CN109564387A - 高敏感肟酯光聚合起始剂以及包含该起始剂的光聚合组合物 - Google Patents
高敏感肟酯光聚合起始剂以及包含该起始剂的光聚合组合物 Download PDFInfo
- Publication number
- CN109564387A CN109564387A CN201780038768.XA CN201780038768A CN109564387A CN 109564387 A CN109564387 A CN 109564387A CN 201780038768 A CN201780038768 A CN 201780038768A CN 109564387 A CN109564387 A CN 109564387A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- oxime ester
- compound
- phenyl carbazole
- photopolymerizable composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 oxime ester Chemical class 0.000 title claims abstract description 160
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000003999 initiator Substances 0.000 title claims abstract description 44
- 230000035945 sensitivity Effects 0.000 title description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims abstract description 13
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000049 pigment Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005251 aryl acyl group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 11
- 239000011248 coating agent Substances 0.000 abstract description 10
- 238000005260 corrosion Methods 0.000 abstract description 8
- 125000006850 spacer group Chemical group 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 56
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000002585 base Substances 0.000 description 43
- 239000007787 solid Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000010408 film Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- ZYNHZTIMNJKVLK-UHFFFAOYSA-N 3-nitro-9h-carbazole Chemical compound C1=CC=C2C3=CC([N+](=O)[O-])=CC=C3NC2=C1 ZYNHZTIMNJKVLK-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000013049 sediment Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 235000000126 Styrax benzoin Nutrition 0.000 description 5
- 244000028419 Styrax benzoin Species 0.000 description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 235000019382 gum benzoic Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000008062 acetophenones Chemical class 0.000 description 4
- 238000007605 air drying Methods 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 description 3
- STGNLGBPLOVYMA-TZKOHIRVSA-N (z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O STGNLGBPLOVYMA-TZKOHIRVSA-N 0.000 description 3
- PHPRWKJDGHSJMI-UHFFFAOYSA-N 1-adamantyl prop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C=C)C3 PHPRWKJDGHSJMI-UHFFFAOYSA-N 0.000 description 3
- KHNZIBAUSLKWSJ-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound C(CCC)N1C(C=CC1=O)=O.C(CCC)N1C(C=CC1=O)=O KHNZIBAUSLKWSJ-UHFFFAOYSA-N 0.000 description 3
- PIRXNUIYQQPJQR-UHFFFAOYSA-N 1-ethylpyrrole-2,5-dione Chemical compound C(C)N1C(C=CC1=O)=O.C(C)N1C(C=CC1=O)=O PIRXNUIYQQPJQR-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 3
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- YPBPJASSEDIBPV-UHFFFAOYSA-N C(CC)N1C(C=CC1=O)=O.C(CC)N1C(C=CC1=O)=O Chemical compound C(CC)N1C(C=CC1=O)=O.C(CC)N1C(C=CC1=O)=O YPBPJASSEDIBPV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000001671 coumarin Nutrition 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
- 230000007547 defect Effects 0.000 description 3
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- 235000019441 ethanol Nutrition 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
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- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
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- OBRYRJYZWVLVLF-UHFFFAOYSA-N 1-ethenyl-4-ethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1 OBRYRJYZWVLVLF-UHFFFAOYSA-N 0.000 description 2
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 2
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- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- BLLZAHSARJPHSO-UHFFFAOYSA-N 2-[2-(4-ethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OCC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 BLLZAHSARJPHSO-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 description 2
- NTHGIYFSMNNHSC-UHFFFAOYSA-N 3-methylbutyl nitrate Chemical compound CC(C)CCO[N+]([O-])=O NTHGIYFSMNNHSC-UHFFFAOYSA-N 0.000 description 2
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- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IZDJJEMZQZQQQQ-UHFFFAOYSA-N dicopper;tetranitrate;pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O IZDJJEMZQZQQQQ-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 229940074654 diuril Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000004744 fabric Substances 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HJYKVGWOAOLIKY-UHFFFAOYSA-N methyl 2-methylidenenonanoate Chemical compound CCCCCCCC(=C)C(=O)OC HJYKVGWOAOLIKY-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000010422 painting Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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Classifications
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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Abstract
本发明提供了一种肟酯苯基咔唑化合物，其可被用来作为光聚合的光起始剂。特别地，与该肟酯苯基咔唑化合物的肟酯部分中的氮原子形成双键的碳原子键结至该苯基咔唑基团，且直接键结至一(C1‑C20)烷基或(C6‑C20)芳基基团。本发明亦提供一种光聚合组合物，其包含该肟酯苯基咔唑化合物。该肟酯苯基咔唑化合物及该光聚合组合物具有改善的溶解度，高度光敏感，且在残膜比、图案稳定性、抗蚀层粘合性等方面展现极佳的物理特性。由于这些优点，该肟酯苯基咔唑化合物及该光聚合组合物适合用于LCD的黑色抗蚀层、彩色抗蚀层、外涂层、柱状间隔物及有机绝缘膜。
Description
技术领域
本发明涉及一种高敏感肟酯光聚合起始剂以及包含该起始剂的光聚合组合物。
背景技术
光敏组合物是通过将光聚合起始剂加入到具有乙烯性不饱和键结(ethylenically unsaturated bond)的聚合性化合物中来制备。由于当使用365nm、405nm及436nm的多色光照射时，光敏组合物可通过聚合性化合物的聚合来固化，其可被用于光固化油墨(photocurable inks)、感光印刷版(photosensitive printing plates)、光致抗蚀层(photoresists)等。为了使该光敏组合物对于用于吸引力印刷的短波长光源具有敏感度，该光聚合起始剂亦需要具有高敏感度。
许多用于光敏组合物中的光聚合起始剂是公知的。例如：PCT国际公开文件WO 02/100903A1描述了具有肟酯部分的光起始剂。此一专利公开揭示了可被用来作为光起始剂的多种肟酯化合物的特定结构及合成方法。然而，在将此等所属技术领域中公知的肟酯化合物用来作为光聚合起始剂，其光分解产物附着到掩膜情况下，在印刷期间将造成图案缺陷，且导致低产率。
由于低的分解温度(≤240℃)，公知的光聚合起始剂在显影后的热固化期间被分解。这样的分解减损了光敏组合物的附着力。由于这些原因，需要具有优异的物理特性如图案稳定性及粘合性的高敏感度光聚合起始剂。
发明内容
因此，本发明的一个目的为提供一种高敏感度光聚合起始剂，包含一肟酯部分，当暴露于光时，不产生附着至掩膜的分解产物，且具有极佳的附着力、图案稳定性及敏感度。
本发明的另一目的为提供一种光起始剂化合物，其适度地溶于用于光聚合组合物的溶剂中，以及一种光敏化合物，其包含该光起始剂化合物。
本发明的又一目的为提供一种光敏组合物，其包含该肟酯化合物作为光起始剂，特别作为抗蚀层(resist)用于形成黑色矩阵(black matrix)、滤色器(color filter)、黑色柱状矩阵(black column matrix)或柱状间隔物图案(column spacer pattern)、具有改善的薄膜特性的有机绝缘膜(organic insulating film)或外涂层(overcoat)。
本发明的一个方面提供了一种肟酯苯基咔唑化合物，其作为用于光交联中的光起始剂，其中与肟酯部分中的氮原子形成双键的碳原子键结至该苯基咔唑基团，且直接键结至(C1-C20)烷基或(C6-C20)芳基基团，且其中该苯基咔唑基团可被一个或多个硝基取代。
该苯基咔唑基团可被一个或二个硝基取代。
本发明的另一方面提供了一种由式1所表示的肟酯苯基咔唑化合物：
其中R1及R2各自独立地为氢(hydrogen)、硝基(nitro)、氰基(cyano)、烷氧基(alkoxy)或卤素(halogen)，条件为R1及R2不同时为氢，R3为(C1-C20)烷基((C1-C20)alkyl)、(C6-C20)芳基((C6-C20)aryl)、(C1-C20)烷氧基((C1-C20)alkoxy)、(C6-C20)芳基(C1-C20)烷基((C6-C20)aryl(C1-C20)alkyl)、羟基(C1-C20)烷基(hydroxy(C1-C20)alkyl)、羟基(C1-C20)烷氧基(C1-C20)烷基(hydroxy(C1-C20)alkoxy(C1-C20)alkyl)、(C3-C20)环烷基((C3-C20)cycloalkyl)、(C1-C20)烷基酰基((C1-C20)alkylacyl)或(C6-C20)芳基酰基((C6-C20)arylacyl)，R4为(C1-C20)烷基、(C6-C20)芳基、(C1-C20)烷氧基、(C6-C20)芳基(C1-C20)烷基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基、(C1-C20)烷基酰基或(C6-C20)芳基酰基；R5及R6各自独立地为氢、(C1-C20)烷基、(C1-C20)烷氧基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基或(C1-C20)烷基酰基，以及n为0或1的整数。
在式1中，R1及R2可各自独立地为氢、硝基、氰基、烷氧基或卤素，条件为R1及R2之一者为硝基。
在式1中，R3可为(C3-C7)烷基或(C6-C7)芳基。
在式1中，R4可为(C1-C3)烷基或(C6-C8)芳基。
在式1中，R5及R6可各自独立地为氢或(C1-C2)烷基。
本发明的另一方面提供了一种光聚合起始剂，其包含该肟酯苯基咔唑化合物。
本发明的另一方面提供了一种光聚合组合物，其包含该肟酯苯基咔唑化合物以及至少一选自可溶于溶剂或碱性水溶液的聚合化合物及具有乙烯性不饱和键的光聚合化合物的化合物。
本发明的另一方面提供了一种光聚合组合物，其包含该肟酯苯基咔唑化合物、至少一选自可溶于溶剂或碱性水溶液的聚合化合物及具有乙烯性不饱和键的光聚合化合物的化合物以及染剂或色素。
本发明的另一方面提供了一种柱间隔物、黑色矩阵、黑色柱状间隔物、滤色器或基材，其具有由该光聚合组合物所形成的有机绝缘膜。
本发明的又一方面提供了一种基材，其具有通过涂布该光聚合组合物所形成的膜。
该膜可为TFT-LCD、OLED或TSP的显示面板。
本发明的肟酯苯基咔唑化合物高度可溶于光敏组合物所使用的溶剂(例如：PGMEA)。由于其高度可溶性，用来作为光交联的起始剂的肟酯苯基咔唑化合物的使用可被极小化。此外，当该溶剂通过蒸发自该光敏组合物的薄膜移除时，可减少结合剂与光起始剂之间的相分离，在交联后达成薄膜特性的改善。因此，该光敏组合物可被用来提供具有良好质量的黑色矩阵、滤色器、柱间隔物、绝缘膜或可光交联的涂布基材。
本发明的肟酯苯基咔唑化合物高度敏感，且在残膜比、图案稳定性、化学抗性及可挠性等方面具有极佳的物理特性，即使小量使用作为该光聚合组合物的光聚合起始剂。由于其优异的特性，使用该肟酯苯基咔唑化合物作为光聚合起始剂，在用于产生用在显示器(如：TFT-LCD、OLED或TSP)的抗蚀层的曝光及后烘烤期间，可最大限度地减少除气(outgassing)的发生。这降低了污染的可能性，因此最大限度地减少缺陷的数量。
附图说明
从下文对于实施方式的描述，结合所附图式，本发明的这些及/或其他的方面及优点将变得显而易知并且更容易理解，其中：
图1是以图形方式比较实施例1、2及3以及比较例1、2、3及4中所制备的肟酯苯基咔唑化合物的敏感度，该肟酯苯基咔唑化合物作为光聚合性组合物的光聚合起始剂。
具体实施方式
现在，本发明将被更为详细地描述。
本发明提供了一种肟酯苯基咔唑化合物，由于在溶剂中适度的溶解度及高敏感度，其可被用来作为具有乙烯性不饱和键的光聚合化合物的光聚合的起始剂。本发明亦提供了一种光敏化合物，其包含该肟酯苯基咔唑化合物。
本发明亦提供了一种光聚合组合物，其包含该肟酯苯基咔唑化合物作为光交联的光起始剂。
作为光交联的光起始剂的肟酯苯基咔唑化合物具有一结构，其中与肟酯部分中的氮原子形成双键的碳原子键结至该苯基咔唑基团，且直接键结至一(C1-C20)烷基或(C6-C20)芳基基团。
苯基咔唑基团优选被一个或多个硝基取代。特别地，以一个硝基取代苯基咔唑基团有效率地改善肟酯苯基咔唑化合物的敏感度及溶解度。当苯基咔唑基团被两个或更多个硝基取代时，可预期高敏感度但造成低溶解度，使得难以使用肟酯苯基咔唑化合物作为光起始剂。
特别地，作为用于光交联中的光起始剂的肟酯苯基咔唑化合物可通过式1表示：
其中R1及R2各自独立地为氢、硝基、氰基、烷氧基或卤素，条件为R1及R2不同时为氢，R3为(C1-C20)烷基、(C6-C20)芳基、(C1-C20)烷氧基、(C6-C20)芳基(C1-C20)烷基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基、(C1-C20)烷基酰基或(C6-C20)芳基酰基，R4为(C1-C20)烷基、(C6-C20)芳基、(C1-C20)烷氧基、(C6-C20)芳基(C1-C20)烷基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基、(C1-C20)烷基酰基或(C6-C20)芳基酰基；R5及R6各自独立地为氢、(C1-C20)烷基、(C1-C20)烷氧基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基或(C1-C20)烷基酰基，以及n为0或1的整数。
作为参照，除非在本文中另有说明，取代基的定义中的烷基由1至20个碳原子所组成。
式1中的R1及R2可各自独立地为氢、硝基、氰基、烷氧基或卤素。当R1及R2的至少一者为硝基时，该肟酯苯基咔唑化合物在敏感度方面是优选的。该卤素可为F、Br或Cl。
式1中的R3可为(C3-C7)烷基或(C6-C7)芳基。当R3为(C3-C7)烷基时，该肟酯苯基咔唑化合物在溶解度方面是优选的。
式中的R4可为，例如：(C1-C3)烷基或(C6-C8)芳基。
特别地，R4为甲基或苯基。
式1中的R5及R6可各自独立地为氢或(C1-C2)烷基。
优选地，R5为氢且R6为氢或甲基。在这种情况下，该肟酯苯基咔唑化合物被赋予了高敏感度。
当R6为氢时，肟酯部分相对于咔唑基团位于对位(para position)。当R6为甲基时，R6及肟酯部分相对于咔唑基团位于邻位(ortho position)及对位。当考虑到立体阻碍时，肟酯部分相对于咔唑基团的对位是更优选的。
举例来说，式1中的n为0或1。当n为1时，肟酯苯基咔唑化合物在较长的波长表现较高的敏感度。
特别地，作为用于光交联的光起始剂的肟酯苯基咔唑化合物或通过式1所表示的肟酯苯基咔唑化合物优选是选自由下列化合物所组成的群组：
式1的肟酯苯基咔唑化合物的合成
制备根据本发明的式1的化合物的方法没有限制。举例来说，式1的化合物可通过反应式1来合成：
在碘化铜(copper iodide,CuI)的存在下，从9H-咔唑(9H-carbazole)及卤素酮(halogen ketone)通过乌耳曼反应(Ullmann reaction)制备咔唑酮化合物(carbazoleketone compound)。使用硝酸铜半水合物(copper nitrate hemipentahydrate,Cu(NO3)2·2.5H2O)硝化咔唑酮化合物，以获得硝基咔唑酮化合物(nitro carbazole ketonecompound)。使用盐酸羟胺(hydroxylamine hydrochloride)胺化硝基咔唑酮化合物，以获得对应的肟化合物(oxime compound)。之后，在作为催化剂的三乙基胺(triethylamine)的存在下，使用乙酰氯(acetyl chloride)乙酰化硝基咔唑肟化合物(nitro carbazoleoxime compound)，以得到式1所表示的肟酯光起始剂。
本发明的光聚合组合物包含作为用于光交联的光起始剂的肟酯苯基咔唑化合物或由式1所表示的肟酯苯基咔唑化合物。
作为用于光交联的光起始剂的肟酯苯基咔唑化合物或由式1所表示的肟酯苯基咔唑化合物可以与一种或多种公知的光聚合起始剂结合使用。
在作为用于光交联的光起始剂的肟酯苯基咔唑化合物或由式1所表示的肟酯苯基咔唑化合物与一种或多种公知的光聚合起始剂结合使用的情况下，基于所有光聚合起始剂的重量，以重量计该肟酯苯基咔唑化合物优选是以50％或更多的量存在。以重量计，作为用于光交联的光起始剂的肟酯苯基咔唑化合物或由式1所表示的肟酯苯基咔唑化合物以50％或更多的量的使用有效地增加光起始剂的溶解度，同时维持光起始剂的敏感度。
作为公知的光起始剂，可以使用例如：苯乙酮类化合物(acetophenones)包含：苯乙酮(acetophenone)、2,2-二乙氧基苯乙酮(2,2-diethoxyacetophenone)、对二甲基苯乙酮(p-dimethylacetophenone)、对二甲基氨基苯丙酮(p-dimethylaminopropiophenone)、二氯苯乙酮(dichloroacetophenone)、三氯苯乙酮(trichloroacetophenone)及对三级丁基苯乙酮(p-tert-butylacetophenone)；二苯甲酮类化合物(benzophenones)包含：二苯酮(benzophenone)、2-氯二苯酮(2-chlorobenzophenone)及p,p’-双二甲基氨基二苯酮(p,p’-bisdimethylaminobenzophenone)；苯偶姻醚类化合物(benzoin ethers)包含：二苯乙二酮(benzil)、苯偶姻(benzoin)、苯偶姻甲基醚(benzoin methyl ether)、苯偶姻异丙基醚(benzoin isopropyl ether)及苯偶姻异丁基醚(benzoin isobutyl ether)；硫化合物(sulfur compounds)包含：芐基二甲基缩酮(benzyl dimethyl ketal)、噻吨(thioxanthene)、2-氯噻吨(2-chlorothioxanthene)、2,4-二乙基噻吨(2,4-diethylthioxanthene)、2-甲基噻吨(2-methylthioxanthene)及2-异丙基噻吨(2-isopropylthioxanthene)；蒽醌类化合物(anthraquinones)包含：2-乙基蒽醌(2-ethylanthraquinone)、八甲基蒽醌(octamethylanthraquinone)、1,2-苯并蒽醌(1,2-benzanthraquinone)及2,3-二苯基蒽醌(2,3-diphenylanthraquinone)；有机过氧化物(organic peroxides)包含：偶氮双异丁腈(azobisisobutyronitrile)、过氧化苯甲酰(benzoyl peroxide)及过氧化异丙苯(cumene peroxide)；硫醇化合物(thiol compounds)包含：2-巯基苯并咪唑(2-mercaptobenzimidazole)、2-巯基苯并恶唑(2-mercaptobenzoxazole)及2-巯基苯并噻唑(2-mercaptobenzothiazole)；咪唑基化合物(imidazolyl compounds)包括：2-(邻氯苯基)-4,5-二(间甲氧基苯基)-咪唑基二聚体(2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl)-imidazolyl dimer)；以及三嗪化合物(triazine compounds)包含：对甲氧基三嗪(p-methoxytriazine)；卤甲基三嗪化合物(halomethyl triazine compounds)包含：2,4,6-参(三氯甲基)-s-三嗪(2,4,6-tris(trichloromethyl)-s-triazine、2-甲基-4,6-双(三氯甲基)-s-三嗪(2-methyl-4,6-bis(trichloromethyl)-s-triazine)、2-[2-(5-甲基呋喃-2-基)乙烯基]-4,6-双(三氯甲基)-s-三嗪(2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine)、2-[2-(呋喃-2-基)乙烯基]-4,6-双(三氯甲基)-s-三嗪(2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine)、2-[2-4(-二乙基氨基-2-甲基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪(2-[2-4(-diethylamino-2-methylphenyl)ethenyl]-4,6-bis(trichloromethyl)-s-triazine)、2-[2-(3,4-二甲氧基苯酚)乙烯基]-4,6-双(三氯甲基)-s-三嗪(2-[2-(3,4-dimethoxyphenol)ethenyl]-4,6-bis(trichloromethyl)-s-triazine)、2-(4-甲氧基苯基)-4,6-双(三氯甲基)-s-三嗪(2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine)、2-(4-乙氧基苯乙烯基)-4,6-双(三氯甲基)-s-三嗪(2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine)、2-(4-甲氧基苯基)-4,6-双(三氯甲基)-s-三嗪(2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine)、2-(4-乙氧基苯乙烯基)-4,6-双(三氯甲基)-s-三嗪(2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine)及2-(4-正丁氧基苯基)-4,6-双(三氯甲基)-s-三嗪(2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine)；及胺基酮(aminoketone)化合物，包含：2-芐基-2-二甲基氨基-1-1(4-吗啉代苯基)丁-1-酮(2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one)。
本发明的光聚合组合物可进一步包含敏化剂。适合用在本发明的光聚合组合物的敏化剂的例子包含：阳离子染料(cationic dyes)如：花青(cyanine)、噻吨(xanthene)、恶嗪(oxazine)、噻嗪(thiazine)、二芳基甲烷(diarylmethane)及三芳基甲烷染料(triarylmethane dyes)；中性染料(neutral dyes)如：部花青素(merocyanine)，香豆素(coumarin)，靛蓝(indigo)，芳香胺(aromatic amine)、酞青素(phthalocyanine)，偶氮(azo)、醌(quinone)及硫噻吨(thioxanthene)光敏染料；以及其它化合物，如：二苯甲酮类化合物(benzophenones)、苯乙酮类化合物(acetophenones)、苯偶姻类化合物(benzoins)、氧硫噻吨类化合物(thioxantones)、蒽醌类化合物(anthraquinones)、咪唑类化合物(imidazoles)、联咪唑类化合物(biimidazoles)、香豆素类化合物(coumarins)、酮香豆素类化合物(ketocoumarins)、三嗪类化合物(triazines)及苯甲酸类化合物(benzoicacids)。
本发明的光聚合组合物可包含一聚合化合物，其可溶于溶剂或碱性水溶液，或一混合物，其含有具有乙烯性不饱和键的光聚合化合物。
可溶于溶剂或碱性水溶液中的聚合化合物可被用来作为粘合剂树脂。该粘合剂树脂可为丙烯酸类(共)聚合物(acrylic(co)polymer)，其选择性地在侧链具有丙烯酸不饱和键。基于光聚合组合物的总重量，该粘合剂树脂的使用量以重量计可介于3至50％的范围。此一范围是优选的，因为图案特性可被控制且赋予薄膜物理特性如：耐热性及耐化学性。
举例来说，该丙烯酸类(共)聚合物可具有2,000至300,000的平均分子量，以及1.0至10.0的密度。更优选地，该丙烯酸类(共)聚合物的平均分子量自4,000至100,000。
举例来说，该丙烯酸类(共)聚合物可为下列单体的(共)聚合物：(甲基)丙烯酸甲酯(methyl(meth)acrylate)、(甲基)丙烯酸乙酯(ethyl(meth)acrylate)、(甲基)丙烯酸丙酯(propyl(meth)acrylate)、(甲基)丙烯酸丁酯(butyl(meth)acrylate)、(甲基)丙烯酸戊酯(pentyl(meth)acrylate)、(甲基)丙烯酸己酯(hexyl(meth)acrylate)、(甲基)丙烯酸环己酯(cyclohexyl(meth)acrylate)、(甲基)丙烯酸庚酯(heptyl(meth)acrylate)、(甲基)丙烯酸辛酯(octyl(meth)acrylate)、(甲基)丙烯酸壬酯(nonyl(meth)acrylate)、(甲基)丙烯酸癸酯(decyl(meth)acrylate)、(甲基)丙烯酸月桂酯(lauryl(meth)acrylate)、(甲基)丙烯酸十二烷基酯(dodecyl(meth)acrylate)、(甲基)丙烯酸十四烷基酯(tetradecyl(meth)acrylate)、(甲基)丙烯酸十八烷基酯(hexadecyl(meth)acrylate)、(甲基)丙烯酸异莰基酯(isobornyl(meth)acrylate)、(甲基)丙烯酸金刚烷基酯(adamantyl(meth)acrylate)、(甲基)丙烯酸二环戊基酯(dicyclopentanyl(meth)acrylate)、(甲基)丙烯酸二环戊烯酯(dicyclopentenyl(meth)acrylate)、(甲基)丙烯酸芐基酯(benzyl(meth)acrylate)、(甲基)丙烯酸2-甲氧基乙酯(2-methoxyethyl(meth)acrylate)、(甲基)丙烯酸2-乙氧基乙酯(2-ethoxyethyl(meth)acrylate)、丙烯酸(acrylic acid)、甲基丙烯酸(methacrylic acid)、伊康酸(itaconic acid)、马来酸(maleic acid)、马来酸酐(maleicanhydride)、马来酸单烷基酯(monoalkyl maleates)、伊康酸单烷基酯(monoalkylitaconates)、富马酸单烷基酯(monoalkyl fumarates)、丙烯酸环氧丙基酯(glycidylacrylate)、甲基丙烯酸环氧丙基酯(glycidyl methacrylate)、(甲基)丙烯酸3,4-环氧丁酯(3,4-epoxybutyl(meth)acrylate)、(甲基)丙烯酸2,3-环氧环己酯(2,3-epoxycyclohexyl(meth)acrylate)、(甲基)丙烯酸3,4-环氧环己基甲酯(3,4-epoxycyclohexyl methyl(meth)acrylate)、(甲基)丙烯酸3-甲基氧环丁烷-3-甲酯(3-methyloxetane-3-methyl(meth)acrylate)、(甲基)丙烯酸3-乙基氧环丁烷-3-甲酯(3-ethyloxetane-3-methyl(meth)acrylate)、苯乙烯(styrene)、α-甲基苯乙烯(α-methylstyrene)、乙酰氧基苯乙烯(acetoxystyrene)、N-甲基马来酰亚胺(N-methylmaleimide)、N-乙基马来酰亚胺(N-ethylmaleimide)、N-丙基马来酰亚胺(N-propylmaleimide)、N-丁基马来酰亚胺(N-butylmaleimide)、N-环己基马来酰亚胺(N-cyclohexylmaleimide)、(甲基)丙烯酰胺((meth)acrylamide)及N-甲基(甲基)丙烯酰胺(N-methyl(meth)acrylamide)。这些单体可被单独使用或结合二或更多个使用。
在侧链中具有丙烯酸不饱和键的丙烯酸(共)聚合物是在40至180℃的温度下，通过含羧基的丙烯酸(共)聚合物与环氧树脂的加成反应所制备的(共)聚合物。特别地，该含羧基的丙烯酸(共)聚合物通过含有羧基的丙烯酸类单体的共聚合所获得，如：丙烯酸(acrylic acid)、甲基丙烯酸(methacrylic acid，伊康酸(itaconic acid)、马来酸(maleic acid)或具有二或多个单体的马来酸单烷基酯(monoalkyl maleate)，该单体选自(甲基)丙烯酸烷基酯(alkyl(meth)acrylates)，如：(甲基)丙烯酸甲酯(methyl(meth)acrylate)，及(甲基)丙烯酸己酯(hexyl(meth)acrylate)、(甲基)丙烯酸环己酯(cyclohexyl(meth)acrylate)、(甲基)丙烯酸异莰基酯(isobornyl(meth)acrylate)、(甲基)丙烯酸金刚烷基酯(adamantyl(meth)acrylate)、(甲基)丙烯酸二环戊基酯(dicyclopentanyl(meth)acrylate)、(甲基)丙烯酸二环戊烯酯(dicyclopentenyl(meth)acrylate)、(甲基)丙烯酸芐基酯(benzyl(meth)acrylate)、(甲基)丙烯酸2-甲氧基乙酯(2-methoxyethyl(meth)acrylate)、(甲基)丙烯酸2-乙氧基乙酯(2-ethoxyethyl(meth)acrylate)、苯乙烯(styrene)、α-甲基苯乙烯(α-methylstyrene)、乙酰氧基苯乙烯(acetoxystyrene)，N-甲基马来酰亚胺(N-methylmaleimide)、N-乙基马来酰亚胺(N-ethylmaleimide)、N-丙基马来酰亚胺(N-propylmaleimide)、N-丁基马来酰亚胺(N-butylmaleimide)、N-环己基马来酰亚胺(N-cyclohexylmaleimide)、(甲基)丙烯酰胺((meth)acrylamide)及N-甲基(甲基)丙烯酰胺(N-methyl(meth)acrylamide)。该环氧树脂选自由丙烯酸环氧丙基酯(glycidyl acrylate)、甲基丙烯酸环氧丙基酯(glycidylmethacrylate)、(甲基)丙烯酸3,4-环氧丁酯(3,4-epoxybutyl(meth)acrylate)、(甲基)丙烯酸2,3-环氧环己酯(2,3-epoxycyclohexyl(meth)acrylate)及(甲基)丙烯酸3,4-环氧环己基甲酯(3,4-epoxycyclohexyl methyl(meth)acrylate)所组成的群组。
可替换地，在侧链具有丙烯酸不饱和键的丙烯酸(共)聚合物可为在40至180℃的温度下，通过含有环氧基的丙烯酸(共)聚合物与含有羧基的丙烯酸类单体的加成反应所制备的(共)聚合物。特别地，含有环氧基的丙烯酸(共)聚合物通过包含环氧基的丙烯酸单体的聚合所获得，如：丙烯酸环氧丙基酯(glycidyl acrylate)、甲基丙烯酸环氧丙基酯(glycidyl methacrylate)、(甲基)丙烯酸3,4-环氧丁酯(3,4-epoxybutyl(meth)acrylate)、(甲基)丙烯酸2,3-环氧环己酯(2,3-epoxycyclohexyl(meth)acrylate)或(甲基)丙烯酸3,4-环氧环己基甲酯(3,4-epoxycyclohexyl methyl(meth)acrylate)，具有二或更多个单体选自(甲基)丙烯酸烷基酯(alkyl(meth)acrylates)，如：(甲基)丙烯酸甲酯(methyl(meth)acrylate)，及(甲基)丙烯酸己酯(hexyl(meth)acrylate)、(甲基)丙烯酸环己酯(cyclohexyl(meth)acrylate)、(甲基)丙烯酸异莰基酯(isobornyl(meth)acrylate)、(甲基)丙烯酸金刚烷基酯(adamantyl(meth)acrylate)、(甲基)丙烯酸二环戊基酯(dicyclopentanyl(meth)acrylate)、(甲基)丙烯酸二环戊烯酯(dicyclopentenyl(meth)acrylate)、(甲基)丙烯酸芐基酯(benzyl(meth)acrylate)、(甲基)丙烯酸2-甲氧基乙酯(2-methoxyethyl(meth)acrylate)、(甲基)丙烯酸2-乙氧基乙酯(2-ethoxyethyl(meth)acrylate)、苯乙烯(styrene)、α-甲基苯乙烯(α-methylstyrene)、乙酰氧基苯乙烯(acetoxystyrene)，N-甲基马来酰亚胺(N-methylmaleimide)、N-乙基马来酰亚胺(N-ethylmaleimide)、N-丙基马来酰亚胺(N-propylmaleimide)、N-丁基马来酰亚胺(N-butylmaleimide)、N-环己基马来酰亚胺(N-cyclohexylmaleimide)、(甲基)丙烯酰胺((meth)acrylamide)及N-甲基(甲基)丙烯酰胺(N-methyl(meth)acrylamide)。该环氧树脂选自由丙烯酸环氧丙基酯(glycidyl acrylate)、甲基丙烯酸环氧丙基酯(glycidylmethacrylate)、(甲基)丙烯酸3,4-环氧丁酯(3,4-epoxybutyl(meth)acrylate)、(甲基)丙烯酸2,3-环氧环己酯(2,3-epoxycyclohexyl(meth)acrylate)及(甲基)丙烯酸3,4-环氧环己基甲酯(3,4-epoxycyclohexyl methyl(meth)acrylate)所组成的群组。含有羧基的丙烯酸类单体可选自由丙烯酸(acrylic acid)、甲基丙烯酸(methacrylic acid)、伊康酸(itaconic acid)、马来酸(maleic acid)及马来酸单烷基酯(monoalkyl maleates)所组成的群组。
本发明亦提供一种光聚合着色组合物，其包含如式1所示的肟酯苯基咔唑化合物，以及染剂或色素。
为了将该组合物应用于产生抗蚀层用以形成滤色器或黑色矩阵，染剂或色素是必需的。合适的染剂或色素的例子包含：青色、洋红、黄色及黑色色素，在红、绿、蓝及减色混色系统中，如：C.I.色素黄色12、13、14、17、20、24、55、83、86、93、109、110、117、125、137、139、147、148、153、154、166及168，C.I.色素橘色36、43、51、55、59及61，C.I.色素红色9、97、122、123、149、168、177、180、192、215、216、217、220、223、224、226、227、228及240，C.I.色素紫色19、23、29、30、37、40及50，C.I.色素蓝色15、15:1、15:4、15:6、22、60及64，C.I.色素绿色7及36，C.I.色素棕色23、25及26，C.I.色素黑色7及泰坦黑。
本发明亦提供一种颜色空间、黑色矩阵、滤色器或基材，其具有由光聚合组合物所形成的有机绝缘膜，或者一种基材，其具有通过涂布该光聚合组合物所形成的膜。举例来说，该膜可被用来作为TFT-LCD、OLED或TSP的显示面板。
该光聚合组合物可被用来形成图案。特别地，可通过施加光聚合组合物至基材上以形成一层、从该层中移除挥发物，如：溶剂、通过光掩膜曝光该无挥发物的层、随后显影来形成图案。本发明亦提供一种该光聚合组合物的固化膜。
该基材可为例如：玻璃、硅、聚碳酸酯、聚酯、芳香族聚酰胺，聚酰胺-亚酰胺、聚酰亚胺、铝或GaAs基材，其表面为平坦。用于施加该光聚合组合物至基材上的方法并无限制。举例来说，可通过旋涂、浇铸、辊涂、狭缝或旋涂来将该光聚合组合物施加至基材上。合适的涂布机，例如：非旋转涂布机可被用来将该光聚合组合物施加至基材上。
随后，通过加热移除挥发物，如：溶剂。所得的层由该光聚合组合物的固体成分所组成。该层随后曝光。举例来说，该层可通过光掩膜被活性能量射线照射。低压汞灯、中压汞灯、高压汞灯、超高压汞灯、氙灯或金属卤素灯适合用来作为曝光光源。激光束亦可被用来作为用于曝光的活性能量射线。
电子射线、α射线、β射线、γ射线、X射线及中子射线亦可作为活性能量射线。举例来说，该光掩膜由玻璃膜及形成于玻璃膜表面的活性能量射线阻挡层所组成。
活性能量射线传输通过未形成光阻挡层的玻璃板的部分。该光聚合组合物对应于光传输部分的图案曝光。其结果在曝光层中产生非照射区域及照射区域。
经曝光的基材使用碱性水溶液显影。举例来说，可通过将曝光层与碱性水溶液接触来显影。特别地，光聚合组合物形成于其上的基材可被浸入碱性水溶液中或被稀释的碱性水溶液喷洒。该碱性水溶液可为例如：碳酸钠(sodium carbonate)、碳酸钾(potassiumcarbonate)、氢氧化钠(sodium hydroxide)、氢氧化钾(potassium hydroxide)、四甲基氢氧化铵(tetramethylammonium hydroxide)或碱性胺(basic amine)的水溶液。通过显影从光聚合组合物层移除非照射区域，但以活性能量射线照射的区域保持不被移除。
通过传统的方法洗涤及干燥经显影的基材。其结果，可以获得所期望的图案。
为了更好地理解本发明，将参考以下实施例及包括比较例详细说明本发明的代表性化合物。然而，本发明并不限于这些实施例，并且可以以各种不同的形式实施。
[实施例1-9]
实施例1
步骤1：1-(4-(9H-咔唑-9-基)苯基)乙酮(1-(4-(9H-carbazol-9-yl)phenyl)ethanone)的合成
9H-咔唑(9H-carbazole)(16.7g,100mmol)、4-溴苯乙酮(4-bromoacetophenone)(25g,125mmol)、CuI(2.0g,10mmol)及18-冠-6(18-crown-6)(1.3g,5mmol)的混合物溶解于二甲基甲酰胺(dimethylformamide)(DMF,100mL)中。所得的溶液在氮气气氛下回流24小时。在反应完成之后，将反应混合物冷却至室温。将该反应混合物倒入300mL的水中，并随后将200mL的二氯甲烷(dimethylene chloride,DMC)加入其中。将该混合物剧烈搅拌并过滤。分离有机层，以Na2SO4干燥，蒸发以得到棕色固体，加入少量(50mL)丙酮，搅拌并过滤，得到浅棕色固体。将该固体溶于乙酸乙酯(ethyl acetate EA)中，通过重结晶纯化以产生标题化合物，其为浅棕色微晶。将滤液浓缩并在室温下静置以获得较大量的产物(总产率：26.5g,78％)。
1H-NMR(δ,ppm),CDCl3:8.20(d,2H),8.15(d,2H),7.70(d,2H),7.49-7.41(m,4H),7.31(t,2H),2.70(s,3H)
步骤2：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙酮(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone)的合成
将步骤1中制备的化合物(5.7g,20mmol)的二氯甲烷(30mL)溶液在0℃下搅拌，然后滴加溶于乙酸(15mL)及乙酸酐(30mL)的混合物的Cu(NO3)2·2.5H2O(5.12g,22mmol)溶液。将所得混合物在室温下搅拌1小时。将反应混合物倒入蒸馏水(200mL)中，得到沉淀物。通过过滤收集该沉淀物，使用水充分地洗涤，并在空气中干燥。通过从乙酸乙酯中重结晶来纯化粗产物。为了≥98％的更高的纯度，使用己烷/乙酸乙酯(4:1)作为洗脱液，通过硅胶柱层析法纯化重结晶产物，得到标题化合物，其为黄色固体(5.8g,75.8％)。
1H-NMR(δ,ppm),CDCl3:9.06(d,1H),8.35-8.21(m,3H),7.70(d,2H),7.56-7.43(m,5H),2.73(s,3H)
步骤3：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙酮肟(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone oxime)的合成
将步骤2中所获得的化合物(2.85g,10mmol)的二氯甲烷(15mL)溶液加入到搅拌的乙醇(30mL)中，然后于其中加入三乙胺(triethylamine)(1.01g,10mmol)。将氢氯酸羟胺(hydroxylamine hydrochloride)(2.8g,30mmol)加入该溶液中。加热所得的溶液以回流3小时。将该反应溶液冷却至室温，倒入200mL的冷水中，以及添加50mL的二氯甲烷。使用分液漏斗分离有机层，并使用蒸馏水(100mL)洗涤三次以除去杂质。将有机层用Na2SO4干燥，并使用旋转蒸发器除去溶剂，得到象牙色固体。使用蒸馏水洗涤该固体，在60℃下真空干燥过夜，得到标题化合物，产率为90％。
1H-NMR(δ,ppm),DMSO-d6:11.44(s,1H),9.30(d,1H),8.34(dd,1H),8.00(d,2H),7.70(d,2H),7.60-7.50(m,3H),7.47-7.42(m,2H),2.27(s,3H)
步骤4：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙-1-酮O-乙酰基肟(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethan-1-one O-acetyl oxime)的合成
将步骤3中得到的化合物(3.0g,10mmol)溶解在用铝箔保护不受光照的反应烧瓶中的二氯甲烷(20mL)中，然后于其中加入三乙胺(1mL)。在0-5℃连续搅拌下将乙酰氯(acetyl chloride)(1.55g,20mmol)滴加至该混合物中。在添加完成后，将所得的混合物在室温下搅拌过夜。将该反应混合物倒入蒸馏水中。搅拌大约10分钟后，将所得的黄色固体过滤、于空气中干燥并从二氯甲烷/甲醇(1/4)中重结晶以获得式1-1的最终肟酯，其为黄色结晶固体(产率：81％)。分离及纯化程序是在黄色室中进行，使其免于遭受≤420nm的光线的照射，因为肟酯在暴露于光照时倾向于分解。
1H-NMR(δ,ppm),CDCl3:9.06(s,1H),8.32(d,1H),8.20(d,1H),8.05(d,2H),7.62(d,2H),7.53(t,1H),7.43-7.38(m,3H),2.51(s,3H),2.32(s,3H)
实施例2-9
除了使用相对应的反应物之外，表1中所示的化合物以与实施例1相同的方式合成。
表1
[比较例1-2]
除了省略步骤2并直接进行步骤3之外，表2中所示的比较例1的化合物以与实施例3相同的方式合成。
除了在步骤2中Cu(NO3)2·2.5H2O以2倍的量使用之外，表2中所示的比较例2的化合物以与实施例3相同的方式合成。
表2
为了参照，比较例1及2各别如式1-34及1-35所示。
[实施例10-18]
实施例10
步骤1：1-(4-(9H-咔唑-9-基)-2-甲基苯基)乙酮(1-(4-(9H-carbazol-9-yl)-2-methylphenyl)ethanone)的合成
9H-咔唑(9H-carbazole)(16.7g,100mmol)、1-(4-溴-2-甲基苯基)乙酮(1-(4-bromo-2-methylphenyl)ethanone)(26.6g,125mmol)、CuI(2.0g,10mmol)及18-冠-6(1.3g,5mmol)的混合物溶解于二甲基甲酰胺(dimethylformamide)(DMF,100mL)中。所得的溶液在氮气气氛下回流24小时。在反应完成之后，将反应混合物冷却至室温。将该反应混合物倒入300mL的水中，并随后将200mL的二氯甲烷(methylene chloride,MC)加入其中。将该混合物剧烈搅拌并过滤。分离有机层，以Na2SO4干燥，蒸发以得到棕色固体，加入少量(50mL)丙酮，搅拌并过滤，得到浅棕色固体。通过硅胶柱层析法纯化该固体，从其它异构体中分离出标题化合物(总产率：15.7g,52％)。
1H-NMR(δ,ppm),CDCl3:8.20(d,2H),8.14(d,2H),7.68(d,2H),7.48-7.40(m,3H),7.32(t,2H),2.70(s,3H),2.68(s,3H)
步骤2：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙酮(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone)的合成
将步骤1中制备的化合物(12.0g,40mmol)的二氯甲烷(60mL)溶液在0℃下搅拌，然后滴加溶于乙酸(30mL)及乙酸酐(60mL)的混合物的Cu(NO3)2·2.5H2O(10.2g,44mmol)溶液。将所得混合物在室温下搅拌1小时。将反应混合物倒入蒸馏水(400mL)中，得到沉淀物。通过过滤收集该沉淀物，使用水充分地洗涤，并在空气中干燥。通过从乙酸乙酯中重结晶来纯化粗产物。为了≥98％的更高的纯度，使用己烷/乙酸乙酯(4:1)作为洗脱液，通过硅胶柱层析法纯化重结晶产物，得到标题化合物，其为黄色固体(10.2g,74.1％)。
1H-NMR(δ,ppm),CDCl3:9.06(d,1H),8.34-8.20(m,3H),7.70(d,2H),7.50-7.32(m,5H),2.80(s,3H),2.73(s,3H)
步骤3：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙酮肟(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone oxime)的合成
将步骤2中所获得的化合物(8.0g,23.2mmol)的二氯甲烷(40mL)溶液加入到搅拌的乙醇(80mL)中，然后于其中加入三乙胺(2.36g,23.2mmol)。将氢氯酸羟胺(4.8g,69.6mmol)加入该溶液中。加热所得的溶液以回流3小时。将该反应溶液冷却至室温，倒入600mL的冷水中，以及添加150mL的二氯甲烷。使用分液漏斗分离有机层，并使用蒸馏水(350mL)洗涤三次以除去杂质。将有机层用Na2SO4干燥，并使用旋转蒸发器除去溶剂，得到象牙色固体。使用蒸馏水洗涤该固体，在60℃下真空干燥过夜，得到标题化合物，产率为89％。
1H-NMR(δ,ppm),DMSO-d6:11.44(s,1H),9.30(d,1H),8.32(dd,1H),8.00(d,2H),7.68(d,2H),7.61-7.53(m,2H),7.46-7.42(m,2H),2.43(s,2H),2.27(s,3H)
步骤4：1-(4-(3-硝基-9H-咔唑-9-基)苯基)乙酮O-乙酰基肟(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone O-acetyl oxime)的合成
将步骤3中得到的化合物(6.0g,20mmol)溶解在用铝箔保护不受光照的反应烧瓶中的二氯甲烷(40mL)中，然后于其中加入三乙胺(1mL)。在0-5℃连续搅拌下将乙酰氯(3.1g,40mmol)滴加至该混合物中。在添加完成后，将所得的混合物在室温下搅拌过夜。将该反应混合物倒入蒸馏水中。搅拌大约10分钟后，将所得的黄色固体过滤、于空气中干燥并从二氯甲烷/甲醇(1/4)中重结晶以获得式1-10的最终肟酯，其为黄色结晶固体(产率：82％)。分离及纯化程序在黄色室中进行，使其免于遭受≤420nm的光线的照射，因为肟酯在暴露于光照时倾向于分解。
1H-NMR(δ,ppm),CDCl3:9.06(s,1H),8.32(d,1H),8.21(d,1H),8.04(d,2H),7.62(d,2H),7.53(t,1H),7.40-7.36(m,3H),2.51(s,3H),2.30(s,3H),2.32(s,3H)
实施例11-18
除了使用相对应的反应物之外，表3中所示的化合物以与实施例10相同的方式合成。
表3
[实施例19-27]
实施例19
步骤1：1-(2-(9H-咔唑-9-基)-4-甲基苯基)乙酮(1-(2-(9H-carbazol-9-yl)-4-methylphenyl)ethanone)的合成
9H-咔唑(16.7g,100mmol)、1-2-溴-4-甲基苯基乙酮(1-2-bromo-4-methylphenyl)ethanone)(26.6g,125mmol)、CuI(2.0g,10mmol)及18-冠-6(1.3g,0.50mmol)的混合物溶解于二甲基甲酰胺(DMF,100mL)中。所得的溶液在氮气气氛下回流24小时。在反应完成之后，将反应混合物冷却至室温。将该反应混合物倒入300mL的水中，并随后将200mL的二氯甲烷(methylene chloride,MC)加入其中。将该混合物剧烈搅拌并过滤。分离有机层，以Na2SO4干燥，蒸发以得到棕色固体，加入少量(50mL)丙酮，搅拌并过滤，得到浅棕色固体。通过硅胶柱层析法纯化该固体，从其它异构体中分离出标题化合物(总产率：7.5g,25％)。
1H-NMR(δ,ppm),CDCl3:8.22(d,2H),8.16(d,2H),7.70(d,2H),7.50-7.41(m,3H),7.31(t,2H),2.70(s,3H),2.42(s,3H)
步骤2：1-(4-甲基-2-(3-硝基-9H-咔唑-9-基)苯基)乙酮(1-(4-methyl-2-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone)的合成
将步骤1中制备的化合物(10g,33.4mmol)的二氯甲烷(60mL)溶液在0℃下搅拌，然后滴加溶于乙酸(30mL)及乙酸酐(60mL)的混合物的Cu(NO3)2·2.5H2O(8.55g,36.7mmol)溶液。将所得混合物在室温下搅拌1小时。将反应混合物倒入蒸馏水(400mL)中，得到沉淀物。通过过滤收集该沉淀物，使用水充分地洗涤，并在空气中干燥。通过从乙酸乙酯中重结晶来纯化粗产物。为了≥98％的更高的纯度，使用己烷/乙酸乙酯(4:1)作为洗脱液，通过硅胶柱层析法纯化重结晶产物，得到标题化合物，其为黄色固体(8.7g,75.6％)。
1H-NMR(δ,ppm),CDCl3:9.05(d,1H),8.34-8.21(m,3H),7.68(d,2H),7.50-7.38(m,4H),2.73(s,3H),2.31(s,3H)
步骤3：1-(4-甲基-2-(3-硝基-9H-咔唑-9-基)苯基)乙酮肟(1-(4-methyl-2-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone oxime)的合成
将步骤2中所获得的化合物(5g,13.9mmol)的二氯甲烷(30mL)溶液加入到搅拌的乙醇(80mL)中，然后于其中加入三乙胺(1.41g,13.9mmol)。将氢氯酸羟胺(2.89g,41.7mmol)加入该溶液中。加热所得的溶液以回流3小时。将该反应溶液冷却至室温，倒入400mL的冷水中，以及添加100mL的二氯甲烷。使用分液漏斗分离有机层，并使用蒸馏水(200mL)洗涤三次以除去杂质。将有机层用Na2SO4干燥，并使用旋转蒸发器除去溶剂，得到象牙色固体。使用蒸馏水洗涤该固体，在60℃下真空干燥过夜，得到标题化合物，产率为85％。
1H-NMR(δ,ppm),DMSO-d6:11.40(s,1H),9.28(d,1H),8.30(dd,1H),8.00(d,2H),7.68(d,2H),7.58-7.50(m,2H),7.47-7.42(m,2H),2.70(s,3H),2.27(s,3H)
步骤4：1-(4-甲基-2-(3-硝基-9H-咔唑-9-基)苯基)乙酮O-乙酰基肟(1-(4-methyl-2-(3-nitro-9H-carbazol-9-yl)phenyl)ethanone O-acetyl oxime)的合成
将步骤3中得到的化合物(4g,11.1mmol)溶解在用铝箔保护不受光照的反应烧瓶中的二氯甲烷(30mL)中，然后于其中加入三乙胺(1.5mL)。在0-5℃连续搅拌下将乙酰氯(1.75g,22.3mmol)滴加至该混合物中。在添加完成后，将所得的混合物在室温下搅拌过夜。将该反应混合物倒入蒸馏水中。搅拌大约10分钟后，将所得的黄色固体过滤、于空气中干燥并从二氯甲烷/甲醇(1/4)中重结晶以获得式1-19的最终肟酯，其为黄色结晶固体(产率：77％)。分离及纯化程序在黄色室中进行，使其免于遭受≤420nm的光线的照射，因为肟酯在暴露于光照时倾向于分解。
1H-NMR(δ,ppm),CDCl3:9.06(s,1H),8.32(d,1H),8.21(d,1H),8.04(d,2H),7.62(d,2H),7.53(t,1H),7.40-7.36(m,3H),2.51(s,3H),2.30(s,3H),2.32(s,3H)
实施例20-27
除了使用相对应的反应物之外，表4中所示的化合物以与实施例19相同的方式合成。
表4
实施例28-33
实施例28
步骤1：1-(4-(9H-咔唑-9-基)苯基)丁-1-酮(1-(4-(9H-carbazol-9-yl)phenyl)butan-1-one)的合成
9H-咔唑(16.7g,100mmol)、1-(4-溴苯基)丁-1-酮(1-(4-bromophenyl)butan-1-one)(28g,125mmol)、CuI(2.0g,10mmol)及18-冠-6(1.3g,0.50mmol)的混合物溶解于二甲基甲酰胺(DMF,100mL)中。所得的溶液在氮气气氛下回流24小时。在反应完成之后，将反应混合物冷却至室温。将该反应混合物倒入300mL的水中，并随后将200mL的二氯甲烷加入其中。将该混合物剧烈搅拌并过滤。分离有机层，以Na2SO4干燥，蒸发以得到棕色固体，加入少量(50mL)丙酮，搅拌并过滤，得到浅棕色固体。将该固体溶于乙酸乙酯(ethyl acetate EA)中，通过重结晶纯化以产生标题化合物，其为浅棕色微晶。将滤液浓缩并在室温下静置以获得较大量的产物(总产率：26g,76.2％)。
1H-NMR(δ,ppm),CDCl3:8.20(d,2H),8.15(d,2H),7.70(d,2H),7.49-7.41(m,4H),7.31(t,2H),2.31(t,2H),1.80(m,2H),1.29(t,3H)
步骤2：1-(4-(3-硝基-9H-咔唑-9-基)苯基)丁-1-酮(1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)butan-1-one)的合成
将步骤1中制备的化合物(10g,29.3mmol)的二氯甲烷(60mL)溶液在0℃下搅拌，然后滴加溶于乙酸(30mL)及乙酸酐(60mL)的混合物的Cu(NO3)2·2.5H2O(7.49g,32.2mmol)溶液。将所得混合物在室温下搅拌1小时。将反应混合物倒入蒸馏水(400mL)中，得到沉淀物。通过过滤收集该沉淀物，使用水充分地洗涤，并在空气中干燥。通过从乙酸乙酯中重结晶来纯化粗产物。为了≥98％的更高的纯度，使用己烷/乙酸乙酯(4:1)作为洗脱液，通过硅胶柱层析法纯化重结晶产物，得到标题化合物，其为黄色固体(8.8g,77.8％)。
1H-NMR(δ,ppm),CDCl3:9.06(d,1H),8.35-8.21(m,3H),7.70(d,2H),7.56-7.43(m,5H),2.69(t,2H),1.82(m,2H),1.31(t,3H)
步骤3：2-(羟基亚胺基)-1-(4-(3-硝基-9H-咔唑-9-基)苯基)丁-1-酮(2-(hydroxyimino)-1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)butan-1-one)的合成
将步骤2中所获得的化合物(5g,12.9mmol)溶解于二氯甲烷(30mL)中，然后于其中加入硝酸异戊酯(isopentyl nitrate,IPN)(1.81g,15.5mmol)。将该混合物于室温中搅拌12小时。通过HCl(0.12g,3.22mmol)的添加停止反应。将100mL的蒸馏水倒入该反应混合物中，并于其中加入100mL的乙酸乙酯(EA)。使用分液漏斗分离有机层，并使用蒸馏水(100mL)洗涤三次以除去杂质。将有机层用Na2SO4干燥，并使用旋转蒸发器除去溶剂，得到象牙色固体。使用蒸馏水洗涤该固体，在60℃下真空干燥过夜，得到标题化合物，产率为76.6％。
1H-NMR(δ,ppm),DMSO-d6:11.20(s,1H),9.30(d,1H),8.32(dd,1H),8.21(d,1H)(m,1H),8.00(d,1H),7.70(d,1H),7.60-7.50(m,2H),7.47-7.42(m,2H),2.52(q,2H),1.34(t,3H)
步骤4：2-(乙酰氧基亚胺基)-1-(4-(3-硝基-9H-咔唑-9-基)苯基)丁-1-酮(2-(acetoxyimino)-1-(4-(3-nitro-9H-carbazol-9-yl)phenyl)butan-1-one)的合成
将步骤3中得到的化合物(3.0g,7.22mmol)溶解在用铝箔保护不受光照的反应烧瓶中的二氯甲烷(20mL)中，然后于其中加入三乙胺(1mL)。在0-5℃连续搅拌下将乙酰氯(1.13g,14.4mmol)滴加至该混合物中。在添加完成后，将所得的混合物在室温下搅拌过夜。将该反应混合物倒入蒸馏水中。搅拌大约10分钟后，将所得的黄色固体过滤、于空气中干燥并从二氯甲烷/甲醇(1/4)中重结晶以获得式1-28的最终肟酯，其为黄色结晶固体(产率：75％)。分离及纯化程序在黄色室中进行，使其免于遭受≤420nm的光线的照射，因为肟酯在暴露于光照时倾向于分解。
1H-NMR(δ,ppm),CDCl3:9.06(s,1H),8.32(d,1H),8.20(d,1H),8.04(d,2H),7.60(d,2H),7.51(t,1H),7.43-7.38(m,3H),2.35(s,3H),2.32(q,2H),1.32(t,3H)
实施例29-33
除了使用相对应的反应物之外，表5中所示的化合物以与实施例28相同的方式合成。
表5
可自BASF在商业上购得的OXE-01及OXE-02分别被制备，以作为比较例3及4的光起始剂。
<附加的实施例1-33及附加的比较例1-4>
透明抗蚀组合物及黑色抗蚀组合物使用实施例1-33及比较例1-4的化合物，通过下列各个步骤制备。
<透明抗蚀组合物>
将17g的丙烯酸粘合剂树脂、13.6g的二新戊四醇六丙烯酸酯(dipentaerythritolhexaacrylate)、1.5g的实施例1-33及比较例1-4的各种化合物、67g的丙二醇单乙醚(propylene glycol monoethyl ether)及500ppm的表面活性剂(FC-430,3M)充分搅拌，以制备透明光敏抗蚀组合物。
<黑色抗蚀组合物>
将30g的碳黑、20g的泰坦黑、13g的聚酯粘合剂树脂、10g的二新戊四醇六丙烯酸酯、2.5g的实施例1-33及比较例1-4的各种化合物、300g的丙二醇单乙醚及500ppm表面活性剂(FC-430,3M)混合在一起，以制备黑色光敏抗蚀组合物。
<物理特性的评价>
如下所述，评价透明光敏抗蚀组合物。
将每一种光敏组合物以800-900rpm在4英寸的圆形玻璃上旋涂15秒，并在热板上以90℃的温度干燥100秒。作为光源的超高压汞灯通过预定的光掩膜将该涂层曝光，通过在25℃下喷雾0.04％氢氧化钾溶液60秒来显影，并用水洗涤以清洁其表面。
经干燥后，该涂层在230℃下烘烤40分钟，以获得图案。该组合物的物理特性通过下列的各别程序评价。其结果显示于表6及图1。
(1)粘着性
在以网格的形式刻画出交叉切口后，使用赛璐玢带(cellophane tape)进行剥离试验。观察交叉切口的剥离状态。当没有交叉切口被剥离时，粘着性被判定为“○”，当一个或多个交叉切口剥离时，粘着性被判定为“X”。
(2)敏感度
将每一种光聚合组合物在4英寸的圆形玻璃上旋涂，并以100℃的温度干燥90秒。作为光源的超高压汞灯通过具有不同透光度的图案化的光掩膜将该涂层曝光，通过在25℃下喷雾0.04％氢氧化钾溶液60秒来显影，并用水洗涤以清洁其表面。使用接触型厚度计测定显影前后的各个图案的厚度。敏感度被定义为显影后图案涂层的厚度达到显影前涂层厚度的80％的曝光剂量。
(3)残膜比
将每一种光聚合组合物在4英寸的圆形玻璃上旋涂，并以100℃的温度干燥90秒。通过具有不同透光度的图案化的光掩膜将该涂层曝光，通过在25℃下喷雾0.04％氢氧化钾溶液60秒来显影，并用水洗涤以清洁其表面。使用接触型厚度计测定显影前后的各个图案的厚度。残膜比定义为显影后的涂层的厚度与显影前的涂层厚度的比(％)。
(4)图案稳定性
在硅芯片上形成每一种光聚合组合物的孔图案。在垂直方向上切割孔图案，并且在电子显微镜下观察图案的横截面。当图案的侧壁相对于基板在55°的角度没有膜损失时，图案稳定性被判定为“○”，当观察到膜损失时，图案稳定性被判定为“X”。
(5)耐化学性
将每一种光聚合组合物在硅芯片上旋涂，随后进行一系列的预烘烤、曝光、显影及后烘烤，以形成抗蚀膜。将抗蚀膜在40℃下浸渍在剥离溶液(stripper solution)中10分钟。研究抗蚀膜的透光率率及厚度的变化。当透光率及厚度变化<2％时，耐化学性被判定为“○”，以及当透光率及厚度变化≥2％时，耐化学性被判定为“X”。
(6)白化
将每一种光聚合组合物在基材上旋涂，随后预烘烤以形成膜。当膜的表面干净没有结晶时，耐白化性被判定为“○”，当膜结晶且涂层表面非常不均匀时为“X”，以及当膜结晶且其表面在曝光及显影后变得混浊时为“△”。
表6
从表6及图1的结果可以看出，作为光聚合组合物的光聚合引发剂的本发明的肟酯苯基咔唑化合物即使少量使用也具有高灵敏度，在残膜比、图案稳定性及耐化学性方面表现出优异的物理性能。此外，使用本发明的肟酯苯基咔唑化合物所形成的薄膜没有发生白化。总之，由于其优异的特性，使用本发明的肟酯苯基咔唑化合物可以最大限度地减少产生用于显示器如TFT-LCD、OLED及TSP的抗蚀剂的曝光及后烘烤过程中的除气的发生。这降低了污染的可能性，因此最大限度地减少缺陷的数量。
Claims (15)
1.一种肟酯苯基咔唑化合物，其作为用于光交联中的光起始剂，其特征在于，与肟酯部分中的氮原子形成双键的碳原子键结至苯基咔唑基团，且直接键结至(C1-C20)烷基或(C6-C20)芳基基团，且其中该苯基咔唑基团被一个或多个硝基取代。
2.如权利要求1所述的肟酯苯基咔唑化合物，其特征在于，该苯基咔唑基团被一个或二个硝基取代。
3.一种肟酯苯基咔唑化合物，其特征在于，所述肟酯苯基咔唑化合物是由式1所表示的：
其中R1及R2各自独立地为氢、硝基、氰基、烷氧基或卤素，条件为R1及R2不同时为氢，R3为(C1-C20)烷基、(C6-C20)芳基、(C1-C20)烷氧基、(C6-C20)芳基(C1-C20)烷基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基、(C1-C20)烷基酰基或(C6-C20)芳基酰基，R4为(C1-C20)烷基、(C6-C20)芳基、(C1-C20)烷氧基、(C6-C20)芳基(C1-C20)烷基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基、(C1-C20)烷基酰基或(C6-C20)芳基酰基；R5及R6各自独立地为氢、(C1-C20)烷基、(C1-C20)烷氧基、羟基(C1-C20)烷基、羟基(C1-C20)烷氧基(C1-C20)烷基、(C3-C20)环烷基或(C1-C20)烷基酰基，以及n为0或1的整数。
4.如权利要求3所述的肟酯苯基咔唑化合物，其特征在于，式1中的R1及R2各自独立地为氢、硝基、氰基、烷氧基或卤素，条件为R1及R2之一者为硝基。
5.如权利要求3所述的肟酯苯基咔唑化合物，其特征在于，式1中的R3为(C3-C7)烷基或(C6-C7)芳基。
6.如权利要求3所述的肟酯苯基咔唑化合物，其特征在于，式1中的R4为(C1-C3)烷基或(C6-C8)芳基。
7.如权利要求3所述的肟酯苯基咔唑化合物，其特征在于，式1中的R5及R6各自独立地为氢或(C1-C2)烷基。
8.一种光聚合起始剂，其特征在于，包含如权利要求1或3所述的肟酯苯基咔唑化合物。
9.一种光聚合组合物，其特征在于，包含如权利要求1或3所述的肟酯苯基咔唑化合物以及至少一个选自可溶于溶剂或碱性水溶液的聚合化合物及具有乙烯性不饱和键的光聚合化合物的化合物。
10.一种光聚合组合物，其特征在于，包含如权利要求1或3所述的肟酯苯基咔唑化合物、至少一个选自可溶于溶剂或碱性水溶液的聚合化合物及具有乙烯性不饱和键的光聚合化合物的化合物以及染剂或色素。
11.一种黑色矩阵，其特征在于，所述黑色矩阵是由如权利要求9所述的光聚合组合物所形成的。
12.一种滤色器，其特征在于，所述滤色器是由如权利要求9所述的光聚合组合物所形成的。
13.一种基材，其特征在于，具有由如权利要求9所述的光聚合组合物所形成的有机绝缘膜。
14.一种基材，其特征在于，具有由涂布如权利要求9所述的光聚合组合物所形成的膜。
15.如权利要求14所述的基材，其特征在于，该膜是显示面板。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101321727A (zh) * | 2005-12-01 | 2008-12-10 | 西巴控股有限公司 | 肟酯光敏引发剂 |
| CN101687794A (zh) * | 2007-05-11 | 2010-03-31 | 巴斯夫欧洲公司 | 肟酯光引发剂 |
| KR20130010621A (ko) * | 2011-07-19 | 2013-01-29 | (주)경인양행 | 옥심 에스테르 화합물 및 그것을 포함하는 광중합 개시제 |
| CN103998427A (zh) * | 2011-12-07 | 2014-08-20 | 巴斯夫欧洲公司 | 肟酯光敏引发剂 |
| JP2015001654A (ja) * | 2013-06-17 | 2015-01-05 | 東レ株式会社 | 積層樹脂ブラックマトリクス基板の製造方法 |
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| KR101808818B1 (ko) * | 2014-11-12 | 2017-12-13 | 주식회사 삼양사 | 액정디스플레이 패널용 블랙매트릭스 포토레지스트 조성물 |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101321727A (zh) * | 2005-12-01 | 2008-12-10 | 西巴控股有限公司 | 肟酯光敏引发剂 |
| CN101687794A (zh) * | 2007-05-11 | 2010-03-31 | 巴斯夫欧洲公司 | 肟酯光引发剂 |
| KR20130010621A (ko) * | 2011-07-19 | 2013-01-29 | (주)경인양행 | 옥심 에스테르 화합물 및 그것을 포함하는 광중합 개시제 |
| CN103998427A (zh) * | 2011-12-07 | 2014-08-20 | 巴斯夫欧洲公司 | 肟酯光敏引发剂 |
| JP2015001654A (ja) * | 2013-06-17 | 2015-01-05 | 東レ株式会社 | 積層樹脂ブラックマトリクス基板の製造方法 |
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