JP6721873B2 - 液晶組成物用自発配向助剤 - Google Patents
液晶組成物用自発配向助剤 Download PDFInfo
- Publication number
- JP6721873B2 JP6721873B2 JP2018145906A JP2018145906A JP6721873B2 JP 6721873 B2 JP6721873 B2 JP 6721873B2 JP 2018145906 A JP2018145906 A JP 2018145906A JP 2018145906 A JP2018145906 A JP 2018145906A JP 6721873 B2 JP6721873 B2 JP 6721873B2
- Authority
- JP
- Japan
- Prior art keywords
- mass
- less
- formula
- group
- coo
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title description 223
- 239000004973 liquid crystal related substance Substances 0.000 title description 142
- 230000002269 spontaneous effect Effects 0.000 title description 21
- 150000001875 compounds Chemical class 0.000 claims description 560
- 125000004432 carbon atom Chemical group C* 0.000 claims description 177
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 125000003342 alkenyl group Chemical group 0.000 description 55
- 239000000758 substrate Substances 0.000 description 52
- 125000003545 alkoxy group Chemical group 0.000 description 39
- 230000000694 effects Effects 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- 230000007704 transition Effects 0.000 description 34
- 239000010410 layer Substances 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- -1 alkylene radical Chemical class 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 230000006872 improvement Effects 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 230000004044 response Effects 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 0 CN*C(CC1)CCC1c(cc1)ccc1-c1ccc(C2CCCCC2)c(*)c1 Chemical compound CN*C(CC1)CCC1c(cc1)ccc1-c1ccc(C2CCCCC2)c(*)c1 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- 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 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 238000001556 precipitation Methods 0.000 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 description 4
- 238000005406 washing Methods 0.000 description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- 125000005653 3,5-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:2])=C(F)C([H])=C1[*:1] 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 2
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MKSCYIVDGPPTPO-UHFFFAOYSA-N CCc(cc1)ccc1-c1ccc(C2CCC(C)CC2)cc1 Chemical compound CCc(cc1)ccc1-c1ccc(C2CCC(C)CC2)cc1 MKSCYIVDGPPTPO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- LPSGKQYEQCREFY-UHFFFAOYSA-N (3-fluoro-4-octoxyphenoxy)boronic acid Chemical compound CCCCCCCCOC1=CC=C(OB(O)O)C=C1F LPSGKQYEQCREFY-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 1
- BARXTOVILCCMTK-UHFFFAOYSA-N 2-bromo-4-(4-dodecoxy-3-fluorophenyl)phenol Chemical compound BrC=1C=C(C=CC=1O)C1=CC(=C(C=C1)OCCCCCCCCCCCC)F BARXTOVILCCMTK-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- ASMRHWUCOVGKEF-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-dioxan-2-one Chemical compound OCC1COC(=O)OC1 ASMRHWUCOVGKEF-UHFFFAOYSA-N 0.000 description 1
- MDOPFYCLQFOWRF-UHFFFAOYSA-N C(C)C(CN(CC)CC)(CC)CC Chemical compound C(C)C(CN(CC)CC)(CC)CC MDOPFYCLQFOWRF-UHFFFAOYSA-N 0.000 description 1
- IRQLAYMFAKYGCQ-UHFFFAOYSA-N CC(=C)C(=O)OC1=CC=C(CCC(O)=O)C=C1OC(=O)C(C)=C Chemical compound CC(=C)C(=O)OC1=CC=C(CCC(O)=O)C=C1OC(=O)C(C)=C IRQLAYMFAKYGCQ-UHFFFAOYSA-N 0.000 description 1
- YSZQTFHOTRKURH-UHFFFAOYSA-N CC1(OCC(CO1)COC1=CC=C(C=C1)C1=CC=C(C=C1)O)C Chemical compound CC1(OCC(CO1)COC1=CC=C(C=C1)C1=CC=C(C=C1)O)C YSZQTFHOTRKURH-UHFFFAOYSA-N 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- FYFPJTIURCOBGQ-UHFFFAOYSA-N tert-butyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)(C)OC(=O)C1=CC(O)=C(O)C(O)=C1 FYFPJTIURCOBGQ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133703—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by introducing organic surfactant additives into the liquid crystal material
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/139—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering based on orientation effects in which the liquid crystal remains transparent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/02—Alignment layer characterised by chemical composition
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133742—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers for homeotropic alignment
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133765—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers without a surface treatment
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
- G02F1/1362—Active matrix addressed cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
WK1は、メチン基、C-CH3、C-C2H5又は窒素原子を表し、
XK1及びYK1は、それぞれ独立して、−CH2−、酸素原子又は硫黄原子を表し、
ZK1は、酸素原子又は硫黄原子を表し、
UK1、VK1及びSK1は、それぞれ独立して、メチン基又は窒素原子を表すが、(K-5)および(K-6)がピリジン環になる組み合わせは除き、一般式(K−1)〜一般式(K−11)中、左端の黒点は結合手を表す。ただしKi1が(K−11)の場合はメソゲン基に少なくとも−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れか一つを含む。)
本実施形態の液晶組成物用自発配向助剤は、メソゲン基にPi1−Spi1−(Pi1は、重合性基を表し、以下の一般式(P−1)〜一般式(P−15)で表される群より選ばれる置換基を表し(式中、右端の黒点は結合手を表す。)、
WK1は、メチン基、C-CH3、C-C2H5又は窒素原子を表し、
XK1及びYK1は、それぞれ独立して、−CH2−、酸素原子又は硫黄原子を表し、
ZK1は、酸素原子又は硫黄原子を表し、
UK1、VK1及びSK1は、それぞれ独立して、メチン基又は窒素原子を表すが、(K-5)および(K-6)がピリジン環になる組み合わせは除き、一般式(K−1)〜一般式(K−8)中、左端の黒点は結合手を表す。ただしKi1が(K−11)の場合はメソゲン基に少なくとも−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れか一つを含む。)
Zi1は、単結合、−CH=CH−、−CF=CF−、−C≡C−、−COO−、−OCO−、−OCOO−、−OOCO−、−CF2O−、−OCF2−、−CH=CHCOO−、−OCOCH=CH−、−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−、又は炭素原子数2〜20のアルキレン基を表し、このアルキレン基中の1個又は隣接しない2個以上の−CH2−は−O−、−COO−又は−OCO−で置換されてもよく、ただしKi1が(K−11)の場合はメソゲン基に少なくとも−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れか一つを含み、
Ai1は、2価の6員環芳香族基、2価の6員環複素芳香族基、2価の6員環脂肪族基、2価の6員環複素脂肪族基を表し、これらの環構造中の水素原子はハロゲン原子、又はPi1−Spi1−、及び一般式Ki1で表される置換基を有する1価の有機基又はRi1で置換されていてもよいが、少なくとも一つはPi1−Spi1−で置換されており、
Zi1及びAi1がそれぞれ複数存在する場合は、それぞれ互いに同一であっても異なっていてもよく、
mi1は、1〜5の整数を表し、
式(i)中、左端の黒点および右端の黒点は結合手を表す。)
で表される部分構造を有する化合物(以下「化合物(i)」ともいう)を1種又は2種以上含有する。
自発配向助剤として化学的安定性を重要視する場合は、Ki1としては(K−1)、(K−3)、(K−8)、(K−9)、(K−10)及び(K−11)が好ましく、液晶の配向性を重要視する場合は、(K−1)、(K−3)、及び(K−11)が好ましく、液晶化合物への溶解性を重要視する場合は、(K−1)、(K−8)及び(K−10)が好ましく、これらのバランスを重要視する場合は、(K−1)、(K−3)、及び(K−11)がより好ましい。また、Pi1は、化学的安定性、重合感度の点から、式(P−1)、(P−2)、(P−7)〜(P−10)、(P−12)のいずれかの置換基が好ましく、取り扱いの簡便性の点から、式(P−1)、(P−2)、(P−9)、(P−10)が、さらに好ましい。
Zii1、Aii1及びmii1は、それぞれ前記一般式(i)におけるZi1、Ai1及びmi1と同じ意味を表し、Rii1及びRii2はそれぞれ独立して、水素原子、炭素原子数1〜40の直鎖又は分岐のアルキル基、ハロゲン化アルキル基、又はPi1−Spi1−を表し、該アルキル基中の−CH2−は−CH=CH−、−C≡C−、−O−、−NH−、−COO−又は−OCO−で置換されてもよいが−O−は連続にはならなく、Rii1及びRii2は少なくとも一つは、Ki1で表される置換基を有する1価の有機基を表し、一般式(ii)中に1つ又は2つ以上のPi1−Spi1−を有しており、1つ又は2つ以上のKi1で表される置換基を有する1価の有機基を有しておりかつ1つ又は2つ以上のRi1を有している。ただしKi1が(K−11)の場合は、Zii1は、−CH2−CH2COO−、−OCOCH2―CH2−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れかである)で表される化合物(以下「化合物(ii)」ともいう)である。
Zi1、Ai1、Ri1及びKi1は、それぞれ前記一般式(i)におけるZi1、Ai1、Ri1及びKi1と同じ意味を表し、
Ai2は前記一般式(i)におけるAi1と同じ意味を表し、
Zi2は前記一般式(i)におけるZi1と同じ意味を表し、
Zi1、Zi2、Ai1、miii1及び/又はAi2がそれぞれ複数存在する場合は、それぞれ互いに同一であっても異なっていてもよく、ただしAi1及びAi2の何れか一つは少なくとも一つのPi1−Spi1−で置換されており、Ki1が(K−11)の場合は、Zii1は少なくとも−CH2−CH2COO−、−OCOCH2―CH2−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れか一つを含み、
miii1は、1〜5の整数を表し、
miii2は、1〜5の整数を表し、
Gi1は、2価、3価、4価のいずれかの分岐構造、または2価、3価、4価のいずれかの脂肪族または芳香族の環構造を表し、
miii3は、Gi1の価数より1小さい整数を表す。)
で表される化合物(以下「化合物(iii)」ともいう)であってよい。
Gi1は、2価、3価、4価のいずれかの分岐構造、又は2価、3価、4価のいずれかの脂肪族または芳香族の環構造を表し、
好ましくは、2価、3価、4価のいずれかの分岐構造は、2置換の炭素原子、3置換の炭素原子、4置換の炭素原子、2置換の窒素原子、3置換の窒素原子、4置換の炭素原子のいずれかであり、
好ましくは、2価、3価、4価のいずれかの脂肪族または芳香族の環構造としは、3置換以上のベンゼン環、または3置換以上のシクロヘキサン環である。
miii3はGi1がZi2と結合する結合手以外の部分とAi1が結合していることを表すものであるため、miii3は、Gi1の価数より1小さい整数を表す。
Ai2は前記一般式(i)におけるAi1と同じ意味を表し、
Zi2は前記一般式(i)におけるZi1と同じ意味を表し、
Zi1、Zi2、Ai1、miii1及び/又はAi2がそれぞれ複数存在する場合は、それぞれ互いに同一であっても異なっていてもよく、
miii1は、1〜5の整数を表し、
miii2は、1〜5の整数を表し、
Bは、3価の分岐構造、または3価の脂肪族または芳香族の環構造を表し、
Cは、4価の分岐構造、または4価の脂肪族または芳香族の環構造を表す。
本実施形態の液晶組成物は、上記一般式(i)で表される部分構造を有する化合物を1種又は2種以上含有する。この液晶組成物は、負の誘電率異方性(Δε)を有する。なお、液晶組成物に含有される一般式(i)で表される部分構造を有する化合物は、その具体例である化合物(ii)並びに式(R−1−1)〜(R−1−32)、及び化合物(iii)並びに式(iii-1)、(iii-2)、及び式(R−1−33)〜(R−1−37)のいずれかで表される化合物を含めて、上記の液晶組成物用自発配向助剤における化合物(i)と同じであるため、ここでは説明を省略する。
RN11、RN12、RN21、RN22、RN31及びRN32は、それぞれ独立して炭素原子数1〜8のアルキル基を表し、該アルキル基中の1個又は隣接していない2個以上の−CH2−は、それぞれ独立して、−CH=CH−、−C≡C−、−O−、−CO−、−COO−又は−OCO−によって置換されていてもよく、
AN11、AN12、AN21、AN22、AN31及びAN32は、それぞれ独立して、
(a) 1,4−シクロヘキシレン基(この基中に存在する1個の−CH2−又は隣接していない2個以上の−CH2−は−O−に置換されてもよい。)、
(b) 1,4−フェニレン基(この基中に存在する1個の−CH=又は隣接していない2個以上の−CH=は−N=に置換されてもよい。)、
(c) ナフタレン−2,6−ジイル基、1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基又はデカヒドロナフタレン−2,6−ジイル基(ナフタレン−2,6−ジイル基又は1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基中に存在する1個の−CH=又は隣接していない2個以上の−CH=は−N=に置換されてもよい。)、及び
(d) 1,4−シクロヘキセニレン基
からなる群より選ばれる基を表し、前記の基(a)、基(b)、基(c)及び基(d)は、それぞれ独立して、シアノ基、フッ素原子又は塩素原子で置換されていてもよく、
ZN11、ZN12、ZN21、ZN22、ZN31及びZN32は、それぞれ独立して、単結合、−CH2CH2−、−(CH2)4−、−OCH2−、−CH2O−、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=N−N=CH−、−CH=CH−、−CF=CF−又は−C≡C−を表し、
XN21は、水素原子又はフッ素原子を表し、
TN31は、−CH2−又は酸素原子を表し、
nN11、nN12、nN21、nN22、nN31及びnN32は、それぞれ独立して0〜3の整数を表すが、nN11+nN12、nN21+nN22及びnN31+nN32は、それぞれ独立して1、2又は3であり、
AN11〜AN32、ZN11〜ZN32がそれぞれ複数存在する場合は、それぞれは互いに同一であっても異なっていてもよい。
RL1及びRL2は、それぞれ独立して炭素原子数1〜8のアルキル基を表し、該アルキル基中の1個又は隣接していない2個以上の−CH2−は、それぞれ独立して、−CH=CH−、−C≡C−、−O−、−CO−、−COO−又は−OCO−によって置換されていてもよく、
nL1は、0、1、2又は3を表し、
AL1、AL2及びAL3は、それぞれ独立して、
(a) 1,4−シクロヘキシレン基(この基中に存在する1個の−CH2−又は隣接していない2個以上の−CH2−は−O−に置換されてもよい。)、
(b) 1,4−フェニレン基(この基中に存在する1個の−CH=又は隣接していない2個以上の−CH=は−N=に置換されてもよい。)、及び
(c) (c)ナフタレン−2,6−ジイル基、1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基又はデカヒドロナフタレン−2,6−ジイル基(ナフタレン−2,6−ジイル基又は1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基中に存在する1個の−CH=又は隣接していない2個以上の−CH=は−N=に置換されてもよい。)
からなる群より選ばれる基を表し、前記の基(a)、基(b)及び基(c)は、それぞれ独立してシアノ基、フッ素原子又は塩素原子で置換されていてもよく、
ZL1及びZL2は、それぞれ独立して、単結合、−CH2CH2−、−(CH2)4−、−OCH2−、−CH2O−、−COO−、−OCO−、−OCF2−、−CF2O−、−CH=N−N=CH−、−CH=CH−、−CF=CF−又は−C≡C−を表し、
nL1が2又は3であってAL2が複数存在する場合は、それらは互いに同一であっても異なっていてもよく、nL1が2又は3であってZL2が複数存在する場合は、それらは互いに同一であっても異なっていてもよいが、一般式(N−1)、(N−2)及び(N−3)で表される化合物を除く。
Zp1は、フッ素原子、シアノ基、水素原子、水素原子がハロゲン原子に置換されていてもよい炭素原子数1〜15のアルキル基、水素原子がハロゲン原子に置換されていてもよい炭素原子数1〜15のアルコキシ基、水素原子がハロゲン原子に置換されていてもよい炭素原子数1〜15のアルケニル基、水素原子がハロゲン原子に置換されていてもよい炭素原子数1〜15のアルケニルオキシ基又は−Spp2−Rp2を表し、
Rp1及びRp2は、以下の式(R−I)〜式(R−IX):
*でSpp1と結合し、
R2〜R6は、それぞれ独立して、水素原子、炭素原子数1〜5個のアルキル基又は炭素原子数1〜5個のハロゲン化アルキル基を表し、
Wは、単結合、−O−又はメチレン基を表し、
Tは、単結合又は−COO−を表し、
p、t及びqは、それぞれ独立して、0、1又は2を表す。)
のいずれかを表し、
Spp1及びSpp2はスペーサー基を表し、
Lp1及びLp2は、それぞれ独立して、単結合、−O−、−S−、−CH2−、−OCH2−、−CH2O−、−CO−、−C2H4−、−COO−、−OCO−、−OCOOCH2−、−CH2OCOO−、−OCH2CH2O−、−CO−NRa−、−NRa−CO−、−SCH2−、−CH2S−、−CH=CRa−COO−、−CH=CRa−OCO−、−COO−CRa=CH−、−OCO−CRa=CH−、−COO−CRa=CH−COO−、−COO−CRa=CH−OCO−、−OCO−CRa=CH−COO−、−OCO−CRa=CH−OCO−、−(CH2)z−C(=O)−O−、−(CH2)z−O−(C=O)−、−O−(C=O)−(CH2)z−、−(C=O)−O−(CH2)z−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−CF2−、−CF2O−、−OCF2−、−CF2CH2−、−CH2CF2−、−CF2CF2−又は−C≡C−(式中、Raはそれぞれ独立して水素原子又は炭素原子数1〜4のアルキル基を表し、zは1〜4の整数を表す。)を表し、
Mp2は、1,4−フェニレン基、1,4−シクロヘキシレン基、アントラセン−2,6−ジイル基、フェナントレン−2,7−ジイル基、ピリジン−2,5−ジイル基、ピリミジン−2,5−ジイル基、ナフタレン−2,6−ジイル基、インダン−2,5−ジイル基、1,2,3,4−テトラヒドロナフタレン−2,6−ジイル基、1,3−ジオキサン−2,5−ジイル基又は単結合を表すが、Mp2は無置換であるか又は炭素原子数1〜12のアルキル基、炭素原子数1〜12のハロゲン化アルキル基、炭素原子数1〜12のアルコキシ基、炭素原子数1〜12のハロゲン化アルコキシ基、ハロゲン原子、シアノ基、ニトロ基若しくは−Rp1で置換されていてもよく、
Mp1は、以下の式(i−11)〜(ix−11):
のいずれかを表し、
Mp1上の任意の水素原子は炭素原子数1〜12のアルキル基、炭素原子数1〜12のハロゲン化アルキル基、炭素原子数1〜12のアルコキシ基、炭素原子数1〜12のハロゲン化アルコキシ基、ハロゲン原子、シアノ基、ニトロ基若しくは−Rp1で置換されていてもよく、
Mp3は、以下の式(i−13)〜(ix−13):
のいずれかを表し、
Mp3上の任意の水素原子は炭素原子数1〜12のアルキル基、炭素原子数1〜12のハロゲン化アルキル基、炭素原子数1〜12のアルコキシ基、炭素原子数1〜12のハロゲン化アルコキシ基、ハロゲン原子、シアノ基、ニトロ基若しくは−Rp1で置換されていてもよく、
mp2〜mp4は、それぞれ独立して0、1、2又は3を表し、
mp1及びmp5は、それぞれ独立して1、2又は3を表し、
Zp1が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Rp1が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Rp2が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Spp1が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Spp2が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Lp1が複数存在する場合にはそれらは互いに同一であっても異なっていてもよく、Mp2が複数存在する場合にはそれらは互いに同一であっても異なっていてもよい。
本実施形態の液晶組成物は、液晶表示素子に適用される。以下、図1,2を適宜参照しながら、本実施形態に係る液晶表示素子の例を説明する。
(実施例1)
撹拌装置、冷却器、及び温度計を備えた反応容器に5−ブロモサリチルアルデヒド 50g、(2,2−ジメチルエチルー1,3−ジオキサン−5−イル)メチル メシラート 75g、炭酸カリウム 35g、N,N−ジメチルホルムアミド 500mlを仕込み、90℃で5時間反応させた。反応終了後、冷却し、酸エチル1Lを加え有機層を水、飽和食塩水で洗浄し、溶媒を留去し(1)で表される化合物 67gを得た。
反応終了後。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、シリカカラムによる精製を行い化合物(6)で表される目的化合物 26gを得た。
融点 81℃
1H−NMR(溶媒:重クロロホルム):δ: 0.88(t,3H),1.29−1.31(m,6H),1.44−1.49(m,2H),1.56(s,3H),1.83(q,2H),1.97(s,2H),2.69−2.76(m,1H),4.05(t,2H),4.16(d,2H),4.35−4.38(m,2H),4.59−4.62(m,2H),5.28(s,2H),5.60(s,1H),6.14(s,1H),6.90(d,1H),7.01(t,1H),7.21−7.29(m,2H),7.46(dd,1H),7.53(d,1H)
13C−NMR(溶媒:重クロロホルム):δ:14.9,17.3,22.7,25.9,27.9,29.6,31.8,64.0,68.7,68.8,72.8,114.7,122.3,125.6,128.4,135.5,138.6,151.0,158.3,166.0
(実施例2)
撹拌装置、冷却器、及び温度計を備えた反応容器に3−(3,4−ビス(メタクリロイルオキシ)フェニル)プロピオン酸 16g、 4‘−((2,2−ジメチルー1,3−ジオキサン−5−イル)メトキシ)−[1,1’−ビフェニル]−4−オール 15g、ジメチルアミノピリジン 500mg、ジクロロメタン 200mlを加え、反応容器を10℃以下に冷却させる。その後、ジイソプロピルカルボジイミド 8gをゆっくり滴下する。滴下終了後、室温で5時間反応させる。反応終了後、有機層を水、飽和食塩水で洗浄し、溶媒を留去した。次いで、テトラヒドロフラン(THF) 150mlを加え、10%塩酸 20mlをゆっくり滴下した。反応終了後、冷却し、酢酸エチルにより目的物を抽出した。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、トルエンによる分散洗浄、アルミナカラムによる精製を行い式(7)で表される目的の化合物 21gを得た。
融点 121℃
(実施例3)
撹拌装置、冷却器、及び温度計を備えた反応容器に上記の化合物(7)10g
ジクロロメタン 300mlを加え10℃以下に冷却する。次いで、クロロギ酸エチル 5.6gをゆっくり滴下する。滴下終了後、30分攪拌する。次いでトリエチトリエチルアミン 5.7gを滴下する。反応終了後。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、シリカカラムによる精製を行い化合物(8)で表される目的化合物 8.5ggを得た。
融点 102℃
1H−NMR(溶媒:重クロロホルム):δ:1.56(s,3H),1.95(t,2H),2.20(t,2H),2.69−2.76(m,1H),4.05(m,2H),4.16(m,4H),5.60(s,2H),6.14(s,2H),6.87−6.99(m,3H),7.05(s,1H),7.21−7.29(m,3H),7.43(d,2H),7.55(d,2H)
13C−NMR(溶媒:重クロロホルム):δ:17.3,27.9,29.6,68.7,68.8,72.8,109.5,114.7,122.3,125.6,128.4,128.3,129.4,135.5,138.6,151.0,158.3,159.7,166.0
(実施例4)
撹拌装置、冷却器、及び温度計を備えた反応容器に5−ブロモサリチルアルデヒド 10g、パラトルエンスルホン酸ピリジニウム塩 1g ジクロロメタン100mlを仕込み、3,4−ジヒドロ−2Hピラン10gのジクロロメタン溶液 20mlを室温で滴下し、5時間反応させた。反応終了後、有機層を水、飽和食塩水で洗浄し、溶媒を留去し式(9)で表される化合物 12gを得た。
油状化合物
1H−NMR(溶媒:重クロロホルム):δ: 1.76(s,6H),4.12(t,12H),4.84(s,2H),5.47(s,3H),5.60(s,1H),6.14(s,1H),6.90−7.02(m,9H),7.15−7.29(m,4H),7.35(s,1H),7.65−7.82(m,4H)
13C−NMR(溶媒:重クロロホルム):δ:17.3,62.9,68.7,68.8,72.8,101.4,109.5,114.7,122.3,125.6,128.4,128.3,135.5,138.6,158.3,159.7,166.0
撹拌装置、冷却器、及び温度計を備えた反応容器に3−ブロモ−4’−(ドデシルオキシ)−3‘−フルオロ−(1,1’−ビフェニル)−4−オール 20g、パラトルエンスルホン酸ピリジニウム塩 0.5g ジクロロメタン100mlを仕込み、3,4−ジヒドロ−2Hピラン 8gのジクロロメタン溶液 20mlを室温で滴下し、5時間反応させた。反応終了後、有機層を水、飽和食塩水で洗浄し、溶媒を留去し式(15)で表される化合物 28gを得た。
融点 55℃
1H−NMR(溶媒:重クロロホルム):δ:0.88(t,3H),1.44−1.49(m,2H),1.51−1.56(m,2H),1.81−1.85(m,2H),1.98(s,3H),2.02−2.03(m,2H),2.73−2.78(m,3H),4.05(t,2H),4.12(d,2H),4.21(t,2H),4.47(m,2H),4.59(m,2H),5.56(s,1H),6.09(s,1H),6.83(d,1H),7.02(t,1H),7.19−7.27(m,4H),7.32(d,1H),7.34(m,1H)
13C−NMR(溶媒:重クロロホルム):δ:14.1,18.3,22.6,25.9,27.0,28.9,29.2,29.3,31.8,64.2,64.4,69.0,69.5,111.2,114.5,115.1,122.1,125.4,128.7,130.4,136.4,138.6,147.0,149.5,155.0,167.0
撹拌装置、冷却器、及び温度計を備えた反応容器に4−オクチルフェノール 18.5g、エチレングリコールモノターシャリーブチルエーテル 12g、トリフェニルホスフィン 35g、ジクロロメタン 300mlを仕込み、反応容器を5℃に冷却した。その後、DIAD 22gを滴下した。滴下終了後、室温で5時間撹拌して反応を終了させた。反応終了後、ジクロロメタン 200mlを加え、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、シリカゲルカラムによる精製により式(20)に示す化合物23gを得た。
た。溶媒を留去し、式(21)で表される化合物18gを得た。
油状化合物
1H−NMR(溶媒:重クロロホルム):δ:0.88(t,6H),1.26−1.49(m,10H),1.63(m,2H),1.98(s,3H),2.02−2.03(m,2H),2.63−2.70(m,4H),3.38−3.41(m,4H),3.80(s,2H),4.21(t,2H),4.22(m,2H),4.47−4.50(m,4H),5.56(s,1H),6.09(s,1H),6.83(d,2H),7.02(t,1H),7.19−7.27(m,4H),7.62(m,2H)
13C−NMR(溶媒:重クロロホルム):δ:14.1,14.8,18.3,22.7,26.3,28.9,29.3,31.8,34.2,35.7,41.4,65.5,67.4,69.0,70.2,111.2,114.5,115.0,124.9,127.0,129.6,133.4,136.0,147.0,149.5,155.0,167.0
下記に示すとおりの化合物と混合比率で構成される組成物:
ック相転移温度(TCN)は−33℃、屈折率異方性(Δn)は0.11、誘電率異方性
(Δε)は−2.8、回転粘性(γ1)は98mPa・sであった。なお、屈折率異方性
(Δn)、誘電率異方性(Δε)、及び回転粘性(γ1)は、いずれも25℃における測
定結果である(以下、同様)。
添加量0.3重量%の化合物(P−J−1)に代えて、下記化合物を表1に示す添加
量でLC−1に添加した以外は、実施例7と同様にして液晶組成物を調製した。
組成物LC−1に代えて、下記に示すとおりの化合物と混合比率で構成される組成物:
実施例25における添加量0.3重量%の化合物(P−J−1)に代えて、それぞれ下記に示す表1または表3に示す添加化合物を、表1または表3に示す添加量でLC−2に添加した以外は、実施例25と同様にして液晶組成物を調製した。
実施例7における添加量0.3重量%の化合物(P−J−1)に代えて、それぞれ下記に示す表3、または表5、表7、表9に示す添加化合物を、表3または表5、表7、表9の該当する添加量で添加した以外は、実施例7と同様にして液晶組成物を調製した。
実施例8における添加量0.3重量%の化合物(P−J−1)に代えて、それぞれ示す添加化合物1を表12に示す添加量で、さらに、表12に示す添加化合物2を、表12に示す添加量にした以外は、実施例8と同様にして液晶組成物を調製した。
化合物(P−J−1)を用いなかった以外は、実施例7と同様にして液晶組成物を調製した。
実施例7において、化合物(P−J−1)を0.3重量%添加したことに代えて、下記化合物を表13に示す添加量でLC−1またはLC−2に添加した以外は、実施例7と同様にして液晶組成物を調製した。
液晶組成物をメンブレンフィルター(Agilent Technologies社製、PTFE 13mm−0.2μm)にてろ過を行い、真空減圧条件にて15分間静置し溶存空気の除去を行った。これをアセトンにて洗浄し十分に乾燥させたバイアル瓶に0.5g秤量し、−25℃の低温環境下に10日間静置した。その後、目視にて析出の有無を観察し、以下の2段階で判定した。
透明な共通電極からなる透明電極層及びカラーフィルタ層を具備した配向膜を有さない第一の基板(共通電極基板)と、アクティブ素子により駆動される透明画素電極を有する画素電極層を有する配向膜を有さない第二の基板(画素電極基板)とを作製した。第一の基板上に液晶組成物を滴下し、第二の基板上で挟持し、シール材を常圧で110℃2時間の条件で硬化させ、セルギャップ3.2μmの液晶セルを得た。このときの垂直配向性および滴下痕などの配向ムラを、偏光顕微鏡を用いて観察し、以下の4段階で評価した。
B:ごく僅かに配向欠陥が有るも許容できるレベル
C:端部なども含め、配向欠陥が多く許容できないレベル
D:配向不良がかなり劣悪
上記(垂直配向性の評価試験)で使用した液晶セルに、10V、100Hzの矩形交流波を印加しながら、高圧水銀ランプを用いて、365nmにおける照度が100m/cm2であるUV光を200秒間照射した。その後、白表示の安定性を、10V、100Hzの矩形交流波を印加しながらセルに物理的な外力を加え、クロスニコルの状態で観察を行い、以下の4段階で評価した。
B:ごく僅かに配向欠陥が有るも許容できるレベル
C:端部なども含め、配向欠陥が多く許容できないレベル
D:配向不良がかなり劣悪
上記(プレチルト角形成の評価試験)にて使用したセルに、さらに、東芝ライテック社製のUV蛍光ランプを60分間照射した(313nmにおける照度1.7mW/cm2)後の、重合性化合物(R1−1−1)の残存量をHPLCにて定量し、残存モノマー量を決定した。モノマーの残存量に応じて、以下の4段階で評価した。
B:300ppm以上500ppm未満。
D:1500ppm以上
上記(プレチルト角形成の評価試験)にて使用したセルギャップ3.2μmのセルに、さらに、東芝ライテック社製のUV蛍光ランプを60分間照射した(313nmにおける照度1.7mW/cm2)。これにより得られたセルに対して、応答速度を測定した。応答速度は、6VにおけるVoffを、25℃の温度条件で、AUTRONIC−MELCHERS社のDMS703を用いて測定した。応答特性を以下の4段階で評価した。
B:5ms以上15ms未満
C:15ms以上25ms未満
D:25ms以上
Claims (3)
- 一般式(ii)で表される化合物。
Z ii1 は、単結合、−COO−、−OCO−、−OCOO−、−OOCO−、−CH=CHCOO−、−OCOCH=CH−、−CH 2 −CH 2 COO−、−OCOCH 2 ―CH 2 −、−CH=C(CH 3 )COO−、−OCOC(CH 3 )=CH−、−CH 2 −CH(CH 3 )COO−、−OCOCH(CH 3 )―CH 2 −、又は炭素原子数2〜20のアルキレン基を表し、このアルキレン基中の1個又は隣接しない2個以上の−CH 2 −は−O−で置換されてもよく、
Z ii1 の少なくとも一つは、単結合であり、
Aii1は、1,4−フェニレン基又は1,4−シクロヘキシル基を表し、これらの環構造中の水素原子はハロゲン原子、P i1 −Sp i1 −(P i1 は後述の通りであり、Sp i1 は炭素原子数1〜18の直鎖状アルキレン基又は単結合を表す。)、又は、Ri1(Ri1は、水素原子、炭素原子数1〜40の直鎖又は分岐のアルキル基、ハロゲン化アルキル基、又は前記Pi1−Spi1−を表し、該アルキル基中の−CH2−は−CH=CH−、−C≡C−、−O−、−NH−、−COO−又は−OCO−で置換されてもよいが、−O−は連続にはならない)で置換されていてもよいが、少なくとも1つのPi1−Spi1−で1,4−フェニレン基の2位,3位,5位若しくは6位又は1,4−シクロヘキシル基の2位,3位,5位若しくは6位が置換されており、
Zii1及びAii1がそれぞれ複数存在する場合は、それぞれ互いに同一であっても異なっていてもよく、
mii1は、2〜4の整数を表し、
Rii1及びRii2はそれぞれ独立して、水素原子、炭素原子数1〜40の直鎖又は分岐のアルキル基、ハロゲン化アルキル基、又はPi1−Spi1−を表し、該アルキル基中の−CH2−は−CH=CH−、−C≡C−、−O−、−NH−、−COO−又は−OCO−で置換されてもよいが−O−は連続にはならなく、
Rii1及びRii2は少なくとも一つはKi1−Rk-を表す。
ただしKi1が(K−11)の場合は、少なくとも一つのZii1は、−CH2−CH2COO−、−OCOCH2―CH2−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れかを表し、
Pi1は、以下の一般式(P−1)〜一般式(P−15)で表される群より選ばれる置換基を表し(式中、右端の黒点は結合手を表す。)、
WK1は、メチン基、C−CH3、C−C2H5又は窒素原子を表し、
XK1及びYK1は、それぞれ独立して、−CH2−、酸素原子又は硫黄原子を表し、 ZK1は、酸素原子又は硫黄原子を表し、
UK1、VK1及びSK1は、それぞれ独立して、メチン基又は窒素原子を表すが、(K−5)および(K−6)がベンゼン環及びピリジン環になる組み合わせは除き、一般式(K−1)〜一般式(K−11)中、左端の黒点は結合手を表す。)
K i1 −R k −は、
−CH 2 −O−K i1
−(CH 2 ) 2 −O−CH 2 −K i1 、
−O−CH 2 −K i1 、
−O−(CH 2 ) 2 −K i1 、
−O−(CH 2 ) 3 −K i1 、
−O−(CH 2 ) 2 −O−K i1 、
−O−(CH 2 ) 2 −O−CH 2 −K i1 、
−O−(CH 2 ) 7 −O−CH 2 −K i1 、
−O−(CH 2 ) 9 −O−CH 2 −K i1 、
−O−(CH 2 ) 8 −O−(CH 2 ) 2 −K i1 、
で表される基のいずれかを表す。) - 一般式(ii−1)で表される請求項1に記載の化合物。
Zii1、Aii1及びmii1は、それぞれ前記同様であり、
Kii1は前記Ki1と同じ意味を表し、
Rii10は水素原子、炭素原子数1〜40の直鎖又は分岐のアルキル基、ハロゲン化アルキル基、又はPi1−Spi1−を表し、該アルキル基中の−CH2−は−CH=CH−、−C≡C−、−O−、−NH−、−COO−又は−OCO−で置換されてもよいが−O−は連続にはならなく、
ただしAii1の少なくとも1つは前記Pi1−Spi1−で1,4−フェニレン基の2位,3位,5位若しくは6位又は1,4−シクロヘキシル基の2位,3位,5位若しくは6位が置換されており、
式(ii−1)で表される化合物においてKii1は前記式一般式(K−1)〜一般式(K−7)及び一般式(K−9)〜一般式(K−11)で表される群より選ばれる置換基である。) - 一般式(ii−2)で表される請求項1に記載の化合物。
Aii1及びAiii1は、それぞれ独立して前記Aii1と同じ意味を表し、
mii1は、2〜5の整数を表し、
Rii1は水素原子、炭素原子数1〜40の直鎖又は分岐のアルキル基、ハロゲン化アルキル基、又は前記Pi1−Spi1−を表し、該アルキル基中の−CH2−は−CH=CH−、−C≡C−、−O−、−NH−、−COO−又は−OCO−で置換されてもよいが−O−は連続にはならず、
Aii1及びAiii1の少なくとも一つは前記Pi1−Spi1−で1,4−フェニレン基の2位,3位,5位若しくは6位又は1,4−シクロヘキシル基の2位,3位,5位若しくは6位が置換されており、
Wkiは、メチン基、C−CH3、C−C2H5を表し、
Xii1は、単結合、−CH=CH−、−CF=CF−、−C≡C−、−COO−、−OCO−、−OCOO−、−OOCO−、−CF2O−、−OCF2−、−CH=CHCOO−、−OCOCH=CH−、−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−を表すが、少なくとも一つは、−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れかを表すが、少なくとも一つのXii1は、−CH2−CH2COO−、−OCOCH2―CH2−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、−OCH2CH2O−の何れかを表し、
Yii1は、単結合、−CH=CH−、−CF=CF−、−C≡C−、−COO−、−OCO−、−OCOO−、−OOCO−、−CF2O−、−OCF2−、−CH=CHCOO−、−OCOCH=CH−、−CH2−CH2COO−、−OCOCH2―CH2−、−CH=C(CH3)COO−、−OCOC(CH3)=CH−、−CH2−CH(CH3)COO−、−OCOCH(CH3)―CH2−、又は炭素原子数2〜20のアルキレン基を表し、このアルキレン基中の1個又は隣接しない2個以上の−CH2−は−O−、−COO−又は−OCO−で置換されてもよい。)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016209592 | 2016-10-26 | ||
JP2016209592 | 2016-10-26 | ||
JP2017109171 | 2017-06-01 | ||
JP2017109171 | 2017-06-01 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018523035A Division JP6447784B2 (ja) | 2016-10-26 | 2017-10-17 | 液晶組成物用自発配向助剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019012272A JP2019012272A (ja) | 2019-01-24 |
JP6721873B2 true JP6721873B2 (ja) | 2020-07-15 |
Family
ID=62024916
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018523035A Active JP6447784B2 (ja) | 2016-10-26 | 2017-10-17 | 液晶組成物用自発配向助剤 |
JP2018145906A Active JP6721873B2 (ja) | 2016-10-26 | 2018-08-02 | 液晶組成物用自発配向助剤 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018523035A Active JP6447784B2 (ja) | 2016-10-26 | 2017-10-17 | 液晶組成物用自発配向助剤 |
Country Status (6)
Country | Link |
---|---|
US (2) | US10927300B2 (ja) |
JP (2) | JP6447784B2 (ja) |
KR (1) | KR20190073351A (ja) |
CN (1) | CN109643037B (ja) |
TW (1) | TWI737834B (ja) |
WO (1) | WO2018079333A1 (ja) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190013740A (ko) * | 2016-06-03 | 2019-02-11 | 디아이씨 가부시끼가이샤 | 액정 조성물용 자발 배향 조제, 그 자발 배향 조제에 적합한 화합물, 액정 조성물, 및 액정 표시 소자 |
TWI737834B (zh) * | 2016-10-26 | 2021-09-01 | 日商迪愛生股份有限公司 | 液晶組成物用自發配向助劑 |
CN111183206B (zh) * | 2017-09-08 | 2023-08-25 | Dic株式会社 | 取向助剂、液晶组合物及液晶显示元件 |
CN111194305B (zh) | 2017-11-17 | 2023-01-03 | Dic株式会社 | 聚合性化合物、以及使用其的液晶组合物和液晶显示元件 |
CN111344277B (zh) * | 2017-12-21 | 2023-03-28 | Dic株式会社 | 聚合性化合物以及使用其的液晶组合物及液晶显示元件 |
WO2019124093A1 (ja) * | 2017-12-21 | 2019-06-27 | Dic株式会社 | 液晶組成物 |
JP6729815B2 (ja) | 2018-03-01 | 2020-07-22 | Dic株式会社 | 重合性化合物並びにそれを使用した液晶組成物及び液晶表示素子 |
US11415840B2 (en) | 2018-05-09 | 2022-08-16 | Dic Corporation | Liquid crystal display device |
JP2020002065A (ja) * | 2018-06-28 | 2020-01-09 | Dic株式会社 | 重合性化合物並びにそれを使用した液晶組成物及び液晶表示素子 |
TWI814843B (zh) * | 2018-07-03 | 2023-09-11 | 日商Dic股份有限公司 | 液晶顯示元件之製造方法 |
TWI791853B (zh) * | 2018-07-03 | 2023-02-11 | 日商Dic股份有限公司 | 基板及液晶顯示元件 |
JP7271896B2 (ja) * | 2018-10-02 | 2023-05-12 | Dic株式会社 | 重合性化合物並びにそれを使用した液晶組成物及び液晶表示素子 |
TW202034045A (zh) * | 2018-10-02 | 2020-09-16 | 日商Dic股份有限公司 | 使用有配向助劑之液晶組成物及液晶顯示元件、以及其製造方法 |
JP7288166B2 (ja) * | 2018-10-10 | 2023-06-07 | Dic株式会社 | 液晶組成物 |
JP6844749B2 (ja) * | 2018-10-11 | 2021-03-17 | Dic株式会社 | 重合性液晶組成物及び液晶表示素子 |
JP7298136B2 (ja) * | 2018-11-08 | 2023-06-27 | Dic株式会社 | 液晶組成物及び液晶表示素子 |
TW202033752A (zh) * | 2018-11-30 | 2020-09-16 | 日商Dic股份有限公司 | 配向助劑、液晶組成物及液晶顯示元件 |
JP7318204B2 (ja) * | 2018-12-18 | 2023-08-01 | Dic株式会社 | 液晶組成物及び液晶表示素子 |
TWI810416B (zh) * | 2018-12-25 | 2023-08-01 | 日商Dic股份有限公司 | 液晶顯示元件 |
JP7331361B2 (ja) * | 2018-12-26 | 2023-08-23 | Dic株式会社 | 液晶表示素子の製造方法及び液晶表示素子 |
TWI719395B (zh) * | 2019-01-25 | 2021-02-21 | 達興材料股份有限公司 | 添加劑及其應用 |
WO2020209035A1 (ja) * | 2019-04-09 | 2020-10-15 | Jnc株式会社 | 化合物、液晶組成物、および液晶表示素子 |
CN113444531A (zh) * | 2020-03-27 | 2021-09-28 | Dic株式会社 | 聚合性化合物、含有聚合性化合物的液晶组合物和使用其的液晶显示元件 |
CN114929839A (zh) | 2020-03-27 | 2022-08-19 | Dic株式会社 | 液晶组合物、液晶显示元件及化合物 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5595915B2 (ja) * | 2007-08-30 | 2014-09-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶ディスプレイ |
EP2292720A1 (en) * | 2009-09-08 | 2011-03-09 | Merck Patent GmbH | Liquid-crystal display |
DE102011108708A1 (de) * | 2010-09-25 | 2012-03-29 | Merck Patent Gmbh | Flüssigkristallanzeigen und flüssigkristalline Medien mit homöotroper Ausrichtung |
JP6377908B2 (ja) * | 2011-02-05 | 2018-08-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | ホメオトロピック配向を有する液晶ディスプレイ |
US9234136B2 (en) | 2011-07-07 | 2016-01-12 | Merck Patent Gmbh | Liquid-crystalline medium |
WO2014090362A1 (en) * | 2012-12-12 | 2014-06-19 | Merck Patent Gmbh | Liquid-crystalline medium |
WO2014094959A1 (en) * | 2012-12-17 | 2014-06-26 | Merck Patent Gmbh | Liquid-crystal displays and liquid-crystalline media having homeotropic alignment |
CN105122127B (zh) * | 2013-03-25 | 2018-06-05 | Dic株式会社 | 液晶显示元件 |
JP6437798B2 (ja) * | 2013-11-19 | 2018-12-12 | 共栄社化学株式会社 | ベンジルフェニルフェノキシ化合物及びそれを含む光学材料用樹脂組成物並びに該組成物を硬化させた硬化物 |
KR20150070027A (ko) * | 2013-12-16 | 2015-06-24 | 메르크 파텐트 게엠베하 | 액정 매질 |
EP3730590A1 (de) | 2014-03-10 | 2020-10-28 | Merck Patent GmbH | Flüssigkristalline medien mit homöotroper ausrichtung |
WO2016015803A1 (de) * | 2014-07-28 | 2016-02-04 | Merck Patent Gmbh | Flüssigkristalline medien mit homöotroper ausrichtung |
US20180023001A1 (en) * | 2015-01-14 | 2018-01-25 | Jnc Corporation | Compound having polymerizable group, liquid crystal composition and liquid crystal display device |
CN107949620B (zh) * | 2015-09-09 | 2022-02-11 | 默克专利股份有限公司 | 液晶介质 |
US10190050B2 (en) | 2016-01-21 | 2019-01-29 | Samsung Display Co., Ltd. | Liquid crystal composition, liquid crystal display device including the same, and method of manufacturing liquid crystal display device |
CN106281363B (zh) * | 2016-07-18 | 2019-01-22 | 深圳市华星光电技术有限公司 | 自取向液晶介质组合物、液晶显示面板及其制作方法 |
CN106281364B (zh) * | 2016-07-21 | 2019-01-22 | 深圳市华星光电技术有限公司 | 自取向液晶介质组合物、液晶显示面板及其制作方法 |
TWI737834B (zh) * | 2016-10-26 | 2021-09-01 | 日商迪愛生股份有限公司 | 液晶組成物用自發配向助劑 |
-
2017
- 2017-10-12 TW TW106134854A patent/TWI737834B/zh active
- 2017-10-17 WO PCT/JP2017/037481 patent/WO2018079333A1/ja active Application Filing
- 2017-10-17 KR KR1020197007082A patent/KR20190073351A/ko not_active Application Discontinuation
- 2017-10-17 US US16/340,798 patent/US10927300B2/en active Active
- 2017-10-17 CN CN201780051758.XA patent/CN109643037B/zh active Active
- 2017-10-17 JP JP2018523035A patent/JP6447784B2/ja active Active
-
2018
- 2018-08-02 JP JP2018145906A patent/JP6721873B2/ja active Active
-
2020
- 2020-11-17 US US16/950,139 patent/US11345857B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2019012272A (ja) | 2019-01-24 |
US20190264108A1 (en) | 2019-08-29 |
US20210071084A1 (en) | 2021-03-11 |
CN109643037B (zh) | 2022-07-01 |
US10927300B2 (en) | 2021-02-23 |
JPWO2018079333A1 (ja) | 2018-10-25 |
US11345857B2 (en) | 2022-05-31 |
CN109643037A (zh) | 2019-04-16 |
TWI737834B (zh) | 2021-09-01 |
WO2018079333A1 (ja) | 2018-05-03 |
TW201829367A (zh) | 2018-08-16 |
KR20190073351A (ko) | 2019-06-26 |
JP6447784B2 (ja) | 2019-01-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6721873B2 (ja) | 液晶組成物用自発配向助剤 | |
JP6547907B2 (ja) | 液晶組成物用自発配向助剤、該自発配向助剤に好適な化合物、液晶組成物、及び液晶表示素子 | |
JP6972525B2 (ja) | 液晶組成物用自発配向助剤 | |
JP6729815B2 (ja) | 重合性化合物並びにそれを使用した液晶組成物及び液晶表示素子 | |
JP6610833B2 (ja) | 液晶組成物用自発配向助剤 | |
JP6690782B2 (ja) | 配向助剤、液晶組成物及び液晶表示素子 | |
JP6399261B1 (ja) | 液晶組成物用自発配向助剤 | |
JP2020052305A (ja) | 液晶表示素子の製造方法 | |
JP2019123875A (ja) | 重合性モノマー、それを用いた液晶組成物及び液晶表示素子 | |
JP6566153B1 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
JP6701611B2 (ja) | 液晶組成物及び液晶表示素子 | |
JP6699799B2 (ja) | 重合性化合物、並びにそれを使用した液晶組成物及び液晶表示素子 | |
WO2020044833A1 (ja) | 液晶組成物 | |
JP6849151B2 (ja) | 重合性化合物含有液晶組成物及び液晶表示素子ならびに重合性化合物 | |
JP7205152B2 (ja) | ネマチック液晶組成物及びこれを用いた液晶表示素子 | |
TW202028436A (zh) | 液晶組成物及液晶顯示元件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180806 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180806 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20190624 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190806 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20191002 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191007 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200205 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200304 |
|
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: 20200520 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200602 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6721873 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |