JP2008106201A - Chiral dopant for nematic or cholesteric liquid crystal - Google Patents
Chiral dopant for nematic or cholesteric liquid crystal Download PDFInfo
- Publication number
- JP2008106201A JP2008106201A JP2006292813A JP2006292813A JP2008106201A JP 2008106201 A JP2008106201 A JP 2008106201A JP 2006292813 A JP2006292813 A JP 2006292813A JP 2006292813 A JP2006292813 A JP 2006292813A JP 2008106201 A JP2008106201 A JP 2008106201A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- naphthalen
- methyl
- ethylimino
- chiral dopant
- 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.)
- Granted
Links
- 239000002019 doping agent Substances 0.000 title claims abstract description 48
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 title claims abstract description 22
- 239000004988 Nematic liquid crystal Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000005259 measurement Methods 0.000 claims abstract description 6
- YUYXUPYNSOFWFV-UHFFFAOYSA-N 4-(4-hexoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 YUYXUPYNSOFWFV-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 biphenyl compound Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000013329 compounding Methods 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- DDISIIIFASBOGP-UHFFFAOYSA-N C(CCCCCCC)OC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12)=O Chemical compound C(CCCCCCC)OC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12)=O DDISIIIFASBOGP-UHFFFAOYSA-N 0.000 claims description 2
- WZQIVPQUBVBLRK-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12 Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12 WZQIVPQUBVBLRK-UHFFFAOYSA-N 0.000 claims description 2
- UNIYWJXKENPIBS-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCC UNIYWJXKENPIBS-UHFFFAOYSA-N 0.000 claims description 2
- WJAQPYPLOMCLTO-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1 WJAQPYPLOMCLTO-UHFFFAOYSA-N 0.000 claims description 2
- CCWMMOHYRDDDIP-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C(=O)OC2=CC=C(C=C2)C=NC(C)C2=CC=CC3=CC=CC=C23)C=C1)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C(=O)OC2=CC=C(C=C2)C=NC(C)C2=CC=CC3=CC=CC=C23)C=C1)=O CCWMMOHYRDDDIP-UHFFFAOYSA-N 0.000 claims description 2
- JZBUYBRQTFGFLP-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12)=O JZBUYBRQTFGFLP-UHFFFAOYSA-N 0.000 claims description 2
- ARMVIEQOFRPAOZ-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)CCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)CCCCCCCC)=O ARMVIEQOFRPAOZ-UHFFFAOYSA-N 0.000 claims description 2
- FALBBXWOZQIZBT-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCC)=O FALBBXWOZQIZBT-UHFFFAOYSA-N 0.000 claims description 2
- LTRDYABBXNKXLU-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCCCC)=O LTRDYABBXNKXLU-UHFFFAOYSA-N 0.000 claims description 2
- PBQVMVJOQARQLG-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=CC=C1)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=CC=C1)=O PBQVMVJOQARQLG-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 230000003321 amplification Effects 0.000 abstract description 4
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 4
- 230000001939 inductive effect Effects 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 description 2
- JZBUYBRQTFGFLP-QXPUDEPPSA-N C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=N[C@H](C)C1=CC=CC2=CC=CC=C12)=O Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)C=N[C@H](C)C1=CC=CC2=CC=CC=C12)=O JZBUYBRQTFGFLP-QXPUDEPPSA-N 0.000 description 2
- WJAQPYPLOMCLTO-HSZRJFAPSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=CC=C1 WJAQPYPLOMCLTO-HSZRJFAPSA-N 0.000 description 2
- FALBBXWOZQIZBT-AREMUKBSSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCC)=O FALBBXWOZQIZBT-AREMUKBSSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002904 solvent Substances 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 1
- DUVJMSPTZMCSTQ-UHFFFAOYSA-N 2-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC=C1C=O DUVJMSPTZMCSTQ-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- IALWCYFULVHLEC-UHFFFAOYSA-N 4-(octyloxy)benzoic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=C1 IALWCYFULVHLEC-UHFFFAOYSA-N 0.000 description 1
- KVOWZHASDIKNFK-UHFFFAOYSA-N 4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=CC=C(C=O)C=C1 KVOWZHASDIKNFK-UHFFFAOYSA-N 0.000 description 1
- WZQIVPQUBVBLRK-RERZGLEZSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12 Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)C=NC(C)C1=CC=CC2=CC=CC=C12 WZQIVPQUBVBLRK-RERZGLEZSA-N 0.000 description 1
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- CCWMMOHYRDDDIP-XGDNGBMYSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C(=O)OC2=CC=C(C=C2)C=NC(C)C2=CC=CC3=CC=CC=C23)C=C1)=O Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C(=O)OC2=CC=C(C=C2)C=NC(C)C2=CC=CC3=CC=CC=C23)C=C1)=O CCWMMOHYRDDDIP-XGDNGBMYSA-N 0.000 description 1
- ARMVIEQOFRPAOZ-AREMUKBSSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)CCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)CCCCCCCC)=O ARMVIEQOFRPAOZ-AREMUKBSSA-N 0.000 description 1
- LTRDYABBXNKXLU-SSEXGKCCSA-N C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCCCC)=O Chemical compound C1(=CC=CC2=CC=CC=C12)[C@@H](C)N=CC1=CC=C(C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCCCC)=O LTRDYABBXNKXLU-SSEXGKCCSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004038 photonic crystal Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
本発明は、ネマチックもしくはコレステリック液晶用キラルドーパントおよび液晶組成物に関する。 The present invention relates to chiral dopants and liquid crystal compositions for nematic or cholesteric liquid crystals.
従来、可視光の波長程度をらせん周期を持つコレステリックフィルムは、その光反射特性を利用して、偏光板、光位相差板、反射防止膜等の光学部材、染料、顔料等に代わる構造色材、光導波路もしくはレーザ発振のためのホトニクスクリスタル材、等の幅広い分野で利用されようとしている。これらの素材の調製で最も重要な課題は、導入すべきキラルドーパントの種類、構造が限られ、その不斉によるキラリティ効果もそれほど大きくなく、多量のキラルドーパントの導入が必要であり、かつ非常に高価であるために、フィルムの価格を高くしてしまうことである。さらに、多量のキラルドーパントの使用はホスト液晶分子の性質を損なうという問題もある。 Conventionally, a cholesteric film having a helical period of about the wavelength of visible light is a structural color material that substitutes for optical members such as polarizing plates, optical phase difference plates, antireflection films, dyes, pigments, etc. by utilizing its light reflection characteristics. It is going to be used in a wide range of fields such as optical waveguides or photonic crystal materials for laser oscillation. The most important issues in the preparation of these materials are that the types and structures of chiral dopants to be introduced are limited, the chirality effect due to the asymmetry is not so great, a large amount of chiral dopants must be introduced, and Because it is expensive, it increases the price of the film. Further, the use of a large amount of chiral dopant has a problem that the properties of the host liquid crystal molecules are impaired.
本発明は、上記のようなキラルドーパントの難点を克服し、安価な化合物を含むキラルドーパントを用いて少量で液晶分子のねじれコンフォメーションの不斉増幅を生じさせ、大きなねじれ力を誘起しうるキラルドーパントを提供する。 The present invention overcomes the drawbacks of chiral dopants as described above, and uses chiral dopants including inexpensive compounds to cause asymmetric amplification of the twisted conformation of liquid crystal molecules in a small amount, and to induce a large twisting force. Providing a dopant;
本発明は上記の課題を解決するために以下の発明を提供する。 The present invention provides the following inventions in order to solve the above problems.
（１）一般式（１） (1) General formula (1)
（ここで、Ａｒは置換されていてもよい芳香族基、Ｒ１、Ｒ２はＣ＊が不斉炭素を形成するための置換基、Ｒ３は (Where Ar is an optionally substituted aromatic group, R 1 and R 2 are substituents for C * to form an asymmetric carbon, and R 3 is
、ならびにＲ４はＸ−Ｂ−Ａ−、を示す。Ａは置換されていてもよい芳香族基、Ｂは平面共役基であり、Ｘは置換されていてもよい芳香族基を含む残基である。）
で表される化合物を含むネマチックもしくはコレステリック液晶用キラルドーパント；
（２）液晶として4’−ヘキシルオキシ−4−シアノビフェニルを含む測定系において、１/ｐｃ（ｐ＝ピッチ（μｍ）、ｃ＝ドーパントのモル分率）で示されるねじれ力が６０/μｍ以上である上記（１）記載のキラルドーパント；
（３）Ａｒがナフチル基、Ｒ１およびＲ２が互いに相異なるアルキル基もしくは水素原子である上記（１）もしくは（２）記載のキラルドーパント；
（４）Ｘが不斉炭素を含む上記（１）〜（３）のいずれか記載のキラルドーパント；
（５）ネマチックもしくはコレステリック液晶に上記（１）〜（４）のいずれか記載のキラルドーパントを配合してなる液晶組成物；
（６）ネマチックもしくはコレステリック液晶がキラルドーパントと非反応性である上記（５）記載の液晶組成物；
（７）ネマチックもしくはコレステリック液晶がビフェニル系化合物である上記（５）もしくは（６）記載の液晶組成物；
（８）ネマチックもしくはコレステリック液晶が室温で液晶性を示す上記（５）〜（７）のいずれか記載の液晶組成物；
（９）キラルドーパントの配合量がネマチックもしくはコレステリック液晶とキラルドーパントの合計量に対し、０.００１〜３０モル％である上記（５）〜（８）のいずれかに記載の液晶組成物；
（１０）４−オクチルオキシ−安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１１）４−オクチル−安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１２）４’−オクチルオキシ−ビフェニル−４−カルボン酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１３）４−ドデシルオキシ−安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１４）ビフェニル−４−カルボン酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１５）４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] −安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル；
（１６）テレフタル酸ビス−｛４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニル｝エステル；
（１７）ビフェニル−４，４’−ジカルボン酸ビス−｛４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニル｝エステル；
（１８）安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル、ならびに
（１９）４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] −安息香酸 ４−オクチルオキシ−フェニルエステル、
である。
, And R 4 represents XBA-. A is an optionally substituted aromatic group, B is a planar conjugated group, and X is a residue containing an optionally substituted aromatic group. )
A chiral dopant for nematic or cholesteric liquid crystals containing a compound represented by:
(2) In a measurement system containing 4′-hexyloxy-4-cyanobiphenyl as a liquid crystal, the twisting force represented by 1 / pc (p = pitch (μm), c = molar fraction of dopant) is 60 / μm or more. The chiral dopant according to the above (1), which is
(3) The chiral dopant according to the above (1) or (2), wherein Ar is a naphthyl group, and R 1 and R 2 are different alkyl groups or hydrogen atoms;
(4) The chiral dopant according to any one of (1) to (3), wherein X contains an asymmetric carbon;
(5) A liquid crystal composition comprising a nematic or cholesteric liquid crystal and the chiral dopant according to any one of (1) to (4) above;
(6) The liquid crystal composition according to the above (5), wherein the nematic or cholesteric liquid crystal is non-reactive with the chiral dopant;
(7) The liquid crystal composition according to the above (5) or (6), wherein the nematic or cholesteric liquid crystal is a biphenyl compound;
(8) The liquid crystal composition according to any one of (5) to (7), wherein the nematic or cholesteric liquid crystal exhibits liquid crystallinity at room temperature;
(9) The liquid crystal composition according to any one of (5) to (8), wherein the compounding amount of the chiral dopant is 0.001 to 30 mol% with respect to the total amount of the nematic or cholesteric liquid crystal and the chiral dopant;
(10) 4-Octyloxy-benzoic acid 4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(11) 4-Octyl-benzoic acid 4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(12) 4'-octyloxy-biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(13) 4-dodecyloxy-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(14) biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(15) 4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester;
(16) terephthalic acid bis- {4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl} ester;
(17) Biphenyl-4,4′-dicarboxylic acid bis- {4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl} ester;
(18) Benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester and (19) 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -benzoic acid 4-octyloxy-phenyl ester,
It is.
本発明によれば、安価な化合物を含むキラルドーパントを用いて少量で液晶分子のねじれコンフォメーションの不斉増幅を生じさせ、大きなねじれ力を誘起しうるキラルドーパントを提供し得る。 According to the present invention, it is possible to provide a chiral dopant capable of inducing a large torsional force by causing asymmetric amplification of a twisted conformation of liquid crystal molecules with a small amount using a chiral dopant including an inexpensive compound.
本発明のキラルドーパントは、一般式（１） The chiral dopant of the present invention has the general formula (1)
で表される化合物を含むネマチックもしくはコレステリック液晶用キラルドーパントであり、Ａｒは置換されていてもよい芳香族基、Ｒ１、Ｒ２はＣ＊が不斉炭素を形成するための置換基、Ｒ３は Is a chiral dopant for nematic or cholesteric liquid crystals containing a compound represented by: Ar is an aromatic group which may be substituted, R 1 and R 2 are substituents for C * to form an asymmetric carbon, R 3 is
、ならびにＲ４はＸ−Ｂ−Ａ−、を示す。ここで、Ａは置換されていてもよい芳香族基、Ｂは平面共役基であり、Ｘは置換されていてもよい芳香族基を含む残基である。 , And R 4 represents XBA-. Here, A is an optionally substituted aromatic group, B is a planar conjugated group, and X is a residue containing an optionally substituted aromatic group.
Ａｒ，ＡおよびＸにおける置換されていてもよい芳香族基は、フェニル基等のベンゼン環、ナフチル基、アンスリル基、フェナンスリル基、等の縮合環、および複素芳香環の残基、ならびにこれらの置換体を含む。すなわち芳香族基としては、たとえば The aromatic group which may be substituted in Ar, A and X includes a benzene ring such as a phenyl group, a condensed ring such as a naphthyl group, an anthryl group, and a phenanthryl group, and a heteroaromatic ring residue, and substitution thereof. Including the body. That is, as an aromatic group, for example
等が挙げられる。 Etc.
Ｒ１、Ｒ２はＣ＊が不斉炭素を形成するための置換基であれば特に制限されないが、Ｒ１およびＲ２は互いに相異なるアルキル基もしくは水素原子であるのが好適であり、アルキル基としてはメチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル基等が挙げられる。さらにＲ１およびＲ２は互いに相異なるかぎり、たとえばＦ，Ｃｌ，Ｂｒ、ＣＦ３，ＣＣｌ３等のハロゲン含有基、等も好適に使用されうる。 R 1 and R 2 are not particularly limited as long as C * is a substituent for forming an asymmetric carbon, but R 1 and R 2 are preferably different alkyl groups or hydrogen atoms from each other. Examples of the group include methyl, ethyl, n-propyl, isopropyl, n-butyl group and the like. Furthermore, as long as R 1 and R 2 are different from each other, for example, halogen-containing groups such as F, Cl, Br, CF 3 , and CCl 3 can be preferably used.
Ｂにおける平面共役基としては、 As a plane conjugated group in B,
等が好適である。 Etc. are suitable.
また、Ｘにおける芳香族基を含む残基としては、その芳香族基のＢとの結合部位に対してパラ位がさらに芳香族を含む残基に結合されているものも好適に使用されうる。たとえばＡｒ〜Ｂの部位を含む２量体構造を有していてもよい。 In addition, as the residue containing an aromatic group in X, a residue in which the para position with respect to the binding site to B of the aromatic group is further bonded to a residue containing an aromatic group can be suitably used. For example, you may have a dimer structure containing the site | part of Ar-B.
本発明のキラルドーパントにおける好適な例は、たとえばＡｒがナフチル基、Ｒ１およびＲ２が互いに相異なるアルキル基もしくは水素原子である。 Preferable examples of the chiral dopant of the present invention include, for example, Ar is a naphthyl group, R 1 and R 2 are different alkyl groups or hydrogen atoms.
本発明のキラルドーパントは、液晶として4’−ヘキシルオキシ−4−シアノビフェニルを含む測定系において、１/ｐｃ（ｐ＝ピッチ（μｍ）、ｃ＝ドーパントのモル分率）で示されるねじれ力（キラル化合物のらせん誘起力の大きさを示す）が６０/μｍ以上であるのが好適であり、さらに好ましくは８０/μｍ以上、もっと好ましくは１００/μｍ以上である。 The chiral dopant of the present invention has a twisting force represented by 1 / pc (p = pitch (μm), c = molar fraction of dopant) in a measurement system containing 4′-hexyloxy-4-cyanobiphenyl as a liquid crystal. (The magnitude of the helical induction force of the chiral compound) is preferably 60 / μm or more, more preferably 80 / μm or more, and even more preferably 100 / μm or more.
本発明の好適なキラルドーパントを例示すると、次のとおりである。 Examples of suitable chiral dopants of the present invention are as follows.
Ｒ−（＋）−４−オクチルオキシ−安息香酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-4-octyloxy-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−４−オクチル−安息香酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-4-octyl-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−４’−オクチルオキシ−ビフェニル−４−カルボン酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-4'-octyloxy-biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−４−ドデシルオキシ−安息香酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-4-dodecyloxy-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−ビフェニル−４−カルボン酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-Biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] −安息香酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル。 R-(+)-4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester.
Ｒ−（＋）−テレフタル酸ビス−｛４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニル｝エステル。 R-(+)-Terephthalic acid bis- {4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl} ester.
Ｒ−（＋）−ビフェニル−４，４’−ジカルボン酸ビス−｛４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]−フェニル｝エステル。 R-(+)-Biphenyl-4,4'-dicarboxylic acid bis- {4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl} ester.
本発明の好適なキラルドーパントは上記の例に限定されず、さらに異性体であるＳ−（−）−体も含みうる。 Suitable chiral dopants of the present invention are not limited to the above examples, and may further include an S-(-)-isomer that is an isomer.
このような本発明のキラルドーパントは、ネマチックもしくはコレステリック液晶に配合され液晶組成物を形成しうる。その系全体はコレステリック液晶相を示す。ネマチックもしくはコレステリック液晶は特に制限されないが、ネマチックもしくはコレステリック液晶用キラルドーパントと非反応性であるのが好適であり、さらに実用上の観点から室温で液晶性を示すものが好適である。具体的には、4’−アルコキシ−4−シアノビフェニル、4’−アルキル−4−シアノビフェニル等のビフェニル化合物、４−（トランス−4’−アルキルシクロヘキシル）ベンゾニトリル等のフェニルシクロヘキサン化合物、トランス−トランス−4−アルキルビシクロヘキシル−４−カルボニトリル等のビシクロへキサン化合物、等が好適に使用される。 Such a chiral dopant of the present invention can be blended with a nematic or cholesteric liquid crystal to form a liquid crystal composition. The entire system exhibits a cholesteric liquid crystal phase. The nematic or cholesteric liquid crystal is not particularly limited, but is preferably non-reactive with a chiral dopant for nematic or cholesteric liquid crystal, and more preferably exhibits liquid crystallinity at room temperature from a practical viewpoint. Specifically, biphenyl compounds such as 4′-alkoxy-4-cyanobiphenyl and 4′-alkyl-4-cyanobiphenyl, phenylcyclohexane compounds such as 4- (trans-4′-alkylcyclohexyl) benzonitrile, trans- Bicyclohexane compounds such as trans-4-alkylbicyclohexyl-4-carbonitrile and the like are preferably used.
本発明のキラルドーパントの配合量は、ネマチックもしくはコレステリック液晶とキラルドーパントの合計量に対し、０.００１〜３０モル％、好ましくは０．０１〜１５モル％である。 The compounding quantity of the chiral dopant of this invention is 0.001-30 mol% with respect to the total amount of a nematic or cholesteric liquid crystal, and a chiral dopant, Preferably it is 0.01-15 mol%.
以下、実施例により本発明をさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.
実施例中、コレステリック液晶の偏光顕微鏡によるらせんピッチ観察は次の方法による。
実施例１
（１）表１に示す化合物１〜１６の合成
化合物１：Ｒ−（＋）−（１−ナフタレン−１−イル−エチル）−（４−オクチルオキシ −ベンジリデン）−アミン
化合物２：Ｒ−（＋）−４−オクチルオキシ−安息香酸 ４−[（１−ナフタレン−１− イル−エチルイミノ）−メチル]−フェニルエステル
化合物３：安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] ４ −[[４−[１−オクチルオキシ]フェノキシ]カルボニル]フェニルエステル
化合物４：Ｒ−（＋）−４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] −安息香酸 ４−オクチルオキシ−フェニルエステル
化合物５：Ｒ−（＋）−４−オクチル−安息香酸４−[（１−ナフタレン−１−イル−エ チルイミノ）−メチル]−フェニルエステル
化合物６：Ｒ−（＋）−４’−オクチルオキシ−ビフェニル−４−カルボン酸４−[（１ −ナフタレン−１−イル−エチルイミノ）−メチル]−フェニルエステル
化合物７：Ｒ−（＋）−（４−エトキシ−ベンジリデン）−（１−ナフタレン−１−イル −エチル）−アミン
化合物８：Ｒ−（＋）−安息香酸 ４−[（１−ナフタレン−１−イル−エチルイミノ） −メチル]−フェニルエステル
化合物９：Ｒ−（＋）−４−ブトキシ−安息香酸 ４−[（１−ナフタレン−１−イル− エチルイミノ）−メチル]−フェニルエステル
化合物１０：Ｒ−（＋）−４−ヘキシルオキシ−安息香酸 ４−[（１−ナフタレン−１ −イル−エチルイミノ）−メチル]−フェニルエステル
化合物１１：Ｒ−（＋）−４−ドデシルオキシ−安息香酸 ４−[（１−ナフタレン−１ −イル−エチルイミノ）−メチル]−フェニルエステル
化合物１２：Ｒ−（＋）−ビフェニル−４−カルボン酸４−[（１−ナフタレン−１−イ ル−エチルイミノ）−メチル]−フェニルエステル
化合物１３：Ｒ−（＋）−（１−ナフタレン−１−イル−エチル） −｛４−[（１−ナフ タレン−１−イル−エチルイミノ）−メチル]−ベンジリデン｝−アミン
化合物１４：Ｒ−（＋）−４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル] −安息香酸４−[（１−ナフタレン−１−イル−エチルイミノ）−メチル]− フェニルエステル
化合物１５：Ｒ−（＋）−テレフタル酸ビス−｛４−[（１−ナフタレン−１−イル−エ チルイミノ）−メチル]−フェニル｝エステル
化合物１６：Ｒ−（＋）−ビフェニル−４，４’−ジカルボン酸ビス−｛４−[（１−ナ フタレン−１−イル−エチルイミノ）−メチル]−フェニル｝エステル
In the examples, observation of the helical pitch of the cholesteric liquid crystal with a polarizing microscope is performed by the following method.
Example 1
(1) Synthetic compounds 1 to 16 shown in Table 1 Compound 1: R-(+)-(1-Naphthalen-1-yl-ethyl)-(4-octyloxy-benzylidene) -amine compound 2: R- ( +)-4-octyloxy-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 3: benzoic acid 4-[(1-naphthalen-1-yl-ethylimino)- Methyl] 4-[[4- [1-octyloxy] phenoxy] carbonyl] phenyl ester compound 4: R-(+)-4-[(1-naphthalen-1-yl-ethylimino) -methyl] -benzoic acid 4 -Octyloxy-phenyl ester compound 5: R-(+)-4-octyl-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 6: R- ( ) -4′-octyloxy-biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 7: R-(+)-(4-ethoxy-benzylidene) -(1-Naphthalen-1-yl-ethyl) -amine compound 8: R-(+)-benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 9: R- (+)-4-Butoxy-benzoic acid 4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 10: R-(+)-4-hexyloxy-benzoic acid 4-[( 1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 11: R-(+)-4-dodecyloxy-benzoic acid 4-[(1-naphthalen-1-yl-ethyl) Mino) -methyl] -phenyl ester compound 12: R-(+)-biphenyl-4-carboxylic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 13: R- ( +)-(1-Naphthalen-1-yl-ethyl)-{4-[(1-naphthalen-1-yl-ethylimino) -methyl] -benzylidene} -amine compound 14: R-(+)-4- [(1-Naphthalen-1-yl-ethylimino) -methyl] -benzoic acid 4-[(1-naphthalen-1-yl-ethylimino) -methyl] -phenyl ester compound 15: R-(+)-bis-terephthalate -{4-[(1-Naphthalen-1-yl-ethylimino) -methyl] -phenyl} ester compound 16: R-(+)-biphenyl-4,4'-dicarboxylic acid bis- {4-[(1 -Naf Talen-1-yl-ethylimino) -methyl] -phenyl} ester
（ａ）化合物１および７の合成
４−オクチルオキシベンズアルデヒドもしくは４−エトキシベンズアルデヒド２２．０ｍｍｏｌおよびＲ-（＋）-1-（１-ナフチル）エチルアミン２０．０ｍｍｏｌを、クロロホルム１００ｍＬおよびエタノール５０ｍＬの混合溶媒中に均一に溶解し、６０℃で５時間、還流した。室温に冷却した後、エタノール８０ｍＬを添加したところ、固体が析出した。析出した固体をエタノールから再結晶化し、４０〜７８％の収率で白色もしくは淡黄色の結晶の目的化合物を得た。
(A) Synthesis of compounds 1 and 7 4-octyloxybenzaldehyde or 2-ethoxybenzaldehyde (22.0 mmol) and R-(+)-1- (1-naphthyl) ethylamine (20.0 mmol) were mixed with chloroform (100 mL) and ethanol (50 mL). The solution was uniformly dissolved therein and refluxed at 60 ° C. for 5 hours. After cooling to room temperature, when 80 mL of ethanol was added, a solid precipitated. The precipitated solid was recrystallized from ethanol to obtain the target compound as white or pale yellow crystals in a yield of 40 to 78%.
（ｂ）化合物２、５、６、８〜１２の合成
対応する安息香酸１０．０ｍｍｏｌおよび４−ヒドロキシベンズアルデヒド１０．０ｍｍｏｌをクロロホルム８０ｍＬに溶解し、１−エチル−３−（３−ジメチルアミノプロピル）−カルボジイミド塩酸塩（ＥＤＣＩ）（東京化成製）１１．０ｍｍｏｌおよび触媒量のＮ，Ｎ’−ジメチルアミノピリジンを添加した。室温で一晩、攪拌した後、エタノールを添加したところ、橙色もしくは暗黄色の固体が析出した。析出した固体をエタノールから再結晶し、５５〜８０％の収率で中間体であるエステル化合物を得た。
(B) Synthesis of Compounds 2, 5, 6, 8-12 The corresponding benzoic acid 10.0 mmol and 4-hydroxybenzaldehyde 10.0 mmol were dissolved in 80 mL of chloroform, and 1-ethyl-3- (3-dimethylaminopropyl) was dissolved. -11.0 mmol of carbodiimide hydrochloride (EDCI) (manufactured by Tokyo Chemical Industry) and a catalytic amount of N, N'-dimethylaminopyridine were added. After stirring overnight at room temperature, ethanol was added to precipitate an orange or dark yellow solid. The precipitated solid was recrystallized from ethanol to obtain an ester compound as an intermediate in a yield of 55 to 80%.
（ａ）と同様の方法で、このエステル化合物１１．０ｍｍｏｌおよびＲ−（＋）−１−（１−ナフチル）エチルアミン１０．０ｍｍｏｌより、４０〜６５％の収率で目的化合物を得た。 The target compound was obtained in a yield of 40 to 65% from 11.0 mmol of this ester compound and 10.0 mmol of R-(+)-1- (1-naphthyl) ethylamine by the same method as (a).
（ｃ）化合物４の合成
（ｂ）と同様の方法で、４−オクチルオキシ安息香酸２０．０ｍｍｏｌおよび４−ホルミルベンズアルデヒド２０ｍｍｏｌから目的化合物を得た。エステル化合物の収率は７４％、エステル化合物からの収率は６０％であった。
(C) Synthesis of Compound 4 The target compound was obtained from 20.0 mmol of 4-octyloxybenzoic acid and 20 mmol of 4-formylbenzaldehyde in the same manner as in (b). The yield of the ester compound was 74%, and the yield from the ester compound was 60%.
（ｄ）化合物３の合成
３，４−ジヒドロ−２Ｈ−ピラン（ＤＨＰ）４０ｍｍｏｌを氷冷条件下でジオキサン５０ｍＬおよびメタノール５０ｍＬの混合溶液に溶解し、この溶液に４−ヒドロキシ安息香酸メチル３０．０ｍｍｏｌおよび触媒量のショウノウスルホン酸（ＣＳＡ）を溶解した。３時間攪拌した後に、反応溶液を氷水に注ぎ、塩酸で中和した。析出した固体をカラムクロマトグラフィ（溶媒 ヘキサン：酢酸エチル＝３：１）により精製したところ、透明な油状化合物が収率８０％で得られた。得られた油状化合物を１，４−ジオキサン６０ｍＬおよびメタノール３０ｍＬの混合溶液に溶解し、水酸化ナトリウム水溶液（６４ｍｍｏｌ/６０ｍＬ）を添加した。一晩攪拌した後、塩酸で中和したところ、白色の粗結晶が得られた。ヘキサン、酢酸エチルで再結晶したところ中間体の安息香酸が収率３０％で得られた。（ｂ）と同様の方法で、この安息香酸２０．０ｍｍｏｌおよび４−ヒドロキシベンズアルデヒドから目的化合物を得た。エステル化合物の収率は６０％、エステル化合物からの収率は７１％であった。
(D) Synthesis of Compound 3 40 mmol of 3,4-dihydro-2H-pyran (DHP) was dissolved in a mixed solution of 50 mL of dioxane and 50 mL of methanol under ice cooling conditions, and 30.0 mmol of methyl 4-hydroxybenzoate was added to this solution. And a catalytic amount of camphorsulfonic acid (CSA) was dissolved. After stirring for 3 hours, the reaction solution was poured into ice water and neutralized with hydrochloric acid. The precipitated solid was purified by column chromatography (solvent hexane: ethyl acetate = 3: 1), whereby a transparent oily compound was obtained in a yield of 80%. The obtained oily compound was dissolved in a mixed solution of 60 mL of 1,4-dioxane and 30 mL of methanol, and an aqueous sodium hydroxide solution (64 mmol / 60 mL) was added. After stirring overnight, the mixture was neutralized with hydrochloric acid to obtain white crude crystals. Recrystallization from hexane and ethyl acetate yielded an intermediate benzoic acid in 30% yield. In the same manner as in (b), the target compound was obtained from 20.0 mmol of this benzoic acid and 4-hydroxybenzaldehyde. The yield of the ester compound was 60%, and the yield from the ester compound was 71%.
（ｅ）化合物１３〜１６の合成
上記の（ａ）もしくは（ｂ）と同様な方法により化合物１３〜１６を得た。
(E) Synthesis of Compounds 13 to 16 Compounds 13 to 16 were obtained in the same manner as (a) or (b) above.
化合物１３：（ａ）法、ただしアルデヒド１当量に対してアミン２当量を用いた。 Compound 13: Method (a), except that 2 equivalents of amine per 1 equivalent of aldehyde were used.
化合物１４：（ｂ）法を用いた。 Compound 14: Method (b) was used.
化合物１５および１６：（ｂ）法、ただしカルボン酸１当量に対して４−ヒドロキシアルデヒド２当量を用い、アルデヒド１当量に対してアミン２当量を用いた。 Compounds 15 and 16: Method (b), except that 2 equivalents of 4-hydroxyaldehyde were used per equivalent of carboxylic acid and 2 equivalents of amine per equivalent of aldehyde.
（２）融点および１Ｈ−ＮＭＲスペクトル
上記のように合成された化合物１〜１６について、融点および１Ｈ−ＮＭＲスペクトル（溶媒：ＣＤＣｌ３）の測定結果は次のとおりであった。
化合物１（融点 ８９℃）
化合物２（融点 ８０℃）
δ１．７６（ｄ,３）、δ４．０４−４．０６（ｔ,２）、δ５．３６−５．３８（ｑ,１）、δ６．９６−６．９８、７．４９−８．２４（ｍ,１３）、δ８．４３（ｓ,１）
化合物３（融点 １５４℃）
δ１．７９（ｄ,３）、δ３．９７（ｔ,２）、δ５．４−５．５（ｍ,１）、δ６．９２−７．１３、７．３７−８．３０（ｍ,１８）、δ８．５１（ｓ,１）
化合物４（融点 １２０℃）
δ３．９６（ｔ,２）、δ５．４１（ｑ,１）、δ６．９２−７．１３、７．５０−８．２４（ｍ,１５）、δ８．５０（ｓ,１）
化合物５（融点 ７９℃）
δ１．７４−１．７６（ｄ,３）、δ５．３６−５．３８（ｑ,１）、δ７．２６−８．１２（ｍ,１２）、δ８．４３（ｓ,１）
化合物６（融点 １４４℃）
δ１．７５（ｄ,３）、δ４．０２（ｔ,２）、δ５．３８−５．３９（ｑ,１）、δ７．００−８．２５（ｍ,１９）、δ８．４５（ｓ,１）
化合物７（融点 ７２℃）
δ１．７２（ｄ,３）、δ４．０４−４．０７（ｑ,２）、δ５．３０−５．３２（ｑ,１）、δ６．９０−６．９２、７．４７−７．８０（ｍ,１１）、δ８．３５（ｓ,１）
化合物８（融点 １２６℃）
δ１．７４−１．７６（ｄ,３）、δ５．３７−５．３８（ｑ,１）、δ７．２６−８．２２（ｍ,１９）、δ８．４４（ｓ,１）
化合物９（融点 １２７℃）
δ１．７４（ｄ,３）、δ４．０３−４．０６（ｔ,２）、δ５．３６−５．３８（ｑ,１）、δ６．９６−８．２４（ｍ,１４）（δ７．２６除く）、δ８．４１（ｓ,１）
化合物１０（融点 １２８℃）
δ１．７４（ｄ,３）、δ４．０４（ｔ,２）、δ５．３６（ｑ,１）、δ６．９６−６．９８、７．４９−８．１４（ｍ,１５）、δ８．４３（ｓ,１）
化合物１１（融点 １３４℃）
δ１．７４（ｄ,３）、δ４．０３−４．０４（ｔ,２）、δ５．３７−５．３８（ｑ,１）、δ６．９６−６．９８、７．４９−８．１５（ｍ,１５）、δ８．４４（ｓ,１）
化合物１２（融点 １３０℃）
δ１．７６（ｄ,３）、δ５．３７−５．３９（ｑ,１）、δ７．４９−８．２８（ｍ,２０）、δ８．４４（ｓ,１）
化合物１３（融点 １７９℃）
δ１．７４−１．７７（ｄ,６）、δ５．３７−５．４０（ｑ,２）、δ７．４９−７．８７（ｍ,１８）、δ８．４４（ｓ,２）
化合物１４（融点 １６９℃）
δ１．７４−１．７９（ｍ,６）、δ５．３９−５．４４（ｍ,２）、δ７．２８−７．９６（ｍ,２２）、δ８．４５（ｓ,１）、δ８．５１（ｓ,１）
化合物１５（融点 １７２℃）
δ１．７７（ｄ,６）、δ５．３７−５．４２（ｑ,２）、δ７．３０−８．３４（ｍ,２８）、δ８．４５（ｓ,２）
化合物１６（融点 １９９℃）
δ１．７５−１．７７（ｄ,６）、δ５．３４−５．４０（ｑ,２）、δ７．３０−８．３３（ｍ,３０）、δ８．４５（ｓ,２）
(2) The melting point and 1 H-NMR spectrum Compound 1-16 synthesized as described above, the melting point and 1 H-NMR spectrum (solvent: CDCl 3) measurement results of were as follows.
Compound 1 (melting point 89 ° C)
Compound 2 (melting point 80 ° C)
δ 1.76 (d, 3), δ 4.04-4.06 (t, 2), δ 5.36-5.38 (q, 1), δ 6.96-6.98, 7.49-8.24 (M, 13), δ 8.43 (s, 1)
Compound 3 (melting point 154 ° C.)
δ 1.79 (d, 3), δ 3.97 (t, 2), δ 5.4-5.5 (m, 1), δ 6.92-7.13, 7.37-8.30 (m, 18 ), Δ 8.51 (s, 1)
Compound 4 (melting point 120 ° C.)
δ 3.96 (t, 2), δ 5.41 (q, 1), δ 6.92-7.13, 7.50-8.24 (m, 15), δ 8.50 (s, 1)
Compound 5 (melting point 79 ° C)
δ1.74-1.76 (d, 3), δ5.36-5.38 (q, 1), δ7.26-8.12 (m, 12), δ8.43 (s, 1)
Compound 6 (melting point 144 ° C.)
δ 1.75 (d, 3), δ 4.02 (t, 2), δ 5.38-5.39 (q, 1), δ 7.00-8.25 (m, 19), δ 8.45 (s, 1)
Compound 7 (melting point 72 ° C)
δ 1.72 (d, 3), δ 4.04-4.07 (q, 2), δ 5.30-5.32 (q, 1), δ 6.90-6.92, 7.47-7.80 (M, 11), δ 8.35 (s, 1)
Compound 8 (melting point 126 ° C.)
δ1.74-1.76 (d, 3), δ5.37-5.38 (q, 1), δ7.26-8.22 (m, 19), δ8.44 (s, 1)
Compound 9 (melting point 127 ° C.)
δ 1.74 (d, 3), δ 4.03-4.06 (t, 2), δ 5.36-5.38 (q, 1), δ 6.96-8.24 (m, 14) (δ 7. 26), δ8.41 (s, 1)
Compound 10 (melting point 128 ° C.)
δ1.74 (d, 3), δ4.04 (t, 2), δ5.36 (q, 1), δ6.96-6.98, 7.49-8.14 (m, 15), δ8. 43 (s, 1)
Compound 11 (melting point 134 ° C.)
δ1.74 (d, 3), δ4.03-4.04 (t, 2), δ5.37-5.38 (q, 1), δ6.96-6.98, 7.49-8.15 (M, 15), δ 8.44 (s, 1)
Compound 12 (melting point 130 ° C.)
δ1.76 (d, 3), δ5.37-5.39 (q, 1), δ7.49-8.28 (m, 20), δ8.44 (s, 1)
Compound 13 (melting point 179 ° C.)
δ1.74-1.77 (d, 6), δ5.37-5.40 (q, 2), δ7.49-7.87 (m, 18), δ8.44 (s, 2)
Compound 14 (melting point 169 ° C.)
δ1.74-1.79 (m, 6), δ5.39-5.44 (m, 2), δ7.28-7.96 (m, 22), δ8.45 (s, 1), δ8. 51 (s, 1)
Compound 15 (melting point 172 ° C.)
δ 1.77 (d, 6), δ 5.37-5.42 (q, 2), δ 7.30-8.34 (m, 28), δ 8.45 (s, 2)
Compound 16 (melting point: 199 ° C.)
δ1.75-1.77 (d, 6), δ5.34-5.40 (q, 2), δ7.30-8.33 (m, 30), δ8.45 (s, 2)
（３）試料調製およびねじれ力測定
表１に示したキラルドーパントと６−ＯＣＢ（4’−ヘキシルオキシ−4−シアノビフェニル）ホスト液晶との混合物の調製方法を示す。たとえば化合物１を１０ｍｏｌ％含有する混合物は次のようにして調製した。化合物１の１０．０ｇ/Ｌクロロホルム溶液０．６８ｍＬを、６−ＯＣＢホスト液晶０．１００ｇと混合し、クロロホルムを蒸発させた。この粗混合物を微粉末に粉砕した。他の混合物も同様に調製した。
(3) Sample preparation and measurement of torsional force A method for preparing a mixture of the chiral dopant shown in Table 1 and 6-OCB (4′-hexyloxy-4-cyanobiphenyl) host liquid crystal is shown. For example, a mixture containing 10 mol% of Compound 1 was prepared as follows. 0.68 mL of 10.0 g / L chloroform solution of Compound 1 was mixed with 0.100 g of 6-OCB host liquid crystal, and chloroform was evaporated. This crude mixture was ground into a fine powder. Other mixtures were prepared similarly.
試料の光学顕微鏡特性はホットステージ（Mettler EP 90 HT）を備えた顕微鏡(Olympus BX50)を用いて測定した。ＤＳＣ示差熱分析データはPerkin-Elmer DSC7示差熱量測定装置を用いて測定した。キラルネマチック相からの選択的な反射バンドはJASCO J-720WI 円二色スペクトロメータにより９００〜４００ｎｍの幅広い範囲で測定した。光学的らせんピッチｎＰが式（２）
λｍ＝ｎＰ （２）
（ここで、ｎ、Ｐおよびλｍはそれぞれ平均屈折率１．５（代表的液晶化合物の平均値）、らせんピッチおよび反射バンドの最大波長である。）
で計算される。
The optical microscope characteristics of the sample were measured using a microscope (Olympus BX50) equipped with a hot stage (Mettler EP 90 HT). DSC differential thermal analysis data was measured using a Perkin-Elmer DSC7 differential calorimeter. The selective reflection band from the chiral nematic phase was measured over a wide range of 900 to 400 nm by JASCO J-720WI circular dichroism spectrometer. The optical helical pitch nP is expressed by the formula (2)
λ m = nP (2)
(Here, n, P, and λ m are the average refractive index 1.5 (average value of typical liquid crystal compounds), the helical pitch, and the maximum wavelength of the reflection band, respectively.)
Calculated by
試料は等方性液体温度から結晶化温度までの冷却および加熱過程で１０分間毎に測定した。表１に測定したねじれ力を示す。 Samples were measured every 10 minutes during the cooling and heating process from the isotropic liquid temperature to the crystallization temperature. Table 1 shows the measured torsional force.
本発明によれば、安価な化合物を含むキラルドーパントを用いて少量で液晶分子のねじれコンフォメーションの不斉増幅を生じさせ、大きなねじれ力を誘起しうるキラルドーパントを提供しうる。 According to the present invention, it is possible to provide a chiral dopant capable of inducing a large torsional force by causing asymmetric amplification of a twisted conformation of liquid crystal molecules with a small amount using a chiral dopant including an inexpensive compound.
Claims (19)
で表される化合物を含むネマチックもしくはコレステリック液晶用キラルドーパント。 General formula (1)
A chiral dopant for nematic or cholesteric liquid crystals containing a compound represented by the formula:
５記載の液晶組成物。 6. A liquid crystal composition according to claim 5, wherein the nematic or cholesteric liquid crystal is non-reactive with the chiral dopant.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20120138609A (en) * | 2011-06-15 | 2012-12-26 | 엘지디스플레이 주식회사 | Method for produsing cholesteric liquid crystal display device |
| KR20130041718A (en) * | 2011-10-17 | 2013-04-25 | 엘지디스플레이 주식회사 | Method for fabricating colesteric liquid crystal display |
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| JP2004285174A (en) * | 2003-03-20 | 2004-10-14 | Nitto Denko Corp | Liquid-crystal polymer and liquid-crystal polymer composition |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120138609A (en) * | 2011-06-15 | 2012-12-26 | 엘지디스플레이 주식회사 | Method for produsing cholesteric liquid crystal display device |
| KR101992883B1 (en) * | 2011-06-15 | 2019-06-25 | 엘지디스플레이 주식회사 | Method for produsing cholesteric liquid crystal display device |
| KR20130041718A (en) * | 2011-10-17 | 2013-04-25 | 엘지디스플레이 주식회사 | Method for fabricating colesteric liquid crystal display |
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