EP0721604A1 - Utilisation de colorants azoiques en optique non lineaire - Google Patents

Utilisation de colorants azoiques en optique non lineaire

Info

Publication number
EP0721604A1
EP0721604A1 EP94927630A EP94927630A EP0721604A1 EP 0721604 A1 EP0721604 A1 EP 0721604A1 EP 94927630 A EP94927630 A EP 94927630A EP 94927630 A EP94927630 A EP 94927630A EP 0721604 A1 EP0721604 A1 EP 0721604A1
Authority
EP
European Patent Office
Prior art keywords
azo dyes
formula
alkyl
phenyl
derived
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP94927630A
Other languages
German (de)
English (en)
Inventor
Gerhard Wagenblast
Ruediger Sens
Karl-Heinz Etzbach
Stefan Beckmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 SE filed Critical BASF SE
Publication of EP0721604A1 publication Critical patent/EP0721604A1/fr
Withdrawn legal-status Critical Current

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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
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/083—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino having -N< (in a ring)
    • 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
    • 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 azo dyes with a diazo component which is derived from an aniline or from a five-membered aromatic heterocyclic amine which contains one to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur heterocyclic ring and can be fused by a benzene, thiophene, pyridine or pyrimidine ring, and a coupling component from the series of pyrrolidin-1-yl or piperidin-1-ylbenzenes or -naphthalenes in the nonlinear optics.
  • a diazo component which is derived from an aniline or from a five-membered aromatic heterocyclic amine which contains one to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur heterocyclic ring and can be fused by a benzene, thiophene, pyridine or pyrimidine ring, and a coupling component from the series of pyrrolidin-1-yl or piperidin-1
  • 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 nonlinear effects.
  • a particular advantage of suitable organic chromophores and their use in polymeric materials is their simple production and processing.
  • the chromophores used in nonlinear optics are usually used either in crystalline or polymer-bound form.
  • azo compounds should have large hyperpolarizability values.
  • the ring A can be fused to benzo and
  • R 1 and R 2 are each independently hydrogen, Ci-C ⁇ - alkyl or Ci-Cg-alkoxy and
  • X represents pyrrolidin-1-yl or piperidin-1-yl, the two last radicals each being Ci-C ß- alkyl, C ⁇ -C 6 -alkoxy, phenyl, vinyl, vinyloxy, vinyloxycarbonyl or a radical of the formula
  • n 0 or 1
  • Y 1 is hydrogen or methyl and Y 2 is hydrogen or phenyl, can be substituted, are advantageously suitable for use in nonlinear optics.
  • azo dyes of the formula I in which D represents the remainder of a diazo component which is derived from an aniline or from a heterocyclic amine from the pyrrole, furan, thiophene, pyrazole, imidazole, oxazole , Isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadia zol, benzofuran, benzthiophene, benzimidazole, benzoxazole, benzthiazole, benzisothiazole, pyridothiophene, pyrimidothiophene or thienothiazole series.
  • azo dyes of the formula I in which D represents the remainder of a diazo component which is derived from an aniline or from a heterocyclic amine from pyrrole, thiophene, pyrazole or thiazole , Isothiazole, triazole, thiadiazole, benzthiophene, benzthiazole, benzisothiazole, pyridothiophene, pyrimidothiophene or thienothiazole series.
  • L 2 hydrogen, C ⁇ -C 6 ⁇ alkyl, halogen, hydroxy, mercapto, C ⁇ -C 6 alkoxy optionally substituted by phenyl or C 1 -C 4 alkoxy, optionally substituted phenoxy, optionally substituted by phenyl Ci-Ce Alkylthio, optionally substituted phenylthio, Ci-C ß -alkylsulfonyl or optionally substituted phenylsulfonyl,
  • L 4 is hydrogen, C ⁇ -C 6 alkyl or phenyl
  • L 6 hydrogen, cyano, C ⁇ -C 4 alkoxycarbonyl, C ⁇ -C 6 alkanoyl, thiocyanato or halogen
  • L 9 cyano, optionally substituted by phenyl C ⁇ -C 6 ⁇ alkyl, optionally substituted by phenyl C ⁇ -C 6 -alkylthio, optionally substituted phenyl, thienyl, C ⁇ -C 4 -alkylthienyl, pyridyl or C ⁇ -C 4 -alkylpyridyl,
  • L 14 is hydrogen, cyano, C ⁇ -C 4 alkoxycarbonyl, nitro or halogen and
  • L 15 , L 16 and L 17 are the same or different and, independently of one another, are in each case hydrogen, C 6 -C 6 -alkyl, C ⁇ -C6 ⁇ alkoxy, halogens, nitro, formyl, cyano, C ⁇ -C 4 -alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or optionally substituted phenylsulfonyl or L 16 is also optionally substituted by nitro-substituted phenylazo.
  • substituted phenyl groups occur in the above-mentioned formulas I and II, unless otherwise noted, substituents such as C ⁇ -C 4 alkyl, chlorine, bromine, nitro or C ⁇ -C 4 alkoxy can be used.
  • the phenyl radicals generally have 1 to 3 substituents.
  • L 2 , L 4 , L 5 , L 8 , L 9 , L 11 , L 12 , L 15 , L 16 , L 17 , R 1 and R 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
  • L 9 radicals are also, for example, benzyl or 1- or 2-phenylethyl.
  • L 2 , L 8 , L 9 and L 11 are, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, benzylthio or 1- or 2-phenylethylthio.
  • L 2 and L 8 are, for example, phenylthio, 2-methylphenylthio, 2-methoxyphenylthio or 2-chlorophenylthio.
  • L 2 , L 8 , L 15 , L 16 , L 17 , R 1 and R 2 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert- Pentyloxy, hexyloxy or 2-methylpentyloxy.
  • L 6 like L 2 , L 8 , L 13 , L 14 , L 15 , L 16 and L 17 , are, for example, fluorine, chlorine or bromine.
  • L 7 like L 1 , L 2 , L 8 , L 15 , L i6 and L 17 , are, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl sec-butylsulfonyl, pentylsulfonylsulfonyl, isopentylsulfonyl, isopentylsulfonyl, isopentylsulfonyl and isopentylsulfonyl , Hexylsulfonyl, phenylsulfonyl, 2-methylphenylsulfonyl, 2-methoxyphenylsulfonyl or 2-chlorophenylsulfonyl.
  • L 3 like L 6 , L 7 , L 8 , L 14 , L 15 , L 16 and L 17 , are, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or sec-butoxycarbonyl.
  • L 2 and L 8 are, for example, 2-methoxyethoxy, 2-ethoxyethoxy, 2- or 3-methoxypropoxy, 2- or 3-ethoxypropoxy, 2- or 4-methoxybutoxy, 2- or 4-ethoxybutoxy, 5-methoxypenty - loxy, 5-ethoxypentyloxy, 6-methoxyhexyloxy, 6-ethoxyhexyloxy, benzyloxy or 1- or 2-phenylethoxy.
  • L 11 radicals are furthermore, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, dipentylamino, dihexylamino or N-methyl-N-ethylamino.
  • L 12 radicals are furthermore, for example, 2-methoxycarbonylethylthio or 2-ethoxycarbonylethylthio.
  • L 9 radicals are furthermore, for example, phenyl, 2-, 3- or 4-methylphenyl, 2, 4-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-methoxyphenyl, 2- or 3-methylthynyl or 2-, 3- or 4-methylpyridyl.
  • L 1 , L 6 and L 7 are furthermore, for example, formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl or hexanoyl.
  • Z 1 cyano, nitro, C ⁇ -C 4 -alkanoyl, optionally substituted benzoyl, C ⁇ -C 4 -alkylsulfonyl, optionally substituted phenylsulfonyl, carboxyl, C ⁇ -C 4 -alkoxycarbonyl, C -C 4 -alkenyloxycarbonyl, phenoxycarbonyl, carbamoyl, C ⁇ -C 4 -mono- or dialkylcarbamoyl, optionally substituted phenylcarbamoyl, optionally substituted phenyl, benzthiazol-2-yl, benzimidazol-2-yl, 5-phenyl-l, 3, 4-thiadiazol-2-yl or 2- Hydroxyquinoxalin-3-yl,
  • Z 4 cyano, C ⁇ -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl
  • Z 5 is hydrogen, C ⁇ -C6 ⁇ alkyl, Ci-C j-alkanoylamino or benzoyl-amino
  • Z 8 is C ⁇ -C 4 alkyl.
  • the remainder is derived from compounds of the formula purple, 111b or IIIc, in which Z 1 is cyano, C ⁇ -C 4 alkanoyl, C ⁇ -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl, Z 2 C ⁇ -C 4 -Alkyl, C ⁇ -C 4 -alkoxy or C -C 4 -alkenyloxy, Z 3 C ⁇ -C 4 -alkoxycarbonyl or C 3 -C 4 -alkenyloxycarbonyl and Z 4 mean cyano.
  • Suitable radicals X are e.g. Pyrrolidin-1-yl, piperidin-1-yl or 2-methacryloyloxymethylpyrrolidin-l-yl.
  • n, Y 1 and Y 2 each have the meaning given above, substituted, or piperidin-1-yl.
  • the azo dyes of the formula I are known per se and are described, for example, in EP-201 896, DE-A-3 108 077, US-A-4 843 153 or GB-A-1 546 803 or can be obtained by the methods mentioned therein become.
  • the azo dyes of the formula I have particularly large molecular hyperpolarizability values ( ⁇ ).
  • 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
  • the shift in the absorption band is then directly proportional to the ⁇ value, ie compounds with a large solvatochromic shift have a large molecular hyperpolyrizability and are therefore well suited for use in nonlinear optical systems (see, for example, Chemistry and Industry, pages 600 to 608, 1990).
  • the suitability of the dyes in communications technology, in electro-optical modulators (e.g. Mach tens inferometers), in optical switches, in frequency mixing or in waveguides should be emphasized.
  • the dyes 4 to 8 listed in the following table can be obtained in an analogous manner.

Landscapes

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

Abstract

L'invention concerne l'utilisation, en optique non linéaire, de colorants azoïques comportant un constituant diazo, dérivé d'une aniline ou d'une amine aromatique hétérocyclique à cinq chaînons qui présente, dans le composé hétérocyclique, entre un et trois atomes hétéro sélectionné(s) dans le groupe comprenant l'azote, l'oxygène et le soufre, et qui peut être annelée par un composé cyclique benzène, thiophène, pyridine ou pyrimidine. Ces colorants azoïques comportent également un constituant copulateur de la série des pyrrolidin-1-yl- ou pipéridin-1-ylbenzènes ou -naphtalènes.
EP94927630A 1993-09-30 1994-09-20 Utilisation de colorants azoiques en optique non lineaire Withdrawn EP0721604A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4333291 1993-09-30
DE4333291A DE4333291A1 (de) 1993-09-30 1993-09-30 Verwendung von Azofarbstoffen in der nichtlinearen Optik
PCT/EP1994/003139 WO1995009382A1 (fr) 1993-09-30 1994-09-20 Utilisation de colorants azoiques en optique non lineaire

Publications (1)

Publication Number Publication Date
EP0721604A1 true EP0721604A1 (fr) 1996-07-17

Family

ID=6499042

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94927630A Withdrawn EP0721604A1 (fr) 1993-09-30 1994-09-20 Utilisation de colorants azoiques en optique non lineaire

Country Status (5)

Country Link
EP (1) EP0721604A1 (fr)
JP (1) JPH09503592A (fr)
KR (1) KR960705257A (fr)
DE (1) DE4333291A1 (fr)
WO (1) WO1995009382A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205347B2 (en) * 2000-10-19 2007-04-17 Trans Photonics, Llc. Substituted-polyaryl chromophoric compounds
JP4567235B2 (ja) * 2001-05-23 2010-10-20 住友化学株式会社 非線形光学素子
KR20130108545A (ko) 2010-09-10 2013-10-04 미쓰비시 가가꾸 가부시키가이샤 헤테로 고리 아조계 색소를 포함하는 잉크 및 그 잉크에 사용되는 색소
JP5935801B2 (ja) 2011-05-20 2016-06-15 三菱化学株式会社 アゾ系化合物及び該化合物を含むインク
CN108467352B (zh) * 2018-05-15 2020-02-21 郑州轻工业学院 一种非线性光学特性可调控的偶氮化合物及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2437274A1 (de) * 1974-08-02 1976-02-12 Hoechst Ag Neue, wasserunloesliche azofarbstoffe und verfahren zu ihrer herstellung
EP0220042A3 (fr) * 1985-10-18 1990-01-17 Imperial Chemical Industries Plc Composé azoique
GB2232680B (en) * 1989-06-16 1992-12-16 James Robinson Ltd Azophenyl compounds
DE4132685A1 (de) * 1991-10-01 1993-04-08 Basf Ag Azofarbstoffe enthaltende polymerisate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9509382A1 *

Also Published As

Publication number Publication date
JPH09503592A (ja) 1997-04-08
WO1995009382A1 (fr) 1995-04-06
DE4333291A1 (de) 1995-04-06
KR960705257A (ko) 1996-10-09

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