JP2004526020A5 - - Google Patents
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- Publication number
- JP2004526020A5 JP2004526020A5 JP2002566283A JP2002566283A JP2004526020A5 JP 2004526020 A5 JP2004526020 A5 JP 2004526020A5 JP 2002566283 A JP2002566283 A JP 2002566283A JP 2002566283 A JP2002566283 A JP 2002566283A JP 2004526020 A5 JP2004526020 A5 JP 2004526020A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- group
- dendrite
- vinyl
- acetylenyl
- 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.)
- Granted
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- 239000000412 dendrimer Substances 0.000 claims description 122
- 229920000736 dendritic polymer Polymers 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 210000001787 dendrite Anatomy 0.000 claims description 72
- 229920002554 vinyl polymer Polymers 0.000 claims description 53
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 52
- -1 acetylenyl group Chemical group 0.000 claims description 43
- 239000007787 solid Substances 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005418 aryl aryl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 150000004032 porphyrins Chemical class 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- AMQQZUHWWJLUGS-UHFFFAOYSA-N 2,3-bis(ethenyl)thiophene Chemical compound C=CC=1C=CSC=1C=C AMQQZUHWWJLUGS-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- NPRDEIDCAUHOJU-UHFFFAOYSA-N [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Pt].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NPRDEIDCAUHOJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 239000003550 marker Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical compound C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 238000000059 patterning Methods 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000003480 eluent Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- 239000010410 layer Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- UZFCFWSOGGWKEN-UHFFFAOYSA-N 3,5-bis[2-[3,5-bis[2-(3,5-ditert-butylphenyl)ethenyl]phenyl]ethynyl]benzaldehyde Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=CC=2C=C(C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=2)C#CC=2C=C(C=C(C=O)C=2)C#CC=2C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=2)=C1 UZFCFWSOGGWKEN-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- UTSLVCQVADCDED-UHFFFAOYSA-N 2-[4-(2-ethylhexoxy)phenyl]ethynyl-trimethylsilane Chemical compound CCCCC(CC)COC1=CC=C(C#C[Si](C)(C)C)C=C1 UTSLVCQVADCDED-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- NKIGODDIBWINDI-UHFFFAOYSA-N 1,3-ditert-butyl-5-[2-[3-(2,2-dibromoethenyl)-5-[2-(3,5-ditert-butylphenyl)ethenyl]phenyl]ethenyl]benzene Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=CC=2C=C(C=C(Br)Br)C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=2)=C1 NKIGODDIBWINDI-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XJJALYOLGFBXGK-UHFFFAOYSA-N 1,3-ditert-butyl-5-[2-[3-[2-(3,5-ditert-butylphenyl)ethenyl]-5-[2-(4-methylphenyl)ethenyl]phenyl]ethenyl]benzene Chemical compound C1=CC(C)=CC=C1C=CC1=CC(C=CC=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=CC(C=CC=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 XJJALYOLGFBXGK-UHFFFAOYSA-N 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- 229910020068 MgAl Inorganic materials 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- OAQVDDQBAQONBV-UHFFFAOYSA-N 3,5-bis[2-[4-(2-ethylhexoxy)phenyl]ethynyl]benzaldehyde Chemical compound C1=CC(OCC(CC)CCCC)=CC=C1C#CC1=CC(C=O)=CC(C#CC=2C=CC(OCC(CC)CCCC)=CC=2)=C1 OAQVDDQBAQONBV-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 6
- IGUZQRQTANOXGS-UHFFFAOYSA-N 1,3-bis[2-(3,5-ditert-butylphenyl)ethenyl]-5-[2-[4-(dimethoxyphosphorylmethyl)phenyl]ethenyl]benzene Chemical compound C1=CC(CP(=O)(OC)OC)=CC=C1C=CC1=CC(C=CC=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=CC(C=CC=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 IGUZQRQTANOXGS-UHFFFAOYSA-N 0.000 description 6
- RYCRYLSIFDCVGD-UHFFFAOYSA-N 1-[2-[4-[2-[3,5-bis[2-(3,5-ditert-butylphenyl)ethenyl]phenyl]ethenyl]phenyl]ethenyl]-3,5-bis(phenylmethoxy)benzene Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=CC=2C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=C(C=CC=3C=CC(C=CC=4C=C(OCC=5C=CC=CC=5)C=C(OCC=5C=CC=CC=5)C=4)=CC=3)C=2)=C1 RYCRYLSIFDCVGD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000005504 styryl group Chemical group 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 5
- FWDQYQWTXWKWKA-UHFFFAOYSA-N (4-methylphenyl)methylphosphanium;chloride Chemical compound [Cl-].CC1=CC=C(C[PH3+])C=C1 FWDQYQWTXWKWKA-UHFFFAOYSA-N 0.000 description 4
- LEAJPWHJWOPKLX-UHFFFAOYSA-N 3,5-bis[2-(3,5-ditert-butylphenyl)ethenyl]benzaldehyde Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=CC=2C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=C(C=O)C=2)=C1 LEAJPWHJWOPKLX-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000001194 electroluminescence spectrum Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- VUIIPZMAPLLLAG-UHFFFAOYSA-N 1,3-ditert-butyl-5-[2-[3-[2-(3,5-ditert-butylphenyl)ethenyl]-5-ethynylphenyl]ethenyl]benzene Chemical group CC(C)(C)C1=CC(C(C)(C)C)=CC(C=CC=2C=C(C=C(C=CC=3C=C(C=C(C=3)C(C)(C)C)C(C)(C)C)C=2)C#C)=C1 VUIIPZMAPLLLAG-UHFFFAOYSA-N 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 125000003609 aryl vinyl group Chemical group 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 229940001584 sodium metabisulfite Drugs 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- DPDOFFVOHWFBEM-UHFFFAOYSA-N 1-(2-ethylhexoxy)-4-ethynylbenzene Chemical compound CCCCC(CC)COC1=CC=C(C#C)C=C1 DPDOFFVOHWFBEM-UHFFFAOYSA-N 0.000 description 2
- UOMCJERKHZESES-UHFFFAOYSA-N 1-(2-ethylhexoxy)-4-iodobenzene Chemical compound CCCCC(CC)COC1=CC=C(I)C=C1 UOMCJERKHZESES-UHFFFAOYSA-N 0.000 description 2
- DPWKHKQDDLVEQE-UHFFFAOYSA-N 1-[2-[4-[2-[3,5-bis[2-(3,5-ditert-butylphenyl)ethenyl]phenyl]ethenyl]phenyl]ethenyl]-3,5-bis[2-[4-(2-ethylhexoxy)phenyl]ethynyl]benzene Chemical compound C1=CC(OCC(CC)CCCC)=CC=C1C#CC1=CC(C=CC=2C=CC(C=CC=3C=C(C=CC=4C=C(C=C(C=4)C(C)(C)C)C(C)(C)C)C=C(C=CC=4C=C(C=C(C=4)C(C)(C)C)C(C)(C)C)C=3)=CC=2)=CC(C#CC=2C=CC(OCC(CC)CCCC)=CC=2)=C1 DPWKHKQDDLVEQE-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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| GB0220080D0 (en) | 2002-08-29 | 2002-10-09 | Isis Innovation | Blended dendrimers |
| GB0311234D0 (en) | 2003-05-16 | 2003-06-18 | Isis Innovation | Organic phosphorescent material and organic optoelectronic device |
| US7364670B2 (en) * | 2003-07-17 | 2008-04-29 | Fujifilm Corporation | Liquid crystalline compound, liquid crystalline composition and retardation film |
| US7344583B2 (en) | 2005-03-31 | 2008-03-18 | 3M Innovative Properties Company | Methods of making metal particles within cored dendrimers |
| JP5144666B2 (ja) | 2006-09-19 | 2013-02-13 | スリーエム イノベイティブ プロパティズ カンパニー | 鋳型化された金属酸化物粒子及び製造方法 |
| KR101249117B1 (ko) * | 2006-11-13 | 2013-03-29 | 삼성전자주식회사 | 메탈로센 덴드리머, 이를 이용한 유기 메모리 소자 및 그의제조방법 |
| EP2123691A1 (en) | 2007-03-09 | 2009-11-25 | Sumitomo Chemical Company, Limited | Polymer compound and composition containing the same |
| KR101458204B1 (ko) * | 2007-04-02 | 2014-11-04 | 삼성전자주식회사 | 메탈로센 코어를 가지는 덴드리머, 이를 이용한 유기메모리 소자 및 그의 제조방법 |
| US9395352B2 (en) | 2007-04-06 | 2016-07-19 | Arizona Board Of Regents On Behalf Of Arizona State University | Devices and methods for target molecule characterization |
| WO2010042514A1 (en) | 2008-10-06 | 2010-04-15 | Arizona Board Of Regents | Nanopore and carbon nanotube based dna sequencer and a serial recognition elements |
| JP5388097B2 (ja) * | 2008-10-28 | 2014-01-15 | 国立大学法人 東京大学 | 液晶材料、液晶材料膜、コーティング材、及び、液晶材料膜製造方法 |
| KR101202351B1 (ko) * | 2010-07-16 | 2012-11-16 | 삼성디스플레이 주식회사 | 덴드리머 및 이를 이용한 유기 발광 소자 |
| US9376446B2 (en) | 2010-10-07 | 2016-06-28 | Hewlett-Packard Development Company, L.P. | Emissive dendrimer composition |
| US10493168B2 (en) * | 2012-02-27 | 2019-12-03 | Oxygen Enterprises, Ltd | Phosphorescent meso-unsubstituted metallo-porphyrin probe molecules for measuring oxygen and imaging methods |
| EA201491551A1 (ru) * | 2012-02-27 | 2015-02-27 | Сергей Виноградов | Улучшенные фосфоресцентные молекулы для измерения содержания кислорода и способы визуализации |
| WO2014059144A1 (en) | 2012-10-10 | 2014-04-17 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Systems and devices for molecule sensing and method of manufacturing thereof |
| JP6056605B2 (ja) * | 2013-03-28 | 2017-01-11 | 富士通株式会社 | 有機色素、及び感光性素子 |
| US10156572B2 (en) | 2014-02-18 | 2018-12-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Three arm Y-shaped bisbiotin ligand |
| US10336713B2 (en) | 2014-02-27 | 2019-07-02 | Arizona Board Of Regents, Acting For And On Behalf Of, Arizona State University | Triazole-based reader molecules and methods for synthesizing and use thereof |
| US10266325B2 (en) | 2016-06-07 | 2019-04-23 | International Business Machines Corporation | Polymer with blue light absorbing units chemically bonded to a polymeric backbone of the polymer |
| KR102731320B1 (ko) | 2024-03-27 | 2024-11-19 | 주식회사 예쓰바이오 | 유기성 폐기물 분해용 균주 및 이를 이용하는 유기성 폐기물의 처리 방법 |
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| JPH01105955A (ja) | 1987-10-19 | 1989-04-24 | Konica Corp | 電子写真感光体 |
| JPH0721629B2 (ja) | 1988-05-02 | 1995-03-08 | 宇部興産株式会社 | ホトレジスト用感光剤 |
| US5041516A (en) | 1989-06-21 | 1991-08-20 | Cornell Research Foundation, Inc. | Dendritic molecules and method of production |
| US5150006A (en) | 1991-08-01 | 1992-09-22 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (II) |
| JP3490727B2 (ja) | 1991-11-28 | 2004-01-26 | 三洋電機株式会社 | 電界発光素子 |
| JP3284766B2 (ja) | 1994-06-29 | 2002-05-20 | 三菱化学株式会社 | 有機電界発光素子 |
| EP0700917B1 (en) | 1994-09-12 | 2002-05-08 | Motorola, Inc. | Light emitting devices comprising organometallic complexes |
| JPH09241265A (ja) | 1996-03-07 | 1997-09-16 | Juzo Nakayama | テトラチエニルシラン誘導体およびその製造方法 |
| CN1208366C (zh) | 1997-10-23 | 2005-06-29 | Isis创新有限公司 | 发光树枝状分子及装置 |
| US5972247A (en) | 1998-03-20 | 1999-10-26 | Eastman Kodak Company | Organic electroluminescent elements for stable blue electroluminescent devices |
| EP1009042A3 (en) | 1998-12-09 | 2002-07-03 | Eastman Kodak Company | Electroliuminescent device with arylethylene derivatives in hole transport layer |
| US6361886B2 (en) | 1998-12-09 | 2002-03-26 | Eastman Kodak Company | Electroluminescent device with improved hole transport layer |
| EP1009043A3 (en) | 1998-12-09 | 2002-07-03 | Eastman Kodak Company | Electroluminescent device with polyphenyl hydrocarbon hole transport layer |
| US6465115B2 (en) | 1998-12-09 | 2002-10-15 | Eastman Kodak Company | Electroluminescent device with anthracene derivatives hole transport layer |
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| GB0002936D0 (en) * | 2000-02-09 | 2000-03-29 | Isis Innovation | Improved dendrimers |
| GB0104177D0 (en) | 2001-02-20 | 2001-04-11 | Isis Innovation | Aryl-aryl dendrimers |
| US7592074B2 (en) | 2001-02-20 | 2009-09-22 | Isis Innovation Limited | Metal-containing dendrimers |
| GB0104176D0 (en) * | 2001-02-20 | 2001-04-11 | Isis Innovation | Asymmetric dendrimers |
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| GB0220092D0 (en) * | 2002-08-29 | 2002-10-09 | Isis Innovation | Reactive dendrimers |
-
2001
- 2001-02-20 GB GBGB0104176.3A patent/GB0104176D0/en not_active Ceased
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2002
- 2002-02-20 DE DE60215473T patent/DE60215473T2/de not_active Expired - Lifetime
- 2002-02-20 JP JP2002566283A patent/JP5346422B2/ja not_active Expired - Fee Related
- 2002-02-20 US US10/468,863 patent/US7537842B2/en not_active Expired - Lifetime
- 2002-02-20 WO PCT/GB2002/000765 patent/WO2002066575A1/en not_active Ceased
- 2002-02-20 AT AT02712104T patent/ATE342948T1/de not_active IP Right Cessation
- 2002-02-20 EP EP02712104A patent/EP1373431B1/en not_active Expired - Lifetime
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2008
- 2008-09-16 JP JP2008236656A patent/JP2009060115A/ja active Pending
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2009
- 2009-05-26 US US12/472,176 patent/US7960557B2/en not_active Expired - Fee Related
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