JP2006022207A - Silicon compound - Google Patents
Silicon compound Download PDFInfo
- Publication number
- JP2006022207A JP2006022207A JP2004201561A JP2004201561A JP2006022207A JP 2006022207 A JP2006022207 A JP 2006022207A JP 2004201561 A JP2004201561 A JP 2004201561A JP 2004201561 A JP2004201561 A JP 2004201561A JP 2006022207 A JP2006022207 A JP 2006022207A
- Authority
- JP
- Japan
- Prior art keywords
- replaced
- silicon compound
- phenyl
- compound
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- -1 ethylphenyl Chemical group 0.000 abstract description 57
- 150000001875 compounds Chemical class 0.000 abstract description 40
- 229920001577 copolymer Polymers 0.000 abstract description 17
- 239000012776 electronic material Substances 0.000 abstract description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- 239000002305 electric material Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006459 hydrosilylation reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- DMEXFOUCEOWRGD-UHFFFAOYSA-N chloro-[chloro(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(Cl)O[Si](C)(C)Cl DMEXFOUCEOWRGD-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- POPVULPQMGGUMJ-UHFFFAOYSA-N octasilsesquioxane cage Chemical class O1[SiH](O[SiH](O2)O[SiH](O3)O4)O[SiH]4O[SiH]4O[SiH]1O[SiH]2O[SiH]3O4 POPVULPQMGGUMJ-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 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 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- 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 1
- 125000006734 (C2-C20) alkoxyalkyl group Chemical group 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OOXOBWDOWJBZHX-UHFFFAOYSA-N n-(dimethylaminosilyl)-n-methylmethanamine Chemical compound CN(C)[SiH2]N(C)C OOXOBWDOWJBZHX-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
本発明は、シルセスキオキサン誘導体を用いて得られるケイ素化合物に関する。このケイ素化合物は、電子材料、光学材料、電子光学材料、塗料、プライマーなどに用いられる。「シルセスキオキサン」は、各ケイ素原子が３個の酸素原子と結合し、各酸素原子が２個のケイ素原子と結合している化合物を示す類名であるが、本発明において用いる「シルセスキオキサン骨格」は、シルセスキオキサン構造およびその一部が変形したシルセスキオキサン類似構造の総称である。 The present invention relates to a silicon compound obtained using a silsesquioxane derivative. This silicon compound is used for electronic materials, optical materials, electro-optical materials, paints, primers, and the like. “Silsesquioxane” is a class name indicating a compound in which each silicon atom is bonded to three oxygen atoms, and each oxygen atom is bonded to two silicon atoms. The “sesquioxane skeleton” is a general term for a silsesquioxane structure and a silsesquioxane-like structure in which a part thereof is deformed.
シルセスキオキサン骨格を含むポリマーは、特異な構造を有するため様々な分野での用途が検討されている。これまで、テトラエトキシシランのようなアルコキシシランを用いたゾル−ゲル法によってシルセスキオキサン構造を有する重合体の合成が行われてきた。しかし、ゾル−ゲル法には、反応時間が長い、反応の制御が難しい、微細な空孔が残りやすいなどの課題が残されている。 Since a polymer containing a silsesquioxane skeleton has a unique structure, its use in various fields has been studied. So far, polymers having a silsesquioxane structure have been synthesized by a sol-gel method using an alkoxysilane such as tetraethoxysilane. However, the sol-gel method still has problems such as a long reaction time, difficulty in controlling the reaction, and easy formation of fine pores.
かご型構造を有するシルセスキオキサンまたはその誘導体を用いた重合体に関する研究が行われている。そしてこの重合体は、耐候性、耐熱性、物理的特性、光学的特性などに優れていると期待されている。例えば、Lichtenhan等は、シルセスキオキサンのかご型構造に欠損があるもの、いわゆる不完全なかご型構造（完全な８面体状ではなく、その１部が欠損した構造）のものをシロキサンで結合した共重合体の製造方法を開示している（特許文献１および２）。この製造方法は、多面体オリゴメリックシルセスキオキサン（polyhedral oligomeric Silsesquioxane）を、アミンなどを官能基とする二官能性のシラン、シロキサン、または有機金属化合物で架橋する方法である。Lichtenhan等は、不完全なかご型構造のシルセスキオキサンをシロキサン等で結合したものを主鎖とする共重合体の製造方法、およびかご型構造のシルセスキオキサンをペンダント共重合成分とし、メタクリル酸を共重合体主鎖成分とした共重合体の製造方法を開示している（非特許文献１）。更に、非特許文献２にてシルセスキオキサンの不完全なかご型構造の隅に位置するＳｉに結合するＯＨと、ビス（ジメチルアミノ）シラン等とを反応させたシルセスキオキサン−シロキサン共重合体の製造方法を開示している（非特許文献２）。 Studies have been conducted on polymers using silsesquioxane having a cage structure or derivatives thereof. This polymer is expected to be excellent in weather resistance, heat resistance, physical properties, optical properties, and the like. For example, Lichtenhan et al. Linked silsesquioxanes with defects in the cage structure, so-called incomplete cage structures (not complete octahedrons, but lacked part of them) with siloxane. The manufacturing method of the made copolymer is disclosed (patent documents 1 and 2). This production method is a method of crosslinking polyhedral oligomeric silsesquioxane with a bifunctional silane, siloxane, or organometallic compound having amine as a functional group. Lichtenhan et al., A method for producing a copolymer having a main chain of silsesquioxane having an incomplete cage structure bonded with siloxane or the like, and a silsesquioxane having a cage structure as a pendant copolymer component, A method for producing a copolymer using methacrylic acid as a copolymer main chain component is disclosed (Non-Patent Document 1). Furthermore, in Non-Patent Document 2, silsesquioxane-siloxane co-polymer obtained by reacting OH bonded to Si located at the corner of an incomplete cage structure of silsesquioxane with bis (dimethylamino) silane or the like. The manufacturing method of a polymer is disclosed (nonpatent literature 2).
一方、完全なかご型構造のシルセスキオキサンとビニル基含有化合物とを反応させる共重合体の製造方法が開示されている（Lichtenhan等、特許文献３）。田中等は水素化オクタシルセスキオキサンとフェニルエチルベンゼンをヒドロシリル化重合させて共重合体が得られることを報告している（非特許文献３）。Laine等は、かご型構造の複数の隅にビニル基を結合させた完全なかご型のシルセスキオキサン化合物と、水素化した完全なかご型のシルセスキオキサン化合物をヒドロシリル化重合させると、ゲル状の共重合体が得られることを報告している（非特許文献４）。Zank等は、かご型構造を有する水素化オクタシルセスキオキサンと水酸基含有化合物またはビニル基含有化合物とを反応させて、有機溶剤可溶性の水素化オクタシルセスキオキサンを有する共重合体を得る製造法を開示している（特許文献４および５）。これらはいずれも、完全なかご型構造を有するシルセスキオキサンが主鎖にグラフトした構造であるか、架橋点となるかのどちらかである。かご型構造を有するシルセスキオキサンをポリマー鎖にグラフトさせた場合、シルセスキオキサンは局所的な分子運動を抑制するためポリマーへの改質効果を示すが、ポリマー鎖構造の変化には寄与しない、一方、シルセスキオキサンが架橋点となった場合、ゲル状の共重合体となり成形性に劣る。 On the other hand, a method for producing a copolymer in which a completely caged silsesquioxane is reacted with a vinyl group-containing compound is disclosed (Lichtenhan et al., Patent Document 3). Tanaka et al. Reported that a copolymer can be obtained by hydrosilylation polymerization of hydrogenated octasilsesquioxane and phenylethylbenzene (Non-patent Document 3). Laine et al. Performed hydrosilylation polymerization of a complete cage silsesquioxane compound in which vinyl groups are bonded to a plurality of corners of a cage structure and a hydrogenated complete cage silsesquioxane compound. It has been reported that a gel-like copolymer is obtained (Non-patent Document 4). Manufacture of hydrogenated octasilsesquioxane having a cage structure and a hydroxyl group-containing compound or vinyl group-containing compound to obtain a copolymer having an organic solvent-soluble hydrogenated octasilsesquioxane The law is disclosed (patent documents 4 and 5). Either of these is either a structure in which silsesquioxane having a complete cage structure is grafted to the main chain or a crosslinking point. When silsesquioxane having a cage structure is grafted to a polymer chain, silsesquioxane exhibits a modification effect on the polymer to suppress local molecular motion, but contributes to changes in the polymer chain structure. On the other hand, when silsesquioxane becomes a crosslinking point, it becomes a gel-like copolymer and is inferior in moldability.
電気・電子材料においては、特に、絶縁性、耐熱性、耐久性、成形性等の更なる改善が求められている。しかしながら、従来のシルセスキオキサン共重合体ではこれらの特性を満たすことはできない。そのために、優れた耐熱性、耐候性、電気絶縁性、硬度、力学的強度、耐薬品性等をもつかご型構造を有するシルセスキオキサンを主鎖とし、結合の位置が明確に限定され、成形性に優れた共重合体が望まれている。しかしながら、主鎖にかご型構造を有するシルセスキオキサンを有する共重合体は、従来の化合物を用いる場合には困難であった。非特許文献５には主鎖型ポリマーとして用いることのできる化合物が開示されているが、Ｔ８構造のシルセスキオキサン骨格を主鎖に導入した共重合体の開示例は１つのみであり、成形体として使用できる可能性も不明であり、知られている特性も限られていた。従って、依然として具体的な用途は十分明らかではなかった。 In electrical / electronic materials, further improvements in insulation, heat resistance, durability, moldability and the like are required. However, conventional silsesquioxane copolymers cannot satisfy these characteristics. Therefore, silsesquioxane having a cage structure with excellent heat resistance, weather resistance, electrical insulation, hardness, mechanical strength, chemical resistance, etc. as the main chain, the position of the bond is clearly limited, A copolymer excellent in moldability is desired. However, a copolymer having a silsesquioxane having a cage structure in the main chain has been difficult when a conventional compound is used. Non-Patent Document 5 discloses a compound that can be used as a main chain type polymer, but there is only one disclosure example of a copolymer in which a silsesquioxane skeleton having a T8 structure is introduced into the main chain, The possibility of being used as a molded body is also unknown, and the known properties are limited. Therefore, the specific application is still not sufficiently clear.
本発明で用いる用語は、次のように定義される。アルキルおよびアルキレンは、どちらも直鎖の基であってもよく、分岐された基であってもよい。このことは、これらの基において任意の水素がハロゲンや環式の基などと置き換えられた場合も、任意の−ＣＨ２−が−Ｏ−、−ＣＨ＝ＣＨ−、シクロアルキレン、シクロアルケニレン、フェニレンなどで置き換えられた場合も同様である。本発明で用いる「任意の」は、位置のみならず個数も任意であることを示す。複数の基が別の基で置き換えられるときには、それぞれの基が異なる別の基で置き換えられてもよい。例えば、アルキルにおいて任意の−ＣＨ２−が−Ｏ−または−ＣＨ＝ＣＨ−で置き換えられてもよい場合には、アルコキシアルケニルまたはアルケニルオキシアルキルであってもよいことを示す。そして、これらの基におけるアルコキシ、アルケニレン、アルケニルおよびアルキレンのいずれの基も、直鎖の基であってもよく、分岐された基であってもよい。但し、本発明において、任意の−ＣＨ２−が−Ｏ−で置き換えられてもよいと記述するときには、連続する複数の−ＣＨ２−が−Ｏ−で置き換えられることはない。 The terms used in the present invention are defined as follows. Alkyl and alkylene may both be a linear group or a branched group. This means that any —CH 2 — is replaced by —O—, —CH═CH—, cycloalkylene, cycloalkenylene, phenylene even when any hydrogen in these groups is replaced with a halogen or a cyclic group. The same applies to the case where they are replaced by the above. “Arbitrary” used in the present invention indicates that not only the position but also the number is arbitrary. When a plurality of groups are replaced with another group, each group may be replaced with a different group. For example, when any —CH 2 — in alkyl may be replaced by —O— or —CH═CH—, this indicates that it may be alkoxyalkenyl or alkenyloxyalkyl. And any group of alkoxy, alkenylene, alkenyl and alkylene in these groups may be a linear group or a branched group. However, in the present invention, when it is described that any —CH 2 — may be replaced by —O—, a plurality of consecutive —CH 2 — is not replaced by —O—.
Ｔ８Ｄ２構造またはその類似構造を有するシルセスキオキサン骨格を主鎖に導入することにより、任意に分子量等を制御でき、求められる物性に調整することが可能となる。Ｓｉに３個の酸素が結合している構造をＴ構造とし、Ｓｉに２個の酸素が結合している構造をＤ構造とするとき、Ｔ８Ｄ２構造は８つのＴ構造と２つのＤ構造とが組み合わされている構造を意味する。注釈なしで用いられるフェニルおよびナフチルはそれぞれ非置換の基を示す。 By introducing a silsesquioxane skeleton having a T8D2 structure or a similar structure into the main chain, the molecular weight and the like can be arbitrarily controlled, and the required physical properties can be adjusted. When a structure in which three oxygens are bonded to Si is a T structure, and a structure in which two oxygens are bonded to Si is a D structure, the T8D2 structure has eight T structures and two D structures. Means a combined structure. Phenyl and naphthyl used without annotation each represent an unsubstituted group.
本発明者等は、下記の式（１）で示される構成単位を有するケイ素化合物を新規に合成し、これを用いて無色透明なコーティング膜を形成できること、加熱溶融により成形体を形成できることを知った。即ち、上記の課題は下記の構成からなる本発明によって解決される。
［１］式（１）で示される構成単位を有するケイ素化合物。
[1] A silicon compound having a structural unit represented by the formula (1).
［２］Ｒ０のすべてがフェニル、シクロペンチルおよびシクロヘキシルから選択される同一の基であり、Ｒ１およびＲ２が独立してフェニルまたはメチルである、［１］項に記載のケイ素化合物。 [2] The silicon compound according to item [1], wherein all of R 0 are the same group selected from phenyl, cyclopentyl and cyclohexyl, and R 1 and R 2 are independently phenyl or methyl.
［３］Ｒ０のすべてがフェニルであり、Ｒ１およびＲ２が独立してフェニルまたはメチルである、［１］項に記載のケイ素化合物。 [3] The silicon compound according to item [1], wherein all of R 0 are phenyl, and R 1 and R 2 are independently phenyl or methyl.
［４］ｍが１〜１０の整数であり、構成単位の繰り返し数が１以上である、［１］〜［３］のいずれか１項に記載のケイ素化合物。 [4] The silicon compound according to any one of [1] to [3], wherein m is an integer of 1 to 10, and the number of repeating structural units is 1 or more.
［５］ｍが１〜３の整数であり、構成単位の繰り返し数が２〜１００である、［１］〜［３］のいずれか１項に記載のケイ素化合物。 [5] The silicon compound according to any one of [1] to [3], wherein m is an integer of 1 to 3, and the number of repeating structural units is 2 to 100.
［６］ｍが１〜３の整数であり、構成単位の繰り返し数が２〜２０である、［１］〜［３］のいずれか１項に記載のケイ素化合物。 [6] The silicon compound according to any one of [1] to [3], wherein m is an integer of 1 to 3, and the number of repeating structural units is 2 to 20.
［７］Ｒ３が−Ｏ−である、［１］項に記載のケイ素化合物。 [7] The silicon compound according to item [1], wherein R 3 is —O—.
［８］Ｒ０のすべてがフェニル、シクロペンチルおよびシクロヘキシルから選択される同一の基であり、Ｒ１およびＲ２が独立してフェニルまたはメチルであり、そしてＲ３が−Ｏ−である、［１］項に記載のケイ素化合物。 [8] All of R 0 are the same group selected from phenyl, cyclopentyl and cyclohexyl, R 1 and R 2 are independently phenyl or methyl, and R 3 is —O—. ] The silicon compound of a term.
［９］Ｒ０のすべてがフェニルであり、Ｒ１およびＲ２が独立してフェニルまたはメチルであり、そしてＲ３が−Ｏ−である、［１］項に記載のケイ素化合物。 [9] The silicon compound according to item [1], wherein all of R 0 are phenyl, R 1 and R 2 are independently phenyl or methyl, and R 3 is —O—.
［１０］［１］項に記載の式（１）において、ｍが１〜１０の整数であり、構成単位の繰り返し数が１以上である、［７］〜［９］のいずれか１項に記載のケイ素化合物。 [10] In any one of [7] to [9], in the formula (1) according to the item [1], m is an integer of 1 to 10 and the number of repeating structural units is 1 or more. The silicon compound described.
［１１］［１］項に記載の式（１）において、ｍが１〜３の整数であり、構成単位の繰り返し数が２〜１００である、［７］〜［９］のいずれか１項に記載のケイ素化合物。 [11] In any one of [7] to [9], in the formula (1) described in the item [1], m is an integer of 1 to 3, and the number of repeating structural units is 2 to 100. The silicon compound as described in.
［１２］［１］項に記載の式（１）において、ｍが１〜３の整数であり、構成単位の繰り返し数が２〜２０である、［７］〜［９］のいずれか１項に記載のケイ素化合物。 [12] In any one of [7] to [9], in the formula (1) according to the item [1], m is an integer of 1 to 3, and the number of repeating structural units is 2 to 20. The silicon compound as described in.
本発明により、Ｔ８Ｄ２構造またはその類似構造を有するＰＳＱ骨格を主鎖に含み、熱可塑性を有する重合体が提供される。本発明の重合体は、透明性、皮膜形成性などに優れていて、フィルム、シートおよび成形体として使用することができる。 According to the present invention, a polymer having a PSQ skeleton having a T8D2 structure or a similar structure in the main chain and having thermoplasticity is provided. The polymer of the present invention is excellent in transparency, film-forming property and the like, and can be used as a film, a sheet and a molded body.
以下の説明においては、式（１）で示される構成単位を有するケイ素化合物を化合物（１）と表記することがある。式（２）で示される化合物を化合物（２）と表記することがある。他の式で示される化合物についても、同様の方法で簡略化して表記することがある。「シルセスキオキサン」を記号「ＰＳＱ」で表記することがある。従って、「シルセスキオキサン誘導体」は「ＰＳＱ誘導体」と表記される。そして、化合物（１）はＰＳＱ誘導体であり、更には主鎖にＰＳＱ骨格を有する重合体である。以下、本発明をさらに詳しく説明する。 In the following description, a silicon compound having a structural unit represented by formula (1) may be referred to as compound (1). A compound represented by the formula (2) may be referred to as a compound (2). The compounds represented by other formulas may be expressed in a simplified manner in the same manner. “Silsesquioxane” may be represented by the symbol “PSQ”. Therefore, “silsesquioxane derivative” is expressed as “PSQ derivative”. Compound (1) is a PSQ derivative, and further a polymer having a PSQ skeleton in the main chain. Hereinafter, the present invention will be described in more detail.
式（１）におけるＲ０は、任意の水素がハロゲンまたは炭素数１〜２０のアルキルで置き換えられてもよいアリール、またはシクロアルキルである。ハロゲンの好ましい例は、フッ素、塩素および臭素である。炭素数１〜２０のアルキルにおいて、任意の水素はフッ素で置き換えられてもよく、任意の−ＣＨ２−は−Ｏ−、シクロアルキレンまたはフェニレンで置き換えられてもよい。Ｒ０の好ましい例は、任意の水素がハロゲンまたは炭素数１〜８のアルキルで置き換えられてもよいフェニル、非置換のナフチル、シクロペンチルおよびシクロヘキシルである。このとき、フェニルの置換基である炭素数１〜８のアルキルにおいて、任意の水素はフッ素で置き換えられてもよく、任意の−ＣＨ２−は−Ｏ−またはフェニレンで置き換えられてもよい。Ｒ０のより好ましい例は、フェニル、アルキルフェニル、アルキルオキシフェニル、フェニルを含む置換基を有するフェニル、ナフチル、シクロペンチルおよびシクロヘキシルである。このとき、フェニル、アルキルフェニル、アルキルオキシフェニルおよびフェニルを含む置換基を有するフェニルにおいては、任意の水素がハロゲンで置き換えられてもよい。そして、Ｒ０の更に好ましい例は、フェニル、シクロペンチルおよびシクロヘキシルである。 R 0 in Formula (1) is aryl in which arbitrary hydrogen may be replaced by halogen or alkyl having 1 to 20 carbons, or cycloalkyl. Preferred examples of halogen are fluorine, chlorine and bromine. In the alkyl having 1 to 20 carbon atoms, arbitrary hydrogen may be replaced with fluorine, and arbitrary —CH 2 — may be replaced with —O—, cycloalkylene, or phenylene. Preferred examples of R 0 are phenyl, unsubstituted naphthyl, cyclopentyl and cyclohexyl in which any hydrogen may be replaced by halogen or alkyl having 1 to 8 carbons. In this case, in the alkyl having 1 to 8 carbon atoms which is a phenyl substituent, arbitrary hydrogen may be replaced with fluorine, and arbitrary —CH 2 — may be replaced with —O— or phenylene. More preferred examples of R 0 are phenyl, alkylphenyl, alkyloxyphenyl, phenyl having a substituent containing phenyl, naphthyl, cyclopentyl and cyclohexyl. At this time, in the phenyl having a substituent including phenyl, alkylphenyl, alkyloxyphenyl and phenyl, any hydrogen may be replaced with a halogen. Further preferred examples of R 0 are phenyl, cyclopentyl and cyclohexyl.
ハロゲン化フェニルの例は、ペンタフルオロフェニル、４−クロロフェニルおよび４−ブロモフェニルである。アルキルフェニルの例は、４−メチルフェニル、４−エチルフェニル、４−プロピルフェニル、４−ブチルフェニル、４−ペンチルフェニル、４−ヘプチルフェニル、４−オクチルフェニル、４−ノニルフェニル、４−デシルフェニル、２，４−ジメチルフェニル、２，４，６−トリメチルフェニル、２，４，６−トリエチルフェニル、４−（１−メチルエチル）フェニル、４−（１，１−ジメチルエチル）フェニル、４−（２−エチルヘキシル）フェニルおよび２，４，６−トリス（１−メチルエチル）フェニルである。アルキルオキシフェニルの例は、４−メトキシフェニル、４−エトキシフェニル、４−プロポキシフェニル、４−ブトキシフェニル、４−ペンチルオキシフェニル、４−ヘプチルオキシフェニル、４−デシルオキシフェニル、４−オクタデシルオキシフェニル、４−（１−メチルエトキシ）フェニル、４−（２−メチルプロポキシ）フェニル、４−（１，１−ジメチルエトキシ）フェニルなどである。フェニルを含む置換基を有するフェニルの例は、４−フェニルオキシフェニル、３−フェニルメチルフェニル、ビフェニルおよびターフェニルである。 Examples of halogenated phenyl are pentafluorophenyl, 4-chlorophenyl and 4-bromophenyl. Examples of alkylphenyl are 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-butylphenyl, 4-pentylphenyl, 4-heptylphenyl, 4-octylphenyl, 4-nonylphenyl, 4-decylphenyl. 2,4-dimethylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triethylphenyl, 4- (1-methylethyl) phenyl, 4- (1,1-dimethylethyl) phenyl, 4- (2-ethylhexyl) phenyl and 2,4,6-tris (1-methylethyl) phenyl. Examples of alkyloxyphenyl are 4-methoxyphenyl, 4-ethoxyphenyl, 4-propoxyphenyl, 4-butoxyphenyl, 4-pentyloxyphenyl, 4-heptyloxyphenyl, 4-decyloxyphenyl, 4-octadecyloxyphenyl 4- (1-methylethoxy) phenyl, 4- (2-methylpropoxy) phenyl, 4- (1,1-dimethylethoxy) phenyl, and the like. Examples of phenyl having substituents including phenyl are 4-phenyloxyphenyl, 3-phenylmethylphenyl, biphenyl and terphenyl.
ベンゼン環の水素の一部がハロゲンで置き換えられ、さらに他の水素がアルキルまたはアルキルオキシで置き換えられたフェニルの例は、３−クロロ−４−メチルフェニル、２，５−ジクロロ−４−メチルフェニル、３，５−ジクロロ−４−メチルフェニル、２，３，５−トリクロロ−４−メチルフェニル、２，３，６−トリクロロ−４−メチルフェニル、３−ブロモ−４−メチルフェニル、２，５−ジブロモ−４−メチルフェニル、３，５−ジブロモ−４−メチルフェニル、２，３−ジフルオロ−４−メチルフェニル、３−クロロ−４−メトキシフェニル、３−ブロモ−４−メトキシフェニル、３，５−ジブロモ−４−メトキシフェニル、２，３−ジフルオロ−４−メトキシフェニル、２，３−ジフルオロ−４−エトキシフェニルおよび２，３−ジフルオロ−４−プロポキシフェニルである。 Examples of phenyl in which a part of hydrogen on the benzene ring is replaced by halogen and another hydrogen is replaced by alkyl or alkyloxy are 3-chloro-4-methylphenyl, 2,5-dichloro-4-methylphenyl 3,5-dichloro-4-methylphenyl, 2,3,5-trichloro-4-methylphenyl, 2,3,6-trichloro-4-methylphenyl, 3-bromo-4-methylphenyl, 2,5 -Dibromo-4-methylphenyl, 3,5-dibromo-4-methylphenyl, 2,3-difluoro-4-methylphenyl, 3-chloro-4-methoxyphenyl, 3-bromo-4-methoxyphenyl, 3, 5-dibromo-4-methoxyphenyl, 2,3-difluoro-4-methoxyphenyl, 2,3-difluoro-4-ethoxyphenyl and 2 3-difluoro-4-propoxy-phenyl.
Ｒ１またはＲ２がアルキルであるとき、その炭素数は１〜４０である。好ましい炭素数は１〜２０である。より好ましい炭素数は１〜８である。そして、その任意の水素はフッ素で置き換えられてもよく、任意の−ＣＨ２−は−Ｏ−またはシクロアルキレンで置き換えられてもよい。アルキルの好ましい例は、炭素数１〜２０の非置換のアルキル、炭素数２〜２０のアルコキシアルキル、炭素数１〜８のアルキルにおいて１個の−ＣＨ２−がシクロアルキレンで置き換えられた基、およびここに列挙したそれぞれの基において任意の水素がフッ素で置き換えられた基である。シクロアルキレンの好ましい炭素数は３〜８であり、５または６がより好ましい。そして、このシクロアルキレンにおいては、隣り合わない２つの炭素原子が架橋されてもよい。 When R 1 or R 2 is alkyl, the carbon number is 1-40. A preferable carbon number is 1-20. A more preferable carbon number is 1-8. Any hydrogen may be replaced with fluorine, and any —CH 2 — may be replaced with —O— or cycloalkylene. Preferred examples of alkyl include unsubstituted alkyl having 1 to 20 carbons, alkoxyalkyl having 2 to 20 carbons, and a group in which one —CH 2 — is substituted with cycloalkylene in alkyl having 1 to 8 carbons, And in each of the groups listed here, any hydrogen is replaced by fluorine. The preferable carbon number of cycloalkylene is 3-8, and 5 or 6 is more preferable. And in this cycloalkylene, two carbon atoms which are not adjacent may be bridged.
炭素数１〜２０の非置換のアルキルの例は、メチル、エチル、プロピル、１−メチルエチル、ブチル、２−メチルプロピル、１，１−ジメチルエチル、ペンチル、ヘキシル、１，１，２−トリメチルプロピル、ヘプチル、オクチル、２，４，４−トリメチルペンチル、ノニル、デシル、ウンデシル、ドデシル、テトラデシル、ヘキサデシル、オクタデシルおよびエイコシルである。炭素数１〜２０のフッ素化アルキルの例は、３，３，３−トリフルオロプロピル、３，３，４，４，５，５，６，６，６−ノナデカフルオロヘキシル、トリデカフルオロ−１，１，２，２−テトラヒドロオクチル、ヘプタデカフルオロ−１，１，２，２−テトラヒドロデシル、パーフルオロ−１Ｈ，１Ｈ，２Ｈ，２Ｈ−ドデシルおよびパーフルオロ−１Ｈ，１Ｈ，２Ｈ，２Ｈ−テトラデシルである。炭素数２〜２０のアルコキシアルキルの例は、３−メトキシプロピル、メトキシエトキシウンデシルおよび３−ヘプタフルオロイソプロポキシプロピルである。炭素数１〜８のアルキルにおいて１個の−ＣＨ２−がシクロアルキレンで置き換えられた基の例は、シクロペンチル、シクロヘキシル、シクロヘキシルメチル、アダマンタンエチル、２−ビシクロヘプチルおよびシクロオクチルである。シクロヘキシルは、メチルの−ＣＨ２−がシクロへキシレンで置き換えられた例である。シクロヘキシルメチルは、エチルの−ＣＨ２−がシクロへキシレンで置き換えられた例である。 Examples of unsubstituted alkyl having 1 to 20 carbon atoms are methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, hexyl, 1,1,2-trimethyl. Propyl, heptyl, octyl, 2,4,4-trimethylpentyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and eicosyl. Examples of fluorinated alkyls having 1 to 20 carbon atoms are 3,3,3-trifluoropropyl, 3,3,4,4,5,5,6,6,6-nonadecafluorohexyl, tridecafluoro- 1,1,2,2-tetrahydrooctyl, heptadecafluoro-1,1,2,2-tetrahydrodecyl, perfluoro-1H, 1H, 2H, 2H-dodecyl and perfluoro-1H, 1H, 2H, 2H- Tetradecyl. Examples of C2-C20 alkoxyalkyl are 3-methoxypropyl, methoxyethoxyundecyl and 3-heptafluoroisopropoxypropyl. Examples of groups in which one —CH 2 — in C 1-8 alkyl is replaced by cycloalkylene are cyclopentyl, cyclohexyl, cyclohexylmethyl, adamantaneethyl, 2-bicycloheptyl and cyclooctyl. Cyclohexyl is an example in which methyl —CH 2 — is replaced by cyclohexylene. Cyclohexylmethyl is an example in which —CH 2 — in ethyl is replaced by cyclohexylene.
Ｒ１またはＲ２が任意の水素がハロゲンまたは炭素数１〜２０のアルキルで置き換えられてもよいアリールであるとき、その好ましい例はＲ０の好ましい例と同じである。Ｒ１またはＲ２は、任意の水素がハロゲンまたは炭素数１〜２０のアルキルで置き換えられてもよいアリールと炭素数１〜１０のアルキレンとで構成されるアリールアルキルであってもよい。アリールの置換基である炭素数１〜２０のアルキルにおいて、任意の水素はフッ素で置き換えられてもよく、任意の−ＣＨ２−は−Ｏ−、シクロアルキレンまたはフェニレンで置き換えられてもよい。アルキレンにおいては、任意の水素はフッ素で置き換えられてもよく、そして任意の−ＣＨ２−は−Ｏ−、−ＣＨ＝ＣＨ−またはシクロアルキレンで置き換えられてもよい。このようなアリールアルキルの好ましい例は、フェニルと炭素数１〜４のアルキレンとで構成されるフェニルアルキルである。このとき、フェニルの任意の水素はメチル、メトキシまたはフッ素で置き換えられてもよく、アルキレンにおけるフェニルに結合する−ＣＨ２−は−Ｏ−で置き換えられてもよい。 When R 1 or R 2 is aryl in which any hydrogen may be replaced by halogen or alkyl having 1 to 20 carbons, preferred examples thereof are the same as the preferred examples of R 0 . R 1 or R 2 may be an arylalkyl composed of aryl in which arbitrary hydrogen may be replaced by halogen or alkyl having 1 to 20 carbons and alkylene having 1 to 10 carbons. In the alkyl having 1 to 20 carbon atoms as the aryl substituent, any hydrogen may be replaced with fluorine, and any —CH 2 — may be replaced with —O—, cycloalkylene, or phenylene. In alkylene, any hydrogen may be replaced with fluorine, and any —CH 2 — may be replaced with —O—, —CH═CH—, or cycloalkylene. A preferred example of such arylalkyl is phenylalkyl composed of phenyl and alkylene having 1 to 4 carbon atoms. At this time, any hydrogen of phenyl may be replaced with methyl, methoxy or fluorine, and —CH 2 — bonded to phenyl in alkylene may be replaced with —O—.
Ｒ１またはＲ２のより好ましい例は、フェニル、ハロゲン化フェニル、少なくとも１つのメチルを有するフェニル、メトキシフェニル、ナフチル、フェニルメチル、フェニルエチル、フェニルブチル、２−フェニルプロピル、１−メチル−２−フェニルエチル、ペンタフルオロフェニルプロピル、４−エチルフェニルエチル、３−エチルフェニルエチル、４−（１，１−ジメチルエチル）フェニルエチル、４−メトキシフェニルプロピル、フェノキシプロピル、シクロペンチルおよびシクロヘキシルである。そして、Ｒ１またはＲ２の更に好ましい例は、フェニル、シクロペンチルおよびシクロヘキシルである。
である。
More preferred examples of R 1 or R 2 are phenyl, phenyl halide, phenyl having at least one methyl, methoxyphenyl, naphthyl, phenylmethyl, phenylethyl, phenylbutyl, 2-phenylpropyl, 1-methyl-2- Phenylethyl, pentafluorophenylpropyl, 4-ethylphenylethyl, 3-ethylphenylethyl, 4- (1,1-dimethylethyl) phenylethyl, 4-methoxyphenylpropyl, phenoxypropyl, cyclopentyl and cyclohexyl. And more preferred examples of R 1 or R 2 are phenyl, cyclopentyl and cyclohexyl.
It is.
式（１）におけるｍは１〜３０の整数である。好ましいｍは１〜１０であり、より好ましいｍは１〜３である。最も好ましいｍは１である。そして、本発明のケイ素化合物における式（１）で示される構成単位の繰り返し数は１以上である。好ましい繰り返し数は２〜１００であり、より好ましい繰り返し数は２〜２０である。
式（１）における好ましいＲ３は、本発明のケイ素化合物の主鎖が全てＳｉおよびＯから構成されることから、−Ｏ−である。
M in Formula (1) is an integer of 1-30. Preferred m is 1 to 10, and more preferred m is 1 to 3. Most preferably m is 1. And the repeating number of the structural unit shown by Formula (1) in the silicon compound of this invention is one or more. A preferable repeating number is 2 to 100, and a more preferable repeating number is 2 to 20.
Preferred R 3 in the formula (1) is —O— because the main chain of the silicon compound of the present invention is entirely composed of Si and O.
化合物（１）は、化合物（２）と化合物（３）とを反応させることにより得ることができる。
本発明で用いる化合物（２）は、例えば、化合物（４）と化合物（５）とを反応させることにより得ることができる。
化合物（５）の代わりに化合物（６）を用いても化合物（２）を合成することができる。但し、このときは架橋反応によるオリゴマー化が起きないように注意が必要である。そして、Ｘが塩素である化合物（２）が得られるので、Ｚが−ＯＨである化合物（３）を入手できない場合には、これを加水分解して−ＯＨに変える必要がある。
そして、化合物（４）は、例えば、式（７）で表される化合物を１価のアルカリ金属水酸化物および水の存在下、有機溶剤の存在下もしくは不存在下で加水分解、縮重合することにより製造することができる。１価のアルカリ金属水酸化物の例は、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウムである。これらのうち、水酸化ナトリウムおよび水酸化カリウムが好ましい。１価のアルカリ金属水酸化物の使用量は、前記のシラン化合物に対するモル比で、０．３〜１．５である。より好ましいモル比は０．４〜０．８である。そして、添加する水の量は、シラン化合物に対するモル比で１．０〜１．５である。より好ましいモル比は１．１〜１．３である。有機溶剤の好ましい例は直鎖状、分岐状または環状の１価のアルコールである。アルコールは縮合過程での構造制御に寄与すると推定される。
反応に用いる溶剤は、反応の進行を阻害しないものであれば特に制限されない。好ましい溶剤の例は、ヘキサンやヘプタンなどの炭化水素系溶剤、ベンゼン、トルエン、キシレンなどの芳香族炭化水素系溶剤、ジエチルエーテル、テトラハイドロフラン（ＴＨＦ）、ジオキサンなどのエーテル系溶剤、塩化メチレン、四塩化炭素などのハロゲン化炭化水素系溶剤、および酢酸エチルなどのエステル系溶剤である。これらの溶剤は単独で使用しても、その複数を組み合わせて使用してもよい。これらの溶剤の中でも、芳香族炭化水素系溶剤、その中でもトルエンが最も好ましい。溶剤は必ずしも必要ではないが、使用する場合には、溶剤に対する原料の好ましい割合は、溶剤の重量に基づいて０．０５〜８０重量％である。より好ましい割合は３０〜７０重量％である。割合は目的によって異なる。ヒドロシリル化反応を用いる場合はヒドロシリル化反応が阻害されることなく進行すれば、原料の重量と得られる反応生成物の重量とにほとんど差がない。従って、この割合は溶剤に対する反応生成物の重量％と同じである。 The solvent used for the reaction is not particularly limited as long as it does not inhibit the progress of the reaction. Examples of preferred solvents include hydrocarbon solvents such as hexane and heptane, aromatic hydrocarbon solvents such as benzene, toluene and xylene, ether solvents such as diethyl ether, tetrahydrofuran (THF) and dioxane, methylene chloride, Halogenated hydrocarbon solvents such as carbon tetrachloride, and ester solvents such as ethyl acetate. These solvents may be used alone or in combination. Of these solvents, aromatic hydrocarbon solvents, and toluene is most preferred. Although a solvent is not necessarily required, when used, a preferable ratio of the raw material to the solvent is 0.05 to 80% by weight based on the weight of the solvent. A more desirable ratio is 30 to 70% by weight. The proportion depends on the purpose. When the hydrosilylation reaction is used, if the hydrosilylation reaction proceeds without being inhibited, there is almost no difference between the weight of the raw material and the weight of the reaction product obtained. This proportion is therefore the same as the weight percent of the reaction product relative to the solvent.
反応は室温で実施してもよい。反応を促進させるために加熱してもよい。反応による発熱または好ましくない反応を制御するために冷却してもよい。必要に応じて触媒を用いることができる。ヒドロシリル化反応では、ヒドロシリル化触媒を添加することによって、反応をより容易に進行させることができる。好ましいヒドロシリル化触媒の例は、カルステッド（Karstedt）触媒、スパイヤー（Spier）触媒、ヘキサクロロプラチニック酸などであり、これらは一般的によく知られた触媒である。これらのヒドロシリル化触媒は、反応性が高いので少量添加すれば十分反応を進めることができる。その使用量は、触媒に含まれる遷移金属のヒドロシリル基に対する割合で、１０−９〜１モル％である。好ましい添加割合は１０−７〜１０−３モル％である。１０−９モル％は、重合を進行させることができ、容認できる時間内で終了させるために必要な添加割合の下限である。製造コストを低く抑えることを考慮すれば、この割合の好ましい上限は１モル％である。 The reaction may be carried out at room temperature. Heating may be used to promote the reaction. Cooling may be used to control the exotherm or undesired reaction. A catalyst can be used as needed. In the hydrosilylation reaction, the reaction can be allowed to proceed more easily by adding a hydrosilylation catalyst. Examples of preferred hydrosilylation catalysts are Karstedt catalyst, Spier catalyst, hexachloroplatinic acid and the like, which are generally well known catalysts. Since these hydrosilylation catalysts have high reactivity, the reaction can proceed sufficiently if added in a small amount. The amount used is 10 −9 to 1 mol% in terms of the ratio of the transition metal contained in the catalyst to the hydrosilyl group. A preferable addition ratio is 10 −7 to 10 −3 mol%. 10 −9 mol% is the lower limit of the addition ratio required to allow the polymerization to proceed and to complete within an acceptable time. Considering keeping the production cost low, the preferable upper limit of this ratio is 1 mol%.
かご型構造の骨格を主鎖に導入することによって得られる本発明の重合体は、主鎖の動きが制限されること等により剛直性が付与され、耐熱性や物理的強度が高くなると予測される。その構造の特異性から高い光学透過性が期待できる。本発明の重合体は、溶解性、耐熱性、機械強度、光学透過性、ガス透過性、誘電率、難燃性、接着性、加工性等の優れた効果を期待できるので、幅広い用途に利用できる。電気・電子材料としての用途の例は、金属溶出防止膜、ガスバリア膜、反射防止膜等の基板用コーティング剤、液状封止剤、層間絶縁膜等の半導体用コーティング剤、マイクロレンズ、導光板、光導波路材料等の光学素子、ディスプレイ基板およびプリント配線用基板等である。必要に応じ、初期の性状を損なわない範囲で、重合体への他の成分、例えば、酸化防止剤、着色剤、充填剤等をブレンドして使用してもよい。 The polymer of the present invention obtained by introducing a skeleton having a cage structure into the main chain is expected to have rigidity and high heat resistance and physical strength due to the movement of the main chain being restricted. The High optical transparency can be expected from the specificity of the structure. The polymer of the present invention can be expected to have excellent effects such as solubility, heat resistance, mechanical strength, optical permeability, gas permeability, dielectric constant, flame retardancy, adhesiveness, workability, etc. it can. Examples of applications as electrical / electronic materials include coating agents for substrates such as metal elution prevention films, gas barrier films, and antireflection films, liquid sealants, semiconductor coating agents such as interlayer insulation films, microlenses, light guide plates, Optical elements such as optical waveguide materials, display substrates, printed wiring boards, and the like. If necessary, other components such as an antioxidant, a colorant, a filler and the like may be blended and used in the polymer as long as the initial properties are not impaired.
実施例により本発明を更に具体的に説明するが、本発明は以下の実施例によって制限されない。なお、実施例における化学式において、Ｍｅはメチルであり、Ｐｈはフェニルである。 The present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples. In the chemical formulas in the examples, Me is methyl and Ph is phenyl.
化合物（８）（１．８ｇ）と化合物（９）（０．２ｇ）をトルエン（１０ｍｌ）に溶解した。この溶液を７０℃まで加熱した後、カルステッド触媒（１μｌ）を添加して同温度で３時間攪拌した。得られた反応液における重合体の分子量をＧＰＣにより測定したところ、数平均分子量（Ｍｎ）＝１７，１００、重量平均分子量（Ｍｗ）＝１０３，５００であった。この反応液をガラス板上に滴下し、トルエンを蒸発させて、ガラス面に接着した平滑で透明な皮膜を得た。反応液からトルエンを蒸発させ得られた白色粉末のうち０．３ｇを直径５ｍｍのチューブ中に入れ８０℃に加熱し、３０分間保持したのち５，０００ｒｐｍで１５分間回転させることによりチューブ状の成型体を得た。
装置：日本分光株式会社製、JASCO GULLIVER 1500 (インテリジェント示差屈折率計 RI-1530)
カラム：東ソー製カラムＧ４０００ＨＸＬ、Ｇ３０００ＨＸＬ、Ｇ２５００ＨＸＬおよびＧ２０００ＨＸＬの４本を、この順序に接続して使用した。
カラム温度：４０℃
展開溶剤：ＴＨＦ
流量：１．０ｍｌ／ｍｉｎ
標準物質：分子量既知のポリスチレン．
Compound (8) (1.8 g) and compound (9) (0.2 g) were dissolved in toluene (10 ml). After this solution was heated to 70 ° C., a Calsted catalyst (1 μl) was added and stirred at the same temperature for 3 hours. When the molecular weight of the polymer in the obtained reaction solution was measured by GPC, the number average molecular weight (Mn) was 17,100 and the weight average molecular weight (Mw) was 103,500. This reaction solution was dropped on a glass plate, and toluene was evaporated to obtain a smooth and transparent film adhered to the glass surface. 0.3 g of the white powder obtained by evaporating toluene from the reaction solution was placed in a tube with a diameter of 5 mm, heated to 80 ° C., held for 30 minutes, and then rotated at 5,000 rpm for 15 minutes to form a tube. Got the body.
Apparatus: JASCO GULLIVER 1500 (intelligent differential refractometer RI-1530) manufactured by JASCO Corporation
Columns: Tosoh columns G4000HXL, G3000HXL, G2500HXL and G2000HXL were connected in this order and used.
Column temperature: 40 ° C
Developing solvent: THF
Flow rate: 1.0 ml / min
Standard substance: polystyrene with known molecular weight.
式（１０）で示される化合物（０．６ｇ）を脱水トルエン（２０ｍｌ）に溶解し、トリエチルアミン（０．４２ｍｌ）を加えたのちに３０分氷浴し冷却した。この溶液に１，３−ジクロロテトラメチルジシロキサン（０．１０ｍｌ）を加え室温で１日撹拌したのち、さらに１，３−ジクロロテトラメチルジシロキサン（０．１０ｍｌ）を加え、室温で７日間撹拌した。こののち、沈殿物をろ過により除き、得られたろ液を水層が中性になるまで水洗した。水洗したろ液にＭｇＳＯ４を加えて水分を除去したのち、有機層を濃縮した。得られた濃縮物をヘキサンを用いて洗浄したのち、沈殿物を乾燥し、０．２６ｇのロウ状物質を得た。さらにヘキサンを用いて洗浄と再沈殿を行い０．１６ｇのロウ状物質を得た。得られたロウ状物質の分子量を測定したところ、Ｍｎ＝２１，０００、Ｍｗ＝２１０，０００であった。
装置：Waters 996 Potodiod Detecter Array
カラム：Ｓｈｏｄｅｘ ＫＦ８０６Ｍ ３００Ｘ８．０ｍｍ
移動相：ＴＨＦ
流速：１．０ｍｌ／ｍｉｎ
温度：３５℃
分子量標準サンプル：分子量既知のポリスチレン
The compound represented by the formula (10) (0.6 g) was dissolved in dehydrated toluene (20 ml), triethylamine (0.42 ml) was added, and the mixture was cooled in an ice bath for 30 minutes. 1,3-Dichlorotetramethyldisiloxane (0.10 ml) was added to this solution and stirred at room temperature for 1 day. Then, 1,3-dichlorotetramethyldisiloxane (0.10 ml) was further added and stirred at room temperature for 7 days. did. Thereafter, the precipitate was removed by filtration, and the obtained filtrate was washed with water until the aqueous layer became neutral. After removing water by adding MgSO 4 to the filtrate washed with water, the organic layer was concentrated. The obtained concentrate was washed with hexane, and then the precipitate was dried to obtain 0.26 g of a waxy substance. Further, washing and reprecipitation were carried out using hexane to obtain 0.16 g of a waxy substance. When the molecular weight of the obtained waxy substance was measured, it was Mn = 21,000 and Mw = 210,000.
Equipment: Waters 996 Potodiod Detecter Array
Column: Shodex KF806M 300X8.0mm
Mobile phase: THF
Flow rate: 1.0 ml / min
Temperature: 35 ° C
Molecular weight standard sample: polystyrene with known molecular weight
式（１１）で示される化合物（１．３１ｇ）を脱水トルエン（３０ｍｌ）に溶解し、トリエチルアミン（０．４２ｍｌ）および１，３−ジクロロテトラメチルジシロキサン（０．２０ｍｌ）を加えて室温で１日撹拌した。このちさらに１，３−ジクロロテトラメチルジシロキサン（０．１０ｍｌ）を加え、室温で１日撹拌した。この後、沈殿物をろ過により除いたのち、得られたろ液を水層が中性になるまで水洗した。水洗したろ液にＭｇＳＯ４を加えて水分を除去した後、有機層を乾燥して白色固体０．８５４ｇを得た。この白色固体をヘキサンで洗浄した後乾燥させ、０．８０５ｇの白色固体を得、さらに再沈殿を行うことにより目的物の白色固体０．１４ｇを得た。得られた白色固体の分子量を測定したところＭｎ＝４，２００，Ｍｗ＝８，０００であった。分子量の測定は実施例２と同じ条件で行った。
表１に示した化合物（２）と化合物（３）を用いて、実施例２または３と同様の方法により化合物（１）を合成し、それぞれの分子量と転移温度を測定した。結果は表１に示すとおりであった。
＜表１＞
<Table 1>
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