KR20200124453A - Compound, photosensitive resin composition comprising the same, photoresist, color filter and display device - Google Patents
Compound, photosensitive resin composition comprising the same, photoresist, color filter and display device Download PDFInfo
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- KR20200124453A KR20200124453A KR1020190047793A KR20190047793A KR20200124453A KR 20200124453 A KR20200124453 A KR 20200124453A KR 1020190047793 A KR1020190047793 A KR 1020190047793A KR 20190047793 A KR20190047793 A KR 20190047793A KR 20200124453 A KR20200124453 A KR 20200124453A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 161
- 239000011342 resin composition Substances 0.000 title claims abstract description 45
- 229920002120 photoresistant polymer Polymers 0.000 title description 3
- 239000000463 material Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 abstract description 20
- 230000008569 process Effects 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 148
- 238000003786 synthesis reaction Methods 0.000 description 147
- -1 9,9-dimethylfluorenyl Chemical group 0.000 description 75
- 125000004432 carbon atom Chemical group C* 0.000 description 50
- 230000000052 comparative effect Effects 0.000 description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 239000000049 pigment Substances 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 16
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 15
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 11
- 235000006708 antioxidants Nutrition 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 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
- 230000007423 decrease Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004474 heteroalkylene group Chemical group 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 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 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- CWBLMSQPWRHFFH-UHFFFAOYSA-N [dimethoxy(propyl)silyl] 2-methylprop-2-enoate Chemical compound CCC[Si](OC)(OC)OC(=O)C(C)=C CWBLMSQPWRHFFH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 150000003949 imides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 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 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940067265 pigment yellow 138 Drugs 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- RFUCOAQWQVDBEU-UHFFFAOYSA-N methyl 2-(hydroxymethyl)prop-2-enoate Chemical compound COC(=O)C(=C)CO RFUCOAQWQVDBEU-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- ALIATVYMFGMEJC-UHFFFAOYSA-N phenyl-[2,4,6-tris(methylamino)phenyl]methanone Chemical compound CNC1=CC(NC)=CC(NC)=C1C(=O)C1=CC=CC=C1 ALIATVYMFGMEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 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
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- KPNZYDNOFDZXNR-UHFFFAOYSA-N tetratert-butyl 4-benzoylcyclohexa-3,5-diene-1,1,2,2-tetracarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)(C(=O)OOC(C)(C)C)C=CC(C(=O)C=2C=CC=CC=2)=C1 KPNZYDNOFDZXNR-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
-
- 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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
본 명세서는 화합물 및 이를 포함하는 감광성 수지 조성물에 관한 것이다. 또한, 본 명세서는 상기 감광성 수지 조성물을 이용하여 제조된 감광재, 컬러필터 및 디스플레이 장치에 관한 것이다.The present specification relates to a compound and a photosensitive resin composition comprising the same. In addition, the present specification relates to a photosensitive material, a color filter, and a display device manufactured by using the photosensitive resin composition.
최근 컬러필터에 있어서 고휘도, 고명암비를 특징으로 하는 성능이 요구되고 있다. 또한, 디스플레이 장치 개발의 주 목적 중 하나는 색순도 향상을 통한 표시소자 성능의 차별화 및 제조 공정상의 생산성 향상에 있다. Recently, a color filter is required to have high luminance and high contrast ratio. In addition, one of the main objectives of the development of a display device is to differentiate display device performance through improved color purity and to improve productivity in a manufacturing process.
기존에 컬러필터의 색재로 사용되는 안료 타입은 입자 분산 상태로 컬러 포토레지스트에 존재하기 때문에, 안료 입자 크기와 분포 조절에 따른 휘도 및 명암비 조절에 어려움이 있었다. 안료 입자의 경우 컬러 필터 내에서 응집되어 용해 및 분산성이 떨어지며 응집(aggregation)되어 있는 큰 입자들로 인하여 빛의 다중 산란(multiple scattering)이 일어난다. 이러한 편광된 빛의 산란은 명암비를 저하시키는 주 요인으로 지목되고 있다. 안료의 초미립화 및 분산 안정화를 통해 휘도 및 명암비 향상을 위한 노력이 계속되고 있으나, 고색순도 표시장치용 색좌표를 구현하기 위한 색재 선정에 있어 자유도가 제한된다. 또한, 이미 개발된 색재료 특히 안료를 이용한 안료분산법은 이를 이용한 컬러필터의 색순도, 휘도 및 명암비를 향상시키는데 한계에 도달했다.Conventionally, since the pigment type used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, they are aggregated in a color filter, so that dissolution and dispersibility are inferior, and multiple scattering of light occurs due to large aggregated particles. The scattering of polarized light has been pointed out as the main factor that lowers the contrast ratio. Efforts have been made to improve brightness and contrast ratio through ultra-fine pigmentation and dispersion stabilization, but the degree of freedom is limited in selecting a color material for realizing color coordinates for high-color purity display devices. In addition, the already developed color material, particularly the pigment dispersion method using a pigment, has reached its limit in improving the color purity, brightness, and contrast ratio of a color filter using the same.
이에 따라서, 색순도를 높여 색재현, 휘도 및 명암비를 향상시킬 수 있는 신규 색재 개발이 요구되고 있다.Accordingly, there is a need to develop a new color material capable of improving color reproduction, brightness, and contrast ratio by increasing color purity.
본 명세서는 화합물, 이를 포함하는 감광성 수지 조성물, 이를 이용하여 제조된 감광재, 컬러필터 및 디스플레이 장치를 제공하고자 한다.The present specification is to provide a compound, a photosensitive resin composition comprising the same, a photosensitive material manufactured using the same, a color filter, and a display device.
본 명세서의 일 실시상태는, 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에 있어서,In Formula 1,
M은 수소; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; 또는 Zr이고, M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,
상기 M이 Al인 경우, M은 -O(P=O)R'R''와 결합되고,When M is Al, M is combined with -O(P=O)R'R'',
상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환 알콕시기; 또는 치환 또는 비치환 아릴옥시기이며, R1 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며,R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
R1 내지 R16 중 적어도 하나는 히드록시기이고, R1 내지 R16 중 히드록시기가 아닌 치환기 중 적어도 하나는 -OR이며,At least one of R1 to R16 is a hydroxy group, and at least one of the substituents other than a hydroxy group of R1 to R16 is -OR,
상기 R은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태는, 상기 화학식 1로 표시되는 화합물; 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 포함하는 감광성 수지 조성물을 제공한다.An exemplary embodiment of the present specification, the compound represented by Formula 1; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.
본 명세서의 일 실시상태는, 상기 감광성 수지 조성물을 포함하는 감광재를 제공한다.An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.
본 명세서의 일 실시상태는, 상기 감광재를 포함하는 컬러필터를 제공한다.An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
본 명세서의 일 실시상태는, 상기 컬러필터를 포함하는 디스플레이 장치를 제공한다.An exemplary embodiment of the present specification provides a display device including the color filter.
본 명세서의 일 실시상태에 따른 화합물은 감광성 수지 조성물에서 색재로 사용될 수 있으며, 유기 용제에 대한 용해도를 가짐으로써 분산 공정을 줄일 수 있어, 종래의 안료를 적용하는 경우 분산 공정을 거쳐야 하는 것과 다르게, 경제적인 방법으로 화합물을 색재로 사용할 수 있다.The compound according to an exemplary embodiment of the present specification may be used as a colorant in the photosensitive resin composition, and has solubility in an organic solvent, so that the dispersion process can be reduced. When applying a conventional pigment, unlike the dispersion process, The compound can be used as a colorant in an economical way.
또한, 본 명세서의 일 실시상태에 따른 화합물은 내열성이 우수하다. In addition, the compound according to an exemplary embodiment of the present specification is excellent in heat resistance.
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서에 있어서, 어떤 부재가 다른 부재 “상에” 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is positioned “on” another member, this includes not only a case where a member is in contact with another member, but also a case where another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.
본 명세서에 있어서, “결합”된다는 것은 원자 간의 공유결합을 의미할 수 있다.In the present specification, "bonding" may mean a covalent bond between atoms.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다. An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에 있어서,In Formula 1,
M은 수소; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; 또는 Zr이고, M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,
상기 M이 Al인 경우, M은 -O(P=O)R'R''와 결합되고,When M is Al, M is combined with -O(P=O)R'R'',
상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환 알콕시기; 또는 치환 또는 비치환 아릴옥시기이며, R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group,
R1 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며,R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
R1 내지 R16 중 적어도 하나는 히드록시기이고, R1 내지 R16 중 히드록시기가 아닌 치환기 중 적어도 하나는 -OR이며,At least one of R1 to R16 is a hydroxy group, and at least one of the substituents other than a hydroxy group of R1 to R16 is -OR,
상기 R은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서에 따른 화합물은 프탈로시아닌(Phthalocyanine) 구조가 적어도 하나의 히드록시기를 포함함으로 인해, 상기 화합물이 색재로 사용되는 경우 유기 용매에 우수한 용해도를 가진다. The compound according to the present specification has excellent solubility in an organic solvent when the compound is used as a colorant because the phthalocyanine structure includes at least one hydroxy group.
프탈로시아닌(Phthalocyanine) 구조에 치환기가 할로겐기(halogen) 또는 수소만 치환되어 있는 화합물의 경우에는 용해도가 부족하다. 따라서, 할로겐기 또는 수소만 치환되어 있는 프탈로시아닌(Phthalocyanine) 구조의 화합물을 컬러필터에 적용하기 위해서는 분산공정을 진행해야 하고, 분산공정에 필요한 분산제, 바인더 등의 추가적인 재료가 필요하다. In the case of a compound in which a substituent group is substituted with only halogen or hydrogen in a phthalocyanine structure, solubility is insufficient. Therefore, in order to apply a phthalocyanine structured compound in which only a halogen group or hydrogen is substituted to a color filter, a dispersion process must be performed, and additional materials such as a dispersant and a binder required for the dispersion process are required.
이에 비해, 본 명세서에 따른 화합물과 같이 프탈로시아닌 구조에 알킬 또는 아릴 옥시기가 치환된 경우, 용해도가 증가되어 분산공정이 필요하지 않으며, 분산공정에 사용되는 추가적인 재료가 필요하지 않다. In contrast, when an alkyl or aryloxy group is substituted in the phthalocyanine structure as in the compound according to the present specification, solubility is increased, so that a dispersion process is not required, and an additional material used in the dispersion process is not required.
프탈로시아닌(Phthalocyanine) 구조는 장파장 영역에 Qy, Qx 2개의 흡수피크를 갖는다(파장 Qx nm > Qy nm). 용해도가 부족한 프탈로시아닌의 경우 Qy와 Qx의 흡수 강도가 유사하나, 용해도가 증가된 프탈로시아닌의 경우 Qx의 흡수 강도가 Qy의 흡수 강도보다 훨씬 크다.Phthalocyanine structure has two absorption peaks Qy and Qx in a long wavelength region (wavelength Qx nm> Qy nm). In the case of phthalocyanine having insufficient solubility, the absorption strength of Qy and Qx is similar, but in the case of phthalocyanine with increased solubility, the absorption strength of Qx is much greater than that of Qy.
구체적으로, 프탈로시아닌 구조를 용해시킬 수 있는 적절한 용매를 선정하고, 상온(25℃)에서 1.0Ⅹ10-5mol/L 농도의 용액을 UV-Vis spectrometer를 이용하여 300~800nm 영역의 흡수를 측정한다. 측정된 단파장 영역(300~400nm)흡수의 최대 흡수파장을 B-band(Soret band)라고 하며, 장파장 영역(600~800nm)흡수의 최대 흡수파장을 Q-band라고 한다. 장파장 영역의 Q-band 흡수에서 단파장을 Qy-band라고 하고, 보다 장파장을 Qx-band라고 한다. Specifically, an appropriate solvent capable of dissolving the phthalocyanine structure is selected, and absorption of a solution having a concentration of 1.0×10 -5 mol/L at room temperature (25° C.) is measured in the region of 300 to 800 nm using a UV-Vis spectrometer. The maximum absorption wavelength of absorption in the measured short wavelength region (300~400nm) is called B-band (Soret band), and the maximum absorption wavelength in absorption in the long wavelength region (600~800nm) is called Q-band. In the Q-band absorption in the long wavelength region, the short wavelength is called Qy-band, and the longer wavelength is called Qx-band.
프탈로시아닌(Phthalocyanine) 구조의 용해도가 낮은 경우 프탈로시아닌 분자간의 응집(aggregation)을 통해 Qy 흡수 강도가 증가한다. 그러나 응집(aggregation)에 의한 산란으로 명암비(CR, Contrast Ratio)의 감소와 다양한 에너지 밴드의 겹침으로 투과율이 감소된다. 프탈로시아닌(Phthalocyanine) 구조의 용해도가 높을 경우 분자간의 응집(aggregation)이 감소되어 명암비(CR, Contrast Ratio)의 증가 및 투과도 향상을 시킬 수 있다. When the solubility of the phthalocyanine structure is low, the Qy absorption strength increases through aggregation between phthalocyanine molecules. However, due to scattering due to aggregation, the transmittance decreases due to the reduction of the contrast ratio (CR) and the overlapping of various energy bands. When the solubility of the phthalocyanine structure is high, aggregation between molecules is reduced, thereby increasing the contrast ratio (CR) and improving the transmittance.
컬러필터에 사용하기 위한 프탈로시아닌 구조의 경우 Qy의 흡수 강도가 중요하다. Qy의 흡수 강도가 강할 경우, 컬러필터의 색좌표를 만족시키기 위한 프탈로시아닌 구조의 사용량을 줄일 수 있고, 이에 따라 공정성을 만족시킬 수 있는 바인더 또는 첨가제 등의 함량을 증가시킬 수 있는 장점을 가진다. In the case of a phthalocyanine structure for use in a color filter, the absorption strength of Qy is important. When the absorption strength of Qy is strong, the amount of the phthalocyanine structure used to satisfy the color coordinate of the color filter can be reduced, and accordingly, the content of a binder or additive that can satisfy fairness can be increased.
용매에 대한 용해도를 향상시키고, 용매가 제거된 이후에 적절한 응집(aggregation)을 유도하면 Qy의 흡수 강도 증가에 따른 색재 함량의 감소, 명암비(CR, Contrast Ratio)의 증가, 투과율을 향상시킬 수 있다. If the solubility of the solvent is improved and appropriate aggregation is induced after the solvent is removed, the colorant content decreases, the contrast ratio (CR) increases, and the transmittance can be improved according to the increase in the absorption strength of Qy. .
이러한 목적을 달성하기 위해 프탈로시아닌 구조에 알킬 또는 아릴 옥시기를 치환기로 도입하여 용해도를 증가시키고, 추가적으로 적어도 하나의 히드록시기를 치환기로 도입하여 분자간의 상호 작용을 통해 응집(aggregation)을 유도하여 Qy 흡수 세기를 증가 시킬 수 있다. 예컨대, 상기 상호 작용은 수소결합을 의미할 수 있다.To achieve this purpose, the solubility is increased by introducing an alkyl or aryloxy group as a substituent in the phthalocyanine structure, and at least one hydroxy group is additionally introduced as a substituent to induce aggregation through interaction between molecules, thereby increasing the Qy absorption strength. Can be increased. For example, the interaction may mean a hydrogen bond.
따라서, 본 명세서에 따른 화합물은 Qy의 흡수세기의 증가를 통해 색재 사용량을 줄일 수 있고, 용해도 증가를 통해 색재 분산에 필요한 재료의 양을 줄임으로써, 경제성을 높일 수 있다. 또한, 명암비(CR, Contrast Ratio) 향상이 가능하고, 우수한 내열성을 가질 수 있다. Therefore, the compound according to the present specification can reduce the amount of colorant used by increasing the absorption intensity of Qy, and increase the economic efficiency by reducing the amount of material required for dispersing the colorant through an increase in solubility. In addition, it is possible to improve the contrast ratio (CR) and have excellent heat resistance.
상기 화학식 1로 표시되는 화합물의 치환기들의 예시는 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents of the compound represented by Formula 1 are described below, but are not limited thereto.
본 명세서에 있어서, 는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification, Means a site bonded to another substituent or a bonding portion.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 히드록시기; 알콕시기; 알킬기; 시클로알킬기; 알케닐기; 시클로알케닐기; 아릴기; 헤테로아릴기; 아크릴로일기; 아크릴레이트기; 에테르기; 및 N, O, S 또는 P 원자 중 1개 이상을 포함하는 헤테로고리기를 포함하는 군에서 선택된 1개 이상의 치환기로 치환되었거나 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Hydroxy group; Alkoxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heteroaryl group; Acryloyl group; Acrylate group; Ether group; And it means that it is substituted with one or more substituents selected from the group containing a heterocyclic group containing one or more of N, O, S, or P atoms, or does not have any substituents.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 인접한 기는 결합하여 “고리”를 형성할 수 있다는 것에서 상기 고리란, 방향족 또는 지방족 고리를 의미한다. 구체적으로, 상기 고리는 방향족 고리일 수 있으며, 아릴기 또는 헤테로아릴기일 수 있다. 상기 아릴기 및 헤테로아릴기는 후술하는 설명이 적용될 수 있다.In the present specification, the ring means an aromatic or aliphatic ring in that adjacent groups can be bonded to form a “ring”. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The aryl group and the heteroaryl group may be described below.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알콕시기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 1 내지 30일 수 있으며, 구체적으로는 1 내지 20일 수 있고, 더욱 구체적으로는 1 내지 10일 수 있다. In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.
본 명세서에 있어서, 상기 아릴옥시기 중의 아릴기는 후술하는 아릴기에 대한 설명이 적용된다.In the present specification, the aryl group in the aryloxy group is described below for the aryl group.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 이소부틸기, tert-부틸기, n-펜틸기, n-헥실기, n-헵틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-oxy And the like, but are not limited to these.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 10이다. 알케닐기의 구체적인 예로는 스틸베닐기(stylbenyl), 스티레닐기(styrenyl)기 등의 아릴기가 치환된 알케닐기가 바람직하나 이들에 한정되지 않는다. In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group are preferably an alkenyl group substituted with an aryl group such as a stylbenyl group and a styrenyl group, but are not limited thereto.
본 명세서에 있어서, 시클로알케닐기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 시클로알케닐기의 예로는 시클로펜테닐렌기, 시클로헥세닐렌기가 바람직하나, 이들에 한정되지 않는다. In the present specification, the cycloalkenyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group are preferably a cyclopentenylene group and a cyclohexenylene group, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 인데닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우, , 등의 스피로플루오레닐기, (9,9-디메틸플루오레닐기), 및 (9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, , Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
본 명세서에 있어서, 상기 헤테로고리기는 이종원자로 O, N 또는 S를 포함하는 헤테고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30, 구체적으로는 탄소수 2 내지 20이다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 트리아진기, 아크리딜기, 피리다진기, 퀴놀리닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨란기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited to these.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 아크릴로일기는 광중합성 불포화기를 의미하며, 예컨대, (메타)아크릴로일기를 들 수 있으나 이에 한정되는 것은 아니다. In the present specification, the acryloyl group refers to a photopolymerizable unsaturated group, for example, a (meth)acryloyl group, but is not limited thereto.
본 명세서에 있어서, 아크릴레이트기는 광중합성 불포화기를 의미하며, 예컨대 (메타)아크릴레이트기를 들 수 있으나 이에 한정되는 것은 아니다. In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, such as a (meth)acrylate group, but is not limited thereto.
본 명세서에 있어서, '(메타)아크릴로일'이란, 아크릴로일 및 메타아크릴로일로 이루어지는 군으로부터 선택되는 적어도 1종을 나타낸다. '(메타)아크릴레이트' 의 표기도 마찬가지의 의미를 갖는다.In the present specification, "(meth)acryloyl" refers to at least one selected from the group consisting of acryloyl and methacryloyl. The notation of'(meth)acrylate' has the same meaning.
본 명세서에서 알킬렌기는 알칸(alkane)에 결합위치가 두 개 있는 것을 의미한다. 상기 알킬렌기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알킬렌기의 탄소수는 특별히 한정되지 않으나, 예컨대 탄소수 1 내지 30, 구체적으로는 1 내지 20, 더욱 구체적으로는 1 내지 10이다.In the present specification, the alkylene group means that the alkane has two bonding sites. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 1 to 30, specifically 1 to 20, and more specifically 1 to 10 carbon atoms.
본 명세서에 있어서, 헤테로알킬렌기는 이종원자로 O, N 또는 S를 포함하는 알칸(alkane)에 결합위치가 두 개 있는 것을 의미한다. 상기 헤테로알킬렌기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 헤테로알킬렌기의 탄소수는 특별히 한정되지 않으나, 예컨대 탄소수 2 내지 30, 구체적으로는 탄소수 2 내지 20, 더욱 구체적으로는 탄소수 2 내지 10이다.In the present specification, the heteroalkylene group means that there are two bonding positions in an alkane containing O, N or S as a hetero atom. The heteroalkylene group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
본 명세서의 일 실시상태에 있어서, M은 수소; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; 또는 Zr이다. In an exemplary embodiment of the present specification, M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr.
본 명세서의 일 실시상태에 있어서, 상기 M이 Al인 경우, M은 -O(P=O)R'R''와 결합된다.In this specification, in the day implementation status , when M is Al, M is combined with -O(P=O)R'R''.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환 알콕시기; 또는 치환 또는 비치환 아릴옥시기이다.In the day implementation state of this specification, the R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 탄소수 6 내지 30의 치환 또는 비치환된 아릴기; 탄소수 1 내지 30의 치환 또는 비치환 알콕시기; 또는 탄소수 6 내지 30의 치환 또는 비치환 아릴옥시기이다.In the day implementation state of this specification, the R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 탄소수 6 내지 20의 치환 또는 비치환된 아릴기; 탄소수 1 내지 20의 치환 또는 비치환 알콕시기; 또는 탄소수 6 내지 20의 치환 또는 비치환 아릴옥시기이다.In the day implementation state of this specification, the R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 탄소수 6 내지 12의 치환 또는 비치환된 아릴기; 탄소수 1 내지 10의 치환 또는 비치환 알콕시기; 또는 탄소수 6 내지 12의 치환 또는 비치환 아릴옥시기이다.In the day implementation state of this specification, the R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryloxy group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 페녹시기이다.In this specification, in the day implementation state , the R'and R'' are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; Or a substituted or unsubstituted phenoxy group.
본 명세서의 일 실시상태에 있어서, 상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 페닐기; 또는 페녹시기이다In this specification, in the day implementation state , the R'and R'' are the same as or different from each other, and each independently a phenyl group; Or a phenoxy group
본 명세서의 일 실시상태에 있어서, M은 Zn; Al;또는 Cu이다.In an exemplary embodiment of the present specification, M is Zn; Al; or Cu.
본 명세서의 일 실시상태에 있어서, M은 Zn이다. In an exemplary embodiment of the present specification, M is Zn.
본 명세서의 일 실시상태에 있어서, M은 Cu이다.In an exemplary embodiment of the present specification, M is Cu.
본 명세서의 일 실시상태에 있어서, M은 Al이다. In this specification, in the day actual condition , M is Al.
본 명세서의 일 실시상태에 있어서, R1 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며, R1 내지 R16 중 적어도 하나는 히드록시기이고, R1 내지 R16 중 히드록시기가 아닌 치환기 중 적어도 하나는 -OR이다. In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR, at least one of R1 to R16 is a hydroxy group, and at least one of substituents other than a hydroxy group of R1 to R16 is -OR.
본 명세서의 일 실시상태에 있어서, R1 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 염소; 브롬; 또는 -OR이며, R1 내지 R16 중 적어도 하나는 히드록시기이고, R1 내지 R16 중 히드록시기가 아닌 치환기 중 적어도 하나는 -OR이다. In the exemplary embodiment of the present specification, R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Goat; bromine; Or -OR, at least one of R1 to R16 is a hydroxy group, and at least one of substituents other than a hydroxy group of R1 to R16 is -OR.
본 명세서의 일 실시상태에 있어서, R은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. In an exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, R은 탄소수 1 내지 30의 치환 또는 비치환된 알킬기; 탄소수 3 내지 30의 치환 또는 비치환된 시클로알킬기; 탄소수 6 내지 30의 치환 또는 비치환된 아릴기; 또는 탄소수 3 내지 30의 치환 또는 비치환된 헤테로고리기이다. In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R은 탄소수 1 내지 20의 치환 또는 비치환된 알킬기; 탄소수 3 내지 20의 치환 또는 비치환된 시클로알킬기; 탄소수 6 내지 20의 치환 또는 비치환된 아릴기; 또는 탄소수 3 내지 20의 치환 또는 비치환된 헤테로고리기이다. In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R은 탄소수 1 내지 10의 치환 또는 비치환된 알킬기; 탄소수 3 내지 10의 치환 또는 비치환된 시클로알킬기; 탄소수 6 내지 12의 치환 또는 비치환된 아릴기; 또는 탄소수 3 내지 12의 치환 또는 비치환된 헤테로고리기이다. In the exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, R은 탄소수 6 내지 12의 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, R은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이다.In the exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.
본 명세서의 일 실시상태에 있어서, R은 페닐기; 메틸기로 치환된 페닐기; tert-부틸기로 치환된 페닐기; 시클로헥실기로 치환된 페닐기; 바이페닐기; 또는 나프틸기이다.In an exemplary embodiment of the present specification, R is a phenyl group; A phenyl group substituted with a methyl group; a phenyl group substituted with a tert-butyl group; A phenyl group substituted with a cyclohexyl group; Biphenyl group; Or a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 2로 표시되는 화합물을 제공한다, In an exemplary embodiment of the present specification, Formula 1 provides a compound represented by Formula 2 below,
[화학식 2][Formula 2]
상기 화학식 2에 있어서,In Formula 2,
M은 상기 화학식 1에서의 정의와 동일하고, M is the same as the definition in Formula 1,
R1 내지 R14 및 R16는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며,R1 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
R1 내지 R14 및 R16 중 적어도 하나는 히드록시기이고,At least one of R1 to R14 and R16 is a hydroxy group,
R 및 Z1은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R and Z1 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, R14는 히드록시기이다. In an exemplary embodiment of the present specification, R14 is a hydroxy group.
본 명세서의 일 실시상태에 있어서, R3, R7, R11 및 R15 중 적어도 하나는 -OR이고, 상기 R은 상기 화학식 1에서의 정의와 동일하다. In an exemplary embodiment of the present specification, at least one of R3, R7, R11, and R15 is -OR, and R is the same as defined in Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, R15는 -OR이고, 상기 R은 상기 화학식 1에서의 정의와 동일하다.In the exemplary embodiment of the present specification, R15 is -OR, and R is the same as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, R2, R6, R10 및 R14 중 적어도 하나는 히드록시기이다. In an exemplary embodiment of the present specification, at least one of R2, R6, R10, and R14 is a hydroxy group.
본 명세서의 일 실시상태에 있어서, R13 및 R16은 염소이다.In an exemplary embodiment of the present specification, R13 and R16 are chlorine.
본 명세서의 일 실시상태에 있어서, R13은 브롬이다.In an exemplary embodiment of the present specification, R13 is bromine.
본 명세서의 일 실시상태에 있어서, R13은 염소이다.In an exemplary embodiment of the present specification, R13 is chlorine.
본 명세서의 일 실시상태에 있어서, R1 내지 R12는 서로 같거나 상이하고, 각각 독립적으로 수소; 염소; 또는 브롬이다.In the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; Goat; Or bromine.
본 명세서의 일 실시상태에 있어서, R1 내지 R12는 수소이다.In this specification, in the day implementation state, R1 to R12 are hydrogen.
본 명세서의 일 실시상태에 있어서, R1 내지 R12는 염소이다. In this specification, in the day implementation state, R1 to R12 are chlorine.
본 명세서의 일 실시상태에 있어서, R1 내지 R12는 브롬이다.In this specification, in the day implementation status , R1 to R12 are bromine.
본 명세서의 또 하나의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 중 어느 하나로 표시될 수 있으나, 반드시 이에 한정되는 것은 아니다.According to another exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following formulas, but is not limited thereto.
본 명세서의 일 실시상태는 상기 화학식 1로 표시되는 화합물; 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 포함하는 감광성 수지 조성물을 제공한다.An exemplary embodiment of the present specification is a compound represented by Formula 1; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.
상기 감광성 수지 조성물은 상기 화학식 1의 화합물 이외에 염료 및 안료 중 적어도 1종을 더 포함할 수 있다. 예컨대, 상기 색재 조성물은 상기 화학식 1의 화합물만을 포함할 수도 있으나, 상기 화학식 1의 화합물과 1종 이상의 염료를 포함하거나, 상기 화학식 1의 화합물과 1종 이상의 안료를 포함하거나, 상기 화학식 1의 화합물, 1종 이상의 염료 및 1종 이상의 안료를 포함할 수도 있다. The photosensitive resin composition may further include at least one of a dye and a pigment in addition to the compound of Formula 1 above. For example, the color material composition may include only the compound of Formula 1, but includes the compound of Formula 1 and at least one dye, the compound of Formula 1 and at least one pigment, or the compound of Formula 1 , One or more dyes and one or more pigments may be included.
상기 감광성 수지 조성물은 안료 분산액을 더 포함할 수 있다. 상기 안료 분산액은 예컨대, Pigment Yellow 138, 139, 185 안료 분산액일 수 있으나 이에 한정되는 것은 아니다. The photosensitive resin composition may further include a pigment dispersion. The pigment dispersion may be, for example, Pigment Yellow 138, 139, 185 pigment dispersion, but is not limited thereto.
상기 바인더 수지는 감광성 수지 조성물로 제조된 막의 강도, 현상성 등의 물성을 나타낼 수 있다면, 특별히 한정하지 않는다. The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of the photosensitive resin composition.
상기 바인더 수지는 막의 기계적 강도를 부여하는 다관능성 모노머와 알칼리 용해성을 부여하는 모노머의 공중합 수지를 이용할 수 있으며, 당 기술분야에서 일반적으로 사용하는 바인더를 더 포함할 수 있다. The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength of the film and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
상기 '막의 기계적 강도를 부여하는 다관능성 모노머'는 불포화 카르복시산 에스테류; 방향족 비닐류; 불포화 에테르류; 불포화 이미드류; 및 산 무수물 중 어느 하나 이상일 수 있다. The'polyfunctional monomer imparting mechanical strength of the film' may include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.
상기 불포화 카르복시산 에스테르류의 구체적인 예로는, 벤질(메타)아크릴레이트, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 디메틸아미노에틸(메타)아크릴레이트, 이소부틸(메타)아크릴레이트, t-부틸(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 2-페녹시에틸(메타)아크릴레이트, 테트라히드로퍼프릴(메타)아크릴레이트, 히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시-3-클로로프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메타)아크릴레이트, 글리세롤(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 에톡시디에틸렌글리콜 (메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시트리프로필렌글리콜(메타)아크릴레이트, 폴리(에틸렌 글리콜) 메틸에테르(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메타)아크릴레이트, 글리시딜(메타)아크릴레이트, 테트라플루오로프로필(메타)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필 (메타)아크릴레이트, 옥타플루오로펜틸(메타)아크릴레이트, 헵타데카플루오로데실(메타)아크릴레이트, 트리브로모페닐(메타)아크릴레이트, 메틸 α-히드록시메틸 아크릴레이트, 에틸 α-히드록시메틸 아크릴레이트, 프로필 α-히드록시메틸 아크릴레이트 및 부틸 α-히드록시메틸 아크릴레이트로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated carboxylic acid esters are benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofurpril (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, acyloctyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) )Acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) Acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.
상기 방향족 비닐류의 구체적인 예로는, 스티렌, α-메틸스티렌, (o,m,p)-비닐 톨루엔, (o,m,p)-메톡시 스티렌, 및 (o,m,p)-클로로 스티렌으로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.
상기 불포화 에테르류의 구체적인 예로는, 비닐 메틸 에테르, 비닐 에틸 에테르, 및 알릴 글리시딜 에테르로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
상기 불포화 이미드류의 구체적인 예로는, N-페닐 말레이미드, N-(4-클로로페닐) 말레이미드, N-(4-히드록시페닐) 말레이미드, 및 N-시클로헥실 말레이미드로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.
상기 산 무수물로는 무수 말레인산, 무수 메틸 말레인산, 테트라하이드로 프탈산 무수물 등이 있으나, 이들에만 한정되는 것은 아니다.Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.
상기 알칼리 용해성을 부여하는 모노머는 산기를 포함한다면 특별히 한정되지 않으며, 예를 들면, (메타)아크릴산, 크로톤산, 이타콘산, 말레인산, 푸마르산, 모노메틸 말레인산, 5-노보넨-2-카복실산, 모노-2-((메타)아크릴로일옥시)에틸 프탈레이트, 모노-2-((메타)아크릴로일옥시)에틸 숙시네이트, ω-카르복시 폴리카프로락톤 모노(메타)아크릴레이트로 이루어지는 군으로부터 선택되는 1 종 이상을 사용하는 것이 바람직하나, 이들에만 한정되는 것은 아니다.The monomer imparting alkali solubility is not particularly limited as long as it includes an acid group, and examples include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ω-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more, but is not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 바인더 수지의 산가는 50 KOH mg/g내지 130 KOH mg/g이고, 중량 평균 분자량은 1,000 g/mol 내지 50,000 g/mol 이다. According to an exemplary embodiment of the present specification, the acid value of the binder resin is 50 KOH mg/g to 130 KOH mg/g, and the weight average molecular weight is 1,000 g/mol to 50,000 g/mol.
상기 바인더 수지의 산가는 0.1N 농도의 수산화칼륨(KOH) 메탄올 용액으로 적정하여 측정할 수 있고, 상기 중량 평균 분자량은 겔투과크로마토그래피(GPC)를 이용하여 측정할 수 있다. The acid value of the binder resin can be measured by titration with a 0.1N concentration of potassium hydroxide (KOH) methanol solution, and the weight average molecular weight can be measured using gel permeation chromatography (GPC).
상기 다관능성 모노머는 광에 의해 포토레지스트상을 형성하는 역할을 하는 모노머로서, 구체적으로는 프로필렌글리콜 메타크릴레이트, 디펜타에리쓰리톨 헥사아크릴레이트, 디펜타에리쓰리톨 아크릴레이트, 네오펜틸글리콜 디아크릴레이트, 6-헥산디올 디아크릴레이트, 1,6-헥산디올 아크릴레이트 테트라에틸렌글리콜 메타크릴레이트, 비스페녹시 에틸알콜 디아크릴레이트, 트리스히드록시에틸이소시아누레이트 트리메타크릴레이트, 트리메틸프로판 트리메타크릴레이트, 디페닐펜타에리쓰톨리톨 헥사아크릴레이트, 펜타에리 쓰리톨 트리메타 크릴레이트, 펜타에리쓰리톨 테트라메타크릴레이트 및 디펜타에리 쓰리톨 헥사메타 크릴레이트로 이루어진 그룹 중에서 선택되는 1종 또는 2종 이상의 혼합물일 수 있다.The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di. Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl Selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate It may be one or a mixture of two or more.
상기 다관능성 모노머는 구체적으로 디펜타에리쓰리톨 헥사아크릴레이트(DPHA)일 수 있다.The polyfunctional monomer may be specifically dipentaerythritol hexaacrylate (DPHA).
상기 광개시제는 빛에 의해 라디칼을 발생시켜 가교를 촉발하는 개시제이면, 특별히 한정되지 않으나, 예를 들면, 아세토페논계 화합물, 비이미다졸계 화합물, 트리아진계 화합물, 및 옥심계 화합물로 이루어진 군으로부터 선택되는 1종 이상일 수 있다. The photoinitiator is not particularly limited as long as it is an initiator that generates a radical by light to trigger crosslinking, but is, for example, selected from the group consisting of an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more.
상기 아세토페논계 화합물은 2-히드록시-2-메틸-1-페닐프로판-1-온, 1-(4-이소프로필페닐)-2-히드록시-2-메틸프로판-1-온, 4-(2-히드록시에톡시)-페닐-(2-히드록시-2-프로필)케톤, 1-히드록시시클로헥실페닐케톤, 벤조인메틸 에테르, 벤조인에틸 에테르, 벤조인이소부틸 에테르, 벤조인부틸 에테르, 2,2-디메톡시-2-페닐아세토페논, 2-메틸-(4-메틸티오)페닐-2-몰폴리노-1-프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온, 2-(4-브로모-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온 또는 2-메틸-1-[4-(메틸티오)페닐]-2-몰폴리노프로판-1-온 등이 있으며, 이에 한정되지 않는다. The acetophenone compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like, but is not limited thereto.
상기 비이미다졸계 화합물로는 2,2-비스(2-클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4',5,5'-테트라키스(3,4,5-트리메톡시페닐)-1,2'-비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4,5,5'-테트라페닐-1,2'-비이미다졸 등이 있으며, 이에 한정되지 않는다. The biimidazole-based compound is 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , Is not limited thereto.
상기 트리아진계 화합물은 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 1,1,1,3,3,3-헥사플로로이소프로필-3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오네이트, 에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 2-에폭시에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 시클로헥실-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 벤질-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 3-{클로로-4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피온아미드, 2,4-비스(트리클로로메틸)-6-p-메톡시스티릴-s-트리아진, 2,4-비스(트리클로로메틸)-6-(1-p-디메틸아미노페닐)-1,3-부타디에닐-s-트리아진, 2-트리클로로메틸-4-아미노-6-p-메톡시스티릴-s-트리아진 등이 있으며, 이에 한정되지 않는다. The triazine compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -Bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionamide, 2,4-bis(trichloro Methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s- Triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.
상기 옥심계 화합물은 1,2-옥타디온-1-(4-페닐치오)페닐-2-(o-벤조일옥심)(시바가이기사, 시지아이124), 에타논-1-(9-에틸)-6-(2-메틸벤조일-3-일)-1-(O-아세틸옥심)(씨지아이242), N-1919(아데카사) 등이 있으며, 이에 한정되지 않는다. The oxime compound is 1,2-octadione-1-(4-phenylthio)phenyl-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii 124), ethanone-1-(9-ethyl) -6-(2-methylbenzoyl-3-yl)-1-(O-acetyloxime)(CGI 242), N-1919 (Adeca), and the like, but are not limited thereto.
상기 광개시제는 구체적으로 2-(아세톡시이미노)-3-시클로헥실-1-(4-페닐티오(페닐)프로판-1-온(2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio)phenyl)propan-1-one)일 수 있다.Specifically, the photoinitiator is 2-(acetoxyimino)-3-cyclohexyl-1-(4-phenylthio(phenyl)propan-1-one (2-(acetoxyimino)-3-cyclohexyl-1-(4-( phenylthio)phenyl)propan-1-one).
상기 용매는 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤, 메틸셀로솔브, 에틸셀로솔브, 테트라히드로퓨란, 1,4-디옥산, 에틸렌글리콜 디메틸 에테르, 에틸렌글리콜 디에틸 에테르, 프로필렌글리콜 디메틸 에테르, 프로필렌글리콜 디에틸 에테르, 디에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 메틸 에틸 에테르, 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,1-트리클로로에탄, 1,1,2-트리클로로에탄, 1,1,2-트리클로로에텐, 헥산, 헵탄, 옥탄, 시클로헥산, 벤젠, 톨루엔, 크실렌, 메탄올, 에탄올, 이소프로판올, 프로판올, 부탄올, t-부탄올, 2-에톡시 프로판올, 2-메톡시 프로판올, 3-메톡시 부탄올, 시클로헥사논, 시클로펜타논, 프로필렌글리콜 메틸 에테르 아세테이트, 프로펠렌글리콜 에틸 에테르 아세테이트, 3-메톡시부틸 아세테이트, 에틸 3-에톡시프로피오네이트, 에틸 셀로솔브아세테이트, 메틸 셀로솔브아세테이트, 부틸 아세테이트, 프로필렌글리콜 모노메틸에테르 및 디프로필렌글리콜 모노메틸에테르로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다.The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.
상기 용매는 구체적으로 프로필렌 글리콜 메틸 에테르 아세테이트(PGMEA)이다. The solvent is specifically propylene glycol methyl ether acetate (PGMEA).
본 명세서의 일 실시상태는 상기 감광성 수지 조성물 총 중량을 기준으로, 상기 화학식 1로 표시되는 화합물 5 내지 60 중량%, 상기 바인더 수지 1 내지 60 중량%, 상기 다관능성 모노머 0.1 내지 50 중량%, 상기 광개시제 0.1 내지 20 중량% 및 상기 용매 10 내지 80 중량%를 포함하는 감광성 수지 조성물을 제공한다.An exemplary embodiment of the present specification is based on the total weight of the photosensitive resin composition, 5 to 60% by weight of the compound represented by Formula 1, 1 to 60% by weight of the binder resin, 0.1 to 50% by weight of the multifunctional monomer, the It provides a photosensitive resin composition comprising 0.1 to 20% by weight of a photoinitiator and 10 to 80% by weight of the solvent.
상기 감광성 수지 조성물은 상기 감광성 수지 조성물 총 중량을 기준으로 안료 분산액을 5 내지 20 중량% 더 포함할 수 있다. The photosensitive resin composition may further include 5 to 20% by weight of a pigment dispersion based on the total weight of the photosensitive resin composition.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로, 상기 화학식 1로 표시되는 화합물의 함량은 5 중량% 내지 60 중량%이고, 상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이고, 상기 광개시제의 함량은 0.1 중량% 내지 20 중량%이며, 상기 다관능성 모노머의 함량은 0.1 중량% 내지 50 중량%이다.According to an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the compound represented by Formula 1 is 5% to 60% by weight, and the content of the binder resin is 1% by weight. To 60% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the polyfunctional monomer is 0.1% to 50% by weight.
상기 고형분의 총 중량이란, 상기 감광성 수지 조성물에서 용매를 제외한 성분 총 중량의 합을 의미한다. 고형분 및 각 성분의 고형분을 기준으로 한 중량%의 기준은 액체크로마토그래피 또는 가스크로마토그래피 등의 당업계에서 쓰이는 일반적인 분석 수단으로 측정할 수 있다. The total weight of the solid content refers to the sum of the total weight of components excluding the solvent in the photosensitive resin composition. The basis of the solid content and the weight percent based on the solid content of each component can be measured by a general analysis means used in the art such as liquid chromatography or gas chromatography.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물은 광가교증감제, 경화촉진제, 밀착촉진제, 계면활성제, 열중합방지제, 자외선흡수제, 산화방지제, 분산제 및 레벨링제로 이루어진 군으로부터 선택되는 1 또는 2 이상의 첨가제를 추가로 포함한다.According to an exemplary embodiment of the present specification, the photosensitive resin composition is 1 or 2 selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, a dispersant, and a leveling agent. It further contains the above additives.
본 명세서의 일 실시상태에 따르면, 상기 첨가제의 함량은 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로 0.1 중량% 내지 20 중량%이다.According to an exemplary embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
상기 광가교증감제는 벤조페논, 4,4-비스(디메틸아미노)벤조페논, 4,4-비스(디에틸아미노)벤조페논, 2,4,6-트리메틸아미노벤조페논, 메틸-o-벤조일벤조에이트, 3,3-디메틸-4-메톡시벤조페논, 3,3,4,4-테트라(t-부틸퍼옥시카보닐)벤조페논 등의 벤조페논계 화합물; 9-플로레논, 2-크로로-9-프로레논, 2-메틸-9-플로레논 등의 플로레논계 화합물; 티옥산톤, 2,4-디에틸 티옥산톤, 2-클로로 티옥산톤, 1-클로로-4-프로필옥시 티옥산톤, 이소프로필티옥산톤, 디이소프로필티옥산톤 등의 티옥산톤계 화합물; 크산톤, 2-메틸크산톤 등의 크산톤계 화합물; 안트라퀴논, 2-메틸 안트라퀴논, 2-에틸 안트라퀴논, t-부틸 안트라퀴논, 2,6-디클로로-9,10- 안트라퀴논 등의 안트라퀴논계 화합물; 9-페닐아크리딘, 1,7-비스(9-아크리디닐)헵탄, 1,5-비스(9-아크리디닐펜탄), 1,3-비스(9-아크리디닐)프로판 등의 아크리딘계 화합물; 벤질, 1,7,7-트리메틸-비시클로[2,2,1]헵탄-2,3-디온, 9,10-펜안트렌퀴논 등의 디카보닐 화합물; 2,4,6-트리메틸벤조일 디페닐포스핀 옥사이드, 비스(2,6-디메톡시벤조일)-2,4,4-트리메틸펜틸 포스핀 옥사이드 등의 포스핀 옥사이드계 화합물; 메틸-4-(디메틸아미노)벤조에이트, 에틸-4-(디메틸아미노)벤조에이트, 2-n-부톡시에틸-4-(디메틸아미노)벤조에이트 등의 벤조에이트계 화합물; 2,5-비스(4-디에틸아미노벤잘)시클로펜타논, 2,6-비스(4-디에틸아미노벤잘)시클로헥사논, 2,6-비스(4-디에틸아미노벤잘)-4-메틸-시클로펜타논 등의 아미노 시너지스트; 3,3-카본닐비닐-7-(디에틸아미노)쿠마린, 3-(2-벤조티아졸일)-7-(디에틸아미노)쿠마린, 3-벤조일-7-(디에틸아미노)쿠마린, 3-벤조일-7-메톡시-쿠마린, 10,10-카르보닐비스[1,1,7,7-테트라메틸-2,3,6,7-테트라히드로-1H,5H,11H-C1]-벤조피라노[6,7,8-ij]-퀴놀리진-11-온 등의 쿠마린계 화합물; 4-디에틸아미노 칼콘, 4-아지드벤잘아세토페논 등의 칼콘 화합물; 2-벤조일메틸렌, 3-메틸-b-나프토티아졸린;으로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. Acridine compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.
상기 경화촉진제로는 경화 및 기계적 강도를 높이기 사용되며, 구체적으로 2-머캅토벤조이미다졸, 2-머캅토벤조티아졸, 2-머캅토벤조옥사졸, 2,5-디머캅토-1,3,4-티아디아졸, 2-머캅토-4,6-디메틸아미노피리딘, 펜타에리쓰리톨-테트라키스(3-머캅토프로피오네이트), 펜타에리쓰리톨-트리스(3-머캅토프로피오네이트), 펜타에리쓰리톨-테트라키스(2-머캅토아세테이트), 펜타에리쓰리톨-트리스(2-머캅토아세테이트), 트리메틸올프로판-트리스(2-머캅토아세테이트), 및 트리메틸올프로판-트리스(3-머캅토프로피오네이트)로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The curing accelerator is used to increase curing and mechanical strength, and specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropio) Nate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane- At least one selected from the group consisting of tris (3-mercaptopropionate) may be used.
본 명세서에서 사용되는 밀착촉진제로는 메타아크릴로일옥시 프로필트리메톡시 실란, 메타아크릴로일옥시 프로필디메톡시 실란, 메타아크릴로일옥시 프로필트리에톡시 실란, 메타아크릴로일옥시 프로필디메톡시실란 등의 메타 아크릴로일 실란 커플링제 중 1종 이상을 선택하여 사용할 수 있고, 알킬 트리메톡시 실란으로서 옥틸트리메톡시 실란, 도데실트리메톡시 실란, 옥타데실트리메톡시 실란 등에서 1종 이상을 선택하여 사용할 수 있다.The adhesion promoter used in this specification is methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents such as may be selected and used, and as an alkyl trimethoxy silane, one or more types of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can choose and use it.
상기 계면활성제는 실리콘계 계면활성제 또는 불소계 계면활성제이며, 구체적으로 실리콘계 계면활성제는 BYK-Chemie 사의 BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 등을 사용할 수 있으며, 불소계 계면활성제로는 DIC(DaiNippon Ink & Chemicals) 사의 F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442 등을 사용할 수 있으나, 이에만 한정되는 것은 아니다.The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used, and as a fluorine-based surfactant, DIC (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like may be used, but are not limited thereto.
상기 산화방지제로는 힌더드 페놀계(Hindered phenol) 산화 방지제, 아민계 산화 방지제, 티오계 산화 방지제 및 포스핀계 산화 방지제로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다. The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.
상기 산화방지제의 구체적인 예로는, 인산, 트리메틸포스페이트 또는 트리에틸포스페이트와 같은 인산계 열안정제; 2,6-디-t-부틸-p-크레졸, 옥타데실-3-(4-하이드록시-3,5-디-t-부틸페닐)프로피오네이트, 테트라비스[메틸렌-3-(3,5-디-t-부틸-4-하이드록시페닐)프로피오네이트]메탄, 1,3,5-트리메틸-2,4,6-트리스(3,5-디-t-부틸-4-하이드록시벤질)벤젠, 3,5-디-t-부틸-4-하이드록시벤질포스파이트 디에틸에스테르, 2,2-티오비스(4-메틸-6-t-부틸페놀), 2,6-디-t-부틸페놀 4,4'-부틸리덴-비스(3-메틸-6-t-부틸페놀), 4,4'-티오비스(3-메틸-6-t-부틸페놀) 또는 비스[3,3-비스-(4'-히드록시-3'-터트-부틸페닐)부탄산]글리콜 에스테르 (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester)와 같은 힌더드 페놀(Hindered phenol)계 1차 산화방지제; 페닐-α-나프틸아민, 페닐-β-나프틸아민, N,N'-디페닐-p-페닐렌디아민 또는 N,N'-디-β-나프틸-p-페닐렌디아민과 같은 아민계 2차 산화방지제; 디라우릴디설파이드, 디라우릴티오프로피오네이트, 디스테아릴티오프로피오네이트, 머캡토벤조티아졸 또는 테트라메틸티우람디설파이드 테트라비스[메틸렌-3-(라우릴티오)프로피오네이트]메탄 등의 티오계 2차 산화방지제; 또는 트리페닐 포스파이트, 트리스(노닐페닐)포스파이트, 트리이소데실포스파이트, 비스(2,4-디부틸페닐) 펜타에리쓰리톨 디포스파이트(Bis (2,4-ditbutylphenyl)Pentaerythritol Diphosphite 또는 (1,1'-비페닐)-4,4'-디일비스포스포노산 테트라키스 [2,4-비스(1,1-디메틸에틸)페닐]에스테르((1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester)와 같은 포스파이트계 2차 산화방지제를 들 수 있다.Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy Benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethylester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-di- t-butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol Hindered phenol-based primary antioxidants such as ester); Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine Secondary antioxidants; Thio, such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane Secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1 ,1'-biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester ((1,1'-Biphenyl)-4,4 And phosphite-based secondary antioxidants such as'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester).
상기 자외선 흡수제로는 2-(3-t-부틸-5-메틸-2-히드록시페닐)-5-클로로-벤조트리아졸, 알콕시 벤조페논 등을 사용할 수 있으나, 이에 한정되지 않고, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다. As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.
상기 열중합방지제로는 예컨대 p-아니솔, 히드로퀴논, 피로카테콜(pyrocatechol), t-부틸카테콜(t-butyl catechol), N-니트로소페닐히드록시아민 암모늄염, N-니트로소페닐히드록시아민 알루미늄염, p-메톡시페놀, 디-t-부틸-p-크레졸, 피로가롤, 벤조퀴논, 4,4-티오비스(3-메틸-6-t-부틸페놀), 2,2-메틸렌비스(4-메틸-6-t-부틸페놀), 2-머캅토이미다졸 및 페노티아진(phenothiazine)으로 이루어진 군으로부터 선택된 1 종 이상을 포함할 수 있으나, 이들로만 한정되는 것은 아니며 당 기술분야에 일반적으로 알려져 있는 것들을 포함할 수 있다.Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy. Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology It may include those generally known in the field.
상기 분산제는 미리 안료를 표면 처리하는 형태로 안료에 내부 첨가시키는 방법, 또는 안료에 외부 첨가시키는 방법으로 사용할 수 있다. 상기 분산제로는 화합물형, 비이온성, 음이온성 또는 양이온성 분산제를 사용할 수 있으며, 불소계, 에스테르계, 양이온계, 음이온계, 비이온계, 양쪽성 계면활성제 등을 들 수 있다. 이들은 각각 또는 2종 이상을 조합하여 사용될 수 있다. The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. Compound type, nonionic, anionic or cationic dispersants can be used as the dispersant, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants and the like can be used. These may be used individually or in combination of two or more.
구체적으로 상기 분산제는 폴리알킬렌글리콜 및 이의 에스테르, 폴리옥시알킬렌 다가 알코올, 에스테르알킬렌옥사이드 부가물, 알코올알킬렌옥사이드 부가물, 설폰산 에스테르, 설폰산염, 카르복실산에스테르, 카르복실산염, 알킬아미드알킬렌옥사이드 부가물 및 알킬아민으로 이루어진 그룹으로부터 선택된 1종 이상이 있으나, 이에 한정되는 것은 아니다.Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylate, There may be at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.
상기 레벨링제로는 폴리머성이거나 비폴리머성일 수 있다. 폴리머성의 레벨링제의 구체적인 예로는 폴리에틸렌이민, 폴리아미드아민, 아민과 에폭사이드의 반응 생성물을 예로 들 수 있고, 비폴리머성의 레벨링제의 구체적인 예로는 비-폴리머 황-함유 및 비-폴리머 질소-함유 화합물을 포함하지만, 이에 한정되지는 않으며, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다.The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but is not limited thereto, all those generally used in the art may be used.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물을 포함하는 감광재를 제공한다. According to an exemplary embodiment of the present specification, a photosensitive material including the photosensitive resin composition is provided.
상기 감광성 수지 조성물을 포함하는 감광재란, 본 명세서의 감광성 수지 조성물을 기재 위에 적절한 방법으로 도포하고 경화하여 박막 또는 패턴형태의 감광재를 형성하는 것이다.The photosensitive material including the photosensitive resin composition refers to forming a photosensitive material in the form of a thin film or pattern by applying and curing the photosensitive resin composition of the present specification on a substrate in an appropriate manner.
상기 도포 방법으로는 특별히 제한되지는 않지만 스프레이 법, 롤 코팅법, 스핀 코팅법 등을 사용할 수 있으며, 일반적으로 스핀 코팅법을 널리 사용한다. 또한, 도포막을 형성한 후 경우에 따라서 감압 하에 잔류 용매를 일부 제거할 수 있다.The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.
본 명세서에 따른 감광성 수지 조성물을 경화시키기 위한 광원으로는, 예컨대 파장이 250 nm 내지 450 ㎚의 광을 발산하는 수은 증기 아크(arc), 탄소 아크, Xe 아크 등이 있으나 반드시 이에 국한되지는 않는다.Light sources for curing the photosensitive resin composition according to the present specification include, for example, a mercury vapor arc, a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.
본 명세서에 따른 감광성 수지 조성물은 박막 트랜지트터 액정 표시장치(TFT LCD) 컬러필터 제조용 안료분산형 감광재, 박막 트랜지트터 액정 표시장치(TFT LCD) 또는 유기 발광 다이오드의 블랙 매트릭스 형성용 감광재, 오버코트층 형성용 감광재, 컬럼 스페이서 감광재, 광경화형 도료, 광경화성 잉크, 광경화성 접착제, 인쇄판, 인쇄배선반용 감광재, 플라즈마 디스플레이 패널(PDP)용 감광재 등에 사용할 수 있으며, 그 용도에 제한을 특별히 두지는 않는다.The photosensitive resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode. , Photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.
본 명세서의 일 실시상태에 따르면, 상기 감광재를 포함하는 컬러필터를 제공한다.According to an exemplary embodiment of the present specification, a color filter including the photosensitive material is provided.
상기 컬러필터는 상기 화학식 1로 표시되는 화합물을 포함하는 수지 조성물을 이용하여 제조될 수 있다. 상기 수지 조성물을 기판상에 도포하여 코팅막을 형성하고, 상기 코팅막을 노광, 현상 및 경화를 함으로써 컬러필터를 형성할 수 있다.The color filter may be manufactured using a resin composition containing the compound represented by Formula 1. A color filter may be formed by applying the resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 내열성이 우수하여, 열처리에 의한 색의 변화가 적어, 컬러 필터의 제조시 경화 과정에 의해서도 색재현율이 높고, 휘도 및 명암비가 높은 컬러필터를 제공할 수 있다. The photosensitive resin composition according to an exemplary embodiment of the present specification has excellent heat resistance and has little change in color due to heat treatment, so that it is possible to provide a color filter having high color reproduction rate and high luminance and contrast ratio even by the curing process when manufacturing a color filter. I can.
상기 기판은 유리판, 실리콘 웨이퍼 및 폴리에테르설폰(Polyethersulfone, PES), 폴리카보네이트(Polycarbonate, PC) 등의 플라스틱 기재의 판 등일 수 있으며, 그 종류가 특별히 제한되는 것은 아니다. The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited.
상기 컬러필터는 적색 패턴, 녹색 패턴, 청색 패턴, 블랙 매트릭스를 포함할 수 있다. The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
또 하나의 실시상태에 따르면, 상기 컬러필터는 오버코트층를 더 포함할 수 있다. According to another exemplary embodiment, the color filter may further include an overcoat layer.
상기 컬러필터의 컬러픽셀 사이에는 콘트라스트를 향상시킬 목적으로 블랙 매트릭스라고 불리는 격자상의 흑색패턴을 배치할 수 있다. 블랙 매트릭스의 재료로서 크롬을 사용할 수 있다. 이 경우, 크롬을 유리기판 전체에 증착시키고 에칭 처리에 의해 패턴을 형성하는 방식을 이용할 수 있다. 그러나, 공정상의 고비용, 크롬의 고반사율, 크롬 폐액에 의한 환경오염을 고려하여, 미세가공이 가능한 안료분산법에 의한 레진 블랙 매트릭스를 사용할 수 있다. A grid-like black pattern called a black matrix may be disposed between the color pixels of the color filter for the purpose of improving contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching treatment may be used. However, in consideration of the high process cost, high reflectance of chromium, and environmental pollution due to chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing may be used.
본 명세서의 일 실시상태에 따른 블랙 매트릭스는 색재로서 블랙안료 또는 블랙 염료를 사용할 수 있다. 예컨대, 카본블랙을 단독으로 사용하거나, 카본블랙과 착색안료를 혼합하여 사용할 수 있으며, 이때 차광성이 부족한 착색안료를 혼합하기 때문에 상대적으로 색재의 양이 증가하더라도 막의 강도 또는 기판에 대한 밀착성이 저하되지 않는 장점이 있다. The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material increases. There is an advantage that does not work.
본 명세서에 따른 컬러필터를 포함하는 디스플레이 장치를 제공한다. A display device including the color filter according to the present specification is provided.
상기 디스플레이 장치는 플라즈마 디스플레이 패널(Plasma Display Panel, PDP), 발광 다이오드(Light Emitting Diode, LED), 유기 발광 소자(Organic Light Emitting Diode, OLED), 액정 표시 장치(Liquid Crystal Display, LCD), 박막 트랜지스터 액정 표시 장치(Thin FIlm Transistor- Liquid Crystal Display, LCD-TFT) 및 음극선관(Cathode Ray Tube, CRT) 중 어느 하나일 수 있다.The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be any one of a liquid crystal display (Thin Film Transistor- Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 기술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.
<실시예><Example>
화합물의 합성Compound synthesis
합성예 1: 3,6-디클로로-4-히드록시-5-페녹시프탈로니트릴(3,6-dichloro-4-hydroxy-5-phenoxyphthalonitrile)Synthesis Example 1: 3,6-dichloro-4-hydroxy-5-phenoxyphthalonitrile (3,6-dichloro-4-hydroxy-5-phenoxyphthalonitrile)
3,6-디클로로-4-메톡시-5-페녹시프탈로니트릴(3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile) 5g(15.667mmol)을 CH2Cl2 100ml에 넣고 교반시키면서, 0℃로 만들었다. 이후 BBr3 3.925g(15.667mmol)을 넣고 상온에서 5시간동안 교반시켜 반응용액을 제조하였다.3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile (3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile) 5g (15.667mmol) in CH 2 Cl 2 100ml while stirring, 0 ℃ Made with Then, 3.925g (15.667mmol) of BBr 3 was added and stirred at room temperature for 5 hours to prepare a reaction solution.
H2O 100ml에 NaHCO3 2.633g(31.334mmol)을 용해시킨 수용액을 반응용액에 서서히 적하시켰다. 유기층을 분리하고, MgSO4를 통과시킨 후 감압하에서 농축하였다. 이를 컬럼크로마토그래피(column chromatography)를 통해 분리하여 합성예 1 화합물을 얻었다.An aqueous solution in which 2.633 g (31.334 mmol) of NaHCO 3 was dissolved in 100 ml of H 2 O was slowly added dropwise to the reaction solution. The organic layer was separated, passed through MgSO 4 , and then concentrated under reduced pressure. This was separated through column chromatography to obtain a compound of Synthesis Example 1.
합성예 2: 4-(2-(tert-부틸)페녹시)-3,6-디클로로-5-히드록시프탈로니트릴(4-(2-(tert-butyl)phenoxy)-3,6-dichloro-5-hydroxyphthalonitrile)Synthesis Example 2: 4-(2-(tert-butyl)phenoxy)-3,6-dichloro-5-hydroxyphthalonitrile (4-(2-(tert-butyl)phenoxy)-3,6-dichloro -5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 4-(2-(tert-butyl)phenoxy)-3,6-dichloro-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 2 화합물을 얻었다.Instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile in Synthesis Example 1, 4-(2-(tert-butyl)phenoxy)-3,6-dichloro-5-methoxyphthalonitrile was used, and the others were carried out in the same manner. , A compound of Synthesis Example 2 was obtained.
합성예 3: 3,6-디클로로-4-(2,4-디-tert-부틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,4-di-tert-butylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 3: 3,6-dichloro-4-(2,4-di-tert-butylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,4-di-tert -butylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,4-di-tert-butylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 3 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,4-di-tert-butylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner. Thus, a compound of Synthesis Example 3 was obtained.
합성예 4: 3,6-디클로로-4-(2,6-디-tert-부틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,6-di-tert-butylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 4: 3,6-dichloro-4-(2,6-di-tert-butylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,6-di-tert -butylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,6-di-tert-butylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 4 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,6-di-tert-butylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner. Thus, a compound of Synthesis Example 4 was obtained.
합성예 5: 4-([1,1'-바이페닐]-2-일록시)-3,6-디클로로-5-히드록시프탈로니트릴(4-([1,1'-biphenyl]-2-yloxy)-3,6-dichloro-5-hydroxyphthalonitrile)Synthesis Example 5: 4-([1,1'-biphenyl]-2-yloxy)-3,6-dichloro-5-hydroxyphthalonitrile (4-([1,1'-biphenyl]-2 -yloxy)-3,6-dichloro-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 4-([1,1'-biphenyl]-2-yloxy)-3,6-dichloro-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 5 화합물을 얻었다.Instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile in Synthesis Example 1, 4-([1,1'-biphenyl]-2-yloxy)-3,6-dichloro-5-methoxyphthalonitrile was used, and the others were the same Proceeding by the method, a compound of Synthesis Example 5 was obtained.
합성예 6: 3,6-디클로로-4-(2-시클로헥실페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2-cyclohexylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 6: 3,6-dichloro-4-(2-cyclohexylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2-cyclohexylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2-cyclohexylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 6 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2-cyclohexylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 6 compound Got it.
합성예 7: 3,6-디클로로-4-히드록시-5-(나프탈렌-1-일록시)프탈로니트릴(3,6-dichloro-4-hydroxy-5-(naphthalen-1-yloxy)phthalonitrile)Synthesis Example 7: 3,6-dichloro-4-hydroxy-5- (naphthalen-1-yloxy) phthalonitrile (3,6-dichloro-4-hydroxy-5- (naphthalen-1-yloxy) phthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-methoxy-5-(naphthalen-1-yloxy)phthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 7 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-methoxy-5-(naphthalen-1-yloxy)phthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and the synthesis Example 7 The compound was obtained.
합성예 8: 3,6-디클로로-4-히드록시-5-(나프탈렌-2-일록시)프탈로니트릴(3,6-dichloro-4-hydroxy-5-(naphthalen-2-yloxy)phthalonitrile)Synthesis Example 8: 3,6-dichloro-4-hydroxy-5- (naphthalen-2-yloxy) phthalonitrile (3,6-dichloro-4-hydroxy-5- (naphthalen-2-yloxy) phthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-methoxy-5-(naphthalen-2-yloxy)phthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 8 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-methoxy-5-(naphthalen-2-yloxy)phthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and the synthesis Example 8 A compound was obtained.
합성예 9: 3,6-디클로로-4-히드록시-5-(o-톨리옥시)프탈로니트릴(3,6-dichloro-4-hydroxy-5-(o-tolyloxy)phthalonitrile)Synthesis Example 9: 3,6-dichloro-4-hydroxy-5- (o-tolyoxy) phthalonitrile (3,6-dichloro-4-hydroxy-5- (o-tolyloxy) phthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-methoxy-5-(o-tolyloxy)phthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 9 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-methoxy-5-(o-tolyloxy)phthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 9 The compound was obtained.
합성예 10: 3,6-디클로로-4-(2,4-디메틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,4-dimethylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 10: 3,6-dichloro-4-(2,4-dimethylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,4-dimethylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,4-dimethylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 10 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,4-dimethylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 10 compound was obtained.
합성예 11: 3,6-디클로로-4-(2,6-디메틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,6-dimethylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 11: 3,6-dichloro-4-(2,6-dimethylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,6-dimethylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,6-dimethylphenoxy)-5-methoxyphthalonitrile사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 11 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,6-dimethylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 11 compound was obtained.
합성예 12: 3,6-디클로로-4-(2,3-디메틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,3-dimethylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 12: 3,6-dichloro-4-(2,3-dimethylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,3-dimethylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,3-dimethylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 12 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,3-dimethylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 12 compound was obtained.
합성예 13: 3,6-디클로로-4-(2,5-디메틸페녹시)-5-히드록시프탈로니트릴(3,6-dichloro-4-(2,5-dimethylphenoxy)-5-hydroxyphthalonitrile)Synthesis Example 13: 3,6-dichloro-4-(2,5-dimethylphenoxy)-5-hydroxyphthalonitrile (3,6-dichloro-4-(2,5-dimethylphenoxy)-5-hydroxyphthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(2,5-dimethylphenoxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 13 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(2,5-dimethylphenoxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner, and Synthesis Example 13 compound was obtained.
합성예 14: 3,6-디클로로-4-히드록시-5-(메시틸옥시)프날로니트릴(3,6-dichloro-4-hydroxy-5-(mesityloxy)phthalonitrile)Synthesis Example 14: 3,6-dichloro-4-hydroxy-5-(mesityloxy)phenalonitrile (3,6-dichloro-4-hydroxy-5-(mesityloxy)phthalonitrile)
합성예 1에서 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile 대신 3,6-dichloro-4-(mesityloxy)-5-methoxyphthalonitrile 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 14 화합물을 얻었다.In Synthesis Example 1, 3,6-dichloro-4-(mesityloxy)-5-methoxyphthalonitrile was used instead of 3,6-dichloro-4-methoxy-5-phenoxyphthalonitrile, and the others were carried out in the same manner to obtain a compound of Synthesis Example 14. .
합성예 15: 화학식 A로 표시되는 화합물의 합성Synthesis Example 15: Synthesis of a compound represented by Formula A
합성예 1 화합물 3g(9.047mmol), ZnCl2 0.37g(2.714mmol)을 1-pentanol 50ml에 넣고, 90℃로 승온하여 30분간 교반시켰다. 이후 DBU(1,8-Diazabicyclo[5.4.0]undec-7-ene) 1.377g(9.047mmol)을 서서히 적하시켰다. 이후 반응물을 135℃로 승온하고 24시간 동안 반응시켰다. 반응물을 상온으로 식히고, MeOH 240ml, H2O 480ml로 제조된 혼합용액에 서서히 적하시켰다. 석출물을 감압하에서 여과시키고, MeOH 120ml, H2O 240ml로 제조된 혼합용액으로 수세하였다. 이를 컬럼크로마토그래피(column chromatography)를 통해 분리하여 합성예 15로 제조된 화합물 A를 얻었다.Synthesis Example 1 Compound 3g (9.047mmol) and ZnCl 2 0.37g (2.714mmol) were added to 1-pentanol 50ml, the temperature was raised to 90°C, and stirred for 30 minutes. Then, 1.377 g (9.047 mmol) of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was slowly added dropwise. Thereafter, the reaction mixture was heated to 135° C. and reacted for 24 hours. The reaction was cooled to room temperature, and slowly added dropwise to a mixed solution prepared with 240 ml of MeOH and 480 ml of H 2 O. The precipitate was filtered under reduced pressure, and washed with a mixed solution prepared with MeOH 120 ml and H 2 O 240 ml. This was separated through column chromatography to obtain Compound A prepared in Synthesis Example 15.
[화합물 A] MALDI-TOF MS : 1278.85 m/z[Compound A] MALDI-TOF MS: 1278.85 m/z
합성예 16: 화학식 B로 표시되는 화합물의 합성Synthesis Example 16: Synthesis of a compound represented by Formula B
합성예 15에서 합성예 1 화합물 대신 합성예 2 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 16으로 제조된 화합물 B를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 2 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound B prepared by Synthesis Example 16.
[화합물 B] MALDI-TOF MS : 1503.1 m/z[Compound B] MALDI-TOF MS: 1503.1 m/z
합성예 17: 화학식 C로 표시되는 화합물의 합성Synthesis Example 17: Synthesis of a compound represented by Formula C
합성예 15에서 합성예 1 화합물 대신 합성예 3 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 17로 제조된 화합물 C를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 3 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound C prepared by Synthesis Example 17.
[화합물 C] MALDI-TOF MS : 1727.35 m/z[Compound C] MALDI-TOF MS: 1727.35 m/z
합성예 18: 화학식 D로 표시되는 화합물의 합성Synthesis Example 18: Synthesis of a compound represented by Formula D
합성예 15에서 합성예 1 화합물 대신 합성예 4 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 18로 제조된 화합물 D를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 4 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound D prepared by Synthesis Example 18.
[화합물 D] MALDI-TOF MS : 1727.35 m/z[Compound D] MALDI-TOF MS: 1727.35 m/z
합성예 19: 화학식 E로 표시되는 화합물의 합성Synthesis Example 19: Synthesis of a compound represented by Formula E
합성예 15에서 합성예 1 화합물 대신 합성예 5 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 19로 제조된 화합물 E를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 5 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound E prepared by Synthesis Example 19.
[화합물 E] MALDI-TOF MS : 1582.98 m/z[Compound E] MALDI-TOF MS: 1582.98 m/z
합성예 20: 화학식 F로 표시되는 화합물의 합성Synthesis Example 20: Synthesis of a compound represented by Formula F
합성예 15에서 합성예 1 화합물 대신 합성예 6 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 20로 제조된 화합물 F를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 6 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain the compound F prepared by Synthesis Example 20.
[화합물 F] MALDI-TOF MS : 1607.16 m/z[Compound F] MALDI-TOF MS: 1607.16 m/z
합성예 21: 화학식 G로 표시되는 화합물의 합성Synthesis Example 21: Synthesis of a compound represented by Formula G
합성예 15에서 합성예 1 화합물 대신 합성예 7 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 21로 제조된 화합물 G를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 7 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound G prepared by Synthesis Example 21.
[화합물 G] MALDI-TOF MS : 1478.91 m/z[Compound G] MALDI-TOF MS: 1478.91 m/z
합성예 22: 화학식 H로 표시되는 화합물의 합성Synthesis Example 22: Synthesis of a compound represented by Formula H
합성예 15에서 합성예 1 화합물 대신 합성예 8 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 22로 제조된 화합물 H를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 8 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound H prepared by Synthesis Example 22.
[화합물 H] MALDI-TOF MS : 1478.91 m/z[Compound H] MALDI-TOF MS: 1478.91 m/z
합성예 23: 화학식 I로 표시되는 화합물의 합성Synthesis Example 23: Synthesis of a compound represented by Formula I
합성예 15에서 합성예 1 화합물 대신 합성예 9 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 23로 제조된 화합물 I를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 9 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound I prepared in Synthesis Example 23.
[화합물 I] MALDI-TOF MS : 1334.91 m/z[Compound I] MALDI-TOF MS: 1334.91 m/z
합성예 24: 화학식 J로 표시되는 화합물의 합성Synthesis Example 24: Synthesis of a compound represented by Formula J
합성예 15에서 합성예 1 화합물 대신 합성예 10 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 24로 제조된 화합물 J를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 10 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound J prepared in Synthesis Example 24.
[화합물 J] MALDI-TOF MS : 1390.98 m/z[Compound J] MALDI-TOF MS: 1390.98 m/z
합성예 25: 화학식 K로 표시되는 화합물의 합성Synthesis Example 25: Synthesis of a compound represented by Formula K
합성예 15에서 합성예 1 화합물 대신 합성예 11 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 25로 제조된 화합물 K를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 11 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound K prepared by Synthesis Example 25.
[화합물 K] MALDI-TOF MS : 1390.98 m/z[Compound K] MALDI-TOF MS: 1390.98 m/z
합성예 26: 화학식 L로 표시되는 화합물의 합성Synthesis Example 26: Synthesis of a compound represented by Formula L
합성예 15에서 합성예 1 화합물 대신 합성예 12 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 26로 제조된 화합물 L를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 12 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound L prepared by Synthesis Example 26.
[화합물 L] MALDI-TOF MS : 1390.98 m/z[Compound L] MALDI-TOF MS: 1390.98 m/z
합성예 27: 화학식 M로 표시되는 화합물의 합성Synthesis Example 27: Synthesis of a compound represented by Formula M
합성예 15에서 합성예 1 화합물 대신 합성예 13 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 27로 제조된 화합물 M를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 13 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound M prepared in Synthesis Example 27.
[화합물 M] MALDI-TOF MS : 1390.98 m/z[Compound M] MALDI-TOF MS: 1390.98 m/z
합성예 28: 화학식 N로 표시되는 화합물의 합성Synthesis Example 28: Synthesis of a compound represented by Formula N
합성예 15에서 합성예 1 화합물 대신 합성예 14 화합물을 사용하고, 그 외는 동일한 방법으로 진행하여, 합성예 28로 제조된 화합물 N를 얻었다.In Synthesis Example 15, the compound of Synthesis Example 14 was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain compound N prepared by Synthesis Example 28.
[화합물 N] MALDI-TOF MS : 1447.04 m/z[Compound N] MALDI-TOF MS: 1447.04 m/z
<비교예><Comparative Example>
비교 합성예 1: 4,5-디브로모-3,6-디히드록시프탈로니트릴(4,5-dibromo-3.6-dihydroxyphthalonitrile)Comparative Synthesis Example 1: 4,5-dibromo-3,6-dihydroxyphthalonitrile (4,5-dibromo-3.6-dihydroxyphthalonitrile)
tert-부탄올(tert-butanol) 30ml에 3,6-디히드록시프탈로니트릴(3,6-dihydroxyphthalonitrile) 5g(31.25mmol)을 넣고 교반시켰다. 45℃로 승온하고, NBS(N-bromosuccinimide) 10.5g(64.5mmol)을 서서히 첨가하고 2시간 동안 교반시켰다. 이후 NBS(N-bromosuccinimide) 10.5g(64.5mmol)를 추가로 첨가하고 2시간 동안 추가 교반시켰다. 이후 반응물을 상온으로 식혔다. 0℃ Sodium metabisulfite 수용액(10g, H2O 60ml)에 반응액을 첨가하고, 0℃를 유지한 상태에서 30분간 교반시켰다. 석출물을 감압하에서 여과하고, ice water 50ml로 수세하였다. 60℃ 진공오븐에서 하루동안 건조시켜 비교예 화합물 1을 얻었다.3,6-dihydroxyphthalonitrile (3,6-dihydroxyphthalonitrile) 5g (31.25mmol) was added to 30ml tert-butanol and stirred. The temperature was raised to 45°C, and 10.5g (64.5mmol) of NBS (N-bromosuccinimide) was slowly added and stirred for 2 hours. Then, 10.5g (64.5mmol) of NBS (N-bromosuccinimide) was additionally added, followed by further stirring for 2 hours. Then, the reaction was cooled to room temperature. The reaction solution was added to 0°C Sodium metabisulfite aqueous solution (10g, H 2 O 60ml), and stirred for 30 minutes while maintaining 0°C. The precipitate was filtered under reduced pressure and washed with 50 ml of ice water. Comparative Example Compound 1 was obtained by drying in a vacuum oven at 60° C. for one day.
비교 합성예 2: 4,5-디클로로-3,6-디히드록시프탈로니트릴(4,5-dichloro-3,6-dihydroxyphthalonitrile)Comparative Synthesis Example 2: 4,5-dichloro-3,6-dihydroxyphthalonitrile (4,5-dichloro-3,6-dihydroxyphthalonitrile)
2,3-dichloro-5,6-dicyano-1,4-hydroquinone 10g(44mmol)을 톨루엔(Toluene) 50ml에 넣고 교반시켰다. Na2SO4 수용액(13.5 g, 78mmol을 H2O 170ml 용해)을 서서히 첨가하고 30분간 교반시켰다. 이후 석출물을 감압하에서 여과시키고, ice water 30ml와 소량의 n-Hexane으로 수세하고 Acetone/H2O로 재결정하였다. 60℃ 진공오븐에서 하루동안 건조시켜 비교예 화합물 2을 얻었다.2,3-dichloro-5,6-dicyano-1,4-hydroquinone 10 g (44 mmol) was added to 50 ml of toluene and stirred. Na 2 SO 4 aqueous solution (13.5 g, 78 mmol dissolved in 170 ml of H 2 O) was slowly added and stirred for 30 minutes. Thereafter, the precipitate was filtered under reduced pressure, washed with 30 ml of ice water and a small amount of n-Hexane, and recrystallized with Acetone/H 2 O. Comparative Example Compound 2 was obtained by drying in a vacuum oven at 60° C. for one day.
비교 합성예 3: 비교 화합물 Ⅰ로 표시되는 화합물Comparative Synthesis Example 3: Compound represented by Comparative Compound I
합성예 15에서 합성예 1 화합물 대신 비교예 1 화합물, ZnCl2 대신 COCl2로 사용하고, 그 외는 동일한 방법으로 진행하여, 비교 합성예 3로 제조된 비교 화합물 Ⅰ를 얻었다.In Synthesis Example 15, the compound of Comparative Example 1 was used instead of the compound of Synthesis Example 1, and COCl 2 was used instead of ZnCl 2 , and the others were carried out in the same manner to obtain Comparative Compound I prepared in Comparative Synthesis Example 3.
[비교 화합물 Ⅰ][Comparative compound Ⅰ]
비교 합성예 4: 비교 화합물 Ⅱ로 표시되는 화합물Comparative Synthesis Example 4: Compound represented by Comparative Compound II
합성예 15에서 합성예 1 화합물 대신 비교예 2 화합물, ZnCl2 대신 CuCl2로 사용하고, 그 외는 동일한 방법으로 진행하여, 비교 합성예 4로 제조된 비교 화합물 Ⅱ를 얻었다.In Synthesis Example 15, the compound of Comparative Example 2 was used instead of the compound of Synthesis Example 1, and CuCl 2 was used instead of ZnCl 2 , and the others were carried out in the same manner to obtain Comparative Compound II prepared by Comparative Synthesis Example 4.
[비교 화합물 Ⅱ][Comparative compound Ⅱ]
비교 합성예 5: 비교 화합물 Ⅲ로 표시되는 화합물Comparative Synthesis Example 5: Compound represented by Comparative Compound III
합성예 15에서 합성예 1 화합물 대신 4-bromo-3-phenoxyphthalonitrile, ZnCl2 대신 COCl2로 사용하고 사용하고, 그 외는 동일한 방법으로 진행하여, 비교 합성예 5로 제조된 비교 화합물 Ⅲ를 얻었다.In Synthesis Example 15, 4-bromo-3-phenoxyphthalonitrile was used instead of the compound of Synthesis Example 1, and COCl 2 was used instead of ZnCl 2 , and the others were carried out in the same manner to obtain Comparative Compound III prepared by Comparative Synthesis Example 5.
[비교 화합물 Ⅲ][Comparative compound Ⅲ]
비교 합성예 6: 비교 화합물 Ⅳ로 표시되는 화합물Comparative Synthesis Example 6: Compound represented by Comparative Compound IV
합성예 15에서 합성예 1 화합물 대신 sodium 3-(3,4-dicyanophenoxy)benzenesulfonate 사용하고, 그 외는 동일한 방법으로 진행하여, 비교 합성예 6로 제조된 비교 화합물 Ⅳ를 얻었다.In Synthesis Example 15, sodium 3-(3,4-dicyanophenoxy)benzenesulfonate was used instead of the compound of Synthesis Example 1, and the others were carried out in the same manner to obtain Comparative Compound IV prepared in Comparative Synthesis Example 6.
[비교 화합물 Ⅳ][Comparative Compound IV]
비교 합성예 7: 비교 화합물 Ⅴ로 표시되는 화합물Comparative Synthesis Example 7: The compound represented by Comparative Compound V
합성예 15에서 합성예 1 화합물 대신 3,4,5-triphenoxyphthalonitrile, ZnCl2 대신 CuCl2로 사용하고, 그 외는 동일한 방법으로 진행하여, 비교 합성예 7로 제조된 비교 화합물 Ⅴ를 얻었다In Synthesis Example 15, 3,4,5-triphenoxyphthalonitrile was used instead of the compound of Synthesis Example 1, and CuCl 2 was used instead of ZnCl 2 , and the others were carried out in the same manner to obtain Comparative Compound V prepared by Comparative Synthesis Example 7
[비교 화합물 Ⅴ][Comparative Compound V]
용해도 측정Solubility measurement
상기 합성예 화합물 A~N, 비교 화합물 Ⅰ~Ⅴ 0.1g에, 희석용제 프로필렌글리콜메틸에테르아세테이트(PGMEA(Propylene glycol methyl ether acetate))를 첨가하고, 화합물 용액을 shaker(Jeio Tech SK-600)로 25℃에서 350rpm으로 1시간 동안 교반 후, 화합물의 용해도 확인 결과 하기 표 1로 나타내었다.To 0.1 g of the Synthesis Example Compounds A to N and Comparative Compounds I to V, propylene glycol methyl ether acetate (PGMEA (Propylene glycol methyl ether acetate)) was added, and the compound solution was shaker (Jeio Tech SK-600). After stirring at 25° C. at 350 rpm for 1 hour, the results of confirming the solubility of the compound are shown in Table 1 below.
[용해도 평가 기준][Solubility evaluation criteria]
희석용제 PGMEA 총량에 대하여 화합물(용질)이 10중량 % 이상 용해: ○Compound (solvent) is dissolved in 10% by weight or more with respect to the total amount of the diluted solvent PGMEA:
희석용제 PGMEA 총량에 대하여 화합물(용질)이 5중량 %이 이상 10 중량 % 미만 용해: △5% by weight or more and less than 10% by weight of the compound (solute) based on the total amount of the diluent PGMEA dissolved: △
희석용제 PGMEA 총량에 대하여 화합물(용질)이 5중량 % 미만 용해: ⅩDissolution of less than 5% by weight of the compound (solvent) based on the total amount of the diluent PGMEA: Ⅹ
상기 표 1로부터, 본 명세서에 따른 화합물 A 내지 N은 비교 화합물 Ⅰ내지 Ⅳ의 화합물 보다 유기용매에 대한 용해도가 우수하여, 색재를 사용하기 위한 추가적인 분산 과정 및 분산제 사용량이 줄어들 수 있어 감광성 수지 조성물에 사용할 경우 우수한 색 특성을 나타낼 수 있음을 확인할 수 있었다.From Table 1, Compounds A to N according to the present specification have better solubility in organic solvents than the compounds of Comparative Compounds I to IV, so that the additional dispersion process and the amount of dispersant used for the use of the coloring material can be reduced, so that the photosensitive resin composition When used, it was confirmed that excellent color characteristics could be displayed.
감광성 수지 조성물의 제조Preparation of photosensitive resin composition
[감광성 수지 조성물 실시예 1의 제조][Preparation of photosensitive resin composition Example 1]
하기 표 2에 나타낸 구성성분으로 혼합하여 감광성 수지 조성물 실시예 1에 따른 감광성 수지 조성물을 제조하였다.A photosensitive resin composition according to Example 1 was prepared by mixing with the components shown in Table 2 below.
용매(프로필렌 글리콜 메틸 에테르 아세테이트)에 화합물을 녹인 후 1시간 동안 상온에서 shaker(Jeio Tech SK-600)로 1시간 동안 교반시켰다. 이후 안료 분산액, 바인더 수지(알칼리 가용성 수지), 다관능성 모노머(광중합성 화합물), 광개시제를 넣고 1시간 동안 상온에서 추가적으로 교반시켰다. 이후 0.2μm 필터(filter)로 불순물을 제거하여, 감광성 수지 조성물을 제조하였다.After dissolving the compound in a solvent (propylene glycol methyl ether acetate), the mixture was stirred for 1 hour with a shaker (Jeio Tech SK-600) at room temperature for 1 hour. Thereafter, a pigment dispersion, a binder resin (alkali-soluble resin), a polyfunctional monomer (photopolymerizable compound), and a photoinitiator were added and further stirred at room temperature for 1 hour. Thereafter, impurities were removed with a 0.2 μm filter to prepare a photosensitive resin composition.
안료 분산액Pigment Yellow 138
Pigment dispersion
다관능성 모노머(광중합성 화합물): 디펜타에리쓰리톨 헥사아크릴레이트(Dipentaerythritol hexaacrylate(DPHA))
광개시제: 2-(아세톡시미노)-3-시클로헥실-1-(4-(페닐티오)페닐)프로판 -1-온(2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio)phenyl)propan-1-one)Binder resin (alkali-soluble resin): a copolymer of benzyl methacrylate and methacrylic acid (molar ratio of 70:30, acid value is 113 KOH mg/g, weight average molecular weight measured by gel permeation chromatography (GPC) 20,000 g/mol , Molecular weight distribution (PDI) 2.0, solid content (SC) 25%, including solvent PGMEA
Polyfunctional monomer (photopolymerizable compound): Dipentaerythritol hexaacrylate (DPHA)
Photoinitiator: 2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio)phenyl)propan-1-one (2-(acetoxyimino)-3-cyclohexyl-1-(4-(phenylthio) phenyl)propan-1-one)
[감광성 수지 조성물 실시예 2~14의 제조][Production of photosensitive resin composition Examples 2 to 14]
상기 감광성 수지 조성물 실시예 1의 제조에서 화합물 A 대신 각각 B~N를 사용하고, 그 이외는 동일한 방법으로 감광성 수지 조성물 실시예 2~14를 제조하였다.In the preparation of the photosensitive resin composition Example 1, each of B to N was used instead of the compound A, and other than that, photosensitive resin composition Examples 2 to 14 were prepared by the same method.
[감광성 수지 조성물 비교예 1~4의 제조][Production of photosensitive resin composition Comparative Examples 1 to 4]
상기 감광성 수지 조성물 실시예 1의 제조에서 화합물 A 대신 각각 비교 화합물 Ⅰ, Ⅱ, Ⅲ, Ⅴ를 사용하고, 그 이외는 동일한 방법으로 감광성 수지 조성물 비교예 1~4를 제조하였다.In the preparation of the photosensitive resin composition Example 1, Comparative Compounds I, II, III, and V were used instead of Compound A, respectively, and Comparative Examples 1 to 4 of the photosensitive resin composition were prepared in the same manner except for that.
기판 제작, 색좌표, 휘도, 명암비 측정Substrate fabrication, color coordinate, luminance, contrast measurement
상기 실시예 1~14 및 비교예 1~4에 따른 감광성 수지 조성물을 기판 제작에 각각 사용하였다. 구체적으로, 상기 실시예 및 비교예에 따른 감광성 수지 조성물을 유리 (5 X 5 cm2) 위에 스핀코팅(spin coating)하고, 100℃에서 100초간 전열처리(prebake)를 실시하여 필름을 형성시켰다.The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 4 were each used in the manufacture of a substrate. Specifically, the photosensitive resin composition according to the Examples and Comparative Examples was spin-coated on glass (5 X 5 cm 2 ), and prebake was performed at 100° C. for 100 seconds to form a film.
제작된 기판을 분광기(MCPD, 오츠카社)를 이용하여 색좌표(x, y)와 휘도(Y)를 측정하였으며, 이를 하기 표 3에 나타내었다.The fabricated substrate was measured for color coordinates (x, y) and luminance (Y) using a spectrometer (MCPD, Otsuka), and are shown in Table 3 below.
제작된 기판을 콘트라스트 측정기(Tsubosaka 社)를 이용하여, 기판의 상-하의 편광판이 평행 및 직교일 때의 휘도를 측정하고 아래의 계산식으로 콘트라스트비를 계산하였으며, 하기 표 3에 나타내었다.The prepared substrate was measured using a contrast meter (Tsubosaka), and the luminance when the upper and lower polarizing plates of the substrate were parallel and orthogonal was measured, and the contrast ratio was calculated by the following calculation formula, and is shown in Table 3 below.
[계산식][formula]
콘트라스트(Contrast ratio, CR)= 기판의 상-하의 편광판이 평행일 때 휘도/ 기판의 상-하 편광판이 직교일 때 휘도Contrast ratio (CR) = luminance when the upper and lower polarizing plates of the substrate are parallel / luminance when the upper and lower polarizing plates of the substrate are orthogonal
상기 표 3에 의할 때, 비교예보다 실시예의 휘도 및 명암비가 높음을 확인할 수 있었다. 이는 본 명세서에 따른 화합물이 프탈로시아닌 구조에 알킬 또는 아릴옥시기를 치환기로 도입함으로써 용해도를 증가시키고, 추가적으로 적어도 하나의 히드록시기를 치환기로 도입하여 분자간의 상호 작용을 통해 응집(aggregation)을 유도하여 Qy 흡수 세기를 증가시킬 수 있어, 휘도 및 명암비가 우수한 것임을 확인할 수 있었다.According to Table 3, it was confirmed that the luminance and contrast ratio of the Example was higher than that of the Comparative Example. This increases the solubility of the compound according to the present specification by introducing an alkyl or aryloxy group as a substituent into the phthalocyanine structure, and additionally introduces at least one hydroxy group as a substituent to induce aggregation through interaction between molecules, thereby inducing Qy absorption intensity. Can be increased, it was confirmed that the luminance and contrast ratio is excellent.
Claims (11)
[화학식 1]
상기 화학식 1에 있어서,
M은 수소; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; 또는 Zr이고,
상기 M이 Al인 경우, M은 -O(P=O)R'R''와 결합되고,
상기 R' 및 R''는 서로 같거나 상이하고 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환 알콕시기; 또는 치환 또는 비치환 아릴옥시기이며,
R1 내지 R16은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며,
R1 내지 R16 중 적어도 하나는 히드록시기이고, R1 내지 R16 중 히드록시기가 아닌 치환기 중 적어도 하나는 -OR이며,
상기 R은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
M is hydrogen; Cu; Zn; Co; Al; Ga; In; Ca; Mo; Mg; Or Zr,
When M is Al, M is combined with -O(P=O)R'R'',
R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted aryloxy group,
R1 to R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
At least one of R1 to R16 is a hydroxy group, and at least one of the substituents other than a hydroxy group of R1 to R16 is -OR,
R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
[화학식 2]
상기 화학식 2에 있어서,
M은 상기 화학식 1에서의 정의와 동일하고,
R1 내지 R14 및 R16는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 히드록시기; 할로겐기; 또는 -OR이며,
R1 내지 R14 및 R16 중 적어도 하나는 히드록시기이고,
R 및 Z1은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. The method according to claim 1, wherein the formula 1 is a compound represented by the following formula 2:
[Formula 2]
In Formula 2,
M is the same as the definition in Formula 1,
R1 to R14 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Hydroxy group; Halogen group; Or -OR,
At least one of R1 to R14 and R16 is a hydroxy group,
R and Z1 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
상기 R은 상기 화학식 1에서의 정의와 동일한 것인 화합물.The method of claim 1, wherein at least one of R3, R7, R11 and R15 is -OR,
Wherein R is the same as defined in Formula 1 above.
.The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following formulas:
.
상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이고,
상기 광개시제의 함량은 0.1 중량% 내지 20 중량%이며,
상기 다관능성 모노머의 함량은 0.1 중량% 내지 50 중량%인 것인 감광성 수지 조성물.The method according to claim 7, wherein the content of the compound represented by Formula 1 based on the total weight of the solid content in the photosensitive resin composition is 5% by weight to 60% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1% to 20% by weight,
The content of the polyfunctional monomer is 0.1% to 50% by weight of the photosensitive resin composition.
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