DE3703495A1 - New perylene carboximide derivs. - useful as fluorescent dyes - Google Patents
New perylene carboximide derivs. - useful as fluorescent dyesInfo
- Publication number
- DE3703495A1 DE3703495A1 DE3703495A DE3703495A DE3703495A1 DE 3703495 A1 DE3703495 A1 DE 3703495A1 DE 3703495 A DE3703495 A DE 3703495A DE 3703495 A DE3703495 A DE 3703495A DE 3703495 A1 DE3703495 A1 DE 3703495A1
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- perylene
- dyes according
- dye
- fluorescence
- 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- Withdrawn
Links
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims abstract description 29
- -1 perylene carboximide Chemical compound 0.000 title abstract description 10
- 239000007850 fluorescent dye Substances 0.000 title abstract description 5
- 239000000975 dye Substances 0.000 claims abstract description 103
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 28
- 239000004065 semiconductor Substances 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000004246 zinc acetate Substances 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 239000000700 radioactive tracer Substances 0.000 claims description 4
- 230000005284 excitation Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- NUZVLYNISQOZOW-UHFFFAOYSA-N 2,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(N)=C1 NUZVLYNISQOZOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000012491 analyte Substances 0.000 claims description 2
- 238000000407 epitaxy Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000004154 testing of material Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 2
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims 1
- 102000006830 Luminescent Proteins Human genes 0.000 claims 1
- 108010047357 Luminescent Proteins Proteins 0.000 claims 1
- 241000505673 Scintilla Species 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910001385 heavy metal Chemical class 0.000 claims 1
- 238000003018 immunoassay Methods 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000012698 light-induced step-growth polymerization Methods 0.000 claims 1
- 238000000504 luminescence detection Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 238000011896 sensitive detection Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 238000012801 analytical assay Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NSPXANJRIVJHEB-UHFFFAOYSA-N 22,25-diazaheptacyclo[12.9.3.01,10.04,9.08,17.011,16.015,20]hexacosa-3,5,7,9,11,13,15(20),16,18-nonaene-21,23,24,26-tetrone Chemical compound C123CC=C4C=CC=C5C6=CC=C(C=7C(=CC=C(C1=C45)C67)C(NC3=O)=O)C(NC2=O)=O NSPXANJRIVJHEB-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
- G03G5/0648—Heterocyclic compounds containing two or more hetero rings in the same ring system containing two relevant rings
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- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
- G03G5/0657—Heterocyclic compounds containing two or more hetero rings in the same ring system containing seven relevant rings
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/054—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means
- H01L31/055—Optical elements directly associated or integrated with the PV cell, e.g. light-reflecting means or light-concentrating means where light is absorbed and re-emitted at a different wavelength by the optical element directly associated or integrated with the PV cell, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01S—DEVICES USING THE PROCESS OF LIGHT AMPLIFICATION BY STIMULATED EMISSION OF RADIATION [LASER] TO AMPLIFY OR GENERATE LIGHT; DEVICES USING STIMULATED EMISSION OF ELECTROMAGNETIC RADIATION IN WAVE RANGES OTHER THAN OPTICAL
- H01S3/00—Lasers, i.e. devices using stimulated emission of electromagnetic radiation in the infrared, visible or ultraviolet wave range
- H01S3/14—Lasers, i.e. devices using stimulated emission of electromagnetic radiation in the infrared, visible or ultraviolet wave range characterised by the material used as the active medium
- H01S3/20—Liquids
- H01S3/213—Liquids including an organic dye
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
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Abstract
Description
Perylenfarbstoffe, die Perylen-3,4 : 9,10-tetracarbonsäurebisimide, sind seit langer Zeit als lichtechte Küpenfarbstoffe oder Pigment farbstoffe bekannt - siehe z. B. Indanthrenrot GG. In neuerer Zeit wurde aber erst bekannt, daß diese Farbstoffe außerdem ein erhebliches Fluoreszenzpotential besitzen (siehe z. B. H. Langhals, Chem. Ber. 118, 4641 (1986)). Die bis dahin für die Fluoreszenzanwendungen hinderliche Schwerlöslichkeit der Farbstoffe konnte durch die Einführung von tert-Butylgruppen überwunden werden. Der nach diesem Konzept entwickelte Farbstoff 8 (H. Langhals, Chem. Ber. 118, 4641 (1986)) ist als bester Kompromiß zwischen einer hohen Fluoreszenzquantenausbeute, einer großen Photostabilität, einer guten Löslichkeit in organischen Lösungsmitteln und einer guten synthetischen Zugänglichkeit aufzufassen.Perylene dyes, the perylene-3,4: 9,10-tetracarboxylic acid bisimides, have long been known as lightfast vat dyes or pigments dyes known - see e.g. B. Indanthrene red GG. More recently but it was only known that these dyes also a considerable Have fluorescence potential (see e.g. H. Langhals, Chem. Ber. 118, 4641 (1986)). Until then for fluorescence applications impeding poor solubility of the dyes could Introduction of tert-butyl groups can be overcome. The after dye 8 developed this concept (H. Langhals, Chem. Ber. 118, 4641 (1986)) is the best compromise between a high one Fluorescence quantum yield, great photostability, one good solubility in organic solvents and good to understand synthetic accessibility.
Der Farbstoff weist mit einer Fluoreszenzquantenausbeute von 99%, einem molaren Extinktionskoeffizient von 95 000 und einer überraschend hohen Lichtechtheit sowie einer guten Löslichkeit in organischen Lösungsmitteln geradezu erstaunliche Eigenschaften auf.The dye has a fluorescence quantum yield of 99%, a molar extinction coefficient of 95,000 and one surprising high lightfastness and good solubility in organic Solvents have amazing properties.
In der vorliegenden Arbeit geht es darum, diese ungewöhnlich guten Eigenschaften noch zu übertreffen.The present work is about these unusually good ones Properties still to be surpassed.
Hier sind generell zwei Punkte bei Fluoreszenzfarbstoffen zu nennen, die möglichst Extremwerte annehmen sollen:There are generally two points in fluorescent dyes, which should assume extreme values if possible:
- 1. Die Photostabilität (Lichtechtheit)1. The photostability (light fastness)
- 2. Die Löslichkeit in organischen Lösungsmitteln.2. Solubility in organic solvents.
Punkt 2 wird insbesondere bei Anwendungen in Farbstoff-Lasern wichtig, da hier je nach Anwendungen zum Teil Extinktionen von über 10 bei einer Schichtdicke von 1 cm angestrebt werden.Point 2 is especially for applications in dye lasers important, since depending on the application, extinctions of over 10 with a layer thickness of 1 cm.
Zu Punkt 1 wurde überraschenderweise gefunden, das Perylenfarbstoffe mit aliphatischen Resten an den Stickstoffen (R = Alkyl in Formel 5) eine noch höhere Photostabilität besitzen als Perylenfarbstoffe mit aromatischen Resten. Die in der Literatur bekannte Methode, die Löslichkeit von Farbstoffen durch das Einführen von langkettigen n-Alkylresten zu erhöhen, versagte aber bei den Pery lenfarbstoffen völlig. Selbst mit R = n-Dodecyl in 5 lag die Löslichkeit um etliche Zehnerpotenzen niedriger als die von 8. Außerdem verändert ein sukzessives Verlängern der Alkylkette die Löslichkeit nur unwesentlich, so daß auch bei erheblich längeren Ketten der erforderliche Fortschritt nicht zu erwarten steht.Surprisingly, point 1 was found to be perylene dyes with aliphatic residues on the nitrogen (R = alkyl in Formula 5) have an even higher photostability than perylene dyes with aromatic residues. The one known in the literature Method, the solubility of dyes by introducing to increase long-chain n-alkyl residues, but failed with the Pery oil dyes completely. The solubility was even with R = n-dodecyl in 5 several powers of ten lower than that of 8. In addition, a gradual lengthening of the alkyl chain changes the Solubility only insignificant, so that even with considerably longer ones Chains the necessary progress is not expected.
Zum Erstaunen fand man jedoch, daß sekundäre Alkylreste, z. B. die synthetisch leicht zugänglichen Reste mit zwei gleichen, langkettigen Alkylgruppen, (5, R = sec-Alkyl) die Löslichkeit der Farbstoffe noch wesentlich über die von 8 steigern können. Die Photo stabilität der Farbstoffe ist höher als die von 8. Die für die Anwendung der Farbstoffe wichtigen UV/VIS-spektroskopischen Eigenschaften sind mit denen von 8 identisch. Mit länger werdenden Alkylketten in 1 steigt die Löslichkeit stetig - ein Maximum ist nach bisherigen Untersuchungen nicht abzusehen. Allerdings nimmt der relative Anteil des Chromophors am Gesamtmolekulargewicht bei länger werdenden Ketten immer mehr ab, so daß das Optimum für praktische Anwendungen beim Farbstoff mit zwei 6-Undecyl resten, also dem Farbstoff 10 liegen dürfte.To the astonishment, however, it was found that secondary alkyl residues, e.g. B. the synthetically easily accessible residues with two identical, long-chain Alkyl groups, (5, R = sec-alkyl) the solubility of the dyes can still significantly increase over that of 8. The photo stability of the dyes is higher than that of 8. The for the application of the dyes important UV / VIS spectroscopic Properties are identical to those of 8. With longer ones Alkyl chains in 1 increase the solubility steadily - a maximum According to previous studies, it is not foreseeable. Indeed the relative proportion of the chromophore to the total molecular weight as chains get longer and longer, so that the optimum for practical dye applications with two 6-undecyl residues, so the dye 10 should be.
Ein ähnliches, überraschendes Löslichkeitsverhalten wird bei den Cycloalkylresten, Farbstoffe 2, beobachtet, die bei Ringen größer als Cyclooctyl eine kontinuierliche Steigerung der Löslichkeit mit größer werdender Ringgröße zeigen. Beim Cyclopentadecylrest ist die Löslichkeit bereits für die meisten Anwendungen ausreichend groß. Aus synthetischen Gründen sind bestimmte Ringgrößen zu bevorzugen (siehe z. B. die Stroy-Synthese). Hier sind besonders Ringe zu nennen mit n = 15, 20, 22, 24, 30, 33, 36 und 40. Dies hat jedoch rein synthetische Gründe. Die UV/VIS-spektroskopischen Eigenschaften der für Anwendungen wichtigen Farbstoffe mit n größer 12 sind sehr ähnlich.A similar, surprising solubility behavior is observed with the cycloalkyl radicals, dyes 2, which show a continuous increase in solubility with rings of larger size in rings larger than cyclooctyl. The solubility of the cyclopentadecyl radical is sufficiently high for most applications. Certain ring sizes are preferred for synthetic reasons (see, for example, Stroy synthesis). Rings with n = 15, 20, 22, 24, 30, 33, 36 and 40 are particularly worth mentioning. However, this has purely synthetic reasons. The UV / VIS spectroscopic properties of the dyes important for applications with n greater than 12 are very similar.
Die Farbstoffe 3 und 4 zeigen ein ähnliches Verhalten wie die Farbstoffe 1 bzw. 2. Die Ausbeuten bei der Synthese sind jedoch wesentlich geringer als die bei den letzteren. Hierdurch wird auch die Darstellung hochreiner Farbstoffe wesentlich aufwendiger, so daß für Fluoreszenzanwendungen die Farbstoffe 1 und 2 zu bevorzugen sind, die in sehr guten Ausbeuten in reinster Form synthetisch zugänglich sind.Dyes 3 and 4 show behavior similar to that Dyes 1 and 2. However, the yields in the synthesis are much less than that of the latter. This will also the representation of highly pure dyes much more complex, so that dyes 1 and 2 are preferred for fluorescence applications are synthetic in very good yields in the purest form are accessible.
Da die UV/VIS-Spektren der Perylenfarbstoffe 5 nur wenig von den Resten R abhängen, wurden Mischungen von Farbstoffen untersucht. Zum Erstaunen wurde gefunden, daß die Löslichkeit eines Farbstoffs nur wenig davon abhängt, ob ein zweiter Farbstoff zugesetzt wird. Die Löslichkeit in bezug auf den Perylenchromophor verhält sich damit annähernd additiv. Es wurde damit ein komplexes Gemisch aliphatischer und aromatischer primärer Amine zu dem entsprechenden Gemisch an Perylenfarbstoffen umgesetzt, das sich nun wie ein sehr leichtlöslicher Perylenfarbstoff verhält und entsprechend für praktische Anwendungen eingesetzt werden kann. Brauchbare Gemische an primären aliphatischen Aminen sind z. B. durch eine radikalische Chlorierung von langkettigen Kohlenwasserstoffen und anschließende Umsetzung mit Ammoniak darstellbar.Since the UV / VIS spectra of the perylene dyes 5 only a little of the Depending on residues R, mixtures of dyes were examined. Surprisingly, it was found that the solubility of a dye little depends on whether a second dye is added. The solubility with respect to the perylene chromophore behaves almost additive. It became a complex mixture aliphatic and aromatic primary amines to the corresponding Mixture of perylene dyes implemented, which is now like a very easily soluble perylene dye behaves and accordingly can be used for practical applications. Usable mixtures primary aliphatic amines are e.g. B. by a radical chlorination of long chain hydrocarbons and subsequent implementation with ammonia.
Die Perylenfarbstoffe zeigen drei starke Absorptionsbanden bei 526.5, 490 und 459 nm. Für Blitzlampen-Anregung in Farbstoff- Lasern wäre ein noch breiteres Absorptionsspektrum bei gleichem Fluoreszenzspektrum wünschenswert. Es wurden daher die Reste 5a bis 5h mit dem Perylenchromophor verknüpft und so erstmals bifluorophore Perylenfarbstoffe erhalten. Die tert-Butylgruppen waren erforderlich, um eine genügende Löslichkeit zu erreichen. Zum Erstaunen wurde gefunden, daß sich 1. die Absorptionsspektren der Teilchromophore additiv verhalten und damit die Farbstärke des Farbstoffs erhöht wird und 2. vollständige Energieübertragung vom Rest R auf den Perylenchromophor erfolgt, so daß das ursprüngliche Fluoreszenzspektrum der Perylenfarbstoffe erhalten bleibt, gleichgültig, bei welcher Wellenlänge angeregt wird.The perylene dyes show three strong absorption bands 526.5, 490 and 459 nm. For flash lamp excitation in dye Lasers would be an even wider absorption spectrum with the same Fluorescence spectrum desirable. The residues 5a linked to the perylene chromophore up to 5 hours and thus bifluorophores for the first time Obtain perylene dyes. The tert-butyl groups were required to achieve sufficient solubility. To the It was astonishing that 1. the absorption spectra of the Partial chromophores behave additively and thus the color strength of the Dye is increased and 2. complete energy transfer from the rest R to the perylene chromophore, so that the original Fluorescence spectrum of the perylene dyes is retained, no matter what wavelength is excited.
Die beschriebenen Farbstoffe lassen sich als Tracer in hoch empfindlichen analytischen Nachweisverfahren auf der Basis der Fluoreszenz einsetzen (siehe auch C. Aubert, J. Fünfschilling, I. Zschokke-Gränacher und H. Langhals, Z. Analyt. Chem. 320, 361 (1985)). Für Tracer-Anwendungen ist es außerdem wichtig, die Pery lenfarbstoffe konvalent mit einem Substrat verknüpfen zu können. Hierfür ist der Farbstoff 6 ein wichtiges Zwischenprodukt, der einmal aus Farbstoff 8 durch eine partielle alkalische Hydrolyse oder aus Farbstoff 9 durch eine Kondensation mit 2,5-Di-tert- butylanilin erhalten werden kann. Dieses Zwischenprodukt läßt sich jeweils mit einer primären Aminogruppe eines Substrats kondensieren, und so wird ein kovalent gebundener Perylenfarbstoff erhalten. Als weitere Beispiele sind Farbstoffe mit R = 2-Hydroxy ethyl und 2-(Methacroyl)ethyl dargestellt worden, die sich über eine Veresterungsreaktion oder eine Polymerisationsreaktion verknüpfen lassen. The dyes described can be used as tracers in high sensitive analytical detection methods based on fluorescence (see also C. Aubert, J. Fünfschilling, I. Zschokke-Gränacher and H. Langhals, Z. Analyt. Chem. 320, 361 (1985)). For tracer applications it is also important to use the Pery to be able to link oil dyes with a substrate. The dye 6 is an important intermediate product for this purpose once from dye 8 by partial alkaline hydrolysis or from dye 9 by condensation with 2,5-di-tert- butylaniline can be obtained. This intermediate can be each condense with a primary amino group of a substrate, and thus a covalently bound perylene dye is obtained. Dyes with R = 2-hydroxy are further examples ethyl and 2- (methacroyl) ethyl have been shown, which are about an esterification reaction or a polymerization reaction link.
Die Darstellung hochreiner Fluoreszenzfarbstoffe ist für alle Fluoreszenzanwendungen wichtig, denn es müssen u. a. Fluoreszenz quencher entfernt werden. Die Reinigung der Farbstoffe stellte aber in der Vergangenheit ein erhebliches präparatives Problem dar, insbesondere bei der Darstellung größerer Mengen. Durch die erfolgreiche Anwendung der Methode der extraktiven Umkristallisation (siehe auch H. Langhals, Chem. Ber. 118, 4641 (1985)) konnte dieses Problem beseitigt werden, so daß die Farbstoffe nun nicht mehr in begrenzter Menge in hochreiner Form zur Verfügung stehen.The representation of high-purity fluorescent dyes is for everyone Fluorescence applications important, because it must a. Fluorescence quencher can be removed. The cleaning of the dyes posed but a significant preparative problem in the past especially when displaying larger quantities. Through the successful application of the extractive recrystallization method (see also H. Langhals, Chem. Ber. 118, 4641 (1985)) this problem can be eliminated so that the dyes are not now more are available in high purity in limited quantities.
Die Synthese der Perylenfarbstoffe kann in an und für sich bekannter Weise durch eine Kondensation des Perylen-3,4 : 9,10-tetracarbonsäure bisanhydrids mit dem entsprechenden primären Amin erfolgen, wobei als Medium Chinolin und Zinkacetat Verwendung finden. Verwendet man statt des Chinolins geschmolzenes Imidazol, so kann die Umsetzung bei niedrigeren Temperaturen vorgenommen werden. Statt der sonst üblichen 200 bis 220°C wird i. allgem. eine ausreichend hohe Reaktionsgeschwindigkeit bereits bei Temperaturen von 140°C erreicht. Dieses Medium hat außerdem den Vorteil, höhere Ausbeuten an Perylentetracarbonsäurebisimiden zu liefern als Chinolin. Außerdem müssen die zu kondensierenden Amine nicht mehr wie beim Chinolin im Überschuß eingesetzt werden, sondern es reichen bereits stöchiometrische Mengen aus, um eine quantitative Umsetzung zu erzielen. Besonders bewährt hat sich das Imidazol bei sterisch ge hinderten Aminen z. B. bei der Darstellung des Farbstoffs 5e.The synthesis of the perylene dyes can be known per se Way by condensation of the perylene-3,4: 9,10-tetracarboxylic acid bisanhydride with the corresponding primary amine, using quinoline and zinc acetate as the medium. If molten imidazole is used instead of quinoline, it can the reaction can be carried out at lower temperatures. Instead of the usual 200 to 220 ° C i. general one sufficient high reaction speed even at temperatures of 140 ° C reached. This medium also has the advantage of higher yields to deliver perylenetetracarboxylic bisimides as quinoline. In addition, the amines to be condensed no longer have to be the same as for Quinoline can be used in excess, but it is enough stoichiometric amounts for quantitative conversion achieve. The imidazole has proven particularly useful for steric ge hindered amines e.g. B. in the representation of the dye 5e.
Die vorgestellten Farbstoffe weisen extreme Eigenschaften auf. Es ergeben sich dadurch breite Anwendungsmöglichkeiten, und es lassen sich mit den Farbstoffen in vielen Fällen technische Verbesserungen erreichen. Im einzelnen sind folgende Anwendungen zu nennen:The dyes presented have extreme properties. This results in wide application possibilities, and it can be technical with the dyes in many cases Achieve improvements. The following are the individual applications to call:
- - Einsatz in Farbstoff-Lasern. Hier kommen die großen Photo stabilitäten, die hohen Fluoreszenzquantenausbeuten und die guten Löslichkeiten zum Tragen. Der Betrieb der Farbstoff-Laser kann in bekannter Weise erfolgen.- Use in dye lasers. Here are the big photos stabilities, the high fluorescence quantum yields and the good ones Solubilities to bear. Operation of the dye laser can be done in done in a known manner.
- - Einsatz in hochempfindlichen analytischen Nachweisverfahren (siehe C. Aubert, F. Fünfschilling, I. Zschokke-Gränacher und H. Langhals, Z. Analyt. Chem. 320, 361 (1985)) unter Verwendung der Fluoreszenz durch Laser-Anregung. Perylenfarbstoffe sind nach diesem Verfahren bei einer Verdünnung von 10-13 mol/l und einer absoluten Menge von 10-18 mol auf 5% genau quantitativ bestimmt worden. Der Einsatz der hier beschriebenen Farbstoffe ist auch für dieses Verfahren sehr vorteilhaft.- Use in highly sensitive analytical detection methods (see C. Aubert, F. Fünfschilling, I. Zschokke-Gränacher and H. Langhals, Z. Analyt. Chem. 320, 361 (1985)) using fluorescence by laser excitation. Perylene dyes were precisely quantified to 5% using this method at a dilution of 10 -13 mol / l and an absolute amount of 10 -18 mol. The use of the dyes described here is also very advantageous for this process.
- - Verwendung der Farbstoffe ganz allgemein als Tracer. Dies kann zum einen direkt durch einen Zusatz der Farbstoffe geschehen, die dann über das Fluoreszenzspektrum identifiziert und quantitativ bestimmt werden können. Es sind hier u. a. Anwendungen in der Geologie, in der Technik (z. B. bei der Produktionsüberwachung), in der Biochemie und Medizin (Ersatz von Radionukliden), in der analytischen Chemie und schließlich ganz allgemein in der Natur wissenschaft zu nennen. Vorteilhaft ist hier die große chemische Beständigkeit der Farbstoffe - sie überstehen z. B. konz. Schwefel säure bei 100°C oder die Bedingungen der radikalischen Polymerisation - und die große Lichtechtheit, die ein Ausbleichen auch in verdünnten Lösungen nicht befürchten lassen.- Use of the dyes in general as a tracer. This can on the one hand, directly by adding the dyes that then identified via the fluorescence spectrum and quantitative can be determined. There are u. a. Applications in geology, in technology (e.g. in production monitoring), in biochemistry and medicine (replacement of radionuclides), in which analytical chemistry and finally more generally in nature to call science. The large chemical is advantageous here Resistance of the dyes - they survive e.g. B. conc. Sulfur acid at 100 ° C or the conditions of radical polymerization - and the great lightfastness that also fades in do not fear diluted solutions.
- - Verwendung der Farbstoffe in Szintillationszählern zum Nachweis und zur quantitativen Bestimmung energiereicher Strahlung (z. B. radioaktive Strahlung). Hier kommt neben den großen Fluoreszenz quantenausbeuten die große Beständigkeit der Farbstoffe zum Tragen. Die Perylenfarbstoffe haben bei einer energiedispersiven Analyse einen Elektronenstrom von 50 µA bei 25 kV Beschleunigungsspannung auf 10 000 Ų während drei Minuten ohne irgendein Anzeichen von Zersetzung überstanden. Andere organische Materialien, wie z. B. Cellulose, werden unter diesen Bedingungen rasch zerstört. Es ist daher eine besondere Langzeitstabilität solcher Szintillatorsysteme zu erwarten.- Use of the dyes in scintillation counters for detection and for the quantitative determination of high-energy radiation (e.g. radioactive radiation). Here comes in addition to the great fluorescence quantum yields the great resistance of the dyes to bear. The perylene dyes have an energy dispersive analysis an electron current of 50 µA at 25 kV acceleration voltage to 10,000 Ų for three minutes without any sign of Survived decomposition. Other organic materials such as B. Cellulose, are quickly destroyed under these conditions. It is therefore a special long-term stability of such scintillator systems expected.
- - Aufgrund der besonderen Eigenschaften der Farbstoffe lassen sie sich allgemein in Lichtsammelsystemen verwenden. Hier ist zum einen der Fluoreszenz-Solarkollektor zu nennen (siehe z. B. H. Langhals, Nachr. Chem. Tech. Lab. 28, 716 (1980)), zum anderen das fluoreszenzaktivierte Display (W. Greubel und G. Baur, Elektronik 26, 6 (1977)).- Due to the special properties of the dyes, they leave are generally used in light collection systems. Here is one to name the fluorescence solar collector (see e.g. H. Langhals, Nachr. Chem. Tech. Lab. 28, 716 (1980)), on the other the fluorescence activated display (W. Greubel and G. Baur, Electronics 26, 6 (1977)).
- - Verwendung der Farbstoffe in Flüssigkristallen: farbige Flüssig kristallanzeigen.- Use of dyes in liquid crystals: colored liquid crystal displays.
- - Die Farbstoffe lassen sich ebenfalls vorteilhaft in Kaltlicht quellen einsetzen, in denen infrarot-freie Fluoreszenzstrahlung verwendet wird. Diese Lichtstrahlung kann dann zur Aushärtung von Kunststoffen verwendet werden, bei der sich die Probe nicht auf heizen darf. Weitere Anwendungen solcher Kaltlichtquellen liegen in der Medizin und Zahnmedizin.- The dyes can also be advantageously used in cold light Use sources in which infrared-free fluorescence radiation is used. This light radiation can then be used to cure Plastics are used where the sample is not on allowed to heat. Further applications of such cold light sources lie in medicine and dentistry.
- - Die Farbstoffe lassen sich bei der Materialprüfung bei der Herstellung von Halbleiterschaltungen verwenden, um z. B. in bekannter Weise Risse oder dgl. zu erkennen. Eine ähnliche Anwendung liegt in der Untersuchung von Mikrostrukturen von integrierten Halbleiter bauelementen.- The dyes can be used in the material testing during manufacture of semiconductor circuits to z. B. in known Way to detect cracks or the like. A similar application lies in the study of microstructures of integrated semiconductors components.
- - Einsatz der Farbstoffe als Photoleiter. Hiermit im Zusammenhang steht die Verwendung in Trockenkopierern, Laserdruckern und anderen Aufzeichnungssystemen (Xerox-Verfahren), sowie bei Videokameras, bei denen die Bilderzeugung oder Aufzeichnung auf der Photoleitung des verwendeten Materials beruht.- Use of the dyes as a photoconductor. In connection with this stands for use in dry copiers, laser printers and others Recording systems (Xerox process) and video cameras, where the imaging or recording on the photoconductor of the material used.
- - Verwendung der Farbstoffe bei fotografischen Verfahren z. B. als Sensibilisatoren oder zur Bildentwicklung.- Use of the dyes in photographic processes such. B. as sensitizers or for image development.
- - Verwendung als Fluorophor in Beleuchtungs- und Anzeigeelementen, z. B. in Leuchtstoffröhren, in Braunschen Röhren und Fluoreszenz anzeigen.- Use as a fluorophore in lighting and display elements, e.g. B. in fluorescent tubes, in Braun tubes and fluorescence Show.
- - Verwendung als Halbleiter in integrierten Schaltungen, Anwendung der Epitaxie.- Use as a semiconductor in integrated circuits, application of epitaxy.
- - Verwendung der Farbstoffe in passiven Anzeigeelementen für vielerlei Anzeige-, Hinweis- und Markierungszwecke, z. B. passive Anzeigeelemente, Hinweis- und Verkehrszeichen, wie Ampeln.- Use of the dyes in passive display elements for various display, information and marking purposes, e.g. B. passive Display elements, information and traffic signs, such as traffic lights.
Die Farbstoffe werden vorzugsweise in einer Konzentration von 0,005 bis 0,5%, besonders bevorzugt in einer Konzentration von 0,01 bis 0,1% bezogen auf das Gewicht eines Trägers eingesetzt. Die Farbstoffe werden in einer Flüssigkeit oder in einem Festkörper gelöst, wobei, je nach Einsatzgebiet, verschiedene geometrische Formen in Frage kommen. Geeignete feste Medien, wie sie z. B. zum Sammeln von Licht in Verbindung mit Solarzellen und in passiven Anzeigeelementen eingesetzt werden, sind z. B. lichtdurchlässige optisch verwendbare Kunststoffe, wie Homo- und Copolymerisate der Acrylsäure und ihren Derivaten und der Methacrylsäure und ihren Derivaten oder Polycarbonate. Des weiteren können die Fluoreszenzfarbstoffe auch in einer Flüssigkeit angewendet werden, z. B. in einem Alkohol, Keton, Halogenkohlenwasserstoff, Ether, Ester, aromatischen oder aliphatischem Kohlenwasserstoff, Nitril, Amin, Nitroverbindungen oder in Gemischen derer. Bevorzugte Lösungs mittel sind beispielsweise Ethanol, Propanol, Methylethylketon, Methylisobutylketon, Aceton, Cyclohexanon, Essigsäureethylester, Essigsäurebutylester, Toluol, Xylol, Chloroform, Perchlorethylen, Glykolmonomethylether, 1,1,1-Trichlorethan etc.The dyes are preferably in a concentration of 0.005 to 0.5%, particularly preferably in a concentration of 0.01 to 0.1% based on the weight of a carrier used. The dyes are in a liquid or in a solid solved, depending on the application, different geometric Forms come into question. Suitable solid media, such as. B. for collecting light in connection with solar cells and in passive Display elements are used, for. B. translucent optically usable plastics, such as homopolymers and copolymers acrylic acid and its derivatives and methacrylic acid and their derivatives or polycarbonates. Furthermore, the Fluorescent dyes can also be applied in a liquid e.g. B. in an alcohol, ketone, halocarbon, ether, Esters, aromatic or aliphatic hydrocarbons, nitriles, Amine, nitro compounds or in mixtures thereof. Preferred solution middle are for example ethanol, propanol, methyl ethyl ketone, Methyl isobutyl ketone, acetone, cyclohexanone, ethyl acetate, Butyl acetate, toluene, xylene, chloroform, perchlorethylene, Glycol monomethyl ether, 1,1,1-trichloroethane etc.
Perylenfarbstoffe können nach folgender allgemeinen Vorschrift dargestellt werden:Perylene dyes can according to the following general rule being represented:
1,0 g (2,5 mmol) Perylen-3,4 : 9,10-tetracarbonsäurebisanhydrid werden mit 10 mmol des betreffenden Amins und 350 mg Zinkacetat vermengt. Nach Zugabe von 5 ml frisch destilliertem Chinolin wird die Mischung 4 h unter N₂-Schutzatmosphäre auf 220°C unter Rückfluß erhitzt. Nach dem Erkalten wird mit 5 ml Wasser und 80 ml Ethanol versetzt, und dann mindestens 4 h stehengelassen. Der aus gefallene Feststoff wird über eine D4-Glasfritte abgesaugt und mit Ethanol gewaschen. Nach dem Trocknen wird mit Toluol extraktiv (H. Langhals, Chem. Ber. 118, 4641 (1985)) umkristallisiert.1.0 g (2.5 mmol) perylene-3,4: 9,10-tetracarboxylic acid bisanhydride with 10 mmol of the relevant amine and 350 mg of zinc acetate blended. After adding 5 ml of freshly distilled quinoline the mixture for 4 h under N₂ protective atmosphere at 220 ° C under reflux heated. After cooling with 5 ml of water and 80 ml Ethanol was added and then left to stand for at least 4 h. The one out fallen solid is suctioned off via a D4 glass frit and washed with ethanol. After drying it becomes extractive with toluene (H. Langhals, Chem. Ber. 118, 4641 (1985)) recrystallized.
Ausbeuten und Elementaranalysen s. Tab. 1.Yields and elementary analyzes s. Tab. 1.
IR(KBr):1709(s), 1672(s) (CONRCO) cm-1 UV/VIS(CHCl₃):λ max (ε) = 526.5 (96300), 490 (58200), 459 (21300), 432 nm (6200)IR (KBr): 1709 (s), 1672 (s) (CONRCO) cm -1 UV / VIS (CHCl₃): λ max (ε) = 526.5 (96300), 490 (58200), 459 (21300), 432 nm (6200)
1,0 g (2,5 mmol) Perylen-3,4 : 9,10-tetracarbonsäurebisanhydrid werden mit 5 mmol des betreffenden Amins und 350 mg Zinkacetat sowie 5 g Imidazol unter N₂-Schutzatmosphäre auf 180°C 4 h erhitzt und dann wie bei Methode A beschrieben aufgearbeitet. Die Reaktions temperatur kann bei Methode B in weiten Grenzen verändert werden. 1.0 g (2.5 mmol) perylene-3,4: 9,10-tetracarboxylic acid bisanhydride with 5 mmol of the relevant amine and 350 mg of zinc acetate and 5 g of imidazole heated to 180 ° C for 4 h under an N₂ protective atmosphere and then worked up as described in Method A. The reaction With method B, temperature can be changed within wide limits will.
Claims (33)
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Application Number | Priority Date | Filing Date | Title |
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DE19873713459 DE3713459A1 (en) | 1987-02-05 | 1987-02-05 | Lightfast, readily soluble diketopyrrolopyrrole fluorescent dyes |
DE3703495A DE3703495A1 (en) | 1987-02-05 | 1987-02-05 | New perylene carboximide derivs. - useful as fluorescent dyes |
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DE19873713459 DE3713459A1 (en) | 1987-02-05 | 1987-02-05 | Lightfast, readily soluble diketopyrrolopyrrole fluorescent dyes |
DE3703495A DE3703495A1 (en) | 1987-02-05 | 1987-02-05 | New perylene carboximide derivs. - useful as fluorescent dyes |
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DE3703495A1 true DE3703495A1 (en) | 1988-08-18 |
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DE3703495A Withdrawn DE3703495A1 (en) | 1987-02-05 | 1987-02-05 | New perylene carboximide derivs. - useful as fluorescent dyes |
DE19873713459 Withdrawn DE3713459A1 (en) | 1987-02-05 | 1987-02-05 | Lightfast, readily soluble diketopyrrolopyrrole fluorescent dyes |
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DE19873713459 Withdrawn DE3713459A1 (en) | 1987-02-05 | 1987-02-05 | Lightfast, readily soluble diketopyrrolopyrrole fluorescent dyes |
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- 1987-02-05 DE DE3703495A patent/DE3703495A1/en not_active Withdrawn
- 1987-02-05 DE DE19873713459 patent/DE3713459A1/en not_active Withdrawn
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