WO2004085359A1 - 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 - Google Patents
長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 Download PDFInfo
- Publication number
- WO2004085359A1 WO2004085359A1 PCT/JP2004/003857 JP2004003857W WO2004085359A1 WO 2004085359 A1 WO2004085359 A1 WO 2004085359A1 JP 2004003857 W JP2004003857 W JP 2004003857W WO 2004085359 A1 WO2004085359 A1 WO 2004085359A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- general formula
- group
- benzene derivative
- formula
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 47
- 239000002178 crystalline material Substances 0.000 title claims abstract description 13
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000004714 phosphonium salts Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000005284 excitation Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 55
- 150000001555 benzenes Chemical class 0.000 description 43
- 239000004973 liquid crystal related substance Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 239000000463 material Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- -1 pentyl decyl group Chemical group 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004990 Smectic liquid crystal Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000032258 transport Effects 0.000 description 12
- 150000003935 benzaldehydes Chemical class 0.000 description 10
- 230000007704 transition Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- SUQRNQJDBIPGQW-UHFFFAOYSA-N 2-dec-9-enoxy-6-(2-phenylethenyl)benzaldehyde Chemical compound C=CCCCCCCCCOC1=CC=CC(C=CC=2C=CC=CC=2)=C1C=O SUQRNQJDBIPGQW-UHFFFAOYSA-N 0.000 description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- GYOUJJNUKBDCMB-UHFFFAOYSA-M benzyl-(2-dec-9-enoxyphenyl)-diphenylphosphanium;bromide Chemical compound [Br-].C=CCCCCCCCCOC1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 GYOUJJNUKBDCMB-UHFFFAOYSA-M 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 150000002605 large molecules Chemical class 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 4
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000001443 photoexcitation Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 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 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- JVVPJOMYWVYPOF-UHFFFAOYSA-N 10-bromodec-1-ene Chemical compound BrCCCCCCCCC=C JVVPJOMYWVYPOF-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KOWAPBWHSRHVHA-UHFFFAOYSA-N [bromo(dec-9-enoxy)methyl]benzene Chemical compound C=CCCCCCCCCOC(Br)C1=CC=CC=C1 KOWAPBWHSRHVHA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 2
- 229910001950 potassium oxide Inorganic materials 0.000 description 2
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 2
- 229960003857 proglumide Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LWHIJIMRCJFSIR-UHFFFAOYSA-N trimethylphosphane triphenylphosphane Chemical compound CP(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 LWHIJIMRCJFSIR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- IKPSIIAXIDAQLG-UHFFFAOYSA-N 1-bromoundecane Chemical compound CCCCCCCCCCCBr IKPSIIAXIDAQLG-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- BIHJQNXEOKKCRK-UHFFFAOYSA-N 2-(2-phenylethenyl)benzaldehyde Chemical compound O=CC1=CC=CC=C1C=CC1=CC=CC=C1 BIHJQNXEOKKCRK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ATLMFJTZZPOKLC-UHFFFAOYSA-N C70 fullerene Chemical compound C12=C(C3=C4C5=C67)C8=C9C%10=C%11C%12=C%13C(C%14=C%15C%16=%17)=C%18C%19=C%20C%21=C%22C%23=C%24C%21=C%21C(C=%25%26)=C%20C%18=C%12C%26=C%10C8=C4C=%25C%21=C5C%24=C6C(C4=C56)=C%23C5=C5C%22=C%19C%14=C5C=%17C6=C5C6=C4C7=C3C1=C6C1=C5C%16=C3C%15=C%13C%11=C4C9=C2C1=C34 ATLMFJTZZPOKLC-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- RZVWXGPOZSWDKV-UHFFFAOYSA-N ctk8h6814 Chemical class C1=CC2=CC=CN=C2C2=C1C1=CC3=CC=CC=C3C=C1C=C2 RZVWXGPOZSWDKV-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 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
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000002535 lyotropic effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- ZYAINOHNPXGGBU-UHFFFAOYSA-M potassium;3-hydroxy-2-methylbenzoate Chemical compound [K+].CC1=C(O)C=CC=C1C([O-])=O ZYAINOHNPXGGBU-UHFFFAOYSA-M 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- 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
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
Definitions
- the present invention relates to a benzene derivative having a long linear conjugated structure, a method for producing the same, and a liquid crystalline material.
- the present invention relates to an optical sensor, an organic electroluminescence element (EL element), a photoconductor, a spatial modulation element, a thin film transistor, a charge transport material of an electrophotographic photoreceptor, a photolithographic, a solar cell, a nonlinear optical material, and an organic material.
- the present invention relates to a novel benzene derivative having a long linear conjugated structure useful as a charge transporting material for semiconductor capacitors and other sensors, a method for producing the same, and a liquid crystal material.
- organic electoluminescence devices using organic materials as hole transporting materials and charge transporting materials constituting the electroluminescence devices have been actively studied.
- charge transport material compounds such as anthracene derivatives, anthraquinoline derivatives, imidazole derivatives, styryl derivatives, hydrazone derivatives, triphenylamine compounds, and poly-N-vinylcarbazole oxaziazol have been known. Has been.
- Liquid crystal compounds are applied to various devices as display materials, for example, clocks, calculators, televisions, personal computers, mobile phones, and the like.
- Liquid crystal materials are classified into thermotropic liquid crystals (temperature transition type liquid crystals) and lyotropic liquid crystals (concentration transition type liquid crystals) based on the means for imparting phase transition. In terms of molecular arrangement, these liquid crystals are classified into three types: smectic liquid crystals, nematic liquid crystals, and cholesteric liquid crystals.
- Liquid crystals have the same optical anisotropy as optically uniaxial crystals, as they are also called anisotropic liquids.
- Orthoscope observation is a normal observation between orthogonal Nicols, and is useful for discriminating the type of liquid crystal and determining the transition temperature of the liquid crystal phase. With this observation, each liquid crystal becomes more smectic liquid crystal due to a special birefringent optical pattern.
- A, B, D, E, F, and G. Hanna et al. Have proposed a charge transport material using a liquid crystalline compound having a liquid crystal phase having a smectic phase and having a charge transporting ability.
- a liquid crystalline charge transporting material having a smectic liquid crystal property and having a reduction potential in the range of ⁇ 0.3 to ⁇ 0.6 (V vs.
- a liquid crystalline charge transporting material containing a mixture containing a smectic liquid crystalline compound Japanese Patent Application Laid-Open No. 11-1989871
- a liquid crystalline charge transport material hole mobility speed is 1 X 1 0- 5 c mVv ⁇ s or more (JP-1 0 3 1 2 7 1 1 No. Publication)
- Materials Japanese Patent Laid-Open Publication No. Hei 11-19909761
- the like are proposed.
- the smectic liquid crystalline compounds proposed above include benzene rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, troborone rings, and other 6-step electron aromatic rings, naphthylene rings, azulene rings, benzofuran rings, indole rings. Ring, indazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, etc. 10 ⁇ -electron aromatic, or phenanthone ring, anthracene etc.
- the present inventors have proposed that a liquid crystalline compound having a smectic B phase as a liquid crystal phase be charged in a liquid crystal state of the smectic B phase or a solid state generated by a phase transition of the smectic B phase.
- a charge transport method in which pressure is applied Japanese Patent Application Laid-Open No. 2000-3518786
- the present invention has been made in view of such prior art, and an object of the present invention is to provide a novel charge transporting method utilizing molecular orientation in a liquid crystal state, which can be expected to have excellent charge transportability without photoexcitation.
- An object of the present invention is to provide a benzene derivative having a long linear conjugated structure, a method for producing the benzene derivative, and a liquid crystalline material containing the compound.
- R 1 or R 2 is a linear or branched alkyl group, an alkoxy group, or the following general formula (2)
- R 3 is a methyl group, a hydrogen atom
- B is an alkylene group, one co—0— (CH 2 ) n—
- the second invention which the present invention intends to provide is represented by the following general formula (3)
- a third invention provided by the present invention includes a benzene derivative having a long linear conjugated structure represented by the general formula (1) or a compound derived therefrom. Liquid crystalline material. BEST MODE FOR CARRYING OUT THE INVENTION
- the novel compound provided by the present invention is a benzene derivative having a long linear shared system structure represented by the general formula (1).
- R 1 and R 2 are a linear or branched alkyl group, an alkoxy group or the general formula (2) ) Represents a group having an unsaturated bond.
- R 1 and R 2 are the same group
- the alkyl group has 1 to 18 carbon atoms, and specific examples include a methyl group, an ethyl group, a butyl group, a pentylene group, a hexyl group, an octyl group, a dodecyl group, a pentyl decyl group, an octadecyl group and the like. Among them, an alkyl group having 6 to 18 carbon atoms is particularly preferable. Further, the alkyl group has a general formula; CH 3 — (CH 2 ) N —CH (CH 3 ) — (CH 2 )
- a branched alkyl group represented by M —CH 2 — (where n is 0 to 7 and m is 0 to 7) can improve solubility in various solvents.
- the alkoxy group is represented by a general formula: C n H 2n + 10 , wherein n in the formula is 1 to 18, particularly preferably 6 to 18.
- R 3 represents a hydrogen atom or a methyl group
- B represents an alkylene group
- -CO-0- (CH 2 ) n- — C 6 H 4 — CH 2
- the alkylene group may be linear or branched, and specifically preferably has 1 to 18 carbon atoms, for example, a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, Examples include alkylene groups such as a pentamethylene group, an ethylethylene group, a propylene group, a butylene group, a hexylene group, an octadecylene group, a nonylene group, a decylene group and a dodecylene group. Also, — CO— 0— (CH 2 )
- the benzene derivative having a long linear conjugated structural portion according to the present invention is a group having an unsaturated bond represented by the general formula (2) wherein R 1 in the general formula (1) is It is particularly preferable that R 2 is an alkyl group because it can be polymerized and can be effectively used as a charge transport material utilizing the molecular orientation of the compound in a liquid crystal state even when polymerized. .
- the benzene derivative having a long linear conjugated structure represented by the general formula (1) is a novel compound, and the compound has a cis or trans configuration or a cis and trans configuration as a conformation. It may be a mixture of bodies.
- reaction formula (1) Reaction formula (1)
- the benzaldehyde derivative represented by the general formula (3) as the first raw material used in the production method of the present invention can be obtained, for example, by the following reaction scheme (2)
- R- -0- -CH CH- -CHO (Wherein, R 1 has the same meaning as described above. R represents a monovalent organic group, and X 1 and X 2 each represent a halogen atom.) By performing the steps (A-1) to (A-4) It can be manufactured.
- the A-1 step is represented by the general formula (7) by reacting a halide (compound (5)) with hydroxybenzyl alcohol (compound (6)) in a solvent in the presence of a base. To obtain a compound.
- R 1 in the formula of the halide is a benzaldehyde derivative represented by the general formula (3) as a first raw material and a long linear conjugated system represented by the general formula (1). It is a group corresponding to R 1 in the formula of the benzene derivative having a structural part, and X 1 in the formula represents a halogen atom such as bromine, chlorine, and iodine.
- the reaction in the A_1 step is 1 to 3 moles, preferably 1 to 1.5 moles, of a halide (compound (5)) with respect to hydroxybenzyl alcohol (compound (6)). 1 to 3 moles, preferably 1 to 1.5 moles, of a base such as potassium oxide, sodium ethoxide, sodium methoxide, etc., in an alcoholic solvent such as methanol, ethanol or the like in an amount of 0 to 100: preferably 60 to 100; The reaction is carried out at 80 for 1 to 20 hours, preferably for 5 to 10 hours.
- step A-2 the compound (compound (7)) obtained in the step A-1 and phosphorus halide (compound (8)) are reacted in a solvent to obtain the compound represented by the general formula (9) ) Is obtained.
- X 2 in the formula of the phosphorus halide represents a halogen atom such as bromine, chlorine, and iodine.
- the reaction in the A-2 step is performed in an amount of 1 to 3 times, preferably 1 to 1.5 times, the amount of the phosphorus halide (compound (8)) based on the compound (compound (7)) obtained in the A-1 step.
- the reaction is carried out in a solvent such as ethyl ether at 1 to 30 C, preferably 0 to 30 at a molar ratio of 1 to 10 hours, preferably 1 to 5 hours.
- step A-3 the compound (compound (9)) obtained in the step A-2 and the phosphine compound (compound (10)) are reacted in a solvent to obtain the compound represented by the general formula (11). Is obtained.
- R in the formula of the phosphine compound represents a monovalent organic group
- the type of R is not particularly limited as long as the compound represented by the general formula (9) can be phosphonidated, and specific compounds include, for example, triphenylphosphine trimethylphosphine, triethylphosphine. Trialkyl phosphines such as phosphine can be used.
- the reaction in the step A-3 is 1 to 3 times, preferably 1 to 1.5 times the phosphine compound (compound (10)) with respect to the compound (compound (9)) obtained in the step A-2.
- the terephthalaldehyde (compound (12)) is 1 to 3 moles, preferably 1 to 1 times the compound (compound (11)) obtained in step A-3. 5 to 1 mole of base such as sodium hydroxide, sodium hydroxide, sodium methoxide, sodium methoxide, etc.
- the reaction is carried out in an alcohol solvent such as ethanol at a temperature of 30 to 30 ° C, preferably at a temperature of 15 to 15 ° C for 3 to 15 hours, preferably 5 to 10 hours.
- the obtained benzaldehyde derivative (compound (3)) can be further heat-treated in a solvent in the presence of iodine, if desired, after the step A-4.
- the benzaldehyde derivative (compound (3)) obtained by this heat treatment selectively becomes a high-purity trans form, and the reaction is carried out while maintaining the conformation even if the reaction based on the above reaction formula (1) is carried out continuously. As a result, the trans form of the target benzene derivative can be selectively obtained at a high yield.
- the amount of iodine added is 0.001 to 0.1 times mol, preferably 0.005 to 0.01 times mol, of the benzaldehyde derivative (compound (3)). 100-180, preferably 130-150 ° C.
- the solvent that can be used include, for example, benzene, toluene, o-xylene, m-xylene, p-xylene, cyclobenzene, o-cyclobenzene, m-cyclobenzene, p-cyclobenzene, etc., and these solvents can be used alone or in combination of two or more. .
- the phosphonium salt represented by the above general formula (4) as the other reaction raw material can be produced, for example, by the following reaction scheme (3) Anti-JS scheme (3)
- the step B-1 is represented by the general formula (14) by reacting a halide (compound (13)) with hydroxybenzyl alcohol (compound (6)) in a solvent in the presence of a base. The purpose is to obtain a product.
- R 2 in the formula of the halide is a phosphonium salt represented by the general formula (4) as a second reaction raw material and a long linear compound represented by the general formula (1).
- This is a group corresponding to R 2 in the formula of the benzene derivative having a conjugated structure portion, and A 1 in the formula represents a halogen atom such as bromine, chlorine, and iodine.
- the reaction in the B-1 step is performed in an amount of 1 to 3 times, preferably 1 to 1.5 times, the molar amount of the halide (compound (13)) with respect to the hydroxybenzyl alcohol (the compound (6)), ⁇ Bases such as potassium oxide, sodium ethoxide, sodium methoxide, etc. 1 to 3 moles, preferably 1 to L. 5 to 5 moles, in an alcoholic solvent such as methanol or ethanol at a mixing ratio of 20 to 100 ° C, preferably The reaction is carried out at 60 to 80 for 1 to 15 hours, preferably 5 to 10 hours.
- step B_2 the compound (compound (14)) obtained in the step B-1 is reacted with a phosphorus halide (compound (15)) in a solvent to give a compound represented by the general formula (16). Is obtained.
- a in the formula of the phosphorus halide corresponds to A in the formula of the phosphonium salt represented by the general formula (4) as the second reaction raw material, and is bromine, chlorine, iodine. And the like.
- the reaction in the B-2 step is carried out in an amount of 1 to 3 times, preferably 1 to 1.5 times, the amount of the phosphorus halide (compound (15)) based on the compound (compound (14)) obtained in the B-1 step.
- step B-3 the compound (compound (16)) obtained in the step B-2 and the phosphine compound (compound (17)) are reacted in a solvent to form a second compound.
- a phosphonium salt represented by the general formula (4) as a raw material is obtained.
- R 4 , R 5 and R s in the formula of the phosphine compound (compound (17)) represent a monovalent organic group, and the types of 4 , R 5 and R 6 are represented by the general formula (16) There is no particular limitation as long as the compound represented by the formula (1) can be phosphonidated.
- Specific compounds include, for example, trialkylphosphine such as triphenylphosphine-trimethylphosphine and triethylphosphine. Can be.
- the phosphine compound (compound (17)) is 1 to 3 times, preferably 1 to 1.1 times the compound (compound (17)) obtained in the step B-2.
- the reaction is carried out in a solvent such as chloroform at a mixing ratio of 5 moles at 30 to 100 ° (preferably at 60 to 80 for 1 to 10 hours, preferably for 1 to 5 hours.
- the method for producing a benzene derivative having a long linear conjugated structure represented by the general formula (1) according to the present invention comprises the benzaldehyde derivative represented by the general formula (3) and the general formula (4).
- the represented phosphonium salt is reacted in a solvent in the presence of a base.
- the amount of the phosphonium salt represented by the general formula (4) is 1 to 3 times, preferably 1 to 1.5 times the mol of the benzaldehyde derivative represented by the general formula (3).
- Examples of the base that can be used include metal hydrides such as sodium hydride, amines such as trimethylamine and triethylamine, alkali hydroxides such as potassium hydroxide and sodium hydroxide, sodium methoxide, and potassium.
- Examples include alkoxides such as methoxide, sodium ethoxide and potassium methoxide, piperidine, pyridine, potassium cresolate, alkyllithium and the like.These may be used alone or in combination of two or more. Not something.
- the amount of the base to be added is 1 to 4 moles, preferably 2 to 3 moles, based on the benzaldehyde derivative represented by the general formula (3).
- reaction solvent examples include ethers such as dioxane, tetrahydrofuran and dibutyl ether, nitriles such as acetonitrile and propionitrile, alcohols such as methanol and ethanol, dimethylformamide, acetone, and the like. More than one species can be used.
- the reaction is carried out at a reaction temperature of 120 to 50 ° C, preferably -5 to 25 ° C, and a reaction time of 1 to 20 hours, preferably 5 to 15 hours. .
- the benzene derivative having a long linear conjugated structure represented by the general formula (1), which is optionally obtained, is further subjected to a heat treatment in a solvent in the presence of iodine.
- a heat treatment in a solvent in the presence of iodine.
- the benzene derivative having a long linear conjugated structure represented by the general formula (1) can be selectively converted to a trans form.
- the iodine is added in an amount of 0.001 to 0.1 times, preferably 0.00 times, the molar amount of the benzene derivative having the long linear conjugated structure represented by the general formula (1).
- the heat treatment temperature is 100 to 180 ° C, preferably 130 to 150 ° C.
- the solvent that can be used include benzene, toluene, o-xylene, m-xylene, p-xylene, benzene, o-dichlorobenzene, m-dichlorobenzene, and p-dichlorobenzene. These solvents can be used alone or in combination of two or more.
- the benzene derivative having a long linear conjugated structure represented by the general formula (1) obtained by force is a novel conjugate having a liquid crystallinity.
- the liquid crystalline material of the present invention comprises a benzene derivative having a long linear conjugated structure represented by the general formula (1) or a compound derived from the benzene derivative having the long linear conjugated structure. It contains.
- the compound derived from the benzene derivative having a long linear conjugated structure represented by the general formula (1) is defined as R 1 in the formula of the benzene derivative having the long linear conjugated structure.
- R 2 is a group having an unsaturated bond represented by the general formula (2), a homopolymer, a copolymer, a high molecular weight compound cross-linked by a cross-linking agent, or hydrosilyl
- a high molecular weight compound obtained by an addition reaction with a high molecular compound having a group hereinafter, referred to as “polymer”).
- polymer for example, when R 1 is a group having an unsaturated bond represented by the general formula (2) and R 2 is an alkyl group, at least the following general formula (18) ) Or the following general formula (19)
- R 3 and B have the same meanings as described above.
- R 2 represents an alkyl group.
- the polymer may have, as a copolymerization component, a repeating unit derived from acrylic acid, methacrylic acid, styrene, or the like.
- a repeating unit represented by the above general formula (18) or the above general formula (19) accounts for 50 mol% or more, preferably 70 mol% or more, more preferably 80 mol% in the copolymer. That is all.
- the molecular weight of the polymer is such that the number average molecular weight is in the range of 1,000 to tens of millions, preferably in the range of tens of thousands to millions.
- the polymer can be produced by the following method. For example, a high molecular weight compound crosslinked by a homopolymer, a copolymer, or a crosslinker represented by the general formula (18) is produced.
- a polymerization reaction is carried out in the presence of a polymerization initiator by a radical polymerization method such as a solution polymerization method, a suspension polymerization method, an emulsion polymerization method, and a norc polymerization method. It can be manufactured by performing.
- a hydrosilyl compound is produced.
- a benzene derivative having a long linear conjugated structure represented by the general formula (1) with an alcohol solution of chloroplatinic acid, chloroplatinic acid, a complex of platinum and an olefin complex, rhodium It can be produced by carrying out a reaction in the presence of an oral dime-based catalyst such as a complex of phenol and potassium.
- the liquid crystalline material according to the present invention is a benzene derivative having a long linear conjugated structure represented by the general formula (1), a composition containing the benzene derivative having the long linear conjugated structure, It is a material exhibiting a liquid crystallinity of a smectic phase as a liquid crystal phase composed of the polymer or a composition containing the polymer.
- composition containing a benzene derivative having a long linear conjugated structure represented by the general formula (1) comprises a benzene derivative having a long linear conjugated structure represented by the general formula (1). At least 30% by weight or more, preferably 50% by weight or more, more preferably 90% by weight or more, which is caused by a liquid crystal compound having a long linear conjugated structure represented by the general formula (1). It shows the liquid crystal state of the smectic phase.
- components in the composition are components that adjust the phase transition temperature of a benzene derivative having a long linear conjugated structure represented by the general formula (1), and include, for example, other liquid crystal compounds, One or more compounds having both ends having an alkyl group or an alkoxy group at both ends having another long linear conjugate system can be used.
- the compound that is a group or an alkoxy group may or may not be a liquid crystalline compound.
- a composition containing a benzene derivative having a long linear conjugated structure represented by the general formula (1) can be prepared as follows. That is, the general formula (1) After dissolving the benzene derivative having a long linear conjugated structure represented by the formula and the above-mentioned desired components in a solvent, the solvent is removed by heating, reduced pressure, or the like, or the long straight line represented by the general formula (1) It can be prepared by mixing a benzene derivative having a structurally conjugated system part with the above-mentioned desired components and melting by heating, or by performing sputtering, vacuum evaporation or the like.
- composition containing the polymer contains the polymer at least 30% by weight or more, preferably 50% by weight or more, more preferably 80% by weight or more, and the general formula (1) This shows the liquid crystal state of the smectic phase caused by the liquid crystal conjugate of a benzene derivative having a long linear conjugated structure represented by the following formula.
- components in such a composition are components that adjust the phase transition temperature of the polymer, and include, for example, other liquid crystal compounds, and alkyl groups or alkoxy groups at both ends having another long linear conjugated system.
- One or more compounds may be used, and a compound having a long linear conjugate system of other components and having an alkyl group or an alkoxy group at both ends may be a liquid crystal compound. It is not necessary.
- These other components can be used alone or in combination of two or more.
- This polymer composition can be prepared as follows. That is, after dissolving the polymer and the desired component in a solvent, the solvent is removed by heating, decompression, or the like, or the polymer and the desired component are mixed, and the mixture is melted with no heat, or sputtering, It can be prepared by performing vacuum evaporation or the like.
- the liquid crystalline material according to the present invention may be, for example, charge-transported by applying a voltage to the liquid crystalline material in a liquid crystal state or applying a voltage to the liquid crystalline material in a solid state generated by a phase transition of the liquid crystal state.
- charge transporting materials include photosensors, organic electroluminescent devices (EL devices), photoconductors, spatial modulation devices, thin film transistors, charge transporting materials for electrophotographic photoreceptors, photolithography, and solar cells. It can be used for non-linear optical materials, organic semiconductor capacitors, and other sensors.
- a benzene derivative (compound (32)) was synthesized according to the following reaction formula (12).
- Synthesis Examples 2-1 to 2-3 were performed in the same manner as in Synthesis Example 2-1 except that 1-bromooctane was replaced with 1-promonanane to obtain a phosphonium salt (compound (34)).
- Synthesis Example 2 Synthesis Example 2-1-2-3 was performed in place of 1-bromooctane in place of 1-bromoundecane to obtain a phosphonium salt.
- the benzene derivative having a long linear conjugated structure represented by the general formula (1) of the present invention is a novel compound, and the benzene derivative having the long linear conjugated structure is a liquid crystal.
- a liquid crystal material containing a compound having a smectic phase as a phase and a benzene derivative having a long linear conjugated structure portion or a compound derived from the derivative may be, for example, a voltage applied to the liquid crystal material in a liquid crystal state. Or a voltage is applied to the liquid crystalline material in a solid state generated by a phase transition of a liquid crystal state.
- a charge transport material that transports electric charges there are, for example, an optical sensor, an organic electroluminescence element (EL element), a photoconductor, a spatial modulation element, a thin film transistor, a charge transport material for an electrophotographic photosensitive member, It is expected that it can be used for photolithography, solar cells, nonlinear optical materials, organic semiconductor capacitors, and other sensors.
- an optical sensor an organic electroluminescence element (EL element), a photoconductor, a spatial modulation element, a thin film transistor, a charge transport material for an electrophotographic photosensitive member, It is expected that it can be used for photolithography, solar cells, nonlinear optical materials, organic semiconductor capacitors, and other sensors.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/548,386 US7422702B2 (en) | 2003-03-24 | 2004-03-22 | Benzene derivative having long, linear conjugated structure, process for producing benzene derivative, and liquid-crystal material |
JP2005504040A JP4476932B2 (ja) | 2003-03-24 | 2004-03-22 | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003-079740 | 2003-03-24 | ||
JP2003079740 | 2003-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004085359A1 true WO2004085359A1 (ja) | 2004-10-07 |
Family
ID=33094854
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/003857 WO2004085359A1 (ja) | 2003-03-24 | 2004-03-22 | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7422702B2 (ja) |
JP (1) | JP4476932B2 (ja) |
KR (1) | KR20050120657A (ja) |
CN (1) | CN100427444C (ja) |
WO (1) | WO2004085359A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006342318A (ja) * | 2004-12-07 | 2006-12-21 | Yuichiro Haramoto | 導電性液晶材料、その製造方法、液晶組成物、液晶半導体素子及び情報記録媒体 |
WO2007138883A1 (ja) * | 2006-05-31 | 2007-12-06 | Yamanashi University | メモリ素子、データ記録方法及びicタグ |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5164329B2 (ja) * | 2006-02-14 | 2013-03-21 | 国立大学法人山梨大学 | 液晶性スチリル誘導体、その製造方法及びそれを用いた液晶性半導体素子 |
JP5291894B2 (ja) * | 2007-05-23 | 2013-09-18 | 国立大学法人山梨大学 | メモリ素子、データ記録方法及びicタグ |
CN101768055B (zh) * | 2010-01-18 | 2013-03-27 | 清华大学 | 一种液晶化合物及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1222863A (en) * | 1967-07-14 | 1971-02-17 | Ciba Geigy Ag | Aromatic compounds containing ehtylene double bonds, processes for their manufacture and use |
JP2004006271A (ja) * | 2002-04-08 | 2004-01-08 | Yuichiro Haramoto | 長い直線的共役系構造部分を持つ液晶分子を用いた電荷輸送方法及び電荷輸送素子 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3991049A (en) * | 1967-07-14 | 1976-11-09 | Ciba-Geigy Ag | Aromatic compounds containing ethylene double bonds, processes for their manufacture and use |
WO2005056499A2 (en) * | 2003-12-04 | 2005-06-23 | Northwestern University | Oligo(p-phenylene vinylene) amphiphiles and methods for self-assembly |
-
2004
- 2004-03-22 JP JP2005504040A patent/JP4476932B2/ja not_active Expired - Fee Related
- 2004-03-22 CN CNB2004800079978A patent/CN100427444C/zh not_active Expired - Fee Related
- 2004-03-22 KR KR1020057017865A patent/KR20050120657A/ko not_active Application Discontinuation
- 2004-03-22 WO PCT/JP2004/003857 patent/WO2004085359A1/ja active Application Filing
- 2004-03-22 US US10/548,386 patent/US7422702B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1222863A (en) * | 1967-07-14 | 1971-02-17 | Ciba Geigy Ag | Aromatic compounds containing ehtylene double bonds, processes for their manufacture and use |
JP2004006271A (ja) * | 2002-04-08 | 2004-01-08 | Yuichiro Haramoto | 長い直線的共役系構造部分を持つ液晶分子を用いた電荷輸送方法及び電荷輸送素子 |
Non-Patent Citations (2)
Title |
---|
NDAYIKENGURUKIYE H, ET AL: "Alkoxylated p-phenylenevinylene oligomers: synthesis and spectroscopic and electrochemical properties", TETRAHEDRON, vol. 53, no. 40, 1997, pages 13811 - 13828, XP004106259 * |
WATAKABE A, ET AL: "Molecular design and monolayer stability of oligo(phenylenevinylene) derivatives", COLLOIDS AND SURFACES, A: PHYSICOCHEMICAL AND ENGINEERING ASPECTS, vol. 87, no. 2, 1994, pages 101 - 116, XP002980574 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006342318A (ja) * | 2004-12-07 | 2006-12-21 | Yuichiro Haramoto | 導電性液晶材料、その製造方法、液晶組成物、液晶半導体素子及び情報記録媒体 |
WO2007138883A1 (ja) * | 2006-05-31 | 2007-12-06 | Yamanashi University | メモリ素子、データ記録方法及びicタグ |
JP2007324314A (ja) * | 2006-05-31 | 2007-12-13 | Univ Of Yamanashi | メモリ素子、データ記録方法及びicタグ |
US7965534B2 (en) | 2006-05-31 | 2011-06-21 | Yamanashi University | Memory device, data recording method and IC tag |
Also Published As
Publication number | Publication date |
---|---|
CN100427444C (zh) | 2008-10-22 |
US7422702B2 (en) | 2008-09-09 |
JP4476932B2 (ja) | 2010-06-09 |
JPWO2004085359A1 (ja) | 2006-06-29 |
KR20050120657A (ko) | 2005-12-22 |
CN1764624A (zh) | 2006-04-26 |
US20060278848A1 (en) | 2006-12-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0106175A2 (en) | Electrically conductive liquid crystalline substance and polymer | |
JP2011231098A (ja) | シクロアルカンジカルボン酸モノエステルの製造方法 | |
JP4271469B2 (ja) | 長い直線的共役系構造部分を持つ液晶分子を用いた電荷輸送方法及び電荷輸送素子 | |
JP4161092B2 (ja) | ポリマー化可能な基を有するスルホン酸型液晶材料、その製造方法、プロトン輸送材料および液晶状態による分子配列を利用したプロトン輸送方法 | |
WO2004085359A1 (ja) | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 | |
US6174455B1 (en) | Liquid crystalline compounds and process for producing the same | |
JP2007191447A (ja) | 新規ジアミン化合物およびその製造法 | |
JP4527662B2 (ja) | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 | |
JP4574549B2 (ja) | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法及び液晶性材料 | |
JP4476933B2 (ja) | 長い直線的共役系構造部分を持つベンゼン誘導体、その製造方法、液晶性材料及び電荷輸送材料 | |
JP4330106B2 (ja) | ポリマー化可能な基を有するホスホン酸型液晶材料、その製造方法、プロトン輸送材料および液晶状態による分子配列を利用したプロトン輸送方法 | |
Oshima et al. | Synthesis and characterization of β‐forming poly [S‐(ω‐N‐carbazolylalkyl)‐L‐cysteine] s | |
Gupta et al. | Synthesis and property studies of linear and kinked poly (pyreneethynylene) s | |
JP2003306531A (ja) | 共役系高分子の電解不斉重合方法と光学活性共役系高分子 | |
JP4396907B2 (ja) | 電荷輸送方法 | |
TW201317329A (zh) | 液晶化合物以及液晶顯示器 | |
US6720039B1 (en) | Liquid crystalline compounds and process for producing the same | |
JP2002356473A (ja) | 液晶化合物と同様な化学構造を持ち、電子輸送性el素子として応用可能なビオロゲン誘導体およびその製造方法 | |
JPH0575762B2 (ja) | ||
JP3092736B2 (ja) | サーモトロピック液晶性高分子材料 | |
Bubnov et al. | New chiral thiols and related side chain liquid crystalline polymers | |
JPH0288691A (ja) | 非線形光学で使用可能な非中心対称性液晶 | |
JPH0563881B2 (ja) | ||
JPH04134050A (ja) | 光学活性化合物、高分子液晶およびそれを含む液晶組成物 | |
JPH05279354A (ja) | チオフェン誘導体およびその製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005504040 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 20048079978 Country of ref document: CN Ref document number: 1020057017865 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 1020057017865 Country of ref document: KR |
|
122 | Ep: pct application non-entry in european phase | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2006278848 Country of ref document: US Ref document number: 10548386 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 10548386 Country of ref document: US |