MXPA05004607A - Dispositivo electroluminiscente. - Google Patents
Dispositivo electroluminiscente.Info
- Publication number
- MXPA05004607A MXPA05004607A MXPA05004607A MXPA05004607A MXPA05004607A MX PA05004607 A MXPA05004607 A MX PA05004607A MX PA05004607 A MXPA05004607 A MX PA05004607A MX PA05004607 A MXPA05004607 A MX PA05004607A MX PA05004607 A MXPA05004607 A MX PA05004607A
- Authority
- MX
- Mexico
- Prior art keywords
- substituted
- interrupted
- independently
- ci8alkyl
- formula
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 28
- -1 pyrimidine compound Chemical class 0.000 claims description 118
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 4
- 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 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 110
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 7
- 239000012044 organic layer Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 53
- 238000002347 injection Methods 0.000 description 51
- 239000007924 injection Substances 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- 230000032258 transport Effects 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000758 substrate Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 19
- 239000011777 magnesium Substances 0.000 description 19
- 150000003230 pyrimidines Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 229910052786 argon Inorganic materials 0.000 description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000004305 biphenyl Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 11
- 229910052749 magnesium Inorganic materials 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229910052790 beryllium Inorganic materials 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910000861 Mg alloy Inorganic materials 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 229910001316 Ag alloy Inorganic materials 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LFMXEURVJLMIKD-UHFFFAOYSA-N 2-(2-phenylphenyl)benzenecarboximidamide hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 LFMXEURVJLMIKD-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 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 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- AKRCGMWXORUMMA-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-iodo-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OC(F)(I)C(F)(F)F AKRCGMWXORUMMA-UHFFFAOYSA-N 0.000 description 2
- WXTUPKOMTOZRJM-UHFFFAOYSA-N 1,3-dinaphthalen-1-ylprop-2-en-1-one Chemical compound C1=CC=C2C(C(C=CC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 WXTUPKOMTOZRJM-UHFFFAOYSA-N 0.000 description 2
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 2
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- SXKBKLGHKDARFJ-UHFFFAOYSA-L zinc;2-(1,3-benzoxazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2O1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2O1 SXKBKLGHKDARFJ-UHFFFAOYSA-L 0.000 description 1
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0225244.3A GB0225244D0 (en) | 2002-10-30 | 2002-10-30 | Electroluminescent device |
| EP03405047 | 2003-01-31 | ||
| PCT/EP2003/011637 WO2004039786A1 (en) | 2002-10-30 | 2003-10-21 | Electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05004607A true MXPA05004607A (es) | 2005-06-08 |
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ID=32232219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05004607A MXPA05004607A (es) | 2002-10-30 | 2003-10-21 | Dispositivo electroluminiscente. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8012602B2 (enExample) |
| EP (1) | EP1556360B1 (enExample) |
| JP (1) | JP4963357B2 (enExample) |
| KR (1) | KR101027635B1 (enExample) |
| AT (1) | ATE384702T1 (enExample) |
| AU (1) | AU2003274050A1 (enExample) |
| BR (1) | BR0315894A (enExample) |
| DE (1) | DE60318876T2 (enExample) |
| MX (1) | MXPA05004607A (enExample) |
| TW (1) | TW200415953A (enExample) |
| WO (1) | WO2004039786A1 (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9923148B2 (en) * | 2002-10-30 | 2018-03-20 | Udc Ireland Limited | Electroluminescent device |
| JP2004277377A (ja) * | 2003-03-18 | 2004-10-07 | Junji Kido | フルオレン系化合物、およびこれを用いた有機電界発光素子 |
| SG146683A1 (en) | 2003-09-17 | 2008-10-30 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as serotonin receptor modulators |
| WO2005053048A1 (en) * | 2003-11-26 | 2005-06-09 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent devices comprising 2-(p-triphenyl)-3-phenyl-pyrazine derivatives |
| CN1950479A (zh) * | 2004-04-29 | 2007-04-18 | 西巴特殊化学品控股有限公司 | 电致发光器件 |
| KR101425423B1 (ko) | 2005-05-30 | 2014-08-01 | 시바 홀딩 인크 | 전계발광 장치 |
| US7598255B2 (en) | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| JP5446096B2 (ja) * | 2007-02-06 | 2014-03-19 | 住友化学株式会社 | 組成物及び該組成物を用いてなる発光素子 |
| KR101489541B1 (ko) * | 2007-09-03 | 2015-02-03 | 메르크 파텐트 게엠베하 | 플루오렌 유도체 |
| US8815416B2 (en) * | 2007-12-27 | 2014-08-26 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent device using a bipyrimidine compound |
| JP5207760B2 (ja) * | 2008-02-07 | 2013-06-12 | ケミプロ化成株式会社 | 新規なピリミジン系またはトリアジン系誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子 |
| JP2009277986A (ja) * | 2008-05-16 | 2009-11-26 | Sony Corp | 有機電界発光素子および表示装置 |
| JP5544775B2 (ja) * | 2008-07-29 | 2014-07-09 | 住友化学株式会社 | 燐光発光性化合物を含む組成物及び該組成物を用いてなる発光素子 |
| KR101288557B1 (ko) * | 2008-12-24 | 2013-07-22 | 제일모직주식회사 | 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
| WO2011005060A2 (ko) * | 2009-07-10 | 2011-01-13 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
| TWI482758B (zh) | 2009-08-21 | 2015-05-01 | Tosoh Corp | 環狀氮雜衍生物及其製造方法和以該環狀氮雜苯衍生物為構成成分之有機電致發光元件 |
| JP5812583B2 (ja) * | 2009-08-21 | 2015-11-17 | 東ソー株式会社 | トリアジン誘導体、その製造方法、及びそれを構成成分とする有機電界発光素子 |
| EP2489664A4 (en) | 2009-10-16 | 2013-04-03 | Idemitsu Kosan Co | FLUORINOUS AROMATIC COMPOUND, MATERIAL FOR AN ORGANIC ELECTROLUMINESCENT ELEMENT AND ORGANIC ELECTROLUMINESCENT ELEMENT THEREWITH |
| FR2956028B1 (fr) | 2010-02-08 | 2012-03-02 | Oreal | Composition cosmetique incluant au moins un compose fluorophore. |
| US20110309344A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising a layer of a pyridine compound and a 8-hydroxypquinolinolato earth alkaline metal, or alkali metal complex |
| JP5664128B2 (ja) * | 2010-10-29 | 2015-02-04 | 三菱化学株式会社 | ピリミジン化合物、有機電界発光素子用材料、有機電界発光素子用組成物、有機電界発光素子、照明装置及び表示装置 |
| KR101979693B1 (ko) * | 2010-12-13 | 2019-05-17 | 유디씨 아일랜드 리미티드 | 전자 응용을 위한 비스피리미딘 |
| US8362246B2 (en) | 2010-12-13 | 2013-01-29 | Basf Se | Bispyrimidines for electronic applications |
| CN103261172B (zh) * | 2010-12-21 | 2016-05-04 | E.I.内穆尔杜邦公司 | 包括嘧啶化合物的电子装置 |
| WO2012137958A1 (ja) | 2011-04-07 | 2012-10-11 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、該化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
| KR101888658B1 (ko) * | 2011-04-15 | 2018-08-14 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
| CN102250015B (zh) | 2011-05-19 | 2013-01-02 | 南方医科大学 | 聚集诱导发光的五取代四氢嘧啶及其制备方法和应用 |
| TWI591059B (zh) * | 2011-08-25 | 2017-07-11 | 半導體能源研究所股份有限公司 | 發光元件,發光裝置,電子裝置,照明裝置以及新穎有機化合物 |
| JP6034146B2 (ja) | 2011-11-11 | 2016-11-30 | 東ソー株式会社 | 含窒素縮環芳香族基を有する環状アジン化合物とその製造方法、及びそれらを構成成分とする有機電界発光素子 |
| KR102261235B1 (ko) | 2011-11-22 | 2021-06-04 | 이데미쓰 고산 가부시키가이샤 | 방향족 복소 고리 유도체, 유기 일렉트로루미네선스 소자용 재료 및 유기 일렉트로루미네선스 소자 |
| CN107342368B (zh) | 2011-11-22 | 2019-05-28 | 出光兴产株式会社 | 芳香族杂环衍生物、有机电致发光元件用材料以及有机电致发光元件 |
| US9059411B2 (en) | 2012-02-29 | 2015-06-16 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| KR101474713B1 (ko) | 2012-05-30 | 2014-12-23 | 주식회사 알파켐 | 신규한 전자 수송 물질 및 이를 이용한 유기 발광 소자 |
| WO2013180376A1 (en) * | 2012-05-30 | 2013-12-05 | Alpha Chem Co., Ltd. | New electron transport material and organic electroluminescent device using the same |
| US9412954B2 (en) * | 2012-07-13 | 2016-08-09 | Lg Chem, Ltd. | Heterocyclic compound and organic electronic element containing same |
| JP6312960B2 (ja) | 2012-08-03 | 2018-04-18 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、照明装置及び複素環化合物 |
| US9444059B2 (en) | 2013-02-21 | 2016-09-13 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
| CN105143186A (zh) | 2013-02-22 | 2015-12-09 | 出光兴产株式会社 | 蒽衍生物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
| KR102117611B1 (ko) | 2013-06-12 | 2020-06-02 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| CN105339365B (zh) | 2013-07-23 | 2018-01-26 | 出光兴产株式会社 | 新型化合物和使用其的有机电致发光元件 |
| JP6290381B2 (ja) | 2013-09-24 | 2018-03-07 | エルジー・ケム・リミテッド | ヘテロ環化合物およびこれを含む有機発光素子 |
| CN105473569B (zh) | 2013-11-13 | 2021-01-01 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
| KR101734459B1 (ko) * | 2014-05-20 | 2017-05-11 | 제일모직 주식회사 | 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 |
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| JP6515684B2 (ja) * | 2014-05-29 | 2019-05-22 | 東ソー株式会社 | ベンゾキナゾリン化合物、その製造方法、およびその用途 |
| WO2015182769A1 (ja) * | 2014-05-29 | 2015-12-03 | 東ソー株式会社 | キナゾリン及びベンゾキナゾリン化合物、その製法及び用途 |
| KR101782881B1 (ko) * | 2014-06-05 | 2017-09-28 | 제일모직 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
| KR102304716B1 (ko) | 2014-06-13 | 2021-09-27 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
| JP6507855B2 (ja) * | 2014-06-18 | 2019-05-08 | 東ソー株式会社 | キナゾリン化合物、その製造方法、およびその用途 |
| KR102313358B1 (ko) * | 2014-07-10 | 2021-10-18 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| MA40552A (fr) | 2014-08-04 | 2021-05-19 | Nuevolution As | Derives de pyrimidine eventuellement condensee substituee par un heterocycle utiles dans le traitement de maladies inflammatoires, metaboliques, oncologiques et auto-immunes |
| US10784446B2 (en) | 2014-11-28 | 2020-09-22 | Idemitsu Kosan Co., Ltd. | Compound, organic electroluminescence element material, organic electroluminescence element and electronic device |
| JP6684085B2 (ja) | 2014-12-19 | 2020-04-22 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
| KR102611317B1 (ko) | 2014-12-24 | 2023-12-07 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| EP3248966B1 (en) * | 2015-01-20 | 2022-12-21 | Hodogaya Chemical Co., Ltd. | Pyrimidine derivatives and organic electroluminescent devices |
| WO2016132250A1 (en) | 2015-02-18 | 2016-08-25 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, light-emitting element, display module, lighting module, light-emitting device, display device, electronic device, and lighting device |
| US20170040546A1 (en) * | 2015-08-04 | 2017-02-09 | Nichem Fine Technology Co., Ltd. | Novel compound and organic electronic device using the same |
| JP7039188B2 (ja) | 2016-06-24 | 2022-03-22 | 株式会社半導体エネルギー研究所 | 燐光発光層用ホスト材料、有機化合物、発光素子、発光装置、電子機器および照明装置 |
| KR101847347B1 (ko) * | 2017-06-30 | 2018-04-09 | 주식회사 두산 | 유기 화합물 및 이를 이용한 유기 전계 발광 소자 |
| US12289992B2 (en) | 2018-10-05 | 2025-04-29 | Samsung Display Co., Ltd. | Display apparatus and light absorber included in display apparatus |
| KR20210018105A (ko) | 2019-08-09 | 2021-02-17 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 디바이스, 발광 장치, 전자 기기, 및 조명 장치 |
| AU2020408107A1 (en) | 2019-12-20 | 2022-04-14 | Nuevolution A/S | Compounds active towards nuclear receptors |
| US11447479B2 (en) | 2019-12-20 | 2022-09-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| JP7713954B2 (ja) | 2020-03-31 | 2025-07-28 | ヌエヴォリューション・アクティーゼルスカブ | 核内受容体に対して活性な化合物 |
| CA3174252A1 (en) | 2020-03-31 | 2021-10-07 | Nuevolution A/S | Compounds active towards nuclear receptors |
| KR20240132446A (ko) * | 2022-01-13 | 2024-09-03 | 호도가야 가가쿠 고교 가부시키가이샤 | 피리미딘 화합물 및 유기 일렉트로루미네센스 소자 |
| US20250144046A1 (en) * | 2022-01-28 | 2025-05-08 | Metastx, Llc | Pharmaceutical compositions and methods of administration |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3319843A1 (de) * | 1983-06-01 | 1984-12-06 | Ali-Akbar Dipl.-Chem. Dr. 4300 Mülheim Pourzal | Verfahren zur herstellung von pyrimidinen aus nitrilen und alkinen |
| CN1022409C (zh) | 1987-11-25 | 1993-10-13 | 赫彻斯特股份公司 | 液晶环丙基烷基杂环化合物制备方法 |
| DE3915804A1 (de) | 1989-05-13 | 1990-11-15 | Hoechst Ag | Cyclopropylalkyl- oder -alkenylverbindungen, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallinen mischungen |
| US5238600A (en) | 1988-06-01 | 1993-08-24 | Hoffmann-La Roche Inc. | Ibimethylenoxy containing liquid crystal compounds |
| US5077142A (en) | 1989-04-20 | 1991-12-31 | Ricoh Company, Ltd. | Electroluminescent devices |
| EP0563009B1 (en) | 1992-03-23 | 1998-05-13 | Ciba SC Holding AG | Organic electroluminescent element |
| DE4423098A1 (de) * | 1994-07-01 | 1996-01-04 | Hoechst Ag | Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien |
| JPH0873440A (ja) * | 1994-08-31 | 1996-03-19 | Nippon Kasei Chem Co Ltd | ピリミジン誘導体の製造方法 |
| EP0711804A3 (de) | 1994-11-14 | 1999-09-22 | Ciba SC Holding AG | Kryptolichtschutzmittel |
| US5770108A (en) | 1995-06-28 | 1998-06-23 | Mitsui Toatsu Chemicals, Inc. | Pyrimidine compound and liquid crystal composition and liquid crystal element using the same |
| DE19628719B4 (de) * | 1996-07-17 | 2006-10-05 | Hans-Werner Prof. Dr. Schmidt | Elektronenleitende Schicht in organischen, elektrolumineszierenden Anordnungen |
| DE19809944A1 (de) | 1997-03-27 | 1998-10-01 | Merck Patent Gmbh | Elektrolumineszierende Flüssigkristallvorrichtung |
| JP3965800B2 (ja) | 1997-12-01 | 2007-08-29 | チッソ株式会社 | トリアリールアミン誘導体を用いた有機電界発光素子 |
| AU1199600A (en) * | 1998-10-02 | 2000-04-26 | Board Of Trustees Of The University Of Illinois, The | Estrogen receptor ligands |
| US6414104B1 (en) | 1999-07-20 | 2002-07-02 | Sri International | Arylamine-substituted poly (arylene vinylenes) and associated methods of preparation and use |
| JP4272778B2 (ja) | 1999-11-04 | 2009-06-03 | キヤノン株式会社 | 結晶薄膜の製造方法 |
| US6225467B1 (en) | 2000-01-21 | 2001-05-01 | Xerox Corporation | Electroluminescent (EL) devices |
| US6670645B2 (en) | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| DE60143106D1 (de) * | 2000-07-17 | 2010-11-04 | Fujifilm Corp | Lichtemittierendes Element und Azolverbindung |
| JP5135657B2 (ja) * | 2001-08-01 | 2013-02-06 | 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及び表示装置 |
| JP4646494B2 (ja) * | 2002-04-11 | 2011-03-09 | 出光興産株式会社 | 新規含窒素複素環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 |
| JP4036041B2 (ja) * | 2002-06-24 | 2008-01-23 | 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及び表示装置 |
| JP4223768B2 (ja) * | 2002-08-30 | 2009-02-12 | 富士フイルム株式会社 | 発光素子 |
| US7867629B2 (en) * | 2003-01-10 | 2011-01-11 | Idemitsu Kosan Co., Ltd. | Nitrogenous heterocyclic derivative and organic electroluminescent element employing the same |
-
2003
- 2003-10-21 DE DE60318876T patent/DE60318876T2/de not_active Expired - Lifetime
- 2003-10-21 EP EP03758029A patent/EP1556360B1/en not_active Expired - Lifetime
- 2003-10-21 JP JP2005501808A patent/JP4963357B2/ja not_active Expired - Lifetime
- 2003-10-21 WO PCT/EP2003/011637 patent/WO2004039786A1/en not_active Ceased
- 2003-10-21 BR BR0315894-2A patent/BR0315894A/pt not_active Application Discontinuation
- 2003-10-21 KR KR1020057007687A patent/KR101027635B1/ko not_active Expired - Lifetime
- 2003-10-21 MX MXPA05004607A patent/MXPA05004607A/es not_active Application Discontinuation
- 2003-10-21 AU AU2003274050A patent/AU2003274050A1/en not_active Abandoned
- 2003-10-21 US US10/531,780 patent/US8012602B2/en not_active Expired - Lifetime
- 2003-10-21 AT AT03758029T patent/ATE384702T1/de not_active IP Right Cessation
- 2003-10-29 TW TW092130068A patent/TW200415953A/zh unknown
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2010
- 2010-06-07 US US12/794,828 patent/US20100240892A1/en not_active Abandoned
Also Published As
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|---|---|
| US20100240892A1 (en) | 2010-09-23 |
| US20060041126A1 (en) | 2006-02-23 |
| WO2004039786A8 (en) | 2005-05-19 |
| KR20050084912A (ko) | 2005-08-29 |
| TW200415953A (en) | 2004-08-16 |
| JP2006510732A (ja) | 2006-03-30 |
| AU2003274050A1 (en) | 2004-05-25 |
| BR0315894A (pt) | 2005-10-04 |
| EP1556360A1 (en) | 2005-07-27 |
| US8012602B2 (en) | 2011-09-06 |
| WO2004039786A1 (en) | 2004-05-13 |
| ATE384702T1 (de) | 2008-02-15 |
| DE60318876T2 (de) | 2009-01-08 |
| JP4963357B2 (ja) | 2012-06-27 |
| DE60318876D1 (de) | 2008-03-13 |
| KR101027635B1 (ko) | 2011-04-07 |
| EP1556360B1 (en) | 2008-01-23 |
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