JP5887172B2

JP5887172B2 - 感光性樹脂組成物、レリーフパターン形成材料、感光性膜、ポリイミド膜、硬化レリーフパターンの製造方法、及び半導体装置

感光性樹脂組成物、レリーフパターン形成材料、感光性膜、ポリイミド膜、硬化レリーフパターンの製造方法、及び半導体装置 Download PDF

Info

Publication number: JP5887172B2
Authority: JP; Japan
Prior art keywords: group; general formula; acid; resin composition; atom
Prior art date: 2011-07-29
Legal status : Active

Application number

JP2012068197A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013050696A (ja

Inventor

恭平荒山

和田　健二

健二和田

雨宮　拓馬

拓馬雨宮

Current Assignee

Fujifilm Corp

Original Assignee

Fujifilm Corp

Priority date

2011-07-29

Filing date

2012-03-23

Publication date

2016-03-16

2012-03-23 Application filed by Fujifilm Corp filed Critical Fujifilm Corp

2012-03-23 Priority to JP2012068197A priority Critical patent/JP5887172B2/ja

2012-07-12 Priority to PCT/JP2012/067852 priority patent/WO2013018524A1/ja

2012-07-12 Priority to CN201280037948.3A priority patent/CN103718109B/zh

2012-07-12 Priority to KR1020147002626A priority patent/KR101780663B1/ko

2013-03-14 Publication of JP2013050696A publication Critical patent/JP2013050696A/ja

2016-03-16 Application granted granted Critical

2016-03-16 Publication of JP5887172B2 publication Critical patent/JP5887172B2/ja

Status Active legal-status Critical Current

2032-03-23 Anticipated expiration legal-status Critical

Links

239000011342 resin composition Substances 0.000 title claims description 95
229920001721 polyimide Polymers 0.000 title claims description 35
239000004065 semiconductor Substances 0.000 title claims description 16
238000004519 manufacturing process Methods 0.000 title claims description 11
239000000463 material Substances 0.000 title claims description 8
-1 oxime sulfonate compound Chemical class 0.000 claims description 297
125000000217 alkyl group Chemical group 0.000 claims description 255
125000003118 aryl group Chemical group 0.000 claims description 210
125000004432 carbon atom Chemical group C* 0.000 claims description 177
239000011347 resin Substances 0.000 claims description 176
229920005989 resin Polymers 0.000 claims description 176
125000001424 substituent group Chemical group 0.000 claims description 154
150000001875 compounds Chemical class 0.000 claims description 136
125000000753 cycloalkyl group Chemical group 0.000 claims description 93
239000002253 acid Substances 0.000 claims description 87
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 86
125000003545 alkoxy group Chemical group 0.000 claims description 79
125000005843 halogen group Chemical group 0.000 claims description 78
125000000962 organic group Chemical group 0.000 claims description 70
125000004093 cyano group Chemical group *C#N 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000002723 alicyclic group Chemical group 0.000 claims description 45
125000003710 aryl alkyl group Chemical group 0.000 claims description 43
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
230000009471 action Effects 0.000 claims description 33
125000001153 fluoro group Chemical group F* 0.000 claims description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
150000002148 esters Chemical class 0.000 claims description 27
125000004104 aryloxy group Chemical group 0.000 claims description 26
229910052731 fluorine Inorganic materials 0.000 claims description 26
125000001309 chloro group Chemical group Cl* 0.000 claims description 25
125000005647 linker group Chemical group 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
230000005855 radiation Effects 0.000 claims description 24
229910052710 silicon Inorganic materials 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000002950 monocyclic group Chemical group 0.000 claims description 21
238000005979 thermal decomposition reaction Methods 0.000 claims description 21
125000003367 polycyclic group Chemical group 0.000 claims description 20
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000006575 electron-withdrawing group Chemical group 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
125000002252 acyl group Chemical group 0.000 claims description 17
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 17
150000007514 bases Chemical class 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 15
239000000758 substrate Substances 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 14
238000011161 development Methods 0.000 claims description 14
230000018109 developmental process Effects 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
229910052702 rhenium Inorganic materials 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 10
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
125000003368 amide group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
239000002318 adhesion promoter Substances 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000000542 sulfonic acid group Chemical group 0.000 claims description 7
125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
239000012528 membrane Substances 0.000 claims description 3
230000007261 regionalization Effects 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 197
239000000243 solution Substances 0.000 description 172
239000007787 solid Substances 0.000 description 167
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 158
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 148
229920005575 poly(amic acid) Polymers 0.000 description 145
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
239000000203 mixture Substances 0.000 description 92
229910052757 nitrogen Inorganic materials 0.000 description 88
230000015572 biosynthetic process Effects 0.000 description 87
238000003786 synthesis reaction Methods 0.000 description 87
238000006243 chemical reaction Methods 0.000 description 76
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 73
238000005227 gel permeation chromatography Methods 0.000 description 72
239000000047 product Substances 0.000 description 56
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 56
150000001732 carboxylic acid derivatives Chemical class 0.000 description 54
150000001733 carboxylic acid esters Chemical class 0.000 description 53
238000001914 filtration Methods 0.000 description 52
239000007788 liquid Substances 0.000 description 50
230000010354 integration Effects 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
239000010408 film Substances 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
230000035882 stress Effects 0.000 description 30
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 29
230000035945 sensitivity Effects 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
125000002947 alkylene group Chemical group 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
229910052799 carbon Inorganic materials 0.000 description 24
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 23
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 22
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 22
239000000126 substance Substances 0.000 description 22
235000012431 wafers Nutrition 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 21
239000012044 organic layer Substances 0.000 description 20
239000004642 Polyimide Substances 0.000 description 19
WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 19
239000013585 weight reducing agent Substances 0.000 description 19
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000001110 calcium chloride Substances 0.000 description 18
229910001628 calcium chloride Inorganic materials 0.000 description 18
125000006165 cyclic alkyl group Chemical group 0.000 description 17
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 17
150000004985 diamines Chemical class 0.000 description 17
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 17
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 15
125000001624 naphthyl group Chemical group 0.000 description 15
125000004430 oxygen atom Chemical group O* 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 13
239000012346 acetyl chloride Substances 0.000 description 13
239000010703 silicon Substances 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
125000004434 sulfur atom Chemical group 0.000 description 13
125000005042 acyloxymethyl group Chemical group 0.000 description 12
125000004849 alkoxymethyl group Chemical group 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
125000005702 oxyalkylene group Chemical group 0.000 description 12
239000002243 precursor Substances 0.000 description 12
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
150000008065 acid anhydrides Chemical class 0.000 description 11
125000004423 acyloxy group Chemical group 0.000 description 11
238000004458 analytical method Methods 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
239000012153 distilled water Substances 0.000 description 11
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 11
239000003513 alkali Substances 0.000 description 10
150000001450 anions Chemical class 0.000 description 10
150000001721 carbon Chemical group 0.000 description 10
125000004122 cyclic group Chemical group 0.000 description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 10
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 10
238000004090 dissolution Methods 0.000 description 9
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
125000005409 triarylsulfonium group Chemical group 0.000 description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
150000001805 chlorine compounds Chemical class 0.000 description 8
238000001723 curing Methods 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
125000004185 ester group Chemical group 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
238000001459 lithography Methods 0.000 description 8
125000006353 oxyethylene group Chemical group 0.000 description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
125000005110 aryl thio group Chemical group 0.000 description 7
125000002993 cycloalkylene group Chemical group 0.000 description 7
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 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
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
239000000178 monomer Substances 0.000 description 6
230000000269 nucleophilic effect Effects 0.000 description 6
125000002130 sulfonic acid ester group Chemical group 0.000 description 6
150000003459 sulfonic acid esters Chemical class 0.000 description 6
238000001308 synthesis method Methods 0.000 description 6
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
239000011592 zinc chloride Substances 0.000 description 6
235000005074 zinc chloride Nutrition 0.000 description 6
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
125000000304 alkynyl group Chemical group 0.000 description 5
150000004984 aromatic diamines Chemical class 0.000 description 5
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 5
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229940081623 rose bengal Drugs 0.000 description 1
229930187593 rose bengal Natural products 0.000 description 1
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229960004889 salicylic acid Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
238000004528 spin coating Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003866 tertiary ammonium salts Chemical class 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
150000004897 thiazines Chemical class 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005556 thienylene group Chemical group 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
229950003937 tolonium Drugs 0.000 description 1
HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
125000005580 triphenylene group Chemical group 0.000 description 1
KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1