JP2015038604A - フォトレジスト組成物、コーティング基板、および電子デバイスを製造する方法 - Google Patents
フォトレジスト組成物、コーティング基板、および電子デバイスを製造する方法 Download PDFInfo
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- JP2015038604A JP2015038604A JP2014144245A JP2014144245A JP2015038604A JP 2015038604 A JP2015038604 A JP 2015038604A JP 2014144245 A JP2014144245 A JP 2014144245A JP 2014144245 A JP2014144245 A JP 2014144245A JP 2015038604 A JP2015038604 A JP 2015038604A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 113
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 239000000758 substrate Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
- 239000001257 hydrogen Substances 0.000 claims abstract description 76
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 230000005855 radiation Effects 0.000 claims abstract description 12
- 125000000732 arylene group Chemical group 0.000 claims abstract description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 238000010276 construction Methods 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 238000005530 etching Methods 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 3
- 150000008027 tertiary esters Chemical class 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 120
- -1 acetal compounds Chemical class 0.000 description 94
- 239000000243 solution Substances 0.000 description 60
- 239000004094 surface-active agent Substances 0.000 description 23
- 150000001241 acetals Chemical class 0.000 description 20
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 description 12
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 12
- 229920006324 polyoxymethylene Polymers 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 229930182556 Polyacetal Natural products 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
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- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-O Thiophenium Chemical compound [SH+]1C=CC=C1 YTPLMLYBLZKORZ-UHFFFAOYSA-O 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 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 5
- 239000000178 monomer Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 4
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 4
- IEHGSIUPPIZJGG-UHFFFAOYSA-N 5-phenyldibenzothiophen-5-ium Chemical compound C1=CC=CC=C1[S+]1C2=CC=CC=C2C2=CC=CC=C21 IEHGSIUPPIZJGG-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 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 3
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 3
- VSNRGUXJQPIFRA-UHFFFAOYSA-N 1,1,2,2-tetrafluorobutane-1-sulfonic acid Chemical compound CCC(F)(F)C(F)(F)S(O)(=O)=O VSNRGUXJQPIFRA-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 239000002184 metal Chemical class 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920001855 polyketal Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- SLEPTJJRHVICMA-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-4-(3-hydroxyadamantane-1-carbonyl)oxybutane-1-sulfonic acid Chemical compound C1C(C2)CC3CC1(O)CC2(C(=O)OCCC(F)(F)C(F)(F)S(O)(=O)=O)C3 SLEPTJJRHVICMA-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
- XDOFKUHHLNYRPM-UHFFFAOYSA-N 2-hydroxypiperidine-1-carboxylic acid Chemical compound OC1CCCCN1C(O)=O XDOFKUHHLNYRPM-UHFFFAOYSA-N 0.000 description 2
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
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- 125000006002 1,1-difluoroethyl group Chemical group 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GRJHONXDTNBDTC-UHFFFAOYSA-N phenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1 GRJHONXDTNBDTC-UHFFFAOYSA-N 0.000 description 1
- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
- 238000010345 tape casting Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VTLHPSMQDDEFRU-UHFFFAOYSA-O telluronium Chemical class [TeH3+] VTLHPSMQDDEFRU-UHFFFAOYSA-O 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Images
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
- G03F7/039—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
-
- 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
- G03F7/0395—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 a backbone with alicyclic moieties
-
- 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
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/36—Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
Abstract
Description
を有する複数の繰り返し単位を含むポリマーと、光酸発生剤、光塩基発生剤、光開始剤、およびそれらの組合せから選択される光活性成分とを含むフォトレジスト組成物である。
を有する1つ以上のビス(アリール)アセタール化合物のSuzuki重縮合によって形成され得る。BX基の例としては−BF3 −M+が挙げられ、M+の各存在は独立してアルカリ金属カチオン、または非置換もしくは置換されたアンモニウムイオン;−B(OH)2;および
である。
Y−Ar3−Y
(式中、YおよびAr3は上記に定義され、Yの各存在は独立して定義される)を有する)
を有するビス(アリール)アセタール化合物のSuzuki重縮合を含む。
BX−Ar3−BX
(式中、BXおよびAr3は上記に定義され、BXの各存在は独立して定義される)を有する)
を有するビス(アリール)アセタール化合物のSuzuki重縮合を含む。
を有するものを含むことを決定した。このような触媒を調製する方法はC.C.C.Johansson Seechurn、S.L.Parisel、およびT.J.Calacot、J.Org.Chem.2011、76、7918−7932に記載されている。
−O−C(H)(R5)−OR6
(式中、R5およびR6は独立して非置換もしくは置換されたC1−18直鎖もしくは分枝アルキル、非置換もしくは置換されたC3−18シクロアルキル、非置換もしくは置換されたC6−18アリール、および非置換もしくは置換されたC3−18ヘテロアリールからなる群から選択され;任意にR5またはR6はポリマー骨格に共有結合する(例えば、R1もしくはR2への結合、またはアセタールの酸素末端が既に結合されていないAr1、Ar2、およびAr3の1つへの結合により))
を有する一価アセタールであり得る。これらの実施形態において、アセタールは環構造の一部である。環構造は
Ar1−O−C−O−Ar2
を含んでも、または含まなくてもよい。
に示されるように、酸素原子を介してAr1、Ar2、またはAr3に結合される二価環状アセタールであり得る。一部の実施形態において、環状アセタールは
Ar1−O−C(R1)(R2)−O−Ar2
を含む環構造の部分である。他の実施形態において、環状アセタールはこのような環構造の部分ではない。
−O−C(R7)(R8)−OR9
(式中、R7、R8、およびR9は独立して非置換もしくは置換されたC1−18直鎖もしくは分枝アルキル、非置換もしくは置換されたC3−18シクロアルキル、非置換もしくは置換されたC6−18アリール、および非置換もしくは置換されたC3−18ヘテロアリールからなる群から選択される)
を有する一価ケタールであってもよい。任意にR7、R8、またはR9は共有結合してポリマー骨格を形成するのでアセタールは環構造の部分である。
に示されるように、酸素原子を介してAr1またはAr2に結合される環状ケタールであり得る。一部の実施形態において、環状ケタールは
Ar1−O−C(R1)(R2)−O−Ar2
を含む環構造の部分である。他の実施形態において、環状ケタールはこのような環構造の部分ではない。
−(O)a−(L1)b−C(=O)−OR13
(式中、aは0または1であり、bは0または1であり、但し、aが1である場合、bは1であり;R13は、非置換もしくは置換されたC1−20直鎖もしくは分枝アルキル(例えば、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、i−ブチル、t−ブチル、ジフェニルメチル、2−フェニルプロパン−2−イル、1,1−ジフェニルエタン−1−イル、トリフェニルメチル)、非置換もしくは置換されたC3−20シクロアルキル(例えば、シクロペンチル、シクロヘキシル、メチルシクロヘキサン−1−イル、エチルシクロヘキサン−1−イル、1−ノルボルニル、1−アダマンチル、2−メチルビシクロ[2.2.1]ヘプタン−2−イル、1−アダマンチル、2−メチルアダマンタン−2−イル)、非置換もしくは置換されたC6−20アリール(例えば、フェニル、1−ナフチル、および2−ナフチル)、および非置換もしくは置換されたC3−20ヘテロアリール(例えば、2−イミダゾリル、4−イミダゾリル、2−ピリジル、3−ピリジル、および4−ピリジル)からなる群から選択され;L1は、非置換もしくは置換されたC1−20直鎖もしくは分枝アルキレン(例えば、メタン−1,1−ジイル(−CH2−)、エタン−1,2−ジイル(−CH2CH2−)、エタン−1,1−ジイル(−CH(CH3)−)、プロパン−2,2−ジイル(−C(CH3)2−))、非置換もしくは置換されたC3−20シクロアルキレン(例えば、1,1−シクロペンタンジイル、1,2−シクロペンタンジイル、1,1−シクロヘキサンジイル、1,4−シクロヘキサンジイル)、非置換もしくは置換されたC6−20アリーレン(例えば、1,3−フェニレン、1,4−フェニレン、1,4−ナフチレン、1,5−ナフチレン、2,6−ナフチレン)、および非置換もしくは置換されたC3−20ヘテロアリーレン(例えば、イミダゾ−2,4−イレン、2,4−ピリジレン、2,5−ピリジレン)からなる群から選択される)
を有し得る。一部の実施形態において、R13およびL1は互いに共有結合してラクトンを形成する。一部の実施形態において、R13は、第三炭素原子、例えば
−(O)c−(L2)d−O−C(=O)−R14
(式中、cは0または1であり、dは0または1であり、但し、cが1である場合、dは1であり;R14は、非置換もしくは置換されたC1−20直鎖もしくは分枝アルキル(例えば、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、i−ブチル、t−ブチル、ジフェニルメチル、2−フェニルプロパン−2−イル、1,1−ジフェニルエタン−1−イル、およびトリフェニルメチル)、非置換もしくは置換されたC3−20シクロアルキル(例えば、シクロペンチル、シクロヘキシル、1−ノルボニル、1−アダマンチル、2−メチルビシクロ[2.2.1]ヘプタン−2−イル、2−メチルアダマンタン−2−イル)、非置換もしくは置換されたC6−20アリール(例えば、フェニル、1−ナフチル、2−ナフチル)、および非置換もしくは置換されたC3−20ヘテロアリール(例えば、2−イミダゾリル、4−イミダゾリル、2−ピリジル、3−ピリジル、4−ピリジル)からなる群から選択され;L2は、非置換もしくは置換されたC1−20直鎖もしくは分枝アルキレン(例えば、メタン−1,1−ジイル(−CH2−)、エタン−1,2−ジイル(−CH2CH2−)、エタン−1,1−ジイル(−CH(CH3)−)、プロパン−2,2−ジイル(−C(CH3)2−)、2−メチルプロパン−1,2−ジイル(−CH2C(CH3)2−)、ジフェニルメチレン(−C(C6H5)2−)、1−フェニルメタン−1,1−ジイル(−CH(C6H5)−)、2−フェニルプロパン−1,2−ジイル(−CH2C(CH3)(C6H5)−)、1,1−ジフェニルエタン−1,2−ジイル(−CH2C(C6H5)2)−)、非置換もしくは置換されたC3−20シクロアルキレン(例えば、1,1−シクロペンタンジイル、1,2−シクロペンタンジイル、1,1−シクロヘキサンジイル、1,4−シクロヘキサンジイル、エチルシクロヘキサン−1,4−ジイル、4−メチルアダマンタン−1,4−ジイル)、非置換もしくは置換されたC6−20アリーレン(例えば、1,3−フェニレン、1,4−フェニレン、1,4−ナフチレン、1,5−ナフチレン、2,6−ナフチレン)、および非置換もしくは置換されたC3−20ヘテロアリーレン(例えば、イミダゾ−2,4−イレン、2,4−ピリジレン、2,5−ピリジレン)からなる群から選択される)
を有し得る。一部の実施形態において、R14およびL2は互いに共有結合してラクトンを形成する。構造−(O)c−(L2)d−O−C(=O)−R14を有するエステルの特定の例は
を有し得る。
−R1−C−R2−
を含む環を形成する。
およびこれらの組合せを有する複数の繰り返し単位を含む。
構造
を有する繰り返し単位を含むポリマー;
構造
を有する繰り返し単位を含むポリマー;
および構造
を有する繰り返し単位;
構造
を有する繰り返し単位を含むポリマー;
構造
を有する繰り返し単位を含むポリマー;
構造
を有する繰り返し単位を含むポリマー、
および構造
を有する繰り返し単位;
構造
を有する繰り返し単位を含むポリマー;
および構造
を有する繰り返し単位;
構造
を有する繰り返し単位を含むポリマー、
および構造
を有する繰り返し単位;
構造
および構造
を有する繰り返し単位;
構造
を有する繰り返し単位を含むポリマー、
および構造
を有する繰り返し単位;
構造
構造
構造
構造
および構造
および構造
および構造
が含まれる。
を有する複数の繰り返し単位を含む。
Claims (10)
- 構造
を有する複数の繰り返し単位を含むポリマー;ならびに
光酸発生剤、光塩基発生剤、光開始剤、およびそれらの組み合わせから選択される光活性成分
を含む、フォトレジスト組成物。 - R1、R2、Ar1、Ar2、またはAr3の少なくとも1つの存在が、ヒドロキシル、アセタール、ケタール、エステル、およびラクトンから選択される少なくとも1つの官能基で置換される、請求項1に記載のフォトレジスト組成物。
- R1、R2、Ar1、Ar2、またはAr3の少なくとも1つの存在が、少なくとも1つのヒドロキシルで置換される、請求項1に記載のフォトレジスト組成物。
- R1、R2、Ar1、Ar2、またはAr3の少なくとも1つの存在が、少なくとも1つの第三級エステルで置換される、請求項1に記載のフォトレジスト組成物。
- Ar1、Ar2、およびAr3の各存在が独立して1,3−フェニレンまたは1,4−フェニレンである、請求項1〜4のいずれかに記載のフォトレジスト組成物。
- Ar1およびAr2が互いに共有結合せずに、−Ar1−O−C−O−Ar2−を含む環構造を形成する、請求項1〜5のいずれかに記載のフォトレジスト組成物。
- R1の各存在が水素であり、
R2の各存在が非置換または置換されたフェニルである、
請求項1〜6のいずれかに記載のフォトレジスト組成物。 - R1の各存在が水素であり、
R2の各存在がフェニル、ヒドロキシフェニル、オルト−メトキシフェニル、メタ−メトキシフェニル、またはパラ−メトキシフェニルである、
請求項1〜6のいずれかに記載のフォトレジスト組成物。 - (a)表面上でパターン化される1つ以上の層を有する基板;および(b)パターン化される1つ以上の層の上の請求項1〜8のいずれかに記載のフォトレジスト組成物の層を含む、コーティング基板。
- (a)請求項1〜8のいずれかに記載のフォトレジスト組成物の層を基板に塗布する工程;(b)前記フォトレジスト組成物層を活性化放射線にパターン様に露光する工程;(c)露光したフォトレジスト組成物層を現像してレジストレリーフ像を提供する工程、および(d)レジストレリーフパターンを下層基板にエッチングする工程を含む、電子デバイスを製造する方法。
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US13/943,007 US9063420B2 (en) | 2013-07-16 | 2013-07-16 | Photoresist composition, coated substrate, and method of forming electronic device |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10466593B2 (en) * | 2015-07-29 | 2019-11-05 | Taiwan Semiconductor Manufacturing Company, Ltd. | Method and apparatus of patterning a semiconductor device |
US9921475B1 (en) * | 2016-08-31 | 2018-03-20 | Rohm And Haas Electronic Materials Llc | Photoacid-generating compound, polymer derived therefrom, photoresist composition including the photoacid-generating compound or polymer, and method of forming a photoresist relief image |
JP2018109701A (ja) * | 2017-01-04 | 2018-07-12 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 化学増幅型ポジ型フォトレジスト組成物およびそれを用いたパターン形成方法 |
US10082736B2 (en) | 2017-01-13 | 2018-09-25 | International Business Machines Corporation | Approach to lowering extreme ultraviolet exposure dose for inorganic hardmasks for extreme ultraviolet patterning |
TWI708760B (zh) | 2017-11-30 | 2020-11-01 | 美商羅門哈斯電子材料有限公司 | 鹽及包括其之光阻劑 |
JP6810728B2 (ja) | 2017-11-30 | 2021-01-06 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | 双性イオン化合物およびそれを含むフォトレジスト |
CN115079517A (zh) | 2017-11-30 | 2022-09-20 | 罗门哈斯电子材料有限责任公司 | 盐和包含其的光致抗蚀剂 |
GB201903420D0 (en) | 2019-03-13 | 2019-04-24 | Nanotronix Inc | Photoresist |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53133429A (en) * | 1977-04-25 | 1978-11-21 | Hoechst Ag | Radiation sensitive copying conposite and method of forming relief |
JPS60205444A (ja) * | 1984-02-25 | 1985-10-17 | ヘキスト・アクチエンゲゼルシヤフト | 感放射組成物及び感放射記録材料 |
JPH03103856A (ja) * | 1989-09-09 | 1991-04-30 | Hoechst Ag | 陽画処理照射感応性混合物およびそれから製造した照射感応性複写材料 |
JP2003066610A (ja) * | 2001-08-27 | 2003-03-05 | Toppan Printing Co Ltd | ポリイミド樹脂及びこれを含有する感光性樹脂組成物 |
JP2003327686A (ja) * | 2002-05-09 | 2003-11-19 | Jsr Corp | レジスト材用単量体および酸解離性樹脂 |
JP2010113142A (ja) * | 2008-11-06 | 2010-05-20 | Sekisui Chem Co Ltd | ポジ型感光性組成物及び導電パターンの形成方法 |
Family Cites Families (85)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL101499C (ja) | 1951-08-20 | |||
US2875047A (en) | 1955-01-19 | 1959-02-24 | Oster Gerald | Photopolymerization with the formation of coherent plastic masses |
US2850445A (en) | 1955-01-19 | 1958-09-02 | Oster Gerald | Photopolymerization |
US3081343A (en) | 1957-10-24 | 1963-03-12 | Bayer Ag | Polyethers from polyacetals and olefins |
GB1090142A (en) | 1965-02-26 | 1967-11-08 | Agfa Gevaert Nv | Photochemical insolubilisation of polymers |
US3479185A (en) | 1965-06-03 | 1969-11-18 | Du Pont | Photopolymerizable compositions and layers containing 2,4,5-triphenylimidazoyl dimers |
US3519605A (en) | 1968-03-04 | 1970-07-07 | Gen Electric | Polyorthocarbonate polymers and copolymers and method of preparing same |
US3549367A (en) | 1968-05-24 | 1970-12-22 | Du Pont | Photopolymerizable compositions containing triarylimidazolyl dimers and p-aminophenyl ketones |
US4180646A (en) | 1975-01-28 | 1979-12-25 | Alza Corporation | Novel orthoester polymers and orthocarbonate polymers |
US4189323A (en) | 1977-04-25 | 1980-02-19 | Hoechst Aktiengesellschaft | Radiation-sensitive copying composition |
US4343885A (en) | 1978-05-09 | 1982-08-10 | Dynachem Corporation | Phototropic photosensitive compositions containing fluoran colorformer |
US4442197A (en) | 1982-01-11 | 1984-04-10 | General Electric Company | Photocurable compositions |
EP0153904B1 (de) | 1984-02-10 | 1988-09-14 | Ciba-Geigy Ag | Verfahren zur Herstellung einer Schutzschicht oder einer Reliefabbildung |
EP0164248B1 (en) | 1984-06-01 | 1991-10-09 | Rohm And Haas Company | Photosensitive coating compositions, thermally stable coatings prepared from them, and the use of such coatings in forming thermally stable polymer images |
DE3441526A1 (de) | 1984-11-14 | 1986-05-15 | Bayer Ag, 5090 Leverkusen | Triazolylmethylcarbinol-arylacetale |
US4603101A (en) | 1985-09-27 | 1986-07-29 | General Electric Company | Photoresist compositions containing t-substituted organomethyl vinylaryl ether materials |
CA1307695C (en) | 1986-01-13 | 1992-09-22 | Wayne Edmund Feely | Photosensitive compounds and thermally stable and aqueous developablenegative images |
US4898928A (en) | 1988-03-07 | 1990-02-06 | Sandoz Pharmaceuticals Corp. | Polyacetal and polyketal hydrogels formed from acetals or ketals and polyols |
DE59106903D1 (de) | 1990-09-06 | 1995-12-21 | Ciba Geigy Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung. |
US5204442A (en) | 1991-02-06 | 1993-04-20 | General Electric Company | Polyether polymers derived from 4,4"-dihydroxy-m-terphenyls |
DE4236106A1 (de) | 1992-10-26 | 1994-04-28 | Hoechst Ag | Azaaromatische Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung in flüssigkristallinen Mischungen |
DE4236103A1 (de) | 1992-10-26 | 1994-04-28 | Hoechst Ag | Verfahren zur Kreuzkupplung von aromatischen Boronsäuren mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten |
US5344742A (en) | 1993-04-21 | 1994-09-06 | Shipley Company Inc. | Benzyl-substituted photoactive compounds and photoresist compositions comprising same |
SI0736012T1 (en) | 1993-12-21 | 2001-02-28 | Boehringer Ingelheim Pharma | Anellated dihydropyridines and their use in the production of pharmaceutical preparations |
US5728835A (en) | 1993-12-27 | 1998-03-17 | Toa Eiyo, Ltd. | Substituted cyclic amine compound, production process thereof and pharmaceutical composition for circulatory organ use containing the same |
DE19502178A1 (de) | 1994-01-27 | 1995-08-03 | Hoechst Ag | Thiadiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Vorprodukte zur Herstellung von Flüssigkristallen |
DE4426671A1 (de) | 1994-07-28 | 1996-02-01 | Hoechst Ag | Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten |
EP0711804A3 (de) | 1994-11-14 | 1999-09-22 | Ciba SC Holding AG | Kryptolichtschutzmittel |
US5661035A (en) | 1995-06-07 | 1997-08-26 | The Regents Of The University Of California | Voltage sensing by fluorescence resonance energy transfer |
US6342379B1 (en) | 1995-06-07 | 2002-01-29 | The Regents Of The University Of California | Detection of transmembrane potentials by optical methods |
IL123701A (en) | 1995-10-13 | 2002-03-10 | Agrevo Uk Ltd | Heterocyclic fungicides and a number of new compounds |
WO1997023449A1 (en) | 1995-12-21 | 1997-07-03 | Rhone-Poulenc Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
US6008266A (en) | 1996-08-14 | 1999-12-28 | International Business Machines Corporation | Photosensitive reworkable encapsulant |
US7147983B1 (en) | 1996-10-07 | 2006-12-12 | Shipley Company, L.L.C. | Dyed photoresists and methods and articles of manufacture comprising same |
DE19710614A1 (de) | 1997-03-14 | 1998-09-17 | Hoechst Ag | (1,2,4)-Thiadiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
IT1299068B1 (it) | 1998-04-10 | 2000-02-07 | Chemi Spa | Legandi fosforati chirali e loro complessi organometallici, utili come catalizzatori in sintesi stereoselettive |
GC0000177A (en) | 1998-12-17 | 2006-03-29 | Smithkline Beecham | Thrombopoietin mimetics |
US6531291B1 (en) | 1999-11-10 | 2003-03-11 | The Trustees Of Columbia University In The City Of New York | Antimicrobial activity of gemfibrozil and related compounds and derivatives and metabolites thereof |
WO2001036386A1 (fr) | 1999-11-17 | 2001-05-25 | Sumitomo Pharmaceuticals Co., Ltd. | Traitement du diabete contenant un derive de dipiperazine |
US20020099070A1 (en) | 2000-08-02 | 2002-07-25 | Konstantinos Agrios | Dihydronaphthyridine potassium channel openers |
US6867250B1 (en) | 2000-10-30 | 2005-03-15 | Cytec Technology Corp. | Non-yellowing ortho-dialkyl aryl substituted triazine ultraviolet light absorbers |
JPWO2002043760A1 (ja) | 2000-12-01 | 2004-04-02 | 住友製薬株式会社 | 糖代謝活性化剤 |
US7091292B2 (en) | 2002-04-24 | 2006-08-15 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
US7060848B2 (en) | 2002-04-24 | 2006-06-13 | Symyx Technologies, Inc. | Bridged bi-aromatic catalysts, complexes, and methods of using the same |
CA2483192A1 (en) | 2002-04-24 | 2003-11-06 | Symyx Technologies, Inc. | Bridged bi-aromatic ligands, complexes, catalysts and processes for polymerizing and poymers therefrom |
US7232639B2 (en) | 2003-02-25 | 2007-06-19 | Nec Corporation | Monomer having fluorine-containing acetal or ketal structure, polymer thereof, and chemical-amplification-type resist composition as well as process for formation of pattern with use of the same |
US6878374B2 (en) | 2003-02-25 | 2005-04-12 | Nitto Denko Corporation | Biodegradable polyacetals |
CN1526752A (zh) * | 2003-03-05 | 2004-09-08 | 希普利公司 | 聚硅氧烷以及含有所述聚硅氧烷的光致抗蚀剂组合物的制备方法 |
WO2005042444A2 (ja) | 2003-11-04 | 2005-05-12 | Takasago Perfumery Co Ltd | 白金錯体及び発光素子 |
JP2006008953A (ja) | 2004-06-29 | 2006-01-12 | Fuji Photo Film Co Ltd | 保護用塗料組成物及び塗装物品 |
CN101160684A (zh) | 2005-03-02 | 2008-04-09 | U芝加哥阿谷尼有限公司 | 用于锂电池的充电过度保护的新型氧化还原穿梭化合物 |
US20090137681A1 (en) | 2005-04-08 | 2009-05-28 | David A Sinclair | Sirtuin Inhibiting Compounds |
WO2007099392A2 (en) | 2005-09-27 | 2007-09-07 | Swiss Federal Institute Of Technology | Convergent synthesis of carbohydrate building blocks |
DE102005050512A1 (de) | 2005-10-21 | 2007-04-26 | Clariant Produkte (Deutschland) Gmbh | Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolen |
JP5140824B2 (ja) | 2006-04-19 | 2013-02-13 | 国立大学法人 東京大学 | リゾホスファチジルスレオニンおよびその誘導体 |
US7875697B2 (en) | 2006-06-29 | 2011-01-25 | Medtronic, Inc. | Poly(orthoester) polymers, and methods of making and using same |
MX2008015765A (es) | 2006-07-27 | 2009-03-26 | Cv Therapeutics Inc | Inhibidores de aldh-2 en el tratamiento de adiccion. |
US8158810B2 (en) | 2006-07-27 | 2012-04-17 | Gilead Sciences, Inc. | ALDH-2 inhibitors in the treatment of addiction |
WO2008021048A2 (en) | 2006-08-07 | 2008-02-21 | President And Fellows Of Harvard College | Adp-ribosyltransferase based methods and compositions |
US7528203B2 (en) | 2006-09-14 | 2009-05-05 | Exxonmobil Chemical Patents Inc. | Cyclic olefin copolymers, and methods of making the same |
JP2008110944A (ja) | 2006-10-31 | 2008-05-15 | Taiyo Corp | 消臭剤組成物 |
WO2008070733A2 (en) | 2006-12-06 | 2008-06-12 | Phenomix Corporation | Macrocyclic hepatitis c serine protease inhibitors and uses therefor |
WO2008088690A2 (en) | 2007-01-12 | 2008-07-24 | Merck & Co., Inc. | A process for preparing diazabicyclo[3.3.1] nonane compounds |
TWI431071B (zh) | 2007-10-17 | 2014-03-21 | Clariant Finance Bvi Ltd | 用於彩色濾光片中的二酮基吡咯并吡咯顏料組成物 |
MX2010005047A (es) | 2007-11-06 | 2010-07-28 | Cv Therapeutics Inc | Inhibidores de aldh-2 en el tratamiento de enfermedades psiquiatricas. |
JP4601079B2 (ja) * | 2007-12-17 | 2010-12-22 | 東京エレクトロン株式会社 | 基板処理方法及び基板処理装置 |
JP2009209090A (ja) | 2008-03-04 | 2009-09-17 | Mitsui Chemicals Inc | 殺虫剤及び該殺虫剤に含まれる化合物、並びに該化合物の使用方法 |
DE102008015526B4 (de) | 2008-03-25 | 2021-11-11 | Merck Patent Gmbh | Metallkomplexe |
DE102008032090A1 (de) | 2008-07-08 | 2010-01-14 | Clariant International Ltd. | PR 254-Pigmentzubereitung zur Verwendung in Colorfiltern |
DE102008032092A1 (de) | 2008-07-08 | 2010-01-14 | Clariant International Ltd. | Binäre Diketopyrrolopyrrol-Pigmentzusammensetzung zur Verwendung in Colorfiltern |
US7993812B2 (en) * | 2009-07-23 | 2011-08-09 | International Business Machines Corporation | Calixarene blended molecular glass photoresists and processes of use |
JP2011074365A (ja) | 2009-09-02 | 2011-04-14 | Sumitomo Chemical Co Ltd | 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法 |
EP2550257B1 (en) | 2010-03-22 | 2016-12-21 | Lead Discovery Center GmbH | Pharmaceutically active disubstituted triazine derivatives |
WO2011159633A1 (en) | 2010-06-15 | 2011-12-22 | Amira Pharmaceuticals, Inc. | Inhalable formulations of lysophosphatdic acid receptor antagonists |
EP2585216B1 (en) | 2010-06-23 | 2019-11-20 | Johnson Matthey PLC | Pi-allylpalladium and pi-allylnickel complexes for use as catalysts in carbon-carbon and carbon-nitrogen coupling reactions |
WO2012004676A2 (en) | 2010-07-06 | 2012-01-12 | Ticona Gmbh | Process for producing high molecular weight polyethylene |
JP2013531111A (ja) | 2010-07-06 | 2013-08-01 | ティコナ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 高分子量ポリエチレンの繊維及び膜、それらの製造及び使用 |
CN102958959B (zh) | 2010-07-06 | 2015-11-25 | 提克纳有限公司 | 产生高分子量聚乙烯的方法 |
EP2591018A2 (en) | 2010-07-06 | 2013-05-15 | Ticona GmbH | Process for producing high molecular weight polyethylene |
WO2012006230A1 (en) | 2010-07-06 | 2012-01-12 | Ticona Gmbh | Process for producing high molecular weight polyethylene |
BR112012032832A2 (pt) | 2010-07-06 | 2016-11-08 | Ticona Gmbh | polietileno de ultra-alto peso molecular, sua produção e uso. |
EP2591022A2 (en) | 2010-07-06 | 2013-05-15 | Ticona GmbH | Shaped high molecular weight polyethylene articles, their production and use |
EP2458440A1 (en) | 2010-11-30 | 2012-05-30 | Rohm and Haas Electronic Materials LLC | Photoacid generators |
CN102584741A (zh) | 2011-01-06 | 2012-07-18 | 中国科学院上海药物研究所 | 酰胺类化合物及其制备方法、组合物和用途 |
EP2796928B1 (en) * | 2011-03-31 | 2015-12-30 | Fujifilm Corporation | Lithographic printing plate precursor and method of preparing the same |
-
2013
- 2013-07-16 US US13/943,007 patent/US9063420B2/en active Active
-
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- 2014-07-14 JP JP2014144245A patent/JP5913461B2/ja active Active
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- 2014-07-16 CN CN201410445524.1A patent/CN104330956B/zh active Active
- 2014-07-16 KR KR1020140090092A patent/KR101650326B1/ko active IP Right Grant
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53133429A (en) * | 1977-04-25 | 1978-11-21 | Hoechst Ag | Radiation sensitive copying conposite and method of forming relief |
JPS60205444A (ja) * | 1984-02-25 | 1985-10-17 | ヘキスト・アクチエンゲゼルシヤフト | 感放射組成物及び感放射記録材料 |
JPH03103856A (ja) * | 1989-09-09 | 1991-04-30 | Hoechst Ag | 陽画処理照射感応性混合物およびそれから製造した照射感応性複写材料 |
JP2003066610A (ja) * | 2001-08-27 | 2003-03-05 | Toppan Printing Co Ltd | ポリイミド樹脂及びこれを含有する感光性樹脂組成物 |
JP2003327686A (ja) * | 2002-05-09 | 2003-11-19 | Jsr Corp | レジスト材用単量体および酸解離性樹脂 |
JP2010113142A (ja) * | 2008-11-06 | 2010-05-20 | Sekisui Chem Co Ltd | ポジ型感光性組成物及び導電パターンの形成方法 |
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