CN110128661B - 共聚物与树脂组合物 - Google Patents
共聚物与树脂组合物 Download PDFInfo
- Publication number
- CN110128661B CN110128661B CN201810757082.2A CN201810757082A CN110128661B CN 110128661 B CN110128661 B CN 110128661B CN 201810757082 A CN201810757082 A CN 201810757082A CN 110128661 B CN110128661 B CN 110128661B
- Authority
- CN
- China
- Prior art keywords
- formula
- group
- repeating unit
- copolymer
- unit represented
- 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.)
- Active
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 29
- 239000011342 resin composition Substances 0.000 title claims description 21
- -1 polysiloxane group Polymers 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 239000003999 initiator Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920002120 photoresistant polymer Polymers 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 239000004065 semiconductor Substances 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 description 11
- 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 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- MKPHQUIFIPKXJL-UHFFFAOYSA-N 1,2-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(O)C(O)OC(=O)C(C)=C MKPHQUIFIPKXJL-UHFFFAOYSA-N 0.000 description 5
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 5
- 244000028419 Styrax benzoin Species 0.000 description 5
- 235000000126 Styrax benzoin Nutrition 0.000 description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 description 5
- 235000019382 gum benzoic Nutrition 0.000 description 5
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- GKZPEYIPJQHPNC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GKZPEYIPJQHPNC-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- LDFUDVLWUQLNIS-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1.C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 LDFUDVLWUQLNIS-UHFFFAOYSA-N 0.000 description 1
- QXCIRTGPUWVRMH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylethanone;propan-2-one Chemical compound CC(C)=O.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 QXCIRTGPUWVRMH-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NNHDHXUFNNAHNN-UHFFFAOYSA-N C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C.C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C Chemical compound C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C.C(C)(C)(C)OOC(C)(C)C1=C(C=CC=C1)C(C)(C)OOC(C)(C)C NNHDHXUFNNAHNN-UHFFFAOYSA-N 0.000 description 1
- JVJCWAOBAKYZSY-UHFFFAOYSA-N C(C)(C)(C)OOC1(CCC(C#C1)(C)OOC(C)(C)C)C.C(C)(C)(C)OOC1(CCC(C#C1)(C)OOC(C)(C)C)C Chemical compound C(C)(C)(C)OOC1(CCC(C#C1)(C)OOC(C)(C)C)C.C(C)(C)(C)OOC1(CCC(C#C1)(C)OOC(C)(C)C)C JVJCWAOBAKYZSY-UHFFFAOYSA-N 0.000 description 1
- YRIBCMYGTPNNPO-UHFFFAOYSA-N C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O Chemical compound C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O YRIBCMYGTPNNPO-UHFFFAOYSA-N 0.000 description 1
- YFQJGQBRLRUKQL-UHFFFAOYSA-N CC(C)(C(C(C(C(C)(C)N1CCOCC1)C(C=C1)=CC=C1SC)=O)C(C=C1)=CC=C1SC)N1CCOCC1 Chemical compound CC(C)(C(C(C(C(C)(C)N1CCOCC1)C(C=C1)=CC=C1SC)=O)C(C=C1)=CC=C1SC)N1CCOCC1 YFQJGQBRLRUKQL-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- LZWJOIFXGGXZOZ-UHFFFAOYSA-N N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C.C(CCC)NC(C(C)C)=O Chemical compound N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C.C(CCC)NC(C(C)C)=O LZWJOIFXGGXZOZ-UHFFFAOYSA-N 0.000 description 1
- CWHYQFDXSMMSJP-UHFFFAOYSA-N N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.C1(CCCCC1)C#N Chemical compound N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.C1(CCCCC1)C#N CWHYQFDXSMMSJP-UHFFFAOYSA-N 0.000 description 1
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VLVQWVAPRCVNPZ-UHFFFAOYSA-N bis(2,2-diphenylethyl) carbonate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)COC(=O)OCC(C=1C=CC=CC=1)C1=CC=CC=C1 VLVQWVAPRCVNPZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- WMRNGPYHLQSTDL-UHFFFAOYSA-N n-cyclohexyl-2-[[1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound C1CCCCC1NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC1CCCCC1 WMRNGPYHLQSTDL-UHFFFAOYSA-N 0.000 description 1
- NPFIXJIFUHTLRP-UHFFFAOYSA-N n-cyclohexyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC1CCCCC1 NPFIXJIFUHTLRP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- AYEFIAVHMUFQPZ-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical compound CC(O)CO.OC(=O)C=C AYEFIAVHMUFQPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- OIQNWJHRBIPDFR-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate 2-tert-butylbenzenecarboperoxoic acid Chemical compound C(C)(C)(C)C1=C(C(=O)OO)C=CC=C1.C(C1=CC=CC=C1)(=O)OOC(C)(C)C OIQNWJHRBIPDFR-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Abstract
本公开提供共聚物，包括：1摩尔份的式1所示的重复单元；3至10摩尔份的式2所示的重复单元；以及5至15摩尔份的式3所示的重复单元；
其中R1为氢或甲基；R2为单键或C1‑3亚烷基；R3为具有芳基与乙烯基的聚硅氧烷基；以及R4与R5的每一个各自为氢、C1‑3的烷基、或具有芳基与乙烯基的聚硅氧烷基。
Description
技术领域
本公开涉及共聚物、更特别地涉及共聚物中的重复单元结构以及包含共聚物的树脂组合物。
背景技术
现有的移动装置或显示器均朝着可挠装置发展。大部分关于可挠装置的研究着重于基板的可挠性，但装置中的单元是否可挠也是装置是否可挠的关键。举例来说，在可挠装置中的层状物常为整片结构，若其不可挠或可挠性不佳，即使基板可挠也无法完成可挠装置。另一方面，上述层状物需具备高耐热性、高穿透性、与低介电性等特性，以符合装置需求。若层状物可进一步感光，则可作为光阻层。如此一来，此光阻层的分辨率将取决于层状物中的组成。
综上所述，目前亟需新的组成用于可挠装置的层状物，甚至作为光阻以形成可挠装置中的图案化单元。
发明内容
本公开一实施例提供共聚物，包括：1摩尔份的式1所示的重复单元；3至10摩尔份的式2所示的重复单元；以及5至15摩尔份的式3所示的重复单元；
其中R1为氢或甲基；R2为单键或C1-3亚烷基；R3为具有芳基与乙烯基的聚硅氧烷基；以及R4与R5的每一个各自为氢、C1-3的烷基、或具有芳基与乙烯基的聚硅氧烷基。
本公开一实施例提供的树脂组合物，包括：1重量份上述的共聚物；0.01至0.1重量份的引发剂；以及0.05至0.6重量份的交联单体。
具体实施方式
本公开一实施例提供共聚物，包括：1摩尔份的式1所示的重复单元；3至10摩尔份的式2所示的重复单元；以及5至15摩尔份的式3所示的重复单元。
上述R1为氢或甲基。在一实施例中，R1为氢。上述R2为单键或C1-3亚烷基。在一实施例中，R2为亚丙基。上述R3为具有芳基与乙烯基的聚硅氧烷基。在一实施例中，R4与R5的每一个各自为氢、C1-3的烷基、或具有芳基与乙烯基的聚硅氧烷基。换言之，式1中的R4和/或R5可与R3相同，也为具有芳基与乙烯基的聚硅氧烷基。在其它实施例中，R4与R5仅为氢或烷基如甲基。式1所示的重复单元中具有芳基与乙烯基的聚硅氧烷基，可提高耐热性、耐化性与兼容性。式2所示的重复单元可提高显影能力。若式2所示的重复单元比例过低，则显影分辨率差(≥10μm)。若式2所示的重复单元比例过高，则显影会过显而造成掉线或不均匀。式3所示的重复单元可提高与式1兼容性与耐热性。若式3所示的重复单元比例过低，则耐热性与兼容性差。若式3所示的重复单元比例过高，则挠曲性差。在一实施例中，上述共聚物的重均分子量介于5000和10000之间。若共聚物的重均分子量过低，则挠曲性差。若共聚物的重均分子量过高，则显影能力差且会影响交联的反应性。
在一实施例中，式1中具有芳基与乙烯基的聚硅氧烷基包括：1摩尔份的式4所示的重复单元；以及0.01至1摩尔份的式5所示的重复单元。
上述Ar为苯基、萘基、芘基、蒽基、菲基、联三亚苯基、或其它合适的芳基。在一实施例中，Ar为苯基。上述R6为C1-3的烷基、烯基、苯基、萘基、芘基、蒽基、菲基、或联三亚苯基。在一实施例中，R6为苯基。上述R7为C1-3的烷基、或苯基。在一实施例中，R7为甲基。式4所示的重复单元具有高耐热特性。若式(4)所示的重复单元比例过低，则耐热性差。若式4所示的重复单元比例过高，则易脆。式5所示的重复单元可进行交联反应，提供耐化特性。若式5所示的重复单元比例过低，则交联度低、无成膜特性。若式5所示的重复单元比例过高，则交联度高、易脆。
在其它实施例中，具有芳基与乙烯基的聚硅氧烷基还包括0至1摩尔份的式6所示的重复单元。
R8与R9的每一个各自为C1-3的烷基。在一实施例中，R8与R9为甲基。式6所示的重复单元可增加树脂与配方兼容性。若式6所示的重复单元比例过低，则可能产生相分离。
在一实施例中，上述具有芳基与乙烯基的聚硅氧烷基的重均分子量介于2000和3000之间。若具有芳基与乙烯基的聚硅氧烷基的重均分子量过低，则无寡聚物特性。若具有芳基与乙烯基的聚硅氧烷基的重均分子量过高，则反应性差，接枝不易。
上述共聚物的形成方法可为取(1)聚合物与(2)具芳基与乙烯基的聚硅氧烷反应而成。上述(1)聚合物可由式7所示的单体、苯乙烯、与马来酸酐聚合而成。在式7中，每个R’各自为氢或C1-3的烷基。至于R1与R2的定义同前述，在此不赘述。
上述(2)具芳基与乙烯基的聚硅氧烷可由式8的硅烷、式9的硅烷、及视情况采用的式10的硅烷反应而成。在式8、式9、与式10中，每个R”各自为氢或C1-3的烷基。至于R6、R7、R8、与R9的定义同前述，在此不赘述。
在一实施例中，可取1重量份上述共聚物，0.01至0.1重量份的引发剂，以及0.05至0.6重量份的交联单体，混合形成树脂组合物。若引发剂的用量过低，则聚合度低无高分子特性。若引发剂的用量过高，则聚合度高易脆。若交联单体的比例过低，则共聚物的交联程度不足而无法固化。若交联单体的比例过高，则易脆。在一实施例中，交联单体可为丙烯酸甘油酯、二季戊四醇六丙烯酸酯、乙二醇二丙烯酸酯(ethylene glycoldiacrylate)、三乙二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、新戊二醇二丙烯酸酯、季戊四醇二丙烯酸酯(pentaerythritoldiacrylate)、季戊四醇三丙烯酸酯(pentaerythritoltriacrylate)、二季戊四醇三丙烯酸酯(dipentaerythritoltriacrylate)、二季戊四醇丙烯酸酯(dipentaerythritolacrylate)、季戊四醇六丙烯酸酯(pentaerythritolhexaacrylate)、双酚A二丙烯酸酯、三羟甲基丙烷三丙烯酸酯、酚醛型环氧丙烯酸酯(novolacepoxyacrylate)、二甲基丙烯酸乙二醇酯、二甲基丙烯酸二乙二醇酯、二甲基丙烯酸三乙二醇酯、二甲基丙烯酸丙二醇酯、二甲基丙烯酸1,4-丁二醇酯、二甲基丙烯酸1,6-己二醇酯、甲基丙烯酸羟乙酯、丙烯酸异辛酯、丙烯酸羟乙酯、甲基丙烯酸甲酯、甲基丙烯酸或丙烯酸等。
在一实施例中，引发剂为光引发剂，而上述树脂组合物为光阻的。上述光引发剂可为苯乙酮类如2-甲基-1-(4-(甲基硫醇基)苯基-2-吗啉基丙基酮(2-methyl-1-(4-(methylthio)phenyl)-2-morpholino-propanone)、1-羟基环己基苯基酮(1-hydroxycyclohexyl phenyl ketone)、二苯乙氧基酮(diethoxyacetophenone)、2-羟基2-甲基-1-苯基-1-丙基-1-酮(2-hydroxy-2-methyl-1-phenyl-propane-1-one)、2-甲苯基-2-(二甲基胺基)-1-[4-(吗啉基)苯基]-1-丁基-1-酮(2-benzyl-2-(dimethylamino)-1-[4-(morpholinyl)phenyl]-1-butanone)、其他合适的苯乙酮；安息香类如安息香(benzoin)、安息香甲基醚(benzoin methyl ether)、安息香二甲醚(benzyl dimethylketal)、其它合适的安息香；二苯基酮类如二苯基酮(benzophenone)、4-苯基二苯基酮(4-phenyl benzophenone)、羟基二苯基酮(hydroxyl benzophenone)、或其它合适的二苯基酮；噻吨酮类如异丙基噻吨酮(isopropyl thioxanthone)、2-氯基噻吨酮(2-chlorothioxanthone)、或其它合适的噻吨酮；蒽醌类如2-乙基蒽醌(2-ethylanthraquinone)、或其它合适的蒽醌。上述的光引发剂除可单独使用外，也可混合使用以得到较快的感光速度，比如异丙基噻吨酮混合2-甲苯基-2-(二甲基胺基)-1-[4-(吗啉基)苯基]-1-丁基-1-酮。
在一实施例中，引发剂为热引发剂，而树脂组合物用于形成半导体装置中的平坦层或介电层。上述半导体装置为可挠。在一实施例中，热引发剂可为偶氮类如2,2’-偶氮二双(2,4-二甲基正戊腈)(2,2’-azobis(2,4-dimethyl valeronitrile))、二甲基-2,2’-偶氮双(2-丙酸甲酯)(dimethyl 2,2’-azobis(2-methylpropionate)、2,2-偶氮双异丁腈(2,2-azobisiso butyronitrile，AIBN)、2,2-偶氮双(2-甲基异丁腈)(2,2-azobis(2-methylisobutyronitrile))、1,1’-偶氮双(环己烷-1-腈)(1,1’-azobis(cyclohexane-1-carbonitrile))、2,2’-偶氮双[N-2-丙烯基-2-甲基丙酰胺](2,2’-azobis[N-(2-propenyl)-2-methyl propionamide])、1-[(氰基-1-甲基乙基)-偶氮基]甲酰胺(1-[(cyano-1-methylethyl)azo]formamide)、2,2’-偶氮双(N-丁基-2-甲基丙酰胺)2,2’-azobis(N-butyl-2-methylpropionamide))、2,2’-偶氮双(N-环己基-2-甲基丙酰胺)(2,2’-azobis(N-cyclo hexyl-2-methylpropionamide)、或其它合适的偶氮类引发剂；过氧化物类包括苯甲酰基过氧化物(benzoyl peroxide)、1,1-双(叔丁基过氧基)环己烷(1,1-bis(tert-butylperoxy)cyclohexane)、2,5-双(叔丁基过氧基)-2,5-二甲基环己烷(2,5-bis(tert-butylperoxy)-2,5-dimethyl cyclohexane)、2,5-双(叔丁基过氧基)-2,5-二甲基-3-环己炔(2,5-bis(tert-butyl peroxy)-2,5-dimethyl-3-cyclohexyne)、双(1-(叔丁基过氧基)-1-甲基乙基)苯(bis(1-(tert-butylpeorxy)-1-methy-ethyl)benzene)、叔丁基过氧化氢(tert-butyl hydroperoxide)、叔丁基过氧化物(tert-butyl peroxide)、叔丁基过氧基苯甲酸酯(tert-butyl peroxybenzoate)、茴香基过氧化氢(cumenehydroperoxide)、环己酮基过氧化物(cyclohexanone peroxide)、二茴香基过氧化物(dicumyl peroxide)、月桂基过氧化物(lauroyl peroxide)、或其它合适的过氧化物。上述的热引发剂除可单独使用外，也可混合使用，视需要而定。
由实验可知，上述树脂组合物在交联硬化后形成的层状物或图案，具有低介电常数、小挠曲半径、高透光度、以及高耐热性(如在高温下不易黄变)等特性。当上述树脂组合物为光阻时，其形成的图案除了上述特征外，其分辨率可达小于30μm。综上所述，上述树脂组合物适用于可挠装置如移动装置与显示器。
为了使本公开的上述和其它目的、特征、和优点能更明显易懂，下文特举几个实施例并配合图示，作如下详细说明：
实施例
制备例1
取不同摩尔份的3-(甲基丙烯酰氧)丙基三甲氧基硅烷、苯乙烯、与马来酸酐作为共聚单体，并以上述单体的总重为基准，取5phr的偶氮二异丁腈(AIBN)作为引发剂。将上述单体与引发剂加入75mL的甲乙酮后混合，加热至80℃后反应4小时以形成共聚物，如式11所示。
在式11中，x、y、与z分别对应3-(甲基丙烯酰氧)丙基三甲氧基硅烷、苯乙烯、与马来酸酐的摩尔分数，且此共聚物属于无规共聚物。上述共聚物的单体用量、数均分子量、重均分子量、固体含量、与25℃下的平均粘度如表1所示。上述共聚物的数均分子量与重均分子量是由凝胶渗透层析仪(GPC，WATERS Model 600)测量，而平均粘度是由粘度仪(BROOKFIELD)在25℃下测得。
表1
制备例2
取不同摩尔份的二苯基硅二醇、二甲氧基二甲基硅烷、与甲基乙烯基二甲氧基硅烷作为聚硅氧烷的单体。以上述单体的总摩尔数为基准，取不同摩尔％的氢氧化钡作为碱催化剂。在氮气下混合单体与碱催化剂，加热至60℃进行溶胶-凝胶反应12小时，再通过减压浓缩去除反应形成的甲醇与水以获得聚硅氧烷，如式12所示。
在式12中，m、n、o分别对应二苯基硅二醇、二甲氧基二甲基硅烷、甲基乙烯基二甲氧基硅烷的摩尔分数，且聚硅氧烷属于无规共聚物。上述聚硅氧烷的单体用量、重均分子量、与固体含量如表2所示。上述聚硅氧烷的重均分子量是由凝胶渗透层析仪(GPC)测量。
表2
制备例3
取制备例1的共聚物与制备例2的聚硅氧烷，加入75mL的甲乙酮后加热至60℃进行反应10小时，如式13所示。
在式13中，x、y、z、m、n、与o的定义如前述，且共聚物与聚硅氧烷基属于无规共聚物。上述共聚物与聚硅氧烷的种类与用量，以及产物的固体含量、与25℃下的平均粘度如表3所示。上述共聚物的平均粘度利用粘度仪(BROOKFIELD)在25℃下测得。
表3
实施例与比较例
取5重量份制备例1或3的产物、0.2重量份的Irgacure OXE 01(购于光彦贸易)作为光引发剂、与1重量份的M400(购于双键化工)作为交联单体，混合后形成树脂组合物。将上述树脂组合物涂布于基板上后，以具有不同线宽图案的测试光罩进行曝光，再显影形成图案，以确认图案的分辨率。此外，取上述树脂组合物涂布于基板上后，直接曝光硬化形成整片层状物，以测量层状物的介电常数(测量方法请参考Chao,H.-W.；Wong,W.-S.；Chang,T.-H.,Characterizing the complex permittivity of high-κdielectrics usingenhanced field method.Review of Scientific Instruments 2015,86(11),114701.)与挠曲半径(测量标准为IEC 62715-6-1)。层状物的介电常数与挠曲半径、与光阻图案的分辨率如表4所示。
表4
由上述可知，具有聚硅氧烷基的共聚物可改善树脂组合物形成的层状物的可挠性，并降低层状物的介电常数。
虽然本公开已经通过几个实施例公开如上，然其并非用以限定本公开，任何本领域技术人员，在不脱离本公开的精神和范围内，当可作任意的更动与润饰，因此本公开的保护范围当视所附的申请专利范围所界定者为准。
Claims (8)
1.一种共聚物，包括：
1摩尔份的式1所示的重复单元；
3至10摩尔份的式2所示的重复单元；以及
5至15摩尔份的式3所示的重复单元；
其中R1为氢或甲基；
R2为单键或C1-3亚烷基；
R3为具有芳基与乙烯基的聚硅氧烷基；以及
R4与R5的每一个各自为氢、C1-3的烷基、或具有芳基与乙烯基的聚硅氧烷基，和
其中具有芳基与乙烯基的聚硅氧烷基包括：
1摩尔份的式4所示的重复单元；以及
0.01至1摩尔份的式5所示的重复单元，
其中Ar为苯基、萘基、芘基、蒽基、菲基、或联三亚苯基；
R6为C1-3的烷基、烯基、苯基、萘基、芘基、蒽基、菲基、或联三亚苯基；以及
R7为C1-3的烷基、或苯基。
2.如权利要求1所述的共聚物，其重均分子量介于5000和10000之间。
3.如权利要求1所述的共聚物，其中具有芳基与乙烯基的聚硅氧烷基的重均分子量介于2000和3000之间。
4.如权利要求1所述的共聚物，其中具有芳基与乙烯基的聚硅氧烷基还包括：
0至1摩尔份的式6所示的重复单元；
其中R8与R9的每一个各自为C1-3的烷基。
5.一种树脂组合物，包括：
1重量份权利要求1所述的共聚物；
0.01至0.1重量份的引发剂；以及
0.05至0.6重量份的交联单体。
6.如权利要求5所述的树脂组合物，其中该引发剂为光引发剂，且该树脂组合物为光阻。
7.如权利要求5所述的树脂组合物，其中该引发剂为热引发剂，且该树脂组合物用于形成半导体装置中的平坦层或介电层。
8.如权利要求7所述的树脂组合物，其中该半导体装置为能挠曲的。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW107104497 | 2018-02-08 | ||
| TW107104497A TWI648298B (zh) | 2018-02-08 | 2018-02-08 | 共聚物與樹脂組合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110128661A CN110128661A (zh) | 2019-08-16 |
| CN110128661B true CN110128661B (zh) | 2021-08-31 |
Family
ID=65803952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810757082.2A Active CN110128661B (zh) | 2018-02-08 | 2018-07-11 | 共聚物与树脂组合物 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US10533088B2 (zh) |
| CN (1) | CN110128661B (zh) |
| TW (1) | TWI648298B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113402648B (zh) * | 2021-07-26 | 2023-03-24 | 上海微陌新材料科技有限公司 | 用于光引发聚合制备苯乙烯-顺酐共聚物的母液、共聚物制备方法及设备 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6153717A (en) * | 1997-05-19 | 2000-11-28 | Industrial Technology Research Institute | Polysiloxane containing tertiary amine groups and method of preparing the same |
| US7297360B2 (en) * | 2002-12-06 | 2007-11-20 | Jsr Corporation | Insulation film |
| CN101233160A (zh) * | 2005-07-26 | 2008-07-30 | 巴斯福股份公司 | 含硅氧烷基团的共聚物、其制备方法和用途 |
| CN105717746A (zh) * | 2014-12-22 | 2016-06-29 | 奇美实业股份有限公司 | 感光性聚硅氧烷组成物、保护膜以及具有保护膜的元件 |
| CN106046735A (zh) * | 2015-04-10 | 2016-10-26 | 中国石油化工股份有限公司 | 一种具有高雾度、高透光率的聚碳酸酯树脂组合物及其制备方法 |
| CN107344985A (zh) * | 2016-05-06 | 2017-11-14 | 财团法人工业技术研究院 | 共聚物和含其的树脂组合物、封装膜及封装结构 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS552237A (en) * | 1978-06-21 | 1980-01-09 | Ricoh Co Ltd | Photoreceptor for electrophotography |
| JPS5780466A (en) * | 1980-11-08 | 1982-05-20 | Kanegafuchi Chem Ind Co Ltd | Dispersion of pigment |
| JPS57105446A (en) * | 1980-12-19 | 1982-06-30 | Kanegafuchi Chem Ind Co Ltd | Curable composition |
| JPS5819361A (ja) * | 1981-07-27 | 1983-02-04 | Kanegafuchi Chem Ind Co Ltd | １液型室温硬化性組成物 |
| US4690993A (en) * | 1985-11-25 | 1987-09-01 | Alcon Laboratories, Inc. | p-(2-Hydroxy hexafluoroisopropyl) styrene [HFIS] monomer for ophthalmic applications |
| US4772672A (en) * | 1986-05-15 | 1988-09-20 | Kansai Paint Company, Limited | Curable compositions and method of curing same |
| GB2212503B (en) * | 1987-11-16 | 1991-11-20 | Kansai Paint Co Ltd | Composition curable at low temperature |
| JPH0651795B2 (ja) * | 1988-09-16 | 1994-07-06 | 信越化学工業株式会社 | メタクリル官能性ジメチルポリシロキサン |
| US5063114A (en) * | 1989-04-06 | 1991-11-05 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Coated material |
| CA2013949C (en) * | 1989-04-06 | 1999-08-24 | Toshiro Nambu | Thermosetting composition |
| JPH08320567A (ja) * | 1995-05-25 | 1996-12-03 | Toyo Ink Mfg Co Ltd | フォトソルダーレジスト組成物 |
| US7015256B2 (en) | 2002-01-28 | 2006-03-21 | Jsr Corporation | Composition for forming photosensitive dielectric material, and transfer film, dielectric material and electronic parts using the same |
| US7285371B2 (en) | 2004-11-30 | 2007-10-23 | Industrial Technology Research Institute | Photosensitive composition and color paste |
| CN100413921C (zh) * | 2005-01-26 | 2008-08-27 | 中国石油化工股份有限公司 | 热塑性树脂组合物 |
| JPWO2006115117A1 (ja) | 2005-04-20 | 2008-12-18 | 関西ペイント株式会社 | 記録媒体原盤用ポジ型レジスト組成物、並びに、それを用いた記録媒体原盤の製造方法及びスタンパの製造方法 |
| WO2007069585A1 (ja) | 2005-12-13 | 2007-06-21 | Kansai Paint Co., Ltd. | 回路基板用ポジ型レジスト組成物、回路基板用ポジ型ドライフィルム、及び、それを用いた回路基板の製造方法 |
| TWI299815B (en) | 2005-12-19 | 2008-08-11 | Ind Tech Res Inst | Color photosensitive composition and formulation method thereof |
| CN1991582B (zh) | 2005-12-31 | 2010-04-21 | 财团法人工业技术研究院 | 负型感光间隙控制材料的组成及其形成方法 |
| TWI330757B (en) | 2006-12-27 | 2010-09-21 | Ind Tech Res Inst | Pigmentary photosensitive material |
| AU2008228842B2 (en) | 2007-03-21 | 2014-01-16 | Avery Dennison Corporation | Pressure sensitive adhesives |
| TWI363784B (en) | 2007-10-01 | 2012-05-11 | Ind Tech Res Inst | High optical contrast pigment and colorful photosensitive composition employing the same and fabrication method thereof |
| JP5206977B2 (ja) | 2009-03-12 | 2013-06-12 | 信越化学工業株式会社 | 新規ポリイミドシリコーン及びこれを含有する感光性樹脂組成物並びにパターン形成方法 |
| TWI418585B (zh) | 2009-10-16 | 2013-12-11 | Ind Tech Res Inst | 光學保護膜 |
| WO2011065342A1 (ja) | 2009-11-27 | 2011-06-03 | Dic株式会社 | 凸版反転印刷用インキ組成物、印刷物、及びカラーフィルタ |
| CN101792633B (zh) | 2010-03-09 | 2013-04-24 | 浙江大学 | 一种抗静电超疏水复合涂层的制备方法 |
| TW201308352A (zh) | 2011-08-08 | 2013-02-16 | Ind Tech Res Inst | 導電膠體及包含此導電膠體之太陽能電池 |
| US8593713B2 (en) | 2011-12-15 | 2013-11-26 | Industrial Technology Research Institute | Ink composition used in electrowetting display device and electrowetting display device employing the same |
| JP6013150B2 (ja) | 2012-11-22 | 2016-10-25 | メルクパフォーマンスマテリアルズマニュファクチャリング合同会社 | ポジ型感光性シロキサン組成物の製造方法 |
| TWI489212B (zh) | 2013-03-29 | 2015-06-21 | Chi Mei Corp | Photosensitive resin composition and its application |
-
2018
- 2018-02-08 TW TW107104497A patent/TWI648298B/zh active
- 2018-07-11 CN CN201810757082.2A patent/CN110128661B/zh active Active
- 2018-08-14 US US16/103,174 patent/US10533088B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6153717A (en) * | 1997-05-19 | 2000-11-28 | Industrial Technology Research Institute | Polysiloxane containing tertiary amine groups and method of preparing the same |
| US7297360B2 (en) * | 2002-12-06 | 2007-11-20 | Jsr Corporation | Insulation film |
| CN101233160A (zh) * | 2005-07-26 | 2008-07-30 | 巴斯福股份公司 | 含硅氧烷基团的共聚物、其制备方法和用途 |
| CN105717746A (zh) * | 2014-12-22 | 2016-06-29 | 奇美实业股份有限公司 | 感光性聚硅氧烷组成物、保护膜以及具有保护膜的元件 |
| CN106046735A (zh) * | 2015-04-10 | 2016-10-26 | 中国石油化工股份有限公司 | 一种具有高雾度、高透光率的聚碳酸酯树脂组合物及其制备方法 |
| CN107344985A (zh) * | 2016-05-06 | 2017-11-14 | 财团法人工业技术研究院 | 共聚物和含其的树脂组合物、封装膜及封装结构 |
Also Published As
| Publication number | Publication date |
|---|---|
| US10533088B2 (en) | 2020-01-14 |
| TWI648298B (zh) | 2019-01-21 |
| TW201934598A (zh) | 2019-09-01 |
| US20190241730A1 (en) | 2019-08-08 |
| CN110128661A (zh) | 2019-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7750059B2 (en) | Polymer solution for nanoimprint lithography to reduce imprint temperature and pressure | |
| US8084545B2 (en) | Photo- and/or thermo-curable copolymer, curable resin compositions, and cured articles | |
| JP4535309B2 (ja) | 光学記録材料 | |
| CN110183665B (zh) | 一种含巯基mtq树脂的制备方法及其应用 | |
| US20100123269A1 (en) | Photosensitive resin composition for imprinting process and method for forming organic layer over substrate | |
| TW200933293A (en) | Photosensitive graft polymer and photosensitive resin composition containing same | |
| KR20100088285A (ko) | 롤 프린트 공법에 적용되는 유기절연막 형성용 잉크조성물 | |
| CN104428713A (zh) | 感光性树脂组合物、导电性配线保护膜和触摸面板构件 | |
| JP2006193718A (ja) | ３，４−エポキシトリシクロ［５．２．１．０２，６］デカン環を有する構造単位を含む共重合体とその製造法 | |
| KR20130074760A (ko) | 경화성 수지 조성물, 경화물 및 광학 물품 | |
| KR20150139900A (ko) | 무용제형 광경화성 수지 조성물 | |
| TW201120571A (en) | Photosensitive resin composition | |
| EP2289958B1 (en) | Curable composition and cured film using same | |
| CN110128661B (zh) | 共聚物与树脂组合物 | |
| Lin et al. | Polyhedral Oligomeric Silsesquioxane Containing Copolymers for Negative‐Type Photoresists | |
| JP2020079930A (ja) | 感光性樹脂組成物 | |
| Lin et al. | Characterization of negative-type photoresists containing polyhedral oligomeric silsesquioxane methacrylate | |
| JP2002023349A (ja) | 感光性樹脂凸版材 | |
| KR20160108160A (ko) | 에칭 레지스트 조성물 및 드라이 필름 | |
| JPWO2016017596A1 (ja) | 感光性樹脂組成物、感光性エレメント、レジストパターンの製造方法及びプリント配線板の製造方法 | |
| CN111040093B (zh) | 一种感光树脂及其制备方法和应用 | |
| CN110709435B (zh) | 可光固化且可热固化共聚物以及使用其的光敏树脂组合物、光敏树脂膜和滤色器 | |
| CN112074551A (zh) | 碱溶性、可光固化且可热固化的共聚物及使用其的光敏树脂组合物、光敏树脂膜和滤色器 | |
| CN108017747B (zh) | 一种碱溶性树脂聚合物、其制备方法和感光性树脂组合物 | |
| JP2005330481A (ja) | 高分子化合物およびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |