TW201811927A - Photosensitive resin composition, photosensitive material, color filter and display device capable of increasing color reproducibility, brightness and contrast ratio - Google Patents
Photosensitive resin composition, photosensitive material, color filter and display device capable of increasing color reproducibility, brightness and contrast ratio Download PDFInfo
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- TW201811927A TW201811927A TW106123549A TW106123549A TW201811927A TW 201811927 A TW201811927 A TW 201811927A TW 106123549 A TW106123549 A TW 106123549A TW 106123549 A TW106123549 A TW 106123549A TW 201811927 A TW201811927 A TW 201811927A
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- chemical formula
- resin composition
- substituted
- photosensitive resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 53
- 239000000463 material Substances 0.000 title claims description 15
- 239000000126 substance Substances 0.000 claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 24
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 21
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 239000000049 pigment Substances 0.000 claims description 44
- -1 nitro, phenoxy, carboxyl Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000000975 dye Substances 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003367 polycyclic group Chemical group 0.000 claims description 18
- 125000000129 anionic group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 239000002270 dispersing agent Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000001000 anthraquinone dye Substances 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 5
- 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 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- YKENVNAJIQUGKU-UHFFFAOYSA-N tetraazaporphin Chemical compound C=1C(C=N2)=NC2=NC(NN2)=NC2=CC(C=C2)=NC2=CC2=NC=1C=C2 YKENVNAJIQUGKU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000001003 triarylmethane dye Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
- 235000006708 antioxidants Nutrition 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 4
- 239000001055 blue pigment Substances 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920006223 adhesive resin Polymers 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- BZCWFJMZVXHYQA-UHFFFAOYSA-N 3-dimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[SiH](OC)CCCOC(=O)C(C)=C BZCWFJMZVXHYQA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
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- 239000001045 blue dye Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- CZPLANDPABRVHX-UHFFFAOYSA-N cascade blue Chemical compound C=1C2=CC=CC=C2C(NCC)=CC=1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 CZPLANDPABRVHX-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
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- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000003017 thermal stabilizer Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本說明書是有關於一種光敏樹脂組成物與包含其的彩色濾光片。This specification relates to a photosensitive resin composition and a color filter including the same.
近年來,對彩色濾光片要求以高亮度、高對比率(contrast ratio)為特徵的性能。另外,顯示元件開發的主要目的之一為由色純度的提升帶來的顯示元件性能的差別化及製造步驟中的生產性的提升。In recent years, the color filter is required to be characterized by high brightness and high contrast ratio. In addition, one of the main purposes of the development of display elements is to differentiate the performance of display elements due to the improvement in color purity and to improve the productivity in manufacturing steps.
先前,用作彩色濾光片的著色劑的顏料類型是以粒子分散狀態存在於彩色光阻劑中,因此,難以藉由調節顏料粒子的尺寸與分佈來調節亮度及對比率。於為顏料粒子的情況下,於彩色濾光片內凝聚,溶解性及分散性差,由於凝聚(aggregation)的大粒子而引起光的多重散射(multiple scattering)。已指出所述偏光的光的散射是使對比率降低的主要原因。為了藉由顏料的超微粒化及分散穩定化來提升亮度及對比率,正在不斷地努力,但就用以實現高色純度的顯示裝置用色座標的著色劑的選定而言,自由度受限。另外,藉由使用已開發出的著色材料、尤其是顏料的顏料分散法來提升彩色濾光片的色純度、亮度及對比率已達到極限。因此,要求開發用於藉由提高色純度來提升色彩再現性、亮度及對比率的著色劑或包含其的光敏樹脂組成物。 [現有技術文獻] [專利文獻]Previously, the type of pigment used as a coloring agent for a color filter existed in the color photoresist in a particle dispersed state, and therefore, it was difficult to adjust the brightness and contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, they aggregate in a color filter, have poor solubility and dispersibility, and cause multiple scattering of light due to aggregation of large particles. It has been pointed out that the scattering of the polarized light is the main reason for the decrease in the contrast ratio. Efforts are being made to improve brightness and contrast ratios by ultra-micronization of pigments and stabilization of dispersion. However, there is a limited degree of freedom in the choice of colorants to achieve color coordinates for display devices with high color purity. . In addition, the color purity, brightness, and contrast ratio of color filters have been increased by using a pigment dispersion method using developed coloring materials, especially pigments. Therefore, it is required to develop a coloring agent or a photosensitive resin composition containing the same for improving color reproducibility, brightness, and contrast by improving color purity. [Prior Art Literature] [Patent Literature]
[專利文獻1]日本專利特開平9-87534號公報[Patent Document 1] Japanese Patent Laid-Open No. 9-87534
[發明所欲解決的課題] 本發明是有關於一種光敏樹脂組成物、使用其所製造的彩色濾光片。[Problems to be Solved by the Invention] The present invention relates to a photosensitive resin composition and a color filter manufactured using the same.
[解決課題之手段] 本發明的一實施形態提供一種光敏樹脂組成物,其特徵在於包含由下述化學式1表示的化合物、與抗氧化劑,且 所述抗氧化劑包含選自由磷酸酯基及亞磷酸酯基所組成的群組中的至少一個基、與羥基苯基。 [化學式1]化學式1中, LA 及LB 彼此相同或不同,分別獨立地為直接鍵結或碳數1~10的伸烷基, RA ~RF 彼此相同或不同,分別獨立地選自由氫、重氫、鹵素原子、硝基、經取代或未經取代的碳數1~30的烷基、經取代或未經取代的碳數1~30的烷氧基、經取代或未經取代的碳數6~30的單環或多環的芳基、及經取代或未經取代的碳數1~30的單環或多環的雜芳基所組成的群組中, R1 ~R6 彼此相同或不同,分別獨立地選自由氫、重氫、鹵素原子、經取代或未經取代的碳數1~6的直鏈或分支鏈的烷基、經取代或未經取代的碳數1~6的烷氧基、磺酸基、磺酸酯基、磺酸鹽基、-SO2 NHR7 基、及-SO2 NR8 R9 所組成的群組中, R7 ~R9 彼此相同或不同,分別獨立地為直鏈或分支鏈的碳數1~10的烷基, X1 ~X5 彼此相同或不同,分別獨立地選自由氫、重氫、陰離子性基、羥基、經取代或未經取代的碳數1~30的烷基、經取代或未經取代的碳數6~30的單環或多環的芳基、及經取代或未經取代的碳數1~30的單環或多環的雜芳基所組成的群組中, 所述X1 ~X5 中的至少一個為陰離子性基, RAA 及RBB 彼此相同或不同,分別獨立地選自由氫、重氫、經取代或未經取代的碳數1~30的烷基、經取代或未經取代的碳數1~30的烷氧基、經取代或未經取代的碳數6~30的單環或多環的芳基、經取代或未經取代的碳數1~30的單環或多環的雜芳基、鹵素原子、硝基、苯氧基、羧基、羧酸酯基、羧酸鹽基、烷氧基羰基、羥基、磺酸基、磺酸酯基、磺酸鹽基、-SO2 NHR'及-SO2 NR''R'''所組成的群組中, a及b彼此相同或不同,分別獨立地為0~4的整數, 於a及b為2以上的情況下,括號中的結構彼此相同或不同, R'、R''及R'''彼此相同或不同,分別獨立地為碳數1~30的烷基。[Means for Solving the Problem] An embodiment of the present invention provides a photosensitive resin composition comprising a compound represented by the following Chemical Formula 1 and an antioxidant, and the antioxidant includes a member selected from the group consisting of a phosphate group and phosphorous acid. At least one group in the group consisting of an ester group, and a hydroxyphenyl group. [Chemical Formula 1] In Chemical Formula 1, L A and L B are the same or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms, and R A to R F are the same or different from each other, and are each independently selected from the group consisting of hydrogen and heavy Hydrogen, halogen atom, nitro, substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted carbon In the group consisting of 6 to 30 monocyclic or polycyclic aryl groups and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms, R 1 to R 6 are the same as each other Or different, each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted carbon number 1 to 6 In the group consisting of alkoxy, sulfonate, sulfonate, sulfonate, -SO 2 NHR 7 and -SO 2 NR 8 R 9 , R 7 to R 9 are the same or different from each other , are each independently an alkyl group linear or branched carbon atoms having 1 to 10, X 1 ~ X 5 are the same or different, each independently selected from the group consisting of hydrogen, deuterium, an anionic group, a hydroxyl group, a substituted Unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted mono to 1 to 30 carbons In a group consisting of a cyclic or polycyclic heteroaryl group, at least one of X 1 to X 5 is an anionic group, and R AA and R BB are the same or different from each other, and are independently selected from hydrogen and deuterium. , Substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted monocyclic or unsubstituted 6 to 30 carbons, or Polycyclic aryl, substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbon atoms, halogen atom, nitro, phenoxy, carboxyl, carboxylate, carboxylate , Alkoxycarbonyl, hydroxy, sulfonic, sulfonate, sulfonate, -SO 2 NHR 'and -SO 2 NR "R'", a and b are the same as each other Or different, they are each independently an integer of 0 to 4, and when a and b are 2 or more, the structures in parentheses are the same or different from each other, and R ', R''andR''' are the same or different from each other, respectively Independently an alkyl group having 1 to 30 carbon atoms
另外,本發明的一實施形態提供一種使用所述光敏樹脂組成物所製造的光敏材料與包含其的彩色濾光片。In addition, one embodiment of the present invention provides a photosensitive material manufactured using the photosensitive resin composition and a color filter including the same.
[發明的效果] 關於本發明的一實施形態的光敏樹脂組成物,於形成彩色濾光片用圖案的情況下,於圖案內實現孔(hole)時,可使感度降低且提高亮度。[Effects of the Invention] When the photosensitive resin composition according to an embodiment of the present invention is used to form a pattern for a color filter, when a hole is formed in the pattern, the sensitivity can be reduced and the brightness can be improved.
以下,對本說明書進行更詳細的說明。 本說明書中,於設為某部分「包含」某構成要素時,只要無特別相反的記載,則該情況是指並不排除其他構成要素,可更包含其他構成要素。 根據本說明書的一實施形態,提供一種包含由所述化學式1表示的化合物及由所述化學式2或化學式3表示的化合物的光敏樹脂組成物。Hereinafter, this specification will be described in more detail. In this specification, when it is assumed that a certain component "includes" a certain component, as long as there is no particularly contrary description, this case means that other components are not excluded, and other components may be further included. According to an embodiment of the present specification, there is provided a photosensitive resin composition including the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 or the chemical formula 3.
本說明書中,「經取代或未經取代的」這一用語是指經選自包含重氫、鹵素原子、烷基、烯基、烷氧基、環烷基、芳基烯基、芳基、芳基氧基、芳烷基、芳烯基、烷基胺基、芳烷基胺基、芳基胺基、雜芳基、咔唑基、丙烯醯基、丙烯酸酯基、醚基、腈基、硝基、羥基、氰基、含有N原子、O原子、S原子或P原子中的一個以上的雜芳基及陰離子性基的群組中的一個以上的取代基所取代或者不具有任何取代基。In the present specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen atom, alkyl, alkenyl, alkoxy, cycloalkyl, arylalkenyl, aryl, Aryloxy, aralkyl, arylalkenyl, alkylamino, aralkylamino, arylamino, heteroaryl, carbazolyl, acryloyl, acrylate, ether, nitrile , Nitro, hydroxy, cyano, one or more substituents in the group containing one or more heteroaryl groups and anionic groups containing N, O, S, or P atoms, or do not have any substitution base.
本說明書中,所述烷基可為直鏈或分支鏈,碳數並無特別限定,可為1~30。作為具體例,有甲基、乙基、丙基、異丙基、丁基、第三丁基、戊基、己基及庚基等,但並不限定於該些。 本說明書中,所述烯基可為直鏈或分支鏈,碳數並無特別限定,可為2~25。作為具體例,可為二苯乙烯(stylbenyl)基、苯乙烯(styrenyl)基等經芳基取代而成的烯基,但並不限定於該些。 本說明書中,所述烷氧基可為直鏈或分支鏈,碳數並無特別限定,可為1~30。 本說明書中,環烷基並無特別限定,可為碳數3~20,尤其可為環戊基、環己基。 本說明書中,作為鹵素原子的例子,有氟、氯、溴或碘。In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, third butyl, pentyl, hexyl, and heptyl. In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, but may be 2 to 25. As a specific example, an alkenyl group substituted with an aryl group, such as a stylbenyl group and a styrenyl group, is not limited to these. In this specification, the alkoxy group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 1 to 30. In this specification, the cycloalkyl group is not particularly limited, and may be 3 to 20 carbon atoms, and particularly may be a cyclopentyl group or a cyclohexyl group. In this specification, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.
本說明書中,芳基可為單環式芳基或多環式芳基。 於所述芳基為單環式芳基的情況下,碳數並無特別限定,可為6~40。具體而言,作為單環式芳基,可列舉苯基、聯苯基或聯三苯基等,但並不限定於此。 於所述芳基為多環式芳基的情況下,碳數並無特別限定,可為10~40。具體而言,作為多環式芳基,可列舉萘基、蒽基、菲基、芘基、苝基、䓛基或茀基等,但並不限定於此。 於所述茀基被取代的情況下,可成為、等螺茀基,(9,9-二甲基茀基)及(9,9-二苯基茀基)等經取代而成的茀基。但是,並不限定於此。In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, the carbon number is not particularly limited, and may be 6 to 40. Specifically, examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a bitriphenyl group, but are not limited thereto. When the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, and may be 10 to 40. Specific examples of the polycyclic aryl group include, but are not limited to, naphthyl, anthracenyl, phenanthryl, fluorenyl, fluorenyl, fluorenyl, and fluorenyl. In the case where the fluorenyl group is substituted, it may become , And so on (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups. However, it is not limited to this.
本說明書中,所述雜芳基為含有O、N、S或P作為異種原子的芳香族的雜環基,碳數並無特別限定,可為1~30。作為雜環基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、聯吡啶基、三嗪基、吖啶基(acridyl)、噠嗪基、喹啉基、異喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基及二苯并呋喃基等,但並不限定於該些。In the present specification, the heteroaryl group is an aromatic heterocyclic group containing O, N, S, or P as a hetero atom, and the carbon number is not particularly limited, and may be 1 to 30. Examples of heterocyclic groups are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acrylyl (Acridyl), pyridazinyl, quinolinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene Group, dibenzothienyl, benzofuranyl, dibenzofuranyl, and the like, but are not limited to these.
本說明書中,伸烷基是指於烷烴(alkane)中有兩個鍵結位置的基團。所述伸烷基可為直鏈、分支鏈或環狀鏈。伸烷基的碳數並無特別限定,可為2~25。In the present specification, an alkylene group refers to a group having two bonding positions in an alkane. The alkylene group may be a straight chain, a branched chain, or a cyclic chain. The number of carbons of the alkylene group is not particularly limited, but may be 2 to 25.
本說明書中,伸芳基(arylene)除了為二價基以外,可應用與所述芳基有關的說明。In this specification, in addition to the arylene group being a divalent group, a description related to the aryl group may be applied.
本說明書中,伸雜芳基除了為二價基以外,可應用與所述伸雜芳基有關的說明。In the present specification, in addition to a divalent aryl group, a description related to the extended aryl group may be applied.
本說明書中,鄰接的基團彼此鍵結而形成經取代或未經取代的環,是指形成經取代或未經取代的脂肪族烴環、經取代或未經取代的芳香族烴環、經取代或未經取代的脂肪族雜環、經取代或未經取代的芳香族雜環或者該些的縮合環。In the present specification, adjacent groups are bonded to each other to form a substituted or unsubstituted ring, which means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, A substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or these condensed rings.
本說明書中,所謂脂肪族烴環,為並非芳香族的環,是指僅包含碳原子與氫原子的環。 具體而言,作為脂肪族烴環的例子,有環丙烷、環丁烷、環丁烯、環戊烷、環戊烯、環己烷、環己烯、1,4-環己二烯、環庚烷、環庚烯、環辛烷、環辛烯等,但並不限定於該些。As used herein, the term "aliphatic hydrocarbon ring" refers to a ring that is not aromatic, and refers to a ring containing only carbon atoms and hydrogen atoms. Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, and a ring. Heptane, cycloheptene, cyclooctane, cyclooctene and the like are not limited thereto.
本說明書中,所謂芳香族烴環,是指僅包含碳原子與氫原子的芳香族的環。本說明書中,具體而言,作為芳香族烴環的例子,有苯基、萘基、蒽基、苯、萘、蒽、菲、苝、螢蒽(fluoranthene)、聯伸三苯、萉、芘、稠四苯、䓛、稠五苯、茀、茚、苊、苯并茀、螺茀等,但並不限定於該些。In the present specification, an aromatic hydrocarbon ring refers to an aromatic ring containing only carbon atoms and hydrogen atoms. In this specification, specifically, examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthryl, benzene, naphthalene, anthracene, phenanthrene, fluorene, fluoranthene, triphenylene, hydrazone, fluorene, Condensed tetrabenzene, fluorene, condensed pentabenzene, fluorene, indene, fluorene, benzofluorene, spirofluorene, and the like are not limited thereto.
本說明書中,所謂脂肪族雜環,是指含有雜原子中的一個以上的脂肪族環。具體而言,作為脂肪族雜環的例子,有氧雜環丙烷(oxirane)、四氫呋喃、1,4-二噁烷(1,4-dioxane)、吡咯啶、哌啶、嗎啉(morpholine)、氧雜環庚烷(oxepan)、氮雜環辛烷(azocane)、硫雜環辛烷(thiocane)等,但並不限定於該些。As used herein, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms. Specifically, examples of the aliphatic heterocyclic ring include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, Oxepan, azocane, thiocane, and the like are not limited thereto.
本說明書中,所謂芳香族雜環,是指含有雜原子中的一個以上的芳香族環。具體而言,作為芳香族雜環的例子,有吡啶、吡咯、嘧啶、噠嗪、呋喃、噻吩、咪唑、吡唑、噁唑、異噁唑、噻唑、異噻唑、三唑、噁二唑、噻二唑、二噻唑、四唑、吡喃、噻喃、二嗪、噁嗪、噻嗪、戴奧辛(dioxin)、三嗪、四嗪、異喹啉、喹啉、氫醌(quinol)、喹唑啉、喹噁啉、萘啶、吖啶、啡啶、二氮雜萘、三氮雜茚、吲哚、吲嗪(indolizine)、苯并噻唑、苯并噁唑、苯并咪唑、苯并噻吩、苯并呋喃、二苯并噻吩、二苯并呋喃、咔唑、苯并咔唑、二苯并咔唑、啡嗪、咪唑并吡啶、啡噁嗪、啡啶、吲哚并咔唑、茚并咔唑等,但並不限定於該些。In the present specification, the term "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms. Specifically, examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, Thiadiazole, dithiazole, tetrazole, pyran, thioan, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinol Oxazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzo Thiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, morphine, indolocarbazole, Indencarbazole and the like are not limited to these.
本說明書中,所述脂肪族烴環、芳香族烴環、脂肪族雜環及芳香族雜環可為單環或多環。In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring, and aromatic heterocyclic ring may be monocyclic or polycyclic.
本說明書的一實施形態中,LA 及LB 彼此相同或不同,分別獨立地為直接鍵結或碳數1~10的伸烷基。 一實施形態中,LA 及LB 分別為伸丙基。In one embodiment of the present specification, L A and L B are the same or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms. In one embodiment, L A and L B are respectively propylene.
本說明書的一實施形態中,RA ~RF 彼此相同或不同,分別獨立地選自由氫、重氫、鹵素原子、硝基、經取代或未經取代的碳數1~30的烷基、經取代或未經取代的碳數1~30的烷氧基、經取代或未經取代的碳數6~30的單環或多環的芳基、及經取代或未經取代的碳數1~30的單環或多環的雜芳基所組成的群組中。 一實施形態中,RA ~RF 為氫。 根據本說明書的一實施形態,R1 ~R6 彼此相同或不同,分別獨立地選自由氫、重氫、經取代或未經取代的碳數1~6的直鏈或分支鏈的烷基、磺酸基、磺酸鹽基、-SO2 NHR7 基、及-SO2 NR8 R9 所組成的群組中。 R7 ~R9 彼此相同或不同,分別獨立地為直鏈或分支鏈的碳數1~10的烷基。 根據本說明書的一實施形態,R1 ~R6 彼此相同或不同,分別獨立地選自由氫、重氫、經取代或未經取代的碳數1~6的直鏈或分支鏈的烷基及磺酸鹽基所組成的群組中。In one embodiment of the present specification, R A to R F are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted carbon 1 ~ 30 is a monocyclic or polycyclic heteroaryl group. In one embodiment, R A to R F are hydrogen. According to an embodiment of the present specification, R 1 to R 6 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms, A sulfonic acid group, a sulfonic acid salt group, -SO 2 NHR 7 group, and -SO 2 NR 8 R 9 group. R 7 to R 9 are the same or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms. According to an embodiment of the present specification, R 1 to R 6 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted linear or branched alkyl groups having 1 to 6 carbon atoms, and Sulfonate group.
本說明書的一實施形態中,X1 ~X5 彼此相同或不同,分別獨立地選自由氫、重氫、陰離子性基、羥基、經取代或未經取代的碳數1~30的烷基、經取代或未經取代的碳數6~30的單環或多環的芳基、及經取代或未經取代的碳數1~30的單環或多環的雜芳基所組成的群組中,所述X1 ~X5 中的至少一個為陰離子性基。In one embodiment of the present specification, X 1 to X 5 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, anionic group, hydroxyl group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A group consisting of a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms Wherein at least one of X 1 to X 5 is an anionic group.
本說明書的一實施形態中,所述陰離子性基為選自由-OH、-SO3 - 、-SO3 H、-SO3 - Z+ 、-CO2 H、-O2 - Z+ 、-CO2 Ra 、-SO3 Rb 及-SO3 NRc Rd 所組成的群組中的至少一者,Z+ 表示N(Re )4 + 、Na+ 或K+ ,Ra ~Re 分別獨立地為選自由經取代或未經取代的碳數1~30的直鏈或分支鏈烷基、經取代或未經取代的碳數6~30的單環或多環的芳基、及經取代或未經取代的碳數1~30的單環或多環的雜芳基所組成的群組中的至少一者。 根據本說明書的其他實施形態,所述陰離子性基可為-SO3 - 或-SO3 - Na+ 。 所述陰離子性基可以其自身具有陰離子,或者亦可與其他陽離子一併以錯合化合物的形式存在。因而,根據經取代的陰離子性基的個數,由化學式1表示的化合物的分子整體的電荷之和可不同。於本發明中的化合物的一個胺基中具有陽離子,因此,分子整體的電荷之和可具有從自經取代的陰離子性基的個數減去1所得的值的陰離子至0的值。A description of the present embodiment, the anionic group is selected from the group consisting of -OH, -SO 3 -, -SO 3 H, -SO 3 - Z +, -CO 2 H, -O 2 - Z +, -CO group 2 R a, -SO 3 R b and -SO 3 NR c R d consisting of at least one, Z + represents a N (R e) 4 +, Na + or K +, R a ~ R e Each is independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and At least one of the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms. According to another embodiment of the present specification, the anionic group may be -SO 3 - or -SO 3 - Na + . The anionic group may have an anion by itself, or may exist in the form of a complex compound together with other cations. Therefore, depending on the number of substituted anionic groups, the sum of the charges of the entire molecules of the compound represented by Chemical Formula 1 may differ. Since a compound in the present invention has a cation in one amine group, the sum of the charges of the entire molecule may have a value of an anion to a value obtained by subtracting 1 from the number of substituted anionic groups.
本說明書的一實施形態中,R'、R''及R'''彼此相同或不同,分別獨立地為碳數1~30的烷基。In one embodiment of the present specification, R ′, R ″, and R ′ ″ are the same or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms.
本說明書的一實施形態中,L1 ~L4 彼此相同或不同,分別獨立地為直接鍵結或碳數1~10的伸烷基。 一實施形態中,L1 ~L4 分別為伸乙基。 一實施形態中,R1 ~R4 分別為2。 本說明書的一實施形態中,R1 ~R4 彼此相同或不同,分別獨立地為氫、重氫或碳數1~30的烷基。 一實施形態中,R1 ~R4 彼此相同或不同,分別獨立地為氫或碳數1~10的直鏈或分支鏈的烷基。 一實施形態中,R1 ~R4 為第三丁基。In one embodiment of the present specification, L 1 to L 4 are the same or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms. In one embodiment, L 1 to L 4 are ethylene. In one embodiment, R 1 to R 4 are 2 respectively. In one embodiment of the present specification, R 1 to R 4 are the same as or different from each other, and are each independently hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms. In one embodiment, R 1 to R 4 are the same or different from each other, and are each independently a hydrogen or a linear or branched alkyl group having 1 to 10 carbon atoms. In one embodiment, R 1 to R 4 are a third butyl group.
根據本說明書的一實施形態,所述抗氧化劑可包含選自由磷酸酯基及亞磷酸酯基所組成的群組中的至少一個基、與羥基苯基。 另外,以所述光敏樹脂組成物的固體成分的總重量為基準,所述抗氧化劑可含有0.05重量份~10重量份,更具體而言,可含有0.1重量份~5重量份。According to an embodiment of the present specification, the antioxidant may include at least one group selected from the group consisting of a phosphate group and a phosphite group, and a hydroxyphenyl group. In addition, based on the total weight of the solid content of the photosensitive resin composition, the antioxidant may contain 0.05 to 10 parts by weight, and more specifically, 0.1 to 5 parts by weight.
本說明書的一實施形態中,所述抗氧化劑可由下述化學式2及化學式3表示。 [化學式2][化學式3] In one embodiment of the present specification, the antioxidant may be represented by the following Chemical Formula 2 and Chemical Formula 3. [Chemical Formula 2] [Chemical Formula 3]
本說明書的一實施形態中,所述光敏樹脂組成物可更包含黏合劑樹脂、多官能性單體、光起始劑、溶媒。In one embodiment of the present specification, the photosensitive resin composition may further include a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.
所述黏合劑樹脂若為可顯示出由樹脂組成物所製造的膜的強度、顯影性等物性者,則並無特別限定。 作為所述黏合劑樹脂,可使用賦予機械強度的多官能性單體與賦予鹼溶解性的單體的共聚樹脂,亦可更包含本技術領域中通常所使用的黏合劑。 一實施形態中,所述黏合劑樹脂可為丙烯酸系黏合劑樹脂。The binder resin is not particularly limited as long as it exhibits physical properties such as strength and developability of a film produced from a resin composition. As the binder resin, a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility may be used, and may further include a binder generally used in the technical field. In one embodiment, the adhesive resin may be an acrylic adhesive resin.
賦予所述膜的機械強度的多官能性單體可為選自包含不飽和羧酸酯類、芳香族乙烯基類、不飽和醚類、不飽和醯亞胺類、酸酐的群組中的任一者以上。 作為所述不飽和羧酸酯類的具體例,可選自由(甲基)丙烯酸苄酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸四氫糠酯、(甲基)丙烯酸羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基-3-氯丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸醯基辛基氧基-2-羥基丙酯、丙三醇(甲基)丙烯酸酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、乙氧基二乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基三丙二醇(甲基)丙烯酸酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚丙二醇(甲基)丙烯酸酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸四氟丙酯、(甲基)丙烯酸1,1,1,3,3,3-六氟異丙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙烯酸十七氟癸酯、(甲基)丙烯酸三溴苯酯、α-羥基甲基丙烯酸甲酯、α-羥基甲基丙烯酸乙酯、α-羥基甲基丙烯酸丙酯及α-羥基甲基丙烯酸丁酯所組成的群組中,但並不限定於該些。 作為所述芳香族乙烯基單量體類的具體例,可選自由苯乙烯、α-甲基苯乙烯、(鄰、間、對)-乙烯基甲苯、(鄰、間、對)-甲氧基苯乙烯及(鄰、間、對)-氯苯乙烯所組成的群組中,但並不限定於該些。 作為所述不飽和醚類的具體例,可選自由乙烯基甲醚、乙烯基乙醚及烯丙基縮水甘油醚所組成的群組中,但並不限定於該些。 作為所述不飽和醯亞胺類的具體例,可選自由N-苯基馬來醯亞胺、N-(4-氯苯基)馬來醯亞胺、N-(4-羥基苯基)馬來醯亞胺及N-環己基馬來醯亞胺所組成的群組中,但並不限定於該些。 作為所述酸酐,有馬來酸酐、甲基馬來酸酐、四氫鄰苯二甲酸酐等,但並不限定於該些。The polyfunctional monomer that imparts mechanical strength to the film may be any member selected from the group consisting of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated sulfonimines, and anhydrides. More than one. Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and (methyl) Base) dimethylaminoethyl acrylate, isobutyl (meth) acrylate, tertiary butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, (formyl) (Ethyl) hexyl acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate , 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, fluorenyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (methyl (Meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethyl Glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, P-nonylphenoxy polyethylene glycol (meth) acrylate, Nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3- (meth) acrylate Hexafluoroisopropyl, octafluoropentyl (meth) acrylate, heptafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, α-hydroxymethyl methacrylate, α-hydroxymethyl The group consisting of ethyl acrylate, α-hydroxymethacrylate, and α-hydroxymethacrylate is not limited to these groups. As specific examples of the aromatic vinyl monomers, free styrene, α-methylstyrene, (ortho, meta, para) -vinyltoluene, (ortho, meta, para) -methoxy The group consisting of styrene and (o-, m-, p-)-chlorostyrene is not limited thereto. Specific examples of the unsaturated ethers include, but are not limited to, a group consisting of vinyl methyl ether, vinyl ether, and allyl glycidyl ether. Specific examples of the unsaturated fluorene imines include N-phenylmaleimide, N- (4-chlorophenyl) maleimide, and N- (4-hydroxyphenyl). The group consisting of maleimide and N-cyclohexylmaleimide is not limited to these. Examples of the acid anhydride include, but are not limited to, maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride.
所述賦予鹼溶解性的單體若為包含酸基者,則並無特別限定,例如較佳為使用選自由(甲基)丙烯酸、巴豆酸、衣康酸、馬來酸、富馬酸、馬來酸單甲酯、5-降冰片烯-2-羧酸、鄰苯二甲酸單-2-((甲基)丙烯醯氧基)乙酯、琥珀酸單-2-((甲基)丙烯醯氧基)乙酯、ω-羧基聚己內酯單(甲基)丙烯酸酯所組成的群組中的一種以上,但並不限定於該些。The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group. For example, a monomer selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, Monomethyl maleate, 5-norbornene-2-carboxylic acid, mono-2-(((meth) acryloxy) ethyl) phthalate, mono-2-((methyl) succinate One or more of the group consisting of acryloxy) ethyl ester and ω-carboxy polycaprolactone mono (meth) acrylate is not limited thereto.
根據本說明書的一實施形態,所述黏合劑樹脂的酸值為50 KOH mg/g~130 KOH mg/g,重量平均分子量為1,000~50,000。According to an embodiment of the present specification, the adhesive resin has an acid value of 50 KOH mg / g to 130 KOH mg / g and a weight average molecular weight of 1,000 to 50,000.
所述多官能性單體為發揮藉由光而形成光阻劑圖像的作用的單體,具體而言,可為選自由丙二醇甲基丙烯酸酯、二季戊四醇六丙烯酸酯、二季戊四醇丙烯酸酯、新戊二醇二丙烯酸酯、6-己二醇二丙烯酸酯、1,6-己二醇丙烯酸酯四乙二醇甲基丙烯酸酯、雙苯氧基乙醇二丙烯酸酯、三羥基乙基異氰脲酸酯三甲基丙烯酸酯、三甲基丙烷三甲基丙烯酸酯、二苯基季戊四醇六丙烯酸酯、季戊四醇三甲基丙烯酸酯、季戊四醇四甲基丙烯酸酯及二季戊四醇六甲基丙烯酸酯所組成的群組中的一種或兩種以上的混合物。The polyfunctional monomer is a monomer that functions to form a photoresist image by light. Specifically, the polyfunctional monomer may be selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, Neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanate Ureate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate One or a mixture of two or more in the group.
所述光起始劑若為藉由光而產生自由基來引發交聯的起始劑,則並無特別限定,例如可為選自由苯乙酮系化合物、聯咪唑系化合物、三嗪系化合物及肟系化合物所組成的群組中的一種以上。The photo-initiator is not particularly limited as long as it is a initiator that generates free radicals to initiate cross-linking. For example, the photo-initiator may be selected from acetophenone-based compounds, biimidazole-based compounds, and triazine-based compounds. And one or more of the group consisting of oxime-based compounds.
所述苯乙酮系化合物有2-羥基-2-甲基-1-苯基丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、4-(2-羥基乙氧基)-苯基-(2-羥基-2-丙基)酮、1-羥基環己基苯基酮、安息香甲醚、安息香乙醚、安息香異丁醚、安息香丁醚、2,2-二甲氧基-2-苯基苯乙酮、2-甲基-(4-甲硫基)苯基-2-嗎啉基-1-丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁烷-1-酮、2-(4-溴-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁烷-1-酮或2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基丙烷-1-酮等,並不限定於此。The acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one and 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1 -Ketone, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ether, benzoin isobutyl ether, Benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholinyl-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butane-1-one, 2- (4-bromo-benzyl-2-dimethylamino- 1- (4-morpholinylphenyl) -butane-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinylpropane-1-one, etc., It is not limited to this.
作為所述聯咪唑系化合物,有2,2-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(鄰氯苯基)-4,4',5,5'-四(3,4,5-三甲氧基苯基)-1,2'-聯咪唑、2,2'-雙(2,3-二氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(鄰氯苯基)-4,4,5,5'-四苯基-1,2'-聯咪唑等,並不限定於此。Examples of the biimidazole-based compound include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) -4,4 ', 5,5'-tetra (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole It is not limited to this.
所述三嗪系化合物有3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸1,1,1,3,3,3-六氟異丙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸乙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸2-環氧基乙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸環己酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸苄酯、3-{氯-4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙醯胺、2,4-雙(三氯甲基)-6-對甲氧基苯乙烯基-均三嗪、2,4-雙(三氯甲基)-6-(1-對二甲基胺基苯基)-1,3-丁二烯基-均三嗪、2-三氯甲基-4-胺基-6-對甲氧基苯乙烯基-均三嗪等,並不限定於此。The triazine compound includes 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propanoic acid, 3- {4- [2,4- Bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanoic acid 1,1,1,3,3,3-hexafluoroisopropyl ester, 2- {4- [2,4- Bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} ethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] Phenylthio} 2-epoxyethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -mesatriazin-6-yl] phenylthio} cyclohexyl acetate, 2- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} benzyl acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) ) -Mesytriazine-6-yl] phenylthio} propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanamide , 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylamino Phenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like are not limited thereto.
所述肟系化合物有1,2-辛二酮, -1-(4-苯硫基)苯基,-2-(鄰苯甲醯基肟)(汽巴-嘉基(Ciba-Geigy)公司製造,CGI-124)、乙酮,-1-(9-乙基)-6-(2-甲基苯甲醯基-3-基)-,1-(O-乙醯基肟)(CGI-242)、N-1919(艾迪科(Adeka)公司製造)等,並不限定於此。The oxime-based compounds include 1,2-octanedione, -1- (4-phenylthio) phenyl, 2- (o-benzoylhydrazine) (Ciba-Geigy) Manufactured, CGI-124), ethyl ketone, -1- (9-ethyl) -6- (2-methylbenzylidene-3-yl)-, 1- (O-acetamidooxime) (CGI -242), N-1919 (manufactured by Adeka), etc., are not limited to this.
所述溶媒可為選自由丙酮、甲基乙基酮、甲基異丁基酮、甲基溶纖劑、乙基溶纖劑、四氫呋喃、1,4-二噁烷、乙二醇二甲醚、乙二醇二乙醚、丙二醇二甲醚、丙二醇二乙醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙醚、氯仿、二氯甲烷、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2-三氯乙烷、1,1,2-三氯乙烯、己烷、庚烷、辛烷、環己烷、苯、甲苯、二甲苯、甲醇、乙醇、異丙醇、丙醇、丁醇、第三丁醇、2-乙氧基丙醇、2-甲氧基丙醇、3-甲氧基丁醇、環己酮、環戊酮、丙二醇甲醚乙酸酯、丙二醇乙醚乙酸酯、3-甲氧基丁基乙酸酯、3-乙氧基丙酸乙酯、乙基溶纖劑乙酸酯、甲基溶纖劑乙酸酯、乙酸丁酯、丙二醇單甲醚及二丙二醇單甲醚所組成的群組中的一種以上,但並不限定於此。The solvent may be selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, and 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 ether, chloroform, dichloromethane, 1,2-diethyl ether Ethyl chloride, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene , Toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tertiary butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, ring Hexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, One or more types of methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether are not limited thereto.
本說明書的一實施形態中,以所述光敏樹脂組成物中的固體成分的總重量為基準,由所述化學式1表示的化合物的含量為0.1重量份~50重量份, 由所述化學式2表示的化合物的含量為0.01重量份~10重量份, 所述黏合劑樹脂的含量為1重量份~60重量份, 所述光起始劑的含量為0.1重量份~20重量份, 所述多官能性單體的含量為0.1重量份~50重量份。In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is 0.1 to 50 parts by weight based on the total weight of solid components in the photosensitive resin composition, and is represented by the chemical formula 2 The content of the compound is 0.01 to 10 parts by weight, the content of the binder resin is 1 to 60 parts by weight, the content of the photoinitiator is 0.1 to 20 parts by weight, and the polyfunctional The content of the sexual monomer is 0.1 to 50 parts by weight.
所謂所述固體成分的總重量,是指樹脂組成物中除溶媒以外的成分的總重量之和。固體成分及各成分的以固體成分為基準的重量份的基準可藉由液相層析法或氣相層析法等本領域中所使用的通常的分析手段進行測定。The total weight of the solid content refers to the sum of the total weight of components other than the solvent in the resin composition. The solid content and the weight basis of the solid content of each component based on the solid content can be measured by a usual analysis means used in the art such as liquid chromatography or gas chromatography.
本說明書的一實施形態中,所述光敏樹脂組成物可更包含染料及顏料中的至少一者。 染料與顏料均發揮吸收所需範圍的波長而表現出顏色的作用,根據對溶媒的溶解度而分為染料與顏料。染料可指對溶媒的溶解度大而容易溶解者,顏料可指溶解度相對低而不容易溶解者。 另外,所述染料可為選自包含蒽醌系染料、四氮雜卟啉系染料及三芳基甲烷系染料的群組中的至少一者。 另外,所述蒽醌系染料可由下述化學式4表示。 [化學式4]所述化學式4中, R11 及R12 分別獨立地為選自由胺基、烷基胺基、二烷基胺基、苯基胺基及二苯基胺基所組成的群組中的至少一者。In one embodiment of the present specification, the photosensitive resin composition may further include at least one of a dye and a pigment. Dyes and pigments both exhibit the function of absorbing wavelengths in the required range and exhibit color. They are classified into dyes and pigments according to their solubility in solvents. Dyes may refer to those with a large solubility in a solvent and are easily soluble, and pigments may refer to those with a relatively low solubility and are not easily soluble. The dye may be at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye. The anthraquinone dye may be represented by the following Chemical Formula 4. [Chemical Formula 4] In the chemical formula 4, R 11 and R 12 are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. By.
另外,根據本說明書的一實施形態,所述蒽醌系染料可為選自下述化合物中的任一者。 In addition, according to an embodiment of the present specification, the anthraquinone-based dye may be any one selected from the following compounds.
另外,根據本說明書的一實施形態,所述四氮雜卟啉系染料可選自下述化合物。 In addition, according to an embodiment of the present specification, the tetraazaporphyrin-based dye may be selected from the following compounds.
另外,根據本說明書的一實施形態,所述三芳基甲烷系染料可為選自下述化合物中的任一者。 In addition, according to an embodiment of the present specification, the triarylmethane-based dye may be any one selected from the following compounds.
另外,本說明書的一實施形態中,所述顏料為藍色顏料。 所述藍色顏料為藍色有機顏料,例如可包含C.I.顏料藍15、C.I.顏料藍15:3、C.I.顏料藍15:4、C.I.顏料藍15:6、C.I.顏料藍60等。 一實施形態中,所述顏料可包含銅酞青系顏料。 另外,所述藍色染料為藍色染料,例如可包含甲基系染料、蒽醌系染料、偶氮系染料、三芳基甲烷系染料、酞青系染料等。 另外,所述藍色顏料為藍色色澱顏料,例如可包含藉由色澱化劑來使如所述般的藍色顏料色澱化而成者等。作為色澱化劑,並無特別限定,例如可使用磷鎢酸、磷鉬酸、磷鎢鉬酸、單寧酸、月桂酸、3,4,5-三羥基苯甲酸、鐵氰化物、亞鐵氰化物等。 作為具體的藍色色澱顏料的例子,可列舉:C.I.顏料藍1、C.I.顏料藍1:2、C.I.顏料藍2、C.I.顏料藍3、C.I.顏料藍8、C.I.顏料藍9、C.I.顏料藍10、C.I.顏料藍12、C.I.顏料藍14、C.I.顏料藍17:1、C.I.顏料藍18、C.I.顏料藍19、C.I.顏料藍24、C.I.顏料藍24:1、C.I.顏料藍53、C.I.顏料藍56、C.I.顏料藍56:1、C.I.顏料藍61、C.I.顏料藍61:1、C.I.顏料藍62、C.I.顏料藍63、C.I.顏料藍78等。In one embodiment of the present specification, the pigment is a blue pigment. The blue pigment is a blue organic pigment, and may include, for example, C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4, C.I. Pigment Blue 15: 6, C.I. Pigment Blue 60, and the like. In one embodiment, the pigment may include a copper phthalocyanine-based pigment. The blue dye is a blue dye, and may include, for example, a methyl dye, an anthraquinone dye, an azo dye, a triarylmethane dye, or a phthalocyanine dye. In addition, the blue pigment is a blue lake pigment, and may include, for example, a blue pigment laked by a lake-forming agent as described above. The lake-forming agent is not particularly limited, and examples thereof include phosphotungstic acid, phosphomolybdic acid, phosphotungstic molybdic acid, tannic acid, lauric acid, 3,4,5-trihydroxybenzoic acid, ferricyanide, and Ferricyanide etc. Examples of specific blue lake pigments include: CI Pigment Blue 1, CI Pigment Blue 1: 2, CI Pigment Blue 2, CI Pigment Blue 3, CI Pigment Blue 8, CI Pigment Blue 9, CI Pigment Blue 10, CI Pigment Blue 12, CI Pigment Blue 14, CI Pigment Blue 17: 1, CI Pigment Blue 18, CI Pigment Blue 19, CI Pigment Blue 24, CI Pigment Blue 24: 1, CI Pigment Blue 53, CI Pigment Blue 56, CI Pigment Blue 56: 1, CI Pigment Blue 61, CI Pigment Blue 61: 1, CI Pigment Blue 62, CI Pigment Blue 63, CI Pigment Blue 78, and the like.
本說明書的一實施形態中,所述光敏樹脂組成物更包含分散劑,所述分散劑可包含含有由下述化學式11表示的重複單元或由下述化學式12表示的重複單元的聚合體。 [化學式11][化學式12]化學式11及化學式12中, R301 及R401 彼此相同或不同,分別獨立地為氫或碳數1~10的烷基, R302 、R303 、R402 及R403 彼此相同或不同,可分別獨立地為氫、碳數1~30的烷基、碳數6~30的芳基或碳數1~30的雜芳基, R302 與R303 或者R402 與R403 彼此鍵結而形成經取代或未經取代的環, Ar3 及Ar4 彼此相同或不同,分別獨立地為直接鍵結、碳數1~10的伸烷基、由-[CH(R311 )-CH(R312 )-O]x -CH(R313 )-CH(R314 )-或-[(CH2 )y1 -O]z -(CH2 )y2 -表示的二價連結基, R311 ~R314 彼此相同或不同,分別獨立地為氫或碳數1~10的烷基, x為1~18的整數,於x為2以上的情況下括號中的結構彼此相同或不同, y1及y2彼此相同或不同,分別獨立地為1~5的整數, z為1~18的整數,於z為2以上的情況下括號中的結構彼此相同或不同, Q為選自由直接鍵結、碳數1~10的伸烷基、碳數6~30的伸芳基、-CONH-、-COO-及碳數1~10的醚基所組成的群組中的任一個或兩個以上連結而成的連結基。In one embodiment of the present specification, the photosensitive resin composition further includes a dispersant, and the dispersant may include a polymer including a repeating unit represented by the following chemical formula 11 or a repeating unit represented by the following chemical formula 12. [Chemical Formula 11] [Chemical Formula 12] In Chemical Formula 11 and Chemical Formula 12, R 301 and R 401 are the same or different from each other, and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms. R 302 , R 303 , R 402, and R 403 may be the same or different from each other, and may be respectively Independently, hydrogen, alkyl having 1 to 30 carbons, aryl having 6 to 30 carbons or heteroaryl having 1 to 30 carbons, R 302 and R 303 or R 402 and R 403 are bonded to each other to form a A substituted or unsubstituted ring, Ar 3 and Ar 4 are the same or different from each other, and are each independently a direct bond, an alkylene group having 1 to 10 carbon atoms, and-[CH (R 311 ) -CH (R 312 ) -O] x -CH (R 313 ) -CH (R 314 ) -or -[(CH 2 ) y1 -O] z- (CH 2 ) y2 -a divalent linking group, R 311 to R 314 are the same as each other Or different, each independently is hydrogen or an alkyl group having 1 to 10 carbon atoms, x is an integer of 1 to 18, and when x is 2 or more, the structures in the brackets are the same or different from each other, and y1 and y2 are the same or different from each other , Are each independently an integer of 1 to 5, z is an integer of 1 to 18, when z is 2 or more, the structures in the brackets are the same or different from each other, and Q is selected from the group consisting of directly bonded and 1 to 10 carbon atoms. Alkyl group, arylene group with 6 to 30 carbon atoms, -CONH- A linking group in which any one or two or more of -COO- and an ether group having 1 to 10 carbon atoms are linked.
一實施形態中,以所述樹脂組成物中的固體成分的總重量為基準,所述分散劑可含有0.5重量份~50重量份。 根據本說明書的一實施形態,所述樹脂組成物可更包含抗氧化劑。 根據本說明書的一實施形態,以所述樹脂組成物中的固體成分的總重量為基準,所述抗氧化劑的含量為0.1重量份~20重量份。In one embodiment, the dispersant may contain 0.5 to 50 parts by weight based on the total weight of solid components in the resin composition. According to an embodiment of the present specification, the resin composition may further include an antioxidant. According to an embodiment of the present specification, a content of the antioxidant is 0.1 to 20 parts by weight based on a total weight of solid components in the resin composition.
根據本說明書的一實施形態,所述樹脂組成物更包含選自由光交聯增感劑、硬化促進劑、密著促進劑、界面活性劑、熱聚合防止劑、紫外線吸收劑、分散劑及調平劑所組成的群組中的一種或兩種以上的添加劑。 根據本說明書的一實施形態,以所述樹脂組成物中的固體成分的總重量為基準,所述添加劑的含量為0.1重量份~20重量份。According to an embodiment of the present specification, the resin composition further comprises a member selected from the group consisting of a photocrosslinking sensitizer, a hardening accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a conditioning agent. One or two or more additives in a group of leveling agents. According to an embodiment of the present specification, a content of the additive is 0.1 to 20 parts by weight based on a total weight of solid components in the resin composition.
所述光交聯增感劑可使用選自由以下化合物所組成的群組中的一種以上:二苯甲酮、4,4-雙(二甲基胺基)二苯甲酮、4,4-雙(二乙基胺基)二苯甲酮、2,4,6-三甲基胺基二苯甲酮、鄰苯甲醯基苯甲酸甲酯、3,3-二甲基-4-甲氧基二苯甲酮、3,3,4,4-四(第三丁基過氧化羰基)二苯甲酮等二苯甲酮系化合物;9-茀酮、2-氯-9-茀酮、2-甲基-9-茀酮等茀酮系化合物;硫雜蒽酮、2,4-二乙基硫雜蒽酮、2-氯硫雜蒽酮、1-氯-4-丙基氧基硫雜蒽酮、異丙基硫雜蒽酮、二異丙基硫雜蒽酮等硫雜蒽酮系化合物;氧雜蒽酮、2-甲基氧雜蒽酮等氧雜蒽酮系化合物;蒽醌、2-甲基蒽醌、2-乙基蒽醌、第三丁基蒽醌、2,6-二氯-9,10-蒽醌等蒽醌系化合物;9-苯基吖啶、1,7-雙(9-吖啶基)庚烷、1,5-雙(9-吖啶基戊烷)、1,3-雙(9-吖啶基)丙烷等吖啶系化合物;苄基、1,7,7-三甲基-雙環[2,2,1]庚烷-2,3-二酮、9,10-菲醌等二羰基化合物;2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(2,6-二甲氧基苯甲醯基)-2,4,4-三甲基戊基氧化膦等氧化膦系化合物;4-(二甲基胺基)苯甲酸甲酯、4-(二甲基胺基)苯甲酸乙酯、2-正丁氧基乙基-4-(二甲基胺基)苯甲酸酯等苯甲酸酯系化合物;2,5-雙(4-二乙基胺基亞苄基)環戊酮、2,6-雙(4-二乙基胺基亞苄基)環己酮、2,6-雙(4-二乙基胺基亞苄基)-4-甲基-環戊酮等胺基增效劑;3,3-羰基乙烯基-7-(二乙基胺基)香豆素、3-(2-苯并噻唑基)-7-(二乙基胺基)香豆素、3-苯甲醯基-7-(二乙基胺基)香豆素、3-苯甲醯基-7-甲氧基-香豆素、10,10-羰基雙[1,1,7,7-四甲基-2,3,6,7-四氫-1H,5H,11H-C1]-苯并吡喃并[6,7,8-ij]-喹嗪-11-酮等香豆素系化合物;4-二乙基胺基查耳酮、4-疊氮基亞苄基苯乙酮等查耳酮化合物;2-苯甲醯基亞甲基、3-甲基-b-萘并噻唑啉。As the photocrosslinking sensitizer, one or more members selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4- Bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl o-benzoyl benzoate, 3,3-dimethyl-4-methyl Benzophenone compounds such as oxybenzophenone, 3,3,4,4-tetrakis (third butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone Fluorenone compounds such as 2-methyl-9-fluorenone; thioanthrone, 2,4-diethylthioxanthone, 2-chlorothiaxanthone, 1-chloro-4-propyloxy Thioxanthone compounds such as thioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthone compounds such as xanthone and 2-methylxanthone ; Anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, third butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone and other anthraquinone compounds; 9-phenylacridine Acridine-based compounds such as 1,7-bis (9-acridyl) heptane, 1,5-bis (9-acridylpentane), 1,3-bis (9-acridyl) propane; Benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone, etc. Carbonyl compounds; 2,4,6-trimethylbenzylidene diphenylphosphine oxide, bis (2,6-dimethoxybenzylidene) -2,4,4-trimethylpentyl oxide Phosphine oxide compounds such as phosphine; methyl 4- (dimethylamino) benzoate, ethyl 4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethyl Amino compounds such as benzoate; 2,5-bis (4-diethylaminobenzylidene) cyclopentanone, 2,6-bis (4-diethylamino) Benzyl) cyclohexanone, 2,6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone and other amine synergists; 3,3-carbonylvinyl-7- (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzylidene-7- (diethylamino) ) Coumarin, 3-benzylidene-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetra Coumarin compounds such as hydrogen-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinazin-11-one; 4-diethylaminochalcone, Chalcone compounds such as 4-azidobenzylideneacetophenone; 2-benzylidenemethylene, 3-methyl-b-naphthothiazoline.
所述硬化促進劑用於提高硬化及機械強度,具體而言,可使用選自由2-巰基苯并咪唑、2-巰基苯并噻唑、2-巰基苯并噁唑、2,5-二巰基-1,3,4-噻二唑、2-巰基-4,6-二甲基胺基吡啶、季戊四醇-四(3-巰基丙酸酯)、季戊四醇-三(3-巰基丙酸酯)、季戊四醇-四(2-巰基乙酸酯)、季戊四醇-三(2-巰基乙酸酯)、三羥甲基丙烷-三(2-巰基乙酸酯)及三羥甲基丙烷-三(3-巰基丙酸酯)所組成的群組中的一種以上。The hardening accelerator is used to improve hardening and mechanical strength. Specifically, a hardening accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2,5-dimercapto- 1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol -Tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tri (2-mercaptoacetate) and trimethylolpropane-tri (3-mercapto Propionate).
作為本說明書中所使用的密著促進劑,可使用選自甲基丙烯醯氧基丙基三甲氧基矽烷、甲基丙烯醯氧基丙基二甲氧基矽烷、甲基丙烯醯氧基丙基三乙氧基矽烷、甲基丙烯醯氧基丙基二甲氧基矽烷等甲基丙烯醯基矽烷偶合劑中的一種以上,作為烷基三甲氧基矽烷,可使用選自辛基三甲氧基矽烷、十二烷基三甲氧基矽烷、十八烷基三甲氧基矽烷等中的一種以上。As the adhesion promoter used in this specification, a member selected from the group consisting of methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, and methacryloxypropyl One or more of methacrylfluorenylsilane coupling agents such as triethoxysilane, methacryloxypropyldimethoxysilane, etc., and as the alkyltrimethoxysilane, one selected from octyltrimethoxy One or more of silane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, and the like.
所述界面活性劑為矽系界面活性劑或氟系界面活性劑,具體而言,作為矽系界面活性劑,可使用畢克化學(BYK-Chemie)公司製造的畢克(BYK)-077、畢克(BYK)-085、畢克(BYK)-300、畢克(BYK)-301、畢克(BYK)-302、畢克(BYK)-306、畢克(BYK)-307、畢克(BYK)-310、畢克(BYK)-320、畢克(BYK)-322、畢克(BYK)-323、畢克(BYK)-325、畢克(BYK)-330、畢克(BYK)-331、畢克(BYK)-333、畢克(BYK)-335、畢克(BYK)-341v344、畢克(BYK)-345v346、畢克(BYK)-348、畢克(BYK)-354、畢克(BYK)-355、畢克(BYK)-356、畢克(BYK)-358、畢克(BYK)-361、畢克(BYK)-370、畢克(BYK)-371、畢克(BYK)-375、畢克(BYK)-380、畢克(BYK)-390等,作為氟系界面活性劑,可使用迪愛生(DIC)(大日本油墨化學工業股份有限公司)公司製造的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等,但並不限定於此。The surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, as the silicon-based surfactant, BYK-077, manufactured by BYK-Chemie, can be used. BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK (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. As fluorine-based surfactants, DIC (Dai Nihon Ink Chemical Industry Co., Ltd.) can be used. F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-4 43, 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, etc., but it is not limited thereto.
作為所述抗氧化劑,可為選自由受阻酚(Hindered phenol)系抗氧化劑、胺系抗氧化劑、硫系抗氧化劑及膦系抗氧化劑所組成的群組中的一種以上,但並不限定於此。 作為所述抗氧化劑的具體例,可列舉:磷酸、磷酸三甲酯或磷酸三乙酯之類的磷酸系熱穩定劑;2,6-二-第三丁基-對甲酚、十八烷基-3-(4-羥基-3,5-二-第三丁基苯基)丙酸酯、四雙[亞甲基-3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]甲烷、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、3,5-二-第三丁基-4-羥基苄基亞磷酸二乙酯、2,2-硫代雙(4-甲基-6-第三丁基苯酚)、2,6-g,t-丁基苯酚4,4'-亞丁基-雙(3-甲基-6-第三丁基苯酚)、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)或雙[3,3-雙-(4'-羥基-3'-第三丁基苯基)丁酸]二醇酯(Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid] glycol ester)之類的受阻酚(Hindered phenol)系一次抗氧化劑;苯基-α-萘基胺、苯基-β-萘基胺、N,N'-二苯基-對苯二胺或N,N'-二-β-萘基-對苯二胺之類的胺系二次抗氧化劑;二月桂基二硫化物、二月桂基硫代丙酸酯、二硬脂基硫代丙酸酯、巰基苯并噻唑或四甲基秋蘭姆二硫化物四雙[亞甲基-3-(月桂基硫代)丙酸酯]甲烷等硫(Thio)系二次抗氧化劑;或者三苯基亞磷酸酯、三(壬基苯基)亞磷酸酯、三異癸基亞磷酸酯、雙(2,4-二丁基苯基)季戊四醇二亞磷酸酯(Bis(2,4-ditbutylphenyl)Pentaerythritol Diphosphite)或(1,1'-聯苯基)-4,4'-二基雙亞膦酸四[2,4-雙(1,1-二甲基乙基)苯基]酯((1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester)之類的亞磷酸酯系二次抗氧化劑。The antioxidant may be one or more selected from the group consisting of a hindered phenol-based antioxidant, an amine-based antioxidant, a sulfur-based antioxidant, and a phosphine-based antioxidant, but is not limited thereto. . Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; 2,6-di-third-butyl-p-cresol, and octadecane 3- (4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-tert-butyl-4-hydroxy) Phenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-third-butyl-4-hydroxybenzyl) benzene, 3,5- Diethyl tertiary butyl-4-hydroxybenzyl phosphite, 2,2-thiobis (4-methyl-6-third butylphenol), 2,6-g, t-butyl Phenol 4,4'-butylene-bis (3-methyl-6-third butylphenol), 4,4'-thiobis (3-methyl-6-third butylphenol) or bis [ 3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) Hindered phenol such as butanoicacid] glycol ester) is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine Or N, N'-di-β-naphthyl-p-phenylenediamine, such as amine secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl Thio-based secondary antioxidants such as propionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; Or triphenyl phosphite, tri (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4 -ditbutylphenyl) Pentaerythritol Diphosphite) or (1,1'-biphenyl) -4,4'-diylbisphosphinic acid tetra [2,4-bis (1,1-dimethylethyl) phenyl] Phosphite-based secondary antioxidants such as (1,1'-Biphenyl) -4,4'-Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).
作為所述紫外線吸收劑,可使用2-(3-第三丁基-5-甲基-2-羥基苯基)-5-氯-苯并三唑、烷氧基二苯甲酮等,並不限定於此,本領域中通常所使用者均能夠使用。As the ultraviolet absorber, 2- (3-thirdbutyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, and It is not limited to this, and can be generally used by users in the art.
作為所述熱聚合防止劑,例如可包含選自由對苯甲醚、對苯二酚、鄰苯二酚(pyrocatechol)、第三丁基兒茶酚(t-butyl catechol)、N-亞硝基苯基羥基胺銨鹽、N-亞硝基苯基羥基胺鋁鹽、對甲氧基苯酚、二-第三丁基-對甲酚、鄰苯三酚、苯醌、4,4-硫代雙(3-甲基-6-第三丁基酚)、2,2-亞甲基雙(4-甲基-6-第三丁基苯酚)、2-巰基咪唑及啡噻嗪(phenothiazine)所組成的群組中的一種以上,但並不限定於該些,亦可包含本技術領域中通常已知者。The thermal polymerization inhibitor may include, for example, a compound selected from p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, and N-nitroso. Phenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-third-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thio Bis (3-methyl-6-tert-butylphenol), 2,2-methylenebis (4-methyl-6-tert-butylphenol), 2-mercaptoimidazole and phenothiazine One or more of the formed groups are not limited to these, and may include those generally known in the art.
所述分散劑可以以下方法來使用:以預先對顏料施加表面處理的形式內部添加於顏料中的方法或者外部添加於顏料中的方法。作為所述分散劑,可使用化合物型、非離子性、陰離子性或陽離子性分散劑,可列舉氟系、酯系、陽離子系、陰離子系、非離子系、兩性界面活性劑等。該些可分別單獨使用或將兩種以上組合使用。The dispersant may be used by a method of internally adding to the pigment or a method of externally adding to the pigment in a form in which a surface treatment is applied to the pigment in advance. As the dispersant, a compound-type, nonionic, anionic, or cationic dispersant can be used, and examples thereof include fluorine-based, ester-based, cationic, anionic, non-ionic, and amphoteric surfactants. These can be used individually or in combination of 2 or more types.
具體而言,作為所述分散劑,有選自由聚烷二醇及其酯、聚氧伸烷基多元醇、酯環氧烷加成物、醇環氧烷加成物、磺酸酯、磺酸鹽、羧酸酯、羧酸鹽、烷基醯胺環氧烷加成物及烷基胺所組成的群組中的一種以上,但並不限定於此。Specifically, the dispersant is selected from the group consisting of polyalkylene glycols and their esters, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, and sulfonic acid. One or more members selected from the group consisting of acid salts, carboxylic acid esters, carboxylic acid salts, alkylamidoalkylene oxide adducts, and alkylamines, but are not limited thereto.
所述調平劑可為聚合物性或非聚合物性。作為聚合物性的調平劑的具體例,可列舉聚乙烯亞胺、聚醯胺胺、胺與環氧化物的反應產物,作為非聚合物性的調平劑的具體例,包含非聚合物含硫化合物及非聚合物含氮化合物,但不限定於此,本領域中通常所使用者均能夠使用。The leveling agent may be polymeric or non-polymeric. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamine, reaction products of amines and epoxides, and specific examples of the non-polymeric leveling agent include non-polymeric sulfur The compound and the non-polymeric nitrogen-containing compound are not limited thereto, and can be generally used by users in the art.
本說明書的一實施形態提供一種光敏樹脂組成物,其包含由下述化學式15表示的化合物、由下述化學式2表示的化合物、染料及分散劑,且所述染料為三芳基甲烷系染料。 [化學式15][化學式2]化學式15中,所述R1 ~R6 、RA ~RD 、RAA 、RBB 及X1 ~X5 的定義及化學式2的定義如上文所提及那樣。One embodiment of the present specification provides a photosensitive resin composition including a compound represented by the following Chemical Formula 15, a compound represented by the following Chemical Formula 2, a dye, and a dispersant, and the dye is a triarylmethane-based dye. [Chemical Formula 15] [Chemical Formula 2] In Chemical Formula 15, the definitions of R 1 to R 6 , R A to R D , R AA , R BB, and X 1 to X 5 and the definition of Chemical Formula 2 are as mentioned above.
本說明書的一實施形態提供一種使用所述樹脂組成物所製造的光敏材料。 更詳細而言,提供一種以適當的方法將本發明的一實施形態的樹脂組成物塗佈於基材上而成的薄膜或圖案狀的光敏材料。 作為所述塗佈方法,並無特別限制,可使用噴霧法、輥塗法、旋塗法等,通常廣泛使用旋塗法。另外,於形成塗佈膜之後,視情況,亦可於減壓下去除一部分殘留溶媒。One embodiment of the present specification provides a photosensitive material produced using the resin composition. More specifically, a thin film or a patterned photosensitive material obtained by applying a resin composition according to an embodiment of the present invention to a substrate by an appropriate method is provided. The coating method is not particularly limited, and a spray method, a roll coating method, a spin coating method, or the like can be used, and a spin coating method is generally widely used. In addition, after forming the coating film, a part of the residual solvent may be removed under reduced pressure as appropriate.
作為用於對本說明書的樹脂組成物進行硬化的光源,例如有使波長為250 nm~450 nm的光發散的水銀蒸汽弧(arc)、碳弧、氙(Xe)弧等,但未必限定於此。Examples of the light source for curing the resin composition of the present specification include a mercury vapor arc (arc), a carbon arc, and a xenon (Xe) arc that emit light having a wavelength of 250 nm to 450 nm. However, the present invention is not limited to this. .
本說明書的樹脂組成物可用於薄膜電晶體液晶顯示裝置(Thin Film Transistor Liquid Crystal Display,TFT LCD)彩色濾光片製造用顏料分散型光敏材料、薄膜電晶體液晶顯示裝置(TFT LCD)或有機發光二極體的黑色矩陣形成用光敏材料、外塗層形成用光敏材料、柱狀間隔物(colomn spacer)光敏材料、光硬化型塗料、光硬化性墨水、光硬化性接著劑、印刷版、印刷配線板用光敏材料、電漿顯示器面板(Plasma Display Panel,PDP)用光敏材料等,其用途並無特別限制。The resin composition of this specification can be used in a thin film transistor liquid crystal display (TFT LCD) color filter manufacturing pigment dispersion type photosensitive material, a thin film transistor liquid crystal display (TFT LCD), or organic light emitting device. Photosensitive material for forming a black matrix of a diode, photosensitive material for forming an overcoat layer, photosensitive material for column spacers (colomn spacer), photocurable paint, photocurable ink, photocurable adhesive, printing plate, printing There are no particular restrictions on the use of photosensitive materials for wiring boards and photosensitive materials for plasma display panels (PDP).
根據本說明書的一實施形態,提供一種包含所述光敏材料的彩色濾光片。 所述彩色濾光片包含所述光敏樹脂組成物。將所述光敏樹脂組成物塗佈於基板上,形成塗佈(coating)膜,對所述塗佈膜進行曝光、顯影及硬化,藉此可形成彩色濾光片。According to an embodiment of the present specification, a color filter including the photosensitive material is provided. The color filter includes the photosensitive resin composition. The photosensitive resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.
本說明書的一實施形態的樹脂組成物可提供一種於圖案內實現孔(hole)時,用於使感度降低且實現高亮度的彩色濾光片。 所述基板可為玻璃板、矽晶圓及聚醚碸(Polyethersulfone,PES)、聚碳酸酯(Polycarbonate,PC)等塑膠基材的板等,其種類並無特別限制。 所述彩色濾光片可包含紅色圖案、綠色圖案、藍色圖案、黑色矩陣。The resin composition according to an embodiment of the present specification can provide a color filter for reducing sensitivity and realizing high brightness when a hole is realized in a pattern. The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (Polycarbonate, PC), and the like, and the type thereof is not particularly limited. The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
進而根據其他實施形態,所述彩色濾光片可更包含外塗層。 於彩色濾光片的彩色畫素之間,為了提升對比度,可配置被稱為黑色矩陣的格子狀的黑色圖案。作為黑色矩陣的材料,可使用鉻。該情況下,可利用以下方式:使鉻蒸鍍於玻璃基板整體上,並實施蝕刻處理來形成圖案。但是,考慮到步驟中的高成本、鉻的高反射率、由鉻的廢液引起的環境污染,亦可使用利用能夠進行微細加工的顏料分散法的樹脂黑色矩陣。Furthermore, according to another embodiment, the color filter may further include an overcoat layer. Between the color pixels of the color filter, in order to improve the contrast, a grid-like black pattern called a black matrix can be arranged. As a material of the black matrix, chromium can be used. In this case, a pattern can be formed by depositing chromium on the entire glass substrate and performing an etching process. However, in consideration of the high cost in the step, the high reflectance of chromium, and environmental pollution caused by the waste liquid of chromium, a resin black matrix using a pigment dispersion method capable of fine processing can also be used.
本說明書的一實施形態的黑色矩陣可使用黑色顏料或黑色染料作為著色劑。例如可單獨使用碳黑,或者將碳黑與著色顏料混合使用,此時,由於將遮光性不足的著色顏料加以混合,故而有如下優點:即使著色劑的量相對增加,膜的強度或者對基板的密著性亦不會降低。In the black matrix according to the embodiment of the present specification, a black pigment or a black dye can be used as a colorant. For example, carbon black can be used alone, or carbon black can be mixed with colored pigments. In this case, because colored pigments with insufficient light-shielding properties are mixed, there are advantages such that even if the amount of colorant is relatively increased, the strength of the film or the The adhesion will not be reduced.
根據本說明書,提供一種包含彩色濾光片的顯示器裝置。 所述顯示器裝置可為電漿顯示器面板(Plasma Display Panel,PDP)、發光二極體(Light Emitting Diode,LED)、有機發光元件(Organic Light Emitting Diode,OLED)、液晶顯示裝置(Liquid Crystal Display,LCD)、薄膜電晶體液晶顯示裝置(Thin Film Transistor-Liquid Crystal Display,LCD-TFT)以及陰極射線管(Cathode Ray Tube,CRT)的任一者。According to the present specification, a display device including a color filter is provided. The display device may be a plasma display panel (PDP), a light emitting diode (Light Emitting Diode, LED), an organic light emitting element (Organic Light Emitting Diode, OLED), or a liquid crystal display device (Liquid Crystal Display, LCD), Thin Film Transistor-Liquid Crystal Display (LCD-TFT), and Cathode Ray Tube (CRT).
以下,為了對本說明書進行具體說明,列舉實施例來詳細地說明。但是,本說明書的實施例可變形為各種其他形態,本說明書的範圍不可解釋為限定於以下描述的實施例。本說明書的實施例供於對本領域中有平均知識者更完整地說明本說明書。Hereinafter, in order to specifically describe this specification, examples will be described in detail. However, the embodiments of this specification can be modified into various other forms, and the scope of this specification cannot be interpreted as being limited to the embodiments described below. The examples in this specification are provided to explain the specification more completely to those with average knowledge in the art.
化合物的合成 為了製造本說明書的一實施形態的光敏樹脂組成物,藉由下述般的反應式1來生成化合物1。 [反應式1]將5 g的A-1(8.710 mmol)、8.233 g的B-1(34.838 mmol)、4.815 g的K2 CO3 (34.5838 mmol)放入100 ml的N-甲基吡咯啶酮(N-Methyl Pyrrolidone,NMP)中,於95℃下攪拌12小時。繼而,於減壓下去除溶媒,將200 ml的水放入析出物中並攪拌1小時。另外,於減壓下對析出物進行過濾,並於80℃下乾燥12小時。繼而,藉由管柱層析法將已乾燥的析出物分離。(溶析液(Eluent)-MC:MeOH) 結果,獲取6 g的化合物1(3.322 mmol),產率為72%。 結果如下所述。 離子化模式=:大氣壓化學遊離(Atmospheric Pressure Chemical Ionization,APCI)+:m/z=949[M+H]+,準確質量(Exact Mass):948 所述化合物1的1 H-NMR的測定結果如下所述。1 H NMR(500 MHz,二甲基亞碸(dimethylsulfoxide,DMSO),ppm):8.03(m,11H), 7.69~7.18(m,10H), 6.99~6.95(t,1H), 6.80~6.01(dd,1H), 5.93~5.85(dd,1H), 4.06~3.79(m,4H), 3.72~3.60(m,4H), 2.17~1.70(m,16H)Synthesis of Compound In order to produce a photosensitive resin composition according to an embodiment of the present specification, Compound 1 is produced by the following reaction formula 1. [Reaction formula 1] Put 5 g of A-1 (8.710 mmol), 8.233 g of B-1 (34.838 mmol), and 4.815 g of K 2 CO 3 (34.5838 mmol) into 100 ml of N-Methylpyrrolidone (N-Methyl Pyrrolidone (NMP), and stirred at 95 ° C for 12 hours. Then, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Then, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 6 g of Compound 1 (3.322 mmol) was obtained with a yield of 72%. The results are described below. Ionization mode =: Atmospheric Pressure Chemical Ionization (APCI) +: m / z = 949 [M + H] +, Exact Mass: 948 1 H-NMR measurement result of the compound 1 As described below. 1 H NMR (500 MHz, dimethylsulfoxide (DMSO), ppm): 8.03 (m, 11H), 7.69 ~ 7.18 (m, 10H), 6.99 ~ 6.95 (t, 1H), 6.80 ~ 6.01 ( dd, 1H), 5.93 ~ 5.85 (dd, 1H), 4.06 ~ 3.79 (m, 4H), 3.72 ~ 3.60 (m, 4H), 2.17 ~ 1.70 (m, 16H)
[反應式2]如所述反應式2般,將1.43 g的C‐1(2.732 mmol)、2.99 g的B‐1(9.490 mmol)、1.31 g的K2 CO3 (9.490 mmol)放入20 ml的NMP中,於95℃下攪拌12小時。繼而,於減壓下去除溶媒,將200 ml的水放入析出物中並攪拌1小時。另外,於減壓下對析出物進行過濾,並於80℃下乾燥12小時。繼而,藉由管柱層析法將已乾燥的析出物分離。(溶析液(Eluent)-MC:MeOH) 結果,獲取1.622 g的化合物2(1.912 mmol),產率為70%。 離子化模式=:APCI+:m/z=977[M+H]+,準確質量(Exact Mass):976[Reaction formula 2] As described in Reaction Scheme 2, 1.43 g of C-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), and 1.31 g of K 2 CO 3 (9.490 mmol) were placed in 20 ml of NMP. Stir at 95 ° C for 12 hours. Then, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Then, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 1.622 g of Compound 2 (1.912 mmol) was obtained in a yield of 70%. Ionization mode =: APCI +: m / z = 977 [M + H] +, Exact Mass: 976
[反應式3]如所述反應式3般,將1.608 g的D-1(2.732 mmol)、2.99 g的B-1(9.490 mmol)、1.31 g的K2 CO3 (9.490 mmol)放入20 ml的NMP中,於95℃下攪拌12小時。繼而,於減壓下去除溶媒,將200 ml的水放入析出物中並攪拌1小時。另外,於減壓下對析出物進行過濾,並於80℃下乾燥12小時。繼而,藉由管柱層析法將已乾燥的析出物分離。(溶析液(Eluent)-MC:MeOH) 結果,獲取1.526 g的化合物3(1.622 mmol),產率為59%。 離子化模式=:APCI+:m/z=963[M+H]+,準確質量(Exact Mass):962[Reaction formula 3] As described in Reaction Scheme 3, 1.608 g of D-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), and 1.31 g of K 2 CO 3 (9.490 mmol) were placed in 20 ml of NMP. Stir at 95 ° C for 12 hours. Then, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Then, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 1.526 g of Compound 3 (1.622 mmol) was obtained with a yield of 59%. Ionization mode =: APCI +: m / z = 963 [M + H] +, Exact Mass: 962
實驗例 以下述表1般的比例製作實施例1~實施例4及比較例1~比較例3。各構成的投入單位為克(g)。Experimental Examples Example 1 to Example 4 and Comparative Example 1 to Comparative Example 3 were produced at the ratios shown in Table 1 below. The input unit of each component is gram (g).
[表1]
基板的製作 將所製作的光敏樹脂組成物旋塗(spincoating)於玻璃(5 cm×5 cm)上,於110℃下實施70秒預熱處理(預烘(prebake))而形成膜。將形成有膜的基板與光罩(photo mask)的間隔設為300 μm,使用曝光機對基板整面照射30 mJ/cm2 的曝光量。 繼而,利用顯影液(KOH,0.04%)對經曝光的基板顯影55秒,於230℃下實施20分鐘後熱處理(後烘(post bake))而製作基板。Fabrication of the substrate The prepared photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and subjected to preheating (prebake) at 70 ° C. for 70 seconds to form a film. The gap between the substrate on which the film was formed and the photo mask was set to 300 μm, and the entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm 2 using an exposure machine. Then, the exposed substrate was developed with a developing solution (KOH, 0.04%) for 55 seconds, and subjected to a post-heat treatment (post bake) at 230 ° C. for 20 minutes to prepare a substrate.
實驗例1. 亮度的測定 針對所述製作的基板,使用分光光度計確認顏色特性,將亮度值示於下述[表2]。 實驗例2. 耐熱性的測定 針對所述製作的基板,使用分光光度計確認顏色特性,於230℃的對流烘箱(convection oven)中進而實施1小時熱處理後,另外確認顏色特性而求出△Eab值,並示於下述[表2]。 [表2]
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