JP2006152290A - 液晶性化合物、およびこれを用いたイオン伝導体 - Google Patents
液晶性化合物、およびこれを用いたイオン伝導体 Download PDFInfo
- Publication number
- JP2006152290A JP2006152290A JP2005323443A JP2005323443A JP2006152290A JP 2006152290 A JP2006152290 A JP 2006152290A JP 2005323443 A JP2005323443 A JP 2005323443A JP 2005323443 A JP2005323443 A JP 2005323443A JP 2006152290 A JP2006152290 A JP 2006152290A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- liquid crystal
- compound
- group
- crystal compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000010416 ion conductor Substances 0.000 title claims abstract description 43
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000003792 electrolyte Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000006353 oxyethylene group Chemical group 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- QQVDJLLNRSOCEL-UHFFFAOYSA-N (2-aminoethyl)phosphonic acid Chemical compound [NH3+]CCP(O)([O-])=O QQVDJLLNRSOCEL-UHFFFAOYSA-N 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- IUDNRKGPFWUYIC-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 IUDNRKGPFWUYIC-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1ccc(C2OCC(*)CO2)cc1 Chemical compound Cc1ccc(C2OCC(*)CO2)cc1 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 239000011245 gel electrolyte Substances 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011244 liquid electrolyte Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QDBZWLAQPHAUGV-UHFFFAOYSA-N (2-methoxyphenyl)phosphonic acid Chemical compound COC1=CC=CC=C1P(O)(O)=O QDBZWLAQPHAUGV-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- UTHULKKJYXJZLV-UHFFFAOYSA-N (3-aminophenoxy)boronic acid Chemical compound NC1=CC=CC(OB(O)O)=C1 UTHULKKJYXJZLV-UHFFFAOYSA-N 0.000 description 1
- CVISDVLTGPAQGC-UHFFFAOYSA-N (3-hydroxyphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(O)=C1 CVISDVLTGPAQGC-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- DIZBQMTZXOUFTD-UHFFFAOYSA-N 2-(furan-2-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CO1 DIZBQMTZXOUFTD-UHFFFAOYSA-N 0.000 description 1
- QQQMJWSOHKTWDZ-UHFFFAOYSA-N 2-[amino(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(N)CC(O)=O QQQMJWSOHKTWDZ-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- IOJDZGGPJSPMQW-UHFFFAOYSA-N 3-(4-pentylcyclohexyl)-4-phenylbenzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC(C#N)=CC=C1C1=CC=CC=C1 IOJDZGGPJSPMQW-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-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
- JPBFKTCKZLMJED-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzonitrile Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 JPBFKTCKZLMJED-UHFFFAOYSA-N 0.000 description 1
- ZRMIETZFPZGBEB-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzonitrile Chemical group C1=CC(O)=CC=C1C1=CC=C(C#N)C=C1 ZRMIETZFPZGBEB-UHFFFAOYSA-N 0.000 description 1
- RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZZKFHBJYRMQKHD-UHFFFAOYSA-N CC(C)(C)P(O)=O Chemical compound CC(C)(C)P(O)=O ZZKFHBJYRMQKHD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 229910012513 LiSbF 6 Inorganic materials 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- QDFHPFSBQFLLSW-KQYNXXCUSA-N adenosine 2'-phosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OP(O)(O)=O QDFHPFSBQFLLSW-KQYNXXCUSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- HXXFSFRBOHSIMQ-FPRJBGLDSA-N alpha-D-galactose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O HXXFSFRBOHSIMQ-FPRJBGLDSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- CQAGLAXSRJMWSA-UHFFFAOYSA-N hydrazinyl hydrogen sulfate Chemical compound NNOS(O)(=O)=O CQAGLAXSRJMWSA-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
- 238000002847 impedance measurement Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- DGFLVXIQGRFWHJ-UHFFFAOYSA-N methoxymethane;4-methylbenzenesulfonic acid Chemical compound COC.CC1=CC=C(S(O)(=O)=O)C=C1 DGFLVXIQGRFWHJ-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- VPRUMANMDWQMNF-UHFFFAOYSA-N phenylethane boronic acid Chemical compound OB(O)CCC1=CC=CC=C1 VPRUMANMDWQMNF-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000010992 reflux Methods 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
- 239000008117 stearic acid Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Primary Cells (AREA)
- Fuel Cell (AREA)
- Hybrid Cells (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Conductive Materials (AREA)
- Secondary Cells (AREA)
Abstract
Description
(垂直方向イオン伝導率の測定方法)
図1に、イオン伝導率の測定に用いたセルを示す。このセルを作製するために、まず、アルゴングローブボックス内にて、予め透明導電膜としてITO膜3を形成した縦15mm、横10mmのガラス板(ITO膜付きガラス電極)4に、試料充填部1として直径(r)6mmの円を打ち抜いた厚み25μmの粘着剤付きポリイミドフィルム(図2参照)をスペーサー2として貼り付けた。次いで、試料充填部1に、加熱して等方性液体状態とした試料(イオン伝導体)を充填し、その後、もう1枚のITO膜付きガラス電極4をITO膜3が充填部1側となるように配置した。
d:スペーサー厚み(cm)、R:実数成分インピーダンス(Ω)、A:極板面積(cm2)
図3に、水平方向イオン伝導率の測定に用いた櫛型電極を示す。この櫛型電極11は、ガラス板上に、ITOを厚み30nmとなるように蒸着し、さらにAgとAuとからなる合金を総厚みが0.8μmとなるように蒸着することにより形成した。互いに対向するように配置した櫛型電極11は、それぞれ3つの櫛部12を有し、各櫛部12の幅Wは2mm、櫛部12の間隔Dは3mm、対向する櫛部の重複幅Vは7mmとした。この櫛型電極11の櫛部12の間に、測定対象とする試料を等方性状態となるように加熱してから塗布し、この試料を覆う領域に縦10mm、横25mmのガラス板を重ねてこの領域(測定領域13)でのみ試料を保持した。その後、垂直方向イオン伝導率の測定と同様にして伝導率σpを求めた。なお、伝導率σpの絶対値は、試料が等方性液体状態のときの測定値で補正した。
偏光顕微鏡(オリンパス製)を用い、液晶相の観察を行なった。
一般式(化1)において、n=3、R1=CN基、R2=オクチルオキシ基、X=COO基に相当する液晶性化合物を、図4に示したスキームに従って合成した。化合物の同定は1Hおよび13C NMR測定により行なった。以下、各化合物は、図4に付した数字により、「化合物1」等と表記する。
2,4−ジヒドロキシ安息香酸(3.02g,19.6mmol)のジメチルホルムアミド(DMF)10mL溶液に炭酸水素ナトリウム(5.00g,59.5mmol)を加え、アルゴン雰囲気にした後、70℃で1時間激しく攪拌した。この溶液にベンジルブロマイド(4.01g,23.4mmol)を加え、さらに70℃で10時間激しく攪拌した。反応溶液を室温に冷ました後、酢酸エチルおよび飽和塩化アンモニウム水溶液を加えて有機層を抽出し、有機層を飽和塩化ナトリウム水溶液で洗浄した。硫酸マグネシウムを加え、有機層を乾操し、ろ過した後、ロータリーエバポレーターを用いて溶媒を減圧留去した。残渣をシリカゲルクロマトグラフィー(展開溶媒:ジクロロメタン)によって精製し、白色固体の化合物3を収率89%(4.26g,17.4mmol)で得た。
化合物3(4.26g,17.4mmol)とオクチルブロマイド(3.69g,19.1mmol)のDMF50mL溶液に炭酸カリウム(8.00g,57.9mmol)を加え、アルゴン雰囲気にした後、70℃で5時間激しく攪拌した。反応溶液に酢酸エチルおよび飽和塩化アンモニウム水溶液を加えて有機層を抽出し、有機層を飽和塩化ナトリウム水溶液で洗浄した。硫酸マグネシウムを加え、有機層を乾焼し、ろ過した後、ロータリーエバポレーターを用いて溶媒を減圧留去した。残渣をシリカゲルクロマトグラフィー(展開溶媒:ヘキサン)によって精製し、白色固体の化合物4を収率68%(4.19g, 11.8mmol)で得た。
化合物4(1.01g,2.83mmol)とトリエチレングリコールモノメチルエーテルモノトシレート(1.06g,3.33mmol)のDMF50mL溶液に炭酸カリウム(1.28g,9.26mmol)を加え、アルゴン雰囲気にした後、70℃で3時間激しく攪拌した。反応溶液に酢酸エチルおよび飽和塩化アンモニウム水溶液を加えて有機層を抽出し、有機層を飽和塩化ナトリウム水溶液で洗浄した。硫酸マグネシウムを加え、有機層を乾焼し、ろ過した後、ロータリーエバボレーターを用いて溶媒を減圧留去した。残渣をシリカゲルクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=5/1)によって精製し、無色粘性液体の化合物5を収率96%(1.37g,2.73mmol)で得た。
化合物5(1.37g,2.73mmol)のエタノール50mL溶液に水酸化ナトリウム(0.63g,15.8mmol)を加え、3時間還流攪拌した。反応溶液を室温に冷ました後、5%塩酸水溶液を加えて中和した。ロータリーエバポレーターを用いて溶媒を減圧留去し、残渣に酢酸エチルと水を加え、有機層を抽出した。有機層に硫酸マグネシウムを加えて乾焼し、ろ過した後、ロータリーエバポレーターを用いて溶媒を減圧留去した。残渣をシリカゲルクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=5/1)によって精製し、無色粘性液体の化合物6を収率71%(0.80g,1.94mmol)で得た。
化合物6(2.64g,6.40mmol)、4’−ヒドロキシ−4−シアノビフェニル(1.58g,8.09mmol)、4−ジメチルアミノピリジン(DMAP)(8.4g, 0.069mmol)、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(ECD)(1.42g,7.41mmol)のジクロロメタン50mL溶液を室温で3時間攪拌した。反応溶液に酢酸エチルと飽和塩化ナトリウム水溶液を加え、有機層を抽出した。有機層に硫酸マグネシウムを加えて乾燥し、ろ過した後、ロータリーエバポレーターを用いて溶媒を減圧留去した。残渣をシリカゲルクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル=4/1)によって精製し、白色固体の化合物1を収率55%(2.06g,3.50mmol)で得た。
一般式(化1)において、n=2、R1=CN基、R2=オクチルオキシ基、X=COO基に相当する液晶性化合物を、トリエチレングリコールモノメチルエーテルモノトシレートに代えて、ジエチレングリコールモノメチルエーテルモノトシレートを使用した以外は、合成例1と同様、図4に示したスキームに従って合成した。化合物の同定は1Hおよび13C NMR測定により行なった。
合成例1により得た液晶化合物と、LiN(CF3SO2)2(キシダ化学製、LiTFSi)とを、モル比で95:5となるように混合した。
合成例1により得た液晶化合物と、一般式(化3)においてR3がペンチル基に相当する4’−ペンチルオキシ−ビフェニル−4−カルボニトリル(ワコーケミカル製、5OCB)と、一般式(化3)においてR3がヘプチル基に相当する4’−ヘプチルオキシ−ビフェニル−4−カルボニトリル(ワコーケミカル製、7OCB)と、一般式(化8)においてR8がペンチル基に相当する4’−(4−ペンチルシクロヘキシル)−ビフェニル−4−カルボニトリル(Valiant Fine Chemicals製、BCH5)と、LiTFSi(キシダ化学製)とを、モル比で、50:21.4:21.4:4.75:5となるように混合した。
合成例2により得た液晶化合物と、一般式(化3)においてR3がペンチル基に相当する5OCB(ワコーケミカル製)と、一般式(化3)においてR3がヘプチル基に相当する7OCBと、LiTFSi(キシダ化学製)とを、モル比で、9.5:42.75:42.75:5となるように混合した。
合成例2により得た液晶化合物と、一般式(化3)においてR3がペンチル基に相当する5OCB(ワコーケミカル製)と、一般式(化3)においてR3がヘプチル基に相当する7OCBと、末端にメトキシ基を有するオキシエチレン単位数が4であるエチレンオキシドオリゴマーに相当するテトラエチレングリコールジメチルエーテル(東京化成製)と、LiTFSi(キシダ化学製)とを、モル比で、3.8:43.7:43.7:3.8:5となるように混合した。
2 スペーサー
3 ITO膜
4 ITO膜付きガラス電極
11 櫛型電極
12 櫛部
13 測定領域
Claims (6)
- 請求項1に記載の液晶性化合物(A)と、電解質とを含むイオン伝導体。
- 前記液晶性化合物(A)とは異なる液晶性化合物であってネマチック液晶相を示す液晶性化合物(B)をさらに含む請求項2に記載のイオン伝導体。
- 前記液晶性化合物(B)を2種以上含む請求項3または4に記載のイオン伝導体。
- エチレンオキシドオリゴマーをさらに含む請求項2〜5のいずれか1項に記載のイオン伝導体。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005323443A JP4896497B2 (ja) | 2004-11-08 | 2005-11-08 | 液晶性化合物、およびこれを用いたイオン伝導体 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004324255 | 2004-11-08 | ||
JP2004324255 | 2004-11-08 | ||
JP2005323443A JP4896497B2 (ja) | 2004-11-08 | 2005-11-08 | 液晶性化合物、およびこれを用いたイオン伝導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006152290A true JP2006152290A (ja) | 2006-06-15 |
JP4896497B2 JP4896497B2 (ja) | 2012-03-14 |
Family
ID=36630947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005323443A Expired - Fee Related JP4896497B2 (ja) | 2004-11-08 | 2005-11-08 | 液晶性化合物、およびこれを用いたイオン伝導体 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4896497B2 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101864927B1 (ko) * | 2015-03-31 | 2018-07-04 | 주식회사 엘지화학 | 액정 소자 |
US10663828B2 (en) | 2015-03-31 | 2020-05-26 | Lg Chem, Ltd. | Liquid crystal device |
US10756348B2 (en) | 2015-08-26 | 2020-08-25 | Evonik Operations Gmbh | Use of certain polymers as a charge store |
US10957907B2 (en) | 2015-08-26 | 2021-03-23 | Evonik Operations Gmbh | Use of certain polymers as a charge store |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001338527A (ja) * | 2000-05-30 | 2001-12-07 | Canon Inc | 電解質および二次電池 |
JP2002105033A (ja) * | 2000-07-24 | 2002-04-10 | Canon Inc | 液晶性化合物、高分子液晶性化合物、それらを含む電解質および二次電池 |
JP2002358821A (ja) * | 2001-03-30 | 2002-12-13 | Japan Science & Technology Corp | 液晶性イオン伝導体とその製造方法 |
-
2005
- 2005-11-08 JP JP2005323443A patent/JP4896497B2/ja not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001338527A (ja) * | 2000-05-30 | 2001-12-07 | Canon Inc | 電解質および二次電池 |
JP2002105033A (ja) * | 2000-07-24 | 2002-04-10 | Canon Inc | 液晶性化合物、高分子液晶性化合物、それらを含む電解質および二次電池 |
JP2002358821A (ja) * | 2001-03-30 | 2002-12-13 | Japan Science & Technology Corp | 液晶性イオン伝導体とその製造方法 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101864927B1 (ko) * | 2015-03-31 | 2018-07-04 | 주식회사 엘지화학 | 액정 소자 |
US10663825B2 (en) | 2015-03-31 | 2020-05-26 | Lg Chem, Ltd. | Liquid crystal device |
US10663828B2 (en) | 2015-03-31 | 2020-05-26 | Lg Chem, Ltd. | Liquid crystal device |
US10756348B2 (en) | 2015-08-26 | 2020-08-25 | Evonik Operations Gmbh | Use of certain polymers as a charge store |
US10957907B2 (en) | 2015-08-26 | 2021-03-23 | Evonik Operations Gmbh | Use of certain polymers as a charge store |
Also Published As
Publication number | Publication date |
---|---|
JP4896497B2 (ja) | 2012-03-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Zhou et al. | Lithium-doped, organic ionic plastic crystal electrolytes exhibiting high ambient-temperature conductivities | |
Lee et al. | Ionic conductivity of a polymer electrolyte with modified carbonate as a plasticizer for poly (ethylene oxide) | |
KR100579650B1 (ko) | 액정성 이온전도체와 그 제조방법 | |
CN106318402B (zh) | 一种负性液晶化合物、组合物及其应用 | |
Cospito et al. | Mesomorphism and electrochemistry of thienoviologen liquid crystals | |
JP3619174B2 (ja) | 高分子液晶性化合物、それらを含む電解質および二次電池 | |
JP4896497B2 (ja) | 液晶性化合物、およびこれを用いたイオン伝導体 | |
JPWO2008081811A1 (ja) | プラスティッククリスタル | |
Bhowmik et al. | Ionic liquid crystals: Synthesis and characterization via NMR, DSC, POM, X-ray diffraction and ionic conductivity of asymmetric viologen bistriflimide salts | |
Ohtake et al. | Liquid-crystalline complexes of a lithium salt with twin oligomers containing oxyethylene spacers. An approach to anisotropic ion conduction | |
Eisele et al. | Structure and ionic conductivity of liquid crystals having propylene carbonate units | |
JP2005239639A (ja) | イオン伝導体 | |
KR100283163B1 (ko) | 시클로헥센일 코아를 갖는 강유전성 액정 화합물 및 이들을 함유하는 조성물 | |
JP2007194150A (ja) | イオン伝導体 | |
US8834743B2 (en) | Dicarboxylate gemini surfactant that forms a lyotropic liquid crystal | |
WO2019221267A1 (ja) | 液晶性化合物、イオン伝導体、電解質フィルム及び二次電池 | |
KR101586356B1 (ko) | 액정 특성을 가지는, 전해질로서 유용한 신규 이미다졸리움 염 | |
JP2005243449A (ja) | イオン伝導体 | |
KR102139215B1 (ko) | 비스피롤리디늄 염 화합물을 포함하는 유기 이온성 결정물질, 이의 제조방법, 이를 포함하는 이차전지용 전해질 및 이차전지용 전해질을 포함하는 장치 | |
KR102139216B1 (ko) | 비스피페리디늄 염 화합물을 포함하는 유기 이온성 결정물질, 이의 제조방법, 이를 포함하는 이차전지용 전해질 및 이차전지용 전해질을 포함하는 장치 | |
JP2007194151A (ja) | イオン伝導体 | |
KR20140052160A (ko) | 덴드론 형태의 액정화합물 및 그 제조방법 | |
KR101388393B1 (ko) | 포스-덴드론 형태의 액정화합물 및 그 제조방법 | |
Onuma et al. | Liquid-crystalline behavior and ion transport properties of block-structured molecules containing a perfluorinated ethylene oxide moiety complexed with a lithium salt | |
JP2006147302A (ja) | イオン伝導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20081010 |
|
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: 20111129 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20111221 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150106 Year of fee payment: 3 |
|
LAPS | Cancellation because of no payment of annual fees |