CN1129245A - 光聚合液晶 - Google Patents
光聚合液晶 Download PDFInfo
- Publication number
- CN1129245A CN1129245A CN95116875A CN95116875A CN1129245A CN 1129245 A CN1129245 A CN 1129245A CN 95116875 A CN95116875 A CN 95116875A CN 95116875 A CN95116875 A CN 95116875A CN 1129245 A CN1129245 A CN 1129245A
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- Prior art keywords
- phenylcarbonyloxy
- ooc
- coo
- formula
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- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- -1 nitro, acetyl Chemical group 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- 150000002237 fumaric acid derivatives Chemical class 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 claims description 4
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 claims description 4
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 claims description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 4
- 235000005513 chalcones Nutrition 0.000 claims description 4
- 150000001851 cinnamic acid derivatives Chemical group 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000001789 chalcones Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical group C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- VCJCOCSICNRTBR-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCCCOC(C=C)=O VCJCOCSICNRTBR-UHFFFAOYSA-N 0.000 description 16
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 13
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- UJBGEOISYISUNC-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCOC(C=C)=O UJBGEOISYISUNC-UHFFFAOYSA-N 0.000 description 5
- LIGKUGJIWQLYGQ-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCOC(C=C)=O LIGKUGJIWQLYGQ-UHFFFAOYSA-N 0.000 description 5
- RQYHQEDMQYEMTH-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCOC(C=C)=O RQYHQEDMQYEMTH-UHFFFAOYSA-N 0.000 description 5
- CDXFUMHDOVSCSQ-UHFFFAOYSA-N C=CC(=O)OCCCCCCCCCCCCOC1=CC=C(C=C1)C(=O)OOC(=O)C2=CC=CC=C2 Chemical compound C=CC(=O)OCCCCCCCCCCCCOC1=CC=C(C=C1)C(=O)OOC(=O)C2=CC=CC=C2 CDXFUMHDOVSCSQ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 4
- IRJLMUXIARJGDF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCCCCCCOC(C=C)=O IRJLMUXIARJGDF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XTDRXXOCFOAXEV-UHFFFAOYSA-N [4-(1-hydroxyethoxy)phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OC(O)C)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 XTDRXXOCFOAXEV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QCXCCZXEMOPNTQ-UHFFFAOYSA-N (4-formylphenyl) 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC1=CC=C(C=O)C=C1 QCXCCZXEMOPNTQ-UHFFFAOYSA-N 0.000 description 2
- MNTKWYBPDFGVIV-UHFFFAOYSA-N 2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]benzoic acid Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(C(=O)O)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 MNTKWYBPDFGVIV-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- ZFAMIWROYLDZIB-UHFFFAOYSA-N 6-(4-benzoylperoxycarbonylphenoxy)hexyl prop-2-enoate Chemical compound C(C1=CC=CC=C1)(=O)OOC(C1=CC=C(C=C1)OCCCCCCOC(C=C)=O)=O ZFAMIWROYLDZIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- OMHAXAGZXQLHOB-UHFFFAOYSA-N [3,4-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 OMHAXAGZXQLHOB-UHFFFAOYSA-N 0.000 description 2
- YPEWZIDIXXUVIX-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(CO)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 YPEWZIDIXXUVIX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- REPOBJYFXIYYSV-UHFFFAOYSA-N 4-(1-hydroxyethoxy)phenol Chemical compound CC(O)OC1=CC=C(O)C=C1 REPOBJYFXIYYSV-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- YDLBYZSHOKLIJR-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCCCOC(C=C)=O YDLBYZSHOKLIJR-UHFFFAOYSA-N 0.000 description 1
- UWCNSZLPFOPCCW-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCOC(C=C)=O Chemical compound C(C1=CC=CC=C1)(=O)OOC(=O)C1=CC=C(C=C1)OCCCOC(C=C)=O UWCNSZLPFOPCCW-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- HSXBZNHNNPLBFF-UHFFFAOYSA-N [3,4-bis[[4-(10-prop-2-enoyloxydecoxy)benzoyl]oxy]phenyl] 4-(10-prop-2-enoyloxydecoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCCOC(=O)C=C)C=C1 HSXBZNHNNPLBFF-UHFFFAOYSA-N 0.000 description 1
- FWCOIHKBJBSOJW-UHFFFAOYSA-N [3,4-bis[[4-(11-prop-2-enoyloxyundecoxy)benzoyl]oxy]phenyl] 4-(11-prop-2-enoyloxyundecoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCCCOC(=O)C=C)C=C1 FWCOIHKBJBSOJW-UHFFFAOYSA-N 0.000 description 1
- WAZFJMQZBTZIEW-UHFFFAOYSA-N [3,4-bis[[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxy]phenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 WAZFJMQZBTZIEW-UHFFFAOYSA-N 0.000 description 1
- NQCSXQAJJVRQDL-UHFFFAOYSA-N [3,4-bis[[4-(5-prop-2-enoyloxypentoxy)benzoyl]oxy]phenyl] 4-(5-prop-2-enoyloxypentoxy)benzoate Chemical compound C1=CC(OCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCOC(=O)C=C)C=C1 NQCSXQAJJVRQDL-UHFFFAOYSA-N 0.000 description 1
- NTVOHYDLPGKOBP-UHFFFAOYSA-N [3,4-bis[[4-(7-prop-2-enoyloxyheptoxy)benzoyl]oxy]phenyl] 4-(7-prop-2-enoyloxyheptoxy)benzoate Chemical compound C1=CC(OCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCOC(=O)C=C)C=C1 NTVOHYDLPGKOBP-UHFFFAOYSA-N 0.000 description 1
- GREBKHWAVIHQFL-UHFFFAOYSA-N [3,4-bis[[4-(8-prop-2-enoyloxyoctoxy)benzoyl]oxy]phenyl] 4-(8-prop-2-enoyloxyoctoxy)benzoate Chemical compound C1=CC(OCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCOC(=O)C=C)C=C1 GREBKHWAVIHQFL-UHFFFAOYSA-N 0.000 description 1
- XFWCBHGHIFFJCH-UHFFFAOYSA-N [3,4-bis[[4-(9-prop-2-enoyloxynonoxy)benzoyl]oxy]phenyl] 4-(9-prop-2-enoyloxynonoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1OC(=O)C=2C=CC(OCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCOC(=O)C=C)C=C1 XFWCBHGHIFFJCH-UHFFFAOYSA-N 0.000 description 1
- ZBTCSYDLYVZCDB-UHFFFAOYSA-N [3-chloro-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(Cl)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 ZBTCSYDLYVZCDB-UHFFFAOYSA-N 0.000 description 1
- NHKGYWOXPXJAPK-UHFFFAOYSA-N [4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl]methyl 2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1COC(=O)C1=CC(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 NHKGYWOXPXJAPK-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 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
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical class CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OITVQUKMNWSDCD-UHFFFAOYSA-N cyclohexa-3,5-diene-1,1,2,4-tetrol Chemical compound OC1C=C(O)C=CC1(O)O OITVQUKMNWSDCD-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000012720 spontaneous thermal polymerization Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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Abstract
本发明涉及通式I的光化学齐聚性或聚合性液晶、含有这种化合物的液晶混合物以及在交联态下使用它们作为光学或电子元件、式I中A1、A2和A3代表光化学齐聚或聚合性内生残基。
Description
本发明涉及光化学齐聚性或聚合性液晶,含这种化合物的液晶混合物,以及其在交联态下作为光学或电子元件的用途。
至少有两个光化学齐聚性或聚合性基团的液晶,能够借助于取向层或电场在基片或晶胞中取向。这些取向的液晶,只要含适量光引发剂就能够通过具有适当波长光线的辐照而聚合。这样产生的交联结构即使在高温下也仍然存留。这样的一些层,例如可以是瑞士专利申请CH 2016/ 94和CH 2017/94中所述的部分杂化层。因此,能够制造一些光学元件,例如阻尼器、波导、光栅和滤光片,以及具有压电性和非线性光学(NLO)性质的累积有色滤光片和电池等。这种光学元件例如在投影系统中找到了用途。
其它一些性质,例如双折射性、折射率和透明度等也必须根据应用的领域而满足不同要求。例如光学阻尼器的网络应当具有高双折射性,以便使此累积光学元件的层厚度能够保持最小。
为了迅速和高效地分散高密度元件操作时产生的热量,在微电子学领域中使用呈电绝缘但是即具有优良导热性的聚合物。此外还需要一些具有低介电常数和高耐热性的绝缘导。均匀取向的液晶网络因其低热膨胀系数、高导热性和稳定性而适于这些用途。
除了在光学和电子元件上一般对光化学齐聚或聚合性液晶感兴趣之外,其它领域也需要这些化合物。因此,这种液晶材料也适用于光数据传输用的包层玻璃纤维上。这种网络的使用提高所说的纤维长轴上的弹性模数,降低热膨胀系数和减小微畸变损失。这导致机械稳定性提高。
由于液晶通常以几种成分混合物的形式使用,所以重要的一点是所说的成分彼此之间应具有良好的可混性。传统的光化学齐聚或聚合性液晶,通常有高熔点和高透明点。然而,在温度稍低于透明点的温度下进行处理时,由于此温度下液晶态下的粘度最低,因而对于良好的取向性来说是有利的,所以能够早期发生自发的热聚合反应。这种热聚合反应导致畴的形成,所以能够显著影响所生成的交联层中的那些光学和热学性质。通过用几种成分制造一些复杂的混合物可以降低熔点,这的确可以在低温下处理,而且带来传统的可聚合的液晶形成结晶的危险。
因此,目前需要生产出满足上述诸要求的光化学齐聚或聚合性化合物。为了在高于室温的温度下于液晶状态下以及溶液中能够极容易处理这些化合物,它们应当具有低熔点和低透明点。此外,这些化合物应当是能够取向和能构成尽可能无畴的结构;而且它们还应当在交联态下具有优良的热稳定性和长期稳定性。
光化学齐聚性或聚合性内生残基A1、A2和A3可以相同或不同。内生残基是本领域普通技术人员已知的,例如载于<Flüssigkristallein Tabellen>(Vol.II,Deutscher Verlag für Grundstoffindustrie,Leipzig,1984)中。这些已知的内生残基在末端有聚合性残基,以便使之适于上述目的。
通式I化合物在通常溶剂(如苯甲醚、N,N′-二甲基乙酰胺或N-甲基吡咯烷酮)中有良好的溶解度,而且以相当低粘度为其特征。所以能将其涂于适当表面上而不产生问题。通常用旋涂法涂布之。而且由于本发明化合物具有液晶相,所以能够在交联之前使之在取向层上定向或者利用电场或磁场使之定向。
优选的式I的化合物是其中的光化学齐聚性或聚合性内生残基A1、A2和A3各独立地代表式II残基的化合物:其中:
C和D各独立地代表被硝基、乙酰基、卤素、甲基和/或氰基取
代或未取代的1,4-亚苯基、2,5-亚吡啶基、2,5-亚嘧
啶基、反式-1,4-亚环己基或反式-1,3-二噁烷-2,5
-亚基;
Z1代表单键、-CH2-CH2-、-CH2O-、-COO-、-OOC-、
-(CH2)4-或-(CH2)3O-;
Z2代表单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-、
-OOC-、-(CH2)4-、-O(CH2)3-或-(CH2)3O-;Z3代表-(CY2)m-、-(CY2)mO-、-(CY2)mCOO-、
-(CY2)mOOC-、-(Si[(CH3)2]O)p-、
-OCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2O-
或-NHCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2NH-;
Y代表氢或氟;
m代表1~16的整数;
p代表1~16的整数;
n代表0或1;以及
R1代表聚合性基团,例如丙烯酸酯、烯丙基醚、烯丙基酯、甲
基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、丙烯酰
亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、环
氧、衣康酸酯、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来
酸衍生物、富马酸衍生物或二聚性基团,例如查尔酮或者被
甲基、甲氧基、氰基和/或卤素取代的或未取代的肉桂酸衍
生物。
术语“被硝基、乙酰基、卤素、甲基和/或氰基取代或未取代的1,4-亚苯基”在本发明范围内指1,4-亚苯基、2-硝基-1,4-亚苯基、3-硝基-1,4-亚苯基、2-乙酰基-1,4-亚苯基、3-乙酰基-1,4-亚苯基、2-氟-1,4-亚苯基、3-氟-1,4-亚苯基、2,3-二氟-1,4-亚苯基、2-氯-1,4-亚苯基、3-氯-1,4-亚苯基、2,3-二氯-1,4-亚苯基、2-氰-1,4-亚苯基、3-氰基-1,4-亚苯基、2,3-二氰基-1,4-亚苯基、2-甲基-1,4-亚苯基、3-甲基-1,4-亚苯基等等。
C、C1、D和D1各独立代表被硝基、乙酰基、卤素、甲基和/或氰基取代或未取代的1,4-亚苯基、2,5-亚吡啶基、2,5-亚嘧啶基、反式-1,4-亚环己基或反式-1,3-二噁烷-2,5-亚基;
Z1和Z11各独立代表单键、-CH2CH2-、-CH2O-、
-COO-、-OOC-、-(CH2)4-或-(CH2)3O-;
Z2和Z21各独立地代表单键、-CH2CH2-、-CH2O-、
-OCH2-、-COO-、-OOC-、-(CH2)4-、-O(CH2)3-
或-(CH2)3O-;
Z3和Z31各独立代表-(CY2)m-、-(CY2)mO-、
-(CY2)mCOO-、-(CY2)mOOC-、-(Si[(CH3)2]O)p-、
-OCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2O-或
-NHCH2(Si[(CH3)2O)pSi[(CH3)2]CH2NH-;
Y代表氢或氟;
m是1~16的整数;
p是1~16的整数;
n是0或1;以及
R1和R11各独立代表聚合性基团,例如丙烯酸酯、烯丙基醚、
烯丙基酯、甲基丙烯酸酯、2-氯-丙烯酸酯、2-苯基丙
烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯
基丙烯酰胺、环氧、衣康酸酯、乙烯基醚、乙烯基酯、苯乙
烯衍生物、马来酸衍生物、富马酸衍生物或二聚性基团,如
查尔酮或被甲基、甲氧基、氰基和/或卤素取代或未取代的
肉桂酸衍生物。
本发明的中间相型化合物能够受环C或C1以及D或D1变化的影响。因此杂环具有产生近晶相的趋势,而亚苯基和亚环己基环具有促进向列的趋势。环C或C1以及D或D1最好各独立代表1,4-亚苯基、2-氟-1,4-亚苯基、3-氟-1,4-亚苯基、吡啶-2,5-亚基或嘧啶-2,5-亚基,特别是1,4-亚苯基、2-氟-1,4-亚苯基或3-氟-1,4-亚苯基。
特别优选的式I-1~I-4化合物,是其中Z1和Z11分别代表-CH2O-、-COO-或-OOC-的化合物以及Z2和Z21分别代表单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-或-OOC-以及Y代表氢的化合物。
在特别洗选的式I-1~I-4的化合物中,所说的残基R1和R11分别代表丙烯酸酯、甲基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、环氧、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来酸衍生物或富马酸衍生物等等;丙烯酸酯、甲基丙烯酸酯和环氧是特别优选的。
R12代表丙烯酸酯、甲基丙烯酸酯或环氧;
Z32代表-(CH2)t-、-(CH2)tO-、-(CH2)tCOO-或
-(CH2)tOOC-;
t代表3~12中整数;
C2代表1,4-亚苯基、2-氟-1,4-亚苯基或3-氟-1,4-
亚苯基;以及
其中内生残基A1、A2和A3彼此不同的本发明的通式1、1-1、1-2和1-3化合物很容易合成得到,可以按照本身已知的方法,例如与路线1~3以及实施例中所述方法相似的方式生产。
式II和II-a的内生残基是已知的或者是与已知的结构相似,而且可以用本身已知的方式制备后与芳环连接。
在每-步骤中混入少量BHT(2,6-二叔丁基-4-甲基苯酚=“丁羟基甲苯”),以便终止所不希望的热交联作用。
反应路线2
路线3
其中内生残基A1、A2和A3相同的式I-4和I-5化合物,可以利用简单且已知的方法制造,例如按照路线4所示由1,2,4-三羟基苯酚和式II的相应酸衍生物如4-[正-(丙烯酸基烷氧基)]苯甲酸制备。此酯化反应可以在二氯甲烷或其它适当溶剂如氯仿中,于N,N′-二环己基碳化二亚胺和4-(二甲基氨基)吡啶存在下进行。原料是已知的,而且在一定程度上是能从市场上买到的。
式I的化合物既可以以单一成分形式使用,也可以以其彼此间混合物和/或与其它液晶成分的混合物形式使用。
本发明的液晶混合物至少含两种成分,其中一种成分是式I化合物。第二种成分和其它成分也可以是式I的加入的化合物或者含或不含光交联性基团的其它已知液晶化合物。此外,混合物中还可以存在一或多种手性化合物。
鉴于式I化合物的良好溶解性以及它们之间彼此的良好可混性,本发明混合物中不同的式I化合物含量可以高,且可以高达100wt%。除了一或多种式I化合物之外,本发明混合物最好还含有一或多种通式III~VIII化合物: 式中,
t代表3~12中整数;
q代表2~12中整数;以及
x代表氢、氟、氧或低级烷基,如甲基、乙基、丙基或丁基。
式I化合物以及含这些化合物的液晶混合物的生产利用下列实施例作更详细地说明。C代表晶体相、S代表近晶相、N代表向列相且r代表各向同性相。
实施例1
室温搅拌下,向4.7克4-[6-丙烯酰氧基己氧基]苯甲酸、0.5克三羟基苯和0.2克4-二甲基氨基吡啶于25ml二氯甲烷中的溶液内加入5.0克N,N′-二环己基碳二亚胺。该反应混合物室温下搅拌过夜,倒入100ml水中,然后用二氯甲烷萃取三次,每次50ml二氯甲烷。合并的有机相用水洗涤二次,每次用100ml水,硫酸镁干燥,过滤,然后浓缩滤液。残余物经硅胶色谱(己烷-乙酸乙酯的3∶1(体积比)洗脱),又经薄层色谱提纯的流出物用乙醇两倍重结晶,得到2.0克1,2,4-三(4-[6-丙烯酰氧基己氧基]-苯基羰氧基)苯,熔点(m.p.)(C-1)44℃,透明点(cl.p.)(N-1)33℃。
按相似方式制备了下列化合物:1,2,4-三(4-[3-丙烯酰氧基丙氧基]苯基羰氧基)苯;1,2,4-三(4-[4-丙烯酰氧基丁氧基]苯基羰氧基)苯;
m.p.(C-1)46℃,Cl.p(N-1)-8℃;1,2,4-三(4-[5-丙烯酰氧基戊氧基]苯基羰氧基)苯;
m.p.(C-1)39℃,Cl.p(N-1)33℃;1,2,4-三(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯;
m.p.(C-1)31℃,Cl.p(N-1)44℃;1,2,4-三(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯;
m.p.(C-1)56℃,Cl.p(N-1)42℃;1,2,4-三(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯;
m.p.(C-1)41℃,Cl.p(N-1)51℃1,2,4-三(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯;
m.p.(C-1)55℃,Cl.p(N-1)46℃;1,2,4-三(4-[11-丙烯酰氧基十一氧基]苯基羰氧基)苯;
m.p.(C-1)44℃,Cl.p(N-1)53℃。
实施例2
室温搅拌下,向0.6克的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸、0.4克[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲醇和0.04克4-二甲氨基吡啶于20ml二氯甲烷的溶液中加入0.2克N,N′-二环己基碳二亚胺。该反应混合物在室温下搅拌过夜,倒入100ml水中后,用二氧甲烷萃取三次(每次50ml)。合并的有机相用水(每次100ml)洗涤两次,硫酸镁干燥,过滤,然后浓缩滤液。残余物经硅胶色谱纯化,己烷/乙酸乙酯(容积比1∶1)洗脱,流出液再经薄层色谱提纯后,用两倍丙酮重结晶后,得到0.4克的[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯。
作为原料所用的[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲醇制备如下:
(a)0℃下滴加0.8克4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛在100ml二噁烷中的溶液,处理0.13克硼氢化钠和15ml水的混合物。该反应混合物于0℃下再搅拌60分钟后,于室温下搅拌10分钟,倒入100ml二氯甲烷中用水(每次100ml)洗涤两次。合并的水相用二氯甲烷(每次50ml)萃取两次。然后用水(每次100ml)洗涤合并的有机相两次,硫酸镁干燥,过滤悬浮液,滤液浓缩。此残余物用于下-步中而不必进一步提纯。
(b)室温搅拌下,向1.0克的4-[6-丙烯酰氧基己氧基]苯甲酸、0.3克4-羟基苯甲醛和0.04克4-二甲氨基吡啶在20ml二氯甲烷中和溶液内加入0.6克的N,N′-双环双环己基碳化二亚胺;该反应混合物室温下搅拌过夜后,倒入100ml水中,然后用二氯甲烷,(每次50ml)萃取三次。合并的有机相用水(每次100ml)洗涤二次,硫酸镁干燥,过滤,然后浓缩滤液。残余物经硅胶色谱提纯,己烷/乙酸乙酯(容积比1∶1)洗脱,流出液再经薄层色谱提纯,用两倍乙醇重结晶,得到0.9克4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛。
按类似方式可以制备下列化合物:
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[3-丙烯酰氧基丙氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[4-丙烯酰氧基丁氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[5-丙烯酰氧基戊氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯基]甲基的2,5-双(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯甲酸酯。
实施例3
按和实施例1相似的方式,使0.6克的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸、0.4克的[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙醇、0.04克的4-二甲氨基吡啶和0.2克的N,N′-双环双环己基碳化二亚胺在20ml二氯甲烷中反应,以便形成[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯。
作为原料使用的[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙醇制备如下:
(a)按和实施例1相似的方式,使0.6克的4-[6-丙烯酰氧基己氧基]苯甲酸、0.2克的(4-羟基苯氧基)乙醇、0.04克的4-二甲氨基吡啶和0.4克的N,N′-双环双环己基碳化二亚胺在50ml二氯甲烷中反应,得出0.4克[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙醇。
按类似方式可以制备下列化合物:
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[3-丙烯酰氧基丙氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[4-丙烯酰氧基丁氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[5-丙烯酰氧基戊氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]乙基的2,5-双(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]丙基的2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]丁基的2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]戊基的2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]己基的2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]庚基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
[4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯氧基]辛基的2,5-双(4-[12-丙烯酰氧基十二烷氧基]苯基羰氧基)苯甲酸酯。
实施例4
按照与实施例1相似的方式,使0.3克的4-[6-丙烯酰氧基己氧基]苯甲酸、0.8克的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸4-羟基丁酯、0.04克的4-二甲氨基吡啶和0.2克的N,N′-双环双环己基碳化二亚胺在50ml二氯甲烷中反应,生成0.5克的4-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丁基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯。
按类似方式可以制备下列化合物:
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
5-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)戊基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
6-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)己基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
7-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)庚基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
8-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)辛基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
9-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)壬基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
10-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)癸基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
11-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)十一烷基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
12-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)十二烷基的2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[5-丙烯酰氧基戊氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯;
3-(4-[6-丙烯酰氧基己氧基]苯基羰氧基)丙基的2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯。
实施例5
由80wt%1,2,4-三(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯和20wt%1-氯-2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯组成的混合物(C-N,<20℃,N-1,38℃),用溶解在苯甲醚(40wt%)中的1wt%光引发剂(IRGACURE,CibaGeigy)处理之后,在2000转/分转速下旋涂在玻璃板上。此玻璃板事先涂有3-(E)-[4-氰基-4′-联苯基]丙烯酸的甲基丙烯酰氧基乙酯,然后用线性偏振光辐照过。以便借助于(PPN)层中的掩膜照相平板印刷上预定的结构。90℃于加热板上干燥旋涂的新层(处于PPN层之上),接着在真空箱中真空下和90℃用氙光辐射。光刻上的原始结构被保留,并且用新网络加以精确复制。一种清楚的双折射作用(Δn)能识别出。此层起着结构光学阻尼器的作用。
Claims (13)
1.通式I的化合物,其中A1、A2和A3代表光化学齐聚性或聚合性内生残基。
2.根据权利要求1的化合物,其中内生残基A1、A2和A3各独立地代表式II的残基。其中:
C和D各独立地代表被硝基、乙酰基、卤素、甲基和/或氰基取代或未取代的1,4-亚苯基、2,5-亚吡啶基、2,5-亚嘧啶基、反式-1,4-亚环己基或反式-1,3-二噁烷-2,5-亚基;
Z1代表单键、-CH2-CH2-、-CH2O-、-COO-、-OOC-、-(CH2)4-或-(CH2)3O-;
Z2代表单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-、-OOC-、-(CH2)4-、-O(CH2)3-或-(CH2)3O-;
Z3代表-(CY2)m-、-(CY2)mO-、-(CY2)mCOO-、-(CY2)mOOC-、-(Si[(CH3)2]O)p-、-OCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2O-
或-NHCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2NH-:
Y代表氢或氟;
m代表1~16的整数;
p代表1~16的整数;
n代表0或1;以及
R1代表聚合性基团,例如丙烯酸酯、烯丙基醚、烯丙基酯、甲基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、环氧、衣康酸酯、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来酸衍生物、富马酸衍生物或二聚性基团,例如查尔酮或者被甲基、甲氧基、氰基和/或卤素取代的或未取代的肉桂酸衍生物。
3.根据权利要求1或2的化合物,其中内生残基A1、A2和A3中的两个具有相同含意。
C、C1、D和D1各独立代表被硝基、乙酰基、卤素、甲基和/或氰基取代或未取代的1,4-亚苯基、2,5-亚吡啶基、2,5-亚嘧啶基、反式-1,4-亚环己基或反式-1,3-二噁烷-2,5-亚基;
Z1和Z11各独立代表单键、-CH2CH2-、-CH2O-、-COO-、-OOC-、-(CH2)4-或-(CH2)3O-;
Z2和Z21各独立地代表单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-、-OOC-、-(CH2)4-、-O(CH2)3-或-(CH2)3O-;
Z3和Z31各独立地代表-(CY2)m-、-(CY2)mO-、-(CY2)mCOO-、-(CY2)mOOC-、-(Si[(CH3)2]O)p-、-OCH2(Si[(CH3)2]O)pSi[(CH3)2]CH2O-或-NHCH2(Si[(CH3)2O)pSi[(CH3)2]CH2NH-
Y代表氢或氟;
m是1~16的整数;
p是1~16的整数;
n是0或1;以及
R1和R11各独立代表聚合性基团,例如丙烯酸酯、烯丙基醚、烯丙基酯、甲基丙烯酸酯、2-氯-丙烯酸酯、2-苯基丙烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、环氧、衣康酸酯、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来酸衍生物、富马酸衍生物或二聚性基团,如查尔酮或被甲基、甲氧基、氰基和/或卤素取代或未取代的肉桂酸衍生物。
5.根据权利要求1或2的下式化合物其中诸符号具有与权利要求2中相同的含意。
6.根据权利要求2~5的化合物,其中Z1和Z11分别代表-CH2O-、-COO-或-OOC-;而且Z2和Z21分别代表单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-或-OOC;而且Y代表氢。
7.根据权利要求6的化合物,其中R1和R11分别代表丙烯酸酯、甲基丙烯酸酯、乙烯基醚或环氧。
9.根据权利要求1、2和5~8中任何一项的式I-5化合物。其中t代表3~12的整数。
10.一种聚合性液晶混合物,所说的混合物由至少两种成分组成,其中至少一种成分是权利要求1中定义的式I化合物。
12.使用权利要求1~9中任何一项中的处于交联态下的化合物制造光学元件。
13.使用权利要求10或11的光化学齐聚性或聚合性液晶混合物制造光学或电子元件。
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US (1) | US5593617A (zh) |
EP (1) | EP0700981B1 (zh) |
JP (1) | JP3973707B2 (zh) |
KR (1) | KR100391530B1 (zh) |
CN (1) | CN1091795C (zh) |
DE (1) | DE59508919D1 (zh) |
HK (1) | HK1011043A1 (zh) |
SG (1) | SG38876A1 (zh) |
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1995
- 1995-08-21 US US08/517,480 patent/US5593617A/en not_active Expired - Fee Related
- 1995-08-28 JP JP21872995A patent/JP3973707B2/ja not_active Expired - Fee Related
- 1995-09-02 EP EP95113802A patent/EP0700981B1/de not_active Expired - Lifetime
- 1995-09-02 DE DE59508919T patent/DE59508919D1/de not_active Expired - Fee Related
- 1995-09-07 KR KR1019950029377A patent/KR100391530B1/ko not_active IP Right Cessation
- 1995-09-08 SG SG1995001310A patent/SG38876A1/en unknown
- 1995-09-11 CN CN95116875A patent/CN1091795C/zh not_active Expired - Fee Related
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CN109467643A (zh) * | 2018-09-29 | 2019-03-15 | 苏州市新广益电子有限公司 | 一种用于fpc行业的lcp胶膜及其制备方法 |
Also Published As
Publication number | Publication date |
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KR960010608A (ko) | 1996-04-20 |
JP3973707B2 (ja) | 2007-09-12 |
DE59508919D1 (de) | 2001-02-01 |
EP0700981B1 (de) | 2000-12-27 |
EP0700981A3 (zh) | 1996-03-27 |
US5593617A (en) | 1997-01-14 |
HK1011043A1 (en) | 1999-07-02 |
JPH08104870A (ja) | 1996-04-23 |
KR100391530B1 (ko) | 2003-11-20 |
CN1091795C (zh) | 2002-10-02 |
SG38876A1 (en) | 1997-04-17 |
EP0700981A2 (de) | 1996-03-13 |
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