CN100360636C - 配位含芴化合物和电致发光装置 - Google Patents
配位含芴化合物和电致发光装置 Download PDFInfo
- Publication number
- CN100360636C CN100360636C CNB2003801100524A CN200380110052A CN100360636C CN 100360636 C CN100360636 C CN 100360636C CN B2003801100524 A CNB2003801100524 A CN B2003801100524A CN 200380110052 A CN200380110052 A CN 200380110052A CN 100360636 C CN100360636 C CN 100360636C
- Authority
- CN
- China
- Prior art keywords
- compound
- phenyl
- hexyl
- group
- ethylhexyl
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 243
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 44
- 239000000758 substrate Substances 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000576 coating method Methods 0.000 claims description 12
- 150000003384 small molecules Chemical class 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 160
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 128
- -1 fluorene compound Chemical class 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
- 238000006243 chemical reaction Methods 0.000 description 73
- 239000000243 solution Substances 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 53
- 239000004305 biphenyl Substances 0.000 description 50
- 239000010410 layer Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 33
- 238000000434 field desorption mass spectrometry Methods 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 26
- 239000000178 monomer Substances 0.000 description 26
- 239000012043 crude product Substances 0.000 description 25
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
- 239000012074 organic phase Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000605 extraction Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 16
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000003513 alkali Substances 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 12
- 238000000151 deposition Methods 0.000 description 12
- 230000008021 deposition Effects 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 238000012546 transfer Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 150000002220 fluorenes Chemical class 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 7
- 238000005424 photoluminescence Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 125000005259 triarylamine group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 229920000547 conjugated polymer Polymers 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229940126639 Compound 33 Drugs 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 150000004646 arylidenes Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 4
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940126208 compound 22 Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 3
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
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- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
Description
化合物 | M<sub>w</sub><sup>a</sup> | PDI | T<sub>d</sub>(℃) | T<sub>g</sub>(℃) | UV<sup>b</sup>(λ<sub>max</sub> nm) | PL<sup>c</sup>(λ<sub>max</sub> nm) | EL(λ<sub>max</sub> nm) |
165 | 16300 | 1.70 | 428 | 183 | 380 | 420(382) | 452 |
167 | 23200 | 2.30 | 441 | 50 | 342 | 396(342) | 412 |
168 | 29200 | 1.97 | 418 | 86 | 376 | 420(380) | 452 |
174 | 34400 | 2.01 | 429 | 138 | 392 | 424(394) | 456 |
190 | 7000 | 1.85 | 426 | 137 | 378 | 424(394) | 476 |
221 | 14100 | 1.80 | 430 | 190 | 362 | 410(364) | 440 |
206 | 38200 | 2.15 | 358 | NO | 392 | 432(394) | 468 |
231 | 39300 | 2.62 | 405 | 123 | 428 | 522(430) | 520 |
215 | 13100 | 1.65 | 433 | 140 | 388 | 426(384) | 456 |
133 | 29000 | 2.27 | 420 | 72 | 358 | 422(360) | 468 |
280 | 976 | 1.21 | 278 | 70 | NA<sup>d</sup> | NA | NA |
282 | 4920 | 1.57 | 454 | 182 | 394<sup>e</sup> | 448(396)<sup>e</sup> | 488 |
278 | 2550 | 1.35 | 449 | 128 | 380<sup>e</sup> | 428(382)<sup>e</sup> | NA |
284 | 1860 | 1.28 | 236 | 54 | 368<sup>e</sup> | 430(370)<sup>e</sup> | NA |
198 | 7990 | 2.52 | 436 | 174 | 384 | 448(386) | 452 |
199 | 6890 | 1.50 | 421 | NO | 384 | 424(386) | NA |
201 | 14100 | 1.68 | 405 | 76 | 388 | 450(378) | 460 |
273 | 5190 | 1.38 | 409 | 175 | 364 | 442(366) | 468 |
Claims (7)
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US10/334,359 US6849348B2 (en) | 2002-12-31 | 2002-12-31 | Complex fluorene-containing compounds |
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JP (1) | JP4897222B2 (zh) |
KR (1) | KR101032696B1 (zh) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107573925A (zh) * | 2016-07-05 | 2018-01-12 | 上海和辉光电有限公司 | 一种有机电致发光化合物 |
Families Citing this family (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6849348B2 (en) * | 2002-12-31 | 2005-02-01 | Eastman Kodak Company | Complex fluorene-containing compounds |
US20040131881A1 (en) * | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED devices |
JP4689969B2 (ja) * | 2003-04-05 | 2011-06-01 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | Iva族およびvia族化合物の調製 |
TW201235442A (en) * | 2003-12-12 | 2012-09-01 | Sumitomo Chemical Co | Polymer and light-emitting element using said polymer |
JP4792738B2 (ja) * | 2003-12-12 | 2011-10-12 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
US7267892B2 (en) * | 2004-02-25 | 2007-09-11 | Eastman Kodak Company | Electroluminescent devices having pendant naphthylanthracene-based polymers |
KR100721551B1 (ko) * | 2004-03-17 | 2007-05-23 | 삼성에스디아이 주식회사 | 백색 발광 유기전계발광소자 및 그를 구비하는유기전계발광표시장치 |
JP2006128624A (ja) * | 2004-09-29 | 2006-05-18 | Canon Inc | 発光素子 |
US20060094859A1 (en) * | 2004-11-03 | 2006-05-04 | Marrocco Matthew L Iii | Class of bridged biphenylene polymers |
JP4904752B2 (ja) * | 2004-11-24 | 2012-03-28 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
WO2006059486A1 (ja) * | 2004-12-02 | 2006-06-08 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタ材料、有機薄膜トランジスタ、電界効果トランジスタ、スイッチング素子、有機半導体材料及び有機半導体膜 |
WO2006070911A1 (ja) * | 2004-12-27 | 2006-07-06 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
JP4904805B2 (ja) * | 2004-12-27 | 2012-03-28 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
JP5256568B2 (ja) * | 2004-12-28 | 2013-08-07 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
JP4896411B2 (ja) * | 2005-02-18 | 2012-03-14 | 住友化学株式会社 | 高分子化合物及びそれを用いた高分子発光素子 |
JP4724440B2 (ja) * | 2005-03-04 | 2011-07-13 | 住友化学株式会社 | 高分子化合物及びそれを用いた高分子発光素子 |
GB0507684D0 (en) * | 2005-04-15 | 2005-05-25 | Cambridge Display Tech Ltd | Pulsed driven displays |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
JP5457619B2 (ja) * | 2005-06-10 | 2014-04-02 | 住友化学株式会社 | ポリアリーレン |
US7576356B2 (en) * | 2005-08-08 | 2009-08-18 | Osram Opto Semiconductors Gmbh | Solution processed crosslinkable hole injection and hole transport polymers for OLEDs |
TWI415920B (zh) * | 2005-08-12 | 2013-11-21 | Sumitomo Chemical Co | 高分子材料及使用該高分子材料之元件 |
ATE509055T1 (de) * | 2005-08-16 | 2011-05-15 | Merck Patent Gmbh | Verfahren zur polymerisation von thiophen- oder selenophenderivaten |
JP2007119763A (ja) * | 2005-09-29 | 2007-05-17 | Sumitomo Chemical Co Ltd | 高分子材料及び高分子発光素子 |
WO2007064034A1 (ja) * | 2005-12-02 | 2007-06-07 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
GB2434915A (en) * | 2006-02-03 | 2007-08-08 | Cdt Oxford Ltd | Phosphoescent OLED for full colour display |
JP5145717B2 (ja) * | 2006-04-13 | 2013-02-20 | 東ソー株式会社 | ベンゾフルオレン化合物及びその用途 |
EP2006278B2 (en) * | 2006-04-13 | 2016-10-12 | Tosoh Corporation | Benzofluorene compound and use thereof |
DE102006025846A1 (de) * | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) * | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US7547757B2 (en) * | 2006-08-01 | 2009-06-16 | Headwaters Technology Innovation, Llc | Methods for manufacturing aryl-aryl coupled polymers |
US7687601B2 (en) * | 2006-10-03 | 2010-03-30 | Headwaters Technology Innovation, Llc | Methods for purifying polymers using solid scavengers |
JP5233228B2 (ja) * | 2006-10-05 | 2013-07-10 | Jnc株式会社 | ベンゾフルオレン化合物、該化合物を用いた発光層用材料及び有機電界発光素子 |
JP5023683B2 (ja) * | 2006-12-12 | 2012-09-12 | 東ソー株式会社 | ベンゾフルオレン誘導体の製造方法およびその中間体 |
US8465848B2 (en) * | 2006-12-29 | 2013-06-18 | E I Du Pont De Nemours And Company | Benzofluorenes for luminescent applications |
JP5439711B2 (ja) * | 2007-01-26 | 2014-03-12 | 東ソー株式会社 | ベンゾフルオレン化合物及びその用途 |
JP5163853B2 (ja) * | 2007-03-22 | 2013-03-13 | 東ソー株式会社 | 有機化合物およびその用途 |
JP4811314B2 (ja) * | 2007-03-27 | 2011-11-09 | セイコーエプソン株式会社 | 有機elデバイス |
JP5369384B2 (ja) * | 2007-03-29 | 2013-12-18 | 住友化学株式会社 | 有機光電変換素子及びその製造に有用な重合体 |
US20080278072A1 (en) * | 2007-04-30 | 2008-11-13 | Lg Chem, Ltd. | Organic light emitting device and method of producing the same |
US20080283827A1 (en) * | 2007-05-15 | 2008-11-20 | Shiying Zheng | Fused-fluorene-containing materials as semiconductor materials for thin film transistors |
JP5374833B2 (ja) * | 2007-05-16 | 2013-12-25 | 東ソー株式会社 | 有機エレクトロルミネセンス材料およびそれを用いた有機エレクトロルミネセンス素子 |
JP5104074B2 (ja) * | 2007-07-03 | 2012-12-19 | 住友化学株式会社 | 重合体及びそれを用いた有機光電変換素子 |
JP5205859B2 (ja) * | 2007-08-09 | 2013-06-05 | 東ソー株式会社 | 新規なベンゾ[c]フルオレン誘導体及びその用途 |
JP5205858B2 (ja) * | 2007-08-09 | 2013-06-05 | 東ソー株式会社 | 新規なベンゾ[c]フルオレン誘導体及びその用途 |
JP5247130B2 (ja) * | 2007-11-27 | 2013-07-24 | キヤノン株式会社 | 縮合多環化合物及びそれを用いた有機発光素子 |
JP2009149846A (ja) * | 2007-11-29 | 2009-07-09 | Sumitomo Chemical Co Ltd | アミン化合物とアクセプタ性化合物とを含む組成物 |
JP5217476B2 (ja) * | 2008-02-08 | 2013-06-19 | Jnc株式会社 | ベンゾフルオレン化合物、該化合物を用いた発光層用材料及び有機電界発光素子 |
DE102008018670A1 (de) * | 2008-04-14 | 2009-10-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP5408902B2 (ja) * | 2008-05-15 | 2014-02-05 | キヤノン株式会社 | ジベンゾ[c,g]フルオレン化合物及びそれを使用した有機発光素子 |
JP5366505B2 (ja) * | 2008-11-06 | 2013-12-11 | キヤノン株式会社 | インデノピレン化合物及びこれを用いた有機発光素子 |
US8431249B2 (en) | 2008-11-06 | 2013-04-30 | Canon Kabushiki Kaisha | Dibenzo[C,G]fluorene compound and organic light-emitting device using same |
US8174000B2 (en) * | 2009-02-11 | 2012-05-08 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
KR101427605B1 (ko) * | 2009-03-31 | 2014-08-07 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
KR20100109293A (ko) * | 2009-03-31 | 2010-10-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
WO2010135248A1 (en) * | 2009-05-18 | 2010-11-25 | The Regents Of The University Of California | Electronically conductive polymer binder for lithium-ion battery electrode |
JP2011012047A (ja) | 2009-06-05 | 2011-01-20 | Tosoh Corp | アミン誘導体及び有機エレクトロルミネッセンス素子 |
KR20100137198A (ko) * | 2009-06-22 | 2010-12-30 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101202347B1 (ko) * | 2009-10-09 | 2012-11-16 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자 |
KR20110057400A (ko) * | 2009-11-24 | 2011-06-01 | 덕산하이메탈(주) | 인데노플루오렌을 포함하는 화합물 및 이를 이용한 유기전자소자, 그 단말 |
JPWO2011074231A1 (ja) * | 2009-12-14 | 2013-04-25 | 出光興産株式会社 | 多環縮環化合物及びそれを用いた有機薄膜トランジスタ |
CN102666549A (zh) * | 2009-12-14 | 2012-09-12 | 出光兴产株式会社 | 多环稠环化合物以及使用该多环稠环化合物的有机薄膜晶体管 |
KR101144356B1 (ko) * | 2009-12-18 | 2012-05-11 | 덕산하이메탈(주) | 인데노페난트렌 구조를 포함하는 화합물 및 이를 이용한 유기전자소자, 그 단말 |
DE102010020567A1 (de) * | 2010-05-14 | 2011-11-17 | Merck Patent Gmbh | Metallkomplexe |
WO2011153105A1 (en) * | 2010-06-02 | 2011-12-08 | The Regents Of The University Of California | Si composite electrode with li metal doping for advanced lithium-ion battery |
JP2011038103A (ja) * | 2010-08-26 | 2011-02-24 | Sumitomo Chemical Co Ltd | 高分子化合物及びそれを用いた高分子発光素子 |
KR101957902B1 (ko) * | 2011-04-13 | 2019-03-14 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
JP5780132B2 (ja) | 2011-05-19 | 2015-09-16 | Jnc株式会社 | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 |
JP5973705B2 (ja) | 2011-06-16 | 2016-08-23 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用の発光材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5982966B2 (ja) | 2011-08-17 | 2016-08-31 | Jnc株式会社 | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 |
JP6063114B2 (ja) | 2011-08-18 | 2017-01-18 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5890980B2 (ja) | 2011-08-18 | 2016-03-22 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用の化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP5952543B2 (ja) | 2011-08-18 | 2016-07-13 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、有機電界発光素子用の化合物、並びに該素子を用いた発光装置、表示装置及び照明装置 |
JP2013118349A (ja) * | 2011-11-02 | 2013-06-13 | Udc Ireland Ltd | 有機電界発光素子、有機電界発光素子用材料並びに該有機電界発光素子を用いた発光装置、表示装置及び照明装置 |
TWI570095B (zh) | 2011-11-04 | 2017-02-11 | 捷恩智股份有限公司 | 苯并茀化合物、使用了該化合物的發光層用材料以及有機電場發光元件 |
JP6021389B2 (ja) * | 2012-04-05 | 2016-11-09 | キヤノン株式会社 | 有機発光素子 |
EP2864339A4 (en) | 2012-06-25 | 2016-04-20 | Univ Jefferson | COMPOSITIONS AND METHOD FOR TREATING CANCER WITH BUTTERANT LIPOGENIC SIGNALING |
WO2014065391A1 (ja) * | 2012-10-26 | 2014-05-01 | Jnc株式会社 | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 |
US9748492B2 (en) | 2012-11-02 | 2017-08-29 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
US20150329772A1 (en) | 2013-01-03 | 2015-11-19 | Merck Patent Gmbh | Materials for Electronic Devices |
KR101326085B1 (ko) * | 2013-01-08 | 2013-11-07 | 덕산하이메탈(주) | 인데노플루오렌을 포함하는 화합물 및 이를 이용한 유기전자소자, 그 단말 |
KR102137472B1 (ko) * | 2013-02-08 | 2020-07-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
WO2015033559A1 (ja) | 2013-09-06 | 2015-03-12 | 出光興産株式会社 | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
CN105431407B (zh) | 2013-09-20 | 2020-09-04 | 出光兴产株式会社 | 有机电致发光元件和电子仪器 |
EP3135726A4 (en) * | 2014-04-21 | 2018-04-18 | Sumitomo Chemical Company, Limited | Composition and polymer compound, and organic semiconductor element containing said composition and said polymer compound |
KR101900370B1 (ko) | 2015-05-13 | 2018-09-19 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치 |
US10696664B2 (en) | 2015-08-14 | 2020-06-30 | Merck Patent Gmbh | Phenoxazine derivatives for organic electroluminescent devices |
KR20180090931A (ko) | 2017-02-03 | 2018-08-14 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
KR20190010419A (ko) * | 2017-07-21 | 2019-01-30 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102048920B1 (ko) | 2017-08-18 | 2019-11-27 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
US10232360B1 (en) * | 2017-09-12 | 2019-03-19 | Chevron Phillips Chemical Company, Lp | Use of organic dopants to enhance acetylene hydrogenation catalysts |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999054385A1 (en) * | 1998-04-21 | 1999-10-28 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
WO2001081294A1 (en) * | 2000-04-26 | 2001-11-01 | Sony International (Europe) Gmbh | End-capped polyfluorenes, films and devices based thereon |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0885461B1 (en) * | 1996-03-04 | 2003-08-13 | DuPont Displays, Inc. | Polyfluorenes as materials for photoluminescence and electroluminescence |
CA2215856A1 (en) * | 1996-09-26 | 1998-03-26 | Eli Lilly And Company | Dihydrobenzofluorene compounds, intermediates, compositions, and methods |
CA2214935A1 (en) * | 1996-09-26 | 1998-03-26 | Henry Uhlman Bryant | Benzofluorene compounds, intermediates, compositions, and methods |
EP1020510A4 (en) * | 1997-05-15 | 2004-12-29 | Sanyo Electric Co | ORGANIC ELECTROLUMINESCENT ELEMENT |
US6184224B1 (en) * | 1998-12-01 | 2001-02-06 | Board Of Regents, The University Of Texas System | Antitumor dibenzofluorene derivatives |
TW460490B (en) * | 1999-05-13 | 2001-10-21 | Nat Science Council | Electroluminiscent conjugated polymers modified with high eletronegative heterocyclic moieties and their applications in polymeric light emitting diodes |
WO2001072713A1 (en) * | 2000-03-27 | 2001-10-04 | Akzo Nobel N.V. | Non-steroidal, tetracyclic compounds for estrogen-related treatments |
JP5034140B2 (ja) * | 2000-03-31 | 2012-09-26 | 住友化学株式会社 | 高分子蛍光体、その製造方法、およびそれを用いた高分子発光素子 |
DE60103442T3 (de) * | 2000-03-31 | 2014-05-15 | Sumitomo Chemical Co. Ltd. | Polymerisches fluoreszentes Material, Verfahren zu ihrer Herstellung, und lumineszentes Polymergerät worin es eingesetzt wird |
WO2001096454A1 (en) * | 2000-06-12 | 2001-12-20 | Maxdem Incorporated | Polymer matrix electroluminescent materials and devices |
US6686065B2 (en) * | 2001-12-12 | 2004-02-03 | Canon Kabushiki Kaisha | [5]-helicene and dibenzofluorene materials for use in organic light emitting devices |
TW200304371A (en) * | 2002-02-22 | 2003-10-01 | Akzo Nobel Nv | Substituted 10-ary1-11H-benzo [b] fluorenes and 7-ary1-5, 6-dihydro-benz [a] anthracenes for selective effects on estrogen receptors |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
US7094902B2 (en) * | 2002-09-25 | 2006-08-22 | 3M Innovative Properties Company | Electroactive polymers |
US20040131881A1 (en) * | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED devices |
US6849348B2 (en) * | 2002-12-31 | 2005-02-01 | Eastman Kodak Company | Complex fluorene-containing compounds |
-
2002
- 2002-12-31 US US10/334,359 patent/US6849348B2/en not_active Expired - Lifetime
-
2003
- 2003-10-30 TW TW092130270A patent/TW200416269A/zh unknown
- 2003-12-19 KR KR1020057012260A patent/KR101032696B1/ko active IP Right Grant
- 2003-12-19 CN CNB2003801100524A patent/CN100360636C/zh not_active Expired - Lifetime
- 2003-12-19 JP JP2004565609A patent/JP4897222B2/ja not_active Expired - Lifetime
- 2003-12-19 WO PCT/US2003/040731 patent/WO2004061048A1/en active Application Filing
-
2004
- 2004-06-23 US US10/875,011 patent/US7348071B2/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999054385A1 (en) * | 1998-04-21 | 1999-10-28 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
WO2001081294A1 (en) * | 2000-04-26 | 2001-11-01 | Sony International (Europe) Gmbh | End-capped polyfluorenes, films and devices based thereon |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107573925A (zh) * | 2016-07-05 | 2018-01-12 | 上海和辉光电有限公司 | 一种有机电致发光化合物 |
CN107573925B (zh) * | 2016-07-05 | 2020-02-21 | 上海和辉光电有限公司 | 一种有机电致发光化合物 |
Also Published As
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KR101032696B1 (ko) | 2011-05-06 |
US20040241496A1 (en) | 2004-12-02 |
JP4897222B2 (ja) | 2012-03-14 |
US20040131880A1 (en) | 2004-07-08 |
KR20050089993A (ko) | 2005-09-09 |
JP2006512395A (ja) | 2006-04-13 |
US7348071B2 (en) | 2008-03-25 |
WO2004061048A1 (en) | 2004-07-22 |
CN1756825A (zh) | 2006-04-05 |
US6849348B2 (en) | 2005-02-01 |
TW200416269A (en) | 2004-09-01 |
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