CN1154102A - Oligomer liquid crystal triphenylene derivatives and their use as charge carrying substances in electrophoto-graphy - Google Patents
Oligomer liquid crystal triphenylene derivatives and their use as charge carrying substances in electrophoto-graphy Download PDFInfo
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- CN1154102A CN1154102A CN 95194331 CN95194331A CN1154102A CN 1154102 A CN1154102 A CN 1154102A CN 95194331 CN95194331 CN 95194331 CN 95194331 A CN95194331 A CN 95194331A CN 1154102 A CN1154102 A CN 1154102A
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- Prior art keywords
- compound
- group
- benzo
- sulphur
- oxygen
- Prior art date
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- 239000000126 substance Substances 0.000 title claims abstract description 7
- 125000005580 triphenylene group Chemical group 0.000 title abstract 2
- 239000004973 liquid crystal related substance Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000005864 Sulphur Substances 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000005605 benzo group Chemical group 0.000 claims description 21
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 10
- -1 siloxanes Chemical class 0.000 claims description 9
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000012071 phase Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 239000003205 fragrance Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 235000015320 potassium carbonate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 150000002987 phenanthrenes Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 235000007715 potassium iodide Nutrition 0.000 description 4
- 229960004839 potassium iodide Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920004482 WACKER® Polymers 0.000 description 3
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 3
- 229940049706 benzodiazepine Drugs 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- SYHPANJAVIEQQL-UHFFFAOYSA-N dicarboxy carbonate Chemical compound OC(=O)OC(=O)OC(O)=O SYHPANJAVIEQQL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DBPFRRFGLYGEJI-UHFFFAOYSA-N ethyl glyoxylate Chemical compound CCOC(=O)C=O DBPFRRFGLYGEJI-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 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 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 1
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 1
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- USYPCJSLOVEJGC-UHFFFAOYSA-N OCCCCCCCCC=CO Chemical compound OCCCCCCCCC=CO USYPCJSLOVEJGC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 125000005070 decynyl 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#C* 0.000 description 1
- ZVDBUOGYYYNMQI-UHFFFAOYSA-N dodec-1-yne Chemical compound CCCCCCCCCCC#C ZVDBUOGYYYNMQI-UHFFFAOYSA-N 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 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
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
- QFQXAVRUGZXRHM-UHFFFAOYSA-N hex-1-ene-1,6-diol Chemical compound OCCCCC=CO QFQXAVRUGZXRHM-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- VRLIPUYDFBXWCH-UHFFFAOYSA-N hydridocarbon(.) Chemical compound [CH] VRLIPUYDFBXWCH-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- OSSQSXOTMIGBCF-UHFFFAOYSA-N non-1-yne Chemical group CCCCCCCC#C OSSQSXOTMIGBCF-UHFFFAOYSA-N 0.000 description 1
- ZTMXPTNYDYAOLY-UHFFFAOYSA-N oct-1-ene-1,8-diol Chemical compound OCCCCCCC=CO ZTMXPTNYDYAOLY-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095068 tetradecene Drugs 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Abstract
Compounds have the general formula (I) Z[-Y<1>-(A-Y<2>)m-X]n, in which the variables have the following meanings: Z stands for an n-valent aliphatic residue with 2 to 20 C atoms or for an n-valent three to seven-membered saturated or unsaturated carbocyclic or heterocyclic residue that may also be benzocyclised, or for an n-valent siloxane or cyclosiloxane residue with up to 10 Si atoms; Y<1>, Y<2> stand for a chemical bond, oxygen, sulphur or a group -CO-O-, -O-CO-, -N(R)-CO- or -CO-N(R)-; m equals 0 or 1; A stands for an alkylene group with 2 to 20 C atoms in which non-adjacent C atoms may be substituted by oxygen, sulphur, -CO-O-, -O-CO- or -N(R)-; n equals 2 to 6; R stands for hydrogen or C1-C4-alkyl; and X stands for a substituted triphenylene residue. Because they recur n times in the compounds, A, Y<1>, Y<2>, m and X may be the same or different.
Description
The present invention relates to the compound of general formula I, relate to these compounds at photorepeater and laser printer, and in electrochemical cell, electronic component and light display instrument as the purposes of charge transfer compound:
Z[-Y
1(A-Y
2)
m-X]
nI, wherein to have following implication: Z be n valency aliphatic group or n valency three to seven yuan of saturated or unsaturated carbocyclic or the heterocyclic groups with 2 to 20 carbon atoms to variable, described ring also can be benzo-fused, or has n valency siloxanes or cyclosiloxane base up to 10 Siliciumatoms, Y
1, Y
2Be chemical bond, oxygen, sulphur or-CO-O-,-O-CO-,-N (R)-CO-or-CO-N (R)-group, m is 0 or 1, A is the alkylidene group with 2 to 20 carbon atoms, wherein non-conterminous carbon atom can by oxygen, sulphur or-CO-O-,-O-CO-or-N (R)-replacement, n is 2 to 6R to be hydrogen or C
1-C
4-alkyl and X benzo [9,10] phenanthrene, wherein A, Y for replacing
1, Y
2, m and X be owing to occur n time in compound, so they can be identical or different.
Organic photoconductor has been known for a long time and be used as electrostatic printing recording materials (Schaffert, IBM J.Res.Develop., 1975,75) especially in xeroprinting.At present, organic photoconductor in photorepeater and laser printer as the molecular dispersoid in the neutral binding agent (Borsenberger, J.Phys.Chem., 1993,11314).This arrangement has 10
-5Cm
2The typical maximum charge hall mobility of/Vs.Yet the charge carrier mobility of this order of magnitude has limited the printing or the reproduction speed of electrostatic printing equipment, therefore it seems and only can further improve this speed by the mobility that improves charged particle carrier.Yet this can not realize by at present used ordinary method.
By people such as Closs (Liquid Crystals, 14 (3), 629 (1993)), people (Liquid Crystals such as Beng, 15 (5), 565 (1993)) and people (Phys.Rev.Lett. such as Adam, 70 (4), 457 (1993)) six pentyloxy benzo [9, the 10] phenanthrene in the mesomorphic phase that studies have shown that have photoconductive property.Because the operating temperature range of photocopying is 20 ℃ to 50 ℃, therefore in this scope, also must observe transport phenomena.This is impossible for six pentyloxy benzos [9,10] phenanthrene.
In addition, photoconductive layer must be able to bear some mechanical stress that (for example) occurs in each procedure of processing (toning of charged image, the transmission of toner image).
The object of the invention is the liquid crystal material that provides new, and this material also has mesomorphic phase and is mechanically stable except photoconductive property in 20 ℃ to 50 ℃ scopes.
We have found that the object of the invention can realize by benzo [9, the 10] phenanthrene derivative of above-mentioned general formula I.
Particularly when n=2, linking group Z be preferably have 2 to 20, the alkylidene group of preferred 2 to 6 carbon atoms, when n=3, be preferably alkylidene group or three-to seven-unit saturated or unsaturated carbocyclic or heterocyclic radical or cyclosiloxane base, particularly as n=4,5 or 6 the time, benzo [9, the 10] phenanthryl that is preferably the cyclosiloxane group or does not replace or replace.
Preferred Z group further is the siloxane groups of following general formula when n=2:
Wherein r is 1 to 9 number, or is the cyclosiloxane group of following general formula when n=3 to 6
Wherein s is 3 to 6 number.
Preferred Z (Y
1-)
nGroup is derived from following Z (Y
1H)
nThose groups of compound:
1,3,5-hexanaphthene tricarboxylic acid, 1,3,5-benzene tricarbonic acid, toxilic acid, fumaric acid, oxalic acid, propanedioic acid, Succinic Acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, nonane diacid, ethylene glycol, propylene glycol, 1,3-dihydroxyl propylene, 1,4-dihydroxyl butylene, 1,5 dihydroxyl amylene, 1,6-dihydroxyl hexene, 1,8-dihydroxyl octene and 1,10-dihydroxyl decene.
Particularly when n 〉=3, preferred Z group is benzo [9, a 10] phenanthryl, preferred especially unsubstituted benzo [9,10] phenanthryl.
The spacer part A is preferably has 3 to 20 carbon atoms, especially preferably has the not branching α of 4 to 12 carbon atoms, ω-alkylidene group.This is specially suitable when Z is straight chain or annular siloxane.Preferably-Y
1-A-Y
2-group is-(CH
2)
P1-,-O-(CH
2)
P2-,-O-(CH
2)
P2-CO-O-,-O-CO-(CH
2)
P2-CO-O-and-O-(CH
2)
P3-O-, wherein p1 is 2 to 12 number, and p2 is 2 to 10 number, and p3 is 2 to 11 number.
If center cell Z is an alkylidene group also, then m is preferably 0, and promptly benzo [9,10] phenanthryl X passes through Y
1Directly be connected with center cell.
Benzo [9,10] the phenanthryl X that replaces preferably has following structure
R wherein
1To R
5Be preferably fluorine, chlorine, bromine, iodine, nitro, cyano group, C
1-C
20-alkyl, C
1-C
20-alkoxyl group, C
1-C
20-alkylthio, C
1-C
20-alkanoyloxy, C
1-C
20-alkenyl, C
1-C
20-alkynyl group, in these groups, carbochain can by non-conterminous Sauerstoffatom or sulphur atom or-COO-,-OCO-or-N (R) group at interval.
Specially suitable radicals R
1To R
5Be:
Alkyl such as methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, octyl group, nonyl, decyl, dodecyl, tetradecyl and hexadecyl.Wherein, the alkyl with 4 to 16 carbon atoms is preferred, and butyl, amyl group, hexyl, heptyl, octyl group and nonyl are particularly preferred.
Carbochain in all aliphatic groups can by non-conterminous Sauerstoffatom or sulphur atom or-COO-,-OCO-or-N (R) group at interval, in the latter, particularly by-NH-or-NCH
3-at interval.
Other suitable substituents R
1To R
5Be in particular and in carbochain, have two keys or triple-linked aliphatic group, for example vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonene base, dodecenyl succinic, tetradecene base, cetene base, ethynyl, proyl, butynyl, pentynyl, hexin base, heptyne base, octyne base, n-heptylacetylene base, decynyl, dodecyne base, 14 carbyne bases or hexadecine base, two keys or triple bond are preferably terminal key.Have with two keys of the luxuriant and rich with fragrance conjugated of benzo [9,10] or triple-linked aliphatic group be particularly preferred.
Some suitable radicals R again
1To R
5Be group with polymerizable groups P, these radicals R
1To R
5The structure that preferably has formula III
-Y
3-A
1-Y
4-p III wherein each variable has following meanings: Y
3, Y
4Be chemical bond, oxygen, sulphur or-CO-O-,-O-CO-,-N (R)-CO-or-CO-N (R)-group, A
1For having the alkylidene group of 2 to 20 carbon atoms, wherein non-conterminous carbon atom can by oxygen, sulphur or-CO-O-,-O-CO-or-N (R)-replacement, P is the polymerizable groups that following formula is represented
-CH=CH
2,
-CH
2-CH=CH
2,-CH=CH-CH
3Or
Has above-mentioned implication with R.
These compounds prepare by ordinary method.Preparation method's (for example) with various substituent benzos [9,10] phenanthrene derivative is described in Makromol.Chem.Rap.Commun by W.Kreuder, H.Ringsdorf, and 4 (1983) 807 and be described in the German patent application 19517208.6.Spacer and polymerizable groups can be introduced by the method for describing in the document that is similar to (for example) document DE-A-39 17 196 and quotes here.
The benzo [9 of formula I of the present invention, 10] phenanthrene derivative is suitable as organic charge transfer compounds and photo-conductor and can be used for for example photorepeater, laser printer and laser facsimile, and is used in the layer of compensation of electrochemical cell, photoelectrochemical cell, electronic component and light display instrument.
Embodiment
Synthesizing among these embodiment undertaken by preceding method.Phase behaviour can followed the Leitz polarizing microscope of Mettler heating steps (Leitz Ortholux II by the polarized light microscopy method
) middle mensuration.The phase sequence that optical method is measured confirms by dsc (using Mettler DSC7).
Photoconductive property is measured (Liquid Crystals, 14 (3), 629 (1993)) in the instrument that people such as (for example) Closs describe.
Following abbreviation is used from start to finish:
Each homogeny phase of I
D
HoSheet type (discotic) hexagonal phase
K
1, K
2, the various crystallization phasess of K
G vitreous state embodiment 1
A) 2-(10-bromine oxygen in last of the ten Heavenly stems base)-3,6,7,10,11-five (pentyloxy)-benzo [9,10] luxuriant and rich with fragrance (1a)
With 15g (49.98mmol) 1,10-dibromo-decane and 5g (7.41mmol) 3,6,7,10,11-five pentyloxys-2-hydroxy benzo [9,10] phenanthrene is dissolved in the 12ml 2 pentanone, and stirs 15 hours down in 70 ℃ after adding 6g (43.41mmol) salt of wormwood.Then with the cooling of this mixture and suction filtration to remove sedimentary Potassium Bromide and excessive salt of wormwood.Flash chromatography separates (CH for the first time
2Cl
2/ PE 1/2) obtain thick product, this thick product is carried out another time flash chromatography separate.Recrystallization obtains straight product 1a in acetonitrile/acetone (1/1).
Output: 5.21gb) compound 1
1.5g (2.22mmol) monohydroxy benzo [9,10] phenanthrene and 2.0g (2.24mmol) compound 1a are dissolved in the 15ml methyl propyl ketone under argon gas.After adding 4g (28.94mmol) salt of wormwood and 50mg potassiumiodide, with this mixture boiled 20 hours.Reaction mixture is cooled off suction filtration then.With flash chromatography (CH
2Cl
2/ PE 1/1) separate twice, then recrystallization is isolated dimer in acetone.
Output: 2.58g embodiment 2
With 5g (6.97mmol) 3,6,7,10,11-five pentyloxys-2-acetoxyl group benzo [9,10] luxuriant and rich with fragrance and 1.41g (10.46mmol) 4-bromobutene is dissolved in the 10ml toluene, and after adding 2g (35.71mmol) potassium hydroxide and 0.2ml tetrabutylammonium, this mixture is stirred 20 hours down at 40 ℃.Filter with 50ml water and 50ml sherwood oil then.With organic phase 2N H
2SO
4, the extraction of saturated NaCl solution and water.Dry on the sodium sulfate and remove through distillation and to obtain thick product after desolvating, this thick product can be in ethanol or acetonitrile recrystallization repeatedly.Before recrystallization by carrying out flash chromatography (CH
2Cl
2/ PE 1/1) separate and to obtain high purity product.
Output: 4.33g
In polymerization reactor, 200mg (0.274mmol) compound 2a and 18.42mg (0.137mmol) tetramethyl disiloxane are dissolved in the 1ml absolute toluene under argon gas.After adding catalyzer (2 μ l SLM 86005 are available from the catalyst solution of Wacker Chemie Burghausen), this mixture was stirred 48 hours down at 50 ℃.In 100ml toluene, precipitate then.The thick product of gained is carried out flash chromatography (CH
2Cl
2/ PE 1/1) separate to remove excessive monomer.At last this dimer is dissolved in the 1ml methylene dichloride, filters and in 100ml methyl alcohol, precipitate through Weissrand strainer (micro-pore diameter=0.2 μ m).
Output: 65mg
Phase behaviour: D
Ho110i embodiment 3
In polymerization reactor, 200mg (0.274mmol) compound 2a and 28mg (0.137mmol) hexam ethylcyclotrisiloxane are dissolved in the 1ml absolute toluene under argon gas.After adding catalyzer (2 μ l SLM 86005 are available from the catalyst solution of Wacker Chemie Burghausen), this mixture was stirred 48 hours down at 60 ℃.In 100ml toluene, precipitate then.The thick product of gained is carried out flash chromatography (CH
2Cl
2/ PE 1/1) separate to remove excessive monomer.At last this dimer is dissolved in the 1ml methylene dichloride, filters and in 100ml methyl alcohol, precipitate through Weissrand strainer (micro-pore diameter=0.2 μ m).
Output: 149mg
Phase behaviour: k
17k
227.5D
Ho90i embodiment 4
In polymerization reactor, 500mg (0.68mmol) compound 2a and 41.23mg (1.71mmol) tetramethyl-ring siloxanes are dissolved in the 1ml absolute toluene under argon gas.After adding catalyzer (2 μ l SLM 86005 are available from the catalyst solution of Wacker Chemie Burghausen), this mixture was stirred 24 hours down at 60 ℃.In 100ml toluene, precipitate then.The thick product of gained is carried out flash chromatography (CH
2Cl
2/ PE 3/1) separate to remove excessive monomer.At last this cyclosiloxane is dissolved in the 1ml methylene dichloride, filters and in 100ml methyl alcohol, precipitate through Weissrand strainer (micro-pore diameter=0.2 μ m).
Output: 402.2mg
Phase behaviour: g-48D
Ho141i embodiment 5
Be similar to embodiment 2a and use following material: 6g (8.37mmol) 3,6,7,10, the 11-five pentyloxys-luxuriant and rich with fragrance 3g of 2-acetoxyl group benzo [9,10] (15.7mmol) 8-bromine octene 2g (35.71mmol) potassium hydroxide 0.2ml tetrabutylammonium reaction and refining) described carrying out by embodiment 2a.Output: 5.29g
In polymerization reactor, 400mg (0.509mmol) compound 5a and 30.63mg (1.27mmol) tetramethyl-ring siloxanes are dissolved in the 1ml absolute toluene under argon gas.After adding catalyzer (2 μ l SLM 86005), this mixture was stirred 18 hours down at 60 ℃.In 100ml toluene, precipitate then.The thick product of gained is carried out flash chromatography (CH
2Cl
2/ PE 3/1) separate to remove excessive monomer.At last this cyclosiloxane is dissolved in the 1ml methylene dichloride, filters and in 100ml methyl alcohol, precipitate through Weissrand strainer (micro-pore diameter=0.2 μ m).
Output: 357mg
Phase behaviour: g-50D
x98.5i embodiment 6a)
Will be in the new incinerating fine powdered salt of wormwood of the 1.88g in the 25ml 2 pentanone (2.79mmol) monohydroxy benzo [9,10] phenanthrene, 0.51g (2.79mmol) 6-bromine hexanol, 1.07g (8.37mmol) and 0.46g (2.79mmol) potassiumiodide reflux 2 days under argon gas.Chilled mixture is filtered, with washed with dichloromethane and with the thick product of gained by flash chromatography (CH
2Cl
2) twice purifying of separation.
Output: 1.52g
In the Schlenk container after adding a small amount of exsiccant methylene dichloride (4 molecular sieve), with 30mg (0.0354mmol) 2,3,6,7,10,11-six (ethoxy carbonyl-methylene radical oxygen base) benzo [9,10] is luxuriant and rich with fragrance to be mixed with 246.9mg (0.3185mmol) compound 6a.Homogeneous solution is stirred several minutes, use nitrogen (at P solvent then
2O
5Last dry) take out of as far as possible.Use argon gas (at P simply in container
2O
5Last dry) clean and be heated to 110 ℃.Under argon gas, 2 catalyst solutions (10 volume % original four-isopropyl titanates (merck) in dry diglyme (4 molecular sieve)) are added in the melt equally.Begin to emit bubble and show have ethanol to emit, begin transesterification thus.Condensation was under atmospheric pressure carried out 1 hour under 120 ℃, was carrying out 1.5 hours and vacuumizing at oil pump to carry out 12 hours (must vacuumize down at oil pump and after 1 hour temperature is risen to 140 ℃ to prevent that melt from solidifying) under (0.007 millibar) under 125 ℃ under water pump vacuumizes.Though can be observed several bubbles (show reaction not exclusively) of formation, stopping condensation reaction after 15 hours altogether.Resistates is dissolved among the absolute THF, and from the luxuriant and rich with fragrance alcohol of excess monomer benzo [9,10], isolates heptamer by preparation GPC (vapor-phase chromatography) (column material Sephadex LH 60, elutriant=distillatory THF on potassium).Obtain required product by first high strength peak.After having very low intensive several peaks (being attributable to the not low molecular weight oligomeric body of complete reaction), show color atlas immediately; Last wash-out goes out the luxuriant and rich with fragrance alcohol of excessive benzo [9,10].Obtain the straight product heptamer by evaporating suitable cut.Because even the THF resistates still is entrained in the glassy oligomer after oil pump vacuumizes down dry a couple of days, therefore must carry out lyophilize to remove remaining THF in benzene.
Output: 154mg embodiment 7
By embodiment 6a) react.Compound: 10.087g (14.94mmol) 3,6,7,10,11-five pentyloxys-2-hydroxy benzo [9,10]
Luxuriant and rich with fragrance 3.334g (14.94mmol) 9-bromine nonyl alcohol 6.2g (44.85mmol) salt of wormwood 2.48g (2.09mm0l) potassiumiodide 40ml2-pentanone output: 7.61g
Compound:
71.10mg (0.0846mmol) 2,3,6,7,10,11-six (ethoxy carbonyl methylene oxygen
Base) benzo [9,10] phenanthrene
510.4mg (0.6246mmol) compound 7a
5 catalyst solutions (in dry diglyme (4 molecular sieve) 10
Volume % original four-isopropyl titanate (merck))
By embodiment 6a) react, but temperature is higher slightly
Output: 428.8mg embodiment 8
By embodiment 6a) react.Compound: 1.412g (2.09mmol) 3,6,7,10,11-five pentyloxys-2-hydroxy benzo [9,10]
Luxuriant and rich with fragrance 0.525g (2.09mmol) 11-bromine decyl alcohol 0.87g (6.27mmol) salt of wormwood 0.347g (2.09mmol) potassiumiodide 25ml2-pentanone output: 1.28g
By embodiment 6b) react, but temperature is than 6b) middle use higher slightly.Use following material:
20.0mg (0.0236mmol) 2,3,6,7,10,11-six (ethoxy carbonyl methylene oxygen
Base) benzo [9,10] luxuriant and rich with fragrance (71,10g)
174.2mg (0.1572mmol) compound 8a
2 catalyst solutions (in dry diglyme (4 molecular sieve) 10
Volume % original four-isopropyl titanate (merck))
Output: 120.1mg embodiment 9
50ml toluene and 0.6ml (7.3mmol) pyridine are added A4.7g (7.3mmol) 3,6,7,10 under nitrogen, in 11-five pentyloxys-2-(hydroxyl-oxethyl) benzos [9, the 10] phenanthrene.In this mixture, be added dropwise to 1M 1,3, the toluene solution 2.2ml of 5-hexanaphthene three carboxyl acyl chlorides under 0 ℃.This mixture was at room temperature stirred 5 hours and stirred 2 hours down, wash with water then at 40 ℃.With the organic phase dried over sodium sulfate.And solvent under reduced pressure removed through distillation.Purifying is undertaken by column chromatography.
Output: 3.4g
Phase behaviour: heating: K 105 D 150 I
Cooling: non-crystallizable.Embodiment 10
Press embodiment 9 by with 1,3,5-benzene tricarbonic acid prepared in reaction compound 10
For Application Example 11 to 13, preparation sheet type (discotic) liquid crystalline cpd between the sheet glass of two indium tin oxide targets (ITO) coating.Electrode area is 2 * 2mm
2Sample layer thickness is about 10 μ m, and 6 μ m barrier films are set.9V voltage is imposed on the battery.Sample temperature is controlled in the specific heating phase of operating with direct current.Be the measuring light electric current, sample is exposed under the periodicity optical signal that frequency is 10Hz, and poor by genlocing commercial measurement light/dark current.Embodiment 11
For present embodiment, the compound of preparation embodiment 1 is also by above-mentioned universal method research photoconductive property.The results are shown in Table 1: table 1
Embodiment 12
| Temperature [℃] | Photoelectric current [PA] | Phase |
| ????50 | ????91 | ????D ho |
| ????60 | ????88 | ????″ |
| ????70 | ????86 | ????″ |
| ????80 | ????86 | ????″ |
| ????90 | ????88 | ????″ |
| ????100 | ????91 | ????″ |
| ????110 | ????94 | ????″ |
| ????120 | ????85 | ????″ |
| ????130 | ????16 | ????D ho |
| ????135 | ????8 | ????I |
For present embodiment, the compound of preparation embodiment 2 is also by above-mentioned universal method research photoconductive property.The results are shown in Table 2 table 2
Embodiment 13
| Temperature [℃] | Photoelectric current [PA] | Phase |
| ????30 | ????95 | ????D ho |
| ????40 | ????58 | ????″ |
| ????50 | ????38 | ????″ |
| ????55 | ????35 | ????″ |
| ????60 | ????33 | ????″ |
| ????65 | ????33 | ????″ |
| ????70 | ????35 | ????″ |
| ????75 | ????36 | ????″ |
| ????80 | ????36 | ????″ |
| ????85 | ????37 | ????″ |
| ????90 | ????16 | ????D ho |
| ????91 | ????5 | ????I |
For present embodiment, the compound of preparation embodiment 4 is also by above-mentioned universal method research photoconductive property.The results are shown in Table 3 table 2
| Temperature [℃] | Photoelectric current [PA] | Phase |
| ????25 | ????1648 | ????D ho |
| ????30 | ????1571 | ????″ |
| ????35 | ????1615 | ????″ |
| ????40 | ????1604 | ????″ |
| ????45 | ????1473 | ????″ |
| ????50 | ????1220 | ????″ |
| ????55 | ????1033 | ????″ |
| ????60 | ????758 | ????″ |
| ????65 | ????549 | ????″ |
| ????70 | ????429 | ????″ |
| ????75 | ????357 | ????″ |
| ????80 | ????330 | ????″ |
| ????90 | ????308 | ????″ |
| ????100 | ????296 | ????″ |
| ????110 | ????308 | ????″ |
| ????120 | ????247 | ????″ |
| ????130 | ????209 | ????D ho |
| ????135 | ????44 | ????I |
Claims (10)
1. the compound of general formula I:
Z[-Y
1(AY
2)
m-X]
nI, wherein to have following implication: Z be n valency aliphatic group or n valency three to seven yuan of saturated or unsaturated carbocyclic or the heterocyclic groups with 2 to 20 carbon atoms to variable, described ring also can be benzo-fused, or has n valency siloxanes or cyclosiloxane base up to 10 Siliciumatoms, Y
1, Y
2Be chemical bond, oxygen, sulphur or-CO-O-,-O-CO-,-N (R)-CO-or-CO-N (R)-group, m is 0 or 1, A is the alkylidene group with 2 to 20 carbon atoms, wherein non-conterminous carbon atom can by oxygen, sulphur or-CO-O-,-O-CO-or-N (R)-replacement, n is 2 to 6R to be hydrogen or C
1-C
4-alkyl and X benzo [9,10] phenanthrene, wherein A, Y for replacing
1, Y
2, m and X be owing to occur n time in compound, so they can be identical or different.
2. compound as claimed in claim 1, wherein Z is for replacing or unsubstituted benzo [9,10] phenanthryl.
3. compound as claimed in claim 1, wherein Z is straight chain or the sub-branched alkyl with 2 to 20 carbon atoms.
4. compound as claimed in claim 1, wherein Z is the siloxane groups of following general formula:
Wherein r is 1 to 9 number, or Z is the cyclosiloxane group of following general formula:
Wherein s is 3 to 6 number.
5. as any one compound of claim 1 to 4, wherein X is benzo [9, the 10] phenanthryl of general formula I I:
R wherein
1To R
5Be identical or different C
1-C
20-alkyl, C
1-C
20-alkoxyl group, C
1-C
20-alkylthio, C
1-C
20-alkanoyloxy, C
1-C
20-alkenyl, C
1-C
20-alkynyl group, fluorine, chlorine, bromine, iodine, cyano group or nitro, in these groups, carbochain can by non-conterminous Sauerstoffatom or sulphur atom or quilt-COO-,-OCO-or-N (R) group at interval.
6. compound as claimed in claim 5, wherein radicals R
1To R
5One or more are polymerizable groups of formula III:
-Y
3-A
1-Y
4-P III wherein each variable has following meanings: Y
3, Y
4Be chemical bond, oxygen, sulphur or-CO-O-,-O-CO-,-N (R)-CO-or-CO-N (R)-group, A
1For having the alkylidene group of 2 to 20 carbon atoms, wherein non-conterminous carbon atom can by oxygen, sulphur or-CO-O-,-O-CO-or-N (R)-replacement, P is polymerizable groups-CH=CH that following formula is represented
2,
-CH
2-CH=CH
2,-CH=CH-CH
3Or
Has the implication of aforesaid right requirement 1 with R.
7. any one compound of claim 1 to 6 is as the purposes of charge transfer compound.
8. any one compound of claim 1 to 6 is used as the purposes of charge transfer compound in photorepeater, laser printer and laser facsimile.
9. any one compound of claim 1 to 6 is used as the purposes of charge transfer compound in electrochemical cell, photoelectrochemical cell and electronic component.
10. be used as the purposes of charge transfer compound in any one the layer of compensation of compound in the light display instrument of claim 1 to 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 95194331 CN1154102A (en) | 1994-06-27 | 1995-06-26 | Oligomer liquid crystal triphenylene derivatives and their use as charge carrying substances in electrophoto-graphy |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4422332.3 | 1994-06-27 | ||
| CN 95194331 CN1154102A (en) | 1994-06-27 | 1995-06-26 | Oligomer liquid crystal triphenylene derivatives and their use as charge carrying substances in electrophoto-graphy |
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| Publication Number | Publication Date |
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| CN1154102A true CN1154102A (en) | 1997-07-09 |
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| CN 95194331 Pending CN1154102A (en) | 1994-06-27 | 1995-06-26 | Oligomer liquid crystal triphenylene derivatives and their use as charge carrying substances in electrophoto-graphy |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101535319B (en) * | 2006-11-01 | 2013-10-16 | 昭和电工株式会社 | Cyclic siloxane compound, organic electroluminescent element, and use thereof |
| CN103484129A (en) * | 2013-08-22 | 2014-01-01 | 北京印刷学院 | Benzophenanthrene chiral dimer discotic liquid crystal compounds and preparation method thereof |
| CN110444766A (en) * | 2019-08-14 | 2019-11-12 | 北京乐华锂能科技有限公司 | A kind of tertiary cathode pole piece and the method for improving anode pole piece high temperature cyclic performance |
-
1995
- 1995-06-26 CN CN 95194331 patent/CN1154102A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101535319B (en) * | 2006-11-01 | 2013-10-16 | 昭和电工株式会社 | Cyclic siloxane compound, organic electroluminescent element, and use thereof |
| US9657040B2 (en) | 2006-11-01 | 2017-05-23 | Samsung Electronics Co., Ltd | Cyclic siloxane compound, organic electroluminescence device, and use of the same |
| CN103484129A (en) * | 2013-08-22 | 2014-01-01 | 北京印刷学院 | Benzophenanthrene chiral dimer discotic liquid crystal compounds and preparation method thereof |
| CN103484129B (en) * | 2013-08-22 | 2016-04-13 | 北京印刷学院 | Benzophenanthrene chiral dimer disc liquid-crystal compounds and preparation method thereof |
| CN110444766A (en) * | 2019-08-14 | 2019-11-12 | 北京乐华锂能科技有限公司 | A kind of tertiary cathode pole piece and the method for improving anode pole piece high temperature cyclic performance |
| CN110444766B (en) * | 2019-08-14 | 2021-09-21 | 创普斯(深圳)新能源科技有限公司 | Ternary positive pole piece and method for improving high-temperature cycle performance of positive pole piece |
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