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WO1995009828A1 - 2,4,5-trifluorobenzenes et leur utilisation dans des melanges de cristaux liquides - Google Patents

2,4,5-trifluorobenzenes et leur utilisation dans des melanges de cristaux liquides Download PDF

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WO1995009828A1
WO1995009828A1 PCT/EP1994/003126 EP9403126W WO9509828A1 WO 1995009828 A1 WO1995009828 A1 WO 1995009828A1 EP 9403126 W EP9403126 W EP 9403126W WO 9509828 A1 WO9509828 A1 WO 9509828A1
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liquid crystal
trans
diyl
formula
atoms
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English (en)
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Hubert Schlosser
Dietmar Jungbauer
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Merck Patent GmbH
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Merck Patent GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone

Definitions

  • electromagnetic radiation as well as to the materials with which they are associated during and after the manufacturing process (e.g.
  • Liquid crystal mixtures and thus on a large number of mesogenic and non-mesogenic compounds of different structures, which enable the mixtures to be adapted to the most varied of applications. This applies both to the areas where nematic LC phases are used in
  • the invention therefore relates to new 2,4,5-trifluorobenzene derivatives of the general formula (I)
  • R 1 is H, a straight chain or branched (with or without asymmetric
  • a 1 , A 2 , A 3 are the same or different 1, 4-phenylene, pyridine-2,5-diyl,
  • Pyrtmidine-2,5-diyl in which one or two H atoms can be replaced by F, trans-1, 4-cyclohexylene, 1, 3-dioxane-2,5-diyl or naphthalene-2,6-diyl;
  • k, l, m, n, o, p are zero or one, provided that the sum k + m + o is greater than zero.
  • R 1 is a straight-chain alkyl having 1 to 15 carbon atoms
  • a 1 , A 2 , A 3 are identical or different 1, 4-phenylene, in which one or two H atoms can be replaced by F, or trans-1, 4-cyclohexylene;
  • M 1 , M 2 , M 3 are the same or different -CH 2 CH 2 -, -C ⁇ C-, -CH 2 O-, -OCH 2 -, -CO-O-, -O-CO-.
  • R 1 means methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl.
  • the compounds according to the invention are chemically and photochemically stable. They have extremely low melting points, some of which are below 10 ° C, and generally have broad nematic phases. Furthermore, they show no tendency to induce higher-order phases in nematic mixtures and are readily soluble.
  • the compounds according to the invention can be prepared by methods known per se from the literature (see, for example, Houben-Weyl, methods of
  • bromo-2,4,5-trifluorobenzene (II) By cross-coupling bromo-2,4,5-trifluorobenzene (II) with organometallic derivatives of Z 2 , e.g. Grignard, lithium and zinc derivatives, and boronic acids of Z 2 using transition metal catalysts, e.g. dichloro [1, 3-bis (diphenylphosphino ) propane] nickel (II), tetrakis (triphenylphosphine) palladium (O) and [1, 1 'bis (diphenylphosphino) ferrocene] palladium (II) dichloride, 2,4,5-trifluorobenzenes of the formula (I) according to the invention (see, for example: PW Jolly in Comprehensive Organometallic Chemistry Vol.
  • 2,4,5-trifluorophenoKV can be esterified with carboxylic acids or
  • radicals Z 1 and / or Z 2 are synthesized by methods known per se and familiar to the person skilled in the art.
  • the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • DE-A 23 44 732, 24 50 088, 24 29 093, 25 02 94, 26 36 684, 27 01 591 and 27 52 975 for compounds with 1,4-cyclohexylene and 1,4-phenylene groups ;
  • DE-A 26 41 724 for compounds with pyrimidine-2,5-diyl groups;
  • disubstituted pyridines and disubstituted pyrimidines can also be found, for example, in the corresponding volumes of the series "The
  • Dioxane derivatives are useful by reacting an appropriate aldehyde (or one of its reactive derivatives) with one
  • Sulfuric acid, benzene or p-toluenesulfonic acid at temperatures between about 20 ° C and about 150 ° C, preferably between 80 ° C and 120 ° C.
  • Acetals are primarily suitable as reactive derivatives of the starting materials.
  • Compounds in which an aromatic ring is substituted by at least one F atom can also be obtained from the corresponding diazonium salts by exchanging the diazonium group for a fluorine atom, e.g. according to the methods of Balz and Schiemann.
  • the acid halides especially the chlorides and bromides
  • the anhydrides for example also mixed anhydrides, azides or esters, in particular alkyl esters with 1 -4 C atoms in the alkyl group.
  • Reactive derivatives of the alcohols or phenols mentioned include, in particular, the corresponding metal alcoholates or phenolates,
  • Hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as carbon tetrachloride, dichloromethane or tetrachlorethylene and sulfoxides such as dimethyl sulfoxide or sulfolane.
  • Ethers of the formula (I) are more appropriate by etherification
  • liquid crystal mixtures intended for use in electro-optical or all-optical elements e.g. Display elements, switching elements, light modulators, elements for image processing, signal processing or generally in the field of non-linear optics are suitable. In general, they are suitable for introducing or spreading a nematic phase in LC mixtures.
  • Liquid crystal mixtures according to the invention in general 0.1 to 70 mol%, preferably 0.5 to 50 mol%, in particular 1 to 25 mol%.
  • constituents of the mixtures according to the invention are preferably selected from the known compounds with nematic or
  • cholesteric phases include, for example, biphenyls, terphenyls, phenylcyclohexanes, bicyclohexanes, cyclohexylbiphenyls, mono-, di- and
  • Trifluorophenyls Generally, there are those available commercially
  • Suitable further constituents of nematic or chiral nematic liquid crystal mixtures according to the invention are examples 4-fluorobenzenes, as for example in EP-A 494 368, WO 92/06 148, EP-A 460 436, DE-A 4 1 1 1 766, DE-A 4 1 1 2 024, DE-A 4 1 1 2 001, DE-A 4 100 288, DE-A 4 101 468, EP-A 423 520, DE-A 392 3064, EP-A 406 468, EP-A 393 577, EP-A 393 490,
  • Phenylcyclohexanes as described for example in DE-A 4 108 448.
  • Liquid-crystalline mixtures which contain compounds of the general formula (I) are particularly suitable for use in electro-optical switching and display devices (displays).
  • Switching and display devices generally include the following components: a liquid-crystalline medium, carrier plates (e.g. made of glass or plastic) coated with electrodes, at least one of which is transparent, at least one orientation layer, spacers, adhesive frames, polarizers and for Color displays thin color filter layers.
  • Other possible components are antireflection, passivation, compensation and barrier layers as well as electrically non-linear elements, such as thin-film transistors (TFT) and metal-insulator-metal (MIM) elements.
  • TFT thin-film transistors
  • MIM metal-insulator-metal
  • phase transition temperatures are determined with the help of a polarizing microscope on the basis of the texture changes.
  • the melting point is determined using a DSC device.
  • Glass transition (Tg) takes place in ° C and the values are between the phase names in the phase sequence.
  • Parentheses are set or the phase sequence is given ascending and descending in temperature.
  • nematic liquid crystals pure or in a mixture
  • the values for the optical and dielectric anisotropy and the electro-optical characteristic curve are recorded at a temperature of 20 ° C., unless stated otherwise.
  • Liquid crystals that have no nematic phase at 20 ° C become too 10% by weight was mixed in ZLI-1565 (commercial nematic liquid crystal mixture from E. Merck, Darmstadt) and the values were extrapolated from the results of the mixture.
  • Electro-optical characteristics are determined on the basis of the transmission of a measuring cell.
  • the cell is positioned between crossed polarizers in front of a light source.
  • There is a light detector behind the cell the sensitivity of which is optimized by filters for the visible area of the light. Analogous to the gradual increase in the voltage applied to the cell, the change in transmission is recorded. Values such as threshold voltage and slope are determined from this.
  • the dielectric anisotropy ( ⁇ ) is the difference between the dielectric constants parallel ( ⁇
  • the electrical variable HR (holding ratio) is in accordance with the
  • the measuring cell is crossed on a rotary table of a polarizing microscope Attached analyzer and polarizer.
  • the measuring cell is positioned by turning it so that a photodiode indicates minimal light transmission (dark state).
  • the microscope illumination is controlled so that the photodiode shows the same light intensity for all cells.
  • the light intensity (bright state) changes and the contrast is calculated from the ratio of the light intensity of these states.
  • the values for the spontaneous polarization P S [nC / cm 2 ], the contrast K and the optical switching time ⁇ [ ⁇ s] are determined, all measurements being carried out at a temperature of 25 ° C.
  • the position of the table with minimum light passage for the two switching states in the cell is determined by rotating the table.
  • the difference between the two positions on the rotary table is twice the effective tilt angle.
  • the photodiode is used to determine the switching time ⁇ by measuring the rise time of the light signal from 10% to 90% signal level.
  • the switching voltage consists of rectangular pulses and is ⁇ 10V / ⁇ m.
  • triphenylphosphine are at 0 ° C in 20 ml
  • the corresponding Grignard reagent is prepared from 1,5 g (71.09 mmol) of 2,4,5-trifluorobromobenzene and 1.90 g (78.20 mmol) of magnesium in 150 ml of diethyl ether, which reacts at 0 ° C. to form a solution of 6.23 g (85.31 mmol)
  • Dimethylformamide is added dropwise in 100 ml of diethyl ether. After 2 h at 0 ° C., the mixture is extracted with diethyl ether and dilute hydrochloric acid, the organic phase is dried over Na 2 SO 4 , evaporated and distilled at atmospheric pressure, after which 8.65 g of 2,4,5-trifluorobenzaldehyde are obtained.
  • Table 1 compares the physical properties of compounds according to the invention with those of individual substances and mixtures known from the literature.
  • the substances according to the invention are those described in Examples 15 (S1 5) and 17 (S1 7); the comparison substances are a compound with an ester group (SE) known from JP-A 58/1 88 839, mesogenic compounds with a parafluorosubstituted phenyl group (SP1, SP2, SP3 and SP4), and a mixture of the substances SP1 , SP2, SP3 and SP4 (MP).
  • SE ester group
  • SP1, SP2, SP3 and SP4 mesogenic compounds with a parafluorosubstituted phenyl group
  • MP mixture of the substances SP1 , SP2, SP3 and SP4
  • the nematic phase lies in the technically relevant area.
  • the compounds according to the invention have a significantly lower ⁇ n at the same reduced temperatures (T / T N l ), which is advantageous.
  • ⁇ is larger than in MP.
  • Table 2 shows physical quantities of compounds according to the invention and compounds known from the literature, in each case 10% by weight in a commercial nematic liquid crystal mixture (ZLI 1 565, E. Merck, Darmstadt,
  • the compounds according to the invention show significantly smaller values for ⁇ n D.
  • Table 3 shows a comparison of the substances according to the invention from Examples 30 (S 30) and 31 (S 31) with the reference SE as pure substance and in a mixture.
  • the pure substances according to the invention have no smectic phases and a much broader nematic phase range than the reference substance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

L'invention concerne des dérivés de 2,4,5-trifluorobenzènes de la formule générale (I), où les symboles et les indices ont la notation suivante: R1 désigne H, un alkyle linéaire ou ramifié (avec ou sans atomes de C asymétrique) ayant entre 1 et 15 ou entre 3 et 15 atomes de C, où un ou deux groupes CH¿2? non adjacents peuvent être remplacés par -O-, -CH=CH-, -C C-, (a) ou -Si(CH3)2- et où un ou plusieurs atomes de H du reste alkyle peuvent être substitués par F; A?1, A2 A3¿ sont identiques ou différents et désignent 1,4 phénylène, pyridine-2,5-diyle, pyrimidine-2,5-diyle, dans lesquels un ou deux atomes de H peuvent être remplacés par F, trans-1,4-cyclohexylène, 1,3-dioxane-2,5-diyle ou naphtalène-2,6-diyle; M?1, M2, M3¿ sont identiques ou différents et désignent -CH¿2?CH2-, -CH=CH-, -C C-, -CH2CH2CH2CH2-, -CH2CH2CH2-O-, -O-CH2CH2CH2-, -CH2CH2CO-O-, -O-CO-CH2CH2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-; k, l, m, n, o et p valent 0 ou 1, à condition que la somme k + m + o soit supérieure à 0. Des composés des formules (B), (C), (D) et (E) sont exclus. Les composés produits selon l'invention sont chimiquement et photochimiquement stables. Ils ont des points de fusion extrêmement bas qui sont en partie inférieurs à 10 °C et ont, de manière générale, des phases nématiques larges. Ces composés n'ont par ailleurs pas tendance à induire des phases d'ordre élevé et ont une bonne solubilité. Ils présentent des valeurs favorables d'anisotropie de l'indice de réfraction comme des constantes diélectriques et se caractérisent par une faible conductibilité (taux de retenue de 99 % et plus), ce qui est extrêmement intéressant pour des applications concernant des transistors à couche mince.
PCT/EP1994/003126 1993-10-01 1994-09-19 2,4,5-trifluorobenzenes et leur utilisation dans des melanges de cristaux liquides Ceased WO1995009828A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4333570A DE4333570A1 (de) 1993-10-01 1993-10-01 2,4,5-Trifluorbenzole und ihre Verwendung in Flüssigkristallmischungen
DEP4333570.5 1993-10-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6911451B1 (en) * 1998-06-05 2005-06-28 Celltech R&D Limited Phenylalanine derivatives
TWI485231B (zh) * 2011-05-26 2015-05-21 Dainippon Ink & Chemicals 具有２－氟苯基氧基甲烷構造之化合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
No relevant documents disclosed *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6911451B1 (en) * 1998-06-05 2005-06-28 Celltech R&D Limited Phenylalanine derivatives
TWI485231B (zh) * 2011-05-26 2015-05-21 Dainippon Ink & Chemicals 具有２－氟苯基氧基甲烷構造之化合物

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