CA2419820A1 - Design and synthesis of advanced nlo materials for electro-optic applications - Google Patents
Design and synthesis of advanced nlo materials for electro-optic applications Download PDFInfo
- Publication number
- CA2419820A1 CA2419820A1 CA002419820A CA2419820A CA2419820A1 CA 2419820 A1 CA2419820 A1 CA 2419820A1 CA 002419820 A CA002419820 A CA 002419820A CA 2419820 A CA2419820 A CA 2419820A CA 2419820 A1 CA2419820 A1 CA 2419820A1
- Authority
- CA
- Canada
- Prior art keywords
- chromophore
- composition
- waveguide
- alkyl
- heteroalkyl
- 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.)
- Abandoned
Links
- 239000000463 material Substances 0.000 title abstract description 34
- 230000015572 biosynthetic process Effects 0.000 title description 9
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 238000013461 design Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 89
- 230000003287 optical effect Effects 0.000 claims abstract description 77
- 229920000642 polymer Polymers 0.000 claims abstract description 53
- 230000008569 process Effects 0.000 claims abstract description 30
- 238000004891 communication Methods 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 164
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 155
- 239000000203 mixture Substances 0.000 claims description 98
- 229910052760 oxygen Inorganic materials 0.000 claims description 76
- 229910052717 sulfur Inorganic materials 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 73
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 238000005859 coupling reaction Methods 0.000 claims description 45
- 230000008878 coupling Effects 0.000 claims description 43
- 238000010168 coupling process Methods 0.000 claims description 43
- 229910052711 selenium Inorganic materials 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 32
- 230000021615 conjugation Effects 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 22
- 230000005684 electric field Effects 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 12
- 229930192474 thiophene Natural products 0.000 claims description 10
- 230000005540 biological transmission Effects 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 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 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000000370 acceptor Substances 0.000 abstract description 65
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 125000004429 atom Chemical group 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 125000005842 heteroatom Chemical group 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 239000000412 dendrimer Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000022244 formylation Effects 0.000 description 15
- 238000006170 formylation reaction Methods 0.000 description 15
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 229920000736 dendritic polymer Polymers 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 8
- 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- -1 methoxy (-OCH3) Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 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 5
- 239000002253 acid Substances 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000002123 temporal effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000000746 allylic group Chemical group 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 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
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000006880 cross-coupling reaction Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 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
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000013307 optical fiber Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NHDUIVYIFKFPDU-UHFFFAOYSA-N 2-[(2-cyanofuran-3-ylidene)methylidene]propanedinitrile Chemical compound N#CC1OC=CC1=C=C(C#N)C#N NHDUIVYIFKFPDU-UHFFFAOYSA-N 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
- 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 0 CCN(CC)c1ccc(C=Cc2c(*)c(*)c(C=O)[s]2)cc1 Chemical compound CCN(CC)c1ccc(C=Cc2c(*)c(*)c(C=O)[s]2)cc1 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910019213 POCl3 Inorganic materials 0.000 description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical group [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000009881 electrostatic interaction Effects 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 102200001405 rs377584435 Human genes 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 210000004722 stifle Anatomy 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
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- KORGVYWUUNNSHE-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine-3-carbaldehyde Chemical compound C1=C2OCC(OC2=CS1)C=O KORGVYWUUNNSHE-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QCCFUWPEUHXQMH-UHFFFAOYSA-N 3,4-dibromothiophene-2-carbaldehyde Chemical compound BrC1=CSC(C=O)=C1Br QCCFUWPEUHXQMH-UHFFFAOYSA-N 0.000 description 1
- XWEYATZFSPHATJ-UHFFFAOYSA-N 3,4-dibutoxythiophene Chemical compound CCCCOC1=CSC=C1OCCCC XWEYATZFSPHATJ-UHFFFAOYSA-N 0.000 description 1
- HUXPLJJZAGFRCQ-UHFFFAOYSA-N 3-methyl-3-sulfanylbutan-2-one Chemical compound CC(=O)C(C)(C)S HUXPLJJZAGFRCQ-UHFFFAOYSA-N 0.000 description 1
- SOTQZDLVHMSDDO-UHFFFAOYSA-N 4-[2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]ethenyl]-N,N-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C2OCC(C(C)(C)O[SiH2]C(C)(C)C)OC2=CS1 SOTQZDLVHMSDDO-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- GYTLXYBBYKWNSS-UHFFFAOYSA-N CC(C)(C(C)=C1C#N)SC1=C(C#N)C#N Chemical compound CC(C)(C(C)=C1C#N)SC1=C(C#N)C#N GYTLXYBBYKWNSS-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000407626 Dithyrea californica Species 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000005700 Stille cross coupling reaction Methods 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000010719 annulation reaction Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- ZEHZNAXXOOYTJM-UHFFFAOYSA-N dicyanoacetylene Chemical class N#CC#CC#N ZEHZNAXXOOYTJM-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 238000010348 incorporation Methods 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
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005442 molecular electronic Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000000382 optic material Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000003825 pressing Methods 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
- 238000009877 rendering 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
- 229910052710 silicon Inorganic materials 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
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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 | |
| US60/226,267 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2419820A1 true CA2419820A1 (en) | 2002-02-21 |
Family
ID=22848219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002419820A Abandoned CA2419820A1 (en) | 2000-08-17 | 2001-08-17 | Design and synthesis of advanced nlo materials for electro-optic applications |
Country Status (9)
| Country | Link |
|---|---|
| US (6) | US6716995B2 (enExample) |
| 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) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10002424A1 (de) * | 2000-01-20 | 2001-07-26 | Siemens Ag | Di(het)arylaminothiophen-Derivate |
| JP2004508430A (ja) | 2000-07-24 | 2004-03-18 | ユニバーシティ オブ ワシントン | 超分極性有機発色団 |
| US6750603B2 (en) * | 2000-08-17 | 2004-06-15 | Lumera Corporation | Second order nonlinear optical chromophores and electro-optic devices therefrom |
| 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 |
| EP1425275B1 (en) * | 2001-09-12 | 2007-11-28 | Pusan National University Industry-University Cooperation Foundation | Novel terthiophene-3-carboxylic acid compound and fabricating method thereof, functionalized conductive terthiophene polymer with the compound as a monomer, and process for dna hybridizatioon detection using the polymer |
| US7001708B1 (en) * | 2001-11-28 | 2006-02-21 | University Of Central Florida Research Foundation, Inc. | Photosensitive polymeric material for worm optical data storage with two-photon fluorescent readout |
| DE10248876B4 (de) * | 2002-10-18 | 2006-07-06 | H.C. Starck Gmbh | Verfahren zur Herstellung linearer organischer Oligomere |
| DE10257539A1 (de) * | 2002-12-10 | 2004-07-01 | H.C. Starck Gmbh | Verfahren zur Herstellung von 2,2'-Di(3,4-ethylendioxythiophen)en |
| US7014796B2 (en) | 2003-01-15 | 2006-03-21 | University Of Washington | Nonlinear optical compounds and methods for their preparation |
| US7291293B2 (en) * | 2003-02-28 | 2007-11-06 | Northwestern University | Vapor deposited electro-optic films self-assembled through hydrogen bonding |
| EP1605733A4 (en) * | 2003-03-14 | 2009-08-05 | Semiconductor Energy Lab | CONJUGATED MOLECULE, ELECTROLUMINESCENT ELEMENT USING THE SAME, AND ELECTRONIC APPARATUS USING THE LIGHT EMITTING ELEMENT |
| JP4453361B2 (ja) * | 2003-12-25 | 2010-04-21 | 富士ゼロックス株式会社 | 非線形光学材料製造用の原料溶液、非線形光学材料、及び非線形光学素子 |
| US7241394B2 (en) * | 2004-01-21 | 2007-07-10 | Lumera Corporation | Process of fabricating polymer sustained microelectrodes |
| WO2005070547A2 (en) * | 2004-01-21 | 2005-08-04 | Lumera Corporation | Polymer sustained microelectrodes, processes for fabricating same, processes for fabricating electro-optic polymer devices incorporating same, and fluorinated sol-gel electro-optic materials |
| US7250712B2 (en) * | 2004-01-21 | 2007-07-31 | Lumera Corporation | Polymer sustained microelectrodes |
| US7425643B1 (en) | 2004-01-26 | 2008-09-16 | University Of Washington | Electron acceptors for nonlinear optical chromophores |
| US20050249248A1 (en) * | 2004-02-10 | 2005-11-10 | He Guang S | Backward stimulated rayleigh-bragg scattering devices based on multi-photon absorbing materials and their applications |
| US7250121B2 (en) * | 2004-05-13 | 2007-07-31 | Nitto Denko Corporation | Non-linear optical device material composition |
| US20050253120A1 (en) * | 2004-05-13 | 2005-11-17 | Michiharu Yamamoto | Non-linear optical device material composition |
| US7344662B2 (en) | 2004-06-24 | 2008-03-18 | Nitto Denko Corporation | Reverse synthetic methods for making organic non-linear optical materials |
| US7528176B2 (en) * | 2004-09-14 | 2009-05-05 | Northwestern University | Carbonyl-functionalized thiophene compounds and related device structures |
| US7317058B2 (en) * | 2004-11-01 | 2008-01-08 | Nitto Denko Corporation | (Meth)acrylate polymer and non-linear optical device material composition |
| US7161726B2 (en) | 2004-11-05 | 2007-01-09 | Lumera Corporation | Linear optical modulators and method of linear optical modulation |
| US7553559B2 (en) | 2005-12-21 | 2009-06-30 | Lg Display Co., Ltd. | Hexatriene derivatives for use as blue emitting materials for organic electroluminescent devices |
| US7723462B2 (en) | 2006-05-03 | 2010-05-25 | Corning Incorporated | Mercaptofunctional high mubeta EO chromophores and high Tg, low optical loss, covalently bonded, high mubeta EO chromophore containing polymers and methods of synthesizing EO materials |
| US20090268999A1 (en) * | 2006-05-16 | 2009-10-29 | Gigoptix, Inc. | Low loss optical polymer and devices made therefrom |
| US20070267606A1 (en) * | 2006-05-16 | 2007-11-22 | Diyun Huang | Low Loss Electro-Optic Polymers Composites |
| US7626185B2 (en) * | 2006-08-11 | 2009-12-01 | Battelle Memorial Institute | Patterning compositions, masks, and methods |
| US20080042127A1 (en) * | 2006-08-17 | 2008-02-21 | Watson Mark D | Transition metal free coupling of highly fluorinated and non-fluorinated pi-electron systems |
| KR100868450B1 (ko) * | 2006-11-20 | 2008-11-11 | 광주과학기술원 | 퍼플루오로싸이클로부탄 기능기를 포함하는 전기변색화합물 |
| US7713428B2 (en) * | 2007-05-24 | 2010-05-11 | Gigoptix, Inc. | Method of fabricating polymer modulators with etch stop clads |
| US20080298736A1 (en) * | 2007-06-04 | 2008-12-04 | Lumera Corporation | Broadband Electro-Optic Polymer Modulators With Integrated Resistors |
| US20080298737A1 (en) * | 2007-06-04 | 2008-12-04 | Lumera Corporation | Integrated Resistor Fabrication Method and Optical Devices Therefrom |
| US7902322B2 (en) * | 2007-11-15 | 2011-03-08 | Diyun Huang | Nonlinear optical chromophores with stabilizing substituent and electro-optic devices |
| US8618241B2 (en) * | 2007-11-15 | 2013-12-31 | Gigoptix, Inc. | Stabilized electro-optic materials and electro-optic devices made therefrom |
| US8934741B2 (en) | 2007-11-16 | 2015-01-13 | Brphotonics Produtos Optoelectronicos LTDA | Integrated circuit with optical data communication |
| US8483524B2 (en) * | 2008-08-14 | 2013-07-09 | Gigoptix, Inc. | Integrated electro-optic device and method of making |
| US8409713B2 (en) | 2007-12-07 | 2013-04-02 | University Of Washington | Crosslinkable polymer host containing a nonlinear optical chromophore guest |
| US8394499B2 (en) * | 2007-12-07 | 2013-03-12 | University Of Washington | Crosslinkable polymer host having pendant nonlinear optical chromophores and containing a nonlinear optical chromophore guest |
| US8153446B2 (en) | 2008-05-23 | 2012-04-10 | Kent State University | Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems |
| WO2009152165A2 (en) | 2008-06-09 | 2009-12-17 | Plextronics, Inc. | Sulfonated polythiophenes comprising fused ring repeat units |
| CN101845040B (zh) * | 2009-03-23 | 2012-05-30 | 中国科学院理化技术研究所 | 树枝状基团修饰的具有D-π-A结构的有机二阶非线性光学发色团及其合成方法和用途 |
| CN101845039B (zh) * | 2009-03-23 | 2012-05-30 | 中国科学院理化技术研究所 | 具有D-π-A结构的二阶非线性光学发色团及其合成方法和用途 |
| US8728934B2 (en) | 2011-06-24 | 2014-05-20 | Tessera, Inc. | Systems and methods for producing flat surfaces in interconnect structures |
| JP2013181108A (ja) * | 2012-03-01 | 2013-09-12 | Kanto Natural Gas Development Co Ltd | 色素増感型光電変換素子用の高活性完全有機色素化合物、およびそれを用いた光電変換素子 |
| JP5826206B2 (ja) | 2012-03-29 | 2015-12-02 | 富士フイルム株式会社 | 非線形光学材料及びそれを用いた非線形光学素子 |
| JP2020535260A (ja) * | 2017-09-27 | 2020-12-03 | アーケマ・インコーポレイテッド | ハロゲン化反応成分から調製される付加及び縮合ポリマー |
| US11661428B1 (en) * | 2017-10-03 | 2023-05-30 | Lightwave Logic, Inc. | Nonlinear optical chromophores, nonlinear optical materials containing the same, and uses thereof in optical devices |
| US10403435B2 (en) | 2017-12-15 | 2019-09-03 | Capacitor Sciences Incorporated | Edder compound and capacitor thereof |
| CN108586441B (zh) * | 2018-05-03 | 2020-12-29 | 上海天马有机发光显示技术有限公司 | 一种化合物、一种有机发光显示装置 |
| US11614670B2 (en) | 2018-09-17 | 2023-03-28 | Lightwave Logic, Inc. | Electro-optic polymer devices having high performance claddings, and methods of preparing the same |
| CA3183470A1 (en) | 2020-06-25 | 2021-12-30 | Cory Pecinovsky | Nonlinear optical chromophores comprising a diamondoid group |
| JP2025501684A (ja) | 2021-12-03 | 2025-01-23 | ライトウェーブ ロジック インコーポレイテッド | 高沸点溶媒を含む非線形光学材料およびその効率的なポーリング方法 |
| CA3239292A1 (en) | 2021-12-10 | 2023-06-15 | Lightwave Logic, Inc. | Nonlinear optical chromophores having tetrahydrocarbazole donor groups, lyotropic compositions containing the same, and methods of poling such compositions |
| US20250011321A1 (en) | 2023-06-29 | 2025-01-09 | Lightwave Logic, Inc. | Nonlinear Optical Chromophores with Indolizine Donor Groups |
| WO2025014694A1 (en) | 2023-07-07 | 2025-01-16 | Lightwave Logic, Inc. | Non-linear optical chromophores with michler's base-type donors |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3420060A (en) * | 1966-04-22 | 1969-01-07 | Mc Donnell Douglas Corp | Pressure induced jet vectoring augmentation apparatus |
| US3516727A (en) * | 1966-10-20 | 1970-06-23 | Technical Operations Inc | Multipass interferometric optical modulator |
| CA1110385A (en) | 1976-06-05 | 1981-10-06 | Wolfgang Steglich | Polymeric activated esters of 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxide |
| JPS6058918B2 (ja) | 1980-01-22 | 1985-12-23 | 宇部興産株式会社 | チオフエン誘導体および農園芸用殺菌剤 |
| US4421761A (en) | 1981-01-27 | 1983-12-20 | Hokko Chemical Industry Co. Ltd. | Thiophene derivatives |
| JPS6165881A (ja) | 1984-09-10 | 1986-04-04 | Tokuyama Soda Co Ltd | Ｎ−置換−クロロアセトアニリド |
| JPH02244059A (ja) | 1989-03-17 | 1990-09-28 | Canon Inc | 電子写真感光体 |
| US5656207A (en) * | 1989-06-24 | 1997-08-12 | Gen Probe Incorporated | Detecting or quantifying multiple analytes using labelling techniques |
| JPH0331850A (ja) | 1989-06-29 | 1991-02-12 | Canon Inc | 電子写真感光体 |
| TW205041B (enExample) | 1989-08-07 | 1993-05-01 | Fujisawa Pharmaceutical Co | |
| US5080991A (en) | 1989-08-21 | 1992-01-14 | Mitsubishi Kasei Corporation | Electrophotographic photoreceptor with a hydrazone |
| JPH03163460A (ja) * | 1989-08-21 | 1991-07-15 | Mitsubishi Kasei Corp | 電子写真用感光体 |
| GB9019347D0 (en) | 1990-09-05 | 1990-10-17 | Ici Plc | Chromophore-containing compounds for opto-electronic applications |
| US5514799A (en) * | 1993-08-02 | 1996-05-07 | Enichem S.P.A. | 1,1-vinyl substituted nonlinear optical materials |
| US5583636A (en) * | 1991-10-23 | 1996-12-10 | Bulow; Jeffrey A. | Interferometric modulator for optical signal processing |
| JP2928829B2 (ja) | 1992-09-30 | 1999-08-03 | カシオ計算機株式会社 | 電子ゲーム装置 |
| US5670090A (en) | 1993-08-05 | 1997-09-23 | California Institute Of Technology | Nonlinear optical materials with reduced aromaticity and bond length alternation |
| DE4335496A1 (de) * | 1993-10-19 | 1995-04-20 | Basf Ag | Diphenylaminverbindungen |
| DE4401911A1 (de) | 1994-01-24 | 1995-08-03 | Basf Ag | Verwendung von Aryl- oder Heteroarylazoanilinen in der nichtlinearen Optik |
| DE4416476A1 (de) * | 1994-05-10 | 1995-11-16 | Basf Ag | Oligothiophene |
| DE19532828A1 (de) | 1994-09-16 | 1996-03-21 | Basf Ag | Methinfarbstoffe auf Basis von Dioxaborinen |
| JPH08108624A (ja) * | 1994-10-07 | 1996-04-30 | Mitsui Toatsu Chem Inc | 光記録媒体 |
| US5679763A (en) | 1995-02-24 | 1997-10-21 | Enichem S.P.A. | Polyquinoline-based nonlinear optical materials |
| US5764842A (en) * | 1995-03-23 | 1998-06-09 | Hitachi, Ltd. | Semiconductor guided-wave optical device and method of fabricating thereof |
| ES2183954T3 (es) | 1995-06-02 | 2003-04-01 | Optilink Ab | Materiales novedosos con funcionalidad fisica. |
| DE19521503A1 (de) * | 1995-06-13 | 1996-12-19 | Basf Ag | Polymerisierbare Azofarbstoffe mit Thiophenstruktur |
| DE19525304A1 (de) * | 1995-07-12 | 1997-01-16 | Basf Ag | Copolymere mit Adamantyl- und Farbstoffseitenketten |
| JP3031850B2 (ja) | 1995-12-15 | 2000-04-10 | 本田技研工業株式会社 | 傘歯車の冷間鍛造成形方法およびその装置 |
| US5834575A (en) | 1996-11-13 | 1998-11-10 | Hitachi Chemical Company, Ltd. | Compounds and polymers, resin compositions, nonlinear optical element and nonlinear optical devices, and production process therefor |
| US6090332A (en) * | 1997-05-16 | 2000-07-18 | California Institute Of Technology | Process of changing the refractive index of a composite containing a polymer and a compound having large dipole moment and polarizability and applications thereof |
| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| AU8991698A (en) * | 1997-09-05 | 1999-03-29 | Cambridge Display Technology Limited | Compounds for electronic devices |
| EP0902043A3 (de) | 1997-09-10 | 1999-08-11 | Basf Aktiengesellschaft | Polyselenophene, Verfahren zu deren Herstellung, und deren Verwendung |
| US5859251A (en) | 1997-09-18 | 1999-01-12 | The United States Of America As Represented By The Secretary Of The Air Force | Symmetrical dyes with large two-photon absorption cross-sections |
| EP0928793B1 (en) | 1998-01-02 | 2002-05-15 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| WO1999057101A1 (en) | 1998-05-05 | 1999-11-11 | F. Hoffmann-La Roche Ag | Pyrazole derivatives as p-38 map kinase inhibitors |
| UA60365C2 (uk) | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| US6051722A (en) | 1998-07-06 | 2000-04-18 | Hitachi Chemical Company, Ltd. | Compounds, polymers, resin compositions and nonlinear optical devices |
| US6067186A (en) * | 1998-07-27 | 2000-05-23 | Pacific Wave Industries, Inc. | Class of high hyperpolarizability organic chromophores and process for synthesizing the same |
| US6361717B1 (en) | 1998-07-27 | 2002-03-26 | Pacific Wave Industries, Inc. | Sterically stabilized second-order nonlinear optical chromophores and devices incorporating the same |
| US6348992B1 (en) | 1998-07-27 | 2002-02-19 | Pacific Wave Industries, Inc. | Sterically stabilized polyene-bridged second-order nonlinear optical chromophores and devices incorporating the same |
| JP2000089268A (ja) * | 1998-09-13 | 2000-03-31 | Toshiro Imai | 非線形光学材料 |
| CA2347741C (en) | 1998-10-22 | 2006-12-12 | F. Hoffmann-La Roche Ag | Thiazole-derivatives |
| GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| GB9823873D0 (en) | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| DE69926542T2 (de) | 1998-12-25 | 2006-04-27 | Teikoku Hormone Mfg. Co., Ltd. | Aminopyrazolderivate |
| JP2000280621A (ja) | 1999-03-30 | 2000-10-10 | Mitsui Chemicals Inc | 光記録媒体 |
| US6197921B1 (en) * | 1999-06-01 | 2001-03-06 | The United States Of America As Represented By The Secretary Of The Air Force | Polymers of 1-(bithien-2-yl)-4-aminobenzene |
| US6130339A (en) | 1999-06-01 | 2000-10-10 | The United States Of America As Represented By The Secretary Of The Air Force | Electro-active monomers comprised of aniline-thiophene units |
| JP2001085713A (ja) | 1999-09-14 | 2001-03-30 | Fuji Photo Film Co Ltd | 光電変換素子および太陽電池 |
| JP3959943B2 (ja) | 1999-09-29 | 2007-08-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
| JP2001209018A (ja) * | 2000-01-26 | 2001-08-03 | Nec Corp | モニタ付き光変調器 |
| KR20070118164A (ko) | 2000-06-15 | 2007-12-13 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 다광자 감광 시스템 |
| US6514434B1 (en) | 2000-06-16 | 2003-02-04 | Corning Incorporated | Electro-optic chromophore bridge compounds and donor-bridge compounds for polymeric thin film waveguides |
| US6584266B1 (en) | 2000-06-16 | 2003-06-24 | Corning Incorporated | Chromophores for polymeric thin films and optical waveguides and devices comprising the same |
| JP2004508430A (ja) * | 2000-07-24 | 2004-03-18 | ユニバーシティ オブ ワシントン | 超分極性有機発色団 |
| 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 |
| US6750603B2 (en) * | 2000-08-17 | 2004-06-15 | Lumera Corporation | Second order nonlinear optical chromophores and electro-optic devices therefrom |
| US7019453B2 (en) * | 2000-08-17 | 2006-03-28 | Lumera Corporation | Polymers having pendant nonlinear optical chromophores and electro-optic devices therefrom |
| US7014796B2 (en) * | 2003-01-15 | 2006-03-21 | University Of Washington | Nonlinear optical compounds and methods for their preparation |
-
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 |
| 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 |
| DE60127420T2 (de) | 2007-11-29 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1313729B1 (en) | Design and synthesis of thiophene derived nlo materials for electro-optic applications | |
| He et al. | Synthesis of chromophores with extremely high electro-optic activity. 1. Thiophene-bridge-based chromophores | |
| CN115996920B (zh) | 包含类金刚烷基团的非线性光学发色团 | |
| US6995884B2 (en) | Fluorinated crosslinked electro-optic materials and electro-optic devices therefrom | |
| JP2004508430A (ja) | 超分極性有機発色団 | |
| Piao et al. | Nonlinear optical side‐chain polymers post‐functionalized with high‐β chromophores exhibiting large electro‐optic property | |
| US7014796B2 (en) | Nonlinear optical compounds and methods for their preparation | |
| US7307173B1 (en) | Pyrroline chromophores | |
| US9023248B2 (en) | Diels-Alder crosslinkable dendritic nonlinear optic chromophores and polymer composites | |
| Zhang et al. | The preparation of two-dimensional spindle-type chromophores for second-order nonlinear optical materials | |
| US20040132960A1 (en) | Polymers having pendant nonlinear optical chromophores and electro-optic devices therefrom | |
| US7425643B1 (en) | Electron acceptors for nonlinear optical chromophores | |
| Lei et al. | Enhancement of electro-optic properties of nonlinear optical chromophores by introducing pentafluorobenzene group into the donor and π-bridge | |
| US7601849B1 (en) | Nonlinear optical compounds and related macrostructures | |
| US7749408B2 (en) | Electro-optic dendrimer-based glass composites | |
| US8648332B2 (en) | Phenyltetraene-based nonlinear optical chromophores | |
| EP1760080A1 (en) | Design and synthesis of thiophene derived NLO materials for electro-optic applications | |
| US20090118521A1 (en) | Nanoengineered organic nonlinear optical glasses | |
| CN101270116B (zh) | 中性-两性键连型二阶非线性光学生色团及其合成方法 | |
| Bhattacharjee | Novel concepts in the design and synthesis of organic nonlinear optical and electro-optic materials | |
| Liu | Design, synthesis and characterization of nonlinear-optic chromophores for electro-optic materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |