CN101370772B - Diketooxime ester compound and use thereof - Google Patents
Diketooxime ester compound and use thereof Download PDFInfo
- Publication number
- CN101370772B CN101370772B CN2007800030236A CN200780003023A CN101370772B CN 101370772 B CN101370772 B CN 101370772B CN 2007800030236 A CN2007800030236 A CN 2007800030236A CN 200780003023 A CN200780003023 A CN 200780003023A CN 101370772 B CN101370772 B CN 101370772B
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- Prior art keywords
- compound
- ester
- group
- acid
- methyl
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- -1 ester compound Chemical class 0.000 title claims description 445
- 150000001875 compounds Chemical class 0.000 claims abstract description 406
- 239000002585 base Substances 0.000 claims description 179
- 239000000203 mixture Substances 0.000 claims description 125
- 239000007870 radical polymerization initiator Substances 0.000 claims description 86
- 239000003795 chemical substances by application Substances 0.000 claims description 66
- 238000009833 condensation Methods 0.000 claims description 40
- 230000005494 condensation Effects 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 36
- 230000001235 sensitizing effect Effects 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 17
- 229920002120 photoresistant polymer Polymers 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000005023 xylyl group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 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 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- KBWZTOAYWHAYJX-UHFFFAOYSA-N butylperoxycyclohexane Chemical compound CCCCOOC1CCCCC1 KBWZTOAYWHAYJX-UHFFFAOYSA-N 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 220
- 239000000243 solution Substances 0.000 description 107
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 83
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 62
- 230000000052 comparative effect Effects 0.000 description 61
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
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- 239000001301 oxygen Substances 0.000 description 52
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 41
- 238000001953 recrystallisation Methods 0.000 description 38
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- 125000004432 carbon atom Chemical group C* 0.000 description 33
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 30
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- 239000002904 solvent Substances 0.000 description 25
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- 125000004423 acyloxy group Chemical group 0.000 description 16
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 15
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 125000002252 acyl group Chemical group 0.000 description 14
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- 239000006185 dispersion Substances 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 14
- 239000012530 fluid Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 12
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- 125000004104 aryloxy group Chemical group 0.000 description 11
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- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical group ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
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- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 7
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- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- BMJHTFWPTJVYJV-UHFFFAOYSA-N trimethyl(pent-2-en-3-yloxy)silane Chemical group CCC(=CC)O[Si](C)(C)C BMJHTFWPTJVYJV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/68—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- 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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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C08F4/00—Polymerisation catalysts
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
Disclosed is a compound represented by the following general formula (1). (1) In the formula, A and B independently represent a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed polycyclic hydrocarbon group, provided that A and B are not condensed polycyclic hydrocarbon groups substituted by a methoxy group at the same time; and X represents a monovalent organic residue.
Description
Technical field
The present invention relates to the diketone oxime ester compound and use radical polymerization initiator, photopolymerizable composition and the picture pattern of this compound.More specifically, the present invention relates to moulding resin, cast resin, light chisel with resin, sealing agent, dental polymer resin, printing-ink, coating, press plate with photoresist, printing with color proof, colour filter with resist, black matrix with resist, liquid crystal with light sensitive spacer, rear projection with screen material, optical fiber, plasma display with timber, dry film photoresist, printed base plate with resist, scolder resist, semi-conductor with photo-resist, microelectronics with the parts manufacturing of resist, micromachine with resist, etching with resist, microlens array, insulating material, hologram material, optical converter, waveguide with material, outer coating agent, powder coated dose, caking agent, tackiness agent, releasing agent, optical recording medium, glue solid, release-coated agent, used radical polymerization initiator, photopolymerizable composition and the picture pattern of the image recording material of microcapsule with the employing of fields such as compsn, various devices.
Background technology
To have the function of light trigger be known (with reference to non-patent literature 1, patent documentation 1,2) to certain oxime ester compound in the past.In addition, with the optical free radical polymerization starter of compsn alpha-ketoxime ester cpds (with reference to patent documentation 3) is disclosed as the photosensitive polyimide presoma of plus or minus type.Certain α is also disclosed, α '-diketone oxime ester compound (with reference to patent documentation 4~8).Certain adjacent acyl group oxime ester compound (with reference to patent documentation 9~11) is further disclosed.These compounds all have the function of polymerization starter, but in recent years for the raising of tackling productivity and the various technologies that newly propose, pursue the high sensitiveization of polymerization starter at large.
In addition, in various fields, adopted the photo-resist method of using photoresist in recent years.The photo-resist method adopts following method usually: form photo-sensitive resin at the substrate surface that desired image will be set through coating or from other base material transfer printings; Follow this photo-sensitive resin across former figure irradiation energy ray; Utilize solvent or alkaline aqueous solution to remove unexposed portion after the exposure, thereby form corresponding image with this former figure by development treatment.About utilizing the example of this photo-resist method, certain negative resist is disclosed as being used to form the material (with reference to patent documentation 12~14) of image display with gap.Also disclose certain negative resist as the electrical and electronic parts manufacturing with, printed base plate manufacturing with material (with reference to patent documentation 15~17).Have the resist compsn of certain adjacent acyl group oxime ester as more high sensitive resist compsn is known recently, and disclose certain negative resist as being used to form the material (with reference to patent documentation 18) of image display with gap as Photoepolymerizationinitiater initiater.In addition, also disclose certain negative resist as the electrical and electronic parts manufacturing with, printed base plate manufacturing with material (with reference to patent documentation 19).These resists are all as resist compsn performance function; But the raising and the new various technologies that propose in order to tackle productivity in recent years; The resist compsn is more and more required to have high function and new function; Particularly require more high sensitive resist compsn, and carrying out the exploitation of various resist compsns energetically.
Non-patent literature 1:European Polymer Journal, 1970,6,933-943
Patent documentation 1: USP the 3rd, 558, No. 309 specification sheetss
Patent documentation 2: USP the 4th, 255, No. 513 specification sheetss
Patent documentation 3: japanese kokai publication hei 7-140, No. 658 communiques
Patent documentation 4: USP the 5th, 019, No. 482 specification sheetss
Patent documentation 5: japanese kokai publication sho 62-184, No. 056 communique
Patent documentation 6: japanese kokai publication sho 62-273, No. 259 communiques
Patent documentation 7: japanese kokai publication sho 62-286, No. 961 communiques
Patent documentation 8: japanese kokai publication sho 62-201, No. 859 communiques
Patent documentation 9: TOHKEMY 2001-233, No. 842 communiques
Patent documentation 10: TOHKEMY 2000-80, No. 068 communique
Patent documentation 11: Japan special table 2004-534, No. 797 communiques
Patent documentation 12: japanese kokai publication hei 11-174464 communique
Patent documentation 13: TOHKEMY 2001-226449 communique
Patent documentation 14: TOHKEMY 2002-341531 communique
Patent documentation 15: japanese kokai publication hei 10-198033 communique
Patent documentation 16: TOHKEMY 2002-236362 communique
Patent documentation 17: TOHKEMY 2002-249644 communique
Patent documentation 18: TOHKEMY 2001-261761 communique
Patent documentation 19: TOHKEMY 2001-302871 communique
Summary of the invention
The problem that invention will solve
The solidification compound that the purpose of a scheme of the present invention is that high sensitive radical polymerization initiator is provided and uses this initiator; Said initiator through the irradiation energy ray particularly light can produce living radical effectively, and make free-radical polymerised compound generation polymerization at short notice.For example industriallization is provided at printing ink, coating, photosensitive printing plate, proof material, resist, hologram material, sealing agent, outer coating material, light chisel with fields such as resin, caking agent practical oligopolymer and polymkeric substance, and radical polymerization initiator that the cured article that obtains having superperformance uses and the photopolymerizable composition that uses this initiator are provided.And then the purpose of a scheme of the present invention is to provide the radical polymerization initiator of excellent storage stability.
The method of dealing with problems
A scheme of the present invention relates to the compound of formula (1).
[changing 1]
In the formula, A and B represent replacement or unsubstituted heterocyclic respectively independently, or replace or unsubstituted condensation polycyclic alkyl.But do not comprise that A and B were by the substituted condensation polycyclic alkyl of methoxyl group when A was identical with B.X representes the organic residue of univalent.A and B can be the same or different.A is preferably and replaces or unsubstituted carbazyl, or replace or unsubstituted naphthyl, more preferably replaces or the group of unsubstituted formula (2) expression, or replaces or the group of unsubstituted formula (3) expression.
[changing 2]
[changing 3]
general formula (3)
(Y representes the organic residue of univalent in the general formula (2).)
In addition, preferred A is the group of replacement or unsubstituted general formula (2) expression, and B is the group that replaces or unsubstituted general formula (3) is represented.
In the group that the substituting group of heterocyclic radical and condensation polycyclic alkyl is preferably selected from is amino by hydroxyl, sulfydryl, cyanic acid, nitro, halogen atom, alkyl, aryl, heterocyclic radical, acyl group, aryloxy, heterocyclic oxy group, acyloxy, alkylthio, arylthio, heterocycle sulfenyl, amino, alkylamino, dialkyl amido, virtue amino, ammonia diaryl base, alkyl virtue amino, benzyl, dibenzyl amino and alkoxyl group form.
In addition, a scheme of the present invention relates to the radical polymerization initiator that comprises above-claimed cpd.
And then a scheme of the present invention relates to the photopolymerizable composition that comprises this radical polymerization initiator and free-radical polymerised compound.Photopolymerizable composition can further comprise alkali soluble resins and/or sensitizing agent.
And then a scheme of the present invention relates to the negative resist that comprises photopolymerizable composition.
And then a scheme of the present invention relates to a kind of formation method of picture pattern, it is characterized in that, at the folded negative resist of layers on substrates, partly the irradiation energy ray makes its curing, removes non-irradiated part through alkaline-based developer.
And then a scheme of the present invention relates to the picture pattern that method forms that forms by this picture pattern.
The effect of invention
Compound of the present invention is α, and α '-diketone oxime ester compound is characterized in that having heterocyclic radical or condensation polycyclic alkyl in 1-position and 3-position.Compound of the present invention has the function of radical polymerization initiator, through the irradiation energy ray particularly light can produce living radical effectively.Thereby,, the compound that has as the remarkable good result of the radical polymerization initiator of polymerizability material can be provided according to the present invention.And,, the solidification compound with superperformance can be provided through using this compound as radical polymerization initiator.
That is to say that a scheme according to the present invention can provide effective real estate to give birth to the radical polymerization initiator of radical.And a scheme according to the present invention can be provided in can the polymeric photopolymerizable composition in the short period of time.And then a scheme according to the present invention can provide susceptibility good photopolymerizable composition.And then a scheme according to the present invention can provide the photopolymerizable composition of excellent storage stability.
In addition; Disclosed content is willing to that with the special 2006-005881 of hope, the special 2006-194241 of hope, spy 2006-019294, the special 2006-019293 of hope, special hope 2006-034037, the special 2006-199929 of hope, the special 2006-034038 of hope and spy are willing to that the theme of 2006-033971 is relevant in this specification sheets, and the content that discloses in these documents all is introduced in this specification sheets.
Embodiment
At first describe to compound of the present invention.Compound of the present invention is characterised in that the structure with above-mentioned general formula (1) expression.A and B can be the same or different in general formula (1).A and B represent heterocyclic radical or condensation polycyclic alkyl respectively independently.Heterocyclic radical and condensation polycyclic alkyl can be substituted, and also can not be substituted.But do not comprise A and B combination by the substituted condensation polycyclic alkyl of methoxyl group.
Can enumerate aromatic series or the aliphatic heterocyclic radical that comprises nitrogen-atoms, Sauerstoffatom, sulphur atom or phosphorus atom as the heterocyclic radical in the general formula (1).Can enumerate 2-thienyl, 2-benzothienyl, naphthalene [2 as concrete example; 3-b] thienyl, 3-thienyl, 2-thienyl, 2-furyl, 2-benzofuryl, pyranyl, isobenzofuran-base, chromenyl, xanthenyl, phenothioxin base (Phenoxathiinyl), 2H-pyrryl, pyrryl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, indolizinyl, pseudoindoyl, 3H-indyl, 2-indyl, 3-indyl, 1H-indazolyl, purine radicals, 4H-quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolyl, cinnolines base, pteridyl, 4aH-carbazyl, 2-carbazyl, 3-carbazyl, β-Ka Lin base, phenanthridinyl, 2-acridyl, perimidinyl, phenanthrolinyl, phenazinyl, phenarsazine base, isothiazolyl, phenothiazinyl, isoxazolyl, furazan base, 3-phenoxazinyl, different chromanyl, chromanyl, pyrrolidyl, pyrrolinyl, imidazolidyl, imidazolinyl, pyrazolidyl, pyrazolinyl, piperidyl, piperazinyl, indolinyl, isoindolinyl, quinuclidinyl, morpholinyl, thioxanthene base, 4-quinolyl, 4-isoquinolyl, 3-phenothiazinyl, 2-phenothioxin base, 3-benzofuryl, dibenzofuran group, coumaran base, 2-sulfo-benzofuryl, xanthene ketone group, dibenzo thienyl, thioxanthene base, oxazolyl, benzoxazolyl, benzothiazolyl, 1; 4-two sulphur naphthyls etc., but be not limited to these.In addition, also can combine at the position of substitution beyond above-mentioned, so long as can form the position of substitution of covalent linkage with carbon atom, not special restriction with the carbon atom of general formula (1).Can enumerate as preferred heterocyclic radical that Wasserstoffatoms is substituted or unsubstituted carbazyl.Be specially the replacement or the unsubstituted carbazyl of general formula (2) expression.The Y of general formula (2) representes the organic residue of univalent, can be with after the identical organic residue of the organic residue of monovalence in the substituent X stated.From easy acquisition raw material, synthetic consideration easily, preferably replace or unsubstituted alkyl as organic residue Y.
Can enumerate the condensation polycyclic alkyl that forms ring structure by 7 above carbon atoms as the condensation polycyclic alkyl in the general formula (1).Can enumerate indenyl, 1 as concrete example; 3-indane dione-base, naphthyl, β-tetralin ketone group, α-Nai Kuilin base, pentalene base, camomile cyclic group and cycloheptadiene base, fluorenyl, Fluorenone base, anthryl, 9 (10H)-anthrone base, anthraquinonyl (anthracenequinonyl), anthraquinonyl (anthraquinonyl), phenanthryl, 9; 10-phenanthrenequione base, diphenylene, s-benzo two indenyls, as-benzo two indenyls, acenaphthylenyl, acenaphthenyl, acenaphthenequinone base, non-that thiazolinyl (Phenalenyl), naphthacene base, 1,2-benzo phenanthryl, pyrenyl, three diphenylenes, benzo [a] anthryl, benzo [a] anthraquinonyl, aceanthrylenyl, aceanthrenyl, aceanthrene quinonyl, acephenanthrylenyl, fluoranthenyl, seven days of the week thiazolinyl, pentacene base, perylene base, picene base, benzo [a] pyrenyl etc.Wherein, owing to obtain easily, reason that the synthetic difficulty is low etc., preferred number of rings is 2 or 3 condensation polycyclic alkyl, but is not limited to this.In addition, can combine at any the position of substitution, so long as can form the position of substitution of covalent linkage with carbon atom, not special restriction with the carbon atom of general formula (1).Can enumerate as preferred condensation polycyclic alkyl that Wasserstoffatoms is substituted or unsubstituted naphthyl.Represent by general formula (3) particularly.
The substituting group that can have as above-mentioned heterocyclic radical and condensation polycyclic alkyl can enumerate that hydroxyl, sulfydryl, cyanic acid, nitro, halogen atom, alkyl, aryl, heterocyclic radical, acyl group, alkoxyl group, aryloxy, heterocyclic oxy group, acyloxy, carbalkoxy, alkylthio, arylthio, heterocycle sulfenyl, amino, alkylamino, dialkyl amido, virtue amino, ammonia diaryl base, alkyl virtue amino, benzyl are amino, dibenzyl amino etc.
Wherein, Owing to reasons such as the low and easy acquisitions of synthetic difficulty, preferably enumerate cyanic acid, nitro, alkyl, aryl, heterocyclic radical, acyl group, alkoxyl group, aryloxy, heterocyclic oxy group, alkylthio, arylthio, heterocycle sulfenyl, dialkyl amido, ammonia diaryl base.More preferably enumerate alkyl, aryl, acyl group, aryloxy, alkylthio, arylthio, dialkyl amido, ammonia diaryl base.
In addition, at least more than one of heterocyclic radical and condensation polycyclic alkyl can be replaced by the substituting group of formula (4) expression.In the general formula (4) Z represent direct combination ,-O-,-S-,-NR '-,-CO-,-COO-,-OCO-.R and R ' represent alkyl, aryl, heterocyclic radical respectively independently.When these were imported heterocyclic radical with the condensation polycyclic alkyl by general formula (4) expression substituent more than 1, though its reason is not clear now, the pattern that is to use photopolymerizable composition formation can be improved to the adaptation of substrate.
[changing 4]
-Z-R
General formula (4)
At this, can enumerate fluorine atom, chlorine atom, bromine atoms, iodine atom as halogen atom.
Can enumerate straight chain shape, branched, monocycle or the condensation polycyclic shape alkyl of carbonatoms 1~18 as alkyl.Can enumerate methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, dodecyl, octadecyl, sec.-propyl, isobutyl-, isopentyl, sec.-butyl, the tertiary butyl, sec.-amyl sec-pentyl secondary amyl, tert-pentyl, uncle's octyl group, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norcamphyl, bornyl, 4-decyl cyclohexyl etc. as concrete example.
Can enumerate the monocycle or the condensation polycyclic aryl of carbonatoms 6~18 as aryl.Can enumerate phenyl, 1-naphthyl, 2-naphthyl, 9-anthryl, 9-phenanthryl, 1-pyrenyl, 5-naphthacene base, 1-indenyl, 2-camomile cyclic group, 1-acenaphthenyl, 9-fluorenyl etc. as concrete example.
Can enumerate monocycle or the condensation polycyclic heterocyclic radical that comprises nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom as heterocyclic radical.Can enumerate 2-furyl, 2-thienyl, 2-indyl, 3-indyl, 2-benzofuryl, 2-benzothienyl, 2-carbazyl, 3-carbazyl, 4-carbazyl, 9-acridyl etc. as concrete example.
Can enumerate the aliphatics bonded carbonyl of straight chain shape, branched, monocycle shape or the condensation polycyclic shape of Wasserstoffatoms or carbonatoms 1~18 as acyl group; Perhaps the monocycle shape of carbonatoms 6~18 or condensation polycyclic shape aryl bonded carbonyl perhaps comprise the monocycle shape or the condensation polycyclic shape heterocyclic radical bonded carbonyl of the carbonatoms 4~18 of nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom.These groups can have unsaturated link(age) in structure.Can enumerate formyl radical as concrete example; Ethanoyl; Propionyl group; Butyryl radicals; Isobutyryl; Pentanoyl; Isovaleryl; Pivaloyl group; Lauroyl; Tetradecanoyl; Hexadecanoyl; Stearyl-; Cyclopentylcarbonyl; Cyclohexyl-carbonyl; Acryl; Methacryloyl; Crotonyl; Isocrotonoyl; Oleoyl; Benzoyl-; The 2-methyl benzoyl; The 4-anisoyl; 1-naphthoyl base; 2-naphthoyl base; Cinnamyl; 3-furoyl base; The 2-Thenoyl; Nicotinoyl; Different nicotinoyl; 9-anthracene acyl group; 5-naphthacene acyl group etc.
Can enumerate straight chain shape, branched, monocycle shape or the condensation polycyclic shape alkoxyl group of carbonatoms 1~50 as alkoxyl group.Can enumerate methoxyl group as concrete example; Oxyethyl group; Propoxy-; Butoxy; Pentyloxy; Hexyloxy; Heptan the oxygen base; Octyloxy; The ninth of the ten Heavenly Stems oxygen base; The last of the ten Heavenly stems oxygen base; Dodecyloxy; Octadecane oxygen base; Isopropoxy; Isobutoxy; Isopentyloxy; Sec.-butoxy; Tert.-butoxy; Secondary pentyloxy; Uncle's pentyloxy; Uncle's octyloxy; Neopentane oxygen base; Cyclopropyl oxygen base; Cyclobutyl oxygen base; Cyclopentyloxy; Cyclohexyl oxygen base; The Buddha's warrior attendant alkoxyl group; Norborneol oxygen base; Borneol oxygen base; 4-decyl cyclohexyl oxygen base; 2-tetrahydrofuran oxygen base; 2-tetrahydrofuran oxygen base etc.Owing to improving, be preferably the alkoxyl group of carbonatoms 2~30, more preferably the alkoxyl group of carbonatoms 2~20 in the photopolymerizable composition and reasons such as the solvability of the solvent of usefulness and resin etc., storage stability.
Can enumerate the monocycle shape or the condensation polycyclic shape aryloxy of carbonatoms 6~18 as aryloxy.Can enumerate phenoxy, 1-naphthyloxy, 2-naphthyloxy, 9-anthracene oxygen base, the luxuriant and rich with fragrance oxygen base of 9-, 1-pyrene oxygen base, 5-naphthacene oxygen base, 1-indenes oxygen base, 2-camomile epoxy group(ing), 1-acenaphthene oxygen base, 9-fluorenes oxygen base etc. as concrete example.
Can enumerate monocycle shape or the condensation polycyclic shape heterocyclic oxy group that comprises nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom as heterocyclic oxy group.Can enumerate 2-furans oxygen base, 2-thiophene oxy, 2-indoxyl, 3-indolol, 2-cumarone oxygen base, 2-thionaphthene oxygen base, 2-carbazole oxygen base, 3-carbazole oxygen base, 4-carbazole oxygen base, 9-acridine oxygen base etc. as concrete example.
Can enumerate the aliphatics bonded carbonyl oxygen base of straight chain shape, branched, monocycle shape or the condensation polycyclic shape of Wasserstoffatoms or carbonatoms 1~18 as acyloxy; Perhaps the monocycle shape of carbonatoms 6~18 or condensation polycyclic shape aryl bonded carbonyl oxygen base perhaps comprise the monocycle shape or the condensation polycyclic shape heterocyclic radical bonded carbonyl oxygen base of the carbonatoms 4~18 of nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom.Can enumerate acetoxyl group as concrete example; Propionyloxy; Butyryl acyloxy; The isobutyl acyloxy; Penta acyloxy; The isoamyl acyloxy; Pivaloyl oxygen base; The bay acyloxy; Tetradecane acyl-oxygen base; N-Hexadecane acyl-oxygen base; Stearoyl-oxy; Cyclopentyl carbonyl oxygen base; Cyclohexyl carbonyl oxygen base; Acryloxy; Methacryloxy; The crotons acyloxy; Different crotons acyloxy; The oil acyloxy; Benzoyloxy; The 1-Naphthoyloxy; The 2-Naphthoyloxy; The cassia bark acyloxy; 3-chaff acyloxy; 2-thenoyl oxygen base; Nicotinylsalicylic oxygen; Different nicotinylsalicylic oxygen; 9-anthracene acyloxy; 5-naphthacene acyloxy etc.
Can enumerate the carbalkoxy of carbonatoms 2~20 as carbalkoxy.Can enumerate methoxycarbonyl, ethoxycarbonyl, the third oxygen carbonyl, butoxy carbonyl, own oxygen carbonyl, hot oxygen carbonyl, last of the ten Heavenly stems oxygen carbonyl, octadecane oxygen carbonyl, carbobenzoxy, trifluoro methoxycarbonyl, 1-naphthalene oxygen carbonyl, 2-naphthalene oxygen carbonyl etc. as concrete example.
Can enumerate straight chain shape, branched, monocycle shape or the condensation polycyclic shape alkylthio of carbonatoms 1~18 as alkylthio.Can enumerate methylthio group, ethylmercapto group, rosickyite base, butylthio, penta sulfenyl, own sulfenyl, hot sulfenyl, last of the ten Heavenly stems sulfenyl, dodecyl sulfenyl, octadecane sulfenyl etc. as concrete example.
Can enumerate the monocycle shape or the condensation polycyclic shape arylthio of carbonatoms 6~18 as arylthio.Can enumerate thiophenyl, 1-naphthalene sulfenyl, 2-naphthalene sulfenyl, 9-anthracene sulfenyl, the luxuriant and rich with fragrance sulfenyl of 9-etc. as concrete example.
Can enumerate monocycle shape or the condensation polycyclic shape heterocycle sulfenyl that comprises nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom as the heterocycle sulfenyl.Can enumerate 2-furans sulfenyl, 2-thiophene thio, 2-pyrroles's sulfenyl, 6-indoles sulfenyl, 2-cumarone sulfenyl, 2-thionaphthene sulfenyl, 2-carbazole sulfenyl, 3-carbazole sulfenyl, 4-carbazole sulfenyl etc. as concrete example.
Can enumerate methylamino-as alkylamino; Ethylamino; Third amino; Fourth is amino; Penta amino; Oneself is amino; Heptan is amino; Hot amino; The ninth of the ten Heavenly Stems is amino; The last of the ten Heavenly stems is amino; Dodecyl is amino; Octadecyl is amino; Isopropylamino; Isobutyl is amino; Isoamylamino; Zhong Ding is amino; Uncle's fourth is amino; Secondary penta amino; Uncle's penta amino; Uncle is hot amino; New penta amino; Cyclopropylamino; The ring fourth is amino; Encircle penta amino; Hexamethylene is amino; Ring is amino heptan; Ring is hot amino; Cyclo-dodecyl is amino; The 1-adamantyl is amino; 2-adamantyl amino etc.
Can enumerate dimethylamino as dialkyl amido; Diethylamino; Dipropyl is amino; Dibutylamino; Diamyl is amino; Dihexyl is amino; Diheptyl is amino; Dioctyl is amino; Dinonyl is amino; Didecyl is amino; Two (dodecyl) amino; Two (octadecyl) amino; Diisopropylaminoethyl; Diisobutyl is amino; Diisoamyl is amino; Methylethyl is amino; Methyl-propyl is amino; Methylbutyl is amino; Methyl-isobutyl is amino; Cyclopropyl is amino; Pyrryl; Piperidyl; Piperazinyl etc.
As fragrant amino can enumerate phenylamino, 1-naphthylamino, 2-naphthylamino, adjacent toluino, a toluino, to toluino, 2-benzidino-, 3-benzidino-, 4-benzidino-, 1-fluorenes amino, 2-fluorenes amino, 2-thiazole amino, p-terphenyl amino etc.
Can enumerate diphenyl amino, xylyl amino, N-phenyl-1-naphthylamino, N-phenyl-2-naphthylamino etc. as ammonia diaryl base.
Can enumerate N-methylbenzene amino, N-methyl-2-pyridyl, N-ethylbenzene amino, N-propylbenzene amino, N-butylbenzene-amino, N-isopropyl benzene amino, N-amylbenzene amino, N-ethylbenzene amino, N-methyl isophthalic acid-naphthylamino etc. as alkyl virtue amino.
And then the substituent Wasserstoffatoms that above-mentioned heterocyclic radical and condensation polycyclic alkyl can have can also be replaced by other substituting group.Can enumerate for example halogen groups such as fluorine atom, chlorine atom, bromine atoms, iodine atom as this substituting group, alkoxyl groups such as methoxyl group, oxyethyl group, tert.-butoxy, phenoxy,, carbalkoxys such as methoxycarbonyl, butoxy carbonyl, carbobenzoxy to aryloxy such as tolyloxys; Acyloxy such as acetoxyl group, propionyloxy, benzoyloxy, acyl groups such as ethanoyl, benzoyl-, isobutyryl, acryl, methacryloyl, methoxalyl, alkyl alkylthio bases such as methyl sulfane base, tertiary butyl sulfane base, alkylaminos such as methylamino-, hexamethylene amino; Dialkyl amidos such as dimethylamino, diethylamino, morpholinyl, piperidyl, phenylamino, amino, alkyl such as methyl, ethyl, the tertiary butyl, dodecyl, aryl such as phenyl, p-methylphenyl, xylyl, cumyl, naphthyl, anthryl, phenanthryl to virtues such as toluinos; Heterocyclic radical such as furyl, thienyl, hydroxyl, carboxyl; Formyl radical, sulfydryl, sulfo group; Methylsulfonyl, p-toluenesulfonyl, amino; Nitro, cyanic acid, trifluoromethyl; Trichloromethyl, trimethyl silyl, phosphinico-; Phosphoryl (phosphono), trimethylammonium ammonium, dimethyl sulfonium base and triphenyl benzoyl methyl sulfonium base etc.
And then the substituting group among A and the B can be integrated and form ring texture with other substituting groups or ring hydrogen atom.
And A and B also can be integrated and form ring texture.
Substituent X in the general formula (1) is represented the organic residue of univalent.Can enumerate alkyl, aryl, thiazolinyl, alkynyl, alkoxyl group, aryloxy, heterocyclic oxy group, acyloxy, alkyl alkylthio base, sulfur alkyl aryl, alkyl sulphinyl, aryl sulfonyl kia, alkyl sulphonyl, aryl sulfonyl, acyl group, carbalkoxy, formamyl, amino-sulfonyl, amino, phosphono (phosphinoyl), heterocyclic radical as the organic residue of univalent.The organic residue of these monovalencies can have substituting group, also can not have substituting group.
At this, as the alkyl of the preferred carbonatoms 1~30 of alkyl.Can enumerate for example methyl; Ethyl; Propyl group; Butyl; Hexyl; Octyl group; Decyl; Dodecyl; Octadecyl; Sec.-propyl; Isobutyl-; Sec.-butyl; The tertiary butyl; The 1-ethyl pentyl group; Cyclopentyl; Cyclohexyl; Trifluoromethyl; The 2-ethylhexyl; Phenacyl-; 1-naphthoyl methyl; 2-naphthoyl methyl; 4-methyl sulfane base phenacyl-; 4-phenyl sulfane base phenacyl-; 4-dimethylamino phenacyl-; 4-cyanic acid phenacyl-; 4-toluyl methyl; 2-toluyl methyl; 3-fluorobenzoyl methyl; 3-trifluoromethyl benzoyl methyl; 3-oil of mirbane formyl methyl etc.
Aryl as the preferred carbonatoms 6~30 of aryl.For example can enumerate phenyl, xenyl, 1-naphthyl, 2-naphthyl, 9-anthryl, 9-phenanthryl, 1-pyrenyl, 5-naphthacene base, 1-indenyl, 2-camomile cyclic group, 9-fluorenyl, terphenyl, tetrad phenyl, o-tolyl, a tolyl, p-methylphenyl, xylyl, adjacent cumyl, a cumyl, to cumyl, mesitylene base, pentalene base, binaphthylyl, three binaphthylyl, tetrad naphthyl and cycloheptadiene base, diphenylene, benzo two indenyls, fluoranthenyl, acenaphthylenyl, aceanthrylenyl, non-that thiazolinyl, fluorenyl, anthryl, dianthranide base, three dianthranide bases, tetrad anthryl, anthraquinonyl, phenanthryl, three diphenylenes, pyrenyl, 1,2-benzo phenanthryl, naphthacene base, seven days of the week thiazolinyl, picene base, perylene base, pentacene base, tetrad phenylene, hexaphenyl, hexacenyl, rubicenyl, coronenyl, three naphthylidenes, seven phenyl, heptaphenyl, pyranthrene base, join ten phenyl etc.
Thiazolinyl as the preferred carbonatoms 2~10 of thiazolinyl.Can enumerate for example vinyl, allyl group, styryl etc.
Alkynyl as the preferred carbonatoms 2~10 of alkynyl.Can enumerate for example ethynyl, proyl, propargyl etc.
Alkoxyl group as the preferred carbonatoms 1~30 of alkoxyl group.For example can enumerate methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, isobutoxy, sec.-butoxy, tert.-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy, last of the ten Heavenly stems oxygen base, dodecyloxy, octadecane oxygen base, ethoxycarbonylmethyl group, the own oxygen carbonyl of 2-ethyl methoxyl group, aminocarboxyl methoxyl group, N, N-dibutylamino carbonyl methoxyl group, N-amino-carbonyl methoxyl group, N-B aminocarbonyl methoxyl group, the hot aminocarboxyl methoxyl group of N-, N-methyl-N-benzylaminocarbonyl methoxyl group, benzyloxy, cyanic acid methoxyl group etc.
Aryloxy as the preferred carbonatoms 6~30 of aryloxy.Can enumerate for example phenoxy, 1-naphthyloxy, 2-naphthyloxy, 2-chlorophenoxy, 2-methylphenoxy, 2-methoxyl group phenoxy, 2-phenoxy butoxy base, 3-chlorophenoxy, 3-4-trifluoromethylphenopendant, 3-cyano-benzene oxygen, 3-nitro-phenoxy, 4-fluorophenoxy, 4-cyano-benzene oxygen, 4-methoxyl group phenoxy, 4-dimethylamino phenoxyl, 4-methyl sulfane phenoxyl, 4-phenyl sulfane phenoxyl etc.
Can enumerate monocycle shape or the condensation polycyclic shape heterocyclic oxy group that comprises nitrogen-atoms, Sauerstoffatom, sulphur atom, phosphorus atom as heterocyclic oxy group.Can enumerate 2-furans oxygen base, 2-thiophene oxy, 2-indoxyl, 3-indolol, 2-carbazole oxygen base, 2-cumarone oxygen base, 2-thionaphthene oxygen base, 3-carbazole oxygen base, 4-carbazole oxygen base, 9-acridine oxygen base etc. as concrete example.
Acyloxy as the preferred carbonatoms 2~20 of acyloxy.Can enumerate for example acetoxyl group, propionyloxy, butyryl acyloxy, penta acyloxy, trifluoromethyl carbonyl oxygen base, benzoyloxy, 1-naphthyl carbonyl oxygen base, 2-naphthyl carbonyl oxygen base etc.
Alkyl alkylthio base as the preferred carbonatoms 1~20 of alkyl alkylthio base.Can enumerate for example methyl sulfane base, ethyl sulfane base, propylthio alkyl, sec.-propyl sulfane base, butyl sulfane base, hexyl sulfane base, cyclohexyl sulfane base, octyl group sulfane base, 2-ethylhexyl sulfane base, decanoyl sulfane base, lauroyl sulfane base, octadecanoyl sulfane base, cyano methyl sulfane base, methoxymethyl sulfane base etc.
Sulfur alkyl aryl as the preferred carbonatoms 6~30 of sulfur alkyl aryl.Can enumerate for example phenyl sulfane base; 1-naphthyl sulfane base; 2-naphthyl sulfane base; 2-chloro-phenyl-sulfane base; 2-aminomethyl phenyl sulfane base; 2-p-methoxy-phenyl sulfane base; 2-butoxy phenyl sulfane base; 3-chloro-phenyl-sulfane base; 3-trifluoromethyl sulfane base; 3-cyano-phenyl sulfane base; 3-nitrophenyl sulfane base; 4-fluorophenyl sulfane base; 4-cyano-phenyl sulfane base; 4-p-methoxy-phenyl sulfane base; 4-methyl sulfane base phenyl sulfane base; 4-phenyl sulfane base phenyl sulfane base; 4-dimethylaminophenyl sulfane base etc.
Alkyl sulphinyl as the preferred carbonatoms 1~20 of alkyl sulphinyl.Can enumerate for example methylsulfinyl, ethyl sulfinyl, propyl group sulfinyl, sec.-propyl sulfinyl, butyl sulfinyl, hexyl sulfinyl, cyclohexyl sulfinyl, octyl group sulfinyl, 2-ethylhexyl sulfinyl, decanoyl sulfinyl, lauroyl sulfinyl, octadecanoyl sulfinyl, cyano methyl sulfinyl, methoxymethyl sulfinyl etc.
Aryl sulfonyl kia as the preferred carbonatoms 6~30 of aryl sulfonyl kia.Can enumerate for example phenyl sulfinyl; 1-naphthyl sulfinyl; 2-naphthyl sulfinyl; 2-chloro-phenyl-sulfinyl; 2-aminomethyl phenyl sulfinyl; 2-p-methoxy-phenyl sulfinyl; 2-butoxy phenyl sulfinyl; 3-chloro-phenyl-sulfinyl; 3-trifluoromethyl sulfinyl; 3-cyano-phenyl sulfinyl; 3-nitrophenyl sulfinyl; 4-fluorophenyl sulfinyl; 4-cyano-phenyl sulfinyl; 4-p-methoxy-phenyl sulfinyl; 4-methyl sulfane base phenyl sulfinyl; 4-phenyl sulfane base phenyl sulfinyl; 4-dimethylaminophenyl sulfinyl etc.
Alkyl sulphonyl as the preferred carbonatoms 1~20 of alkyl sulphonyl.Can enumerate for example methyl sulphonyl, ethylsulfonyl, sulfonyl propyl base, sec.-propyl alkylsulfonyl, butyl alkylsulfonyl, hexyl alkylsulfonyl, cyclohexyl alkylsulfonyl, octyl group alkylsulfonyl, 2-ethylhexyl alkylsulfonyl, decanoyl alkylsulfonyl, lauroyl alkylsulfonyl, octadecanoyl alkylsulfonyl, cyano methyl alkylsulfonyl, methoxymethyl alkylsulfonyl etc.
Aryl sulfonyl as the preferred carbonatoms 6~30 of aryl sulfonyl.Can enumerate for example phenyl sulfonyl; 1-naphthyl alkylsulfonyl; 2-naphthyl alkylsulfonyl; 2-chloro-phenyl-alkylsulfonyl; 2-aminomethyl phenyl alkylsulfonyl; 2-p-methoxy-phenyl alkylsulfonyl; 2-butoxy phenyl alkylsulfonyl; 3-chloro-phenyl-alkylsulfonyl; 3-trifluoromethyl alkylsulfonyl; 3-cyano-phenyl alkylsulfonyl; 3-nitrophenyl alkylsulfonyl; 4-fluorophenyl alkylsulfonyl; 4-cyano-phenyl alkylsulfonyl; 4-p-methoxy-phenyl alkylsulfonyl; 4-methyl sulfane base phenyl sulfonyl; 4-phenyl sulfane base phenyl sulfonyl; 4-dimethylaminophenyl alkylsulfonyl etc.
Acyl group as the preferred carbonatoms 2~20 of acyl group.Can enumerate for example ethanoyl; Propionyl group; Butyryl radicals; The trifluoromethyl carbonyl; Pentanoyl; Benzoyl-; The 1-naphthoyl; The 2-naphthoyl; 4-methyl sulfane base benzoyl-; 4-phenyl sulfane base benzoyl-; 4-dimethylamino benzoyl-; 4-diethylamino benzoyl-; The 2-chlorobenzene formacyl; The 2-methyl benzoyl; The 2-anisoyl; 2-butyl phenyl ether formyl radical; The 3-chlorobenzene formacyl; 3-trifluoromethyl benzoyl-; 3-cyanic acid benzoyl-; The 3-nitro benzoyl; The 4-fluoro benzoyl; 4-cyanic acid benzoyl-; 4-anisoyl etc.
Carbalkoxy as the preferred carbonatoms 2~20 of carbalkoxy.Can enumerate for example methoxycarbonyl; Ethoxycarbonyl; The third oxygen carbonyl; Butoxy carbonyl; Own oxygen carbonyl; Hot oxygen carbonyl; The last of the ten Heavenly stems oxygen carbonyl; Octadecane oxygen carbonyl; Carbobenzoxy; The trifluoro methoxycarbonyl; The 1-naphthalene oxygen carbonyl; The 2-naphthalene oxygen carbonyl; 4-methyl sulfane base carbobenzoxy; 4-phenyl sulfane base carbobenzoxy; 4-dimethylamino carbobenzoxy; 4-diethylamino carbobenzoxy; 2-chlorobenzene oxygen carbonyl; 2-methylenedioxy phenoxy carbonyl; 2-methoxyl group carbobenzoxy; 2-phenoxy butoxy carbonyl; 3-chlorobenzene oxygen carbonyl; 3-trifluoromethyl carbobenzoxy; 3-cyanic acid carbobenzoxy; 3-nitro carbobenzoxy; 4-fluorobenzene oxygen carbonyl; 4-cyanic acid carbobenzoxy; 4-methoxyl group carbobenzoxy etc.
Formamyl as the preferred total carbon atom number 1~30 of formamyl.Can enumerate for example N-methylamino formyl radical, N-ethylamino formyl radical, N-propyl group formamyl, N-butyl formamyl, N-hexyl formamyl, N-cyclohexyl carboxyamide base, N-octyl group formamyl, N-decyl formamyl, N-octadecyl formamyl, N-phenyl amino formyl radical, N-2-aminomethyl phenyl formamyl, N-2-chloro-phenyl-formamyl, N-2-isopropyl phenyl formamyl, N-2-(2-ethylhexyl) phenyl amino formyl radical, N-3-chloro-phenyl-formamyl, N-3-nitrophenyl formamyl, N-3-cyano-phenyl formamyl, N-4-p-methoxy-phenyl formamyl, N-4-cyano-phenyl formamyl, N-4-methyl sulfane base phenyl amino formyl radical, N-4-phenyl sulfane base phenyl amino formyl radical, N-methyl-N-phenyl amino formyl radical, N; N-formyl-dimethylamino, N; N-dibutylamino formyl radical, N, N-diphenyl amino formyl radical etc.
Amino-sulfonyl as the preferred total carbon atom number 0~30 of amino-sulfonyl.Can enumerate for example amino-sulfonyl, N-alkyl amino sulfonyl, N-n-aryl sulfonyl, N, N-dialkyl amino sulfonyl, N, N-ammonia diaryl base alkylsulfonyl, N-alkyl-N-n-aryl sulfonyl etc.More specifically can enumerate N-methylamino alkylsulfonyl, N-ethylamino alkylsulfonyl, N-propyl group amino-sulfonyl, N-butyl amino-sulfonyl, N-hexyl amino-sulfonyl, N-cyclohexyl amino-sulfonyl, N-octyl group amino-sulfonyl, N-2-ethylhexyl amino-sulfonyl, N-decyl amino-sulfonyl, N-octadecyl amino-sulfonyl, N-phenyl amino alkylsulfonyl, N-2-aminomethyl phenyl amino-sulfonyl, N-2-chloro-phenyl-amino-sulfonyl, N-2-p-methoxy-phenyl amino-sulfonyl, N-2-isopropyl phenyl amino-sulfonyl, N-3-chloro-phenyl-amino-sulfonyl, N-3-nitrophenyl amino-sulfonyl, N-3-cyano-phenyl amino-sulfonyl, N-4-p-methoxy-phenyl amino-sulfonyl, N-4-cyano-phenyl amino-sulfonyl, N-4-dimethylaminophenyl amino-sulfonyl, N-4-methyl sulfane base phenyl amino alkylsulfonyl, N-4-phenyl sulfane base phenyl amino alkylsulfonyl, N-methyl-N-phenyl amino alkylsulfonyl, N; N-dimethylamino alkylsulfonyl, N; N-dibutylamino alkylsulfonyl, N, N-diphenyl amino alkylsulfonyl etc.
Amino as the preferred total carbon atom number 0~50 of amino.For example can enumerate-NH
2, N-alkylamino, N-virtue amino, N-amido, N-sulfonamido, N, N-dialkyl amido, N, N-ammonia diaryl base, N-alkyl-N-virtue amino, N, N-disulfonyl base amino etc.More specifically can enumerate N-methylamino-, N-ethylamino, N-third amino, N-isopropylamino, N-fourth amino, uncle's N-fourth amino, the own amino of N-, N-hexamethylene amino, the hot amino of N-, the own amino of N-2-ethyl, N-amino in the last of the ten Heavenly stems, N-octadecyl amino, N-benzyl amino, N-phenylamino, N-2-methylbenzene amino, N-2-chlorobenzene amino, N-2-anisole amino, N-2-isopropoxy phenylamino, N-2-(2-ethylhexyl) phenylamino, N-3-chlorobenzene amino, N-3-oil of mirbane amino, N-3-cyanic acid phenylamino, N-3-trifluoromethyl phenylamino, N-4-anisole amino, N-4-cyanic acid phenylamino, N-4-trifluoromethyl phenylamino, N-4-methyl sulfane base phenylamino, N-4-phenyl sulfane base phenylamino, N-4-dimethylamino phenylamino, N-methyl-N-phenylamino, N; N-dimethylamino, N; N-diethylamino, N; N-dibutylamino, N; N-diphenyl amino, N; The N-diacetyl is amino, N, and the N-dibenzoyl is amino, N, and N-(dibutyl carbonyl) is amino, N; N-(dimethyl methyl acyl group) is amino, N; N-(diethylammonium alkylsulfonyl) is amino, N, and N-(dibutyl alkylsulfonyl) is amino, N, N-(phenylbenzene alkylsulfonyl) amino etc.
Phosphono as the preferred total carbon atom number 2~50 of phosphono.Can enumerate for example dimethyl phosphine acyl group, diethyl phosphonyl, dipropyl phosphono, diphenylphosphine acyl group, dimethoxy phosphono, diethoxy phosphonium mesitoyl base, dibenzoyl phosphono, two (2,4, the 6-trimethylphenyl) phosphono etc.
Aromatic series or aliphatic heterocyclic radical as heterocyclic radical preferred package nitrogen atom, Sauerstoffatom, sulphur atom, phosphorus atom.For example can enumerate thienyl, benzo [b] thienyl, naphthalene [2,3-b] thienyl, thienyl, furyl, pyranyl, isobenzofuran-base, chromenyl, xanthenyl, phenothioxin base, 2H-pyrryl, pyrryl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, indolizinyl, pseudoindoyl, 3H-indyl, indyl, 1H-indazolyl, purine radicals, 4H-quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolyl, cinnolines base, pteridyl, 4aH-carbazyl, carbazyl, β-Ka Lin base, phenanthridinyl, 2-acridyl, perimidinyl, phenanthrolinyl, phenazinyl, phenarsazine base, isothiazolyl, phenothiazinyl, isoxazolyl, furazan base, phenoxazinyl, different chromanyl, chromanyl, pyrrolidyl, pyrrolinyl, imidazolidyl, imidazolinyl, pyrazolidyl, pyrazolinyl, piperidyl, piperazinyl, indolinyl, isoindolinyl, quinuclidinyl, morpholinyl, thioxanthene base etc.
As stated, organic residue can have substituting group, and this substituting group can also be replaced by other substituting groups.
Can enumerate for example halogens such as fluorine atom, chlorine atom, bromine atoms, iodine atom as other substituting groups, alkoxyl groups such as methoxyl group, oxyethyl group, tert.-butoxy, phenoxy,, carbalkoxys such as methoxycarbonyl, butoxy carbonyl, carbobenzoxy to aryloxy such as tolyloxys; Acyloxy such as acetoxyl group, propionyloxy, benzoyloxy, acyl groups such as ethanoyl, benzoyl-, isobutyryl, acryl, methacryloyl, methoxalyl, alkyl alkylthio bases such as methyl sulfane base, tertiary butyl sulfane base, alkylaminos such as methylamino-, hexamethylene amino; Dialkyl amidos such as dimethylamino, diethylamino, morpholinyl, piperidyl, phenylamino, amino, alkyl such as methyl, ethyl, the tertiary butyl, dodecyl, aryl such as phenyl, p-methylphenyl, xylyl, cumyl, naphthyl, anthryl, phenanthryl to virtues such as toluinos; Hydroxyl, carboxyl, formyl radical, sulfydryl; Sulfo group, methylsulfonyl, p-toluenesulfonyl, amino; Nitro, cyanic acid, trifluoromethyl; Trichloromethyl, trimethyl silyl, phosphinico-; Phosphoryl, trimethylammonium ammonium, dimethyl sulfonium base and triphenyl benzoyl methyl sulfonium base etc.
In these substituent X, preferably can have substituent alkyl, can have substituent aryl, can have substituent acyl group, can have substituent phosphinyl, can have substituent heterocyclic radical etc.Wherein more preferably can have substituent alkyl, can have substituent aryl.Can enumerate methyl, ethyl, propyl group, butyl, the tertiary butyl, trifluoromethyl, phenyl, benzyl etc. as its concrete example, but the present invention is not limited to these examples.
In the represented compound of general formula of the present invention (1), preferably at least one of A and B is for replacing or unsubstituted carbazyl or replace or compound of unsubstituted naphthyl.At this moment, the substituent part on carbazyl and the naphthyl can combine with the carbon atom of carbazyl or naphthyl or other substituent parts, and is integrated and form ring structure.In addition, for carbazyl and naphthyl,, can combine at any the position of substitution so long as can form the position of substitution of covalent linkage with the carbon atom of the adjacency of general formula (1).
Above-mentioned carbazyl and naphthyl can also be replaced by other substituting groups.Can enumerate the identical substituting group of group cited in the substituting group that can have as other substituting groups with A and B.
In the compound of general formula (1) expression, at least one of preferred A and B is for replacement or unsubstituted general formula (2) perhaps replaces or the compound of the group that unsubstituted general formula (3) is represented.For the group of general formula (2) and general formula (3) expression,, can combine at any the position of substitution so long as can form the position of substitution of covalent linkage with the carbon atom of the adjacency of general formula (1).
Y representes the organic residue of univalent in the general formula (2), can enumerate with above-mentioned substituent X in the identical group of the organic residue of monovalence.From easy acquisition raw material, synthetic consideration easily, preferably replace or unsubstituted alkyl.
In the compound of general formula (1) expression, A and B not simultaneously, A replaces or the group of unsubstituted general formula (2) expression, B replaces or group that unsubstituted general formula (3) is represented.
The group of general formula (2) and general formula (3) expression can be replaced by other substituting groups.Can enumerate the identical substituting group of group cited in the substituting group that can have as other such substituting groups with A and B.Other substituting groups as in the general formula (2) are preferably acyl group, more preferably enumerate to replace or unsubstituted benzoyl-, replacement or unsubstituted alkyl carbonyl.
The concrete example of expression compound of the present invention in table 1, but the present invention is not limited to these concrete examples.
[changing 5]
At first, it is routine that expression A, A different with B and B are selected from the combination of A, B and X under condensation polycyclic hydrocarbon and the heterocyclic situation.
Table 1
Then, it is routine that expression A, A identical with B and B are selected from the combination of A, B and X under the heterocyclic situation.
[table 2]
Then, it is routine that expression A, A identical with B and B are selected from the combination of A, B and X under the situation of the condensation polycyclic hydrocarbon that was replaced by the substituting group beyond the alkoxyl group.
Table 3
Then, it is routine that expression A, A identical with B and B are selected from the combination of A, B and X under the situation of the condensation polycyclic hydrocarbon that was replaced by the alkoxyl group of carbonatoms more than 2.
Table 4
[radical polymerization initiator (a)]
Then, describe to radical polymerization initiator of the present invention (a).Radical polymerization initiator of the present invention is characterised in that, comprises the compound of the structure with above-mentioned general formula (1) expression, can enumerate with above-mentioned compound of the present invention in the cited identical compound of material.
In the radical polymerization initiator of the present invention (a), the A in the preferred formula (1) is selected from the compound of replacement or unsubstituted carbazyl and replacement or unsubstituted naphthyl.At this moment, the substituent part on carbazyl and the naphthyl can combine with the carbon atom of carbazyl or naphthyl or other substituent parts, and is integrated and form ring structure.In addition, for carbazyl and naphthyl,, can combine at any the position of substitution so long as can form the position of substitution of covalent linkage with the carbon atom of the adjacency of general formula (1).
Above-mentioned carbazyl and naphthyl can also be replaced by other substituting groups.Can enumerate the identical substituting group of group cited in the substituting group that can have as other substituting groups with A and B.Preferably replace or unsubstituted carbazyl or replacement or unsubstituted naphthyl as the A in the general formula (1); This is owing to obtain raw material, synthetic easily easily; Reason is not clear now in detail although also have, and compound decomposes the reasons such as efficient height that produce radical through rayed.
In the compound of general formula (1) expression, more preferably the A in the general formula (1) is selected from and replaces or unsubstituted general formula (2) or replace or the compound of the group that unsubstituted general formula (3) is represented.For the group of general formula (2) and general formula (3) expression,, can combine at any the position of substitution so long as can form the position of substitution of covalent linkage with the carbon atom of the adjacency of general formula (1).
Y representes the organic residue of univalent in the general formula (2), can enumerate with above-mentioned substituent X in the identical group of the organic residue of monovalence.From easy acquisition raw material, easily synthetic, can improve to and the solvent or the dissolving resin property equal angles of usefulness consider, preferably replace or unsubstituted alkyl.
The group of the group of above-mentioned general formula (2) expression and general formula (3) expression can be replaced by other substituting groups.Can enumerate the identical substituting group of group cited in the substituting group that can have as other such substituting groups with A and B.A in the preferred formula (1) is the situation of the group of replacement or unsubstituted general formula (2) or replacement or unsubstituted general formula (3) expression; This is owing to obtain raw material, synthetic easily easily; Reason is not clear now in detail although also have, and compound decomposes the reasons such as efficient height that produce radical through rayed.
In the compound of general formula (1) expression, more preferably the A in the general formula (1) is the group of replacement or unsubstituted general formula (2) expression, and B is the group that replaces or unsubstituted general formula (3) is represented.At this moment, although reason is not clear now in detail, compound decomposes the efficient height that produces radical through rayed, can bring into play the function of more high sensitive initiator.
In addition, other substituting groups in the group of general formula (2) expression are preferably acyl group, more preferably enumerate to replace or unsubstituted benzoyl-, replacement or unsubstituted alkyl carbonyl.The group of general formula (2) expression is by the substituted situation of these substituting groups, and compound will decompose with rayed amount still less, produces radical effectively, thereby preferred, but its detailed reason is not clear now.
Parent material when the compound of synthetic general formula (1) expression and radical polymerization initiator (a) is the oxime of formula (5) expression.
[changing 6]
(in the formula, A is identical with the definition of general formula (1) with B.)
The oxime of general formula (5) expression can be through for example Org.React., 7, < 1953 >, 327 or Japanization association compiles, the 4th edition, the whole bag of tricks of record obtain in the experimental chemistry lecture, the 14th volume 1316 pages (ball is kind).And then, also can obtain by the compound method of the oxime of record in the commercially available textbook (for example J.March, Advanced Organic OrganicChemistry, 4th Edition, Wiley Interscience, 1992).In addition, the initial feed beta-diketon when synthesizing oxime can be through for example Tetrahedron:Asymmetry, 14, < 2003 >; 2739, Chem.Ber., 113, < 1980 >, 1507, Helvetica Chimica Acta; 84, < 2001 >, 2316, Organic Syntheses, Coll.Vol.III; Pp 251, Bull.Chem.Soc.Jpn., 71, < 1998 >, the whole bag of tricks of record obtains in 2253.These documents all enroll in this specification sheets as a reference.
One of optimum oxime compound method is to utilize the nitrosification of the active methylene group of nitrous acid or nitrous acid alkane ester.For example at Organic Syntheses Coll.Vol.VI, pp 840, Organic Syntheses Coll.Vol.III, pp 191and 513, Organic Syntheses Coll.Vol.II, pp 202; 204 and 363, J.Am.Chem.Soc., 47, < 1925 >, 2033, J.Chem.Soc.; 117, < 1920 >, 590, J.Chem.Soc., 51; < 1929 >, put down in writing reaction conditions in 2264, be suitable for making oxime.Nitrous acid is generated by Sodium Nitrite usually.Nitrous acid alkane ester for example is methyl nitrite, nitrous acid isopropyl ester, butyl nitrite, Isopentyl nitrite.These documents all enroll in this specification sheets as a reference.
The oxime that the compound of general formula (1) expression and radical polymerization initiator (a) are represented with general formula (5) is as parent material.And; Can make as follows: by the method for document record for example the oxime that obtains of aforesaid method and acyl chlorides or acid anhydrides in the such inert solvent of for example THF, benzene or N; At alkali for example in the presence of the such tertiary amine of triethylamine, perhaps in the such basic solvent of pyridine, react.
Such reaction is known to those skilled in the art, generally under-15 ℃~+ 50 ℃, preferred 0~30 ℃, carries out.
Whole oxime ester bases exists with two stereoscopic configurations (Z) or (E).Can separate its isomer with domestic method, but also can adopt mixture of isomers as light-initiated kind.Thereby, the invention still further relates to the stereoscopic configurations mixture of isomers of the compound of general formula (1).
The compound of general formula of the present invention (1) expression and radical polymerization initiator (a) can through ultimate analysis and
1H-NMR confirms.
Known in the past by α, the most common not longer wavelength of specific absorption ultraviolet region of the radical polymerization initiator that α '-diketone oxime ester compound constitutes, thereby lack active near ultraviolet near infrared light.But; The radical polymerization initiator (a) that the oxime ester compound of being represented by general formula of the present invention (1) constitutes; Through A and B are imported heterocyclic radical, the condensation polycyclic alkyl can have absorption band near ultraviolet to visibility region, and has activity in these near ultraviolets to the zone than visible longer wavelength.
And then the radical polymerization initiator (a) of general formula of the present invention (1) expression can not make up the absorbing wavelength zone substituting group different with absorption intensity simultaneously at A and B, so the wavelength region may of absorption band and absorption intensity become easy and control.In addition, can improve to and the solvent and the monomeric solvability of usefulness.
In addition, when the A in the general formula (1) was identical with B, the ME of the compound of general formula (1) became simple and easy.
[free-radical polymerised compound (b)]
Then, describe to free-radical polymerised compound of the present invention (b).Free-radical polymerised compound of the present invention (b) is the compound with alkene class unsaturated link(age) of free redical polymerization.What is called has the compound of alkene class unsaturated link(age) of free redical polymerization so long as in molecule, have the compound of the alkene class unsaturated link(age) of at least one free redical polymerization; Can be any compound, can have chemical forms such as monomer, oligopolymer, polymkeric substance.These compounds can only use a kind of, also can use with the system of arbitrary ratio mixing more than two kinds in order to improve target property.
Example as the compound of this alkene class unsaturated link(age) with free redical polymerization can be enumerated unsaturated carboxylic acid and salt, ester, ammonia ester, acid amides and acid anhydrides such as vinylformic acid, methylacrylic acid, methylene-succinic acid, Ba Dousuan, iso-crotonic acid, toxilic acid; Vinyl cyanide; Vinylbenzene; Also have free-radical polymerised compounds such as various unsaturated polyesters, unsaturated polyether, unsaturated polyester acid amides, unsaturated polyurethanes, the present invention is not limited to this.Below enumerate the example of free-radical polymerised compound.
The example of esters of acrylic acid:
The example of monofunctional alkyl esters of acrylic acid:
Methyl acrylate, ethyl propenoate, propyl acrylate, isopropyl acrylate, Bing Xisuandingzhi, vinylformic acid isopentyl ester, NSC 11786, ethyl acrylate, Octyl acrylate, decyl acrylate, lauryl acrylate, vinylformic acid octadecane ester, IBOA, cyclohexyl acrylate, vinylformic acid two cyclopentenes esters, vinylformic acid dicyclopentenyl 2-ethoxyethyl acetate, benzyl acrylate.
The example of simple function hydroxy acryl acid ester class:
2-Hydroxy ethyl acrylate, vinylformic acid-2-hydroxy propyl ester, 2-hydroxy-3-chloropropyl acrylate, vinylformic acid-2-hydroxyl-3-phenoxy propyl ester, vinylformic acid-2-hydroxyl-3-allyloxy propyl ester, vinylformic acid-2-acryloxy ethyl-2-hydroxy propyl ester.
The example of simple function Halogen esters of acrylic acid:
Vinylformic acid-2,2,2-trifluoro ethyl ester, vinylformic acid-2,2; 3,3-tetrafluoro propyl ester, vinylformic acid-1H-hexafluoro isopropyl ester, vinylformic acid-1H, 1H, 5H-octafluoro pentyl ester, vinylformic acid-1H; 1H, 2H, 2H-17 fluorine esters in the last of the ten Heavenly stems, vinylformic acid-2,6-two bromo-4-butyl phenyl esters, vinylformic acid-2; 4,6-tribromophenoxy ethyl ester, 2,4,6-tribromophenol 3EO addition propenoate.
Simple function contains the example of ether esters of acrylic acid:
Vinylformic acid-2-methoxyl group ethyl ester, 1,3 butylene glycol methyl ether propenoate, vinylformic acid butoxy ethyl ester, methoxyl group triethylene glycol propenoate, methoxy poly (ethylene glycol) #400 propenoate, methoxyl group dipropylene glycol propenoate, methoxyl group tripropylene glycol propenoate, methoxyl group W 166 propenoate, ethoxydiglycol propenoate, vinylformic acid ethyl carbitol ester, acrylic acid-2-ethyl hexyl carbitol ester, tetrahydrofurfuryl acrylate, vinylformic acid phenoxy ethyl, phenoxy glycol ether propenoate, phenoxy polyethylene glycol acrylate, tolyl polyethylene glycol acrylate, vinylformic acid are to the Nonylphenoxy ethyl ester, to Nonylphenoxy polyethylene glycol acrylate, glycidyl acrylate.
Simple function contains the example of carboxy acrylic ester class:
Senecioate-carboxyl ethyl ester, mono succinate acryloxy ethyl ester, ω-carboxyl polycaprolactone single-acrylate, 2-acrylyl oxy-ethyl phthalandione hydrogen ester, 2-acryloyl-oxy propyl group phthalandione hydrogen ester, 2-acryloyl-oxy propyl group six hydrogen phthalandione hydrogen esters, 2-acryloyl-oxy propyl group tetrahydrochysene phthalandione hydrogen ester.
The example of other monofunctional acrylates:
N; N-dimethyl amino ethyl acrylate, N, N-dimethylaminopropyl propenoate, vinylformic acid morpholine ethyl ester, trimethylsiloxy ethyl propylene acid esters, phenylbenzene-2-acryloxy ethyl phosphonic acid ester, 2-acryloxy ethyl acid phosphoric acid ester, caprolactone modification-2-acryloxy ethyl acid phosphoric acid ester.
The example of two functional acrylate's classes:
1; 4-butylene glycol diacrylate, 1; The caprolactone affixture diacrylate, 1 of 6-hexanediyl ester, glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyoxyethylene glycol #200 diacrylate, polyoxyethylene glycol #300 diacrylate, polyoxyethylene glycol #400 diacrylate, polyoxyethylene glycol #600 diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, four propylene glycol diacrylates, W 166 #400 diacrylate, W 166 #700 diacrylate, neopentylglycol diacrylate, NSC 6366 PO modification diacrylate, hydroxypivalic acid DOPCP diacrylate, hydroxypivalic acid DOPCP; 6-pinakon two (2-hydroxyl-3-acryloxy propyl group) ether, two (4-propenyloxy group polyethoxye phenyl) propane, 1,9-nonanediol diacrylate, pentaerythritol diacrylate, pentaerythritol diacrylate monostearate, pentaerythritol diacrylate mono benzoate, bisphenol a diacrylate, EO modified bisphenol A diacrylate, PO modified bisphenol A diacrylate, Hydrogenated Bisphenol A 99 diacrylate, the modified hydrogenated bisphenol a diacrylate of EO, the modified hydrogenated bisphenol a diacrylate of PO, Bisphenol F diacrylate, EO modified bisphenol F diacrylate, PO modified bisphenol F diacrylate, EO modification tetrabromo-bisphenol diacrylate, tristane dihydroxymethyl diacrylate, tricarbimide EO modification diacrylate.
The example of trifunctional esters of acrylic acid:
Glycerine PO modification triacrylate, Viscoat 295, TriMethylolPropane(TMP) EO modification triacrylate, TriMethylolPropane(TMP) PO modification triacrylate, tricarbimide EO modification triacrylate, tricarbimide EO modification 6-caprolactone modification triacrylate, 1; 3,5-triacryl six hydrogen-s-triazine, pentaerythritol triacrylate, Dipentaerythritol triacrylate tripropionate.
The example of the esters of acrylic acid that four senses are above:
Tetramethylol methane tetraacrylate, Dipentaerythritol tetraacrylate, Dipentaerythritol five propenoate mono-propionates, dipentaerythritol acrylate, tetramethylol methane tetraacrylate, oligomer ester tetraacrylate, three (acryloxy) SULPHOSUCCINIC ACID ESTER.
The example of methyl acrylic ester:
The example of monofunctional alkyl methyl acrylic ester:
TEB 3K; Jia Jibingxisuanyizhi; Propyl methacrylate; Isopropyl methacrylate; NSC 20956; The methacrylic isoamyl valerate; N-Hexyl methacrylate; The own ester of methylacrylic acid-2-; Methylacrylic acid-2-ethylhexyl; Octyl methacrylate; Decyl-octyl methacrylate; Lauryl methacrylate(LMA); Methylacrylic acid octadecane ester; Isobornyl methacrylate; Cyclohexyl methacrylate; Methylacrylic acid two cyclopentenes esters; Methylacrylic acid dicyclopentenyl 2-ethoxyethyl acetate; Benzyl methacrylate.
The example of simple function hydroxyl methyl acrylic ester:
Methylacrylic acid-2-hydroxy methacrylate, methylacrylic acid-2-hydroxy propyl ester, methylacrylic acid-2-hydroxyl-3-chlorine propyl ester, methylacrylic acid-2-hydroxyl-3-phenoxy propyl ester, methylacrylic acid-2-hydroxyl-3-allyloxy propyl ester, methylacrylic acid-2-acryloxy ethyl-2-hydroxy propyl ester.
The example of simple function Halogen methyl acrylic ester:
Methylacrylic acid-2,2,2-trifluoro ethyl ester, methylacrylic acid-2,2; 3,3-tetrafluoro propyl ester, methylacrylic acid-1H-hexafluoro isopropyl ester, methylacrylic acid-1H, 1H, 5H-octafluoro pentyl ester, methylacrylic acid-1H; 1H, 2H, 2H-17 fluorine esters in the last of the ten Heavenly stems, methylacrylic acid-2,6-two bromo-4-butyl phenyl esters, methylacrylic acid-2; 4,6-tribromophenoxy ethyl ester, 2,4,6-tribromophenol 3EO addition methacrylic ester.
Simple function contains the example of ether methyl acrylic ester:
Methylacrylic acid-2-methoxyl group ethyl ester, 1,3 butylene glycol methyl ether methacrylic ester, methylacrylic acid butoxy ethyl ester, methoxyl group triethylene glycol methacrylic ester, methoxy poly (ethylene glycol) #400 methacrylic ester, methoxyl group dipropylene glycol methacrylic ester, methoxyl group tripropylene glycol methacrylic ester, methoxyl group W 166 methacrylic ester, ethoxydiglycol methacrylic ester, methylacrylic acid-2-ethylhexyl carbitol ester, tetrahydrofurfuryl methacrylate, methylacrylic acid phenoxy ethyl, phenoxy glycol ether methacrylic ester, phenoxy polyethylene glycol methacrylate-styrene polymer, tolyl polyethylene glycol methacrylate-styrene polymer, methylacrylic acid are to the Nonylphenoxy ethyl ester, to Nonylphenoxy polyethylene glycol methacrylate-styrene polymer, SY-Monomer G.
Simple function contains the example of carboxyl methyl acrylic ester:
Methylacrylic acid-β-carboxyl ethyl ester, mono succinate methacryloxy ethyl ester, ω-carboxyl polycaprolactone monomethacrylates, 2-methylacryoyloxyethyl phthalandione hydrogen ester, 2-methacryloxypropyl phthalandione hydrogen ester, 2-methacryloxypropyl six hydrogen phthalandione hydrogen esters, 2-methacryloxypropyl tetrahydrochysene phthalandione hydrogen ester.
The example of other simple function methacrylic esters:
Dimethylaminoethyl acrylate methyl base amino methyl, methylacrylic acid-N; N-dimethylamino ethyl ester, methylacrylic acid-N, N-dimethylamino propyl ester, methylacrylic acid morpholine ethyl ester, methylacrylic acid trimethylsiloxy ethyl ester, phenylbenzene-2-methacryloxyethyl SULPHOSUCCINIC ACID ESTER, 2-methacryloxyethyl acid phosphoric acid ester, caprolactone modification-2-methacryloxyethyl acid phosphoric acid ester.
The example of two sense methyl acrylic esters:
1; 4-butylene glycol dimethacrylate, 1; The caprolactone affixture dimethacrylate, 1 of 6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, TEG dimethacrylate, polyoxyethylene glycol #200 dimethacrylate, polyoxyethylene glycol #300 dimethacrylate, polyoxyethylene glycol #400 dimethacrylate, polyoxyethylene glycol #600 dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, four Ucar 35 dimethacrylates, W 166 #400 dimethacrylate, W 166 #700 dimethacrylate, TD 1523, NSC 6366 PO modification dimethacrylate, hydroxypivalic acid DOPCP dimethacrylate, hydroxypivalic acid DOPCP; 6-pinakon two (2-hydroxy-3-methyl acryloxy propyl group) ether, 1; 9-nonanediol dimethacrylate, dimethyl pentaerythritol acrylate, dimethyl pentaerythritol acrylate monostearate, dimethyl pentaerythritol acrylate mono benzoate, 2,2-two (4-metacryloxy polyethoxye phenyl) propane, bisphenol a dimethacrylate, EO modified bisphenol A dimethacrylate, PO modified bisphenol A dimethacrylate, Hydrogenated Bisphenol A 99 dimethacrylate, the modified hydrogenated bisphenol a dimethacrylate of EO, the modified hydrogenated bisphenol a dimethacrylate of PO, Bisphenol F dimethacrylate, EO modified bisphenol F dimethacrylate, PO modified bisphenol F dimethacrylate, EO modification tetrabromo-bisphenol dimethacrylate, tristane dihydroxymethyl dimethacrylate, tricarbimide EO modification dimethacrylate.
The example of trifunctional methyl acrylic ester:
Glycerine PO modification trimethacrylate, trimethylolethane trimethacrylate methacrylic ester, trimethylolpropane trimethacrylate, TriMethylolPropane(TMP) EO modification trimethacrylate, TriMethylolPropane(TMP) PO modification trimethacrylate, tricarbimide EO modification trimethacrylate, tricarbimide EO modification 6-caprolactone modification trimethacrylate, 1; 3,5-trimethylammonium acryl six hydrogen-s-triazine, pentaerythritol acrylate trimethyl, Dipentaerythritol trimethacrylate tripropionate.
The example of the methyl acrylic ester that four senses are above:
Tetramethylolmethane tetramethyl-propenoate, Dipentaerythritol pentamethyl-propenoate mono-propionate, Dipentaerythritol hexamethyl propenoate, tetramethylol methane tetramethyl-propenoate, oligomer ester tetramethyl-propenoate, three (methacryloxy) SULPHOSUCCINIC ACID ESTER.
The example of allyl ester class:
Glycidyl allyl ether, dially phthalate, trimellitic acid triallyl, triallyl isocyanurate.
The example of amides:
Acrylic amide, N hydroxymethyl acrylamide, diacetone acrylamide, N; N-DMAA, N; N-diethylammonium acrylic amide, N-NSC 11448, acryloyl morpholine, USAF RH-1, N-methylol methacrylamide, two acetone USAF RH-1s, N; N-dimethylmethacryl amide, N, N-diethylmethyl acrylic amide, N-isopropyl methyl acrylic amide, methacryloyl morpholine.
The example of styrenic:
Vinylbenzene, para hydroxybenzene ethene, to chloro-styrene, to bromstyrol, p-methylstyrene, to methoxy styrene, to tert.-butoxy vinylbenzene, to tertbutyloxycarbonyl vinylbenzene, to tertbutyloxycarbonyl Styrene oxide 98min., 2,4-phenylbenzene-4-methyl-1-pentene.
The example of other vinyl compounds:
Vinyl acetate, monochloro vinyl acetate, vinyl benzoate, trimethylacetic acid vinyl acetate, vinyl butyrate, vinyl laurate, hexanodioic acid divinyl ester, methacrylic vinyl acetate, Vinyl crotonate, 2 ethyl hexanoic acid vinyl acetate, N-VCz, N-vinyl pyrrolidone etc.
Above-mentioned free-radical polymerised compound (b) can easily obtain as the commercially available article of the manufacturers shown in following.Can enumerate for example " the light propenoate (ラ イ ト ア Network リ レ one ト) " of common prosperity society oil chemistry industry (strain) society manufacturing; " light ester (ラ イ ト エ ス テ Le) "; " epoxy ester "; " ammonia ester propenoate " and " high functionality oligopolymer " series; " NK ester " and " NK oligopolymer " series that Xin Zhong village chemistry (strain) society makes; Hitachi changes into " FANCRYL " series that industry (strain) society makes; " ARONIX M " series that East Asia synthetic chemistry (strain) society makes; " functional monomer " series that big eight chemical industry (strain) society makes; " special propenyl monomer " series that Osaka organic chemistry industry (strain) society makes; " ACRYESTER " and " DIABEAM oligopolymer (ダ イ ヤ PVC one system オ リ go マ one) " series that society of Mitsubishi's beautiful sun (strain) makes; " カ ヤ ラ Star De " and " カ ヤ マ one " series that Japan chemical drug (strain) society makes; " vinylformic acid/methacrylate monomers " series that (strain) Japanese catalyst society makes; " NICHIGO-UV purple light ammonia ester origoester acrylate " series that Japan synthetic chemical industry (strain) society makes; " vinyl carboxylates monomer " series that SHIN-ETSU HANTOTAI's vinyl acetate (strain) society makes; " functional monomer " series that (strain) Xing Renshe makes etc.
And then free-radical polymerised compound (b) can be enumerated the compound of putting down in writing in the document shown in following.Can enumerate " the linking agent handbook (1981 that the third-class people in Shanxi compiles under the mountain for example; Great achievement society); Add " UVEB solidifies handbook (raw material volume) " (1985 that rattan looks volume clearly; The meeting of polymer publication); ラ De テ Star Network research association compiles; Clear " actual techniques of new photoresist " compiled of Japanese red pine (1987; CMC); " the high molecular precise treatment of Thermocurable " that rattan far away has just been compiled (1986; CMC); Flood " the vibrin handbook (1988 of the flourish youth work in mountain; Nikkan Kogyo Shimbun); " application of UVEB curing technology and the market " that ラ De テ Star Network research association compiles (2002; CMC) etc.These documents are all enrolled in this specification sheets as a reference.
Free-radical polymerised compound of the present invention (b) can only use a kind of, also can mix more than two kinds by arbitrary ratio and uses in order to improve desired characteristics.
[tackiness agent]
Polymkeric substance, multipolymers such as the tackiness agent that uses can be enumerated polyacrylate(s), gathers the alpha-alkyl esters of acrylic acid as mixing with photopolymerizable composition of the present invention, polyamide-based, polyvinyl acetal class, polyoxymethylene class, polyurethanes, polycarbonate-based, polystyrene type, polyvinylesters class.More specifically can enumerate Rohm tech inc, polymethylmethacrylate, polyethyl methacrylate, PVK, PVP K120, polyvinyl butyral, PVA, novolac resin, resol, epoxy resin, Synolac, the known organic high molecular polymer of industry that also has " actual techniques of new photoresist " (, CMC in 1987) and " 10188 commodity chemical " that the clear prison of Japanese red pine repaiies 657~767 pages (1988, chemical industry day newspaper office) to put down in writing.These documents are all enrolled in this specification sheets as a reference.
[alkali soluble resins (c)]
And then, when photopolymerizable composition of the present invention is used for image and forms purpose such as purposes as photo anti-corrosion agent material, can add and use carbonyl bearing polymer as follows.Carbonyl bearing polymer has solvability to the alkaline water dissolubility.Therefore, if the film that partly solidify to use optical polymerism composition of the present invention to make according to the difference to the solubleness of alkaline aqueous solution, can form the pattern of so-called negative resist.
The effect of alkali soluble resins of the present invention (c) performance tackiness agent and when forming picture pattern, so long as the resin that the developing solution that uses in its development treatment operation, preferred especially alkaline-based developer are had solubility, just not special restriction.Wherein preferred alkali soluble resins as carboxy-containing copolymer.Especially preferably have 1 above carboxyl ethylenically unsaturated monomers (hereinafter to be referred as containing the carboxyl unsaturated monomer) but and the multipolymer (hereinafter to be referred as carboxy-containing copolymer) of the ethylenically unsaturated monomers of other copolymerization (hereinafter to be referred as copolymerization property unsaturated monomer).
Can enumerate unsaturated monocarboxylic classes such as vinylformic acid, methylacrylic acid, Ba Dousuan, α-Lv Bingxisuan, TRANSCINNAMIC ACID as the example that contains the carboxyl unsaturated monomer; Unsaturated dicarboxylic acid or its anhydrides such as toxilic acid, maleic anhydride, fumaric acid, methylene-succinic acid, itaconic anhydride, pyrocitric acid, pyrocitric acid acid anhydride, methylfumaric acid; Unsaturated polycarboxylic acid or its anhydrides that ternary is above, list [(methyl) acryloxyalkyl] the ester class of the polycarboxylic acid that binary such as mono succinate (2-acryloxy ethyl) ester, mono succinate (2-methacryloxyethyl) ester, phthalic acid list (2-acryloxy ethyl) ester, phthalic acid list (2-methacryloxyethyl) ester are above; ω-carboxyl polycaprolactone single-acrylate, ω-carboxyl polycaprolactone monomethacrylates etc. have list (methyl) esters of acrylic acid of the polymkeric substance of carboxyl and hydroxyl etc. at two ends.These contain in the carboxyl unsaturated monomer, and mono succinate (2-acryloxy ethyl) ester and phthalic acid list (2-acryloxy ethyl) ester are sold with the trade(brand)name of M-5300 and M-5400 (East Asia synthetic (strain) makes) respectively.The above-mentioned carboxyl unsaturated monomer that contains can use separately or mix more than 2 kinds and uses.
In addition; As copolymerization property unsaturated monomer for example can enumerate vinylbenzene, alpha-methyl styrene, adjacent Vinyl toluene, a Vinyl toluene, to Vinyl toluene, to chloro-styrene, O-methoxy vinylbenzene, meta-methoxy vinylbenzene, to methoxy styrene, adjacent vinyl benzyl methyl ether, a vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinyl benzyl glycidyl ether, a vinyl benzyl glycidyl ether, to aromatic ethenyl compounds such as vinyl benzyl glycidyl ethers; Indenes classes such as indenes, 1-methyl indenes; Unsaturated carboxylate types such as methyl acrylate, TEB 3K, ethyl propenoate, Jia Jibingxisuanyizhi, vinylformic acid n-propyl, n propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-BMA, NSC 20949, Propenoic acid, 2-methyl, isobutyl ester, sec-butyl acrylate, the secondary butyl ester of methylacrylic acid, tert-butyl acrylate, methacrylic tert-butyl acrylate, 2-Hydroxy ethyl acrylate, methylacrylic acid-2-hydroxy methacrylate, vinylformic acid-2-hydroxy propyl ester, methylacrylic acid-2-hydroxy propyl ester, vinylformic acid-3-hydroxy propyl ester, methylacrylic acid-3-hydroxy propyl ester, vinylformic acid-2-hydroxyl butyl ester, methylacrylic acid-2-hydroxyl butyl ester, vinylformic acid-3-hydroxyl butyl ester, methylacrylic acid-3-hydroxyl butyl ester, vinylformic acid-4-hydroxyl butyl ester, methylacrylic acid-4-hydroxyl butyl ester, allyl acrylate, allyl methacrylate(AMA), benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, vinylformic acid-2-methoxyl group ethyl ester, methylacrylic acid-2-methoxyl group ethyl ester, vinylformic acid-2-phenoxy ethyl, methylacrylic acid-2-methoxyl group ethyl ester, methoxyl group glycol ether propenoate, methoxyl group glycol ether methacrylic ester, methoxyl group triethylene glycol propenoate, methoxyl group triethylene glycol methacrylic ester, MPEG propenoate, MPEG methacrylic ester, methoxyl group dipropylene glycol propenoate, methoxyl group dipropylene glycol methacrylic ester, IBOA, isobornyl methacrylate, vinylformic acid Dicyclopentadiene (DCPD) ester, methylacrylic acid Dicyclopentadiene (DCPD) ester, vinylformic acid-2-hydroxyl-3-phenoxy propyl ester, methylacrylic acid-2-hydroxyl-3-phenoxy propyl ester, glycerine mono acrylic ester, glycerin monomethyl acrylic ester; Vinylformic acid-2-amino ethyl ester, methylacrylic acid-2-amino ethyl ester, vinylformic acid-2-dimethylamino ethyl ester, methylacrylic acid-2-dimethylamino ethyl ester, the amino propyl ester of vinylformic acid-2-, the amino propyl ester of methylacrylic acid-2-, vinylformic acid-2-dimethylamino propyl ester, methylacrylic acid-2-dimethylamino propyl ester, the amino propyl ester of vinylformic acid-3-, the amino propyl ester of methylacrylic acid-3-, vinylformic acid-3-dimethylamino propyl ester, methylacrylic acid-unsaturated carboxylic acid aminoalkyl ester classes such as 3-dimethylamino propyl ester; Unsaturated carboxylic acid such as glycidyl acrylate, SY-Monomer G glycidyl ester class; Vinyl carboxylates classes such as vinyl acetate, propionate, vinyl butyrate, vinyl benzoate; Unsaturated ethers such as methoxy ethylene, ethyl vinyl ether, glycidyl allyl ether; Vinyl cyanide based compounds such as vinyl cyanide, methacrylonitrile, α-Lv Bingxijing, vinyl cyanide fork; Unsaturated acyl amines such as acrylic amide, USAF RH-1, α-propenyl chloride acid amides, N-2-hydroxyethyl acrylic amide, N-2-hydroxyethyl methacrylamide; Unsaturated acid imides such as maleimide, N-phenylmaleimide, N-cyclohexyl maleimide; 1; Aliphatics conjugated dienes such as 3-divinyl, isoprene, chloro pentadiene, the end of polymer molecular chains such as PS, polymethyl acrylate, polymethylmethacrylate, the positive butyl ester of ROHM, Vinalac 5920, ZGK 5 has the macromonomer class of single acryl or monomethyl acryl etc.These copolymerization property unsaturated monomers can use separately or mix more than 2 kinds and use.
As preferred (P) monomer component of the carboxy-containing copolymer among the present invention and (Q) multipolymer of monomer component (below be called carboxy-containing copolymer (R)); Wherein said (P) monomer component is for being neccessary composition with vinylformic acid and/or methylacrylic acid; What according to circumstances also contain at least a compound that is selected from mono succinate (2-acryloxy ethyl) ester, mono succinate (2-methacryloxyethyl) ester, ω-carboxyl polycaprolactone single-acrylate and the ω-carboxyl polycaprolactone monomethacrylates contains carboxyl unsaturated monomer composition, and said (Q) monomer component is to be selected from least a in vinylbenzene, methyl acrylate, methacrylic ester, 2-Hydroxy ethyl acrylate, methylacrylic acid-2-hydroxy methacrylate, allyl acrylate, allyl methacrylate(AMA), benzyl acrylate, benzyl methacrylate, glycerine mono acrylic ester, glycerin monomethyl acrylic ester, N-phenylmaleimide, polystyrene macromolecular monomer and the polymethylmethacrylate macromonomer.
Can enumerate (methyl) vinylformic acid/(methyl) methyl acrylate copolymer as the concrete example of carboxy-containing copolymer (R); (methyl) vinylformic acid/(methyl) benzyl acrylate multipolymer; (methyl) vinylformic acid/(methyl) 2-Hydroxy ethyl acrylate/(methyl) benzyl acrylate multipolymer; (methyl) vinylformic acid/(methyl) methyl acrylate/polystyrene macromolecular monomer copolymer; (methyl) vinylformic acid/(methyl) methyl acrylate/polymethylmethacrylate macromonomer multipolymer; (methyl) vinylformic acid/(methyl) benzyl acrylate/polystyrene macromolecular monomer copolymer; (methyl) vinylformic acid/(methyl) benzyl acrylate/polymethylmethacrylate macromonomer multipolymer; (methyl) vinylformic acid/(methyl) 2-Hydroxy ethyl acrylate/(methyl) benzyl acrylate/polystyrene macromolecular monomer copolymer; (methyl) vinylformic acid/(methyl) 2-Hydroxy ethyl acrylate/(methyl) benzyl acrylate/polymethylmethacrylate macromonomer multipolymer; Methylacrylic acid/vinylbenzene/(methyl) benzyl acrylate/N-phenylmaleimide multipolymer; (methyl) vinylformic acid/mono succinate [2-(methyl) acryloxy ethyl] ester/vinylbenzene/(methyl) benzyl acrylate/N-phenylmaleimide multipolymer; (methyl) vinylformic acid/mono succinate [2-(methyl) acryloxy ethyl] ester/vinylbenzene/(methyl) allyl acrylate/N-phenylmaleimide multipolymer; (methyl) vinylformic acid/vinylbenzene/(methyl) benzyl acrylate/glycerine list (methyl) propenoate/N-phenylmaleimide multipolymer; (methyl) vinylformic acid/ω-carboxyl polycaprolactone list (methyl) propenoate/vinylbenzene/(methyl) benzyl acrylate/glycerine list (methyl) propenoate/N-phenylmaleimide multipolymer etc.
The substituting group that exists in the carboxy-containing copolymer molecule can also be modified by other materials.For example the part through making the carboxyl that exists in this polymkeric substance and known has monomer that glycidyl is equal to the functional group of carboxyl reaction and reacts and modify, and the cross-linking set relevant with radical polymerization can also be set in molecule.Glycidyl (methyl) alkyl acrylate can be used as such monomer, for example glycidyl (methyl) vinylformic acid, glycidyl (methyl) methyl acrylate, glycidyl (methyl) ethyl propenoate, glycidyl (methyl) Bing Xisuandingzhi, glycidyl (methyl) ethyl acrylate can be enumerated.In addition, the hydroxyl that exists in this polymkeric substance through with the condensations such as (clear and electrician's (strain) make " カ レ Application ズ MOI ") of 2-acryloxy ethyl isocyanate, 2-methacryloyl ethyl isocyanate, same polymerization crosslinking point also can be set.
The copolymerization ratio that contains the carboxyl unsaturated monomer in the carboxy-containing copolymer is generally 5~50 weight %.At this moment, for example fruit is less than 5 weight % for above-mentioned copolymerization ratio, and the resist compsn that obtains tends to reduce to the solvability of alkaline-based developer.On the other hand, if surpass 50 weight %, then the solvability to alkaline-based developer becomes excessive, when developing through alkaline-based developer, often is easy to generate resist film from the base material film be full of cracks with imaging surface that comes off.(GPC, eluent: the polystyrene conversion weight-average molecular weight of THF) measuring (below be called Mw) is generally 3,000~300,000 to alkali soluble resins of the present invention, is preferably 5,000~100,000 by GPC.In addition, (GPC, eluent: the polystyrene conversion number-average molecular weight of THF) measuring (below be called Mn) is generally 3,000~60,000 to alkali soluble resins of the present invention, is preferably 5,000~25,000 by GPC.Among the present invention through using this have specific Mw and the alkali soluble resins of Mn; Can obtain the excellent radioactive rays responsive type compsn of development property; Can form picture pattern thus, be difficult to produce that residue, ground pollute, film is residual etc. on the substrate of irradiating part not with on the light shield layer when developing simultaneously with clear pattern edge.In addition, the ratio (Mw/Mn) of the Mw of alkali soluble resins of the present invention and Mn is preferably 1~5, preferred especially 1~4.
Alkali soluble resins (c) as beyond the above-mentioned carboxy-containing copolymer can be enumerated the resin that phenolic varnish type resin or polycarboxylated styrene etc. have phenol property hydroxyl, and their modification body is also included within the alkali soluble resins of the present invention (c).
Among the present invention, alkali soluble resins (c) can use separately or mix more than 2 kinds and use.
The usage quantity of alkali soluble resins among the present invention (c) is 10~500 weight parts with respect to 100 weight part free-radical polymerised compounds (b).
[sensitizing agent (d)]
In order to promote polymerization, photopolymerizable composition of the present invention can also add sensitizing agent (d).Because sensitizing agent can improve the activity to the light of ultraviolet near infrared region, promote the situation of polymerizability preferably to add sensitizing agent at needs.
Can enumerate with chalcone derivative and dibenzalacetone etc. as the concrete example of this sensitizing agent and to be the unsaturated ketone of representative, to be 1 of representative, polymethin dyes such as 2-derovatives, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivative, xanthene verivate, thioxanthene derivative, xanthone verivate, thioxanthone derivates, coumarin derivatives, ketone group coumarin derivatives, cyanines verivate, portion's cyanines verivate, Oxonol verivate, acridine derivatives, azine derivatives, thiazine derivative, oxazine verivate, dihydroindole verivate, azulene derivatives, azulene salt derivative, the sour cyanines verivate in side, derivatives of porphyrin, tetraphenylporphyrin verivate, triarylmethane derivatives, four benzoporphyrin derivatives, four pyrazinyl tetraazatetradecane porphyrin verivates, phthalocyanine derivates, four azepine tetraazatetradecane porphyrin verivates, four quinoxalinyl tetraazatetradecane porphyrin verivates, naphthalocyanine derivative, inferior phthalocyanine derivates, pyridinium derivative, sulfo-pyridinium derivative, Tetraphyline verivate, A Nule (anulene) verivate, volution pyran derivate, spiral shell ring oxazine verivate, sulfo-volution pyran derivate, carbazole derivative, metal arene complex compound, organic ruthenium complex compound, Mi Qile (Michler) ketone derivatives etc. with benzyl quinone and camphorquinone etc.In addition; " the sensitizing agent of record among " specific function material " (, CMC in 1986) that people such as " functional pigmented chemistry " (, CMC in 1981) that people such as pigment handbook (, talk society in 1986), the former letter in great river compile, gloomy loyal three youths in pond compile, but be not limited to these that concrete example can enumerate also that people such as the former letter in great river compiles.In addition, the light that also can enumerate ultraviolet near infrared region shows the sensitizing agent that absorbs.These materials can use more than 2 kinds according to arbitrary proportion as required.Above-mentioned document is all enrolled in this specification sheets as a reference.Can enumerate thioxanthone derivates, Mi Qile ketone derivatives etc. as the sensitizing agent of sensitization Photoepolymerizationinitiater initiater of the present invention especially aptly in the above-mentioned sensitizing agent.More specifically can enumerate 2; 4-diethyl thioxanthone, 2-clopenthixal ketone, 2; 4-two clopenthixal ketones, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 1-chloro-4-propoxy-thioxanthone, 4; 4 '-two (dimethylamino) benzophenone, 4,4 '-two (diethylamino) benzophenone etc., but be not limited to these.
The radical polymerization initiator (a) and the sensitizing agent (c) of general formula (1) expression can be arbitrary proportions, but the scope of preferred 100/1~1/100 (weight ratio), more preferably 50/1~1/50 scope, further preferred 20/1~1/30 scope.
Photopolymerizable composition of the present invention can mix with the tackiness agent of organic high molecular polymer etc., is applied on the polymeric films such as sheet glass, aluminium sheet, other metal sheets, polyethylene terephthalate and uses.
[other Photoepolymerizationinitiater initiaters]
Photopolymerizable composition of the present invention only has very high susceptibility because of radical polymerization initiator (a), but for the surface cure property that improves photopolymerizable composition and the adaptation of raising and substrate etc., can also with other polymerization starters usefulness also.
Can mix with photopolymerizable composition of the present invention and other polymerization starters of usefulness are listed below: special public clear 59-1281 communique, special public clear 61-9621 communique and the special pyrrolotriazine derivatives of opening clear 60-60104 communique record; The spy opens clear 59-1504 communique and the special organo-peroxide of opening clear 61-243807 communique record; The diazonium compound of special public clear 43-23684 communique, special public clear 44-6413 communique, special public clear 47-1604 communique and No. 3567453 specification sheets record of USP; The organic azide of No. 2848328 specification sheets of USP, No. 2852379 specification sheets of USP and No. 2940853 specification sheets record of USP; The o-quinone two nitrine classes of special public clear 36-22062 communique, special public clear 37-13109 communique, special public clear 38-18015 communique and special public clear 45-9610 communique record; The iodine compound of opening clear 59-140203 communique and the 1307th page of (1977) record of " macromole " the 10th volume with the public clear 55-39162 communique of spy, spy is all cpds of representative; The spy opens the azo cpd of clear 59-142205 communique record; The metal arene complex compound of Te Kaiping 1-54440 communique, No. 109851 specification sheets of European patent, No. 126712 specification sheets of European patent, the 174th page of (1986) record of " J.IMAG.SCI. " the 30th volume; The spy opens two luxuriant titanium classes of clear 61-151197 communique record; " COORDINATION CHEMISTRYREVIEW " the 84th volume the 85th~277 page (1988) and special is opened the transition metal complex that contains transition metal such as ruthenium of flat 2-182701 communique record; The aluminate complex compound of Te Kaiping 3-209477 communique record; The borate cpd of Te Kaiping 2-157760 communique record; The spy opens clear 55-127550 communique and the spy opens 2 of clear 60-202437 communique record; 4; 5-triarylimidazoles dipolymer, the Organohalogen compounds of the clear 59-107344 communique record of carbon tetrabromide and Te Kai, the spy opens the sulfonium complex compound or the oxygen sulfonium complex compound of flat 5-255347 communique record; The spy opens clear 54-99185 communique and the special keto-amine compound of opening clear 63-264560 communique record, and the spy opens 2001-264530 communique, spy and opens that 2001-261761 communique, spy are opened the 2000-80068 communique, the spy opens 2001-233842 communique, special table 2004-534797 communique, USP3558309 specification sheets (1971), USP4202697 specification sheets (1980) and the special oxime ester compound of opening clear 61-24558 communique record etc.These documents are all enrolled in this specification sheets as a reference.Have the compound of the alkene class unsaturated link(age) of free redical polymerization with respect to 100 weight parts, these polymerization starters preferably contain the scope of 0.01~10 weight part.
In addition, polymerization takes place in order to prevent to preserve, photopolymerizable composition of the present invention can also add thermal polymerization inhibitor.
[thermal polymerization inhibitor]
Can enumerate p methoxy phenol, quinhydrones, alkyl replacement quinhydrones, pyrocatechol, tert-butyl catechol, phenothiazine etc. as the concrete example that can add the thermal polymerization inhibitor in the photopolymerizable composition of the present invention to.With respect to the compound of the alkene class unsaturated link(age) that has free redical polymerization with respect to 100 weight parts, these thermal polymerization inhibitors preferably contain the scope of 0.001~5 weight part.
[polymerization promotor and chain-transfer agent]
In addition, in order further to promote polymerization, it is polymerization promotor, the chain-transfer agent of representative that photopolymerizable composition of the present invention can also add with amine and mercaptan, disulphide etc.
Polymerization promotor and the concrete example of chain-transfer agent as adding in the photopolymerizable composition of the present invention can be enumerated for example N-phenylglycine, trolamine, N; Amines such as N-Diethyl Aniline; The thio-alcohol of the clear 64-13144 communique record of No. 4414312 specification sheets of USP and Te Kai; The disulfides of Te Kaiping 2-291561 communique record; The thion class of the clear 64-17048 communique record of No. 3558322 specification sheets of USP and Te Kai, the spy opens the adjacent acyl group thiol oxime acid esters and the N-alkoxy pyridines thion class of flat 2-291560 communique record.These documents are all enrolled in this specification sheets as a reference.
Particularly chain-transfer agent can suppress oxygen polymeric is hindered, even under the height shading, also can promote uniform photocuring reaction, thereby promotes the situation of polymerizability preferably to add at needs.Just there is not special restriction as chain-transfer agent so long as have the compound of such function, but preferred mercaptan compound, preferred especially multi-functional thiol's compound.
The thiol group that has at least more than one as the compound with thiol group that can be used as chain-transfer agent so long as at intramolecularly can use from any selection of the chain-transfer agent that was used for photopolymerizable composition in the past with regard to not special restriction.Can enumerate for example 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 5-chloro-2-mercaptobenzothiazole, 2-sulfydryl-5-methoxyl group benzo thiazole, 5-methyl isophthalic acid as this compound with thiol group; 3; 4-thiadiazole-2-mercaptan, 5-sulfydryl-1-methyl tetrazolium, 3-sulfydryl-4-methyl-4H-1; 2,4-triazole, 2-sulfydryl-1-Methylimidazole, 2-mercaptothiazoline, octane mercaptan etc., but be not limited to this.
Can enumerate compound as preferred especially multi-functional thiol's compound with 2 above thiol groups.Can enumerate for example hexane two mercaptan, decane two mercaptan, 1; 4-dimethyl-sulfydryl benzene, 1; 4-butyleneglycol two (3-mercaptopropionic acid ester), 1; 4-butyleneglycol two (thioglycollate), ethylene glycol bisthioglycolate (3-mercaptopropionic acid ester), ethylene glycol bisthioglycolate (thioglycollate), trimethylolpropane tris (3-mercaptopropionic acid ester), trimethylolpropane tris (thioglycollate), tetramethylolmethane four (3-mercaptopropionic acid ester), tetramethylolmethane four (3-thioglycollate), 2; 5-hexane two mercaptan, 2; 9-decane two mercaptan, 1; 4-two (1-mercaptoethyl benzene), phthalandione two (1-sulfydryl ethyl ester), phthalandione two (2-sulfydryl propyl ester), phthalandione two (3-sulfydryl butyl ester), phthalandione two (3-sulfydryl isobutylate), ethylene glycol bisthioglycolate (3-sulfydryl butyric ester), glycol ether two (3-sulfydryl butyric ester), Ucar 35 two (3-sulfydryl butyric ester), 1; 4-butyleneglycol two (3-sulfydryl butyric ester), 1,3 butylene glycol two (3-sulfydryl butyric ester), 1,2-butyleneglycol two (3-sulfydryl butyric ester), trimethylolpropane tris (3-sulfydryl butyric ester), tetramethylolmethane four (3-sulfydryl butyric ester), Dipentaerythritol six (3-sulfydryl butyric ester), ethylene glycol bisthioglycolate (2-mercaptoisobutyric acid ester), glycol ether two (2-mercaptoisobutyric acid ester), Ucar 35 two (2-mercaptoisobutyric acid ester), 1; 4-butyleneglycol two (2-mercaptoisobutyric acid ester), trimethylolpropane tris (2-mercaptoisobutyric acid ester), tetramethylolmethane four (2-mercaptoisobutyric acid ester), Dipentaerythritol six (2-mercaptoisobutyric acid ester), ethylene glycol bisthioglycolate (3-mercaptoisobutyric acid ester), glycol ether two (3-mercaptoisobutyric acid ester), Ucar 35 two (3-mercaptoisobutyric acid ester), 1; 4-butyleneglycol two (3-mercaptoisobutyric acid ester), trimethylolpropane tris (3-mercaptoisobutyric acid ester), tetramethylolmethane four (3-mercaptoisobutyric acid ester), Dipentaerythritol six (3-mercaptoisobutyric acid ester), 1,8-ethohexadiol two (3-sulfydryl butyric ester), 1,8-ethohexadiol two (2 mercaptopropionic acid ester), 1; 8-ethohexadiol two (3-mercaptoisobutyric acid ester), 2; 4,6-tri-thiol-S-triazine, 2-(N, N-dibutylamino)-4; 6-dimercapto-S-triazine etc., but be not limited to this.
These chain-transfer agents can use separately or make up and use more than 2 kinds among the present invention.
With respect to 100 weight parts radical polymerization initiator of the present invention (a), the usage quantity of chain-transfer agent is preferably 5~3000 weight parts, more preferably 20~1000 weight parts.
[solvent]
Operation property in order to improve coating and to form film, photopolymerizable composition of the present invention can add the use solvent.The solvent that adds can be removed through heat drying or vacuum-drying after coating basically.Can enumerate following material as the solvent that can make an addition to photopolymerizable composition of the present invention: ketones such as methylethylketone, pimelinketone, 2-heptanone, 3-heptanone; (gathering) alkane glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetic ester, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetic ester, diethylene glycol monoethyl ether acetic ester, propylene glycol monomethyl ether acetate, dihydroxypropane single-ether acetic ester; (gathering) alkane glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diglycol monotertiary positive propyl ether, ethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol ethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, Ucar 35 list positive propyl ether, Ucar 35 mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol list ether, dipropylene glycol list positive propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol list ether; Ester classes such as vinyl acetic monomer, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, butyl propionate, ethyl n-butyrate, isopropyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, oxo ritalin, oxo vinyl acetic monomer, oxo N-BUTYL ACETATE, Methoxy Methyl Acetate, Methoxy acetic acid ethyl ester, Methoxy acetic acid butyl ester; Ester classes such as oxyethyl group ritalin, oxyethyl group vinyl acetic monomer, 3-oxygen methyl propionate, 3-oxygen ethyl propionate, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, 2-oxygen methyl propionate, 2-oxygen ethyl propionate, 2-methoxypropionic acid methyl esters, 2-methoxy propyl acetoacetic ester, 2-ethoxy-propionic acid methyl esters, 2-ethoxyl ethyl propionate, 2-oxygen-2 Methylpropionic acid methyl esters, 2-oxygen-2 Methylpropionic acid ethyl ester, 2-methoxyl group-2 Methylpropionic acid methyl esters, 2-methoxyl group-2 Methylpropionic acid ethyl ester, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, Propyl pyruvate, methyl acetoacetate, ethyl 3-oxobutanoate, 2-oxy butyrate methyl esters, 2-oxy butyrate ethyl ester; Toluene, YLENE etc. are aromatic hydrocarbon based; Amides such as N-Methyl pyrrolidone, DMAC N,N etc.
Above-mentioned solvent can be separately or suitable mix more than 2 kinds and using.
[tinting material]
Photopolymerizable composition of the present invention can contain tinting material.The tone of tinting material is not special to be limited, and can be any one of pigment, dyestuff or natural pigment.Owing to pursue high meticulous colour developing and thermotolerance recently, thereby as preferred color developing height of the tinting material among the present invention and the high tinting material of thermotolerance, the high tinting material of particularly heat-resisting decomposability.Usually use pigment (preferred especially pigment dyestuff), carbon black.Can enumerate (C.I. as above-mentioned pigment dyestuff at " Color Index "; The Society of Dyners and Colourists society distribution) be classified as the compound of pigment in, can enumerating particularly is described below has the compound of color index (C.I.) sequence number.
C.I. Pigment Yellow 73 1; C.I. Pigment Yellow 73 3; C.I. pigment Yellow 12; C.I. pigment yellow 13; C.I. pigment Yellow 14; C.I. Pigment Yellow 73 15; C.I. Pigment Yellow 73 16; C.I. pigment yellow 17; C.I. Pigment Yellow 73 20; C.I. Pigment Yellow 73 24; C.I. Pigment Yellow 73 31; C.I. Pigment Yellow 73 55; C.I. Pigment Yellow 73 60; C.I. Pigment Yellow 73 61; C.I. Pigment Yellow 73 65; C.I. Pigment Yellow 73 71; C.I. Pigment Yellow 73 73; C.I. Pigment Yellow 73 74; C.I. pigment yellow 81; C.I. pigment yellow 83; C.I. Pigment Yellow 73 93; C.I. Pigment Yellow 73 95; C.I. Pigment Yellow 73 97; C.I. Pigment Yellow 73 98; C.I. Pigment Yellow 73 100; C.I. Pigment Yellow 73 101; C.I. Pigment Yellow 73 104; C.I. Pigment Yellow 73 106; C.I. Pigment Yellow 73 108; C.I. Pigment Yellow 73 109; C.I. Pigment Yellow 73 110; C.I. Pigment Yellow 73 113; C.I. Pigment Yellow 73 114; C.I. Pigment Yellow 73 116; C.I. Pigment Yellow 73 117; C.I. Pigment Yellow 73 119; C.I. pigment Yellow 12 0; C.I. pigment Yellow 12 6; C.I. pigment Yellow 12 7; C.I. pigment Yellow 12 8; C.I. pigment Yellow 12 9; C.I. pigment yellow 13 8; C.I. pigment yellow 13 9; C.I. Pigment Yellow 73 150; C.I. Pigment Yellow 73 151; C.I. Pigment Yellow 73 152; C.I. Pigment Yellow 73 153; C.I. pigment yellow 154; C.I. Pigment Yellow 73 155; C.I. Pigment Yellow 73 156; C.I. Pigment Yellow 73 166; C.I. Pigment Yellow 73 168; C.I. pigment yellow 17 5; C.I. Pigment Yellow 73 180; C.I. Pigment Yellow 73 185;
C.I. pigment orange 1, C.I. pigment orange 5, C.I. pigment Orange 13, C.I. pigment orange 14, C.I. pigment orange 16, C.I. pigment orange 17, C.I. pigment orange 24, C.I. pigment orange 34, C.I. pigment orange 36, C.I. pigment orange 38, C.I. pigment orange 40, C.I. pigment orange 43, C.I. pigment orange 46, C.I. pigment orange 49, C.I. pigment orange 51, C.I. pigment orange 61, C.I. pigment orange 63, C.I. pigment orange 64, C.I. pigment orange 71, C.I. pigment orange 73; C.I. pigment violet 1, C.I. pigment violet 19, C.I. pigment Violet 23, C.I. pigment violet 29, C.I. pigment violet 32, C.I. pigment violet 36, C.I. pigment violet 38;
C.I. Pigment red 1; C.I. Pigment red 2; C.I. pigment red 3; C.I. pigment red 4; C.I. Pigment red 5; C.I. Pigment red 6; C.I. Pigment red 7; C.I. pigment Red 8; C.I. Pigment Red 9; C.I. Pigment red 10; C.I. Pigment red 11; C.I. Pigment red 12; C.I. Pigment red 14; C.I. Pigment red 15; C.I. Pigment red 16; C.I. Pigment red 17; C.I. Pigment red 18; C.I. Pigment red 19; C.I. pigment red 21; C.I. Pigment red 22; C.I. Pigment red 23; C.I. pigment red 30; C.I. pigment red 31; C.I. pigment red 32; C.I. pigment red 37; C.I. pigment red 38; C.I. pigment red 40; C.I. pigment red 41; C.I. pigment red 42; C.I. pigment red 4 8:1; C.I. pigment red 4 8:2; C.I. pigment red 4 8:3; C.I. pigment red 4 8:4; C.I. pigment red 4 9:1; C.I. pigment red 4 9:2; C.I. Pigment red 50:1; C.I. Pigment red 52:1; C.I. Pigment red 53:1; C.I. Pigment red 57; C.I. Pigment red 57:1; C.I. Pigment red 57:2; C.I. Pigment red 58:2; C.I. Pigment red 58:4; C.I. Pigment red 60:1; C.I. Pigment red 63:1; C.I. Pigment red 63:2; C.I. Pigment red 64:1; C.I. pigment red 81: 1; C.I. pigment Red 83; C.I. pigment Red 88; C.I. Pigment Red 9 0:1; C.I. Pigment Red 97; C.I. Pigment red 101; C.I. Pigment red 102; C.I. Pigment red 104; C.I. Pigment red 105; C.I. Pigment red 106; C.I. Pigment red 108; C.I. Pigment Red 112; C.I. Pigment red 113; C.I. Pigment red 114; C.I. pigment red 122; C.I. pigment red 123; C.I. Pigment red 144; C.I. pigment red 146; C.I. pigment red 149; C.I. Pigment red 150; C.I. Pigment red 151; C.I. Pigment red 166; C.I. Pigment red 168; C.I. Pigment red 170; C.I. Pigment red 171; C.I. Pigment red 172; C.I. Pigment red 174; C.I. Pigment red 175; C.I. Pigment red 176; C.I. Pigment red 177; C.I. Pigment red 178; C.I. Pigment red 179; C.I. Pigment red 180; C.I. Pigment red 185; C.I. Pigment red 187; C.I. Pigment red 188; C.I. Pigment red 190; C.I. Pigment red 193; C.I. Pigment red 194; C.I. Pigment red 202; C.I. Pigment red 206; C.I. Pigment Red 207; C.I. Pigment red 208; C.I. Pigment red 209; C.I. pigment red 21 5; C.I. pigment red 21 6; C.I. Pigment red 220; C.I. Pigment red 224; C.I. Pigment red 226; C.I. Pigment red 242; C.I. Pigment red 243; C.I. Pigment red 245; C.I. Pigment red 254; C.I. Pigment red 255; C.I. Pigment red 264; C.I. Pigment red 265;
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; C.I. pigment Green 7, C.I. pigment green 36; C.I. pigment brown 23, C.I. pigment brown 25; C.I. Pigment black 1, C.I. Pigment black 7.
In addition, these pigment dyestuffs can be made with extra care through for example sulfuric acid recrystallization method, solvent wash method or their combination etc. and use.
In addition, can enumerate titanium oxide, permanent white, lime carbonate, zinc oxide, lead sulfate, lead and yellow-collation, zinc yellow, RED IRON OXIDE (III), cadmium red, ultramarine, dark purple, chromoxide green, cobalt green, umber, black, the synthetic iron oxide black of titanium, carbon black etc. as the concrete example of mineral dye.Among the present invention above-mentioned pigment dyestuff and mineral dye can be separately separately or mix more than 2 kinds and use, and can be with pigment dyestuff and mineral dye and usefulness.With respect to 100 weight part free-radical polymerised compounds (b), the usage quantity of tinting material is generally 0~6000 weight part among the present invention.
Among the present invention, above-mentioned each pigment can carry out modification to its particle surface and uses as required with polymkeric substance.Can enumerate the for example special polymkeric substance of opening record in the flat 8-259876 communique etc., commercially available various colo(u)rant dispersion with polymkeric substance or oligopolymer etc. as the polymkeric substance of the particle surface of modified pigment.Above-mentioned document is all enrolled specification sheets as a reference.
[dispersion agent]
Tinting material among the present invention can use with dispersion agent as required.Can enumerate for example tensio-active agent such as pigment derivative and positively charged ion system, negatively charged ion system, nonionic system, both sexes, silicone-based, fluorine system as this dispersion agent.Concrete example as above-mentioned tensio-active agent can be enumerated Voranol EP 2001 classes such as polyoxyethylene laurel ether, polyoxyethylene stearyl ether, polyoxyl 10 oleyl ether; Polyxyethylated phenylate classes such as T 46155 n-octyl phenylate, T 46155 n-nonyl phenylate; Polyethylene glycol di such as polyethylene glycol dilaurate, polyglycol distearate class; The Sorbitol Powder fatty acid ester; Fatty acid modified polyester; The tertiary amine modified polyurethane; Gather piperazines etc., also have following trade(brand)name: KP (SHIN-ETSU HANTOTAI's chemical industry (strain) manufacturing), conflux (Port リ Off ロ one) (manufacturing of chemical company of common prosperity society), F-TOP (opening up Ke Mu manufacturing company (ト one ケ system プ ロ ダ Network Star) makes), the floating gram of MAG (メ ガ Off ア Star Network) (big Japanese ink chemical industrial company makes), Off ロ ラ one De (Sumitomo 3M manufactured), AsahiGuard, Suo Fulong (サ one Off ロ Application) (above, Asahi Glass manufactured), Disperbyk (Bi Ke chemistry (Japan) manufactured), the plain Paasche of Suo Lu (ソ Le ス パ one ス) (Jie Likang (ZENECA) manufactured) etc. in addition.These tensio-active agents can separately or mix more than 2 kinds and use.With respect to 100 weight part tinting materials, the usage quantity of tensio-active agent is generally below 70 weight parts, is preferably 0~55 weight part.
[additive]
Photopolymerizable composition of the present invention can also mix oxygen scavengers such as using phosphine, phosphonate, phosphite according to purpose and reductive agent, photographic fog prevent agent, fading prevents that agent, halation from preventing agent, white dyes, tensio-active agent, tinting material, extender, softening agent, fire retardant, inhibitor, UV light absorber, whipping agent, mould inhibitor, static inhibitor, magnetic substance or giving the additive, diluting solvent etc. of other various characteristicses.
[picture pattern formation method]
Photopolymerizable composition of the present invention can be with the negative resist that acts on following situation: be coated on the base material, partly the exposure energy ray makes its curing, removes unexposed part through alkaline-based developer and forms picture pattern.Picture pattern formation method to using photopolymerizable composition of the present invention describes.At first, behind the fluid composition of coating photopolymerizable composition on the surface of base material, carry out prebake and evaporating solvent, formation is filmed.Then, this is filmed after photomask partly makes public to the pattern-like consistent with mask, use alkaline-based developer to develop, the unexposed portion of filming is removed in dissolving.Subsequently, carry out the later stage as required and cure (postbake), can form the target image pattern.
, base material can adopt known coating processes such as spraying, rotary coating, slot coated, roller coat when being coated with the fluid composition of photopolymerizable composition.Coating thickness can suitably change according to purposes, and common dried thickness is 0.1~200 μ m, preferred 0.2~100 μ m.
In addition, also can use photopolymerizable composition of the present invention, photopolymerizable composition of the present invention promptly is set on basement membrane, clamp this polymerization rerum natura compsn with protective membrane as required according to the known form that is called dry film of industry.Basement membrane can be formed by polyester, Vestolen PP 7052, Vilaterm of for example with the polyethylene terephthalate being representative etc.This dry film is peeled off said protection film usually, driving fit on the base material that will form the resist pattern, as required at heating condition, also have and to be laminated under the pressurized conditions on the base material and to use.Use the situation pattern exposure of photopolymerizable composition of the present invention can not peel off above-mentioned basement membrane and implement with the dry film form, remove above-mentioned basement membrane and implement alkaline development this moment after exposure.
Photopolymerizable composition of the present invention can carry out polymerization through the energy of giving generations such as ultraviolet ray, visible rays, near infrared ray etc., electron rays when polyreaction, obtain subject polymer.In addition, the definition of the ultraviolet ray described in this specification sheets, near-ultraviolet ray, visible light, near infrared ray, infrared rays etc. is based on " rock ripple physics and chemistry is learned dictionary the 4th edition " (, the rock ripple in 1987) of people such as Kubo bright five volume.
Thereby photopolymerizable composition of the present invention can obtain subject polymer, cured article through giving the energy that various light sources produce such as low pressure mercury lamp, medium pressure mercury lamp, high voltage mercury lamp, ultrahigh pressure mercury lamp, xenon lamp, carbon arc lamp, metal halide lamp, luminescent lamp, tungsten lamp, argon laser, helium cadmium laser, He-Ne Lasers, krypton ion laser, various semiconductor laser, YAG laser, photodiode, CRT light source, plasma light source, electron rays, gamma-rays, ArF PRK, KrF PRK, F2 laser.
Therefore; Photopolymerizable composition of the present invention can be applied to coat the various printing ink on the substrate, various brush plate material, photo-resist, electronic photo, directly brush various recording mediums such as sensitive materialss such as plate material, hologram material, microcapsule with tackiness agent, also has caking agent, tackiness agent, tackiness agent, sealing agent and various coating.
Can when making public, use the energy-ray of above-mentioned light source for picture pattern formation method of the present invention.Special optimal wavelength is at the energy-ray of 190~450nm scope.Exposure is owing to depending on that also thickness cannot treat different things as the same, but is generally 0.5~100000J/m
2
Can enumerate the film or the substrate of for example glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamidoimide, polyimide, epoxy glass manufacturing as the base material that uses in the picture pattern formation method of the present invention, but be not limited to this.In addition, as required also can be in advance these base materials be implemented to utilize the suitable pre-treatments such as medicine processing, plasma treatment, ion plating, sputter, gas-phase reaction method, vacuum evaporation of silane coupling agent etc.
As the developing method that adopts in the picture pattern formation method of the present invention can be for example to contain in liquid method, pickling process, shower method, the spray method etc. any one.Development time is 20~30 ℃ of following preferred 5~300 seconds.In addition; Can use for example inorganic bases such as sodium hydroxide, Pottasium Hydroxide, yellow soda ash, water glass, Starso, ammonia as alkaline-based developer; Primary amine such as ethamine, Tri N-Propyl Amine class; Secondary amine such as DIETHANOL AMINE, di-n-propyl amine class; Tertiary amines such as Trimethylamine, methyl DIETHANOL AMINE, ethyl dimethyl amine, triethylamine, alkanol tertiary amines such as dimethylethanolamine, methyldiethanolamine, trolamine, pyrroles, piperidines, N-methyl piperidine, N-crassitude, 30-diazabicyclo [5.4.0]-7-undecylene, 1; 5-diazabicyclo [4.3.0]-tertiary amines such as 5-nonene, the aqueous solution of basic cpds such as quaternary ammonium salt such as TMAH, tetraethyl ammonium hydroxide.In addition, in the aqueous solution of above-mentioned basic cpd, also can add water-miscible organic solvent and/or tensio-active agents such as methyl alcohol, ethanol in right amount.
Photopolymerizable composition of the present invention for through the irradiation energy ray particularly light can generate living radical effectively, and the free-radical polymerised compound high sensitive photopolymerizable composition of polymeric at short notice.Thereby the photopolymerizable composition of the application of the invention can provide suitable to the negative resist with alkali-developable of photo anti-corrosion agent material and the picture pattern formation method of using this negative resist.And then, through adopting this picture pattern formation method suitable picture pattern can be provided.
Embodiment
Below through embodiment and comparative example the present invention is described at length, but the present invention is not limited in following content.
The compound that in embodiment and comparative example, adopts is shown in table 5~8.
Table 5
Table 6
Table 7
Table 8
(I) radical polymerization initiator (a) is synthetic
Synthetic example 1
Synthesizing of compound (101)
With 20.0g (90.8mmol) 1-furans-2-base-3-thiophene-2-base-propane-1, the 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with dripping 11.24g (109mmol) nitrite tert-butyl in 1 hour.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; Use normal hexane wash residual thing again; Thereby obtain 1-furans-2-base-3-thiophene-2-base-propane-1,2 of 22.3g, 3-triketone-2-oxime (yield 93.6%).
Then, in 250ml benzene, stir 1-furans-2-base-3-thiophene-2-base-propane-1,2 of 15.0g (60.2mmol), the sodium-acetate of 3-triketone-2-oxime and 4.94g (60.2mmol) adds the acetic anhydride of 7.37g (72.2mmol), reflux 3 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 16.1g compound (101) (yield 92.1%).
Synthetic example 2
Synthesizing of compound (102)
With 18.0g (58.0mmol) 1-(4-methoxynaphthalene-1-yl)-3-thiophene-2-base-propane-1; The 3-diketone is dissolved in the mixing solutions of 180ml THF and 90ml concentrated hydrochloric acid, then under stirring at room with dripping 7.18g (69.7mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 6 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time); Carry out drying with sal epsom; The filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again, thereby obtains 1-(4-methoxynaphthalene-1-yl)-3-thiophene-2-base-propane-1 of 18.6g; 2,3-triketone-2-oxime (yield 94.6%).
Then, in 300ml benzene, stir 15.0g (44.2mmol) 1-(4-methoxynaphthalene-1-yl)-3-thiophene-2-base-propane-1,2,3-triketone-2-oxime and 3.63g (44.2mmol) sodium-acetate add 5.41g (53.0mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (102) (yield 97.3%) of the faint yellow crystal habit of 16.4g.
Synthetic example 3
Synthesizing of compound (103)
With 22.0g (34.3mmol) 1-(9; 9-dihexyl-9H-fluorenes-2-yl)-3-(9; 10-dimethoxy phenanthrene-2-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 260ml THF and 180ml concentrated hydrochloric acid, then under stirring at room with dripping 4.25g (41.2mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 8 hours.Reaction solution is injected the 1L frozen water, extract with the 800ml chloroform.Organic layer is washed (500ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With chloroform-hexane residue is carried out recrystallization again; Thereby obtain 18.4g 1-(9,9-dihexyl-9H-fluorenes-2-yl)-3-(9,10-dimethoxy phenanthrene-2-yl)-propane-1; 2,3-triketone-2-oxime (yield 80.2%).
Then, in 300ml benzene, stir 16.0g (23.9mmol) 1-(9,9-dihexyl-9H-fluorenes-2-yl)-3-(9; 10-dimethoxy phenanthrene-2-yl)-and propane-1,2,3-triketone-2-oxime and 1.96g (23.9mmol) sodium-acetate; Add 2.93g (28.7mmol) acetic anhydride then, reflux 5 hours.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (103) (yield 78.9%) of 13.4g yellow crystal form.
Synthetic example 4
Synthesizing of compound (104)
With 20.0g (46.5mmol) 1-(4; 6-two-dimethylamino-[1; 3; 5] triazine-2-yl)-3-(9-ethyl-9H-carbazole-3-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with 40 minutes Dropwise 5 .75g (55.7mmol) nitrite tert-butyls.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With methylene dichloride-hexane residue is carried out recrystallization again, thus obtain 18.8g 1-(4,6-two-dimethylamino-[1; 3; 5] triazine-2-yl)-and 3-(9-ethyl-9H-carbazole-3-yl)-propane-1,2,3-triketone-2-oxime (yield 88.1%).
Then, in 240ml benzene, stir 13.5g (29.4mmol) 1-(4,6-two-dimethylamino-[1; 3; 5] triazine-2-yl)-and 3-(9-ethyl-9H-carbazole-3-yl)-propane-1,2,3-triketone-2-oxime and 2.41g (29.4mmol) sodium-acetate; Add 3.60g (35.3mmol) acetic anhydride then, reflux 4 hours.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out redeposition again, thereby obtains the compound (104) (yield 93.2%) of 13.7g yellow powder form.
Synthetic example 5
Synthesizing of compound (105)
With 17.2g (51.9mmol) 1-benzo [b] thiophene-2-base-3-quinolyl-4-propane-1; The 3-diketone is dissolved in the mixing solutions of 320ml THF and 160ml concentrated hydrochloric acid, then under stirring at room with dripping 6.42g (62.3mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 1L frozen water, extract with the 650ml chloroform.Organic layer is washed (400ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With chloroform-hexane residue is carried out recrystallization again; Thereby obtain 16.0g 1-benzo [b] thiophene-2-base-3-quinolyl-4-propane-1,2,3-triketone-2-oxime (yield 85.6%).
Then, in 240ml benzene, stir 12.0g (33.3mmol) 1-benzo [b] thiophene-2-base-3-quinolyl-4-propane-1,2,3-triketone-2-oxime and 2.73g (33.3mmol) sodium-acetate add 4.08g (40.0) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (105) (yield 91.1%) of the faint yellow crystal habit of 12.2g.
Synthetic example 6
Synthesizing of compound (106)
With 25.0g (73.0mmol) 1-naphthalene-2-base-3-(2-oxygen-2H-chromene-3-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 250ml THF and 125ml concentrated hydrochloric acid, then under stirring at room with dripping 9.04g (87.6mmol) nitrite tert-butyl in 1 hour.After drip finishing, stirring at room 3 hours.Reaction solution is injected the 1L frozen water, extract with the 1L chloroform.Organic layer is washed (600ml * 3 time); Carry out drying with sal epsom; The filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again, thereby obtains 25.8g 1-naphthalene-2-base-3-(2-oxygen-2H-chromene-3-yl)-propane-1; 2,3-triketone-2-oxime (yield 95.2%).
Then, in 400ml benzene, stir 20.0g (53.9mmol) 1-naphthalene-2-base-3-(2-oxygen-2H-chromene-3-yl)-propane-1,2,3-triketone-2-oxime and 4.42g (53.9mmol) sodium-acetate add 6.60g (64.6mmol) acetic anhydride, reflux 6 hours then.Subsequently; Reaction solution is injected the 500ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (106) (yield 94.4%) of the faint yellow crystal habit of 21.0g.
Synthetic example 7
Synthesizing of compound (107)
With 15.0g (38.3mmol) 1-(9-ethyl-9H-carbazole-3-yl)-3-naphthalene-1-base-propane-1; The 3-diketone is dissolved in the mixing solutions of 150ml THF and 75ml concentrated hydrochloric acid, then under stirring at room with dripping 4.74g (46.0mmol) nitrite tert-butyl in 15 minutes.After drip finishing, stirring at room 24 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 2 time); Carry out drying with sal epsom; The filtration drying agent is also heated up in a steamer and is desolvated, and with chloroform-hexane residue is carried out recrystallization again, thereby obtains 14.2g 1-(9-ethyl-9H-carbazole-3-yl)-3-naphthalene-1-base-propane-1; 2,3-triketone-2-oxime (yield 88.3%).
Then, in 200ml benzene, stir 10.0g (23.8mmol) 1-(9-ethyl-9H-carbazole-3-yl)-3-naphthalene-1-base-propane-1,2,3-triketone-2-oxime and 1.95g (23.8mmol) sodium-acetate add 2.9g (28.4mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (150ml * 2 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again, thereby obtains the compound (107) (yield 79.0%) of 8.7g pale yellow powder form.
Synthetic example 8
Synthesizing of compound (108)
With 20.0g (39.2mmol) 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-3-naphthalene-1-base-propane-1; The 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with dripping 4.86g (47.1mmol) nitrite tert-butyl in 20 minutes.After drip finishing, stirring at room 10 hours.Reaction solution is injected the 700ml frozen water, extract with the 600ml chloroform.Organic layer is washed (300ml * 2 time); Heat up in a steamer and desolvate, with chloroform-hexane residue is carried out recrystallization again, thereby obtain 19.3g 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-3-naphthalene-1-base-propane-1; 2,3-triketone-2-oxime (yield 91.3%).
Then; In 340ml benzene, stir 17.0g (31.6mmol) 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-3-naphthalene-1-base-propane-1,2,3-triketone-2-oxime and 2.59g (31.6mmol) sodium-acetate; Add 3.86g (37.8mmol) acetic anhydride then, reflux 4 hours.Subsequently; Reaction solution is injected the 700ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 2 time); After dried over sodium sulfate; The filtration drying agent is also heated up in a steamer and is desolvated, and with chloroform-hexane residue is carried out recrystallization again, thereby obtains the compound (108) (yield 95.1%) of the faint yellow crystal habit of 17.4g.
Synthetic example 9
Synthesizing of compound (201)
With 24.0g (102mmol) 1,3-two thiophene-2-base-propane-1,3-diketone are dissolved in the mixing solutions of 240ml THF and 120ml concentrated hydrochloric acid, then under stirring at room with dripping 12.57g (122mmol) nitrite tert-butyl in 1 hour.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated, and with normal hexane residue is washed, thereby obtains 25.4g 1,3-two thiophene-2-base-propane-1,2,3-triketone-2-oxime (yield 94.2%).
Then, in 250ml benzene, stir 18.0g (67.8mmol) 1,3-two thiophene-2-base-propane-1,2,3-triketone-2-oxime and 5.57g (67.8mmol) sodium-acetate add 8.31g (81.4mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 18.7g compound (201) (yield 89.5%).
Synthetic example 10
Synthesizing of compound (202)
With 18.5g (54.7mmol) 1,3-bisbenzothiazole-2-base-propane-1,3-diketone are dissolved in the mixing solutions of 185ml THF and 93ml concentrated hydrochloric acid, then under stirring at room with dripping 6.76g (65.6mmol) nitrite tert-butyl in 40 minutes.After drip finishing, stirring at room 4 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With methylene dichloride-hexane residue is carried out recrystallization again, thereby obtain 18.8g 1,3-bisbenzothiazole-2-base-propane-1; 2,3-triketone-2-oxime (yield 93.6%).
Then, in 250ml benzene, stir 13.0g (35.4mmol) 1,3-bisbenzothiazole-2-base-propane-1,2,3-triketone-2-oxime and 2.90g (35.4mmol) sodium-acetate add 4.33g (42.5mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 250ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (202) (yield 96.8%) of the faint yellow crystal habit of 14.0g.
Synthetic example 11
Synthesizing of compound (203)
With 18.0g (39.3mmol) 1; 3-two-(9-ethyl-9H-carbazole-3-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with dripping 4.86g (47.1mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 6 hours.Reaction solution is injected the 600ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With chloroform-hexane residue is carried out recrystallization again, thereby obtain 15.9g 1,3-two-(9-ethyl-9H-carbazole-3-yl)-propane-1; 2,3-triketone-2-oxime (yield 83.0%).
Then, in 200ml benzene, stir 10.0g (20.5mmol) 1,3-two-(9-ethyl-9H-carbazole-3-yl)-propane-1,2,3-triketone-2-oxime and 1.68g (20.5mmol) sodium-acetate add 2.51g (24.6mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains the compound (203) (yield 80.7%) of the faint yellow crystal habit of 8.77g.
Synthetic example 12
Synthesizing of compound (204)
With 20.0g (47.6mmol) 1; 3-two-(7-methoxyl group-2-oxygen-2H-chromene-3-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with 45 minutes Dropwise 5 .89g (57.1mmol) nitrite tert-butyls.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time); Carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again; Thereby obtain 19.7g 1; 3-two-(7-methoxyl group-2-oxygen-2H-chromene-3-yl)-propane-1,2,3-triketone-2-oxime (yield 92.1%).
Then, in 300ml benzene, stir 15.0g (33.4mmol) 1,3-two-(7-methoxyl group-2-oxygen-2H-chromene-3-yl)-propane-1; 2; 3-triketone-2-oxime and 2.74g (33.4mmol) sodium-acetate add 4.09g (40.1mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 400ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out redeposition again, thereby obtains the compound (204) (yield 94.8%) of the faint yellow crystal habit of 15.6g.
Synthetic example 13
Synthesizing of compound (301)
With 20.0g (48.0mmol) 1; 3-two-(4-methyl sulfane base-naphthalene-1-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with 30 minutes Dropwise 5 .94g (57.6mmol) nitrite tert-butyls.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 19.9g 1,3-two-(4-methyl sulfane base-naphthalene-1-yl)-propane-1; 2,3-triketone-2-oxime (yield 93.2%).
Then, in 250ml benzene, stir 15.0g (33.7mmol) 1,3-two-(4-methyl sulfane base-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 2.76g (33.7mmol) sodium-acetate add 4.12g (40.4mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 15.0g compound (301) (yield 91.6%).
Synthetic example 14
Synthesizing of compound (302)
With 22.5g (54.8mmol) 1; 3-two-(4-dimethylamino-naphthalene-1-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 225ml THF and 113ml concentrated hydrochloric acid, then under stirring at room with dripping 6.78g (65.8mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time); Carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again; Thereby obtain 22.8g 1; 3-two-(4-dimethylamino-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime (yield 94.6%).
Then, in 300ml benzene, stir 18.0g (41.0mmol) 1,3-two-(4-dimethylamino-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 3.36g (41.0mmol) sodium-acetate add 5.02g (49.1mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 500ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 18.6g compound (302) (yield 94.4%).
Synthetic example 15
Synthesizing of compound (303)
With 12.0g (16.3mmol) 1; 3-two-(9; 9-dihexyl-9H-fluorenes-2-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 120ml THF and 60ml concentrated hydrochloric acid, then under stirring at room with dripping 2.01g (19.5mmol) nitrite tert-butyl in 15 minutes.After drip finishing, stirring at room 6 hours.Reaction solution is injected the 400ml frozen water, extract with the 400ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With chloroform-hexane residue is carried out recrystallization again, thereby obtain 10.3g 1,3-two-(9; 9-dihexyl-9H-fluorenes-2-yl)-and propane-1,2,3-triketone-2-oxime (yield 82.8%).
Then, in 100ml benzene, stir 8.0g (10.4mmol) 1,3-two-(9,9-dihexyl-9H-fluorenes-2-yl)-propane-1,2,3-triketone-2-oxime and 0.86g (10.4mmol) sodium-acetate add 1.28g (12.5mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 7.57g compound (303) (yield 89.7%).
Synthetic example 16
Synthesizing of compound (304)
With 17.5g (30.8mmol) 1; 3-two-(9-propoxy-methyl-Fei-2-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 175ml THF and 88ml concentrated hydrochloric acid, then under stirring at room with dripping 3.81g (36.9mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time); Carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated, and with methylene dichloride-hexane residue is carried out recrystallization again; Thereby obtain 16.2g 1; 3-two-(9-propoxy-methyl-Fei-2-yl)-propane-1,2,3-triketone-2-oxime (yield 88.1%).
Then, in 200ml benzene, stir 13.0g (21.8mmol) 1,3-two-(9-propoxy-methyl-Fei-2-yl)-propane-1,2,3-triketone-2-oxime and 1.78g (21.8mmol) sodium-acetate add 2.66g (26.1mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 400ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out redeposition again, thereby obtains 12.6g compound (304) (yield 90.3%).
Synthetic example 17
Synthesizing of compound (305)
With 12.0g (21.4mmol) 1; 3-two-[4-(2,4, the 6-trimethylphenyl)-naphthalene-1-yl]-propane-1; The 3-diketone is dissolved in the mixing solutions of 120ml THF and 60ml concentrated hydrochloric acid, then under stirring at room with dripping 2.65g (25.7mmol) nitrite tert-butyl in 20 minutes.After drip finishing, stirring at room 16 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed, thereby obtain 11.7g 1,3-two-[4-(2; 4; The 6-trimethylphenyl)-naphthalene-1-yl]-propane-1,2,3-triketone-2-oxime (yield 92.8%).
Then, in 180ml benzene, stir 10.0g (17.0mmol) 1,3-two-[4-(2; 4, the 6-trimethylphenyl)-naphthalene-1-yl]-propane-1,2; 3-triketone-2-oxime and 1.39g (17.0mmol) sodium-acetate add 2.08g (20.3mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the chloroform extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with chloroform-hexane residue is carried out recrystallization again, thereby obtains 9.4g compound (305) (yield 87.7%).
Synthetic example 18
Synthesizing of compound (306)
With 18.0g (35.4mmol) 1,3-two-(4-phenoxy naphthalene-1-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 180ml THF and 90ml concentrated hydrochloric acid, then under stirring at room with dripping 4.38g (42.5mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 17.9g 1,3-two-(4-phenoxy naphthalene-1-yl)-propane-1; 2,3-triketone-2-oxime (yield 94.1%).
Then, in 250ml benzene, stir 15.0g (27.9mmol) 1,3-two-(4-phenoxy naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 2.29g (27.9mmol) sodium-acetate add 3.42g (33.5mmol) acetic anhydride, reflux 3 hours then.Subsequently; Reaction solution is injected the 400ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 14.7g compound (306) (yield 90.6%).
Synthetic example 19
Synthesizing of compound (307)
With 21.5g (39.8mmol) 1; 3-two-(4-phenyl sulfane base-naphthalene-1-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 215ml THF and 108ml concentrated hydrochloric acid, then under stirring at room with dripping 4.92g (47.7mmol) nitrite tert-butyl in 25 minutes.After drip finishing, stirring at room 6 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 20.8g 1,3-two-(4-phenyl sulfane base-naphthalene-1-yl)-propane-1; 2,3-triketone-2-oxime (yield 91.7%).
Then, in 270ml benzene, stir 16.0g (28.1mmol) 1,3-two-(4-phenyl sulfane base-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 2.30g (28.1mmol) sodium-acetate add 3.44g (33.7mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 500ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 15.2g compound (307) (yield 88.2%).
Synthetic example 20
Synthesizing of compound (308)
With 10.0g (14.0mmol) 1; 3-two-[4-(two tolyl-amino)-naphthalene-1-yl]-propane-1; The 3-diketone is dissolved in the mixing solutions of 100ml THF and 50ml concentrated hydrochloric acid, then under stirring at room with dripping 1.73g (16.8mmol) nitrite tert-butyl in 15 minutes.After drip finishing, stirring at room 24 hours.Reaction solution is injected the 350ml frozen water, extract with the 500ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 8.64g 1,3-two-[4-(two tolyl-amino)-naphthalene-1-yl]-propane-1; 2,3-triketone-2-oxime (yield 83.0%).
Then, in 150ml benzene, stir 7.50g (10.1mmol) 1,3-two-[4-(two tolyl-amino)-naphthalene-1-yl]-propane-1; 2; 3-triketone-2-oxime and 0.83g (10.1mmol) sodium-acetate add 1.24g (12.1mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the chloroform extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with chloroform-hexane residue is carried out recrystallization again, thereby obtains 6.32g compound (308) (yield 79.8%).
Synthetic example 21
Synthesizing of compound (401)
With 25.0g (60.6mmol) 1,3-two-(4-oxyethyl group-naphthalene-1-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 250ml THF and 125ml concentrated hydrochloric acid, then under stirring at room with dripping 7.50g (72.7mmol) nitrite tert-butyl in 45 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 800ml frozen water, extract with the 750ml chloroform.Organic layer is washed (500ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 25.6g 1,3-two-(4-oxyethyl group-naphthalene-1-yl)-propane-1; 2,3-triketone-2-oxime (yield 95.6%).
Then, in 300ml benzene, stir 18.0g (40.8mmol) 1,3-two-(4-oxyethyl group-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 3.34g (40.8mmol) sodium-acetate add 5.0g (48.9mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 500ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 19.0g compound (401) (yield 96.4%).
Synthetic example 22
Synthesizing of compound (402)
With 14.0g (23.3mmol) 1; 3-two-(9; 10-diethoxy-Fei-2-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 140ml THF and 70ml concentrated hydrochloric acid, then under stirring at room with dripping 2.88g (28.0mmol) nitrite tert-butyl in 20 minutes.After drip finishing, stirring at room 4 hours.Reaction solution is injected the 300ml frozen water, extract with the 300ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With methylene dichloride-hexane residue is carried out recrystallization again; Thereby obtain 13.7g 1,3-two-(9,10-diethoxy-Fei-2-yl)-propane-1; 2,3-triketone-2-oxime (yield 93.1%).
Then, in 150ml benzene, stir 10.0g (15.9mmol) 1,3-two-(9,10-diethoxy-Fei-2-yl)-propane-1,2,3-triketone-2-oxime and 1.3g (41.0mmol) sodium-acetate add 1.95g (19.1mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 10.1g compound (402) (yield 94.8%).
Synthetic example 23
Synthesizing of compound (403)
With 22g (16.3mmol) 1,3-two-(6-isobutoxy-naphthalene-2-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 220ml THF and 110ml concentrated hydrochloric acid, then under stirring at room with 30 minutes Dropwise 5 .8g (56.3mmol) nitrite tert-butyls.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 700ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With chloroform-hexane residue is carried out recrystallization again, thereby obtain 21.9g 1,3-two-(6-isobutoxy-naphthalene-2-yl)-propane-1; 2,3-triketone-2-oxime (yield 93.7%).
Then, in 300ml benzene, stir 18.0g (36.2mmol) 1,3-two-(6-isobutoxy-naphthalene-2-yl)-propane-1,2,3-triketone-2-oxime and 2.97g (36.2mmol) sodium-acetate add 4.43g (43.4mmol) acetic anhydride, reflux 6 hours then.Subsequently; Reaction solution is injected the 800ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 18.7g compound (403) (yield 96.0%).
Synthetic example 24
Synthesizing of compound (404)
With 15.0g (21.8mmol) 1; 3-two-(9; 9-dibutoxy-9H-fluorenes-2-yl)-propane-1, the 3-diketone is dissolved in the mixing solutions of 150ml THF and 75ml concentrated hydrochloric acid, then under stirring at room with dripping 2.69g (26.1mmol) nitrite tert-butyl in 15 minutes.After drip finishing, stirring at room 7 hours.Reaction solution is injected the 400ml frozen water, extract with the 300ml chloroform.Organic layer is washed (200ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With methylene dichloride-hexane residue is carried out recrystallization again; Thereby obtain 12.9g 1,3-two-(9,9-dibutoxy-9H-fluorenes-2-yl)-propane-1; 2,3-triketone-2-oxime (yield 82.4%).
Then, in 100ml benzene, stir 8.5g (11.8mmol) 1,3-two-(9,9-dibutoxy-9H-fluorenes-2-yl)-propane-1,2,3-triketone-2-oxime and 0.97g (11.8mmol) sodium-acetate add 1.45g (14.2mmol) acetic anhydride, reflux 5 hours then.Subsequently; Reaction solution is injected the 300ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (200ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out redeposition again, thereby obtains 8.1g compound (404) (yield 90.5%).
Synthetic example 25
Synthesizing of compound (405)
With 20.0g (38.4mmol) 1; 3-two-(4-cyclohexyl oxygen-naphthalene-1-yl)-propane-1; The 3-diketone is dissolved in the mixing solutions of 200ml THF and 100ml concentrated hydrochloric acid, then under stirring at room with dripping 4.76g (46.1mmol) nitrite tert-butyl in 30 minutes.After drip finishing, stirring at room 5 hours.Reaction solution is injected the 500ml frozen water, extract with the 500ml chloroform.Organic layer is washed (300ml * 3 time), carry out drying with sal epsom, the filtration drying agent is also heated up in a steamer and is desolvated; With normal hexane residue is washed again, thereby obtain 19.6g 1,3-two-(4-cyclohexyl oxygen-naphthalene-1-yl)-propane-1; 2,3-triketone-2-oxime (yield 92.9%).
Then, in 300ml benzene, stir 16.0g (29.1mmol) 1,3-two-(4-cyclohexyl oxygen-naphthalene-1-yl)-propane-1,2,3-triketone-2-oxime and 2.39g (29.1mmol) sodium-acetate add 3.57g (34.9mmol) acetic anhydride, reflux 4 hours then.Subsequently; Reaction solution is injected the 500ml frozen water, use the ethyl acetate extraction crude product, organic layer is washed (300ml * 3 time); After dried over mgso; The filtration drying agent is also heated up in a steamer and is desolvated, and with vinyl acetic monomer-hexane residue is carried out recrystallization again, thereby obtains 16.5g compound (405) (yield 95.8%).
The results of elemental analyses of synthetic radical polymerization initiator of the present invention is shown in table 9~12 in above-mentioned synthetic routine 1~25.
The results of elemental analyses of table 9 synthetic radical polymerization initiator
The results of elemental analyses of table 10 synthetic radical polymerization initiator
The results of elemental analyses of table 11 synthetic radical polymerization initiator
The results of elemental analyses of table 12 synthetic radical polymerization initiator
(II) modulation of photopolymerizable composition and susceptibility evaluation
Embodiment 1~21
Will be as compound 6 weight parts shown in table 13~16 of radical polymerization initiator of the present invention (a), as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound (b), as the polymethyl acrylate of tackiness agent (weight-average molecular weight about 30000, number-average molecular weight about 10000) 100 weight parts, cooperate the modulation coating fluid as pimelinketone 1600 weight parts of solvent.Use spin coater that this coating fluid is applied on the stainless steel plate, in baking oven 40 ℃ of dryings 10 minutes.The thickness that removes after desolvating through drying is 1.5 μ m.This coated film is seen through the light (9.0mW/cm of the BPF. irradiation high voltage mercury lamp of 350~380nm light across alternative
2), measure the IR spectrum (reflection) of photopolymerizable composition simultaneously, the characteristic absorption of monitoring propenyl is 810cm
-1Intensity.Based on the mensuration result of this IR, be benchmark with the rayed previous crops, calculate the ratio of the propenyl that the moment after beginning 15 seconds from rayed is consumed owing to polymerization, the result is shown in table 13~16.
Comparative example 1~3
Will be as 6 weight parts of the compound shown in the table 13 of radical polymerization initiator, as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound, as the polymethylmethacrylate of tackiness agent (weight-average molecular weight about 30000, number-average molecular weight about 10000) 100 weight parts, cooperate the modulation coating fluid as pimelinketone 1600 weight parts of solvent.According to this coating fluid being carried out film forming, rayed with same step and the condition of the foregoing description, calculate the monomeric rate of consumption of moment propenyl after beginning 15 seconds from rayed, the result is shown in Table 13.
Table 13
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 1 | Compound (101) | 14.5 |
Embodiment 2 | Compound (102) | 18.6 |
Embodiment 3 | Compound (103) | 12.8 |
Embodiment 4 | Compound (104) | 15.0 |
Embodiment 5 | Compound (105) | 13.1 |
Embodiment 6 | Compound (106) | 17.4 |
Embodiment 7 | Compound (107) | 21.1 |
Embodiment 8 | Compound (108) | 25.2 |
Comparative example 1 | Compound (1) | 2.3 |
Comparative example 2 | Compound (2) | 1.2 |
Comparative example 3 | Compound (3) | 3.1 |
Table 14
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 9 | Compound (201) | 14.1 |
Embodiment 10 | Compound (202) | 13.8 |
Embodiment 11 | Compound (203) | 14.7 |
Embodiment 12 | Compound (204) | 16.3 |
Table 15
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 13 | Compound (301) | 18.8 |
Embodiment 14 | Compound (302) | 17.4 |
Embodiment 15 | Compound (303) | 14.1 |
Embodiment 16 | Compound (304) | 15.3 |
Table 16
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 17 | Compound (401) | 19.4 |
Embodiment 18 | Compound (402) | 16.1 |
Embodiment 19 | Compound (403) | 18.6 |
Embodiment 20 | Compound (404) | 14.3 |
Embodiment 21 | Compound (405) | 18.7 |
Use the photopolymerizable composition (embodiment 1~21) and the known α of use of radical polymerization initiator of the present invention; α '-two ketoxime ester is compared as the situation (comparative example 1~3) of radical polymerization initiator; Can more effectively generate radical during rayed, and make the propenyl polymerization.That is, the general formula of the application of the invention (1) expression, with in the 1-position with the 3-position has heterocyclic radical or the condensation polycyclic alkyl is the α of characteristics, α '-diketone oxime ester compound can be realized high sensitive as radical polymerization initiator.
Embodiment 22~75
Will be as compound 5 weight parts shown in table 17~20 of radical polymerization initiator of the present invention (a), as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound (b), as the compound (5) of sensitizing agent (c) or compound (6) 0 or 1 weight part, as the polymethyl acrylate of tackiness agent (weight-average molecular weight about 30000, number-average molecular weight about 10000) 100 weight parts, cooperate the modulation coating fluid as pimelinketone 1600 weight parts of solvent.Use spin coater that this coating fluid is applied on the stainless steel plate, in baking oven 40 ℃ of dryings 10 minutes.The thickness that removes after desolvating through drying is 1.5 μ m.This coated film is seen through the light (10.0mW/cm of the BPF. irradiation high voltage mercury lamp of 350~380nm light across alternative
2), measure the IR spectrum (reflection) of photopolymerizable composition simultaneously, the characteristic absorption of monitoring propenyl is 810cm
-1Intensity.Based on the mensuration result of this IR, be benchmark with the rayed previous crops, calculate (rayed amount 100mJ/cm after beginning 10 seconds from rayed
2) the ratio of the propenyl that is consumed owing to polymerization of the moment, the result is shown in table 17~20.
Comparative example 4~9
Will be as compound 5 weight parts shown in the table 17 and 20 of radical polymerization initiator, as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound, as the compound (5) of sensitizing agent or compound (6) 0 or 1 weight part, as the polymethyl acrylate of tackiness agent (weight-average molecular weight about 30000, number-average molecular weight about 10000) 100 weight parts, cooperate the modulation coating fluid as pimelinketone 1600 weight parts of solvent.According to this coating fluid being carried out film forming, rayed, calculate (rayed amount 100mJ/cm after beginning 10 seconds from rayed with same step and the condition of the foregoing description
2) the monomeric rate of consumption of moment propenyl, the result is shown in the table 17 and 20.
Table 17
Example number | Radical polymerization initiator | Sensitizing agent | The rate of consumption of propenyl (%) |
Embodiment 22 | Compound (101) | Do not have | 11.7 |
Embodiment 23 | Compound (101) | Compound (5) | 19.6 |
Embodiment 24 | Compound (101) | Compound (6) | 21.5 |
Embodiment 25 | Compound (102) | Do not have | 14.8 |
Embodiment 26 | Compound (102) | Compound (5) | 17.8 |
Embodiment 27 | Compound (102) | Compound (6) | 19.2 |
Embodiment 28 | Compound (106) | Do not have | 13.1 |
Embodiment 29 | Compound (106) | Compound (5) | 18.1 |
Embodiment 30 | Compound (106) | Compound (6) | 17.4 |
Embodiment 31 | Compound (107) | Do not have | 17.2 |
Embodiment 32 | Compound (107) | Compound (5) | 20.6 |
Embodiment 33 | Compound (107) | Compound (6) | 21.5 |
Embodiment 34 | Compound (108) | Do not have | 22.4 |
Embodiment 35 | Compound (108) | Compound (5) | 23.9 |
Embodiment 36 | Compound (108) | Compound (6) | 23.3 |
Comparative example 4 | Compound (1) | Do not have | 1.8 |
Comparative example 5 | Compound (1) | Compound (5) | 2.8 |
Comparative example 6 | Compound (1) | Compound (6) | 4.3 |
Table 18
Example number | Radical polymerization initiator | Sensitizing agent | The rate of consumption of propenyl (%) |
Embodiment 37 | Compound (201) | Do not have | 10.5 |
Embodiment 38 | Compound (201) | Compound (5) | 18.6 |
Embodiment 39 | Compound (201) | Compound (6) | 21.2 |
Embodiment 40 | Compound (202) | Do not have | 10.2 |
Embodiment 41 | Compound (202) | Compound (5) | 16.3 |
Embodiment 42 | Compound (202) | Compound (6) | 18.4 |
Embodiment 43 | Compound (203) | Do not have | 11.0 |
Embodiment 44 | Compound (203) | Compound (5) | 17.8 |
Embodiment 45 | Compound (203) | Compound (6) | 17.1 |
Embodiment 46 | Compound (204) | Do not have | 12.1 |
Embodiment 47 | Compound (204) | Compound (5) | 19.6 |
Embodiment 48 | Compound (204) | Compound (6) | 21.0 |
Table 19
Example number | Radical polymerization initiator | Sensitizing agent | The rate of consumption of propenyl (%) |
Embodiment 49 | Compound (301) | Do not have | 16.2 |
Embodiment 50 | Compound (301) | Compound (5) | 20.6 |
Embodiment 51 | Compound (301) | Compound (6) | 23.2 |
Embodiment 52 | Compound (302) | Do not have | 15.0 |
Embodiment 53 | Compound (302) | Compound (5) | 18.4 |
Embodiment 54 | Compound (302) | Compound (6) | 21.5 |
Embodiment 55 | Compound (303) | Do not have | 10.8 |
Embodiment 56 | Compound (303) | Compound (5) | 16.7 |
Embodiment 57 | Compound (303) | Compound (6) | 15.1 |
Embodiment 58 | Compound (304) | Do not have | 12.1 |
Embodiment 59 | Compound (304) | Compound (5) | 17.1 |
Embodiment 60 | Compound (304) | Compound (6) | 18.8 |
Table 20
Example number | Radical polymerization initiator | Sensitizing agent | The rate of consumption of propenyl (%) |
Embodiment 61 | Compound (401) | Do not have | 17.1 |
Embodiment 62 | Compound (401) | Compound (5) | 21.7 |
Embodiment 63 | Compound (401) | Compound (6) | 24.2 |
Embodiment 64 | Compound (402) | Do not have | 13.9 |
Embodiment 65 | Compound (402) | Compound (5) | 17.3 |
Embodiment 66 | Compound (402) | Compound (6) | 18.6 |
Embodiment 67 | Compound (403) | Do not have | 16.0 |
Embodiment 68 | Compound (403) | Compound (5) | 20.6 |
Embodiment 69 | Compound (403) | Compound (6) | 22.0 |
Embodiment 70 | Compound (404) | Do not have | 12.4 |
Embodiment 71 | Compound (404) | Compound (5) | 16.9 |
Embodiment 72 | Compound (404) | Compound (6) | 16.1 |
Embodiment 73 | Compound (405) | Do not have | 16.2 |
Embodiment 74 | Compound (405) | Compound (5) | 20.3 |
Embodiment 75 | Compound (405) | Compound (6) | 21.8 |
Comparative example 7 | Compound (3) | Do not have | 2.4 |
Comparative example 8 | Compound (3) | Compound (5) | 3.1 |
Comparative example 9 | Compound (3) | Compound (6) | 4.8 |
The photopolymerizable composition (embodiment 22~75) that uses radical polymerization initiator of the present invention is with 100mJ/cm
2Few like this exposure just can generate radical, and makes the propenyl polymerization, forms the very high photopolymerizable composition of susceptibility.And then, for the embodiment that in photopolymerizable composition, contains sensitizing agent, to compare with the embodiment that in photopolymerizable composition, does not contain sensitizing agent, the polymerization susceptibility improves.In addition, with the known α of use, α '-two ketoxime ester is compared as the comparative example 4~9 of radical polymerization initiator, and embodiments of the invention 22~75 susceptibilitys are obviously high.That is, do not have high sensitive even photopolymerizable composition of the present invention does not contain sensitizing agent yet, but through and can form the higher photopolymerizable composition of susceptibility with sensitizing agent.
Embodiment 76~96 and comparative example 10~12
(modulation of acrylics solution (1))
Add 800 weight part pimelinketone to reaction soln, when container feeds nitrogen, be heated to 100 ℃, under this temperature with the mixture that dripped following monomer and thermal polymerization in 1 hour and carry out polyreaction.
Vinylbenzene 60.0 weight parts
Methylacrylic acid 60.0 weight parts
TEB 3K 65.0 weight parts
NSC 20956 65.0 weight parts
Diisopropyl azodicarboxylate 10.0 weight parts
After the dropping, further after 3 hours, add the solution that dissolves 2.0 weight part Diisopropyl azodicarboxylates with 50.0 weight part pimelinketone, further continue reaction 1 hour, obtain the solution of the acrylics of weight-average molecular weight about 40,000 at 100 ℃ 100 ℃ of reactions.After being cooled to room temperature, about 2g resin solution of taking a sample was measured nonvolatile component 180 ℃ of heat dryings 20 minutes, and adding pimelinketone to nonvolatile component to previous synthetic resin solution is 20%, thus modulation acrylics solution (1).
Add, mix Dipentaerythritol five propenoate (Sartomer company, SR399) 100 weight parts as free-radical polymerised compound (b), as comprise acrylics solution (1) 500 weight part of the solution of alkali soluble resins (c), as pimelinketone 400 weight parts of solvent, as compound 6 weight parts shown in table 21~23 of radical polymerization initiator (a), modulate uniform photopolymerizable composition solution.
Disc filter with aperture 0.2 μ m filters above-mentioned photopolymerizable composition solution, uses spin coater to be applied on the stainless steel plate (#600 grinding), in baking oven, removes and desolvates 80 ℃ of heat dryings 3 minutes.The thickness that is formed at the photopolymerizable composition on the stainless steel plate after the drying is 2 μ m.This photopolymerizable composition film is seen through the light (9.0mW/cm of the BPF. irradiation high voltage mercury lamp of 350~380nm light across alternative
2), measure the IR spectrum of photopolymerizable composition film, be 810cm by the characteristic absorption of propenyl
-1The change calculations of absorption intensity go out with respect to before the rayed in the rate of consumption of rayed propenyl after 15 seconds.The result is shown in table 21~23.
Table 21
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 76 | Compound (101) | 14.5 |
Embodiment 77 | Compound (102) | 18.6 |
Embodiment 78 | Compound (103) | 12.8 |
Embodiment 79 | Compound (104) | 15.0 |
Embodiment 80 | Compound (105) | 13.1 |
Embodiment 81 | Compound (106) | 17.4 |
Embodiment 82 | Compound (107) | 21.1 |
Embodiment 83 | Compound (108) | 25.2 |
Comparative example 10 | Compound (1) | 2.3 |
Comparative example 11 | Compound (2) | 1.2 |
Comparative example 12 | Compound (3) | 3.1 |
Table 22
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 84 | Compound (201) | 14.1 |
Embodiment 85 | Compound (202) | 13.8 |
Embodiment 86 | Compound (203) | 14.7 |
Embodiment 87 | Compound (204) | 16.3 |
Table 23
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) |
Embodiment 88 | Compound (401) | 19.4 |
Embodiment 89 | Compound (402) | 16.1 |
Embodiment 90 | Compound (403) | 18.6 |
Embodiment 91 | Compound (404) | 14.3 |
Embodiment 92 | Compound (405) | 18.7 |
Embodiment 93 | Compound (301) | 18.8 |
Embodiment 94 | Compound (302) | 17.4 |
Embodiment 95 | Compound (303) | 14.1 |
Embodiment 96 | Compound (304) | 15.3 |
Use the photopolymerizable composition (embodiment 76~96) and the known α of use of radical polymerization initiator of the present invention (a); α '-two ketoxime ester is compared as the situation (comparative example 10~12) of radical polymerization initiator; Can more effectively generate radical during rayed, and make the propenyl polymerization.That is, the general formula of the application of the invention (1) expression, with in the 1-position with the 3-position has heterocyclic radical or the condensation polycyclic alkyl is the α of characteristics, α '-diketone oxime ester compound can be realized high sensitive as radical polymerization initiator.In addition; Photopolymerizable composition before the rayed that on stainless steel plate, forms among the embodiment 76~96 was flooded about 1 minute in the tetramethylammonium hydroxide aqueous solution of 0.2 weight % concentration at 20 ℃; The result can confirm that photopolymerizable composition of the present invention with suitable speed dissolving, is developed by alkaline-based developer.
(III) modulation of photopolymerizable composition and storage stability test
Embodiment 97~103
Modulation comprises the coating fluid of photopolymerizable composition, and this photopolymerizable composition comprises: as compound 6 weight parts shown in the table 24 and 25 of radical polymerization initiator of the present invention (a), as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound (b), as polymethyl acrylate 100 weight parts of tackiness agent, as pimelinketone 1600 weight parts of solvent.This coating fluid is carried out film forming, rayed with the foregoing description 76~96 same step and conditions, calculate the monomeric rate of consumption of propenyl in the moment after beginning 15 seconds from rayed, the result is shown in the table 24 and 25.And then, implementing the storage stability test according to following method, its result is shown in the table 24 and 25.
(storage stability test I)
Will be in embodiment and comparative example synthetic coating fluid in the dark, 40 ℃ preserved for 2 weeks.Subsequently, have or not gelation to estimate storage stability through this coating fluid.
G: storage stability good (, not finding gelation) with not variation before the preservation
N: storage stability relatively poor (discovery gelation)
Comparative example 13
Except radical polymerization initiator (a) 6 weight parts with the foregoing description 97~103 replace with compound (7) 6 weight parts, carry out identical modulation, carry out identical evaluation.The result is shown in Table 24.
Table 24
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) | Storage stability |
Embodiment 97 | Compound (301) | 18.8 | G |
Embodiment 98 | Compound (302) | 17.4 | G |
Comparative example 13 | Compound (7) | 18.5 | N |
Table 25
Example number | Radical polymerization initiator | The rate of consumption of propenyl (%) | Storage stability |
Embodiment 99 | Compound (401) | 19.4 | G |
Embodiment 100 | Compound (402) | 16.1 | G |
Embodiment 101 | Compound (403) | 18.6 | G |
Embodiment 102 | Compound (404) | 14.3 | G |
Embodiment 103 | Compound (405) | 18.7 | G |
Use the photopolymerizable composition (embodiment 97~103) of radical polymerization initiator of the present invention when rayed, can more effectively generate radical, and make the propenyl polymerization, and under 40 ℃, the preservation condition in 2 week, do not find gelation.But, using known α, α '-two ketoxime ester is as the situation (comparative example 13) of radical polymerization initiator, though be high sensitive, under 40 ℃, the preservation condition in 2 week, finds gelation.That is, the compound of the general formula of the application of the invention (1) expression can be realized high sensitive and improve storage stability as radical polymerization initiator.In addition, can know that the A in the general formula (1) is identical condensation polycyclic alkyl with B and has alkoxyl group as substituent situation, through forming the alkoxyl group of carbonatoms more than 2, can improve storage stability by the comparison of embodiment 99 and comparative example 13.
Embodiment 104~111
Modulation comprises the sensitization liquid of photopolymerizable composition, and this photopolymerizable composition comprises: as compound 6 weight parts shown in the table 26 of radical polymerization initiator of the present invention (a), as dipentaerythritol acrylate 100 weight parts of free-radical polymerised compound (b), as polymethyl acrylate 100 weight parts of tackiness agent, as pimelinketone 1600 weight parts of solvent.Through following method this sensitization liquid is implemented the storage stability test, confirm raising effect by the storage stability of substituting group generation.The evaluation and the embodiment 97~103 of storage stability test likewise carry out, and its result is shown in Table 26.
Comparative example 14
Except radical polymerization initiator (a) 6 weight parts with the foregoing description 104~111 replace with compound (7) 6 weight parts, carry out identical modulation, carry out identical evaluation.The result is shown in Table 26.
Table 26
Example number | Radical polymerization initiator | Storage stability |
Embodiment 104 | Compound (301) | G |
Embodiment 105 | Compound (302) | G |
Embodiment 106 | Compound (303) | G |
Embodiment 107 | Compound (304) | G |
Embodiment 108 | Compound (305) | G |
Embodiment 109 | Compound (306) | G |
Embodiment 110 | Compound (307) | G |
Embodiment 111 | Compound (308) | G |
Comparative example 14 | Compound (7) | N |
Embodiment 112~126
Add, mix Dipentaerythritol five propenoate (Sartomer company, SR399) 100 weight parts as free-radical polymerised compound (b), as comprise acrylics solution (1) 500 weight part of the solution of alkali soluble resins (c), as pimelinketone 400 weight parts of solvent, as compound 6 weight parts shown in the table 27 of radical polymerization initiator (a), modulate uniform photopolymerizable composition solution.Through implementing the storage stability test with above-mentioned same method, its result is shown in Table 27 to this photopolymerizable composition solution.
Table 27
Example number | Radical polymerization initiator | Storage stability |
Embodiment 112 | Compound (401) | G |
Embodiment 113 | Compound (402) | G |
Embodiment 114 | Compound (403) | G |
Embodiment 115 | Compound (404) | G |
Embodiment 116 | Compound (405) | G |
Embodiment 117 | Compound (301) | G |
Embodiment 118 | Compound (302) | G |
Embodiment 119 | Compound (303) | G |
Embodiment 120 | Compound (304) | G |
Embodiment 121 | Compound (305) | G |
Embodiment 122 | Compound (306) | G |
Embodiment 123 | Compound (307) | G |
Embodiment 124 | Compound (308) | G |
Embodiment 125 | Compound (309) | G |
Embodiment 126 | Compound (310) | G |
The photopolymerizable composition (embodiment 112~126) that uses radical polymerization initiator of the present invention is not found gelation under 40 ℃, the preservation condition in 2 week.That is, the compound of the general formula of the application of the invention (1) expression can improve storage stability as radical polymerization initiator.
Embodiment 127~135
Modulation comprises the sensitization liquid of photopolymerizable composition, and this photopolymerizable composition comprises: as compound 6 weight parts shown in the table 28 of radical polymerization initiator of the present invention (a), as pentaerythritol triacrylate 100 weight parts of free-radical polymerised compound (b), as polymethyl acrylate 100 weight parts of tackiness agent, as pimelinketone 1600 weight parts of solvent.Through following method this sensitization liquid is implemented the storage stability test.Its result is shown in Table 28.
(storage stability test II)
After synthetic sensitization liquid in embodiment and comparative example measured viscosity, in the dark, 50 ℃ preserved 10 days.Subsequently, measuring the viscosity of this sensitization liquid, is that benchmark calculates the ratio that viscosity changes with the viscosity before preserving, and estimates storage stability.Viscosity adopts oscillatory viscometer VM-100 (yamaichi Electronics Co., Ltd.'s manufacturing) to measure at 25 ℃.
A: viscosity changes in 0~10%
B: confirm that 11~40% viscosity increases
C: confirm that 41~80% viscosity increases
D: confirm that the viscosity more than 81% increases
Comparative example 15
Except radical polymerization initiator (a) 6 weight parts with the foregoing description 127~135 replace with compound (7) 6 weight parts, carry out identical modulation, carry out identical evaluation.The result is shown in Table 28.
Table 28
Example number | Radical polymerization initiator | Storage stability |
Embodiment 127 | Compound (401) | A |
Embodiment 128 | Compound (402) | A |
Embodiment 129 | Compound (403) | A |
Embodiment 130 | Compound (404) | A |
Embodiment 131 | Compound (405) | A |
Embodiment 132 | Compound (301) | A |
Embodiment 133 | Compound (203) | A |
Embodiment 134 | Compound (101) | A |
Embodiment 135 | Compound (102) | A |
Comparative example 15 | Compound (7) | C |
Use the photopolymerizable composition (embodiment 127~135) of radical polymerization initiator of the present invention not find that under 50 ℃, 10 days preservation condition tangible viscosity increases.But, using known α, α '-two ketoxime ester confirms that as the situation (comparative example 15) of radical polymerization initiator viscosity increases under 50 ℃, 10 days preservation condition.That is, the compound of the general formula of the application of the invention (1) expression can improve storage stability as radical polymerization initiator.
(IV) modulation of photopolymerizable composition and susceptibility are measured
Embodiment 136~189 and comparative example 16~19
(modulation of acrylics solution (2))
In reaction vessel, add following solvents, monomer and thermal polymerization, carry out the nitrogen displacement subsequently, stir lentamente then, simultaneously solution temperature is increased to about 70 ℃, keep this temperature to carry out polyreaction in 5 hours.
2,2 '-azo two (2, the 4-methyl pentane nitrile), 5 weight parts
Glycol ether methyl ethyl ether 200 weight parts
Methylacrylic acid 20 weight parts
SY-Monomer G 45 weight parts
Vinylbenzene 10 weight parts
Cyclohexyl methacrylate 25 weight parts
Through above-mentioned reaction, obtain the acrylics solution of weight-average molecular weight about 22,000.After being cooled to room temperature, about 2g resin solution of taking a sample is measured nonvolatile component at 70 ℃ of drying under reduced pressure, and adding pimelinketone to nonvolatile component to previous synthetic resin solution is 20%, thus modulation acrylics solution (2).
Add, mix Dipentaerythritol five propenoate (Sartomer company, SR399) 100 weight parts as free-radical polymerised compound (b), as comprise acrylics solution (2) 500 weight parts of the solution of alkali soluble resins (c), as propylene glycol monomethyl ether acetate 200 weight parts of solvent, as the compound (weight part is documented in respectively in table 29~31) shown in table 29~31 of radical polymerization initiator (a) and sensitizing agent (d), modulate uniform photopolymerizable composition solution.
Disc filter with aperture 0.2 μ m filters above-mentioned photopolymerizable composition solution, uses spin coater to be applied on the sheet glass of thickness 1mm, in baking oven, removes and desolvates 80 ℃ of heat dryings 3 minutes.The thickness that is formed at the photopolymerizable composition film on the sheet glass after the drying is 5 μ m.To this photopolymerizable composition film; Use Japanese beam split (strain) SS-25CP type to divide light illuminator; Irradiation energy with 13 phasic change high voltage mercury lamps is that irradiation time is made public; Then developed 1 minute with 1% aqueous sodium carbonate at 20 ℃, the insoluble necessary minimum energy of photopolymerizable composition is defined as susceptibility under the illumination wavelength of 365nm, and the result is shown in table 29~31.
Table 29
Example number | Radical polymerization initiator | Addition (weight part) | Sensitizing agent | Addition (weight part) | Susceptibility (mJ/cm 2) |
Embodiment 136 | Compound (101) | 10 | Do not have | 0 | 35 |
Embodiment 137 | Compound (101) | 10 | Compound (5) | 2 | 25 |
Embodiment 138 | Compound (101) | 10 | Compound (6) | 2 | 20 |
Embodiment 139 | Compound (102) | 10 | Do not have | 0 | 30 |
Embodiment 140 | Compound (102) | 10 | Compound (5) | 2 | 25 |
Embodiment 141 | Compound (102) | 10 | Compound (6) | 2 | 20 |
Embodiment 142 | Compound (106) | 10 | Do not have | 0 | 30 |
Embodiment 143 | Compound (106) | 10 | Compound (5) | 2 | 25 |
Embodiment 144 | Compound (106) | 10 | Compound (6) | 2 | 25 |
Embodiment 145 | Compound (107) | 10 | Do not have | 0 | 25 |
Embodiment 146 | Compound (107) | 10 | Compound (5) | 2 | 20 |
Embodiment 147 | Compound (107) | 10 | Compound (6) | 2 | 20 |
Embodiment 148 | Compound (108) | 10 | Do not have | 0 | 20 |
Embodiment 149 | Compound (108) | 10 | Compound (5) | 2 | 20 |
Embodiment 150 | Compound (108) | 10 | Compound (6) | 2 | 20 |
Comparative example 16 | Compound (1) | 15 | Do not have | 0 | >100 |
Comparative example 17 | Compound (1) | 15 | Compound (5) | 5 | >100 |
Comparative example 18 | Compound (1) | 15 | Compound (6) | 5 | >100 |
Comparative example 19 | Compound (4) | 20 | Do not have | 0 | 60 |
Table 30
Example number | Radical polymerization initiator | Addition (weight part) | Sensitizing agent | Addition (weight part) | Susceptibility (mJ/cm 2) |
Embodiment 151 | Compound (201) | 10 | Do not have | 0 | 35 |
Embodiment 152 | Compound (201) | 10 | Compound (5) | 2 | 25 |
Embodiment 153 | Compound (201) | 10 | Compound (6) | 2 | 20 |
Embodiment 154 | Compound (202) | 10 | Do not have | 0 | 35 |
Embodiment 155 | Compound (202) | 10 | Compound (5) | 2 | 30 |
Embodiment 156 | Compound (202) | 10 | Compound (6) | 2 | 25 |
Embodiment 157 | Compound (203) | 10 | Do not have | 0 | 35 |
Embodiment 158 | Compound (203) | 10 | Compound (5) | 2 | 25 |
Embodiment 159 | Compound (203) | 10 | Compound (6) | 2 | 25 |
Embodiment 160 | Compound (204) | 10 | Do not have | 0 | 30 |
Embodiment 161 | Compound (204) | 10 | Compound (5) | 2 | 25 |
Embodiment 162 | Compound (204) | 10 | Compound (6) | 2 | 20 |
Table 31
Example number | Radical polymerization initiator | Addition (weight part) | Sensitizing agent | Addition (weight part) | Susceptibility (mJ/cm 2) |
Embodiment 163 | Compound (401) | 10 | Do not have | 0 | 30 |
Embodiment 164 | Compound (401) | 10 | Compound (5) | 2 | 25 |
Embodiment 165 | Compound (401) | 10 | Compound (6) | 2 | 20 |
Embodiment 166 | Compound (402) | 10 | Do not have | 0 | 40 |
Embodiment 167 | Compound (402) | 10 | Compound (5) | 2 | 30 |
Embodiment 168 | Compound (402) | 10 | Compound (6) | 2 | 25 |
Embodiment 169 | Compound (403) | 10 | Do not have | 0 | 35 |
Embodiment 170 | Compound (403) | 10 | Compound (5) | 2 | 25 |
Embodiment 171 | Compound (403) | 10 | Compound (6) | 2 | 20 |
Embodiment 172 | Compound (404) | 10 | Do not have | 0 | 40 |
Embodiment 173 | Compound (404) | 10 | Compound (5) | 2 | 30 |
Embodiment 174 | Compound (404) | 10 | Compound (6) | 2 | 30 |
Embodiment 175 | Compound (405) | 10 | Do not have | 0 | 30 |
Embodiment 176 | Compound (405) | 10 | Compound (5) | 2 | 20 |
Embodiment 177 | Compound (405) | 10 | Compound (6) | 2 | 20 |
Embodiment 178 | Compound (301) | 10 | Do not have | 0 | 30 |
Embodiment 179 | Compound (301) | 10 | Compound (5) | 2 | 25 |
Embodiment 180 | Compound (301) | 10 | Compound (6) | 2 | 20 |
Embodiment 181 | Compound (302) | 10 | Do not have | 0 | 35 |
Embodiment 182 | Compound (302) | 10 | Compound (5) | 2 | 25 |
Embodiment 183 | Compound (302) | 10 | Compound (6) | 2 | 20 |
Embodiment 184 | Compound (303) | 10 | Do not have | 0 | 40 |
Embodiment 185 | Compound (303) | 10 | Compound (5) | 2 | 30 |
Embodiment 186 | Compound (303) | 10 | Compound (6) | 2 | 30 |
Embodiment 187 | Compound (304) | 10 | Do not have | 0 | 35 |
Embodiment 188 | Compound (304) | 10 | Compound (5) | 2 | 25 |
Embodiment 189 | Compound (304) | 10 | Compound (6) | 2 | 25 |
With the known α of use; α '-two ketoxime ester is compared as the comparative example 19 of radical polymerization initiator with the known alpha-ketoxime ester of use as the comparative example 16~18 of radical polymerization initiator, uses the photopolymerizable composition (embodiment 136~189) of radical polymerization initiator of the present invention (a) to have tangible high sensitive.In addition, even photopolymerizable composition of the present invention and with sensitizing agent does not have sufficiently high susceptibility yet, but through and can realize higher susceptibility with sensitizing agent.
(V) making of picture pattern and evaluation
Embodiment 190~243 and comparative example 20~23
To the photopolymerizable composition film on the glass substrate of making in embodiment 136~189 and the comparative example 16~19, utilize the pattern mask (20 μ m * 20 μ m resolving power) of regulation, the exposure energy that shines the about 100 μ m of 15 exposing clearances in second, 365nm is 10mW/cm
2The light of high voltage mercury lamp.Subsequently, developed for 60 seconds in room temperature, remove unexposed portion with the tetramethylammonium hydroxide aqueous solution of 0.2 weight %, after the pure water washing, in baking oven at 230 ℃ to the cured article heating that obtains 30 minutes.The pattern form that on glass substrate, obtains with following method evaluation.The result is shown in table 32~34.
(pattern form evaluation method)
The pattern form that on substrate, obtains through observation by light microscope, thus carry out the rectilinearity evaluation of pattern.Opinion rating is described below.
G: rectilinearity is good
N: rectilinearity is relatively poor
-: because curing is insufficient, do not observe pattern
In addition; The pattern of under 121 ℃, 100%RH, 2atm, 23 hours condition, making in to embodiment 190~243 and comparative example 20~23 forms substrate implement PCT (pressure kettle) test after; Paste the cellulose film adhesive tape at 20 μ m drafting departments, through carrying out stripping test, the evaluation pattern generating adaptation.The result is shown in table 32~34.
Opinion rating is described below.
G: do not find peeling off of 20 μ m patterns
N: find peeling off of 20 μ m patterns
-: because curing is insufficient, can not estimate
Table 32
Example number | The photopolymerizable composition that uses | Pattern form (rectilinearity) | The pattern adaptation |
Embodiment 190 | Embodiment 136 | G | G |
Embodiment 191 | Embodiment 137 | G | G |
Embodiment 192 | Embodiment 138 | G | G |
Embodiment 193 | Embodiment 139 | G | G |
Embodiment 194 | Embodiment 140 | G | G |
Embodiment 195 | Embodiment 141 | G | G |
Embodiment 196 | Embodiment 142 | G | G |
Embodiment 197 | Embodiment 143 | G | G |
Embodiment 198 | Embodiment 144 | G | G |
Embodiment 199 | Embodiment 145 | G | G |
Embodiment 200 | Embodiment 146 | G | G |
Embodiment 201 | Embodiment 147 | G | G |
Embodiment 202 | Embodiment 148 | G | G |
Embodiment 203 | Embodiment 149 | G | G |
Embodiment 204 | Embodiment 150 | G | G |
Comparative example 20 | Comparative example 16 | - | - |
Comparative example 21 | Comparative example 17 | - | - |
Comparative example 22 | Comparative example 18 | - | - |
Comparative example 23 | Comparative example 19 | N | N |
Table 33
Example number | The photopolymerizable composition that uses | Pattern form (rectilinearity) | The pattern adaptation |
Embodiment 205 | Embodiment 151 | G | G |
Embodiment 206 | Embodiment 152 | G | G |
Embodiment 207 | Embodiment 153 | G | G |
Embodiment 208 | Embodiment 154 | G | G |
Embodiment 209 | Embodiment 155 | G | G |
Embodiment 210 | Embodiment 156 | G | G |
Embodiment 211 | Embodiment 157 | G | G |
Embodiment 212 | Embodiment 158 | G | G |
Embodiment 213 | Embodiment 159 | G | G |
Embodiment 214 | Embodiment 160 | G | G |
Embodiment 215 | Embodiment 161 | G | G |
Embodiment 216 | Embodiment 162 | G | G |
Table 34
Example number | The photopolymerizable composition that uses | Pattern form (rectilinearity) | The pattern adaptation |
Embodiment 217 | Embodiment 163 | G | G |
Embodiment 218 | Embodiment 164 | G | G |
Embodiment 219 | Embodiment 165 | G | G |
Embodiment 220 | Embodiment 166 | G | G |
Embodiment 221 | Embodiment 167 | G | G |
Embodiment 222 | Embodiment 168 | G | G |
Embodiment 223 | Embodiment 169 | G | G |
Embodiment 224 | Embodiment 170 | G | G |
Embodiment 225 | Embodiment 171 | G | G |
Embodiment 226 | Embodiment 172 | G | G |
Embodiment 227 | Embodiment 173 | G | G |
Embodiment 228 | Embodiment 174 | G | G |
Embodiment 229 | Embodiment 175 | G | G |
Embodiment 230 | Embodiment 176 | G | G |
Embodiment 231 | Embodiment 177 | G | G |
Embodiment 232 | Embodiment 178 | G | G |
Embodiment 233 | Embodiment 179 | G | G |
Embodiment 234 | Embodiment 180 | G | G |
Embodiment 235 | Embodiment 181 | G | G |
Embodiment 236 | Embodiment 182 | G | G |
Embodiment 237 | Embodiment 183 | G | G |
Embodiment 238 | Embodiment 184 | G | G |
Embodiment 239 | Embodiment 185 | G | G |
Embodiment 240 | Embodiment 186 | G | G |
Embodiment 241 | Embodiment 187 | G | G |
Embodiment 242 | Embodiment 188 | G | G |
Embodiment 243 | Embodiment 189 | G | G |
Use the situation (embodiment 190~243) of photopolymerizable composition of the present invention; The rectilinearity of the pattern form that on glass substrate, obtains is good; On the contrary; Use the rectilinearity of the pattern form that the situation (comparative example 20~23) of photopolymerizable composition of the present invention obtains on glass substrate relatively poor, perhaps can not observe pattern form owing to solidify insufficient.In addition, according to photopolymerizable composition of the present invention, the pattern that on glass substrate, obtains is good to the adaptation of substrate, on the contrary, uses situation (comparative example 20~23) pattern of photopolymerizable composition of the present invention insufficient to the adaptation of substrate.
(VI) making of picture pattern and evaluation
Embodiment 244~248 and comparative example 24~27
(modulation of acrylics solution (3))
Add 370 parts of pimelinketone to reaction vessel;, container is being heated to 80 ℃ when feeding nitrogen; Under this temperature with dripping 15.0 parts of 20.0 parts of methylacrylic acids, 10.0 parts of TEB 3Ks, 55.0 parts of n-BMAs, methylacrylic acid-2-hydroxy methacrylate, 2 in 1 hour; The mixture that 2 '-Diisopropyl azodicarboxylate is 4.0 parts, and carry out polyreaction.After dripping end, further after 3 hours, add the solution that 1.0 parts of Diisopropyl azodicarboxylates is dissolved into 50 parts of pimelinketone, further continue reaction 1 hour, obtain acrylics solution at 80 ℃ 80 ℃ of reactions.
After being cooled to room temperature, about 2g acrylics solution of taking a sample was measured nonvolatile component 180 ℃ of heat dryings 20 minutes, and adding pimelinketone to nonvolatile component to previous synthetic acrylics solution is 20%.The weight-average molecular weight of the acrylics that obtains is 40000.
(modulation of red pigment dispersion)
After mixing the mixture of following composition equably, after 2 hours,, make red pigment dispersion with the strainer filtration of 5 μ m with EIGER shredder (EIGER Japanese firm makes MINI MODEL M-250MKII) dispersion.
11.0 parts of diketopyrrolo-pyrrole series pigments (C.I.Pigment Red 254)
(the not red B-CF of Ciba manufactured Ilyushin lattice (イ Le ガ Off オ one レ Star De B-CF))
1.0 parts in diketopyrrolo-pyrrole series pigments verivate (following formula (6))
[changing 7]
(3) 40.0 parts of acrylics solution
48.0 parts of pimelinketone
(modulation of veridian dispersion-s)
After mixing the mixture of following composition equably, after 2 hours,, make the veridian dispersion-s with the strainer filtration of 5 μ m with EIGER shredder (EIGER Japanese firm makes MINI MODEL M-250MKII) dispersion.
Except pigment being changed to following pigment, pigment derivative being changed to the following pigment derivative, likewise make the veridian dispersion-s with red pigment dispersion.
7.1 parts of copper halide phthualocyanine pigments (C.I.Pigment Green 36)
(Toyo Ink is made society and is made the green 6YK of Li Aonuo (リ オ ノ one Le グ リ one Application 6YK))
3.9 parts of monoazo series pigments (C.I.PigmentYellow 150)
(bright Sheng (LANXESS) manufactured E4GN-GT)
1.0 parts in triazine series pigments verivate (following formula (7))
[changing 8]
(modulation of blue pigment dispersion)
Except pigment being changed to following pigment, pigment derivative being changed to the following pigment derivative, likewise make blue pigment dispersion with red pigment dispersion.
11.0 parts of ε type copper phthalocyanine series pigments (C.I.Pigment Blue 15:6)
(the Heliogenblue L-6700F that BASF AG makes)
1.0 parts in phthualocyanine pigment verivate (following formula (8))
[changing 9]
Cu-pc; Copper phthalocyanine residue formula (8)
(modulation of black pigment dispersion-s)
Except pigment being changed to the following pigment, likewise make the black pigment dispersion-s with red pigment dispersion.
12.0 parts of carbon blacks (Mitsubishi Chemical society makes " MA77 ")
(modulation of photopolymerizable composition)
Form with the cooperation shown in the table 35 mixture is mixed after evenly, the strainer filtration with 1 μ m obtains each photopolymerizable composition.
Table 35
Embodiment 244 | Embodiment 245 | Embodiment 246 | Embodiment 247 | Embodiment 248 | Comparative example 24 | Comparative example 25 | Comparative example 26 | Comparative example 27 | |
Color | Red | Red | Green | Blue | Black | Red | Green | Blue | Black |
Pigment dispersion | 58.33 | 58.33 | 66.67 | 53.33 | 75.00 | 58.33 | 66.67 | 53.33 | 75.00 |
Acrylics solution (3) | 20.36 | 20.36 | 11.19 | 14.79 | 9.00 | 24.67 | 11.19 | 14.79 | 9.00 |
Free-radical polymerised compound (b) | 3.06 | 3.06 | 3.03 | 4.17 | 2.20 | 2.20 | 3.03 | 4.17 | 2.20 |
Radical polymerization initiator (a)-1 | 1.20 | 0.96 | 1.40 | 2.20 | 1.00 | ||||
Radical polymerization initiator (a)-2 | 1.20 | 1.40 | 2.20 | 1.00 | |||||
Sensitizing agent (d) | 0.24 | ||||||||
Solvent | 17.04 | 17.04 | 17.71 | 25.50 | 12.80 | 13.60 | 17.71 | 25.50 | 12.80 |
Add up to | 100.00 | 100.00 | 100.00 | 100.00 | 100.00 | 100.00 | 100.00 | 100.00 | 100.00 |
Free-radical polymerised initiator (a)-1: the compound of table 5 (107)
Free-radical polymerised initiator (a)-2: the compound of table 5 (1)
Free-radical polymerised initiator (b): Viscoat 295
(" NK ester ATMPT " that chemistry society in Xin Zhong village makes)
Sensitizing agent (d): 2,4-diethyl thioxanthone (compound of table 5 (5))
(formation of picture pattern)
On the glass substrate of 10cm * 10cm, be coated with the photopolymerizable composition that obtains through method of spin coating, the thickness after making the later stage cure is the thickness shown in the table 36, then in clean baking oven 70 ℃ of prebake 15 minutes.Then, this substrate is cooled to room temperature after, use ultrahigh pressure mercury lamp across the photomask exposure ultraviolet ray.Subsequently, use 23 ℃ aqueous sodium carbonate that this substrate is carried out spray development after, wash with ion exchanged water, air-dry.Subsequently, in clean baking oven, cure 30 minutes, thereby on substrate, form the picture pattern of striated 230 ℃ of later stages.
(evaluation)
The shape of the picture pattern that forms to the susceptibility of the photopolymerizable composition that obtains and by aforesaid method with following method is estimated.The result is shown in the table 36.
(susceptibility)
Irradiation exposure when the picture pattern that forms is accomplished according to the picture size of photomask is set at the susceptibility of photopolymerizable composition.Opinion rating is described below.
A: not enough 50mJ/cm
2
B:50mJ/cm
2More than, not enough 100mJ/cm
2
C:100mJ/cm
2More than, not enough 300mJ/cm
2
D:300mJ/cm
2More than
(pattern form)
The shape of the picture pattern that the rectilinearity through (1) pattern, the cross-sectional shape evaluation of (2) pattern form.
About (1), estimate through observation by light microscope.Opinion rating is described below.
A: rectilinearity is good
B: the part rectilinearity is relatively poor
C: rectilinearity is relatively poor
About (2), estimate through scanning electron microscope (SEM) observation.Opinion rating is described below.
A: along conical by its shape
B: non-conical by its shape
C: contrary conical by its shape
(residual film ratio evaluation)
Will be through overexposure (100mJ/cm
2), development, the later stage ratio that cures the thickness that the thickness measured after the operation measures with respect to the coated film that forms photopolymerizable composition and dry back is set at residual film ratio.Opinion rating is described below.
More than the A:80%
B:75% is above, less than 80%
C:70% is above, less than 75%
D: less than 70%
Table 36
Embodiment 244 | Embodiment 245 | Embodiment 246 | Embodiment 247 | Embodiment 248 | Comparative example 24 | Comparative example 25 | Comparative example 26 | Comparative example 27 | |
Color | Red | Red | Green | Blue | Black | Red | Green | Blue | Black |
Thickness (μ m) | 1.40 | 1.40 | 1.80 | 1.80 | 1.10 | 1.40 | 1.80 | 1.80 | 1.10 |
Susceptibility | A | A | A | A | A | D | D | D | D |
The pattern rectilinearity | A | A | A | A | A | C | C | C | C |
The pattern cross-sectional shape | A | A | A | A | A | C | C | B | C |
Residual film ratio | A | A | A | A | A | D | D | D | D |
Shown in table 36; Use the photopolymerizable composition of radical polymerization initiator of the present invention to be high sensitive; The rectilinearity of the pattern that obtains and cross-sectional shape are also good; On the contrary, in the susceptibility of the photopolymerizable composition of comparative example 24~27, the rectilinearity of pattern and the cross-sectional shape any one relatively poor, do not obtain the good compsn of over-all properties.
Claims (9)
1. the compound of a formula (1):
[changing 1]
In the formula; A and B represent 2-thienyl, 2-furyl, naphthyl, fluorenyl, quinolyl, phenanthryl, 2-carbazyl, 3-carbazyl or benzothiazolyl respectively independently; But do not comprise that A and B were by the substituted condensation polycyclic alkyl of methoxyl group when A was identical with B; A and B can be selected from methyl, ethyl, propyl group, butyl, amyl group, hexyl, methoxyl group, oxyethyl group, propoxy-, butoxy, cyclohexyl oxygen base, isopropoxy, methoxycarbonyl, acetoxyl group, phenoxy, dimethylamino, diethylamino, methylthio group, the amino group replacement of xylyl, and X representes methyl, ethyl, propyl group or butyl.
2. compound according to claim 1, wherein, said A is different with B.
3. compound according to claim 1, wherein, said A is identical with B.
4. a radical polymerization initiator comprises any described compound in the claim 1~3.
5. a photopolymerizable composition comprises described radical polymerization initiator of claim 4 and free-radical polymerised compound.
6. photopolymerizable composition according to claim 5, it further comprises alkali soluble resins.
7. according to claim 5 or 6 described photopolymerizable compositions, it further comprises sensitizing agent.
8. a negative resist comprises any described photopolymerizable composition in the claim 5~7.
9. the formation method of a picture pattern is characterized in that, at the folded described negative resist of claim 8 of layers on substrates, partly the irradiation energy ray makes its curing, removes non-irradiated part through alkaline-based developer.
Applications Claiming Priority (19)
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JP005881/2006 | 2006-01-13 | ||
JP2006005881 | 2006-01-13 | ||
JP2006005887A JP5023495B2 (en) | 2006-01-13 | 2006-01-13 | Radical polymerization initiator and polymerizable composition |
JP005887/2006 | 2006-01-13 | ||
JP2006019293A JP4887806B2 (en) | 2006-01-27 | 2006-01-27 | Radical polymerization initiator and polymerizable composition |
JP2006019294A JP4887807B2 (en) | 2006-01-27 | 2006-01-27 | Radical polymerization initiator and polymerizable composition |
JP019294/2006 | 2006-01-27 | ||
JP019293/2006 | 2006-01-27 | ||
JP033971/2006 | 2006-02-10 | ||
JP2006034038A JP4734591B2 (en) | 2006-02-10 | 2006-02-10 | Polymerizable composition, negative resist using the same, and image pattern forming method using the same |
JP2006034037 | 2006-02-10 | ||
JP2006033971A JP2007211175A (en) | 2006-02-10 | 2006-02-10 | Polymerizable composition and negative type resist using the same and method for forming image pattern using the same |
JP034038/2006 | 2006-02-10 | ||
JP034037/2006 | 2006-02-10 | ||
JP194241/2006 | 2006-07-14 | ||
JP2006194241A JP4007399B2 (en) | 2006-01-13 | 2006-07-14 | Oxime ester compound, radical polymerization initiator and polymerizable composition |
JP199929/2006 | 2006-07-21 | ||
JP2006199929A JP4020153B2 (en) | 2006-02-10 | 2006-07-21 | Polymerizable composition, negative resist using the same, and image pattern forming method using the same |
PCT/JP2007/050287 WO2007080947A1 (en) | 2006-01-13 | 2007-01-12 | Diketooxime ester compound and use thereof |
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JP5527965B2 (en) * | 2008-02-22 | 2014-06-25 | Jsr株式会社 | Radiation-sensitive composition for green pixel formation, color filter, and color liquid crystal display element |
JP5566378B2 (en) * | 2008-06-06 | 2014-08-06 | ビーエーエスエフ ソシエタス・ヨーロピア | Oxime ester photoinitiator |
JP2010215575A (en) * | 2009-03-18 | 2010-09-30 | Toyo Ink Mfg Co Ltd | New oxime ester compound, radical polymerization initiator containing the same, polymerizable composition, negative type resist by using the same and method for forming image pattern by using the same |
JP5317809B2 (en) * | 2009-04-20 | 2013-10-16 | 富士フイルム株式会社 | Colored curable composition, colored pattern forming method, color filter, and liquid crystal display device |
CN101941939B (en) * | 2010-07-21 | 2013-05-29 | 深圳市有为化学技术有限公司 | Polyfunctional carbazole derivative oxime ester compound and preparation method and light polymerization initiator thereof |
US9051397B2 (en) | 2010-10-05 | 2015-06-09 | Basf Se | Oxime ester |
KR102059430B1 (en) * | 2011-08-09 | 2019-12-26 | 제이에스알 가부시끼가이샤 | Microlens array, and stereoscopic image display device |
CN102675097B (en) * | 2012-03-31 | 2014-06-11 | 江苏利田科技股份有限公司 | Method for cleanly producing methoxyl propanediol acrylate and analogs thereof |
EP2913323B1 (en) * | 2012-09-28 | 2018-09-12 | Tokyo Ohka Kogyo Co., Ltd. | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
WO2015064958A1 (en) * | 2013-11-04 | 2015-05-07 | 한국화학연구원 | Novel oxime ester biphenyl compound, photo initiator and photosensitive resin composition containing same |
KR101435652B1 (en) * | 2014-01-17 | 2014-08-28 | 주식회사 삼양사 | NOVEL FLUORENYL β-OXIME ESTER COMPOUNDS, PHOTOPOLYMERIZATION INITIATOR AND PHOTORESIST COMPOSITION CONTAINING THE SAME |
JP6195590B2 (en) * | 2015-05-25 | 2017-09-13 | 東京応化工業株式会社 | Photosensitive composition, pattern forming method, cured film, insulating film, and display device |
JP6195645B2 (en) * | 2015-07-21 | 2017-09-13 | 東京応化工業株式会社 | Colored photosensitive composition |
KR20180044227A (en) * | 2015-08-24 | 2018-05-02 | 가부시키가이샤 아데카 | Oxime ester compound and polymerization initiator containing the compound |
JP6621643B2 (en) * | 2015-10-22 | 2019-12-18 | 株式会社Adeka | Oxime ester compound and polymerization initiator containing the compound |
JP6788971B2 (en) * | 2016-01-14 | 2020-11-25 | 東京応化工業株式会社 | Photosensitive composition |
JP7008508B2 (en) * | 2016-09-30 | 2022-01-25 | 株式会社Dnpファインケミカル | Photosensitive colored resin compositions for color filters, color filters, and display devices |
CN109305951A (en) * | 2017-07-26 | 2019-02-05 | 湖北固润科技股份有限公司 | Cumarin oxime ester compound and its preparation and application |
CN108250660B (en) * | 2017-12-22 | 2021-03-09 | 万华化学集团股份有限公司 | Electroplating-grade PC/ABS alloy material and preparation method thereof |
CN110551098B (en) * | 2019-06-17 | 2021-03-12 | 湖北固润科技股份有限公司 | Oxime ester photoinitiator containing five-membered aromatic heterocyclic structure and preparation and application thereof |
CN110330501B (en) * | 2019-06-25 | 2021-05-07 | 湖北固润科技股份有限公司 | Long-wavelength coumarin oxime ester compounds and preparation and application thereof |
WO2020258014A1 (en) * | 2019-06-25 | 2020-12-30 | 湖北固润科技股份有限公司 | Long-wavelength coumarin oxime ester compound, preparation therefor, and application thereof |
CN111266195B (en) * | 2020-03-05 | 2021-09-07 | 中南大学 | Zinc oxide ore flotation combined collecting agent and application thereof |
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