TWI589596B - 包括具有光酸產生官能基及鹼溶解度增強官能基的重複單元的聚合物及相關光阻劑組合物及電子裝置形成方法 - Google Patents
包括具有光酸產生官能基及鹼溶解度增強官能基的重複單元的聚合物及相關光阻劑組合物及電子裝置形成方法 Download PDFInfo
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- TWI589596B TWI589596B TW104132896A TW104132896A TWI589596B TW I589596 B TWI589596 B TW I589596B TW 104132896 A TW104132896 A TW 104132896A TW 104132896 A TW104132896 A TW 104132896A TW I589596 B TWI589596 B TW I589596B
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- polymer
- photoacid
- photoacid generating
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- 229920000642 polymer Polymers 0.000 title claims description 58
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 42
- 125000000524 functional group Chemical group 0.000 claims description 29
- -1 ketal group Chemical group 0.000 claims description 27
- 239000003513 alkali Substances 0.000 claims description 21
- 150000001450 anions Chemical class 0.000 claims description 21
- 230000002708 enhancing effect Effects 0.000 claims description 20
- 150000001768 cations Chemical class 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000007942 carboxylates Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 229920001515 polyalkylene glycol Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000008053 sultones Chemical group 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims 6
- 125000000686 lactone group Chemical group 0.000 claims 4
- 125000004036 acetal group Chemical group 0.000 claims 3
- 125000003158 alcohol group Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
- 125000003827 glycol group Chemical group 0.000 claims 2
- 230000003252 repetitive effect Effects 0.000 claims 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 18
- ZMDWMSFWJATBFR-UHFFFAOYSA-N 2-but-2-en-2-yloxy-1,1-difluoroethanesulfonic acid Chemical compound CC=C(C)OCC(F)(F)S(=O)(=O)O ZMDWMSFWJATBFR-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 229940116333 ethyl lactate Drugs 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003999 initiator Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- JCMYDLGBKHROIX-UHFFFAOYSA-N 1,1-difluoro-2-(2-methylprop-2-enoylperoxy)ethanesulfonic acid Chemical compound FC(COOC(C(=C)C)=O)(S(=O)(=O)O)F JCMYDLGBKHROIX-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229920001519 homopolymer Polymers 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VCLSNCZXGYJVHN-UHFFFAOYSA-N 1,1-difluoro-3-[2-(2-methylprop-2-enoyloxy)ethoxy]-3-oxopropane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCOC(=O)CC(F)(F)S(=O)(=O)O VCLSNCZXGYJVHN-UHFFFAOYSA-N 0.000 description 7
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- SXTDHNTZQIAQHD-UHFFFAOYSA-N (2,2-difluoro-2-sulfooxyethyl) 2-methylprop-2-enoate Chemical compound FC(COC(C(=C)C)=O)(OS(=O)(=O)O)F SXTDHNTZQIAQHD-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 5
- 229920006029 tetra-polymer Polymers 0.000 description 5
- HVQYCNNKJPWNFZ-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]-1,3-dimethylbenzene Chemical group COCCOCCOC1=C(C)C=CC=C1C HVQYCNNKJPWNFZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- PBKGNJXLJQARIN-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 PBKGNJXLJQARIN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ICURIFUTRQEJPA-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)cyclohexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CC(C(O)(C(F)(F)F)C(F)(F)F)CC(C(O)(C(F)(F)F)C(F)(F)F)C1 ICURIFUTRQEJPA-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JQDQRYVNMDWLJV-UHFFFAOYSA-N (2-ethoxy-2,2-difluoroethyl) 2-methylprop-2-enoate Chemical compound FC(COC(C(=C)C)=O)(OCC)F JQDQRYVNMDWLJV-UHFFFAOYSA-N 0.000 description 2
- NNEJUQJGPQVEHZ-UHFFFAOYSA-N 1,1-difluoro-2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethanesulfonic acid Chemical compound FC(COCCOC(C(=C)C)=O)(S(=O)(=O)O)F NNEJUQJGPQVEHZ-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- DOZALMQRVQMIQK-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-(4-dibenzothiophen-5-ium-5-yl-2,6-dimethylphenoxy)acetate Chemical compound CC=1C=C([S+]2C3=CC=CC=C3C3=CC=CC=C32)C=C(C)C=1OCC(=O)OC1(CC)CCCC1 DOZALMQRVQMIQK-UHFFFAOYSA-N 0.000 description 1
- IDNDBZMCTVQNCN-UHFFFAOYSA-N 1,1-difluoro-2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCC(F)(F)S(O)(=O)=O IDNDBZMCTVQNCN-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ILXLZIZZDNSXNK-UHFFFAOYSA-N 2,2-difluoroethyl 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOCC(F)F ILXLZIZZDNSXNK-UHFFFAOYSA-N 0.000 description 1
- VAHNPAMCADTGIO-UHFFFAOYSA-N 2-methoxyethyl propanoate Chemical compound CCC(=O)OCCOC VAHNPAMCADTGIO-UHFFFAOYSA-N 0.000 description 1
- ZEUUTMRKMHVAIG-UHFFFAOYSA-N 2-oxooxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1=O ZEUUTMRKMHVAIG-UHFFFAOYSA-N 0.000 description 1
- PPXAHQRRLKQYTG-UHFFFAOYSA-N 2-phenylpropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C1=CC=CC=C1 PPXAHQRRLKQYTG-UHFFFAOYSA-N 0.000 description 1
- JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QITITIHFVBIFEI-UHFFFAOYSA-N CC(=C)C(=NO)OCC(OC1=C(C2=C(C=C1)SC3=CC=CC=C32)C4=CC=CC=C4)(F)F Chemical compound CC(=C)C(=NO)OCC(OC1=C(C2=C(C=C1)SC3=CC=CC=C32)C4=CC=CC=C4)(F)F QITITIHFVBIFEI-UHFFFAOYSA-N 0.000 description 1
- ZHCTWYMYWPECIJ-UHFFFAOYSA-O CCC1(CCCC1)OC(COC(C(C)=C1)=C(C)C=C1[S+]1C(C=CC(C2(F)F)OOC(C(C)=C)=O)=C2C2=C1C=CC=C2)=NO Chemical compound CCC1(CCCC1)OC(COC(C(C)=C1)=C(C)C=C1[S+]1C(C=CC(C2(F)F)OOC(C(C)=C)=O)=C2C2=C1C=CC=C2)=NO ZHCTWYMYWPECIJ-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- NGDPCAMPVQYGCW-UHFFFAOYSA-N dibenzothiophene 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3C2=C1 NGDPCAMPVQYGCW-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OKOHFSWRKRCHAD-UHFFFAOYSA-N ethane ethanesulfonic acid Chemical compound CC.CCS(O)(=O)=O OKOHFSWRKRCHAD-UHFFFAOYSA-N 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- DDMCDMDOHABRHD-UHFFFAOYSA-N methyl 2-hydroxybutanoate Chemical compound CCC(O)C(=O)OC DDMCDMDOHABRHD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AWMAOFAHBPCBHJ-UHFFFAOYSA-M sodium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound [Na+].C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C AWMAOFAHBPCBHJ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- C08F228/00—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 bond to sulfur or by a heterocyclic ring containing sulfur
- C08F228/02—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 bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US201462062347P | 2014-10-10 | 2014-10-10 |
Publications (2)
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| TW201613985A TW201613985A (en) | 2016-04-16 |
| TWI589596B true TWI589596B (zh) | 2017-07-01 |
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| JP (1) | JP6111306B2 (https=) |
| KR (1) | KR101786641B1 (https=) |
| CN (1) | CN105504118B (https=) |
| TW (1) | TWI589596B (https=) |
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| US9557642B2 (en) | 2014-10-10 | 2017-01-31 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| US9527936B2 (en) | 2014-10-10 | 2016-12-27 | Rohm And Haas Electronic Materials Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9551930B2 (en) | 2014-10-10 | 2017-01-24 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| JP6543222B2 (ja) * | 2016-06-03 | 2019-07-10 | 株式会社三共 | 遊技機 |
| JP6846127B2 (ja) * | 2016-06-28 | 2021-03-24 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
| WO2018042810A1 (ja) * | 2016-08-31 | 2018-03-08 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
| WO2018194123A1 (ja) * | 2017-04-20 | 2018-10-25 | Jsr株式会社 | 感放射線性樹脂組成物及びレジストパターン形成方法 |
| JP7407576B2 (ja) * | 2019-12-03 | 2024-01-04 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
| CN111138410A (zh) * | 2019-12-28 | 2020-05-12 | 上海博栋化学科技有限公司 | 含金刚烷结构的光刻胶产酸树脂单体及其合成方法 |
| JP7719654B2 (ja) * | 2020-08-05 | 2025-08-06 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
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| US12393118B2 (en) | 2021-05-28 | 2025-08-19 | Dupont Electronic Materials International, Llc | Composition for photoresist underlayer |
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| US20150346599A1 (en) * | 2014-05-29 | 2015-12-03 | Rohm And Haas Electronic Materials Llc | Photo-destroyable quencher and associated photoresist composition, and device-forming method |
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| US9551930B2 (en) * | 2014-10-10 | 2017-01-24 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| US9557642B2 (en) * | 2014-10-10 | 2017-01-31 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| US9527936B2 (en) * | 2014-10-10 | 2016-12-27 | Rohm And Haas Electronic Materials Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
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2015
- 2015-08-24 US US14/833,273 patent/US9606434B2/en active Active
- 2015-10-06 TW TW104132896A patent/TWI589596B/zh active
- 2015-10-07 KR KR1020150140861A patent/KR101786641B1/ko active Active
- 2015-10-07 JP JP2015198976A patent/JP6111306B2/ja active Active
- 2015-10-09 CN CN201510650560.6A patent/CN105504118B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105504118A (zh) | 2016-04-20 |
| TW201613985A (en) | 2016-04-16 |
| US20160102158A1 (en) | 2016-04-14 |
| JP6111306B2 (ja) | 2017-04-05 |
| JP2016104849A (ja) | 2016-06-09 |
| US9606434B2 (en) | 2017-03-28 |
| KR20160042776A (ko) | 2016-04-20 |
| CN105504118B (zh) | 2019-04-30 |
| KR101786641B1 (ko) | 2017-10-19 |
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