JP6648438B2 - 液晶性化合物、液晶組成物およびその重合体 - Google Patents
液晶性化合物、液晶組成物およびその重合体 Download PDFInfo
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- JP6648438B2 JP6648438B2 JP2015152078A JP2015152078A JP6648438B2 JP 6648438 B2 JP6648438 B2 JP 6648438B2 JP 2015152078 A JP2015152078 A JP 2015152078A JP 2015152078 A JP2015152078 A JP 2015152078A JP 6648438 B2 JP6648438 B2 JP 6648438B2
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- 150000001875 compounds Chemical class 0.000 title claims description 314
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 223
- 239000000203 mixture Substances 0.000 title claims description 208
- 229920000642 polymer Polymers 0.000 title claims description 27
- -1 pyridine-2,5-diyl Chemical group 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 230000003287 optical effect Effects 0.000 claims description 40
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000005907 alkyl ester group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001589 carboacyl group Chemical group 0.000 claims description 22
- 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 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 15
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 15
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- 239000010408 film Substances 0.000 description 138
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000002904 solvent Substances 0.000 description 52
- 239000012044 organic layer Substances 0.000 description 47
- 239000000758 substrate Substances 0.000 description 43
- 239000012299 nitrogen atmosphere Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
- 239000006185 dispersion Substances 0.000 description 30
- 230000007704 transition Effects 0.000 description 30
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 26
- 238000000576 coating method Methods 0.000 description 24
- 238000001914 filtration Methods 0.000 description 24
- 239000010410 layer Substances 0.000 description 24
- 239000011248 coating agent Substances 0.000 description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000011259 mixed solution Substances 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 0 CC(C)c1ccc(C(C)=C)c2c1C=C(C)I*2 Chemical compound CC(C)c1ccc(C(C)=C)c2c1C=C(C)I*2 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000002736 nonionic surfactant Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 230000001747 exhibiting effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920006254 polymer film Polymers 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 239000002985 plastic film Substances 0.000 description 6
- 229920006255 plastic film Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 5
- 239000012986 chain transfer agent Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000004210 ether based solvent Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 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 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000009832 plasma treatment Methods 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- HZQLUIZFUXNFHK-UHFFFAOYSA-N 1-(bromomethyl)-4-phenylbenzene Chemical group C1=CC(CBr)=CC=C1C1=CC=CC=C1 HZQLUIZFUXNFHK-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000004001 thioalkyl group Chemical group 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-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
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 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
- PWSZACWUDDFZMQ-UHFFFAOYSA-N 2,4-Diphenyl-1-butene Chemical compound C=1C=CC=CC=1C(=C)CCC1=CC=CC=C1 PWSZACWUDDFZMQ-UHFFFAOYSA-N 0.000 description 2
- FIOCEWASVZHBTK-UHFFFAOYSA-N 2-[2-(2-oxo-2-phenylacetyl)oxyethoxy]ethyl 2-oxo-2-phenylacetate Chemical compound C=1C=CC=CC=1C(=O)C(=O)OCCOCCOC(=O)C(=O)C1=CC=CC=C1 FIOCEWASVZHBTK-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
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- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
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- 238000004904 shortening Methods 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Description
光軸方向の屈折率がその直交する方向の屈折率より大きいため、屈折率楕円体では、ポジティブC−プレートに分類される。このポジティブC−プレートは、他の光学機能を有するフィルムと組み合わせることによって、水平配向した液晶モードいわゆるIPS(In-Plane Switching)モード等の光学補償、例えば偏光板の視野角特性の改善に応用できる(非特許文献1〜3、特許文献2および3)。
A1およびA2はそれぞれ独立して1,4−フェニレン、1,4−シクロへキシレン、1,4−シクロへキセニレン、ピリジン−2,5−ジイルまたはナフタレン−2,6−ジイルであり、これらにおいて、少なくとも一つの水素はフッ素、塩素、シアノ、ヒドロキシ、ホルミル、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
Z1およびZ2はそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−COS−、−SCO−、−OCOO−、−CONH−、−NHCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−OCH2CH2O−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−OCOCH2CH2−、−CH2CH2OCO−、−COOCH2CH2−、−CH=CH−、−N=CH−、−CH=N−、−N=CCH3−、−CCH3=N−、−N=N−または−C≡C−であり;
mおよびnは、それぞれ独立して0〜3の整数であり、かつ1≦m+n≦4の関係であり;
X1は−O−、−S−または−NR3−であり、R3は水素、炭素数1〜5のアルキル、または炭素数1〜5のアルカノイルであり;
Q1は水素、ハロゲンまたは1価の有機基であり;
R1およびR2はそれぞれ独立して水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数2〜20のアルケニル、炭素数1〜20のアルコキシ、炭素数1〜20のアルキルエステルまたは式(2)で表される基である。
[2] 式(1)中、Q1が式(3)または(4)で表される基である [1]に記載の化合物。
Z3はそれぞれ独立して単結合、−COO−または−COS−であり;
Z4はそれぞれ独立して単結合、−CH=CH−、−N=CH−、−CH=N−、−N=CCH3−、−CCH3=N−、−N=N−または−C≡C−であり;
R5は水素、フッ素、塩素、シアノ、炭素数1〜20のアルキルであり、該アルキルにおいて−CH2−は−O−、−S−、−CO−、−COO−、−OCO−、−OCOO−、で置き換えられてもよく、該アルキルにおいて水素はハロゲンで置き換えられてもよく;
A3はそれぞれ独立して、2価の、5員環もしくは6員環の芳香環、またはそれらの縮合環であり、A4は1価の、5員環若しくは6員環の芳香環、またはそれらの縮合環であり、A3およびA4における芳香環またはそれらの縮合環の少なくとも一つの水素はフッ素、塩素、シアノ、ニトロ、トリフルオロメチル、トリフルオロメトキシ、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステル、炭素数1〜5のアルカノイルまたは炭素数1〜5のチオアルキルで置き換えられてもよく;
pは0〜2の整数である。)
[4] 式(1)中、X1が−S−である、[1]〜[3] のいずれか1項に記載の化合物。
Z1およびZ2がそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−OCOCH2CH2−、−CH2CH2OCO−または−COOCH2CH2−である、[1]〜[4]のいずれか1項に記載の化合物。
[7] 式(1)中、A1およびA2のうち少なくとも一つが1,4−シクロへキシレンである、[1]〜[6] のいずれか1項に記載の化合物。
[12] [1]〜[10] のいずれか1項に記載の化合物の少なくとも1つと、式(M1)および式(M2)で表される化合物群から選ばれる少なくとも1つとを含有する液晶組成物。
AMはそれぞれ独立して1,4−フェニレン、1,4−シクロへキシレン、1,4−シクロへキセニレン、ピリジン−2,5−ジイル、ナフタレン−2,6−ジイル、フルオレノン−2,7−ジイルまたはフルオレン−2,7−ジイルであり、これらにおいて、少なくとも一つの水素はフッ素、塩素、シアノ、ヒドロキシ、ホルミル、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
ZMはそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−COS−、−SCO−、−OCOO−、−CONH−、−NHCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−OCOCH2CH2−、−CH=CH−、−N=CH−、−CH=N−、−N=CCH3−、−CCH3=N−、−N=N−または−C≡C−であり;
XMは水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数2〜20のアルケニル、炭素数1〜20のアルコキシまたは炭素数1〜20のアルキルエステルであり;
qは1〜4の整数であり;
aは0〜20の整数であり;
RMは水素またはメチルであり;
YMは単結合、−O−、−COO−、−OCO−または−OCOO−である。)
AMは独立して1,4−フェニレンまたは1,4−シクロへキシレンであるが、AMのうち少なくとも一つは1,4−シクロへキシレンであり、これらにおいて、少なくとも一つの水素はフッ素、塩素、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
ZMはそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−CH2CH2−、−CH2CH2COO−または−OCOCH2CH2−であり;
qは1または2の整数であり;
XMは水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数1〜20のアルケニル、炭素数1〜20のアルコキシまたは炭素数1〜20のアルキルエステルであり;
aは0〜20の整数であり;
RMは水素またはメチルであり
YMは単結合、−O−、−COO−、−OCO−または−OCOO−である。)
[15] [11]〜[14]のいずれか1項に記載の液晶組成物において、さらに二色性色素化合物を少なくとも1つ含有する液晶組成物。
[16] [11]〜[15]のいずれか1項に記載の液晶組成物に紫外光を照射して得られる重合体。
[17] [16]に記載の重合体が光学的異方性を有する光学異方性フィルム。
[18] [17]に記載の光学異方性フィルムを有する偏光板。
[19] [17]に記載の光学異方性フィルムを有する表示素子。
[20] [18]に記載の偏光板を有する表示素子。
本発明の効果である屈折率異方性の波長分散制御の目的には、一般式(1)で表される化合物が用いられる。この時これらの一般式(1)で表される化合物から1種類を選択しても良いが、2種類以上を選択し用いても良い。
式(1−1−1)〜式(1−3−5)において、R3は水素、炭素数1〜5のアルキル、炭素数1〜5のアルカノイルであり、R5は水素、フッ素、塩素、シアノ、炭素数1〜20のアルキルであり、該アルキルにおいて−CH2−は−O−、−S−、−CO−、−COO−、−OCO−、−OCOO−、で置き換えられてもよく、該アルキルにおいて水素はハロゲンで置き換えられてもよく、R6は水素、フッ素、塩素、シアノ、ニトロ、トリフルオロメチル、トリフルオロメトキシ、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステル、炭素数1〜5のアルカノイルまたは炭素数1〜5のチオアルキルである。
本発明の液晶組成物は、式(1)で表される化合物の群から選択される少なくとも1つの化合物を含有する。本発明の液晶組成物は、比較的低い温度でネマチック相やスメクチック相の液晶相を有する。本発明の液晶組成物を、ラビング処理等の配向処理がなされているプラスチック基板上やプラスチックの薄膜で表面が被覆された支持基板上に塗工して製膜する場合、ホモジニアス配向やハイブリッド配向となる。また、本発明の液晶組成物に、後述する非重合性あるいは重合性の光学活性化合物を添加した場合にはツイスト配向となる。本発明の液晶組成物に後述するカルド構造を有する化合物、または単官能の液晶化合物を加えるとホメオトロピック配向が得られやすくなる。
aは0〜20の整数であり;RMは水素またはメチルであり;YMは単結合、−O−、−COO−、−OCO−または−OCOO−である。
上記式(M1)および(M2)で表される化合物において、式(M1)で表される化合物の方がより好ましく、式(M1)中、AMは独立して1,4−フェニレンまたは1,4−シクロへキシレンであるが、AMのうち少なくとも一つは1,4−シクロへキシレンであり、該1,4−フェニレンまたは1,4−シクロへキシレンにおいて、少なくとも一つの水素はフッ素、塩素、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;ZMはそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−CH2CH2−、−CH2CH2COO−または−OCOCH2CH2−であり;qは1または2の整数であり;XMは水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数1〜20のアルケニル、炭素数1〜20のアルコキシまたは炭素数1〜20のアルキルエステルであり;aは0〜20の整数であり;RMは水素またはメチルであり;YMは単結合、−O−、−COO−、−OCO−または−OCOO−である化合物が好ましい。
本発明の液晶組成物は、さらに界面活性剤を含んでもよい。界面活性剤としては非イオン性界面活性剤が好ましく、非イオン性界面活性剤が液晶組成物に含まれた場合には、その液晶組成物から形成される塗布膜の平滑性を向上させる効果がある。
シリコーン系非イオン性界面活性剤の市販品としては、例えば、未変性シリコーンあるいは変性シリコーンを主成分とした共栄社化学(株)製のポリフローATF―2、グラノール100、グラノール115、グラノール400、グラノール410、グラノール435、グラノール440、グラノール450、グラノールB−1484、ポリフローKL−250、ポリフローKL−260、ポリフローKL−270、ポリフローKL−280、BYK−300、BYK−302、BYK−306、BYK−307、BYK−310、BYK−315、BYK−320、BYK−322、BYK−323、BYK−325、BYK−330、BYK−331、BYK−333、BYK−337、BYK−341、BYK−342、BYK−344、BYK−345、BYK−346、BYK−347、BYK−348、BYK−370、BYK−375、BYK−377、BYK−378、BYK−3500、BYK−3510、およびBYK−3570などが挙げられる。
次に、その他の重合性化合物、添加物、有機溶剤を例示する。これらの化合物は市販品でもよい。
液晶組成物には、保存時の重合開始を防止するために重合防止剤を添加することができる。公知の重合防止剤を使用できるが、その好ましい例は、2,5−ジ(t−ブチル)ヒドロキシトルエン(BHT)、ハイドロキノン、メチレンブルー、ジフェニルピクリン酸ヒドラジド(DPPH)、フェノチアジン、N,N−ジメチル−4−ニトロソアニリンなどのニトロソ化合物、o−ヒドロキシベンゾフェノン、および2H−1,3−ベンゾチアジン−2,4−(3H)ジオンなどのベンゾチアジン誘導体である。
紫外線吸収剤としては、例えば、チヌビンPS、チヌビンP、チヌビン99−2、チヌビン109、チヌビン213、チヌビン234、チヌビン326、チヌビン328、チヌビン329、チヌビン384−2、チヌビン571、チヌビン900、チヌビン928、チヌビン1130、チヌビン400、チヌビン405、チヌビン460、チヌビン479、チヌビン5236、アデカスタブLA−32、アデカスタブLA−34、アデカスタブLA−36、アデカスタブLA−31、アデカスタブ1413、およびアデカスタブLA−51などが挙げられる。「チヌビン」はBASFジャパン(株)の商品名であり、「アデカスタブ」はADEKAの商品名である。これら紫外線吸収剤は単独で使用してもよく、2つ以上を混合して使用してもよい。また、これら紫外線吸収剤は市販品であってもよい。
アセテート系溶剤としては、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、アセト酢酸メチル、および1−メトキシ−2−プロピルアセテートなどが好ましい。
液晶フィルムは、液晶表示素子(特に、アクティブマトリックス型およびパッシブマトリックス型の液晶表示素子)に適用する光学補償素子として有効である。この液晶フィルムを光学補償膜として使用するのに適している液晶表示素子の型の例は、IPS型(イン・プレーン・スイッチング)、OCB型(光学的に補償された複屈折)、TN型(ツィステッド・ネマティック)、STN型(スーパー・ツィステッド・ネマティック)、ECB型(電気的に制御された複屈折)、DAP型(整列相の変形効果)、CSH型(カラー・スーパー・ホメオトロピック)、VAN/VAC型(垂直配向したネマチック/コレステリック)、OMI型(光学モード干渉)、SBE型(超複屈折効果)などである。さらにゲスト−ホスト型、強誘電性型、反強誘電性型などの表示素子用の位相レターダーとして、この液晶フィルムを使用することもできる。なお、液晶フィルムに求められるチルト角の厚み方向の分布や厚みなどのパラメーターの最適値は、補償すべき液晶表示素子の種類とその光学パラメーターに強く依存するので、素子の種類によって異なる。
<化合物の構造確認>
500MHzのプロトンNMR(ブルカー:DRX-500)の測定により合成した化合物の構造を確認した。記載した数値はppmを表し、sはシングレット、dはダブレット、tはトリプレット、mはマルチプレットを表す。
偏光顕微鏡を備えた融点測定装置のホットプレートに試料を置き、3℃/分の速度で昇温した。相が別の相に転移する温度を測定した。Cは結晶、Nはネマチック相、Sはスメクチック相、Iは等方性液体を意味する。NI点は、ネマチック相の上限温度またはネマチック相から等方性液体への転移温度である。「C 50 N 63 I」は、50℃で結晶からネマチック相に転移し、63℃でネマチック相から等方性液体へ転移したことを示す。括弧内はモノトロピックの液晶相を示す。
窒素雰囲気下において、室温で250Wの超高圧水銀灯(ウシオ電機社製、マルチライト−250)を用いて30mW/cm2(365nm)の強度の光を30秒間照射した。
(1)ラビング処理済み配向膜付きガラス基板の作製
厚さ1.1mmのガラス基板に、低プレチルト角(水平配向モード)用ポリアミック酸(リクソンアライナー:PIA−5370 JNC(株)製)をスピンコートし、スピンコートした塗膜から溶剤を80℃のホットプレート上で除去後、該塗膜を230℃で30分間、オーブンで焼成したものを、レーヨン布を利用してラビング処理した。
クロスニコルに配置した2枚の偏光板の間に位相差フィルムを形成した基板を挟持して観察し、基板を水平面内で回転させ、明暗の状態を確認した。位相差フィルムを形成した基板を偏光顕微鏡観察し、配向欠陥の有無を確認した。
シンテック(株)製のOPTIPRO偏光解析装置を用い、位相差フィルムを形成した基板に波長が550nmおよび450nmの光を照射した。これらの光の入射角度をフィルム面に対して90°から減少させながらレタデーションを測定した。レタデーション(retardation;位相遅れ、リタデーションとも呼ばれる)はΔn×dで表される。記号Δnは光学異方性値であり、記号dは重合体フィルムの厚さである。
液晶フィルム付きガラス基板の液晶フィルムの層を削りだして、その段差を微細形状測定装置(KLA TENCOR(株)製 アルファステップIQ)を用いて測定した。
ホモジニアス配向を有する液晶フィルムについて求めた光の入射角度がフィルム面に対して90°の時のレタデーションと膜厚値から、光学異方性(Δn)=レタデーション(Re)/膜厚(d)として算出した。
波長分散の特性として、以下の式から求められる値を指標とした。
波長分散の特性=450nmの光で測定したリタデーション(Re450nm)/550nmの光で測定したリタデーション(Re550nm)。
すなわち、上記波長分散の特性値が小さい方が、低波長分散性が高く、1以下の値の場合に逆波長分散特性を有することを示す。
JIS規格「JIS−K−5400 8.4 鉛筆引掻試験」の方法に準じて測定した。すなわち、鉛筆硬度計(吉光精機製C−221)を用い、45°の角度で固定した鉛筆(三菱鉛筆(株)Uni)の芯による引掻きで、キズが生じる時の鉛筆の芯の硬さを測定した。
相転移温度(℃):C 95 I
1H-NMR(CDCl3;δppm):7.96(s,1H),7.28(d,1H),7.17(d,1H),3.92(s,3H),2.65−2.55(m,2H),2.22(d,4H),1.92(d,4H),1.68−1.57(m,4H),1.38−1.19(m,18H),1.07−0.97(m,4H),0.90(t,6H).
下記に示す化合物(1−1−19−1)を以下のようにして合成した。
化合物(ex−3)5.0g、フェノール2.0g、およびDMAP0.5gを、ジクロロメタン50mLに加え、窒素雰囲気下冷却しながら撹拌した。そこへ、DCC4.5gのジクロロメタン溶液10mLを滴下した。滴下後、室温で16時間撹拌した。析出した沈殿物を濾別し、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した。減圧下でジクロロメタンを留去し、残査をカラムクロマトグラフィー(シリカゲル、溶離液:トルエン)で精製し、メタノールで再結晶することにより、化合物(ex−4)4.8gを得た。
相転移温度(℃):C 110 I
1H-NMR(CDCl3;δppm):8.08(s,1H),7.45(t,2H),7.31(d,2H),7.27−7.22(m,2H),7.19(d,1H),2.65−2.56(m,2H),2.22(d,4H),1.92(d,4H),1.69−1.58(m,4H),1.36−1.19(m,18H),1.07−0.97(m,4H),0.89(t,6H).
下記に示す化合物(1−1−7−1)を以下のようにして合成した。
化合物(ex−7)5.0g、ベンジルメルカプタン3.2g、および水酸化カリウム2.9gを、N,N−ジメチルホルムアミド(DMF)50mlに加え、窒素雰囲気下100℃で加熱しながら4時間撹拌した。反応液に水を注ぎこみ、析出物を濾別し、水およびメタノールで洗浄した。得られた結晶を、トルエンおよびメタノールの混合溶液で再結晶することにより、化合物(ex−8)3.5gを得た。
相転移温度(℃):C 62 I
1H-NMR(CDCl3;δppm):7.69(s,2H),7.46(t,2H),7.41(t,1H),7.36(s,1H),7.26−7.20(m,2H),6.44(d,2H),6.19−6.12(m,2H),5.86(d,2H),4.88−4.80(m,2H),4.20(t,4H),2.76−2.67(m,2H),2.38−2.28(m,8H),2.21−2.13(m,4H),1.90−1.79(m,4H),1.77−1.68(m,8H),1.59−1.42(m,8H).
下記に示す化合物(1−1−5−1)を以下のようにして合成した。
相転移温度(℃):C 129 N 180 < I
(“180 < I”は、180℃付近で重合してしまい透明点が測定不能であるが、仮に重合することがなければ、180℃以上にネマチック相から等方性液体への転移温度があると予想される、という意味である)
1H-NMR(CDCl3;δppm):7.70(d,2H),7.44(t,2H),7.41−7.36(m,2H),7.16−7.11(m,2H),7.00(d,4H),6.90(d,4H),6.41(d,2H),6.17−6.09(m,2H),5.83(d,2H),4.24(t,4H),3.99(t,4H),2.78−2.69(m,2H),2.67−2.59(m,2H),2.43−2.30(m,8H),1.93−1.67(m,16H).
下記に示す化合物(1−1−6−1)を以下のようにして合成した。
相転移温度(℃):C 90 (N 70 ) I
1H-NMR(CDCl3;δppm):7.67(d,2H),7.44(t,2H),7.38(t,1H),7.33(s,1H),7.15−7.08(m,6H),6.83(d,4H),6.40(d,2H),6.17−6.08(m,2H),5.81(d,2H),4.85−4.76(m,2H),4.17(t,4H),3.94(t,4H),2.90(t,4H),2.73−2.65(m,2H),2.62(t,4H),2.31−2.24(m,4H),2.15−2.07(m,4H),1.86−1.67(m,12H),1.56−1.41(m,12H).
下記に示す化合物(1−1−6−2)を実施例3に記載の合成法においてベンジルメルカプタンを4‐クロロベンジルメルカプタンに変更した以外は同様な方法で合成した。
相転移温度(℃):C 90 (N 39 ) I
1H-NMR(CDCl3;δppm):7.60(d,2H),7.41(d,2H),7.30(s,1H),7.15−7.08(m,6H),6.82(d,4H),6.40(d,2H),6.16−6.09(m,2H),5.81(d,2H),4.84−4.76(m,2H),4.17(t,4H),3.94(t,4H),2.90(t,4H),2.72−2.58(m,6H),2.31−2.23(m,4H),2.15−2.07(m,4H),1.86−1.67(m,12H),1.56−1.42(m,12H).
下記に示す化合物(1−1−15−1)を以下のようにして合成した。
相転移温度(℃):C 104 (N 79 ) I
1H-NMR(CDCl3;δppm):8.10(d,1H),7.91(d,1H),7.71(s,1H),7.53(t,1H),7.44(t,1H),7.24(d,1H),7.18−7.11(m,5H),6.83(d,4H),6.40(d,2H),6.16−6.09(m,2H),5.81(d,2H),4.87−4.77(m,2H),4.17(t,4H),3.94(t,4H),2.92(t,4H),2.77−2.58(m,6H),2.34−2.24(m,4H),2.18−2.09(m,4H),1.87−1.67(m,12H),1.57−1.42(m,12H).
下記に示す化合物(1−1−20−1)を以下のようにして合成した。
相転移温度(℃):C 103 I
1H-NMR(CDCl3;δppm):7.75(d,2H),7.69−7.62(m,4H),7.48(t,2H),7.41−7.36(m,2H),7.15−7.09(m,6H),6.83(d,4H),6.40(d,2H),6.16−6.08(m,2H),5.82(d,2H),4.85−4.77(m,2H),4.17(t,4H),3.94(t,4H),2.91(t,4H),2.74−2.57(m,6H),2.33−2.25(m,4H),2.16−2.08(m,4H),1.87−1.66(m,12H),1.55−1.41(m,12H).
下記に示す化合物(1−1−6−3)を実施例8に記載の合成法において4−ブロモメチルビフェニルを4−シアノベンジルブロミドに変更した以外は同様の方法で合成した。
相転移温度(℃):C 109 I
1H-NMR(CDCl3;δppm):7.78(d,2H),7.73(m,2H),7.44(s,1H),7.19−7.08(m,6H),6.93(d,4H),6.40(d,2H),6.16−6.08(m,2H),5.82(d,2H),4.85−4.77(m,2H),4.17(t,4H),3.94(t,4H),2.91(t,4H),2.74−2.57(m,6H),2.33−2.23(m,4H),2.16−2.07(m,4H),1.87−1.66(m,12H),1.55−1.41(m,12H).
下記に示す化合物(1−1−6−4)を実施例8に記載の合成法において4−ブロモメチルビフェニルを4−トリフルオロメチルベンジルブロミドに変更した以外は同様の方法で合成した。
相転移温度(℃):C 119 (N 35) I
1H-NMR(CDCl3;δppm):7.78(d,2H),7.70(m,2H),7.41(s,1H),7.18−7.10(m,6H),6.83(d,4H),6.40(d,2H),6.16−6.08(m,2H),5.82(d,2H),4.85−4.77(m,2H),4.17(t,4H),3.94(t,4H),2.91(t,4H),2.74−2.57(m,6H),2.33−2.23(m,4H),2.16−2.07(m,4H),1.87−1.66(m,12H),1.55−1.41(m,12H).
下記に示す化合物(1−1−21−1)を以下のようにして合成した。
相転移温度(℃):C 122 (N 99) I
1H-NMR(CDCl3;δppm):8.17(d,2H),7.90(s,1H),7.63−7.55(m,3H),7.30(d,1H),7.21(d,1H),7.13(d,4H),6.84(d,4H),6.40(d,2H),6.16−6.08(m,2H),5.82(d,2H),4.85−4.77(m,2H),4.17(t,4H),3.94(t,4H),2.91(t,4H),2.74−2.57(m,6H),2.33−2.25(m,4H),2.16−2.08(m,4H),1.87−1.66(m,12H),1.55−1.41(m,12H).
[実施例12]
上記合成した本発明化合物と以下に示す化合物(M2−7−1)、(M1−15−1)、(M1−16−1)および(M1−17−1)を用いて液晶組成物(S−1〜S−12)を作製した。
実施例12に記載の方法と同様に上記化合物(M2−7−1)、(M1−15−1)および(M1−16−1)と下記化合物(C−1)を用いて液晶組成物(SC−1〜SC−3)を作製した
[実施例14]
実施例12および実施例13で作製した液晶組成物(S−1)〜(S−12)を、ラビング処理済配向膜付きガラス基板上へスピンコートにより塗布した。この基板を80℃で2分間加熱し、室温で1分間冷却し、溶剤が除去した重合性液晶層を空気中で紫外線により重合させて、液晶の配向状態を固定させた光学異方性フィルムを得た。これら得られた光学異方フィルムを偏光顕微鏡観察および偏光解析装置で確認したところ、配向欠陥がなく均一なホモジニアス配向を有していた。
実施例14に記載の方法と同様に、比較例1で作製した液晶組成物(SC−1)〜(SC−3)から光学異方性フィルムを得た。これら得られた光学異方フィルムを偏光顕微鏡観察および偏光解析装置で確認したところ、(SC−1)および(SC−2)は配向欠陥がなく均一なホモジニアス配向を有していることが確認できた。(SC−3)は結晶が析出し配向欠陥が生じ均一なホモジニアス配向を有する膜は得られなかった。
[実施例15〜26、比較例3〜4]
実施例14および比較例2で作製した光学異方性フィルムのフィルム面に対して90度のレタデーションの波長450nmの測定値(Re450)および波長550nmの測定値(Re550)、膜厚、波長550nmでのΔn、および波長分散特性を表4および表5に示す。
実施例14および比較例2で作製した光学異方性フィルムを200℃30分焼成後のフィルム面に対して90度の波長550nmのレタデーションを測定した結果を表6および7に示す。ここで表6および7中、残存Reは初期のRe値を100としたときの200℃30分焼成後のReの値を示す。
実施例14および比較例2で作製した光学異方性フィルムの膜表面の機械的強度を鉛筆硬度試験により測定した結果を表8および9に示す。ここで表8および9中、硬度(平行)は光学異方性フィルムの配向方向と平行な方向に引掻いた場合のキズが生じる時の鉛筆の芯の型さを示し、硬度(垂直)は光学異方性フィルムの配向方向と垂直な方向に引掻いた場合のキズが生じる時の鉛筆の芯の硬さを示す。
[実施例27]
本発明化合物と以下に示す化合物(M2−1−1)および(M1−12−1)を用いて液晶組成物(S−13)を作製した。
[実施例28]
実施例27で作製した液晶組成物(S−13)を、ガラス基板(松浪スライドガラス:S−1112)上にスピンコートにより塗布した。この基板を80℃で2分間加熱、室温で1分間冷却し、溶剤が除去された塗膜を紫外線により窒素気流下で重合させて、均一なホメオトロピック配向を有する液晶フィルムを得た。
[実施例29]
実施例28で作成した光学異方性フィルムのフィルム面に対して遅相軸方向に45度のレタデーションの波長450nmの測定値(Re450)および波長550nmの測定値(Re550)より算出した波長分散特性は1.0439であった。
Claims (11)
- 式(1)で表される化合物。
A1およびA2はそれぞれ独立して1,4−フェニレン、または1,4−シクロへキシレンであり、これらにおいて、少なくとも一つの水素が、フッ素、塩素、トリフルオロアセチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
Z 1 は独立して−COO−、または−CH 2 CH 2 COO−、であり、Z 2 は独立して−OCO−、または−OCOCH 2 CH 2 −、であり;
mおよびnは、それぞれ独立して1〜2の整数であり;
式(1)の縮合環に直接結合するA 1 −Z 1 及びZ 2 −A 2 はそれぞれ独立して、Z 1 が−COO−、Z 2 が−OCO−であり、A 1 およびA 2 が、1,4−シクロヘキシレンであり、
X1は−S−であり、
Q1は式(4−1)〜式(4−9)のいずれか1つで表される基であり;
R1およびR2はそれぞれ独立して、式(2)で表される基である。
Y2は単結合または炭素数1〜20を有するアルキレンであり、該アルキレンにおいて少なくとも一つの−CH2−は−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく;
PGは式(PG−1)で表される重合性の基である。*は結合部位を示す。
- 請求項1に記載の化合物の少なくとも1つを含有する液晶組成物。
- 請求項1に記載の化合物の少なくとも1つと、式(M1)および式(M2)で表される化合物群から選ばれる少なくとも1つとを含有する液晶組成物。
AMはそれぞれ独立して1,4−フェニレン、1,4−シクロへキシレン、1,4−シクロへキセニレン、ピリジン−2,5−ジイル、フルオレノン−2,7−ジイルまたはナフタレン−2,6−ジイルであり、これらにおいて、少なくとも一つの水素が、フッ素、塩素、シアノ、ヒドロキシ、ホルミル、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
ZMはそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−COS−、−SCO−、−OCOO−、−CONH−、−NHCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−OCOCH2CH2−、−CH=CH−、−N=CH−、−CH=N−、−N=CCH3−、−CCH3=N−、−N=N−または−C≡C−であり;
XMは水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数2〜20のアルケニル、炭素数1〜20のアルコキシまたは炭素数1〜20のアルキルエステルであり;
qは1〜4の整数であり;
aは0〜20の整数であり;
RMは水素またはメチルであり
YMは単結合、−O−、−COO−、−OCO−または−OCOO−である。) - 請求項1に記載の化合物の少なくとも1つと式(M1)で表される化合物の少なくとも1つを含有する液晶組成物。
AMは独立して、1,4−フェニレンまたは1,4−シクロへキシレンであるが、AMのうち少なくとも一つは1,4−シクロへキシレンであり、これらにおいて、少なくとも一つの水素が、フッ素、塩素、トリフルオロアセチル、ジフルオロメチル、トリフルオロメチル、炭素数1〜5のアルキル、炭素数1〜5のアルコキシ、炭素数1〜5のアルキルエステルまたは炭素数1〜5のアルカノイルで置き換えられてもよく;
ZMはそれぞれ独立して単結合、−OCH2−、−CH2O−、−COO−、−OCO−、−CH2CH2−、−CH2CH2COO−または−OCOCH2CH2−であり;
qは1または2の整数であり;
XMは水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシ、シアノ、炭素数1〜20のアルキル、炭素数1〜20のアルケニル、炭素数1〜20のアルコキシまたは炭素数1〜20のアルキルエステルであり;
aは0〜20の整数であり;
RMは水素またはメチルであり
YMは単結合、−O−、−COO−、−OCO−または−OCOO−である。) - 請求項2〜4のいずれか1項に記載の液晶組成物において、さらにキラルな化合物を少なくとも1つ含有する液晶組成物。
- 請求項2〜5のいずれか1項に記載の液晶組成物において、さらに二色性色素化合物を少なくとも1つ含有する液晶組成物。
- 請求項2〜6のいずれか1項に記載の液晶組成物に紫外光を照射して得られる重合体。
- 請求項7に記載の重合体が光学的異方性を有する光学異方性フィルム。
- 請求項8に記載の光学異方性フィルムを有する偏光板。
- 請求項8に記載の光学異方性フィルムを有する表示素子。
- 請求項9に記載の偏光板を有する表示素子。
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