TWI869664B

TWI869664B - 聚醯亞胺、樹脂組合物、聚醯亞胺膜及其製造方法

聚醯亞胺、樹脂組合物、聚醯亞胺膜及其製造方法 Download PDF

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Publication number: TWI869664B
Authority: TW; Taiwan
Prior art keywords: general formula; polyimide; group; polyamide; organic group
Prior art date: 2021-04-02

Application number

TW111112434A

Other languages

English (en)

Chinese (zh)

Other versions

TW202246391A (zh

Inventor

加藤聡

佐藤雄太

柏田健

金田隆行

頼末友裕

Original Assignee

日商旭化成股份有限公司

Priority date

2021-04-02

Filing date

2022-03-31

Publication date

2025-01-11

2022-03-31 Application filed by 日商旭化成股份有限公司 filed Critical 日商旭化成股份有限公司

2022-12-01 Publication of TW202246391A publication Critical patent/TW202246391A/zh

2025-01-11 Application granted granted Critical

2025-01-11 Publication of TWI869664B publication Critical patent/TWI869664B/zh

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239000011342 resin composition Substances 0.000 title claims abstract description 165
229920001721 polyimide Polymers 0.000 title claims description 482
239000004642 Polyimide Substances 0.000 title claims description 282
238000004519 manufacturing process Methods 0.000 title description 62
229920002312 polyamide-imide Polymers 0.000 claims abstract description 139
239000004962 Polyamide-imide Substances 0.000 claims abstract description 106
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 68
239000003054 catalyst Substances 0.000 claims abstract description 67
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
239000003960 organic solvent Substances 0.000 claims abstract description 24
HUZQMNBPSVTFAG-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1C=NC=C1.C(C)(C)(C)OC(=O)N1C=NC=C1 Chemical compound C(C)(C)(C)OC(=O)N1C=NC=C1.C(C)(C)(C)OC(=O)N1C=NC=C1 HUZQMNBPSVTFAG-UHFFFAOYSA-N 0.000 claims abstract description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 15
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 11
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 10
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims abstract description 10
GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims abstract description 9
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 claims description 176
125000000962 organic group Chemical group 0.000 claims description 167
150000004985 diamines Chemical class 0.000 claims description 145
239000004952 Polyamide Substances 0.000 claims description 138
229920002647 polyamide Polymers 0.000 claims description 138
-1 imidazole compound Chemical class 0.000 claims description 131
239000000126 substance Substances 0.000 claims description 122
125000004432 carbon atom Chemical group C* 0.000 claims description 108
239000002904 solvent Substances 0.000 claims description 107
239000002243 precursor Substances 0.000 claims description 86
229910052736 halogen Inorganic materials 0.000 claims description 76
150000002367 halogens Chemical class 0.000 claims description 76
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 claims description 71
238000009835 boiling Methods 0.000 claims description 65
239000002253 acid Substances 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 47
229920001577 copolymer Polymers 0.000 claims description 39
150000008064 anhydrides Chemical class 0.000 claims description 31
229920000768 polyamine Polymers 0.000 claims description 27
NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 25
CXISKMDTEFIGTG-UHFFFAOYSA-N [4-(1,3-dioxo-2-benzofuran-5-carbonyl)oxyphenyl] 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(OC=2C=CC(OC(=O)C=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)=O)=C1 CXISKMDTEFIGTG-UHFFFAOYSA-N 0.000 claims description 25
229920000642 polymer Polymers 0.000 claims description 25
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 22
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 21
QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 claims description 20
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 18
125000005647 linker group Chemical group 0.000 claims description 18
102100031503 Barrier-to-autointegration factor-like protein Human genes 0.000 claims description 17
101000729827 Homo sapiens Barrier-to-autointegration factor-like protein Proteins 0.000 claims description 17
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 14
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 10
JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 claims description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 claims description 7
XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 claims description 7
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 claims description 7
LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 claims description 7
KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 claims description 7
RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 claims description 7
TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 claims description 7
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 7
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 7
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 7
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
229960003512 nicotinic acid Drugs 0.000 claims description 5
235000001968 nicotinic acid Nutrition 0.000 claims description 5
239000011664 nicotinic acid Substances 0.000 claims description 5
229920001400 block copolymer Polymers 0.000 claims 4
239000010408 film Substances 0.000 description 262
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 211
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 129
239000009719 polyimide resin Substances 0.000 description 112
239000000758 substrate Substances 0.000 description 97
239000000243 solution Substances 0.000 description 88
239000002966 varnish Substances 0.000 description 88
230000015572 biosynthetic process Effects 0.000 description 81
238000003786 synthesis reaction Methods 0.000 description 77
238000011156 evaluation Methods 0.000 description 74
238000000034 method Methods 0.000 description 65
229910052757 nitrogen Inorganic materials 0.000 description 65
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
238000007872 degassing Methods 0.000 description 57
150000001875 compounds Chemical class 0.000 description 47
238000000576 coating method Methods 0.000 description 46
238000001723 curing Methods 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
125000006158 tetracarboxylic acid group Chemical group 0.000 description 44
239000011248 coating agent Substances 0.000 description 42
239000011521 glass Substances 0.000 description 42
238000010438 heat treatment Methods 0.000 description 40
230000002829 reductive effect Effects 0.000 description 38
QZQQBWVFOFYUBV-UHFFFAOYSA-N cyclobutanesulfonic acid Chemical group OS(=O)(=O)C1CCC1 QZQQBWVFOFYUBV-UHFFFAOYSA-N 0.000 description 37
230000000052 comparative effect Effects 0.000 description 36
238000003303 reheating Methods 0.000 description 35
229920005989 resin Polymers 0.000 description 35
239000011347 resin Substances 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 34
230000007547 defect Effects 0.000 description 34
239000002210 silicon-based material Substances 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
125000000524 functional group Chemical group 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
125000000217 alkyl group Chemical group 0.000 description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
229920005575 poly(amic acid) Polymers 0.000 description 22
238000003756 stirring Methods 0.000 description 22
239000010410 layer Substances 0.000 description 21
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 20
125000003118 aryl group Chemical group 0.000 description 20
238000006116 polymerization reaction Methods 0.000 description 20
239000007787 solid Substances 0.000 description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 18
229910052731 fluorine Inorganic materials 0.000 description 17
239000001257 hydrogen Substances 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 17
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
239000011737 fluorine Substances 0.000 description 15
239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 14
229910052581 Si3N4 Inorganic materials 0.000 description 14
230000009477 glass transition Effects 0.000 description 14
HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
LOCTYHIHNCOYJZ-UHFFFAOYSA-N (4-aminophenyl) 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1OC(=O)C1=CC=C(N)C=C1 LOCTYHIHNCOYJZ-UHFFFAOYSA-N 0.000 description 13
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
125000001931 aliphatic group Chemical group 0.000 description 13
238000005227 gel permeation chromatography Methods 0.000 description 13
239000012299 nitrogen atmosphere Substances 0.000 description 13
229910052710 silicon Inorganic materials 0.000 description 13
239000010703 silicon Substances 0.000 description 13
239000004094 surface-active agent Substances 0.000 description 13
230000002194 synthesizing effect Effects 0.000 description 13
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
238000005452 bending Methods 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
230000008859 change Effects 0.000 description 12
238000001035 drying Methods 0.000 description 12
150000003949 imides Chemical group 0.000 description 12
239000004973 liquid crystal related substance Substances 0.000 description 12
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 11
239000012298 atmosphere Substances 0.000 description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
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 11
125000004122 cyclic group Chemical group 0.000 description 11
239000000178 monomer Substances 0.000 description 11
230000003287 optical effect Effects 0.000 description 11
239000001301 oxygen Substances 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
238000003860 storage Methods 0.000 description 11
235000012431 wafers Nutrition 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
150000001408 amides Chemical group 0.000 description 10
230000008569 process Effects 0.000 description 10
OVASAEXSPYGGES-UHFFFAOYSA-N C1C2C(C(OC3=O)=O)C3C1CC2(C1=O)CCC21CC1CC2C2C(=O)OC(=O)C12 Chemical compound C1C2C(C(OC3=O)=O)C3C1CC2(C1=O)CCC21CC1CC2C2C(=O)OC(=O)C12 OVASAEXSPYGGES-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000006068 polycondensation reaction Methods 0.000 description 9
238000010992 reflux Methods 0.000 description 9
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
239000000010 aprotic solvent Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
229920001296 polysiloxane Polymers 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
125000003944 tolyl group Chemical group 0.000 description 8
238000011282 treatment Methods 0.000 description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
125000004018 acid anhydride group Chemical group 0.000 description 7
125000002723 alicyclic group Chemical group 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
125000006159 dianhydride group Chemical class 0.000 description 7
239000004205 dimethyl polysiloxane Substances 0.000 description 7
235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
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239000004065 semiconductor Substances 0.000 description 7
238000002834 transmittance Methods 0.000 description 7
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 6
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PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 6
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125000003277 amino group Chemical group 0.000 description 6
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BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
229910021420 polycrystalline silicon Inorganic materials 0.000 description 6
229920002223 polystyrene Polymers 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002994 raw material Substances 0.000 description 6
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 5
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