JP2011051985A - ヘテロ環化合物及び有機発光素子 - Google Patents
ヘテロ環化合物及び有機発光素子 Download PDFInfo
- Publication number
- JP2011051985A JP2011051985A JP2010193061A JP2010193061A JP2011051985A JP 2011051985 A JP2011051985 A JP 2011051985A JP 2010193061 A JP2010193061 A JP 2010193061A JP 2010193061 A JP2010193061 A JP 2010193061A JP 2011051985 A JP2011051985 A JP 2011051985A
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- layer
- electrode
- substituted
- 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
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 239000000126 substance Substances 0.000 claims abstract description 35
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000004431 deuterium atom Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 4
- 238000002347 injection Methods 0.000 claims description 68
- 239000007924 injection Substances 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000010408 film Substances 0.000 claims description 38
- -1 anthracene compound Chemical class 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 14
- 125000006267 biphenyl group Chemical group 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000004528 spin coating Methods 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012528 membrane Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 238000001771 vacuum deposition Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004896 high resolution mass spectrometry Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 3
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 3
- MINMDCMSHDBHKG-UHFFFAOYSA-N 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(=C(S1)C)N=C1N1CCOCC1 MINMDCMSHDBHKG-UHFFFAOYSA-N 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
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 3
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 2
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- PJUAIXDOXUXBDR-UHFFFAOYSA-N 3-iodo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(I)=CC=C2N1C1=CC=CC=C1 PJUAIXDOXUXBDR-UHFFFAOYSA-N 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- 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 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- YPJRZWDWVBNDIW-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-UHFFFAOYSA-N 0.000 description 1
- VMFMUJZRXZXYAH-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound C=CC(=O)NC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=1N1CCN(C)CC1 VMFMUJZRXZXYAH-UHFFFAOYSA-N 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 239000002120 nanofilm Substances 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 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 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/12—All metal or with adjacent metals
- Y10T428/12493—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.]
- Y10T428/12771—Transition metal-base component
- Y10T428/12861—Group VIII or IB metal-base component
- Y10T428/12944—Ni-base component
Abstract
【解決手段】下記化学式1で表示されるヘテロ環化合物及びこれを含む有機膜を備える有機発光素子:
上記化学式1で、R1ないしR11はそれぞれ独立して、水素原子、重水素原子、C1−C50アルキル基、C3−C50シクロアルキル基、C1−C50アルコキシ基、C5−C50アリールオキシ基、C5−C50アリールチオ基、C5−C60アリール基、C5−C50アリール基で置換されたアミノ基、C4−C60ヘテロアリール基、C6−C60縮合多環基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシル基またはカルボキシル基を示し、R1ないしR11は、隣接する置換基の1組が互いに結合し、芳香環を形成する。
【選択図】図1
Description
R1ないしR11は、隣接する置換基の1組が互いに結合し、芳香環を形成する。
R1ないしR11は、隣接する置換基の1組が互いに結合し、芳香環を形成する。
計算値;439.0936、実測値;439.0923
1H−NMR、400MHz、CD2Cl2:δ7.88−6.89(m、22H)、δ2.43(s、3H)、δ2.33(s、3H)、δ1.73(s、6H)、δ1.34(s、9H)
13C−NMR:141.3、140.3、139.2、138.8、136.9、136.0、135.7、135.1、133.4、133.1、132.6、131.2、131.0、130.6、130.2、129.6、129.1、128.6、128.4、128.0、127.6、125.3、125.5、125.1、124.8、124.5、124.3、123.9、123.3、121.9、121.1、120.6、116.5、115、4、38.5、34.4、31.3、30.2、12.8、11.5
1H−NMR、400MHz、CD2Cl2:δ8.10−7.84(m、2H)、δ7.68−6.89(m、36H)
13C−NMR:140.3、140.0、139.1、138.8、137.9、136.8、135.7、135.1、134.4、133.8、132.6、131.0、130.6、130.0、129.6、129.0、128.2、128.0、127.2、127.0、126.3、125.5、125.1、124.8、124.5、124.3、123.9、123.3、121.9、121.1、120.6、120.1、119.6、118.5、118.3、116.5、115.4
1H−NMR、400MHz、CD2Cl2:δ7.98−6.69(m、44H)
13C−NMR:140.1、140.0、139.1、138.9、138.5、137.4、137.1、136.3、135.2、135.1、134.7、134.4、133.8、133.4、132.9、132.6、131.8、131.0、130.6、130.0、129.6、129.0、128.6、128.4、128.2、128.0、127.2、127.0、126.3、125.5、125.1、124.8、124.5、124.3、123.9、123.3、122.8、122.2、121.9、121.1、120.6、120.1、119.6、118.5、118.3、116.5、115.4
1H−NMR、400MHz、CD2Cl2:δ7.90−7.02(m、37H)
13C−NMR:140.4、140.2、139.7、138.9、138.3、137.6、137.5、137.3、135.2、135.1、134.7、134.4、133.7、133.3、132.9、132.3、131.8、131.5、130.7、130.0、129.3、129.0、128.6、128.4、128.2、128.0、127.6、127.0、126.3、125.5、125.1、124.8、124.5、124.3、123.9、122.8、122.2、121.9、120.6、119.6、118.5、118.3
1H−NMR、400MHz、CD2Cl2:δ7.90−7.02(m、37H)、δ2.43(s、3H)、δ2.32(s、3H)、δ1.32(s、6H)、δ1.28(s、6H)
13C−NMR:141.4、141.2、140.5、140.0、139.7、138.6、138.3、137.6、137.3、136.5、136.1、135.2、135.1、134.7、134.4、133.7、133.3、132.9、132.3、131.8、131.5、130.7、130.0、129.3、129.0、128.6、128.4、128.2、128.0、127.6、127.0、126.6、125.5、125.2、124.8、124.6、124.4、123.2、122.2、120.6、119.6、118.5、26.5、26.3、18.4、18.2、13.2、13.1
1H−NMR、400MHz、CD2Cl2:δ8.02−7.02(m、23H)、δ2.43(s、3H)、δ2.32(s、3H)、δ1.62(s、6H)、δ1.47(s、9H)、δ1.45(s、9H)
13C−NMR:140.5、140.1、139.4、138.6、138.4、137.6、137.0、136.7、136.2、135.2、135.1、134.8、134.4、133.7、133.3、132.9、132.3、131.8、131.5、130.3、130.0、129.3、129.0、128.6、128.4、128.2、128.0、127.6、127.0、126.8、125.6、125.2、124.9、124.6、124.4、122.2、120.6、119.6、118.5、26.6、26.3、18.4、18.2、13.2、13.1
アノードは、コーニング15Ωcm2(1,200Å)ITOガラス基板を50mm×50mm×0.7mmサイズに切り、イソプロピルアルコールと純水とを利用し、それぞれ5分間超音波洗浄した後、30分間紫外線を照射してオゾンに露出させて洗浄して作製し、真空蒸着装置にこのガラス基板を設置した。
発光層の形成時に、上記化合物11の代わりに、化合物29を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
発光層の形成時に、上記化合物11の代わりに、化合物43を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
発光層の形成時に、上記化合物11の代わりに、化合物56を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
発光層の形成時に、上記化合物11の代わりに、化合物74を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
発光層の形成時に、上記化合物11の代わりに、化合物82を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
電子輸送層の形成時に、Alq3の代わりに、本実施例の化合物82を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
発光層の形成時に、上記化合物11の代わりに、既知の青色ドーパントである1,4−ビス−(2,2−ジフェニルビニル)ビフェニル(DPVBi)を利用したことを除いては、実施例1と同様に、有機発光素子を製作した。
Claims (18)
- 下記化学式1で表示されるヘテロ環化合物:
R1ないしR11は、隣接する置換基の1組が互いに結合し、芳香環を形成する。 - 前記R1は、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基及びフルオレニル基から選択される非置換の一環ないし三環のアリール基またはカルバゾリル基;またはC1−C5アルキル基、C1−C5アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン原子で置換された、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基及びフルオレニル基から選択される一環ないし三環のアリール基またはカルバゾリル基である、請求項1に記載のヘテロ環化合物。
- 前記R7は、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基及びフルオレニル基から選択される非置換の一環ないし三環のアリール基またはカルバゾリル基;非置換のC12−C50アリールアミン基;C1−C5アルキル基、C1−C5アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン原子で置換された、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基及びフルオレニル基から選択される一環ないし三環のアリール基またはカルバゾリル基;またはC1−C5アルキル基、C1−C5アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン原子で置換された、C12−C50アリールアミン基である、請求項1または2に記載のヘテロ環化合物。
- 前記R2またはR3はそれぞれ独立して、メチル基またはフェニル基である、請求項1ないし3のいずれか1項に記載のヘテロ環化合物。
- 前記R5またはR10はそれぞれ独立して、t−ブチル基、フェニル基、ナフチル基またはフルオレニル基である、請求項1ないし4のいずれか1項に記載のヘテロ環化合物。
- 第1電極と、第2電極と、前記第1電極と前記第2電極との間に介在された有機膜とを備える有機発光素子であって、前記有機膜が請求項1ないし6のいずれか1項に記載のヘテロ環化合物を含む、有機発光素子。
- 前記有機膜が、電子注入層または電子輸送層を含む、請求項7に記載の化合物を含む有機発光素子。
- 前記有機膜が、電子注入機能及び電子輸送機能を共に有する単一膜を含む、請求項7に記載の有機発光素子。
- 前記有機膜が、発光層を含む、請求項7に記載の有機発光素子。
- 前記有機膜が発光層を含み、前記発光層が前記ヘテロ環化合物を蛍光またはリン光のホストとして使う、請求項7に記載の有機発光素子。
- 前記有機膜が発光層を含み、前記発光層が前記ヘテロ環化合物をドーパントとして使う、請求項7に記載の有機発光素子。
- 前記有機膜が、発光層、電子注入層または電子輸送層を含み、前記発光層は、アントラセン化合物、アリールアミン化合物、またはスチリル化合物を含む、請求項7に記載の有機発光素子。
- 前記有機膜が、発光層、電子注入層または電子輸送層を含み、前記発光層は、リン光化合物を含む赤色発光層、緑色発光層、青色発光層または白色発光層を含む、請求項7に記載の有機発光素子。
- 前記有機膜が、正孔注入層、正孔輸送層、電子阻止層、発光層、正孔阻止層、電子輸送層及び電子注入層ならなる群から選択される1層以上の層をさらに含む、請求項7に記載の有機発光素子。
- 第1電極/正孔注入層/発光層/第2電極、第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/第2電極、または第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極の構造を有する、請求項15に記載の有機発光素子。
- 1層以上の層が前記ヘテロ環化合物を使用して湿式工程で形成される、請求項7ないし16のいずれか1項に記載の有機発光素子。
- 請求項7ないし17のいずれか1項に記載の有機発光素子を備え、前記有機発光素子の第1電極が、薄膜トランジスタのソース電極またはドレイン電極と電気的に連結された、平板表示装置。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020090082566A KR101193182B1 (ko) | 2009-09-02 | 2009-09-02 | 유기 발광 소자 |
KR10-2009-0082566 | 2009-09-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011051985A true JP2011051985A (ja) | 2011-03-17 |
JP5216823B2 JP5216823B2 (ja) | 2013-06-19 |
Family
ID=43128215
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010193061A Active JP5216823B2 (ja) | 2009-09-02 | 2010-08-31 | ヘテロ環化合物及び有機発光素子 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8431241B2 (ja) |
EP (1) | EP2301920B1 (ja) |
JP (1) | JP5216823B2 (ja) |
KR (1) | KR101193182B1 (ja) |
CN (1) | CN102001988B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012204092A (ja) * | 2011-03-24 | 2012-10-22 | Panasonic Corp | 有機エレクトロルミネッセンス素子、照明器具、及び食品保管装置 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101213495B1 (ko) * | 2010-06-03 | 2013-01-14 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR101891773B1 (ko) * | 2011-10-18 | 2018-08-27 | 삼성디스플레이 주식회사 | 신규한 헤테로고리 화합물 및 이를 포함한 유기발광 소자 |
KR102288845B1 (ko) * | 2015-01-12 | 2021-08-11 | 삼성디스플레이 주식회사 | 터치 센서를 포함하는 표시 장치 |
CN110330502A (zh) * | 2019-07-10 | 2019-10-15 | 吉林奥来德光电材料股份有限公司 | 有机发光化合物及其制备方法和应用 |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0416853A (ja) * | 1990-05-11 | 1992-01-21 | Citizen Watch Co Ltd | 電子写真用感光体 |
JPH0416851A (ja) * | 1990-05-11 | 1992-01-21 | Citizen Watch Co Ltd | 電子写真用感光体 |
JPH0431868A (ja) * | 1990-05-29 | 1992-02-04 | Citizen Watch Co Ltd | 電子写真用感光体 |
JP2010034450A (ja) * | 2008-07-31 | 2010-02-12 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2010073987A (ja) * | 2008-09-19 | 2010-04-02 | Idemitsu Kosan Co Ltd | 有機薄膜太陽電池用材料 |
JP2010087408A (ja) * | 2008-10-02 | 2010-04-15 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2010219302A (ja) * | 2009-03-17 | 2010-09-30 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2010225861A (ja) * | 2009-03-24 | 2010-10-07 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2011037831A (ja) * | 2009-08-10 | 2011-02-24 | Samsung Mobile Display Co Ltd | 有機発光素子 |
JP2011037854A (ja) * | 2009-08-10 | 2011-02-24 | Samsung Mobile Display Co Ltd | 縮合環化合物及び有機発光素子 |
JP2012510988A (ja) * | 2008-12-05 | 2012-05-17 | グレイセル・ディスプレイ・インコーポレーテッド | 新規な有機発光化合物及びこれを用いた有機発光素子 |
JP2012520872A (ja) * | 2009-03-20 | 2012-09-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL77055A (en) | 1984-11-15 | 1989-08-15 | Wellcome Found | Aromatic polycyclic alkylamines,their preparation and pharmaceutical compositions containing them |
US6583168B1 (en) | 1997-11-25 | 2003-06-24 | Applera Corporation | Sulfonated diarylrhodamine dyes |
EP1666561A1 (en) * | 1998-12-28 | 2006-06-07 | Idemitsu Kosan Company Limited | Organic electroluminescent element |
JP4025136B2 (ja) | 2002-07-31 | 2007-12-19 | 出光興産株式会社 | アントラセン誘導体、有機エレクトロルミネッセンス素子用発光材料及び有機エレクトロルミネッセンス素子 |
ATE555182T1 (de) | 2002-08-23 | 2012-05-15 | Idemitsu Kosan Co | Organische elektrolumineszenz vorrichtung und anthracenderivat |
US7887931B2 (en) * | 2003-10-24 | 2011-02-15 | Global Oled Technology Llc | Electroluminescent device with anthracene derivative host |
KR100573137B1 (ko) * | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
CA2606804A1 (en) | 2005-05-03 | 2006-11-09 | Ranbaxy Laboratories Limited | Antimicrobial agents |
DE102005023437A1 (de) * | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
KR20080114784A (ko) | 2006-04-03 | 2008-12-31 | 이데미쓰 고산 가부시키가이샤 | 비스안트라센 유도체 및 그것을 이용한 유기 전기발광 소자 |
US7723722B2 (en) | 2007-03-23 | 2010-05-25 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, anthracene derivative, and light-emitting element, light-emitting device, and electronic device using anthracene derivative |
KR20100000772A (ko) * | 2008-06-25 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR101551207B1 (ko) * | 2008-09-04 | 2015-09-08 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
-
2009
- 2009-09-02 KR KR1020090082566A patent/KR101193182B1/ko active IP Right Grant
-
2010
- 2010-08-12 US US12/855,523 patent/US8431241B2/en active Active
- 2010-08-31 EP EP10174612.1A patent/EP2301920B1/en active Active
- 2010-08-31 CN CN201010269550.5A patent/CN102001988B/zh active Active
- 2010-08-31 JP JP2010193061A patent/JP5216823B2/ja active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0416853A (ja) * | 1990-05-11 | 1992-01-21 | Citizen Watch Co Ltd | 電子写真用感光体 |
JPH0416851A (ja) * | 1990-05-11 | 1992-01-21 | Citizen Watch Co Ltd | 電子写真用感光体 |
JPH0431868A (ja) * | 1990-05-29 | 1992-02-04 | Citizen Watch Co Ltd | 電子写真用感光体 |
JP2010034450A (ja) * | 2008-07-31 | 2010-02-12 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2010073987A (ja) * | 2008-09-19 | 2010-04-02 | Idemitsu Kosan Co Ltd | 有機薄膜太陽電池用材料 |
JP2010087408A (ja) * | 2008-10-02 | 2010-04-15 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2012510988A (ja) * | 2008-12-05 | 2012-05-17 | グレイセル・ディスプレイ・インコーポレーテッド | 新規な有機発光化合物及びこれを用いた有機発光素子 |
JP2010219302A (ja) * | 2009-03-17 | 2010-09-30 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2012520872A (ja) * | 2009-03-20 | 2012-09-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2010225861A (ja) * | 2009-03-24 | 2010-10-07 | Mitsui Chemicals Inc | 有機トランジスタ |
JP2011037831A (ja) * | 2009-08-10 | 2011-02-24 | Samsung Mobile Display Co Ltd | 有機発光素子 |
JP2011037854A (ja) * | 2009-08-10 | 2011-02-24 | Samsung Mobile Display Co Ltd | 縮合環化合物及び有機発光素子 |
Non-Patent Citations (8)
Title |
---|
JPN6012055969; Journal of the American Chemical Society 123(48), 2001, 11940-11944 * |
JPN7012004362; Chemische Berichte 98(9), 19650901, 2814-2821 * |
JPN7012004363; Chemische Berichte 100(8), 19670801, 2649-2654 * |
JPN7012004364; Chemische Berichte 98(2), 19650201, 588-592 * |
JPN7012004365; Chemische Berichte 96(3), 19630301, 699-706 * |
JPN7012004366; Journal of Molecular Structure 375(1), 19960101, 117-126 * |
JPN7012004367; Zeitschrift Fur Analytische Chemie 263(1), 19730101, 19-23 * |
JPN7012004368; Journal of Heterocyclic Chemistry 21(2), 1984, 273-282 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012204092A (ja) * | 2011-03-24 | 2012-10-22 | Panasonic Corp | 有機エレクトロルミネッセンス素子、照明器具、及び食品保管装置 |
Also Published As
Publication number | Publication date |
---|---|
JP5216823B2 (ja) | 2013-06-19 |
KR101193182B1 (ko) | 2012-10-19 |
EP2301920B1 (en) | 2013-07-17 |
CN102001988B (zh) | 2014-10-01 |
CN102001988A (zh) | 2011-04-06 |
EP2301920A1 (en) | 2011-03-30 |
US8431241B2 (en) | 2013-04-30 |
US20110049486A1 (en) | 2011-03-03 |
KR20110024532A (ko) | 2011-03-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5211104B2 (ja) | 有機発光素子 | |
JP5258846B2 (ja) | 有機発光素子 | |
JP5683877B2 (ja) | 有機発光素子 | |
JP4589223B2 (ja) | フェニルカルバゾール系化合物とその製造方法及び有機電界発光素子 | |
JP5119485B2 (ja) | アミン系化合物、これを含む有機発光素子、及びその有機発光素子を具備した平板表示装置 | |
JP5823731B2 (ja) | 有機発光素子 | |
JP5588789B2 (ja) | ヘテロアリールアミン化合物及びそれを用いた有機発光素子 | |
JP5514627B2 (ja) | 有機発光素子 | |
JP5676182B2 (ja) | ヘテロ環化合物及びこれを含む有機発光素子 | |
KR101937257B1 (ko) | 신규한 헤테로고리 화합물 및 이를 포함한 유기발광 소자 | |
JP5900946B2 (ja) | 有機発光素子 | |
JP5676180B2 (ja) | ヘテロ環化合物及びこれを利用した有機発光素子 | |
JP5258845B2 (ja) | 有機発光素子 | |
JP5216823B2 (ja) | ヘテロ環化合物及び有機発光素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20120921 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121030 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130130 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130219 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130304 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5216823 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160308 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |