CN109765758B - 含硅底层 - Google Patents
含硅底层 Download PDFInfo
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- CN109765758B CN109765758B CN201811294466.1A CN201811294466A CN109765758B CN 109765758 B CN109765758 B CN 109765758B CN 201811294466 A CN201811294466 A CN 201811294466A CN 109765758 B CN109765758 B CN 109765758B
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- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 81
- 239000010703 silicon Substances 0.000 title claims abstract description 81
- 239000000178 monomer Substances 0.000 claims abstract description 133
- 229920000642 polymer Polymers 0.000 claims abstract description 121
- 239000000203 mixture Substances 0.000 claims abstract description 90
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000000413 hydrolysate Substances 0.000 claims abstract description 5
- 150000003254 radicals Chemical class 0.000 claims description 62
- 239000000758 substrate Substances 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 238000000576 coating method Methods 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 239000011248 coating agent Substances 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 239000004971 Cross linker Substances 0.000 claims description 30
- 229920002120 photoresistant polymer Polymers 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229910001868 water Inorganic materials 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 4
- 229910003849 O-Si Inorganic materials 0.000 claims description 3
- 229910003872 O—Si Inorganic materials 0.000 claims description 3
- 229910018557 Si O Inorganic materials 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- -1 methoxysilyl groups Chemical group 0.000 description 99
- 239000010410 layer Substances 0.000 description 80
- 230000005494 condensation Effects 0.000 description 68
- 238000009833 condensation Methods 0.000 description 67
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 19
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 18
- 235000012431 wafers Nutrition 0.000 description 17
- 229920000620 organic polymer Polymers 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 150000002596 lactones Chemical group 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 10
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 239000003381 stabilizer Substances 0.000 description 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 239000003623 enhancer Substances 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- 150000001241 acetals Chemical group 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Chemical group 0.000 description 5
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 5
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000001020 plasma etching Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 235000010338 boric acid Nutrition 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- 229940018557 citraconic acid Drugs 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 210000002381 plasma Anatomy 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 2
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 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
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 2
- MIMUSZHMZBJBPO-UHFFFAOYSA-N 6-methoxy-8-nitroquinoline Chemical compound N1=CC=CC2=CC(OC)=CC([N+]([O-])=O)=C21 MIMUSZHMZBJBPO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Chemical group 0.000 description 2
- CNNYQGIUGXJEJJ-UHFFFAOYSA-N [Ge+2].C[O-].C[O-] Chemical compound [Ge+2].C[O-].C[O-] CNNYQGIUGXJEJJ-UHFFFAOYSA-N 0.000 description 2
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- WWIYWFVQZQOECA-UHFFFAOYSA-M tetramethylazanium;formate Chemical compound [O-]C=O.C[N+](C)(C)C WWIYWFVQZQOECA-UHFFFAOYSA-M 0.000 description 1
- MANNXDXMUHZSRP-UHFFFAOYSA-M tetramethylazanium;trifluoromethanesulfonate Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F MANNXDXMUHZSRP-UHFFFAOYSA-M 0.000 description 1
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- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
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- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
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- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
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- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- LIJDDOXRYWAXQG-UHFFFAOYSA-N tripentoxyalumane Chemical compound CCCCCO[Al](OCCCCC)OCCCCC LIJDDOXRYWAXQG-UHFFFAOYSA-N 0.000 description 1
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C09D143/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
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Abstract
提供采用可湿法剥离的底层组合物制造电子器件的方法,所述组合物包含以下各项的缩合物和/或水解物:包含作为聚合单元的一种或多种具有可缩合含硅部分的第一不饱和单体的聚合物,其中所述可缩合含硅部分悬垂于所述聚合物主链上;和一种或多种可缩合硅单体。
Description
本发明一般涉及底层和其使用方法,并且特别地涉及可湿法剥离的含硅底层和其在制造电子器件中的用途。
在常规的光刻工艺中,使用抗蚀图作为用于通过合适的蚀刻工艺如通过反应性离子蚀刻(RIE)将图案转印到衬底的掩模。所用抗蚀剂厚度的持续降低使抗蚀图不适合作为用于通过RIE工艺进行的图案转印的掩模。因此,已经研发出使用三个、四个或更多个层作为用于图案转印的掩模的替代性工艺。举例来说,在三层工艺中,将含硅抗反射层安置于底层/有机平坦化层与抗蚀剂层之间。由于这些层具有对含氟和氧的RIE化学物质的替代性选择性,所以此三层方案提供从含Si层顶部上的抗蚀图到底层下的衬底的高度选择性图案转印。
含硅底层对氧化物蚀刻化学物质的抗性允许此层起蚀刻掩模的作用。这类含硅底层由交联硅氧烷网构成。这些材料的抗蚀刻性由硅含量引起,并且更高的硅含量提供更好的抗蚀刻性。在目前的193nm光刻工艺中,这类含硅底层含有≥30%硅。这些材料中的这类高硅含量和硅氧烷网状结构使得移除其具有挑战性。含氟等离子体和氢氟酸(HF)都可以用于移除(或剥离)这些含硅层。然而,F-等离子体和HF都不仅会移除这些含硅材料,而且还会移除其它需要保留的材料如衬底。使用较高浓度如≥5wt%的氢氧化四甲基铵(TMAH)进行的湿法剥离可以用于移除这些含硅层中的至少一些,但是这些较高浓度的TMAH也有损坏衬底的风险。具有相对较低量(≤17%)的硅的含硅层有时可以使用“食人鱼酸(piranhaacid)”(浓H2SO4+30%H2O2)移除,但是这类方法还没有在具有更高硅含量的含硅材料的情况下实现商业上的成功。
Cao等人的《朗缪尔(Langmuir)》,2008,24,12771-12778已经报道通过自由基共聚合N-异丙基丙烯酰胺和甲基丙烯酸3-(三甲氧基硅烷基)丙酯,随后通过水解和缩合甲氧基硅烷基进行交联而形成的微凝胶。Cao等人描述了可以用于生物学应用的这类材料,所述应用如受控药物释放材料、生物传感器和组织工程。美国专利第9,120,952号采用类似于Cao等人参考文献中所公开的那些材料的材料以用于化学机械平面化处理。
美国专利第8,932,953B2号公开了用于形成含硅抗蚀剂底层的组合物,其中所述组合物含有组分(i)和组分(ii)的组合。在此专利中,组分(i)是有具有式(A)和式(B)的重复单元并且能够产生酚式羟基的聚合物,并且组分(ii)是通过水解-缩合含有至少一种或多种具有式(C)的可水解化合物和一种或多种具有式(D)的可水解化合物的混合物而获得的含硅化合物。
也就是说,美国专利第8,932,953号中的组合物是(i)具有悬垂的芳基部分和悬垂的Si-O键的特定有机聚合物和(ii)特定硅氧烷聚合物的组合,其中悬垂的芳基部分能够产生酚式羟基。这种组分(i)和(ii)的组合在美国专利第8,932,953号是必要的以便获得能够形成抗蚀剂底层膜的组合物,所述膜不仅具有优异的储存稳定性和粘附性,而且具有在正显影和负显影中都不变化的图案化特性。通过蚀刻工艺移除由此专利的组合物形成的膜。
底层领域的最新进展已经提供了可以通过湿法剥离技术容易地移除的特定含硅材料。一个缺点是这类含硅材料的底层易于在暴露于显影剂如氢氧化四甲基铵(TMAH)时遭受溶解或溶胀,这会导致形成于这些底层上的光致抗蚀剂图案的塌缩。仍然需要可以通过湿法剥离来移除并且对光致抗蚀剂图案塌缩更具有抗性的含硅底层。
本发明提供一种组合物,其包含:(a)一种或多种溶剂;(b)以下各项的缩合物和/或水解物:(i)一种或多种包含作为聚合单元的一种或多种具有可缩合含硅部分的第一不饱和单体的缩合含硅聚合物,其中可缩合含硅部分悬垂于聚合物主链上,和(ii)一种或多种可缩合硅单体;和(c)一种或多种不含Si-O键的交联剂。一种或多种交联剂能够与一种或多种含硅聚合物反应以形成共价键。
另外,本发明提供一种组合物,其包含:(a)一种或多种溶剂;(b)一种或多种有具有悬垂式结合的硅氧烷部分的有机聚合物链的缩合聚合物;和(c)一种或多种不含Si-O键的交联剂。
本发明进一步提供一种方法,其包含:(a)用上文所述的组合物中的任一种涂布衬底以形成涂层;(b)固化涂层以形成聚合物底层;(c)在聚合物底层上设置一层光致抗蚀剂;(d)以图案方式暴露光致抗蚀剂层以形成潜像;(e)显影潜像以形成其中具有浮雕图像的图案化光致抗蚀剂层;(f)将浮雕图像转印到衬底上;以及(g)通过湿法剥离来移除聚合物底层。本发明的聚合物底层是固化涂层,其包含作为聚合单元的一种或多种具有悬垂的硅氧烷部分的缩合聚合物和一种或多种不含Si-O键的交联剂。
更进一步地,本发明提供一种具有固化涂层的涂布衬底,所述固化涂层包含以下作为聚合单元:(a)以下各项的一种或多种缩合物和/或水解物:(i)一种或多种包含作为聚合单元的一种或多种具有可缩合含硅部分的第一不饱和单体的聚合物,其中可缩合含硅部分悬垂于聚合物主链上,和(ii)一种或多种可缩合硅单体;和(b)一种或多种不含Si-O键的交联剂。可替代地,本发明提供一种具有固化涂层的涂布衬底,所述固化涂层包含以下作为聚合单元:(a)一种或多种有具有悬垂式结合的硅氧烷部分的有机聚合物链的缩合聚合物;和(b)一种或多种不含Si-O键的交联剂。
应理解,当元素被称为与另一种元素“邻接”或“位于另一种元素上”时,其可以直接与另一种元素邻接或在另一种元素上,或二者之间可能存在插入元素。相反,当元素被称为与另一种元素“直接邻接”或“直接位于另一种元素上”时,不存在插入元素。应理解,尽管可以使用术语第一、第二、第三等来描述各种元素、组分、区域、层和/或部分,但是这些元素、组分、区域、层和/或部分不应受到这些术语的限制。这些术语仅用于将一种元素、组分、区域、层或部分与另一种元素、组分、区域、层或部分区分开。因此,在不脱离本发明的教示内容的情况下,下文论述的第一元素、组分、区域、层或部分可以被称为第二元素、组分、区域、层或部分。
如本说明书通篇所使用,除非上下文另外清楚地指示,否则以下缩写应具有以下含义:℃=摄氏度;g=克;mg=毫克;除非另外说明,否则ppm=百万分之重量份;μm=μ=微米;nm=纳米;L=升;mL=毫升;sec.=秒;min.=分钟;hr.=小时;以及Da=道尔顿。除非另外说明,否则所有量都是重量%并且所有比率都是摩尔比。所有数值范围都是包括性的并且可以按任何顺序组合,不同之处在于显然这类数值范围限制于总计100%。除非另外说明,否则“Wt%”是指以参考组合物的总重量计的重量%。冠词“一(a/an)”和“所述”是指单数和复数。如本文所使用的术语“和/或”包括一个或多个相关所列项目的任一个和所有组合。Mw是指重均分子量并且是通过使用聚苯乙烯标准物进行的凝胶渗透色谱法(GPC)测定的。所报道的pKa值是针对在25℃下的水溶液而言的,其可以例如通过如通过使用获自Sirius Analytical Instruments Ltd.的电位pH计进行的电位滴定(potentiometric titration)来实验性测定,或可以例如通过使用高级化学发展(Advanced Chemistry Development,ACD)实验室软件版本11.02来计算。除非另外说明,否则本文所报道的所有测量都在室温下进行。
如本说明书通篇所使用,术语“烷基”包括直链、支链和环烷基。术语“烷基”是指烷烃基团,并且包括烷烃单价基团、二价基团(亚烷基)和更高价基团。如果任何烷基或杂烷基未指明碳数目,则随后预期1-12个碳。术语“杂烷基”是指在基团内用一个或多个杂原子如氮、氧、硫、磷替换一个或多个碳原子的烷基,例如醚或硫醚。术语“烯基”是指烯烃基,并且包括烯烃单价基团、二价基团(亚烯基)和更高价基团。除非另外规定,否则“烯基”是指直链、支链和环状烯烃基团。术语“炔基”是指炔烃基,并且包括炔烃单价基团、二价基团和更高价基团。“炔基”是指直链和支链炔烃基团。如果任何烯基或炔基未指明碳数目,则随后预期2-12个碳。“有机残基”是指具有任何有机部分的基团,其除了碳和氢之外还可以任选地含有一个或多个杂原子,如氧、氮、硅、磷和卤素。有机残基可以含有一个或多个芳基或非芳基环或芳基和非芳基环。术语“烃基”是指具有任何烃的基团,其可以是脂肪族的、环状的、芳香族的或其组合,并且其除了碳和氢之外还可以任选地含有一个或多个杂原子,如氧、氮、硅、磷和卤素。烃基部分可以含有芳基或非芳基环或芳基和非芳基环,如一种或多种脂环或芳香环或脂环和芳香环。当烃基部分含有两个或更多个脂环时,这类脂环可以是独立的、稠合的或螺环的。脂环族烃基部分包括单脂环(如环戊基和环己基)以及双环(如二环戊二烯基、降冰片基和降冰片烯基)。当烃基部分含有两个或更多个芳香环时,这类环可以是独立的或稠合的。术语“固化”是指增加材料或组合物的分子量的任何方法,如聚合或缩合。“可固化的”是指能够在特定条件下固化的任何材料。术语“低聚物”是指二聚物、三聚物、四聚物以及其它能够进行进一步固化的相对低分子量材料。术语“聚合物”包括低聚物并且是指均聚物、共聚物、三元共聚物、四元共聚物等。如本文所使用的术语“(甲基)丙烯酸酯”和“(甲基)丙烯酸”分别指丙烯酸酯和甲基丙烯酸酯以及丙烯酸和甲基丙烯酸。
可用于本发明的组合物包含缩合含硅聚合物(本文中也称为“缩合聚合物”)。本发明组合物的涂层和由其形成的膜和底层是可湿法剥离的,并且与常规的可湿法剥离的含硅底层相比具有减少的图案塌缩。如本文所使用的术语“缩合聚合物”是指以下各项的缩合物和/或水解物:(i)一种或多种包含作为聚合单元的一种或多种具有可缩合含硅部分的第一不饱和单体的聚合物,其中可缩合含硅部分悬垂于聚合物主链上;和(ii)一种或多种可缩合硅单体,或可替代地,有具有悬垂式结合的硅氧烷部分的有机聚合物链的聚合物。如本文所使用的术语“缩合物和/或水解物”是指缩合产物、水解产物、水解-缩合产物或前述物质中的任一者的组合。术语“水解产物”是指部分水解或完全水解的产物。
本发明的缩合聚合物有具有悬垂式结合的硅氧烷部分的有机聚合物链(或主链)。有机聚合物链包含作为聚合单元(优选自由基聚合单元)的一种或多种具有可缩合含硅部分的第一不饱和单体。在聚合(优选自由基聚合)一种或多种第一不饱和单体和任何任选的第二不饱和单体时,所得有机聚合物链具有一种或多种悬垂的可缩合含硅部分。然后用一种或多种可缩合硅单体缩合和/或水解有机聚合物链的一种或多种悬垂的可缩合含硅部分以形成具有悬垂式结合的硅氧烷部分的本发明的缩合聚合物。如本文所使用的术语“硅氧烷部分”是指具有至少一个(Si-O)单元的部分。本发明的缩合聚合物可以任选地并且优选地具有包含作为聚合单元的一种或多种第二不饱和单体的聚合物链。第一不饱和单体和任何第二不饱和单体中的每一个优选包含一个可自由基聚合的双键或三键、更优选可自由基聚合的碳-碳双键或三键并且甚至更优选一个可自由基聚合的碳-碳双键。本发明的缩合聚合物优选不含有具有两个或更多个可自由基聚合的双键的单体的重复单元。
具有可缩合含硅部分的任何不饱和单体适合用作第一不饱和单体以形成本发明的缩合聚合物。可以使用一种或多种第一不饱和单体。优选是具有可缩合含硅部分的烯键式不饱和单体。优选第一不饱和单体是那些有具有以下式(1)的可缩合含硅部分的第一不饱和单体
-L-SiR1 bY1 3-b (1)
其中L是单键或二价连接基团;各R1独立地选自H、C1-10烷基、C2-20烯基、C5-20芳基和C6-20芳烷基;各Y1独立地选自卤素、C1-10烷氧基、C5-10芳氧基和C1-10羧基;b是0到2的整数;并且*表示与单体的连接点。L优选是二价连接基团。二价连接基团进一步优选包含选自氧和硅的一个或多个杂原子。合适的二价连接基团是具有1到20个碳原子和任选的一个或多个杂原子的有机基团。优选二价连接基团具有式-C(=O)-O-L1-,其中L1是单键或具有1到20个碳原子的有机基团。各R1优选独立地选自C1-10烷基、C2-20烯基、C5-20芳基和C6-20芳烷基。各Y1优选独立地选自卤素、C1-6烷氧基、C5-10芳氧基、C1-6羧基,并且更优选选自卤素、C1-6烷氧基和C1-6羧基。b优选是0或1,并且更优选b=0。
优选至少一种第一不饱和单体具有式(2)
其中L是单键或二价连接基团;各R1独立地选自H、C1-10烷基、C2-20烯基、C5-20芳基和C6-20芳烷基;R2和R3各自独立地选自H、C1-4烷基、C1-4卤代烷基、卤素、C5-20芳基、C6-20芳烷基和CN;R4选自H、C1-10烷基、C1-10卤代烷基、卤素、C5-20芳基、C6-20芳烷基和C(=O)R5;R5选自OR6和N(R7)2;R6选自H、C1-20烷基、C5-20芳基和C6-20芳烷基;各R7独立地选自H、C1-20烷基和C5-20芳基;各Y1独立地选自卤素、C1-10烷氧基、C5-10芳氧基、C1-10羧基;并且b是0到2的整数。L优选是二价连接基团。二价连接基团进一步优选包含选自氧和硅的一个或多个杂原子。合适的二价连接基团是具有1到20个碳原子和任选的一个或多个杂原子的有机基团。优选二价连接基团具有式-C(=O)-O-L1-,其中L1是单键或具有1到20个碳原子的有机基团。各R1优选独立地选自C1-10烷基、C2-20烯基、C5-20芳基和C6-20芳烷基。各Y1优选独立地选自卤素、C1-6烷氧基、C5-10芳氧基、C1-6羧基,并且更优选选自卤素、C1-6烷氧基和C1-6羧基。b优选是0或1,并且更优选b=0。各R2和R3优选独立地选自H、C1-4烷基、C1-4卤代烷基、C5-20芳基和C6-20芳烷基并且更优选选自H、C1-4烷基、C5-20芳基和C6-20芳烷基。各R2和R3又更优选独立地选自H、甲基、乙基、丙基、丁基、苯基、萘基、苄基和苯乙基。R4优选选自H、C1-10烷基、C1-10卤代烷基、C5-20芳基、C6-20芳烷基和C(=O)R5并且更优选选自H、C1-10烷基、C5-20芳基、C6-20芳烷基和C(=O)R5。R5优选是OR6。R6优选选自H、C1-10烷基、C5-10芳基和C6-15芳烷基。各R7优选独立地选自H、C1-10烷基和C6-20芳基。
合适的具有可缩合含硅部分的第一不饱和单体一般可以从多种来源如西格玛奥德里奇(Sigma-Aldrich)(密苏里州圣路易斯(St.Louis,Missouri))商购获得,或可以通过所属领域已知的方法来制备。这类单体可以原样使用或可以进行进一步纯化。示例性第一不饱和单体包括但不限于:烯丙基二甲氧基硅烷;烯丙基二氯硅烷;(甲基)丙烯酸(三甲氧基硅烷基)甲酯;(甲基)丙烯酸(三甲氧基硅烷基)乙酯;(甲基)丙烯酸(三甲氧基硅烷基)丙酯;(甲基)丙烯酸(三甲氧基硅烷基)丁酯;(甲基)丙烯酸(三乙氧基硅烷基)甲酯;(甲基)丙烯酸(三乙氧基硅烷基)乙酯;(甲基)丙烯酸(三乙氧基硅烷基)丙酯;(甲基)丙烯酸(三乙氧基硅烷基)丁酯;(甲基)丙烯酸(三氯硅烷基)甲酯;(甲基)丙烯酸(三氯硅烷基)乙酯;(甲基)丙烯酸(三氯硅烷基)丙酯;(甲基)丙烯酸(三氯硅烷基硅烷基)丁酯;(甲基)丙烯酸(甲基二甲氧基硅烷基)丙酯;乙烯基三乙酰氧基硅烷;(甲基)丙烯酸(三乙酰氧基硅烷基)丙酯;4-((三甲氧基硅烷基)丙基)苯乙烯;4-(三甲氧基硅烷基)苯乙烯;和乙烯基三甲氧基硅烷。
本发明的缩合聚合物的有机聚合物链优选进一步包含作为聚合单元的一种或多种第二不饱和单体,其中这类第二单体不含可缩合含硅部分。优选第二不饱和单体是烯键式不饱和单体。缩合聚合物优选具有进一步包含作为聚合单元的一种或多种具有以下式(3)的第二不饱和单体的有机聚合物链
其中Z选自具有1到30个碳原子的有机残基和水中pKa是-5到13的酸性质子、具有1到30个碳原子的有机残基和可酸分解的基团、具有发色团部分的有机残基、-C(=O)R13和CN;R10、R11和R12各自独立地选自H、C1-4烷基、C1-4卤代烷基、任选的经取代C5-20芳基、卤素、-C(=O)R14、C6-10芳基、CN;R13和R14各自独立地是OR15或N(R16)2;R15选自H、C1-20烷基、任选的经取代C5-30芳基、C6-20芳烷基和具有内酯部分的单价有机残基;并且各R16独立地选自H、C1-20烷基和C6-20芳基;其中Z和R10可以一起形成5到7元不饱和环。Z优选选自具有1到30个碳原子的有机残基和水中pKa是-5到13的酸性质子、具有1到30个碳原子的有机残基和可酸分解的基团、具有5到40个碳原子并具有发色团部分的有机残基以及-C(=O)R13。优选卤素是氟。R10、R11和R12优选各自独立地选自H、C1-4烷基、C1-4卤代烷基、卤素、-C(=O)R14和C6-10芳基并且更优选选自H、甲基、三氟甲基、氟和-C(=O)R14。R13和R14优选各是OR15。R15优选选自H、C1-20烷基、C6-20芳基,C6-20芳烷基和具有内酯部分的单价有机残基。如本文所使用的术语“芳基”是指芳香碳环和芳香杂环。“任选的经取代”芳基是指未经取代芳基和经取代芳基。“经取代芳基”是指其氢中的一个或多个经选自以下各者中的一个或多个取代基替换的任何芳基(或芳香族)部分:卤素、C1-6烷基、C1-6卤代烷基、C1-6烷氧基、C1-6-卤代烷氧基、苯基和苯氧基,优选选自卤素、C1-6烷基、C1-6烷氧基、苯基和苯氧基,并且更优选选自卤素、C1-6烷基和苯基。经取代芳基优选具有1到3个取代基并且更优选1或2个取代基。本发明的缩合聚合物优选具有进一步包含作为聚合单元的两种或更多种不同的具有式(4)的第二不饱和单体的有机聚合物链。具有式(1)+式(2)的第一不饱和单体的总摩尔数与任何任选的第二不饱和单体(如那些具有式(3)的第二不饱和单体)的总摩尔数的摩尔比是100:0到25:75,优选95:5到25:75,并且更优选75:25到25:75。
其中Z是具有1到30个碳原子的有机残基和水中pKa是-5到13的酸性质子的优选的具有式(3)的单体是那些具有以下式(3a)的单体
其中L1是单键或二价连接基团;AM是具有酸性质子并且水中pKa是-5到13的酸性部分;R10a、R11a和R12a各自独立地选自H、C1-4烷基、C1-4卤代烷基、任选的经取代C6-20芳基、卤素、-C(=O)R14a和CN;R14a选自OR15a和N(R16a)2;R15a选自H、C1-20烷基、C5-30芳基、C6-20芳烷基和具有内酯结构部分的单价有机残基;并且各R16a独立地选自H、C1-20烷基和C6-20芳基;其中L1、R10a、R11a和R12a中的任何两个可以与其所附接的碳一起形成5到7元环。R11a和R12a优选各自独立地选自H、C1-4烷基、C1-4卤代烷基、任选的经取代C6-20芳基和卤素,并且更优选选自H、C1-4烷基、C1-4卤代烷基和任选的经取代C6-10芳基。优选卤素是氟。R10a优选选自H、C1-10烷基、C1-10卤代烷基、任选的经取代C6-20芳基和-C(=O)R14a,并且更优选选自H、C1-10烷基、C1-10卤代烷基、任选的经取代C6-10芳基和-C(=O)R14a。R14a优选是OR15a。R15a优选是H、C1-20烷基、C5-30芳基和C6-20芳烷基,并且更优选H。各R16a优选选自H和C1-20烷基。L1优选是单共价键或具有1到20个碳原子和任选的一个或多个杂原子的二价有机基团,L1更优选是单共价键或具有1到20个碳原子和任选的一个或多个氧原子的二价烃基,并且L1再更优选选自单共价键、任选地包含一个或多个氧原子的二价C1-20-脂肪族部分、二价任选的经取代C6-20芳基部分和二价任选的经取代C7-20烷芳基部分。适用于AM的酸性部分具有选自以下各者中的一种或多种酸性基团:羧酸、磺酸、亚磺酸、氨基磺酸、膦酸、硼酸、芳香族羟基、羟基-六氟异丙基和其组合和酸盐;优选选自以下:羧酸、磺酸、膦酸、硼酸和其组合和酸盐;更优选选自以下:羧酸、磺酸、膦酸、硼酸和其组合;并且再更优选羧酸。AM再更优选选自-C(=O)-OH、-S(=O)2-OH、-P(=O)(OH)2、-B(OH)2、C6-20羟基芳基、巯基和C1-12羟基-全氟烷基,并且更优选选自-C(=O)-OH、-S(=O)2-OH、-P(=O)(OH)2、-B(OH)2、C6-20羟基芳基、巯基和C1-6羟基-全氟烷基(如六氟异丙醇基),并且更优选AM是-C(=O)-OH。L1和R10a或R11a和R12a可以与其所附接的碳一起形成5到7元不饱和环,优选5到6元不饱和环,并且更优选5到6元不饱和碳环。-R10a和R11a或R12a和L1可以与其所附接的碳一起形成5到7元饱和或不饱和环,优选5到6元饱和或不饱和环,并且更优选5到6元饱和或不饱和碳环。
其它优选的具有式(3)的第二不饱和单体是那些具有式以下(4)的第二不饱和单体
其中ADG是可酸分解的基团;R20选自H、C1-4烷基、C1-4卤代烷基、卤素和CN。R20优选选自H、C1-4烷基、C1-4氟烷基、氟和CN,更优选选自H、C1-4烷基、三氟甲基、氟和CN,甚至更优选选自H、甲基、三氟甲基、氟和CN,并且最优选R20是H或甲基。在式(4)中,ADG是具有2到30个碳原子的可酸分解的基团。如本文所使用的术语“可酸分解的基团”是指能够被酸分解以形成具有与可酸分解的基团相比增加的碱水溶解度的不同官能团的任何官能团。合适的可酸分解的基团包括但不限于其中C4-30烃基部分通过叔碳原子结合到氧原子的-O-C4-30烃基部分、具有酸酐部分的C2-30烃基部分、具有酰亚胺部分的C2-30烃基部分和包含缩醛官能团的C4-30有机残基。优选可酸分解的基团是其中C4-30烃基部分通过叔碳原子结合到氧原子的-O-C4-30烃基部分和包含缩醛官能团的C4-30有机残基,并且更优选是其中C4-20烃基部分通过叔碳原子结合到氧原子的-O-C4-30烃基部分和包含缩醛官能团的C4-20有机残基。如本文所使用的术语“缩醛”还涵盖“缩酮”、“半缩醛”和“半缩酮”。示例性可酸分解的基团包括但不限于-NR21R22、-OR23和-O-C(=O)-R24,其中R21和R22各自独立地选自H、C1-20烷基和C5-10芳基;R23是通过叔碳(即分别结合到三个其它碳的碳)结合到氧的C4-30有机残基或包含缩醛官能团的C4-30有机残基;并且R24选自H、C1-30烷基和C5-30芳基。R23优选具有4到20个碳原子。R23进一步优选是支链或环状部分。当R23含有环状部分时,这类环状部分通常在环中具有4到8个原子,并且优选在环中具有5或6个原子。R23可以任选地含有一个或多个杂原子,如氧。R23优选是任选地含有一个或多个杂原子的支链脂肪族或脂环族部分。
优选的具有式(4)的第二不饱和单体是那些具有以下式(4a)的第二不饱和单体
其中R23选自通过叔碳结合到氧的C4-20有机残基或包含缩醛官能团的C4-20有机残基;并且R20选自H、C1-4烷基、C1-4卤代烷基、卤素和CN。R23更优选具有以下式(5a)或(5b)中所示的结构
其中R24、R25和R26各自独立地是具有1到6个碳原子的有机残基;R24和R25可以一起形成4到8元环;L2是二价连接基团或单化学键;A表示缩醛官能团;并且*表示与酯氧的连接点。R24、R25和R26优选各自独立地选自C1-6烷基。当R24和R25一起形成4到8元环时,这种环可以是单环或可以是双环,并且可以任选地含有选自氧、硫和氮、优选氧和硫并且更优选氧的一个或多个杂原子。R24和R25优选可以一起形成5到8元环。合适的4到8元环包括但不限于环戊基、环己基、环庚基、环辛基、降冰片基和氧杂双环[2.2.1]庚基,优选环戊基、环己基、降冰片基和氧杂双环[2.2.1]庚基,并且更优选环戊基和环己基。合适的二价连接基团包括C1-10亚烷基并且优选C1-5亚烷基。缩醛官能团优选是5或6元环的环缩酮并且更优选由丙酮形成的环缩酮。R23的示例性部分包括但不限于:叔丁基;2,3-二甲基-2-丁基;2,3,3-三甲基-2-丁基;2-甲基-2-丁基;2-甲基-2-戊基;3-甲基-3-戊基;2,3,4-三甲基-3-戊基;2,2,3,4,4-五甲基-3-戊基;1-甲基-1-环戊基;1-乙基-1-环戊基;1,2-二甲基-1-环戊基;1,2,5-三甲基-1-环戊基;1,2,2-三甲基-环戊基;1,2,2,5-四甲基-1-环戊基;1,2,2,5,5-五甲基-1-环戊基;1-甲基-1-环己基;1-乙基-1-环己基;1,2-二甲基-1-环己基;1,2,6-三甲基-1-环己基;1,2,2,6-四甲基-1-环己基;1,2,2,6,6-五甲基-1-环己基;2,4,6-三甲基-4-庚基;3-甲基-3-降冰片基;3-乙基-3-降冰片基;6-甲基-2-氧杂双环[2.2.1]庚-6-基;和2-甲基-7-氧杂双环[2.2.1]庚-2-基。R5优选选自叔丁基;2,3-二甲基-2-丁基;2,3,3-三甲基-2-丁基;2-甲基-2-丁基;2-甲基-2-戊基;3-甲基-3-戊基;2,3,4-三甲基-3-戊基;2,2,3,4,4-五甲基-3-戊基;1-甲基-1-环戊基;1-乙基-1-环戊基;1,2-二甲基-1-环戊基;1,2,5-三甲基-1-环戊基;1,2,2-三甲基-环戊基;1,2,2,5-四甲基-1-环戊基;1,2,2,5,5-五甲基-1-环戊基;1-甲基-1-环己基;1-乙基-1-环己基;1,2-二甲基-1-环己基;1,2,6-三甲基-1-环己基;1,2,2,6-四甲基-1-环己基;1,2,2,6,6-五甲基-1-环己基;和2,4,6-三甲基-4-庚基。L2优选是二价连接基团。适用于L2的二价连接基团是具有1到20个原子并且更优选1到20个碳原子的有机残基。L2的二价连接基团可以任选地含有一个或多个杂原子,如氧、氮或其组合。合适的具有式(3)、(4)和(4a)的单体可以商购获得或通过所属领域已知的各种方法制备,如美国专利第6,136,501号、第6,379,861号;和第6,855,475号中所公开。
其它优选的具有式(3)的单体是那些具有以下式(6)的单体
其中R20a独立地选自H、C1-4烷基、C1-4卤代烷基、卤素和CN;R30是具有内酯部分的单价有机残基。在式(6)中,R30是包含内酯部分的C4-20单价有机残基。R30可以包含任何合适的内酯部分并且优选包含可以任选地经取代的5到7元内酯。内酯环上的合适的取代基是C1-10烷基部分。适用于R30的内酯部分是那些具有以下式(7)的内酯部分
其中E是5到7元环内酯;各R31独立地选自C1-10烷基;r是0到3的整数;Y是化学键或具有1到10个碳原子的二价连接残基;并且*表示与酯的氧原子的连接点。优选各R31独立地选自C1-6烷基并且更优选C1-4烷基。R31的实例是甲基、乙基、正丙基、异丙基、正丁基、仲丁基和异丁基。优选地,r=0或1。适用于Y的二价连接残基包括但不限于具有1到20个碳原子的二价有机残基。适用于Y的二价有机残基包括但不限于C1-20烃基部分、含C1-20杂原子的烃基部分和经取代C1-20烃基部分。术语“含C1-20杂原子的烃基部分”是指在烃基链内具有一个或多个杂原子如氮、氧、硫、磷的烃基部分。示例性杂原子包括但不限于-O-、-S-、-N(H)-、-N(C1-20烃基)-、-C(=O)-O-、-S(=O)-、-S(=O)2-、-C(=O)-NH-等。“经取代C1-20烃基部分”是指具有一个或多个氢被一个或多个取代基(如卤素、氰基、羟基、氨基、巯基等)替换的任何烃基部分。R30优选选自γ-丁内酯(GBLO)、β-丁内酯、γ-戊内酯、δ-戊内酯和己内酯,并且更优选R30是GBLO。具有式(6)的单体一般是可商购获得的或可以通过所属领域已知的方法制备。
在一个优选实施例中,本发明的缩合聚合物具有进一步包含作为聚合单元的一种或多种包含发色团的第二不饱和单体的聚合物链。合适的发色团是吸收目标波长的辐射的任何芳香族(芳基)部分。这类发色团是未经取代芳香族部分,如苯基、苄基、萘基、蒽基等,或可以经羟基、C1-10烷基、C2-10烯基、C2-10炔基和C5-30芳基中的一个或多个取代,优选是未经取代或经羟基取代的,并且更优选是未经取代的。缩合聚合物优选具有包含作为聚合单元的一种或多种具有发色团部分的具有式(3)的第二不饱和单体的有机聚合物链。优选发色团部分选自吡啶基、苯基、萘基、苊基、芴基、咔唑基、蒽基、菲基、芘基、蔻基、并四苯基、并五苯基、四苯基、苯并并四苯基、三亚苯基、苝基、苄基、苯乙基、甲苯基、二甲苯基、苯乙烯基、乙基萘基、乙基蒽基、二苯并噻吩基、噻吨酮基、吲哚基、吖啶基、联苯基、苯氧基-苯基、联萘基等,并且更优选苯基、萘基、蒽基、菲基、苄基等。用于本发明的发色团优选不含有具有结构*-C(Rx)2-O-Lg的取代基的芳香环,其中各Rx独立地是H或1到15个碳的烷基,其中各Rx可以一起形成脂肪环;Lg是H、具有1到10个碳的脂肪族单价烃或单价芳香族基团,并且*表示与芳香环的连接点。
示例性第二不饱和单体包括但不限于:乙烯基芳香族单体,如苯乙烯、α-甲基苯乙烯、β-甲基苯乙烯、芪、乙烯基亚萘、苊和乙烯基吡啶;经羟基取代的乙烯基芳香族单体,如羟基苯乙烯、邻香豆酸、间香豆酸、对香豆酸和羟基乙烯基亚萘;经羧基取代的乙烯基芳香族单体,如乙烯基苯甲酸;烯键式不饱和羧酸,如肉桂酸、马来酸、富马酸、巴豆酸、柠康酸、衣康酸、3-吡啶(甲基)丙烯酸、2-苯基(甲基)丙烯酸、(甲基)丙烯酸、2-亚甲基丙二酸、环戊烯羧酸、甲基环戊烯羧酸、环己烯羧酸和3-己烯-1,6-二羧酸;烯键式不饱和羧酸的羟基芳基酯,如(甲基)丙烯酸羟基苯酯、(甲基)丙烯酸羟基苄酯、(甲基)丙烯酸羟基萘酯和(甲基)丙烯酸羟基蒽酯;烯键式不饱和酸酐单体,如马来酸酐、柠康酸酐和衣康酸酐;烯键式不饱和酰亚胺单体,如马来酰亚胺;烯键式不饱和羧酸酯,如巴豆酸酯、衣康酸酯和(甲基)丙烯酸酯;(甲基)丙烯腈;(甲基)丙烯酰胺;等。合适的(甲基)丙烯酸酯单体包括但不限于(甲基)丙烯酸C7-10芳烷酯、(甲基)丙烯酸C1-10羟烷酯、(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸C1-10巯基烷酯和(甲基)丙烯酸C1-10烷酯。示例性(甲基)丙烯酸酯单体包括但不限于丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸羟乙酯、甲基丙烯酸羟乙酯、丙烯酸羟丙酯、甲基丙烯酸羟丙酯、甲基丙烯酸巯基丙酯、甲基丙烯酸缩水甘油酯、丙烯酸甲酯和甲基丙烯酸甲酯。
本发明的缩合聚合物优选具有有机聚合物链,所述有机聚合物链包含作为聚合单元的一种或多种具有式(2)的第一不饱和单体和一种或多种具有式(3)的第二不饱和单体,优选一种或多种具有式(2)的第一不饱和单体和两种或更多种具有式(3)的第二不饱和单体,甚至更优选一种或多种具有式(2)的第一不饱和单体和一种或多种具有式(6)的第二不饱和单体,并且再更优选一种或多种具有式(2)的第一不饱和单体、一种或多种具有式(6)的第二不饱和单体和一种或多种具有发色团部分的具有式(3)的第二种不饱和单体。当本发明的缩合聚合物的有机聚合物链包含一种或多种具有式(2)的第一不饱和单体和一种或多种具有式(3)的第二不饱和单体作为聚合单元时,这类单体以1:99到99:1具有式(2)的总单体与具有式(3)的总单体的摩尔比存在。具有式(2)的总单体与具有式(3)的总单体的摩尔比优选是95:5到5:95,更优选90:10到10:90,并且又更优选50:50到5:95。一种或多种任选的第二不饱和单体的用量可以是具有式(1)和(2)的总第一不饱和单体的摩尔量的0到3倍。当本发明的缩合聚合物包含相对较高百分比的含有发色团的第二不饱和单体作为聚合单元时,这类聚合物显示出降低的通过湿法剥离移除的能力。本发明的缩合聚合物优选包含0到50mol%含有发色团的第二不饱和单体作为聚合单元。
任何可缩合硅单体可以用于形成本发明的缩合聚合物,其条件是可缩合硅单体不同于具有可缩合硅部分的第一不饱和单体,并且可缩合硅单体与悬垂式结合到有机聚合物主链上的可缩合硅部分缩合。如本文所使用的术语“主链”是指主聚合物链。如本文所使用的“可缩合硅单体”是指具有一种或多种可缩合或可水解部分的硅单体。如本文所使用的“可缩合部分”或“可水解部分”是指能够在用于形成本发明的缩合聚合物的条件下进行缩合或水解的任何部分。示例性可缩合或可水解部分包括但不限于卤素、烷氧基、羧酸根、羟基、烯氧基、肟基、氨基等。合适的可缩合硅单体是那些具有以下式(8)的可缩合硅单体
Si(R50)p(X)4-p (8)
其中p是0到3的整数;各R50独立地选自C1-30烃基部分和经取代C1-30烃基部分;并且各X独立地选自卤素、C1-10烷氧基、-OH、-O-C(O)-R50和-(O-Si(R51)2)p2-X1;X1独立地选自卤素、C1-10烷氧基、-OH、-O-C(O)-R50;各R51独立地选自R50和X;并且p2是1到10的整数。p优选是0到2的整数,更优选0到1的整数并且又更优选p=0。X优选选自C1-10烷氧基、-OH、-O-C(O)-R50和-(O-Si(R51)2)p2-X1,并且更优选C1-10烷氧基和-OH。X1优选选自C1-10烷氧基和-OH。R50的经取代C1-30烃基部分是指其氢中的一个或多个经选自以下各者中的一个或多个取代基替换的的任何C1-30烃基部分:羟基、巯基、C1-20烷氧基、氨基、C1-20烷氨基、二C1-20烷氨基、氰基、卤素、环氧化物、-C(=O)O-R17、-C(=O)-N(R17)2和-C(=O)-O-C(=O)-R17,其中各R17选自H和C1-20烷基。R50的合适的C1-30烃基部分不限于C1-30烷基、C2-30烯基、C2-30炔基、C3-30环烷基和C6-30芳基,并且优选C1-20烷基、C2-20烯基、C2-20炔基、C3-20环烷基和C6-25芳基。硅单体通常是指与单体中的硅结合的可水解部分的数量。举例来说,“M单体”是指具有一个可水解部分的硅单体,如具有式(R50)3SiX的单体,“D单体”是指具有两个可水解部分的硅单体,如具有式(R50)2SiX2的单体,“T单体”是指具有三个可水解部分的硅单体,如具有式R50SiX3的单体,并且“Q单体”是指具有四个可水解部分的硅单体,如具有式SiX4的单体,其中每个单体中的X和R50如上所述。M、D、T和Q单体中的任一种可以单独使用,或前述单体中的任一种的混合物可以用于制备本发明的缩合聚合物。可缩合硅单体优选是一种或多种选自式(8a)、(8b)、(8c)和(8d)的单体
R50 3SiX (8a)
R50 2SiX2 (8b)
R50SiX3 (8c)
SiX4 (8d)
其中各X和R50如上针对式(8)所述。优选使用一种或多种Q单体即具有式(8d)的单体来制备本发明的缩合聚合物。这类可缩合硅单体一般可商购获得并且可以原样使用或可以进行进一步纯化。
可用于形成本发明的缩合聚合物的可缩合硅单体包括但不限于甲基三氯硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三乙酰氧基硅烷、乙基三氯硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、乙基三乙酰氧基硅烷、丙基三氯硅烷、丙基三甲氧基硅烷、丙基三乙氧基硅烷、丙基三乙酰氧基硅烷、羟丙基三氯硅烷、羟丙基三甲氧基硅烷、羟丙基三乙氧基硅烷、羟丙基三乙酰氧基硅烷、巯丙基三氯硅烷、巯丙基三甲氧基硅烷、巯丙基三乙氧基硅烷、巯丙基三乙酰氧基硅烷、环戊基三氯硅烷、环戊基三甲氧基硅烷、环戊基三乙氧基硅烷、环戊基三乙酰氧基硅烷、乙烯基三氯硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三乙酰氧基硅烷、苯基三氯硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、苯基三乙酰氧基硅烷、联苯基三氯硅烷、联苯基三甲氧基硅烷、联苯基三乙氧基硅烷、联苯基三乙酰氧基硅烷、二甲基二氯硅烷、二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、二甲基二乙酰氧基硅烷、二乙基二氯硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、二乙基二乙酰氧基硅烷、二苯基二氯硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、二苯基二乙酰氧基硅烷、甲基苯基二氯硅烷、甲基苯基二甲氧基硅烷、甲基苯基二乙氧基硅烷、甲基苯基二乙酰氧基硅烷、甲基乙烯基二氯硅烷、甲基乙烯基二甲氧基硅烷、甲基乙烯基二乙氧基硅烷、甲基乙烯基二乙酰氧基硅烷、二乙烯基二氯硅烷、二乙烯基二甲氧基硅烷、二乙烯基二乙氧基硅烷、二乙烯基二乙酰氧基硅烷、四氯硅烷、四甲氧基硅烷、四乙氧基硅烷和四乙酰氧基硅烷。优选可固化硅单体是四甲氧基硅烷和四乙氧基硅烷。
任选地,一种或多种蚀刻选择性改进剂也可以与一种或多种可缩合硅烷单体以及上述一种或多种聚合物缩合。合适的蚀刻选择性改进剂是那些具有以下式(9)的蚀刻选择性改进剂
G(X2)m4 (9)
其中G是元素周期表第13到15族的元素,不包括碳和硅;各X2独立地是卤素或OR52;各R52独立地是H或具有1到30个碳原子的有机基团;并且m4等于G的化合价。R52优选选自H、C1-10烷基、-C(O)-C1-10烷基和C6-10芳基,并且更优选选自H、C1-10烷基和-C(O)-C1-10烷基。G优选是选自以下各者中的元素:硼、铝、镓、钇、锗、钛、锆、铪、铋、锡、磷、钒、砷、锑、铌和钽,更优选选自硼、铝和锗,并且甚至更优选G是硼。具有式(9)的合适的化合物包括但不限于:硼酸三甲酯、硼酸三乙酯、硼酸三丙酯、硼酸三丁酯、硼酸三戊酯、硼酸三己酯、硼酸环戊酯、硼酸三环己酯、硼酸三烯丙酯、硼酸三苯酯、甲氧基乙醇硼、硼酸、三氧化二硼;甲醇铝、乙醇铝、丙醇铝、丁醇铝、戊醇铝、己醇铝、环戊醇铝、环己醇铝、烯丙醇铝、苯氧化铝、乙氧基乙醇铝、二丙氧基乙基-乙酰乙酸铝、二丁氧基乙基-乙酰乙酸铝、丙氧基-双-乙基-乙酰乙酸铝、丁氧基-双-乙基-乙酰乙酸铝、2,4-戊二酸铝、2,2,6,6-四甲基-3,5-庚二酸铝、甲醇锗、乙醇锗、丙醇锗、丁醇锗、戊醇锗、己醇锗、环戊醇锗、环己醇锗、烯丙醇锗、苯氧化锗和乙氧基乙醇锗。合适的蚀刻选择性改进剂是那些公开于美国专利第8,951,917中的蚀刻选择性改进剂。
本发明的缩合聚合物可以通过首先根据所属领域熟知的方法聚合一种或多种第一不饱和单体和任何任选的第二不饱和单体以形成未缩合聚合物来制备。本发明的单体优选通过自由基聚合来聚合,如那些用于制备(甲基)丙烯酸酯或苯乙烯聚合物的程序。可以使用广泛多种的自由基引发剂和条件中的任一种。制备所述聚合物的其它合适的聚合方法包括但不限于狄尔斯-阿尔德(Diels-Alder)、活性阴离子、缩合、交叉偶合、RAFT、ATRP等。接下来,使一种或多种未缩合聚合物经受使可缩合含硅部分缩合和/或水解的条件以形成本发明的缩合聚合物。这类缩合和/或水解条件是所属领域所熟知的,并且通常包括使一种或多种未缩合聚合物与含水酸或含水碱接触,并且优选含水酸。举例来说,可以使本发明的未缩合聚合物中的一种或多种与包含水、酸和任选的一种或多种有机溶剂的组合物接触并任选地进行加热。优选酸是无机酸,如HCl。本发明的缩合聚合物可以是部分缩合的或完全缩合的。“部分缩合的”是指存在于所述聚合物中的可缩合含硅部分的一部分经历缩合或水解反应。“完全缩合的”是指存在于所述聚合物中的可缩合含硅部分的全部都经历缩合或水解反应。本发明的未缩合聚合物的Mw通常是1000到10000Da、优选2000到8000Da并且更优选2500到6000Da。本发明的缩合聚合物的Mw通常是5000到75000Da、优选10000到50000Da并且更优选20000到40000Da。所属领域的技术人员应了解,缩合聚合物的混合物可适用于本发明的方法。
除了一种或多种上述缩合聚合物之外,本发明的组合物进一步包含一种或多种不含Si-O键的交联剂和一种或多种有机溶剂。任何交联剂可适用于本发明的涂料组合物,其条件是这类交联剂不含Si-O键并且具有多个能够在固化时与缩合聚合物反应的官能团。交联剂具有至少2个、优选至少3个并且更优选至少4个能够在固化时与缩合聚合物反应的官能团。能够在固化时与缩合聚合物反应的示例性官能团包括但不限于羟基、环氧基、氧杂环丁烷基团、硫醇基、内酯部分、异硫氰酸酯基、酸酐部分、马来酰亚胺部分、羧酸基团、炔基、卤素、醛基、烯丙基醚部分、亚胺基、不饱和酮部分等。优选官能团是羟基。交联剂优选具有至少2个相同官能团,更优选至少3个并且甚至更优选至少4个相同官能团。当官能团是羟基时,这种羟基可以是伯、仲或叔脂肪族羟基或芳香族羟基,并且更优选伯脂肪族羟基或仲脂肪族羟基。合适的交联剂可以是聚合的或非聚合的。可以用于本发明组合物的聚合交联剂可以是直链、支链、星形或枝状聚合物。当交联剂是聚合交联剂时,能够在固化时与缩合聚合物反应的官能团可以是位于聚合物链上或与悬垂式结合到聚合物链或其组合的末端基团。交联剂优选是非聚合脂肪族多元醇、具有悬垂式结合的羟基的聚合物或其混合物。作为上限,聚合交联剂的每个末端和/或每个重复单元可以具有能够在固化时与缩合聚合物反应的官能团。优选最多50mol%、更优选最多40mol%、甚至更优选最多30mol%并且又更优选10到30mol%的聚合交联剂的重复单元具有能够在固化时与缩合聚合物反应的官能团。可以用于本发明的优选聚合交联剂是羟基封端的环氧烷聚合物和具有悬垂式结合的羟基的聚合物。一般来说,缩合聚合物与交联剂的重量比是95:5到60:40,优选90:10到70:30,更优选85:15到70:30。
合适的非聚合交联剂具有至少2个、优选至少3个、更优选至少4个并且又更优选4到6个能够在固化时与缩合聚合物反应的官能团。一般来说,非聚合交联剂具有10个或更少的能够在固化期间与缩合聚合物反应的官能团。典型的非聚合交联剂是那些有具有2到40个、优选3到30个并且更优选4到30个碳原子的有机残基和2到10个羟基、优选2到8个羟基、更优选3到8个羟基并且又更优选4到6个羟基的非聚合交联剂。任选地,合适的非聚合交联剂可以是烷氧基化的,即其每个羟基可以与平均小于或等于2摩尔环氧烷(如环氧乙烷和/或环氧丙烷)反应。举例来说,如果非聚合交联剂具有4个羟基如季戊四醇,则其可以与最多8摩尔环氧烷(即每个羟基平均2摩尔环氧烷)反应。示例性非聚合交联剂是但不限于甘油、三羟甲基乙烷、三羟甲基丙烷、赤藻糖醇、季戊四醇、二季戊四醇、三季戊四醇、二(三羟甲基丙烷)、2-羟甲基-1,3-丙二醇、山梨糖醇、木糖醇、具有2到6摩尔环氧乙烷的乙氧基化甘油、具有2到6摩尔环氧丙烷的丙氧基化甘油、具有2到6摩尔环氧乙烷的乙氧基化三羟甲基乙烷、具有2到6摩尔环氧丙烷的丙氧基化三羟甲基乙烷、具有2到6摩尔环氧乙烷的乙氧基化三羟甲基丙烷、具有2到6摩尔环氧丙烷的丙氧基化三羟甲基丙烷、具有3到8摩尔环氧乙烷的乙氧基化赤藻糖醇、具有3到8摩尔环氧丙烷的丙氧基化赤藻糖醇、具有3到8摩尔环氧乙烷的乙氧基化季戊四醇、具有3到8摩尔环氧丙烷的丙氧基化季戊四醇、具有4到12摩尔环氧乙烷的乙氧基化二季戊四醇、具有4到12摩尔环氧丙烷的丙氧基化二季戊四醇、具有6到16摩尔环氧乙烷的乙氧基化三季戊四醇、具有6到16摩尔环氧丙烷的丙氧基化三季戊四醇、具有3到8摩尔环氧乙烷的乙氧基化二(三羟甲基丙烷)、具有3到8摩尔环氧丙烷的丙氧基化二(三羟甲基丙烷)和其混合物。优选非聚合交联剂是三羟甲基丙烷、赤藻糖醇、季戊四醇、二季戊四醇、三季戊四醇、2-羟甲基-1,3-丙二醇、具有2到6摩尔环氧乙烷的乙氧基化三羟甲基乙烷、具有2到6摩尔环氧丙烷的丙氧基化三羟甲基乙烷、具有2到6摩尔环氧乙烷的乙氧基化三羟甲基丙烷、具有2到6摩尔环氧丙烷的丙氧基化三羟甲基丙烷、具有3到8摩尔环氧乙烷的乙氧基化赤藻糖醇、具有3到8摩尔环氧丙烷的丙氧基化赤藻糖醇、具有3到8摩尔环氧乙烷的乙氧基化季戊四醇、具有3到8摩尔环氧丙烷的丙氧基化季戊四醇、具有4到12摩尔环氧乙烷的乙氧基化二季戊四醇、具有4到12摩尔环氧丙烷的丙氧基化二季戊四醇、具有6到16摩尔环氧乙烷的乙氧基化三季戊四醇、具有6到16摩尔环氧丙烷的丙氧基化三季戊四醇、具有3到8摩尔环氧乙烷的乙氧基化二(三羟甲基丙烷)、具有3到8摩尔环氧丙烷的丙氧基化二(三羟甲基丙烷)和其混合物。
可以用于本发明组合物的一类聚合交联剂是具有C2-4-亚烷氧基重复单元和2个或更多个末端羟基的环氧烷聚合物和具有悬垂式结合的羟基的聚合物。优选环氧烷聚合物具有3个或更多个末端羟基并且更优选4个或更多个末端羟基。示例性亚烷氧基重复单元是亚乙氧基、亚丙氧基、亚丁氧基和其组合。优选环氧烷聚合物是具有平均3-30个亚乙氧基单元的乙氧基化甘油、具有平均3-30个亚丙氧基单元的丙氧基化甘油、具有平均3-30个亚乙氧基单元的乙氧基化三羟甲基丙烷、具有平均3-30个丙烯氧基单元的丙氧基化三羟甲基丙烷、具有平均3-30个亚乙氧基单元的乙氧基化季戊四醇、具有平均3-30个亚丙氧基单元的丙氧基化季戊四醇、具有平均3-30个亚乙氧基单元和平均3-30个亚丙氧基单元的乙氧基化季戊四醇/丙氧基化季戊四醇、具有平均4-30个亚乙氧基单元的乙氧基化二季戊四醇、具有平均4-30个亚丙氧基单元的丙氧基化二季戊四醇和其组合。
可以用于本发明组合物的优选聚合交联剂是具有悬垂式结合的羟基的聚合物,并且优选包含作为聚合单元的一种或多种有具有式*-L3-OH的经羟基取代部分的不饱和单体,其中*表示与单体的连接点;并且L3是C1-30二价连接基团。具有经羟基取代的悬垂基团的聚合交联剂优选包含作为聚合单元的一种或多种具有以下式(10)的单体
其中R60和R61独立地是H、C1-10烷基、C6-20芳基、C1-10卤代烷基、卤素或-L3-OH;R62是H、C1-4烷基、C1-4卤代烷基、卤素、CN或-L3-OH;L3是C1-30二价连接基团。R60和R61优选独立地是H或-L3-OH并且更优选H。R62优选是H、C1-4烷基、C1-4卤代烷基、卤素或CN;并且更优选H或甲基。L3优选是任选地具有1到10个杂原子的C1-30有机残基。优选的具有式(10)的单体是具有式(10A)的(甲基)丙烯酸C2-10羟烷酯和具有式(10B)的(甲基)丙烯酸亚烷氧酯
其中R62a是H或甲基;R63是C2-10亚烷基;R62b是H或甲基;并且p4是O-C2-3亚烷基单元的平均数并且是1到10的整数。具有式(10A)和(10B)的示例性单体是丙烯酸羟乙酯、甲基丙烯酸羟乙酯、丙烯酸羟丙酯、甲基丙烯酸羟丙酯、具有平均1-10个乙烯氧基单元的乙氧基化(甲基)丙烯酸酯和具有平均1-10个丙烯氧基单元的丙氧基化(甲基)丙烯酸酯。具有悬垂式结合的羟基的优选聚合交联剂是那些包含作为聚合单元的一种或多种具有式(10)的单体和一种或多种选自(甲基)丙烯酸、(甲基)丙烯酸C1-20烷酯、(甲基)丙烯酸C6-20芳酯、(甲基)丙烯酸C7-20芳烷酯、乙烯基芳香族单体的单体、具有以下式(4)的单体以及具有以下式(6)的单体的聚合交联剂
其中ADG是如上所述的可酸分解的基团;R20和R20a各自独立地选自H、C1-4烷基、C1-4卤代烷基、卤素和CN;并且R30是具有如上所述的内酯部分的单价有机残基。聚合交联剂优选包含作为聚合单元的5到50mol%、更优选5到40mol%、甚至更优选5到30mol%并且又更优选10到30mol%具有式(10)的单体。其它优选的具有式(10)的单体包括羟基苯乙烯和羟基(乙烯基萘)。
多种有机溶剂和水可以用于本发明组合物,其条件是这类溶剂溶解所述组合物的组分。本发明组合物优选包含一种或多种有机溶剂和任选的水。有机溶剂可以单独使用或可以使用有机溶剂的混合物。合适的有机溶剂包括但不限于:酮,如环己酮和甲基-2-正戊酮;醇,如3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇和1-乙氧基-2-丙醇;醚,如丙二醇甲醚(PGME)、丙二醇乙醚(PGEE)、乙二醇单甲醚、丙二醇单乙醚、乙二醇单乙醚、丙二醇二甲醚和二乙二醇二甲醚;酯,如丙二醇单甲醚乙酸酯(PGMEA)、丙二醇单乙醚乙酸酯、乳酸乙酯(EL)、羟基异丁酸甲酯(HBM)、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯和丙二醇单叔丁醚乙酸酯;内酯,如γ-丁内酯;离子液体;和前述物质的任何组合。优选溶剂是PGME、PGEE、PGMEA、EL、HBM、和其组合。
本发明组合物可以进一步包含一种或多种任选的组分,如固化催化剂、涂料增强剂、一种或多种稳定剂等。用于本发明组合物的这类任选的组分的量的选取完全在所属领域的技术人员的能力范围内。
合适的固化催化剂包括但不限于热酸生成剂、光酸生成剂、光碱生成剂和季铵盐,优选热酸生成剂和季铵盐,并且更优选季铵盐。热酸生成剂是在曝露于热量时释放酸的任何化合物。热酸生成剂是所属领域所熟知的,并且一般可商购获得,如可从康涅狄格州诺沃克(Norwalk,Connecticut)的King Industries商购获得。示例性热酸生成剂包括但不限于胺封端的强酸,如胺封端的磺酸,如胺封端的十二烷基苯磺酸。广泛多种的光酸生成剂是所属领域已知的,并且一般也可商购获得,如可从和光纯药工业株式会社(Wako PureChemical Industries,Ltd.)和巴斯夫股份公司(BASF SE)商购获得。合适的季铵盐是:卤化季铵;羧酸季铵;磺酸季铵;硫酸氢季铵;等。优选季铵盐包括:卤化苄基三烷基铵,如氯化苄基三甲基铵和氯化苄基三乙基铵;卤化四烷基铵,如卤化四甲基铵、卤化四乙基铵和卤化四丁基铵;羧酸四烷基铵,如甲酸四甲基铵、乙酸四甲基铵、三氟甲磺酸四甲基铵、乙酸四丁基铵和三氟甲磺酸四丁基铵;磺酸四烷基铵,如磺酸四甲基铵和磺酸四丁基铵;等。优选固化催化剂是卤化四烷基铵,并且更优选氯化四烷基铵。这类季铵盐一般可商购获得,如可从西格玛奥德里奇商购获得,或可以通过所属领域已知的程序制备。这类任选的固化催化剂在本发明组合物中的用量占总固体的0到10%,优选占总固体的0.01%到7%,并且更优选占总固体的0.05%到5%。
任选地将涂料增强剂添加到本发明组合物中以改进涂布于衬底上的组合物膜或层的质量。这类涂料增强剂可以起增塑剂、表面流平剂等的作用。这类涂料增强剂为所属领域的技术人员所熟知并且一般可商购获得。示例性涂料增强剂是:长链烷醇,如油醇、鲸蜡醇等;二醇,如三丙二醇、四乙二醇等;和表面活性剂。尽管可以使用任何合适的表面活性剂作为涂料增强剂,但这类表面活性剂通常是非离子型表面活性剂。示例性非离子型表面活性剂是那些含有亚烷氧基键如亚乙基氧基键、亚丙基氧基键或亚乙基氧基键与亚丙基氧基键的组合的表面活性剂。优选在本发明组合物中使用一种或多种涂料增强剂。涂料增强剂在本发明组合物中的用量通常占总固体的0到10%,优选占总固体的0.5%到10%,并且更优选占总固体的1%到8%。
可以任选地将一种或多种稳定剂添加到本发明组合物中。这类稳定剂可以用于防止在储存期间含硅部分的不希望的水解或缩合。已知各种这类稳定剂,并且含硅聚合物稳定剂优选是酸。适用于硅氧烷聚合物的酸稳定剂包括但不限于羧酸、羧酸酐、无机酸等以及前述物质中的任一种的混合物。示例性稳定剂包括乙酸、草酸、丙二酸、丙二酸酐、苹果酸、马来酸、马来酸酐、富马酸、柠康酸、戊二酸、戊二酸酐、己二酸、琥珀酸、琥珀酸酐、硝酸和其混合物。羧酸是优选稳定剂,并且稳定剂更优选是乙酸、草酸、丙二酸、苹果酸、马来酸、富马酸、柠康酸、戊二酸、己二酸、琥珀酸和其混合物。这类稳定剂的用量占总固体的0到20%,优选占总固体的0.1%到15%,更优选占总固体的0.5%到10%,并且又更优选占总固体的1%到10%。
本发明的组合物是通过按任何顺序组合以下各项来制备的:一种或多种本发明的缩合聚合物;一种或多种溶剂;和任何任选的组分。所述组合物可以原样使用,或可以进行进一步纯化,如通过过滤。
本发明的方法包含(a)用上述组合物涂布衬底以形成涂层;(b)固化涂层以形成聚合物底层;(c)在聚合物底层上设置一层光致抗蚀剂;(d)以图案方式暴露光致抗蚀剂层以形成潜像;(e)显影潜像以形成其中具有浮雕图像的图案化光致抗蚀剂层;(f)将浮雕图像转印到衬底上;以及(g)通过湿法剥离来移除聚合物底层。
包含本发明组合物的涂层可以通过任何合适的方式如旋涂、缝模涂布、刮涂、帘式涂布、辊涂、喷涂、浸涂等涂布到电子器件衬底上。优选是旋涂。在典型的旋涂法中,将本发明组合物涂覆到以500rpm到4000rpm速率旋转15秒到90秒时间的衬底上,在衬底上得到所需缩合聚合物层。所属领域的技术人员应了解,缩合聚合物混合物层的厚度可以通过改变旋转速度以及组合物的固体含量来调节。
广泛多种的电子器件衬底可以用于本发明中,如:封装衬底,如多片组件;平板显示器衬底;集成电路衬底;用于发光二极管(LED)包括有机发光二极管(OLED)的衬底;半导体晶片;多晶硅衬底;等。这类衬底典型地由以下各者中的一个或多个构成:硅、多晶硅、氧化硅、氮化硅、氮氧化硅、锗化硅、砷化镓、铝、蓝宝石、钨、钛、钛-钨、镍、铜和金。合适的衬底可以呈晶片形式,如那些用于制造集成电路、光学传感器、平板显示器、集成光学电路和LED的晶片。如本文所使用的术语“半导体晶片”意在涵盖“电子器件衬底”、“半导体衬底”、“半导体器件”和用于各种程度的互连的各种封装件,包括单芯片晶片、多芯片晶片、各种程度的封装件或需要焊料连接(solder connection)的其它组装件。这类衬底可以是任何合适的尺寸。优选晶片衬底直径是200mm到300mm,但具有较小和较大直径的晶片也可以适当地根据本发明来采用。如本文所使用的术语“半导体衬底”包括具有一个或多个半导体层或结构的任何衬底,所述半导体层或结构可以任选地包括半导体器件的活动或可操作部分。半导体器件是指其上已经或正在批量制造至少一种微电子器件的半导体衬底。
在涂布到衬底上之后,涂层任选地在相对较低的温度下进行软烘烤以从底层中移除任何溶剂和其它相对挥发性组分。通常在≤200℃、优选100℃到200℃并且更优选100℃到150℃的温度下烘烤衬底。烘烤时间通常是10秒到10分钟、优选30秒到5分钟并且更优选60秒到90秒。当衬底是晶片时,这种烘烤步骤可以通过在热板上加热晶片来执行。这种软烘烤步骤可以作为固化涂层的一部分来执行或可以一同省略。
然后固化包含本发明的缩合聚合物和交联剂的涂层以形成底层。充分固化涂层以使得膜不与随后涂覆的有机层(如直接设置在涂层上的光致抗蚀剂层或其它有机层)互混,同时仍保持底层膜的所需抗反射特性(n和k值)和蚀刻选择性。涂层可以在含氧气氛(如空气)中或在惰性气氛(如氮气)中并且在足以提供固化底层的条件(如加热)下固化。此固化步骤优选在热板式设备上进行,但烘箱固化可以用于获得同等结果。这类固化通常通过在≤350℃并且优选200℃到250℃的固化温度下加热缩合聚合物层来进行。可替代地,可以使用两步固化方法或斜坡式温度变化固化方法。这类两步和斜坡式温度变化固化条件为所属领域的技术人员所熟知。所选固化温度对于用于释放酸以帮助固化缩合聚合物膜的任何热酸生成剂而言是足够的。固化时间可以是10秒到10分钟、优选30秒到5分钟、更优选45秒到5分钟并且又更优选45秒到90秒。最终固化温度的选择主要取决于所需固化速率,其中较高的固化温度需要较短的固化时间。在此固化步骤之后,底层表面可以任选地通过用钝化剂如二硅氮烷化合物(如六甲基二硅氮烷)处理来钝化,或通过脱水烘烤步骤来移除任何吸附的水。这类用二硅氮烷化合物进行的钝化处理通常在120℃下进行。
在固化包含缩合聚合物和交联剂的涂层以形成底层之后,可以在底层上设置一个或多个处理层如光致抗蚀剂层、硬掩模层、底部抗反射涂层(或BARC层)等。举例来说,可以通过如旋涂将光致抗蚀剂层直接设置于底层的表面上。可替代地,可以将BARC层直接涂覆在底层上,随后固化BARC层,并且将光致抗蚀剂层直接涂布在固化BARC层上。在另一个替代方案中,首先将有机底层涂布在衬底上并固化,随后将本发明的缩合聚合物层涂布在固化有机底层上,接着固化涂层以形成底层,可以将任选的BARC层直接涂布在底层上,随后固化任选的BARC层,并且将光致抗蚀剂层直接涂布在固化BARC层上。可以适当地使用广泛多种的光致抗蚀剂,如那些用于193nm光刻中的光致抗蚀剂,如那些可以获自陶氏电子材料(DowElectronic Materials)(马萨诸塞州马尔伯勒(Marlborough,Massachusetts))以EPICTM品牌出售的光致抗蚀剂。合适的光致抗蚀剂可以是正性显影抗蚀剂或负性显影抗蚀剂或可以是常规的负性抗蚀剂。随后使用图案化光化辐射使光致抗蚀剂层成像(暴露),并且接着使用适当的显影剂使暴露的光致抗蚀剂层显影,得到图案化光致抗蚀剂层。本发明的一个优点在于,与常规的可湿法剥离的含硅底层相比,在与显影剂接触时图案化光致抗蚀剂层的图案塌缩减少。接下来,将图案从光致抗蚀剂层转印到任何任选的BARC层上,随后通过适当的蚀刻技术如在适当等离子体情况下的干法蚀刻转印到底层上。在这种蚀刻步骤期间通常也移除光致抗蚀剂。接下来,使用适当的技术如在O2等离子体情况下的干法蚀刻将图案转印到存在的任何有机底层上,并且随后在适当时转印到衬底上。在这些图案转印步骤之后,使用常规的技术移除底层和任何任选的有机底层。随后根据常规的方式进一步处理电子器件衬底。
包含本发明的缩合聚合物的涂层和本文所述的底层是可湿法剥离的。“可湿法剥离的”是指通过使涂层或底层与常规的湿法剥离组合物接触来移除并且优选地实质上移除(≥95%膜厚度)本发明的涂层和底层,所述湿法剥离组合物如:(1)含水碱组合物,如碱水溶液(通常约5%)或氢氧化四甲铵水溶液(通常≥5wt%);(2)含水氟离子剥离剂,如氟化铵/二氟化铵混合物;(3)无机酸(如硫酸或盐酸)与过氧化氢的混合物;或(4)氨、水和任选的过氧化氢的混合物。本发明的聚合物并且特别地本发明的底层的一个特别优点是其在与氨与过氧化氢的混合物接触时是湿法可剥离的。合适的硫酸与过氧化氢的混合物是浓硫酸+30%过氧化氢。可以使用多种氨与水混合物。合适的氨、水和过氧化氢的混合物是呈1:1:5到1:10:50重量比如1:1:10、1:1:40、1:5:40或1:1:50重量比的氨+过氧化氢+水的混合物。这类混合物通常在室温到约75℃的温度下使用。优选≥97%并且更优选≥99%膜厚度的聚合物层或底层是通过使聚合物层或硅氧烷底层与(i)硫酸与过氧化氢或的混合物或(ii)氢氧化铵与过氧化氢的混合物接触来移除。
本发明的聚合物层的另一个优点在于,其易于移除以允许衬底如晶片的再加工。在这种再加工过程中,将包含一种或多种本发明的缩合聚合物的上述组合物涂布在衬底上。然后任选地软烘烤涂布聚合物层,接着进行固化以形成底层。接下来,在底层上涂布光致抗蚀剂层,并使抗蚀剂层成像和显影。然后可以移除各图案化抗蚀剂层和底层以允许晶片的再加工。在合适的温度下使底层与上述湿法剥离组合物中的任一种接触,所述湿法剥离组合物如氢氧化四甲基铵水溶液组合物(通常≥5wt%)和氟离子剥离剂水溶液(如氟化铵/二氟化铵混合物),从而移除底层,得到不含或实质上不含底层的衬底,并且可以根据需要容易地进行额外的再加工。这种再加工包括在衬底上涂布另一层本发明的缩合聚合物并如上所述加工聚合物涂层。
实例1.在氮气层下在75℃下在2小时内将溶解于1,3-二氧杂环戊烷(304g)中的甲基丙烯酸叔丁酯(tBMA)(173g)、γ丁内酯(GBLMA)(166g)和甲基丙烯酸3-(三甲氧基硅烷基)丙酯(TMSPMA)(60.6g)溶液和溶解于2:1v/v四氢呋喃/乙腈(60.6g)中的V-65引发剂(60.6g)溶液都逐滴添加到3-二氧杂环戊烷(710g)中。添加后,将反应溶液再保持75℃下两小时,冷却到室温并沉淀到庚烷:MTBE(1:1v/v,14L)中。通过真空过滤收集沉淀聚合物并真空烘箱干燥24小时,得到呈白色固体状的聚合物1(tBMA/GBLMA/TMSPMA 50/40/10)(271g,68%)。相对于聚苯乙烯标准物而言通过GPC测定Mw并且发现是5700Da。
实例2.根据实例1的程序使用下表1中列出的单体来合成下表2中报告的聚合物2到12。所用各单体的量以mol%报告于表2中。分离聚合物2到12,产率是20-99%,并且在表2中报告Mw。
表1
表2
实例3.重复实例2的程序并预期得到表3中所报告的聚合物13-18。表3中所报告的单体数是指实例2的表1中的单体。
表3
实例4.在10分钟内将含盐酸(在水中37wt%,7.76g)的水(25.9g)溶液添加到TEOS(63.5g,50mol%)与含实例1的聚合物1(50.0g,50mol%)的THF(270g)的混合物中并在在室温下搅拌1小时。将反应混合物加热到63℃持续20小时,然后冷却到室温。添加PGEE(200g),在减压下移除挥发性物种,并用PGEE稀释所得溶液,得到呈澄清溶液状的缩合聚合物1(在PGEE中10wt%,600g)。相对于聚苯乙烯标准物而言通过GPC测定Mw(28,100Da)。
实例5.根据实例4的程序使用实例1和2的聚合物1到12和下表4中列出的单体来合成下表5中所报告的缩合聚合物2到26。所用各单体的量以mol%报告于表5中。分离缩合聚合物2到12,产率是20-99%,并且在表5中报告Mw。
表4
表5
实例6.组合以下组分:1.6wt%缩合聚合物1;0.09wt%含0.1wt%氯化四丁基铵溶液的PGEE;49wt%PGEE;49.2wt%2-羟基异丁酸甲酯;0.009wt%乙酸;和0.2wt%涂料增强剂。通过0.2μm聚四氟乙烯注射器过滤混合物,得到比较配制物1。
实例7.重复实例6的程序以通过用表6中所报告的缩合聚合物代替缩合聚合物1来制备比较配制物2到8。
表6
实例8.重复实例6的程序,不同之处在于用85/15w/w缩合聚合物1与丙氧基化季戊四醇的混合物代替缩合聚合物1作为交联剂,所述混合物平均具有5摩尔环氧丙烷(式(11),a+b+c+d≈5),得到配制物1。
实例9.重复实例6的程序以通过用表7中所报告的缩合聚合物/交联剂混合物代替缩合聚合物1,得到配制物2-15。交联剂C1是平均具有5摩尔具有式(11)的环氧丙烷的丙氧基化季戊四醇。交联剂C2是具有呈25/25/25/25摩尔比的甲基丙烯酸叔丁酯/甲基丙烯酸α-γ丁内酯/甲基丙烯酸羟乙酯/甲基丙烯酸的聚合物。交联剂C3是具有呈50/25/25摩尔比的甲基丙烯酸叔丁酯/甲基丙烯酸α-γ-丁内酯/甲基丙烯酸羟乙酯的聚合物。交联剂C4是具有呈60/40摩尔比的甲基丙烯酸和甲基丙烯酸羟乙酯的聚合物。
表7
实例10.将实例6和7的比较配制物以及实例8和9的本发明的配制物以1500rpm旋涂在裸200mm硅晶片上,并在240℃下使用ACT-8Clean Track(Tokyo Electron Co.)烘烤60秒。用来自Therma-wave Co.的OptiProbeTM仪器测量烘烤后每个涂膜的厚度。然后使用1/1/40wt/wt/wt 30%NH4OH/30%H2O2/水的混合物评估每个涂布样品的SC-1可湿法剥离性。将SC-1混合物加热到60℃,并将每个涂布晶片的试样浸入溶液中1分钟。将试样从SC-1混合物中移除并用去离子水冲洗,再次测量膜厚度。将每个样品的膜厚度损失计算为与剥离剂接触前后的膜厚度差。在蚀刻后任选地测试如上所述制备的单独膜的SC-1可剥离性。使用来自Plasma-Therm Co.的RIE790用氧气、25sscm流量、180W功率和6毫托压力进行蚀刻60秒。表8中报告了以膜移除速率(以为单位)形式获得的剥离结果。
如上所述将呈1.7%或3.5%固体的实例6和7的比较配制物以及实例8和9的本发明的配制物涂布在200mm硅晶片上,并且目标厚度是或并且如上所述进行测量(固化后)。将一池市售0.26N TMAH显影剂(MF CD-26)施加到每个晶片上60秒,之后用DI水冲洗晶片,旋转干燥并重新测量膜厚度。对每个晶片进行105℃/60秒的最终干燥烘烤并测量最终膜厚度。表8中报告了以膜移除速率(以为单位)形式报告的每个膜的厚度损失,所述损失由此TMAH剥离产生。负膜剥离值表示膜厚度的增加。
表8
Claims (14)
1.一种用于形成含硅底层的组合物,其包含:
(a)一种或多种溶剂;
(b)以下各项的缩合物和/或水解物:
(i)一种或多种缩合含硅聚合物,所述缩合含硅聚合物包含作为聚合单元的一种或多种具有可缩合含硅部分的第一不饱和单体,以及一种或多种不含可缩合含硅部分的第二不饱和单体,其中至少一种第一不饱和单体具有式(1):
其中L是单键或二价连接基团;各R1独立地选自H、C1-10烷基、C2-20烯基、C5-20芳基和C6-20芳烷基;R2和R3各自独立地选自H、C1-4烷基、C1-4卤代烷基、卤素、C5-20芳基、C6-20芳烷基和CN;R4选自H、C1-10烷基、C1-10卤代烷基、卤素、C5-20芳基、C6-20芳烷基和C(=O)R5;R5选自OR6和N(R7)2;R6选自H和C1-20烷基;各R7独立地选自H、C1-20烷基和C6-20芳基;各Y1独立地选自卤素、C1-10烷氧基、C5-10芳氧基、C1-10羧基;并且b是0到2的整数,至少一种第二不饱和单体具有式(3)
其中Z是具有内酯部分的单价有机残基;并且R10独立地选自H、C1-4烷基、C1-4卤代烷基、卤素和CN,和
(ii)一种或多种具有式(8)的可缩合硅单体:
Si(R50)p(X)4-p(8)
其中p是0到3的整数;各R50独立地选自C1-30烃基部分和经取代C1-30烃基部分;并且各X独立地选自卤素、C1-10烷氧基、-OH、-O-C(O)-R50和-(O-Si(R51)2)p2-X1;X1独立地选自卤素、C1-10烷氧基、-OH、-O-C(O)-R50;各R51独立地选自R50和X;并且p2是1到10的整数;和
(c)一种或多种不含Si-O键且具有至少两个羟基的交联剂。
2.根据权利要求1所述的组合物,其中所述交联剂选自具有C2-4-亚烷氧基重复单元和2个或更多个末端羟基的环氧烷聚合物和具有两个或更多个悬垂式结合的羟基的聚合物。
3.根据权利要求1或2所述的组合物,其中p=0或1。
4.根据权利要求1或2所述的组合物,其中所述(c)交联剂具有四个或更多个羟基。
5.根据权利要求1或2所述的组合物,其中L是二价连接基团。
6.根据权利要求5所述的组合物,其中所述二价连接基团是具有1到20个碳原子和任选的一个或多个杂原子的有机基团。
7.根据权利要求5所述的组合物,其中所述二价连接基团具有式-C(=O)-O-L1-,其中L1是单键或具有1到20个碳原子的有机基团。
8.根据权利要求1或2所述的组合物,其中所述缩合物和/或水解物进一步包含作为聚合单元的一种或多种除了具有式(3)的单体之外的不含可缩合含硅部分的第二不饱和单体。
9.根据权利要求8所述的组合物,其中至少一种除了具有式(3)的单体之外的第二不饱和单体具有酸性质子并且水中pKa是-5到13。
11.根据权利要求1或2所述的组合物,其中所述缩合物和/或水解物进一步包含作为聚合单元的一种或多种具有发色团部分的不饱和单体。
12.根据权利要求11所述的组合物,其中所述发色团部分悬垂于所述聚合物主链上。
13.一种用于形成含硅底层的方法,其包含:
(a)用根据权利要求1-12中任一项所述的组合物涂布衬底以形成涂层;
(b)固化所述涂层以形成聚合物底层;
(c)在所述聚合物底层上设置一层光致抗蚀剂;
(d)以图案方式暴露所述光致抗蚀剂层以形成潜像;
(e)显影所述潜像以形成其中具有浮雕图像的图案化光致抗蚀剂层;
(f)将所述浮雕图像转印到所述衬底上;以及
(g)通过湿法剥离来移除所述聚合物底层。
14.根据权利要求13所述的方法,其中所述聚合物底层是通过湿法剥离来移除的。
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