JP2002363123A - 光活性化合物および感光性樹脂組成物 - Google Patents

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Publication number

JP2002363123A

JP2002363123A JP2002094756A JP2002094756A JP2002363123A JP 2002363123 A JP2002363123 A JP 2002363123A JP 2002094756 A JP2002094756 A JP 2002094756A JP 2002094756 A JP2002094756 A JP 2002094756A JP 2002363123 A JP2002363123 A JP 2002363123A

Authority

JP

Japan

Prior art keywords

group

bis

tert

hydroxy

synthesis

Prior art date

2001-03-29

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 161
• 239000011342 resin composition Substances 0.000 title claims description 52
• -1 hydroxy, carboxy Chemical group 0.000 claims abstract description 300
• 125000005647 linker group Chemical group 0.000 claims abstract description 70
• 125000006239 protecting group Chemical group 0.000 claims abstract description 51
• 230000002209 hydrophobic effect Effects 0.000 claims abstract description 43
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 34
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 33
• 239000003504 photosensitizing agent Substances 0.000 claims abstract description 20
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
• 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 13
• 229920005989 resin Polymers 0.000 claims description 78
• 239000011347 resin Substances 0.000 claims description 78
• 125000001424 substituent group Chemical group 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• 239000002585 base Substances 0.000 claims description 34
• 239000000178 monomer Substances 0.000 claims description 29
• 238000000034 method Methods 0.000 claims description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
• 125000002723 alicyclic group Chemical group 0.000 claims description 25
• 229910052710 silicon Inorganic materials 0.000 claims description 24
• 125000004450 alkenylene group Chemical group 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 23
• 229920001577 copolymer Polymers 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 20
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 18
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
• 125000000732 arylene group Chemical group 0.000 claims description 18
• 125000005702 oxyalkylene group Chemical group 0.000 claims description 18
• 239000010703 silicon Substances 0.000 claims description 18
• 125000004419 alkynylene group Chemical group 0.000 claims description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
• 125000005027 hydroxyaryl group Chemical group 0.000 claims description 15
• VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 12
• 229930185605 Bisphenol Natural products 0.000 claims description 12
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
• 125000003368 amide group Chemical group 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• 238000010438 heat treatment Methods 0.000 claims description 12
• 125000001033 ether group Chemical group 0.000 claims description 11
• JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 10
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 9
• 239000000758 substrate Substances 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 125000000101 thioether group Chemical group 0.000 claims description 8
• 230000009471 action Effects 0.000 claims description 7
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000004185 ester group Chemical group 0.000 claims description 7
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
• 150000001924 cycloalkanes Chemical class 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 4
• 239000003513 alkali Substances 0.000 claims description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
• 230000008030 elimination Effects 0.000 claims description 3
• 238000003379 elimination reaction Methods 0.000 claims description 3
• 125000005116 aryl carbamoyl group Chemical group 0.000 claims 1
• 125000000686 lactone group Chemical group 0.000 claims 1
• 230000035945 sensitivity Effects 0.000 abstract description 16
• 229920002120 photoresistant polymer Polymers 0.000 abstract description 2
• 230000015572 biosynthetic process Effects 0.000 description 209
• 238000003786 synthesis reaction Methods 0.000 description 209
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 173
• YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 132
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 109
• 238000005160 1H NMR spectroscopy Methods 0.000 description 108
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
• 239000002904 solvent Substances 0.000 description 50
• 238000001953 recrystallisation Methods 0.000 description 44
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 43
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 38
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 37
• 239000000243 solution Substances 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 23
• GDFUWFOCYZZGQU-UHFFFAOYSA-N 4-propoxybenzoic acid Chemical compound CCCOC1=CC=C(C(O)=O)C=C1 GDFUWFOCYZZGQU-UHFFFAOYSA-N 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 229910052739 hydrogen Inorganic materials 0.000 description 20
• 239000010410 layer Substances 0.000 description 20
• 150000002989 phenols Chemical class 0.000 description 20
• 229920000642 polymer Polymers 0.000 description 20
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 19
• ISTOAGOBQCQLFG-UHFFFAOYSA-N [4-(4-bromophenyl)phenyl] tert-butyl carbonate Chemical group C1=CC(OC(=O)OC(C)(C)C)=CC=C1C1=CC=C(Br)C=C1 ISTOAGOBQCQLFG-UHFFFAOYSA-N 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 18
• 239000000203 mixture Substances 0.000 description 18
• VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical group C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 17
• 238000010898 silica gel chromatography Methods 0.000 description 16
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 15
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 15
• 239000005457 ice water Substances 0.000 description 15
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 14
• 229930195733 hydrocarbon Natural products 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
• 229920003986 novolac Polymers 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 11
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 11
• 238000011161 development Methods 0.000 description 10
• 230000018109 developmental process Effects 0.000 description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
• 238000004090 dissolution Methods 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• HBMCQTHGYMTCOF-UHFFFAOYSA-N 4-hydroxyphenyl acetate Chemical compound CC(=O)OC1=CC=C(O)C=C1 HBMCQTHGYMTCOF-UHFFFAOYSA-N 0.000 description 8
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 239000004215 Carbon black (E152) Substances 0.000 description 8
• 125000005037 alkyl phenyl group Chemical group 0.000 description 8
• 230000002194 synthesizing effect Effects 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• XFUQJWQKYYIACT-UHFFFAOYSA-N (4-bromophenyl) tert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(Br)C=C1 XFUQJWQKYYIACT-UHFFFAOYSA-N 0.000 description 7
• NMKZRVMAECEGMV-UHFFFAOYSA-N 1-ethynyl-4-propoxybenzene Chemical group CCCOC1=CC=C(C#C)C=C1 NMKZRVMAECEGMV-UHFFFAOYSA-N 0.000 description 7
• 239000004925 Acrylic resin Substances 0.000 description 7
• 229920000178 Acrylic resin Polymers 0.000 description 7
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• 150000002430 hydrocarbons Chemical class 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 7
• 235000013824 polyphenols Nutrition 0.000 description 7
• 239000004065 semiconductor Substances 0.000 description 7
• KXUKRZZEHBUWKN-UHFFFAOYSA-N tert-butyl (4-hydroxyphenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C(O)C=C1 KXUKRZZEHBUWKN-UHFFFAOYSA-N 0.000 description 7
• UFPKPYIACUJDFD-UHFFFAOYSA-N tert-butyl (4-phenylmethoxyphenyl) carbonate Chemical compound C1=CC(OC(=O)OC(C)(C)C)=CC=C1OCC1=CC=CC=C1 UFPKPYIACUJDFD-UHFFFAOYSA-N 0.000 description 7
• 229920002554 vinyl polymer Polymers 0.000 description 7
• NUPWGLKBGVNSJX-UHFFFAOYSA-N 1-bromo-4-propylbenzene Chemical compound CCCC1=CC=C(Br)C=C1 NUPWGLKBGVNSJX-UHFFFAOYSA-N 0.000 description 6
• JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 6
• KVNNDSUUTJORDP-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxycarbonyloxy]benzoic acid Chemical compound CC(C)(C)OC(=O)OC1=CC=C(C(O)=O)C=C1 KVNNDSUUTJORDP-UHFFFAOYSA-N 0.000 description 6
• GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 235000010233 benzoic acid Nutrition 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 239000004305 biphenyl Substances 0.000 description 6
• 229910052799 carbon Inorganic materials 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 6
• IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
• 235000013849 propane Nutrition 0.000 description 6
• 238000011160 research Methods 0.000 description 6
• 125000003944 tolyl group Chemical group 0.000 description 6
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
• 125000006585 (C6-C10) arylene group Chemical group 0.000 description 5
• NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 5
• UVFFOABHOIMLNB-UHFFFAOYSA-N 1-ethynyl-4-propylbenzene Chemical group CCCC1=CC=C(C#C)C=C1 UVFFOABHOIMLNB-UHFFFAOYSA-N 0.000 description 5
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
• 229920001665 Poly-4-vinylphenol Polymers 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 235000010290 biphenyl Nutrition 0.000 description 5
• ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 5
• 238000000576 coating method Methods 0.000 description 5
• 239000003480 eluent Substances 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 229910052736 halogen Inorganic materials 0.000 description 5
• 150000002367 halogens Chemical class 0.000 description 5
• 125000005059 halophenyl group Chemical group 0.000 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 5
• 239000012046 mixed solvent Substances 0.000 description 5
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 239000001294 propane Substances 0.000 description 5
• LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
• 150000003839 salts Chemical class 0.000 description 5
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 5
• DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
• XEXHCQJRVMVJMY-UHFFFAOYSA-N (4-bromophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Br)C=C1 XEXHCQJRVMVJMY-UHFFFAOYSA-N 0.000 description 4
• OCGNQJCQAQWYOI-UHFFFAOYSA-N 1-(chloromethyl)-4-propylbenzene Chemical compound CCCC1=CC=C(CCl)C=C1 OCGNQJCQAQWYOI-UHFFFAOYSA-N 0.000 description 4
• DVDHNHPHNIXHCU-UHFFFAOYSA-N 1-bromo-4-[[(4-bromophenyl)-phenylmethoxy]-phenylmethyl]benzene Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC=CC=1)OC(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 DVDHNHPHNIXHCU-UHFFFAOYSA-N 0.000 description 4
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
• 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 4
• ACCMUAPHRVODJN-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzoic acid Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ACCMUAPHRVODJN-UHFFFAOYSA-N 0.000 description 4
• YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 4
• YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 239000002841 Lewis acid Substances 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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