WO1996000208A1 - Derives oligomeres de triphenylene a cristaux liquides et leur utilisation comme substances de transport de charge en electrophotographie - Google Patents

Derives oligomeres de triphenylene a cristaux liquides et leur utilisation comme substances de transport de charge en electrophotographie Download PDF

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Publication number
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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Prior art keywords
atoms
compounds according
compounds
group
radicals
Prior art date
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PCT/EP1995/002484
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German (de)
English (en)
Inventor
Lukas HÄUSSLING
Karl Siemensmeyer
Karl-Heinz Etzbach
Helmut Ringsdorf
Peter Schumacher
Dietrich Haarer
Dieter Adam
Juergen Simmerer
Wolfgang Paulus
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Basf Aktiengesellschaft
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Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to EP95924939A priority Critical patent/EP0767776A1/fr
Priority to JP8502817A priority patent/JPH10502065A/ja
Publication of WO1996000208A1 publication Critical patent/WO1996000208A1/fr

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    • 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 System
    • 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 System
    • 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.

Abstract

Des composés répondent à la formule générale (I) Z[-Y?1-(A-Y2)¿m-X]n, dans laquelle les variables ont la signification suivante: Z désigne un reste aliphatique n-valent avec 2 à 20 atomes de carbone ou un reste carbocyclique ou hétérocyclique saturé ou insaturé n-valent, ayant trois à sept éléments, qui peut également être benzocyclisé, ou un reste siloxane ou cyclosiloxane n-valent ayant jusqu'à 10 atomes de Si; Y1, Y2 désignent des liaisons chimiques, oxygène, soufre ou un groupe -CO-O-, -O-CO-, -N(R)-CO- ou -CO-N(R)-; m vaut 0 ou 1; A désigne un groupe alkylène avec 2 à 20 atomes de carbone, dans lequel des atomes de carbone non adjacents peuvent être substitués par oxygène, soufre ou -CO-O-, -O-CO- ou -N(R)-; n est compris entre 2 et 6; R désigne hydrogène ou alcoyle C¿1?-C4; et X désigne un reste triphénylène substitué. Etant donné que A, Y?1, Y2¿, m et X reviennent n fois dans les composés ils peuvent être identiques ou différents. Ces composés sont utiles comme porteurs de charge.
PCT/EP1995/002484 1994-06-27 1995-06-26 Derives oligomeres de triphenylene a cristaux liquides et leur utilisation comme substances de transport de charge en electrophotographie WO1996000208A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95924939A EP0767776A1 (fr) 1994-06-27 1995-06-26 Derives oligomeres de triphenylene a cristaux liquides et leur utilisation comme substances de transport de charge en electrophotographie
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

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4422332.3 1994-06-27
DE4422332A DE4422332A1 (de) 1994-06-27 1994-06-27 Oligomere flüssigkristalline Triphenylenderivate und ihre Verwendung als Ladungstransportsubstanzen in der Elektrophotographie

Publications (1)

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WO1996000208A1 true WO1996000208A1 (fr) 1996-01-04

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Country Link
EP (1) EP0767776A1 (fr)
JP (1) JPH10502065A (fr)
DE (1) DE4422332A1 (fr)
WO (1) WO1996000208A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0847228A2 (fr) * 1996-12-09 1998-06-10 Toyo Ink Manufacturing Co., Ltd. Substance pour dispositif organique électroluminescent et son utilisation
EP0860417A2 (fr) * 1997-02-19 1998-08-26 Dai Nippon Printing Co., Ltd. Composés liquides cristallins et procédé de préparation
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 (9)

* Cited by examiner, † Cited by third party
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0140133A2 (fr) * 1983-09-21 1985-05-08 BASF Aktiengesellschaft Polymères formateurs de phases liquides cristallines
EP0386576A2 (fr) * 1989-03-06 1990-09-12 BASF Aktiengesellschaft Agent de transfert de charge liquide cristallin discotique à bas poids moléculaire
EP0527376A1 (fr) * 1991-08-10 1993-02-17 BASF Aktiengesellschaft Photoconducteurs organiques ayant des propriétés cristallines liquides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0140133A2 (fr) * 1983-09-21 1985-05-08 BASF Aktiengesellschaft Polymères formateurs de phases liquides cristallines
EP0386576A2 (fr) * 1989-03-06 1990-09-12 BASF Aktiengesellschaft Agent de transfert de charge liquide cristallin discotique à bas poids moléculaire
EP0527376A1 (fr) * 1991-08-10 1993-02-17 BASF Aktiengesellschaft Photoconducteurs organiques ayant des propriétés cristallines liquides

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 112, no. 26, 25 June 1990, Columbus, Ohio, US; abstract no. 242068b, N SIMONET-GUEGEN ET AL page 449; column 1; *
CHEMICAL ABSTRACTS, vol. 113, no. 24, 10 December 1990, Columbus, Ohio, US; abstract no. 221896a, H RINGSDORF ET AL page 668; column 2; *
H RINGSDORF ET AL, MACROMOLECULAR SYMPOSIA, vol. 64, WEPF VERLAG CH, pages 19 - 32 *
H SPEISS ET AL, MAKROMOLEKULARE CHEMIE, RAPID COMMUNICATIONS, vol. 14, no. 6, BASEL CH, pages 329 - 338 *
J. ELECTROANAL. CHEM. INTERFACIAL ELECTROCHEM., vol. 280, no. 1, pages 195 - 198 *
LIQ. CRYST., vol. 8, no. 3, pages 375 - 388 *
S ZAMIR ET AL, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 5, DC US, pages 1973 - 1980 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6245449B1 (en) 1996-12-09 2001-06-12 Toyo Ink Manufacturing Co., Ltd. Material for organoelectroluminescence device and use thereof
EP1191020A3 (fr) * 1996-12-09 2003-01-15 Toyo Ink Manufacturing Co., Ltd. Matériau pour dispositif organique électroluminescent et utilisation de ce matériau
EP0847228A3 (fr) * 1996-12-09 1998-09-02 Toyo Ink Manufacturing Co., Ltd. Substance pour dispositif organique électroluminescent et son utilisation
EP0847228A2 (fr) * 1996-12-09 1998-06-10 Toyo Ink Manufacturing Co., Ltd. Substance pour dispositif organique électroluminescent et son utilisation
US6150042A (en) * 1996-12-09 2000-11-21 Toyo Ink Manufacturing Co., Ltd. Material for organoelectro-luminescence device and use thereof
EP1191020A2 (fr) * 1996-12-09 2002-03-27 Toyo Ink Manufacturing Co., Ltd. Matériau pour dispositif organique électroluminescent et utilisation de ce matériau
EP0860417A3 (fr) * 1997-02-19 1999-07-28 Dai Nippon Printing Co., Ltd. Composés liquides cristallins et procédé de préparation
US6174455B1 (en) 1997-02-19 2001-01-16 Dai Nippon Printing Co., Ltd. Liquid crystalline compounds and process for producing the same
EP0860417A2 (fr) * 1997-02-19 1998-08-26 Dai Nippon Printing Co., Ltd. Composés liquides cristallins et procédé de préparation
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

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Publication number Publication date
JPH10502065A (ja) 1998-02-24
DE4422332A1 (de) 1996-01-04
EP0767776A1 (fr) 1997-04-16

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