JPH0437760A - Photosensitive resin composition - Google Patents
Photosensitive resin compositionInfo
- Publication number
- JPH0437760A JPH0437760A JP2145117A JP14511790A JPH0437760A JP H0437760 A JPH0437760 A JP H0437760A JP 2145117 A JP2145117 A JP 2145117A JP 14511790 A JP14511790 A JP 14511790A JP H0437760 A JPH0437760 A JP H0437760A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- alkaline
- compd
- radiation
- photosensitive resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims description 17
- 230000005855 radiation Effects 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- -1 m-substituted benzene ring Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000001312 dry etching Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 239000012953 triphenylsulfonium Substances 0.000 description 2
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 2
- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- WZKZYRSMAQLVTF-UHFFFAOYSA-N (2-butylphenyl)-phenyliodanium Chemical compound C(CCC)C1=C(C=CC=C1)[I+]C1=CC=CC=C1 WZKZYRSMAQLVTF-UHFFFAOYSA-N 0.000 description 1
- OYWSURWXROADBH-UHFFFAOYSA-N (2-nitrophenyl)methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O OYWSURWXROADBH-UHFFFAOYSA-N 0.000 description 1
- FTEDICXUYBLEMB-UHFFFAOYSA-N 1,2-benzoxathiine Chemical compound C1=CC=C2OSC=CC2=C1 FTEDICXUYBLEMB-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- IYUOYLLVOZNGKW-UHFFFAOYSA-N 2-azidonaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(N=[N+]=[N-])=CC(=O)C2=C1 IYUOYLLVOZNGKW-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- IIGPLHDJKDEXJA-UHFFFAOYSA-N 2h-1,2,3-benzoxadiazine Chemical compound C1=CC=C2C=NNOC2=C1 IIGPLHDJKDEXJA-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- DMMLYDCVMZEUMT-UHFFFAOYSA-N benzo[h]cinnoline Chemical compound C1=NN=C2C3=CC=CC=C3C=CC2=C1 DMMLYDCVMZEUMT-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- YCZWJBIXAUQULS-UHFFFAOYSA-M bis(4-methylphenyl)iodanium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1[I+]C1=CC=C(C)C=C1 YCZWJBIXAUQULS-UHFFFAOYSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
- LZGYEBMWMJOPPV-UHFFFAOYSA-N dioxadiazine Chemical compound O1ON=NC=C1 LZGYEBMWMJOPPV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005553 polystyrene-acrylate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
この発明は１例えば超ＬＳＩなどの半導体デバイスの微
細パターンを形成するために使用する放射線感応性レジ
ストに用いる、感光性樹脂組成物量するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Fields] This invention relates to the production of photosensitive resin compositions used in radiation-sensitive resists used for forming fine patterns of semiconductor devices such as VLSIs. be.
［従来の技術］
半導体デバイスの高集積化が求められる中、クォーター
ミクロンレベルの微細加工技術の開発が進められている
。この技術を実現するために、いくつかの手法が検討さ
れているが、なかでも光リソグラフィー技術で使用する
光源を短波長化するためにエキシマレーザを露光線源に
使用したり、光学干渉などの問題が無視できる電子線、
Ｘ線を露光線源に使用するなどの露光技術が注目されて
いる。[Background Art] Amid the demand for higher integration of semiconductor devices, development of microfabrication technology at the quarter-micron level is progressing. Several methods are being considered to realize this technology, including the use of an excimer laser as an exposure source to shorten the wavelength of the light source used in optical lithography, and the use of optical interference. Electron beams with negligible problems,
Exposure techniques that use X-rays as an exposure source are attracting attention.
従来、光リソグラフィー用のレジストとして、ノボラッ
ク樹脂とナフトキノンアジドとからなるしシストが知ら
れており、それらは、高解像度、ドライエツチング耐性
、高感度など、優れた特性を有している。BACKGROUND ART Hitherto, as a resist for photolithography, a cyst made of a novolac resin and naphthoquinone azide has been known, and these have excellent properties such as high resolution, dry etching resistance, and high sensitivity.
しかしながら、露光線源の波長が短波長化するにしたが
って感光波長の不適合や、短波長に対するレジスト自身
の透過率の不良などの間層が発生する。However, as the wavelength of the exposure radiation source becomes shorter, problems such as incompatibility of the sensitizing wavelength and poor transmittance of the resist itself to shorter wavelengths occur.
また、電子線、Ｘ線用のレジストとして、ポリメタクリ
レート樹脂やポリオレフィンスルホン樹脂などのポジ型
レジストや、クロルメチル化ポリスチレンなどのネガ型
レジストが開発されている。しかし、前者はドライエツ
チング耐性の低さと低感度という欠点を、後者は現像液
による膨潤のための解像度低下という欠点を持っている
。Furthermore, as resists for electron beams and X-rays, positive resists such as polymethacrylate resins and polyolefin sulfone resins, and negative resists such as chloromethylated polystyrene have been developed. However, the former has the disadvantages of low dry etching resistance and low sensitivity, and the latter has the disadvantage of reduced resolution due to swelling by the developer.
さらに特開昭６０−１７５０４６号公報には、露光前は
アルカリ溶液に対して溶解抵抗を持ち、放射線の露光を
受けるとその部分がアルカリ可溶性となる。アルカリ可
溶性フェノール樹脂と放射線感応性オニウム塩との組成
物が開示されている。また特開昭６３−５９１３１号公
報には、アルカリ可溶性の高分子化合物と、高エネルギ
ー放射線の照射によってエステルが分解し、カルボン酸
を生成するアルカリ不溶性有機酸エステルとの組成物が
開示されており、いずれも高感度のレジストを得るのが
目的である。Furthermore, Japanese Patent Application Laid-open No. 60-175046 discloses that before exposure, the material has dissolution resistance to an alkaline solution, and when exposed to radiation, that portion becomes alkali-soluble. Compositions of alkali-soluble phenolic resins and radiation-sensitive onium salts are disclosed. Furthermore, JP-A-63-59131 discloses a composition of an alkali-soluble polymer compound and an alkali-insoluble organic acid ester whose ester is decomposed by irradiation with high-energy radiation to produce a carboxylic acid. The purpose of both methods is to obtain a highly sensitive resist.
一方、レジストの欠点を補うための、レジストプロセス
の検討も行われており、半導体基板上に厚い平坦化有機
層を形成し、上層のレジストパターンをドライエツチン
グによって順次下層に転写し、アスペクト比の高いレジ
ストパターンを形成するという多層プロセスが開発され
ている。On the other hand, in order to compensate for the deficiencies of resist, studies are being conducted on resist processes, in which a thick planarized organic layer is formed on a semiconductor substrate, and the resist pattern on the upper layer is sequentially transferred to the lower layer by dry etching to improve the aspect ratio. Multilayer processes have been developed to form high resist patterns.
口発明が解決しようとする課題］
しかし、上記公報に開示されている組成物は、諸性能の
ある程度の向上はみられるものの、実用的なレベルにま
で向上させることは困難であり、又多層化する方法は、
レジストパターンの転写を行うためにドライエツチング
処理を数回行わねばならず、きわめて繁雑な工程処理と
長い処理時間を必要とするという課題がある。[Problems to be Solved by the Invention] However, although the composition disclosed in the above publication shows some improvement in various performances, it is difficult to improve it to a practical level, and it is difficult to improve it to a practical level. The way to do it is
In order to transfer the resist pattern, dry etching processing must be performed several times, which poses a problem in that extremely complicated process processing and long processing time are required.
この発明は、かかる課題を解決するためになされたもの
で、放射線露光に対する高い感度と、クオターミクロン
レベルの解像度を有するポジ型の放射線感応レジストを
得ることのできる感光性樹脂組成物提供することを目的
とする。The present invention was made in order to solve these problems, and it is an object of the present invention to provide a photosensitive resin composition capable of obtaining a positive radiation-sensitive resist having high sensitivity to radiation exposure and resolution at the quarter micron level. With the goal.
［課題を解決するための手段］
この発明の感光性樹脂組成物は、アルカリ可溶性高分子
化合物、放射線に感光し酸を発生する化合物並びに下記
一般式（ｆ）および（ＩＩ）で示される化合物の内の少
なくとも一種を含有するものである。[Means for Solving the Problems] The photosensitive resin composition of the present invention contains an alkali-soluble polymer compound, a compound that is sensitive to radiation and generates an acid, and a compound represented by the following general formulas (f) and (II). It contains at least one of the following.
Ａｒ（Ｘ−Ｃ−Ｒ２）＊ （１
）Ｙ（Ａｒ（Ｘ−Ｃ−Ｒ２）ａｈ （
Ｉｆ ）■
（式中Ａｒは一置換のベンゼン環または複素環化合物を
示し、Ｙは一、−０−、−５Ｏ２−、−ＣＨ２−、−Ｃ
ｏ−、−Ｃ（ＣＨ３）２−および−Ｃ（ＣＦ３）２−（
７）内の一種を示し、Ｘは−ｃｏｏ−，−ｏｃｏ。Ar(X-C-R2)* (1
)Y(Ar(X-C-R2)ah (
If)
o-, -C(CH3)2- and -C(CF3)2-(
7), X is -coo-, -oco.
、５０３−の内の一種を示し、Ｒ１，Ｒ２，Ｒ３は同一
であっても異なっていてもよく、各々水素原子、アルキ
ル基、アルコキシ基、アルケニル基５アルキニル基、フ
ェニル基、置換フェニル基を示し、またこれらのうち２
つがａｈａをなしていてもよい、但しｍは１から４の整
数を示す、）
［作用］
こ、の発明において、アルカリ可溶性の高分子化合物は
丘記一般式（１）および（■）で表される化合物の内の
少なくとも一種との間で相互作用を及ぼひ合い、アルカ
リ水溶液に不溶となる。しかし、放射線の照射を受ける
と、共存している放射線を受けて酸を発生する化合物か
ら発生した酸の効果により、上記一般式（１）および（
ＩＩ）で表される化合物の内の少なくとも一種が分解し
て、放射線の照射を受けた部分がアルカリ可溶性になる
。その結果ポジ型パターン形成が可能となる。この分解
反応が起こるためには酸の発生が必須であるが、加熱工
程を加えることにより大幅な感度向上が可能となる場合
が多い。, 503-, and R1, R2, and R3 may be the same or different, and each represents a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, a phenyl group, or a substituted phenyl group. and 2 of these
may form aha, provided that m represents an integer from 1 to 4) [Function] In this invention, the alkali-soluble polymer compound is represented by the general formulas (1) and (■). It interacts with at least one of the compounds in the alkaline solution and becomes insoluble in the alkaline aqueous solution. However, when irradiated with radiation, the above general formulas (1) and (
At least one of the compounds represented by II) decomposes, and the portion irradiated with radiation becomes alkali-soluble. As a result, positive pattern formation becomes possible. Although acid generation is essential for this decomposition reaction to occur, it is often possible to significantly improve sensitivity by adding a heating step.
［実施例］
この発明に係わる上記一般式（’Ｉ ）および（ＩＩ）
で表される化合物は、Ｘが−０００−である場合は各々
該当するカルボン酸ハロゲン化物とアルコールを第３級
アミン中で縮合反応させる一般的な方法で合成でき、−
ｏｃｏｏ−である場合は各々該当するヒドロキシ化合物
と炭酸ハロゲン化物を第３級アミン中で縮合反応させる
方法あるいは該当するヒドロキシ化合物とジカーボネイ
トを縮合する方法によって合成でき、−５０３−である
場合は各々該当するスルホン酸ハロゲン化物アルコール
を第３級アミン中で縮合反応させる方法あるいは、スル
ホン酸銀塩と臭化物とを縮合反応させる方法によって合
成することができる。上記一般式（１）および（ＩＩ）
で表される化合物におけるＡｒは、例えばベンゼン、ナ
フタレン、アントラセン、ベンゾフェノン、ナフトキノ
ン、アントラキノン、ピリジン、ピラジン、ピリミジン
、ピリダジン、トリアジン、テトラジン、ビロール、イ
ミダゾール、ピラゾール、トリアゾール、フェナントレ
ン、フェナントレン、ベンゾシンノリン、キノキサリン
、フェナジン、アザベンゾナフテン、ポリアザフェナン
トレン、オキサジアジン、ベンゾオキサジアジン、ジオ
キサジアジン、インドール、ベンゾイミダゾール、カル
バソール、キノリン、アクリジン、ピロコリン、フラン
、ベンゾフラン、クロモン、クロメン、キサントン、チ
オフェン、ベンゾチオフェン、オキサゾール、イソオキ
サゾール、チアゾール、ベンゾチアゾール、オキサゾリ
ン、オキサゾリジン、ベンゾオキサチイン、イサチン、
インドレニン、ピペリドン、イソキノリン、アクリドン
、トロビノン、フラボン、ピロン、ピロリドン＝４Ｈ−
ビランー４−オンなどがあげられ、これらはアルキル基
、アルケニル基、アルキニル基、アルコキシ基、ハロゲ
ン原子、などで置換されていてもよい。[Example] The above general formulas ('I) and (II) according to this invention
When X is -000-, the compound represented by can be synthesized by a general method of condensing the corresponding carboxylic acid halide and alcohol in a tertiary amine, and -
If it is ocoo-, it can be synthesized by a method of condensing the corresponding hydroxy compound and a carbonic acid halide in a tertiary amine, or by a method of condensing the corresponding hydroxy compound and dicarbonate, and if it is -503-, each It can be synthesized by a method in which a corresponding sulfonic acid halide alcohol is subjected to a condensation reaction in a tertiary amine, or by a method in which a sulfonic acid silver salt and a bromide are subjected to a condensation reaction. General formulas (1) and (II) above
Ar in the compound represented by is, for example, benzene, naphthalene, anthracene, benzophenone, naphthoquinone, anthraquinone, pyridine, pyrazine, pyrimidine, pyridazine, triazine, tetrazine, virol, imidazole, pyrazole, triazole, phenanthrene, phenanthrene, benzocinnoline, Quinoxaline, phenazine, azabenzonaphthene, polyazaphenanthrene, oxadiazine, benzoxadiazine, dioxadiazine, indole, benzimidazole, carbazole, quinoline, acridine, pyrocholine, furan, benzofuran, chromone, chromene, xanthone, thiophene, benzothiophene, oxazole , isoxazole, thiazole, benzothiazole, oxazoline, oxazolidine, benzoxathiin, isatin,
Indolenine, piperidone, isoquinoline, acridone, trobinone, flavone, pyrone, pyrrolidone = 4H-
Examples include bilan-4-one, which may be substituted with an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a halogen atom, or the like.
この発明に係わるアルカリ可溶性の高分子化合物（ベー
スポリマー）としては１例えば−０Ｈ１−ＣＯＯＨ５Ｎ
Ｈ２などのようなアルカリ可溶性の官能基を有する高分
子化合物（共重合体を含む）を任意に使用することがで
き、例えばポリアクリル酸、ポリメタクリル酸、ポリ−
α−クロロアクリル酸、ポリヒドロキシスチレン、ポリ
−α−メチルヒドロキシスチレン、ポリスチレンカルボ
ン酸、ポリアミノスチレン、ポリアリルアミンなどの単
独重合体あるいはこれらとポリスチレンまたはポリメチ
ルメタクリレートなどとの共重合体、フェノールノボラ
ック清脂、クレゾールノボラック樹脂、ナフトールノボ
ラック樹脂などが挙げられ、これら２種以上を併せて用
いでもよい。The alkali-soluble polymer compound (base polymer) according to this invention is 1, for example -0H1-COOH5N.
Polymer compounds (including copolymers) having alkali-soluble functional groups such as H2 can be optionally used, such as polyacrylic acid, polymethacrylic acid, poly-
Homopolymers of α-chloroacrylic acid, polyhydroxystyrene, poly-α-methylhydroxystyrene, polystyrene carboxylic acid, polyaminostyrene, polyallylamine, etc. or copolymers of these with polystyrene or polymethyl methacrylate, etc., phenol novolac Examples include oil, cresol novolac resin, naphthol novolac resin, and two or more of these may be used in combination.
この発明に係わる放射線の照射を受けて酸を発生する化
合物（光酸発生剤）としては、例えばトリフェニルスル
ホニウムテトラフルオロボレイト、トリフェニルスルホ
ニウムへキサフルオロアンチモネイト、トリフェニルス
ルホニウムへキサフルオロアルシネイト、トリフェニル
スルホニウムへキサフルオロホスフェイト、トリフェニ
ルスルホニウムトリフルオロスルホネイト、４−チオフ
ェノキシジフェニルスルホニウムテトラブルオロボレイ
ト、４−千オフ二ノキシジフェニルスルホニウムヘキサ
フルオロアンチモネイト、４−千オフェノキシジフェニ
ルスルホニウムヘキサフルオロアルシネイト、４−千オ
フェノキシジフェニルスルホニウムへキサフルオロホス
フェイト、４−千オフエノキシジフェニルスルホニウム
トリフルオロスルホネイト、４−ｔｅｒｔ−プチルフェ
ニルジフェニルスルホニウムテトラフルオロボレイト、
４−ｔｅｒｔ−プチルフェニルジフェニルスルホニウム
ヘキサフルオロアンチモネイト、４−ｔｅｒｔ、−ブチ
ルフエニルジフェニルスルホニウムヘキサフルオロアル
シネイト、４−ｔ、ｅｒｔ、−ブチルフエニルジフェニ
ルスルホニウムへキサフルオロホスフェイト、４−ｔ、
ｅｒｔ−ブチルフェニルジフェニルスルホニウムトリフ
ルオロスルホネイト、トリス（４−メチルフェニル）ス
ルホニウムテトラフルオロボレイト５トリス（４−メチ
ルフェニル）スルホニウムヘキサフルオロアンチモネイ
ト、トリス（４−メチルフェニル）スルホニウムヘキサ
フルオロアルシネイト、トリス（４−メチルフェニル）
スルホニウムへキサフルオロホスフェイト、トリス（４
−メチルフェニル）スルホニウムトリフルオロスルホネ
イト、トリス（４−メトキシフェニル）スルホニウムテ
トラフルオロボレイト、トリス（４−メトキシフェニル
）スルホニウムヘキサフルオロアンチモネイト、トリス
（４−メトキシフェニル）スルホニウムヘキサフルオロ
アルシネイト、トリス（４−メトキシフェニル）スルホ
ニウムへキサフルオロホスフェイト、トリス（４−メト
キシフェニル）スルホニウムトリフルオロスルホネイト
、ジフェニルヨウドニウムテトラフルオロボレイト、ジ
フェニルヨウドニウムヘキサフルオロアンチモネイト、
ジフェニルヨウドニウムヘキサフルオロアルシネイト、
ジフェニルヨウドニウムへキサフルオロホスフェイト５
ジフエニルヨウドニウムトリフルオロスルホネ−１’
）、３，３’−ジニトロジフェニルヨウドニウムテトラ
フルオロボレイト、３．３’−ジニトロジフェニルヨウ
ドニウムヘキサフルオロアンチモネイト、３．３’−ジ
ニトロジフェニルヨウドニウムヘキサフルオロアルシネ
イト、３．３’−ジニトロジフェニルヨウドニウムへキ
サフルオロホスフェイト、３．３’−ジニトロジフェニ
ルヨウドニウムトリフルオロスルホネイト、４．４’−
ジメチルジフェニルヨウドニウムテトラフルオロボレイ
ト、４．４’−ジメチルジフェニルヨウドニウムヘキサ
フルオロアンチモネイト、４．４’−ジメチルジフェニ
ルヨウドニウムヘキサフルオロアルシネイト、４．４’
−ジメチルジフェニルヨウドニウムへキサフルオロホス
フェイト、４．４’−ジメチルジフェニルヨウドニウム
トリフルオロスルホネイト、４．４′−ジｔｅｒｔ−プ
チルジフェニルヨウドニウムテトラフルオ口ボレイト、
４．４’−ジｔｅｒｔ−プチルジフェニルヨウドニウム
ヘキサフルオロアンチモネイト、４゜４′−ジｔｅｒｔ
−プチルジフェニルヨウドニウムヘキサブルオロアルシ
ネイト、４．４’−ジｔｅｒｔ−プチルジフェニルヨウ
ドニウムへキサフルオロホスフェイト、４゜４′−ジし
ｃｒｔ−プチルジフェニルヨウドニウムトリフルオロス
ルホネイトなどのオニウム塩や、２，４，６．−トリス
（トリクロロメチル）トリアジン、２−アリル４．６−
ビス（トリクロロメチル）トリアジン、α、α、α。Examples of compounds (photoacid generators) that generate acid upon irradiation with radiation according to this invention include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, and triphenylsulfonium hexafluoroarsinate. , triphenylsulfonium hexafluorophosphate, triphenylsulfonium trifluorosulfonate, 4-thiophenoxydiphenylsulfonium tetrafluoroborate, 4-thousofenoxydiphenylsulfonium hexafluoroantimonate, 4-thousofenoxydiphenylsulfonium hexafluoroarcinate, 4-thousophenoxydiphenylsulfonium hexafluorophosphate, 4-thousophenoxydiphenylsulfonium trifluorosulfonate, 4-tert-butylphenyldiphenylsulfonium tetrafluoroborate,
4-tert-butylphenyldiphenylsulfonium hexafluoroantimonate, 4-tert, -butylphenyldiphenylsulfonium hexafluoroarsinate, 4-t, ert, -butylphenyldiphenylsulfonium hexafluorophosphate, 4-t,
ert-butylphenyldiphenylsulfonium trifluorosulfonate, tris(4-methylphenyl)sulfonium tetrafluoroborate 5 tris(4-methylphenyl)sulfonium hexafluoroantimonate, tris(4-methylphenyl)sulfonium hexafluoroarsinate, Tris (4-methylphenyl)
Sulfonium hexafluorophosphate, tris(4
-Methylphenyl)sulfonium trifluorosulfonate, tris(4-methoxyphenyl)sulfonium tetrafluoroborate, tris(4-methoxyphenyl)sulfonium hexafluoroantimonate, tris(4-methoxyphenyl)sulfonium hexafluoroarsinate, tris (4-methoxyphenyl)sulfonium hexafluorophosphate, tris(4-methoxyphenyl)sulfonium trifluorosulfonate, diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluoroantimonate,
diphenyliodonium hexafluoroarsinate,
Diphenyliodonium hexafluorophosphate 5
Diphenyliodonium trifluorosulfone-1'
), 3,3'-dinitrodiphenyliodonium tetrafluoroborate, 3.3'-dinitrodiphenyliodonium hexafluoroantimonate, 3.3'-dinitrodiphenyliodonium hexafluoroarsinate, 3.3'-dinitro Diphenyliodonium hexafluorophosphate, 3.3'-dinitrodiphenyliodonium trifluorosulfonate, 4.4'-
Dimethyldiphenyliodonium tetrafluoroborate, 4.4'-dimethyldiphenyliodonium hexafluoroantimonate, 4.4'-dimethyldiphenyliodonium hexafluoroarsinate, 4.4'
-dimethyldiphenyliodonium hexafluorophosphate, 4,4'-dimethyldiphenyliodonium trifluorosulfonate, 4,4'-di-tert-butyldiphenyliodonium tetrafluoroborate,
4.4'-di-tert-butyldiphenyliodonium hexafluoroantimonate, 4°4'-di-tert
-Onium salts such as butyldiphenyliodonium hexafluoroarsinate, 4.4'-di-tert-butyldiphenyliodonium hexafluorophosphate, 4°4'-di-crt-butyldiphenyliodonium trifluorosulfonate Ya, 2, 4, 6. -tris(trichloromethyl)triazine, 2-allyl 4.6-
Bis(trichloromethyl)triazine, α, α, α.
−トリブロモメチルーフェニルスルホン、α、α、α。-Tribromomethyl-phenylsulfone, α, α, α.
α′、α 、α′、−へキサクロロキシリレン、２，２
−ビス（３，５−ジブロム−４−ヒドロキシフェニル）
−１，１，１，３゜３．３−ヘキサフルオロプロパン、
１，１．１− ）リス（３，５−ジブロム−４−ヒドロ
キシフェニル）エタンなどのハロゲン含有化合物や、２
−ニトロペンジルトシレイト、２．６−シニトロペンジ
ルトシレイト、２，４−ジニトロペンジルトシレイト、
メチルスルホン酸２−ニトロベンジルエステル、＃酸２
−ニトロベンジルエステル、ｐ−ニトロベンジル−９，
１０−ジメトキシアントラセン−２＝スルホネイトなど
のスルホン酸エステルなどを挙げることができ、これら
２種以上を併せて用いてもよい。α', α, α', -hexachloroxylylene, 2,2
-bis(3,5-dibromo-4-hydroxyphenyl)
-1,1,1,3゜3.3-hexafluoropropane,
1,1.1- ) halogen-containing compounds such as lis(3,5-dibromo-4-hydroxyphenyl)ethane,
-Nitropenzyl tosylate, 2,6-sinitropenzyl tosylate, 2,4-dinitropenzyl tosylate,
Methylsulfonic acid 2-nitrobenzyl ester, #acid 2
-nitrobenzyl ester, p-nitrobenzyl-9,
Examples include sulfonic acid esters such as 10-dimethoxyanthracene-2=sulfonate, and two or more of these may be used in combination.
一般的に、この発明の実施例の感光性樹脂組成物は、上
記この発明に係わる化合物を溶解し、かつそれらと反応
しない溶媒と共に用いるが、その溶媒として例えば、メ
チルセロソルブ、エチルセロソルブ、ジメチルグライム
、ジエチルグライム、シクロペンタノン、シクロヘキサ
ノン、γ−ブチロラクトン、酢酸イソアミルなどが一般
的である。好ましくは沸点が１００から２２０℃の範囲
が適当である。沸点がこれより低いものではむらができ
やすく、沸点がこれより高いと溶媒の乾燥が容易ではな
い。Generally, the photosensitive resin compositions of the embodiments of the present invention are used together with a solvent that dissolves the compounds according to the present invention and does not react with them, such as methyl cellosolve, ethyl cellosolve, dimethyl glyme, etc. , diethyl glyme, cyclopentanone, cyclohexanone, γ-butyrolactone, isoamyl acetate, etc. are common. Preferably, the boiling point is in the range of 100 to 220°C. If the boiling point is lower than this, unevenness tends to occur, and if the boiling point is higher than this, it is difficult to dry the solvent.
この発明の実施例の感光性樹脂組成物の含有割合は、上
記一般式（１）および（ＩＩ）で表される化合物の内の
少なくとも一種を５〜８０重量％であるのが好ましく、
より好ましくは１０〜４０重量％である。また。The content ratio of the photosensitive resin composition of the example of this invention is preferably 5 to 80% by weight of at least one of the compounds represented by the above general formulas (1) and (II),
More preferably, it is 10 to 40% by weight. Also.
アルカリ可溶性の高分子化合物は、２０〜９５重量％で
あるのが好ましく、より好ましくは６０〜９０重量％で
ある。放射線の照射を受けて酸を発生する化合物は、０
．０５〜２０重量％であるのが好ましく、より好ましく
は０．５〜１０重量％である。上記一般式（Ｉ）および
（Ｕ）で表される化合物の少なくとも一種が５型破％末
黄の場合、パターニングが行いにくくなる傾向が生じ。The content of the alkali-soluble polymer compound is preferably 20 to 95% by weight, more preferably 60 to 90% by weight. Compounds that generate acid when irradiated with radiation are 0
．． It is preferably 0.5 to 20% by weight, more preferably 0.5 to 10% by weight. When at least one of the compounds represented by the above general formulas (I) and (U) has a 5% yellowish appearance, patterning tends to become difficult.
８０貫量％を超えた場合には、他の成分との均一な相溶
性が得られにくくなるので形成されるパターンの不良が
発生しやすくなる。また放射線の照射を受けて酸を発生
する化合物が０．０５重量％未満の場合には良好なパタ
ーンを形成することができにくくなり、２０重量％を超
えた場合には他の成分との均一な相溶性が得られにくく
なるので、形成されるパターンの不良が発生しやすくな
る。If it exceeds 80% by mass, it becomes difficult to obtain uniform compatibility with other components, and the formed pattern is likely to be defective. Furthermore, if the amount of the compound that generates acid upon irradiation with radiation is less than 0.05% by weight, it will be difficult to form a good pattern, and if it exceeds 20% by weight, it will not be uniform with other components. Since it becomes difficult to obtain good compatibility, defects in the formed pattern are likely to occur.
次に、この発明の実施例の感光性樹脂組成物を用いてパ
ターン形成を行う場合について説明する。この発明の実
施例の感光性樹脂組成物の溶液を、シリコンウェハなど
の基板上に塗布し、プリベイクを行ない、ＵＶ光、Ｄｅ
ｅｐＵＶ光、Ｘ線、電子線などの放射線を照射した後、
８０から１５０℃程度の加熱を３０秒から２０分行ない
、次いで現像を行ってパターン形成を行うことができる
。レジストの現像液としては、アンモニア、トリエチル
アミン、ジメチルアミノメタノール、テトラメチルアン
モニウムヒドロキサイド、水酸化ナトリウム、水酸化カ
リウム、炭酸ナトリウム、コリンなどの水溶液を用いる
ことが出来る。Next, the case where pattern formation is performed using the photosensitive resin composition of the example of this invention will be explained. A solution of the photosensitive resin composition of the example of this invention is applied onto a substrate such as a silicon wafer, prebaked, and exposed to UV light and Deposit.
After irradiating with radiation such as epUV light, X-rays, and electron beams,
A pattern can be formed by heating at about 80 to 150° C. for 30 seconds to 20 minutes, and then developing. As the resist developer, an aqueous solution of ammonia, triethylamine, dimethylaminomethanol, tetramethylammonium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, choline, or the like can be used.
なお、この発明の実施例の感光性樹脂組成物が。Note that the photosensitive resin compositions of Examples of this invention are as follows.
基板とレジストとの密着性を向上させるための密着性向
上剤、例えば、アミノシラザン、アミノアルコキシシラ
ザン、アルキルアルコキシシラザンなどをはじめ、その
他必要に応じて目的にあった化合物を含有してもよい。Adhesion improvers for improving the adhesion between the substrate and the resist, such as aminosilazane, aminoalkoxysilazane, alkylalkoxysilazane, etc., and other compounds suitable for the purpose may be contained as necessary.
以下にこの発明の感光性樹脂組成物を具体的な実施例を
挙げて説明するが、これらだけに限定されるものではな
い、なお１表１に上記一般式（Ｉ）で表わされる化合物
を、表２には一般式（ＩＩ）で表わされる化合物を示す
。The photosensitive resin composition of the present invention will be described below with reference to specific examples, but the invention is not limited to these. Table 1 shows the compounds represented by the general formula (I), Table 2 shows compounds represented by general formula (II).
実施例１
しｃｒｔ−ブチルアルコール１０ｇとピリジン９ｇを２
０■ｌのテトラヒドロフランに混合し、これにイソフタ
ル酸クロライド１０ｇを２０置ｌのテトラヒドロフラン
に溶解した溶液を室温で滴下し、その後４時間反応を続
けた０反応後沈澱をろ過し、ろ液を濃縮し水に投入して
白色固体を得た。炭酸ナトリウム水溶液と水で充分洗浄
した後、昇華法により精製し白色の化合物（表１中、化
合物１）を得た。Example 1 10 g of crt-butyl alcohol and 9 g of pyridine were mixed into 2
A solution of 10 g of isophthalic acid chloride dissolved in 20 liters of tetrahydrofuran was added dropwise at room temperature, and the reaction was continued for 4 hours. After the reaction, the precipitate was filtered and the filtrate was concentrated. The mixture was poured into water to obtain a white solid. After thorough washing with an aqueous sodium carbonate solution and water, the product was purified by sublimation to obtain a white compound (Compound 1 in Table 1).
この化合物ｌを２ｇ、Ｐ−ビニルフェノール重合体８ｇ
および酸発生剤としてトリフエニスルホニウムトリフレ
イト０．０４ｇをジグライムに溶解させ、０．２μ諺の
フィルターでろ過してこの発明の一実施例の感光性樹脂
組成物の溶液を作製した。2g of this compound l, 8g of P-vinylphenol polymer
Then, 0.04 g of triphenysulfonium triflate as an acid generator was dissolved in diglyme and filtered through a 0.2μ filter to prepare a solution of a photosensitive resin composition according to an embodiment of the present invention.
この溶液を、３０００ｒ、ｐ、ｍの回転数のスピンコー
ターを使用してシリコンウェハ上に塗布し、８０℃で１
５分間オーブン中でプレキュア−した、この基板を室温
に冷却し、 ２５０ｎ曹のＤｅｅｐ ＵＶ光で約８鳳Ｊ
／ｃ曹２の露光を行った。露光後１１０℃のオーブンで
１０分間加熱を行い、２％テトラメチルアンモニウム水
溶液に２分間浸漬させた。This solution was coated on a silicon wafer using a spin coater with a rotation speed of 3000 r, p, m, and then heated at 80 °C for 1
Precured in an oven for 5 minutes, the substrate was cooled to room temperature and cured with 250 nm of deep UV light for approximately 8 hours.
/c So2 exposure was performed. After exposure, it was heated in an oven at 110° C. for 10 minutes, and then immersed in a 2% aqueous tetramethylammonium solution for 2 minutes.
この操作により良好なパターンが得られた。また露光線
源をＤｅｅｐ ＵＶ光の代わりに加速電圧２０ｋＶの電
子線を１．５μＣ／ｃ腸２照射した場合にもＤｅｅｐ
ＩＪＶ光と同様に良好なパターンが得られた。A good pattern was obtained by this operation. In addition, when the exposure radiation source is Deep
A good pattern was obtained similarly to the IJV light.
実施例２〜１２２
表１および２で示した化合物を用い、実施例１と同様に
表３に示した条件で、この発明の実施例の感光性樹脂組
成物の溶液を得た０次に、実施例１と同様に、この溶液
の感度と解像度を調べ結果を表３に示す。Examples 2 to 122 Solutions of photosensitive resin compositions of Examples of this invention were obtained using the compounds shown in Tables 1 and 2 and under the conditions shown in Table 3 in the same manner as in Example 1. As in Example 1, the sensitivity and resolution of this solution were investigated and the results are shown in Table 3.
その結果、どの実施例も０．３５μｍ以上の解像度を示
し、 ２０ｍｊ／ａｍ２以下の感度を有することが示さ
れた。As a result, it was shown that all the examples exhibited a resolution of 0.35 μm or more and a sensitivity of 20 mj/am2 or less.
［発明の効果］
以上説明した通り、この発明はアルカリ可溶性高分子化
合物、放射線に感光し酸を発生する化合物並びに下記一
般式（Ｉ）および（ＩＩ）で示される化合物の内の少な
くとも一種を含有するものを用いることにより、放射線
露光に対する高い感度と、クオターミクロンレベルの解
像度を有するポジ型の放射線感応レジストを得ることの
できる感光性樹脂組成物を得ることができ１例えば、超
微側パターンが必要となる半導体素子の製造に有効に利
用でき、この感光性樹脂組成物を用いることにより、高
感度で、高解像度のパターニングを行うことができる。[Effects of the Invention] As explained above, the present invention contains at least one of an alkali-soluble polymer compound, a compound that is sensitive to radiation and generates an acid, and a compound represented by the following general formulas (I) and (II). By using a photosensitive resin composition, it is possible to obtain a photosensitive resin composition capable of obtaining a positive radiation-sensitive resist having high sensitivity to radiation exposure and a resolution on the quarter micron level. This photosensitive resin composition can be effectively used in the production of semiconductor devices that require the following, and by using this photosensitive resin composition, patterning can be performed with high sensitivity and high resolution.
Ｙ（Ａｒ（Ｘ−Ｃ−Ｒ２）−）？ （
■）（式中Ａ「はＩＩ置換のベンゼン環または複素環化
合物を示し、Ｙは−、−０−，−５０２−、−ＣＨ２−
、−Ｃｏ−、−Ｃ（ＣＨ３）、−および−Ｃ（ＣＦ３）
２−７７）内の一種ヲ示し、ｘバーｃｏｏ−、−ｏｃｏ
。Y(Ar(X-C-R2)-)? (
■) (In the formula, A" represents a II-substituted benzene ring or a heterocyclic compound, and Y is -, -0-, -502-, -CH2-
, -Co-, -C(CH3), - and -C(CF3)
2-77), x bar coo-, -oco
.
、５０３−の内の一種を示し、Ｒ１，Ｒ２，Ｒ３は同一
であっても異なっていてもよく、各々水素原子、アルキ
ル基、アルコキシ基、アルケニル基、アルキニル基、フ
ェニル基、置換フェニル基を示し、またこれらのうち２
つが環構造をなしていてもよい、但しＩは１から４の整
数を示す、）, 503-, and R1, R2, and R3 may be the same or different, and each represents a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, a phenyl group, or a substituted phenyl group. and 2 of these
may form a ring structure, provided that I represents an integer from 1 to 4)
Claims (1)
生する化合物並びに下記一般式（ I ）および（II）で
示される化合物の内の少なくとも一種を含有する感光性
樹脂組成物。 ▲数式、化学式、表等があります▼（ I ） ▲数式、化学式、表等があります▼（II） （式中Ａｒはｍ置換のベンゼン環または複素環化合物を
示し、Ｙは−、−Ｏ−、−ＳＯ＿２−、−ＣＨ＿２−、
−ＣＯ−、−Ｃ（ＣＨ＿３）＿２−および−Ｃ（ＣＦ＿
３）＿２−の内の一種を示し、Ｘは−ＣＯＯ−、−ＯＣ
ＯＯ−、ＳＯ＿３−の内の一種を示し、Ｒ＿１、Ｒ＿２
、Ｒ＿３は同一であっても異なつていてもよく、各々水
素原子、アルキル基、アルコキシ基、アルケニル基、ア
ルキニル基、フェニル基、置換フェニル基を示し、また
これらのうち２つが環構造をなしていてもよい。但しｍ
は１から４の整数を示す。）[Scope of Claims] A photosensitive resin composition containing at least one of an alkali-soluble polymer compound, a compound that is sensitive to radiation and generates an acid, and a compound represented by the following general formulas (I) and (II). ▲Contains mathematical formulas, chemical formulas, tables, etc.▼(I) ▲Contains mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, Ar represents an m-substituted benzene ring or a heterocyclic compound, and Y represents -, -O- , -SO_2-, -CH_2-,
-CO-, -C(CH_3)_2- and -C(CF_
3) Indicates one of _2-, X is -COO-, -OC
Indicates one type of OO-, SO_3-, R_1, R_2
, R_3 may be the same or different and each represents a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, a phenyl group, or a substituted phenyl group, and two of them form a ring structure. You can leave it there. However, m
represents an integer from 1 to 4. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145117A JP2676981B2 (en) | 1990-06-01 | 1990-06-01 | Photosensitive resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145117A JP2676981B2 (en) | 1990-06-01 | 1990-06-01 | Photosensitive resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0437760A true JPH0437760A (en) | 1992-02-07 |
| JP2676981B2 JP2676981B2 (en) | 1997-11-17 |
Family
ID=15377788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2145117A Expired - Lifetime JP2676981B2 (en) | 1990-06-01 | 1990-06-01 | Photosensitive resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2676981B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04212159A (en) * | 1990-09-07 | 1992-08-03 | Nippon Telegr & Teleph Corp <Ntt> | Positive type resist material |
| JPH055985A (en) * | 1990-11-26 | 1993-01-14 | Minnesota Mining & Mfg Co <3M> | Optical image formable composition containing alkoxy alkyl ester dissolution inhibitor |
| JPH08202029A (en) * | 1995-01-30 | 1996-08-09 | Nec Corp | Resist material |
| EP1375463A4 (en) * | 2001-03-29 | 2009-09-02 | Osaka Gas Co Ltd | Optically active compound and photosensitive resin composition |
| US20150056557A1 (en) * | 2013-08-23 | 2015-02-26 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive-type photosensitive resin composition and method for producing resist pattern using the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6327829A (en) * | 1986-06-13 | 1988-02-05 | マイクロサイ，インコーポレイテッド | Resist composition and use thereof |
| JPH01300250A (en) * | 1988-05-30 | 1989-12-04 | Tosoh Corp | Photoresist composition |
-
1990
- 1990-06-01 JP JP2145117A patent/JP2676981B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6327829A (en) * | 1986-06-13 | 1988-02-05 | マイクロサイ，インコーポレイテッド | Resist composition and use thereof |
| JPH01300250A (en) * | 1988-05-30 | 1989-12-04 | Tosoh Corp | Photoresist composition |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04212159A (en) * | 1990-09-07 | 1992-08-03 | Nippon Telegr & Teleph Corp <Ntt> | Positive type resist material |
| JPH055985A (en) * | 1990-11-26 | 1993-01-14 | Minnesota Mining & Mfg Co <3M> | Optical image formable composition containing alkoxy alkyl ester dissolution inhibitor |
| JPH08202029A (en) * | 1995-01-30 | 1996-08-09 | Nec Corp | Resist material |
| EP1375463A4 (en) * | 2001-03-29 | 2009-09-02 | Osaka Gas Co Ltd | Optically active compound and photosensitive resin composition |
| US20150056557A1 (en) * | 2013-08-23 | 2015-02-26 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive-type photosensitive resin composition and method for producing resist pattern using the same |
| US9323152B2 (en) * | 2013-08-23 | 2016-04-26 | Tokyo Ohka Kogyo Co., Ltd | Chemically amplified positive-type photosensitive resin composition and method for producing resist pattern using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2676981B2 (en) | 1997-11-17 |
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