CN106866722B - 一种含苯并环丁烯官能化的有机硅化合物及其制备方法 - Google Patents
一种含苯并环丁烯官能化的有机硅化合物及其制备方法 Download PDFInfo
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- CN106866722B CN106866722B CN201710019153.4A CN201710019153A CN106866722B CN 106866722 B CN106866722 B CN 106866722B CN 201710019153 A CN201710019153 A CN 201710019153A CN 106866722 B CN106866722 B CN 106866722B
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- benzocyclobutene
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- compound containing
- organic silicon
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- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 7
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 238000004100 electronic packaging Methods 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims abstract description 3
- 238000004528 spin coating Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- -1 organic compound salt Chemical class 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000002894 organic compounds Chemical class 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002390 rotary evaporation Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000012686 silicon precursor Substances 0.000 claims description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- AUKWRHADVIQZRJ-UHFFFAOYSA-N adamantane-1,4-diol Chemical group C1C(C2)CC3C(O)C1CC2(O)C3 AUKWRHADVIQZRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- ICLZNGAELWYHKL-CAPFRKAQSA-N (E)-3-[5-[5-[4-(N-phenylanilino)phenyl]thiophen-2-yl]thiophen-2-yl]prop-2-enoic acid Chemical compound OC(=O)\C=C\c1ccc(s1)-c1ccc(s1)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 ICLZNGAELWYHKL-CAPFRKAQSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000002981 blocking agent Substances 0.000 claims 1
- 125000004355 nitrogen functional group Chemical group 0.000 claims 1
- 239000005022 packaging material Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000002861 polymer material Substances 0.000 abstract description 4
- 239000003504 photosensitizing agent Substances 0.000 abstract description 3
- 238000007306 functionalization reaction Methods 0.000 abstract description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 238000011417 postcuring Methods 0.000 abstract description 2
- 150000001540 azides Chemical class 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000005046 Chlorosilane Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000007341 Heck reaction Methods 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- YBNBOGKRCOCJHH-UHFFFAOYSA-N hydroxy-[4-[hydroxy(dimethyl)silyl]phenyl]-dimethylsilane Chemical compound C[Si](C)(O)C1=CC=C([Si](C)(C)O)C=C1 YBNBOGKRCOCJHH-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- RVIZJROSQMQZCG-UHFFFAOYSA-N adamantane-1,2-diol Chemical group C1C(C2)CC3CC1C(O)C2(O)C3 RVIZJROSQMQZCG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000805 composite resin Substances 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- KTPJNXMWWFGEMB-UHFFFAOYSA-N hydroxy-[4-[hydroxy(dimethyl)silyl]-1-phenylcyclohexa-2,4-dien-1-yl]-dimethylsilane Chemical group C[Si](C)(C1=CCC(C=C1)(C2=CC=CC=C2)[Si](C)(C)O)O KTPJNXMWWFGEMB-UHFFFAOYSA-N 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- MLIWQXBKMZNZNF-PWDIZTEBSA-N (2e,6e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)C\C1=C/C1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-PWDIZTEBSA-N 0.000 description 1
- IGWSIIBEBKJTKR-UHFFFAOYSA-N 2,4,6,8-tetrachloro-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound Cl[SiH]1O[SiH](O[SiH](O[SiH](O1)Cl)Cl)Cl IGWSIIBEBKJTKR-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical class CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 1
- GMHHTGYHERDNLO-UHFFFAOYSA-N 4-bromobicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound BrC1=CC=C2CCC2=C1 GMHHTGYHERDNLO-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ODYNJSYEGZCCEP-UHFFFAOYSA-N C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)[SiH](O[SiH2]O)O Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)[SiH](O[SiH2]O)O ODYNJSYEGZCCEP-UHFFFAOYSA-N 0.000 description 1
- MWSSEOQESHQYNR-UHFFFAOYSA-N C1(=CC=CC=C1)[SiH]1[SiH]=[SiH]C=C1 Chemical compound C1(=CC=CC=C1)[SiH]1[SiH]=[SiH]C=C1 MWSSEOQESHQYNR-UHFFFAOYSA-N 0.000 description 1
- NDKBSLOMSLZZBG-UHFFFAOYSA-N C1CC=2C1=CC=CC2.BrC2=CC=CC=C2 Chemical compound C1CC=2C1=CC=CC2.BrC2=CC=CC=C2 NDKBSLOMSLZZBG-UHFFFAOYSA-N 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QMSHNOSTJCZXMU-UHFFFAOYSA-N [Li].C1CC=2C1=CC=CC2 Chemical compound [Li].C1CC=2C1=CC=CC2 QMSHNOSTJCZXMU-UHFFFAOYSA-N 0.000 description 1
- ICQPGUZILLEXRE-UHFFFAOYSA-N [SiH3]O.[Li] Chemical compound [SiH3]O.[Li] ICQPGUZILLEXRE-UHFFFAOYSA-N 0.000 description 1
- IPRVKUPKUIJURA-UHFFFAOYSA-N adamantane-1,2,2-triol Chemical compound C1C(C2)CC3CC1C(O)(O)C2(O)C3 IPRVKUPKUIJURA-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DITWCTLKOLJYFI-UHFFFAOYSA-N hydroxy-[4-[4-[hydroxy(dimethyl)silyl]phenyl]phenyl]-dimethylsilane Chemical group C1=CC([Si](C)(O)C)=CC=C1C1=CC=C([Si](C)(C)O)C=C1 DITWCTLKOLJYFI-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000001955 polymer synthesis method Methods 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明属于聚合物材料技术领域,具体为含苯并环丁烯官能化的有机硅化合物及其制备方法。本发明通过含苯并环丁烯有机硅前驱体在碱性条件下与含有羟基的底物反应制备得到含苯并环丁烯官能化的有机硅化合物,并可通过减压蒸馏或者柱色谱提纯。这种含苯并环丁烯官能团的有机硅化合物可用于聚合反应,可以通过在均三甲苯溶剂中于150~180℃下预聚得到一定分子量的预聚体,进一步通过旋涂、后固化制备薄膜;含双键的单体预聚体中也可以加入叠氮型光敏剂,用于制备光刻胶,可应用在电子封装、集成电路等领域。
Description
技术领域
本发明属于聚合物材料技术领域,具体涉及含苯并环丁烯官能化的有机硅化合物及其制备方法。
背景技术
苯并环丁烯是一种优秀的聚合物材料,苯并环丁烯单体加热后可发生开环聚合,生成高交联、低介电聚合物材料。由于苯并环丁烯官能团的引入通常是利用Heck反应等方法引入,需要钯贵金属催化剂,后处理较为繁琐。如陶氏化学公司开发的Cyclotene 系列苯并环丁烯树脂单体,其化学结构如下所示:
程元荣,孔令强,肖斐等人在专利(申请号201310750579.9)金刚烷基苯并环丁烯单体及其聚合物的合成方法一文中,披露了一系列含金刚烷结构的苯并环丁烯单体,其结构通式如下:
其是先将金刚烷醇化合物和含双键的氯硅烷反应,从而引入双键;再利用4-溴苯并环丁烯和双键进行Heck反应,从而实现苯并环丁烯的引入。
由于苯并环丁烯官能团的引入通常是利用Heck反应等方法引入,需要钯贵金属催化剂,后处理较为繁琐。
本城啓司、江口弘、山中一広等人在专利WO2012144481A1中披露了一种含有苯并环丁烯官能团的环状有机硅化合物及其合成方法。其合成路线如下所示:
其是先利用正丁基锂和4-溴苯并环丁烯反应生成苯并环丁烯锂盐,再和三乙烯三甲基环三硅烷反应生成含有苯并环丁烯和双键的硅醇锂盐;利用四甲基环四硅氧烷的氯化反应,生成四氯化的环四硅氧烷,再和含有苯并环丁烯和双键的硅醇锂盐反应制备。这个路线用到了正丁基锂试剂以及氯化反应,路线相对比较危险和复杂。
左晓彪等人利用含有苯并环丁烯官能团的有机硅和苯撑硅醇反应,生成了苯并环丁烯作为侧基的硅氧烷聚合物。
这种方法所需的原料尤其是硅氮烷需要经过多步合成,相对较为复杂。
发明内容
本发明的目的在于提供一种含苯并环丁烯官能团的有机硅化合物及其制备方法。
本发明提供的含苯并环丁烯官能团的有机硅化合物的制备方法,是以含苯并环丁烯有机硅前驱体作为封端剂,与含有羟基的有机化合物或者其形成的有机化合物盐的反应底物进行反应制备。即在溶剂存在下,通过碱催化剂催化发生水解,经自缩聚反应,制备含苯并环丁烯官能团的有机化合物;其中,反应温度为-30℃--100℃;反应在普通大气条件下进行,或者在氮气、氩气等惰性气体保护下进行;反应时间为1小时到12小时。反应结束后,反应溶液经过过滤、洗涤、有机溶剂萃取、干燥、旋转蒸发浓缩后,通过柱层析或者减压蒸馏或者重结晶等方法进行提纯,得到含苯并环丁烯官能团的有机硅化合物。
本发明中,所述含苯并环丁烯官能团的有机硅前驱体结构如下:
R1、R2可以是氢原子、脂肪烃基(如甲基、乙基、乙烯基、烯丙基,炔丙基等)、芳香烃基(如苯基、苯并环丁烯-4-基等);
R1、R2两个官能团可以是相同的,也可以是不同的;
R3为卤素、甲氧基、乙氧基、异丙氧基中的当中之一;
所述含苯并环丁烯官能团的有机硅前驱体的典型结构可以是下述之一种:
所述反应底物为含有多羟基的有机化合物,其结构式为:A(-OH)n,其中,OH为羟基,A为除去羟基的残基,n为整数大于等于2。
所述反应底物具体可以是异山梨醇、含多个羟基的金刚烷化合物如金刚烷二醇、金刚烷三醇等;也可以是含有羟基的有机硅化合物如硅烷(硅醇)、含羟基的硅油以及有机硅树脂,如二苯基硅二醇,苯基三硅醇,1,4-双(二甲基羟基硅基)苯,4,4’-双(二甲基羟基硅基)联苯、1,1,3,3-四苯基1,3-二羟基二硅氧烷、羟基硅油、含羟基的梯形聚苯基倍半硅氧烷、含硅醇的非闭合笼型倍半硅氧烷等。部分含硅醇的有机硅结构如下:
相应有机化合物的典型结构有:
相应有机化合物不包括:
其中,R1、R2如前所述;R4为苯基、甲基、乙基等。
碱催化所用的催化剂可以是四甲基氢氧化铵、四乙基氢氧化铵、氢氧化钠、氢氧化钾、氨水、吡啶、三乙胺、二乙胺、4-二甲胺基吡啶、咪唑、N-甲基咪唑、2-甲基-咪唑、含咪唑结构的盐、氧化钙等中的一种或者多种;所用的溶剂可以是四氢呋喃、乙醚、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺,2-甲基四氢呋喃、二氯甲烷、甲苯、丙酮、丁酮、环己酮、乙酸乙酯、乙酸丙酯、乙酸丁酯等溶剂一种或者多种混合溶剂中进行。
反应结束后,反应液可通过柱层析或者重结晶等方法进行提纯得到产物。
本发明制备的含苯并环丁烯官能团的有机硅化合物结构式(结构式1)如下:
(结构式1)。
R1、R2可以是氢原子、脂肪烃基(如甲基、乙基、乙烯基、烯丙基,炔丙基等)、芳香烃基(如苯基、苯并环丁烯-4-基等);
R1、R2两个官能团可以是相同的,也可以是不同的;
R1、R2也可以是连在一起的,其含苯并环丁烯官能团的有机硅化合物结构式如下:
(结构式2)。
本发明合成的苯并环丁烯官能化的有机化合物,可用于聚合物的制备。尤其是应用于太阳能电池、显示器件、LED、MEMS等电子器件或者光电器件的封装胶,也可用作光学器件或者光学薄膜材料,还可作为半导体、集成电路领域用的低介电层间介质材料、低介电光刻胶等应用。也可以用于高性能树脂复合材料的制备。
本发明合成的苯并环丁烯官能化的有机化合物用于聚合反应时,可以通过在均三甲苯溶剂中于150~180℃下预聚得到一定分子量的预聚体,可通过旋涂、后固化,制备的薄膜。含双键的单体预聚体中也可以加入含双叠氮官能团的光敏剂如2,6-二(4-叠氮苯亚甲基)-4甲基环己酮,用于光刻胶的制备。可应用在电子封装、集成电路等领域。
本发明旨在提供一种新方法合成苯并环丁烯官能化的有机化合物用于聚合物的制备。尤其是应用于太阳能电池、显示器件、LED、MEMS等电子器件或者光电器件的封装胶,也可用作光学器件或者光学薄膜材料,还可作为半导体、集成电路领域用的低介电层间介质材料、低介电光刻胶等应用。也可以用于高性能树脂复合材料的制备。
具体实施方式
下面通过具体实施例进一步描述本发明。
实施例1. 利用甲基乙烯基苯并环丁烯-4-基氯硅烷和金刚烷二醇反应,制备含金刚烷的苯并环丁烯有机硅化合物
将1,4-金刚烷二醇(1.682g, 10 mmol)、10ml四氢呋喃、咪唑(1.80g, 26.4mmol)、DMAP(0.122g, 1.0 mmol)加入到三口瓶中,将甲基乙烯基苯并环丁烯-4-基氯硅烷(4.593g,22 mmol)、5ml四氢呋喃加入到恒压滴液漏斗中。室温下缓慢滴加甲基乙烯基苯并环丁烯-4-基氯硅烷与四氢呋喃混合溶液至三口瓶中。反应液中马上生成白色沉淀。滴加结束后,继续反应2小时。反应结束后,加入乙酸乙酯(30ml*3)萃取,有机层去离子水洗涤(30ml*2),无水硫酸镁干燥。过滤后,旋蒸除去溶剂,通过减压蒸馏或者过硅胶柱提纯(400目硅胶,流动相石油醚和乙酸乙酯)。得到产物为无色透明粘稠液体,产率90%。1H-NMR(CDCl3, 500MHz):0.46(s, 6H), 1.43(s, 2H), 1.70(s, 8H),1.91(s, 2H),2.21(s,2H), 3.23(s, 8H), 5.80~5.86(dd, 2H),6.05~6.10(dd, 2H), 6.27~6.30 (dd, 2H),7.09~7.11(d, 2H),7.32(s, 2H),7.46~7.48(d, 2H)。
该单体经过高温固化后,测得5%热失重温度为449℃。
实施例2. 利用甲基乙烯基BCB氯硅烷和1,4-双(羟基二甲基硅基)苯反应,制备含苯撑的结构苯并环丁烯有机硅化合物
将1,4-双(羟基二甲基硅基)苯(0.6g,3.5mmol)、10ml四氢呋喃、加入到三口瓶中,将甲基乙烯基苯并环丁烯-4-基氯硅烷(1.4g, 7mmol)、三乙胺1.2ml、5ml四氢呋喃加入到恒压滴液漏斗中。室温下缓慢滴加甲基乙烯基苯并环丁烯-4-基氯硅烷、三乙胺和四氢呋喃混合溶液至三口瓶中。反应液中马上生成白色沉淀。滴加结束后,继续反应2小时。反应结束后,加入乙酸乙酯(30ml*3)萃取,有机层去离子水洗涤(30ml*2),无水硫酸镁干燥。过滤后,旋蒸除去溶剂,通过减压蒸馏或者过硅胶柱提纯(400目硅胶,流动相石油醚和乙酸乙酯)。得到产物为无色透明粘稠液体,产率86%。1H-NMR(CDCl3, 500MHz):0.34~0.344(s,12H),0.39(s,6H),3.17(s,8H), 5.77~5.81(dd,2H), 6.01~6.05(dd,2H), 6.20~6.27(dd,2H),7.03~7.05(d, 2H), 7.23(s,2H), 7.39~7.40(d,2H), 7.53(s,4H)。
该单体经过高温固化后,测得5%热失重温度为463℃。
实施例3.利用甲基乙烯基BCB氯硅烷和1,4-双(羟基二甲基硅基)联苯反应,制备含联苯撑的结构苯并环丁烯有机硅化合物
将1,4-双(羟基二甲基硅基)联苯(2.12g,7mmol)、三乙胺2.4ml、20ml四氢呋喃、加入到三口瓶中,将甲基乙烯基苯并环丁烯-4-基氯硅烷(2.8g,14mmol)、5ml四氢呋喃加入到恒压滴液漏斗中。室温下缓慢滴加甲基乙烯基苯并环丁烯-4-基氯硅烷和四氢呋喃混合溶液至三口瓶中。反应液中马上生成白色沉淀。滴加结束后,继续反应2小时。反应结束后,加入乙酸乙酯(30ml*3)萃取,有机层去离子水洗涤(30ml*2),无水硫酸镁干燥。过滤后,旋蒸除去溶剂,通过减压蒸馏或者过硅胶柱提纯(400目硅胶,流动相石油醚和乙酸乙酯)。得到产物为无色透明粘稠液体,产率82%。1H-NMR(CDCl3, 500MHz):0.53(s,12H), 0.56(s,6H),3.31(s, 8H), 5.93~5.98(dd,2H), 6.17~6.21 (dd,2H), 6.37~6.44(dd,2H), 7.18~7.20(d,2H),7.40(s,2H),7.56~7.58(d,2H), 7.72~7.79(m,4H)。
该经过高温固化后,测得5%热失重温度为452℃。
实施例4.利用甲基乙烯基BCB氯硅烷和二苯基硅二醇反应
将二苯基硅二醇(1.73g,8mmol)、三乙胺(2.02g)、20ml四氢呋喃加入到三口瓶中,用注射器称取甲基乙烯基苯并环丁烯-4-基氯硅烷(4.18g,20mmol)。冰浴条件下缓慢滴加甲基乙烯基苯并环丁烯-4-基氯硅烷至三口瓶中。反应液中马上生成白色沉淀。滴加结束后,在室温条件下继续反应2小时。反应结束后,加入乙酸乙酯(30ml*3)萃取,有机层去离子水洗涤(30ml*2),无水硫酸镁干燥。过滤后,旋蒸除去溶剂,通过减压蒸馏或者过硅胶柱提纯(400目硅胶,流动相石油醚和乙酸乙酯)。得到产物为无色透明粘稠液体,产率75%。1H-NMR(CDCl3, 500MHz):7.55 (d, 2H), 7.35(d, 2H),7.28(t, 2H), 7.17(s, 1H), 6.98(d, 1H), 6.18 (dd,1H), 5.99 (dd,1H), 5.76(dd,1H), 3.15(s, 4H), 0.335(s,3H)。
该单体经过高温固化后,测得5%热失重温度为472℃。
Claims (4)
1.一种含苯并环丁烯官能团的有机硅化合物的制备方法,其特征在于,以含苯并环丁烯有机硅前驱体作为封端剂,与含有羟基的有机化合物或者其形成的有机化合物盐的反应底物进行反应,即在溶剂存在下,通过碱催化剂催化发生水解,经自缩聚反应,制备含苯并环丁烯官能团的有机化合物;其中,反应温度为-30℃--100℃;反应在普通大气条件下进行,或者在氮气、氩气保护下进行;反应时间为1小时到12小时;反应结束后,反应溶液经过过滤、洗涤、有机溶剂萃取、干燥、旋转蒸发浓缩,再通过柱层析或者减压蒸馏或者重结晶方法进行提纯,得到含苯并环丁烯官能团的有机硅化合物;其中:
所述含苯并环丁烯官能团的有机硅前驱体是下述结构:
所述反应底物选自1,4-金刚烷二醇和以下含有羟基的有机硅化合物:
2.根据权利要求1所述的制备方法,其特征在于,所述催化剂选自四甲基氢氧化铵、四乙基氢氧化铵、氢氧化钠、氢氧化钾、氨水、吡啶、三乙胺、二乙胺、4-二甲胺基吡啶、咪唑、N-甲基咪唑、2-甲基-咪唑、含咪唑结构的盐、氧化钙中的一种或者多种;所用的溶剂是选自四氢呋喃、乙醚、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺,2-甲基四氢呋喃、二氯甲烷、甲苯、丙酮、丁酮、环己酮、乙酸乙酯、乙酸丙酯、乙酸丁酯中一种或者多种。
3.由权利要求1或2之一所述的制备方法制备得到的含苯并环丁烯官能团的有机硅化合物。
4.如权利要求3所述的含苯并环丁烯官能团的有机硅化合物在制备聚合物电子封装材料中的应用,其特征在于,通过在溶剂中于150~180℃下预聚得到一定分子量的预聚体,通过旋涂、固化,制备得薄膜;或者在含双键的单体预聚体中加入含双叠氮官能团的光敏剂2,6-二(4-叠氮苯亚甲基)-4甲基环己酮,制备得光刻胶。
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