CN102964515A - Resin for interlayer insulating film and protective film, and photosensitive resin composition - Google Patents
Resin for interlayer insulating film and protective film, and photosensitive resin composition Download PDFInfo
- Publication number
- CN102964515A CN102964515A CN2012102032455A CN201210203245A CN102964515A CN 102964515 A CN102964515 A CN 102964515A CN 2012102032455 A CN2012102032455 A CN 2012102032455A CN 201210203245 A CN201210203245 A CN 201210203245A CN 102964515 A CN102964515 A CN 102964515A
- Authority
- CN
- China
- Prior art keywords
- resin
- methyl
- acid
- acrylic monomer
- interlayer dielectric
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011347 resin Substances 0.000 title claims abstract description 103
- 229920005989 resin Polymers 0.000 title claims abstract description 103
- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 239000011229 interlayer Substances 0.000 title claims abstract description 20
- 230000001681 protective effect Effects 0.000 title claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 88
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 87
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 30
- 239000004593 Epoxy Substances 0.000 claims abstract description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000005977 Ethylene Substances 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 24
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910000077 silane Inorganic materials 0.000 claims abstract description 20
- -1 propyl diester Chemical class 0.000 claims description 104
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 34
- 150000008065 acid anhydrides Chemical class 0.000 claims description 24
- 238000010276 construction Methods 0.000 claims description 21
- 239000012528 membrane Substances 0.000 claims description 18
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 8
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 5
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003999 initiator Substances 0.000 abstract description 9
- 230000035515 penetration Effects 0.000 abstract description 9
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000002585 base Substances 0.000 description 41
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 34
- 150000002148 esters Chemical class 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 125000004494 ethyl ester group Chemical group 0.000 description 17
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 238000005530 etching Methods 0.000 description 8
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 150000002924 oxiranes Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 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 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 3
- 229960000846 camphor Drugs 0.000 description 3
- 229930008380 camphor Natural products 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XWUNIDGEMNBBAQ-UHFFFAOYSA-N Bisphenol A ethoxylate diacrylate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCCOC(=O)C=C)C=C1 XWUNIDGEMNBBAQ-UHFFFAOYSA-N 0.000 description 2
- WQUYGVLLSSYSRD-UHFFFAOYSA-N C(C=C)(=O)OCC(C)O.CC=CC(=O)O Chemical compound C(C=C)(=O)OCC(C)O.CC=CC(=O)O WQUYGVLLSSYSRD-UHFFFAOYSA-N 0.000 description 2
- WXNOGBYAKIIZTE-UHFFFAOYSA-N CC(=C)C(O)=O.CO[SiH](OC)OC Chemical compound CC(=C)C(O)=O.CO[SiH](OC)OC WXNOGBYAKIIZTE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FIIMPIBOJUPHNA-UHFFFAOYSA-N O1CCCC1.CC=CC(=O)O Chemical compound O1CCCC1.CC=CC(=O)O FIIMPIBOJUPHNA-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- HIVQCJOGAHNXBO-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] propanoate Chemical compound CCC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C HIVQCJOGAHNXBO-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- JVASZXZJOJUKDT-UHFFFAOYSA-N bis(1-aminocyclohexa-2,4-dien-1-yl)methanone Chemical compound C1C=CC=CC1(N)C(=O)C1(N)CC=CC=C1 JVASZXZJOJUKDT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 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
- 238000004090 dissolution Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
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- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
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- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
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- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
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- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
The invention provides a resin for an interlayer insulating film and a protective film, which is a copolymer obtained by reacting an acrylic monomer containing an epoxy structure, a silane-containing acrylic monomer, an aromatic ring-containing acrylic monomer and an unsaturated carboxylic acid and/or an anhydride thereof selected from the group consisting of the acrylic monomers. The invention also provides a photosensitive resin composition, which comprises the resin, a polymerizable compound with an ethylene type unsaturated bond, a photopolymerization initiator and a solvent. The resin of the invention can provide excellent surface hardness, adhesive force and penetration rate, so that the resin meets the requirement of industrial utilization.
Description
Technical field
The present invention relates to a kind of resin combination, especially a kind of alkali-soluble acrylic resin and Photosensitve resin composition thereof are for the manufacture of interlayer dielectric and protective membrane.
Background technology
At present; the photosensitive resin material has been widely used in the fields such as printed circuit board (PCB) (PCB), unicircuit (IC), display panels (LCD) and MEMS (micro electro mechanical system) (MEMS), is used for making protective layer or the insulation layer of photoresist for example and electronic package.JP2007-156139 has disclosed a kind of Photosensitve resin composition, can be used for making the light interval body in the display panels, and splendid elasticity is provided.Sensitive materials refers to the aitiogenic material of light, intramolecule (Intra-reaction) or intermolecular (Inter-reaction) occuring behind the absorb light energy change (for example change in polarity, splitting of chain or chain are crosslinked), and causes exposure region and unexposed area to the difference on the developing solution generation dissolution rate.For example, negative photosensitive material produces crosslinking reaction and becomes and is insoluble in developing solution after exposure; Otherwise the positive type light sensitive material then becomes after exposure and is soluble in developing solution, so that exposure region can use developing solution to remove.Photoetching technique (photolithography) namely is the characteristic of utilizing sensitive materials, makes fine pattern in the electronic package by steps such as exposure, developments.In the photolithographic fabrication operation, utilize such as radiation such as UV-light, electron beam or X-rays, see through light shield (photomask), the sensitive materials that is covered on the base material is optionally exposed, recycling exposure region and the difference of unexposed area on dissolution rate are developed, so that the pattern on the light shield (for example: line pattern) be transferred on the sensitive materials.
Because development trend microminiaturized and high integration (Integration), many characteristics of resin material also need to promote thereupon.Therefore, for the diversification that meets the requirement such as high resolving power and satisfy resin material is used, the photosensitive resin material must have high photosensitivity, high penetration, high surface hardness, high heat resistance, high flat degree, high resistance etching, low heat expansion property, and to the characteristics such as high adhesive force of base material etc., so that the performance of product excellence to be provided, and the reliability of improving product and qualification rate.JP 3994429(JP 2000-162769) disclosed a kind of resin combination that can be used for forming film in display panels, integrated circuit (IC) apparatus or the solid-state image capturing apparatus (solid state image pickup device), it can provide good surface smoothness (surface smoothness), thermotolerance (heat resistance), transparency (transparency) and chemical resistant properties (chemical resistance).180311 of TW have disclosed a photoresist that is used for short wavelength's imaging (short wavelength imaging), can provide good resolving power and to the sticking power of copper base material.In addition, TW I336711 has disclosed a kind of eurymeric photoresist, polynuclear plane and high polarity unit is imported in the resin, to improve dry etching patience and developing solution affinity.TW I342467 has then disclosed a kind of negative light resistance agent, outside the compositions such as resin, photo-sensitive initiators, adds the mixture of water-insoluble and water-soluble monomer in composition, to increase the contrast of developing.
But for meet the demand of industry, still need badly have high adhesive force and can be water-fastness, etch resistant etc., and provide simultaneously the resin material of the characteristics such as high surface hardness and high penetration.
Summary of the invention
The invention provides a kind of resin, can be used for Photosensitve resin composition, the demand of utilizing to meet industry.Resin of the present invention is by comprising the acrylic monomer, the acrylic monomer that contains silane that contain epoxy construction, containing the acrylic monomer of aromatic nucleus and be selected from and be different from the multipolymer that this contains epoxy construction, contains silane and contains the unsaturated carboxylic acid of acrylic monomer of aromatic nucleus and at least one (that is unsaturated carboxylic acid and/or its acid anhydrides) of acid anhydrides reacts.According to the present invention, this resin is alkali soluble resin, and its weight-average molecular weight is 5000 to 30000.
One specific embodiment according to the present invention, unsaturated carboxylic acid is selected from one of vinylformic acid and methacrylic acid, and this acid anhydrides system is selected from one of acrylic anhydride and methacrylic anhydride.
One specific embodiment according to the present invention, the acrylic monomer that contains epoxy construction are selected from the acrylic monomer that contains epoxy cyclohexane ring (epoxycyclohexane ring).
In the part example of the present invention, resin is the multipolymer of unsaturated carboxylic acid and/or its acid anhydrides and acrylic monomer, and this acrylic monomer comprises metha crylic monomer and methacrylate ester monomer.One specific embodiment according to the present invention, this acrylic monomer that contains epoxy construction is methacrylic acid 3,4-epoxycyclohexyl methyl ester.One specific embodiment according to the present invention, the acrylic monomer that contains silane are methacrylic acid 3-(Trimethoxy silane base) propyl diester.One specific embodiment according to the present invention, the acrylic monomer that contains phenyl ring is benzyl methacrylate.To be binding on the ester group part with this epoxy construction group, silicon group and aromatic group.
The present invention also provides a kind of Photosensitve resin composition, and it comprises resin of the present invention, has the polymerizable compound of ethylene type unsaturated link(age), Photoepolymerizationinitiater initiater and solvent.
One specific embodiment according to the present invention, the content of this resin take the gross weight of this Photosensitve resin composition as benchmark, is 10 to 30wt%.
One specific embodiment according to the present invention, the polymerizable compound that this has the ethylene type unsaturated link(age) is the polyfunctional compound with ethylene type unsaturated link(age), and this polyfunctional compound can carry out polymerization or crosslinked with this resin.This has the content of the polymerizable compound of ethylene type unsaturated link(age), take the gross weight of this Photosensitve resin composition as benchmark, is 5 to 20wt%.
One specific embodiment according to the present invention, the content of this Photoepolymerizationinitiater initiater take the gross weight of this Photosensitve resin composition as benchmark, is 0.5 to 5wt%.
In the part example of the present invention, Photosensitve resin composition comprises solvent.The content of solvent take the gross weight of this Photosensitve resin composition as benchmark, is 50 to 80wt%.
Resin provided by the invention and Photosensitve resin composition thereof can promote its sticking power when high surface hardness and high penetration are provided, to represent the characteristic such as excellent water-fastness, etch resistant, the utmost point meets the demand of industry.
Embodiment
Below, by particular specific embodiment explanation embodiments of the present invention, those skilled in the art can understand other advantage of the present invention and effect by content disclosed in the present specification.The present invention also can be implemented or used by other different specific embodiment, and the every details in this specification sheets can based on different viewpoints and application, not carried out various modifications and change under the spirit departing from this creation yet.
Unless otherwise indicated herein, employed singulative " " reaches " being somebody's turn to do " and comprises most individual otherwise in specification sheets and claims.
Unless otherwise indicated herein, otherwise in specification sheets and claims employed term "or" generally include " and/or " implication.
Term as used herein " weight-average molecular weight " is the value that is converted into polystyrene weight-average molecular weight (Mw) of utilizing gel permeation chromatography (GPC) to measure take tetrahydrofuran (THF) (THF) as solvent.
Term as used herein " acrylic acid series " comprises acrylic acid series and metha crylic.Term as used herein " (methyl) vinylformic acid ... " expression comprises or does not comprise the literal in the bracket.For example, " (methyl) vinylformic acid " comprises vinylformic acid and methacrylic acid, and " (methyl) acrylic anhydride " comprises acrylic anhydride and methacrylic anhydride, by that analogy.
The invention provides a kind of resin, by comprising the acrylic monomer, the acrylic monomer that contains silane that contain epoxy construction, containing the acrylic monomer of aromatic nucleus and be selected from and be different from this acrylic monomer that contains epoxy construction, contain the acrylic monomer of silane and contain the unsaturated carboxylic acid of acrylic monomer of aromatic nucleus and at least one multipolymer that reacts in the acid anhydrides thereof.
According to the present invention, this resin is alkali soluble resin, can be used for Photosensitve resin composition.One specific embodiment according to the present invention, the weight-average molecular weight of resin are 5000 to 30000.
Be used for the unsaturated carboxylic acid of resin of the present invention, there is no particular restriction.The example of unsaturated carboxylic acid includes but not limited to: (methyl) vinylformic acid, butenoic acid (crotonic acid), maleic acid, FUMARIC ACID TECH GRADE, methyl-maleic acid (citroconic acid), methylfumaric acid, methylene-succinic acid (itaconic acid), Sorbic Acid and combination thereof etc.Be used for the unsaturated carboxylic acid anhydrides of resin of the present invention, there is no particular restriction.The example of unsaturated carboxylic acid anhydrides includes but not limited to the acid anhydrides of above-mentioned unsaturated carboxylic acid and combination thereof etc.
One specific embodiment according to the present invention contains at least a unsaturated carboxylic acid or its acid anhydrides in the resin.One specific embodiment according to the present invention, preferred (methyl) vinylformic acid of unsaturated carboxylic acid.One specific embodiment according to the present invention, preferred (methyl) acrylic anhydride of unsaturated acid anhydride.In the part example of these specific embodiments, resin of the present invention is that unsaturated carboxylic acid and this contain epoxy construction, siliceous and contain the multipolymer of the acrylic monomer of aromatic nucleus.
According to the present invention, the acrylic monomer (calling acrylic monomer in the following text) that unsaturated carboxylic acid and/or its acid anhydrides and this contain epoxy construction, contain silane and contain aromatic nucleus forms multipolymer.In one specific embodiment, when forming multipolymer, the consumption of this unsaturated carboxylic acid and/or its acid anhydrides take the total amount of this unsaturated carboxylic acid and/or its acid anhydrides and this acrylic monomer as benchmark, is 10 to 40 % by mole.
One specific embodiment according to the present invention, resin are the multipolymers of unsaturated carboxylic acid and acrylic monomer, and this acrylic monomer comprises the acrylic monomer that contains epoxy construction, contain the acrylic monomer of silane and contain the acrylic monomer of aromatic nucleus.
The acrylic monomer that contains epoxy construction that is used for resin of the present invention is not particularly limited, if contain epoxide group and can with unsaturated carboxylic acid and/or its acid anhydrides copolymerization.For example, the acrylic monomer that contains epoxy construction can be selected from but be not limited to contain the polymerizable esters of unsaturated carboxylic acids (polymerizable unsaturated carboxylic acid ester) of epoxy construction, such as, contain (methyl) acrylate, its derivative, its analogue of epoxide group etc., and combination.
The example that contains (methyl) acrylate of epoxide group and derivative thereof etc. includes but not limited to: (methyl) acrylate and the derivative thereof that contain oxyethane ring (oxirane ring), for example, (methyl) acrylic acid epoxy ethyl ester (oxiranyl (meth) acrylates), (methyl) Glycidyl Acrylate ((methyl) glycidyl acrylate), (methyl) vinylformic acid 2-methyl epoxypropyl ester, (methyl) vinylformic acid 2-ethyl epoxypropyl ester, (methyl) vinylformic acid 2-epoxy ethyl ethyl ester, (methyl) vinylformic acid 2-glycidoxy ethyl ester (2-glycidyloxyethyl (meth) acrylates), (methyl) vinylformic acid 3-glycidoxy propyl diester, (methyl) acrylic acid epoxy propoxy-phenylester (glycidyloxyphenyl (meth) acrylates) etc., and combination; (methyl) acrylate and the derivative thereof that contain epoxy cyclohexane ring (epoxycyclohexane ring), for example, (methyl) vinylformic acid 3,4-epoxycyclohexyl ester, (methyl) vinylformic acid 3,4-epoxycyclohexyl methyl ester, (methyl) vinylformic acid 2-(3,4-epoxycyclohexyl) ethyl ester, (methyl) vinylformic acid 2-(3,4-epoxycyclohexyl methoxyl group) ethyl ester, (methyl) vinylformic acid 3-(3,4-epoxycyclohexyl methoxyl group) propyl diester etc., and combination; (methyl) acrylate and the derivative thereof that contain 5,6-epoxy-2-dicyclo [2.2.1] heptane ring (5,6-epoxy-2-bicyclo[2.2.1] heptane ring), for example, (methyl) vinylformic acid 5,6-epoxy-2-dicyclo [2.2.1] heptyl ester etc.; Contain 3,4-epoxy, three ring [5.2.1.0
2,6] (methyl) acrylate and the derivative thereof of decane; The vinyl ether and the derivative thereof that contain epoxide group; The allyl ethers and the derivative thereof that contain epoxide group; Its analogue etc.; And combination.
One specific embodiment according to the present invention has at least a acrylic monomer that contains epoxy construction in the resin.One specific embodiment according to the present invention, the acrylic monomer that contains epoxy construction is selected from (methyl) acrylate of containing the epoxy cyclohexane ring, its derivative, its analogue etc., and combination, be preferably and be selected from methacrylic acid 3,4-epoxycyclohexyl methyl ester, vinylformic acid 3,4-epoxycyclohexyl methyl ester and combination thereof, more preferably methacrylic acid 3,4-epoxycyclohexyl methyl ester.
One specific embodiment according to the present invention, when forming multipolymer, this contains the consumption of the acrylic monomer of epoxy construction, take the total amount of unsaturated carboxylic acid and/or its acid anhydrides and all acrylic monomers as benchmark, is 10 to 50 % by mole.
The acrylic monomer that contains silane that is used for resin of the present invention is not particularly limited, if contain silane and can with unsaturated carboxylic acid and/or its acid anhydrides copolymerization.For example, the acrylic monomer that contains silane can be selected from but be not limited to: contain the polymerizable esters of unsaturated carboxylic acids of silane, such as, contain (methyl) acrylate, its derivative, its analogue of silane etc., and combination.
The example that contains (methyl) acrylate of silane and derivative thereof etc. includes but not limited to: methacrylic acid 3-(Trimethoxy silane base) propyl diester (3-(trimethoxysilyl) propyl methacrylate), vinylformic acid 3-(Trimethoxy silane base) propyl diester, methacrylic acid 2-(Trimethoxy silane base) ethyl ester, methacrylic acid Trimethoxy silane ylmethyl ester, methacrylic acid 3-(triethoxysilicane alkyl) propyl diester, vinylformic acid 3-(triethoxysilicane alkyl) propyl diester, methacrylic acid 2-(triethoxysilicane alkyl) ethyl ester, methacrylic acid triethoxysilicane alkyl methyl ester, methacryloxypropyl three (methoxy ethoxy) silane (methacryloxypropyltri (methoxyethoxy) silane), 3-(methacryloxy) propyl group methyl dimethoxysilane, 3-(acryloxy propyl group) methyl dimethoxysilane, 3-(methacryloxy) propyl-dimethyl Ethoxysilane, 3-(acryloxy) propyl-dimethyl Ethoxysilane, 3-[three (trimethyl silicane alcoxyl base) silylation] the propyl methyl acid esters, 3-[three (dimethyl vinyl silanes oxygen base)] the propyl methyl acid esters, 3-(trichlorosilane base) propyl methyl acid esters, N-3-(methacryloxy-2-hydroxypropyl)-APTES, its derivative, its analogue etc., and combination.Preferable methyl vinylformic acid 3-(Trimethoxy silane base) propyl diester, vinylformic acid 3-(Trimethoxy silane base) propyl diester, methacrylic acid 2-(Trimethoxy silane base) ethyl ester, methacrylic acid Trimethoxy silane ylmethyl ester, methacrylic acid 3-(triethoxysilicane alkyl) propyl diester, vinylformic acid 3-(triethoxysilicane alkyl) propyl diester, methacrylic acid 2-(triethoxysilicane alkyl) ethyl ester, its derivative, its analogue etc., and combination.
One specific embodiment according to the present invention has at least a acrylic monomer that contains silane in the resin.One specific embodiment according to the present invention, the acrylic monomer that contains silane is selected from methacrylic acid 3-(Trimethoxy silane base) propyl diester, vinylformic acid 3-(Trimethoxy silane base) propyl diester, methacrylic acid 3-(triethoxysilicane alkyl) propyl diester, vinylformic acid 3-(triethoxysilicane alkyl) propyl diester and combination thereof.Be preferably and be selected from methacrylic acid 3-(Trimethoxy silane base) propyl diester, vinylformic acid 3-(Trimethoxy silane base) propyl diester and combination thereof, more preferably methacrylic acid 3-(Trimethoxy silane base) propyl diester.
One specific embodiment according to the present invention, when forming multipolymer, this contains the consumption of the acrylic monomer of silane, take the total amount of unsaturated carboxylic acid and/or its acid anhydrides and all acrylic monomers as benchmark, is 10 to 30 % by mole.
The acrylic monomer that contains aromatic nucleus that is used for resin of the present invention is not particularly limited, if contain aromatic nucleus and can with unsaturated carboxylic acid and/or its acid anhydrides copolymerization.For example, the acrylic monomer that contains aromatic nucleus can be selected from but be not limited to: the polymerizable esters of unsaturated carboxylic acids that contains aromatic nucleus, such as (methyl) acrylate that contains aromatic nucleus, its derivative, its analogue etc., and combination, wherein the carbon number of this aromatic nucleus is 6 to 10 carbon atoms.
The example that contains (methyl) acrylate of aromatic nucleus and derivative thereof etc. includes but not limited to: phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, CA, the methyl methacrylate phenyl ester, vinylformic acid 2-nitro phenyl ester (2-nitro phenyl acrylate), methacrylic acid 2-nitro phenyl ester, vinylformic acid 4-nitro phenyl ester, methacrylic acid 4-nitro phenyl ester, methacrylic acid 2-p-Nitrobenzyl (2-Nitro benzyl methacrylate), methacrylic acid 4-p-Nitrobenzyl, vinylformic acid 2-chlorobenzene ester (2-Chloro phenyl acrylate), methacrylic acid 2-chlorobenzene ester, vinylformic acid 4-chlorobenzene ester, methacrylic acid 4-chlorobenzene ester, vinylformic acid 2,4,6-trichlorine phenyl ester, methacrylic acid 2,4,6-trichlorine phenyl ester, Pentachlorophenyl Acrylate, the methacrylic acid pentachlorophenyl ester, vinylformic acid 2,4, the 6-tribromophenyl, methacrylic acid 2,4, the 6-tribromophenyl, vinylformic acid pentabromo-phenyl ester, methacrylic acid pentabromo-phenyl ester, vinylformic acid benzyl chloride ester, methacrylic acid benzyl chloride ester, vinylformic acid 1-phenyl chlorocarbonate, methacrylic acid 1-phenyl chlorocarbonate, vinylformic acid 2-phenyl chlorocarbonate, methacrylic acid 2-phenyl chlorocarbonate, vinylformic acid 3-phenyl propyl ester, methacrylic acid 3-phenyl propyl ester, vinylformic acid tetrahydrochysene benzene dimethyl ester, methacrylic acid tetrahydrochysene benzene dimethyl ester, methacrylic acid phenylbenzene methyl esters, vinylformic acid 2-phenoxy ethyl, methacrylic acid 2-phenoxy ethyl, vinylformic acid 2-hydroxyl-3-phenoxy group propyl ester, methacrylic acid 2-hydroxyl-3-phenoxy group propyl ester, vinylformic acid phenoxy group binaryglycol ester, methacrylic acid phenoxy group binaryglycol ester, vinylformic acid phenoxy group TEG ester, methacrylic acid phenoxy group TEG ester, vinylformic acid phenoxy group six glycol esters, methacrylic acid phenoxy group six glycol esters, its derivative, its analogue etc., and combination.
One specific embodiment according to the present invention has at least a acrylic monomer that contains aromatic nucleus in the resin.One specific embodiment according to the present invention, the acrylic monomer that contains aromatic nucleus is selected from phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, CA, methyl methacrylate phenyl ester, its derivative, its analogue etc., and combination.Be preferably and be selected from phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, CA, methyl methacrylate phenyl ester and combination, more preferably benzyl methacrylate.
One specific embodiment according to the present invention, when forming multipolymer, this contains the consumption of the acrylic monomer of aromatic nucleus, take the total amount of unsaturated carboxylic acid and/or its acid anhydrides and all acrylic monomers as benchmark, is 10 to 20 % by mole.
In addition, one example according to the present invention also can optionally add reactive monomer to adjust the characteristic of resin, such as but not limited to surface hardness, pliability, sticking power, viscosity etc.One specific embodiment according to the present invention can optionally add reactive monomer and unsaturated carboxylic acid and/or its acid anhydrides copolymerization, with the preparation resin.In the part example of these specific embodiments, reactive monomer is selected from the ethylene type unsaturated monomer.In one specific embodiment, reactive monomer optionally is selected from simple function group monomer and polyfunctional monomer.In the part example of these specific embodiments, reactive monomer is multi-functional ethylene type unsaturated monomer.
For example, the ethylene type unsaturated monomer can be but is not limited to: esters of unsaturated carboxylic acids; Unsaturated aromatic monomer; The monomer of amide-containing; Propionate, vinyl-acetic ester etc.; And combination.
The example of ethylene type unsaturated monomer includes but not limited to: (methyl) acrylate and derivative thereof, for example, (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) Ethyl acrylate, (methyl) Octyl acrylate, (methyl) lauryl acrylate, (methyl) stearyl acrylate ester, (methyl) cyclohexyl acrylate, (methyl) allyl acrylate, (methyl) vinylformic acid three ring decyl ester (tricyclodecanyl (meth) acrylate), (methyl) phenyl acrylate, (methyl) benzyl acrylate, (methyl) vinylformic acid oxa-ring butyl ester (oxetanyl (meth) acrylates), (methyl) vinylformic acid 3-methyl-3-oxa-ring butyl ester, (methyl) vinylformic acid 3-ethyl-3-oxa-ring butyl ester, (methyl) vinylformic acid (3-methyl-3-oxa-cyclobutyl) methyl esters ((3-methyl-3-oxetanyl) methyl (meth) acrylates), (methyl) vinylformic acid (3-ethyl-3-oxa-cyclobutyl) methyl esters, (methyl) vinylformic acid 2-(3-methyl-3-oxa-cyclobutyl) ethyl ester, (methyl) vinylformic acid 2-(3-ethyl-3-oxa-cyclobutyl) ethyl ester, (methyl) vinylformic acid 2-[(3-methyl-3-oxa-cyclobutyl) methoxyl group] ethyl ester (2-[(3-methyl-3-oxetanyl) methyloxy] ethyl (meth) acrylates), (methyl) vinylformic acid 2-[(3-ethyl-3-oxa-cyclobutyl) methoxyl group] ethyl ester, (methyl) vinylformic acid 3-[(3-methyl-3-oxa-cyclobutyl) methoxyl group] propyl ester, (methyl) vinylformic acid 3-[(3-ethyl-3-oxa-cyclobutyl) methoxyl group] propyl ester, (methyl) vinylformic acid 2-hydroxyl ethyl ester, (methyl) vinylformic acid tetrahydrofuran (THF) methyl esters, (methyl) vinylformic acid 2-hydroxypropyl acrylate, (methyl) vinylformic acid 2-(three ring [5.2.1.0
2,6] last of the ten Heavenly stems oxygen base) ethyl ester (2-(tricyclo[5.2.1.0
2,6] decyloxy) ethyl (meth) acrylates) etc., and combination.
Other example such as vinylbenzene, Vinyl toluene (such as: adjacent Vinyl toluene, a Vinyl toluene, to Vinyl toluene), α-vinyltoluene, chloro-styrene etc., and combination; Acrylamide derivative, for example, (methyl) acrylamide, N methacrylamide, N-ethyl-methyl acrylamide, N hydroxymethyl acrylamide, N-methylol methacrylamide, N-methoxymethyl acrylamide, N-ethoxyl methyl acrylamide, N-butoxymethyl acrylamide, vinyl cyanide etc. and combination thereof; Maleimide derivatives; Propionate, vinyl-acetic ester, vinyl benzoate etc. and combination thereof; Iso-butylene; And combination.
The reactive monomer that adds in the resin can use commercially available polyfunctional compound, such as, but not limited to Nikalac MX-302 (by Sanwa Chemical Co., Ltd. makes); Aronix M-400, M-402, M-403, M-404, M-408, M-450, M-305, M-309, M-310, M-313, M-315, M-320, M-325, M-326, M-327, M-350, M-360, M-208, M-210, M-215, M-220, M-225, M-233, M-240, M-245, M-260, M-270, M-1100, M-1200, M-1210, M-1310, M-1600, M-221, M-203, TO-924, TO-1270, TO-1231, TO-595, TO-756, TO-1343, TO-1382, TO-902, TO-904, TO-905, TO-1330 (by Toagosei Co., Ltd. makes); Kayarad D-310, D-330, DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-120, DN-0075, DN-2475, SR-295, SR-355, SR-399E, SR-494, SR-9041, SR-368, R-415, SR-444, SR-454, SR-492, SR-499, SR-502, SR-9020, SR-9035, SR-111, SR-212, SR-213, SR-230, SR-259, SR-268, SR-272, SR-344, SR-349, SR-368, SR-601, SR-602, SR-610, SR-9003, PET-30, T-1420, GPO-303, TC-120S, HDDA, NPGDA, TPGDA, PEG400DA, MANDA, HX-220, HX-620, R-551, R-712, R-167, R-526, R-551, R-712, R-604, R-684, TMPTA, THE-330, TPA-320, TPA-330, KS-HDDA, KS-TPGDA, KS-TMPTA (by Nippon Kayaku Co., Ltd. makes); LightAcrylate PE-4A, DPE-6A, DTMP-4A (by Kyoeisha Chemical Co., Ltd. makes) etc., and combination.
One specific embodiment according to the present invention, preferred (methyl) acrylate of reactive monomer and derivative thereof.In the part example of this embodiment, resin is the multipolymer of unsaturated carboxylic acid and/or its acid anhydrides and acrylic monomer, and this acrylic monomer comprises the acrylic monomer that contains epoxy construction, the acrylic monomer that contains silane, the acrylic monomer that contains aromatic nucleus and reactive monomer.
When forming multipolymer, the consumption of this reactive monomer take the total amount of unsaturated carboxylic acid and/or its acid anhydrides, all acrylic monomers as benchmark, is 40 to 90 % by mole.
The preparation of resin can utilize polyreaction to carry out, and polyreaction is carried out under the existence of radical initiator usually.There is no particular restriction for radical initiator, can use general employed radical initiator in this technical field.Can use one or more radical initiator.When using the mixture of two or more radical initiators, blending ratio is not particularly limited.The consumption of radical initiator take the total amount of unsaturated carboxylic acid and/or its acid anhydrides, all acrylic monomers as benchmark, is preferably 1 to 10wt%.The temperature of polymerization is generally 50 to 80 ℃, and take 60 to 70 ℃ as good.
Polyreaction is carried out under the existence of solvent usually, the preferred solvent that is enough to each composition, radical initiator and prepared resin in the dissolving resin that uses.There is no particular restriction for solvent, can use general employed solvent in this technical field.Can use one or more solvent.When the mixture of the solvent that uses two or more, blending ratio is not particularly limited.The amount of solvent is also unrestricted, take the total amount of unsaturated carboxylic acid and/or its acid anhydrides, all acrylic monomers as benchmark, is preferably 50 to 80wt%.
Resin of the present invention is alkali soluble resin, can be used for Photosensitve resin composition.
The present invention also provides Photosensitve resin composition.One specific embodiment according to the present invention, Photosensitve resin composition comprise resin of the present invention, have polymerizable compound and the Photoepolymerizationinitiater initiater of ethylene type unsaturated link(age).
The content of this resin, take the gross weight of this Photosensitve resin composition as benchmark, be 10 to 30wt%, be preferably 15 to 25wt%, one specific embodiment according to the present invention, the resin that preparation is finished mixes with the polymerizable compound with ethylene type unsaturated link(age) and Photoepolymerizationinitiater initiater, to obtain Photosensitve resin composition.
Be used for the polymerizable compound with ethylene type unsaturated link(age) of Photosensitve resin composition of the present invention, behind the absorb light energy, can carry out polymerized/cross-linked with resin.There is no particular restriction to be used for the polymerizable compound with ethylene type unsaturated link(age) of the present invention, as long as can carry out polymerized/cross-linked with resin behind the absorb light energy.One specific embodiment according to the present invention, the polymerizable compound with ethylene type unsaturated link(age) are selected from monomer and/or the oligomer with ethylene type unsaturated link(age).One specific embodiment according to the present invention, the polymerizable compound of tool ethylene type unsaturated link(age) optionally are selected from the person that has the simple function group and/or have the polyfunctional group person's (used " polyfunctional group " has usual meaning, refer to contain surpass 1 functional group) herein.In the part example of these specific embodiments, the polymerizable compound with ethylene type unsaturated link(age) is selected from multi-functional polymerizable compound.
Example with polymerizable compound of ethylene type unsaturated link(age) includes but not limited to: (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) Ethyl acrylate, (methyl) Octyl acrylate, (methyl) lauryl acrylate, (methyl) stearyl acrylate ester, (methyl) cyclohexyl acrylate, (methyl) allyl acrylate, (methyl) vinylformic acid three ring decyl ester, (methyl) phenyl acrylate, (methyl) benzyl acrylate, (methyl) vinylformic acid oxa-ring butyl ester, (methyl) vinylformic acid 3-methyl-3-oxa-ring butyl ester, (methyl) vinylformic acid 3-ethyl-3-oxa-ring butyl ester, (methyl) vinylformic acid (3-methyl-3-oxa-cyclobutyl) methyl esters, (methyl) vinylformic acid (3-ethyl-3-oxa-cyclobutyl) methyl esters, (methyl) vinylformic acid 2-(3-methyl-3-oxa-cyclobutyl) ethyl ester, (methyl) vinylformic acid 2-(3-ethyl-3-oxa-cyclobutyl) ethyl ester, (methyl) vinylformic acid 2-[(3-methyl-3-oxa-cyclobutyl) methoxyl group] ethyl ester, (methyl) vinylformic acid 2-[(3-ethyl-3-oxa-cyclobutyl) methoxyl group] ethyl ester, (methyl) vinylformic acid 3-[(3-methyl-3-oxa-cyclobutyl) methoxyl group] propyl ester, (methyl) vinylformic acid 3-[(3-ethyl-3-oxa-cyclobutyl) methoxyl group] propyl ester, (methyl) vinylformic acid 2-hydroxyl ethyl ester, (methyl) vinylformic acid tetrahydrofuran (THF) methyl esters, (methyl) vinylformic acid 2-hydroxypropyl acrylate, (methyl) vinylformic acid 2-(three ring [5.2.1.0
2,6] last of the ten Heavenly stems oxygen base) ethyl ester etc., and combination; Vinylbenzene, Vinyl toluene (such as: adjacent Vinyl toluene, a Vinyl toluene, to Vinyl toluene), α-vinyltoluene, chloro-styrene etc., and combination; Acrylamide derivative, for example, (methyl) acrylamide, N methacrylamide, N-ethyl-methyl acrylamide, N hydroxymethyl acrylamide, N-methylol methacrylamide, N-methoxymethyl acrylamide, N-ethoxyl methyl acrylamide, N-butoxymethyl acrylamide, vinyl cyanide etc. and combination thereof; Maleimide derivatives; Propionate, vinyl-acetic ester, vinyl benzoate etc. and combination thereof; Iso-butylene; And combination.
Polymerizable compound with ethylene type unsaturated link(age) can use commercially available polyfunctional compound, such as, but not limited to Nikalac MX-302 (by Sanwa Chemical Co., Ltd. makes); AronixM-400, M-402, M-403, M-404, M-408, M-450, M-305, M-309, M-310, M-313, M-315, M-320, M-325, M-326, M-327, M-350, M-360, M-208, M-210, M-215, M-220, M-225, M-233, M-240, M-245, M-260, M-270, M-1100, M-1200, M-1210, M-1310, M-1600, M-221, M-203, TO-924, TO-1270, TO-1231, TO-595, TO-756, TO-1343, TO-1382, TO-902, TO-904, TO-905, TO-1330 (by Toagosei Co., Ltd. makes); Kayarad D-310, D-330, DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-120, DN-0075, DN-2475, SR-295, SR-355, SR-399E, SR-494, SR-9041, SR-368, R-415, SR-444, SR-454, SR-492, SR-499, SR-502, SR-9020, SR-9035, SR-111, SR-212, SR-213, SR-230, SR-259, SR-268, SR-272, SR-344, SR-349, SR-368, SR-601, SR-602, SR-610, SR-9003, PET-30, T-1420, GPO-303, TC-120S, HDDA, NPGDA, TPGDA, PEG400DA, MANDA, HX-220, HX-620, R-551, R-712, R-167, R-526, R-551, R-712, R-604, R-684, TMPTA, THE-330, TPA-320, TPA-330, KS-HDDA, KS-TPGDA, KS-TMPTA (by Nippon Kayaku Co., Ltd. makes); Light Acrylate PE-4A, DPE-6A, DTMP-4A (by Kyoeisha Chemical Co., Ltd. makes) etc., and combination.
One specific embodiment according to the present invention has the content of the polymerizable compound of ethylene type unsaturated link(age), take the gross weight of this Photosensitve resin composition as benchmark, is 5 to 20wt%, and preferred 10 to 15wt%
There is no particular restriction to be used for the Photoepolymerizationinitiater initiater of Photosensitve resin composition of the present invention, can use the Photoepolymerizationinitiater initiater that can cause Raolical polymerizable behind the absorb light energy.
The example of Photoepolymerizationinitiater initiater includes but not limited to: bitter almond oil camphor and alkane ether thereof, for example, bitter almond oil camphor, benzoin methylether, ethoxybenzoin, benzoin iso-propylether, bitter almond oil camphor phenylate (benzoin phenyl ether), benzoin acetate; Methyl phenyl ketone, for example, methyl phenyl ketone, 2,2-dimethoxy-2-phenyl methyl phenyl ketone, 2,2-diethoxy-2-phenyl methyl phenyl ketone, 1,1-dichloroacetophenone; Aminoacetophenone, for example, 2-methyl isophthalic acid-[4-(methylthio group) phenyl]-2-morpholinyl third-1-ketone, 2-phenmethyl-2-dimethylin-1-(4-morpholinyl phenyl)-Ding-1-ketone; Anthraquinone, for example, 2-methylanthraquinone, 2-ethyl-anthraquinone, 2-tertiary butyl anthraquinone, 1-chloroanthraquinone, 2-amyl anthraquinone (2-amylanthraquinone); Thioxanthone (thioxanthone) and oxygen green onion ketone (xanthone), for example, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, CTX, 2,4-di-isopropyl thioxanthone; Ketal, for example, methyl phenyl ketone dimethyl ketal, benzyl dimethyl ketone; Benzophenone, for example, benzophenone, 4, two (N, the N'-two-methyl-amido) benzophenone (4,4'-bis (N, N'-di-methyl-amino) benzophenone), 4 of 4'-, two (N, the N'-two-ethyl-amido) benzophenone of 4'-; Acridine derivatives (acridine derivative); Azophenlyene derivative (phenazine derivative); Quinoxaline derivatices (quinoxaline derivative); Triphenylphosphine; Phosphine oxide, for example, (2,6-dimethoxy benzoyl)-2,4,4-amyl group phosphine oxide ((2,6-dimethoxybenzoyl)-2,4,4-pentyl phosphine oxide), (bis (2 for two (2,4,6-trimethylbenzoyl) phenyl phosphine oxide, 4,6-trimethylbenzoyl)-phenyl phosphine oxide), 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide (2,4,6-trimethylbenzoyl-diphenyl phosphine oxide), ethyl-2,4,6-trimethylbenzoyl-phenyl phosphine oxide (ethyl-2,4,6-trimethylbenzoyl-phenyl phosphinate); 1-phenyl-1,2-propanedione-2-O-benzoyl oximes (1-phenyl-1,2-propanedione2-O-benzoyl oxime); 4-(2-hydroxyl-oxethyl) phenyl-(2-propyl group)-ketone (4-(2-hydroxyethoxy) Phenyl-(2-propyl) ketone); 1-aminophenyl ketone (1-aminophenyl ketone) and 1-photoinitiator (1-hydroxy phenyl ketone), for example, 1-hydroxycyclohexylphenylketone, 2-hydroxyl isopropyl phenyl ketone, phenyl 1-hydroxyl nezukone (phenyl 1-hydroxyisopropyl ketone), 4-isopropyl phenyl 1-hydroxyl nezukone (4-isopropylphenyl 1-hydroxyisopropyl ketone); Various superoxide (peroxide); And combination.
One specific embodiment according to the present invention, the content of Photoepolymerizationinitiater initiater take the gross weight of this Photosensitve resin composition as benchmark, is 0.5 to 5wt%, is preferably 1 to 3wt%.
One specific embodiment according to the present invention, Photosensitve resin composition can optionally comprise solvent.The employed solvent of Photosensitve resin composition is not particularly limited, as long as the composition of Photosensitve resin composition can be dispersed or dissolved, and does not react with these compositions, and, have the volatility of appropriateness and suitable drying rate, and after volatilization, can provide even and level and smooth filming to get final product.Can use general employed solvent in this technical field.
The example of solvent includes but not limited to: ethers, for example, 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, the diglycol monotertiary positive propyl ether, the diglycol monotertiary n-butyl ether, triethylene glycol monomethyl ether, triglycol list ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol list positive propyl ether, the propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, DPE, dipropylene glycol list positive propyl ether, the dipropylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, tripropylene glycol list ether, diglyme, the glycol ether MEE, diethyl carbitol and tetrahydrofuran (THF) etc.; Ketone, for example, methylethylketone, pimelinketone, 2-heptanone and 3-heptanone etc.; The ester class, for example, ethyl lactate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, the diethylene glycol monomethyl ether acetic ester, the diethylene glycol monoethyl ether acetic ester, propylene glycol methyl ether acetate, propylene glycol methyl ether acetate (PGMEA), 2 hydroxy propanoic acid formic acid, the 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, the 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, 3-ethoxyethyl propionic ester, ethoxy ethyl acetate, hydroxyl ethyl acetate, 2-hydroxy-3-methyl methyl-butyrate, 3-methyl-3-methoxyl group butylacetic acid ester, 3-methyl-3-methoxyl group butyl propionic ester, ethyl acetate, the acetic acid n Propanoic acid, isopropyl acetate, n-butyl acetate, isobutyl acetate, the positive the eleventh of the twelve Earthly Branches acid of formic acid, Isoamyl Acetate FCC, n-butyl propionate, ethyl butyrate, propyl butyrate, isopropyl butyrate, the positive butyl ester of butyric acid, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, the pyruvic acid n-propyl, methyl acetoacetate, methyl aceto acetate and 2-3-hydroxyethyl butyrate etc.; The fragrance same clan, for example, toluene and dimethylbenzene etc.; The acid amides same clan, for example, N-Methyl pyrrolidone, DMF and N,N-dimethylacetamide etc.Preferred pimelinketone, ethyl lactate, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate and 3-ethoxyethyl propionic ester.Can use one or more solvents.When using the mixture of two or more solvents, blending ratio is not particularly limited.
In addition, above-mentioned solvent also can also be used with Benzyl base ether, two n-hexyl ethers, second eyeball acetone, isophorone, caproic acid, enanthic acid, 1-octanol, the high boiling solvents such as the 1-naphthalene is pure, Benzyl is pure, the sour Benzyl ester of vinegar, ethyl benzoate, oxalic acid diethyl ester, ethyl maleate, gamma-butyrolactone, NSC 11801, propylene carbonate, ethyleneglycol monophenylether acetic ester.
In one specific embodiment, the content of solvent take the gross weight of this Photosensitve resin composition as benchmark, is 50 to 80wt%, is preferably 55 to 75wt%.
One specific embodiment according to the present invention, Photosensitve resin composition can optionally comprise additive.The example of additive includes but not limited to: properties-correcting agent (modifer), malleableize agent (toughener), stablizer (stabilizer), defoamer, dispersion agent (dispersant), flow agent (leveling agent), thickening material (thickening agent), toughener (reinforcing agent), coupler (coupling agent), increase and scratch agent (flexibility-imparting agent), softening agent (plasticizer), sensitizer (sensitizers), water, fire retardant, antioxidant, static inhibitor, hot-setter, tensio-active agent, pigment, dyestuff, filler, antisettling agent and analogue etc. thereof, and combination.
In one specific embodiment, the content of additive take the gross weight of this Photosensitve resin composition as benchmark, is no more than 5wt% usually.
One specific embodiment according to the present invention, Photosensitve resin composition can be used for making photoresist, especially negative light resistance agent.In the part example of these specific embodiments, Photosensitve resin composition is applied to base material after, drying, exposure, development are with patterning.In the part example of these specific embodiments, after putting on the Photosensitve resin composition patterning of base material, can further carry out etching or plating to base material.
Photosensitve resin composition can put on various base materials and (comprise inorganic materials, organic materials or its mixture etc.), such as, but not limited to: glass substrate, silicon substrate (as: silicon, silicon-dioxide, silicon-dioxide through mixing, silicon nitride, polysilicon etc.), the Al substrate, the GaAs substrate, tantalum substrate, copper base, ceramic substrate, aluminium/copper mixture substrate, polycarbonate substrate, polyester substrate, the polymeric amide substrate, the polyamideimide-based plate, polyimide substrate, the cellulose acetate substrate, polystyrene, styrene-acrylonitrile copolymer, phenol resin, Resins, epoxy etc. and analogue thereof.These substrates also can carry out the pre-treatments such as medicine (such as, organosilane coupler etc.) is processed, the processing of electricity slurry, sputter processing, ion plating processing, gas-phase reaction processing, vacuum evaporation processing.When base material was silicon substrate, its surface also can be formed with current potential coupling assembly (Charge Couple Device, CCD), thin film transistor (Thin Film Transistor, TFT) etc.
After Photosensitve resin composition is applied to base material, can heat to carry out soft roasting.Then, utilize suitable light shield with suitable light source the base material that applies Photosensitve resin composition to be carried out the selectivity exposure, to obtain required pattern.After exposure is finished, base material be impregnated in the alkaline developer, until the photoresist layer of unexposed area is complete or almost dissolved.Afterwards base material is taken out and heat-treat (hard roasting).
One specific embodiment according to the present invention, Photosensitve resin composition can be used for making protective layer or the insulation layer in the electronic package.
Photosensitve resin composition of the present invention can provide suitable development capability and high penetration, and promotes simultaneously its surface hardness and sticking power, represents the characteristics such as excellent water-fastness, etch resistant, the reliability of improving product and qualification rate.
The present invention will be described more specifically by embodiment, but this embodiment is not be used to limiting category of the present invention.Unless specialize, in the following example and comparing embodiment, be used for representing that the content of any composition and " % " of any amount of substance reach " weight part " take weight as benchmark.
Embodiment
The preparation of resin
Resin 1: be in the flask of 6L at the internal volume that has stirrer, thermometer, reflux cooling pipe, dropping funnel and nitrogen ingress pipe, the MEDG (Diethylene Glycol monomethyl ethyl ether (Methyl Ethyl Di Glycol)) 270 that packs into restrains, and is warming up to 65 ℃ of constant temperature after the stirring.In addition with 2,2 '-azobis isobutyronitrile (polymerization starter), 14.2 grams, 2,4-phenylbenzene-4-methyl-1-pentene (chain-transfer agent) 4 grams, 3-(Trimethoxy silane base) propyl methyl acid esters 33.5 grams (A-174, mol ratio=18%), vinylformic acid 2-(three ring [5.2.1.0
2,6] last of the ten Heavenly stems oxygen base) ethyl ester 31.7 gram (TCDMA, mol ratio=19%), methacrylic acid 12.3 gram (MAA, mol ratio=19%), methacrylic acid 3,4-epoxycyclohexyl methyl ester 40.0 gram (M-100, mol ratio=26%), benzyl methacrylate 25.3 gram (BzMA, mol ratio=18%) stirring makes its dissolving in the adding flask, be warming up to 75 ℃ and constant temperature after the dissolving 2.5 hours, obtain resin copolymer solution, solid holdup 31.8 % by weight, molecular-weight average (Mw) is 8000.
Resin 2 is prepared according to above-mentioned resin 1 mode to resin 6, and wherein resin 4 to resin 6 is applied to comparative example, forms such as table one:
Table one
A-174: methacrylic acid 3-(Trimethoxy silane base) propyl diester
STYRENE: vinylbenzene
TCDMA: methacrylic acid three ring decyl ester
MAA: methacrylic acid
M-100: methacrylic acid 3,4-epoxycyclohexyl methyl ester
THFMA: Tetrahydrofurfuryl Methacrylate
BzMA: benzyl methacrylate
HEMA: methacrylic acid-2-hydroxy methacrylate
Solid holdup: in the weighing bottle of constant weight, take by weighing 1 gram sample (resin copolymer solution), drying is 12 hours in 105 ℃ of thermostatic drying chambers, weigh after the cooling, calculate solid holdup, general compliance rate of inferring thus polymerization, unconverted monomer can exist with the form of liquid, and polymkeric substance exists with solid.
Be used for the preparation of the resin combination of interlayer dielectric and protective membrane
Embodiment 1
Evenly hybrid resin 1(to be converted into the solid content of resin be 15.60 grams) solution 50 grams, CGI 242(Photoepolymerizationinitiater initiater, made by BASF (BASF) company) 2 grams, vinylformic acid two new Doutrate (Aronix M 400, polymerizable compound with ethylene type unsaturated link(age)) 15 grams and propylene glycol monomethyl ether (solvent) 33 grams, be configured to the resin combination of 100 grams, then the strainer with 0.2 μ m (micron) filters this solution, to obtain resin combination.
Embodiment 2 to 3
The resin 1 that replaces among the embodiment 1 with resin 2 and resin 3 respectively according to the step of embodiment 1, prepares respectively resin combination.
Comparative example 1 to 3
The resin 1 that replaces among the embodiment 1 with resin 4, resin 5, resin 6 respectively according to the step of embodiment 1, prepares respectively resin combination.
Test
Then, with following method the composition of above-mentioned gained is carried out the test of sticking power (adhesion), surface hardness (surface hardness), penetration coefficient (transmittance) and development capability etc.
Respectively with the resin combination of above-mentioned gained, be uniformly coated in the mode of rotary coating (rotating speed 1000rpm, 7 seconds) and be coated with the ITO(indium tin oxide) the conductive glass base material on.In baking oven, carried out soft roasting (Pre-bake) 10 minutes with 100 ° of C.See through light shield, and with 150mJ/cm
2Exposure energy to resin combination expose (Exposure).After 30 seconds, in baking oven, firmly baked (Post-bake) 30 minutes with 230 ° of C with mobile washed with de-ionized water (Rinse).According to following method, the film that resin combination is formed on the base material is tested, with the characteristic of assessment resin combination.
(1) sticking power after the washing
The base material that will be formed with the resin combination film is immersed in the deionized water, keeps under 80 ℃ 1 hour.Then, with hundred lattice scrapers and the 3M adhesive tape test resin combination sticking power (ASTMD3359 method of testing) to base material, with the sticking power of assessment etching rear film to base material, in evaluation score, the sticking power of 5B is best, and 4B takes second place, and 0B is the poorest.
(2) sticking power after the etching
The base material that will be formed with the resin combination film is immersed in (HCl:215ml, 37wt% in the acid etching liquid of iron(ic) chloride; H
2O:69.2ml; FeCl3:16.8ml, 15wt%), under 40 ℃, kept 3 minutes.Then, with hundred lattice scrapers and the 3M adhesive tape test sticking power (ASTM D3359 method of testing) to base material, with the sticking power of assessment etching rear film to base material, in evaluation score, the sticking power of 5B is best, and 4B takes second place, and 0B is the poorest.
The results are shown in the following table two, as shown in Table 2, with the prepared Photosensitve resin composition of the resin of the embodiment of the invention, etching solution is had good resistance, and after etching, base material is showed excellent sticking power.
(3) surface hardness
To the film that is formed by resin combination, carry out pencil test (Pencil Scratch Hardness Test), with the surface hardness of assessment film.The results are shown in the following table, it is characterized in that, 6B represents that hardness is the poorest, and 6H represents hardness optimal, for example: if use H pencil surface without scratch, use 2H pencil surface also without scratch, but use 3H pencil surface that scratch is arranged, judge that then the hardness of test film is 2H.
As shown in Table 2, with the prepared Photosensitve resin composition of the resin of the embodiment of the invention, provide good surface hardness.
(4) 230 ℃ of penetration coefficients
Utilize microspectrophotometer (MX-50, OLYMPUS company system), with the wavelength of 400nm, measure the light transmittance of the film that is formed by resin combination.
The results are shown in the following table two, as shown in Table 2, with the prepared Photosensitve resin composition of the resin of the embodiment of the invention, when good sticking power and surface hardness is provided, also can keep high penetration coefficient.
(5) development capability
Respectively with resin combination, with aforementioned manner be coated with, soft roasting after with the light shield exposure of the figure that comprises the 30um perforate.And behind 25 ° of C development 60sec, after 30 seconds, firmly bake rear in microscopically measurement perforate value with mobile washed with de-ionized water (Rinse) with KOH 0.04%.Its result such as table two:
Table two
The Photosensitve resin composition that the resin of the embodiment of the invention is prepared, suitable development capability and penetration coefficient can be provided, and promote simultaneously its surface hardness and sticking power, represent the characteristics such as excellent water-fastness, etch resistant, the reliability of improving product and yield, the demand that real symbol industry is utilized.
Above-described embodiment is illustrative composition of the present invention and preparation method only, but not is used for restriction the present invention.Any these those skilled in the art all can be under spirit of the present invention and category, and above-described embodiment is modified and changed.Therefore, the scope of the present invention should be contained such as claims.
Claims (15)
1. resin that is used for interlayer dielectric and protective membrane is by comprising the acrylic monomer, the acrylic monomer that contains silane that contain epoxy construction, containing the acrylic monomer of aromatic nucleus and be selected from and be different from this and contain epoxy construction, contain silane and contain the unsaturated carboxylic acid of acrylic monomer of aromatic nucleus and at least one multipolymer that reacts in the acid anhydrides thereof.
2. the resin for interlayer dielectric and protective membrane according to claim 1 is characterized in that, this unsaturated carboxylic acid is selected from one of vinylformic acid and methacrylic acid, and this acid anhydrides is selected from one of acrylic anhydride and methacrylic anhydride.
3. the resin for interlayer dielectric and protective membrane according to claim 2 is characterized in that, this unsaturated carboxylic acid is methacrylic acid.
4. the resin for interlayer dielectric and protective membrane according to claim 1 is characterized in that, the acrylic monomer that contains epoxy construction is to be selected from the acrylic monomer that contains the epoxy cyclohexane ring.
5. the resin for interlayer dielectric and protective membrane according to claim 4 is characterized in that, this acrylic monomer that contains epoxy construction is methacrylic acid 3,4-epoxycyclohexyl methyl ester or vinylformic acid 3,4-epoxycyclohexyl methyl ester.
6. the resin for interlayer dielectric and protective membrane according to claim 1 is characterized in that, this acrylic monomer that contains silane is methacrylic acid 3-(Trimethoxy silane base) propyl diester.
7. the resin for interlayer dielectric and protective membrane according to claim 1 is characterized in that, this acrylic monomer that contains aromatic nucleus is benzyl methacrylate.
8. the resin for interlayer dielectric and protective membrane according to claim 1 is characterized in that, this acrylic monomer that contains aromatic nucleus is methacrylic acid three ring decyl ester.
9. the resin for interlayer dielectric and protective membrane according to claim 1, its weight-average molecular weight is 5000 to 30000.
10. a Photosensitve resin composition that is used for interlayer dielectric and protective membrane comprises each described resin, the polymerizable compound with ethylene type unsaturated link(age), Photoepolymerizationinitiater initiater and solvent in the claim 1 to 9.
11. the Photosensitve resin composition for interlayer dielectric and protective membrane according to claim 10 is characterized in that, the content of this resin take the gross weight of this Photosensitve resin composition as benchmark, is 10 to 30wt%.
12. the Photosensitve resin composition for interlayer dielectric and protective membrane according to claim 10 is characterized in that this has the content of the polymerizable compound of ethylene type unsaturated link(age), take the gross weight of this Photosensitve resin composition as benchmark, is 5 to 20wt%.
13. the Photosensitve resin composition for interlayer dielectric and protective membrane according to claim 10 is characterized in that, the content of this Photoepolymerizationinitiater initiater take the gross weight of this Photosensitve resin composition as benchmark, is 0.5 to 5wt%.
14. the Photosensitve resin composition for interlayer dielectric and protective membrane according to claim 10; it is characterized in that; this has the polymerizable compound of ethylene type unsaturated link(age); be the polyfunctional compound with ethylene type unsaturated link(age), and this polyfunctional compound can carry out polymerization or crosslinked with this resin.
15. the Photosensitve resin composition for interlayer dielectric and protective membrane according to claim 10 is characterized in that, the content of this solvent take the gross weight of this Photosensitve resin composition as benchmark, is 50 to 80wt%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW100131216A TW201310166A (en) | 2011-08-31 | 2011-08-31 | Resin and composition thereof for manufacture insulator layer and over coat |
| TW100131216 | 2011-08-31 |
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| CN102964515A true CN102964515A (en) | 2013-03-13 |
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| JP (1) | JP5564083B2 (en) |
| CN (1) | CN102964515B (en) |
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| CN104698753A (en) * | 2013-12-09 | 2015-06-10 | 罗门哈斯电子材料韩国有限公司 | Negative-type photosensitive resin composition |
| CN104950575A (en) * | 2014-03-24 | 2015-09-30 | Jsr株式会社 | Radiation-sensitive resin composition, method for forming spacer and interlayer insulating film for display device, and display device |
| CN107344985A (en) * | 2016-05-06 | 2017-11-14 | 财团法人工业技术研究院 | Copolymer, resin composition containing same, packaging film and packaging structure |
| CN107728428A (en) * | 2016-08-11 | 2018-02-23 | 东友精细化工有限公司 | Chemical amplification type photosensitive polymer combination and the dielectric film being produced from it |
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| CN103555118B (en) * | 2013-10-18 | 2016-01-13 | 江西省科学院应用化学研究所 | A kind of preparation method containing methyl siliconic acid graftomer water-resisting agent |
| JP6221862B2 (en) * | 2014-03-14 | 2017-11-01 | Jsr株式会社 | Radiation-sensitive composition, display element spacer or interlayer insulating film, and method for forming them |
| JP6458236B2 (en) * | 2014-09-26 | 2019-01-30 | ナトコ株式会社 | Alkali-soluble resin, photosensitive resin composition and use thereof |
| JP6627308B2 (en) * | 2015-07-27 | 2020-01-08 | Jnc株式会社 | Thermosetting composition |
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| CN107344985A (en) * | 2016-05-06 | 2017-11-14 | 财团法人工业技术研究院 | Copolymer, resin composition containing same, packaging film and packaging structure |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2013053312A (en) | 2013-03-21 |
| TW201310166A (en) | 2013-03-01 |
| JP5564083B2 (en) | 2014-07-30 |
| CN102964515B (en) | 2015-08-19 |
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