WO2022264994A1 - 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 - Google Patents
樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 Download PDFInfo
- Publication number
- WO2022264994A1 WO2022264994A1 PCT/JP2022/023722 JP2022023722W WO2022264994A1 WO 2022264994 A1 WO2022264994 A1 WO 2022264994A1 JP 2022023722 W JP2022023722 W JP 2022023722W WO 2022264994 A1 WO2022264994 A1 WO 2022264994A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- group
- formula
- acid
- resin composition
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 172
- 239000011347 resin Substances 0.000 title claims abstract description 172
- 239000011342 resin composition Substances 0.000 title claims abstract description 165
- 239000004065 semiconductor Substances 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 357
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 80
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- -1 maleimide compound Chemical class 0.000 claims description 309
- 238000000016 photochemical curing Methods 0.000 claims description 96
- 239000003999 initiator Substances 0.000 claims description 60
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 59
- 150000008065 acid anhydrides Chemical class 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000004020 conductor Substances 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 abstract description 54
- 238000006243 chemical reaction Methods 0.000 abstract description 52
- 238000011161 development Methods 0.000 abstract description 34
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 238000000034 method Methods 0.000 description 97
- 239000010410 layer Substances 0.000 description 78
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 72
- 239000002904 solvent Substances 0.000 description 65
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 47
- 238000002834 transmittance Methods 0.000 description 44
- 239000003822 epoxy resin Substances 0.000 description 41
- 229920000647 polyepoxide Polymers 0.000 description 40
- 239000003054 catalyst Substances 0.000 description 38
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 37
- 239000002966 varnish Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- 230000018109 developmental process Effects 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
- 239000005011 phenolic resin Substances 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 239000000126 substance Substances 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002835 absorbance Methods 0.000 description 21
- 239000000945 filler Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229910001868 water Inorganic materials 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- 229920003986 novolac Polymers 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 230000001747 exhibiting effect Effects 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000004643 cyanate ester Substances 0.000 description 14
- 238000005886 esterification reaction Methods 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 229920001568 phenolic resin Polymers 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- 238000003475 lamination Methods 0.000 description 12
- 230000009257 reactivity Effects 0.000 description 12
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-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
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 150000001491 aromatic compounds Chemical class 0.000 description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 239000003759 ester based solvent Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 8
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 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 8
- 239000011521 glass Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- 125000000962 organic group Chemical group 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
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229920002799 BoPET Polymers 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000005453 ketone based solvent Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000178 monomer Substances 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
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 5
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 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
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical class C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000005917 3-methylpentyl group Chemical group 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 150000005130 benzoxazines Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920001721 polyimide Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 2
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FWHUTKPMCKSUCV-UHFFFAOYSA-N 1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-carboxylic acid Chemical compound C1C(C(=O)O)CCC2C(=O)OC(=O)C12 FWHUTKPMCKSUCV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XAZPKEBWNIUCKF-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XAZPKEBWNIUCKF-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 2
- QCNWZROVPSVEJA-UHFFFAOYSA-N Heptadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCC(O)=O QCNWZROVPSVEJA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Chemical group 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- INHGSGHLQLYYND-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(OC#N)C=C1 INHGSGHLQLYYND-UHFFFAOYSA-N 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- RSHYBLDYLNAJJV-UHFFFAOYSA-N anthracene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C3C=C21 RSHYBLDYLNAJJV-UHFFFAOYSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QNSOHXTZPUMONC-UHFFFAOYSA-N benzene-1,2,3,4,5-pentacarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O QNSOHXTZPUMONC-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910001593 boehmite Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 2
- WTNDADANUZETTI-UHFFFAOYSA-N cyclohexane-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1 WTNDADANUZETTI-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical class O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229940117955 isoamyl acetate Drugs 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000010680 novolac-type phenolic resin Substances 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 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 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
- IQVLXQGNLCPZCL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)NCCCCC(NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O IQVLXQGNLCPZCL-UHFFFAOYSA-N 0.000 description 1
- JRBJLOCMQWBLDF-UHFFFAOYSA-N (2,6-dichlorophenyl) cyanate Chemical compound ClC1=CC=CC(Cl)=C1OC#N JRBJLOCMQWBLDF-UHFFFAOYSA-N 0.000 description 1
- VSHAQOZVUZJKCO-UHFFFAOYSA-N (2,6-ditert-butylphenyl) cyanate Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OC#N VSHAQOZVUZJKCO-UHFFFAOYSA-N 0.000 description 1
- SMTQKQLZBRJCLI-UHFFFAOYSA-N (2-cyanatophenyl) cyanate Chemical compound N#COC1=CC=CC=C1OC#N SMTQKQLZBRJCLI-UHFFFAOYSA-N 0.000 description 1
- ULYBHRQVCDELMO-UHFFFAOYSA-N (2-ethyl-4-nitrophenyl) cyanate Chemical compound CCC1=CC([N+]([O-])=O)=CC=C1OC#N ULYBHRQVCDELMO-UHFFFAOYSA-N 0.000 description 1
- SHBUQGBESNZMCH-UHFFFAOYSA-N (2-nitrophenyl) cyanate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC#N SHBUQGBESNZMCH-UHFFFAOYSA-N 0.000 description 1
- NGGIZAWDYJYQBS-UHFFFAOYSA-N (2-tert-butyl-4-cyanatophenyl) cyanate Chemical compound CC(C)(C)C1=CC(OC#N)=CC=C1OC#N NGGIZAWDYJYQBS-UHFFFAOYSA-N 0.000 description 1
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 description 1
- KXVFBCSUGDNXQF-DZDBOGACSA-N (2z,4z,6z,8z,10z)-tetracosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C=C/C(O)=O KXVFBCSUGDNXQF-DZDBOGACSA-N 0.000 description 1
- QSMZSCNZPOTAQR-UHFFFAOYSA-N (3,5-dimethylphenyl) cyanate Chemical compound CC1=CC(C)=CC(OC#N)=C1 QSMZSCNZPOTAQR-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
- UBWVCMYZYWVZFK-UHFFFAOYSA-N (3-chloro-2-methylphenyl) cyanate Chemical compound CC1=C(Cl)C=CC=C1OC#N UBWVCMYZYWVZFK-UHFFFAOYSA-N 0.000 description 1
- YVOQQUGUJXFKOC-UHFFFAOYSA-N (3-chlorophenyl) cyanate Chemical compound ClC1=CC=CC(OC#N)=C1 YVOQQUGUJXFKOC-UHFFFAOYSA-N 0.000 description 1
- UVKWYPJUDVBJBS-UHFFFAOYSA-N (3-cyanato-2,4,6-trimethylphenyl) cyanate Chemical compound CC1=CC(C)=C(OC#N)C(C)=C1OC#N UVKWYPJUDVBJBS-UHFFFAOYSA-N 0.000 description 1
- OSHDNORJIBTCJW-UHFFFAOYSA-N (3-cyanato-5-methylphenyl) cyanate Chemical compound CC1=CC(OC#N)=CC(OC#N)=C1 OSHDNORJIBTCJW-UHFFFAOYSA-N 0.000 description 1
- QQZZMAPJAKOSNG-UHFFFAOYSA-N (3-cyanatophenyl) cyanate Chemical compound N#COC1=CC=CC(OC#N)=C1 QQZZMAPJAKOSNG-UHFFFAOYSA-N 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- MJTRGJDBPFGULK-UHFFFAOYSA-N (4-acetamidophenyl) cyanate Chemical compound CC(=O)NC1=CC=C(OC#N)C=C1 MJTRGJDBPFGULK-UHFFFAOYSA-N 0.000 description 1
- MUAFEFAYKJZTHJ-UHFFFAOYSA-N (4-acetylphenyl) cyanate Chemical compound CC(=O)C1=CC=C(OC#N)C=C1 MUAFEFAYKJZTHJ-UHFFFAOYSA-N 0.000 description 1
- GVJYBKRRHMMTMH-UHFFFAOYSA-N (4-benzoyl-1-cyanatocyclohexa-2,4-dien-1-yl) cyanate Chemical compound O(C#N)C1(CC=C(C(=O)C2=CC=CC=C2)C=C1)OC#N GVJYBKRRHMMTMH-UHFFFAOYSA-N 0.000 description 1
- VESOYJBKIYTTEL-UHFFFAOYSA-N (4-benzoylphenyl) cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(=O)C1=CC=CC=C1 VESOYJBKIYTTEL-UHFFFAOYSA-N 0.000 description 1
- IJYLPQZZHPXEIH-UHFFFAOYSA-N (4-cyanato-1,5-dimethylcyclohexa-2,4-dien-1-yl) cyanate Chemical compound O(C#N)C1=C(CC(C=C1)(C)OC#N)C IJYLPQZZHPXEIH-UHFFFAOYSA-N 0.000 description 1
- GUGZCSAPOLLKNG-UHFFFAOYSA-N (4-cyanatophenyl) cyanate Chemical compound N#COC1=CC=C(OC#N)C=C1 GUGZCSAPOLLKNG-UHFFFAOYSA-N 0.000 description 1
- FFUGFEZHSFMOTP-UHFFFAOYSA-N (4-cyclohexylphenyl) cyanate Chemical compound C1=CC(OC#N)=CC=C1C1CCCCC1 FFUGFEZHSFMOTP-UHFFFAOYSA-N 0.000 description 1
- LKOYFNVMCUKOJD-UHFFFAOYSA-N (4-ethenylphenyl) cyanate Chemical compound C=CC1=CC=C(OC#N)C=C1 LKOYFNVMCUKOJD-UHFFFAOYSA-N 0.000 description 1
- BYMZMVNQWJIIDN-UHFFFAOYSA-N (4-formylphenyl) cyanate Chemical compound O=CC1=CC=C(OC#N)C=C1 BYMZMVNQWJIIDN-UHFFFAOYSA-N 0.000 description 1
- HZSITCSNYNWEMM-UHFFFAOYSA-N (4-methoxynaphthalen-1-yl) cyanate Chemical compound O(C#N)C1=CC=C(C2=CC=CC=C12)OC HZSITCSNYNWEMM-UHFFFAOYSA-N 0.000 description 1
- RFXSQXFVJCZAMW-UHFFFAOYSA-N (4-methoxyphenyl) cyanate Chemical compound COC1=CC=C(OC#N)C=C1 RFXSQXFVJCZAMW-UHFFFAOYSA-N 0.000 description 1
- UGMKNMPRUHJNQK-UHFFFAOYSA-N (4-methylphenyl) cyanate Chemical compound CC1=CC=C(OC#N)C=C1 UGMKNMPRUHJNQK-UHFFFAOYSA-N 0.000 description 1
- OQOBDFYUAMYTRM-UHFFFAOYSA-N (4-methylsulfanylphenyl) cyanate Chemical compound CSC1=CC=C(OC#N)C=C1 OQOBDFYUAMYTRM-UHFFFAOYSA-N 0.000 description 1
- SGACLTVKXIFYLM-UHFFFAOYSA-N (4-phenylphenyl) cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=CC=C1 SGACLTVKXIFYLM-UHFFFAOYSA-N 0.000 description 1
- UNSRRHDPHVZAHH-YOILPLPUSA-N (5Z,8Z,11Z)-icosatrienoic acid Chemical compound CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(O)=O UNSRRHDPHVZAHH-YOILPLPUSA-N 0.000 description 1
- HXQHFNIKBKZGRP-URPRIDOGSA-N (5Z,9Z,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C\C=C/CC\C=C/CCCC(O)=O HXQHFNIKBKZGRP-URPRIDOGSA-N 0.000 description 1
- CCXJDBFHWLSUFE-UHFFFAOYSA-N (6-methoxynaphthalen-2-yl) cyanate Chemical compound O(C#N)C1=CC2=CC=C(C=C2C=C1)OC CCXJDBFHWLSUFE-UHFFFAOYSA-N 0.000 description 1
- PWGMXFQYTQPRLC-UHFFFAOYSA-N (7-methoxynaphthalen-2-yl) cyanate Chemical compound O(C#N)C1=CC2=CC(=CC=C2C=C1)OC PWGMXFQYTQPRLC-UHFFFAOYSA-N 0.000 description 1
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 description 1
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- OBDUMNZXAIUUTH-HWKANZROSA-N (e)-tetradec-2-ene Chemical group CCCCCCCCCCC\C=C\C OBDUMNZXAIUUTH-HWKANZROSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- CGSKOGYKWHUSLC-UHFFFAOYSA-N 1-(4-aminophenyl)-1,3,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC=C(N)C=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 CGSKOGYKWHUSLC-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 1
- FERLGYOHRKHQJP-UHFFFAOYSA-N 1-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCOCCN1C(=O)C=CC1=O FERLGYOHRKHQJP-UHFFFAOYSA-N 0.000 description 1
- OYRSKXCXEFLTEY-UHFFFAOYSA-N 1-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCOCCOCCN1C(=O)C=CC1=O OYRSKXCXEFLTEY-UHFFFAOYSA-N 0.000 description 1
- MDEDKSYUWOWMHU-UHFFFAOYSA-N 1-[2-ethyl-4-[[3-ethyl-5-methyl-4-(3-methyl-2,5-dioxopyrrol-1-yl)phenyl]methyl]-6-methylphenyl]-3-methylpyrrole-2,5-dione Chemical compound C(C)C=1C=C(C=C(C=1N1C(C(C)=CC1=O)=O)C)CC1=CC(=C(C(=C1)C)N1C(C(C)=CC1=O)=O)CC MDEDKSYUWOWMHU-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- MBNMVPPPCZKPIJ-UHFFFAOYSA-N 1-[3-[3-[3-(2,5-dioxopyrrol-1-yl)phenoxy]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(OC=2C=C(OC=3C=C(C=CC=3)N3C(C=CC3=O)=O)C=CC=2)=C1 MBNMVPPPCZKPIJ-UHFFFAOYSA-N 0.000 description 1
- WXXSHAKLDCERGU-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)butyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCN1C(=O)C=CC1=O WXXSHAKLDCERGU-UHFFFAOYSA-N 0.000 description 1
- UGJHILWNNSROJV-UHFFFAOYSA-N 1-[4-[3-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1OC1=CC=CC(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)=C1 UGJHILWNNSROJV-UHFFFAOYSA-N 0.000 description 1
- BDDKHONBQBEGMA-UHFFFAOYSA-N 1-[4-[[3,5-diethyl-4-(3-methyl-2,5-dioxopyrrol-1-yl)phenyl]methyl]-2,6-diethylphenyl]-3-methylpyrrole-2,5-dione Chemical compound C=1C(CC)=C(N2C(C(C)=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N1C(=O)C=C(C)C1=O BDDKHONBQBEGMA-UHFFFAOYSA-N 0.000 description 1
- DRDFUKFBOJQEEO-UHFFFAOYSA-N 1-[4-[[3,5-dimethyl-4-(3-methyl-2,5-dioxopyrrol-1-yl)phenyl]methyl]-2,6-dimethylphenyl]-3-methylpyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C(C(=C1)C)=C(C)C=C1CC(C=C1C)=CC(C)=C1N1C(=O)C(C)=CC1=O DRDFUKFBOJQEEO-UHFFFAOYSA-N 0.000 description 1
- NHWYMYDMYCNUKI-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(CC)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N1C(=O)C=CC1=O NHWYMYDMYCNUKI-UHFFFAOYSA-N 0.000 description 1
- RUORVEVRVBXRIO-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-dimethylphenyl]methyl]-2,6-dimethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(C)=CC=1CC(C=C1C)=CC(C)=C1N1C(=O)C=CC1=O RUORVEVRVBXRIO-UHFFFAOYSA-N 0.000 description 1
- GQWVSMZIXHLFQM-UHFFFAOYSA-N 1-[5-(2,5-dioxopyrrol-1-yl)-4-methylpentyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC(C)CCCN1C(=O)C=CC1=O GQWVSMZIXHLFQM-UHFFFAOYSA-N 0.000 description 1
- XNMVBFGQPBLPKO-UHFFFAOYSA-N 1-[5-(2,5-dioxopyrrol-1-yl)pentyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCN1C(=O)C=CC1=O XNMVBFGQPBLPKO-UHFFFAOYSA-N 0.000 description 1
- XQCDLHVXAXBMGW-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)-3,5,5-trimethylhexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC(C)(C)CC(C)CCN1C(=O)C=CC1=O XQCDLHVXAXBMGW-UHFFFAOYSA-N 0.000 description 1
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- FLNMXNRQDBBBJL-UHFFFAOYSA-N 1-[[3-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1CC(CN2C(C=CC2=O)=O)CCC1 FLNMXNRQDBBBJL-UHFFFAOYSA-N 0.000 description 1
- JZHXUFCBZBJDGE-UHFFFAOYSA-N 1-[[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1CCC(CN2C(C=CC2=O)=O)CC1 JZHXUFCBZBJDGE-UHFFFAOYSA-N 0.000 description 1
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- BVEIKFLZWBDLJG-UHFFFAOYSA-N 1-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCC BVEIKFLZWBDLJG-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- HHVCCCZZVQMAMT-UHFFFAOYSA-N 1-hydroxy-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(O)C(=O)C=C1C1=CC=CC=C1 HHVCCCZZVQMAMT-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dipropyldiphenylmethane Chemical compound COC1=CC(CCC)=CC(CC=2C(=C(OC)C=C(CCC)C=2)O)=C1O ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 0.000 description 1
- ILIKFPWSIPNAPS-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorooxetane Chemical compound FC1(F)OC(F)(F)C1(F)F ILIKFPWSIPNAPS-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- XLXVRIOQCHHBTC-UHFFFAOYSA-N 2,2-bis(phenoxycarbonyl)propanedioic acid Chemical compound C=1C=CC=CC=1OC(=O)C(C(O)=O)(C(=O)O)C(=O)OC1=CC=CC=C1 XLXVRIOQCHHBTC-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- XHYFCIYCSYEDCP-UHFFFAOYSA-N 2,2-dimethyloxetane Chemical compound CC1(C)CCO1 XHYFCIYCSYEDCP-UHFFFAOYSA-N 0.000 description 1
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- WAXBZQUSTLNLPU-UHFFFAOYSA-N 2,5-dioxo-3-phenylpyrrole-1-carboxylic acid Chemical compound O=C1N(C(=O)O)C(=O)C=C1C1=CC=CC=C1 WAXBZQUSTLNLPU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- MTJUELTVQKBEPR-UHFFFAOYSA-N 2-(chloromethyl)oxetane Chemical compound ClCC1CCO1 MTJUELTVQKBEPR-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- PKKMTXYTMIUYND-UHFFFAOYSA-N 2-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropoxy]methyl]-2-methylpropane-1,3-diol Chemical compound OCC(C)(CO)COCC(C)(CO)CO PKKMTXYTMIUYND-UHFFFAOYSA-N 0.000 description 1
- QPCRFBDJGSEXTM-UHFFFAOYSA-N 2-[[3-hydroxy-2-(hydroxymethyl)propoxy]methyl]propane-1,3-diol Chemical compound OCC(CO)COCC(CO)CO QPCRFBDJGSEXTM-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- CCOKFYVEROKSGU-UHFFFAOYSA-N 2-butyladamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1C(CCCC)C2(C(O)=O)C3 CCOKFYVEROKSGU-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- POUAVEAWTZEXOD-UHFFFAOYSA-N 2-ethyladamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1C(CC)C2(C(O)=O)C3 POUAVEAWTZEXOD-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- IZBNQJCHUQYWLS-UHFFFAOYSA-N 2-methyladamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC1C(C)C2(C(O)=O)C3 IZBNQJCHUQYWLS-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- CPFRUJWRXRBCLM-UHFFFAOYSA-N 2-phenylethyl cyanate Chemical compound N#COCCC1=CC=CC=C1 CPFRUJWRXRBCLM-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
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- CPBJMKMKNCRKQB-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 CPBJMKMKNCRKQB-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- RVGLUKRYMXEQAH-UHFFFAOYSA-N 3,3-dimethyloxetane Chemical compound CC1(C)COC1 RVGLUKRYMXEQAH-UHFFFAOYSA-N 0.000 description 1
- BGDOLELXXPTPFX-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzoxazine Chemical group C1=CC=C2ONCCC2=C1 BGDOLELXXPTPFX-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
- BQQGVSONEPNPAB-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound CCOC(OCC)[SiH2]CCCOC(=O)C(C)=C BQQGVSONEPNPAB-UHFFFAOYSA-N 0.000 description 1
- LOOUJXUUGIUEBC-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propane-1-thiol Chemical compound COC(OC)[SiH2]CCCS LOOUJXUUGIUEBC-UHFFFAOYSA-N 0.000 description 1
- VLZDYNDUVLBNLD-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound COC(OC)[SiH2]CCCOC(=O)C(C)=C VLZDYNDUVLBNLD-UHFFFAOYSA-N 0.000 description 1
- YRNCACXJEDBLDE-UHFFFAOYSA-N 3-(methoxymethyl)-3-methyloxetane Chemical compound COCC1(C)COC1 YRNCACXJEDBLDE-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- VXPSQDAMFATNNG-UHFFFAOYSA-N 3-[2-(2,5-dioxopyrrol-3-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C(=CC=CC=2)C=2C(NC(=O)C=2)=O)=C1 VXPSQDAMFATNNG-UHFFFAOYSA-N 0.000 description 1
- MOSSLXZUUKTULI-UHFFFAOYSA-N 3-[3-(2,5-dioxopyrrol-3-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(C=2C(NC(=O)C=2)=O)C=C1C1=CC(=O)NC1=O MOSSLXZUUKTULI-UHFFFAOYSA-N 0.000 description 1
- VCFJLCCBKJNFKQ-UHFFFAOYSA-N 3-[4-(2,5-dioxopyrrol-3-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC(=CC=2)C=2C(NC(=O)C=2)=O)=C1 VCFJLCCBKJNFKQ-UHFFFAOYSA-N 0.000 description 1
- GSHIDYWGMUZEOL-UHFFFAOYSA-N 3-[[2-[(2,5-dioxopyrrol-3-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C(=CC=CC=2)CC=2C(NC(=O)C=2)=O)=C1 GSHIDYWGMUZEOL-UHFFFAOYSA-N 0.000 description 1
- RVFQOYLBPXHFKR-UHFFFAOYSA-N 3-[[3-[(2,5-dioxopyrrol-3-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=C(CC=3C(NC(=O)C=3)=O)C=CC=2)=C1 RVFQOYLBPXHFKR-UHFFFAOYSA-N 0.000 description 1
- KAWODUAUIIOGGH-UHFFFAOYSA-N 3-[[4-[(2,5-dioxopyrrol-3-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC(CC=3C(NC(=O)C=3)=O)=CC=2)=C1 KAWODUAUIIOGGH-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 1
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- UMIADIZYYGHJBZ-UHFFFAOYSA-N 3-methyl-1-[4-[4-[2-[4-[4-(3-methyl-2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C(C=C1)=CC=C1OC1=CC=C(C(C)(C)C=2C=CC(OC=3C=CC(=CC=3)N3C(C(C)=CC3=O)=O)=CC=2)C=C1 UMIADIZYYGHJBZ-UHFFFAOYSA-N 0.000 description 1
- VJQHJNIGWOABDZ-UHFFFAOYSA-N 3-methyloxetane Chemical compound CC1COC1 VJQHJNIGWOABDZ-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-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
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- SMSVFCGGVBWUJL-UHFFFAOYSA-N 4-(2,5-dioxopyrrol-1-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1N1C(=O)C=CC1=O SMSVFCGGVBWUJL-UHFFFAOYSA-N 0.000 description 1
- NCPQROHLJFARLL-UHFFFAOYSA-N 4-(2,5-dioxopyrrol-1-yl)butanoic acid Chemical compound OC(=O)CCCN1C(=O)C=CC1=O NCPQROHLJFARLL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- VPBBZXIPVBVLFZ-UHFFFAOYSA-N 4-phenylbutyl cyanate Chemical compound O(C#N)CCCCC1=CC=CC=C1 VPBBZXIPVBVLFZ-UHFFFAOYSA-N 0.000 description 1
- WOJKKJKETHYEAC-UHFFFAOYSA-N 6-Maleimidocaproic acid Chemical compound OC(=O)CCCCCN1C(=O)C=CC1=O WOJKKJKETHYEAC-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- UNSRRHDPHVZAHH-UHFFFAOYSA-N 6beta,11alpha-Dihydroxy-3alpha,5alpha-cyclopregnan-20-on Natural products CCCCCCCCC=CCC=CCC=CCCCC(O)=O UNSRRHDPHVZAHH-UHFFFAOYSA-N 0.000 description 1
- KIFWEUZANBOIJW-UHFFFAOYSA-N 8-phenyloctyl cyanate Chemical compound N#COCCCCCCCCC1=CC=CC=C1 KIFWEUZANBOIJW-UHFFFAOYSA-N 0.000 description 1
- JWBBBJFKVIQIFQ-UHFFFAOYSA-N 9-phenylnonyl cyanate Chemical compound O(C#N)CCCCCCCCCC1=CC=CC=C1 JWBBBJFKVIQIFQ-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- CPNXAOWDQMNJMA-UHFFFAOYSA-N O(C#N)C1=CC=C(C=C1)C1=C(C(=O)O)C=CC(=C1)OC#N.O(C#N)C1=CC=C(C=C1)OC(C1=CC=C(C=C1)OC#N)=O Chemical compound O(C#N)C1=CC=C(C=C1)C1=C(C(=O)O)C=CC(=C1)OC#N.O(C#N)C1=CC=C(C=C1)OC(C1=CC=C(C=C1)OC#N)=O CPNXAOWDQMNJMA-UHFFFAOYSA-N 0.000 description 1
- QXXAKKCSUSFSEN-UHFFFAOYSA-N OC#N.C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 Chemical compound OC#N.C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QXXAKKCSUSFSEN-UHFFFAOYSA-N 0.000 description 1
- DJNJIDKOTOXHPO-UHFFFAOYSA-N OCC(COCC(CC)(CO)CO)(C)CO Chemical compound OCC(COCC(CC)(CO)CO)(C)CO DJNJIDKOTOXHPO-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 229930040373 Paraformaldehyde Chemical class 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- HXQHFNIKBKZGRP-UHFFFAOYSA-N Ranuncelin-saeure-methylester Natural products CCCCCC=CCC=CCCC=CCCCC(O)=O HXQHFNIKBKZGRP-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N Tetradecane Natural products CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 1
- 235000021322 Vaccenic acid Nutrition 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- FJVCXYGDZUZPBL-UHFFFAOYSA-N [1-(2-cyanatonaphthalen-1-yl)naphthalen-2-yl] cyanate Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OC#N)=C(OC#N)C=CC2=C1 FJVCXYGDZUZPBL-UHFFFAOYSA-N 0.000 description 1
- CMHBPGYKMXHYBG-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] cyanate Chemical compound FC(F)(F)C1=CC=CC(OC#N)=C1 CMHBPGYKMXHYBG-UHFFFAOYSA-N 0.000 description 1
- SUXGZGQKIFLKOR-UHFFFAOYSA-N [4-(2-phenylpropan-2-yl)phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=CC=C1 SUXGZGQKIFLKOR-UHFFFAOYSA-N 0.000 description 1
- JSYZVYJUHKETFH-UHFFFAOYSA-N [4-(4-cyanato-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl] cyanate Chemical group O(C#N)C1=C(C(=C(C(=C1F)F)C1=C(C(=C(C(=C1F)F)OC#N)F)F)F)F JSYZVYJUHKETFH-UHFFFAOYSA-N 0.000 description 1
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 description 1
- HEJGXMCFSSDPOA-UHFFFAOYSA-N [4-(4-cyanatophenyl)phenyl] cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=C(OC#N)C=C1 HEJGXMCFSSDPOA-UHFFFAOYSA-N 0.000 description 1
- CNUHQZDDTLOZRY-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfanylphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1SC1=CC=C(OC#N)C=C1 CNUHQZDDTLOZRY-UHFFFAOYSA-N 0.000 description 1
- BUPOATPDNYBPMR-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfonylphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1S(=O)(=O)C1=CC=C(OC#N)C=C1 BUPOATPDNYBPMR-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- JNCRKOQSRHDNIO-UHFFFAOYSA-N [4-[(4-cyanato-3,5-dimethylphenyl)methyl]-2,6-dimethylphenyl] cyanate Chemical compound CC1=C(OC#N)C(C)=CC(CC=2C=C(C)C(OC#N)=C(C)C=2)=C1 JNCRKOQSRHDNIO-UHFFFAOYSA-N 0.000 description 1
- CGWCRUVZAOUGMY-UHFFFAOYSA-N [4-[(4-cyanatophenyl)-(4-phenylphenyl)methyl]phenyl] cyanate Chemical group O(C#N)C1=CC=C(C=C1)C(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)OC#N CGWCRUVZAOUGMY-UHFFFAOYSA-N 0.000 description 1
- PYICCSHCIIAPJE-UHFFFAOYSA-N [4-[(4-cyanatophenyl)-diphenylmethyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1C(C=1C=CC(OC#N)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PYICCSHCIIAPJE-UHFFFAOYSA-N 0.000 description 1
- NNVFMMULSKOXSJ-UHFFFAOYSA-N [4-[(4-cyanatophenyl)-phenylmethyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1C(C=1C=CC(OC#N)=CC=1)C1=CC=CC=C1 NNVFMMULSKOXSJ-UHFFFAOYSA-N 0.000 description 1
- AWWJTNMLTCVUBS-UHFFFAOYSA-N [4-[1,1-bis(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C=1C=CC(OC#N)=CC=1)(C)C1=CC=C(OC#N)C=C1 AWWJTNMLTCVUBS-UHFFFAOYSA-N 0.000 description 1
- HMACMCXSFRLKGZ-UHFFFAOYSA-N [4-[1,2,2-tris(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound O(C#N)C1=CC=C(C=C1)C(C(C1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N HMACMCXSFRLKGZ-UHFFFAOYSA-N 0.000 description 1
- MWQTYOOOVAXQHW-UHFFFAOYSA-N [4-[1,3-bis(4-cyanatophenyl)propyl]phenyl] cyanate Chemical compound O(C#N)C1=CC=C(C=C1)C(CCC1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N MWQTYOOOVAXQHW-UHFFFAOYSA-N 0.000 description 1
- CVALTECDYLAZLK-UHFFFAOYSA-N [4-[1-(4-cyanato-3-cyclohexylphenyl)cyclohexyl]-2-cyclohexylphenyl] cyanate Chemical compound C1(CCCCC1)C=1C=C(C=CC1OC#N)C1(CCCCC1)C1=CC(=C(C=C1)OC#N)C1CCCCC1 CVALTECDYLAZLK-UHFFFAOYSA-N 0.000 description 1
- HRBBOHNWEWQELI-UHFFFAOYSA-N [4-[1-(4-cyanato-3-methylphenyl)-3-oxo-2-benzofuran-1-yl]-2-methylphenyl] cyanate Chemical compound O(C#N)C1=C(C=C(C=C1)C1(OC(C2=CC=CC=C12)=O)C1=CC(=C(C=C1)OC#N)C)C HRBBOHNWEWQELI-UHFFFAOYSA-N 0.000 description 1
- XDDXAEDWFZJGSJ-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-1-phenylethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C=1C=CC(OC#N)=CC=1)(C)C1=CC=CC=C1 XDDXAEDWFZJGSJ-UHFFFAOYSA-N 0.000 description 1
- WHXGQAGLFTWDAD-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-2,2-dimethylpropyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)(C)C)C1=CC=C(OC#N)C=C1 WHXGQAGLFTWDAD-UHFFFAOYSA-N 0.000 description 1
- VRJVYJZCNABROM-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-2-methylbutyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)CC)C1=CC=C(OC#N)C=C1 VRJVYJZCNABROM-UHFFFAOYSA-N 0.000 description 1
- DUEAQFNVHPRQKJ-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-2-methylpropyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)C)C1=CC=C(OC#N)C=C1 DUEAQFNVHPRQKJ-UHFFFAOYSA-N 0.000 description 1
- OTFDZGDENDYXCY-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-3,3,5-trimethylcyclohexyl]phenyl] cyanate Chemical compound O(C#N)C1=CC=C(C=C1)C1(CC(CC(C1)C)(C)C)C1=CC=C(C=C1)OC#N OTFDZGDENDYXCY-UHFFFAOYSA-N 0.000 description 1
- ALTSFBKKGZFYFL-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-3-methylbutyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CC(C)C)C1=CC=C(OC#N)C=C1 ALTSFBKKGZFYFL-UHFFFAOYSA-N 0.000 description 1
- CUVGYGLIVYYKLM-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)-3-oxo-2-benzofuran-1-yl]phenyl] cyanate Chemical compound C12=CC=CC=C2C(=O)OC1(C=1C=CC(OC#N)=CC=1)C1=CC=C(OC#N)C=C1 CUVGYGLIVYYKLM-UHFFFAOYSA-N 0.000 description 1
- ZFWZYLYLPMWAQM-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)butyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CCC)C1=CC=C(OC#N)C=C1 ZFWZYLYLPMWAQM-UHFFFAOYSA-N 0.000 description 1
- RZBUVWIMPWGGRK-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)cyclohexyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1C1(C=2C=CC(OC#N)=CC=2)CCCCC1 RZBUVWIMPWGGRK-UHFFFAOYSA-N 0.000 description 1
- BWVPAGYFWDPBIW-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)cyclopentyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1C1(C=2C=CC(OC#N)=CC=2)CCCC1 BWVPAGYFWDPBIW-UHFFFAOYSA-N 0.000 description 1
- SIZDMAYTWUINIG-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)C1=CC=C(OC#N)C=C1 SIZDMAYTWUINIG-UHFFFAOYSA-N 0.000 description 1
- YTLAVSHTYSTXGG-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)pentyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CCCC)C1=CC=C(OC#N)C=C1 YTLAVSHTYSTXGG-UHFFFAOYSA-N 0.000 description 1
- LNZIRNRHIJPNRY-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)propyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CC)C1=CC=C(OC#N)C=C1 LNZIRNRHIJPNRY-UHFFFAOYSA-N 0.000 description 1
- OXRLCQGMPCWRFK-UHFFFAOYSA-N [4-[2,2-dichloro-1-(4-cyanatophenyl)ethenyl]phenyl] cyanate Chemical group C=1C=C(OC#N)C=CC=1C(=C(Cl)Cl)C1=CC=C(OC#N)C=C1 OXRLCQGMPCWRFK-UHFFFAOYSA-N 0.000 description 1
- KHBNIEBZWXZEPA-UHFFFAOYSA-N [4-[2-(4-cyanato-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenyl] cyanate Chemical compound CC1=C(OC#N)C(C)=CC(C(C)(C)C=2C=C(C)C(OC#N)=C(C)C=2)=C1 KHBNIEBZWXZEPA-UHFFFAOYSA-N 0.000 description 1
- LCCSXIORAPRMIY-UHFFFAOYSA-N [4-[2-(4-cyanato-3-phenylphenyl)propan-2-yl]-2-phenylphenyl] cyanate Chemical compound C=1C=C(OC#N)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(OC#N)C=1C1=CC=CC=C1 LCCSXIORAPRMIY-UHFFFAOYSA-N 0.000 description 1
- YNVGXUXBZCUQEQ-UHFFFAOYSA-N [4-[2-(4-cyanato-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenyl] cyanate Chemical compound C1=C(OC#N)C(C(C)C)=CC(C(C)(C)C=2C=C(C(OC#N)=CC=2)C(C)C)=C1 YNVGXUXBZCUQEQ-UHFFFAOYSA-N 0.000 description 1
- VJLQKGRQOAVLKN-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)-3,3-dimethylbutan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C(C)(C)C)C1=CC=C(OC#N)C=C1 VJLQKGRQOAVLKN-UHFFFAOYSA-N 0.000 description 1
- LYVKPFCEPYMYIN-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)-3-methylbutan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C(C)C)C1=CC=C(OC#N)C=C1 LYVKPFCEPYMYIN-UHFFFAOYSA-N 0.000 description 1
- OKOGUHSERRTCOI-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)-4-methylpentan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(CC(C)C)C1=CC=C(OC#N)C=C1 OKOGUHSERRTCOI-UHFFFAOYSA-N 0.000 description 1
- UPCZANMLPOWPAD-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)butan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(CC)C1=CC=C(OC#N)C=C1 UPCZANMLPOWPAD-UHFFFAOYSA-N 0.000 description 1
- NHZITVMFMHBTBL-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)hexan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(CCCC)C1=CC=C(OC#N)C=C1 NHZITVMFMHBTBL-UHFFFAOYSA-N 0.000 description 1
- KGRJSARQPLMHSD-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)pentan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(CCC)C1=CC=C(OC#N)C=C1 KGRJSARQPLMHSD-UHFFFAOYSA-N 0.000 description 1
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 1
- QODYBLNVIHQJIW-UHFFFAOYSA-N [4-[2-[3-[2-(4-cyanatophenyl)propan-2-yl]phenyl]propan-2-yl]phenyl] cyanate Chemical compound C=1C=CC(C(C)(C)C=2C=CC(OC#N)=CC=2)=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 QODYBLNVIHQJIW-UHFFFAOYSA-N 0.000 description 1
- ZPMIQPVBNFKPAM-UHFFFAOYSA-N [4-[2-[4-[2-(4-cyanatophenyl)propan-2-yl]phenyl]propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(C(C)(C)C=2C=CC(OC#N)=CC=2)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 ZPMIQPVBNFKPAM-UHFFFAOYSA-N 0.000 description 1
- JGZANMKVIUZPKB-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-1-adamantyl]phenyl] cyanate Chemical compound O(C#N)C1=CC=C(C=C1)C12CC3(CC(CC(C1)C3)C2)C2=CC=C(C=C2)OC#N JGZANMKVIUZPKB-UHFFFAOYSA-N 0.000 description 1
- SEBSTXOGSGMBQA-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-1-methyl-2-oxoindol-3-yl]phenyl] cyanate Chemical compound C12=CC=CC=C2N(C)C(=O)C1(C=1C=CC(OC#N)=CC=1)C1=CC=C(OC#N)C=C1 SEBSTXOGSGMBQA-UHFFFAOYSA-N 0.000 description 1
- KHNZTNGNKBPUEM-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2,2,4-trimethylpentan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)(C)C)(C(C)C)C1=CC=C(OC#N)C=C1 KHNZTNGNKBPUEM-UHFFFAOYSA-N 0.000 description 1
- MVKJIDGYEARQJO-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2,2-dimethylhexan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)(C)C)(CCC)C1=CC=C(OC#N)C=C1 MVKJIDGYEARQJO-UHFFFAOYSA-N 0.000 description 1
- SABGMTGLIYMFLH-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2,2-dimethylpentan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)(C)C)(CC)C1=CC=C(OC#N)C=C1 SABGMTGLIYMFLH-UHFFFAOYSA-N 0.000 description 1
- PPQOSMROARHRSD-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2,4-dimethylhexan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)C)(C(C)CC)C1=CC=C(OC#N)C=C1 PPQOSMROARHRSD-UHFFFAOYSA-N 0.000 description 1
- GSDUKIJGTSHOOD-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2-methylheptan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)C)(CCCC)C1=CC=C(OC#N)C=C1 GSDUKIJGTSHOOD-UHFFFAOYSA-N 0.000 description 1
- BCFLPWOICZLPEV-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-2-methylhexan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)C)(CCC)C1=CC=C(OC#N)C=C1 BCFLPWOICZLPEV-UHFFFAOYSA-N 0.000 description 1
- IELUNLXGZJSZCC-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)-3-oxoprop-1-enyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(=O)C=CC1=CC=C(OC#N)C=C1 IELUNLXGZJSZCC-UHFFFAOYSA-N 0.000 description 1
- GTJHXCHRCZRACK-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)heptan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CC)(CCCC)C1=CC=C(OC#N)C=C1 GTJHXCHRCZRACK-UHFFFAOYSA-N 0.000 description 1
- SIVPMTCZSPKNJC-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)hexan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CC)(CCC)C1=CC=C(OC#N)C=C1 SIVPMTCZSPKNJC-UHFFFAOYSA-N 0.000 description 1
- ZSFDETFCXJDSDY-UHFFFAOYSA-N [4-[3-(4-cyanatophenyl)octan-3-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(CC)(CCCCC)C1=CC=C(OC#N)C=C1 ZSFDETFCXJDSDY-UHFFFAOYSA-N 0.000 description 1
- VCTHWSNFKPDIFC-UHFFFAOYSA-N [4-[4-(4-cyanatophenyl)-3-methylheptan-4-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C(C)CC)(CCC)C1=CC=C(OC#N)C=C1 VCTHWSNFKPDIFC-UHFFFAOYSA-N 0.000 description 1
- XFCYBOMYXFWJKW-UHFFFAOYSA-N [4-[9-(4-cyanato-3-methylphenyl)fluoren-9-yl]-2-methylphenyl] cyanate Chemical compound C1=C(OC#N)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(OC#N)=CC=2)=C1 XFCYBOMYXFWJKW-UHFFFAOYSA-N 0.000 description 1
- NRAWVVBFCLDHDQ-UHFFFAOYSA-N [4-[9-(4-cyanato-3-phenylphenyl)fluoren-9-yl]-2-phenylphenyl] cyanate Chemical compound N#COC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C(OC#N)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 NRAWVVBFCLDHDQ-UHFFFAOYSA-N 0.000 description 1
- RMPWNGZEITYIQC-UHFFFAOYSA-N [4-[[4,6-bis(4-cyanato-N-methylanilino)-1,3,5-triazin-2-yl]-methylamino]phenyl] cyanate Chemical compound CN(C1=CC=C(C=C1)OC#N)C1=NC(=NC(=N1)N(C1=CC=C(C=C1)OC#N)C)N(C1=CC=C(C=C1)OC#N)C RMPWNGZEITYIQC-UHFFFAOYSA-N 0.000 description 1
- KHHRTIJOAOQNBD-UHFFFAOYSA-N [4-[bis(4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1C(C=1C=CC(OC#N)=CC=1)C1=CC=C(OC#N)C=C1 KHHRTIJOAOQNBD-UHFFFAOYSA-N 0.000 description 1
- BAQMVMPLBZLJLP-UHFFFAOYSA-N [4-[tris(4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound O(C#N)C1=CC=C(C=C1)C(C1=CC=C(C=C1)OC#N)(C1=CC=C(C=C1)OC#N)C1=CC=C(C=C1)OC#N BAQMVMPLBZLJLP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 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 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- LBVBDLCCWCJXFA-UHFFFAOYSA-N adamantane-1,2-dicarboxylic acid Chemical compound C1C(C2)CC3CC1C(C(=O)O)C2(C(O)=O)C3 LBVBDLCCWCJXFA-UHFFFAOYSA-N 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 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
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VBSLSHMYAWTHQM-UHFFFAOYSA-N anthracene-1,2,3,4,9-pentacarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C3C(C(O)=O)=C21 VBSLSHMYAWTHQM-UHFFFAOYSA-N 0.000 description 1
- HGMQPWXYDSTESW-UHFFFAOYSA-N anthracene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C=C(C(C(O)=O)=C(C(C(=O)O)=C3)C(O)=O)C3=CC2=C1 HGMQPWXYDSTESW-UHFFFAOYSA-N 0.000 description 1
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002255 azelaic acid Drugs 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 229910052916 barium silicate Inorganic materials 0.000 description 1
- HMOQPOVBDRFNIU-UHFFFAOYSA-N barium(2+);dioxido(oxo)silane Chemical compound [Ba+2].[O-][Si]([O-])=O HMOQPOVBDRFNIU-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960002130 benzoin Drugs 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- KYQRDNYMKKJUTH-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)CC1C2 KYQRDNYMKKJUTH-UHFFFAOYSA-N 0.000 description 1
- LKXGYGYFPTZHLC-UHFFFAOYSA-N bicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2CCC1(C(=O)O)C2 LKXGYGYFPTZHLC-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- OZGHELYGAUYWFC-UHFFFAOYSA-N bis(4-cyanatophenyl) carbonate Chemical compound C=1C=C(OC#N)C=CC=1OC(=O)OC1=CC=C(OC#N)C=C1 OZGHELYGAUYWFC-UHFFFAOYSA-N 0.000 description 1
- HXTBYXIZCDULQI-UHFFFAOYSA-N bis[4-(methylamino)phenyl]methanone Chemical compound C1=CC(NC)=CC=C1C(=O)C1=CC=C(NC)C=C1 HXTBYXIZCDULQI-UHFFFAOYSA-N 0.000 description 1
- FLOVDPVBGCRANV-UHFFFAOYSA-N bis[6-(6-chlorohexyl)-1-hydroxycyclohexa-2,4-dien-1-yl]methanone Chemical compound C1=CC=CC(CCCCCCCl)C1(O)C(=O)C1(O)C=CC=CC1CCCCCCCl FLOVDPVBGCRANV-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- HXTLWOZJMYIANK-UHFFFAOYSA-N butyl acetate;methanol Chemical compound OC.CCCCOC(C)=O HXTLWOZJMYIANK-UHFFFAOYSA-N 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
- IJRVQAXSAHHCNH-UHFFFAOYSA-M butyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](C)(C)C IJRVQAXSAHHCNH-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- YBGHFLPNIGPGHX-UHFFFAOYSA-N calcium;octan-1-olate Chemical compound [Ca+2].CCCCCCCC[O-].CCCCCCCC[O-] YBGHFLPNIGPGHX-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DGYCRMHMDADXLD-UHFFFAOYSA-N cyclobut-2-ene-1,1,2-tricarboxylic acid Chemical compound C1C=C(C1(C(=O)O)C(=O)O)C(=O)O DGYCRMHMDADXLD-UHFFFAOYSA-N 0.000 description 1
- UQFFSTQNDQYSAT-UHFFFAOYSA-N cyclobut-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=C1 UQFFSTQNDQYSAT-UHFFFAOYSA-N 0.000 description 1
- DIHZWJQLZIPGLR-UHFFFAOYSA-N cyclobut-3-ene-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)C=CC1(C(O)=O)C(O)=O DIHZWJQLZIPGLR-UHFFFAOYSA-N 0.000 description 1
- CMLOVBIZVAKNJA-UHFFFAOYSA-N cyclobutane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCC1(C(O)=O)C(O)=O CMLOVBIZVAKNJA-UHFFFAOYSA-N 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- CXUKMALSQXRODE-UHFFFAOYSA-N cyclobutene-1-carboxylic acid Chemical compound OC(=O)C1=CCC1 CXUKMALSQXRODE-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- XANGSDQSJJTJLP-UHFFFAOYSA-N cyclohept-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC=C1 XANGSDQSJJTJLP-UHFFFAOYSA-N 0.000 description 1
- WRJINBFZTQADKT-UHFFFAOYSA-N cycloheptane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCCC1 WRJINBFZTQADKT-UHFFFAOYSA-N 0.000 description 1
- FNFJZXAWCAEGNI-UHFFFAOYSA-N cycloheptene-1-carboxylic acid Chemical compound OC(=O)C1=CCCCCC1 FNFJZXAWCAEGNI-UHFFFAOYSA-N 0.000 description 1
- YRMXLGJOOSNONR-UHFFFAOYSA-N cyclohex-2-ene-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1=CCCCC1(C(O)=O)C(O)=O YRMXLGJOOSNONR-UHFFFAOYSA-N 0.000 description 1
- OVHKECRARPYFQS-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC=C1 OVHKECRARPYFQS-UHFFFAOYSA-N 0.000 description 1
- ZQPFJZNUMOMMJB-UHFFFAOYSA-N cyclohex-3-ene-1,1,2,2,3-pentacarboxylic acid Chemical compound C1CC(C(C(=C1)C(=O)O)(C(=O)O)C(=O)O)(C(=O)O)C(=O)O ZQPFJZNUMOMMJB-UHFFFAOYSA-N 0.000 description 1
- ZCUJUGHEDABDFN-UHFFFAOYSA-N cyclohex-3-ene-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC=CC1(C(O)=O)C(O)=O ZCUJUGHEDABDFN-UHFFFAOYSA-N 0.000 description 1
- LPGAWKVIEJZGPL-UHFFFAOYSA-N cyclohex-4-ene-1,1,2,2,3,3-hexacarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=CC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O LPGAWKVIEJZGPL-UHFFFAOYSA-N 0.000 description 1
- WLWKIJKUDWYINL-UHFFFAOYSA-N cyclohexane-1,1,2,2,3,3-hexacarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O WLWKIJKUDWYINL-UHFFFAOYSA-N 0.000 description 1
- DTLWQZBOAYMHTO-UHFFFAOYSA-N cyclohexane-1,1,2,2,3-pentacarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O DTLWQZBOAYMHTO-UHFFFAOYSA-N 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- MNUSMUGFHGAOIW-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCCC1(C(O)=O)C(O)=O MNUSMUGFHGAOIW-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000005725 cyclohexenylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LGMKYPATFVWGFR-UHFFFAOYSA-N cyclooct-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCCC=C1 LGMKYPATFVWGFR-UHFFFAOYSA-N 0.000 description 1
- RELFMIMPBVFVKQ-UHFFFAOYSA-N cyclooctane-1,1-dicarboxylic acid Chemical class OC(=O)C1(C(O)=O)CCCCCCC1 RELFMIMPBVFVKQ-UHFFFAOYSA-N 0.000 description 1
- URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 description 1
- VHXADKWNENAESO-UHFFFAOYSA-N cyclooctene-1-carboxylic acid Chemical compound OC(=O)C1=CCCCCCC1 VHXADKWNENAESO-UHFFFAOYSA-N 0.000 description 1
- NVBOVISCMMTFAM-UHFFFAOYSA-N cyclopent-2-ene-1,1,2-tricarboxylic acid Chemical compound C1(C(=CCC1)C(=O)O)(C(=O)O)C(=O)O NVBOVISCMMTFAM-UHFFFAOYSA-N 0.000 description 1
- MJEFJRILSAASHY-UHFFFAOYSA-N cyclopent-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC=C1 MJEFJRILSAASHY-UHFFFAOYSA-N 0.000 description 1
- IIBGXAZFYWEUQJ-UHFFFAOYSA-N cyclopent-3-ene-1,1,2,2,3-pentacarboxylic acid Chemical compound C1C=C(C(C1(C(=O)O)C(=O)O)(C(=O)O)C(=O)O)C(=O)O IIBGXAZFYWEUQJ-UHFFFAOYSA-N 0.000 description 1
- XKKWNZFMDFDOHG-UHFFFAOYSA-N cyclopent-3-ene-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC=CC1(C(O)=O)C(O)=O XKKWNZFMDFDOHG-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- MTGGGUZRAGKYEM-UHFFFAOYSA-N cyclopentane-1,1,2,2,3-pentacarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O MTGGGUZRAGKYEM-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- CQBJLRWOCFHFAB-UHFFFAOYSA-N cyclopentane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCC1(C(O)=O)C(O)=O CQBJLRWOCFHFAB-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- BOYPCDZNVGHJKC-UHFFFAOYSA-N cycloprop-2-ene-1,1,2-tricarboxylic acid Chemical compound C1=C(C1(C(=O)O)C(=O)O)C(=O)O BOYPCDZNVGHJKC-UHFFFAOYSA-N 0.000 description 1
- KLMUOAOHVRFGIB-UHFFFAOYSA-N cycloprop-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)C=C1 KLMUOAOHVRFGIB-UHFFFAOYSA-N 0.000 description 1
- YKXAGRCDGMWYRO-UHFFFAOYSA-N cyclopropane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CC1(C(O)=O)C(O)=O YKXAGRCDGMWYRO-UHFFFAOYSA-N 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 1
- ZYYZWCHPJMNJGY-UHFFFAOYSA-N cyclopropene-1-carboxylic acid Chemical compound OC(=O)C1=CC1 ZYYZWCHPJMNJGY-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- KVFVBPYVNUCWJX-UHFFFAOYSA-M ethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](C)(C)C KVFVBPYVNUCWJX-UHFFFAOYSA-M 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- PQDRJEDWHXYDCQ-UHFFFAOYSA-L fluoro-dioxido-oxo-lambda5-phosphane 4-methoxybenzenediazonium Chemical compound [O-]P([O-])(F)=O.COc1ccc(cc1)[N+]#N.COc1ccc(cc1)[N+]#N PQDRJEDWHXYDCQ-UHFFFAOYSA-L 0.000 description 1
- CBYZIWCZNMOEAV-UHFFFAOYSA-N formaldehyde;naphthalene Chemical class O=C.C1=CC=CC2=CC=CC=C21 CBYZIWCZNMOEAV-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000006358 imidation reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SODPLIPUBHWQPC-UHFFFAOYSA-N methyl 4-cyanatobenzoate Chemical compound COC(=O)C1=CC=C(OC#N)C=C1 SODPLIPUBHWQPC-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- AMVXVPUHCLLJRE-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)hexane-1,6-diamine Chemical compound CO[Si](OC)(OC)CCCNCCCCCCN AMVXVPUHCLLJRE-UHFFFAOYSA-N 0.000 description 1
- MNJJTHFKDZQVKH-UHFFFAOYSA-N n'-[3-(diethoxymethylsilyl)propyl]ethane-1,2-diamine Chemical compound CCOC(OCC)[SiH2]CCCNCCN MNJJTHFKDZQVKH-UHFFFAOYSA-N 0.000 description 1
- XFFPIAQRIDTSIZ-UHFFFAOYSA-N n'-[3-(dimethoxymethylsilyl)propyl]ethane-1,2-diamine Chemical compound COC(OC)[SiH2]CCCNCCN XFFPIAQRIDTSIZ-UHFFFAOYSA-N 0.000 description 1
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- KJPLRQFMMRYYFL-UHFFFAOYSA-N naphthalen-2-yl cyanate Chemical compound C1=CC=CC2=CC(OC#N)=CC=C21 KJPLRQFMMRYYFL-UHFFFAOYSA-N 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- WRYWBRATLBWSSG-UHFFFAOYSA-N naphthalene-1,2,4-tricarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C21 WRYWBRATLBWSSG-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- NOHFYJWXIIYRIP-UHFFFAOYSA-N phenyl 4-cyanatobenzoate Chemical compound C=1C=C(OC#N)C=CC=1C(=O)OC1=CC=CC=C1 NOHFYJWXIIYRIP-UHFFFAOYSA-N 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006290 polyethylene naphthalate film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- USJNXSKTHZGXJF-UHFFFAOYSA-N silane 3-triethoxysilylpropylurea Chemical class [SiH4].N(C(=O)N)CCC[Si](OCC)(OCC)OCC USJNXSKTHZGXJF-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KRZQYDMOEZDDGE-UHFFFAOYSA-N sodium;octan-1-olate Chemical compound [Na+].CCCCCCCC[O-] KRZQYDMOEZDDGE-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- SHCSTZVSTVNCAY-UHFFFAOYSA-L tetramethylazanium;chloride;hydroxide Chemical compound [OH-].[Cl-].C[N+](C)(C)C.C[N+](C)(C)C SHCSTZVSTVNCAY-UHFFFAOYSA-L 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000005029 thianthrenes Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- MHRLWUPLSHYLOK-UHFFFAOYSA-N thiomorpholine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CSCC(C(O)=O)N1 MHRLWUPLSHYLOK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- RKLXSINPXIQKIB-UHFFFAOYSA-N trimethoxy(oct-7-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC=C RKLXSINPXIQKIB-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- XQEGZYAXBCFSBS-UHFFFAOYSA-N trimethoxy-(4-methylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C(C)C=C1 XQEGZYAXBCFSBS-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- OLNCQUXQEJCISO-UHFFFAOYSA-M trimethyl(propyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](C)(C)C OLNCQUXQEJCISO-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- JBCJMTUHAXHILC-UHFFFAOYSA-N zinc;octanoic acid Chemical compound [Zn+2].CCCCCCCC(O)=O JBCJMTUHAXHILC-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/36—Amides or imides
- C08F22/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/46—Manufacturing multilayer circuits
Definitions
- the present invention relates to resin compositions, resin sheets, multilayer printed wiring boards, and semiconductor devices.
- the resin composition used as the material of the insulating layer is mainly a thermosetting resin, and holes for obtaining electrical connection between the insulating layers are generally made by laser processing.
- drilling holes by laser processing has the problem that the processing time becomes longer as the number of holes in a high-density substrate increases. Therefore, in recent years, by using a resin composition that allows the exposed area to be cured (exposure process) and the unexposed area to be removed (development process) by irradiation with light, etc., it is possible to perform batch drilling in the exposure and development processes. There is a demand for a resin sheet that makes this possible.
- a method of exposure a method of exposing through a photomask using a mercury lamp as a light source is used, and a material that can be suitably exposed to the light source of this mercury lamp is desired.
- This exposure method using a mercury lamp as a light source uses ghi crosstalk (g-line wavelength 436 nm, h-line wavelength 405 nm, i-line wavelength 365 nm), etc., and a general-purpose photocuring initiator can be selected.
- a direct drawing exposure method has also been introduced in which drawing is performed directly on a photosensitive resin composition layer without using a photomask based on digital data of a pattern.
- This direct writing exposure method has better alignment accuracy than the exposure method that uses a photomask, and can produce highly detailed patterns.
- the light source uses monochromatic light such as a laser.
- a DMD (Digital Micromirror Device) type apparatus capable of forming a high-definition resist pattern uses a light source with a wavelength of 405 nm (h-line).
- Alkaline development is used as the development method because it can obtain high-definition patterns.
- Patent Document 1 describes a resin composition containing a bismaleimide compound (curable resin) and a photoradical polymerization initiator (curing agent) as a photosensitive resin composition used for laminates and resin sheets. ing.
- Patent Document 2 describes a resin composition containing a polyvalent carboxy group-containing compound obtained by reacting a bismaleimide with a monoamine and then reacting an acid anhydride, and a curable resin such as an epoxy resin. There is a description. Patent Document 2 describes a polyvalent carboxy group-containing compound capable of obtaining a cured product having alkali developability.
- Patent Document 1 a bismaleimide compound is used as the curable resin, but since the maleimide compound usually has poor light transparency, when the maleimide compound is included, the light does not sufficiently reach the photocuring initiator, The photocuring initiator hardly generates radicals and its reactivity is very low. Therefore, in Patent Document 1, the maleimide compound is cured by performing additional heating before development. Moreover, since the resin composition described in Patent Document 1 does not have sufficient alkali developability in the first place, an unexposed resin composition remains even after development. Therefore, also from this point, in Patent Document 1, a high-definition resist pattern cannot be obtained, and cannot be used for manufacturing a high-density printed wiring board.
- the polyvalent carboxyl group-containing compound described in Patent Document 2 is obtained by reacting bismaleimide with monoamine and then reacting with an acid anhydride, so the process is complicated. Moreover, since an aromatic amine compound is used as the monoamine, this polyvalent carboxy group-containing compound contains an amide group having an aromatic ring in its structure. Therefore, since this polyvalent carboxyl group-containing compound has poor light transmittance and inhibits the photocuring reaction, it is actually difficult to use it in a photosensitive resin composition.
- An object of the present invention is to provide a resin composition, a resin sheet, a multilayer printed wiring board, and a semiconductor device capable of imparting excellent alkali developability.
- the present inventors have found that in the exposure step and development step in the production of a multilayer printed wiring board, the compound (A) containing a specific carboxy group and one or more carboxy groups other than the compound (A)
- a resin composition containing the compound (B) containing it is possible to suitably obtain a cured product without inhibiting the photocuring reaction, and it is possible to impart excellent alkali developability to the resin composition.
- the present invention has been completed.
- the present invention includes the following contents.
- each R 1 independently represents a group represented by the following formula (2) or a hydrogen atom.
- Each R 2 independently represents a hydrogen atom or a straight group having 1 to 6 carbon atoms. A chain or branched alkyl group, provided that at least one of R 1 is a group represented by the following formula (2).
- the compound (B) containing one or more carboxy groups is an acid anhydride of a fully hydrogenated aromatic polycarboxylic acid, an acid anhydride of a partially hydrogenated aromatic polycarboxylic acid, and an acid-modified epoxy ( The resin composition according to any one of [1] to [4], comprising at least one selected from the group consisting of meth)acrylates.
- R 3 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 4 is It represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms, and each R 5 independently represents a hydrogen atom or 1 to 1 carbon atoms.
- resin sheet [8] The resin sheet according to [7], wherein the resin layer has a thickness of 1 to 50 ⁇ m. [9] having an insulating layer and a conductor layer formed on one or both sides of the insulating layer, wherein the insulating layer contains the resin composition according to any one of [1] to [6]; Multilayer printed wiring board. [10] A semiconductor device comprising the resin composition according to any one of [1] to [6].
- a cured product in the exposure step and development step in the production of a multilayer printed wiring board, a cured product can be suitably obtained without inhibiting the photocuring reaction, and excellent alkali developability can be imparted. can.
- FIG. 1 is a 1 H-NMR chart of an amic acid compound (MA-TMDA).
- FIG. 2 is a 1 H-NMR chart of a maleimide compound (TMDM).
- 3 is a 1 H-NMR chart of the compound (A-1) obtained in Synthesis Example 2.
- this embodiment the form for carrying out the present invention (hereinafter referred to as "this embodiment") will be described in detail.
- the following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents.
- the present invention can be appropriately modified and implemented within the scope of the gist thereof.
- (meth)acrylic means both “acrylic” and its corresponding "methacrylic
- (meth)acrylate means both “acrylate” and its corresponding “methacrylate”
- (meth)acryloyl means both “acryloyl” and the corresponding "methacryloyl”.
- resin solid content or “resin solid content in the resin composition” refers to compound (A), compound (B), photocuring initiation agent (D), additives, solvents, and components excluding fillers.
- D The sum of the components excluding additives, solvents, and fillers is 100 parts by mass.
- the resin composition of the present embodiment includes a compound (A) represented by formula (1) (also referred to as component (A) or compound (A)) and a compound other than compound (A) represented by formula (1). , and a compound (B) containing one or more carboxy groups (also referred to as component (B) or compound (B)).
- the resin composition of the present embodiment contains compound (A) and compound (B), and is suitably used for producing a multilayer printed wiring board. By using the resin composition, it is possible to suitably obtain a cured product without inhibiting the photocuring reaction in the exposure and development steps in the production of a multilayer printed wiring board, and imparts excellent alkali developability after exposure. can do.
- the resin composition of this embodiment contains the compound (A) represented by formula (1).
- each R 1 independently represents a group represented by formula (2) or a hydrogen atom
- each R 2 independently represents a hydrogen atom or a straight chain having 1 to 6 carbon atoms. Alternatively, it represents a branched alkyl group. However, at least one of R 1 is a group represented by formula (2).
- -* represents a bond with the oxygen atom (O) directly linked to R 1 in formula (1).
- the resin composition containing the compound (A) together with the compound (B) described below is used in the exposure step and the development step in the production of the multilayer printed wiring board, so that the photocuring reaction is not inhibited and the resin composition is preferably cured.
- excellent alkali developability can be imparted to the resin composition in the unexposed areas. The reason for this is not clear, but the inventors presume as follows. That is, in the exposure step in the production of the multilayer printed wiring board, the compound (A) does not have a functional group involved in the photo-curing reaction in the exposure step and does not inhibit the photo-curing reaction.
- compound (A) does not have a skeleton that inhibits light transmittance, and has very excellent light transmittance. Therefore, even if the compound (B) is included together with the compound (A), photopolymerization proceeds and a cured product can be preferably obtained. And since the compound (A) does not participate in the photo-curing reaction, it can exist in the resin composition in the unexposed area. Therefore, in the development step, when the alkaline developer flows into the unexposed area, the alkaline component in the alkaline developer and the carboxy group in the compound (A) can form a suitable salt.
- the resin composition of the present embodiment contains compound (B) containing one or more carboxy groups together with compound (A). Since the compound (B) has a different structure from the compound (A), it can be mixed in the composition together with a component related to photocuring separately from the compound (A). having one or more, the alkaline developer is likely to flow. Therefore, it is presumed that, in the unexposed areas, areas where the alkaline developer is difficult to permeate are less likely to occur, the solubility in the alkaline developer is improved, and even better alkaline developability can be imparted.
- the compound (B) has one or more carboxy groups, the inclusion of the compound (B) makes it easier to form a salt with an alkali component in the alkali developer in the unexposed area. , it is presumed that even better alkali developability can be imparted.
- N-methylpyrrolidone solution containing 1% by mass of compound (A) is prepared, and an active energy ray containing a wavelength of 365 nm (i-line) is used to detect N-methyl pyrrolidone containing 1% by mass of compound (A).
- the transmittance of the pyrrolidone solution is measured, the transmittance is 5% or more.
- Such a compound (A) exhibits very good light transmittance.
- the transmittance of an N-methylpyrrolidone solution containing 1% by mass of the compound (A) is measured using an active energy ray having a wavelength of 405 nm (h-line), the transmittance is 5% or more. is. Even in this case, it exhibits very good light transmittance.
- the transmittance at a wavelength of 405 nm (h-line) is 8% or more, 10% or more, 20% or more, 30% or more, and 40% or more, in that order, since a resin composition with excellent photocurability can be obtained. is a preferable range.
- the upper limit of the transmittance at a wavelength of 365 nm (i-line) and the transmittance at a wavelength of 405 nm (h-line) is, for example, 99.9% or less.
- each R 1 in formula (1) independently represents a group represented by formula (2) or a hydrogen atom. Since R 1 can impart better alkali developability, it preferably contains two or more groups represented by formula (2), and more preferably contains three or more groups. A group represented by 2) is more preferable.
- R 1 when the position of the carbonyl group is the 1-position with respect to the cyclohexane ring, if a carboxy group is bonded at the 2-position with respect to the carbonyl group, another A carboxy group may be attached to any of the 3- to 6-positions on the cyclohexane ring.
- the compound (A) has a steric structure of the carbonyl group and the two carboxy groups bonded to the cyclohexane ring. It exists as a mixture of the and trans isomers. That is, compound (A) may be a single type or a mixture containing two or more isomers.
- At least one of R 1 is preferably a group represented by formula (3) because it can impart better alkali developability. That is, in the group represented by formula (3), the steric structure of the carbonyl group bonded to the 1-position of the cyclohexane ring and the carboxy group at the 2-position is preferably cis. The other carboxyl group may have a cis or trans conformation. Since R 1 can impart even better alkali developability, it preferably contains two or more groups represented by formula (3), more preferably three or more groups. A group represented by (3) is more preferable. Although it is not certain that when at least one of R 1 is a group represented by formula (3), better alkali developability can be imparted, the present inventors presume as follows.
- the carboxy group at the 2-position and the alkaline component in the alkaline developer form a salt in the resin composition. It can take a three-dimensional structure that is easier to form. In addition, it can have a steric structure that is easily compatible with the carboxy group in the compound (B) described below. Therefore, it is presumed that the water solubility is further improved and the inflow of the alkaline developer into the resin composition is further promoted.
- -* represents a bond with an oxygen atom (O) directly linked to R 1 in formula (1).
- Each R 2 independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
- Linear or branched alkyl groups having 1 to 6 carbon atoms include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 2-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 2-pentyl group, tert-pentyl group, 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, n-hexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, and 2-methylpentan-3-yl groups.
- R 2 is preferably a linear alkyl group having 1 to 6 carbon atoms from the viewpoint of exhibiting better solubility in a solvent, such as methyl, ethyl, n-propyl, 2-butyl. More preferred are isobutyl, tert-butyl, and n-pentyl groups, and even more preferred are methyl, ethyl, and n-propyl groups.
- Compound (A) can impart better alkali developability, and from the viewpoint of exhibiting better solubility in solvents, the compound represented by formula (5) and the compound represented by formula (6) It is preferably a compound, more preferably a compound represented by Formula (5).
- the content of the compound (A) can impart better alkali developability, and can express better curability without inhibiting the photocuring reaction in the resin composition. It is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 15 parts by mass, and 1.0 to 15 parts by mass with respect to 100 parts by mass of the resin solid content in the product is more preferable, more preferably 1.5 to 10 parts by mass, even more preferably 2.0 to 10 parts by mass.
- the content of the compound (A) is more excellent. Since it can impart alkali developability and can express better curability without inhibiting the photocuring reaction in the resin composition, the compound (A), the compound (B), the maleimide compound (C), and the photocuring It is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and 1.0 to 10 parts by mass with respect to the total 100 parts by mass of the initiator (D). is more preferable, and 2.0 to 9.0 parts by mass is even more preferable.
- Compound (A) can be produced by a known method.
- an alcohol compound represented by formula (7) and an acid anhydride represented by formula (8) (cyclohexane-1,2,4-tricarboxylic acid acid-1,2-anhydride).
- the acid anhydride represented by formula (8) since the structure of two carbonyl groups and one carboxy group bonded to the cyclohexane ring has a three-dimensional structure, the cis-form, the trans-form, and the cis-form and the trans-form Exists as a mixture of bodies. That is, the acid anhydride represented by formula (8) may be of one type alone, or may be a mixture containing two or more isomers.
- each R 6 independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
- R 2 in the above formula (1) can be referred to, including preferred embodiments thereof.
- Examples of alcohol compounds represented by formula (7) include ditrimethylolethane, ditrimethylolpropane, ditrimethylolbutane, ditrimethylolpentane, 2,2′-(oxybis(methylene))bis(propane-1,3- diol), 2,2′-(oxybis(methylene))bis(2-methylpropane-1,3-diol), and 2-((2,2-bis(hydroxymethyl)butoxy)methyl)-2-methyl propane-1,3-diol and the like.
- the acid anhydride represented by the formula (9) can be imparted with better alkali developability when a cured product is produced using the compound (A).
- the esterification reaction can be carried out with or without a solvent.
- the solvent is not particularly limited as long as it does not react with the alcohol compound and the acid anhydride.
- solvents include halogen solvents such as dichloromethane, chloroform, dichloroethane, and chlorobenzene; aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, and acetonitrile; Ketone solvents such as isobutyl ketone, cyclopentanone, and cyclohexanone; Cellosolve solvents such as 2-ethoxyethanol and propylene glycol monomethyl ether; Aliphatic alcohol solvents such as methanol, ethanol, propanol, isopropanol, and butanol; aromatic group-containing phenol solvents such as; ethyl lactate, methyl acetate, ethyl acetate, butyl
- halogen solvents aprotic polar solvents, ketone solvents, and ester solvents are preferable because they can dissolve alcohol compounds and acid anhydrides more sufficiently.
- Dichloromethane is preferred as the halogen solvent.
- Dimethylacetamide is preferred as the aprotic polar solvent.
- Methyl ethyl ketone is preferred as the ketone solvent.
- Propylene glycol monomethyl ether is preferred as the cellosolve solvent.
- Preferred ester solvents are butyl acetate, ⁇ -butyrolactone, and propylene glycol monomethyl ether acetate.
- the amount used is usually 20 to 2000 parts by mass with respect to a total of 100 parts by mass of the alcohol compound and acid anhydride.
- the esterification reaction may be carried out without a catalyst or with a catalyst.
- the catalyst When using a catalyst, the catalyst includes acidic compounds such as hydrochloric acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, nitric acid, trifluoroacetic acid, and trichloroacetic acid; sodium hydroxide, potassium hydroxide, water metal hydroxides such as calcium oxide and magnesium hydroxide; amine compounds such as triethylamine, tripropylamine, diisopropylethylamine, and tributylamine; aniline, N-methylaniline, N,N-dimethylaniline, and benzylamine; Aliphatic amines having an aromatic ring; heterocyclic compounds such as pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene, imidazole, triazole, and tetrazole; tetramethyl ammonium hydroxide
- catalysts can be used singly or in admixture of two or more.
- amine compounds, aliphatic amines having an aromatic ring, and heterocyclic compounds are preferred, and triethylamine and 4-dimethylaminopyridine are more preferred, from the viewpoint of better reactivity.
- the amount used is usually 0.0001 to 1000 parts by mass per 1 part by mass of the alcohol compound.
- the method of adding the catalyst is, for example, a method of adding directly to the alcohol compound and / or acid anhydride, or adding a solution dissolved in a soluble solvent or the like to the alcohol compound, acid anhydride, and / or a solvent containing these addition method.
- the esterification reaction temperature is not particularly limited depending on the amount of catalyst and the solvent used, but is usually -20 to 150°C.
- the reaction time is also not particularly limited, but is usually 0.5 to 100 hours. The reaction may be completed in one step or may be carried out in two or more steps.
- the alcohol compound represented by formula (7) and the acid anhydride represented by formula (8) have relatively high reactivity, they can be esterified even without a catalyst.
- the acid anhydride represented by the formula (8) preferably contains the acid anhydride represented by the formula (9) because of its higher reactivity with the alcohol compound.
- no catalyst means that no or only a very small amount of a catalyst that contributes to the esterification reaction is added. Specifically, it means that the amount of the catalyst is 50 ppm or less with respect to 1 part by mass of the alcohol compound represented by the formula (7) during the reaction. Moreover, during the reaction, it is preferable that the amount of the catalyst contributing to the esterification reaction is 0 ppm.
- halogen solvents, ketone solvents, and ester solvents can be used as the solvent because the alcohol compound and the acid anhydride can be dissolved more sufficiently, and the resulting compound (A) can also be more sufficiently dissolved. is preferred.
- halogen solvents and ester solvents are more preferable from the viewpoint of being able to exhibit even better solubility and further suppressing the hydrolysis of the acid anhydride.
- an ester solvent is more preferable because the alcohol compound and the acid anhydride can be reacted more favorably, the hydrolysis of the acid anhydride can be further suppressed, and the environmental load can be reduced.
- Dichloromethane is preferable as the halogen solvent because it can exhibit better solubility.
- ketone solvent methyl ethyl ketone is preferable from the viewpoint of exhibiting better solubility.
- ester solvent butyl acetate, ⁇ -butyrolactone, and propylene glycol monomethyl ether acetate are preferable from the viewpoint of exhibiting better solubility.
- the amount of the solvent used is usually 20 to 2000 parts by mass with respect to a total of 100 parts by mass of the alcohol compound and the acid anhydride, and is 20 to 1000 parts by mass to further reduce the environmental load. is preferred, and 20 to 500 parts by mass is more preferred.
- the reaction temperature for esterification can be appropriately set depending on the solvent used, but it is usually -20 to 150°C, and since the esterification proceeds more favorably, it is 0 to 150°C. more preferably 20 to 120°C.
- the reaction time is usually 0.5 to 100 hours. Side reactions are suppressed and the esterification proceeds more favorably, so the reaction time is preferably 0.5 to 80 hours. More preferably, it is 0.5 to 50 hours.
- the reaction may be completed in one step or may be performed in two or more steps.
- the alcohol compound and the acid anhydride can be more fully esterified without a catalyst, so the cost of the catalyst can be reduced, the step of removing the catalyst can be omitted, and impurities can be removed. is less likely to occur, and a compound of relatively high purity can be obtained. Therefore, under these production conditions, it is possible to omit the step of isolating the compound (A) from the reaction mixture described below and the purification step.
- the reaction temperature and reaction time are as described above. The reason for this is not clear, but the inventors presume as follows. That is, the ester solvent can further suppress hydrolysis of the acid anhydride represented by formula (8), and can further suppress side reactions other than the intended esterification reaction. Therefore, it is presumed that impurities are less likely to occur compared to other solvents, and that the target product with higher purity can be obtained.
- the target compound (A) when the target compound precipitates from the reaction solvent, it can be isolated by filtration or centrifugation.
- the solvent is distilled off under reduced pressure, a suitable poor solvent is added to the reaction mixture, or the reaction mixture is discharged into the poor solvent to precipitate, It can be isolated by filtration or centrifugation.
- poor solvents include hydrocarbons such as hexane, heptane, cyclohexane, toluene, and xylene. These solvents can be used singly or in admixture of two or more.
- the isolated compound (A) needs to be further purified, it can be purified by adopting a known method.
- Such methods include, for example, a distillation purification method, a recrystallization method, a column chromatography method, a sludge treatment, and an activated carbon treatment.
- the resulting compound (A) can be identified by known methods such as NMR (nuclear magnetic resonance spectroscopy).
- the purity of compound (A) can be analyzed, for example, by GPC, liquid chromatography, IR spectroscopy, and the like.
- Volatile components such as by-products and residual solvent in compound (A) can be quantitatively analyzed by, for example, GPC and gas chromatography.
- the halide remaining in the compound (A) can be identified, for example, by a liquid chromatograph mass spectrometer, and can also be quantified by ion chromatography after decomposition by potentiometric titration using a silver nitrate solution or combustion method. .
- the resin composition of the present embodiment contains a compound (B) containing one or more carboxy groups other than the compound (A) represented by formula (1).
- Compound (B) is not particularly limited as long as it contains one or more carboxy groups.
- the carboxyl group may be a salt such as a sodium salt or a potassium salt, or when two or more carboxyl groups are contained in the molecule, they may be an acid anhydride formed by linking them together.
- the molecule of the compound (B) may contain a functional group such as an epoxy group or a (meth)acryloyl group.
- Compound (B) can be used singly or in combination of two or more.
- a cured product can be obtained more preferably without inhibiting the photocuring reaction. can be done. Further, in the development step, a resin composition containing the compound (B) together with the compound (A) can be obtained, and after exposure, the resin composition in the unexposed areas can be imparted with better alkali developability. .
- N-methylpyrrolidone solution containing 1% by mass of compound (B) is prepared, and an active energy ray having a wavelength of 365 nm (i-line) is used to extract N-methyl containing 1% by mass of compound (B).
- the transmittance is preferably 5% or more.
- Such a compound (B) exhibits very good light transmittance.
- the transmittance of an N-methylpyrrolidone solution containing 1% by mass of the compound (B) is measured using an active energy ray having a wavelength of 405 nm (h-line), the transmittance is 5% or more. is preferable, and in this case also very excellent light transmittance is exhibited.
- a compound (B) when such a compound (B) is used, for example, when producing a printed wiring board having a high-density and high-definition wiring formation (pattern) using a direct drawing exposure method, an active material containing a wavelength of 405 nm (h-line) is used. Even when an energy beam is used, the photoradical reaction of maleimide occurs efficiently.
- the transmittance at a wavelength of 365 nm (i-line) is 8% or more, 10% or more, 20% or more, 30% or more, and 40% or more, in that order, since a resin composition with excellent photocurability can be obtained. is a preferable range.
- the transmittance at a wavelength of 405 nm (h-line) is 8% or more, 10% or more, 20% or more, 30% or more, and 40% or more, in that order, since a resin composition with excellent photocurability can be obtained. is a preferable range.
- the upper limit of the transmittance at a wavelength of 365 nm (i-line) and the transmittance at a wavelength of 405 nm (h-line) is, for example, 99.9% or less, and may be 100% or less.
- the compound (B) preferably contains 1 to 10 carboxy groups, more preferably 2 to 4 on average, in order to obtain better alkali developability.
- the molecular weight of the compound (B) is preferably 50 to 10,000, more preferably 100 to 8,000, even more preferably 130 to 6,000, further preferably 150 to 5,000, from the viewpoint of further improving developability. It is even more preferred to have
- the mass average molecular weight of compound (B) is preferably 50 to 10,000, more preferably 100 to 8,000, and even more preferably 150 to 5,000, from the viewpoint of further improving developability.
- Examples of the compound (B) include formic acid, aliphatic compounds containing one or more carboxy groups, aromatic compounds containing one or more carboxy groups, hetero compounds containing one or more carboxy groups, and anhydrides. . These compounds (B) can be used singly or in admixture of two or more.
- aliphatic compounds containing one or more carboxyl groups include chain aliphatic monocarboxylic acids, alicyclic monocarboxylic acids, chain aliphatic polycarboxylic acids, and alicyclic polycarboxylic acids. . These compounds have hydrogen atoms and substituents such as alkyl groups, alkoxy groups, aryloxy groups, aryl groups, aminoalkyl groups, hydroxy groups, amino groups, and carboxyalkyl groups in their molecules. good too. In addition, when these compounds have two or more carboxyl groups in the molecule, they may be acid anhydrides formed by linking them together.
- these compounds When these compounds have a carboxyalkyl group in the molecule, they may be an acid anhydride formed by combining the carboxyalkyl group and the carboxy group. When these compounds have two or more carboxyalkyl groups in the molecule, they may be acid anhydrides formed by linking them together.
- alkyl groups include methyl group, ethyl group, n-propyl group, i-propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n -heptyl group, and n-octyl group.
- alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-hexanoxy, and 2-methylpropoxy groups.
- Aryloxy groups include, for example, a phenoxy group and a p-tolyloxy group.
- Aryl groups include, for example, phenyl, toluyl, benzyl, methylbenzyl, xylyl, mesityl, naphthyl, and anthryl groups.
- aminoalkyl groups include aminomethyl, aminoethyl, aminopropyl, aminodimethyl, aminodiethyl, aminodipropyl, aminobutyl, aminohexyl, and aminononyl groups.
- Carboxyalkyl groups include, for example, carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl, carboxyhexyl, and carboxynonyl groups.
- Chain aliphatic monocarboxylic acids include, for example, acetic acid, propionic acid, isobutyric acid, butyric acid, isovaleric acid, valeric acid, caproic acid, lactic acid, succinic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecane unsaturated fatty acids such as oleic acid, elaidic acid, erucic acid, nervonic acid, linolenic acid, stearidonic acid, eicosapentaenoic acid, linoleic acid and linolenic acid; and chain aliphatic monocarboxylic acids containing one or more groups represented by formula (11) in the molecule.
- alicyclic monocarboxylic acids examples include cyclopropanecarboxylic acid, cyclopropenecarboxylic acid, cyclobutanecarboxylic acid, cyclobutenecarboxylic acid, cyclopentanecarboxylic acid, cyclopentenecarboxylic acid, cyclohexanecarboxylic acid, cyclohexenecarboxylic acid, and cycloheptanecarboxylic acid.
- Acids monocyclic carboxylic acids such as cycloheptenecarboxylic acid, cyclooctanecarboxylic acid, and cyclooctenecarboxylic acid, norbornanecarboxylic acid, tricyclodecanecarboxylic acid, tetracyclododecanecarboxylic acid, adamantanecarboxylic acid, methyladamantanecarboxylic acid , polycyclic or bridged alicyclic carboxylic acids such as ethyladamantanecarboxylic acid and butyladamantanecarboxylic acid, and alicyclic monocarboxylic acids containing one or more groups represented by formula (11) in the molecule is mentioned.
- chain aliphatic polycarboxylic acids include carboxylic acids in which one or more carboxy groups are further added to chain aliphatic monocarboxylic acids.
- carboxylic acids in which one or more carboxy groups are further added to chain aliphatic monocarboxylic acids.
- propiondioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, dodecanedioic acid, tetradecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, and octadecanedioic acid and in the molecule represented by formula (11) and chain aliphatic polycarboxylic acids containing one or more groups.
- alicyclic polycarboxylic acids include carboxylic acids in which one or more carboxy groups are further added to alicyclic monocarboxylic acids.
- carboxylic acids in which one or more carboxy groups are further added to alicyclic monocarboxylic acids.
- Examples of the base skeleton of aromatic compounds containing one or more carboxyl groups include benzoic acid, phenyleneacetic acid, salicylic acid, phthalic acid, trimellitic acid, pyromellitic acid, pentacarboxybenzene, hexacarboxybenzene, naphthalenecarboxylic acid, and naphthalene.
- Aromatic compounds have, for example, hydrogen atoms and alkyl groups, alkoxy groups, aryloxy groups, aryl groups, aminoalkyl groups, hydroxy groups, amino groups, carboxyalkyl groups, etc. on the aromatic rings of these parent skeletons. It may have a substituent.
- aromatic compounds containing one or more carboxy groups include aromatic compounds containing one or more groups represented by formula (11) and one or more carboxy groups in the molecule.
- hetero compound containing one or more carboxy groups examples include furan, thiophene, pyrrole, imidazole, pyran, pyridine, pyrimidine, pyrazine, pyrrolidine, piperidine, piperazine, morpholine, indole, purine, quinoline, isoquinoline, and quinuclidine. , chromenes, thianthrenes, phenothiazines, phenoxazines, xanthenes, acridines, phenazines, and carbazoles.
- Hetero compounds have, for example, hydrogen atoms and substituents such as alkyl groups, alkoxy groups, aryloxy groups, aryl groups, aminoalkyl groups, hydroxy groups, amino groups, and carboxyalkyl groups on their parent skeleton. You may have In addition, when these compounds have two or more carboxyl groups in the molecule, they may be acid anhydrides formed by linking them together. When these compounds have a carboxyalkyl group in the molecule, they may be an acid anhydride formed by combining the carboxyalkyl group and the carboxy group. When these compounds have two or more carboxyalkyl groups in the molecule, they may be acid anhydrides formed by linking them together. For these substituents, reference can be made to the above. Hetero compounds containing one or more carboxy groups also include hetero compounds containing one or more groups represented by formula (11) and one or more carboxy groups in the molecule.
- the entire unexposed area is more likely to collapse, and in addition, the alkaline developer can flow more easily, and the resin composition can be provided with excellent alkaline developability.
- It is preferably at least one selected from the group consisting of complete hydrides, acid anhydrides of partially hydrogenated aromatic polycarboxylic acids, and acid-modified epoxy (meth)acrylates.
- Acid anhydrides of fully hydrogenated aromatic polycarboxylic acids and acid anhydrides of partially hydrogenated aromatic polycarboxylic acids include, for example, 1,2,4-cyclohexanetricarboxylic acid-1,2-anhydride, and acid anhydrides such as 1,2,4,5-cyclohexanetetracarboxylic dianhydride; 1,2,3-benzenetricarboxylic acid, 1,2,4-naphthalenetricarboxylic acid, 3,3′,4,4 '-benzophenonetetracarboxylic acid, 2,2',3,3'-benzophenonetetracarboxylic acid, 2,3,3',4'-benzophenonetetracarboxylic acid, 3,3',4,4'-biphenyltetracarboxylic acid acid, 2,2',3,3'-biphenyltetracarboxylic acid, 2,3,3',4'-biphenyltetracarboxylic acid, 4,4'-oxyd
- the acid anhydride of the fully hydrogenated aromatic polycarboxylic acid and the acid anhydride of the partially hydrogenated aromatic polycarboxylic acid are more likely to crumble in the entire unexposed area.
- monocyclic cycloalkanes such as cyclopentane and cyclohexane
- monocyclic cycloalkenes such as cyclopropene and cyclohexene
- bicyclic alkanes bicyclic alkenes such as norbornene and norbornadiene
- more preferably monocyclic cycloalkanes or monocyclic cycloalkenes are more likely to crumble in the entire unexposed area.
- Such preferred acid anhydrides include, for example, 1,2,4-cyclohexanetricarboxylic acid-1,2-anhydride and 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride.
- 1,2,4-Cyclohexanetricarboxylic acid is used because the entire unexposed area is even more likely to crumble, and in addition, the alkali developer is even more likely to flow in, and the resin composition can be imparted with even better alkali developability.
- Acid-1,2-anhydride is more preferred, and cis,cis-1,2,4-cyclohexanetricarboxylic acid-1,2-anhydride is even more preferred.
- the acid-modified epoxy (meth)acrylate includes an epoxy resin (i), at least one compound (ii) selected from the group consisting of acrylic acid and methacrylic acid, a carboxylic acid-containing compound, and an anhydride of the carboxylic acid-containing compound. compounds obtained by reacting with at least one compound (iii) selected from the group consisting of substances.
- Examples of such acid-modified epoxy (meth)acrylates include chain aliphatic monocarboxylic acids containing one or more groups represented by formula (11) in the molecule, and groups represented by formula (11) in the molecule.
- an aromatic compound containing one or more carboxy groups one or more groups represented by formula (11) in the molecule and one or more carboxy groups
- aromatic compounds and hetero compounds containing one or more carboxy groups include hetero compounds containing one or more groups represented by formula (11) and one or more carboxy groups in the molecule.
- the entire unexposed area is more likely to collapse, and in addition, the alkali developer is more likely to flow in, and the resin composition can be imparted with even better alkali developability.
- Compounds containing at least one group represented by formula (10) and at least one group represented by formula (11) in the molecule are preferred.
- -* represents a bond
- R 7 represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
- Linear or branched alkyl groups having 1 to 6 carbon atoms include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 2-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 2-pentyl group, tert-pentyl group, 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, n-hexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, and 2-methylpentan-3-yl groups.
- R 7 is preferably a hydrogen atom or a straight-chain alkyl group having 1 to 6 carbon atoms from the viewpoint of further improving the reactivity of photocuring.
- a propyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, and an n-pentyl group are more preferred, and a hydrogen atom, a methyl group, an ethyl group, and an n-propyl group are even more preferred.
- the entire unexposed area is even more likely to crumble, and in addition, the alkali developer is even more likely to flow in, so that even better alkali developability can be imparted to the resin composition.
- each R 8 independently represents a hydrogen atom or a methyl group. Among these, from the viewpoint of further improving the reactivity of the photo-curing reaction, it is preferable to contain a hydrogen atom, and more preferably all of R 8 are hydrogen atoms.
- Each R 9 independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 22 carbon atoms.
- the hydrocarbon group is a linear or branched aliphatic hydrocarbon group having 1 to 22 carbon atoms, preferably 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms; 3 to 22 carbon atoms, preferably 3 to 14, more preferably 3 to 10 alicyclic hydrocarbon groups; and 6 to 22, preferably 6 to 14, more preferably 6 to 10, aromatic hydrocarbon groups having carbon atoms.
- Aliphatic hydrocarbon groups include, for example, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, isopropyl group, isobutyl group, sec-butyl group, t-butyl group, neopentyl group, 1,1-dimethylpropyl group, 1,1-diethylpropyl group, 1-ethyl-1-methylpropyl group, 1,1,2,2-tetramethylpropyl group, 1,1-dimethylbutyl and linear or branched alkyl groups such as 1,1,3-trimethylbutyl; linear or branched alkenyl groups such as vinyl, allyl, and isopropenyl; ethynyl, propargyl linear or branched alkynyl groups such as groups.
- alicyclic hydrocarbon groups include cyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methyl-1-cyclohexyl, and adamantyl groups; cyclopentadienyl groups; Cyclic unsaturated hydrocarbon groups such as an indenyl group and a fluorenyl group can be mentioned.
- aromatic hydrocarbon groups include unsubstituted aryl groups such as phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, and anthracenyl groups; tolyl, dimethylphenyl, isopropylphenyl, t-butyl Aryl groups such as a phenyl group and an alkyl group-substituted aryl group such as a di-t-butylphenyl group;
- At least one hydrogen atom of these hydrocarbon groups may be substituted with another hydrocarbon group.
- Hydrocarbon groups in which at least one hydrogen atom is substituted with another hydrocarbon group include, for example, aryl group-substituted alkyl groups such as benzyl group and cumyl group; cyclic saturated hydrocarbon group-substituted alkyl groups such as cyclohexylmethyl group. is mentioned.
- R 9 preferably contains a methyl group, more preferably all of R 9 are methyl groups.
- Each R 10 independently represents a group represented by formula (10), a group represented by formula (11), or a hydroxy group. Among these, from the viewpoint of further improving the releasability after development, it is preferable to include a hydroxy group. Further, among R 10 , it is also preferable to use a compound containing a group represented by formula (10) from the viewpoint of further improving developability. Among R 10 , it is also preferable to use a compound containing a group represented by formula (11) from the viewpoint of further improving photocuring reactivity.
- R 7 represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms. Among them, from the viewpoint of further improving the reactivity of the photocuring reaction, a hydrogen atom or a methyl group is preferable, and a hydrogen atom is more preferable.
- the acid value of the compound represented by formula (12) is preferably 30 mgKOH/g or more from the viewpoint of further improving the developability, and is preferably 50 mgKOH/g or more because the developability is further improved. More preferred.
- the acid value of the compound is preferably 120 mgKOH/g or less, and is 110 mgKOH/g or less because dissolution can be further prevented. is more preferable.
- “acid value” shows the value measured by the method according to JISK0070:1992.
- any one or more of compounds (A1) to (A5) may be included, reactivity of the photocuring reaction, heat resistance of the cured product, peelability after development, and It is preferable because the developability can be further improved, and it is more preferable to contain at least the compound (A1), and it is more preferable to contain any two or more of (A1) to (A5), and the compound (A1) and the compound It is more preferable to include any one or more of (A2) to (A5).
- the compound represented by formula (12) preferably includes at least compounds (A2) and (A3).
- a commercial product can also be used as the compound represented by formula (12).
- KAYARAD® ZCR-6001H, KAYARAD® ZCR-6002H, KAYARAD® ZCR-6006H, KAYARAD® ZCR-6007H, and KAYARAD® ZCR-601H above, product name, manufactured by Nippon Kayaku Co., Ltd. and the like.
- the content of the compound (B) makes the entire unexposed area more likely to crumble, and in addition, makes it easier for the alkaline developer to flow into the resin composition, thereby imparting even better alkaline developability to the resin composition. Therefore, it is preferably 1.0 to 90 parts by mass, more preferably 2.0 to 80 parts by mass, based on a total of 100 parts by mass of compound (A) and compound (B). It is more preferably 0 to 70 parts by mass, and even more preferably 4.0 to 65 parts by mass.
- the content of the compound (B) makes the entire unexposed area more likely to crumble, and in addition, makes it easier for the alkaline developer to flow into the resin composition, thereby imparting even better alkaline developability to the resin composition. Therefore, it is preferably 0.05 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, and 0.2 to 15 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition. parts, and even more preferably 0.3 to 10 parts by mass.
- the resin composition contains the maleimide compound (C) described below and the photo-curing initiator (D) described below together with the compound (A), the content of the compound (B) contributes to better alkali development.
- the compound (A), the compound (B), the maleimide compound (C), and the photocuring initiator can be used because they can impart properties and can express better curability without inhibiting the photocuring reaction in the resin composition.
- the total 100 parts by mass of (D) it is preferably 0.05 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, and 0.2 to 15 parts by mass. More preferably, it is still more preferably 0.25 to 10 parts by mass.
- the resin composition of the present embodiment preferably further contains a maleimide compound (C) (also referred to as component (C) or compound (C)).
- the maleimide compound (C) is not particularly limited as long as it is a compound having one or more maleimide groups in the molecule.
- Examples of such a maleimide compound (C) include bismaleimide (C1) described later, a compound represented by formula (15), a compound represented by formula (16), and a compound represented by formula (17).
- a compound with excellent light transmittance is preferably used as the maleimide compound (C).
- the total content of the maleimide compound (C) can impart better alkali developability, without inhibiting the photocuring reaction in the resin composition. Since it is possible to express good curability, it is preferably 10 to 100 parts by mass, more preferably 20 to 100 parts by mass, with respect to 100 parts by mass of the resin solid content in the resin composition. More preferably 30 to 100 parts by mass.
- the lower limit of the total content of the maleimide compound (C) may be 60 parts by mass or more, or may be 70 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. It may be 80 parts by mass or more.
- the content of the maleimide compound (C) can impart better alkali developability.
- the compound (A), the compound (B), the maleimide compound (C), and the photocuring initiator (D) It is preferably from 30 to 97 parts by mass, more preferably from 40 to 96 parts by mass, and even more preferably from 50 to 95 parts by mass with respect to 100 parts by mass in total.
- the lower limit of the content of the maleimide compound (C) is 60 parts by mass or more with respect to a total of 100 parts by mass of the compound (A), the compound (B), the maleimide compound (C), and the photocuring initiator (D). , 70 parts by mass or more, or 80 parts by mass or more.
- bismaleimide (C1) is included because it can express better curability, has better solubility in solvents, a low melting point, and better low water absorption.
- the compound represented by the formula (15), the compound represented by the formula (16), the compound represented by the formula (17), the compound represented by the formula (18) a compound represented by formula (19), and a compound represented by formula (20).
- the maleimide compound (C) can exhibit better curability, is superior in heat resistance and thermal stability, has better solubility in solvents, a low melting point, and even better low water absorption.
- bismaleimide (C1) preferably contains at least one selected from the group consisting of the compounds represented by, together with the bismaleimide (C1), from the group consisting of the compounds represented by the formula (15) and the compounds represented by the formula (16) It is more preferable to include at least one selected.
- the resin composition of the present embodiment can exhibit better curability, has better solubility in solvents, a low melting point, and better low water absorption, so the bismaleimide compound (C1) (also referred to as component (C1)) is preferably further included.
- the bismaleimide compound (C1) contains a structural unit represented by formula (4) and maleimide groups at both ends of the molecular chain.
- R 3 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 4 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- Each R 5 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms.
- Each n 1 independently represents an integer of 1-10.
- maleimide compounds have extremely low water solubility and do not have reactivity with alkaline components in alkaline developing solutions, making it difficult to obtain alkaline developability.
- the resin composition contains the bismaleimide compound (C1) together with the compound (A) and the compound (B), it has excellent photocurability and very good alkali developability. The reason for this is not clear, but the inventors presume as follows.
- the resin composition contains a compound (A) capable of imparting excellent alkali developability to the resin composition without inhibiting the photocuring reaction, and suitably controlling the water solubility in the unexposed area, and and a compound (B) capable of imparting alkali developability.
- the bismaleimide compound (C1) has a relatively long chain and flexible structure, and does not have a structure that causes an interaction with an alkaline component in an alkaline developer. Therefore, in the development step, when the alkaline developer flows into the unexposed area (resin composition), the alkaline component in the alkaline developer, the compound (A) and the compound The carboxy group in (B) can quickly and suitably form a salt, improving the water solubility.
- the bismaleimide compound (C1) is involved in the alkaline developer together with the compound (A) and the compound (B) as the compound (A) and the compound (B) dissolve in the alkaline developer. Can be dissolved in alkaline developer. Therefore, the resin composition is presumed to have excellent alkali developability.
- the resin composition has excellent photocurability by containing the bismaleimide compound (C1) together with the compound (A) and the compound (B) for the following reasons. I'm guessing.
- maleimide compounds have poor light transmittance, so when a resin composition contains a maleimide compound, light does not sufficiently reach the photocuring initiator dispersed in the resin composition, causing the photocuring initiator to generate radicals. unlikely to occur. Therefore, the radical photoreaction of the maleimide compound is generally difficult to proceed, and even if the radical polymerization or dimerization reaction of maleimide alone proceeds, the reactivity is very low.
- the bismaleimide compound (C1) has the constitutional unit represented by the formula (4), that is, the alicyclic skeleton, and thus has very excellent light transmittance.
- Compound (A) also has very good light transmittance. Therefore, sufficient light reaches the photocuring initiator, photoradical reaction of maleimide occurs efficiently, and the compound (A), the compound (B) and the bismaleimide compound (C1) are blended as necessary.
- Photocuring can be performed using various active energy rays (light rays) together with the maleimide compound (C) and the photocuring initiator (D) described below.
- a chloroform solution containing 1% by mass of the bismaleimide compound (C1) is prepared, and an active energy ray having a wavelength of 365 nm (i-line) is used to purify the chloroform solution containing 1% by mass of the bismaleimide compound (C1).
- the transmittance of the film is measured, the transmittance is 5% or more, indicating very excellent light transmittance.
- the transmittance of a chloroform solution containing 1% by mass of the bismaleimide compound (C1) was measured using an active energy ray having a wavelength of 405 nm (h-line), the transmittance was found to be 5% or more. , which exhibits very good light transmission.
- the transmittance at a wavelength of 365 nm (i-line) is preferably 8% or more, more preferably 10% or more, from the viewpoint of exhibiting more excellent light transmittance.
- the transmittance at a wavelength of 405 nm (h-line) is preferably 8% or more, and preferably 10% or more, from the viewpoint of producing a printed wiring board having a higher density and finer wiring formation (pattern). more preferred.
- the upper limit of the transmittance at a wavelength of 365 nm (i-line) and the transmittance at a wavelength of 405 nm (h-line) is, for example, 99.9% or less.
- photocuring initiators tend to have low absorbance for light in the long wavelength region. For example, when an active energy ray containing a wavelength of 405 nm (h-line) is used, since the light of this wavelength is a relatively long wavelength, it is not absorbed by a normal photocuring initiator, and this light is preferably absorbed. Polymerization does not proceed unless a photocuring initiator capable of generating radicals is used.
- the photocuring initiator (D) described later when the absorbance of a chloroform solution containing 0.01% by mass of the photocuring initiator (D) is measured, light with a wavelength of 405 nm (h line)
- a photo-curing initiator exhibiting an extremely excellent light absorption property such as an absorbance of 0.1 or more.
- the bismaleimide compound (C1) is excellent in light transmittance as described above, for example, even when an active energy ray containing a wavelength of 365 nm or an active energy ray containing a wavelength of 405 nm is used, the light reaches the photocuring initiator sufficiently. , the radical reaction using the radicals generated from the photocuring initiator proceeds favorably, and photocuring becomes possible even in a composition containing a large amount of the bismaleimide compound (C1). And the resin composition is excellent in alkali developability and photocurability. Moreover, the obtained cured product is excellent in heat resistance, insulation reliability, and thermal stability. Therefore, according to this embodiment, it is possible to suitably form the protective film and the insulating layer in the multilayer printed wiring board and the semiconductor device.
- the bismaleimide compound (C1) is not particularly limited as long as it exhibits the effects of the present invention, but it preferably has a weight average molecular weight of 100 to 5000 in terms of obtaining a suitable viscosity and suppressing an increase in the viscosity of the varnish. , 300-4500.
- R 3 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms. show.
- R 3 is preferably a linear or branched alkylene group, more preferably a linear alkylene group, because a more suitable viscosity can be obtained and the increase in the viscosity of the varnish can be more controlled. preferable.
- the number of carbon atoms in the alkylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- Examples of linear or branched alkylene groups include methylene, ethylene, propylene, 2,2-dimethylpropylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, and decylene.
- the number of carbon atoms in the alkenylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- Linear or branched alkenylene groups include, for example, vinylene group, 1-methylvinylene group, arylene group, propenylene group, isopropenylene group, 1-butenylene group, 2-butenylene group, 1-pentenylene group, 2 -pentenylene group, isopentylene group, cyclopentenylene group, cyclohexenylene group, dicyclopentadienylene group, and the like.
- R 4 represents a linear or branched alkylene group having 1 to 16 carbon atoms or a linear or branched alkenylene group having 2 to 16 carbon atoms.
- R 4 is preferably a straight-chain or branched alkylene group, more preferably a straight-chain alkylene group, because a more suitable viscosity can be obtained and the increase in the viscosity of the varnish can be more controlled. preferable.
- the number of carbon atoms in the alkylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- the above R 3 can be referred to.
- the number of carbon atoms in the alkenylene group is preferably from 2 to 14, more preferably from 4 to 12, in order to obtain a more suitable viscosity and control the increase in viscosity of the varnish.
- the above R 3 can be referred to.
- R 3 and R 4 may be the same or different, but are preferably the same from the viewpoint of easier synthesis of the bismaleimide compound (C1).
- each R 5 is independently a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. show.
- Each R 5 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms, since a more suitable viscosity can be obtained and the viscosity increase of the varnish can be more controlled. More preferably, among R 5 , 1 to 5 groups (R 5 ) are linear or branched alkyl groups having 1 to 16 carbon atoms, and the remaining groups (R 5 ) are hydrogen atoms.
- 1 to 3 groups (R 5 ) among R 5 are linear or branched alkyl groups having 1 to 16 carbon atoms, and the remaining groups (R 5 ) are hydrogen atoms. preferable.
- the number of carbon atoms in the alkyl group is preferably from 2 to 14, more preferably from 4 to 12, from the viewpoint that more suitable viscosity can be obtained and the increase in viscosity of the varnish can be more controlled.
- Linear or branched alkyl groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, 1-ethylpropyl group, n-butyl group, 2-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 2-pentyl group, tert-pentyl group, 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, n-hexyl group, 2-hexyl group, 3-hexyl group, n-heptyl, n-octyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylpent
- the number of carbon atoms in the alkenyl group is preferably from 2 to 14, more preferably from 4 to 12, from the viewpoint that a more suitable viscosity can be obtained and the viscosity increase of the varnish can be more controlled.
- Linear or branched alkenyl groups include, for example, vinyl, allyl, 4-pentenyl, isopropenyl, isopentenyl, 2-heptenyl, 2-octenyl, and 2-nonenyl groups. be done.
- each n 1 independently represents an integer of 1-10.
- the bismaleimide compound (C1) has maleimide groups at both ends of the molecular chain. Both ends mean both ends in the molecular chain of the bismaleimide compound (C1), for example, when the structural unit represented by formula (4) is at the end of the molecular chain of the bismaleimide compound (C1) means that the maleimido group is at the chain end of R 3 or at the chain end at the N atom of the maleimide ring or at both ends.
- the bismaleimide compound (C1) may have maleimide groups other than both ends of the molecular chain.
- the maleimide group is represented by formula (13), and the N atom is bonded to the molecular chain of the bismaleimide compound (C1).
- the maleimide groups bonded to the bismaleimide compound (C1) may all be the same or different, but the maleimide groups at both ends of the molecular chain are preferably the same.
- each R 11 independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Both R 11 are preferably hydrogen atoms from the viewpoint of more favorable photocuring.
- the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 to 2, from the viewpoint of more favorable photocuring.
- the linear or branched alkyl group the above R 5 can be referred to.
- Examples of such a bismaleimide compound (C1) include maleimide compounds represented by formula (14). These may be used singly or in admixture of two or more.
- a represents an integer of 1-10. It is preferable that a is an integer of 1 to 6 from the viewpoint that a more suitable viscosity can be obtained and the increase in viscosity of the varnish can be more controlled.
- a commercially available product can also be used as the bismaleimide compound (C1).
- Examples of commercially available products include MIZ-001 (trade name, including maleimide compound of formula (14)) manufactured by Nippon Kayaku Co., Ltd.
- the content of the bismaleimide compound (C1) makes it possible to obtain a cured product containing the bismaleimide compound as a main component, to further improve the photocurability, and to achieve superior heat resistance and From the viewpoint of obtaining thermal stability, it is preferably contained in 10 to 90 parts by mass, more preferably 30 to 80 parts by mass, in 100 parts by mass of the resin solid content in the resin composition, and 40 to 70 parts by mass. It is more preferable to contain 45 to 65 parts by mass.
- the content of the bismaleimide compound (C1) is based on the bismaleimide compound as the main component.
- Bismaleimide compound (C1) and other than bismaleimide compound (C1) from the viewpoint that a cured product can be obtained, photocurability can be further improved, and excellent heat resistance and thermal stability can be obtained. 10 to 90 parts by mass, preferably 30 to 80 parts by mass, even more preferably 40 to 70 parts by mass, and 45 to 65 parts by mass It is more preferable to contain parts by mass.
- maleimide compounds other than the bismaleimide compound (C1) include the compound represented by (15), the compound represented by formula (16), the compound represented by formula (17), and the compound represented by formula (18). It is preferable to include at least one selected from the group consisting of a compound, a compound represented by formula (19), and a compound represented by formula (20), and a compound represented by formula (15), a formula ( 16), and more preferably at least one selected from the group consisting of the compound represented by formula (17), the compound represented by formula (15) and the compound represented by formula (16) It is more preferable to contain at least one selected from the group consisting of the compounds represented.
- the bismaleimide compound (C1) can be used singly or in an appropriate mixture of two or more.
- a bismaleimide compound (C1) can be produced by a known method.
- 1,2,4,5-cyclohexanetetracarboxylic dianhydride, a monomer containing a diamine including dimer diamine and the like, and maleic anhydride are generally heated at about 80 to 250°C, preferably about 100 to 200°C.
- the polyaddition reaction is usually carried out for about 0.5 to 50 hours, preferably about 1 to 20 hours to obtain a polyadduct.
- the polyadduct is subjected to an imidation reaction at a temperature of usually about 60 to 120° C., preferably about 80 to 100° C., for about 0.1 to 2 hours, preferably about 0.1 to 0.5 hours.
- the bismaleimide compound (C1) can be obtained by a dehydration ring-closure reaction.
- Dimer diamine is obtained, for example, by reductive amination reaction of dimer acid, and the amination reaction is performed by a known method such as a reduction method using ammonia and a catalyst (for example, described in JP-A-9-12712). method).
- a dimer acid is a dibasic acid obtained by dimerizing an unsaturated fatty acid by an intermolecular polymerization reaction or the like. Although it depends on synthesis conditions and purification conditions, it usually contains a small amount of monomer acid, trimer acid, etc. in addition to dimer acid. A double bond remains in the molecule obtained after the reaction.
- a dimer acid is obtained, for example, by polymerizing an unsaturated fatty acid using a Lewis acid and a Bronsted acid as a catalyst.
- a dimer acid can be produced by a known method (for example, the method described in JP-A-9-12712).
- unsaturated fatty acids include crotonic acid, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, nervonic acid, linoleic acid, pinolenic acid, eleostearic acid, mead acid, dihomo-gamma-linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, boseopentaenoic acid, osponded acid, sardine acid, tetracosapentaenoic acid, docosahexaenoic acid, and herring acid.
- the number of carbon atoms in the unsaturated fatty acid is generally 4-24, preferably 14-20.
- the diamine-containing monomer is dissolved or dispersed in slurry in an organic solvent in advance, for example, in an inert atmosphere such as argon or nitrogen, to form a diamine-containing monomer solution and preferably.
- 1,2,4,5-Cyclohexanetetracarboxylic dianhydride can be dissolved in an organic solvent or dispersed in a slurry state, or added in a solid state to the above-mentioned diamine-containing monomer solution. preferable.
- An arbitrary bismaleimide compound (C1) is obtained by preparing the number of moles of 1,2,4,5-cyclohexanetetracarboxylic dianhydride and the total number of moles of the monomer containing diamine and the maleimide compound. be able to.
- solvents can be used in the polyaddition reaction and imidization reaction.
- solvents include amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and isophorone; Esters such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -butyrolactone, ethyl lactate, methyl acetate, ethyl acetate, and butyl acetate; methanol, ethanol , and aliphatic alcohols having 1 to 10 carbon atoms such as propanol; aromatic group-containing phenols such as phenol and cresol; aromatic group-containing alcohols such as benzyl
- a catalyst in the imidization reaction for example, tertiary amines and dehydration catalysts can be used.
- Preferred tertiary amines are heterocyclic tertiary amines such as pyridine, picoline, quinoline, and isoquinoline.
- Dehydration catalysts include, for example, acetic anhydride, propionic anhydride, n-butyric anhydride, benzoic anhydride, and trifluoroacetic anhydride.
- the amount of the catalyst to be added is, for example, about 0.5 to 5.0 times the molar equivalent of the imidizing agent with respect to the amide group, and 0.5 to 10.0 times the molar amount of the dehydration catalyst with respect to the amide group. Equivalent weights are preferred.
- this solution may be used as the bismaleimide compound (C1) solution, or a poor solvent may be added to the reaction solvent to turn the bismaleimide compound (C1) into a solid.
- poor solvents include water, methyl alcohol, ethyl alcohol, 2-propyl alcohol, ethylene glycol, triethylene glycol, 2-butyl alcohol, 2-pentyl alcohol, 2-hexyl alcohol, cyclopentyl alcohol, cyclohexyl alcohol, phenol, and t-butyl alcohol.
- the photoradical reactivity of maleimide compounds is usually very low.
- the bismaleimide compound (C1) is very excellent in light transmittance.
- Compound (A) also has very good light transmittance. Therefore, the bismaleimide compound (C1) is optionally blended with the compound (A), the compound (B), and an optionally blended maleimide compound (C) other than the bismaleimide compound (C1).
- the photocuring initiator (D) described later sufficient light reaches the photocuring initiator, the photoradical reaction of maleimide occurs efficiently, and various active energy rays can be used for photocuring. can.
- the compound (A) and the bismaleimide compound (C1) are excellent in light transmittance, even when various active energy rays, especially an active energy ray containing a wavelength of 365 nm or an active energy ray containing a wavelength of 405 nm, are used, light is emitted. It sufficiently reaches the photo-curing initiator, a radical reaction using radicals generated from the photo-curing initiator proceeds, and photo-curing becomes possible even in a composition containing a maleimide compound. And the resin composition is excellent in alkali developability and photocurability. Moreover, since the obtained cured product is excellent in heat resistance, insulation reliability, and thermal stability, it is possible to suitably form a protective film and an insulating layer.
- R 12 , R 13 and R 14 each independently represent a hydrogen atom or an optionally substituted linear or branched alkyl group having 1 to 8 carbon atoms. show.
- Linear or branched alkyl groups having 1 to 8 carbon atoms which may have a substituent include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert -butyl group, n-pentyl group, 1-ethylpropyl group, 2,2-dimethylpropyl group, cyclopentyl group, hexyl group, heptyl group and the like.
- a hydrogen atom in these alkyl groups may be substituted with a fluorine atom, a halogen atom such as a chlorine atom, a cyano group, or the like.
- a fluorine atom such as a chlorine atom, a cyano group, or the like.
- a halogen atom such as a chlorine atom, a cyano group, or the like.
- it is preferably a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group, more preferably a methyl group, an ethyl group, or an isopropyl group, and still more preferably a methyl group.
- the compound represented by formula (15) exhibits even better photocurability, heat resistance, thermal stability, solubility in solvents, low melting point, low water absorption, and compatibility with other resins. From the viewpoint of achieving the above, the compound represented by Formula (21) (also referred to as TMDM in the present embodiment) is even more preferable.
- R 15 , R 16 and R 17 are each independently a hydrogen atom, a hydroxy group, or an optionally substituted linear or branched C 1-6 Indicates an alkyl group.
- n 3 represents an integer of 1-10.
- R 5 in the above formula (4) can be referred to.
- Alkyl groups include methyl, ethyl, n-propyl, and isopropyl from the viewpoint of exhibiting better solubility in solvents, a lower melting point, lower water absorption, and better compatibility with other resins. group is preferred, and methyl group is more preferred.
- R 15 , R 16 , and R 17 are linear or branched alkyl groups having 1 to 6 carbon atoms from the viewpoint of exhibiting better solubility in solvents. and preferably R 16 is a hydrogen atom. Preferable alkyl groups are as described above. n 3 is preferably an integer of 1 to 10, more preferably an integer of 1 to 6, from the viewpoint of better solubility in solvents, more suitable viscosity, and better control of the viscosity increase of the varnish. is more preferable.
- n 21 is an integer of 1-5.
- n 22 is an integer of 1-10.
- each R 18 independently represents a hydrogen atom, a methyl group, or an ethyl group
- each R 19 independently represents a hydrogen atom or a methyl group.
- R 18 is preferably a methyl group or an ethyl group from the viewpoint of exhibiting better solubility in solvents, a low melting point, low water absorption, and better compatibility with other resins.
- R 19 is preferably a hydrogen atom from the viewpoint of exhibiting better solubility in solvents, a low melting point, low water absorption, and better compatibility with other resins.
- maleimide compound represented by the formula (17) a commercially available product may be used, for example, BMI-70 (trade name) represented by the formula (24) manufactured by K.I. Kasei Co., Ltd. may be mentioned.
- each R 20 independently represents a hydrogen atom or a methyl group.
- n 4 represents an integer of 1-10.
- the maleimide compound represented by the formula (18) a commercially available product may be used, and examples thereof include MIR-3000 (trade name) manufactured by Nippon Kayaku Co., Ltd. represented by the formula (25).
- n 31 is an integer of 1-10.
- each R 21 independently represents a hydrogen atom, a methyl group, or an ethyl group.
- R 21 is preferably a methyl group or an ethyl group from the viewpoint of exhibiting better solubility in solvents, a low melting point, low water absorption, and better compatibility with other resins.
- the maleimide compound represented by formula (19) a commercially available product may be used, for example, BMI-80 (trade name) represented by formula (26) and manufactured by K.I. Kasei Co., Ltd. may be mentioned.
- each R 22 independently represents a hydrogen atom or a methyl group.
- n 5 represents an integer of 1-10.
- R 22 is preferably a hydrogen atom from the viewpoint of exhibiting better solubility in solvents, a low melting point, low water absorption, and better compatibility with other resins.
- n 5 is more preferably an integer of 1 to 5 from the viewpoints of better solubility in solvents, more suitable viscosity, and better control over the increase in viscosity of the varnish.
- maleimide compound represented by formula (20) a commercially available product may be used, for example, BMI-2300 (trade name) manufactured by Daiwa Kasei Kogyo Co., Ltd. represented by formula (27).
- n 41 is an integer of 1-5.
- it is preferably contained in 10 to 90 parts by mass, more preferably 20 to 70 parts by mass, and 30 to 60 parts by mass in 100 parts by mass of the resin solid content in the resin composition. more preferably 35 to 55 parts by mass.
- the total content of these maleimide compounds provides better heat resistance.
- it is preferably contained in an amount of 10 to 90 parts by mass, preferably 20 to 70 parts by mass, with respect to a total of 100 parts by mass of the bismaleimide compound (C1) and these maleimide compounds. is more preferable, more preferably 30 to 60 parts by mass, even more preferably 35 to 55 parts by mass.
- the resin composition of the present embodiment preferably further contains a photocuring initiator (D) (also referred to as component (D) or initiator (D)).
- the photocuring initiator (D) is not particularly limited, and those known in the field generally used in photocurable resin compositions can be used.
- the photocuring initiator (D) is used together with the compound (A), the compound (B), and the optionally blended maleimide compound (C) for photocuring using various active energy rays. be done.
- Examples of the photocuring initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether; benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl Peroxides and organic peroxides exemplified by di-tert-butyl-di-perphthalate; 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl) -acylphosphine oxides such as phenylphosphine oxide, benzoyl-diphenyl-phosphine oxide and bisbenzoyl-phenylphosphine oxide; acetophenone, 2,2-diethoxy-2-phenylacetophenone, 2,2-diethoxy-2 -phenylacetophenone, 1,1-d
- the photo-curing initiator (D) a commercially available product such as IGM Resins B.V. V. Omnirad (registered trademark) 369 (trade name) manufactured by IGM Resins B.I. V. Omnirad (registered trademark) 819 (trade name) manufactured by IGM Resins B.I. V. Company Omnirad (registered trademark) 819DW (trade name), IGM Resins B.I. V. Company Omnirad (registered trademark) 907 (trade name), IGM Resins B.I. V. Company Omnirad (registered trademark) TPO (trade name), IGM Resins B.I. V. Company Omnirad (registered trademark) TPO-G (trade name), IGM Resins B.I. V.
- the photocuring initiator (D) is prepared by preparing a chloroform solution containing 0.01% by mass, and using an active energy ray containing a wavelength of 365 nm (i-line), the photocuring initiator (D) is 0.01 mass.
- the absorbance of the chloroform solution contained in % is measured, the absorbance is preferably 0.1 or more, and this photocuring initiator (D) exhibits very excellent absorbance.
- the absorbance of a chloroform solution containing 0.01% by mass of a photocuring initiator (D) is measured using an active energy ray having a wavelength of 405 nm (h-line), the absorbance is 0.1.
- a photocuring initiator (D) for example, when producing a printed wiring board having a high-density and high-definition wiring formation (pattern) using a direct drawing exposure method, a wavelength of 405 nm (h-line) Photoradical reaction of maleimide occurs efficiently even when an active energy ray containing is used.
- the absorbance at a wavelength of 365 nm (i-line) is more preferably 0.15 or more because a resin composition having excellent photocurability can be obtained.
- the absorbance at a wavelength of 405 nm (h-line) is more preferably 0.15 or more because a resin composition with excellent photocurability can be obtained.
- the upper limit of the absorbance at a wavelength of 365 nm (i-line) and the absorbance at a wavelength of 405 nm (h-line) is, for example, 99.9 or less.
- oxime esters and acylphosphine oxides are preferable, and oxime esters are more preferable, because they have higher sensitivity to various active energy rays.
- oxime esters ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl, has higher sensitivity to various active energy rays and is superior in solvent solubility. ]-, 1-(O-acetyloxime) is preferred.
- acylphosphine oxides As acylphosphine oxides, various active energy rays, especially active energy rays including i-line with a wavelength of 365 nm and active energy rays including h-line with a wavelength of 405 nm, have a higher absorbance. Compounds represented by (28) are preferred.
- each R 23 independently represents a substituent represented by formula (29) or a phenyl group.
- each R 24 independently represents a hydrogen atom or a methyl group.
- -* represents a bond with the phosphorus atom (P) directly connected to R 23 in formula (28).
- a chloroform solution containing 0.01% by mass of this compound was prepared, and the absorbance of this chloroform solution was measured using an active energy ray containing a wavelength of 365 nm (i-line).
- the absorbance is 0.1 or more, showing very excellent absorbance for light with a wavelength of 365 nm (i-line). Therefore, this compound suitably generates radicals with respect to light with a wavelength of 365 nm (i-line).
- the absorbance is preferably 0.15 or more.
- the upper limit is, for example, 10.0 or less, and may be 5.0 or less, or 2.0 or less.
- a chloroform solution containing 0.01% by mass of this compound was prepared, and the absorbance of this chloroform solution was measured using an active energy ray containing a wavelength of 405 nm (h-line).
- the absorbance is 0.1 or more, showing very excellent absorbance for light with a wavelength of 405 nm (h-line). Therefore, this compound suitably generates radicals with respect to light with a wavelength of 405 nm (h-line). More preferably, the absorbance is 0.15 or more.
- the upper limit is, for example, 10.0 or less, may be 5.0 or less, or may be 2.0 or less.
- each R 23 independently represents a substituent represented by formula (29) or a phenyl group. At least one of R 23 is preferably a substituent represented by formula (29).
- each R 24 independently represents a hydrogen atom or a methyl group. At least one of R 24 is preferably a methyl group, and more preferably all are methyl groups.
- Examples of the compound represented by formula (28) include acylphos such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide. fin oxides. Among these, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide is preferred because it has superior light transmittance. These compounds can be used singly or in admixture of two or more.
- Acylphosphine oxides exhibit extremely excellent light absorption to active energy rays including a wavelength of 405 nm (h-line), and for example, at a wavelength of 405 nm (h-line), the maleimide compound (C) is preferably radicalized. can be polymerized. Therefore, according to the present embodiment, particularly when used for a multilayer printed wiring board, in the exposure process, it does not inhibit the photocuring reaction, has excellent photocurability, and has excellent alkali in the development process. It is possible to suitably manufacture a resin composition capable of imparting developability, a resin sheet using the same, a multilayer printed wiring board, and a semiconductor device.
- the content of the photocuring initiator (D) allows the photocuring to proceed more sufficiently without inhibiting the photocuring reaction in the resin composition, and makes the exposed area more sufficiently insoluble in alkali developability. From this point of view, it is preferably 0.1 to 50 parts by mass, more preferably 0.2 to 30 parts by mass, and 0.3 to 10 parts by mass in 100 parts by mass of the resin solid content in the resin composition. It is more preferably 1.0 to 8.0 parts by mass.
- the resin composition contains the maleimide compound (C) together with the compound (A) and the compound (B), the content of the photocuring initiator (D) inhibits the photocuring reaction in the resin composition.
- the compound (A), the compound (B), the maleimide compound (C), and the photocuring initiator With respect to the total 100 parts by mass of D), it is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 15 parts by mass, and further preferably 0.3 to 10 parts by mass. It is preferably 1.0 to 8.0 parts by mass, more preferably.
- a filler can be used in the resin composition of the present embodiment in order to further improve various properties such as coating properties and heat resistance. It is preferable that the filler has insulating properties and does not impair the permeability to various active energy rays used for photocuring.
- fillers include silica (e.g., natural silica, fused silica, amorphous silica, hollow silica, etc.), aluminum compounds (e.g., boehmite, aluminum hydroxide, alumina, aluminum nitride, etc.), boron compounds (e.g., boron nitride, etc.), magnesium compounds (e.g., magnesium oxide, magnesium hydroxide, etc.), calcium compounds (e.g., calcium carbonate, etc.), molybdenum compounds (e.g., molybdenum oxide, zinc molybdate, etc.), barium compounds (e.g., barium sulfate, barium silicate, etc.), talc (e.g., natural talc, calcined talc, etc.), mica, glass (e.g., short fiber glass, spherical glass, fine powder glass, E glass, T glass, and D glass etc.), silicone powder, fluororesin fillers, a
- These fillers may be surface-treated with a silane coupling agent or the like, which will be described later.
- Silica is preferable, and fused silica is more preferable, from the viewpoint of further improving the heat resistance of the cured product and obtaining better coating properties.
- Specific examples of silica include SFP-130MC (trade name) manufactured by Denka Corporation, SC2050-MB (trade name), SC1050-MLE (trade name) and YA010C-MFN (trade name) manufactured by Admatechs Co., Ltd. ), and YA050C-MJA (trade name).
- the particle size of the filler is not particularly limited, it is usually 0.005 to 10 ⁇ m, preferably 0.01 to 1.0 ⁇ m, from the viewpoint of obtaining more ultraviolet light transmittance of the resin composition.
- the content of the filler is usually based on 100 parts by mass of the resin solid content in the resin composition, from the viewpoint of improving the light transmittance of the resin composition and the heat resistance of the cured product. It is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, and even more preferably 100 parts by mass or less. In addition, when a filler is contained, the lower limit is usually 1 part by mass.
- silane coupling agent and wetting and dispersing agent A silane coupling agent and/or a wetting and dispersing agent may be used in combination with the resin composition of the present embodiment in order to further improve the dispersibility of the filler and the adhesive strength between the polymer and/or resin and the filler. can.
- silane coupling agents are not particularly limited as long as they are silane coupling agents generally used for surface treatment of inorganic substances.
- Silane N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane, N-(2-aminoethyl)-3-aminopropyldi ethoxymethylsilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, [3-(6-aminohexylamino)propyl]trimethoxysilane, and [3-(N , N-dimethylamino)-propyl]trimethoxysilane; ⁇ -glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, Epoxysilanes such as sidoxypropy
- the content of the silane coupling agent in the resin composition is usually 0.1 to 10 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.
- the wetting and dispersing agent is not particularly limited as long as it is a dispersion stabilizer used for paints. Specific examples include DISPERBYK (registered trademark)-110 (trade name), 111 (trade name), 118 (trade name), 180 (trade name), and 161 (trade name) manufactured by Big Chemie Japan Co., Ltd. , BYK®-W996 (trade name), W9010 (trade name), and W903 (trade name). These wetting and dispersing agents can be used singly or in combination of two or more.
- the content of the wetting and dispersing agent is usually 0.1 to 10 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.
- the compound (A), the compound (B), the maleimide compound (C ), various types of compounds and resins such as cyanate ester compounds, phenolic resins, oxetane resins, benzoxazine compounds, epoxy resins, and other compounds other than the photocuring initiator (D) can be used.
- these compounds and resins when exposed to various active energy rays, especially active energy rays containing a wavelength of 365 nm (i-line) and active energy rays containing a wavelength of 405 nm (h-line), the resin composition is preferably exposed to light and photocured.
- active energy rays containing a wavelength of 365 nm (i-line) and active energy rays containing a wavelength of 405 nm (h-line) the resin composition is preferably exposed to light and photocured.
- These compounds and resins can be used singly or in admixture of two or more.
- the cyanate ester compound is not particularly limited as long as it is a resin having an aromatic moiety substituted with at least one cyanato group (cyanate ester group) in the molecule.
- Ar 1 represents a benzene ring, a naphthalene ring, or a single bond of two benzene rings. When there are more than one, they may be the same or different.
- Ra is each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and 1 carbon atom A group in which an alkyl group of ⁇ 6 and an aryl group of 6 to 12 carbon atoms are bonded.
- the aromatic ring in Ra may have a substituent, and the substituents in Ar 1 and Ra can be selected at arbitrary positions.
- p represents the number of cyanato groups bonded to Ar 1 and each independently represents an integer of 1-3.
- q represents the number of Ra atoms bonded to Ar 1 , and is 4-p when Ar 1 is a benzene ring, 6-p when it is a naphthalene ring, and 8-p when two benzene rings are single bonded.
- . t represents the average number of repetitions and is an integer of 0 to 50, and the cyanate ester compound may be a mixture of compounds with different t.
- a divalent organic group having 1 to 50 carbon atoms (a hydrogen atom may be substituted with a hetero atom), a divalent nitrogen atom having 1 to 10
- the organic group for example, -N-R-N-, where R represents an organic group
- the alkyl group for Ra in formula (30) may have either a linear or branched chain structure or a cyclic structure (eg, cycloalkyl group, etc.). Further, the hydrogen atom in the alkyl group in formula (30) and the aryl group in Ra is substituted with a halogen atom such as a fluorine atom and a chlorine atom, an alkoxy group such as a methoxy group and a phenoxy group, or a cyano group. may be a halogen atom such as a fluorine atom and a chlorine atom, an alkoxy group such as a methoxy group and a phenoxy group, or a cyano group.
- alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl and 2,2-dimethylpropyl. group, cyclopentyl group, hexyl group, cyclohexyl group, trifluoromethyl group and the like.
- alkenyl groups include vinyl, (meth)allyl, isopropenyl, 1-propenyl, 2-butenyl, 3-butenyl, 1,3-butandienyl, and 2-methyl-2-propenyl. , 2-pentenyl group, and 2-hexenyl group.
- aryl groups include phenyl, xylyl, mesityl, naphthyl, phenoxyphenyl, ethylphenyl, o-, m- or p-fluorophenyl, dichlorophenyl, dicyanophenyl and trifluorophenyl. groups, methoxyphenyl groups, o-, m- or p-tolyl groups, and the like.
- Alkoxy groups include, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, and tert-butoxy groups.
- divalent organic group having 1 to 50 carbon atoms in X of formula (30) include methylene group, ethylene group, trimethylene group, cyclopentylene group, cyclohexylene group, trimethylcyclohexylene group, and biphenylylmethylene. dimethylmethylene-phenylene-dimethylmethylene group, fluorenediyl group, and phthalidodiyl group.
- a hydrogen atom in the divalent organic group may be substituted with a halogen atom such as a fluorine atom and a chlorine atom, an alkoxy group such as a methoxy group and a phenoxy group, a cyano group, and the like.
- divalent organic group having 1 to 10 nitrogen atoms in X of formula (30) include an imino group and a polyimide group.
- examples of the organic group for X in formula (30) include those having a structure represented by formula (31) and those having a structure represented by formula (32).
- Ar 2 represents a benzenediyl group, a naphthalenediyl group, or a biphenyldiyl group, and when u is an integer of 2 or more, they may be the same or different.
- Rb, Rc, Rf, and Rg each independently have at least one hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trifluoromethyl group, or a phenolic hydroxy group represents an aryl group.
- Rd and Re are each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group.
- u represents an integer of 0 to 5;
- Ar 3 represents a benzenediyl group, a naphthalenediyl group, or a biphenyldiyl group, and when v is an integer of 2 or more, they may be the same or different.
- Ri and Rj are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a benzyl group, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, and a trifluoromethyl group. , or an aryl group substituted with at least one cyanato group.
- v represents an integer of 0 to 5, it may be a mixture of compounds with different v.
- X in formula (30) includes a divalent group represented by the following formula.
- Each Rk independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- Ar 2 in formula (31) and Ar 3 in formula (32) include two carbon atoms represented by formula (31) or two oxygen atoms represented by formula (32), a benzenediyl group bonded to the 1,3-position or 1,3-position; , 3′- or 3,4′-positions, and two carbon atoms or two oxygen atoms attached to the 2,6-positions, 1,5-positions, 1,6-positions, 1, Naphthalenediyl groups bonded to 8-position, 1,3-position, 1,4-position, or 2,7-position can be mentioned.
- the alkyl group and aryl group for Rb, Rc, Rd, Re, Rf and Rg in formula (31) and Ri and Rj in formula (32) are the same as in formula (30).
- cyanato-substituted aromatic compound represented by formula (30) include cyanatobenzene, 1-cyanato-2-, 1-cyanato-3-, 1-cyanato-4-methylbenzene, 1-cyanato -2-, 1-cyanato-3-, or 1-cyanato-4-methoxybenzene, 1-cyanato-2,3-, 1-cyanato-2,4-, 1-cyanato-2,5-, 1- cyanato-2,6-, 1-cyanato-3,4- or 1-cyanato-3,5-dimethylbenzene, cyanatoethylbenzene, cyanatobutylbenzene, cyanatooctylbenzene, cyanatononylbenzene, 2-(4 -cyanatophenyl)-2-phenylpropane (4- ⁇ -cumylphenol cyanate), 1-cyanato-4-cyclohexylbenzene, 1-cyanato-4-vinylbenzene, 1-cyanato-4
- cyanate ester compounds can be used singly or in an appropriate mixture of two or more.
- cyanate ester compound represented by formula (30) includes phenol novolak resin and cresol novolac resin (by a known method, phenol, alkyl-substituted phenol or halogen-substituted phenol and formalin, paraformaldehyde, etc.
- Ar 4 —(CH 2 OR) 2 (R represents an alkyl group) and a phenolic compound reacted in the presence of an acidic catalyst or Ar A bis(hydroxymethyl) compound represented by 4- (CH 2 OH) 2 and a phenol compound are reacted in the presence of an acidic catalyst, or an aromatic aldehyde compound, an aralkyl compound and a phenol compound are polymerized.
- phenol-modified xylene formaldehyde resin by a known method, a xylene formaldehyde resin and a phenolic compound are reacted in the presence of an acidic catalyst
- modified naphthalene formaldehyde resin by a known method, a naphthalene formaldehyde resin and a hydroxy-substituted aromatic compound in the presence of an acidic catalyst
- a phenol-modified dicyclopentadiene resin or a phenol resin having a polynaphthylene ether structure
- a known method a phenolic hydroxy group in one molecule
- Polyhydric hydroxy naphthalene compounds having two or more in the presence of a basic catalyst, such as those obtained by dehydration condensation cyanated by the same method as described above, and these prepolymers, etc. mentioned.
- These cyanate ester compounds can be used singly or in admixture of two or more.
- the method for producing these cyanate ester compounds is not particularly limited, and known methods can be used.
- a specific example is a method of obtaining or synthesizing a hydroxy group-containing compound having a desired skeleton, and modifying the hydroxy group by a known technique to form a cyanate.
- Methods for cyanating a hydroxy group include, for example, the methods described in Ian Hamerton, "Chemistry and Technology of Cyanate Ester Resins," Blackie Academic & Professional.
- Cured products using these cyanate ester compounds have excellent properties such as glass transition temperature, low thermal expansion, and plating adhesion.
- the content of the cyanate ester compound is 0.01 to 40 parts per 100 parts by mass in total of the maleimide compound (C) and the cyanate ester compound. part by mass.
- phenolic resin generally known phenolic resins having two or more hydroxy groups in one molecule can be used.
- phenolic resin generally known phenolic resins having two or more hydroxy groups in one molecule can be used.
- bisphenol A type phenol resin bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolak resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolac type phenol resin, biphenyl Aralkyl-type phenolic resins, cresol novolac-type phenolic resins, polyfunctional phenolic resins, naphthol resins, naphthol novolak resins, polyfunctional naphthol resins, anthracene-type phenolic resins, naphthalene skeleton-modified novolac-type phenolic resins, phenol aralkyl-type phenolic resins, naphthol aralkyl
- the content of the phenolic resin is 0.01 to 40 parts by mass with respect to the total 100 parts by mass of the maleimide compound (C) and the phenolic resin. .
- oxetane resins can be used.
- OXT-101 manufactured by Toagosei Co., Ltd.
- the content of the oxetane resin is 0.01 to 40 parts by mass with respect to a total of 100 parts by mass of the maleimide compound (C) and the phenolic resin. .
- benzoxazine compound generally known compounds can be used as long as they are compounds having two or more dihydrobenzoxazine rings in one molecule.
- bisphenol A-type benzoxazine BA-BXZ (trade name, manufactured by Konishi Chemical Industry Co., Ltd.)
- bisphenol F-type benzoxazine BF-BXZ (trade name, manufactured by Konishi Chemical Industry Co., Ltd.)
- bisphenol S-type benzoxazine BS -BXZ trade name, manufactured by Konishi Chemical Industry Co., Ltd.
- Pd-type benzoxazine trade name, manufactured by Shikoku Chemical Industry Co., Ltd.
- Fa-type benzoxazine (trade name, manufactured by Shikoku Chemical Industry Co., Ltd.)
- phenolphthalein-type benzoxazines (trade name, manufactured by Shikoku Chemical Industry Co., Ltd.)
- benzoxazine compounds can be used singly or in admixture of two or more
- the content of the benzoxazine compound is 0.01 to 40 parts by mass with respect to the total 100 parts by mass of the maleimide compound (C) and the benzoxazine compound. is.
- Epoxy resins are not particularly limited, and generally known ones can be used.
- epoxy resin a commercially available product can be used. is about 4), and a naphthalene-type epoxy resin represented by formula (34) (HP-4710 (trade name) manufactured by DIC Corporation).
- epoxy resins can be used singly or in an appropriate mixture of two or more.
- the content of the epoxy resin is 0.01 to 40 parts by mass with respect to the total 100 parts by mass of the maleimide compound (C) and the epoxy resin. .
- ⁇ Other compounds> Other compounds include vinyl ethers such as ethyl vinyl ether, propyl vinyl ether, hydroxyethyl vinyl ether, and ethylene glycol divinyl ether; styrenes such as styrene, methylstyrene, ethylstyrene, and divinylbenzene; triallyl isocyanurate, trimethallyl Examples include isocyanurate and bisallylnadimide. These compounds can be used singly or in admixture of two or more.
- the content of the other compound is 0.01 to 40 parts by mass with respect to 100 parts by mass in total of the maleimide compound (C) and the other compound. is.
- the resin composition of the present embodiment may contain an organic solvent, if necessary.
- an organic solvent By using an organic solvent, it is possible to adjust the viscosity during preparation of the resin composition.
- the type of organic solvent is not particularly limited as long as it can dissolve part or all of the resin in the resin composition.
- organic solvents include halogen solvents such as dichloromethane, chloroform, dichloroethane, and chlorobenzene; aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, and acetonitrile; acetone, methyl ethyl ketone, and methyl isobutyl ketone.
- ketone solvents such as , cyclopentanone, and cyclohexanone
- cellosolve solvents such as 2-ethoxyethanol and propylene glycol monomethyl ether
- aliphatic alcohol solvents such as methanol, ethanol, propanol, isopropanol, and butanol
- aromatic group-containing phenol solvents ester solvents such as ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, methyl methoxypropionate, methyl hydroxyisobutyrate, ⁇ -butyrolactone, and propylene glycol monomethyl ether acetate
- Aromatic hydrocarbon solvents such as xylene and the like are included.
- the compound (A) and the compound (B), the compound (C) to be blended as necessary, and the photocuring initiator (D), and further to other resins and compounds From the viewpoint of exhibiting excellent solubility, aprotic polar solvents, ketone solvents, cellosolve solvents, and ester solvents are preferable, and from the viewpoint of exhibiting further excellent solubility, aprotic polar solvents, ketone solvents, and ester Solvents are more preferred. Dimethylacetamide is preferred as the aprotic polar solvent. Methyl ethyl ketone is preferred as the ketone solvent. Propylene glycol monomethyl ether is preferred as the cellosolve solvent. Preferred ester solvents are butyl acetate, ⁇ -butyrolactone, and propylene glycol monomethyl ether acetate. These organic solvents can be used singly or in admixture of two or more.
- the resin composition of the present embodiment includes various high-performance resins such as thermosetting resins, thermoplastic resins, oligomers thereof, and elastomers that have not been mentioned so far, as long as the properties of the present embodiment are not impaired.
- Molecular compounds; flame-retardant compounds not mentioned heretofore; additives and the like can also be used in combination. These are not particularly limited as long as they are commonly used.
- flame-retardant compounds include nitrogen-containing compounds such as melamine and benzoguanamine; oxazine ring-containing compounds; phosphorus compounds such as phosphate compounds of phosphorus compounds, aromatic condensed phosphates, and halogen-containing condensed phosphates. mentioned.
- Additives include UV absorbers, antioxidants, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, defoamers, surface conditioners, brighteners, polymerization inhibitors, and heat A hardening accelerator etc. are mentioned. These components can be used singly or in admixture of two or more. The content of the other components in the resin composition is usually 0.1 to 10 parts by weight per 100 parts by weight of the resin solid content in the resin composition.
- the resin composition of the present embodiment comprises a compound (A) and a compound (B), and optionally a maleimide compound (C), a photocuring initiator (D), fillers, other resins, and other compounds. , and additives can be appropriately mixed.
- the method for producing the resin composition includes, for example, a method in which each component described above is sequentially added to a solvent and thoroughly stirred.
- each component such as the compound (A) and the compound (B) in the resin composition is improved by performing a stirring and dispersing treatment using a stirring tank equipped with a stirrer having an appropriate stirring capacity. can be improved.
- Stirring, mixing, and kneading processes include, for example, a stirring device for dispersion such as an ultrasonic homogenizer, a device for mixing such as three rolls, a ball mill, a bead mill, and a sand mill, or a revolving or rotating type It can be appropriately carried out using a known device such as a mixing device.
- an organic solvent can be used as necessary during the preparation of the resin composition.
- the type of organic solvent is not particularly limited as long as it can dissolve the resin in the resin composition, and specific examples thereof are as described above.
- the resin composition can be suitably used as a varnish when producing the resin sheet of this embodiment, which will be described later.
- a varnish can be obtained by a well-known method.
- the varnish is prepared by adding 10 to 900 parts by mass, preferably 30 to 500 parts by mass of an organic solvent to 100 parts by mass of the components excluding the organic solvent in the resin composition, and performing the known treatment (stirring, mixing , and kneading treatment, etc.).
- the organic solvent used for preparing the varnish is not particularly limited, and specific examples thereof are as described above.
- the resin composition of the present embodiment can be suitably used for producing a multilayer printed wiring board, and can be preferably used for applications requiring an insulating resin composition.
- examples include photosensitive films, photosensitive films with supports, prepregs, resin sheets, circuit boards (laminated board applications, multilayer printed wiring board applications, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulants, and hole filling. It can be used for resins, part embedding resins, and the like.
- the resin composition is excellent in photocurability and alkali developability, and therefore can be suitably used as an insulating layer of a multilayer printed wiring board or as a solder resist.
- a cured product is obtained by curing the resin composition.
- the cured product can be obtained, for example, by melting or dissolving the resin composition in a solvent, pouring it into a mold, and curing it under normal conditions using light.
- the wavelength region of light is preferably in the range of 100 to 500 nm where curing proceeds efficiently with a photopolymerization initiator or the like.
- the resin sheet of the present embodiment is a support-attached resin sheet having a support and a resin layer disposed on one or both sides of the support, wherein the resin layer contains the resin composition of the present embodiment.
- a resin sheet can be produced by coating a resin composition on a support and drying the resin composition.
- the resin layer in the resin sheet has excellent photocurability and alkali developability.
- a known support can be used, and is not particularly limited, but is preferably a resin film.
- resin films include polyimide film, polyamide film, polyester film, polyethylene terephthalate (PET) film, polybutylene terephthalate (PBT) film, polypropylene (PP) film, polyethylene (PE) film, polyethylene naphthalate film, and polyvinyl alcohol. film, triacetyl acetate film, and the like. Among them, PET film is preferred.
- a release agent is preferably applied to the surface of the resin film so that it can be easily separated from the resin layer.
- the thickness of the resin film is preferably in the range of 5-100 ⁇ m, more preferably in the range of 10-50 ⁇ m. When the thickness is less than 5 ⁇ m, the support tends to be torn when the support is peeled off before alkali development. There is As used herein, the thickness can be measured using, for example, a micrometer.
- the resin film preferably has excellent transparency in order to reduce scattering of light during exposure.
- the resin layer may be protected with a protective film.
- a protective film By protecting the resin layer side with a protective film, it is possible to prevent dust from adhering to the surface of the resin layer and scratches on the surface of the resin layer.
- the protective film a film made of the same material as the resin film can be used.
- the thickness of the protective film is preferably in the range of 1-50 ⁇ m, more preferably in the range of 5-40 ⁇ m. If the thickness is less than 1 ⁇ m, the protective film tends to be difficult to handle, and if it exceeds 50 ⁇ m, it tends to be inexpensive.
- the protective film preferably has a lower adhesive strength between the resin layer and the protective film than the adhesive strength between the resin layer and the support.
- Examples of the method for producing a resin sheet include a method for producing a resin sheet by applying a resin composition to a support such as a PET film and drying it to remove the organic solvent. Coating can be performed by a known method using, for example, a roll coater, comma coater, gravure coater, die coater, bar coater, lip coater, knife coater, squeeze coater, and the like. Drying can be carried out, for example, by heating in a dryer at 60 to 200° C. for 1 to 60 minutes.
- the amount of the organic solvent remaining in the resin layer is preferably 5% by mass or less with respect to the total mass of the resin layer from the viewpoint of further preventing diffusion of the organic solvent in subsequent steps.
- the thickness of the resin layer is preferably 1 to 50 ⁇ m from the viewpoint of improving handleability.
- the resin sheet can be preferably used for manufacturing insulating layers of multilayer printed wiring boards.
- the multilayer printed wiring board of the present embodiment has an insulating layer and conductor layers formed on one or both sides of the insulating layer, and the insulating layer contains the resin composition of the present embodiment.
- the insulating layer can also be obtained, for example, by stacking one or more resin sheets and curing them.
- the number of laminations of each of the insulating layer and the conductor layer can be appropriately set according to the intended use. Also, the order of the insulating layer and the conductor layer is not particularly limited.
- the conductor layer may be a metal foil used for various printed wiring board materials, and examples thereof include metal foils of copper, aluminum, and the like. Copper metal foils include copper foils such as rolled copper foils and electrolytic copper foils.
- the thickness of the conductor layer is usually 1-100 ⁇ m. Specifically, it can be produced by the following method.
- the resin layer side of the resin sheet is laminated on one side or both sides of the circuit board using a vacuum laminator.
- circuit substrates include glass epoxy substrates, metal substrates, ceramic substrates, silicon substrates, semiconductor sealing resin substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates.
- the circuit board means a board having a patterned conductor layer (circuit) formed on one side or both sides of the board as described above.
- a board in which one or both sides of the outermost layer of the multilayer printed wiring board is a patterned conductor layer (circuit) is also a circuit board.
- the insulating layer laminated on the multilayer printed wiring board may be an insulating layer obtained by stacking one or more resin sheets of the present embodiment and curing.
- the insulating layer may be obtained by stacking one or more of the resin sheet of the embodiment and a known resin sheet different from each other.
- the method of stacking the resin sheet of the present embodiment and a known resin sheet different from the resin sheet of the present embodiment is not particularly limited.
- the surface of the conductor layer may be roughened in advance by blackening and/or copper etching.
- the resin sheet and the circuit board are preheated as necessary to pressurize and heat the resin layer of the resin sheet. while crimping it onto the circuit board.
- a method of laminating a resin layer of a resin sheet on a circuit board under reduced pressure by a vacuum lamination method is preferably used.
- the conditions of the lamination process are, for example, a pressure bonding temperature (laminating temperature) of 50 to 140° C., a pressure of 1 to 15 kgf/cm 2 , a pressure bonding time of 5 to 300 seconds, and an air pressure of 20 mmHg or less under reduced pressure. Lamination is preferred. Moreover, the lamination process may be of a batch type or a continuous type using rolls. A vacuum lamination method can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a two-stage build-up laminator manufactured by Nikko Materials Co., Ltd., and the like.
- a predetermined portion of the resin layer is irradiated with various active energy rays as a light source to cure the resin layer in the irradiated portion.
- Compound (A) does not inhibit the photocuring reaction in the exposure step.
- the irradiation may be performed through a mask pattern, or a direct writing method for direct irradiation may be used.
- Active energy rays include, for example, ultraviolet rays, visible rays, electron beams, and X-rays.
- the wavelength of the active energy ray is, for example, in the range of 200-600 nm.
- the irradiation dose is about 5 to 1000 mJ/cm 2 .
- the active energy ray for example, has a wavelength of 365 nm (i-line). It is preferable to use an active energy ray containing. When an active energy ray containing a wavelength of 365 nm (i-line) is used, the dose is approximately 5 to 10,000 mJ/cm 2 .
- an active energy ray containing, for example, a wavelength of 405 nm (h-line) is used as the active energy ray.
- the dose is approximately 5 to 10,000 mJ/cm 2 .
- Exposure through a mask pattern includes a contact exposure method in which the mask pattern is brought into close contact with the multilayer printed wiring board, and a non-contact exposure method in which a lens or mirror is used for projection exposure without close contact. can be used. Further, when a support exists on the resin layer, exposure may be performed from above the support, or exposure may be performed after peeling off the support.
- the part that is not photocured (unexposed part) is removed by direct alkali development, followed by development to form a pattern of the insulating layer. can do. Further, when a support exists on the resin layer, after removing the support after the exposure step, the portion which is not photocured (unexposed portion) is removed by alkali development, followed by development. Thereby, the pattern of the insulating layer can be formed. Since the unexposed resin layer containing the resin composition of the present embodiment contains the compound (A) and the compound (B), it has excellent alkali developability and quickly removes the unexposed resin composition. can be removed. Therefore, a printed wiring board having a high-definition pattern can be obtained.
- the developer is not particularly limited as long as it selectively elutes the unexposed portions, but tetramethylammonium hydroxide aqueous solution, sodium carbonate aqueous solution, potassium carbonate aqueous solution, sodium hydroxide aqueous solution, and An alkaline developer such as an aqueous potassium hydroxide solution is used. In this embodiment, it is more preferable to use a tetramethylammonium hydroxide aqueous solution.
- alkaline developers can be used singly or in combination of two or more.
- alkali developing method known methods such as dipping, puddle, spraying, rocking immersion, brushing, and scraping can be used. In pattern formation, these developing methods may be used in combination, if necessary.
- a developing method it is preferable to use a high-pressure spray because the resolution is further improved. A spray pressure of 0.02 to 0.5 MPa is preferable when a spray method is employed.
- a post-baking process is performed to form an insulating layer (hardened material).
- the post-baking process include an ultraviolet irradiation process using a high-pressure mercury lamp, a heating process using a clean oven, and the like, and these processes can be used in combination.
- the irradiation dose can be adjusted as necessary, for example, irradiation can be performed at a dose of approximately 0.05 to 10 J/cm 2 .
- the heating conditions can be appropriately selected as necessary, preferably in the range of 150 to 220° C. for 20 to 180 minutes, more preferably in the range of 160 to 200° C. and 30 to 150 minutes.
- Conductor layer forming step After forming the insulating layer (hardened material), a conductor layer is formed on the surface of the insulating layer by dry plating.
- the surface of the insulating layer may be subjected to surface modification treatment before dry plating.
- known methods such as plasma etching treatment, reverse sputtering treatment, and corona treatment can be used.
- dry plating known methods such as vapor deposition, sputtering, and ion plating can be used.
- a vapor deposition method vacuum vapor deposition method
- a vapor deposition method can form a metal film on an insulating layer, for example, by placing a multilayer printed wiring board in a vacuum vessel and heating and evaporating metal.
- a multilayer printed wiring board is placed in a vacuum chamber, an inert gas such as argon is introduced, a direct current voltage is applied, and the ionized inert gas collides with the target metal, and is ejected.
- a metal film can be formed on the insulating layer from a metal.
- a conductor layer is formed by electroless plating, electrolytic plating, or the like.
- a method for subsequent pattern formation for example, a subtractive method, a semi-additive method, or the like can be used.
- the semiconductor device of this embodiment includes the resin composition of this embodiment. Specifically, it can be produced by the following method.
- a semiconductor device can be manufactured by mounting a semiconductor chip on a conductive portion of a multilayer printed wiring board.
- the conductive portion means a portion of the multilayer printed wiring board that transmits an electric signal, and the portion may be a surface or an embedded portion.
- the semiconductor chip is not particularly limited as long as it is an electric circuit element made of a semiconductor.
- the method of mounting a semiconductor chip when manufacturing a semiconductor device is not particularly limited as long as the semiconductor chip functions effectively. Specifically, a wire bonding mounting method, a flip chip mounting method, a mounting method using a bumpless build-up layer (BBUL), a mounting method using an anisotropic conductive film (ACF), and a mounting method using a non-conductive film (NCF). etc.
- a semiconductor device can also be manufactured by forming an insulating layer containing a resin composition on a semiconductor chip or a substrate on which a semiconductor chip is mounted.
- the shape of the substrate on which the semiconductor chips are mounted may be wafer-like or panel-like. After forming, it can be manufactured using the same method as the multilayer printed wiring board described above.
- the mixture was liquid-separated, and the aqueous layer was extracted with 50 mL of ethyl acetate three times. All the organic layers were combined and washed once with 100 mL of water, once with 10 mL of saturated brine, and twice with 5 mL of saturated brine. After drying with magnesium sulfate and separating the solid content by filtration, the solvent was distilled off at 40° C. to obtain a yellow solid. The obtained yellow solid was dissolved in 6.5 mL of acetone, and the acetone solution was poured into 300 mL of water.
- the content of the compound (A-1) contained in the reaction solution obtained above was measured by the following method.
- a sample solution was prepared by adding 50 mg of the reaction solution to 4500 mg of THF (tetrahydrofuran), and the solution was subjected to GPC measurement under the following conditions. From the obtained elution curve, the peak area was calculated, and the GPC area fraction (content rate) of each component contained in the reaction solution was calculated. The peak area was calculated from the area between the elution curve and the baseline, and peaks that were not completely separated were calculated by vertical division.
- Example 1 (Preparation of resin composition and resin sheet) As the compound (A), 6.75 parts by mass of the compound (A-1) obtained in Synthesis Example 2, and as the compound (B), cis,cis-1,2,4-cyclohexanetricarboxylic acid-1,2 - Anhydride (H-TMAn-S (trade name) manufactured by Mitsubishi Gas Chemical Co., Ltd.) 0.36 parts by mass, and MIZ-001 manufactured by Nippon Kayaku Co., Ltd.
- H-TMAn-S trade name
- MIZ-001 manufactured by Nippon Kayaku Co., Ltd.
- This varnish is dropped onto a PET film having a thickness of 25 ⁇ m (Unipeel (registered trademark) TR1-25 (trade name) manufactured by Unitika Ltd.) and spin-coated (500 rpm for 10 seconds, then 1000 rpm for 30 seconds) to form a coating film. formed.
- the obtained coating film was dried at 90° C. for 5 minutes to obtain a resin sheet having a PET film as a support and a resin layer having a thickness of 5 ⁇ m.
- the resulting resin sheet is placed on a silicon wafer (manufactured by Advantech Co., Ltd., thickness: 625 ⁇ m, with an oxide film (thickness: 1 ⁇ m)) so that the resin surface of the resin sheet faces the oxide film side.
- a silicon wafer manufactured by Advantech Co., Ltd., thickness: 625 ⁇ m, with an oxide film (thickness: 1 ⁇ m)
- ⁇ Vacuum drawing (5.0 hPa or less) was performed for 30 seconds using a product manufactured by Materials Co., Ltd.).
- lamination molding was performed at a pressure of 10 kgf/cm 2 and a temperature of 100° C. for 30 seconds.
- lamination molding was carried out at a pressure of 7 kgf/cm 2 and a temperature of 100° C. for 60 seconds to obtain a laminate for evaluation in which a silicon wafer, a resin layer and a support were laminated.
- Example 2 As the compound (A), 4.50 parts by mass of the compound (A-1) obtained in Synthesis Example 2, and as the compound (B), cis,cis-1,2,4-cyclohexanetricarboxylic acid-1,2 - 1.44 parts by mass of anhydride (H-TMAn-S (trade name) manufactured by Mitsubishi Gas Chemical Co., Ltd.) and MIZ-001 (trade name, mass average molecular weight manufactured by Nippon Kayaku Co., Ltd.) as a maleimide compound (C) (Mw): 3000, 60 parts by mass of the compound represented by the formula (14); ) 25 parts by mass, as a maleimide compound (C), 15 parts by mass of TMDM (the compound represented by the formula (21) obtained in Synthesis Example 1), and as a photocuring initiator (D), bis(2, 3.70 parts by mass of 4,6-trimethylbenzoyl)-phenylphosphine oxide (OMnirad (registered trademark) 819 (trade name)
- Example 3 As the compound (A), 5.25 parts by mass of the compound (A-1) obtained in Synthesis Example 2, and as the compound (B), cis,cis-1,2,4-cyclohexanetricarboxylic acid-1,2 - 1.08 parts by mass of anhydride (H-TMAn-S (trade name) manufactured by Mitsubishi Gas Chemical Co., Ltd.) and MIZ-001 (trade name, mass average molecular weight manufactured by Nippon Kayaku Co., Ltd.) as a maleimide compound (C) (Mw): 3000, 60 parts by mass of the compound represented by the formula (14); ) 25 parts by mass, as maleimide compound (C), 15 parts by mass of TMDM (compound represented by formula (21) obtained in Synthesis Example 1), and as photocuring initiator (D), ethanone, 1- [9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyloxime) (Ir
- Example 4 As the compound (A), 6.85 parts by mass of the compound (A-1) obtained in Synthesis Example 2, and as the compound (B), KAYARAD (registered trademark) ZCR-6007H (trade name, compound (A1) and , a mixture containing any one or more of the compounds (A2) to (A5)) 2.86 parts by mass, and as the maleimide compound (C), Nippon Kayaku Co., Ltd. MIZ-001 (trade name, mass average Molecular weight (Mw): 3000, compound represented by formula (14)) 60 parts by mass, and as maleimide compound (C), Gun Ei Chemical Industry Co., Ltd.
- BCPH01 (trade name, represented by formula (22) compound) 25 parts by mass, 15 parts by mass of TMDM (compound represented by formula (21) obtained in Synthesis Example 1) as a maleimide compound (C), and bis(2 ,4,6-Trimethylbenzoyl)-phenylphosphine oxide (OMNIRAD (registered trademark) 819 (trade name) manufactured by IGM Resins B.V.) 3.70 parts by mass, and ethanone, 1-[9-ethyl-6 -(2-Methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (BASF Japan Co., Ltd.
- Irgacure registered trademark
- OXE02 trade name
- N-Phenyl-3-aminopropyltrimethoxysilane manufactured by Tokyo Chemical Industry Co., Ltd.
- 213.3 parts by mass of methyl ethyl ketone (MEK) are added and heated to 90 ° C.
- Hot A varnish resin composition
- a resin sheet and a laminate for evaluation were obtained in the same manner as in Example 1 using the obtained varnish.
- Example 5 As the compound (A), 5.54 parts by mass of the compound (A-1) obtained in Synthesis Example 2, and as the compound (B), KAYARAD (registered trademark) ZCR-6007H (trade name, compound (A1) and , a mixture containing any one or more of the compounds (A2) to (A5)) 8.59 parts by mass, and as the maleimide compound (C), Nippon Kayaku Co., Ltd. MIZ-001 (trade name, mass average Molecular weight (Mw): 3000, compound represented by formula (14)) 60 parts by mass, and as maleimide compound (C), Gun Ei Chemical Industry Co., Ltd.
- BCPH01 (trade name, represented by formula (22) compound) 25 parts by mass, 15 parts by mass of TMDM (compound represented by formula (21) obtained in Synthesis Example 1) as a maleimide compound (C), and bis(2 ,4,6-Trimethylbenzoyl)-phenylphosphine oxide (OMNIRAD (registered trademark) 819 (trade name) manufactured by IGM Resins B.V.) 3.70 parts by mass, and ethanone, 1-[9-ethyl-6 -(2-Methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (BASF Japan Co., Ltd.
- Irgacure registered trademark
- OXE02 trade name
- N-Phenyl-3-aminopropyltrimethoxysilane manufactured by Tokyo Chemical Industry Co., Ltd.
- 213.3 parts by mass of methyl ethyl ketone (MEK) are added and heated to 90 ° C.
- Hot A varnish resin composition
- a resin sheet and a laminate for evaluation were obtained in the same manner as in Example 1 using the obtained varnish.
- BCPH01 (trade name, represented by formula (22) compound) 25 parts by mass, 15 parts by mass of TMDM (compound represented by formula (21) obtained in Synthesis Example 1) as a maleimide compound (C), and bis(2 ,4,6-Trimethylbenzoyl)-phenylphosphine oxide (OMNIRAD (registered trademark) 819 (trade name) manufactured by IGM Resins B.V.) 3.70 parts by mass, and ethanone, 1-[9-ethyl-6 -(2-Methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (BASF Japan Co., Ltd.
- Irgacure registered trademark
- OXE02 trade name
- N-Phenyl-3-aminopropyltrimethoxysilane manufactured by Tokyo Chemical Industry Co., Ltd.
- 213.3 parts by mass of methyl ethyl ketone (MEK) are added and heated to 90 ° C.
- Hot A varnish resin composition
- a resin sheet and a laminate for evaluation were obtained in the same manner as in Example 1 using the obtained varnish.
- BCPH01 (trade name, compound represented by the formula (22)) 25 parts by mass
- TMDM the formula (21) obtained in Synthesis Example 1 as the maleimide compound (C) compound represented) 15 parts by mass
- D a photocuring initiator
- OMnirad bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide 819 manufactured by IGM Resins B.V.
- maleimide compound (C) Nippon Kayaku Co., Ltd. MIZ-001 (trade name, mass average molecular weight (Mw): 3000, compound represented by formula (14)) 60 parts by mass, and maleimide compound (C) As, BCPH01 manufactured by Gun Ei Chemical Industry Co., Ltd. (trade name, compound represented by formula (22)) 25 parts by mass, and as maleimide compound (C), TMDM (formula (21) obtained in Synthesis Example 1 and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (OMnirad (registered trademark) manufactured by IGM Resins B.V.) as a photocuring initiator (D).
- MIZ-001 trade name, mass average molecular weight (Mw): 3000, compound represented by formula (14)
- maleimide compound (C) BCPH01 manufactured by Gun Ei Chemical Industry Co., Ltd. (trade name, compound represented by formula (22)) 25 parts by mass
- maleimide compound (C) TMDM (formul
- the enthalpy (J/g) was defined as the peak area when a horizontal line was drawn from the end point of the graph. Curability was evaluated according to the following criteria. "AA”: The enthalpy was 1 (J/g) or more. “CC”: Enthalpy was less than 1 (J/g). An enthalpy of 1 (J/g) or more means that curing of the resin proceeds sufficiently by exposure at a predetermined wavelength.
- a wavelength of 200 to 200 nm is applied from above the support.
- An active energy ray containing 600 nm was applied at an illumination intensity of 18 mW and an irradiation dose of 200 mJ/cm 2 .
- the surface of the silicon wafer was heated at 90° C. for 60 seconds. After that, it was cooled to room temperature.
- the support PET film
- TMAH tetramethylammonium hydroxide
- developer manufactured by Tokuyama Co., Ltd.
- the peelability after development was visually evaluated according to the following criteria. "AA”: No peeling of the exposed resin layer after development. "CC”: Peeling of the exposed resin layer occurs after development.
- ⁇ Alkali developability> Using a light source (MA-20 (trade name) manufactured by Mikasa Co., Ltd.) capable of irradiating an active energy ray containing a wavelength of 200 to 600 nm to the obtained laminate for evaluation, via patterns (via diameters of 30 ⁇ m, 40 ⁇ m, 50 ⁇ m and 60 ⁇ m), the support was irradiated from above with an active energy ray containing a wavelength of 200 to 600 nm at an illuminance of 18 mW and a dose of 200 mJ/cm 2 . Then, using a hot plate heated to 90° C., the surface of the silicon wafer was heated at 90° C. for 60 seconds. After that, it was cooled to room temperature.
- MA-20 trade name
- TMAH tetramethylammonium hydroxide
- developer manufactured by Tokuyama Co., Ltd.
- alkali developability was evaluated according to the following criteria.
- AA Vias with a diameter of 30 ⁇ m or less can be formed after development.
- BB Vias larger than ⁇ 30 ⁇ m and smaller than 60 ⁇ m can be formed after development.
- CC A via with a diameter of less than 60 ⁇ m cannot be formed after development.
- the alkali developability could not be measured because the resin sheet was separated from the silicon wafer after development.
- the resin composition of the present embodiment is industrially useful because it does not inhibit the photocuring reaction in the exposure step in the production of a multilayer printed wiring board and can impart excellent alkali developability in the development step.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Inorganic Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
[1]下記式(1)で表される化合物(A)と、下記式(1)で表される化合物(A)以外の、カルボキシ基を1つ以上含む化合物(B)と、を含む、樹脂組成物。
[4]光硬化開始剤(D)を更に含む、[1]~[3]のいずれかに記載の樹脂組成物。
[5]前記カルボキシ基を1つ以上含む化合物(B)が、芳香族ポリカルボン酸の完全水素化物の酸無水物、芳香族ポリカルボン酸の部分水素化物の酸無水物、及び酸変性エポキシ(メタ)アクリレートからなる群より選択される少なくとも1種を含む、[1]~[4]のいずれかに記載の樹脂組成物。
前記マレイミド化合物(C)が、下記式(4)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む、ビスマレイミド化合物(C1)を含む、[3]に記載の樹脂組成物。
[8]前記樹脂層の厚さが1~50μmである、[7]に記載の樹脂シート。
[9]絶縁層と、前記絶縁層の片面又は両面に形成された導体層と、を有し、前記絶縁層が、[1]~[6]のいずれかに記載の樹脂組成物を含む、多層プリント配線板。
[10][1]~[6]のいずれかに記載の樹脂組成物を含む、半導体装置。
本実施形態の樹脂組成物は、式(1)で表される化合物(A)(成分(A)又は化合物(A)とも称する)と、式(1)で表される化合物(A)以外の、カルボキシ基を1つ以上含む化合物(B)(成分(B)又は化合物(B)とも称する)と、を含む。本実施形態の樹脂組成物は、化合物(A)及び化合物(B)を含み、多層プリント配線板の作製に好適に用いられる。樹脂組成物を用いることで、多層プリント配線板の作製における露光工程及び現像工程において、光硬化反応を阻害しないで好適に硬化物を得ることができ、露光後においては優れたアルカリ現像性を付与することができる。
本実施形態の樹脂組成物は、式(1)で表される化合物(A)を含む。
すなわち、多層プリント配線板の作製における露光工程において、化合物(A)は、露光工程における光硬化反応に関与する官能基を有さず、光硬化反応を阻害しない。また、化合物(A)は、光透過性を阻害する骨格を有さず、非常に優れた光透過性も有する。そのため、化合物(A)と共に化合物(B)を含んでも、光重合が進行し、硬化物を好適に得ることができる。
そして、化合物(A)は、光硬化反応に関与しないので、未露光部における樹脂組成物中に存在することができる。そのため、現像工程において、未露光部にアルカリ現像液が流入すると、アルカリ現像液中のアルカリ成分と、化合物(A)中のカルボキシ基とが、好適に塩を形成することができる。それにより、未露光部の水溶性が向上するため、未露光部に、マレイミド化合物(C)及び光硬化開始剤(D)等の光硬化に関与する成分が含まれていても、これらの成分を巻き込みながら、これらの成分と一緒にアルカリ現像液に溶解することができる。一方、化合物(A)は、光硬化に関与する成分と共に組成物中に混在しているため、化合物(A)のみでは、化合物(A)とこれらの成分との間にアルカリ現像液が浸透しにくい箇所が局所的に生じ、溶解性が低い箇所が生じる。その結果、化合物(A)のみでは、未露光部に溶け残りが生じ、高精細なレジストパターンが得られない。しかし、本実施形態の樹脂組成物は、化合物(A)と共に、カルボキシ基を1つ以上含む化合物(B)を含む。化合物(B)は、化合物(A)と構造が異なることから、化合物(A)とは別に光硬化に関する成分と共に組成物中に混在することができ、加えて、化合物(B)は、カルボキシ基を1つ以上有することから、アルカリ現像液が流入しやすくなる。そのため、未露光部において、アルカリ現像液が浸透にくい箇所が生じにくくなり、アルカリ現像液への溶解性が向上し、一層優れたアルカリ現像性を付与できると推定している。また、化合物(B)は1つ以上のカルボキシ基を有することから、化合物(B)を含むことで、未露光部において、アルカリ現像液中のアルカリ成分と塩をより形成しやすくなることからも、一層優れたアルカリ現像性を付与することができると推定している。
炭素数1~6の直鎖状若しくは分岐状のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、2-ブチル基、イソブチル基、tert-ブチル基、n-ペンチル基、2-ペンチル基、tert-ペンチル基、2-メチルブチル基、3-メチルブチル基、2,2-ジメチルプロピル基、n-ヘキシル基、2-ヘキシル基、3-ヘキシル基、2-メチルペンチル基、3-メチルペンチル基、4-メチルペンチル基、及び2-メチルペンタン-3-イル基が挙げられる。
R2としては、溶剤に対するより良好な溶解性を発現する観点から、炭素数1~6の直鎖状のアルキル基であることが好ましく、メチル基、エチル基、n-プロピル基、2-ブチル基、イソブチル基、tert-ブチル基、及びn-ペンチル基であることがより好ましく、メチル基、エチル基、及びn-プロピル基であることが更に好ましい。
化合物(A)は、公知の方法により製造することができ、例えば、式(7)で表されるアルコール化合物と式(8)で表される酸無水物(シクロヘキサン-1,2,4-トリカルボン酸-1,2-無水物)とをエステル化反応させる工程を含むことで得ることができる。なお、式(8)で表される酸無水物は、シクロヘキサン環に結合する2つのカルボニル基と1つのカルボキシ基との構造が立体構造を有するため、シス体、トランス体、及びシス体とトランス体の混合物として存在する。すなわち、式(8)で表される酸無水物は、1種単独であってもよく、又は2種以上の異性体を含む混合物であってもよい。
炭素数1~6の直鎖状若しくは分岐状のアルキル基としては、その好ましい態様も含めて、前記の式(1)におけるR2を参照できる。
このような溶媒としては、例えば、ジクロロメタン、クロロホルム、ジクロロエタン、及びクロロベンゼン等のハロゲン溶媒;ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド、テトラヒドロフラン、ジオキサン、及びアセトニトリル等の非プロトン性極性溶媒;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン、及びシクロヘキサノン等のケトン溶媒;2-エトキシエタノール、及びプロピレングリコールモノメチルエーテル等のセロソルブ溶媒;メタノール、エタノール、プロパノール、イソプロパノール、及びブタノール等の脂肪族アルコール溶媒;フェノール、及びクレゾール等の芳香族基含有フェノール溶媒;乳酸エチル、酢酸メチル、酢酸エチル、酢酸ブチル、酢酸イソアミル、メトキシプロピオン酸メチル、ヒドロキシイソ酪酸メチル、γ-ブチロラクトン、及びプロピレングリコールモノメチルエーテルアセテート等のエステル溶媒;トルエン、及びキシレン等の芳香族炭化水素溶媒が挙げられる。これらの溶媒は、1種単独又は2種以上を適宜混合して使用することができる。
ハロゲン溶媒としては、ジクロロメタンが好ましい。非プロトン性極性溶媒としては、ジメチルアセトアミドが好ましい。ケトン溶媒としては、メチルエチルケトンが好ましい。セロソルブ溶媒としては、プロピレングリコールモノメチルエーテルが好ましい。エステル溶媒としては、酢酸ブチル、γ-ブチロラクトン、及びプロピレングリコールモノメチルエーテルアセテートが好ましい。
この理由については定かではないが、本発明者らは次のように推定している。すなわち、ハロゲン溶媒、ケトン溶媒、及びエステル溶媒を用いることで、式(8)で表される酸無水物の加水分解がより好適に抑制され、目的とするエステル化反応以外の副反応をより抑制することができる。そのため、不純物が生じにくく、純度の高い目的物を得ることができると推定している。
この理由については定かではないが、本発明者らは次のように推定している。すなわち、エステル溶媒は、式(8)で表される酸無水物の加水分解をより抑制することができ、目的とするエステル化反応以外の副反応をより抑制することができる。そのため、不純物が、他の溶媒に比して、より生じにくく、より純度の高い目的物を得ることができると推定している。
単離した化合物(A)を更に精製する必要がある場合には、公知方法を採用して精製すればよい。このような方法としては、例えば、蒸留精製法、再結晶法、カラムクロマトグラフィー法、スラッジ処理、及び活性炭処理などが挙げられる。
本実施形態の樹脂組成物は、式(1)で表される化合物(A)以外の、カルボキシ基を1つ以上含む化合物(B)を含む。化合物(B)は、化合物中に、カルボキシ基を1つ以上含めば、特に限定されない。カルボキシ基は、ナトリウム塩、及びカリウム塩などの塩であってもよく、分子内にカルボキシ基を2以上含む場合には、それらが互いに連結して形成された酸無水物であってもよい。また、化合物(B)の分子内に、エポキシ基、(メタ)アクリロイル基等の官能基を含んでもよい。化合物(B)は、1種単独又は2種以上を適宜混合して使用することも可能である。
カルボキシ基を1つ以上含む脂肪族化合物としては、例えば、鎖状脂肪族モノカルボン酸、脂環式モノカルボン酸、鎖状脂肪族多価カルボン酸、及び脂環式多価カルボン酸が挙げられる。これらの化合物には、分子内に、水素原子、並びにアルキル基、アルコキシ基、アリールオキシ基、アリール基、アミノアルキル基、ヒドロキシ基、アミノ基、及びカルボキシアルキル基等の置換基を有していてもよい。また、これらの化合物は、分子内に、カルボキシ基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を有する場合には、カルボキシアルキル基とカルボキシ基が互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。
アルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、tert-ブトキシ基、n-ヘキサノキシ基、及び2-メチルプロポキシ基等が挙げられる。
アリールオキシ基としては、例えば、フェノキシ基、及びp-トリルオキシ基が挙げられる。
アリール基としては、例えば、フェニル基、トルイル基、ベンジル基、メチルベンジル基、キシリル基、メシチル基、ナフチル基、及びアントリル基が挙げられる。
アミノアルキル基としては、例えば、アミノメチル基、アミノエチル基、アミノプロピル基、アミノジメチル基、アミノジエチル基、アミノジプロピル基、アミノブチル基、アミノヘキシル基、及びアミノノニル基等が挙げられる。
カルボキシアルキル基としては、例えば、カルボキシメチル基、カルボキシエチル基、カルボキシプロピル基、カルボキシブチル基、カルボキシヘキシル基、及びカルボキシノニル基等が挙げられる。
カルボキシ基を1つ以上含む芳香族化合物の母体骨格としては、例えば、安息香酸、フェニレン酢酸、サリチル酸、フタル酸、トリメリット酸、ピロメリット酸、ペンタカルボキシベンゼン、ヘキサカルボキシベンゼン、ナフタレンカルボン酸、ナフタレンジカルボン酸、ナフタレントリカルボン酸、ナフタレンテトラカルボン酸、アントラセンカルボン酸、アントラセンジカルボン酸、アントラセントリカルボン酸、アントラセンテトラカルボン酸、アントラセンペンタカルボン酸等が挙げられる。芳香族化合物は、これらの母体骨格の芳香環上に、例えば、水素原子、並びにアルキル基、アルコキシ基、アリールオキシ基、アリール基、アミノアルキル基、ヒドロキシ基、アミノ基、及びカルボキシアルキル基等の置換基を有していてもよい。また、これらの化合物は、分子内に、カルボキシ基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を有する場合には、カルボキシアルキル基とカルボキシ基が互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。これらの置換基については、前記を参照できる。また、カルボキシ基を1つ以上含む芳香族化合物としては、分子中に式(11)で表される基を1つ以上と、カルボキシ基を1つ以上含む芳香族化合物も挙げられる。
カルボキシ基を1つ以上含むヘテロ化合物の母体骨格としては、例えば、フラン、チオフェン、ピロール、イミダゾール、ピラン、ピリジン、ピリミジン、ピラジン、ピロリジン、ピペリジン、ピペラジン、モルホリン、インドール、プリン、キノリン、イソキノリン、キヌクリジン、クロメン、チアントレン、フェノチアジン、フェノキサジン、キサンテン、アクリジン、フェナジン、及びカルバゾール等のヘテロ環に、1つ以上のカルボキシ基を含む化合物が挙げられる。ヘテロ化合物は、これらの母体骨格上に、例えば、水素原子、並びにアルキル基、アルコキシ基、アリールオキシ基、アリール基、アミノアルキル基、ヒドロキシ基、アミノ基、及びカルボキシアルキル基等の置換基を有していてもよい。また、これらの化合物は、分子内に、カルボキシ基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を有する場合には、カルボキシアルキル基とカルボキシ基が互いに連結して形成された酸無水物であってもよい。これらの化合物は、分子内に、カルボキシアルキル基を2つ以上有する場合には、それらが互いに連結して形成された酸無水物であってもよい。これらの置換基については、前記を参照できる。また、カルボキシ基を1つ以上含むヘテロ化合物としては、分子中に式(11)で表される基を1つ以上と、カルボキシ基を1つ以上含むヘテロ化合物も挙げられる。
炭素数1~6の直鎖状若しくは分岐状のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、2-ブチル基、イソブチル基、tert-ブチル基、n-ペンチル基、2-ペンチル基、tert-ペンチル基、2-メチルブチル基、3-メチルブチル基、2,2-ジメチルプロピル基、n-ヘキシル基、2-ヘキシル基、3-ヘキシル基、2-メチルペンチル基、3-メチルペンチル基、4-メチルペンチル基、及び2-メチルペンタン-3-イル基が挙げられる。R7としては、光硬化の反応性をより向上させる点から、水素原子、又は炭素数1~6の直鎖状のアルキル基であることが好ましく、水素原子、メチル基、エチル基、n-プロピル基、2-ブチル基、イソブチル基、tert-ブチル基、及びn-ペンチル基であることがより好ましく、水素原子、メチル基、エチル基、及びn-プロピル基であることが更に好ましい。
R9は、各々独立に、水素原子、又は置換基を有してもよい炭素数1~22の炭化水素基を示す。
炭化水素基としては、炭素原子数1~22、好ましくは1~14、さらに好ましくは1~10の直鎖状又は分岐状の脂肪族炭化水素基;炭素原子数3~22、好ましくは3~14、更に好ましくは3~10の脂環族炭化水素基;炭素原子数6~22、好ましくは6~14、更に好ましくは6~10の芳香族炭化水素基が挙げられる。
R9は、硬化物の耐熱性をより向上させる観点から、メチル基を含むことが好ましく、より好ましくはR9の全てがメチル基である。
本実施形態の樹脂組成物は、マレイミド化合物(C)(成分(C)又は化合物(C)とも称する)を更に含むことが好ましい。
本実施形態の樹脂組成物は、より良好な硬化性を発現させることができ、溶剤に対するより良好な溶解性、低融点、及びより良好な低吸水性を有することから、ビスマレイミド化合物(C1)(成分(C1)とも称する)を更に含むことが好ましい。ビスマレイミド化合物(C1)は、式(4)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む。
通常、マレイミド化合物は光透過性が悪いため、樹脂組成物がマレイミド化合物を含むと、樹脂組成物中に分散している光硬化開始剤まで十分に光が届かず、光硬化開始剤がラジカルを発生し難い。そのため、一般的にマレイミド化合物の光ラジカル反応は進行し難く、仮にマレイミド単体のラジカル重合や二量化反応が進行しても、その反応性は非常に低い。しかし、ビスマレイミド化合物(C1)は、式(4)で表される構成単位、すなわち、脂環骨格を有するので、光透過性に非常に優れる。また、化合物(A)も非常に優れた光透過性を有する。そのため、光硬化開始剤まで十分に光が届き、マレイミドの光ラジカル反応が効率的に起き、化合物(A)、化合物(B)及びビスマレイミド化合物(C1)と、必要に応じて配合される、マレイミド化合物(C)及び後述の光硬化開始剤(D)と共に、種々の活性エネルギー線(光線)を用いて光硬化させることができる。
そして、樹脂組成物は、アルカリ現像性及び光硬化性に優れる。また、得られる硬化物は、耐熱性、絶縁信頼性、及び熱安定性に優れる。そのため、本実施形態によれば、多層プリント配線板及び半導体装置における、保護膜、及び絶縁層を好適に形成することができる。
ビスマレイミド化合物(C1)の式(4)中、R3は、炭素数1~16の直鎖状若しくは分岐状のアルキレン基、又は炭素数2~16の直鎖状若しくは分岐状のアルケニレン基を示す。R3としては、より好適な粘度が得られ、ワニスの粘度上昇がより制御できる点から、直鎖状若しくは分岐状のアルキレン基であることが好ましく、直鎖状のアルキレン基であることがより好ましい。
直鎖状若しくは分岐状のアルキレン基としては、例えば、メチレン基、エチレン基、プロピレン基、2,2-ジメチルプロピレン基、ブチレン基、ペンチレン基、ヘキシレン基、ヘプチレン基、オクチレン基、ノニレン基、デシレン基、ドデシレン基、ウンデシレン基、トリデシレン基、テトラデシレン基、ペンタデシレン基、ヘキサデシレン基、ネオペンチレン基、ジメチルブチレン基、メチルヘキシレン基、エチルヘキシレン基、ジメチルヘキシレン基、トリメチルヘキシレン基、メチルヘプチレン基、ジメチルヘプチレン基、トリメチルヘプチレン基、テトラメチルヘプチレン基、エチルヘプチレン基、メチルオクチレン基、メチルノニレン基、メチルデシレン基、メチルドデシレン基、メチルウンデシレン基、メチルトリデシレン基、メチルテトラデシレン基、及びメチルペンタデシレン基が挙げられる。
直鎖状若しくは分岐状のアルケニレン基としては、例えば、ビニレン基、1-メチルビニレン基、アリレン基、プロペニレン基、イソプロペニレン基、1-ブテニレン基、2-ブテニレン基、1-ペンテニレン基、2-ペンテニレン基、イソペンチレン基、シクロペンテニレン基、シクロヘキセニレン基、及びジシクロペンタジエニレン基等が挙げられる。
直鎖状若しくは分岐状のアルキレン基としては、前記のR3が参照できる。
直鎖状若しくは分岐状のアルケニレン基としては、前記のR3が参照できる。
直鎖状若しくは分岐状のアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、1-エチルプロピル基、n-ブチル基、2-ブチル基、イソブチル基、tert-ブチル基、n-ペンチル基、2-ペンチル基、tert-ペンチル基、2-メチルブチル基、3-メチルブチル基、2,2-ジメチルプロピル基、n-ヘキシル基、2-ヘキシル基、3-ヘキシル基、n-へプチル基、n-オクチル基、2-メチルペンチル基、3-メチルペンチル基、4-メチルペンチル基、2-メチルペンタン-3-イル基、及びn-ノニル基が挙げられる。
直鎖状若しくは分岐状のアルケニル基としては、例えば、ビニル基、アリル基、4-ペンテニル基、イソプロペニル基、イソペンテニル基、2-ヘプテニル基、2-オクテニル基、及び2-ノネニル基が挙げられる。
マレイミド基は、式(13)で表され、N原子がビスマレイミド化合物(C1)の分子鎖に結合している。また、ビスマレイミド化合物(C1)に結合されるマレイミド基は、全て同一であっても異なっていてもよいが、分子鎖の両末端のマレイミド基は同一であることが好ましい。
アルキル基の炭素数としては、より好適に光硬化する点から、1~3であることが好ましく、1~2であることがより好ましい。
直鎖状若しくは分岐状のアルキル基としては、前記のR5が参照できる。
ビスマレイミド化合物(C1)は、公知の方法により製造することができる。例えば、1,2,4,5-シクロヘキサンテトラカルボン酸二無水物と、ダイマージアミン等を含むジアミンを含むモノマーと、無水マレイン酸とを、通常80~250℃程度、好ましくは100~200℃程度の温度において、通常0.5~50時間程度、好ましくは1~20時間程度、重付加反応させて重付加物を得る。その後、通常60~120℃程度、好ましくは80~100℃程度の温度において、通常0.1~2時間程度、好ましくは0.1~0.5時間程度、重付加物をイミド化反応、すなわち、脱水閉環反応させることで、ビスマレイミド化合物(C1)を得ることができる。
1,2,4,5-シクロヘキサンテトラカルボン酸二無水物のモル数と、ジアミンを含むモノマー及びマレイミド化合物との全量のモル数とを調製することで、任意のビスマレイミド化合物(C1)を得ることができる。
触媒の添加量は、例えば、イミド化剤を、アミド基に対して、0.5~5.0倍モル当量程度、脱水触媒を、アミド基に対して、0.5~10.0倍モル当量とすることが好ましい。
そして、樹脂組成物は、アルカリ現像性及び光硬化性に優れる。また、得られる硬化物は、耐熱性、絶縁信頼性、及び熱安定性に優れるため、保護膜、及び絶縁層を好適に形成することができる。
式(15)で表される化合物は、次の化合物である。
置換基を有してもよい、炭素数1~8の直鎖状若しくは分岐状のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、イソブチル基、tert-ブチル基、n-ペンチル基、1-エチルプロピル基、2,2-ジメチルプロピル基、シクロペンチル基、ヘキシル基、及びヘプチル基等が挙げられる。これらのアルキル基中の水素原子は、フッ素原子、及び塩素原子等のハロゲン原子、並びにシアノ基等で置換されていてもよい。これらのアルキル基の中でも、光硬化性、耐熱性、及び熱安定性により優れ、並びに溶剤に対する良好な溶解性、低融点、低吸水性、及び他の樹脂との良好な相溶性を発現する観点から、メチル基、エチル基、イソプロピル基、及びtert-ブチル基であることが好ましく、メチル基、エチル基、及びイソプロピル基であることがより好ましく、メチル基であることが更に好ましい。
式(16)で表される化合物は、次の化合物である。
炭素数1~6の直鎖状若しくは分岐状のアルキル基としては、前記の式(4)中におけるR5が参照できる。アルキル基としては、溶剤に対するより良好な溶解性、低融点、低吸水性、及び他の樹脂とのより良好な相溶性を発現する観点から、メチル基、エチル基、n-プロピル基、及びイソプロピル基が好ましく、メチル基であることがより好ましい。
また、R15、R16、及びR17においては、より優れた溶剤に対する溶解性を発現する観点から、R15及びR17が、炭素数1~6の直鎖状若しくは分岐状のアルキル基であり、かつ、R16が、水素原子であることが好ましい。なお、好ましいアルキル基については、前記のとおりである。
n3は、溶剤に対する溶解性により優れ、より好適な粘度が得られ、かつ、ワニスの粘度上昇がより制御できる点から、1~10の整数であることが好ましく、1~6の整数であることがより好ましい。
式(17)で表される化合物は、次の化合物である。
R18としては、溶剤に対するより良好な溶解性、低融点、低吸水性、及び他の樹脂とのより良好な相溶性を発現する観点から、メチル基、又はエチル基であることが好ましい。
R19としては、溶剤に対するより良好な溶解性、低融点、低吸水性、及び他の樹脂とのより良好な相溶性を発現する観点から、水素原子であることが好ましい。
式(18)で表される化合物は、次の化合物である。
式(18)で表されるマレイミド化合物としては、市販品を用いてもよく、例えば、式(25)で表される日本化薬(株)製MIR-3000(商品名)が挙げられる。
式(19)で表される化合物は、次の化合物である。
R21としては、溶剤に対するより良好な溶解性、低融点、低吸水性、及び他の樹脂とのより良好な相溶性を発現する観点の点から、メチル基、又はエチル基であることが好ましい。
式(19)で表されるマレイミド化合物としては、市販品を用いてもよく、例えば、式(26)で表されケイ・アイ化成(株)製BMI-80(商品名)が挙げられる。
式(20)で表される化合物は、次の化合物である。
R22としては、溶剤に対するより良好な溶解性、低融点、低吸水性、及び他の樹脂とのより良好な相溶性を発現する観点の点から、水素原子であることが好ましい。
n5としては、溶剤に対する溶解性により優れ、より好適な粘度が得られ、ワニスの粘度上昇がより制御できる点の点から、1~5の整数であることがより好ましい。
本実施形態の樹脂組成物は、光硬化開始剤(D)(成分(D)又は開始剤(D)とも称する)を更に含むことが好ましい。光硬化開始剤(D)は、特に限定されず、一般に光硬化性樹脂組成物で用いられる分野で公知のものを使用することができる。光硬化開始剤(D)は、化合物(A)と、化合物(B)と、必要に応じて配合されるマレイミド化合物(C)等と共に、種々の活性エネルギー線を用いて光硬化させるために用いられる。
p-メトキシフェニルジアゾニウムフロロホスホネート、及びN,N-ジエチルアミノフェニルジアゾニウムヘキサフロロホスホネート等のルイス酸のジアゾニウム塩;ジフェニルヨードニウムヘキサフロロホスホネート、及びジフェニルヨードニウムヘキサフロロアンチモネート等のルイス酸のヨードニウム塩;トリフェニルスルホニウムヘキサフロロホスホネート、及びトリフェニルスルホニウムヘキサフロロアンチモネート等のルイス酸のスルホニウム塩;トリフェニルホスホニウムヘキサフロロアンチモネート等のルイス酸のホスホニウム塩;その他のハロゲン化物;トリアジン系開始剤;ボーレート系開始剤;その他の光酸発生剤等のカチオン系光重合開始剤が挙げられる。
これらの光硬化開始剤(D)は、1種単独又は2種以上を適宜混合して使用することも可能である。
式(29)中、R24は、各々独立に、水素原子又はメチル基を示す。R24のうち、1つ以上がメチル基であることが好ましく、全てメチル基であることがより好ましい。
本実施形態の樹脂組成物には、塗膜性や耐熱性等の諸特性をより向上させるために、充填材を用いることができる。充填材としては、絶縁性を有し、光硬化に用いる種々の活性エネルギー線に対する透過性を阻害しないものであることが好ましい。
これらの充填材は、後述のシランカップリング剤等で表面処理されていてもよい。
本実施形態の樹脂組成物には、充填材の分散性、ポリマー及び/又は樹脂と、充填材との接着強度をより向上させるために、シランカップリング剤及び/又は湿潤分散剤を併用することできる。
これらのシランカップリング剤としては、一般に無機物の表面処理に使用されているシランカップリング剤であれば、特に限定されない。例えば、3-アミノプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン、3-アミノプロピルジメトキシメチルシラン、3-アミノプロピルジエトキシメチルシラン、N-β-(アミノエチル)-γ-アミノプロピルトリメトキシシラン、N-(2-アミノエチル)-3-アミノプロピルトリエトキシシラン、N-(2-アミノエチル)-3-アミノプロピルジメトキシメチルシラン、N-(2-アミノエチル)-3-アミノプロピルジエトキシメチルシラン、N-フェニル-3-アミノプロピルトリメトキシシラン、N-フェニル-3-アミノプロピルトリエトキシシラン、[3-(6-アミノヘキシルアミノ)プロピル]トリメトキシシラン、及び[3-(N,N-ジメチルアミノ)-プロピル]トリメトキシシランなどのアミノシラン系;γ-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリエトキシシラン、3-グリシドキシプロピルジメトキシメチルシラン、3-グリシドキシプロピルジエトキシメチルシラン、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、及び[8-(グリシジルオキシ)-n-オクチル]トリメトキシシランなどのエポキシシラン系;ビニルトリス(2-メトキシエトキシ)シラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ジメトキシメチルビニルシラン、ジエトキシメチルビニルシラン、トリメトキシ(7-オクテン-1-イル)シラン、及びトリメトキシ(4-ビニルフェニル)シランなどのビニルシラン系;3-メタクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルトリエトキシシラン、3-メタクリロキシプロピルジメトキシメチルシラン、3-メタクリロキシプロピルジエトキシメチルシランなどのメタクリルシラン系;3-アクリロキシプロピルトリメトキシシラン、及び3-アクリロキシプロピルトリエトキシシランなどのアクリルシラン系;3-イソシアネートプロピルトリメトキシシラン、及び3-イソシアネートプロピルトリエトキシシランなどのイソシアネートシラン系;トリス-(トリメトキシシリルプロピル)イソシアヌレートなどのイソシアヌレートシラン系;3-メルカプトプロピルトリメトキシシラン、及び3-メルカプトプロピルジメトキシメチルシランなどのメルカプトシラン系;3-ウレイドプロピルトリエトキシシランなどのウレイドシラン系;p-スチリルトリメトキシシランなどのスチリルシラン系;N-β-(N-ビニルベンジルアミノエチル-γ-アミノプロピルトリメトキシシラン塩酸塩などのカチオニックシラン系;[3-(トリメトキシシリル)プロピル]コハク酸無水物などの酸無水物系;フェニルトリメトキシシラン、フェニルトリエトキシシラン、ジメトキシメチルフェニルシラン、ジエトキシメチルフェニルシラン、及びp-トリルトリメトキシシランなどのフェニルシラン系;トリメトキシ(1-ナフチル)シランなどのアリールシラン系が挙げられる。これらのシランカップリング剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
樹脂組成物において、湿潤分散剤の含有量は、通常、樹脂組成物中の樹脂固形分100質量部に対して、0.1~10質量部である。
本実施形態では、本発明の効果を奏する限り、硬化した硬化物の難燃性、耐熱性、及び熱膨張特性等の特性に応じて、化合物(A)、化合物(B)、マレイミド化合物(C)、光硬化開始剤(D)以外の、シアン酸エステル化合物、フェノール樹脂、オキセタン樹脂、ベンゾオキサジン化合物、エポキシ樹脂、及びその他の化合物等、様々な種類の化合物及び樹脂を用いることができる。また、これらの化合物及び樹脂は、種々の活性エネルギー線、とりわけ、波長365nm(i線)を含む活性エネルギー線、及び波長405nm(h線)を含む活性エネルギー線で露光した場合に、樹脂組成物が感光して、光硬化することが好ましい。
これらの化合物及び樹脂は、1種単独又は2種以上を適宜混合して使用することも可能である。
シアン酸エステル化合物としては、シアナト基(シアン酸エステル基)が少なくとも1個置換された芳香族部分を分子内に有する樹脂であれば特に限定されない。
また、式(30)におけるアルキル基及びRaにおけるアリール基中の水素原子は、フッ素原子、及び塩素原子等のハロゲン原子、メトキシ基、及びフェノキシ基等のアルコキシ基、又はシアノ基等で置換されていてもよい。
アルケニル基の具体例としては、ビニル基、(メタ)アリル基、イソプロペニル基、1-プロペニル基、2-ブテニル基、3-ブテニル基、1,3-ブタンジエニル基、2-メチル-2-プロペニル、2-ペンテニル基、及び2-ヘキセニル基等が挙げられる。
アリール基の具体例としては、フェニル基、キシリル基、メシチル基、ナフチル基、フェノキシフェニル基、エチルフェニル基、o-,m-又はp-フルオロフェニル基、ジクロロフェニル基、ジシアノフェニル基、トリフルオロフェニル基、メトキシフェニル基、及びo-,m-又はp-トリル基等が挙げられる。
アルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、及びtert-ブトキシ基等が挙げられる。
式(30)のXにおける窒素数1~10の2価の有機基としては、イミノ基、及びポリイミド基等が挙げられる。
式(31)のAr2及び式(32)のAr3の具体例としては、式(31)に示す2個の炭素原子、又は式(32)に示す2個の酸素原子が、1,4位又は1,3位に結合するベンゼンジイル基、2個の炭素原子又は2個の酸素原子が4,4'位、2,4'位、2,2'位、2,3'位、3,3'位、又は3,4'位に結合するビフェニルジイル基、及び、2個の炭素原子又は2個の酸素原子が、2,6位、1,5位、1,6位、1,8位、1,3位、1,4位、又は2,7位に結合するナフタレンジイル基が挙げられる。
式(31)のRb、Rc、Rd、Re、Rf、及びRg、並びに式(32)のRi、及びRjにおけるアルキル基及びアリール基は、式(30)におけるものと同義である。
フェノール樹脂としては、1分子中に2個以上のヒドロキシ基を有するフェノール樹脂であれば、一般に公知のものを使用できる。例えば、ビスフェノールA型フェノール樹脂、ビスフェノールE型フェノール樹脂、ビスフェノールF型フェノール樹脂、ビスフェノールS型フェノール樹脂、フェノールノボラック樹脂、ビスフェノールAノボラック型フェノール樹脂、グリシジルエステル型フェノール樹脂、アラルキルノボラック型フェノール樹脂、ビフェニルアラルキル型フェノール樹脂、クレゾールノボラック型フェノール樹脂、多官能フェノール樹脂、ナフトール樹脂、ナフトールノボラック樹脂、多官能ナフトール樹脂、アントラセン型フェノール樹脂、ナフタレン骨格変性ノボラック型フェノール樹脂、フェノールアラルキル型フェノール樹脂、ナフトールアラルキル型フェノール樹脂、ジシクロペンタジエン型フェノール樹脂、ビフェニル型フェノール樹脂、脂環式フェノール樹脂、ポリオール型フェノール樹脂、リン含有フェノール樹脂、重合性不飽和炭化水素基含有フェノール樹脂、及び水酸基含有シリコーン樹脂類等が挙げられる。これらのフェノール樹脂は、1種単独又は2種以上を適宜混合して使用することも可能である。
オキセタン樹脂としては、一般に公知のものを使用できる。例えば、オキセタン、2-メチルオキセタン、2,2-ジメチルオキセタン、3-メチルオキセタン、3,3-ジメチルオキセタン等のアルキルオキセタン、3-メチル-3-メトキシメチルオキセタン、3,3-ジ(トリフルオロメチル)パーフルオロオキセタン、2-クロロメチルオキセタン、3,3-ビス(クロロメチル)オキセタン、ビフェニル型オキセタン、OXT-101(東亞合成(株)製、商品名)、OXT-121(東亞合成(株)製、商品名)、及びOXT-221(東亞合成(株)製、商品名)等が挙げられる。これらのオキセタン樹脂は、1種単独又は2種以上を適宜混合して使用することも可能である。
ベンゾオキサジン化合物としては、1分子中に2個以上のジヒドロベンゾオキサジン環を有する化合物であれば、一般に公知のものを用いることができる。例えば、ビスフェノールA型ベンゾオキサジンBA-BXZ(商品名、小西化学工業(株)製)、ビスフェノールF型ベンゾオキサジンBF-BXZ(商品名、小西化学工業(株)製)、ビスフェノールS型ベンゾオキサジンBS-BXZ(商品名、小西化学工業(株)製)、P-d型ベンゾオキサジン(商品名、四国化成工業(株)製)、F-a型ベンゾオキサジン(商品名、四国化成工業(株)製)、及びフェノールフタレイン型ベンゾオキサジン等が挙げられる。これらのベンゾオキサジン化合物は、1種単独又は2種以上を適宜混合して使用することも可能である。
エポキシ樹脂としては、特に限定されず、一般に公知のものを使用できる。例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールE型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビスフェノールAノボラック型エポキシ樹脂、ビフェニル型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、キシレンノボラック型エポキシ樹脂、多官能フェノール型エポキシ樹脂、ナフタレン型エポキシ樹脂、ナフタレン骨格変性ノボラック型エポキシ樹脂、ナフチレンエーテル型エポキシ樹脂、フェノールアラルキル型エポキシ樹脂、アントラセン型エポキシ樹脂、3官能フェノール型エポキシ樹脂、4官能フェノール型エポキシ樹脂、トリグリシジルイソシアヌレート、グリシジルエステル型エポキシ樹脂、脂環式エポキシ樹脂、ジシクロペンタジエンノボラック型エポキシ樹脂、ビフェニルノボラック型エポキシ樹脂、フェノールアラルキルノボラック型エポキシ樹脂、ナフトールアラルキルノボラック型エポキシ樹脂、アラルキルノボラック型エポキシ樹脂、ナフトールアラルキル型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ポリオール型エポキシ樹脂、リン含有エポキシ樹脂、グリシジルアミン、ブタジエン等の二重結合をエポキシ化した化合物、水酸基含有シリコーン樹脂類とエピクロルヒドリンとの反応により得られる化合物、及びこれらのハロゲン化物が挙げられる。これらのエポキシ樹脂は、1種単独又は2種以上を適宜混合して使用することも可能である。
その他の化合物としては、エチルビニルエーテル、プロピルビニルエーテル、ヒドロキシエチルビニルエーテル、及びエチレングリコールジビニルエーテル等のビニルエーテル類;スチレン、メチルスチレン、エチルスチレン、及びジビニルベンゼン等のスチレン類;トリアリルイソシアヌレート、トリメタアリルイソシアヌレート、及びビスアリルナジイミド等が挙げられる。これらの化合物は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物には、必要に応じて、有機溶剤を含有していてもよい。有機溶剤を用いると、樹脂組成物の調製時における粘度を調整することができる。有機溶剤の種類は、樹脂組成物中の樹脂の一部又は全部を溶解可能なものであれば、特に限定されない。有機溶剤としては、例えば、ジクロロメタン、クロロホルム、ジクロロエタン、及びクロロベンゼン等のハロゲン溶媒;ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド、テトラヒドロフラン、ジオキサン、及びアセトニトリル等の非プロトン性極性溶媒;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン、及びシクロヘキサノン等のケトン溶媒;2-エトキシエタノール、及びプロピレングリコールモノメチルエーテル等のセロソルブ溶媒;メタノール、エタノール、プロパノール、イソプロパノール、及びブタノール等の脂肪族アルコール溶媒;フェノール、及びクレゾール等の芳香族基含有フェノール溶媒;乳酸エチル、酢酸メチル、酢酸エチル、酢酸ブチル、酢酸イソアミル、メトキシプロピオン酸メチル、ヒドロキシイソ酪酸メチル、γ-ブチロラクトン、及びプロピレングリコールモノメチルエーテルアセテート等のエステル溶媒;トルエン、及びキシレン等の芳香族炭化水素溶媒等が挙げられる。
非プロトン性極性溶媒としては、ジメチルアセトアミドが好ましい。ケトン溶媒としては、メチルエチルケトンが好ましい。セロソルブ溶媒としては、プロピレングリコールモノメチルエーテルが好ましい。エステル溶媒としては、酢酸ブチル、γ-ブチロラクトン、及びプロピレングリコールモノメチルエーテルアセテートが好ましい。
これらの有機溶剤は、1種単独又は2種以上を適宜混合して使用することも可能である。
本実施形態の樹脂組成物には、本実施形態の特性が損なわれない範囲において、これまでに挙げられていない熱硬化性樹脂、熱可塑性樹脂、及びそのオリゴマー、並びにエラストマー類等の種々の高分子化合物;これまでに挙げられていない難燃性の化合物;添加剤等の併用も可能である。これらは一般に使用されているものであれば、特に限定されない。例えば、難燃性の化合物では、メラミンやベンゾグアナミン等の窒素含有化合物;オキサジン環含有化合物;リン系化合物のホスフェート化合物、芳香族縮合リン酸エステル、及び含ハロゲン縮合リン酸エステル等のリン系化合物が挙げられる。添加剤としては、紫外線吸収剤、酸化防止剤、蛍光増白剤、光増感剤、染料、顔料、増粘剤、滑剤、消泡剤、表面調整剤、光沢剤、重合禁止剤、及び熱硬化促進剤等が挙げられる。これらの成分は、1種単独又は2種以上を適宜混合して使用することも可能である。
樹脂組成物において、その他の成分の含有量は、通常、樹脂組成物中の樹脂固形分100質量部に対して、それぞれ0.1~10質量部である。
本実施形態の樹脂組成物は、化合物(A)及び化合物(B)と、必要に応じて、マレイミド化合物(C)、光硬化開始剤(D)、充填材、及びその他の樹脂、その他の化合物、並びに添加剤等を適宜混合することにより調製することができる。樹脂組成物の製造方法は、例えば、前記した各成分を順次溶剤に配合し、十分に撹拌する方法が挙げられる。
本実施形態の樹脂組成物は、多層プリント配線板の作製に好適に用いることができ、絶縁性の樹脂組成物が必要とされる用途に好ましく使用することができる。例えば、感光性フィルム、支持体付き感光性フィルム、プリプレグ、樹脂シート、回路基板(積層板用途、多層プリント配線板用途等)、ソルダーレジスト、アンダーフィル材、ダイボンディング材、半導体封止材、穴埋め樹脂、及び部品埋め込み樹脂等に使用することができる。それらの中でも、樹脂組成物は、光硬化性及びアルカリ現像性に優れるため、多層プリント配線板の絶縁層用として、又はソルダーレジスト用として好適に使用することができる。
硬化物は、樹脂組成物を硬化させて得られる。硬化物は、例えば、樹脂組成物を溶融又は溶媒に溶解させた後、型内に流し込み、光を用いて通常の条件で硬化させることにより得ることができる。光の波長領域は、光重合開始剤等により効率的に硬化が進む100~500nmの範囲で硬化させることが好ましい。
本実施形態の樹脂シートは、支持体と、支持体の片面又は両面に配された樹脂層と、を有し、樹脂層が、本実施形態の樹脂組成物を含む、支持体付き樹脂シートである。樹脂シートは、樹脂組成物を支持体上に塗布、及び乾燥して製造することができる。樹脂シートにおける樹脂層は、優れた光硬化性及びアルカリ現像性を有する。
樹脂層側を保護フィルムで保護することにより、樹脂層表面へのゴミ等の付着やキズを防止することができる。保護フィルムとしては、樹脂フィルムと同様の材料により構成されたフィルムを用いることができる。保護フィルムの厚さは、1~50μmの範囲であることが好ましく、5~40μmの範囲であることがより好ましい。厚さが1μm未満では、保護フィルムの取り扱い性が低下する傾向にあり、50μmを超えると廉価性に劣る傾向にある。なお、保護フィルムは、樹脂層と支持体との接着力に対して、樹脂層と保護フィルムとの接着力の方が小さいものが好ましい。
塗布方法は、例えば、ロールコーター、コンマコーター、グラビアコーター、ダイコーター、バーコーター、リップコーター、ナイフコーター、及びスクイズコーター等を用いた公知の方法で行うことができる。乾燥は、例えば、60~200℃の乾燥機中で、1~60分加熱させる方法等により行うことができる。
本実施形態の多層プリント配線板は、絶縁層と、絶縁層の片面又は両面に形成された導体層とを有し、絶縁層が、本実施形態の樹脂組成物を含む。絶縁層は、例えば、樹脂シートを1枚以上重ねて硬化して得ることもできる。絶縁層と導体層のそれぞれの積層数は、目的とする用途に応じて適宜積層数を設定することができる。また、絶縁層と導体層の順番も特に限定されない。導体層としては、各種プリント配線板材料に用いられる金属箔であってもよく、例えば、銅、及びアルミニウム等の金属箔が挙げられる。銅の金属箔としては、圧延銅箔、及び電解銅箔等の銅箔が挙げられる。導体層の厚みは、通常、1~100μmである。具体的には、以下の方法により製造することができる。
ラミネート工程では、樹脂シートの樹脂層側を、真空ラミネーターを用いて回路基板の片面又は両面にラミネートする。回路基板としては、例えば、ガラスエポキシ基板、金属基板、セラミック基板、シリコン基板、半導体封止樹脂基板、ポリエステル基板、ポリイミド基板、BTレジン基板、及び熱硬化型ポリフェニレンエーテル基板等が挙げられる。なお、回路基板とは、前記のような基板の片面又は両面にパターン加工された導体層(回路)が形成された基板をいう。また、導体層と絶縁層とを交互に積層してなる多層プリント配線板において、多層プリント配線板の最外層の片面又は両面がパターン加工された導体層(回路)となっている基板も回路基板に含まれる。なお、多層プリント配線板に積層されている絶縁層は、本実施形態の樹脂シートを1枚以上重ねて硬化して得られた絶縁層であってもよく、本実施形態の樹脂シートと、本実施形態の樹脂シートと異なる公知の樹脂シートとをそれぞれ1枚以上重ねて得られた絶縁層であってもよい。なお、本実施形態の樹脂シートと、本実施形態の樹脂シートと異なる公知の樹脂シートとの重ね方は、特に限定されない。導体層表面には、黒化処理、及び/又は銅エッチング等により予め粗化処理が施されていてもよい。ラミネート工程において、樹脂シートが保護フィルムを有している場合には、保護フィルムを剥離除去した後、必要に応じて樹脂シート及び回路基板をプレヒートし、樹脂シートの樹脂層を加圧及び加熱しながら回路基板に圧着する。本実施形態においては、真空ラミネート法により減圧下で回路基板に樹脂シートの樹脂層をラミネートする方法が好適に用いられる。
露光工程では、ラミネート工程により、回路基板上に樹脂層が設けられた後、樹脂層の所定部分に光源として、種々の活性エネルギー線を照射し、照射部の樹脂層を硬化させる。化合物(A)は、露光工程において、光硬化反応を阻害しない。
照射は、マスクパターンを通してもよいし、直接照射する直接描画法を用いてもよい。活性エネルギー線としては、例えば、紫外線、可視光線、電子線、及びX線等が挙げられる。活性エネルギー線の波長としては、例えば、200~600nmの範囲である。紫外線を用いる場合、その照射量はおおむね5~1000mJ/cm2である。また、ステップアンドリピート方式で投影露光を行うステッパーを用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際しては、活性エネルギー線として、例えば、波長365nm(i線)を含む活性エネルギー線を用いることが好ましい。波長365nm(i線)を含む活性エネルギー線を用いた場合、その照射量は、おおむね5~10,000mJ/cm2である。直接描画露光法を用いて高密度で高精細な配線形成(パターン)を有するプリント配線板を製造するに際しては、活性エネルギー線として、例えば、波長405nm(h線)を含む活性エネルギー線を用いることが好ましい。波長405nm(h線)を含む活性エネルギー線を用いた場合、その照射量は、おおむね5~10,000mJ/cm2である。
マスクパターンを通す露光法には、マスクパターンを多層プリント配線板に密着させて行う接触露光法と、密着させずにレンズやミラーを使用して投影露光する非接触露光法とがあるが、どちらを用いてもかまわない。また、樹脂層上に支持体が存在している場合は、支持体上から露光してもよいし、支持体を剥離後に露光してもよい。
樹脂層上に支持体が存在していない場合には、露光工程後、直接アルカリ現像にて光硬化されていない部分(未露光部)を除去し、現像することにより、絶縁層のパターンを形成することができる。
また、樹脂層上に支持体が存在している場合には、露光工程後、その支持体を除去した後に、アルカリ現像にて光硬化されていない部分(未露光部)を除去し、現像することにより、絶縁層のパターンを形成することができる。
本実施形態の樹脂組成物を含む未露光の樹脂層は、化合物(A)及び化合物(B)が含まれているため、優れたアルカリ現像性を有し、速やかに未露光の樹脂組成物を除去することができる。そのため、高精細なパターンを有するプリント配線板を得ることができる。
本実施形態では、アルカリ現像工程終了後、ポストベーク工程を行い、絶縁層(硬化物)を形成する。ポストベーク工程としては、高圧水銀ランプによる紫外線照射工程やクリーンオーブンを用いた加熱工程等が挙げられ、これらを併用することも可能である。紫外線を照射する場合は、必要に応じてその照射量を調整することができ、例えば、0.05~10J/cm2程度の照射量で照射を行うことができる。また加熱の条件は、必要に応じて適宜選択できるが、好ましくは150~220℃で20~180分間の範囲、より好ましくは160~200℃で30~150分間の範囲で選択される。
絶縁層(硬化物)を形成後、乾式めっきにより絶縁層表面に導体層を形成する。
なお、導体層の形成に際して、乾式めっき前に、絶縁層表面に対して、表面改質処理を行ってもよい。表面改質処理としては、プラズマエッチング処理、逆スパッタ処理、及びコロナ処理等の公知の方法を使用することができる。
乾式めっきとしては、蒸着法、スパッタリング法、及びイオンプレーティング法等の公知の方法を使用することができる。蒸着法(真空蒸着法)は、例えば、多層プリント配線板を真空容器内に入れ、金属を加熱蒸発させることにより、絶縁層上に金属膜を形成することができる。スパッタリング法も、例えば、多層プリント配線板を真空容器内に入れ、アルゴン等の不活性ガスを導入し、直流電圧を印加して、イオン化した不活性ガスをターゲット金属に衝突させ、叩き出された金属により絶縁層上に金属膜を形成することができる。
本実施形態の半導体装置は、本実施形態の樹脂組成物を含む。具体的には、以下の方法により製造することができる。多層プリント配線板の導通箇所に、半導体チップを実装することにより半導体装置を製造することができる。ここで、導通箇所とは、多層プリント配線板における電気信号を伝える箇所のことであって、その場所は表面であっても、埋め込まれた箇所であってもよい。また、半導体チップは、半導体を材料とする電気回路素子であれば特に限定されない。
[合成例1]
次のようにして、式(21)で表される化合物(TMDM)を合成した。
〔アミド酸化合物(以下、MA-TMDAと略記する。)の合成〕
まず、式(35)で表されるMA-TMDAを下記の方法にて合成した。
反応溶液を一部分取し、水と、酢酸エチルとを加えて振盪した。その後、有機層を取り出して、硫酸マグネシウムで乾燥した。上澄みを40℃で溶媒留去し、黄色オイルを得た。1H-NMR測定を行い、式(35)で表されるMA-TMDAであることを確認した。
式(35)で表されるMA-TMDAの1H-NMRの帰属を以下に示す。また、1H-NMRチャートを図1に示す。
前記の反応溶液に、p-トルエンスルホン酸一水和物0.67g(3.5mmol)を加え、127℃で2.5時間加熱還流した。室温(25℃)まで冷却した後、冷却後の反応溶液を、飽和炭酸水素ナトリウム水溶液50mLと、酢酸エチル100mLとの混合溶液に撹拌しながら注いだ。更に、水100mLと、酢酸エチル100mLとを加えて撹拌し、5分間静置した。その後、分液し、水層を酢酸エチル50mLで3回抽出した。有機層を全て合わせて、水100mLで1回、飽和食塩水10mLで1回、飽和食塩水5mLで2回洗浄した。硫酸マグネシウムで乾燥して、固体分を濾別した後、40℃で溶媒留去し、黄色固体を得た。
得られた黄色固体をアセトン6.5mLに溶解させ、アセトン溶液を水300mLに注いだ。析出した固体をろ取し、少量のイソプロピルアルコール(IPA)で洗浄した後、50℃で20時間減圧乾燥して黄色固体5.71質量部を得た。1H-NMR測定を行い、式(21)で表されるマレイミド化合物(TMDM)であること確認した。
TMDMの1H-NMRの帰属を以下に示す。また、1H-NMRチャートを図2に示す。
[合成例2]
次のようにして、式(6)で表される化合物(化合物(A-1)とも称する)を合成した。
200mLのフラスコに、ジトリメチロールプロパン(東京化成工業(株)製)12.52g(50mmol)と、シス,シス-シクロヘキサン-1,2,4-トリカルボン酸-1,2-無水物(三菱ガス化学(株)製、H-TMAn-S(商品名))41.62g(210mmol)と、4-ジメチルアミノピリジン6.10g(50mmol)と、トリエチルアミン22.26gと、ジクロロメタン150gとを加え、室温(25℃)で9時間撹拌した。
化合物(A-1)の1H-NMRの帰属を以下に示す。また、1H-NMRチャートを図3に示す。
THF(テトラヒドロフラン)4500mgに反応溶液50mgを加えて試料溶液とし、その溶液を下記の条件にて、GPC測定を行った。得られた溶出曲線から、ピーク面積を算出して、反応溶液中に含まれる各成分のGPC面積分率(含有率)を算出した。なお、ピーク面積は、溶出曲線とベースライン間との面積から算出し、分離が完全でないピークについては、垂直分割することで算出した。
測定機器:(株)島津製作所製Prominence(商品名)
カラム:昭和電工(株)製KF-801(商品名)、昭和電工(株)製KF-802(商品名)、昭和電工(株)製KF-803(商品名)、及び昭和電工(株)製KF-804(商品名)
流速:1mL/min
カラム温度:40℃
検出器:RI(Refractive Index、屈折率)検出器
(樹脂組成物及び樹脂シートの作製)
化合物(A)として、合成例2で得られた化合物(A-1)を6.75質量部と、化合物(B)として、シス,シス-1,2,4-シクロヘキサントリカルボン酸-1,2-無水物(三菱ガス化学社製H-TMAn-S(商品名))0.36質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。このワニスを厚さ25μmのPETフィルム(ユニチカ(株)製ユニピール(登録商標)TR1-25(商品名))上に滴下し、スピンコート(500rpmで10秒間、その後1000rpmで30秒間)により塗膜を形成した。得られた塗膜を90℃で5分間乾燥して、PETフィルムを支持体とし樹脂層の厚さが5μmである樹脂シートを得た。
得られた樹脂シートを、シリコンウェハー((株)アドバンテック製、厚さ:625μm、酸化膜(厚み1μm)付き)の酸化膜側に樹脂シートの樹脂面が向くように配置し、真空ラミネーター(ニッコー・マテリアルズ(株)製)を用いて、30秒間真空引き(5.0hPa以下)を行った。その後、圧力10kgf/cm2、温度100℃で30秒間の積層成形を行った。さらに圧力7kgf/cm2、温度100℃で60秒間の積層成形を行うことでシリコンウェハーと樹脂層と支持体とが積層された評価用積層体を得た。
化合物(A)として、合成例2で得られた化合物(A-1)を4.50質量部と、化合物(B)として、シス,シス-1,2,4-シクロヘキサントリカルボン酸-1,2-無水物(三菱ガス化学社製H-TMAn-S(商品名))1.44質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(A)として、合成例2で得られた化合物(A-1)を5.25質量部と、化合物(B)として、シス,シス-1,2,4-シクロヘキサントリカルボン酸-1,2-無水物(三菱ガス化学社製H-TMAn-S(商品名))1.08質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))5.00質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(A)として、合成例2で得られた化合物(A-1)を6.85質量部と、化合物(B)として、KAYARAD(登録商標)ZCR-6007H(商品名、化合物(A1)と、化合物(A2)~(A5)のいずれか1種以上とを含む混合物)2.86質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(A)として、合成例2で得られた化合物(A-1)を5.54質量部と、化合物(B)として、KAYARAD(登録商標)ZCR-6007H(商品名、化合物(A1)と、化合物(A2)~(A5)のいずれか1種以上とを含む混合物)8.59質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(A)として、合成例2で得られた化合物(A-1)を7.50質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(B)として、シス,シス-1,2,4-シクロヘキサントリカルボン酸-1,2-無水物(三菱ガス化学社製H-TMAn-S(商品名))3.58質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
化合物(B)として、KAYARAD(登録商標)ZCR-6007H(商品名、化合物(A1)と、化合物(A2)~(A5)のいずれか1種以上とを含む混合物)31.03質量部と、マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
マレイミド化合物(C)として、日本化薬(株)製MIZ-001(商品名、質量平均分子量(Mw):3000、式(14)で表される化合物)60質量部と、マレイミド化合物(C)として、群栄化学工業(株)製BCPH01(商品名、式(22)で表される化合物)25質量部と、マレイミド化合物(C)として、TMDM(合成例1で得られた式(21)で表される化合物)15質量部と、光硬化開始剤(D)として、ビス(2,4,6-トリメチルベンゾイル)-フェニルフォスフィンオキサイド(IGM Resins B.V.社製Omnirad(登録商標)819(商品名))3.70質量部と、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)(BASFジャパン(株)製Irgacure(登録商標)OXE02(商品名))1.30質量部と、N-フェニル-3-アミノプロピルトリメトキシシラン(東京化成工業(株)製)3.00質量部とを混合し、メチルエチルケトン(MEK)213.3質量部を加えて、90℃に加熱したホットプレート上で加熱してワニス(樹脂組成物)を得た。
得られたワニスを用いて、実施例1と同様の方法で樹脂シート、及び評価用積層体を得た。
実施例及び比較例で得られた樹脂シート、及び評価用積層体を、以下の方法により測定し、評価した。それらの結果を表1に示す。
<光硬化性>
波長200~600nmを含む活性エネルギー線を照射可能な光源(ユーヴィックス(株)製Omnicure(登録商標)S2000(商品名))を付属したフォトDSC(ティー・エイ・インスツルメント・ジャパン(株)製DSC-2500(商品名))を用い、得られた樹脂シートに、波長200~600nmを含む活性エネルギー線を、照度30mW、露光時間3.5分間照射して、横軸が時間(sec)、縦軸がヒートフロー(mW)のグラフを得た。
得られたグラフにおいて、グラフの終点から、水平に線を引いた際のピーク面積をエンタルピー(J/g)とした。硬化性は、以下の基準に従って評価した。
「AA」:エンタルピーが1(J/g)以上であった。
「CC」:エンタルピーが1(J/g)未満であった。
なお、エンタルピーが1(J/g)以上とは、所定の波長における露光により、樹脂の硬化が十分に進行することを意味した。
得られた評価用積層体に、波長200~600nmを含む活性エネルギー線を照射可能な光源(ミカサ(株)製MA-20(商品名))を用いて、支持体の上から、波長200~600nmを含む活性エネルギー線を、照度18mW、照射量200mJ/cm2にて照射した。その後、90℃に加熱したホットプレートを用いて、シリコンウェハー面から90℃で60秒加熱した。その後、室温まで冷却した。その後、支持体(PETフィルム)を剥離し、35℃の2.38%TMAH(水酸化テトラメチルアンモニウム)水溶液(現像液、(株)トクヤマ社製)中で180秒間振とうした。
現像後の剥離性は、以下の基準に従って目視にて評価した。
「AA」:現像後に露光した樹脂層の剥離が生じない。
「CC」:現像後に露光した樹脂層の剥離が生じる。
得られた評価用積層体に、波長200~600nmを含む活性エネルギー線を照射可能な光源(ミカサ(株)製MA-20(商品名))を用いて、ビアパターン(ビア径30μm、40μm、50μm、及び60μm)を有するクロムマスクを介して、支持体の上から、波長200~600nmを含む活性エネルギー線を、照度18mW、照射量200mJ/cm2にて照射した。その後、90℃に加熱したホットプレートを用いて、シリコンウェハー面から90℃で60秒加熱した。その後、室温まで冷却した。その後、支持体(PETフィルム)を剥離し、35℃の2.38%TMAH(水酸化テトラメチルアンモニウム)水溶液(現像液、(株)トクヤマ社製)中で180秒間振とうした。その後、光学顕微鏡を用いてビアパターンを観察し、アルカリ現像性を以下の基準に従って評価した。
「AA」:現像後に、φ30μm以下のビアが形成できる。
「BB」:現像後に、φ30μmより大きく60μm未満のビアが形成できる。
「CC」:現像後に、φ60μm未満のビアが形成できない。
なお、比較例3では、現像後において、樹脂シートがシリコンウェハーから剥離したため、アルカリ現像性を測定できなかった。
Claims (10)
- マレイミド化合物(C)を更に含む、請求項1に記載の樹脂組成物。
- 光硬化開始剤(D)を更に含む、請求項1に記載の樹脂組成物。
- 前記カルボキシ基を1つ以上含む化合物(B)が、芳香族ポリカルボン酸の完全水素化物の酸無水物、芳香族ポリカルボン酸の部分水素化物の酸無水物、及び酸変性エポキシ(メタ)アクリレートからなる群より選択される少なくとも1種を含む、請求項1に記載の樹脂組成物。
- 前記マレイミド化合物(C)が、
下記式(4)で表される構成単位と、分子鎖の両末端にマレイミド基と、を含む、ビスマレイミド化合物(C1)を含む、請求項3に記載の樹脂組成物。
- 支持体と、
前記支持体の片面又は両面に配された樹脂層と、を有し、
前記樹脂層が、請求項1に記載の樹脂組成物を含む、
樹脂シート。 - 前記樹脂層の厚さが1~50μmである、請求項7に記載の樹脂シート。
- 絶縁層と、
前記絶縁層の片面又は両面に形成された導体層と、
を有し、
前記絶縁層が、請求項1に記載の樹脂組成物を含む、多層プリント配線板。 - 請求項1に記載の樹脂組成物を含む、半導体装置。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP22824982.7A EP4357376A1 (en) | 2021-06-15 | 2022-06-14 | Resin composition, resin sheet, multilayer printed wiring board, and semiconductor device |
KR1020237028568A KR20240021144A (ko) | 2021-06-15 | 2022-06-14 | 수지 조성물, 수지 시트, 다층 프린트 배선판, 및 반도체 장치 |
CN202280042912.8A CN117500851A (zh) | 2021-06-15 | 2022-06-14 | 树脂组合物、树脂片、多层印刷电路板和半导体装置 |
JP2023508068A JP7298798B2 (ja) | 2021-06-15 | 2022-06-14 | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021-099134 | 2021-06-15 | ||
JP2021099134 | 2021-06-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022264994A1 true WO2022264994A1 (ja) | 2022-12-22 |
Family
ID=84526465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/023722 WO2022264994A1 (ja) | 2021-06-15 | 2022-06-14 | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP4357376A1 (ja) |
JP (1) | JP7298798B2 (ja) |
KR (1) | KR20240021144A (ja) |
CN (1) | CN117500851A (ja) |
TW (1) | TW202306942A (ja) |
WO (1) | WO2022264994A1 (ja) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0912712A (ja) | 1995-06-27 | 1997-01-14 | Lion Corp | ダイマージアミン由来のポリアミド樹脂及び該ポリアミドを含有する合成樹脂製光学用材料 |
JP2014234500A (ja) * | 2013-06-05 | 2014-12-15 | 日本化薬株式会社 | 半導体製造工程用粘着材料 |
JP2015229734A (ja) | 2014-06-05 | 2015-12-21 | Dic株式会社 | 硬化性樹脂組成物、硬化物および硬化剤 |
JP2017039894A (ja) * | 2015-08-21 | 2017-02-23 | 日本化薬株式会社 | 多価カルボン酸およびそれを含有する多価カルボン酸組成物、エポキシ樹脂組成物、熱硬化性樹脂組成物、それらの硬化物並びに光半導体装置 |
WO2018056466A1 (ja) | 2016-09-26 | 2018-03-29 | 日立化成株式会社 | 樹脂組成物、半導体用配線層積層体及び半導体装置 |
WO2020262579A1 (ja) * | 2019-06-28 | 2020-12-30 | 三菱瓦斯化学株式会社 | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 |
WO2021117760A1 (ja) * | 2019-12-11 | 2021-06-17 | 三菱瓦斯化学株式会社 | 化合物及びその製造方法、樹脂組成物、樹脂シート、多層プリント配線板、並びに半導体装置 |
JP2021099134A (ja) | 2019-12-23 | 2021-07-01 | 昭和電工マテリアルズ株式会社 | 焼結含油軸受およびその製造方法 |
-
2022
- 2022-06-14 TW TW111122014A patent/TW202306942A/zh unknown
- 2022-06-14 WO PCT/JP2022/023722 patent/WO2022264994A1/ja active Application Filing
- 2022-06-14 CN CN202280042912.8A patent/CN117500851A/zh active Pending
- 2022-06-14 KR KR1020237028568A patent/KR20240021144A/ko unknown
- 2022-06-14 JP JP2023508068A patent/JP7298798B2/ja active Active
- 2022-06-14 EP EP22824982.7A patent/EP4357376A1/en active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0912712A (ja) | 1995-06-27 | 1997-01-14 | Lion Corp | ダイマージアミン由来のポリアミド樹脂及び該ポリアミドを含有する合成樹脂製光学用材料 |
JP2014234500A (ja) * | 2013-06-05 | 2014-12-15 | 日本化薬株式会社 | 半導体製造工程用粘着材料 |
JP2015229734A (ja) | 2014-06-05 | 2015-12-21 | Dic株式会社 | 硬化性樹脂組成物、硬化物および硬化剤 |
JP2017039894A (ja) * | 2015-08-21 | 2017-02-23 | 日本化薬株式会社 | 多価カルボン酸およびそれを含有する多価カルボン酸組成物、エポキシ樹脂組成物、熱硬化性樹脂組成物、それらの硬化物並びに光半導体装置 |
WO2018056466A1 (ja) | 2016-09-26 | 2018-03-29 | 日立化成株式会社 | 樹脂組成物、半導体用配線層積層体及び半導体装置 |
WO2020262579A1 (ja) * | 2019-06-28 | 2020-12-30 | 三菱瓦斯化学株式会社 | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 |
WO2021117760A1 (ja) * | 2019-12-11 | 2021-06-17 | 三菱瓦斯化学株式会社 | 化合物及びその製造方法、樹脂組成物、樹脂シート、多層プリント配線板、並びに半導体装置 |
JP2021099134A (ja) | 2019-12-23 | 2021-07-01 | 昭和電工マテリアルズ株式会社 | 焼結含油軸受およびその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP4357376A1 (en) | 2024-04-24 |
CN117500851A (zh) | 2024-02-02 |
TW202306942A (zh) | 2023-02-16 |
JPWO2022264994A1 (ja) | 2022-12-22 |
JP7298798B2 (ja) | 2023-06-27 |
KR20240021144A (ko) | 2024-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6850447B1 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
JP7016485B2 (ja) | 化合物及びその製造方法、樹脂組成物、樹脂シート、多層プリント配線板、並びに半導体装置 | |
KR102479615B1 (ko) | 수지 조성물, 수지 시트, 다층 프린트 배선판, 및 반도체 장치 | |
JP7291297B2 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
JP7298798B2 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
JP7305110B2 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
WO2022264984A1 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
JP7302760B2 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 | |
TWI836473B (zh) | 樹脂組成物、樹脂片、多層印刷配線板、及半導體裝置 | |
WO2021117764A1 (ja) | 化合物及びその製造方法、樹脂組成物、樹脂シート、多層プリント配線板、並びに半導体装置 | |
TWI841812B (zh) | 化合物及其製造方法、樹脂組成物、樹脂片、多層印刷電路板、以及半導體裝置 | |
WO2024079924A1 (ja) | 樹脂組成物、樹脂シート、多層プリント配線板、及び半導体装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22824982 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2023508068 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 18567082 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280042912.8 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2022824982 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2022824982 Country of ref document: EP Effective date: 20240115 |