JP4470315B2 - 感光性ポリイミド前駆体組成物 - Google Patents
感光性ポリイミド前駆体組成物 Download PDFInfo
- Publication number
- JP4470315B2 JP4470315B2 JP2000325032A JP2000325032A JP4470315B2 JP 4470315 B2 JP4470315 B2 JP 4470315B2 JP 2000325032 A JP2000325032 A JP 2000325032A JP 2000325032 A JP2000325032 A JP 2000325032A JP 4470315 B2 JP4470315 B2 JP 4470315B2
- Authority
- JP
- Japan
- Prior art keywords
- synthesis example
- group
- mol
- organic group
- varnish
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 229920001721 polyimide Polymers 0.000 title claims description 40
- 239000004642 Polyimide Substances 0.000 title claims description 33
- 239000002243 precursor Substances 0.000 title claims description 24
- 229920000642 polymer Polymers 0.000 claims description 29
- 125000000962 organic group Chemical group 0.000 claims description 28
- -1 vinyl ether compound Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000006358 imidation reaction Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 70
- 238000003786 synthesis reaction Methods 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000002966 varnish Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 26
- 238000011161 development Methods 0.000 description 22
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002835 absorbance Methods 0.000 description 11
- 125000005462 imide group Chemical group 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 229920005575 poly(amic acid) Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
- 102100026735 Coagulation factor VIII Human genes 0.000 description 3
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000710 polymer precipitation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 2
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 2
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 229940117360 ethyl pyruvate Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- QVIJIEXWEFBCPP-UHFFFAOYSA-N (3-aminophenyl)carbamic acid Chemical compound NC1=CC=CC(NC(O)=O)=C1 QVIJIEXWEFBCPP-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- IQFUADQPSYSDIP-UHFFFAOYSA-N (4-aminophenyl)carbamic acid Chemical compound NC1=CC=C(NC(O)=O)C=C1 IQFUADQPSYSDIP-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- UNYPOFWEGVYMRJ-UHFFFAOYSA-N 1-azidoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N=[N+]=[N-] UNYPOFWEGVYMRJ-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- LFZLVJBOEONQHV-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(N(C)C)=C1 LFZLVJBOEONQHV-UHFFFAOYSA-N 0.000 description 1
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 description 1
- RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 description 1
- MTEZSDOQASFMDI-UHFFFAOYSA-N 1-trimethoxysilylpropan-1-ol Chemical compound CCC(O)[Si](OC)(OC)OC MTEZSDOQASFMDI-UHFFFAOYSA-N 0.000 description 1
- NKNIZOPLGAJLRV-UHFFFAOYSA-N 2,2-diphenylpropane-1,1-diamine Chemical compound C=1C=CC=CC=1C(C(N)N)(C)C1=CC=CC=C1 NKNIZOPLGAJLRV-UHFFFAOYSA-N 0.000 description 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QHDSBTKCTUXBEG-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N QHDSBTKCTUXBEG-UHFFFAOYSA-N 0.000 description 1
- NXLQPXAUWAWQOB-UHFFFAOYSA-N 2-[2-[2-(2-aminoethyl)phenoxy]phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1OC1=CC=CC=C1CCN NXLQPXAUWAWQOB-UHFFFAOYSA-N 0.000 description 1
- NODBCGAUEYHBND-UHFFFAOYSA-N 2-[2-[[2-(2-aminoethyl)phenyl]methyl]phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1CC1=CC=CC=C1CCN NODBCGAUEYHBND-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- HUVMDVMRZUVXIK-UHFFFAOYSA-N 2-azido-1,3-diphenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=O)C(N=[N+]=[N-])=CC1=CC=CC=C1 HUVMDVMRZUVXIK-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- FZLHLGUYHAXYNA-UHFFFAOYSA-N 2-fluoro-3,3-bis(fluorooxycarbonyl)-2-(trifluoromethyl)butanedioic acid Chemical compound OC(=O)C(F)(C(F)(F)F)C(C(O)=O)(C(=O)OF)C(=O)OF FZLHLGUYHAXYNA-UHFFFAOYSA-N 0.000 description 1
- JSUCXITZANSMPG-UHFFFAOYSA-M 2-hydroxypropyl(trimethyl)azanium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CC(O)C[N+](C)(C)C JSUCXITZANSMPG-UHFFFAOYSA-M 0.000 description 1
- AKVUWTYSNLGBJY-UHFFFAOYSA-N 2-methyl-1-morpholin-4-ylprop-2-en-1-one Chemical compound CC(=C)C(=O)N1CCOCC1 AKVUWTYSNLGBJY-UHFFFAOYSA-N 0.000 description 1
- RASDUGQQSMMINZ-UHFFFAOYSA-N 2-methyl-1-piperidin-1-ylprop-2-en-1-one Chemical compound CC(=C)C(=O)N1CCCCC1 RASDUGQQSMMINZ-UHFFFAOYSA-N 0.000 description 1
- VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- XBTHNZXADRSYPR-UHFFFAOYSA-N 3-(1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C(C=2C=CC=CC=2)(C(F)(F)F)C(F)(F)F)=C1N XBTHNZXADRSYPR-UHFFFAOYSA-N 0.000 description 1
- DOJDHOJUHISJIT-UHFFFAOYSA-N 3-(3-amino-2-phenoxyphenoxy)-2-phenoxyaniline Chemical compound C=1C=CC=CC=1OC=1C(N)=CC=CC=1OC1=CC=CC(N)=C1OC1=CC=CC=C1 DOJDHOJUHISJIT-UHFFFAOYSA-N 0.000 description 1
- NHJNWRVCOATWGF-UHFFFAOYSA-N 3-(3-amino-2-phenoxyphenyl)sulfonyl-2-phenoxyaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C(=C(N)C=CC=2)OC=2C=CC=CC=2)=C1OC1=CC=CC=C1 NHJNWRVCOATWGF-UHFFFAOYSA-N 0.000 description 1
- SMBSZJBWYCGCJP-UHFFFAOYSA-N 3-(diethylamino)chromen-2-one Chemical compound C1=CC=C2OC(=O)C(N(CC)CC)=CC2=C1 SMBSZJBWYCGCJP-UHFFFAOYSA-N 0.000 description 1
- OIMHDSCGRKQKOR-UHFFFAOYSA-N 3-(diethylamino)propyl 2-azidobenzoate Chemical compound C(C)N(CC)CCCOC(C1=C(C=CC=C1)N=[N+]=[N-])=O OIMHDSCGRKQKOR-UHFFFAOYSA-N 0.000 description 1
- AFELPJWTIKEPQP-UHFFFAOYSA-N 3-(diethylamino)propyl benzoate Chemical compound CCN(CC)CCCOC(=O)C1=CC=CC=C1 AFELPJWTIKEPQP-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- JHFFZUDXMFVENY-UHFFFAOYSA-N 3-[(3-amino-2-chlorophenyl)methyl]-2-chloroaniline Chemical compound NC1=CC=CC(CC=2C(=C(N)C=CC=2)Cl)=C1Cl JHFFZUDXMFVENY-UHFFFAOYSA-N 0.000 description 1
- DIRYWKMUDQKIKC-UHFFFAOYSA-N 3-[2-(3-amino-2-phenoxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-phenoxyaniline Chemical compound NC1=CC=CC(C(C=2C(=C(N)C=CC=2)OC=2C=CC=CC=2)(C(F)(F)F)C(F)(F)F)=C1OC1=CC=CC=C1 DIRYWKMUDQKIKC-UHFFFAOYSA-N 0.000 description 1
- AYYAHNKZUPFRSL-UHFFFAOYSA-N 3-[2-[3-amino-2-(trifluoromethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(C=2C(=C(N)C=CC=2)C(F)(F)F)(C(F)(F)F)C(F)(F)F)=C1C(F)(F)F AYYAHNKZUPFRSL-UHFFFAOYSA-N 0.000 description 1
- OILQCHXXZLKFGZ-UHFFFAOYSA-N 3-[2-[3-amino-2-(trifluoromethyl)phenyl]propan-2-yl]-2-(trifluoromethyl)aniline Chemical compound C=1C=CC(N)=C(C(F)(F)F)C=1C(C)(C)C1=CC=CC(N)=C1C(F)(F)F OILQCHXXZLKFGZ-UHFFFAOYSA-N 0.000 description 1
- ILDLZHYKUHDWOE-UHFFFAOYSA-N 3-[3-amino-2-(trifluoromethyl)phenoxy]-2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(OC=2C(=C(N)C=CC=2)C(F)(F)F)=C1C(F)(F)F ILDLZHYKUHDWOE-UHFFFAOYSA-N 0.000 description 1
- OHUYOONRBRAWFG-UHFFFAOYSA-N 3-[3-amino-2-(trifluoromethyl)phenyl]sulfonyl-2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C(=C(N)C=CC=2)C(F)(F)F)=C1C(F)(F)F OHUYOONRBRAWFG-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- FCSBHOKNHNSTOX-UHFFFAOYSA-N 3-[[3-amino-2-(trifluoromethyl)phenyl]methyl]-2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(CC=2C(=C(N)C=CC=2)C(F)(F)F)=C1C(F)(F)F FCSBHOKNHNSTOX-UHFFFAOYSA-N 0.000 description 1
- CPVJWBWVJUAOMV-UHFFFAOYSA-N 3-benzoyl-7-(diethylamino)chromen-2-one Chemical compound O=C1OC2=CC(N(CC)CC)=CC=C2C=C1C(=O)C1=CC=CC=C1 CPVJWBWVJUAOMV-UHFFFAOYSA-N 0.000 description 1
- ITBCGMPMZYVWED-UHFFFAOYSA-N 3-n-(trifluoromethyl)benzene-1,3-diamine Chemical compound NC1=CC=CC(NC(F)(F)F)=C1 ITBCGMPMZYVWED-UHFFFAOYSA-N 0.000 description 1
- AAYMVIUILSVWQK-UHFFFAOYSA-N 3-n-bromobenzene-1,3-diamine Chemical compound NC1=CC=CC(NBr)=C1 AAYMVIUILSVWQK-UHFFFAOYSA-N 0.000 description 1
- XAXXXFOWCPSWLO-UHFFFAOYSA-N 3-n-chlorobenzene-1,3-diamine Chemical compound NC1=CC=CC(NCl)=C1 XAXXXFOWCPSWLO-UHFFFAOYSA-N 0.000 description 1
- FWPNSTBELLMQOW-UHFFFAOYSA-N 3-n-methoxybenzene-1,3-diamine Chemical compound CONC1=CC=CC(N)=C1 FWPNSTBELLMQOW-UHFFFAOYSA-N 0.000 description 1
- JJZNCUHIYJBAMS-UHFFFAOYSA-N 3-phenyl-2h-1,2-oxazol-5-one Chemical compound N1OC(=O)C=C1C1=CC=CC=C1 JJZNCUHIYJBAMS-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- CMUXNSYLMJIRAH-UHFFFAOYSA-N 4-(4-amino-2,3-diethylphenoxy)-2,3-diethylaniline Chemical compound CCC1=C(N)C=CC(OC=2C(=C(CC)C(N)=CC=2)CC)=C1CC CMUXNSYLMJIRAH-UHFFFAOYSA-N 0.000 description 1
- DUVBGRVKPIKDLU-UHFFFAOYSA-N 4-(4-amino-2,3-diethylphenyl)sulfonyl-2,3-diethylaniline Chemical compound CCC1=C(N)C=CC(S(=O)(=O)C=2C(=C(CC)C(N)=CC=2)CC)=C1CC DUVBGRVKPIKDLU-UHFFFAOYSA-N 0.000 description 1
- XRLCJMLUANVBPF-UHFFFAOYSA-N 4-(4-amino-2,3-dimethylphenoxy)-2,3-dimethylaniline Chemical compound C1=C(N)C(C)=C(C)C(OC=2C(=C(C)C(N)=CC=2)C)=C1 XRLCJMLUANVBPF-UHFFFAOYSA-N 0.000 description 1
- SEGMKCGUJKPKPK-UHFFFAOYSA-N 4-(4-amino-2,3-dimethylphenyl)sulfonyl-2,3-dimethylaniline Chemical compound C1=C(N)C(C)=C(C)C(S(=O)(=O)C=2C(=C(C)C(N)=CC=2)C)=C1 SEGMKCGUJKPKPK-UHFFFAOYSA-N 0.000 description 1
- LPDSNGAFAJYVKH-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-dichloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(Cl)=C1Cl LPDSNGAFAJYVKH-UHFFFAOYSA-N 0.000 description 1
- OAKUJYMZERNLLT-UHFFFAOYSA-N 4-(dimethylamino)butyl 2-methylprop-2-enoate Chemical compound CN(C)CCCCOC(=O)C(C)=C OAKUJYMZERNLLT-UHFFFAOYSA-N 0.000 description 1
- WCCQZESRKMUJCJ-UHFFFAOYSA-N 4-[(4-amino-2,3-diethylphenyl)methyl]-2,3-diethylaniline Chemical compound CCC1=C(N)C=CC(CC=2C(=C(CC)C(N)=CC=2)CC)=C1CC WCCQZESRKMUJCJ-UHFFFAOYSA-N 0.000 description 1
- JFUHWBNORCWIMT-UHFFFAOYSA-N 4-[(4-amino-2,3-dimethylphenyl)methyl]-2,3-dimethylaniline Chemical compound C1=C(N)C(C)=C(C)C(CC=2C(=C(C)C(N)=CC=2)C)=C1 JFUHWBNORCWIMT-UHFFFAOYSA-N 0.000 description 1
- OXPBIEBZZYZTTL-UHFFFAOYSA-N 4-[2-(4-amino-2,3-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,3-dimethylaniline Chemical compound C1=C(N)C(C)=C(C)C(C(C=2C(=C(C)C(N)=CC=2)C)(C(F)(F)F)C(F)(F)F)=C1 OXPBIEBZZYZTTL-UHFFFAOYSA-N 0.000 description 1
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 4-amino-2-aminobenzoic acid Natural products NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 1
- FBQJXMJJBAXPCF-UHFFFAOYSA-N 4-n-(trifluoromethoxy)benzene-1,4-diamine Chemical compound NC1=CC=C(NOC(F)(F)F)C=C1 FBQJXMJJBAXPCF-UHFFFAOYSA-N 0.000 description 1
- BAFJJKUNTDYHGT-UHFFFAOYSA-N 4-n-(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(NC(F)(F)F)C=C1 BAFJJKUNTDYHGT-UHFFFAOYSA-N 0.000 description 1
- RWGGISRILXKSCH-UHFFFAOYSA-N 4-n-bromobenzene-1,4-diamine Chemical compound NC1=CC=C(NBr)C=C1 RWGGISRILXKSCH-UHFFFAOYSA-N 0.000 description 1
- YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 description 1
- IHWPTLPROWODBQ-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine Chemical compound CONC1=CC=C(N)C=C1 IHWPTLPROWODBQ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- MLLCMYICVZZOPN-UHFFFAOYSA-N C(C)N(CC)CCOC(C1=C(C=CC=C1)N=[N+]=[N-])=O Chemical compound C(C)N(CC)CCOC(C1=C(C=CC=C1)N=[N+]=[N-])=O MLLCMYICVZZOPN-UHFFFAOYSA-N 0.000 description 1
- AZOWAZWIDBFJDK-UHFFFAOYSA-N C(CCC)[Sn].C(CCCCCCCCCCC)(=O)O Chemical compound C(CCC)[Sn].C(CCCCCCCCCCC)(=O)O AZOWAZWIDBFJDK-UHFFFAOYSA-N 0.000 description 1
- FCJZRPWRGYDRGS-UHFFFAOYSA-N CN(C)CCCOC(C1=C(C=CC=C1)N=[N+]=[N-])=O Chemical compound CN(C)CCCOC(C1=C(C=CC=C1)N=[N+]=[N-])=O FCJZRPWRGYDRGS-UHFFFAOYSA-N 0.000 description 1
- RWKPMPIKXBXOSG-UHFFFAOYSA-O C[NH+](C)CCOC(C(C=CC=C1)C1=S(=O)=O)=O.[N-]=[N+]=[N-] Chemical compound C[NH+](C)CCOC(C(C=CC=C1)C1=S(=O)=O)=O.[N-]=[N+]=[N-] RWKPMPIKXBXOSG-UHFFFAOYSA-O 0.000 description 1
- WIXMQOAHDYVHQQ-UHFFFAOYSA-O C[NH+](C)CCOC(C1=CC=CC=C1)=O.[N-]=[N+]=[N-] Chemical compound C[NH+](C)CCOC(C1=CC=CC=C1)=O.[N-]=[N+]=[N-] WIXMQOAHDYVHQQ-UHFFFAOYSA-O 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 1
- DLEPYXFUDLQGDW-UHFFFAOYSA-N FC(F)(F)NC1=CC=C(C2=CC=C(NC(F)(F)F)C=C2)C=C1 Chemical compound FC(F)(F)NC1=CC=C(C2=CC=C(NC(F)(F)F)C=C2)C=C1 DLEPYXFUDLQGDW-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- DZELFEHHVQERNV-UHFFFAOYSA-N NC1=C(C(=C(C=C1)C(C(F)(F)F)(C(F)(F)F)C1=C(C(=C(C=C1)N)CC)CC)CC)CC Chemical compound NC1=C(C(=C(C=C1)C(C(F)(F)F)(C(F)(F)F)C1=C(C(=C(C=C1)N)CC)CC)CC)CC DZELFEHHVQERNV-UHFFFAOYSA-N 0.000 description 1
- VORQHDAAEKVOEA-UHFFFAOYSA-N NC1=C(C(=C(C=C1)C(C)(C)C1=C(C(=C(C=C1)N)C)C)C)C Chemical compound NC1=C(C(=C(C=C1)C(C)(C)C1=C(C(=C(C=C1)N)C)C)C)C VORQHDAAEKVOEA-UHFFFAOYSA-N 0.000 description 1
- VBXUFYXJFUCXIF-UHFFFAOYSA-N NC1=C(C(=C(C=C1)C(C)(C)C1=C(C(=C(C=C1)N)CC)CC)CC)CC Chemical compound NC1=C(C(=C(C=C1)C(C)(C)C1=C(C(=C(C=C1)N)CC)CC)CC)CC VBXUFYXJFUCXIF-UHFFFAOYSA-N 0.000 description 1
- YRVXURDYAUVLND-UHFFFAOYSA-N NC=1C(=C(C=CC1)C(C(F)(F)F)(C(F)(F)F)C1=C(C(=CC=C1)N)Cl)Cl Chemical compound NC=1C(=C(C=CC1)C(C(F)(F)F)(C(F)(F)F)C1=C(C(=CC=C1)N)Cl)Cl YRVXURDYAUVLND-UHFFFAOYSA-N 0.000 description 1
- HGUOIXZHLJAMIA-UHFFFAOYSA-N NC=1C(=C(C=CC1)C(C)(C)C1=C(C(=CC=C1)N)Cl)Cl Chemical compound NC=1C(=C(C=CC1)C(C)(C)C1=C(C(=CC=C1)N)Cl)Cl HGUOIXZHLJAMIA-UHFFFAOYSA-N 0.000 description 1
- DTZFXWBRKFVPAU-UHFFFAOYSA-N NCCC1=C(C=CC=C1)C(C(F)(F)F)(C(F)(F)F)C1=C(C=CC=C1)CCN Chemical compound NCCC1=C(C=CC=C1)C(C(F)(F)F)(C(F)(F)F)C1=C(C=CC=C1)CCN DTZFXWBRKFVPAU-UHFFFAOYSA-N 0.000 description 1
- ZKHKCGGSMSHFFY-UHFFFAOYSA-N NCCC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)CCN Chemical compound NCCC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)CCN ZKHKCGGSMSHFFY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 description 1
- LVWCTLNZXFKHCO-UHFFFAOYSA-N [2-[2-(aminomethyl)phenoxy]phenyl]methanamine Chemical compound NCC1=CC=CC=C1OC1=CC=CC=C1CN LVWCTLNZXFKHCO-UHFFFAOYSA-N 0.000 description 1
- HZLFRJVKDLCECR-UHFFFAOYSA-N [2-[2-(aminomethyl)phenyl]sulfonylphenyl]methanamine Chemical compound NCC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1CN HZLFRJVKDLCECR-UHFFFAOYSA-N 0.000 description 1
- NCEJSPHZTWECET-UHFFFAOYSA-N [2-[2-[2-(aminomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenyl]methanamine Chemical compound NCC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1CN NCEJSPHZTWECET-UHFFFAOYSA-N 0.000 description 1
- CJTMOHJCBRIPPT-UHFFFAOYSA-N [2-[[2-(aminomethyl)phenyl]methyl]phenyl]methanamine Chemical compound NCC1=CC=CC=C1CC1=CC=CC=C1CN CJTMOHJCBRIPPT-UHFFFAOYSA-N 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- OWMBTIRJFMGPAC-UHFFFAOYSA-N dimethylamino 2-methylprop-2-enoate Chemical compound CN(C)OC(=O)C(C)=C OWMBTIRJFMGPAC-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JQPARKNWUCPYTK-UHFFFAOYSA-M ethyl(trimethyl)azanium;2-methylprop-2-enoate Chemical compound CC[N+](C)(C)C.CC(=C)C([O-])=O JQPARKNWUCPYTK-UHFFFAOYSA-M 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- UFDGMXHPQNDESO-UHFFFAOYSA-N methyl n-(4-aminophenyl)carbamate Chemical compound COC(=O)NC1=CC=C(N)C=C1 UFDGMXHPQNDESO-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GVBMMNAPRZDGEY-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CCN(CC)CCNC(=O)C(C)=C GVBMMNAPRZDGEY-UHFFFAOYSA-N 0.000 description 1
- CXSANWNPQKKNJO-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]prop-2-enamide Chemical compound CCN(CC)CCNC(=O)C=C CXSANWNPQKKNJO-UHFFFAOYSA-N 0.000 description 1
- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-UHFFFAOYSA-N 0.000 description 1
- WDQKICIMIPUDBL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C=C WDQKICIMIPUDBL-UHFFFAOYSA-N 0.000 description 1
- GFOCCLOYMMHTIU-UHFFFAOYSA-N n-[3-(diethylamino)propyl]prop-2-enamide Chemical compound CCN(CC)CCCNC(=O)C=C GFOCCLOYMMHTIU-UHFFFAOYSA-N 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- JGGQWILNAAODRS-UHFFFAOYSA-N n-methyl-4-[4-(methylamino)phenyl]aniline Chemical compound C1=CC(NC)=CC=C1C1=CC=C(NC)C=C1 JGGQWILNAAODRS-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- ZAEQTGTVGUJEFV-UHFFFAOYSA-N phenylmethanesulfonate;pyridin-1-ium Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 ZAEQTGTVGUJEFV-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229940095050 propylene Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940074411 xylene Drugs 0.000 description 1
Images
Landscapes
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000325032A JP4470315B2 (ja) | 1999-10-28 | 2000-10-25 | 感光性ポリイミド前駆体組成物 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11-306779 | 1999-10-28 | ||
| JP30677999 | 1999-10-28 | ||
| JP2000325032A JP4470315B2 (ja) | 1999-10-28 | 2000-10-25 | 感光性ポリイミド前駆体組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001194784A JP2001194784A (ja) | 2001-07-19 |
| JP2001194784A5 JP2001194784A5 (enExample) | 2007-12-06 |
| JP4470315B2 true JP4470315B2 (ja) | 2010-06-02 |
Family
ID=26564862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000325032A Expired - Fee Related JP4470315B2 (ja) | 1999-10-28 | 2000-10-25 | 感光性ポリイミド前駆体組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4470315B2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4175837B2 (ja) * | 2002-07-02 | 2008-11-05 | 株式会社日本触媒 | 画像形成用感光性樹脂組成物 |
| US8071273B2 (en) | 2008-03-31 | 2011-12-06 | Dai Nippon Printing Co., Ltd. | Polyimide precursor, resin composition comprising the polyimide precursor, pattern forming method using the resin composition, and articles produced by using the resin composition |
| JP5428442B2 (ja) * | 2008-03-31 | 2014-02-26 | 大日本印刷株式会社 | ポリイミド前駆体、ポリイミド前駆体樹脂組成物、及び電子部品 |
| JP5428181B2 (ja) * | 2008-03-31 | 2014-02-26 | 大日本印刷株式会社 | ポリイミド前駆体の製造方法、及びそれを用いたポリイミドの製造方法 |
| JP5428179B2 (ja) * | 2008-03-31 | 2014-02-26 | 大日本印刷株式会社 | ポリイミド前駆体樹脂組成物、及び電子部品 |
| JP5428180B2 (ja) * | 2008-03-31 | 2014-02-26 | 大日本印刷株式会社 | ポリイミド前駆体樹脂組成物、及び電子部品 |
| JP7761420B2 (ja) * | 2020-09-25 | 2025-10-28 | 旭化成株式会社 | 感光性樹脂組成物 |
| JP2023113573A (ja) * | 2022-02-03 | 2023-08-16 | Jfeケミカル株式会社 | ポリイミド前駆体 |
-
2000
- 2000-10-25 JP JP2000325032A patent/JP4470315B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001194784A (ja) | 2001-07-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3526829B2 (ja) | ポリアミド酸エステル | |
| JP6935982B2 (ja) | 樹脂組成物、硬化レリーフパターンの製造方法、及び半導体装置 | |
| JP4470315B2 (ja) | 感光性ポリイミド前駆体組成物 | |
| JP2002121382A (ja) | ポリイミド前駆体組成物 | |
| US6090525A (en) | Actinic radiation sensitive polymer composition | |
| JP2004091572A (ja) | ポリアミド酸エステル組成物 | |
| CN117186403B (zh) | 一种负性光敏性树脂、树脂组合物及其制备方法与应用 | |
| JPH0540339A (ja) | ポリイミドのパターン形成方法 | |
| GB2216532A (en) | Heat resistant and photosensitive aromatic polyamide resins and method of preparing same | |
| JP4051759B2 (ja) | 化学線感応性重合体組成物 | |
| JPH06332178A (ja) | 感光性ポリイミド前駆体組成物 | |
| JP4164974B2 (ja) | アルカリ現像可能な感光性ポリイミド前駆体組成物 | |
| JP2003121997A (ja) | ネガ型感光性樹脂組成物 | |
| JPH0990629A (ja) | 感光性樹脂組成物及びこれを用いた半導体装置の製造法 | |
| JP3855365B2 (ja) | ポリイミドコーティング剤組成物及びポリイミドコーティング膜 | |
| JPH03115461A (ja) | 感光性樹脂組成物 | |
| JPS61238809A (ja) | 感光性ポリイミドの樹脂液組成物 | |
| JPH06301209A (ja) | 感光性ポリイミド前駆体組成物 | |
| JP2002122990A (ja) | 感光性ポリイミド前駆体組成物 | |
| JPH10316855A (ja) | 化学線感応性重合体組成物 | |
| JPH10301281A (ja) | 感光性ポリイミド前駆体組成物 | |
| JP2003241371A (ja) | 感光性樹脂組成物およびその製造方法 | |
| JP2001089563A (ja) | ポリイミド前駆体組成物 | |
| JPH10239841A (ja) | 感光性ポリイミド前駆体組成物 | |
| JPH05224419A (ja) | ポリイミド微細パターンの形成方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071019 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071019 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100120 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100209 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100222 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| R151 | Written notification of patent or utility model registration |
Ref document number: 4470315 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140312 Year of fee payment: 4 |
|
| LAPS | Cancellation because of no payment of annual fees |