JP4945894B2 - 光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 - Google Patents
光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 Download PDFInfo
- Publication number
- JP4945894B2 JP4945894B2 JP2004331414A JP2004331414A JP4945894B2 JP 4945894 B2 JP4945894 B2 JP 4945894B2 JP 2004331414 A JP2004331414 A JP 2004331414A JP 2004331414 A JP2004331414 A JP 2004331414A JP 4945894 B2 JP4945894 B2 JP 4945894B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- phenylene
- compound
- independently
- crystal composition
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 162
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 94
- 230000003287 optical effect Effects 0.000 title claims description 57
- 229920000642 polymer Polymers 0.000 title claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 142
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- -1 methylene, ethylene, trimethylene Chemical group 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003566 oxetanyl group Chemical group 0.000 claims description 15
- 125000000466 oxiranyl group Chemical group 0.000 claims description 14
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 113
- 239000010408 film Substances 0.000 description 113
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
- 239000002904 solvent Substances 0.000 description 63
- 238000012360 testing method Methods 0.000 description 57
- 238000006116 polymerization reaction Methods 0.000 description 53
- 238000000034 method Methods 0.000 description 52
- 239000000758 substrate Substances 0.000 description 46
- 239000011521 glass Substances 0.000 description 41
- 239000004642 Polyimide Substances 0.000 description 35
- 238000005259 measurement Methods 0.000 description 35
- 229920001721 polyimide Polymers 0.000 description 35
- 239000012046 mixed solvent Substances 0.000 description 33
- 238000004528 spin coating Methods 0.000 description 33
- 238000002156 mixing Methods 0.000 description 32
- 230000002349 favourable effect Effects 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 229920002284 Cellulose triacetate Polymers 0.000 description 17
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 17
- 239000010409 thin film Substances 0.000 description 17
- 238000000576 coating method Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 150000002431 hydrogen Chemical class 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 230000000379 polymerizing effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 6
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- JZDQKBZKFIWSNW-UHFFFAOYSA-N (4-methoxyphenyl)-phenyliodanium Chemical compound C1=CC(OC)=CC=C1[I+]C1=CC=CC=C1 JZDQKBZKFIWSNW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000006039 1-hexenyl group Chemical group 0.000 description 2
- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(C)(CC(C)(C)Oc(ccc1ccccc11)c1-c1c(cccc2)c2ccc1*)C(*)(**)P Chemical compound CCC(C)(CC(C)(C)Oc(ccc1ccccc11)c1-c1c(cccc2)c2ccc1*)C(*)(**)P 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 2
- 239000012953 triphenylsulfonium Substances 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 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
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical class CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- BZNWHCKKWLBKFW-UHFFFAOYSA-N (2,4,6-trinitro-3,5-diphenylphenyl)hydrazine Chemical compound [O-][N+](=O)C=1C(C=2C=CC=CC=2)=C([N+]([O-])=O)C(NN)=C([N+]([O-])=O)C=1C1=CC=CC=C1 BZNWHCKKWLBKFW-UHFFFAOYSA-N 0.000 description 1
- AJCKDCLHJRQBNT-UHFFFAOYSA-N (2,5-ditert-butylphenyl)methanol Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(CO)=C1 AJCKDCLHJRQBNT-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- CVBASHMCALKFME-UHFFFAOYSA-N (4-methoxyphenyl)-diphenylsulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 CVBASHMCALKFME-UHFFFAOYSA-N 0.000 description 1
- DJFZWUYNTIZEKY-UHFFFAOYSA-M (4-methoxyphenyl)-diphenylsulfanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 DJFZWUYNTIZEKY-UHFFFAOYSA-M 0.000 description 1
- GDYCLAOHWKCIHQ-UHFFFAOYSA-M (4-methoxyphenyl)-diphenylsulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 GDYCLAOHWKCIHQ-UHFFFAOYSA-M 0.000 description 1
- HHUWEOXSSNBWJK-UHFFFAOYSA-N (4-methoxyphenyl)-diphenylsulfanium;triphenylsulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HHUWEOXSSNBWJK-UHFFFAOYSA-N 0.000 description 1
- WMHLKXSYGGEXNQ-UHFFFAOYSA-M (4-methoxyphenyl)-phenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC)=CC=C1[I+]C1=CC=CC=C1 WMHLKXSYGGEXNQ-UHFFFAOYSA-M 0.000 description 1
- YXSLFXLNXREQFW-UHFFFAOYSA-M (4-methoxyphenyl)-phenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC)=CC=C1[I+]C1=CC=CC=C1 YXSLFXLNXREQFW-UHFFFAOYSA-M 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- KYLXYSWUYYPCHF-UHFFFAOYSA-N (diphenyl-lambda3-iodanyl) 2,2,2-trifluoroacetate Chemical compound C=1C=CC=CC=1I(OC(=O)C(F)(F)F)C1=CC=CC=C1 KYLXYSWUYYPCHF-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OURODNXVJUWPMZ-UHFFFAOYSA-N 1,2-diphenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical class C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- WYMUYYZQUXYMJI-UHFFFAOYSA-M 2,2,2-trifluoroacetate;triphenylsulfanium Chemical compound [O-]C(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WYMUYYZQUXYMJI-UHFFFAOYSA-M 0.000 description 1
- VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical compound FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- KODNTHAUOGOFJY-UHFFFAOYSA-N 2,4-diethylxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3OC2=C1 KODNTHAUOGOFJY-UHFFFAOYSA-N 0.000 description 1
- 125000005732 2,6-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:1])=C(F)C([H])=C1[*:2] 0.000 description 1
- LNPHVNNRZGCOBK-UHFFFAOYSA-N 2-(dodecylazaniumyl)acetate Chemical compound CCCCCCCCCCCCNCC(O)=O LNPHVNNRZGCOBK-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- DNDBXYWKDTXSPJ-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]propan-1-ol Chemical compound OCC(C)N(CCO)CCO DNDBXYWKDTXSPJ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- YVYFTQAVOXKAEM-UHFFFAOYSA-N 4-methoxy-5-phenyl-2,4-bis(trichloromethyl)-1,3-dihydrotriazine Chemical compound COC1(C(Cl)(Cl)Cl)NN(C(Cl)(Cl)Cl)NC=C1C1=CC=CC=C1 YVYFTQAVOXKAEM-UHFFFAOYSA-N 0.000 description 1
- YXZXRYDYTRYFAF-UHFFFAOYSA-M 4-methylbenzenesulfonate;triphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YXZXRYDYTRYFAF-UHFFFAOYSA-M 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 1
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 1
- 208000023514 Barrett esophagus Diseases 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- YKVOBYDIHNCFJJ-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C2=CC=CC=C2N=C2C=CC=CC12.C(CCC)OC1=CC=C(C=CC=2OC(=NN2)C(Cl)(Cl)Cl)C=C1 Chemical compound C1(=CC=CC=C1)C=1C2=CC=CC=C2N=C2C=CC=CC12.C(CCC)OC1=CC=C(C=CC=2OC(=NN2)C(Cl)(Cl)Cl)C=C1 YKVOBYDIHNCFJJ-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- RPDGEBZYHFJOIL-UHFFFAOYSA-N FC(F)F.COC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound FC(F)F.COC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 RPDGEBZYHFJOIL-UHFFFAOYSA-N 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 101150059062 apln gene Proteins 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- IFTBZZXJUCYKGU-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 IFTBZZXJUCYKGU-UHFFFAOYSA-N 0.000 description 1
- OZCAIDYQMMBPSW-UHFFFAOYSA-L bis(4-tert-butylphenyl)iodanium diphenyliodanium trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 OZCAIDYQMMBPSW-UHFFFAOYSA-L 0.000 description 1
- UHGVULRLVZYBQE-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 UHGVULRLVZYBQE-UHFFFAOYSA-M 0.000 description 1
- UEJFJTOGXLEPIV-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 UEJFJTOGXLEPIV-UHFFFAOYSA-M 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 150000001862 citronellol derivatives Chemical class 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- AGFLUIPDTLQXFW-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 AGFLUIPDTLQXFW-UHFFFAOYSA-M 0.000 description 1
- WEYUQUMMYNRIPP-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 WEYUQUMMYNRIPP-UHFFFAOYSA-M 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- UMIKAXKFQJWKCV-UHFFFAOYSA-M diphenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=CC=CC=1[I+]C1=CC=CC=C1 UMIKAXKFQJWKCV-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010891 electric arc Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 229940051250 hexylene glycol Drugs 0.000 description 1
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical class C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- PCRAJOWHMTYSKR-UHFFFAOYSA-N iodobenzene;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.IC1=CC=CC=C1 PCRAJOWHMTYSKR-UHFFFAOYSA-N 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- MCPLVIGCWWTHFH-UHFFFAOYSA-L methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- NGAVKPIEGZEJAO-UHFFFAOYSA-N naphtho[1,2-g]phthalazine Chemical compound N1=NC=C2C=C3C4=CC=CC=C4C=CC3=CC2=C1 NGAVKPIEGZEJAO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000012788 optical film Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polarising Elements (AREA)
Description
これらの光学素子は、光学異方性を有する重合性の液晶を液晶状態で重合し固定化することによって得られる。したがって、液晶状態において適切な配向制御を行った後、重合させることによって、ホモジニアス配向、チルト配向、ハイブリッド配向、ホメオトロピック配向およびツイスト配向等の種々の光学異方性を有する重合体を得ることができる。
第一成分である化合物(1−1)〜(1−3)は、重合前の特性として、広いネマチック相範囲、良好な配向性、他の液晶性化合物との高い相溶性を有し、目的に応じたΔnの調整、下限温度と上限温度の調整が可能であり、重合後の特性として、透明性、耐熱性、耐湿性および種々の基材に対する密着性に優れており、また、塗膜する際に溶媒を用いる場合に、溶媒に対する溶解性に優れている。
第一成分として、化合物(1−1)〜(1−3)、第二成分として、化合物(2−1)〜(2−3)、を含有する組成物の場合の好ましい割合は次のとおりである。
好ましいR1は、ハロゲン、−CN、−NCS、−OCF3、−OCF2H、炭素数2〜10のアルケニル、炭素数1〜10のアルキル、アルキルまたはアルケニル中の−CH2−は、−O−で置き換えられてもよい。好ましいR2は、水素であり、好ましいR3は、メチルまたはエチルであり、好ましいR4は、ハロゲン、−CN、炭素数2〜10のアルケニル、炭素数1〜10のアルキルであり、アルケニルまたはアルキル中の任意の−CH2−は、−O−、で置き換えられてもよく、アルケニルまたはアルキル中の任意の水素はハロゲンで置き換えられてもよく、アルケニルまたはアルキル中の1つの水素はオキシラニル、オキセタニルで置き換えられてもよい。好ましいP1は、水素、ハロゲンまたは(C)である。ただし、P1の中で少なくとも2つは(C)である。
好ましいA2は、1,4−シクロへキシレン、1,4−フェニレン、少なくとも1つの水素がハロゲンまたは炭素数1〜10のアルキルで置き換えられた1,4−フェニレンであり、このアルキル中の任意の水素は、ハロゲンで置き換えられてもよい。
好ましい化合物(1−1)は、化合物(1−1−1)〜(1−1−441)である。好ましい化合物(1−2)は、化合物(1−2−1)〜(1−2−229)である。好ましい化合物(1−3)は、化合物(1−3−1)〜(1−3−50)である。
化合物(1−2−116)は、ハイドロキノン誘導体と置換安息香酸誘導体とのエステル化反応により合成できる。より具体的には、例えば特願2003−567に記載の方法により合成できる。化合物(1−3)および(2−3)は、有機合成化学の手法を組み合わせることにより合成できる。具体的な方法は、ホーベン−ワイル(Houben-Wyle, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart)、オーガニック シンセシーズ(Organic Syntheses, John Wily & Sons, Inc.)、オーガニック リアクションズ(Organic Reactions, John Wily & Sons Inc.)、コンプリヘンシブ オーガニック シンセシス(Comprehensive Organic Synthesis, Pergamon Press)、新実験化学講座(丸善)などに記載されている。より具体的には、特願2001−317433に記載の方法を適用できる。式(3−1)および式(3−2)で示されるビナフトール誘導体は、例えば、Mol.Cryst.and Liq.Cryst.,2001.,Vol.364,pp825〜834、EP0217239明細書、およびWO02/06195明細書に記載された方法によって合成できる。
本発明の組成物は通常の光カチオン重合開始剤を添加して使用する。光カチオン重合開始剤には、ジアリールヨードニウム塩(以下DASと略す)、トリアリールスルホニウム塩(以下TASと略す)などがあげられる。
光重合開始剤の好ましい添加量は、液晶組成物に対して、0.01〜10重量%である。より好ましくは、0.01〜5重量%である。
下記のアクリレート系の組成物IIを、以下の2つの方法により、まず基板に塗布した。(1)シクロペンタノンに30%の濃度で溶解し、スピンコート法によってラビング処理を施したポリイミド付きガラス基板に塗布し、(2)トルエンとシクロペンタノンの混合溶媒(混合比(重量比)は2:1)に30%の濃度で溶解し、バーコーターを用いて、ラビング処理を施したTACフィルムに塗布した。次に、いずれの場合も、70℃、3分間の条件にて溶媒を除去し、重合することによってホモジニアス配向を有する光学薄膜を得た。
A−6OBBC 30%
A−6OBEB(CF3)ErBO6−A 27%
A−6OBEFL(1)ErBO6−A 40%
IRG907 3%
E−2OBEBO2−E 49%
E−1O6OBEFL(1)ErBO6O1−E 48%
DTS−102 3%
X(1)−4OBEB(1)ErBO4−X(1) 20%
X(1)−6OBEB(1)ErBO6−X(1) 37%
X(1)−1O6OBEFL(1)ErO6O1−X(1) 40%
DTS−102 3%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 48%
DTS−102 3%
E−6OBEB(DCF3)ErBO6−E 30%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 30%
X(1)−1O6OBEFL(2)ErBO6O1−X(1) 17%
DTS−102 3%
E−2OBEBO2−E 20%
X(2)−1O4OBEFL(1)ErBO4O1−X(2) 15%
X(1)−1O6OBEFL(2)ErBO6O1−X(1) 32%
DTS−102 3%
E−3HHB(F)F 37%
X(1)−1O6OHEFL(1)ErHO6O1−X(1) 30%
DTS−102 3%
E−4OBBC 40%
X(1)−6OBEB(1)ErBO6−X(1) 52%
DTS−102 3%
E−3HHB(F)F 30%
E−6OBEB(1)ErBO6−E 27%
X(1)−3HHB(F)F 30%
DTS−102 3%
E−6OBEB(1)ErBO6−E 28%
X(1)−1O4OBBC 20%
X(1)−6OBEB(1)ErBO6−X(1) 29%
DTS−102 3%
X(1)−6OBEB(1)ErBO6−X(1) 49%
DTS−102 3%
X(2)−1O4OBBC 49%
DTS−102 3%
X(2)−1O4OBBC 27%
X(1)−3HHB(F)F 30%
DTS−102 3%
E−2OBEBO2−E 20%
E−1O6OBEFL(1)ErBO6O1−E 30%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 30%
DTS−102 3%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 44%
Yが炭素数5のアルキルである化合物(3−1−6) 10%
DTS−102 3%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 46%
Yが炭素数5のアルキルである化合物(3−1−6) 4%
DTS−102 3%
E−6OBEB(DCF3)ErBO6−E 10%
X(2)−1O4OBEFL(1)ErBO4O1−X(2) 10%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 34%
Yが炭素数5のアルキルであり、v=5である化合物(3−1−10 10%
DTS−102 3%
X(1)−1O4OBBC 43%
Yが炭素数5のアルキルである化合物(3−1−6) 10%
DTS−102 3%
E−6OBEB(1)ErBO6−E 30%
X(1)−6OBEB(1)ErBO6−X(1) 42%
Yが炭素数5のアルキルである化合物(3−1−6) 10%
DTS−102 3%
E−2OBEBO2−E 20%
E−6OBEB(1)ErBO6−E 30%
X(1)−6OBEB(1)ErBO6−X(1) 31%
Yが炭素数3のアルキルである化合物(3−2−2) 6%
DTS−102 3%
E−2OBEBO2−E 15%
E−6OBEB(1)ErBO6−E 20%
X(1)−3HHB(F)F 29%
Yが炭素数3のアルキルである化合物(3−2−2) 13%
DTS−102 3%
X(1)−1O4OB(F)EB(DCF3)ErBr(F)O4O1−X(1)10%
X(1)−1O4OBEFL(1)ErBO4O1−X(1) 38%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 39%
DTS−102 3%
E−1O4OBBC 20%
X(1)−1O4OBEFL(1)ErBO4O1−X(1) 26%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 27%
DTS−102 3%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 8%
E−1O4OBEFL(1)ErBO4O1−E 39%
E−1O6OBEFL(1)ErBO6O1−E 40%
DTS−102 3%
E−1O6OBBr(F)BO6O1−E 34%
E−1O6OBTBTBO6O1−E 33%
X(1)−1O6OBEFL(1)ErBO6O1−X(1) 10%
DTS−102 3%
E−1O4OBEFL(1)ErBO4O1−E 34%
E−1O6OBEFL(1)ErBO6O1−E 33%
DTS−102 3%
X(2)−1O6OBEFL(1)ErBO6O1−X(2) 33%
X(2)−1O6OBBC 31%
DTS−102 3%
上記組成物を、トルエンとシクロペンタノンの混合溶媒(混合比(重量比)は2:1)に、20%の濃度で溶解し、(1)スピンコート法によってラビング処理を施したポリイミド付きガラス基板に塗布し、(2)バーコーターを用いて、ラビング処理を施したTACフィルムに塗布し、いずれの場合も、70℃、3分間の条件にて溶媒を除去し、大気中下で重合させることによって良好な配向性を有する光学異方性膜を得た。ガラス基板に形成した光学異方性膜は、正面のレタデーションが172nmでありホモジニアス配向であった。測定温度および測定波長は、25℃および550nmである。得られた異方性膜は、耐熱性試験において、レタデーション変化率が3%未満であり耐熱性に優れていた。また、密着性試験においても、残存した升目の数が100であり良好な結果となった。
E−1O4OBEFL(1)ErBO4O1−E 30%
X(2)−1O6OBEFL(1)ErBO6O1−X(2) 30%
Yが炭素数5のアルキルである化合物(3−1−7) 9%
DTS−102 1%
E−1O4OBEFL(1)ErBO4O1−E 23%
X(2)−1O4OB(F)EB(DCF3)ErBr(F)O4O1−X(2)23%
X(2)−1O6OBEFL(1)ErBO6O1−X(2) 22%
Yが炭素数5のアルキルである化合物(3−1−7) 9%
DTS−102 1%
E−1O4OBEFL(1)ErBO4O1−E 23%
X(2)−1O6OB(F)2EB(DCF3)Er2Br(F)O6O1−X(2)
化合物(2−2−236)
23%
X(2)−1O6OBEFL(1)ErBO6O1−X(2) 22%
Yが炭素数5のアルキルである化合物(3−1−7) 9%
DTS−102 1%
Claims (17)
- 第一成分として、オキシラニルを有する化合物、第二成分として、オキセタニルを有する化合物を含有する液晶組成物であって、オキシラニルを有する化合物が式(1−1)または(1−2)で示される化合物の何れかであり、オキセタニルを有する化合物が式(2−1)または(2−2)で示される化合物の何れかであり、そして液晶組成物の全重量に対して、第一成分が5〜95重量%であり、第二成分が5〜95重量%である液晶組成物:
式(1−1)および式(1−2)において、R1はフッ素または−CNであり;R2は水素であり;Z1は独立して、単結合または−O−であり;Z2は独立して、単結合または炭素数1〜5のアルキレンであり;Z3は独立して、単結合、−COO−、−OCO−、−OCO−CH=CH−、−CH=CH−COO−、−(CH2)2−COO−または−OCO−(CH2)2−であり;A1は独立して、1,4−シクロへキシレンまたは1,4−フェニレンであり、1,4−フェニレンにおける任意の水素はハロゲンまたはメチルで置き換えられてもよく;pは1〜3の整数である。
式(2−1)および式(2−2)において、R1はフッ素または−CNであり;R3はメチルであり;Z1は独立して、単結合または−O−であり;Z2は独立して、単結合または炭素数1〜5のアルキレンであり;Z3は独立して、単結合、−COO−、−OCO−、−OCO−CH=CH−、−CH=CH−COO−、−(CH2)2−COO−または−OCO−(CH2)2−であり;A1は独立して、1,4−シクロへキシレンまたは1,4−フェニレンであり、1,4−フェニレンにおける任意の水素はハロゲンまたはメチルで置き換えられてもよく;pは1〜3の整数である。 - 式(1−1)、(1−2)、(2−1)及び(2−2)において、p=1または2である請求項1に記載の液晶組成物。
- 式(1−1)、(1−2)、(2−1)及び(2−2)において、R1は−CNまたはFであり;R2は水素であり;R3はメチルであり;Z1は単結合または−O−であり;Z2はメチレン、エチレン、トリメチレン、テトラメチレンまたはペンタメチレンであり;Z3は単結合、−COO−または−OCO−であり;A1は1,4−フェニレン、2−フルオロ−1,4−フェニレン、3−フルオロ−1,4−フェニレン、2,3−ジフルオロ−1,4−フェニレン、2−メチル−1,4−フェニレン、3−メチル−1,4−フェニレン、2,3−ジメチル−1,4−フェニレンまたは1,4−シクロヘキシレンであり;pは1または2である請求項1に記載の液晶組成物。
- 第三成分として、式(3−1)または(3−2)で表される光学活性を有する化合物を更に含有する請求項1〜3の何れか1項に記載の液晶組成物。
ここで、P1は、独立して、水素または(C)であり、ただし、P1の中で少なくとも2つは(C)であり;P2は(C)であり;R4は、炭素数1〜5のアルキルであり、このアルキル中の任意の−CH2−は、−O−で置き換えられてもよく、このアルキル中の1つの水素はオキセタニルで置き換えられてもよく;Z5は独立して、単結合、−O−、−COO−または−OCO−であり;X2は水素であり;A3は独立して、1,4−シクロへキシレンまたは1,4−フェニレンであり;sは0であり;tは1〜3の整数である。 - 非重合性の液晶性化合物を含有する請求項1〜5の何れか1項に記載の液晶組成物。
- 重合性化合物のみからなる請求項1〜3及び5の何れか1項に記載の液晶組成物。
- 非重合性の液晶性化合物を含有する請求項6に記載の液晶組成物から得られる重合体組成物。
- 重合性化合物のみからなる請求項7に記載の液晶組成物から得られる重合体。
- 1μm以上200μm未満のピッチを有する請求項8に記載の重合体組成物。
- 1μm以上200μm未満のピッチを有する請求項9に記載の重合体。
- 選択反射の波長域が350nm以上800nm未満である請求項8に記載の重合体組成物。
- 選択反射の波長域が350nm以上800nm未満である請求項9に記載の重合体。
- 選択反射の波長域が350nm未満である請求項8に記載の重合体組成物。
- 選択反射の波長域が350nm未満である請求項9に記載の重合体。
- 請求項8、10、12若しくは14の何れか1項に記載の重合体組成物または請求項9、11、13若しくは15の何れか1項に記載の重合体からなるフィルム。
- 請求項16に記載のフィルムを用いた光学補償素子。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004331414A JP4945894B2 (ja) | 2003-11-19 | 2004-11-16 | 光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003388976 | 2003-11-19 | ||
JP2003388976 | 2003-11-19 | ||
JP2004331414A JP4945894B2 (ja) | 2003-11-19 | 2004-11-16 | 光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005171235A JP2005171235A (ja) | 2005-06-30 |
JP4945894B2 true JP4945894B2 (ja) | 2012-06-06 |
Family
ID=34741914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004331414A Expired - Fee Related JP4945894B2 (ja) | 2003-11-19 | 2004-11-16 | 光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4945894B2 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006273989A (ja) * | 2005-03-29 | 2006-10-12 | Sumitomo Chemical Co Ltd | エポキシ化合物およびエポキシ樹脂硬化物 |
JP2007039414A (ja) * | 2005-08-05 | 2007-02-15 | Chisso Corp | 軸不斉シクロヘキサン光学活性化合物、液晶組成物、液晶表示素子、成形体 |
JP2007121996A (ja) * | 2005-09-28 | 2007-05-17 | Fujifilm Corp | 光学補償シートならびに、これを用いた偏光板および液晶表示装置 |
ATE479735T1 (de) | 2006-10-12 | 2010-09-15 | Merck Patent Gmbh | Flüssigkristallanzeige |
KR101065916B1 (ko) * | 2007-05-22 | 2011-09-19 | 주식회사 엘지화학 | 중합성 액정 조성물 및 이를 사용한 광학 필름 및 장치 |
JP5493629B2 (ja) * | 2008-11-07 | 2014-05-14 | Jnc株式会社 | 重合性液晶組成物 |
WO2011007669A1 (ja) | 2009-07-17 | 2011-01-20 | チッソ株式会社 | 光反応性基を有する液晶性ポリイミドよりなる位相差膜を有する液晶表示装置 |
JP5750861B2 (ja) * | 2009-12-17 | 2015-07-22 | Jnc株式会社 | オキシラニル基を有する重合性液晶化合物、重合性液晶組成物および重合体 |
US8877302B2 (en) | 2011-11-29 | 2014-11-04 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal composition, liquid crystal element, and liquid crystal display device |
US8968841B2 (en) | 2012-03-29 | 2015-03-03 | Semiconductor Energy Laboratory Co., Ltd. | Binaphthyl compound, liquid crystal composition, liquid crystal element, and liquid crystal display device |
JP2014019654A (ja) * | 2012-07-13 | 2014-02-03 | Dic Corp | 重合性アセチレン化合物 |
JP6337497B2 (ja) * | 2014-02-18 | 2018-06-06 | Dic株式会社 | 重合性化合物及び光学異方体 |
WO2019160016A1 (ja) * | 2018-02-14 | 2019-08-22 | 富士フイルム株式会社 | 光学フィルム、偏光板および画像表示装置 |
KR20220022356A (ko) | 2020-08-18 | 2022-02-25 | 삼성전자주식회사 | 에폭시 화합물, 이로부터 얻어지는 조성물, 반도체 장치, 전자 장치, 물품 및 물품 제조 방법 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3999400B2 (ja) * | 1999-03-31 | 2007-10-31 | 富士フイルム株式会社 | コレステリック液晶性組成物および液晶表示装置 |
EP1337602B1 (en) * | 2000-10-04 | 2006-04-12 | Koninklijke Philips Electronics N.V. | Polymerizable liquid crystalline dioxetanes, their preparation and use |
JP4576832B2 (ja) * | 2003-01-06 | 2010-11-10 | チッソ株式会社 | 重合性化合物およびその重合体 |
JP4569189B2 (ja) * | 2003-06-23 | 2010-10-27 | チッソ株式会社 | 液晶性化合物、液晶組成物およびそれらの重合体 |
JP4561218B2 (ja) * | 2003-07-30 | 2010-10-13 | チッソ株式会社 | 光硬化性フルオレン誘導体およびそれらを含む組成物 |
JP4576928B2 (ja) * | 2003-08-29 | 2010-11-10 | チッソ株式会社 | 光学活性な液晶性化合物、組成物及びそれらの重合体 |
-
2004
- 2004-11-16 JP JP2004331414A patent/JP4945894B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2005171235A (ja) | 2005-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7425354B2 (en) | Photopolymerizable liquid crystal composition, its polymer or polymer composition, and optical compensation element | |
JP4788123B2 (ja) | 光重合性液晶組成物、その重合体または重合体組成物及び光学異方性膜 | |
JP6525031B2 (ja) | 重合性組成物及びそれを用いた光学異方体 | |
KR101441092B1 (ko) | 중합성 조성물 | |
JP4945894B2 (ja) | 光重合性液晶組成物、その重合体または重合体組成物及び光学補償素子 | |
US7407691B2 (en) | Photopolymerizable oxetane derivative and liquid-crystal composition containing it | |
EP2039707B1 (en) | Polymerizable composition | |
JP5293979B2 (ja) | 重合性ビナフタレン誘導体 | |
EP2660631B1 (en) | Birefringent lens material for stereoscopic image display device, and method of manufacturing birefringent lens for stereoscopic image display device | |
JP4561218B2 (ja) | 光硬化性フルオレン誘導体およびそれらを含む組成物 | |
JP2008100982A (ja) | 三官能性化合物、組成物およびその重合体 | |
JPWO2019003934A1 (ja) | 重合性液晶組成物、それを用いた光学フィルム、及びその製造方法。 | |
JP6547912B2 (ja) | 重合性組成物、及び、それを用いた光学異方体 | |
JP2005263778A (ja) | 重合性ビナフタレン誘導体 | |
KR20170103775A (ko) | 중합성 액정 조성물 및 당해 조성물을 사용해서 제작한 광학 이방체, 위상차막, 반사 방지막, 액정 표시 소자 | |
JP2006342332A (ja) | 環状エーテル系重合性液晶組成物、ホメオトロピック配向液晶フィルム、およびホメオトロピック配向液晶フィルムの製造方法 | |
JP2003055661A (ja) | 重合性液晶組成物及びこれを用いた光学異方体 | |
US7794802B2 (en) | Polymerizable liquid crystal compound, composition and polymer | |
JP4412084B2 (ja) | ホメオトロピック配向液晶フィルム | |
US7560146B2 (en) | Polymerizable liquid crystal composition | |
JP5051417B2 (ja) | 光開始剤及び重合性組成物 | |
JP7251197B2 (ja) | 重合性液晶化合物、重合性組成物、重合体、位相差フィルム及びその製造方法、転写用積層体、光学部材及びその製造方法、並びに表示装置 | |
WO2022173034A1 (ja) | インキ組成物、物品及びその製造方法 | |
JP2010217356A (ja) | 光学異方性膜、液晶セル用基板、及び液晶表示装置 | |
JP5070797B2 (ja) | 側方オキシラン化合物およびその重合体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070604 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20101116 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101220 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20110331 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110405 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110419 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120207 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120220 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150316 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4945894 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |