CN105339457B - 用于增强化学物质产生的试剂 - Google Patents
用于增强化学物质产生的试剂 Download PDFInfo
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- CN105339457B CN105339457B CN201480036174.1A CN201480036174A CN105339457B CN 105339457 B CN105339457 B CN 105339457B CN 201480036174 A CN201480036174 A CN 201480036174A CN 105339457 B CN105339457 B CN 105339457B
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- reagent
- alkyl
- paint film
- wavelength
- hydrogen atom
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- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 53
- 230000002708 enhancing effect Effects 0.000 title claims abstract description 9
- 239000000126 substance Substances 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000003973 paint Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 239000002243 precursor Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000010894 electron beam technology Methods 0.000 claims description 17
- 229920002120 photoresistant polymer Polymers 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 230000008929 regeneration Effects 0.000 claims description 3
- 238000011069 regeneration method Methods 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 238000005530 etching Methods 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 13
- 230000005284 excitation Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000005670 electromagnetic radiation Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000012431 wafers Nutrition 0.000 description 6
- 239000003504 photosensitizing agent Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
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- 125000006239 protecting group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000012744 reinforcing agent Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- -1 aryl methanol Chemical compound 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 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
- 239000007848 Bronsted acid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- MWMWRSCIFDZZGW-UHFFFAOYSA-N (2-oxooxolan-3-yl) prop-2-enoate Chemical compound C=CC(=O)OC1CCOC1=O MWMWRSCIFDZZGW-UHFFFAOYSA-N 0.000 description 1
- CZJVBHWJFDFPSW-UHFFFAOYSA-N 2-[(3-hydroxy-1-adamantyl)methyl]prop-2-enoic acid Chemical class C1C(C2)CC3CC2(O)CC1(CC(=C)C(=O)O)C3 CZJVBHWJFDFPSW-UHFFFAOYSA-N 0.000 description 1
- VMODAALDMAYACB-UHFFFAOYSA-N 2-methyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2C3 VMODAALDMAYACB-UHFFFAOYSA-N 0.000 description 1
- XPWDSLOABSVORW-UHFFFAOYSA-N C(C)(C)(C)C1=C(C=CC=C1)IC1=C(C=CC=C1)C(C)(C)C Chemical compound C(C)(C)(C)C1=C(C=CC=C1)IC1=C(C=CC=C1)C(C)(C)C XPWDSLOABSVORW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical class C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 1
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical compound C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/24—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/38—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the fluorene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/40—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the anthracene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
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- 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
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- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- 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
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- G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
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Abstract
本发明公开了一种增强光酸产生剂的酸产生的试剂和含有所述试剂的组合物。
Description
相关申请案的交叉参考
本申请案根据35U.S.C.第119(e)章要求2013年6月24日提交的美国临时专利申请案第61/838,751号的权益,所述申请案的公开内容特此以全文引用的方式并入本文中。
技术领域
本发明的数个方面涉及增强化学物质如酸和碱的产生的试剂的领域。由所述试剂形成的中间物可充当同样增强化学物质产生的光敏化剂。
背景技术
现行高分辨率光刻工艺是基于化学放大型抗蚀剂(CAR)并且用以图案化尺寸小于100nm的特征。
形成尺寸小于100nm的图案特征的方法公开于US 7851252(2009年2月17日提交)中,其全文的内容以引用的方式并入本文中。
发明内容
本发明中公开了一种增强化学物质产生的试剂和一种组合物。所述试剂通常有助于布忍司特酸(Bronsted acid)或碱从前体产生。此外,所述试剂可以适用于产生路易斯酸(Lewis acid)和碱。所述试剂通常产生具有还原性特征的中间物(如羰游基自由基)且所述中间物增强酸从前体产生。换句话说,所述试剂充当酸产生增强剂(AGE)。
所述中间物转化成充当光敏化剂的产物。在形成所述产物之后,所述产物的照射产生其激发态,其激发态可将能量或电子转移到前体或接受来自前体的能量或电子。所述前体在接受能量或电子或供给能量或电子之后产生化学物质。由于AGE的数个实例需要有高电子供体特征来增强电子转移到前体,故所述AGE在芳环上具有至少一个供电子基团(如烷氧基和羟基)。化学物质与化合物的反应引起化合物的分解以及化学物质的再生。换句话说,所述试剂以化学放大方式增强化学物质的产生,即使在一组方法中改变激发方式。
所述AGE试剂的典型实例为含有芳基的甲醇。举例来说,含有试剂的组合物、将形成化学物质的前体以及将与所述化学物质反应的化合物可作为光致抗蚀剂施加以制造如半导体装置和电光装置的电子装置。举例来说,在组合物的涂料膜在第一步中曝露于极紫外线(EUV)光和电子束(EB)之后,涂料膜可曝露于强度高于EUV光或EB(如UV光和可见光)的强度的光。组合物可应用于涉及使用光酸产生剂(PAG)和含保护基(如酯基和醚基)的树脂的化学放大反应,所述保护基将通过与化学物质(如由PAG产生的酸)反应而分解。
作为典型AGE的芳基甲醇的氧化反应易于发生形成相应的羰基化合物。为了获得所述AGE的长期稳定性,AGE的羟基优选地利用保护基(如四氢吡喃基、酯基和醚基)保护。
在涉及本发明的一个方面的某些实施例中,试剂的特征在于:中间物将由所述试剂产生;所述中间物能够增强化学物质从前体产生;且由所述中间物产生的产物的共轭长度长于所述试剂的共轭长度。
在涉及本发明的一个方面的某些实施例中,试剂的特征在于:中间物将由所述试剂产生;所述中间物能够增强化学物质从前体产生;且由所述中间物产生的产物的最高占用分子轨道(HOMO)的水平高于所述试剂的最高占用分子轨道(HOMO)的水平。
关于上述试剂中的任一者,优选的是,化学物质与第一化合物或前体的反应将再生化学物质。
关于上述试剂中的任一者,优选的是,中间物将通过将能量馈送给试剂或接受所述能量的接受体来由所述试剂产生。
关于上述试剂中的任一者,优选的是。中间物具有还原性特征。
关于上述试剂中的任一者,优选的是,中间物为自由基。
关于上述试剂中的任一者,优选的是,中间物放出氢原子和具有还原性特征的氢离子中的至少一者。
所述中间物的一个实例为羰游基自由基,其可易于放出氢原子。
所述化学物质的一个实例为酸或碱。
关于上述试剂中的任一者,优选的是,能量的馈送通过所述试剂使用波长等于或短于15nm的光和电子束(EB)中的至少一者的第一照射来进行。
关于上述试剂中的任一者,优选的是,能量的馈送通过所述试剂使用波长为第一波长的第一光或电子束的第一照射来进行;且所述产物的第二照射能够增强化学物质从前体产生。
关于上述试剂中的任一者,优选的是,能量的馈送通过所述试剂使用波长为第一波长的第一光或电子束的第一照射来进行;且所述产物使用第二光的第二照射能够增强化学物质从前体产生。
关于上述试剂中的任一者,优选的是,所述第一光的第一波长短于所述第二光的第二波长。
在涉及本发明的一个方面的某些实施例中,组合物包括上述试剂和前体中的任一者。
关于所述组合物,优选的是,所述组合物进一步包括第一化合物。
关于所述组合物,优选的是,第一化合物能够与化学物质反应。
关于所述组合物,优选的是,所述产物的第二照射能够增强化学物质从前体产生。
关于所述组合物,优选的是,所述第二照射通过波长等于或长于100nm的第二光进行。
关于所述组合物,优选的是,所述第二照射通过波长等于或长于300nm的光进行。
关于所述组合物,优选的是,所述产物充当第二照射的敏化剂。
关于所述组合物,优选的是,所述产物能够通过所述第二照射激发以形成所述产物的激发态;且所述前体能够通过接受来自所述产物的激发态的电子来产生所述化学物质。
关于所述组合物,优选的是,所述产物能够通过所述第二照射激发以形成所述产物的激发态;所述前体能够通过接受来自所述产物的激发态的电子来产生所述化学物质;且所述第一化合物与所述化学物质的反应能够发生,同时所述反应伴有化学物质的再生。
在涉及本发明的一个方面的某些实施例中,组合物包括:由式(I)中的一者代表的试剂;和可充当酸的产生源的前体。
化学物质1
在式(I)中,优选的是,R1为氢原子;R2是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基;并且R3是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基。
关于所述组合物,优选的是,R2经由至少一个键连接于R3。
关于所述组合物,优选的是,R2和R3中的至少一者为芳香族基团。
关于所述组合物,优选的是,所述产物通过氧化中间物来形成。
在涉及本发明的一个方面的某些实施例中,组合物包括:试剂;和可通过接受能量或至少一个氢原子来产生酸的前体。优选的是,所述试剂包括:羟基;和含有键结于所述羟基的碳原子以及氢原子的第一环状部分;和由所述试剂形成的中间物转化成所述产物。
关于所述组合物,优选的是,所述试剂进一步包括第二环状部分;且所述第一环状部分含有至少两个还含于所述第二环状部分中的原子。
在涉及本发明的一个方面的某些实施例中,组合物包括:由式(II)中的一者代表的试剂;和充当酸的产生源的前体。
化学物质2
在式(II)中,优选的是,R1为氢原子;R2是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基;R3是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基;并且R4为羟基的保护基。
在涉及本发明的一个方面的某些实施例中,组合物包括:由式(III)中的一者代表的试剂;和可充当酸的产生源的前体。
化学物质3
在式(III)中,优选的是,R1为氢原子;R2是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基;R3是氢原子、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基或含有至少一个除碳原子和氢原子以外的原子的取代基;并且R4为含有碳原子的基团。
关于所述组合物,优选的是,R4为酯基、烷基和四氢吡喃基中的一者。
关于上述试剂中的任一者,优选的是,所述试剂为待利用酸或碱脱除保护基的基团。
关于上述组合物中的任一者,优选的是,所述试剂含有待利用由所述前体形成的化学物质脱除保护基的基团。
在涉及本发明的一个方面的某些实施例中,制造装置的方法在于所述方法通过使用所述组合物中的任一者进行。
在涉及本发明的一个方面的某些实施例中,一种方法包括:向基材涂覆根据技术方案15所述的组合物的溶液,使得包括所述组合物的涂料膜在所述基材上形成;且使用第一电磁射线和第一粒子射线中的至少一者第一照射所述涂料膜,使得所述涂料膜的第一部分经所述电磁射线和所述粒子射线中的至少一者照射,而所述涂料膜的第二部分不经所述电磁射线和所述粒子射线中的至少一者照射;使用第二电磁射线和第二粒子射线中的至少一者第二照射所述涂料膜;移除所述第一部分;且以蚀刻所述第1部分在上的所述基材的第3部分的方式对所述基材进行蚀刻。
关于所述方法,优选的是:波长为第一波长的第一电磁射线;波长为第二波长的第二电磁射线;且所述第一波长短于所述第二波长。
关于所述方法,优选的是,所述第一波长等于或短于15nm。
关于所述方法,优选的是:所述第一波长等于或短于15nm;且所述第二波长等于或长于300nm。
关于所述方法,优选的是,第二照射在无掩模的情况下进行。
在涉及本发明的一个方面的某些实施例中,上述方法中的任一者通过使用设备进行。
附图说明
在图中,说明了当前被视为实施本发明的最佳方式的内容。
[图1]图1展示使用包括酸产生增强剂的光致抗蚀剂的装置如集成电路(IC)的制造工艺。
具体实施方式
实验程序:
合成2,4-二甲氧基-4'-甲氧基二苯甲酮
将2.00g 2,4-二羟基-4'-羟基二苯甲酮、1.95g硫酸二甲酯和2.14g碳酸钾溶解于16.0g丙酮中。在回流温度下搅拌混合物8小时。此后,将混合物冷却到摄氏25度且其在添加80.0g水之后经进一步搅拌。接着,用20.0g乙酸乙酯萃取,且有机相用水洗涤。其后,蒸馏掉乙酸乙酯,且所得物通过硅胶柱色谱(乙酸乙酯:己烷=3:97)纯化。由此,获得1.43g 2,4-二甲氧基-4'-甲氧基二苯甲酮。
合成(2,4-二甲氧基苯基)-(4'-甲氧基苯基)-甲醇(实例1).
将1.0g 2,4-二甲氧基-4'-甲氧基二苯甲酮和0.01g氢氧化钾溶解于12.0g甲醇中。向甲醇溶液中添加0.42g硼氢化钠。在回流温度下搅拌混合物3小时。此后,向80g水中添加混合物。接着,用20.0g乙酸乙酯萃取,且有机相用水洗涤。其后,蒸馏掉乙酸乙酯。由此,获得0.90g(2,4-二甲氧基苯基)-(4'-甲氧基苯基)-甲醇。
化学物质4
实例1
制备含有5.0gα-甲基丙烯酰氧基-γ-丁内酯、6.03g 2-甲基金刚烷-2-甲基丙烯酸酯和4.34g 3-羟基金刚烷-1-甲基丙烯酸酯、0.51g二甲基-2,2'-偶氮双(2-甲基丙酸酯)和26.1g四氢呋喃的溶液。在搅拌和沸腾下持续4小时添加制备的溶液到放置在烧瓶中的20.0g四氢呋喃中。在添加制备的溶液之后,将混合物加热到回流后持续2小时,并且冷却到室温。逐滴添加混合物到含有160g己烷和18g四氢呋喃的混合液体中(在剧烈搅拌下)使共聚物沉淀。通过过滤来分离共聚物。共聚物的纯化通过在利用70g己烷洗涤两次之后真空干燥来进行,且由此获得8.5g白色共聚物粉末。
化学物质5
制备用于评估的样品(“评估样品”)
评估样品通过以下方式制备:将23.5mg(2,4-二甲氧基苯基)-(4'-甲氧基苯基)-甲醇、600mg树脂A和24.9mg九氟丁磺酸二苯基碘鎓盐作为光酸产生剂(PAG)溶解在8000mg环己酮中。
敏感性的评估
在将评估样品中的每一者施加到Si晶片之前,将六甲基二硅氮烷(HMDS,东京化工(Tokyo Chemical Industry))以2000rpm在Si晶片的表面上旋涂20秒且在摄氏110度下烘烤1分钟。接着,将评估样品中的每一者旋涂在已用HMDS以2000rpm处理20秒的Si晶片表面上以形成涂料膜。涂料膜的预烘烤在摄氏110度下进行60秒。接着,将评估样品的涂料膜曝露于来自EUV光源的极紫外线(EUV)输出。在EUV光曝露之后,在周围条件下用UV光照射涂料膜。在UV光曝露之后,曝露后烘烤(PEB)在摄氏100度下进行60秒。涂料膜用NMD-3(四甲基氢氧化铵2.38%,东京应化工(Tokyo Ohka Kogyo))在摄氏25度下显影60秒,且用去离子水冲洗10秒。使用膜厚度测量工具测量的涂料膜的厚度为约150nm。
敏感性(E0敏感性)通过使用30keV EBL系统JSM-6500F(日本电子株式会社(JEOL),光束电流:12.5pA,<1E-4Pa)与Beam Draw(东京技术(Tokyo Technology))以及使用FL-6BL(亮线主要为320nm到380nm,东芝(Toshiba))的UV曝露测量形成由2mm线(其中涂料膜的厚度不为零)和2mm空间(其中涂料膜的厚度为零)构成的图案的剂量大小来评估。
即使UV曝露是在无掩模的情况下进行,2mm空间也形成于已曝露于EUV光的涂料膜的部分中。这指示了充当UV光的光敏化剂的产物是在曝露于EUV光的部分中产生。
表1展示针对评估样品1到4测量的对应于E0敏感性的剂量大小。表1指示针对E0敏感性的UV曝露的剂量随着EUV光曝露的剂量的增加而减小。
[表1]
评估样品的根据EUV光和UV曝露的E0光的剂量
实例2、3、4和5中的每一者也优选地用作AGE代替(2,4-二甲氧基苯基)-(4'-甲氧基苯基)-甲醇。实例中的每一者转化成可在EUV光或电子束曝露之后充当光敏化剂的相应的酮。
化学物质6
实例1-5也利用保护基(如四氢吡喃基和酯)保护。
合成双-(4-甲氧基苯基)甲醇.
将2.0g 4,4'-二甲氧基二苯甲酮和0.02g氢氧化钾溶解于16.0g甲醇中。将0.94g硼氢化钠添加到甲醇中。在回流温度下搅拌混合物3小时。此后,将混合物添加到80g水中。接着,用20.0g乙酸乙酯萃取且有机相用水洗涤。其后,蒸馏掉乙酸乙酯。由此,获得1.79g双-(4-甲氧基苯基)甲醇。
合成2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃(实例6)
化学物质7
合成2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃(实例6)
实例6
将2.75g 2H-二氢吡喃和0.74g对甲苯磺酸吡啶鎓溶解于30.0g二氯甲烷中。经30分钟将利用8.0g二氯甲烷溶解的2.0g双-(4-甲氧基苯基)甲醇逐滴添加到含有2H-二氢吡喃和对甲苯磺酸吡啶鎓的混合物中,此后在摄氏25度下搅拌混合物3小时。此后,在添加3%碳酸钠水溶液之后进一步搅拌混合物。接着,用20.0g乙酸乙酯萃取,且有机相用水洗涤。其后,蒸馏掉乙酸乙酯。由此,获得1.99g 2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃。
制备评估样品5和6
通过将300mg树脂A、36.7mg九氟丁磺酸二苯基碘鎓作为光酸产生剂(PAG)和13.7mg香豆素6作为指示剂溶解于2000mg环己酮中来制备评估样品5。
通过将14.1mg 2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃、300mg树脂A、36.7mg九氟丁磺酸4,4'-二-(叔丁基苯基)碘鎓作为PAG和13.7mg香豆素6作为指示剂溶解于2000mg环己酮中来制备评估样品6。
评估酸产生的效率
通过旋涂评估样品5和6在4英寸石英晶片上形成膜。膜中的每一者通过EUV光光刻设备用量为0、10、20、30和40μC/cm2输出的EUV光照射。在EUV光照射之后,通过绘制534nm下的吸光度获得膜的效率,每个膜的吸光度分配到由对应量的EUV产生的质子化香豆素6的量。
表2展示了评估样品5和6的相对酸产生效率。在表2中,将评估样品5的酸产生效率用作基准。表2中所示的结果指示,酸产生效率通过由从2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃形成的羰游基自由基还原光酸产生剂而改良。这指示了2-[双-(4-甲氧基-苯基)-甲氧基]-四氢-吡喃的四氢吡喃基通过曝露EUV光产生的酸裂解且产生双-(4-甲氧基苯基)甲醇。
[表2]
表2评估样品5和6的相对酸产生效率
相对酸产生效率 | |
评估实例5 | 1.0 |
评估实例6 | 1.1 |
如由结果理解,具有还原性特征的利用酸可离解基团保护的反应中间物也视为增强酸产生的效率。
实例6与酸的反应产生相应的醇。相应的醇被氧化成可充当光敏化剂的相应的酮。因此,如果在含有实例6和PAG的溶液曝露于EUV光或电子束之后使用波长长于220nm的光照射,那么酸产生的效率被进一步增强。
包括通过利用上述程序的工艺获得的实例6作为AGE的光致抗蚀剂可应用于如集成电路(IC)的装置的制造工艺。
图1展示了使用包括酸产生增强剂(AGE)的光致抗蚀剂制造装置(如集成电路(IC))的工艺,所述酸产生增强剂通过所述工艺通过以上程序获得。
提供硅晶片。硅晶片的表面通过在氧气存在下加热硅晶片来氧化。
包括AGE、树脂A和PAG的化学放大组合物(CAR)的溶液通过旋涂涂覆到Si晶片的表面以形成涂料膜。涂料膜经预烘烤。
在预烘烤Si晶片之后,经由掩模使用EUV光照射涂料膜。树脂A的脱除保护基反应通过由光酸产生剂的光反应且利用AGE辅助生成的酸诱导。
可使用电子束代替EUV光。
在EUV照射涂料膜之后,在无任何掩模的情况下使用波长等于或长于300nm的光照射涂料膜。
已使用EUV光和波长等于或长于300nm的光照射的涂料膜的显影在预烘烤之后进行。
将涂料膜和硅晶片曝露于等离子体。此后,移除其余膜。
利用图1中所示的工艺制造电子装置,如集成电路。与现有光致抗蚀剂相比,装置归因于用光照射的劣化得到遏制,因为照射膜的时间缩短了。
AGE可键结到聚合物链。举例来说,实例1-6的母体部分中的至少每一者可经由醚基或酯基成为聚合物链。
Claims (8)
1.一种化学放大型光致抗蚀剂组合物,其包含试剂、前体及第一化合物,所述试剂包含选自由下述式(I)所表示的第一试剂、下述式(II)所表示的第二试剂、以及含有包含羟基和该羟基及氢原子所键合的碳原子的第一环状部分的第三试剂所组成的群中的任一试剂,
中间物由所述试剂产生,
所述中间物为羰游基自由基,其增强酸从前体产生,
由所述中间物产生的产物为酮,其具有的共轭长度长于所述试剂的共轭长度,
所述中间物的产生是由馈送能量而引起,
该能量的馈送是通过对所述试剂或接受所述能量的接受体使用波长15nm以下的光及电子束中的至少一者的第一照射来进行,
所述酸从前体产生是通过波长300nm以上的光的第二照射而增强,
所述第一化合物是通过所述酸进行脱除保护基反应的树脂,
所述化学放大型光致抗蚀剂组合物用于包含下述(1)至(3)的装置的制造方法,
(1)向基材涂覆包括所述化学放大型光致抗蚀剂组合物的涂料膜,使该涂料膜在所述基材上形成;
(2)使用波长15nm以下的光和电子束中的至少一者第一照射所述涂料膜,使得所述涂料膜的第一部分经所述波长15nm以下的光和电子束中的至少一者照射,而所述涂料膜的第二部分不经所述波长15nm以下的光和电子束中的至少一者照射;
(3)使用波长300nm以上的光第二照射所述涂料膜,
[化1]
所述式中,R1为氢原子,
R2为苯基、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基、或含有至少一个除碳原子及氢原子以外的原子的取代基,
R3为氢原子、苯基、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基、或含有至少一个除碳原子及氢原子以外的原子的取代基,
[化2]
所述式中,R1为氢原子,
R2为苯基、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基、或含有至少一个除碳原子及氢原子以外的原子的取代基,
R3为氢原子、苯基、烷基羰基、芳基羰基、烷基、烯基、芳烷基、炔基、含有环状或多环状部分的烷基、或含有至少一个除碳原子及氢原子以外的原子的取代基,
R4为羟基的保护基或包含碳原子的基。
2.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中R2经由至少一个键连接于R3。
3.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中R2及R3中的至少一者为芳香族基团。
4.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中R4为酯基、烷基及四氢吡喃基中的一者。
5.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中所述化学物质与第一化合物或所述前体的反应再生所述化学物质。
6.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中所述产物是通过所述中间物的氧化而产生。
7.根据权利要求1所述的化学放大型光致抗蚀剂组合物,其中所述第三试剂进一步包括第二环状部分,
所述第一环状部分含有至少两个还含于所述第二环状部分中的原子。
8.一种制造装置的方法,所述方法包含:
向基材涂覆根据权利要求1至7中任一项所述的化学放大型光致抗蚀剂组合物的溶液,使得包括所述组合物的涂料膜在所述基材上形成;且
使用波长15nm以下的光和电子束中的至少一者第一照射所述涂料膜,使得所述涂料膜的第一部分经所述波长15nm以下的光和电子束中的至少一者照射,而所述涂料膜的第二部分不经所述波长15nm以下的光和电子束中的至少一者照射;
使用波长300nm以上的光第二照射所述涂料膜;
移除所述第一部分;且
以蚀刻所述第1部分在上的所述基材的第3部分的方式对所述基材进行蚀刻。
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WO2014208102A1 (en) * | 2013-06-27 | 2014-12-31 | Toyo Gosei Co., Ltd. | Reagent for Enhancing Generation of Chemical Species |
US10031416B2 (en) | 2013-08-07 | 2018-07-24 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
CN103654412B (zh) | 2013-08-08 | 2016-04-20 | 宋剑芳 | 一种便携式手工操作咖啡机 |
US9567277B2 (en) | 2013-10-08 | 2017-02-14 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
JP2015134904A (ja) | 2013-11-18 | 2015-07-27 | 東洋合成工業株式会社 | 化学種発生向上化合物 |
CN106030417B (zh) * | 2014-02-21 | 2020-02-28 | 东京毅力科创株式会社 | 光增感化学放大型抗蚀剂材料及使用了其的图案形成方法、以及半导体器件、光刻用掩模和纳米压印用模板的制造方法 |
EP3109703B1 (en) * | 2014-02-21 | 2020-12-30 | Tokyo Electron Limited | Photosensitization chemical-amplification type resist material, and method for forming pattern using same |
JP6175455B2 (ja) * | 2015-01-22 | 2017-08-02 | 東京エレクトロン株式会社 | レジストパターン形成方法 |
JP6512994B2 (ja) * | 2015-08-20 | 2019-05-15 | 国立大学法人大阪大学 | 化学増幅型レジスト材料 |
JP6774814B2 (ja) * | 2015-08-20 | 2020-10-28 | 国立大学法人大阪大学 | 化学増幅型レジスト材料及びパターン形成方法 |
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US20170059992A1 (en) * | 2015-08-26 | 2017-03-02 | Jsr Corporation | Resist pattern-forming method and chemically amplified radiation-sensitive resin composition |
KR20170031053A (ko) | 2015-09-10 | 2017-03-20 | 제이에스알 가부시끼가이샤 | 레지스트 패턴 형성 방법 |
JP6507958B2 (ja) | 2015-09-10 | 2019-05-08 | Jsr株式会社 | 化学増幅型レジスト材料及びレジストパターン形成方法 |
US10018911B2 (en) | 2015-11-09 | 2018-07-10 | Jsr Corporation | Chemically amplified resist material and resist pattern-forming method |
US9989849B2 (en) * | 2015-11-09 | 2018-06-05 | Jsr Corporation | Chemically amplified resist material and resist pattern-forming method |
KR102170659B1 (ko) * | 2015-11-25 | 2020-10-27 | 오사카 유니버시티 | 레지스트패턴 형성방법 및 레지스트재료 |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2722264C2 (de) | 1977-05-17 | 1984-06-28 | Merck Patent Gmbh, 6100 Darmstadt | Verwendung von substituierten Oxyalkylphenonen als Photosensibilisatoren |
JP3042701B2 (ja) * | 1990-10-30 | 2000-05-22 | 株式会社日立製作所 | パターン形成法 |
JPH07239547A (ja) * | 1993-04-16 | 1995-09-12 | Hitachi Ltd | レジスト及びそのパターン形成方法 |
JPH10293396A (ja) * | 1997-04-17 | 1998-11-04 | Konica Corp | 画像形成材料及び画像形成方法 |
EP0919867B1 (de) | 1997-11-28 | 2003-05-21 | Infineon Technologies AG | Chemisch verstärkter Resist für die Elektronenstrahllithographie |
JP3517144B2 (ja) * | 1998-01-30 | 2004-04-05 | 株式会社東芝 | 感光性組成物 |
US6177229B1 (en) | 1998-01-30 | 2001-01-23 | Kabushiki Kaisha Toshiba | Photosensitive composition |
JP2002311586A (ja) * | 2001-04-18 | 2002-10-23 | Fuji Photo Film Co Ltd | 電子線又はx線用ネガ型レジスト組成物 |
JP4079729B2 (ja) * | 2002-09-09 | 2008-04-23 | 富士フイルム株式会社 | ネガ型レジスト組成物 |
US7514764B2 (en) | 2005-03-23 | 2009-04-07 | Wisconsin Alumni Research Foundation | Materials and methods for creating imaging layers |
US20060269879A1 (en) | 2005-05-24 | 2006-11-30 | Infineon Technologies Ag | Method and apparatus for a post exposure bake of a resist |
JP2005284322A (ja) * | 2005-06-27 | 2005-10-13 | Konica Minolta Holdings Inc | 樹脂フィルムの製造方法 |
JP5421585B2 (ja) * | 2008-12-24 | 2014-02-19 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物 |
US8334986B2 (en) * | 2010-02-25 | 2012-12-18 | Corning Incorporated | Methods and apparatus for the measurement of film thickness |
US8124319B2 (en) * | 2010-04-12 | 2012-02-28 | Nanya Technology Corp. | Semiconductor lithography process |
US20120040288A1 (en) * | 2010-08-11 | 2012-02-16 | Microchem Corp. | Epoxy formulations with controllable photospeed |
JP2012168526A (ja) * | 2011-01-26 | 2012-09-06 | Sanyo Chem Ind Ltd | 感光性組成物 |
JP5795221B2 (ja) * | 2011-09-26 | 2015-10-14 | 株式会社東芝 | パターン形成方法 |
JP5261756B1 (ja) | 2012-03-30 | 2013-08-14 | 株式会社フジクラ | 多層配線基板 |
KR101779683B1 (ko) * | 2013-02-20 | 2017-09-18 | 오사카 유니버시티 | 레지스트패턴 형성방법, 레지스트잠상 형성장치, 레지스트패턴 형성장치 및 레지스트재료 |
CN105308146A (zh) | 2013-05-13 | 2016-02-03 | 东洋合成工业株式会社 | 试剂和抗蚀剂组合物 |
CN105339457B (zh) | 2013-06-24 | 2018-07-20 | 东洋合成工业株式会社 | 用于增强化学物质产生的试剂 |
US20150060728A1 (en) | 2013-09-05 | 2015-03-05 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
US9567277B2 (en) | 2013-10-08 | 2017-02-14 | Toyo Gosei Co., Ltd. | Reagent for enhancing generation of chemical species |
JP2015134904A (ja) | 2013-11-18 | 2015-07-27 | 東洋合成工業株式会社 | 化学種発生向上化合物 |
JP2015200874A (ja) | 2014-02-21 | 2015-11-12 | 東洋合成工業株式会社 | 化学種発生向上剤 |
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JP2016528305A (ja) | 2016-09-15 |
JP6525269B2 (ja) | 2019-06-05 |
US9650357B2 (en) | 2017-05-16 |
KR20160023728A (ko) | 2016-03-03 |
US20160194300A1 (en) | 2016-07-07 |
WO2014208076A1 (en) | 2014-12-31 |
TW201512162A (zh) | 2015-04-01 |
CN105339457A (zh) | 2016-02-17 |
TWI642654B (zh) | 2018-12-01 |
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