CN103524735A - Photosensitive polyimide - Google Patents
Photosensitive polyimide Download PDFInfo
- Publication number
- CN103524735A CN103524735A CN201310413998.3A CN201310413998A CN103524735A CN 103524735 A CN103524735 A CN 103524735A CN 201310413998 A CN201310413998 A CN 201310413998A CN 103524735 A CN103524735 A CN 103524735A
- Authority
- CN
- China
- Prior art keywords
- group
- photosensitive polyimide
- polyimide polymer
- photosensitive
- integer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000004642 Polyimide Substances 0.000 title claims abstract description 70
- 229920001721 polyimide Polymers 0.000 title claims abstract description 70
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 35
- -1 methoxy, ethoxy Chemical group 0.000 claims description 28
- 125000000962 organic group Chemical group 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 abstract description 15
- 239000013039 cover film Substances 0.000 abstract description 13
- 150000002513 isocyanates Chemical class 0.000 abstract description 11
- 239000010408 film Substances 0.000 abstract description 7
- 229910000679 solder Inorganic materials 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 28
- 0 CC1C(C)=CC(C(*C(c2cc(C)c(C)cc2)=O)=O)=CC1 Chemical compound CC1C(C)=CC(C(*C(c2cc(C)c(C)cc2)=O)=O)=CC1 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 15
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 description 14
- 239000001294 propane Substances 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 239000012787 coverlay film Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SXGMVGOVILIERA-UHFFFAOYSA-N (2R,3S)-2,3-diaminobutanoic acid Natural products CC(N)C(N)C(O)=O SXGMVGOVILIERA-UHFFFAOYSA-N 0.000 description 4
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 description 4
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- DIOSHTLNZVXJOF-UHFFFAOYSA-N 2,5-bis(3-oxobutanoylamino)benzenesulfonic acid Chemical compound CC(=O)CC(=O)NC1=CC=C(NC(=O)CC(C)=O)C(S(O)(=O)=O)=C1 DIOSHTLNZVXJOF-UHFFFAOYSA-N 0.000 description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GQPVFBDWIUVLHG-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)COC(=O)C(C)=C GQPVFBDWIUVLHG-UHFFFAOYSA-N 0.000 description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- JFIIYSNVUJCUNP-UHFFFAOYSA-N 1-methoxypropane-1,2-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(O)C(C)O JFIIYSNVUJCUNP-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- IAKGBURUJDUUNN-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-3-methylbutane-1,4-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(C)C(CO)(CO)CO IAKGBURUJDUUNN-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- VSZARHUCMHICLD-UHFFFAOYSA-N 4,6-bis(prop-2-enoxy)-1h-1,3,5-triazin-2-one Chemical compound C=CCOC=1N=C(OCC=C)NC(=O)N=1 VSZARHUCMHICLD-UHFFFAOYSA-N 0.000 description 2
- RQBIGPMJQUKYAH-UHFFFAOYSA-N 4-(3,4-diaminophenoxy)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=C(N)C(N)=C1 RQBIGPMJQUKYAH-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 2
- WORATQNXUKXKDD-UHFFFAOYSA-N 9-hydroxynonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCO WORATQNXUKXKDD-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 2
- GCNKJQRMNYNDBI-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(2-methylprop-2-enoyloxymethyl)butyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CC)COC(=O)C(C)=C GCNKJQRMNYNDBI-UHFFFAOYSA-N 0.000 description 2
- IALCDEGIETXROH-UHFFFAOYSA-N [2-ethyl-4-(prop-2-enoyloxymethyl)hexyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CC)CC(CC)COC(=O)C=C IALCDEGIETXROH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 2
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 2
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 2
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 2
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 2
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- DTQZKOBDNLNBCU-UHFFFAOYSA-N 1-methylimidazole Chemical compound CN1C=CN=C1.CN1C=CN=C1 DTQZKOBDNLNBCU-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(O)COCCO ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 0.000 description 1
- BBLIBMSYZJACPQ-UHFFFAOYSA-N 2-(4-propylphenoxy)ethyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OCCOC(=O)C(C)=C)C=C1 BBLIBMSYZJACPQ-UHFFFAOYSA-N 0.000 description 1
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 1
- COORVRSSRBIIFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCO COORVRSSRBIIFJ-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- 239000012957 2-hydroxy-2-methyl-1-phenylpropanone Substances 0.000 description 1
- IVAATAQAFOAALG-UHFFFAOYSA-N 2h-cyclopenta[c]pyridine Chemical compound C1=CNC=C2C=CC=C21 IVAATAQAFOAALG-UHFFFAOYSA-N 0.000 description 1
- WDMIHJIBZGYESW-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC=1C=C(C(=O)O)C=C(C1)N.NC=1C=C(C(=O)O)C=C(C1)N WDMIHJIBZGYESW-UHFFFAOYSA-N 0.000 description 1
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 description 1
- ZRZCNDIPIZYLSC-UHFFFAOYSA-N 4-[(4-aminophenoxy)methoxy]aniline Chemical compound C1=CC(N)=CC=C1OCOC1=CC=C(N)C=C1 ZRZCNDIPIZYLSC-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention relates to isocyanate modified photosensitive polyimide. The photosensitive polyimide has excellent heat resistance, chemical resistance and flexibility and can be used as a liquid state photoresist or dry film photoresist or can be applied to a solder resist, a cover film or a printed circuit board.
Description
The present application is a divisional application of an invention patent application having an application date of 25/01/2008, an application number of 200810007025.9 and an invention name of "photosensitive polyimide".
Technical Field
The present invention relates to isocyanate modified photosensitive polyimide. The photosensitive polyimide has excellent heat resistance, chemical resistance and flexibility, and can be used as a liquid photoresist or a dry film photoresist, or used for a solder resist, a cover film or a printed circuit board.
Background
Nowadays, electronic products are becoming thinner and smaller, and the sizes of various electronic components are also being reduced. Due to the advantages of flexible printed wiring boards in terms of flexibility and weight, the demand for flexible printed wiring boards has increased.
Currently, the cover film materials can be classified into three types, the first type is a photosensitive cover film (photosensitive cover film), the second type is a non-photosensitive cover film (non-photosensitive cover film), and the third type is a thermoplastic cover film (thermoplastic cover film). The first type of photosensitive coverlay film is classified into a polyimide-based coverlay film (PI-based coverlay) and a non-polyimide-based coverlay film (non-PI-based coverlay), wherein the application of the polyimide-based coverlay film is limited due to factors such as poor heat resistance and high coefficient of thermal expansion ("CTE"). The second type of non-photosensitive coverlay is not as practical as the photosensitive coverlay because processing is more complicated than that of the photosensitive coverlay. As for the thermoplastic cover film, it requires post-processing for hole formation, and therefore is inferior in convenience to the photosensitive cover film.
U.S. Pat. No. 6,605,353 discloses photosensitive polyimides modified with epoxy. However, since the polymer is obtained by reacting an epoxide with an acid, the reactivity is poor, and the ring-opened OH functional group reacts with an epoxy group (epoxy), and thus, problems such as stability and thermal stability are encountered.
In order to improve the heat resistance and the processing convenience of the cover film, there is still a need in the art for photosensitive polyimides that can solve the above problems.
Disclosure of Invention
The present invention provides an isocyanate-modified photosensitive polyimide which has preferable reactivity, and is excellent in stability, thermal stability, and can be hardened at low temperature. The photosensitive polyimide of the present invention can be used as a liquid photoresist or for a dry film photoresist, and can be used to form a thick film.
The invention also provides a photosensitive composition containing the photosensitive polyimide, which can be used as a protective film material. Therefore, the photosensitive composition of the present invention can be applied to a solder resist as a protective film material, a cover film material and a printed wiring board.
Detailed Description
The photosensitive polyimide polymer of the present invention has the following structure of formula (I):
Wherein
A and C may be the same or different and are each independently a tetravalent organic group;
wherein R represents an unsaturated group containing a vinyl group or a group selected from:
wherein
R1 is a substituted or unsubstituted saturated or unsaturated organic group having C1-C20; and
r2 is an unsaturated group containing a vinyl group.
D is a divalent organic group;
n is an integer greater than 0, and
m is equal to 0 or an integer greater than 0.
Preferably, the above-mentioned unsaturated group containing a vinyl group is selected from the following groups:
wherein:
r4 and R5 are each H or a substituted or unsubstituted alkyl group having C1-C5, and
r6 is a covalent bond or a substituted or unsubstituted organic group having C1-C20.
More preferably, the vinyl group-containing unsaturated group is selected from the group consisting of:
wherein z is an integer of 0 to 6.
Particularly preferably, the vinyl group-containing unsaturated group is selected from the group consisting of:
wherein each z represents an integer of 0 to 6.
Preferably, the above-mentioned R1 group may be selected from the following groups:
wherein
o, p, q and r are each 0 or an integer greater than 0;
r4, R5 and R6 have the definitions described above;
r7 is H or a substituted or unsubstituted organic group having C1-C12; and
r8 is a covalent bond or an organic group selected from:
more preferably, the R1 group is selected from the group consisting of:
the tetravalent organic groups a and C contained in the photosensitive polyimide polymer of formula (I) of the present invention are not particularly limited, and are, for example, tetravalent aromatic groups or tetravalent aliphatic groups. Preferably, A and C are each selected from the group consisting of:
the photosensitive polyimide polymer of formula (I) of the present invention contains B derived from a diamine having reactive functional groups including OH, COOH, NH2Or SH, preferably OH, NH2. Preferably, B is independently selected from the group consisting of:
wherein:
r9 is H, methyl or ethyl;
s is an integer of 1 to 4;
t is an integer of 0 to 5;
u is equal to 0 or an integer greater than 0;
v is an integer greater than 0; and is
R11 each represents a covalent bond or a group selected from:
wherein:
w and x are each an integer greater than 0, and
r12 is a covalent bond or a substituted or unsubstituted organic group having C1-C18.
More preferably, B in the above formula (I) is selected from the group consisting of:
wherein R' has the definition as described above.
Most preferably, B in formula (I) above is selected from the group consisting of:
wherein R' has the definition as described above.
D contained in the photosensitive polyimide of formula (I) of the present invention is derived from a diamine monomer which may or may not have a reactive functional group. Preferably, D is independently selected from the group consisting of:
wherein:
r' is-H, C1-C4 alkyl, C1-C4 perfluoroalkyl, methoxy, ethoxy, halogen, OH, COOH, NH2Or SH;
r9 and R11 have the definitions described above;
c is an integer of 0 to 4;
a is an integer greater than 0; and is
b is an integer greater than 0.
More preferably, D in the above formula (I) is each selected from the group consisting of:
wherein y is an integer of 1 to 12, preferably an integer of 1 to 6.
The photosensitive polyimide polymer of the present invention can be obtained by a polymerization method known to those skilled in the art, and can be prepared, for example, by a method comprising the steps of:
(a) reacting a dianhydride monomer having the following formula (1) with a monomer having the formulaOf a diamine monomer of the formula (I) and a compound of the formula (H)2N-P2-NH2To form a compound having the following formula (2):
wherein:
g can be a reactive functional group, for example OH, the following steps are performed:
(b) adding to the product of step (a) an isocyanate compound having the formula O ═ C ═ N — R to form a compound of formula (3)
f+g=i。
In the above-described method for preparing a photosensitive polyimide polymer, dianhydride monomers which can be used in the method of the present invention may be generally aliphatic or aromatic, and preferred examples include, but are not limited to, dianhydrides having the following structures:
wherein,
E. f and H each represent a covalent bond or a substituted or unsubstituted saturated or unsaturated, cyclic or acyclic organic group having C1-C20;
r3 is a covalent bond or is selected from the group consisting of:
preferably, the dianhydride useful in the present invention is selected from the following compounds:
or mixtures thereof.
In the above-mentioned process for producing a photosensitive polyimide polymer, the diamine monomer (I) is usedMust have a reactive functional group (e.g. OH, COOH, NH)2SH, etc.). Diamine monomer (I) useful in the present invention is exemplified by, but not limited to:
wherein:
r9 is H, methyl or ethyl;
s is an integer of 1 to 4;
t is an integer of 0 to 5;
u is equal to 0 or an integer greater than 0;
v is an integer greater than 0;
r11 each represents a covalent bond or a group selected from;
wherein:
w and x are each an integer greater than 0, and
r12 is a covalent bond or a substituted or unsubstituted organic group having C1-C18.
Preferably, the diamine monomer is selected from the group consisting of:
wherein R' has the definition as described above.
More preferably, the diamine monomer is selected from the group consisting of:
wherein R' has the definition as described above.
In the above-mentioned process for producing a photosensitive polyimide polymer, a diamine monomer is usedBody (II) H2N-P2-NH2And, without particular limitation, it may or may not have a reactive functional group. Diamine monomers (II) having no reactive functional groups useful in the present invention are well known to those skilled in the art, such as, but not limited to:
wherein:
r' is-H, C1-C4 alkyl, C1-C4 perfluoroalkyl, methoxy, ethoxy or halogen, OH, COOH, NH2Or SH;
r9 and R11 have the definitions described above;
c is an integer of 0 to 4;
a is an integer greater than 0; and is
b is an integer greater than 0.
Preferably, the above diamine monomer (II) is a diamine selected from the group consisting of:
in order to provide photosensitive groups to the polyimide polymer to facilitate the application of a radiation curing mechanism to the polymer, the present invention uses a photosensitive group-containing isocyanate to modify the polyimide polymer so that it has photosensitive groups, for example, C ═ C double bonds, after modification. The isocyanate may be a mono-isocyanate or a di-isocyanate, preferably a mono-isocyanate. The isocyanate used in the present invention may be reacted with hydroxyl (-OH), carboxyl (-COOH), mercapto (-SH), or amino (-NH) groups in the polyimide polymer2) The reactive groups react to modify the polyimide polymer. The isocyanates used in the present invention have the following structures: o = C = N-R, whichWherein R is R or a group having the structure:
wherein:
r and R2 each represent an optically active group containing an unsaturated group of a vinyl group; and
r1 is a substituted or unsubstituted saturated or unsaturated organic group having C1-C20.
According to a specific embodiment of the present invention, the above-mentioned unsaturated group containing a vinyl group is a group selected from:
wherein:
r4 and R5 are each H or a substituted or unsubstituted alkyl group having C1-C5, and
r6 is a covalent bond or a substituted or unsubstituted organic group having C1-C20;
r1 mentioned above is a group selected from:
wherein:
o, p, q and r are each 0 or an integer greater than 0;
r4, R5 and R6 have the definitions described above;
r7 is H or a substituted or unsubstituted organic group having C1-C12; and
r8 is a covalent bond or is selected from organic groups having:
the invention also provides a photosensitive composition, which comprises at least 1% of photosensitive polyimide polymer with the structure of the formula (I), a photoinitiator and a solvent. The photosensitive composition of the present invention can be used for a liquid photoresist or a dry film photoresist, or for a solder resist, a coverlay film or a printed wiring board. The weight percentage of each component in the photosensitive composition can be adjusted according to the product requirement, generally speaking, the content of the photosensitive polyimide polymer of the formula (I) is at least 1 weight percent, preferably 10-50 weight percent based on the total weight of the whole composition; the photoinitiator is present in an amount of at least 0.001 wt%, preferably between 0.01 and 1 wt%, based on the total weight of the overall composition.
The photoinitiator suitable for use in the above composition according to the present invention is not particularly limited, and may be selected from the group consisting of: benzophenone (benzophenone), benzoin, 2-hydroxy-2-methyl-1-phenylpropanone (2-hydroxy-2-methyl-1-phenyl-propan-1-one), 2-dimethoxy-1,2-diphenylethan-1-one (2,2-dimethoxy-1,2-diphenylethan-1-one), 1-hydroxycyclohexylphenylketone (1-hydroxycyclohexylphenylketone), 2,4, 6-trimethylbenzoyldiphenylphosphine oxide (2,4, 6-trimethylbenzoyldiphenylphosphine oxide), N-phenylglycine, 9-phenylacridine (9-phenylacridine), benzyldimethyl ketal (benzyldimethyllketone), 4' -bis (diethylamine) benzophenone, 2,4,5-triarylimidazole dimers (2,4,5-triarylimidazole dimers) and mixtures thereof; the preferred photoinitiator is benzophenone.
According to the present invention, the solvent suitable for use in the above composition is not particularly limited, and is, for example, but not limited to, selected from the group consisting of: n-methylpyrrolidone (NMP), Dimethylacetamide (DMAC), Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), toluene (tolumene), xylene (xylene), and mixtures thereof.
To increase the degree of photocrosslinking, the photosensitive composition of the present invention may optionally be added with an amount of reactive monomer or short chain oligomer to form crosslinks (Crosslinking) between molecules. According to the present invention, the reactive monomer or oligomer suitable for use in the above composition is not particularly limited, and may be selected from the group consisting of: 1,6-hexanediol diacrylate (1,6-hexanediol diacrylate), neopentyl glycol diacrylate (neopentylglycol diacrylate), ethylene glycol diacrylate (ethylene glycol diacrylate), pentaerythritol diacrylate (pentaerythrityl diacrylate), trimethylolpropane triacrylate (trimethylolpropane triacrylate), pentaerythritol triacrylate (pentaerythrityl triacrylate), dipentaerythritol hexaacrylate (dipentaerythrityl methacrylate), tetramethylolpropane tetraacrylate (tetramethylolpropane tetraacrylate), tetraethylene glycol diacrylate (tetraethylene glycol diacrylate), 1,6-hexanediol dimethacrylate (1,6-hexanediol diacrylate), neopentyl glycol dimethacrylate (neopentyl glycol dimethacrylate), pentaerythritol dimethacrylate (trimethylolpropane dimethacrylate), pentaerythritol dimethacrylate (trimethacrylate), pentaerythritol dimethacrylate (trimethylolpropane dimethacrylate), pentaerythritol methacrylate (trimethacrylate), pentaerythritol methacrylate (trimethacrylate), pentaerythritol methacrylate (trimethacrylate (trimethylolpropane triacrylate (trimethacrylate), pentaerythritol methacrylate (trimethylolpropane triacrylate (pentaerythritol methacrylate), pentaerythritol methacrylate, pentaerythritol, Dipentaerythritol hexamethacrylate, tetramethylpropylene tetramethacrylate, tetraethylene glycol dimethacrylate, methoxydiethylene glycol methacrylate, methoxypolyethylene glycol methacrylate, β -methacryloyloxyethylhydrodienoate, 3-chloro-2-hydroxypropyl methacrylate, 3-chloro-2-hydroxyphenylmethacrylate, methacryloyloxypropylmethacrylate, and methoxypolyethylene glycol methacrylate, and polyoxyethylene glycol methacrylate, and polyoxyethylene glycol methacrylate, and polyoxyethylene methacrylate, Beta-acryloxyethylhydrogensuccinate (beta-acryloxyethylhydrogensuccinate), laurylacrylate (laurylacrylate), ethyleneglycol dimethacrylate (ethyleneglycol dimethacrylate), diethyleneglycol dimethacrylate (diethyleneglycol dimethacrylate), triethyleneglycol dimethacrylate (triethyleneglycol dimethacrylate), polyethyleneglycol dimethacrylate (polyethyleneglycol dimethacrylate), 1, 3-butyleneglycol dimethacrylate (1, 3-butylglycol dimethacrylate), polypropyleneglycol dimethacrylate (polypropyleneglycoldimethacrylate), 2-hydroxy-1, 3-dimethylpropyleneoxy propane (2-hydroxy-1, 3-dimethoxypropane), 2-bis [4- (methacryloxyethoxy) phenyl ] propane (2, 2-dioxy [4- (2, 2-dioxy) phenyl ] propane (2,2-bis [4- (2, 4-dimethoxyphenyl ] propane), 2-bis [4- (2, 4-dimethoxyphenyl ] propane (2, 2-dimethoxyphenyl) propane (2, 2-dimethoxypropyl) propane, 2-bis [4- (methacryloxypolyethoxy) phenyl ] propane, 2-bis [4- (methacryloxypolyethoxy) phenyl ] propane (2,2-bis [4- (methacryloxypolyethoxy) phenyl ] propane), polyethylene glycol diacrylate (polyethylene glycol diacrylate), tripropylene glycol diacrylate (tripropylene glycol diacrylate), polypropylene glycol diacrylate (polypropyleneglycol diacrylate), 2-bis [4- (acryloxydiethoxy) phenyl ] propane (2,2-bis [4- (acryloxyethoxy) phenyl ] propane), 2-bis [4- (acryloxypolyethoxy) phenyl ] propane (2,2-bis [4- (acryloxypolyethoxy) phenyl ] propane), 2-hydroxy-1-3-methyl-3-propylene-2-bis [4- (acryloxypolyethoxy) phenyl ] propane (2,2-bis [4- (acryloxypolyethoxy) phenyl ] propane), Trimethylolpropane trimethacrylate (trimethylolpropane trimethacrylate), tetramethylolmethane triacrylate (tetramethylolmethane tetraacrylate), methoxypropylene glycol methacrylate (methoxypropylene glycol methacrylate), methoxytriethylene glycol acrylate (monomethylolmethane glycol acrylate), nonylphenoxypolyethylene glycol acrylate (nonylphenoxypolyethylene glycol acrylate), polyoxyethylene glycol acrylate (polyoxyethylene glycol acrylate), polyoxyethylene-2-acrylate (polyoxyethylene glycol acrylate), isopropylethylene glycol acrylate (polyoxyethylene glycol acrylate), polyoxyethylene-4-butylene glycol methacrylate (polyoxyethylene-1-polyoxyethylene glycol acrylate), polyoxyethylene-4-polyoxyethylene glycol acrylate (polyoxyethylene-4-polyoxyethylene glycol methacrylate), polyoxyethylene-4-polyoxyethylene glycol methacrylate (polyoxyethylene-1-polyoxyethylene glycol methacrylate), polyoxyethylene-4-polyoxyethylene glycol acrylate (polyoxyethylene-4-polyoxyethylene glycol methacrylate), 5-pentanediol dimethacrylate (3-methyl-1,5-pentanediol dimethacrylate), 1,6-hexanediol methacrylate (1,6-hexanediol methacrylate), 1,9-nonanediol methacrylate (1,9-nonanediol methacrylate), 2,4-diethyl-1,5-pentanediol dimethacrylate (2, 4-diethylene-1, 5-pentanediol dimethacrylate), 1,4-cyclohexanedimethanol dimethacrylate (1, 4-cyclohexanedimethanoldimethacrylate), dipropylene glycol diacrylate (dipropylene glycol diacrylate), tricyclodecanetrimethacrylate (tricyclohexylenediacrylate), 2-dihydrobis [4-acryloxypolyethoxy ] phenyl ] propane (2, 2-dihydrobis [4-acryloxy ] phenyl ] propane (2, 2-dihydrophenoxy [ 4-propoxy ] propane), 2-propenedioxy ] propane (2, 4-propenyloxyphenoxy [ 2, 4-propenyloxypropylpropane (2, 2-propenyloxypropylphenoxy ] propane), 2-bis [ 4-acryloxypropylphenyl ] propane), 2,4-diethyl-1,5-pentanediol diacrylate (2,4-diethyl-1,5-pentanediol diacrylate), ethoxylated trimethylolpropane triacrylate (ethoxylated trimethylolpropane triacrylate), propoxylated trimethylolpropane triacrylate (ethoxylated trimethylolpropane triacrylate), tris (ethacrylate) (isocyanuric acid), pentaerythritol tetraacrylate (pentaerythrityl tetraacrylate), ethoxylated pentaerythritol tetraacrylate (ethoxylated pentaerythritol tetraacrylate), propoxylated pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol tetraacrylate (allyl methacrylate), pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol tetraacrylate (pentaerythritol methacrylate), pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol tetraacrylate (pentaerythritol methacrylate), pentaerythritol tetraacrylate (allyl methacrylate), pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol tetraacrylate (pentaerythritol methacrylate), pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol tetraacrylate (pentaerythritol methacrylate), pentaerythritol tetraacrylate (pentaerythritol tetraacrylate), pentaerythritol (pentaerythritol methacrylate), pentaerythritol (pentaerythritol methacrylate), pentaerythritol (pentaerythritol methacrylate), pentaerythritol (pentaerythritol methacrylate), pentaerythritol, 1,3, 5-triacrylhexahydro-s-tris (1,3,5-triacryloylhexahydro-s-triazine), triallyl1,3, 5-benzoate (triallyl1,3, 5-benzazole), triallylamine (triallylamine), triallyl citrate (triallyl citrate), triallyl phosphate (triallyl phosphate), alloparbital (allophanatal), diallylamine (diallylamine), diallyldimethylsilane (diallyldimethacrylate), diallyldisulfide (diallyl disulfide), diallylether (diallyl ether), diallyl cyanurate (diallyl cyanurate), diallyl isopropoxide (diallyl isopropoxide), diallyl terephthalate (diallyl maleate), 1, 3-diallyl-2 (diallyl-2-diallyl-maleate), diallyl maleate (diallyl maleate), diallyl-2-diallyl maleate, diallyl maleate (diallyl maleate), diallyl-diallyl maleate, diallyl-2-diallyl maleate, diallyl maleate (diallyl maleate), diallyl maleate, diallyl-maleate, diallyl-maleate, diallyl-maleate, diallyl-diallyl, 4,4'-isopropylidene diphenol dimethacrylate (4,4' -isopropylidene diphenol) and 4,4'-isopropylidene diphenol diacrylate (4,4' -isopropylidene diphenol). The reactive monomers or oligomers used in the photosensitive composition of the invention, when present, are present in an amount of at least 0.1% by weight, preferably from 0.1 to 20% by weight, based on the total weight of the total composition.
The following examples are intended to illustrate the present invention without limiting the scope thereof, and any changes and modifications that can be made by one skilled in the art without departing from the spirit of the present invention are intended to be included within the scope thereof.
In the examples, the abbreviations used are defined as follows:
and (3) PMDA: pyromellitic dianhydride (pyromellitic dianhydride)
DABA: 3, 5-diaminobenzoic acid (3,5-diamino benzoic acid)
6 FDA: 4,4'-hexafluoroisopropylidene diphthalic dianhydride (4,4' -hexafluoroisopropylidene-2,2-bis- (phthalic acid anhydride)
BAPA: 2,2'-bis (3-amino-4-hydroxyphenyl) propane (2,2' -bis (3-amino-4-hydroxyphenyl) propane)
MBAA: bis (4-amino-3-carboxyphenyl) methane (bis (4-amino-3-carboxyphenyl) methane)
MEMG: bis (4-aminophenoxy) methane
TAB-E: 3,3',4,4' -Tetraaminodiphenyl ether (3,3',4,4' -tetraaminodiphenylether)
IEM: 2-Isocyanatoethyl methacrylate (2-Isocyanoethyl methacrylate)
1-MI: 1-methylimidazole (1-methylimidazole)
HEMA: 2-hydroxyethyl methacrylate (2-hydroxyhexyl methacrylate)
HMC: 4'-hydroxy-4-methoxychalcone (4' -hydroxy-4-methoxychalcone)
TMDC: tetramethylene diisocyanate (tetramethylene diisocyanate)
IPDI: isophorone diisocyanate (isophoron diisocyanate)
PTZ: phenothiazine (phenothiazine)
DMAC: dimethylacetamide (dimethyl acetamide)
NMP: n-methylpyrrolidone (N-methylpyrrolidinone)
Example 1: synthesis of polyimide having carboxyl group (P1)
43.62g (0.2mol) of PMDA and 30.43g (0.2mol) of DABA were weighed, 300mL of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, then heated to 50 ℃ and stirred for 4 hours. After 4 hours, 50mL of xylene were added and water was removed at 150 ℃ with a dean-stark apparatus. After the water removal was completed, a polyimide solution having an acid group (P1) was obtained.
Example 2: synthesis of carboxyl isocyanate-modified polyimide (I-P1)
370g of P1 was weighed, and 1-MI1.4g, IEM15.5g and PTZ0.1g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (I-P1) in which the desired carboxyl group was modified with an isocyanate.
Example 3: synthesis of polyimide having hydroxyl group (P2)
88.85g (0.2mol) of 6FDA and 57.26g (0.2mol) of BAPA were weighed, 300mL of NMP was added, and the mixture was stirred at room temperature for 1 hour, then heated to 50 ℃ and stirred for 4 hours. After 4 hours, 50mL of xylene were added and water was removed at 150 ℃ with a dean-stark apparatus. After the water removal was completed, a polyimide solution having a hydroxyl group (P2) was obtained.
Example 4: synthesis of polyimide with hydroxyl group modified with isocyanate (I-P2)
440g of P2 was weighed, and 1-MI1.67g, IEM36.86g and PTZ0.12g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (I-P2) in which the desired hydroxyl group was modified with an isocyanate.
Example 5: synthesis of polyimide having carboxyl group modified with diisocyanate (DI-P1)
370g of P1 was weighed, and 1-MI1.4g, HEMA13.01g, TMDC14.01g and PTZ0.1g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a desired carboxyl group diisocyanate-modified polyimide (DI-P1).
Example 6: synthesis of polyimide with hydroxyl group modified with diisocyanate (DI-P2)
440g of P2 was weighed, and 1-MI1.67g, HEMA13.01g, TMDC14.01g and PTZ0.12g were added thereto and stirred at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (DI-P2) in which the desired hydroxyl group was modified with a diisocyanate.
Example 7: synthesis of polyimide having carboxyl group (P3)
43.62g (0.2mol) of PMDA, 15.22g (0.1mol) of DABA and 23.03g (0.1mol) of MEMG were weighed, 300mL of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, then heated to 50 ℃ and stirred for 4 hours. After 4 hours, 50mL of xylene were added and water was removed at 150 ℃ with a dean-stark apparatus. After the water removal was completed, a polyimide solution having a carboxyl group (P1) was obtained.
Example 8: synthesis of carboxyl isocyanate-modified polyimide (I-P3)
420g of P3 was weighed, and 1-MI0.7g, IEM7.75g and PTZ0.1g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (I-P3) in which the desired carboxyl group was modified with an isocyanate.
Example 9: synthesis of polyimide having carboxyl group modified with diisocyanate (DI-P3)
420g of P3 was weighed, and 1-MI0.7g, HEMA6.5g, TMDC7g and PTZ0.11g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a desired carboxyl group diisocyanate-modified polyimide (DI-P3).
Example 10: synthesis of polyimide having hydroxyl group (P4)
88.85g (0.2mol) of 6FDA and 28.63g (0.1mol) of BAPA and 23.03g (0.1mol) of MEMG are weighed out, 300mL of NMP are added, stirred at room temperature for 1 hour, warmed to 50 ℃ and stirred for 4 hours. After 4 hours, 50mL of xylene were added and water was removed at 150 ℃ with a dean-stark apparatus. After the water removal was completed, a polyimide solution having a hydroxyl group (P4) was obtained.
Example 11: synthesis of polyimide with hydroxyl group modified with diisocyanate (DI-P4)
490g of P4 was weighed, and 1-MI0.85g, HEMA6.51g, IPDI11.12g and PTZ0.11g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (DI-P4) in which the desired hydroxyl group was modified with a diisocyanate.
Example 12: synthesis of polyimide with hydroxyl group modified with diisocyanate (DI-P5)
490g of P4 were weighed, and 1-MI0.85g, HMC25.43g, IPDI22.23g and PTZ0.11g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (DI-P5) in which the desired hydroxyl group was modified with a diisocyanate.
Example 13: synthesis of polyimide having amino group (P6)
43.62g (0.2MOL) of PMDA, 23.03g (0.1MOL) of TAB-E and 28.63g (0.1MOL) of DABA were weighed, 300mL of NMP was added thereto, and the mixture was stirred at room temperature for 1 hour, then heated to 50 ℃ and stirred for 4 hours. After 4 hours, 50mL of xylene were added and water was removed at 150 ℃ with a dean-stark apparatus. After the water removal was completed, a polyimide solution having an amino group (P6) was obtained.
Example 14: synthesis of amino isocyanate-modified polyimide (I-P6)
440g of P6 was weighed, and 1-MI0.85g, IEM15.5g and PTZ0.1g were added thereto, followed by stirring at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a polyimide (I-P6) in which the desired amino group was modified with an isocyanate.
Example 15: synthesis of amino diisocyanate-modified polyimide (DI-P6)
440g of P6 was weighed, 1-MI1.45g, HEMA6.51g, IPDI11.12g and PTZ0.11g were added, and the mixture was stirred at room temperature for 1 hour. After 1 hour, the temperature was raised to 60 ℃ and the mixture was stirred for 6 hours to obtain a desired amino diisocyanate-modified polyimide (DI-P6).
Claims (13)
1. A photosensitive polyimide polymer with the structure of formula (I),
Wherein:
a and C may be the same or different and are each independently a tetravalent organic group;
wherein R represents an unsaturated group containing a vinyl group or a group selected from:
wherein:
r1 is a substituted or unsubstituted saturated or unsaturated organic group having C1-C20, and
r2 is a vinyl-containing unsaturated group;
each D is independently a divalent organic group;
n is an integer greater than 0, and
m is equal to 0 or an integer greater than 0.
2. A photosensitive polyimide polymer as defined in claim 1, wherein the vinyl group-containing unsaturated group is a group selected from:
wherein:
r4 and R5 are each H or substituted or unsubstituted alkyl having C1-C5, and
r6 is a covalent bond or a substituted or unsubstituted organic group having C1-C20.
4. A photosensitive polyimide polymer as claimed in claim 1, wherein R1 is a group selected from:
wherein:
o, p, q and r are each 0 or an integer greater than 0;
r4, R5 and R6 have the definitions as set forth in claim 2;
r7 are each H or a substituted or unsubstituted organic group having C1-C12; and is
R8 is a covalent bond or is selected from organic groups having:
7. a photosensitive polyimide polymer according to claim 1, wherein the divalent organic groups of B are each selected from the group consisting of:
wherein:
r9 is H, methyl or ethyl;
s is an integer of 1 to 4;
t is an integer of 0 to 5;
u is equal to 0 or an integer greater than 0;
v is an integer greater than 0; and is
R11 each represents a covalent bond or a group selected from;
wherein:
w and x are each an integer greater than 0, and
r12 is a covalent bond or a substituted or unsubstituted organic group having C1-C18.
9. A photosensitive polyimide polymer according to claim 1, wherein D is selected from the group consisting of:
r' is-H, C1-C4 alkyl, C1-C4 perfluoroalkyl, methoxy, ethoxy, halogen, OH, COOH, NH2Or SH;
r9 and R11 have the definitions as set forth in claim 7;
c is an integer of 0 to 4;
a is an integer greater than 0; and is
b is an integer greater than 0.
11. A photosensitive composition comprising at least 1% of the photosensitive polyimide polymer of claim 1, and at least one photoinitiator, based on the total weight of the composition.
12. The photosensitive composition of claim 11, further comprising a reactive monomer or oligomer.
13. The photosensitive composition according to claim 11 or 12, which is used for a liquid photoresist or a dry film photoresist.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05232701A (en) * | 1992-02-20 | 1993-09-10 | Hitachi Chem Co Ltd | Photosensitive resin compound |
US5472823A (en) * | 1992-01-20 | 1995-12-05 | Hitachi Chemical Co., Ltd. | Photosensitive resin composition |
JP2006169409A (en) * | 2004-12-16 | 2006-06-29 | Kaneka Corp | Polyimide precursor and photosensitive resin composition using it |
CN101068852A (en) * | 2004-12-16 | 2007-11-07 | 日本化药株式会社 | Unsaturated group-containing polyimide resin, photosensitive resin composition containing same, and cured product thereof |
-
2008
- 2008-01-25 CN CN201310413998.3A patent/CN103524735A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5472823A (en) * | 1992-01-20 | 1995-12-05 | Hitachi Chemical Co., Ltd. | Photosensitive resin composition |
JPH05232701A (en) * | 1992-02-20 | 1993-09-10 | Hitachi Chem Co Ltd | Photosensitive resin compound |
JP2006169409A (en) * | 2004-12-16 | 2006-06-29 | Kaneka Corp | Polyimide precursor and photosensitive resin composition using it |
CN101068852A (en) * | 2004-12-16 | 2007-11-07 | 日本化药株式会社 | Unsaturated group-containing polyimide resin, photosensitive resin composition containing same, and cured product thereof |
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