WO1996000208A1 - Oligomere flüssigkristalline triphenylenderivate und ihre verwendung als ladungstransportsubstanzen in der elektrophotographie - Google Patents
Oligomere flüssigkristalline triphenylenderivate und ihre verwendung als ladungstransportsubstanzen in der elektrophotographie Download PDFInfo
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- WO1996000208A1 WO1996000208A1 PCT/EP1995/002484 EP9502484W WO9600208A1 WO 1996000208 A1 WO1996000208 A1 WO 1996000208A1 EP 9502484 W EP9502484 W EP 9502484W WO 9600208 A1 WO9600208 A1 WO 9600208A1
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- 239000000126 substance Substances 0.000 title claims abstract description 8
- 125000005580 triphenylene group Chemical group 0.000 title abstract description 6
- 239000004973 liquid crystal related substance Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002947 alkylene 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
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- -1 aliphatic radical Chemical class 0.000 claims description 13
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HZMLBSCDATVLIH-UHFFFAOYSA-N (3,6,7,10,11-pentapentoxytriphenylen-2-yl) acetate Chemical group C1=C(OC(C)=O)C(OCCCCC)=CC2=C(C=C(C(OCCCCC)=C3)OCCCCC)C3=C(C=C(OCCCCC)C(OCCCCC)=C3)C3=C21 HZMLBSCDATVLIH-UHFFFAOYSA-N 0.000 description 2
- ZXYHFBOHVNFGHI-UHFFFAOYSA-N 1,2,3,4,5,6-hexapentoxytriphenylene Chemical group CCCCCOC1=C(OCCCCC)C(OCCCCC)=C2C3=C(OCCCCC)C(OCCCCC)=CC=C3C3=CC=CC=C3C2=C1OCCCCC ZXYHFBOHVNFGHI-UHFFFAOYSA-N 0.000 description 2
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- OMGCRTCWEYZECK-UHFFFAOYSA-N ethyl 2-[3,6,7,10,11-pentakis(2-ethoxy-2-oxoethoxy)triphenylen-2-yl]oxyacetate Chemical group C(C)OC(=O)COC1=CC=2C3=CC(=C(C=C3C3=CC(=C(C=C3C=2C=C1OCC(=O)OCC)OCC(=O)OCC)OCC(=O)OCC)OCC(=O)OCC)OCC(=O)OCC OMGCRTCWEYZECK-UHFFFAOYSA-N 0.000 description 2
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- 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
- 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
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- 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
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
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- CATVHUNBFWPEKR-UHFFFAOYSA-N triphenylen-1-ol Chemical group C1=CC=CC2=C3C(O)=CC=CC3=C(C=CC=C3)C3=C21 CATVHUNBFWPEKR-UHFFFAOYSA-N 0.000 description 2
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- 125000005069 octynyl group Chemical group [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
- 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method 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
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 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
- 150000003643 triphenylenes Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/07—Polymeric photoconductive materials
- G03G5/078—Polymeric photoconductive materials comprising silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/328—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a triphenylene ring system
Definitions
- the present invention relates to compounds of general formula I.
- Z is an n-valent aliphatic radical with 2 to 20 C atoms or an n-valent three- to seven-membered saturated or unsaturated carbocyclic or heterocyclic radical, which can also be benzo-fused or an n-valent siloxane or cyclosiloxane radical with up to 10 Si atoms
- A is an alkylene group with 2 to 20 carbon atoms, in which non-adjacent carbon atoms can be replaced by oxygen, sulfur, —CO — 0—, —0 — CO— or —N (R) -,
- R is hydrogen or -CC 4 alkyl
- X is a substituted triphenylene radical, 35 where A, Y 1 , Y 2 , m and X, because they occur n times in the compounds, can be the same or different and the use of these compounds as charge transport compounds in photocopiers and laser printers and in electrochemical cells, 40 electronic components and optical display devices.
- Organic photoconductors have been known for a long time and are used primarily in xerography as electrophotographic recording materials (Schaffert, IBM J. Res. Develop., 45 1971, 75). Organic photoconductors are currently used in molecular dispersion in a neutral binder in photocopiers and laser printers (Borsenberger, J. Phys. Chem., 1993, 11314). Such arrangements have a typical maximum carrier mobility of 10 ⁇ 5 cm 2 / Vs. Charge carrier mobility in this order of magnitude, however, limits the printing or copying speed of electrophotographic devices, so that a further increase in speed only appears possible by increasing the charge carrier mobility. However, this cannot be achieved with the conventional methods currently used.
- a photoconductor layer must be able to withstand a certain mechanical load, such as occurs in individual process steps (concreting the charge image, transferring the toner image).
- the object of the present invention was therefore to provide new liquid-crystalline materials which, in addition to photoconductive properties, have a liquid-crystalline phase in the temperature range between 20 ° C. and 50 ° C. and are mechanically loadable.
- s is a number from 3 to 6.
- Preferred groupings Z (—Y 1 -) n are those which are derived from the compounds Z (- ⁇ Y 1 H) n listed below:
- 1,3,5-cyclohexane tricarboxylic acid 1,3,5-benzenetricarboxylic acid, maleic acid, fumaric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, sebacic acid, ethylene glycol, propylene glycol, 1,3-dihydroxypropylene, 1,4- Dihydroxybutylene, 1, 5-dihydroxypentylene, 1,6-dihydroxyhexylene, 1, 8-dihydroxy octylene and 1, 10-dihydroxydecylene.
- a preferred group Z is a triphenylene radical, particularly preferably an unsubstituted triphenylene radical.
- the spacing-apart molecular part A is preferably an unbranched ⁇ , ⁇ -alkylene group with 3 to 20 C atoms, particularly preferably with 4 to 12 C atoms. This applies in particular to the case where Z is a linear or cyclic siloxane radical.
- Preferred groupings —Y 1 —A — Y 2 - are for example
- p 1 is a number from 2 to 12
- p 2 is a number from 2 to 10
- p 3 is a number from 2 to 11.
- m is preferably 0, ie the triphenylene radical X is linked directly to the central unit via Y 1 .
- the substituted triphenylene radicals X preferably have the following structure
- radicals R 1 to R 5 are preferably fluorine, chlorine, bromine, iodine, nitro, cyano, C 1 -C 2 o -alkyl, C 1 -C 2 -alko y, C 1 -C 2 -alkylthio, C 1 -C 2 o-Alkanoyl, -C-C 2 o-alkenyl, -C-C 2 o-alkynyl mean, the carbon chains in these radicals also by non-adjacent oxygen or sulfur atoms or by —COO—, —OCO— or —N (R) - Groups can be interrupted.
- radicals R 1 to R 5 are in particular:
- Alkyl radicals such as methyl, ethyl, propyl, butyl, pentyl, hexyl,
- alkyl radicals having 4 to 16 carbon atoms are preferred, particularly preferably the butyl, pentyl, hexyl, heptyl, octyl and nonyl radicals.
- carbon chains can be interrupted by non-adjacent oxygen or sulfur atoms or by —COO—, —OCO— or - (R) groups, in particular the latter by —NH— or - CH 3 -.
- substituents R 1 to R 5 are especially aliphatic groups which have double or triple bonds in their carbon chain, for example ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl, tetradecenyl, hexadecenyl , Ethynyl, propynyl,
- radicals which have a polymerizable group P are also suitable as further radicals R 1 to R 5 . These radicals R 1 to R 5 preferably have a structure of the formula III
- Y 3 , Y 4 is a chemical bond, oxygen, sulfur or a group —CO — 0—, —0 — CO—, —N (R) —CO— or —CO — NCR) -,
- a 1 is an alkylene group with 2 to 20 C atoms, in which non-adjacent C atoms can be replaced by oxygen, sulfur, CO — 0—, —0 — CO—, or —N (R) -,
- P is a polymerizable group of the formula
- R has the meaning given above.
- the compounds are prepared by customary methods.
- the preparation of the differently substituted triphenylene derivatives is, for example, by W. reuder, H. Ringsdorf, Makromol. Chem. Rap. Commun, 4, 807 (1983) and in the earlier German patent application 19517208.6.
- the introduction of pre-spacers and polymerizable groups can be carried out analogously to literature regulations, such as are described, for example, in DE-A-39 17 196 and the literature cited therein.
- triphenylene derivatives of the formula I according to the invention are suitable as organic charge transport compounds and photoconductors and can be used, for example, in photocopiers, laser printers and laser fax machines, in electrochemical and photo-electrochemical cells and electronic components and in compensation layers of optical display devices. Examples
- phase behavior was determined by polarization microscopy in a Leitz polarization microscope (Leitz Ortholux II ® ) in connection with a Mettler heating table.
- the optically determined phase sequence was verified by differential scanning calorimetry with a Mettler DSC 7.
- Dimers dissolved in 1 ml methylene chloride, filtered through a white rim filter (pore diameter 0.2 ⁇ ) and precipitated in 100 ml methanol.
- the desired product is obtained with the first high-intensity peak.
- the elugram has several, very low-intensity peaks which cannot be assigned to fully converted low-molecular-weight oligomers; the excess triphenylene alcohol is eluted last.
- the heptamer is obtained as pure substance by spinning in the corresponding fractions. Since residues of THF are still occluded in the glassy oligomer even after drying for several days in an oil pump vacuum, freeze-drying must be carried out from benzene in order to remove the remaining THF.
- Example 9 Analogously to Example 9, the example compound ___ was obtained by reaction with 1, 3, 5-benzenetricarboxylic acid. manufactured.
- the discotically liquid-crystalline compounds between two indium tin oxide (ITO) coated glass plates were prepared.
- the electrode area is 2 * 2 mm 2 .
- the layer thickness of the sample is approx. 10 ⁇ , set by a spacer film of 6 ⁇ m. A voltage of 9 V is applied to this cell.
- the temperature of the sample takes place in a special heating table operated with direct current.
- photocurrent measurement the sample is exposed to a periodic light signal with a frequency of 10 Hz and the difference between light and dark current is measured using the lock-in technique. 17th
- Example 1 the compound from Example 1 was prepared in accordance with the general instructions given above and examined for photoconductive properties. The result is summarized in Table 1.
- Example 2 the compound from Example 2 was prepared in accordance with the general instructions given above and examined for photoconductive properties. The result is summarized in Table 2.
- Example 4 the compound from Example 4 was prepared in accordance with the general instructions given above and examined for photoconductive properties. The result is summarized in Table 3.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8502817A JPH10502065A (ja) | 1994-06-27 | 1995-06-26 | オリゴマー液晶トリフェニレン誘導体及び電子写真における電荷輸送物質としての該オリゴマー液晶トリフェニレン誘導体の使用 |
EP95924939A EP0767776A1 (de) | 1994-06-27 | 1995-06-26 | Oligomere flüssigkristalline triphenylenderivate und ihre verwendung als ladungstransportsubstanzen in der elektrophotographie |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4422332A DE4422332A1 (de) | 1994-06-27 | 1994-06-27 | Oligomere flüssigkristalline Triphenylenderivate und ihre Verwendung als Ladungstransportsubstanzen in der Elektrophotographie |
DEP4422332.3 | 1994-06-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996000208A1 true WO1996000208A1 (de) | 1996-01-04 |
Family
ID=6521533
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/002484 WO1996000208A1 (de) | 1994-06-27 | 1995-06-26 | Oligomere flüssigkristalline triphenylenderivate und ihre verwendung als ladungstransportsubstanzen in der elektrophotographie |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0767776A1 (de) |
JP (1) | JPH10502065A (de) |
DE (1) | DE4422332A1 (de) |
WO (1) | WO1996000208A1 (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0847228A2 (de) * | 1996-12-09 | 1998-06-10 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
EP0860417A2 (de) * | 1997-02-19 | 1998-08-26 | Dai Nippon Printing Co., Ltd. | Flüssigkristallverbindungen und Verfahren zur Herstellung |
US7175889B2 (en) | 2003-03-17 | 2007-02-13 | Fuji Photo Film Co., Ltd. | Retardation film and compound |
US7723524B2 (en) | 2003-09-29 | 2010-05-25 | Daiichi Pharmaceutical Co., Ltd. | 8-cyanoquinolonecarboxylic acid derivative |
DE10229169B4 (de) * | 2002-06-28 | 2011-08-11 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 80686 | Neue diskotische Verbindungen und Verfahren zur Herstellung optisch anisotroper Elemente |
US9657040B2 (en) | 2006-11-01 | 2017-05-23 | Samsung Electronics Co., Ltd | Cyclic siloxane compound, organic electroluminescence device, and use of the same |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19517208A1 (de) * | 1995-05-11 | 1996-11-14 | Basf Ag | Derivate des Triphenylens |
US5766510A (en) * | 1995-08-25 | 1998-06-16 | Dai Nippon Printing Co., Ltd. | Liquid crystalline compound and use thereof |
US6224787B1 (en) * | 1997-03-10 | 2001-05-01 | Dai Nippon Printing Co., Ltd. | Liquid crystalline charge transport material |
US6143452A (en) * | 1998-09-29 | 2000-11-07 | Konica Corporation | Electrophotographic photoreceptor |
DE10037391A1 (de) | 2000-08-01 | 2002-02-14 | Covion Organic Semiconductors | Strukturierbare Materialien, Verfahren zu deren Herstellung und deren Verwendung |
JP5496748B2 (ja) * | 2003-08-04 | 2014-05-21 | ユー・ディー・シー アイルランド リミテッド | トリフェニレン化合物 |
TWI246356B (en) * | 2003-10-17 | 2005-12-21 | Lg Chemical Ltd | New organic compound and organic light emitting device using the same |
US8449989B2 (en) | 2003-10-17 | 2013-05-28 | Lg Chem, Ltd. | Organic compound and organic light emitting device using the same |
JP5187549B2 (ja) * | 2007-06-27 | 2013-04-24 | 株式会社リコー | 新規なトリフェニレン化合物及びその製造方法、電子写真感光体、画像形成方法、画像形成装置および画像形成装置用プロセスカートリッジ |
WO2024111519A1 (ja) * | 2022-11-22 | 2024-05-30 | 積水化学工業株式会社 | ポリオルガノシロキサン |
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- 1994-06-27 DE DE4422332A patent/DE4422332A1/de not_active Withdrawn
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- 1995-06-26 JP JP8502817A patent/JPH10502065A/ja active Pending
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US6245449B1 (en) | 1996-12-09 | 2001-06-12 | Toyo Ink Manufacturing Co., Ltd. | Material for organoelectroluminescence device and use thereof |
EP1191020A3 (de) * | 1996-12-09 | 2003-01-15 | Toyo Ink Manufacturing Co., Ltd. | Material für eine organische Elektrolumineszenzvorrichtung und seine Verwendung |
EP0847228A3 (de) * | 1996-12-09 | 1998-09-02 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
EP0847228A2 (de) * | 1996-12-09 | 1998-06-10 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
US6150042A (en) * | 1996-12-09 | 2000-11-21 | Toyo Ink Manufacturing Co., Ltd. | Material for organoelectro-luminescence device and use thereof |
EP1191020A2 (de) * | 1996-12-09 | 2002-03-27 | Toyo Ink Manufacturing Co., Ltd. | Material für eine organische Elektrolumineszenzvorrichtung und seine Verwendung |
EP0860417A3 (de) * | 1997-02-19 | 1999-07-28 | Dai Nippon Printing Co., Ltd. | Flüssigkristallverbindungen und Verfahren zur Herstellung |
US6174455B1 (en) | 1997-02-19 | 2001-01-16 | Dai Nippon Printing Co., Ltd. | Liquid crystalline compounds and process for producing the same |
EP0860417A2 (de) * | 1997-02-19 | 1998-08-26 | Dai Nippon Printing Co., Ltd. | Flüssigkristallverbindungen und Verfahren zur Herstellung |
DE10229169B4 (de) * | 2002-06-28 | 2011-08-11 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., 80686 | Neue diskotische Verbindungen und Verfahren zur Herstellung optisch anisotroper Elemente |
US7175889B2 (en) | 2003-03-17 | 2007-02-13 | Fuji Photo Film Co., Ltd. | Retardation film and compound |
US7723524B2 (en) | 2003-09-29 | 2010-05-25 | Daiichi Pharmaceutical Co., Ltd. | 8-cyanoquinolonecarboxylic acid derivative |
US9657040B2 (en) | 2006-11-01 | 2017-05-23 | Samsung Electronics Co., Ltd | Cyclic siloxane compound, organic electroluminescence device, and use of the same |
Also Published As
Publication number | Publication date |
---|---|
EP0767776A1 (de) | 1997-04-16 |
DE4422332A1 (de) | 1996-01-04 |
JPH10502065A (ja) | 1998-02-24 |
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