated compound having a hydroxyl group or a carboxyl group.
一具体例において、上記不飽和結合を有する重合性化合物には、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ブチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ラウリル（メタ）アクリレートなどの（メタ）アクリル酸のアルキルエステル、グリシジル（メタ）アクリレート、エチレンオキシド基の数が２〜１４のポリエチレングリコールモノ（メタ）アクリレート、エチレングリコールジ（メタ）アクリレート、エチレンオキシド基の数が２〜１４のポリエチレングリコールジ（メタ）アクリレート、プロピレンオキシド基の数が２〜１４のポリプロピレングリコールジ（メタ）アクリレート、トリメチロールプロパンジ（メタ）アクリレート、ビスフェノールＡジグリシジルエーテルアクリル酸付加物、ジヒドロキシエチル（メタ）アクリレートのフタル酸ジエステル、ジヒドロキシエチル（メタ）アクリレートのトルエンジイソシアネート付加物、トリメチロールプロパントリ（メタ）アクリレート、ペンタエリトリトールトリ（メタ）アクリレート、ペンタエリトリトールテトラ（メタ）アクリレート、ジペンタエリトリトールペンタ（メタ）アクリレート、ジペンタエリトリトールヘキサ（メタ）アクリレート、ジペンタエリトリトールトリ（メタ）アクリレートのように多価アルコールとα，β−ジ不飽和カルボン酸をエステル化して得られる化合物、トリメチロールプロパントリグリシジルエーテルアクリル酸付加物のように多価グリシジル化合物のアクリル酸付加物などが挙げられ、これらは単独で用いてもよく、２種以上を併用してもよい。 In one specific example, the polymerizable compound having an unsaturated bond includes methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and lauryl (meth) acrylate. Alkyl ester of (meth) acrylic acid, glycidyl (meth) acrylate, polyethylene glycol mono (meth) acrylate having 2 to 14 ethylene oxide groups, ethylene glycol di (meth) acrylate, polyethylene having 2 to 14 ethylene oxide groups Glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate having 2 to 14 propylene oxide groups, trimethylolpropane di (meth) acrylate, bisphenol A diglycidyl ether acrylic acid Additive, phthalic acid diester of dihydroxyethyl (meth) acrylate, toluene diisocyanate adduct of dihydroxyethyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate , Dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol tri (meth) acrylate obtained by esterification of polyhydric alcohol and α, β-diunsaturated carboxylic acid , Acrylic acid adducts of polyvalent glycidyl compounds such as trimethylolpropane triglycidyl ether acrylic acid adducts, and these may be used alone or in combination of two or more. It may be used in combination.
本発明の遮光用感光性樹脂組成物に含まれる着色剤［Ｃ］は、組成物から形成された膜に遮光性を与える役割を果たす。 The colorant [C] contained in the light-shielding photosensitive resin composition of the present invention plays a role of giving a light-shielding property to a film formed from the composition.
本発明の感光性樹脂組成物１００重量％に含まれる上記着色剤含量は、特に限定されないが、例えば、３〜４０重量％、より具体的には５〜３０重量％であってもよい。感光性樹脂組成物内の着色剤含量が少な過ぎると、遮光性が低下する場合があり、逆に多過ぎると、遮光膜パターン形成のための工程性が低下する場合がある。 The content of the colorant contained in 100% by weight of the photosensitive resin composition of the present invention is not particularly limited, but may be, for example, 3 to 40% by weight, more specifically 5 to 30% by weight. If the content of the colorant in the photosensitive resin composition is too small, the light-shielding property may be deteriorated. On the contrary, if it is too large, the processability for forming the light-shielding film pattern may be deteriorated.
一具体例において、上記着色剤は、カーボンブラック、チタンブラック、アニリンブラック、ペリレンブラック、ラクタムブラック、及びＣ．Ｉ．ピグメントブラック７などを単独で用いてもよく、２種以上を併用してもよい。 In one embodiment, the colorants include carbon black, titanium black, aniline black, perylene black, lactam black, and C.I. I. Pigment Black 7 and the like may be used alone or in combination of two or more kinds.
本発明の遮光用感光性樹脂組成物は前述した本発明の光開始剤［Ｄ］を含む。 The light shielding photosensitive resin composition of the present invention contains the photoinitiator [D] of the present invention described above.
遮光用フォトレジストの反射率を最小化し、色差発生を抑制し、深部硬化を容易にする観点から、本発明の感光性樹脂組成物１００重量％に含まれる上記光開始剤の含量は、式（１）〜式（３）の化合物をそれぞれ独立して、０．０１〜１０重量％、より効果的には、０．１〜５重量％で使用することが有効であるが、これに限定されない。 From the viewpoint of minimizing the reflectance of the light-shielding photoresist, suppressing the occurrence of color difference, and facilitating the deep curing, the content of the photoinitiator contained in 100% by weight of the photosensitive resin composition of the present invention is represented by the formula ( It is effective to use the compounds of 1) to formula (3) each independently in an amount of 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, but not limited thereto. .
本発明の遮光用感光性樹脂組成物は、上記［Ａ］〜［Ｄ］成分以外に、必要に応じて、接着補助剤として、エポキシ基又はアミン基を有するシリコーン系化合物をさらに含んでもよい。 The light-shielding photosensitive resin composition of the present invention may further contain a silicone compound having an epoxy group or an amine group as an adhesion aid, in addition to the components [A] to [D] described above.
上記シリコーン系化合物は、ＩＴＯ電極と感光性樹脂組成物との接着力を向上させ、硬化後の耐熱特性を向上させるために使用することができる。その使用量は、組成物１００重量％に対して、０．０００１〜３重量％であってもよいが、これらに限定されない。 The silicone compound can be used to improve the adhesive force between the ITO electrode and the photosensitive resin composition and improve the heat resistance after curing. The amount used may be 0.0001 to 3% by weight with respect to 100% by weight of the composition, but is not limited thereto.
一具体例において、上記エポキシ基又はアミン基を有するシリコーン系化合物は、（３−グリシドオキシプロピル）トリメトキシシラン、（３−グリシドオキシプロピル）トリエトキシシラン、（３−グリシドオキシプロピル）メチルジメトキシシラン、（３−グリシドオキシプロピル）メチルジエトキシシラン、（３−グリシドオキシプロピル）ジメチルメトキシシラン、（３−グリシドオキシプロピル）ジメチルエトキシシラン、３，４−エポキシブチルトリメトキシシラン、３，４−エポキシブチルトリエトキシシラン、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、２−（３，４−エポキシシクロヘキシル）エチルトリエトキシシラン、アミノプロピルトリメトキシシランなどが挙げられ、これらは単独で用いてもよく、２種以上を併用してもよい。 In one specific example, the silicone compound having an epoxy group or an amine group is (3-glycidoxypropyl) trimethoxysilane, (3-glycidoxypropyl) triethoxysilane, (3-glycidoxypropyl). Methyldimethoxysilane, (3-glycidoxypropyl) methyldiethoxysilane, (3-glycidoxypropyl) dimethylmethoxysilane, (3-glycidoxypropyl) dimethylethoxysilane, 3,4-epoxybutyltrimethoxysilane 3,4-epoxybutyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, aminopropyltrimethoxysilane and the like. , These are for single use At best, it may be used in combination of two or more thereof.
また、本発明の遮光用感光性樹脂組成物は、必要に応じて、光増減剤、熱重合禁止剤、消泡剤、レベリング剤、分散剤などの相容化剤をさらに含んでもよい。 Further, the light-shielding photosensitive resin composition of the present invention may further contain a compatibilizer such as a photosensitizer, a thermal polymerization inhibitor, a defoaming agent, a leveling agent, and a dispersant, if necessary.
また、本発明の遮光用感光性樹脂組成物は、必要に応じて、チオキサントン系化合物、ケトン系化合物、ビイミダゾール系化合物、トリアジン系化合物、Ｏ−アシルオキシム系化合物、又はチオール系化合物よりなる群から選ばれる１種、又は２種以上の化合物をさらに含んでもよい。 Further, the light-shielding photosensitive resin composition of the present invention is, if necessary, a group consisting of a thioxanthone compound, a ketone compound, a biimidazole compound, a triazine compound, an O-acyl oxime compound, or a thiol compound. One or two or more compounds selected from the above may be further included.
本発明の遮光用感光性樹脂組成物は、溶媒を加え、基板の上にスピンコートした後、マスクを用いてＵＶ露光し、アルカリ現像液で現像する方法によりパターンを形成するために用いる。粘度を１〜５０ｃｐｓ範囲内に調整するために、組成物１００重量％に対して、１０〜９５重量％の溶媒を添加することが好ましい。 The light-shielding photosensitive resin composition of the present invention is used to form a pattern by a method in which a solvent is added, spin coating is performed on a substrate, UV exposure is performed using a mask, and development is performed with an alkali developing solution. In order to adjust the viscosity within the range of 1 to 50 cps, it is preferable to add 10 to 95% by weight of the solvent to 100% by weight of the composition.
上記溶媒としては、バインダー樹脂、光開始剤、及びその他化合物との相容性を考慮し、酢酸エチル、酢酸ブチル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジメチルエチルエーテル、メチルメトキシプロピオネート、エチルエトキシプロピオネート（ＥＥＰ）、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート（ＰＧＭＥＡ）、プロピレングリコールメチルエーテルプロピオネート（ＰＧＭＥＰ）、プロピレングリコールメチルエーテル、プロピレングリコールプロピルエーテル、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールメチルアセテート、ジエチレングルコールエチルアセテート、アセトン、メチルイソブチルケトン、シクロヘキサノン、ジメチルホルムアミド（ＤＭＦ）、Ｎ，Ｎ−ジメチルアセトアミド（ＤＭＡｃ）、Ｎ−メチル−２−ピロリドン（ＮＭＰ）、γ−ブチロラクトン、ジエチルエーテル、エチレングリコールジメチルエーテル、ジグリム（Ｄｉｇｌｙｍｅ）、テトラヒドロフラン（ＴＨＦ）、メタノール、エタノール、プロパノール、イソ−プロパノール、メチルセロソルブ、エチルセロソルブ、ジエチレングリコールメチルエーテル、ジエチレングリコールエチルエーテル、ジプロピレングリコールメチルエーテル、トルエン、キシレン、ヘキサン、ヘプタン、オクタンなどの溶媒を単独で用いてもよく、２種以上を混合して用いてもよい。 As the solvent, in consideration of compatibility with a binder resin, a photoinitiator, and other compounds, ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxy propionate ( EEP), ethyl lactate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol methyl ether propionate (PGMEP), propylene glycol methyl ether, propylene glycol propyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl acetate, diethylene glycol Coleethyl acetate, acetone, methyl isobutyl ketone, cyclohexanone, dimethylform Amide (DMF), N, N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), γ-butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme (Diglyme), tetrahydrofuran (THF), methanol, ethanol. , Propanol, iso-propanol, methyl cellosolve, ethyl cellosolve, diethylene glycol methyl ether, diethylene glycol ethyl ether, dipropylene glycol methyl ether, toluene, xylene, hexane, heptane, octane and the like may be used alone, two or more kinds. You may mix and use.
一具体例において、本発明の遮光用感光性樹脂組成物は、上記のような溶媒を含んでもよい。この場合、組成物内の溶媒含量は、組成物の全重量から他の成分の量を除いた残りの量である。 In one specific example, the light-shielding photosensitive resin composition of the present invention may contain a solvent as described above. In this case, the solvent content in the composition is the remaining amount of the total weight of the composition minus the amounts of other components.
本発明をより詳細に理解するために、以下に本発明の代表化合物の実施例及び比較例を通して本発明を詳細に説明する。しかし、本発明による実施例は、他の形態に多様に変形することができ、本発明の範囲が以下に詳述する実施例に限定されると解釈してはならない。本発明の実施例は、この分野の平均的な知識を有する人に対して本発明をより完全に説明するために提供される。 In order to understand the present invention in more detail, the present invention will be described in detail through examples and comparative examples of representative compounds of the present invention. However, the embodiments according to the present invention may be variously modified into other forms, and the scope of the present invention should not be construed as being limited to the embodiments described in detail below. The embodiments of the present invention are provided to more fully explain the present invention to those of ordinary skill in the art.
合成例：アルカリ可溶性樹脂の製造
ａ）樹脂Ａ−１の製造
プロピレングリコールメチルエーテルアセテート（ＰＧＭＥＡ）２００ｍＬにアゾビスイソブチロニトリル（ＡＩＢＮ）１．５ｇを添加し、メタクリル酸、グリシジルメタクリル酸、メチルメタクリル酸、及びジシクロペンタニルアクリル酸を、それぞれ２０：２０：４０：２０のモル比（アクリルモノマーの固形分：４０重量％）で添加した後、窒素雰囲気下、７０℃で５時間撹拌して重合させ、アクリル重合体樹脂Ａ−１を製造した。このようにして製造された共重合体の重量平均分子量は、２５，０００であることを確認した。
Synthesis example: Production of alkali-soluble resin a) Production of resin A-1 1.5 g of azobisisobutyronitrile (AIBN) was added to 200 mL of propylene glycol methyl ether acetate (PGMEA), and methacrylic acid, glycidyl methacrylic acid, and methyl were added. Methacrylic acid and dicyclopentanyl acrylic acid were added at a molar ratio of 20: 20: 40: 20 (solid content of acrylic monomer: 40% by weight), respectively, and then stirred at 70 ° C. for 5 hours under a nitrogen atmosphere. And polymerized to produce acrylic polymer resin A-1. It was confirmed that the weight average molecular weight of the copolymer thus produced was 25,000.
ｂ）樹脂Ａ−２の製造
メチル３−（トリエトキシシリル）プロピオネート６２．５ｇ（０．０５ｍｏｌｅ）、ビシクロヘプタニルトトリエトキシシラン５１．６ｇ（０．０４ｍｏｌｅ）、メチルトリメトキシシラン６．８ｇ（０．０１ｍｏｌｅ）、プロピレングリコールモノメチルエーテルアセテート２００ｇを秤量して混合し、得られた溶液を撹拌し、３５％塩酸水溶液１０．４ｇ（０．０２ｍｏｌｅ）、水４７．２ｇ、及びテトラヒドロフラン５０ｇ混合液を滴下した。滴下終了後、反応温度を８５℃に昇温し、昇温された温度で６時間反応させた。反応終了後、適量のテトラヒドロフランとメタノールを留去し、エーテルと水を添加して抽出し、有機相を回収し、残留アルコール及び溶媒を留去してシロキサン樹脂５４ｇを得た。得られたシロキサン樹脂をプロピレングリコールモノメチルエーテルアセテート１２５．５ｇに溶解した。このようにして製造したシロキサン重合体樹脂Ａ−２の重量平均分子量は６，０００であった。
b) Production of Resin A-2 62.5 g (0.05 mole) of methyl 3- (triethoxysilyl) propionate, 51.6 g (0.04 mole) of bicycloheptanyltotriethoxysilane, and 6.8 g (0 of methyltrimethoxysilane). 0.01 mole) and 200 g of propylene glycol monomethyl ether acetate are weighed and mixed, the resulting solution is stirred, and 10.4 g (0.02 mole) of 35% hydrochloric acid aqueous solution, 47.2 g of water, and 50 g of tetrahydrofuran are added dropwise. did. After completion of dropping, the reaction temperature was raised to 85 ° C., and the reaction was carried out at the elevated temperature for 6 hours. After completion of the reaction, appropriate amounts of tetrahydrofuran and methanol were distilled off, ether and water were added for extraction, the organic phase was recovered, and residual alcohol and solvent were distilled off to obtain 54 g of a siloxane resin. The obtained siloxane resin was dissolved in 125.5 g of propylene glycol monomethyl ether acetate. The siloxane polymer resin A-2 thus produced had a weight average molecular weight of 6,000.
ｃ）樹脂Ａ−３の製造
９，９−ビス（４−グリシジルオキシフェニル）フルオレン２３１ｇ、塩化テトラブチルアンモニウム１５０ｍｇ、及びプロピオン酸７４ｇを１２０℃に加熱し、１２時間反応させた。プロピオン酸をＧＣで分析することにより反応を停止させ、固相の中間体を得た（収率：９２％）。得られた固相の中間体２８０ｇをプロピレングリコールメチルエーテルアセテート（ＰＧＭＥＡ）４００ｍＬに溶解した後、３，３’，４，４’−ビフェニルテトラカルボン酸二無水物１０１．４ｇ、塩化テトラブチルアンモニウム５００ｍｇを加え、１２０℃で反応させた。最後に、フタル酸無水物３５ｇを混合し、９０℃で反応させた後、反応を停止させてカルド系重合体樹脂Ａ−３を得た。重量平均分子量は３，８００であった。
c) Production of Resin A-3 231 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 150 mg of tetrabutylammonium chloride and 74 g of propionic acid were heated to 120 ° C. and reacted for 12 hours. The reaction was stopped by analyzing propionic acid by GC to obtain a solid-phase intermediate (yield: 92%). After dissolving 280 g of the obtained solid-phase intermediate in 400 mL of propylene glycol methyl ether acetate (PGMEA), 101.4 g of 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride and 500 mg of tetrabutylammonium chloride. Was added and reacted at 120 ° C. Finally, 35 g of phthalic anhydride was mixed and reacted at 90 ° C., and then the reaction was stopped to obtain a cardo polymer resin A-3. The weight average molecular weight was 3,800.
ｃ）樹脂Ａ−４の製造
９，９−ビス（４−グリシジルオキシフェニル）フルオレン２３１ｇ、塩化テトラブチルアンモニウム１５０ｍｇ、２，６−ジ−t−ブチル−４−メチルフェノール１００ｍｇ、及びアクリル酸７２ｇを１２０℃に加熱し、１２時間反応させた。アクリル酸をＧＣで分析することにより反応を停止させ、固相の中間体を得た（収率：９２％）。得られた固相の中間体２８０ｇをプロピレングリコールメチルエーテルアセテート（ＰＧＭＥＡ）４００ｍＬに溶解した後、３，３’，４，４'−ビフェニルテトラカルボン酸二無水物１０１．４ｇ、塩化テトラブチルアンモニウム５００ｍｇを添加し、１２０℃で反応させた。最後に、フタル酸無水物３５ｇを混合し、９０℃で反応させた後、反応を停止させてカルド系重合体樹脂Ａ−４を得た。重量平均分子量は４，８００であった。
c) Production of Resin A-4 231 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 150 mg of tetrabutylammonium chloride, 100 mg of 2,6-di-t-butyl-4-methylphenol, and 72 g of acrylic acid. It heated at 120 degreeC and was made to react for 12 hours. The reaction was stopped by analyzing acrylic acid by GC to obtain a solid-phase intermediate (yield: 92%). After dissolving 280 g of the obtained solid-phase intermediate in 400 mL of propylene glycol methyl ether acetate (PGMEA), 101.4 g of 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride and 500 mg of tetrabutylammonium chloride. Was added and reacted at 120 ° C. Finally, 35 g of phthalic anhydride was mixed and reacted at 90 ° C., then the reaction was stopped to obtain a cardo type polymer resin A-4. The weight average molecular weight was 4,800.
ｄ）Ａ−５樹脂の製造
２，２−ビス（３−アミノ−４−ヒドロキシフェニル）−ヘキサフルオロプロパン２０．１ｇ、及び２，２’−ビス（トリフルオロメチル）４，４’−ジアミノビフェニル１７．６ｇをプロピレングリコールメチルエーテルアセテート（ＰＧＭＥＡ）１８０ｍＬに溶解した後、５−（２,５−ジオキソテトラヒドロフリル）−３−メチル−３−シクロヘキセン−１，２−ジカルボン酸無水物１４．５ｇをゆっくり添加し、反応させた後、４，４’−（ヘキサフルオロイソプロピリデン）ジフタル酸無水物２４．４ｇを添加し、２５℃で４時間、５０℃で２０時間反応させ、イミド系重合体樹脂Ａ−５を得た。重量平均分子量は２，８００であった。
d) Production of A-5 resin 2,2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane 20.1 g and 2,2'-bis (trifluoromethyl) 4,4'-diaminobiphenyl After dissolving 17.6 g in 180 mL of propylene glycol methyl ether acetate (PGMEA), 14.5 g of 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride Was slowly added and reacted, and then 24.4 g of 4,4 ′-(hexafluoroisopropylidene) diphthalic anhydride was added and reacted at 25 ° C. for 4 hours and at 50 ° C. for 20 hours to give an imide polymer. Resin A-5 was obtained. The weight average molecular weight was 2,800.
ｅ）Ａ−６樹脂の製造
４，４’−ジアミノジフェニルエーテル１１４ｇ、１，３−ビス（３−アミノプロピル）テトラメチルジシロキサン１２．３ｇ、及び３−アミノフェノール８１．８ｇをＮ−メチル−２−ピロリドン（ＮＭＰ）８００ｇに溶解した。その後、ビス（３，４−ジカルボキシフェニル）エーテル二無水物３１０ｇを、ＮＭＰ２００ｇと共に添加し、２０℃で１時間、５０℃で４時間反応させた。この後、キシレン１５０ｇ添加し、１５０℃で５時間撹拌した後、反応を停止させた。反応終了後の樹脂を精製水に沈殿させて洗浄した後、８０℃の真空乾燥機で２０時間乾燥してイミド系重合体樹脂Ａ−６を得た。重量平均分子量は１５，０００であった。
e) Production of A-6 resin 114 g of 4,4′-diaminodiphenyl ether, 12.3 g of 1,3-bis (3-aminopropyl) tetramethyldisiloxane, and 81.8 g of 3-aminophenol were added to N-methyl-2. -Dissolved in 800 g of pyrrolidone (NMP). Thereafter, 310 g of bis (3,4-dicarboxyphenyl) ether dianhydride was added together with 200 g of NMP and reacted at 20 ° C. for 1 hour and at 50 ° C. for 4 hours. Then, 150 g of xylene was added and stirred at 150 ° C. for 5 hours, and then the reaction was stopped. The resin after the completion of the reaction was precipitated in purified water and washed, and then dried in a vacuum dryer at 80 ° C. for 20 hours to obtain an imide polymer resin A-6. The weight average molecular weight was 15,000.
実施例１〜２８、及び比較例１〜６：感光性樹脂組成物の製造
紫外線遮断膜、及び撹拌機付き反応混合槽に、［Ａ］アルカリ可溶性樹脂２０重量％（固形分５０重量％、溶媒（ＰＧＭＥＡ）に溶解）、［Ｂ］ジペンタエリトリトールヘキサアクリレート５重量％、［Ｃ］ラクタムブラック２０重量％（固形分２５重量％、ＰＧＭＥＡ中に分散）、［Ｄ］光開始剤０．５重量％、及び添加剤として、ＦＣ−４３０（３Ｍ社製のレベリング剤、０．１重量％）を添加し、室温で撹拌した後、組成物が合計１００重量％になるように残りの溶媒を加えて感光性樹脂組成物を製造した。各実施例及び比較例で使用したアルカリ可溶性樹脂の種類、及び光開始剤の種類と含量を下記表１に示す。
Examples 1-28 and Comparative Examples 1-6: Production of Photosensitive Resin Composition [A] Alkali-soluble resin 20% by weight (solid content 50% by weight, solvent) in an ultraviolet blocking film and a reaction mixing tank equipped with a stirrer. (Dissolved in PGMEA), [B] dipentaerythritol hexaacrylate 5% by weight, [C] lactam black 20% by weight (solid content 25% by weight, dispersed in PGMEA), [D] photoinitiator 0.5% by weight %, And FC-430 (3M leveling agent, 0.1% by weight) as an additive, and after stirring at room temperature, the rest of the solvent was added so that the total composition was 100% by weight. To produce a photosensitive resin composition. Table 1 below shows the types of alkali-soluble resins used in each of the examples and comparative examples, and the types and contents of photoinitiators.
＜物性評価＞
上記実施例１〜２８、及び比較例１〜６で製造した感光性樹脂組成物について、感度、パターン特性などの性能を測定し、その評価結果を下記表２に示した。
<Physical property evaluation>
Performances such as sensitivity and pattern characteristics of the photosensitive resin compositions produced in Examples 1 to 28 and Comparative Examples 1 to 6 were measured, and the evaluation results are shown in Table 2 below.
１）限界寸法に対する露光量
ガラス基板上に、樹脂組成物をスピンコートし、１２０℃で９０秒間予熱して、厚さ約１．３μｍの塗膜を形成した。フォトマスクを用いて２０ｍＪ／ｃｍ２から１０ｍＪ／ｃｍ２に増圧された高圧水銀灯で露光した後、２．３８％テトラメチルアンモニウムヒドロキシド（ＴＭＡＨ）水溶液中で現像した。その後、純水で洗浄し、乾燥した後、２３０℃、対流式オーブンで３０分間加熱して遮光用パターンを形成した。感度は陰刻パターンのＣ．Ｄ．（Ｃｒｉｔｉｃａｌ ｄｉｍｅｎｓｉｏｎ）の大きさが飽和される露光量を各サンプルの感度として示した。
1) Exposure dose for critical dimension A resin composition was spin-coated on a glass substrate and preheated at 120 ° C. for 90 seconds to form a coating film having a thickness of about 1.3 μm. After exposure with a high-pressure mercury lamp was boosted from 20 mJ / cm 2 to 10 mJ / cm 2 using a photomask, and developed with a 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution. Then, after washing with pure water and drying, it was heated in a convection oven at 230 ° C. for 30 minutes to form a light shielding pattern. The sensitivity is C. D. The exposure amount at which the size of (Critical dimension) is saturated is shown as the sensitivity of each sample.
２）現像工程接着のための露光量
ガラス基板上に、フォトレジストをスピンコートし、１２０℃で９０秒間予熱して、厚さ約１．３μｍの塗膜を形成した。フォトマスクを用いて２０ｍＪ／ｃｍ２から１０ｍＪ／ｃｍ２に増圧された高圧水銀灯で露光した後、２．３８％ＴＭＡＨ水溶液中で現像した。現象後、１０μｍ未満の微細線パターンの剥離が見られない露光量でパターン密着性を評価した。
2) Exposure Step for Adhesion in Development Step A photoresist was spin-coated on a glass substrate and preheated at 120 ° C. for 90 seconds to form a coating film having a thickness of about 1.3 μm. After exposure with a high-pressure mercury lamp was boosted from 20 mJ / cm 2 to 10 mJ / cm 2 using a photomask, and then developed in 2.38% TMAH aqueous solution. After the phenomenon, the pattern adhesion was evaluated by the exposure amount in which the fine line pattern of less than 10 μm was not peeled off.
３）表面硬化度
上記感度評価にて決定された露光量で露光、及び現象を行った後、遮光膜の１０ｍｍ×１０ｍｍの表面に発生したピンホール数に基づいて、以下のように表面硬化度を決定した。○：ピンホールが０〜３個未満、△：ピンホール数が３〜７個未満、×：ピンホール数が７個以上。
3) Surface Hardness The degree of surface hardening is as follows based on the number of pinholes generated on the surface of the light-shielding film of 10 mm × 10 mm after the exposure and the phenomenon with the exposure amount determined in the above sensitivity evaluation. It was determined. ◯: 0 to less than 3 pinholes, Δ: 3 to less than 7 pinholes, ×: 7 or more pinholes.
４）現象工程の特性
上記感度評価、及び現像にて決定した露光量で露光した後、未露光部の現像時間をＢＴ、露光部微細線パターン１０μｍの剥離時間をＢＰとし、現象工程の範囲（ＢＰ−ＢＴ）を判定した。
4) Characteristics of Phenomenon Process After exposure with the exposure amount determined in the sensitivity evaluation and development described above, the development time of the unexposed area is BT, the peeling time of the exposed fine line pattern 10 μm is BP, and the range of the phenomenon step ( BP-BT) was determined.
５）パターン直進性
スピンコーターを用いて、遮光用組成物を基板上に塗布した後、プリベーク、露光、ポストベーク、及び現像を行い、形成された遮光用パターンの直進性を確認した。直進性は以下のように決定した。○：パターンの潰れや裂け目がない、△：パターンの潰れや裂け目の何れかがある、×：パターンの潰れや裂け目が両方ある。
5) Pattern Straightness A light-shielding composition was applied onto a substrate using a spin coater, and then prebaked, exposed, post-baked, and developed to confirm the straightness of the formed light-shielding pattern. Straightness was determined as follows. ◯: No pattern crushing or tearing, Δ: Either pattern crushing or tearing, ×: Both pattern crushing or tearing.
Claims (12)
で示される群、下記式（２）
で示される群、又は下記式（３）
で示される群から選ばれる２以上の群の化合物を含有する光開始剤。 The following formula (1)
Group represented by the following formula (2)
Or a group represented by the following formula (3)
A photoinitiator containing compounds of two or more groups selected from the group represented by:
式（２）の化合物が、下記の群
式（３）の化合物が、下記の群
Compounds of formula (2) are
Compounds of formula (3) are
［Ｂ］不飽和結合を有する重合性化合物；
［Ｃ］着色剤；及び
［Ｄ］請求項１〜４のいずれか１項に記載の光開始剤；
を含む遮光用感光性樹脂組成物。 [A] Alkali-soluble resin;
[B] a polymerizable compound having an unsaturated bond;
[C] a colorant; and [D] the photoinitiator according to any one of claims 1 to 4.
A light-shielding photosensitive resin composition containing:
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