WO1995020181A1 - Colorants au methine utiles en optique non lineaire - Google Patents

Colorants au methine utiles en optique non lineaire Download PDF

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Publication number
WO1995020181A1
WO1995020181A1 PCT/EP1995/000128 EP9500128W WO9520181A1 WO 1995020181 A1 WO1995020181 A1 WO 1995020181A1 EP 9500128 W EP9500128 W EP 9500128W WO 9520181 A1 WO9520181 A1 WO 9520181A1
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WO
WIPO (PCT)
Prior art keywords
formula
dyes
optionally substituted
phenyl
alkyl
Prior art date
Application number
PCT/EP1995/000128
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German (de)
English (en)
Inventor
Stefan Beckmann
Karl-Heinz Etzbach
Andreas Johann Schmidt
Rüdiger Sens
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1995020181A1 publication Critical patent/WO1995020181A1/fr

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3611—Organic materials containing Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3611—Organic materials containing Nitrogen
    • G02F1/3612—Heterocycles having N as heteroatom
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3613—Organic materials containing Sulfur
    • G02F1/3614—Heterocycles having S as heteroatom

Definitions

  • the present invention relates to the use of methine or aza ⁇ kthin dyes in nonlinear optics, polymers derived from these dyes, their use in nonlinear optics, new methine dyes, thiazole aldehydes as their intermediates and a process for their preparation.
  • nonlinear optical properties of organic compounds are used in many areas of optoelectronics. Examples of this are applications in frequency doubling, in phase modulators, optical amplifiers, interferometers, optical switches or in communications technology.
  • organic materials in particular polymers with special chromophores, can have nonlinear optical properties, some of which are greater than those of comparable inorganic materials.
  • the currently most commonly used materials are inorganic crystals, e.g. from potassium dihydrogen phosphate or lithium niobate. These crystals are complex and expensive to manufacture and, because of their rigid structure, are difficult to use in optical devices. Another disadvantage is their low non-linear effects.
  • a particular advantage of suitable organic chromophores and their use in polymeric materials is their simple manufacture and processing.
  • the chromophores used in nonlinear optics are usually used either in crystalline or polymer-bound form.
  • such dyes should have high hyperpolarizability values, good thermal stability, good contract with the polymers used in nonlinear optical systems and good film-forming properties with copolymers.
  • R 3 L C.
  • R 1 halogen, cyano or thiocyanato
  • R 2 Ci-C ⁇ -alkyl which is optionally substituted by phenyl and can be interrupted by 1 or 2 oxygen atoms in ether function, or optionally substituted phenyl,
  • R 3 is a 5- or 6-membered aromatic carbocyclic or heterocyclic radical
  • R 3 radicals in formula I can be derived, for example, from components from the aniline, indole, aminoquinoline, aminonaphthalene, aminothiazole or aminothiophene series.
  • radicals are, for example, those of the formulas IXa to IXj
  • n 0 or 1
  • Z 3 and Z 4 are the same or different and, independently of one another, each represent hydrogen, C 1 -C 8 -alkyl, which is optionally substituted and can be interrupted by 1 or 2 oxygen atoms in ether function, C 3 -C 4 -alkenyl , C 5 -C 7 cycloalkyl, phenyl or tolyl or together with the compound they connect ⁇ the nitrogen atom for a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms,
  • Z 6 represents hydrogen, halogen, C 1 -C 8 -alkyl, optionally substituted phenyl, optionally substituted benzyl, cyclohexyl, thienyl, hydroxy or C 1 -C 8 monoalkylamino.
  • substituted alkyl groups occur in the above-mentioned formulas, unless otherwise noted, as substituents, for example cyano, phenyl, tolyl, hydroxyl, C 1 -C 6 -alkanoyloxy, acryloyloxy, methacryloyloxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 -Alkyl- aminocarbonyloxy or -CC 4 alkoxycarbonyloxy, where in the latter case the alkoxy group may be substituted by phenyl or -CC 4 alkoxy. They usually have 1 or 2 substituents.
  • halogen, C 1 -C 4 -alkyl or C 1 -C 4 alkoxy can be used as substituents. They usually have 1 to 3 substituents.
  • Suitable radicals R 2 , Z 1 , Z 2 , Z 3 , Z 4 , z 6 and Z 7 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • R 2 , Z 1 , Z 3 , Z, Z 6 and Z 7 are furthermore, for example, pentyl
  • R 2 , Z 1 , Z 3 , Z 4 and Z 7 are furthermore, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3- Ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3, 6-dioxaheptyl, 3, 6-dioxaoctyl, 4, 8-dioxanonyl, 3,7-dioxaoctyl, 3, 7 -Dioxanonyl, 4,7-dioxaoctyl, 4, 7-dioxanonyl, or 4, 8-dioxadecy1.
  • R 2 , Z 3 and Z 4 are, for example, benzyl, 2-methylbenzyl or 1- or 2-phenylethyl.
  • R 2 and Z 6 are, for example, phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4 -Isopropylphenyl, 2-, 3- or 4-butylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2-, 3- or 4-isobutoxyphenyl, 2 , 4-dimethoxyphenyl, 2-, 3- or 4-chlorophenyl or 2, 4-dichlorophenyl.
  • Z 3 and Z 4 are furthermore, for example, 2-cyanoethyl, 2- or 3-cyanopropyl, 2-acetyloxyethyl, 2- or 3-acetyloxypropyl, 2-isobutyryloxyethyl, 2- or 3-isobutyryloxypropyl, 2-methoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2-ethoxycarbonylethyl, 2- or 3-ethoxycarbonylpropyl, 2-dimethylaminocarbonyloxyethyl, 2-diethylaminocarbonyloxyethyl, 2- or 3-dimethylaminocarbonyloxypropyl, 2- or 3-diethylaminocarbonyloxypropyl, 2-methoxycarbonyloxyethyl, 2- or 3-methoxycarbonyloxypropyl, 2-ethoxycarbonyloxyethyl, 2- or 3-ethoxycarbonyloxypropyl, 2-butoxycarbonyloxyeth
  • Z 1 radicals are furthermore, for example, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino, mono- or dimethylaminosulfonylamino, mono- or diethylaminosulfonylamino, mono- or dipropylaminosulfonylamino or mono- sulfonylamino or mono- or di-amino-amino-mono- or di-amino-amino-mono- or di-amino-amino-mono- or di-amino-amino-mono- or di-amino-amino-mono- or di-amino-amino-mono- or di-amino-amino-methyl-N-ethylaminosulfonyl) amino.
  • Residues Z 1 and Z 2 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy or sec-butoxy.
  • Z 6 radicals are also, for example, benzyl, 2-methylbenzyl, 2,4-dimethylbenzyl, 2-methoxybenzyl, 2,4-dimethoxybenzyl, methylamino, ethylamino, propylamino, isopropylamino, butylamino, pentylamino, hexylamino, heptylamino or octylamino or 2-ethylhexylamino.
  • Z 3 and Z 4 together with the nitrogen atom connecting them represent a 5- or 6-membered saturated heterocyclic radical which may have further heteroatoms, for example pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N- (-C-C 4 Alkyl) piperazinyl come into consideration.
  • dyes of the formula I in which R 3 is derived from a component from the aniline, aminothiazole or aminothiophene series is particularly preferred, in particular residues of the formula IXa, iXg, ixh or ixi.
  • the present invention further provides dyes of the formula II
  • R 3 is a 5- or 6-membered aromatic carbocyclic or heterocyclic radical.
  • Dyes of the formula II in which R 2 is a radical which is derived from a component from the aniline, indole, aminoquinoline, aminonaphthalene, aminothiazole or aminothiophene series are preferred.
  • Dyes of the formula II in which R 1 is cyano or thiocyanato, in particular cyano, are furthermore preferred.
  • Dyes of the formula II in which R 2 is phenyl are also preferred.
  • Dyes of the formula II in which R 3 is derived from a component from the aniline, aminothiazole or aminothiophene series are particularly preferred, in particular residues of the formula IXa, IXg, IXh or IXi.
  • dyes of the formula II in which R 3 is a radical of the formula IXa or IXi are dyes of the formula II in which R 3 is a radical of the formula IXa or IXi.
  • the dyes of the formula II can be prepared by methods known per se.
  • Z 3 and Z 4 are identical or different and are each independently hydrogen, Ci-Cs-alkyl, which is optionally substituted and can be interrupted by 1 or 2 oxygen atoms in ether function, C 3 -C 4 alkenyl, C 5 -C 7 Cycloalkyl, phenyl or tolyl or together with the nitrogen atom connecting them for a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms, and
  • Z 6 is hydrogen, halogen, Ci-C ⁇ -alkyl, optionally substituted phenyl, optionally substituted benzyl, cyclohexyl, thienyl, hydroxy or Ci-Cs-monoalkylamino.
  • This implementation takes the form of a Vilsmeier reaction.
  • Suitable organic diluents are e.g. Methylene chloride or chloroform.
  • Suitable inorganic acid halides are, for example, phosphorus oxychloride or phosgene.
  • X groups are, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino or diisobutylamino.
  • the process is usually carried out at a temperature of -50 to + 80 ° C, preferably -30 to + 20 ° C, at atmospheric pressure.
  • the molar ratio of thiazole IV: aminoacrolein V is generally 1: 1 to 1: 5.
  • the process according to the invention is expediently carried out by introducing a solution of aminoacrolein in the organic diluent and adding a solution of the inorganic acid halide at a temperature of from -50 to 0.degree. Then you add the thiazole IV at a temperature of -30 to + 30 ° C. The mixture is then stirred for 0.5 to 5 hours at the temperature specified in more detail above, the reaction mixture is hydrolyzed and worked up by methods known per se, e.g. by separating the target product by filtration.
  • the new process gives the thiazolaldehydes in a simple manner in high yield and purity.
  • the present invention further relates to dyes-containing polymers which, as characteristic monomer units, have a bivalent radical derived from a dye of the formula I and radicals of the formulas VI, VII and VIII
  • Q 1 is hydroxy, -C 6 alkoxy, oxiranylmethoxy, phenoxy, amino or C 1 -C mono- or dialkylamino,
  • Q 2 is hydrogen or methyl
  • the proportion of the monomer units of the bivalent radicals derived from formula I is 1 to 100 mol%, that of formula VI 0 to 99 mol%, that of formula VII 0 to 99 mol% and that of formula VIII 0 up to 75 mol%, in each case based on the polymer, and the average molecular weight of the polymer is 1,000 to 500,000.
  • a divalent radical derived from a dye of the formula I obeys the formula IX
  • YC -C ⁇ o-alkylene and Ar are a divalent 5- or 6-membered aromatic carbocyclic or heterocyclic radical which is derived from the radical R 3 and is bonded to Y via a nitrogen atom, and L, R 1 , R 2 and Q 2 each have the meaning given above.
  • the new polymers can be prepared by methods known per se, as described, for example, in J. Polymer Sei., Part A, Polymer Chem., Volume 28, pages 1 to 13, 1990. Appropriately, a corresponding dye of the formula I is used with an acrylic compound of the formula X.
  • Q 2 and W each have the abovementioned meaning, in the above molar ratio in an inert solvent (for example toluene or xylene) in the presence of a radical initiator (for example azo-bis-isobutyronitrile).
  • an inert solvent for example toluene or xylene
  • a radical initiator for example azo-bis-isobutyronitrile
  • the polymers containing dyes of the formula I are also advantageously suitable for use in non-linear optics.
  • the compounds according to the invention are thermally stable and have particularly large molecular hyperpolarizability values ( ⁇ ).
  • the dyes have good compatibility with the polymers used in nonlinear optical systems and good film-forming properties in copolymers.
  • the determination of the molecular hyperpolarizability can e.g. according to the solvatochromism measurement method (see, for example, Z. Natur ⁇ aba, volume 20a, pages 1441 to 1471, 1965, or J. Org. Chem., volume 54, pages 3775 to 3778, 1989.
  • the position of the absorption band of one is determined Compound in various solvents, eg in dioxane and dimethyl sulfoxide, the shift in the absorption band is then directly proportional to the ß-value, ie compounds with a large solvato-chromic shift show a high molecular hyperpolyrizability and are therefore well suited for use in nonlinear optical systems (see for example Chemistry and Industry, pages 600 to 608, 1990).
  • tricyanophenylpropene was heated in 40 ml acetic anhydride at 80 ° C for 2 hours. The mixture was then cooled to 20 ° C., suction filtered, washed with methanol and diethyl ether and dried at 50 ° C. under reduced pressure.

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  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne l'utilisation en optique non linéaire de colorants au méthine répondant à la formule (I), dans laquelle R1 désigne halogène, cyano ou thiocyanato; R2 désigne alkyle C¿1?-C8 le cas échéant substitué ou phényle le cas échéant substitué; R?3¿ désigne un reste carbocyclique ou hétérocyclique aromatique à 5 ou 6 membres; et L désigne azote ou un reste répondant à la formule CH ou CH=CH-CH. L'invention concerne en outre des polymères dérivés de ces colorants, leur utilisation en optique non linéaire, de nouveaux colorants au méthine, des thiazolaldéhydes qui sont leurs produits intermédiaires ainsi que leur procédé de préparation.
PCT/EP1995/000128 1994-01-24 1995-01-13 Colorants au methine utiles en optique non lineaire WO1995020181A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944401912 DE4401912A1 (de) 1994-01-24 1994-01-24 Methinfarbstoffe in der nichtlinearen Optik
DEP4401912.2 1994-01-24

Publications (1)

Publication Number Publication Date
WO1995020181A1 true WO1995020181A1 (fr) 1995-07-27

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WO (1) WO1995020181A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5623075A (en) * 1994-07-05 1997-04-22 Basf Aktiengesellschaft Thiazolemethine dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4422333A1 (de) * 1994-06-27 1996-01-04 Basf Ag Methin- und Azomethinfarbstoffe auf Basis von Naphthochinonen in der nichtlinearen Optik

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB862443A (en) * 1956-05-21 1961-03-08 Kodak Ltd Improvements in dye-sensitized photographic emulsions
DE1137024B (de) * 1962-09-27 Bayer Ag Verfahren zur Herstellung von substituierten 2-Aminothiazol-(5)-aldehyden
GB2001094A (en) * 1977-07-16 1979-01-24 Basf Ag Dyestuffs
FR2455591A1 (fr) * 1979-05-03 1980-11-28 Sandoz Sa Nouveaux derives du thiazole utilisables comme colorants et leur preparation
EP0326133A2 (fr) * 1988-01-27 1989-08-02 Nippon Telegraph And Telephone Corporation Matériaux organiques à réponse optique non-linéaire et dispositif à réponse optique non-linéaire
EP0524598A1 (fr) * 1991-07-22 1993-01-27 Eastman Kodak Company Dispersions de particules solides de colorants filtrants pour éléments photographiques
US5196147A (en) * 1988-03-28 1993-03-23 Teijin Limited Organic nonlinear optical substance
EP0572898A2 (fr) * 1992-06-04 1993-12-08 BASF Aktiengesellschaft Polymères contenant des colorants de type méthinique ou azaméthinique
EP0576350A1 (fr) * 1992-06-24 1993-12-29 Sanofi Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1137024B (de) * 1962-09-27 Bayer Ag Verfahren zur Herstellung von substituierten 2-Aminothiazol-(5)-aldehyden
GB862443A (en) * 1956-05-21 1961-03-08 Kodak Ltd Improvements in dye-sensitized photographic emulsions
GB2001094A (en) * 1977-07-16 1979-01-24 Basf Ag Dyestuffs
FR2455591A1 (fr) * 1979-05-03 1980-11-28 Sandoz Sa Nouveaux derives du thiazole utilisables comme colorants et leur preparation
EP0326133A2 (fr) * 1988-01-27 1989-08-02 Nippon Telegraph And Telephone Corporation Matériaux organiques à réponse optique non-linéaire et dispositif à réponse optique non-linéaire
US5196147A (en) * 1988-03-28 1993-03-23 Teijin Limited Organic nonlinear optical substance
EP0524598A1 (fr) * 1991-07-22 1993-01-27 Eastman Kodak Company Dispersions de particules solides de colorants filtrants pour éléments photographiques
EP0572898A2 (fr) * 1992-06-04 1993-12-08 BASF Aktiengesellschaft Polymères contenant des colorants de type méthinique ou azaméthinique
EP0576350A1 (fr) * 1992-06-24 1993-12-29 Sanofi Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
M.MATSUOKA ET AL.: "cyanovinylheteroaromatics for organic nonlinear optics", MOLECULAR CRYSTALS AND LIQUID CRYSTALS (INC NONLINEAR OPTICS )., vol. 182a, READING GB *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5623075A (en) * 1994-07-05 1997-04-22 Basf Aktiengesellschaft Thiazolemethine dyes

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