DE60127420T2 - Design und synthese von nlo-materialien für electro-optische anwendungen, die von thiophen abgeleitet sind - Google Patents
Design und synthese von nlo-materialien für electro-optische anwendungen, die von thiophen abgeleitet sind Download PDFInfo
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- DE60127420T2 DE60127420T2 DE60127420T DE60127420T DE60127420T2 DE 60127420 T2 DE60127420 T2 DE 60127420T2 DE 60127420 T DE60127420 T DE 60127420T DE 60127420 T DE60127420 T DE 60127420T DE 60127420 T2 DE60127420 T2 DE 60127420T2
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- Prior art keywords
- chromophore
- alkyl
- aryl
- heteroalkyl
- independently
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- 239000000463 material Substances 0.000 title claims abstract description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 23
- 230000015572 biosynthetic process Effects 0.000 title description 8
- 238000003786 synthesis reaction Methods 0.000 title description 7
- 238000013461 design Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 74
- 230000003287 optical effect Effects 0.000 claims abstract description 60
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 238000004891 communication Methods 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims description 168
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 145
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 238000005859 coupling reaction Methods 0.000 claims description 41
- 230000008878 coupling Effects 0.000 claims description 39
- 238000010168 coupling process Methods 0.000 claims description 39
- 239000011159 matrix material Substances 0.000 claims description 30
- 230000021615 conjugation Effects 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 230000005684 electric field Effects 0.000 claims description 14
- 229930192474 thiophene Natural products 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical group FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 230000006855 networking Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 230000002277 temperature effect Effects 0.000 claims 1
- 239000000370 acceptor Substances 0.000 abstract description 76
- 230000008569 process Effects 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 57
- 125000004429 atom Chemical group 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- 125000005842 heteroatom Chemical group 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YFCHAINVYLQVBG-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethanol Chemical compound O1C(CO)COC2=CSC=C21 YFCHAINVYLQVBG-UHFFFAOYSA-N 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000412 dendrimer Substances 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 0 CCC(C(C)(C)*C1=C(C#N)C#N)=C1C#N Chemical compound CCC(C(C)(C)*C1=C(C#N)C#N)=C1C#N 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
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- 238000006170 formylation reaction Methods 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- 125000004122 cyclic group Chemical group 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
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- -1 methyl-substituted phenols Chemical class 0.000 description 10
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- 239000000377 silicon dioxide Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
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- 230000007774 longterm Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- 238000006880 cross-coupling reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
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- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000013307 optical fiber Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- 239000011593 sulfur Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910052714 tellurium Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 238000003682 fluorination reaction Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
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- 238000006317 isomerization reaction Methods 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
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- 239000002808 molecular sieve Substances 0.000 description 1
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- COCAUCFPFHUGAA-MGNBDDOMSA-N n-[3-[(1s,7s)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=C(F)C([C@@]23N=C(SCC[C@@H]2C3)N)=CC=1NC(=O)C1=CC=C(Cl)C=N1 COCAUCFPFHUGAA-MGNBDDOMSA-N 0.000 description 1
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- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- VGLZLQGIJHAREE-UHFFFAOYSA-N tert-butyl-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethoxy)-dimethylsilane Chemical compound O1C(CO[Si](C)(C)C(C)(C)C)COC2=CSC=C21 VGLZLQGIJHAREE-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Modulation, Optical Deflection, Nonlinear Optics, Optical Demodulation, Optical Logic Elements (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Glass Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22626700P | 2000-08-17 | 2000-08-17 | |
| US226267P | 2000-08-17 | ||
| PCT/US2001/025779 WO2002014305A2 (en) | 2000-08-17 | 2001-08-17 | Design and synthesis of advanced nlo materials for electro-optic applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60127420D1 DE60127420D1 (de) | 2007-05-03 |
| DE60127420T2 true DE60127420T2 (de) | 2007-11-29 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60127420T Expired - Fee Related DE60127420T2 (de) | 2000-08-17 | 2001-08-17 | Design und synthese von nlo-materialien für electro-optische anwendungen, die von thiophen abgeleitet sind |
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| Country | Link |
|---|---|
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| EP (1) | EP1313729B1 (enExample) |
| JP (2) | JP5153047B2 (enExample) |
| CN (1) | CN1466583A (enExample) |
| AT (1) | ATE357444T1 (enExample) |
| AU (1) | AU2001286527A1 (enExample) |
| CA (1) | CA2419820A1 (enExample) |
| DE (1) | DE60127420T2 (enExample) |
| WO (1) | WO2002014305A2 (enExample) |
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| DE10002424A1 (de) * | 2000-01-20 | 2001-07-26 | Siemens Ag | Di(het)arylaminothiophen-Derivate |
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| US7019453B2 (en) * | 2000-08-17 | 2006-03-28 | Lumera Corporation | Polymers having pendant nonlinear optical chromophores and electro-optic devices therefrom |
| US7109355B2 (en) | 2000-08-17 | 2006-09-19 | Lumera Corporation | Fluorinated π-bridge second order nonlinear optical chromophores and electro-optic devices therefrom |
| WO2002014305A2 (en) * | 2000-08-17 | 2002-02-21 | Lumera Corporation | Design and synthesis of advanced nlo materials for electro-optic applications |
| JP4984343B2 (ja) * | 2000-09-29 | 2012-07-25 | 株式会社日立製作所 | 有機電界発光素子及びそれを用いた光電子素子 |
| ATE409714T1 (de) * | 2001-07-25 | 2008-10-15 | Merck Patent Gmbh | Mono-, oligo and poly-3-(1,1- difluoroalkyl)thiophene und ihre verwendung als ladungstransportmaterial |
| US7601849B1 (en) * | 2001-08-02 | 2009-10-13 | University Of Washington | Nonlinear optical compounds and related macrostructures |
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-
2001
- 2001-08-17 WO PCT/US2001/025779 patent/WO2002014305A2/en not_active Ceased
- 2001-08-17 AU AU2001286527A patent/AU2001286527A1/en not_active Abandoned
- 2001-08-17 US US09/932,831 patent/US6716995B2/en not_active Expired - Lifetime
- 2001-08-17 AT AT01965981T patent/ATE357444T1/de not_active IP Right Cessation
- 2001-08-17 JP JP2002519445A patent/JP5153047B2/ja not_active Expired - Fee Related
- 2001-08-17 DE DE60127420T patent/DE60127420T2/de not_active Expired - Fee Related
- 2001-08-17 CA CA002419820A patent/CA2419820A1/en not_active Abandoned
- 2001-08-17 CN CNA018162584A patent/CN1466583A/zh active Pending
- 2001-08-17 EP EP01965981A patent/EP1313729B1/en not_active Expired - Lifetime
-
2003
- 2003-03-13 US US10/387,715 patent/US6822384B2/en not_active Expired - Fee Related
- 2003-05-16 US US10/439,621 patent/US6864375B2/en not_active Expired - Lifetime
-
2004
- 2004-02-10 US US10/775,836 patent/US7206111B2/en not_active Expired - Fee Related
-
2007
- 2007-03-21 US US11/689,378 patent/US20070232811A1/en not_active Abandoned
-
2008
- 2008-04-25 US US12/110,256 patent/US7888387B2/en not_active Expired - Lifetime
-
2012
- 2012-03-26 JP JP2012069652A patent/JP2012123425A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20090231678A1 (en) | 2009-09-17 |
| WO2002014305A2 (en) | 2002-02-21 |
| ATE357444T1 (de) | 2007-04-15 |
| US6822384B2 (en) | 2004-11-23 |
| AU2001286527A1 (en) | 2002-02-25 |
| DE60127420D1 (de) | 2007-05-03 |
| US20040192940A1 (en) | 2004-09-30 |
| US20030205701A1 (en) | 2003-11-06 |
| US7206111B2 (en) | 2007-04-17 |
| CA2419820A1 (en) | 2002-02-21 |
| JP2012123425A (ja) | 2012-06-28 |
| US20020160282A1 (en) | 2002-10-31 |
| US7888387B2 (en) | 2011-02-15 |
| US20070232811A1 (en) | 2007-10-04 |
| CN1466583A (zh) | 2004-01-07 |
| US6864375B2 (en) | 2005-03-08 |
| US20030201713A1 (en) | 2003-10-30 |
| EP1313729B1 (en) | 2007-03-21 |
| WO2002014305A3 (en) | 2002-10-24 |
| US6716995B2 (en) | 2004-04-06 |
| JP2004506630A (ja) | 2004-03-04 |
| JP5153047B2 (ja) | 2013-02-27 |
| EP1313729A2 (en) | 2003-05-28 |
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