CN106893032B - 芳基环丁烯 - Google Patents
芳基环丁烯 Download PDFInfo
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- CN106893032B CN106893032B CN201611155313.XA CN201611155313A CN106893032B CN 106893032 B CN106893032 B CN 106893032B CN 201611155313 A CN201611155313 A CN 201611155313A CN 106893032 B CN106893032 B CN 106893032B
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- Prior art keywords
- aryl
- diallyl
- substituted
- alkyl
- group
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- -1 Aryl cyclobutene Chemical compound 0.000 title claims description 85
- 229920000642 polymer Polymers 0.000 claims abstract description 109
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 38
- 238000000576 coating method Methods 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims description 140
- 150000003254 radicals Chemical class 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 239000000758 substrate Substances 0.000 claims description 32
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000006649 (C2-C20) alkynyl group Chemical class 0.000 claims description 10
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- FYRWKWGEFZTOQI-UHFFFAOYSA-N 3-prop-2-enoxy-2,2-bis(prop-2-enoxymethyl)propan-1-ol Chemical compound C=CCOCC(CO)(COCC=C)COCC=C FYRWKWGEFZTOQI-UHFFFAOYSA-N 0.000 claims description 6
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 claims description 6
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UBJVUCKUDDKUJF-UHFFFAOYSA-N Diallyl sulfide Chemical compound C=CCSCC=C UBJVUCKUDDKUJF-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 claims description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 claims description 3
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 3
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- 229960003742 phenol Drugs 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- GZWLFCGQNCRLIN-UHFFFAOYSA-N 1,2-bis(prop-2-enoxy)benzene Chemical compound C=CCOC1=CC=CC=C1OCC=C GZWLFCGQNCRLIN-UHFFFAOYSA-N 0.000 claims description 2
- QRWVOJLTHSRPOA-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)urea Chemical compound C=CCNC(=O)NCC=C QRWVOJLTHSRPOA-UHFFFAOYSA-N 0.000 claims description 2
- AANPQJBOJRZUNO-UHFFFAOYSA-N 1,4-bis(prop-2-enoxy)benzene Chemical compound C=CCOC1=CC=C(OCC=C)C=C1 AANPQJBOJRZUNO-UHFFFAOYSA-N 0.000 claims description 2
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 claims description 2
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 claims description 2
- LPRQSQCAHSRGRZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,5-dihydro-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NCCN1 LPRQSQCAHSRGRZ-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- CARNFEUGBMWTON-UHFFFAOYSA-N 3-(2-prop-2-enoxyethoxy)prop-1-ene Chemical compound C=CCOCCOCC=C CARNFEUGBMWTON-UHFFFAOYSA-N 0.000 claims description 2
- XSSOJMFOKGTAFU-UHFFFAOYSA-N 3-[2-(2-prop-2-enoxyethoxy)ethoxy]prop-1-ene Chemical compound C=CCOCCOCCOCC=C XSSOJMFOKGTAFU-UHFFFAOYSA-N 0.000 claims description 2
- NZEDMAWEJPYWCD-UHFFFAOYSA-N 3-prop-2-enylsulfonylprop-1-ene Chemical compound C=CCS(=O)(=O)CC=C NZEDMAWEJPYWCD-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229910019946 S-S Inorganic materials 0.000 claims description 2
- 229910019939 S—S Inorganic materials 0.000 claims description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 2
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 claims description 2
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 2
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 claims description 2
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 claims description 2
- AOESAXAWXYJFNC-UHFFFAOYSA-N bis(prop-2-enyl) propanedioate Chemical compound C=CCOC(=O)CC(=O)OCC=C AOESAXAWXYJFNC-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- CJIPLMHXHKPZGM-UHFFFAOYSA-N n,n-bis(prop-2-enyl)aniline Chemical compound C=CCN(CC=C)C1=CC=CC=C1 CJIPLMHXHKPZGM-UHFFFAOYSA-N 0.000 claims description 2
- BGDTWOQNFJNCKH-UHFFFAOYSA-N n-ethyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(CC)CC=C BGDTWOQNFJNCKH-UHFFFAOYSA-N 0.000 claims description 2
- WGESLFUSXZBFQF-UHFFFAOYSA-N n-methyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(C)CC=C WGESLFUSXZBFQF-UHFFFAOYSA-N 0.000 claims description 2
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 description 21
- 239000002318 adhesion promoter Substances 0.000 description 18
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 17
- 239000004065 semiconductor Substances 0.000 description 15
- 235000012431 wafers Nutrition 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 125000001624 naphthyl group Chemical group 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 13
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 8
- 238000005194 fractionation Methods 0.000 description 8
- 238000003475 lamination Methods 0.000 description 8
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 239000008199 coating composition Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 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
- 238000004132 cross linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 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
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007766 curtain coating Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000012949 free radical photoinitiator Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
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Abstract
本发明提供具有改进的物理特性,如伸长率的芳基环丁烯聚合物。还提供组合物和涂布此类芳基环丁烯聚合物的方法。
Description
本发明大体上涉及聚合物材料领域,并且更具体来说涉及可用于电子装置制造中的芳基环丁烯类聚合物。
芳基环丁烯类聚合物在多种电子应用,如微电子封装和互连应用中被用作电介质材料。芳基环丁烯类聚合物具有用于这些应用的多种令人希望的特性。然而,这些聚合物遭受某些机械局限性,如低断裂韧性、低伸长率以及差的拉伸强度,这限制这些的聚合物在某些电子应用中的使用。
一种提高芳基环丁烯类聚合物的机械特性的方法公开于美国专利第6,420,093号中。此专利权公开提供具有提高韧性的苯并环丁烯类聚合物的组合物,所述组合物包含a)选自芳基环丁烯单体、芳基环丁烯低聚物和其组合的至少一种前体化合物;以及b)具有包含烯系不饱和基(也就是说,一或多个碳-碳双键)和末端丙烯酸酯或甲基丙烯酸脂基团的主链的聚合物或低聚物。公开于此专利中的增韧添加剂在聚合物主链中具有大量的碳-碳双键。然而,当这些组合物用于某些光图案化应用时,由于包含添加的聚合物或低聚物的碳-碳双键的竞争反应,苯并环丁烯聚合物提高的伸长率韧性损失。此外,在添加的聚合物主链中剩余碳-碳双键可导致材料随时间变黄,这对于某些应用可以是不利的。因此,存在对可以提供具有提高的机械特性的芳基环丁烯类材料的替代材料的需求。
公布的欧洲专利申请EP527272 A1公开具有改进的特性,如改进的柔性、强度和抗裂特性的苯并环丁烯(BCB)树脂。本专利申请中的BCB树脂通过使双苯并环丁烯(双BCB)单体与相比于双BCB单体中的不饱和基团具有较高亲二烯物活性的不饱和化合物(亲二烯物单体)反应制备。亲二烯物单体具有单一烯系或炔系不饱和基团位点。一种此类亲二烯物单体为顺丁烯二酸酐。亲二烯物单体以相对于双BCB单体相对较低的量(每摩尔双BCB 0.001到0.2摩尔)使用且用于控制双BCB单体的聚合度。基本上,亲二烯物单体(用其单一亲二烯物部分)用于终止生长聚合物链,进而减少聚合物链的分子量。尽管这些聚合物的某些特性可改进,其它特性可能受此方法困扰,如具有相比于常规BCB树脂降低的耐化学性。确切地说,当这些常规聚合物用于光致介电材料中时,较低分子量聚合物将减少曝光区与未曝光区之间的对比度(或溶解速率差异),导致不佳分辨率和未曝光区中的相对大的膜厚度损失。
日本公布专利申请JP2004224817公开用于预浸体材料中的含有苯并环丁烯树脂和某些烯丙基取代的双马来酰亚胺衍生物的树脂组合物。双马来酰亚胺衍生物为双马来酰亚胺化合物与2摩尔烯丙基取代的环戊二烯的Diels-Alder反应产物,其中环戊二烯与马来酰亚胺部分中的碳-碳双键反应。当暴露于相对较高温度(如通常在各种半导体加工和封装操作期间遇到的那些)时,此日本公开案中公开的树脂易经历逆Diels-Alder反应,其导致树脂裂解。
本发明提供一种包含一或多种芳基环丁烯第一单体和一或多种具有两个或更多个烯丙基部分的第二单体作为聚合单元的聚合物;其中一或多种第二单体不含芳基环丁烯部分;且其中一或多种第二单体不为烯丙基取代的双马来酰亚胺衍生物。优选地,第二单体不含双马来酰亚胺部分,并且更优选地,第二单体不含由烯丙基取代的环戊二烯衍生物和双马来酰亚胺化合物形成的双马来酰亚胺衍生物。
本发明还提供包含上文所述的聚合物和一或多种有机溶剂的组合物。
本发明进一步提供一种形成上文所述的聚合物的方法,其包含聚合一或多种芳基环丁烯第一单体和一或多种具有两个或更多个烯丙基部分的第二单体。
另外,本发明进一步提供一种在衬底上形成膜的方法,其包含:提供衬底;在衬底表面上涂布上文所述的组合物的层;和固化涂层。
本发明另外提供包含由上文所述的组合物形成的固化膜的衬底。
除非上下文另外明确指示,否则如本说明书通篇所使用,以下缩写应具有以下含义:℃=摄氏度;min.=分钟;hr.=小时;g=克;L=升;μm=微米(micron/micrometer);nm=纳米;mm=毫米;mL=毫升;MPa=兆帕斯卡;Mw=重量平均分子量;Mn=数目平均分子量;且AMU=原子质量单位。除非另外指出,否则“重量%”是指按参考组合物的总重量计的重量百分比。
术语“烷基”包括直链、分支链以及环状烷基。同样地,“烯基”是指直链、分支链和环状烯基。术语“炔基”是指直链或分支链炔基。“芳基”是指芳族碳环和芳族杂环。如本文中所用,术语“脂族”是指可以是直链或分支链的含开链碳的部分,如烷基、烯基和炔基部分。又如本文所用,术语“脂环族”是指环状脂族部分,如环烷基和环烯基。此类脂环族部分是非芳族的,但可包括一或多个碳-碳双键。除非上下文另外明确指示,否则“经取代”烷基、烯基或炔基意指烷基、烯基或炔基上的一或多个氢经一或多个选自卤基、羟基、C1-10烷氧基、氨基、单或二-C1-10烃基取代的氨基、C5-20芳基和经取代C5-20芳基置换。除非上下文另外明确指示,否则“经取代”芳基意指芳基上的一或多个氢经一或多个选自卤基、羟基、C1-10烷基、C2-10烯基、C2-10炔基、C1-10烷氧基、氨基、单或二-C1-10烃基取代的氨基、C5-20芳基和经取代C5-20芳基的取代基置换。“烷基”是指烷烃基团,且包括烷烃二价基团(烯烃)和高碳基团。同样,术语“烯基”、“炔基”和“芳基”分别是指烯烃、炔烃和芳烃的对应单价、二价或高碳基团。“卤基”是指氟、氯、溴以及碘。术语“(甲基)丙烯酸酯”是指甲基丙烯酸酯和丙烯酸酯,并且同样地,术语(甲基)丙烯酰胺是指甲基丙烯酰胺和丙烯酰胺。
术语“固化”意指增加材料或组合物的分子量的任何方法,如聚合或缩合。“可固化”是指能够在某些条件下固化的任何材料。术语“聚合物”还包括低聚物。术语“低聚物”是指能够进一步固化的相对低分子量材料,如二聚物、三聚物、四聚物、五聚物、六聚物等,包括B级材料。如本文所用,“芳族有机残基”包含仅具有芳族特征的有机残基(如苯基),以及含有芳族和脂族部分的组合的有机残基。冠词“一(a)”、“一个(an)”以及“所述(the)”是指单数和复数。除非另外指出,否则所有量都是重量百分比并且所有比率都是摩尔比。所有数字范围包括端点并且可按任何顺序组合,除了此类数字范围明显地限于总计为100%。
本发明提供某些包含一或多种第一芳基环丁烯单体和一或多种第二单体作为聚合单元的芳基环丁烯聚合物,第二单体具有两个或更多个烯丙基部分。此类芳基环丁烯聚合物具有相比于常规芳基环丁烯类聚合物改进的拉伸强度和/或伸长率。优选地,本发明芳基环丁烯聚合物为低聚的。更优选地,一或多种第二单体不含苯并环丁烯部分,并且甚至更优选地不含芳基环丁烯部分。
适用于制备本发明芳基环丁烯聚合物的芳基环丁烯第一单体包括(但不限于)具有式(1)的那些单体:
其中B1为n价键联基团;Ar为多价芳基且环丁烯环的碳原子结合到Ar的相同芳环上的相邻碳原子;m为1或更大的整数;n为1或更大的整数;R1和R2中的每一个独立地为单价基团;两个R1部分可与其所连接的碳结合在一起以形成羰基或硫羰基;且其中两个R2部分可与其所连接的碳结合在一起以形成羰基或硫羰基。优选地,多价芳基基团,Ar可由1到3个芳族碳环或杂芳族环构成。优选的是Ar包含单一芳环,并且更优选地苯环。当Ar为苯环时,单体为苯并环丁烯(BCB)单体。芳基任选地经1到3个选自以下的基团取代:C1-6烷基、三-C1-6烷基硅烷基、C1-6烷氧基、卤基和羧基,优选地经以下中的一或多个取代:C1-6烷基、三-C1-3烷基硅烷基、C1-3烷氧基、氯和羧基,并且更优选地经以下中的一或多个取代:C1-3烷基、三-C1-3烷基硅烷基、C1-3烷氧基和羧基。优选的是Ar未经取代或经羧基取代。优选地n=1或2,并且更优选地n=1。优选地m=1-4,更优选地m=2-4,且更优选地m=2。优选地,每一R1和R2独立地选自H、C1-6烷基、C1-6烯基、C1-6烷氧基、羧基、含C2-6羧基的部分、含C2-6酮的部分、含C1-6酰胺基的部分、C2-6烷氧基烷醇、C2-6烷氧基酯和卤基,并且更优选地选自H、C1-3烷基和C1-3烷氧基和卤基。适合的单价B1基团优选地具有式-[C(R3)2-C(R4)2]xZ1或-[C(R3)=CR4]xZ1,其中每一R3和R4独立地选自氢、C1-6烷基和芳基;Z选自氢、C1-6烷基、C6-10芳基、硅氧基芳基、-CO2R5;每一R5独立地选自H、C1-6烷基、C1-6羟烷基、C6-10芳基、C6-10羟基芳基、C7-20芳烷基、C7-20羟基芳烷基和C7-20烷芳基;且x=1或2。优选地,R3和R4独立地选自H、C1-3烷基和芳基,并且更优选地选自H和C1-3烷基。优选地,R5为H、C1-3烷基、C1-6羟基烷基、C6-10芳基、C6-10羟基芳基和C7-20羟基芳烷基。Z1优选地为硅烷氧基或-CO2R5。优选的硅烷氧基具有式-[Si(R6)2-O]p-Si(R6)2-,其中每一R6独立地选自H、C1-6烷基、芳基、芳烷基和烷芳基;且p为1或更大的整数。优选地,R6选自C1-3烷基、C6-10芳基和C7-20芳烷基。适合的芳烷基包括苯甲基、苯乙基和苯丙基。优选地,B1包含一或多个碳-碳双键(烯系不饱和性)。
优选地,芳基环丁烯聚合物包含一或多个式(2)的双苯并环丁烯单体作为聚合单元:
其中每一R7和R8独立地选自H、C1-6烷基、C1-6烯基、C1-6烷氧基、卤基、羧基、含C2-6羧基的部分、含C2-6酮的部分、含C1-6酰胺基的部分、C2-6烷氧基烷醇、C2-6烷氧基酯、-O-C1-20烷基、-(C=O)-C1-20烷基、-O-(C=O)-C1-20烷基、-(C=O)-O-C1-20烷基、-O-C6-20芳基、-C(O)-C6-20芳基、-O-C(O)-C6-20芳基和-C(O)-O-C6-20芳基,且优选地选自H、C1-3烷基、C1-3烷氧基和卤基;其中两个R7部分可与其所连接的碳结合在一起以形成羰基或硫羰基;且其中两个R8部分可与其所连接的碳结合在一起以形成羰基或硫羰基;每一R9独立地选自C1-6烷基、三-C1-6烷基硅烷基、C1-6烷氧基和卤基;每一R10独立地为二价有机基团,其可为饱和或烯系不饱和的;每一R11独立地选自H、C1-6烷基、C7-20芳烷基和苯基;p为1或更大的整数;且q为0到3的整数。每一R7和R8优选地独立地选自H、C1-3烷基和C1-3烷氧基,并且更优选地,每一R7和R8为H。优选地,每一R9独立地选自C1-6烷基、三-C1-3烷基硅烷基、C1-3烷氧基和氯,并且更优选地选自C1-3烷基、三-C1-3烷基硅烷基和C1-3烷氧基。优选地,每一R10独立地选自C2-6烷基、C2-6烯基和C2-6炔基,并且更优选地,每一R10独立地选自-CH2CH2-、-CH=CH-和-C≡C-。每一R11优选地选自C1-3烷基,并且更优选地,每一R11为甲基。优选地,p=1-5,更优选地p=1-3,且更优选地p=1。优选地,q=0。尤其优选的式(2)的芳基环丁烯单体为1,3-双(2-双环[4.2.0]辛-1,3,5-三烯-3-基-乙烯基)-1,1,3,3-四甲基二硅氧烷(DVS-bisBCB),其具有式(3)。
本发明芳基环丁烯聚合物优选地包含一或多个式(4)的苯并环丁烯单体作为聚合单元:
其中每一R12和R13独立地选自H、C1-6烷基、C1-6烯基、C1-6烷氧基、卤基、羧基、含C2-6羧基的部分、含C2-6酮的部分、含C1-6酰胺基的部分、C2-6烷氧基烷醇、C2-6烷氧基酯、-O-C1-20烷基、-(C=O)-C1-20烷基、-O-(C=O)-C1-20烷基、-(C=O)-O-C1-20烷基、-O-C6-20芳基、-(C=O)-C6-20芳基、-O-(C=O)-C6-20芳基和-(C=O)-O-C6-20芳基,且优选地选自H、C1-3烷基和C1-3烷氧基;其中两个R12部分可与其所连接的碳结合在一起以形成羰基或硫羰基;且其中两个R13部分可与其所连接的碳结合在一起以形成羰基或硫羰基;每一R14独立地选自C1-6烷基、三-C1-6烷基硅烷基、C1-6烷氧基和卤基;Y为-SO3R15或具有3到15个碳原子且具有至少一个-OH部分或经保护羧基部分的单价基团;R15为H或具有1到20个碳原子的单价基团;且f为0到2的整数。术语“含C1-6酰胺基的部分”是指具有1到6个碳原子且具有-C(O)-NX2部分的任何部分,其中X可为H或烃基部分。每一R12和R13优选地独立地选自H、C1-3烷基、C1-3烷氧基和卤基,并且更优选地,每一R12和R13为H。优选地,每一R14独立地选自C1-6烷基、三-C1-3烷基硅烷基、C1-3烷氧基和氯,并且更优选地选自C1-3烷基、三-C1-3烷基硅烷基和C1-3烷氧基。Y的单价基团可为脂族和/或芳族的。通常,Y具有1到5个-OH部分,优选地1到3个、更优选地1或2个并且更优选地1个-OH部分。Y可为具有3到15个碳原子且具有至少一个-OH部分的饱和或不饱和单价基团,且优选地为烯系不饱和的。更优选地,Y的至少一个-OH部分为-CO2H或-SO3H。优选地,R15为H、C1-10烷基、C7-16芳烷基或C6-12芳基。优选的式(4)化合物为如下化合物:其中Y选自-CH=CHC(=O)OR16、-CH=CH-CH2OH、-CH2-CH=CHC6H4OH和-CH=CHCH2C6H4OH;其中R16选自H、C2-8羟基烷基和C4-8烷基,具有一或多个直接结合到羧基部分的氧的季碳。更优选地,式(4)化合物为如下化合物:其中Y为-CH=CHC(=O)OR16,且更优选地-CH=CHC(=O)OH。优选地,f=0。
本发明的聚合物可包含一种芳基环丁烯第一单体或两种或更多种相异的芳基环丁烯第一单体作为聚合单元。优选地,本发明聚合物包含两个相异的芳基环丁烯单体。当使用两种相异的芳基环丁烯单体时,第一相异的芳基环丁烯单体与第二相异的芳基环丁烯单体的摩尔比为1:99到99:1,优选地5:95到95:5,并且更优选地25:75到75:25。另外优选地,本发明聚合物包含一或多种包含一或多个选自羧酸、经保护羧酸和磺酸的部分的芳基环丁烯单体作为聚合单元。还优选的是本发明聚合物包含一或多种上文所述的式(2)的芳基环丁烯单体作为聚合单元。甚至更优选地,本发明聚合物包含一或多种上文所述的式(2)的芳基环丁烯单体和一或多种包含一或多个选自羧酸、经保护羧酸和磺酸的部分的芳基环丁烯单体作为聚合单元。
任何具有两个或更多个烯丙基部分且不含芳基环丁烯部分,且与一或多种芳基环丁烯第一单体共聚合以形成本发明芳基环丁烯聚合物的单体可适当地用作本发明的第二单体,其条件是一或多种第二单体不为烯丙基取代的双马来酰亚胺衍生物。适用作第二单体的化合物可为单体或低聚物。第二单体具有两个或更多个烯丙基部分,且可具有2到20个烯丙基部分。优选地,第二单体具有2到10个、更优选地2到6个、且更优选地2到4个烯丙基部分。适合的烯丙基部分是选自烯丙醚部分、烯丙酯部分、烯丙胺部分、烯丙酰胺部分、烯丙酮部分和烯丙基芳基部分,且优选地为烯丙醚部分、烯丙酯部分和烯丙基芳基部分。在一个优选实施例中,第二单体优选地不含羧酸、经保护羧酸和磺酸部分。
优选地,一或多种第二单体是选自式(5)化合物:
其中每一R17独立地选自H和C1-30单价烃基残基;E选自O、S、S-S、N(R18)、C(O)、-O-C(O)-O-、-N(R18)-C(O)-、-N(R18)-C(O)-N(R18)-、S(O)2、C6-20芳基、经取代C6-20芳基和-O-G1-O-;每一R18独立地选自H、C1-12烷基、C2-12烯基、C6-10芳基和经取代C6-10芳基;G1为n+1价有机残基;且n为1到5的整数。优选地,n=1到3,并且更优选地n=1或2。优选地,每一R17独立地选自H、C1-30烷基、经取代C1-30烷基、C2-30烯基、经取代C2-30烯基、C2-30炔基、经取代C2-30炔基、C5-30芳基和经取代C5-30芳基,更优选地选自H、C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C6-20芳基和经取代C6-20芳基,并且甚至更优选地,每一R17为H。优选地,E选自O、S、N(R18)、C(O)、-O-C(O)-O-、-N(R18)-C(O)-N(R18)-、S(O)2、C6-20芳基、经取代C6-20芳基和-O-G1-O-,并且更优选地选自O、C(O)、-O-C(O)-O-、C6-20芳基、经取代C6-20芳基和-O-G1-O-。优选地,每一R18独立地选自H、C1-10烷基、C2-10烯基、C6-10芳基和经取代C6-10芳基。
在式(5)中,G1优选地为具有1到100个碳原子、更优选地1到80个、更优选地1到60个并且甚至更优选地1到50个碳原子的n+1价有机残基。G1的有机残基可含有一或多个选自氧、氮和硫,优选地氧和氮,并且更优选地氧的杂原子。G1的有机残基可另外含有一或多个选自羟基、伯氨基、仲氨基或叔氨基、酮、酯、醚、硫醚、二硫醚和磺酰基的部分。更优选地,G1选自-C(O)-R19-C(O)-、C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C2-20炔基、经取代C2-20炔基、(C2-8亚烷氧基)y1、C6-30芳基、经取代C6-30芳基和-Ar1-G2-Ar2-;其中R19选自化学键、C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C2-20炔基、经取代C2-20炔基、C6-20芳基和经取代C6-20芳基;y1为1到100的整数;Ar1和Ar2独立地为C6-20芳基或经取代C6-20芳基;G2选自化学键、C(O)、S(O)2、C1-20烷基、经取代C1-20烷基和-(CR20R21-Ar3)y2CR20R21-;R20和R21中的每一个独立地选自H、OH、C1-10烷基、C1-10烷氧基和C6-20芳基;每一Ar3独立地选自C6-20芳基和经取代C6-20芳基;且y2为1到50的整数。G1更优选地选自-C(O)-R19-C(O)-、C1-20烷基、经取代C1-20烷基、C2-20烯基、(C2-8亚烷氧基)y1、C6-30芳基、经取代C6-30芳基和-Ar1-G2-Ar2-;且更优选地选自-C(O)-R19-C(O)-、C1-20烷基、经取代C1-20烷基、(C2-4亚烷氧基)y1、C6-30芳基、经取代C6-30芳基和-Ar1-G2-Ar2-。优选地,R19选自C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C2-20炔基、经取代C2-20炔基、C6-20芳基和经取代C6-20芳基,并且更优选地选自C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C6-20芳基和经取代C6-20芳基。优选地,y1为1到75、并且更优选地1到50的整数。优选地,y2为1到30的整数。优选地,Ar1和Ar2独立地选自苯基、经取代苯基、萘基和经取代萘基。G2优选地选自化学键、C(O)、S(O)2、C1-15烷基、卤基C1-15烷基和(CR20R21-Ar3)y2CR20R21。优选地,R20和R21中的每一个独立地选自H、C1-10烷基和C6-20芳基。每一Ar3独立地选自苯基、经取代苯基、萘基和经取代萘基。
优选的式(5)单体为如下单体:其中E选自O、N(R18)、C(O)、-O-C(O)-O-、-N(R18)-C(O)-N(R18)-、C6-20芳基、经取代C6-20芳基和-O-G1-O-,以及式(6)-(8)的单体:
其中每一A1独立地选自化学键、-CH2-、O和-C(O)O-;Ar4选自C6-10芳基和经取代C6-10芳基;且t1=1到2;
其中每一A2独立地选自化学键、-CH2-、O和C(O)O-;每一Ar5选自C6-10芳基和经取代C6-10芳基;G3选自化学键、O、S、S(O)2、C(O)、C1-10烷基、卤基取代的C1-10烷基和(CR22R23-Ar5)y3CR22R23;R22和R23中的每一个独立地选自H、C1-10烷基和C6-20芳基;Ar5独立地选自C6-20芳基和经取代C6-20芳基;y3为1到50的整数;t2=1到2;且t3=1到2;
其中每一A3独立地选自化学键、-CH2-、O和-C(O)O-;G4为C1-20烷基、羟基C1-20烷基、C2-20烯基、(C2-6亚烷氧基)y4、C6-20芳基取代的C1-20烷基和含杂原子的C2-20烯基;y4为1到50的整数;且t4=1到3;其中R16和G1如上文所述。Ar4优选地为苯基、经取代苯基、萘基、经取代萘基,并且更优选地为苯基和萘基。每一Ar5优选地独立地选自苯基、经取代苯基、萘基、经取代萘基,并且更优选地苯基和萘基。优选地,G3选自化学键、O、S(O)2、C(O)、-CH2-、-C(CH3)2-、-C(CF3)2-和(CR22R23-Ar5)y3CR22R23。优选地,R22和R23中的每一个独立地选自H、C1-10烷基、苯基、经取代苯基、萘基和经取代萘基。优选地,每一Ar5独立地选自苯基、经取代苯基、萘基和经取代萘基。优选地,G4为C1-16烷基、羟基C1-16烷基、C2-16烯基、(C2-4亚烷氧基)y4、C6-20芳基取代的C1-16烷基和含氧的C2-16烯基。
例示性式(5)的第二单体包括(但不限于):二烯丙醚;二烯丙基硫醚;二烯丙基二硫醚;二烯丙基胺;三烯丙基胺;二烯丙基甲胺;二烯丙基乙胺;二烯丙基丙胺;N,N-二烯丙基苯胺;二烯丙基酮;碳酸二烯丙酯;N,N'-二烯丙基脲;二烯丙基砜;邻、间和对二烯丙基苯;1,3,5-三烯丙基苯;二烯丙基苯甲醚;二烯丙基萘;1,5-二烯丙基萘-2,6-二醇;二烯丙氧基联苯,如4,4'-二烯丙氧基联苯和2,2'-二烯丙氧基联苯;双酚A二烯丙醚;双酚S二烯丙醚;双酚F二烯丙醚;双酚AF二烯丙醚;二烯丙氧基萘,如1,2-二烯丙氧基萘、1,5-二烯丙氧基萘、1,8-二烯丙氧基萘、2,7-二烯丙氧基萘和2,3-二烯丙氧基萘;二烯丙氧基联萘;1,3-二烯丙氧基苯;1,2-二烯丙氧基苯;1,4-二烯丙氧基苯;1,3,5-三烯丙氧基苯;1,2,3-三烯丙氧基苯;1,2,4-三烯丙氧基苯;1,3-二烯丙氧基-5-羟基苯;三羟甲基丙烷二烯丙醚;三羟甲基丙烷三烯丙醚;异戊四醇二烯丙醚;异戊四醇三烯丙醚;异戊四醇四烯丙醚;2,2-二甲基丙烷-1-3-二烯丙醚;乙二醇二烯丙醚;二乙二醇二烯丙醚;丙二醇二烯丙醚;二丙二醇二烯丙醚;三丙二醇二烯丙醚;1,4-丁烷二烯丙醚;邻苯二甲酸二烯丙酯;间苯二甲酸二烯丙酯;对苯二甲酸二烯丙酯;苯三甲酸三烯丙酯;草酸二烯丙酯;丙二酸二烯丙酯;丁二酸二烯丙酯;顺丁烯二酸二烯丙酯;戊二酸二烯丙酯;己二酸二烯丙酯;六-3-烯二甲酸二烯丙酯;噻吩二甲酸二烯丙酯;呋喃二甲酸二烯丙酯;联吡啶二甲酸二烯丙酯;吡啶二甲酸二烯丙酯;2,5-双((烯丙氧基)甲基)四氢呋喃;和9,9-双((烯丙氧基)甲基)芴。
适用作本发明的第二单体的化合物一般可商购或可通过所属领域中已知的多种方法制备。举例来说,如邻苯二甲酸酐或丁二酸酐的羧酸酐可与2当量烯丙基溴化镁在适合的溶剂中反应以分别获得对应的二烯丙酯,如邻苯二甲酸二烯丙酯和丁二酸二烯丙酯。
本发明芳基环丁烯聚合物可任选地另外包含一或多种包含一或多个二烯或亲二烯物部分的第三单体作为聚合单元。此类第三单体不同于第一和第二单体。包含一个亲二烯物部分的第三单体可用于对生长芳基环丁烯聚合物链封端,有效地相对于在不存在此类第三单体的情况下制备的芳基环丁烯聚合物减少分子量。包含两种或更多个亲二烯物部分的第三单体可用于赋予芳基环丁烯聚合物其它特征。此类第三单体的选择在所属领域的技术人员的能力内。
用于形成本发明聚合物的芳基环丁烯第一单体的总摩尔数与第二单体的总摩尔数的比率可在99:1到1:99、优选地99:1到50:50、并且更优选地90:10到60:40范围内变化。任选的第三单体可以按用于形成本发明芳基环丁烯聚合物的单体的总摩尔数计0到40摩尔%、优选地0到30摩尔%、并且更优选地1到15摩尔%的量使用。通常,本发明芳基环丁烯聚合物具有1000到50,000AMU、且优选地1500到35,000AMU、并且更优选地2,500到25,000的重量平均分子量(Mw)。
本发明的芳基环丁烯聚合物可通过任何适合的方法,如在美国专利第4,812,588号;第5,136,069号;第5,138,081号;和国际专利申请第WO 94/25903号中描述的那些方法制备。一般来说,本发明聚合物通过通常在适合溶剂中将本发明芳基环丁烯第一单体和一或多种第二单体以及任何任选的第三单体中的一或多者加热到所用特定单体的聚合起始温度而制备。尽管不希望受理论束缚,相信这些单体通过Diels-Alder环加成聚合,因此不需要催化剂引发剂或固化剂以发生聚合。通常,这些单体的聚合在≥150℃、并且优选地≥170℃的温度下引发,但取决于所选择的特定单体,可使用更低或更高的温度。本发明单体进行聚合的温度受环丁烯环上的任何取代基影响。一般来说,当环丁烯环未经取代时,聚合在≥170℃下起始。环丁烯环上的供电子或吸电子取代基一般低于聚合起始温度。适合的聚合溶剂是溶解一种或多种单体并且沸点高于单体的聚合温度的任何有机溶剂。例示性有机溶剂包括极性非质子溶剂,如酰胺和砜。聚合时间通常是1到60小时。对于某些应用,可能需要在低聚物阶段终止聚合。由一或多种本发明的单体构成的此类低聚物可主要由二聚体、三聚体、四聚体等构成,并且随后可进一步聚合。如本文所用,术语“本发明的单体”和“本发明单体”打算包括本文中所描述的个别化合物,以及随后进一步经聚合的其二聚体、三聚体和四聚体。本发明聚合物可按原样使用或可通过添加如水或甲醇的非溶剂以从溶液沉淀聚合物并且其后去除有机溶剂而分离。
本发明聚合物的组合物通常包含一或多种本发明的芳基环丁烯聚合物和一或多种有机溶剂。适合的有机溶剂是本发明聚合物可溶的那些有机溶剂。尤其适用的有机溶剂为适用于制造或调配芳基环丁烯聚合物的任何溶剂。例示性有机溶剂包括(但不限于):芳族烃,如甲苯、二甲苯和均三甲苯;醇,如2-甲基-1-丁醇、4-甲基-2-戊醇和甲基异丁基甲醇;酯,如乳酸乙酯、丙二醇甲醚乙酸酯、2-羟基异丁酸甲酯、3-甲氧基丙酸甲酯和乙酸3-甲氧基-1-丁酯;内酯,如γ-丁内酯;内酰胺,如N-甲基吡咯烷酮;醚,如丙二醇甲醚和二丙二醇二甲醚异构体(可以PROGLYDETM DMM购自陶氏化学公司(The Dow Chemical Company));酮,如环己酮和甲基环己酮;和其混合物。
适用于本发明组合物的适合的任选添加剂包括(但不限于)以下各者中的一或多者:固化剂、表面活性剂、不同于本发明单体的交联剂、无机填充剂、有机填充剂、塑化剂、粘着促进剂、金属钝化材料等,和前述中的任一者的组合。适合的表面活性剂为所属领域的技术人员所熟知,并且非离子表面活性剂是优选的。此类表面活性剂可以0到10g/L并且优选地0到5g/L的量存在。任何适合的无机填充剂可任选地用于本发明组合物,并且为所属领域的技术人员所熟知。例示性无机填充剂包括(但不限于)二氧化硅、碳化硅、氮化硅、氧化铝、碳化铝、氮化铝、氮化硼、氧化锆等,以及其混合物。无机填充剂可呈以下形式:粉末、杆形、球形或任何其它适合的形状。此类无机填充剂可具有任何适合的尺寸。按组合物的总重量计,无机填充剂可以0到80重量%的量使用。不同于本发明的单体的任何交联单体可用作交联剂,其条件是其与组合物中的芳基环丁烯聚合物在用于固化组合物的条件下交联。适合的交联剂包括(但不限于)含多元胺、聚硫醇、环氧树脂和(甲基)丙烯酸酯的交联剂。此类交联剂的选择在所属领域的技术人员的能力内。此类交联剂通常以按组合物中的可聚合组分的总重量计0到20重量%并且优选地0到10重量%的量使用。还可将一或多种非交联单体添加到本发明组合物中,并且其通常以按组合物中的可聚合组分的总重量计0到20重量%的量存在。此类非交联单体含有能够与本发明组合物中的苯并环丁烯类组分聚合的1或2个可聚合部分。优选地,金属钝化材料为铜钝化剂。适合的铜钝化剂在所属领域中众所周知,并且包括咪唑和苯并三唑。
多种固化剂可用于本发明组合物中。适合的固化剂可有助于固化苯并环丁烯类材料,并且可通过热或光活化。例示性固化剂包括(但不限于)热生引发剂和光敏性化合物(光生引发剂)。此类固化剂的选择在所属领域的技术人员的能力内。优选的热生引发剂为自由基引发剂,如(但不限于)偶氮二异丁腈、过氧化二苯甲酰和过氧化二异丙苯。优选的光敏固化剂为以Irgacure品牌购自BASF的自由基光引发剂和包括DNQ化合物的磺酸酯的重氮基萘醌(DNQ)化合物。例示性自由基光引发剂为Iracure 379(2-二甲胺基-2-(4-甲基-苯甲基)-1-(4-吗啉-4-基-苯基)-丁-1-酮)和Iracure 907(2-甲基-1-[4-(甲硫基)苯基]-2-(4-吗啉基)-1-丙酮)。适合的DNQ化合物为如下的任何化合物:具有DNQ部分,如DNQ磺酸酯部分,并且在本发明组合物中充当光敏化合物,即其在暴露于适当辐射时充当溶解抑制剂。适合的DNQ化合物公开于美国专利第7,198,878号和第8,143,360号中。光敏化合物的量在按芳基环丁烯聚合物的总重量计的0到30重量%范围内变化。当存在时,光敏组分通常以按苯并环丁烯类组分的总重量计5到30重量%、优选地5到25重量%并且更优选地10到25重量%的量使用。
在本发明组合物中可使用任何适合的粘着促进剂,并且此类粘着促进剂的选择充分地在所属领域的技术人员的能力内。优选的粘着促进剂为含硅烷材料,并且更优选地含三烷氧基硅烷材料。例示性粘着促进剂包括(但不限于):双(三烷氧基硅烷基烷基)苯,如双(三甲氧基硅烷基乙基)苯;氨基烷基三烷氧基硅烷,如氨丙基三甲氧基硅烷、氨丙基三乙氧基硅烷、三甲氧基硅烷基丙基马来酰胺酸、三乙氧基硅烷基丙基马来酰胺酸和苯基氨丙基三乙氧基硅烷;和其它硅烷偶合剂,以及前述的混合物。特别适合的粘合促进剂包括可购自陶氏电子材料公司(Dow Electronic Materials)(Marlborough,Massachusetts)的AP3000、AP 8000和AP 9000S。本发明可交联组合物通常含有按组合物的总重量计0到15重量%、优选地0.5到10重量%、更优选地1到10重量%、更优选地2到10重量%的粘着促进剂。
本发明组合物是通过按任何次序组合一或多种本发明聚合物和任何任选的有机溶剂或额外组分制备。当本发明组合物含有如光敏化合物的固化剂时,优选的是固化剂首先溶解于适合的有机溶剂中,接着与一或多种本发明聚合物和任何任选的表面活性剂组合,且接着与任何任选的粘着促进剂组合。
本发明组合物中的任一者适用于在衬底上形成具有改进的拉伸强度和伸长率的芳基环丁烯聚合物的层。此类芳基环丁烯聚合物层适用作介电层、永久粘结性粘着剂,适用作应力缓冲层等。本发明组合物可通过任何适合的方法涂覆在衬底上。除其它方法外,用于安置本发明组合物的合适的方法包括(但不限于)旋涂、帘幕式涂覆、喷涂、滚涂、浸涂、气相沉积和层合,如真空层合。在半导体制造行业中,旋涂是利用现有设备和工艺的优选方法。在旋涂中,可调节组合物的固体含量以及旋转速度以便在所施用的表面上获得所需厚度的组合物。通常,本发明组合物是在400到4000rpm的旋转速度下旋涂。分配在所述晶片或衬底上的本发明组合物的量取决于在所述组合物中总固体含量,所希望的所得层的厚度以及本领域的技术人员熟知的其它因素。当浇铸,如通过旋涂本发明组合物的膜或层时,在膜的沉积期间许多(或所有)溶剂蒸发。优选地,在安置在表面上之后,加热(烘焙)所述组合物以去除任何残留的溶剂。典型的烘烤温度是90到160℃,但可适当地使用其它温度。此类去除残余溶剂的烘烤通常进行大约2分钟,但也可适当使用更长或更短的时间。通常通过加热一段时间固化芳基环丁烯低聚物。适合的固化温度在180到250℃或更高的范围内。通常固化时间范围为1分钟至600分钟。
在替代优选方法中,本发明组合物可形成为干膜,并且通过层合安置在衬底表面上。可使用包括真空层合技术的多种适合的层合技术,并且所属领域的技术人员熟知所述技术。在形成干膜中,本发明组合物首先使用狭缝式涂布、凹版印刷或另一适当方法安置(如涂布)到适合的膜支撑薄片,如聚酯薄片,优选地聚对苯二甲酸乙二酯(PET)薄片,或聚酰亚胺薄片,如KAPTONTM聚酰亚胺的前表面上。随后在如90到140℃的适合温度下将组合物软烘烤如1到30分钟的适当时间以去除任何溶剂。随后在室温下将如聚乙烯的聚合物膜覆盖薄片滚轧层合于干燥组合物上,以在储存和处理期间保护所述组合物。为了将干燥组合物安置于衬底上,首先去除覆盖薄片。然后,支撑薄片上的干燥组合物使用滚轧层合或真空层合层合到衬底表面上。层合温度可在20到120℃范围内。随后去除(剥离)支撑薄片,使得干燥组合物留在表面上。
广泛多种电子装置衬底可以用于本发明中。电子装置衬底为用于任何电子装置制造中的任何衬底。例示性电子装置衬底包括(但不限于)半导体晶片、玻璃、蓝宝石硅酸盐材料、氮化硅材料、碳化硅材料、显示装置衬底、环氧树脂成型化合物晶片、电路板衬底以及热稳定聚合物。如本文所用,术语“半导体晶片”意图涵盖“半导体衬底”、“半导体装置”以及用于各种互连水平的各种封装,包括单芯片晶片、多芯片晶片,用于各种水平的封装,用于发光二极管(LED)的衬底或需要焊接连接的其它组件。半导体晶片,如硅晶片、砷化镓晶片和硅锗晶片可以经图案化或未经图案化。如本文所用,术语“半导体衬底”包括具有包括半导体装置的活性或可操作部分的一或多个半导体层或结构的任何衬底。术语“半导体衬底”经定义以意指包含半导体材料,如半导体装置的任何构造。半导体装置是指在其上已经或正在制造至少一个微电子装置的半导体衬底。热稳定聚合物包括(但不限于)针对用于固化所述芳基环丁烯材料,如聚酰亚胺(例如,KaptonTM聚酰亚胺,购自DuPont,Wilmington,Delaware)稳定的任何聚合物。
当使用不含粘着促进剂的本发明的组合物时,待用本发明组合物涂布的衬底的表面可任选地首先与适合的粘着促进剂或所处理蒸气接触。此类处理改良本发明芳基环丁烯聚合物与衬底表面的粘着。任何适合的方法,如旋涂、浸涂、喷涂、帘幕式涂覆、滚涂、气相沉积等可用于使衬底表面与粘着促进剂接触。旋涂是用于使衬底表面与粘着促进剂接触的优选方法。可使用任何适合的粘着促进剂,并且此类粘着促进剂的选择充分地在所属领域的技术人员的能力内。优选的粘着促进剂为含硅烷材料,并且更优选地含三烷氧基硅烷材料。适用于预处理衬底表面的例示性粘着促进剂为上文所描述的那些粘着促进剂。所属领域中已知的各种蒸气处理(如等离子体处理)可用以增加本发明的芳基环丁烯聚合物与衬底表面的粘着。在某些应用中,可优选地在用本发明组合物涂覆表面之前使用粘着促进剂处理衬底表面。
本发明芳基环丁烯类聚合物适用于形成相比于由常规苯并环丁烯类聚合物制备的涂层具有改进的拉伸强度、伸长率和/或减少的残余应力的芳基环丁烯类涂层。
实例1:在氮气吹扫的反应容器中,将苯并环丁烯丙烯酸(BCB-AA,14.63g,84.00mmol)、作为第一单体的DVS-bisBCB(12.66g,32.40mmol)和作为第二单体的邻苯二甲酸二烯丙酯(0.887g,3.60mmol)于乙酸3-甲氧基丁酯(41g)中的混合物加热到175℃后维持24小时。温度接着降低到165℃且继续反应,同时监测通过周期性地去除小样品和通过使用聚苯乙烯标准物的凝胶渗透色谱法测量所得聚合物的Mw建立的分子量。当观测的Mw为4800-6500AMU时,反应器冷却到80℃且混合物热过滤通过1μm聚丙烯过滤器,得到聚合物1。
实例2:重复实例1的程序,除了单体的量为如下:含BCB-AA(14.63g,84.00mmol)、作为第一单体的DVS-bisBCB(11.25g,28.80mmol)和作为第二单体的邻苯二甲酸二烯丙酯(1.773g,7.20mmol)的乙酸3-甲氧基丁酯(41g)如前所述地进行B分级,得到聚合物2。
实例3:重复实例1的程序,除了单体的量为如下:含BCB-AA(14.63g,84.00mmol)、作为第一单体的DVS-bisBCB(9.845g,25.20mmol)和作为第二单体的邻苯二甲酸二烯丙酯(2.660g,10.80mmol)的乙酸3-甲氧基丁酯(41g)如前所述地进行B分级,得到聚合物3。
实例4:重复实例1的程序,除了单体的量为如下:含BCB-AA(17.68g,101.5mmol)、作为第一单体的DVS-bisBCB(15.29g,39.15mmol)和作为第二单体的间苯二甲酸二烯丙酯(1.07g,4.35mmol)的乙酸3-甲氧基丁酯(50g)如前所述地进行B分级,得到聚合物4。
实例5:重复实例1的程序,除了单体的量为如下:含BCB-AA(18.29g,105mmol)、作为第一单体的DVS-bisBCB(14.06g,36mmol)和作为第二单体的间苯二甲酸二烯丙酯(2.22g,9.00mmol)的乙酸3-甲氧基丁酯(51g)如前所述地进行B分级,得到聚合物5。
实例6:重复实例1的程序,除了单体的量为如下:含BCB-AA(18.29g,105mmol)、作为第一单体的DVS-bisBCB(12.31g,31.5mmol)和作为第二单体的间苯二甲酸二烯丙酯(3.32g,13.5mmol)的乙酸3-甲氧基丁酯(50g)如前所述地进行B分级,得到聚合物6。
实例7:重复实例1的程序,除了单体的量为如下:含BCB-AA(18.29g,105mmol)、作为第一单体的DVS-bisBCB(15.82g,40.5mmol)和作为第二单体的4,4'-双A-二酚-二烯丙醚(1.388g,4.50mmol)的乙酸3-甲氧基丁酯(51g)如前所述地进行B分级,得到聚合物7。
实例8:重复实例1的程序,除了单体的量为如下:含BCB-AA(18.29g,105mmol)、作为第一单体的DVS-bisBCB(14.06g,36.0mmol)和作为第二单体的4,4'-双A-二酚-二烯丙醚(2.776g,9.00mmol)的乙酸3-甲氧基丁酯(50g)如前所述地进行B分级,得到聚合物8。
实例9:重复实例1的程序,除了单体的量为如下:含BCB-AA(18.9g,108.5mmol)、作为第一单体的DVS-bisBCB(12.72g,32.55mmol)和作为第二单体的4,4'-双A-二酚-二烯丙醚(4.302g,13.95mmol)的乙酸3-甲氧基丁酯(52g)如前所述地进行B分级,得到聚合物9。
实例10:重复实例1的程序,除了单体的量为如下:含BCB-AA(12.72g,73.0mmol)、作为第一单体的DVS-bisBCB(10.19g,26.1mmol)和作为第二单体的三羟甲基丙烷二烯丙醚(1.08g,5.04mmol)的Proglyde DMM(36.6g)如前所述地进行B分级,得到聚合物10。
实例11:重复实例1的程序,除了单体的量为如下:含BCB-AA(13.2g,75.8mmol)、作为第一单体的DVS-bisBCB(8.54g,21.8mmol)和作为第二单体的三羟甲基丙烷二烯丙醚(2.37g,11.0mmol)的Proglyde DMM(36.0g)如前所述地进行B分级,得到聚合物11。
实例12:重复实例1的程序,除了单体的量为如下:含BCB-AA(13.8g,79mmol)、作为第一单体的DVS-bisBCB(6.76g,17.3mmol)和作为第二单体的三羟甲基丙烷二烯丙醚(3.76g,17.5mmol)的Proglyde DMM(40g)如前所述地进行B分级,得到聚合物12。
实例13:重复实例1的程序,除了单体的量为如下:含BCB-AA(14.4g,82.7mmol)、作为第一单体的DVS-bisBCB(4.63g,11.6mmol)和作为第二单体的三羟甲基丙烷二烯丙醚(5.2g,24.4mmol)的Proglyde DMM(37g)如前所述地进行B分级,得到聚合物13。
实例14:重复实例1的程序,除了单体的量为如下:含BCB-AA(12.6g,72.6mmol)、作为第一单体的DVS-bisBCB(10.2g,26.1mmol)和作为第二单体的异戊四醇三烯丙醚(1.36g,5.3mmol)的Proglyde DMM(36g)如前所述地进行B分级,得到聚合物14。
实例15:重复实例1的程序,除了单体的量为如下:含BCB-AA(13.0g,74.9mmol)、作为第一单体的DVS-bisBCB(8.35g,21.4mmol)和作为第二单体的异戊四醇三烯丙醚(2.80g,10.9mmol)的Proglyde DMM(37g)如前所述地进行B分级,得到聚合物15。
实例16:重复实例1的程序,除了单体的量为如下:含BCB-AA(13.5g,77.5mmol)、作为第一单体的DVS-bisBCB(6.47g,16.6mmol)和作为第二单体的异戊四醇三烯丙醚(4.33g,16.9mmol)的Proglyde DMM(32g)如前所述地进行B分级,得到聚合物16。
实例17:重复实例1的程序,除了单体的量为如下:含BCB-AA(13.3g,76.3mmol)、作为第一单体的DVS-bisBCB(4.54g,11.6mmol)和作为第二单体的异戊四醇三烯丙醚(5.71g,22.3mmol)的Proglyde DMM(36g)如前所述地进行B分级,得到聚合物17。
实例18:重复实例1的程序,除了改变单体的量且如表1中所示地改变第二单体且预期得到表1中指定的聚合物。
表1
第二单体 | BCB-AA/DVS-bisBCB/第二单体摩尔比 | 样品 |
三羟甲基丙烷三烯丙醚 | 2/4/1 | 聚合物18 |
异戊四醇四烯丙醚 | 1/2/1 | 聚合物19 |
三烯丙胺 | 2/4/1 | 聚合物20 |
二烯丙酮 | 2/4/1 | 聚合物21 |
双酚AF二烯丙醚 | 2/3.5/1.5 | 聚合物22 |
双酚S二烯丙醚 | 2/3.5/1.5 | 聚合物23 |
1,3-二烯丙氧基苯 | 1/1.5/1 | 聚合物24 |
顺丁烯二酸二烯丙酯 | 1/3/1.5 | 聚合物25 |
丁二酸二烯丙酯 | 1/2/1 | 聚合物26 |
双酚F二烯丙醚 | 1/3/1.5 | 聚合物27 |
呋喃-2,5-二甲酸二烯丙酯 | 2/4/1.5 | 聚合物28 |
实例19:通过将含3.216g重氮基萘醌(DNQ)光敏化合物(PAC)的2.930g丙二醇甲醚乙酸酯(PGMEA)、1.604g乙酸3-甲氧基丁酯、1.755g苯甲醚和0.62g DCTL-7604表面活性剂溶解于瓶中的PGMEA溶剂中制备涂料组合物。PAC为平均具有65摩尔%酯化酚的4,4'-((2-羟基苯基)亚甲基)双(2,3,6-三甲基苯酚)的2,1,5-DNQ磺酸酯。随后,4.679g 50重量%溶液N-540环氧交联剂于PGMEA中的溶液与12.504g来自实例1的聚合物1(41重量%,于乙酸3-甲氧基丁酯)和0.288g作为粘着促进剂的三乙氧基硅烷基丙基马来酰胺酸(50重量%,于PGMEA中)一起添加。将瓶滚动12小时以形成均质溶液。在去泡之后,溶液过滤通过0.45μm尼龙过滤器,随后用于得到涂料组合物1。
实例20:分别使用来自实例2和3的聚合物2和3重复实例19的程序,分别得到涂料组合物2和3。
比较实例1:重复实例19的程序,除了用比较聚合物1替换聚合物1以得到比较涂料组合物1。比较聚合物1为仅由作为聚合单元的摩尔比为70:30的BCB-AA和DVS-双BCB组成的可商购芳基环丁烯聚合物。
实例21:涂料组合物1到3和比较涂料组合物1中的每一者使用Site Trac TT5-XP涂布机在1735rpm下持续30秒溅镀于200mm特级铜涂布的硅晶片上,接着进行90℃软烘烤90秒以进一步去除溶剂。每一涂层的膜厚度为大致5.5μm。经涂布晶片接着在Blue M Ultra-Temp烘箱(型号IGF-6680F-4)中在氮气下在250℃下硬固化60分钟。每一涂层的最终膜厚度为大致5μm,且晶片裂解为10mm×90mm样品。晶片样品经受10%过硫酸铵溶液以将聚合物膜提离晶片样品。膜小心地用水冲洗且使其完全干燥。一旦干燥,样品使用透明胶带安装于具有25.4mm标距的伸长模板上。在使用5毫米/秒的十字头速度和Instron Bluehill2软件的Instron 33R4464型号仪器上进行伸长率测量。拉伸强度值通过断裂负荷除以初始最小截面积计算。每一样品的平均拉伸强度和伸长率%连同本发明样品与比较样品之间的拉伸强度和伸长率%差异一起报导于表2中。如从这些结果可见,相比于由常规芳基环丁烯聚合物形成的膜,由本发明的芳基环丁烯聚合物形成的膜具有改进的伸长率和拉伸强度。
表2
涂料组合物 | 平均拉伸强度 | Δ拉伸强度MPa | 伸长率% | Δ伸长率% |
比较 | 110.25 | 13.49 | ||
1 | 114.14 | 3.89 | 18.07 | 4.58 |
2 | 121.6 | 11.35 | 23.12 | 9.63 |
3 | 120.36 | 10.11 | 20.75 | 7.26 |
Claims (8)
1.一种聚合物,其包含一或多种下式(2)表示的芳基环丁烯单体;一种或多种包含一或多个选自羧酸、经保护羧酸和磺酸的部分的芳基环丁烯单体;和一或多种下式(5)表示的具有两个或更多个烯丙基部分的单体作为聚合单元:
其中每一R7和R8独立地选自H、C1-6烷基、C1-6烯基、C1-6烷氧基、卤基、羧基、含C2-6羧基的部分、含C2-6酮的部分、含C1-6酰胺基的部分、C2-6烷氧基烷醇、C2-6烷氧基酯、-O-C1-20烷基、-(C=O)-C1-20烷基、-O-(C=O)-C1-20烷基、-(C=O)-O-C1-20烷基、-O-C6-20芳基、-C(O)-C6-20芳基、-O-C(O)-C6-20芳基和-C(O)-O-C6-20芳基;其中两个R7部分可与其所连接的碳结合在一起以形成羰基或硫羰基;且其中两个R8部分可与其所连接的碳结合在一起以形成羰基或硫羰基;每一R9独立地选自C1-6烷基、三-C1-6烷基硅烷基、C1-6烷氧基和卤基;每一R10独立地为二价有机基团,其可为饱和或烯系不饱和的;每一R11独立地选自H、C1-6烷基、C7-20芳烷基和苯基;p为1或更大的整数;且q为0到3的整数
其中每一R17独立地选自H和C1-30单价烃基残基;E选自O、S、S-S、N(R18)、C(O)、-O-C(O)-O-、-N(R18)-C(O)-、-N(R18)-C(O)-N(R18)-、S(O)2、C6-20芳基、经取代C6-20芳基和-O-G1-O-;每一R18独立地选自H、C1-12烷基、C2-12烯基、C6-10芳基和经取代C6-10芳基;G1选自-C(O)-R19-C(O)-、C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C2-20炔基、经取代C2-20炔基、(C2-8亚烷氧基)y1、C6-30芳基、经取代C6-30芳基和-Ar1-G2-Ar2-;其中R19选自化学键、C1-20烷基、经取代C1-20烷基、C2-20烯基、经取代C2-20烯基、C2-20炔基、经取代C2-20炔基、C6-20芳基和经取代C6-20芳基;y1为1到100的整数;Ar1和Ar2独立地为C6-20芳基或经取代C6-20芳基;G2选自化学键、C(O)、S(O)2、C1-20烷基、经取代C1-20烷基和-(CR20R21-Ar3)y2CR20R21-;R20和R21中的每一个独立地选自H、OH、C1-10烷基、C1-10烷氧基和C6-20芳基;每一Ar3独立地选自C6-20芳基和经取代C6-20芳基;且y2为1到50的整数。
2.根据权利要求1所述的聚合物,其中每一R17=H。
3.根据权利要求1所述的聚合物,其中E选自O、N(R18)、C(O)、-O-C(O)-O-、-N(R18)-C(O)-N(R18)-、C6-20芳基、经取代C6-20芳基和-O-G1-O-。
4.根据权利要求1所述的聚合物,其中所述具有两个或更多个烯丙基部分的一种或多种单体是式(6)-(8)的单体:
其中每一A1独立地选自化学键、-CH2-、O和-C(O)O-;Ar4选自C6-10芳基和经取代C6-10芳基;且t1=1到2;
其中每一A2独立地选自化学键、-CH2-、O和C(O)O-;每一Ar5选自C6-10芳基和经取代C6-10芳基;G3选自化学键、O、S、S(O)2、C(O)、C1-10烷基、卤基取代的C1-10烷基和(CR22R23-Ar5)y3CR22R23;R22和R23中的每一个独立地选自H、C1-10烷基和C6-20芳基;Ar5独立地选自C6-20芳基和经取代C6-20芳基;y3为1到50的整数;t2=1到2;且t3=1到2;
其中每一A3独立地选自化学键、-CH2-、O和-C(O)O-;G4为C1-20烷基、羟基C1-20烷基、C2-20烯基、(C2-6亚烷氧基)y4、C6-20芳基取代的C1-20烷基和含杂原子的C2-20烯基;y4为1到50的整数;且t4=1到3。
5.根据权利要求1所述的聚合物,其中所述具有两个或更多个烯丙基部分的一种或多种单体选自二烯丙醚;二烯丙基硫醚;二烯丙基二硫醚;二烯丙基胺;三烯丙基胺;二烯丙基甲胺;二烯丙基乙胺;二烯丙基丙胺;N,N-二烯丙基苯胺;二烯丙基酮;碳酸二烯丙酯;N,N'-二烯丙基脲;二烯丙基砜;邻、间和对二烯丙基苯;1,3,5-三烯丙基苯;二烯丙基苯甲醚;二烯丙基萘;1,5-二烯丙基萘-2,6-二醇;二烯丙氧基联苯;双酚A二烯丙醚;双酚S二烯丙醚;双酚F二烯丙醚;双酚AF二烯丙醚;二烯丙氧基萘;二烯丙氧基联萘;1,3-二烯丙氧基苯;1,2-二烯丙氧基苯;1,4-二烯丙氧基苯;1,3,5-三烯丙氧基苯;1,2,3-三烯丙氧基苯;1,2,4-三烯丙氧基苯;1,3-二烯丙氧基-5-羟基苯;三羟甲基丙烷二烯丙醚;三羟甲基丙烷三烯丙醚;异戊四醇二烯丙醚;异戊四醇三烯丙醚;异戊四醇四烯丙醚;2,2-二甲基丙烷-1-3-二烯丙醚;乙二醇二烯丙醚;二乙二醇二烯丙醚;丙二醇二烯丙醚;二丙二醇二烯丙醚;三丙二醇二烯丙醚;1,4-丁烷二烯丙醚;邻苯二甲酸二烯丙酯;间苯二甲酸二烯丙酯;对苯二甲酸二烯丙酯;苯三甲酸三烯丙酯;草酸二烯丙酯;丙二酸二烯丙酯;丁二酸二烯丙酯;顺丁烯二酸二烯丙酯;戊二酸二烯丙酯;己二酸二烯丙酯;六-3-烯二甲酸二烯丙酯;噻吩二甲酸二烯丙酯;呋喃二甲酸二烯丙酯;联吡啶二甲酸二烯丙酯;吡啶二甲酸二烯丙酯;2,5-双((烯丙氧基)甲基)四氢呋喃;和9,9-双((烯丙氧基)甲基)芴。
6.一种组合物,其包含根据权利要求1所述的聚合物和一或多种有机溶剂。
7.根据权利要求6所述的组合物,其进一步包含一或多种固化剂。
8.一种在衬底上形成膜的方法,其包含:提供衬底;在所述衬底的表面上涂布根据权利要求7所述的组合物的层;任选地干燥所述涂层;和固化所述涂层。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4921931A (en) * | 1989-03-17 | 1990-05-01 | Shell Oil Company | Thermosetting resin compositions |
US4954584A (en) * | 1989-06-12 | 1990-09-04 | Shell Oil Company | Thermosetting resin compositions |
US5300735A (en) * | 1990-03-19 | 1994-04-05 | Hitachi, Ltd. | Interconnected multilayer boards and fabrication processes thereof |
CN1350770A (zh) * | 2000-02-02 | 2002-05-22 | 陶氏化学公司 | 增韧的苯并环丁烯为基础的聚合物及其在制造印刷线路板中的应用 |
CN103788881A (zh) * | 2012-10-30 | 2014-05-14 | 罗门哈斯电子材料有限公司 | 粘附促进剂 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4812588A (en) | 1987-12-14 | 1989-03-14 | The Dow Chemical Company | Polyorganosiloxane-bridged bisbenzocyclobutene monomers |
EP0402975B1 (en) * | 1989-06-12 | 1994-08-10 | Shell Internationale Researchmaatschappij B.V. | Benzocyclobutene carboxylate esters |
US5136069A (en) | 1991-03-28 | 1992-08-04 | The Dow Chemical Company | Process for preparing vinylically-unsaturated compounds (II) |
US5138081A (en) | 1991-04-30 | 1992-08-11 | The Dow Chemical Company | Process for purifying vinylically-unsaturated organosilicon compounds |
DE9110089U1 (de) | 1991-08-12 | 1992-01-02 | Schäfer, Hans-Günter, 1000 Berlin | Transport-Sarg mit abnehmbarer Sarg-Bodenplatte |
US5854302A (en) | 1993-04-29 | 1998-12-29 | The Dow Chemical Company | Partially polymerized divinylsiloxane linked bisbenzocyclobutene resins and methods for making said resins |
JPH09194549A (ja) * | 1996-01-11 | 1997-07-29 | Nitto Denko Corp | 熱硬化性樹脂 |
US7019093B2 (en) | 2002-10-18 | 2006-03-28 | Dow Global Technologies Inc. | Aqueous developable, photosensitive benzocyclobutene-based oligomers and polymers with high moisture resistance |
JP2004224817A (ja) | 2003-01-20 | 2004-08-12 | Sumitomo Bakelite Co Ltd | 樹脂組成物、これを用いたプリプレグおよび積層板 |
WO2006044338A1 (en) | 2004-10-13 | 2006-04-27 | Dow Global Technologies Inc. | Aqueous developable benzocyclobutene-based polymer composition and method of use of such compositions |
-
2016
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4921931A (en) * | 1989-03-17 | 1990-05-01 | Shell Oil Company | Thermosetting resin compositions |
US4954584A (en) * | 1989-06-12 | 1990-09-04 | Shell Oil Company | Thermosetting resin compositions |
US5300735A (en) * | 1990-03-19 | 1994-04-05 | Hitachi, Ltd. | Interconnected multilayer boards and fabrication processes thereof |
CN1350770A (zh) * | 2000-02-02 | 2002-05-22 | 陶氏化学公司 | 增韧的苯并环丁烯为基础的聚合物及其在制造印刷线路板中的应用 |
CN103788881A (zh) * | 2012-10-30 | 2014-05-14 | 罗门哈斯电子材料有限公司 | 粘附促进剂 |
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