CN109789644A - 形成介电膜的组合物 - Google Patents
形成介电膜的组合物 Download PDFInfo
- Publication number
- CN109789644A CN109789644A CN201880001950.2A CN201880001950A CN109789644A CN 109789644 A CN109789644 A CN 109789644A CN 201880001950 A CN201880001950 A CN 201880001950A CN 109789644 A CN109789644 A CN 109789644A
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- CN
- China
- Prior art keywords
- methyl
- acrylate
- dielectric film
- weight
- composition
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 128
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 67
- 229920000642 polymer Polymers 0.000 claims abstract description 62
- 239000004642 Polyimide Substances 0.000 claims abstract description 44
- 229920001721 polyimide Polymers 0.000 claims abstract description 43
- 239000011256 inorganic filler Substances 0.000 claims abstract description 25
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- -1 carboxyethyl (methyl) acrylate Chemical compound 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 64
- 239000000758 substrate Substances 0.000 claims description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 47
- 238000004132 cross linking Methods 0.000 claims description 31
- 239000000377 silicon dioxide Substances 0.000 claims description 22
- 239000003431 cross linking reagent Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 239000010936 titanium Substances 0.000 claims description 18
- 229910052719 titanium Inorganic materials 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- 239000004065 semiconductor Substances 0.000 claims description 15
- 229910052726 zirconium Inorganic materials 0.000 claims description 14
- 229910052735 hafnium Inorganic materials 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000608 laser ablation Methods 0.000 claims description 8
- 239000010954 inorganic particle Substances 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001259 photo etching Methods 0.000 claims description 4
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 claims description 4
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical group C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000484 niobium oxide Inorganic materials 0.000 claims description 3
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- KJMGIINCIYPCFQ-UHFFFAOYSA-N 2-methylhex-2-enedioic acid Chemical compound OC(=O)C(C)=CCCC(O)=O KJMGIINCIYPCFQ-UHFFFAOYSA-N 0.000 claims description 2
- SZRYWLOKYVAAIM-UHFFFAOYSA-J C(=O)(O)CCC=C(C(=O)[O-])C.[Hf+4].C(=O)(O)CCC=C(C(=O)[O-])C.C(=O)(O)CCC=C(C(=O)[O-])C.C(=O)(O)CCC=C(C(=O)[O-])C Chemical compound C(=O)(O)CCC=C(C(=O)[O-])C.[Hf+4].C(=O)(O)CCC=C(C(=O)[O-])C.C(=O)(O)CCC=C(C(=O)[O-])C.C(=O)(O)CCC=C(C(=O)[O-])C SZRYWLOKYVAAIM-UHFFFAOYSA-J 0.000 claims description 2
- VDAFMNDBIAJQMH-UHFFFAOYSA-N C(C=C)(=O)OC.[Hf] Chemical compound C(C=C)(=O)OC.[Hf] VDAFMNDBIAJQMH-UHFFFAOYSA-N 0.000 claims description 2
- 229910004613 CdTe Inorganic materials 0.000 claims description 2
- HEWYAFSDYSSEGE-UHFFFAOYSA-N [Ti].COC(=O)C=C Chemical compound [Ti].COC(=O)C=C HEWYAFSDYSSEGE-UHFFFAOYSA-N 0.000 claims description 2
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002113 barium titanate Inorganic materials 0.000 claims description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 2
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000449 hafnium oxide Inorganic materials 0.000 claims description 2
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 claims description 2
- OWBUQVKUUAKCBW-UHFFFAOYSA-N methyl prop-2-enoate zirconium Chemical compound COC(C=C)=O.[Zr] OWBUQVKUUAKCBW-UHFFFAOYSA-N 0.000 claims description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- UKDIAJWKFXFVFG-UHFFFAOYSA-N potassium;oxido(dioxo)niobium Chemical compound [K+].[O-][Nb](=O)=O UKDIAJWKFXFVFG-UHFFFAOYSA-N 0.000 claims description 2
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- VXYRUJSDSBANQI-UHFFFAOYSA-N 2-methylprop-2-enoic acid;titanium Chemical compound [Ti].CC(=C)C(O)=O VXYRUJSDSBANQI-UHFFFAOYSA-N 0.000 claims 1
- ZBWDIIRDTGVUFN-UHFFFAOYSA-N C(=O)(O)CCC=C(C(=O)OOCCCC)C Chemical compound C(=O)(O)CCC=C(C(=O)OOCCCC)C ZBWDIIRDTGVUFN-UHFFFAOYSA-N 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 21
- 229910052799 carbon Inorganic materials 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 30
- 239000000945 filler Substances 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 23
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 22
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 20
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 17
- 239000002131 composite material Substances 0.000 description 17
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- 239000005020 polyethylene terephthalate Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000002318 adhesion promoter Substances 0.000 description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000005855 radiation Effects 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- YVNRUPSDZZZUQJ-UHFFFAOYSA-N [O].NC1=CC=CC=C1 Chemical compound [O].NC1=CC=CC=C1 YVNRUPSDZZZUQJ-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 229940116333 ethyl lactate Drugs 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- 229920005575 poly(amic acid) Polymers 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 239000011241 protective layer Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000003475 lamination Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 4
- 238000010422 painting Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 3
- 229940005561 1,4-benzoquinone Drugs 0.000 description 3
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 229940113088 dimethylacetamide Drugs 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 239000013047 polymeric layer Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000004040 pyrrolidinones Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
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- MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- 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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- 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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/105—Esters of polyhydric alcohols or polyhydric phenols of pentaalcohols
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- 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
- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
- C08F267/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of amides or imides
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/1003—Preparatory processes
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- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
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- 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
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- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
本发明涉及含有至少一种完全酰亚胺化的聚酰亚胺聚合物;至少一种无机填料;至少一种含金属的(甲基)丙烯酸酯化合物;和至少一种催化剂的形成介电膜的组合物。由这种组合物形成的介电膜可以具有相对低的热膨胀系数(CTE)和相对高的光学透明度。
Description
相关申请的交叉引用
本申请要求2017年11月6日提交的美国临时申请序列号62/581,895和2017年9月11日提交的美国临时申请序列号62/556,723的优先权。在先申请通过引用整体并入本文。
背景技术
移动计算应用的持续扩展需要在更小的器件占用空间中封装不断增长的计算能力。半导体器件的设计者依赖于使用各种新的芯片架构来满足新的器件要求。这些新架构不仅对新集成电路的设计者提出了重大挑战,而且对将使用这些器件的封装材料的设计者也提出了重大挑战。
发明内容
由于新的先进器件在很大程度上依赖晶圆和面板级封装(WLP和PLP)以及3D集成,因此对于封装应用的介电材料要求不断发展。对于先进封装设计的介电膜的一个重要要求是低热膨胀系数(CTE)。近年来,在成膜组合物中使用了诸如二氧化硅颗粒的填料以降低所得膜的CTE。该方法的缺点在于随着填料量的增加,膜的透明度降低,并且通过使用光化辐射图案化这种介电膜变得困难。另外,这种介电膜的机械性能随着填料量的增加而受到影响。本公开涉及新颖的组合物,其令人惊讶地降低所形成的介电膜的CTE量,同时保持膜透明。另外,由此形成的膜保持其机械性能,例如断裂伸长率和杨氏模量。
一方面,本发明的特征在于一种形成介电膜的组合物,包含:
a)至少一种完全酰亚胺化的聚酰亚胺聚合物;
b)至少一种无机填料;
c)至少一种含金属的(甲基)丙烯酸酯化合物;和
d)至少一种能够引发聚合反应的催化剂。
在另一方面,本发明的特征在于由本文所述的组合物形成的介电膜(例如,能自己立住的膜)。在一些实施方案中,介电膜可包括(例如,在交联之前):a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种含金属的(甲基)丙烯酸酯(例如,未交联的含金属的(甲基)丙烯酸酯);d)至少一种能够引发聚合反应的催化剂。在一些实施方案中,介电膜可包括(例如,在交联之后):a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种交联的含金属的(甲基)丙烯酸酯。
在另一方面,本发明的特征在于一种干膜,包括载体衬底;由载体衬底支撑的本文所述的介电膜。
在另一方面,本发明的特征在于一种用于制造图案化的介电膜的方法,包括以下步骤:
a)在衬底上涂覆(例如,通过旋涂)本文所述的形成介电膜的组合物,以形成介电膜;以及
b)通过激光烧蚀工艺或光刻工艺图案化该膜以形成图案化的介电膜。
在又一方面,本发明的特征在于一种用于制备干膜结构的方法。该方法包括:
(A)用本文所述的形成介电膜的组合物涂覆含有至少一个塑料膜的载体衬底;
(B)干燥涂覆的组合物以形成介电膜;以及
(C)任选地将保护层施加到介电膜上。
具体实施方式
如本文所用,术语“完全酰亚胺化”是指本发明的聚酰亚胺聚合物为至少约90%(例如,至少约95%、至少约98%、至少约99%、或约100%)酰亚胺化。如本文所用,含金属的(甲基)丙烯酸酯(MCA)是指含有金属和(甲基)丙烯酸酯配体的化合物。MCA的(甲基)丙烯酸酯配体具有足够的反应性,以使MCA能够参与含MCA的膜的自由基诱导的交联。如本文所用,术语“(甲基)丙烯酸酯”包括丙烯酸酯和甲基丙烯酸酯。如本文所用,催化剂(例如引发剂)是当暴露于热源和/或辐射源时能够引发聚合或交联反应的化合物。如本文所用,交联剂是含有两个或更多个能在催化剂存在下进行交联或聚合反应的烯基或炔基的化合物。
在一些实施方案中,本发明的特征在于一种形成介电膜的组合物,包含
a)至少一种完全酰亚胺化的聚酰亚胺聚合物;
b)至少一种无机填料;
c)至少一种含金属的(甲基)丙烯酸酯化合物;和
d)至少一种能够引发聚合反应的催化剂。
在一些实施方案中,通过至少一种二胺与至少一种二羧酸二酐反应来制备形成介电膜的组合物的至少一种完全酰亚胺化的聚酰亚胺聚合物。
合适的二胺的实例包括但不限于1-(4-氨基苯基)-1,3,3-三甲基茚满-5-胺(其他名称包括4,4'-[1,4-亚苯基-双(1-甲基亚乙基)]二苯胺)、1-(4-氨基苯基)-1,3,3-三甲基-2H-茚满-5-胺、1-(4-氨基苯基)-1,3,3-三甲基-茚满-5-胺、[1-(4-氨基苯基)-1,3,3-三甲基-茚满-5-基]胺、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚满-5-胺、5-氨基-6-甲基-1-(3'-氨基-4'-甲基苯基)-1,3,3-三甲基茚满、4-氨基-6-甲基-1-(3'-氨基-4'-甲基苯基)-1,3,3-三甲基茚满、5,7-二氨基-1,1-二甲基茚满、4,7-二氨基-1,1-二甲基茚满、5,7-二氨基-1,1,4-三甲基茚满、5,7-二氨基-1,1,6-三甲基茚满、5,7-二氨基-1,1-二甲基-4-乙基茚满、对苯二胺、间苯二胺、邻苯二胺、3-甲基-1,2-苯二胺、1,2-二氨基乙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,5-二氨基戊烷、1,6-二氨基己烷、1,7-二氨基庚烷、1,8-二氨基辛烷、1,9-二氨基壬烷、1,10-二氨基癸烷、1,2-二氨基环己烷、1,4-二氨基环己烷、1,3-环己烷双(甲胺)、5-氨基-1,3,3-三甲基环己烷甲胺、2,5-二氨基三氟甲苯、3,5-二氨基三氟甲苯、1,3-二氨基-2,4,5,6-四氟苯、4,4'-二氨基苯胺、3,4'-二氨基二苯醚、3,3'-二氨基二苯醚、3,3'-二氨基二苯基砜、4,4'-二氨基二苯基砜、4,4'-异亚丙基二苯胺、4,4'-二氨基二苯基甲烷、2,2-双(4-氨基苯基)丙烷、4,4'-二氨基二苯基丙烷、4,4'-二氨基二苯基硫醚、4,4'-二氨基二苯基砜、4-氨基苯基-3-氨基苯甲酸酯、2,2'-二甲基-4,4'-二氨基联苯、3,3'-二甲基-4,4'-二氨基联苯、2,2'-双(三氟甲基)联苯胺、3,3'-双(三氟甲基)联苯胺、2,2-双[4-(4-氨基苯氧基苯基)]六氟丙烷、2,2-双(3-氨基-4-甲基苯基)-六氟丙烷、2,2-双(3-氨基苯基)-1,1,1,3,3,3-六氟丙烷、1,3-双-(4-氨基苯氧基)苯、1,3-双-(3-氨基苯氧基)苯、1,4-双-(4-氨基苯氧基)苯、1,4-双-(3-氨基苯氧基)苯、1-(4-氨基苯氧基)-3-(3-氨基苯氧基)苯、2,2'-双-(4-苯氧基苯胺)异亚丙基、双(对-β-氨基-叔丁基苯基)醚、对-双-2-(2-甲基-4-氨基戊基)苯、对-双(1,1-二甲基-5-氨基戊基)苯、3,3'-二甲基-4,4'-二氨基联苯、4,4'-二氨基二苯甲酮、3'-二氯联苯胺、2,2-双[4-(4-氨基苯氧基)苯基]丙烷、4,4'-[1,3-亚苯基双(1-甲基-亚乙基)]二苯胺、4,4'-[1,4-亚苯基双(1-甲基-亚乙基)]二苯胺、2,2-双[4-(4-氨基苯氧基)苯基]砜、2,2-双[4-(3-氨基苯氧基)苯]、1,4-双(4-氨基苯氧基)苯、1,3-双(4-氨基苯氧基)苯、(1,3'-双(3-氨基苯氧基)苯和9H-芴-2,6-二胺。这些二胺中的任何一种可以单独使用或以任何比例组合使用,只要所得聚酰亚胺聚合物满足本发明的要求即可。
四羧酸二酐单体的实例包括但不限于1-(3',4'-二羧基苯基)-1,3,3-三甲基茚满-5,6-二羧酸二酐、1-(3',4'-二羧基苯基)-1,3,3-三甲基茚满-6,7-二羧酸二酐、1-(3',4'-二羧基苯基)-3-甲基茚满-5,6-二羧酸二酐、1-(3',4'-二羧基苯基)-3-甲基茚满-6,7-二羧酸酐、吡嗪-2,3,5,6-四羧酸二酐、噻吩-2,3,4,5-四羧酸二酐、2,3,5,6-吡啶四羧酸二酐、降冰片烷-2,3,5,6-四羧酸二酐、双环[2.2.2]辛-7-烯-3,4,8,9-四羧酸二酐、四环[4.4.1.02,5.07,10]十一烷-1,2,3,4-四羧酸二酐、3,3',4,4'-二苯甲酮四羧酸二酐、3,3',4,4'-二苯砜四羧酸二酐、3,3',4,4'-二苯醚四羧酸二酐、2,3,3',4'-二苯醚四羧酸二酐、2,2-[双(3,4-二羧基苯基)]六氟丙烷二酐、乙二醇双(无水偏苯三酸)和5-(2,5-二氧代四氢)-3-甲基-3-环己烯-1,2-二羧酸酐。更优选的四羧酸二酐单体包括2,2-[双(3,4-二羧基苯基)]六氟丙烷二酐、3,3',4,4'-二苯甲酮四羧酸二酐、3,3',4,4'-二苯基砜四羧酸二酐和3,3',4,4'-二苯基醚四羧酸二酐。这些四羧酸二酐中的任何一种都可以单独使用或以任何比例组合使用,只要所得聚酰亚胺聚合物满足本发明的要求即可。
通常,由此形成的聚酰亚胺聚合物可溶于有机溶剂中。在一些实施方案中,聚酰亚胺聚合物在25℃在有机溶剂中的溶解度可为至少约50mg/mL(例如,至少约100mg/mL或至少约200mg/mL)。有机溶剂的实例包括但不限于内酯,诸如γ-丁内酯、ε-己内酯、γ-己内酯和δ-戊内酯;环酮,诸如环戊酮和环己酮;线性酮,诸如甲乙酮(MEK);酯,诸如乙酸正丁酯;酯醇,诸如乳酸乙酯;醚醇,诸如四氢糠醇;二醇酯,诸如丙二醇甲醚乙酸酯;吡咯烷酮,诸如N-甲基吡咯烷酮。
在一些实施方案中,为了合成完全酰亚胺化的聚酰亚胺(PI)聚合物,首先制备聚酰亚胺前体聚合物。在一些实施方案中,PI前体聚合物是聚酰胺酸(PAA)聚合物。在一些实施方案中,PI前体是聚酰胺酯(PAE)聚合物。在一些实施方案中,一种或多种二胺与一种或多种四羧酸二酐在至少一种(例如,两种、三种或更多种)聚合溶剂中组合以形成聚酰胺酸(PAA)聚合物。在一些实施方案中,所形成的PAA聚合物通过化学或热的方式酰亚胺化,以形成PI聚合物。在一些实施方案中,在聚合物合成期间或在聚合物合成之后,通过使用合适的试剂对PAA聚合物进行封端。在一些实施方案中,形成的PAA聚合物被酯化以形成聚酰胺酯(PAE)聚合物。在一些实施方案中,通过四羧酸半酯与一种或多种二胺在至少一种聚合溶剂中的组合形成PAE聚合物。在一些实施方案中,通过使用合适的试剂对PAE聚合物进行封端。在一些实施方案中,封端的PI聚合物由PAA聚合物或含有封端基团的PAE聚合物合成。在一些实施方案中,这种PI聚合物在酰亚胺化后被封端。
在一些实施方案中,将化学酰亚胺化剂(例如,脱水剂)加入PAA聚合物中,以催化聚酰胺酸基团的闭环脱水过程以形成酰亚胺官能团,从而形成PI聚合物。合适的脱水剂的实例包括但不限于三氟甲磺酸、甲磺酸、对甲苯磺酸、乙磺酸、丁磺酸、全氟丁烷磺酸、乙酸酐、丙酸酐和丁酸酐。此外,该脱水过程可以通过进一步加入碱性催化剂来催化。合适的碱性催化剂的实例包括但不限于吡啶、三乙胺、三丙胺、三丁胺、二环己基甲胺、2,6-二甲基吡啶、3,5-二甲基吡啶、甲基吡啶、4-二甲基氨基吡啶(DMAP)等。
合成封端和非封端的PI前体聚合物的方法是本领域技术人员熟知的。此类方法的实例公开于例如专利号US2,731,447、US3,435,002、US3,856,752、US3,983,092、US4,026,876、US4,040,831、US4,579,809、US4,629,777、US4,656,116、US4,960,860、US4,985,529、US5,006,611、US5,122,436、US5,252,534、US5,4789,15、US5,773,559、US5,783,656、US5,969,055、US9,617,386的美国专利和申请号US20040265731、US20040235992和US2007083016的美国申请,其内容通过引用并入到本文中。
用于制备PI聚合物或其前体的聚合溶剂通常是一种或两种或更多种极性非质子溶剂的组合。合适的极性非质子溶剂包括但不限于二甲基甲酰胺(DMF)、二甲基乙酰胺(DMAc)、N-甲酰基吗啉(NFM)、N-甲基吡咯烷酮(NMP)、N-乙基吡咯烷酮(NEP)、二甲基亚砜(DMSO)、γ-丁内酯(GBL)、六甲基磷酸三酰胺(HMPT)、四氢呋喃(THF)、甲基四氢呋喃、1,4-二恶烷及其混合物。
在一些实施方案中,本文所述的聚酰亚胺聚合物的重均分子量(Mw)为至少约5,000道尔顿(例如,至少约10,000道尔顿、至少约20,000道尔顿、至少约25,000道尔顿、至少约30,000道尔顿、至少约35,000道尔顿、至少约40,000道尔顿、或至少约45,000道尔顿)和/或至多约100,000道尔顿(例如,至多约90,000道尔顿、至多约80,000道尔顿、至多约70,000道尔顿、至多约65,000道尔顿、至多约60,000道尔顿、至多约55,000道尔顿、或至多约50,000道尔顿)。在一些实施方案中,完全酰亚胺化的聚酰亚胺聚合物的重均分子量(Mw)为约20,000道尔顿至约70,000道尔顿或约30,000道尔顿至约80,000道尔顿。重均分子量可通过凝胶渗透色谱法获得,并使用聚苯乙烯标准计算。
在一些实施方案中,聚酰亚胺(A)的量为形成介电膜的组合物的总重量的至少约3重量%(例如,至少约6重量%、至少约9重量%、至少约12重量%、或至少约15重量%)和/或至多约40重量%(例如,至多约35重量%、至多约30重量%、至多约25重量%、或至多约20重量%)。在一些实施方案中,形成介电膜的组合物中的聚酰亚胺(A)的量为组合物中的固体量的至少约10重量%(例如,至少约12.5重量%、至少约15重量%、至少约20重量%、或至少约25重量%)和/或至多约60重量%(例如,至多约55重量%、至多约50重量%、至多约45重量%、至多约40重量%、至多约35重量%、或至多约30重量%)。所述组合物中的固体量是指组合物的总重量减去组合物中溶剂的量(即,由组合物形成的固体介电膜的总重量)。
在一些实施方案中,本文所述的形成介电膜的组合物中的无机填料可包括无机颗粒。在一些实施方案中,无机颗粒选自由以下组成的组:二氧化硅、氧化铝、二氧化钛、氧化锆、氧化铪、CdSe、CdS、CdTe、CuO、氧化锌、氧化镧、氧化铌、氧化钨、氧化锶、钛酸钙、钛酸钠、硫酸钡、钛酸钡、锆酸钡和铌酸钾。优选地,无机填料为平均尺寸约0.1-2.0微米的颗粒形式。在一些实施方案中,填料是含有铁磁材料的无机颗粒。合适的铁磁材料包括元素金属(例如铁、镍和钴)或它们的氧化物、硫化物和羟基氧化物,以及金属间化合物例如Awaruite(Ni3Fe),Wairaruite(CoFe),Co17Sm2和Nd2Fe14B。
当无机颗粒是二氧化硅时,它可以是亲水的或疏水的。疏水性二氧化硅填料可以通过亲水性、气相二氧化硅的表面改性或通过表面改性的二氧化硅填料的直接形成来制备。表面改性的二氧化硅填料的直接形成通常通过官能硅烷的水解缩合来完成。可用于本发明的表面改性的二氧化硅填料可在其表面上具有反应性和/或无反应性的基团。可用于本发明的填料(例如,二氧化硅填料)具有至多约2微米(例如,至多约1.5微米、至多约1微米、至多约0.75微米、至多约0.5微米、至多约0.25微米、或至多约0.2微米)和/或至少约0.1微米(例如,至少约0.2微米、至少约0.3微米、至少约0.5微米、或至少约1微米)的粒度(例如,平均粒度)。填料尺寸分布可以是窄的(例如,基本上是单分散的)或宽的。所需的填料尺寸和分布可通过本领域技术人员已知的许多技术中的任何一种来实现,包括但不限于碾磨、研磨和过滤。在一些实施方案中,二氧化硅填料分散在有机溶剂中。溶剂中的分散可以通过本领域技术人员已知的各种方法完成,包括但不限于介质研磨和高剪切混合。用于二氧化硅填料分散的溶剂没有特别限制。优选的溶剂包括酯、醚、内酯、酮、酰胺和醇。更优选的溶剂包括GBL、环戊酮、环己酮、乳酸乙酯和正丁醇。
在一些实施方案中,本发明的形成介电膜的组合物中的填料(例如,二氧化硅填料)的量为组合物总重量的至少约2重量%(例如,至少约4重量%、至少约6重量%、至少约8重量%、或至少约10重量%)和/或至多约20重量%(例如,至多约18重量%、至多约15重量%、或至多约12重量%)。在一些实施方案中,本发明的形成介电膜的组合物中填料(例如,二氧化硅填料)的量为组合物中固体量的至少约5重量%(例如,至少约10重量%、至少约14重量%、至少约17重量%、或至少约20重量%)和/或至多约40重量%(例如,至多约35重量%、至多约30重量%、或至多约25重量%)。不希望受理论束缚,据信填料(例如二氧化硅填料)的存在能够降低形成介电膜的组合物的CTE。
用于本发明的含金属的(甲基)丙烯酸酯(MCA)通常与形成介电膜的组合物中的其它成分具有足够的相容性,并且在混合时易于分散或溶解在组合物中。MCA可以作为固体或溶液掺入到形成介电膜的组合物中。通常,含有MCA的组合物在25℃静置至少24小时后没有相分离(即,变得明显不均匀)。另外,由含MCA的组合物形成的介电膜通常明显透明且均匀。
用于本发明中的MCA的合适金属原子包括钛、锆、铪和锗。在一些实施方案中,MCA包括至少一个金属原子和至少一个(例如,一个、两个、三个或四个)(甲基)丙烯酸酯基团。优选的MCA含有与每个金属原子连接的三个或四个(甲基)丙烯酸酯基团。合适的MCA的实例包括但不限于四(甲基)丙烯酸钛、四(甲基)丙烯酸锆、或四(甲基)丙烯酸铪、钛丁氧基三(甲基)丙烯酸酯、钛二丁氧基二(甲基)丙烯酸酯、钛三丁氧基(甲基)丙烯酸酯、锆丁氧基三(甲基)丙烯酸酯、锆二丁氧基二(甲基)丙烯酸酯、锆三丁氧基(甲基)丙烯酸酯、铪丁氧基三(甲基)丙烯酸酯,铪二丁氧基二(甲基)丙烯酸酯、铪三丁氧基(甲基)丙烯酸酯、钛四(羧乙基(甲基)丙烯酸酯)、锆四(羧乙基(甲基)丙烯酸酯)、铪四(羧乙基(甲基)丙烯酸酯)、钛丁氧基三(羧乙基(甲基)丙烯酸酯)、钛二丁氧基二(羧乙基(甲基)丙烯酸酯)、钛三丁氧基(羧乙基(甲基)丙烯酸酯)、锆丁氧基三(羧乙基(甲基)丙烯酸酯)、锆二丁氧基二(羧乙基(甲基)丙烯酸酯)、锆三丁氧基(羧乙基(甲基)丙烯酸酯)、铪丁氧基三(羧乙基(甲基)丙烯酸酯)、铪二丁氧基二(羧乙基(甲基)丙烯酸酯)或铪三丁氧基(羧乙基(甲基)丙烯酸酯)。通常,MCA的(甲基)丙烯酸酯基团具有足够的反应性,以使MCA能够参与由自由基引起的含MCA的膜的交联或聚合,所述自由基可以由形成介电膜的组合物中存在的一种或多种催化剂产生。交联或聚合可在形成介电膜的组合物中的至少两种MCA之间或至少一种MCA和至少一种非MCA交联剂中发生。在一些实施方案中,MCA是交联剂(例如,当MCA包含两个或更多个(甲基)丙烯酸酯基团时)。在一些实施方案中,MCA是适于聚合或起链终止剂作用的单体(例如,当MCA仅包含一个(甲基)丙烯酸酯基团时)。在一些实施方案中,MCA在由本文所述组合物形成的交联介电膜中不交联(例如,当MCA仅包含一个(甲基)丙烯酸酯基团时)。
在一些实施方案中,形成介电膜的组合物中的MCA的量为组合物的总重量的至少约0.5重量%(例如,至少约1重量%、至少约2重量%、至少约3重量%、至少约4重量%、或至少约5重量%)和/或至多约20重量%(例如,至多约18重量%、至多约16重量%、至多约14重量%、至多约12重量%、或至多约10重量%)。在一些实施方案中,形成介电膜的组合物中的MCA的量为组合物中的固体量的至少约1重量%(例如,至少约2重量%、至少约4重量%、至少约6重量%、至少约8重量%、或至少约10重量%)和/或至多约25重量%(例如,至多约20重量%、至多约18重量%、至多约16重量%、至多约14重量%、或至多约12重量%)。
令人惊讶地观察到,在形成介电膜的组合物中存在至少一种MCA和至少一种无机填料可以大大降低CTE,同时保持所得膜的光学透明度和韧性。
在一些实施方案中,MCA和无机填料的总量为形成介电膜的组合物中固体量的至少约20重量%(例如,至少约25重量%、至少约30重量%、至少约35重量%)和/或至多约50重量%(例如,至多约45重量%、至多约40重量%、至多约35重量%、或至多约30重量%)。不希望受理论束缚,据信,当MCA和无机填料的总量在上述范围内时,由此形成的介电膜可以有效地实现相对低的CTE和相对高的光学透明度。不希望受理论束缚,据信如果MCA和无机填料的总量小于组合物中固体量的20%,则所得的介电膜可能不具有所需的CTE(例如,CTE低于50ppm/℃)。此外,不希望受理论束缚,如果MCA和无机填料的总量大于组合物中固体量的50%,则所得介电膜可能是脆性的。
在一些实施方案中,形成介电膜的组合物中无机填料和MCA之间的重量比为至少约1:1(例如,至少约1.5:1、至少约2:1、至少约2.5:1)和/或至多约5:1(例如,至多约4.5:1、至多约4:1、至多约3.5:1、或至多约3:1)。不希望受理论束缚,据信当无机填料和MCA之间的重量比在上述范围内时,由此形成的介电膜可以有效地实现相对低的CTE和相对高的光学透明度。
在一些实施方案中,本发明的形成介电膜的组合物可包含至少一种催化剂(例如,引发剂)。当暴露于热源和/或辐射源时,催化剂能够引发交联或聚合反应。
在一些实施方案中,使用的催化剂是光引发剂,其中光引发剂是当暴露于高能辐射时能够产生自由基的化合物。高能辐射的非限制性实例包括电子束、紫外光和X射线。不希望受理论束缚,据信光引发剂引发交联或聚合反应,其涉及MCA化合物的(甲基)丙烯酸酯基团和/或组合物中存在的能够进行交联或聚合反应的其他实体。此类实体的实例包括交联剂(例如,非MCA交联剂)和带有烯基和炔基官能团的聚酰亚胺。
光引发剂的具体实例包括但不限于1,8-辛二酮、1,8-双[9-(2-乙基己基)-6-硝基-9H-咔唑-3-基]-1,8-双(O-乙酰基肟)、2-羟基-2-甲基-1-苯基丙-1-酮、1-羟基环己基苯基酮(来自BASF的Irgacure 184)、1-羟基环己基苯基酮和二苯甲酮的混合物(来自BASF的Irgacure 500)、2,4,4-三甲基戊基氧化膦(来自BASF的Irgacure 1800、1850和1700)、2,2-二甲氧基-2-苯乙酮(来自BASF的Irgacure 651)、双(2,4,6-三甲基苯甲酰基)苯基氧化膦(来自BASF的Irgacure 819)、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉基丙烷-1-酮(来自BASF的Irgacure 907)、(2,4,6-三甲基苯甲酰基)二苯基氧化膦(来自BASF的LucerinTPO)、2-(苯甲酰氧基亚氨基)-1-[4-(苯硫基)苯基]-1-辛酮(来自BASF的Irgacure OXE-01)、1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]乙酮1-(O-乙酰基肟)(来自BASF的Irgacure OXE-2)、乙氧基(2,4,6-三甲基苯甲酰基)苯基氧化膦(来自BASF的Lucerin TPO-L)、氧化膦、羟基酮和二苯甲酮衍生物的混合物(来自Arkema的ESACURE KTO46)、2-羟基-2-甲基-1-苯基丙烷-1-酮(来自Merck的Darocur 1173)、2-(苯甲酰氧基亚氨基)-1-[4-(苯硫基)苯基]-1-辛酮(OXE-01,购自BASF)、1-(O-乙酰基肟)-1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]乙酮(OXE-02,购自BASF)、NCI-831(ADEKA Corp.)、NCI-930(ADEKA Corp.)、N-1919(ADEKA Corp.)、二苯甲酮、2-氯噻吨酮、2-甲基噻吨酮、2-异丙基噻吨酮、苯并二甲基缩酮、1,1,1-三氯苯乙酮、二乙氧基苯乙酮、间氯苯乙酮、苯丙酮、蒽醌、二苯并噻吩酮等。
非离子型光引发剂的具体实例包括(5-甲苯甲酰基磺酰氧基亚氨基-5H-噻吩-2-亚基)-2-甲基苯基-乙腈(来自BASF的Irgacure121)、对甲基苯磺酸苯甲酯、对甲苯磺酸苯偶姻、(对甲苯磺酰氧基)甲基苯偶姻、3-(对甲苯磺酰氧基)-2-羟基-2-苯基-1-苯基丙基醚、N-(对十二烷基苯磺酰氧基)-1,8-萘二甲酰亚胺、N-(苯基-磺酰氧基)-1,8-萘酰亚胺、双(环己基磺酰基)重氮甲烷、1-对甲苯磺酰基-1-环己基羰基重氮甲烷、对甲苯磺酸2-硝基苄酯、对甲苯磺酸2,6-二硝基苄酯、对三氟甲基苯磺酸2,4-二硝基苄酯等。
在一些实施方案中,光敏剂可用于形成介电膜的组合物,其中光敏剂可吸收193nm至405nm波长范围内的光。光敏剂的实例包括但不限于9-甲基蒽、蒽甲醇、苊烯、噻吨酮、甲基-2-萘基酮、4-乙酰基联苯和1,2-苯并芴。
在通过加热引发交联或聚合反应的实施方案中,所用催化剂是热引发剂,其中热引发剂是当暴露于约70℃至约250℃的温度时能够产生自由基的化合物。不希望受理论束缚,据信热引发剂引发交联或聚合反应,其涉及MCA化合物的(甲基)丙烯酸酯基团和/或组合物中存在的能够进行交联或聚合反应的其他实体。此类实体的实例包括交联剂(例如,非MCA交联剂)和带有烯基和炔基官能团的聚酰亚胺。
热引发剂的具体实例包括但不限于过氧化苯甲酰、过氧化环己酮、过氧化月桂酰、过氧化苯甲酸叔戊酯、叔丁基过氧化氢、二叔丁基过氧化氢、过氧化二异丙苯、氢过氧化枯烯、过氧化琥珀酸、二(正丙基)过氧二碳酸酯、2,2-偶氮二(异丁腈)、2,2-偶氮二(2,4-二甲基戊腈)、2,2-偶氮二异丁酸二甲酯、4,4-偶氮二(4-氰基戊酸)、偶氮二环己腈、2,2-偶氮双(2-甲基丁腈)等。
在一些实施方案中,两种或更多种催化剂的组合可用于形成介电膜的组合物中。催化剂的组合可以是所有热引发剂、所有光引发剂或至少一种热引发剂和至少一种光引发剂的组合。
在一些实施方案中,形成介电膜的组合物中催化剂的量为组合物总重量的至少约0.25重量%(例如,至少约0.5重量%、至少约0.75重量%、至少约1.0重量%、或至少约1.5重量%)和/或至多约4.0重量%(例如,至多约3.5重量%、至多约3.0重量%、至多约2.5重量%、或至多约2.0重量%)。在一些实施方案中,形成介电膜的组合物中催化剂的量为组合物中的固体量的至少约0.5重量%(例如,至少约1.0重量%、至少约1.5重量%、至少约2.0重量%、或至少约2.5重量%)和/或至多约5.0重量%(例如,至多约4.5重量%、至多约4.0重量%、至多约3.5重量%、或至多约3.0重量%)。
本发明的形成介电膜的组合物可任选地含有至少一种有机溶剂。在一些实施方案中,有机溶剂是环境友好的并且可用于电子封装制造。在一些实施方案中,有机溶剂可具有至多约210℃的沸点(例如,至多约200℃、至多约190℃、至多约180℃、至多约170℃、至多约160℃、或至多约150℃),以确保干膜形成后的残留溶剂低于5%并且干燥膜的速度大于约2英尺/分钟(例如,约3英尺/分钟、约4英尺/分钟、约5英尺/分钟、或约6英尺/分钟)。在一些实施方案中,在形成膜的组合物中使用的无机颗粒可以容易地分散在有机溶剂中以形成均匀的膜。在一些实施方案中,均匀的膜不显示任何无机颗粒的附聚并且没有雾状物。在一些实施方案中,聚酰亚胺聚合物可具有在25℃在有机溶剂中至少约50mg/mL(例如,至少约100mg/mL或至少约200mg/mL)的溶解度。有机溶剂的实例包括但不限于内酯如γ-丁内酯、环酮如环戊酮和环己酮、线性酮如甲基乙基酮(MEK)、酯如乙酸正丁酯、酯醇如乳酸乙酯、醚醇如四氢糠醇、酰胺如N,N-二甲基乙酰胺、亚砜如二甲基亚砜(DMSO)、醚如四氢呋喃(THF)、吡咯烷酮如N-甲基吡咯烷酮、二醇酯如丙二醇甲醚醋酸酯。优选的溶剂包括γ-丁内酯、环戊酮、环己酮或其混合物。在一些实施方案中,有机溶剂可包括芳族溶剂,例如二甲苯、甲苯、乙苯、均三甲苯和苯甲醚。上述有机溶剂可以单独使用或组合使用,只要它完全溶解除了不溶性填料之外组合物的所有组分,浇铸良好的膜并且不干扰混合反应。
在一些实施方案中,形成介电膜的组合物中有机溶剂的量为形成介电膜的组合物的总重量的至少约35重量%(例如,至少约40重量%、至少约45重量%、至少约50重量%、至少约55重量%、至少约60重量%、或至少约65重量%)和/或至多约98重量%(例如,至多约95重量%、至多约90重量%、至多约85重量%、至多约80重量%、至多约75重量%或至多约70重量%)。
在一些实施方案中,本发明的形成介电膜的组合物还可包含至少一种交联剂(例如,非MCA交联剂)。在一些实施方案中,交联剂含有两个或更多个烯基或炔基。通常,交联剂能够在催化剂存在下进行交联或聚合反应。
在一些实施方案中,至少一种交联剂是至少一种氨基甲酸酯丙烯酸酯低聚物。术语“氨基甲酸酯丙烯酸酯低聚物”是指一类氨基甲酸酯(甲基)丙烯酸酯化合物,其含有氨基甲酸酯键并具有(甲基)丙烯酸酯(例如丙烯酸酯或甲基丙烯酸酯)官能团,例如氨基甲酸酯多(甲基)丙烯酸酯、多氨基甲酸酯(甲基)丙烯酸酯和多氨基甲酸酯多(甲基)丙烯酸酯。氨基甲酸酯(甲基)丙烯酸酯低聚物的类型已经由例如Coady等人的专利号US4,608,409和Chisholm等人的专利号US6,844,950的美国专利描述,其内容通过引用并入本文中。可用于本发明的氨基甲酸酯丙烯酸酯低聚物的具体实例包括但不限于CN9165US、CN9167US、CN972、CN9782、CN9783和CN992。这些和其它氨基甲酸酯丙烯酸酯低聚物可从Arkema(Sartomer)商购获得。
在一些实施方案中,交联剂含有至少两个(甲基)丙烯酸酯基团。在一些实施方案中,交联剂选自由以下组成的组:1,6-己二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、1,12-十二烷二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、环己烷二甲醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙氧基化(3)甘油三(甲基)丙烯酸酯、二乙烯基苯、乙氧基化双酚-A-双(甲基)丙烯酸酯、二乙二醇双(烯丙基碳酸酯)、三羟甲基丙烷三(甲基)丙烯酸酯、双三羟甲基丙烷四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五-/六-(甲基)丙烯酸酯、异氰脲酸酯三(甲基)丙烯酸酯、双(2-羟乙基)-异氰脲酸酯二(甲基)丙烯酸酯、1,3-丁二醇三(甲基)丙烯酸酯、1,4-丁二醇三(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、(甲基)丙烯酸酯改性脲醛树脂、(甲基)丙烯酸酯改性三聚氰胺甲醛树脂和(甲基)丙烯酸酯改性纤维素。
在一些实施方案中,形成介电膜的组合物中交联剂的量为组合物总重量的至少约2.5重量%(例如,至少约5重量%、至少约7.5重量%、至少约10重量%、至少约12.5重量%、或至少约15重量%)和/或至多约30重量%(例如,至多约27.5重量%、至多约25重量%、至多约22.5重量%、至多约20重量%、或至多约17.5重量%)。在一些实施方案中,形成介电膜的组合物中交联剂的量为组合物中的固体量的约5重量%(例如,至少约10重量%、至少约15重量%、至少约20重量%、至少约25重量%、或至少约30重量%)和/或至多约60重量%(例如,至多约55重量%、至多约50重量%、至多约45重量%、至多约40重量%、或至多约35重量%)。不希望受理论束缚,据信交联剂可改善由本文所述组合物形成的介电膜的机械性能和耐化学性。
本发明的形成介电膜的组合物可任选地包括一种或多种其他组分,例如助粘剂、填料、表面活性剂、增塑剂、着色剂和染料。
在一些实施方案中,本发明的形成介电膜的组合物还包含一种或多种助粘剂。合适的助粘剂描述于出版物“Silane Coupling Agent”EdwinP.Plueddemann,1982 PlenumPress,New York”。助粘剂的种类包括但不限于巯基烷氧基硅烷、氨基烷氧基硅烷、环氧烷氧基硅烷、缩水甘油氧基烷氧基硅烷、巯基硅烷、氰基硅烷和咪唑硅烷。在一些实施方案中,助粘剂包含烷氧基甲硅烷基和含有碳-碳多键的官能团,所述含有碳-碳多键的官能团选自取代或未取代的烯基和取代或未取代的炔基。
如果使用的话,形成介电膜的组合物中任选的助粘剂的量为组合物的总重量的至少约0.3重量%(例如,至少约0.5重量%、至少约0.7重量%、或至少约1重量%)和/或至多约4重量%(例如,至多约3重量%、至多约2重量%、或至多约1.5重量%)。在一些实施方案中,形成介电膜的组合物中任选的助粘剂的量为组合物中的固体量的至少约0.5重量%(例如,至少约1重量%、至少约2重量%、或至少约2.5重量%)和/或至多约8重量%(例如,至多约6重量%、至多约5重量%、至多约4重量%、或至多约3重量%)。
本发明的形成介电膜的组合物还可任选地含有一种或多种表面活性剂。如果使用表面活性剂,则表面活性剂的量为组合物的总重量的至少约0.001重量%(例如,至少约0.01重量%或至少约0.1重量%)和/或至多约2重量%(例如,至多约1重量%或至多约0.5重量%)。在一些实施方案中,表面活性剂的量为组合物中的固体量的至少约0.002重量%(例如,至少约0.02重量%或至少约0.2重量%)和/或至多约4重量%(例如,至多约1重量%或至多约0.5重量%)。合适的表面活性剂的实例包括但不限于JP-A-62-36663、JP-A-61-226746、JP-A-61-226745、JP-A-62-170950、JP-A-63-34540、JP-A-7-230165、JP-A-8-62834、JP-A-9-54432和JP-A-9-5988中描述的表面活性剂。
本发明的形成介电膜的组合物可任选地含有一种或多种增塑剂。如果使用,任选的增塑剂的量为组合物的总重量的至少约1重量%(例如,至少约2重量%或至少约3重量%)和/或至多约10重量%(例如,至多约7.5重量%至多约5重量%)。在一些实施方案中,任选的增塑剂的量为组合物中的固体量的至少约2重量%(例如,至少约4重量%或至少约6重量%)和/或至多约20重量%(例如,至多约14重量%或至多约10%重量)。
本发明的形成介电膜的组合物可任选地含有一种或多种铜钝化剂。铜钝化剂的实例包括三唑化合物、咪唑化合物和四唑化合物。三唑化合物可包括三唑、苯并三唑、取代的三唑和取代的苯并三唑。取代基的实例包括C1-C8烷基、氨基、硫醇、巯基、亚氨基、羧基和硝基。三唑化合物的具体实例包括苯并三唑、1,2,4-三唑、1,2,3-三唑、甲苯基三唑、5-甲基-1,2,4-三唑、5-苯基-苯并三唑、5-硝基-苯并三唑、3-氨基-5-巯基-1,2,4-三唑、1-氨基-1,2,4-三唑、羟基苯并三唑、2-(5-氨基-戊基)-苯并三唑、1-氨基-1,2,3-三唑、1-氨基-5-甲基-1,2,3-三唑、3-氨基-1,2,4-三唑、3-巯基-1,2,4-三唑、3-异丙基-1,2,4-三唑、5-苯硫基-苯并三唑、卤代-苯并三唑(卤代=F、Cl、Br或I)、萘并三唑等。咪唑化合物的实例包括但不限于2-烷基-4-甲基咪唑、2-苯基-4-烷基咪唑、2-甲基-4(5)-硝基咪唑、5-甲基-4-硝基咪唑、4-咪唑甲醇盐酸盐、2-巯基-1-甲基咪唑。四唑化合物的实例包括但不限于1-H-四唑、5-甲基-1H-四唑、5-苯基-1H-四唑、5-氨基-1H-四唑、1-苯基-5-巯基-1H-四唑、5,5'-双-1H-四唑、1-甲基-5-乙基四唑、1-甲基-5-巯基四唑、1-羧甲基-5-巯基四唑等。
在一些实施方案中,如果使用的话,任选的铜钝化剂的量为形成介电膜的组合物的总重量的至少约0.01重量%(例如至少约0.05重量%、至少约0.1重量%或至少约0.5重量%)和/或至多约2重量%(例如,至多约1.5重量%或至多约1重量%)。在一些实施方案中,任选的铜钝化剂的量为组合物中的固体量的至少约0.02重量%(例如,至少约0.1重量%、至少约0.2重量%或至少约1重量%)和/或至多约4重量%(例如,至多约3重量%或至多约2重量%)。
在一些实施方案中,聚酰亚胺可以由不包括结构(1)的硅氧烷二胺的二胺制备:
其中R1和R2各自独立地为二价脂族或芳族基团(例如,C1-6二价脂族基团或C6-12二价芳族基团),R3、R4、R5和R6各自独立地为一价脂族或芳族基团(例如,C1-6一价脂族基团或C6-12一价芳族基团),m为1-100的一整数。
结构(III)的硅氧烷二胺单体的实例包括但不限于:
在一些实施方案中,本发明的形成介电膜的组合物可以具体地不包括以下溶剂的一种或多种(如果多于一种,则不包括其任何组合)。这些溶剂可选自由以下组成的组:线性酮,诸如甲乙酮(MEK);酯,诸如乙酸乙酯;酯醇,诸如乳酸乙酯;醚醇,诸如四氢糠醇;和二醇酯,诸如丙二醇甲醚醋酸酯(PGMEA)。
在一些实施方案中,本发明的形成介电膜的组合物可以具体地不包括下列助粘剂的一种或多种(如果多于一种,则不包括其任何组合)。这些助粘剂可选自由以下组成的组:含伯胺的助粘剂(诸如3-氨基丙基三乙氧基硅烷和间氨基苯基三乙氧基硅烷)、含仲胺的助粘剂(诸如N-环己基氨基三甲氧基硅烷)、含叔胺的助粘剂(诸如二乙氨基乙基三乙氧基硅烷)、含尿素的助粘剂(如脲基丙基三甲氧基硅烷)、含有酸酐的助粘剂(诸如3-(三乙氧基甲硅烷基)丙基琥珀酸酐)、含环氧树脂的助粘剂(诸如2-(3,4-环氧环己基)乙基三乙氧基硅烷)、含有异氰酸酯的助粘剂(诸如3-异氰酸基丙基三乙氧基硅烷)和含硫的助粘剂(诸如3-巯基丙基三甲氧基硅烷)。
在一些实施方案中,本发明的形成介电膜的组合物可以具体地不包含一种或多种(如果多于一种,则不包含其任何组合)添加剂组分。这些组分可选自由以下组成的组:非聚酰亚胺聚合物、非交联非聚酰亚胺聚合物、表面活性剂、增塑剂、着色剂、染料、水、氧清除剂、季铵氢氧化物、胺、碱金属和碱土金属碱(如NaOH、KOH、LiOH、氢氧化镁和氢氧化钙)、含氟单体化合物、氧化剂(如过氧化物、过氧化氢、硝酸铁、碘酸钾、高锰酸钾、硝酸、亚氯酸铵、氯酸铵、碘酸铵、过硼酸铵、高氯酸铵、高碘酸铵、过硫酸铵、亚氯酸四甲基铵、氯酸四甲基铵、碘酸四甲基铵、过硼酸四甲基铵、高氯酸四甲基铵、高碘酸四甲基铵、过硫酸四甲基铵、过氧化氢脲和过氧乙酸)、磨料、硅酸盐、腐蚀抑制剂(例如、非唑类腐蚀抑制剂)、胍、胍盐、无机酸(如磺酸、硫酸、亚硫酸、亚硝酸、硝酸、亚磷酸和磷酸)、有机酸(如羟基羧酸和羧酸和多元羧酸)、吡咯烷酮、聚乙烯吡咯烷酮和金属卤化物。
在一些实施方案中,本发明的特征在于由本文所述的形成介电膜的组合物形成的介电膜。在一些实施方案中,当介电膜尚未通过暴露于辐射源或热源而交联时,介电膜可包括:a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种含金属的(甲基)丙烯酸酯;和d)至少一种催化剂。在一些实施方案中,介电膜还可包含至少一种交联剂(例如以上关于形成介电膜的组合物所述的那些)。
在一些实施方案中,当通过暴露于辐射源或热源使介电膜交联时,介电膜可包含:a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;和c)至少一种交联的含金属的(甲基)丙烯酸酯。在一些实施方案中,交联的介电膜中的至少一种完全酰亚胺化的聚酰亚胺聚合物可以是未交联的。在一些实施方案中,交联的介电膜中的至少一种完全酰亚胺化的聚酰亚胺聚合物可以是交联的(例如,与其自身或与含金属的(甲基)丙烯酸酯交联)。在这样的实施方案中,形成介电膜的组合物中的至少一种完全酰亚胺化的聚酰亚胺聚合物可含有一个或多个双键或三键(例如封端基团)。
在一些实施方案中,本发明的特征在于一种制备干膜结构的方法。该方法包括:
(A)用本文所述的形成介电膜的组合物(例如,含有a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种含金属的(甲基)丙烯酸酯;d)至少一种催化剂;e)任选地至少一种溶剂,和f)任选地至少一种交联剂的组合物)涂覆载体衬底(例如,包括至少一个塑料膜的衬底)以形成涂覆组合物;
(B)干燥涂覆组合物以形成介电膜;以及
(C)任选地将保护层施加到介电膜上。
在一些实施方案中,载体衬底是单层或多层塑料膜,其可包括一种或多种聚合物(例如,聚对苯二甲酸乙二醇酯)。在一些实施方案中,载体衬底具有优异的光学透明性,并且对用于在聚合物层中形成浮雕图案的光化辐射基本上是透明的。载体衬底的厚度优选在至少约10μm(例如,至少约15μm、至少约20μm、至少约30μm、至少约40μm、至少约50μm或至少约60μm)至至多约150μm(例如,至多约140μm、至多约120μm、至多约100μm、至多约90μm、至多约80μm、或至多约70μm)的范围内。
在一些实施方案中,保护层衬底是单层或多层膜,可包括一种或多种聚合物(例如,聚乙烯或聚丙烯)。载体衬底和保护层的实例已在例如公开号2016/0313642的美国申请中描述,其内容通过引用并入本文中。在一些实施方案中,干膜结构中的介电膜尚未暴露于用于例如形成交联膜的辐射源或热源。
在一些实施方案中,干膜的介电膜可以作为能自己立住的介电膜从载体层分离。能自己立住的介电膜是可以在不使用任何支撑层(例如载体层)的情况下保持其物理完整性的膜。在一些实施方案中,能自己立住的介电膜可包括(例如,在交联之前):a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种含金属的(甲基)丙烯酸酯(例如,未交联的含金属的(甲基)丙烯酸酯);和d)至少一种能够引发聚合反应的催化剂。在一些实施例中,能自己立住的介电膜可以暴露于辐射源或热源以形成交联的能自己立住的介电膜。在一些实施方案中,交联的能自己立住的介电膜可包括:a)至少一种完全酰亚胺化的聚酰亚胺聚合物;b)至少一种无机填料;c)至少一种交联的含金属的(甲基)丙烯酸酯。在一些实施例中,在预层压介电膜之后,可以使用真空层压机用平面压缩方法或热辊压缩方法在约50℃至约140℃将能自己立住的介电膜(交联或未交联)层压到衬底(例如,半导体衬底)上。
在一些实施例中,在预层压干膜结构的介电膜之后,使用真空层压机用平面压缩法或热辊压缩法在约50℃至约140℃将干膜结构的介电膜层压到衬底(例如,半导体衬底)上。当采用热辊层压时,可以将干膜结构放入热辊层压机中,可选的保护层可以从介电膜/载体衬底上剥离,并且可以使用辊以及热和压力使介电膜接触衬底并层压到衬底上,以形成包含衬底、介电膜和载体衬底的制品。然后可以将介电膜暴露于辐射源或热源(例如,通过载体衬底)以形成交联的介电膜。在一些实施例中,可以在将介电膜暴露于辐射源或热源之前移除载体衬底。
在一些实施方案中,通过包含以下步骤的方法由本发明的形成介电膜的组合物制备交联的介电膜:
a)将本文所述的形成介电膜的组合物涂覆在衬底(例如半导体衬底)上以形成介电膜;
b)任选地在约50℃至约150℃的温度烘烤膜约20秒至约240秒;以及
c)将介电膜暴露于辐射源或热源。
用于制备介电膜的涂覆方法包括但不限于旋涂(spin coating)、喷涂、辊涂、棒涂、旋涂(rotation coating)、狭缝涂覆、压缩涂覆、幕式淋涂(curtain coating)、模涂(die coating)、线棒涂覆、刮刀涂覆和干膜的层压。半导体衬底可以具有圆形形状,例如晶圆,或者可以是面板。在一些实施例中,半导体衬底可以是硅衬底、铜衬底、铝衬底、氧化硅衬底、氮化硅衬底、玻璃衬底、有机衬底、覆铜层压板或介电材料衬底。
本发明的介电膜的膜厚度没有特别限制。在一些实施方案中,介电膜的膜厚度为至少约3微米(例如,至少约4微米、至少约5微米、至少约7微米、至少约10微米、至少约15微米、至少约20微米、或至少约25微米)和/或至多约100微米(例如,至多约80微米、至多约60微米、至多约50微米、至多约40微米、或在约30微米)。
在一些实施方案中,介电膜可具有相对小的膜厚度(例如,至多约5微米、至多约4微米、或至多约3微米)。
然后可以将介电膜暴露于辐射源或热源(例如,形成交联膜)。用于辐射曝光的辐射的非限制性实例包括电子束、紫外光和X射线,优选紫外光。通常,可以使用低压汞灯、高压汞灯、超高压汞灯或卤素灯作为辐射源。曝光剂量没有特别限制,本领域技术人员可以容易地确定适当的量。在一些实施方案中,曝光剂量为至少约100mJ/cm2(例如,至少约250mJ/cm2或至少约500mJ/cm2)且至多约2,000mJ/cm2(例如,至多约1,500mJ/cm2或至多约1,000mJ/cm2)。在一个实施方案中,曝光剂量为250mJ/cm2至1000mJ/cm2。
如果介电膜暴露于热,则加热温度为至少约70℃(例如,至少约100℃、至少约130℃、或至少约150℃)和/或至多约250℃(例如,至多约220℃、至多约200℃、或至多约180℃)。加热时间为至少约10分钟(例如,至少约20分钟、至少约30分钟、至少约40分钟、或至少约50分钟)和/或至多约5小时(例如,至多约4小时、至多约3小时、至多约2小时或至多约1小时)。在一个实施方案中,加热温度为150℃至250℃持续30分钟至3小时。
本发明的介电膜的显著特征是其令人惊讶的高光学透明度和低CTE。在一些实施方案中,本发明的介电膜具有在50-150℃温度范围内测量的至少约50%(例如,至少约55%、至少约60%、至少约65%、至少约70%、至少约75%、至少约80%、至少约85%、至少约88%、至少约90%、至少约92%、或至少约94%)的光学透明度。在450nm至700nm波长范围测量光学透明度。在一些实施方案中,本发明的介电膜具有在50-150℃的温度范围内测量的至多约50ppm/℃的CTE(例如,至多约45ppm/℃、至多约40ppm/℃、至多约35ppm/℃、或至多约30ppm/℃)和/或至少约10ppm/℃(例如,至少约15ppm/℃、至少约20ppm/℃、或至少25ppm/℃)的CTE。
在一些实施方案中,本发明的特征在于一种用于产生图案化的介电膜的方法,包括以下步骤:
a)在衬底上涂覆本发明的形成介电膜的组合物,以形成介电膜;
b)将介电膜暴露于辐射源或热源;以及
c)图案化该膜以形成具有开口的图案化的介电膜。
步骤a)和b)可以与前面讨论的相同。
在一些实施方案中,制备图案化的介电膜的方法包括通过光刻工艺将介电膜转换为图案化的介电膜。在这种情况下,转换可以包括使用图案化的掩模将介电膜暴露于高能辐射(例如上面描述的)。在介电膜暴露于高能辐射之后,该方法可以进一步包括使暴露的介电膜显影以形成图案化的介电膜。
在暴露之后,可以在至少约50℃(例如,至少约55℃、至少约60℃、或至少约65℃)至至多约100℃(例如,至多约95℃、或至多约90℃、至多约85℃、至多约80℃、至多约75℃、或至多约70℃)热处理介电膜至少约60秒(例如,至少约65秒、或至少约70秒)至至多约240秒(例如,至多约180秒、至多约120秒或至多约90秒)。通常使用热板或烘箱完成热处理。
在曝光和热处理之后,可以通过使用显影剂使介电膜显影以除去未曝光部分。可以通过例如浸渍法或喷雾法进行显影。在显影之后,可以在层压衬底上的介电膜中产生微孔和细线。
在一些实施方案中,可以通过使用有机显影剂来使介电膜显影。此类显影剂的实例可包括但不限于γ-丁内酯(GBL)、二甲基亚砜(DMSO)、N,N-二乙基乙酰胺、甲基乙基酮(MEK)、甲基异丁基酮(MIBK)、2-庚酮、环戊酮(CP)、环己酮、乙酸正丁酯(nBA)、丙二醇甲醚乙酸酯(PGMEA)、丙二醇甲醚(PGME)、乳酸乙酯(EL)、乳酸丙酯、3-甲基-3-甲氧基丁醇、四氢化萘、异佛尔酮、乙二醇单丁醚、二乙二醇单乙醚、二乙二醇单乙醚乙酸酯、二乙二醇二甲醚、二乙二醇甲乙醚、三乙二醇单乙醚、二丙二醇单甲醚、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、丙二酸二乙酯、乙二醇、1,4:3,6-二脱水山梨糖醇、异山梨醇二甲醚、1,4:3,6-二脱水山梨醇2,5-二乙基醚(2,5-二乙基异山梨醇)及其混合物。优选的显影剂是γ-丁内酯(GBL)、环戊酮(CP)、环己酮、乳酸乙酯(EL)、乙酸正丁酯(nBA)和二甲基亚砜(DMSO)。更优选的显影剂是γ-丁内酯(GBL)、环戊酮(CP)和环己酮。这些显影剂可单独使用或两种或多种组合使用,以优化对于特定组合物和光刻工艺的图像质量。
在一些实施方案中,可以通过使用含水显影剂来使介电膜显影。当显影剂是水溶液时,它优选含有一种或多种含水碱。合适的碱的实例包括但不限于无机碱(例如氢氧化钾、氢氧化钠)、伯胺(例如乙胺、正丙胺)、仲胺(例如二乙胺、二正丙胺)、叔胺(例如,三乙胺)、醇胺(例如,三乙醇胺)、季铵氢氧化物(例如,氢氧化四甲基铵或氢氧化四乙基铵)、以及它们的混合物。所用碱的浓度将根据例如所用聚合物的碱溶解度而变化。最优选的含水显影剂是含有四甲基氢氧化铵(TMAH)的显影剂。合适的TMAH浓度范围为约1%至约5%。
在一些实施方案中,在通过有机显影剂显影之后,可以使用有机清洗溶剂进行任选的清洗处理。本领域技术人员将知道哪种清洗方法适合于给定的应用。有机清洗溶剂的合适实例包括但不限于醇,例如异丙醇、甲基异丁基甲醇(MIBC)、丙二醇单甲醚(PGME)、戊醇;酯,例如乙酸正丁酯(nBA)、乳酸乙酯(EL)和丙二醇单甲醚乙酸酯(PGMEA);酮,例如甲乙酮;及其混合物。可以使用清洗溶剂进行清洗处理以除去残留物。
在一些实施方案中,在显影步骤或任选的清洗处理步骤之后,可以在至少约120℃(例如,至少约130℃、至少约140℃,至少约150℃,至少约160℃,至少约170℃,或至少约180℃)至至多约250℃(例如,至多约240℃、至多约230℃、至多约220℃、至多约210℃、至多约200℃或至多约190℃)进行任选的烘烤步骤(例如,显影后烘烤)。烘烤时间为至少约5分钟(例如,至少约10分钟、至少约20分钟、至少约30分钟、至少约40分钟、至少约50分钟、或至少约60分钟)和/或至多约5小时(例如,至多约4小时、至多约3小时、至多约2小时、或至多约1.5小时)。该烘烤步骤可以从剩余的介电膜中除去残留的溶剂,并且可以进一步交联剩余的介电膜。显影后烘烤可以在空气中进行,或者优选在氮气覆盖下进行,并且可以通过任何合适的加热装置进行。
在一些实施例中,制备图案化介电膜的工艺包括通过激光烧蚀技术将介电膜转换为图案化的介电膜。使用准分子激光束的直接激光烧蚀工艺通常是干燥的、一步材料去除以在介电膜中形成开口(或图案)。在一些实施例中,激光的波长为351nm或更小(例如,351nm、308nm、248nm或193nm)。合适的激光烧蚀工艺的实例包括但不限于专利号US7,598,167、US6,667,551和US6,114,240的美国专利中描述的方法,其内容通过引用并入本文中。使用常规介电膜的激光烧蚀工艺产生大量碎屑。去除这种烧蚀碎屑通常需要通过化学和/或等离子体处理进行额外的清洁工艺步骤,这增加了该工艺的复杂性和成本。本发明的介电膜的优点在于,当通过激光烧蚀工艺图案化介电膜时,形成很少碎屑或没有形成碎屑,这导致较少的工艺复杂性和较低的成本。
在一些实施方案中,图案化的介电膜的最小特征的纵横比(即,高度与宽度的比率)为至多约3/1(例如,至多约2/1、至多约1/1、至多约1/2、或至多约1/3)和/或至少约1/25(例如,至少约1/20、至少约1/15、至少约1/10和至少约1/5)。
在一些实施例中,图案化的介电膜的最小特征的纵横比为至少约1/2(例如,至少约1/1、至少约2/1或至少约3/1)。
通常,上述方法可用于形成要在半导体器件中使用的制品。这种制品的实例包括半导体衬底、用于电子器件的柔性膜、线隔离、线涂层、线漆或着墨衬底。由这种制品制成的半导体器件的实例可以包括集成电路、发光二极管、太阳能电池和晶体管。
在一些实施方案中,本发明的特征在于三维物体,包含通过本文所述的方法形成的至少一个图案化的膜。在一些实施方案中,三维物体可包括至少两个堆叠体(例如,至少三个堆叠体)中的图案化的膜。
在一些实施方案中,上述方法产生包括电子衬底和层压到电子衬底上的图案化的介电膜层(例如,包含浮雕图案)的制品,其中图案化的介电膜层包括至少一种聚酰亚胺聚合物。在初始介电膜厚度为5微米或更小的实施方案中,由此形成的图案化的介电膜层可具有至多约5微米(例如,至多约4微米或至多约3微米)的膜厚度并且包括具有至多约3微米(例如,至多约2微米)的特征尺寸(例如,宽度)的至少一种元件。
在本文引用的所有出版物(例如,专利、专利申请公开和文章)的内容通过引用整体并入本文。
提供以下实施例以更清楚地说明本发明的原理和实践。应该理解的是,本发明不限于所描述的示例。
实施例
合成例1(P-1)
6FDA/DAPI聚酰亚胺的制备
在25℃将固体4,4'-(六氟异亚丙基)双(邻苯二甲酸酐)(6FDA)(2.370kg,5.33mol)加入到NMP(9.86kg)中的1-(4-氨基苯基)-1,3,3-三甲基茚满-5胺(也称为4,4'-[1,4-亚苯基-双(1-甲基亚乙基)]二苯胺(DAPI))(1.473kg,5.51mol)的溶液中。将反应温度升至40℃并使混合物反应6小时。然后,加入乙酸酐(1.125kg)和吡啶(0.219kg),将反应温度升至100℃并允许反应进行12小时。
将上述反应混合物冷却至室温并转移至配备有机械搅拌器的较大容器中。将反应溶液用乙酸乙酯稀释,并用水洗涤1小时。停止搅拌后,使混合物不受干扰地静置。一旦发生相分离,就除去水相。用乙酸乙酯和丙酮的混合物稀释有机相,并用水洗涤两次。所有洗涤中使用的有机溶剂(乙酸乙酯和丙酮)和水的量示于表1中。
表1
洗涤1 | 洗涤2 | 洗涤3 | |
乙酸乙酯(kg) | 20.5 | 4.1 | 4.1 |
丙酮(kg) | --- | 2.3 | 2.3 |
水(kg) | 22.0 | 26.0 | 26.0 |
向洗涤的有机相中加入环戊酮(10.5kg),通过真空蒸馏浓缩溶液,得到聚合物溶液P-1。最终聚合物的固含量%为32.96%,通过GPC测得的重均分子量(Mw)为49,200道尔顿。
调配物实施例1-8和对比调配物实施例1-2
根据表2制备调配物实施例1-8和对比调配物实施例1-2(FE-1至FE-8和CFE-1至CFE-2)。通过机械搅拌将调配物组分混合16-24小时。
表2
1CN992(Sartomer)
2二氧化硅来自Evonik,具有0.2微米的中等尺寸
3钛羧酸乙酯(Purelight Labs)
4NCI-831(Adeka Corp.)
5甲基丙烯酰氧基丙基三甲氧基硅烷(Gelest)
方法实施例1-8和对比方法实施例1-2
通过在聚对苯二甲酸乙二醇酯(PET)衬底上棒涂各组合物并在90℃干燥10分钟来制备基于FE-1至FE-8和CFE-1至CFE-2的能自己立住的干膜(SSDF)。使用i线曝光以500mJ/cm2曝光该膜。获得名义上膜厚度为20微米的干膜。将所得膜从PET上剥离,形成能自己立住的干膜。将这些能自己立住的干膜置于Kapton片上并在真空下在170℃烘烤2小时。使用Q400 TMA热机械分析仪(TMA)测量能自己立住的干膜的CTE值,该分析仪被设计为用于精确测量安装在探针上的能自己立住的干膜随着它在程序温度范围内被加热时尺寸上的微小变化。在拉伸模式下测量膜纵向的CTE。使用JDC精密样品切割器制备宽度为3mm的能自己立住的干膜样品。使用长度为16mm的样品架安装样品并将该样品置于TMA膜膨胀探针上。加热能自己立住的干膜并使用TA软件计算CTE。表3显示了能自己立住的干膜的组成和测量的CTE值。
表3
1CN992(Sartomer)
2钛羧酸乙酯(Purelight Labs)
当与方法实施例1-6(表3)比较时,对比方法实施例1证明了使用MCA降低能自己立住的膜的CTE的重要性。具体地,表3显示,即使具有28重量%的二氧化硅,当膜中不存在MCA时,对比方法实施例1中的能自己立住的干膜的CTE当在50℃至150℃范围测量时高达155ppm/℃。令人惊奇的是,在方法实施例1-6中的能自己立住的干膜中存在MCA使CTE降低至51ppm/℃或更低。
当与方法实施例1-6(表3)比较时,方法实施例7证明了总二氧化硅和MCA负载降低能自己立住的干膜的CTE的效果。方法实施例7中的膜包含总量为18重量%的二氧化硅和MCA(即10重量%二氧化硅和8重量%MCA)。测试结果表明该膜显示出在50℃至150℃范围内62ppm/℃的CTE。而方法实施例1-6中的膜包含总量为21-40重量%的二氧化硅和MCA。测试结果表明,这些膜的CTE为51ppm/℃或更低。
当与方法实施例1-6(表3)比较时,对比方法实施例2证明了使用二氧化硅与MCA组合以降低能自己立住的干膜的CTE的重要性。具体地,表3显示,即使具有15重量%的MCA,当膜中不存在二氧化硅时,对比方法实施例2中的能自己立住的干膜的CTE当在50℃至150℃范围内测量时为83ppm/℃。令人惊奇的是,在方法实施例1-6的能自己立住的膜中存在二氧化硅和MCA使CTE降低至51ppm/℃或更低。
当填料(如二氧化硅)和MCA的总量超过能自己立住的膜的总重量的50重量%时,方法实施例8表明所得膜变得半透明和易碎。结果,无法测量其CTE。因此,认为通过仅增加填料(例如,二氧化硅)的量不能实现上述方法实施例1-6中的低CTE,适当量的填料(例如,二氧化硅)和MCA的组合对于实现低CTE、透明和坚韧的能自己立住的干膜至关重要。
介电常数测量实施例1
通过在聚对苯二甲酸乙二醇酯(PET)衬底上棒涂组合物FE-1并在90℃干燥10分钟来制备能自己立住的干膜。获得膜厚度为25微米的干膜。将得到的干膜在105℃的干燥室中烘烤2小时。使用分体式圆柱谐振器法(IPC-TM-650,测试编号2-5-5-13)测量干膜的两个堆叠体的介电常数和损耗角正切,如表4所示。
表4
在表4中,Udk是介电常数测量的不确定性,Udf是损耗角正切测量的不确定性。表4中的结果表明,由FE-1制备的干膜对半导体封装应用表现出可接受的介电性能。
调配物实施例9
调配物实施例9(FE-9)通过使用以下制备:13.00g聚合物(Poly-1)、27.36g环戊酮、31.20g环己酮、1.73g正丁醇、0.65g甲基丙烯酰氧基丙基三甲氧基硅烷、0.39g NCI-831、2.60g钛丙烯酸羧乙酯、7.80g表面处理过的二氧化硅、13g四甘醇二丙烯酸酯(SR268)、1.46g三羟甲基丙烷三丙烯酸酯(SR 351LV)、0.78g环戊酮中0.05%的Polyfox 6320溶液和0.03g对苯醌。在机械搅拌24小时后,将调配物用于以下测试。
光刻方法实施例1
将光敏FE-9旋涂在硅晶圆上,并使用热板在70℃烘烤180秒,以形成厚度约为15微米的涂层。用宽波段UV曝光工具(Carl Süss MA-56)通过具有所需曝光图案的掩模对光敏聚酰亚胺膜进行曝光。曝光后,将曝光的膜在50℃加热3分钟。
在曝光后烘烤之后,通过使用环戊酮作为显影剂(2×75秒显影)除去未曝光部分,然后用PGMEA清洗显影的膜15秒以形成图案。实现了在250mJ/cm2的感光速度下20微米的分辨率。膜中的图案化特征表现出15/20或0.75的纵横比。
激光烧蚀方法实施例1
将FE-6(表2)旋涂在硅晶圆上,并使用热板在95℃烘烤10分钟,以形成厚度为约10.50微米的涂层。然后用500mJ/cm2的宽波段UV曝光工具(Carl Süss MA-56)对膜进行泛光曝光。通过使用XeCl激光器在308nm的波长以100Hz的频率激光烧蚀该膜。获得8微米的分辨率,并且在900mJ/cm2下获得1.258nm/脉冲的蚀刻速率。膜中的图案化特征表现出10/8或1.25的纵横比。
光学透明度测量实施例1
将FE-6(表2)旋涂在厚度为3.0μm的透明4英寸玻璃晶片上,并在95℃软烘烤180秒。通过使用CARY 400 Conc紫外-可见分光光度计在450nm至700nm波长范围内测量该能自己立住的干膜的吸光度。该膜的透明度在700nm处为98.8%,在600nm处为98.1%,在500nm处为92.3%,在400nm处为89.4%。换句话说,由FE-6形成的膜在整个可见光谱上表现出优异的透明度。
吸光度测量实施例2
将FE-6(表2)旋涂在厚度为3.0μm的透明4英寸玻璃晶片上,并在95℃软烘烤180秒。通过使用CARY 400 Conc紫外-可见分光光度计在300至405nm波长范围内测量该能自己立住的干膜的吸光度。该膜的吸光度在308nm处为0.248μm-1,在355nm处为0.094μm-1,在365nm处为0.094μm-1,在405nm处为0.048μm-1。换句话说,由FE-6形成的膜在测试的UV光谱上表现出相对低的吸光度。
干膜实施例DF-1
使用来自Fujifilm USA(Greenwood,SC)的反向微棒涂覆机以2英尺/分钟(61厘米/分钟)的线速度以及60微米微细间隙将FE-1(表2)的光敏溶液施加到宽度为16.2英寸、厚度为35微米、用作载体衬底的聚对苯二甲酸乙二醇酯(PET)膜(TA 30,由Toray PlasticsAmerica,Inc制造)上,并在194°F干燥,得到厚度约为37.0微米的光敏聚合物层。在该聚合物层上,通过辊压缩法将宽度为16英寸、厚度为30微米的双轴取向聚丙烯膜(BOPP,由ImpexGlobal,Houston,TX制造)铺在光敏聚合物层上,以用作保护层。由此形成的干膜(DF-1)包含载体衬底、聚合物层和保护层。
干膜的层压(实施例L1)
在通过剥离除去保护层之后,将干膜结构DF-1(6“×6”)的光敏聚合物层置于4英寸Wafernet铜涂覆晶圆上。通过真空层压(0.2-0.4托)20秒将聚合物层成功地层压到Cu涂覆晶圆上,然后经受40psi的压力和0.2-0.4托的真空180秒。层压温度为90℃。使用由OPTEK,NJ制造的DPL-24A差压层压机完成层压过程。
调配物实施例10
调配物实施例10(FE-10)通过使用以下制备:26.00g聚合物(Poly-1)、46.88g环戊酮、80.00g环己酮、0.78g 3-(三乙氧基甲硅烷基)丙基琥珀酸酐、1.30g 1-(O-乙酰基肟)-1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]乙酮(OXE-02,购自BASF)、6.20g锆丙烯酸羧乙酯、10.50g具有0.5微米的中等尺寸的氧化铝、13g四乙二醇二甲基丙烯酸酯(SR 209,购自Sartomer)、16.99克CN992(购自Sartomer)、0.78克环戊酮中的0.05%Polyfox 6320溶液和0.06g对苯醌。在机械搅拌24小时后,使用该调配物且无需过滤。
方法实施例9
通过在聚对苯二甲酸乙二醇酯(PET)衬底上棒涂并在95℃干燥8分钟来制备基于FE-10的能自己立住的干膜(SSDF)。使用i线曝光将膜暴露在500mJ/cm2下。获得干膜。将所得膜从PET上剥离,形成能自己立住的干膜。
调配物实施例11
调配物实施例11(FE-11)通过使用以下制备:26.00g聚合物(Poly-1)、46.88g环戊酮、80.00g环己酮、0.78gγ-羟基丙基三甲氧基硅烷、1.30g 2-(苯甲酰氧基亚氨基)-1-[4-(苯硫基)苯基]-1-辛酮(OXE-01,购自BASF)、7.00g四(甲基)丙烯酸铪、10.50g具有0.4微米的中等尺寸的二氧化钛、15g三乙二醇二甲基丙烯酸酯(SR 205,购自Sartomer)、18.00g二季戊四醇五丙烯酸酯CN992、0.78g环戊酮中的0.05%的Polyfox 6320溶液和0.06g对苯醌。在机械搅拌36小时后,使用该调配物且无需过滤。
方法实施例10
通过在聚对苯二甲酸乙二醇酯(PET)衬底上棒涂并在85℃干燥12分钟来制备基于FE-11的能自己立住的干膜(SSDF)。使用i线曝光将膜暴露在600mJ/cm2下。获得干膜。将所得膜从PET上剥离,形成能自己立住的干膜。
调配物实施例12
调配物实施例12(FE-12)通过使用以下制备:13.00g聚合物(Poly-1)、23.44g环戊酮、39.00g环己酮、0.39g甲基丙烯酰基氧基甲基三乙氧基硅烷、0.8g过氧化苯甲酰、4.00g钛丁氧基三(甲基)丙烯酸酯、5.00g具有0.6微米的中等尺寸的氧化铌、7.0g三甘醇二丙烯酸酯、8.00g季戊四醇二丙烯酸酯、0.4g环戊酮中0.05%的Polyfox 6320溶液和0.03g对苯醌。在机械搅拌30小时后,使用该调配物且无需过滤。
方法实施例11
通过在聚对苯二甲酸乙二醇酯(PET)衬底上棒涂并在90℃干燥12分钟来制备基于FE-12的能自己立住的干膜(SSDF)。使用i线曝光将膜暴露在550mJ/cm2下。获得干膜。将所得膜从PET上剥离,形成能自己立住的干膜。
Claims (36)
1.一种形成介电膜的组合物,包括:
a)至少一种完全酰亚胺化的聚酰亚胺聚合物;
b)至少一种无机填料;
c)至少一种含金属的(甲基)丙烯酸酯;和
d)至少一种能够引发聚合反应的催化剂。
2.根据权利要求1所述的组合物,其中,所述至少一种无机填料包括无机颗粒,所述无机颗粒选自由以下组成的组:二氧化硅、氧化铝、二氧化钛、氧化锆、氧化铪、CdSe、CdS、CdTe、CuO、氧化锌、氧化镧、氧化铌、氧化钨、氧化锶、钛酸钙、钛酸钠、硫酸钡、钛酸钡、锆酸钡和铌酸钾。
3.根据权利要求2所述的组合物,其中,所述无机颗粒具有约0.1微米至约2微米的粒度。
4.根据权利要求1所述的组合物,其中,所述至少一种无机填料的量为所述组合物的约2重量%至约20重量%。
5.根据权利要求1所述的组合物,其中,所述至少一种含金属的(甲基)丙烯酸酯的金属原子选自由钛、锆、铪和锗组成的组。
6.根据权利要求1所述的组合物,其中,所述至少一种含金属的(甲基)丙烯酸酯包含至少一个金属原子和至少一个(甲基)丙烯酸酯基团。
7.根据权利要求1所述的组合物,其中,所述至少一种含金属的(甲基)丙烯酸酯包括四(甲基)丙烯酸钛、四(甲基)丙烯酸锆、四(甲基)丙烯酸铪、钛丁氧基三(甲基)丙烯酸酯、钛二丁氧基二(甲基)丙烯酸酯、钛三丁氧基(甲基)丙烯酸酯、锆丁氧基三(甲基)丙烯酸酯、锆二丁氧基二(甲基)丙烯酸酯、锆三丁氧基(甲基)丙烯酸酯、铪丁氧基三(甲基)丙烯酸酯、铪二丁氧基二(甲基)丙烯酸酯、铪三丁氧基(甲基)丙烯酸酯、钛四(羧乙基(甲基)丙烯酸酯)、锆四(羧乙基(甲基)丙烯酸酯)、铪四(羧乙基(甲基)丙烯酸酯)、钛丁氧基三(羧乙基(甲基)丙烯酸酯)、钛二丁氧基二(羧乙基(甲基)丙烯酸酯)、钛三丁氧基(羧乙基(甲基)丙烯酸酯)、锆丁氧基三(羧乙基(甲基)丙烯酸酯)、锆二丁氧基二(羧乙基(甲基)丙烯酸酯)、锆三丁氧基(羧乙基(甲基)丙烯酸酯)、铪丁氧基三(羧乙基(甲基)丙烯酸酯)、铪二丁氧基二(羧乙基(甲基)丙烯酸酯)或铪三丁氧基(羧乙基(甲基)丙烯酸酯)。
8.根据权利要求1所述的组合物,其中,所述至少一种含金属的(甲基)丙烯酸酯的量为所述组合物的约0.5重量%至约20重量%。
9.根据权利要求1所述的组合物,其中,至少一种无机填料和至少一种含金属的(甲基)丙烯酸酯的重量比为约1:1至约5:1。
10.根据权利要求1所述的组合物,其中,所述至少一种完全酰亚胺化的聚酰亚胺聚合物的量为所述组合物的约3重量%至约40重量%。
11.根据权利要求1所述的组合物,其中,所述至少一种催化剂包括光引发剂或热引发剂。
12.根据权利要求1所述的组合物,其中,所述至少一种催化剂的量为所述组合物的约0.25重量%至约4重量%。
13.根据权利要求1所述的组合物,还包含至少一种溶剂。
14.根据权利要求13所述的组合物,其中,所述至少一种溶剂的量为所述组合物的约35重量%至约98重量%。
15.根据权利要求1所述的组合物,还包含至少一种交联剂。
16.根据权利要求15所述的组合物,其中,所述交联剂包含两个或更多个烯基或炔基。
17.根据权利要求15所述的组合物,其中,所述交联剂是氨基甲酸酯(甲基)丙烯酸酯。
18.根据权利要求15所述的组合物,其中,所述交联剂的量为组合物的约2.5重量%至约30重量%。
19.一种介电膜,由权利要求1所述的组合物形成。
20.一种干膜,包括:
载体衬底;和
由所述载体衬底支撑的根据权利要求19所述的介电膜。
21.一种介电膜,包括:
a)至少一种完全酰亚胺化的聚酰亚胺聚合物;
b)至少一种无机填料;和
c)至少一种交联的含金属的(甲基)丙烯酸酯。
22.根据权利要求21所述的介电膜,其中,所述至少一种无机填料和所述至少一种交联的含金属的(甲基)丙烯酸酯的总量为所述膜的至少约20重量%。
23.根据权利要求22所述的介电膜,其中,所述至少一种无机填料和所述至少一种交联的含金属的(甲基)丙烯酸酯的总量为所述膜的至多约50重量%。
24.根据权利要求21所述的介电膜,其中,所述介电膜的CTE为至多约50ppm。
25.根据权利要求21所述的介电膜,其中,所述介电膜具有至少50%的光学透明度。
26.根据权利要求21所述的介电膜,其中,所述介电膜具有至多约50ppm的CTE和至少50%的光学透明度。
27.根据权利要求21所述的介电膜,其中,所述介电膜是图案化的膜。
28.根据权利要求21所述的介电膜,其中,所述介电膜是能自己立住的介电膜。
29.一种三维物体,包括权利要求21所述的介电膜。
30.一种半导体器件,包括权利要求29所述的三维物体。
31.根据权利要求30所述的半导体器件,其中所述半导体器件是集成电路、发光二极管、太阳能电池或晶体管。
32.一种制备图案化的介电膜的方法,包括以下步骤:
涂覆权利要求1所述的形成介电膜的组合物,以形成介电膜;以及
通过激光烧蚀工艺或光刻工艺图案化所述介电膜以形成图案化的介电膜。
33.一种三维物体,通过权利要求32所述的方法形成。
34.一种半导体器件,包括权利要求33所述的三维物体。
35.根据权利要求34所述的半导体器件,其中,所述半导体器件是集成电路、发光二极管、太阳能电池或晶体管。
36.一种能自己立住的介电膜,包括:
a)至少一种完全酰亚胺化的聚酰亚胺聚合物;
b)至少一种无机填料;
c)至少一种含金属的(甲基)丙烯酸酯;和
d)至少一种能够引发聚合反应的催化剂。
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EP3478777B1 (en) | 2020-11-18 |
EP3478482A4 (en) | 2019-07-17 |
JP2020533418A (ja) | 2020-11-19 |
TW201912677A (zh) | 2019-04-01 |
JP2020533419A (ja) | 2020-11-19 |
TW201912717A (zh) | 2019-04-01 |
KR20200053388A (ko) | 2020-05-18 |
CN109789644B (zh) | 2023-01-31 |
EP3478777A1 (en) | 2019-05-08 |
KR102494132B1 (ko) | 2023-01-31 |
JP7140686B2 (ja) | 2022-09-21 |
KR102456361B1 (ko) | 2022-10-19 |
US10563014B2 (en) | 2020-02-18 |
EP3478482B1 (en) | 2020-12-16 |
CN109790405B (zh) | 2022-07-15 |
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