CN105745200B - Novel organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- CN105745200B CN105745200B CN201480063398.1A CN201480063398A CN105745200B CN 105745200 B CN105745200 B CN 105745200B CN 201480063398 A CN201480063398 A CN 201480063398A CN 105745200 B CN105745200 B CN 105745200B
- Authority
- CN
- China
- Prior art keywords
- organic electroluminescent
- substituted
- unsubstituted
- compound
- group
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 119
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 60
- 239000000463 material Substances 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 22
- 125000001072 heteroaryl group Chemical group 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000001769 aryl amino group Chemical group 0.000 description 11
- -1 aryl carbazole Chemical group 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000007740 vapor deposition Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000005103 alkyl silyl group Chemical group 0.000 description 6
- 125000005104 aryl silyl group Chemical group 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 1
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 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 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ROPCXUHUYPCFCP-UHFFFAOYSA-N 2,3-diphenylbenzene-1,4-diamine Chemical compound C=1C=CC=CC=1C=1C(N)=CC=C(N)C=1C1=CC=CC=C1 ROPCXUHUYPCFCP-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- UVIFHAPRMMAMAR-UHFFFAOYSA-N [Al+3].C1(=CC=CC=C1)C1=CC=C(C=C1)O Chemical compound [Al+3].C1(=CC=CC=C1)C1=CC=C(C=C1)O UVIFHAPRMMAMAR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 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 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 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
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
-
- 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
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compounds according to the present invention can be used in a light-emitting layer and have excellent light-emitting efficiency; and an organic electroluminescent device comprising the organic electroluminescent compound of the present invention has a long life span and improved current efficiency and power efficiency.
Description
Technical Field
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices containing the same.
Background
Electroluminescent (EL) devices are self-emissive devices that have the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time. Organic EL devices were originally developed by Eastman Kodak (Eastman Kodak) by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer (see appl. phys. lett.) -51, 913, 1987.
An organic EL device generally includes an anode, a cathode, and an organic layer formed between the two electrodes and emits light when holes injected from the anode and electrons injected from the cathode form an excited state by recombination thereof and then the excited state returns to a ground state. The organic layer of the organic EL device may be composed of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an emission layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and the like; the material used in the organic layer may be classified into a hole injecting material, a hole transporting material, an electron blocking material, a light emitting material, a hole blocking material, an electron transporting material, an electron injecting material, and the like.
The most important factor determining the luminous efficiency in an organic EL device is a light emitting material. There is a need for luminescent materials having the following characteristics: high quantum efficiency, high mobility of electrons and holes, formability of a uniform light emitting material layer, and stability. A mixed system of dopant/host materials can be used as a luminescent material to improve color purity, luminous efficiency, and stability. If a dopant/host material system is used, then the choice of host material is important, as host material can greatly affect the efficiency and performance of the light emitting device. Among conventional techniques, 4, 4 '-N, N' -dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. Pioneer et al currently develop high-efficiency organic EL devices by using Bathocuproine (BCP), bis (2-methyl-8-quinolinato) (4-phenylphenol) aluminum (III) (BAlq), etc., which are used in the hole blocking layer, as host materials.
Although these phosphorescent host materials provide good luminescent characteristics, they have the following disadvantages: (1) due to its low glass transition temperature and poor thermal stability, it may decompose during high temperature deposition processes in vacuum. (2) The power efficiency of an organic EL device is given by [ (pi/voltage) × current efficiency ], and is inversely proportional to the voltage. Organic EL devices comprising phosphorescent host materials provide higher current efficiency (cd/a) and have higher driving voltages than devices comprising fluorescent host materials. Therefore, the organic EL device using the conventional phosphorescent host material has no advantage in power efficiency (lm/W). (3) In addition, the operating life and luminous efficacy of the organic EL device are unsatisfactory.
The present invention can minimize crystallization by heat during and after vapor deposition at high temperature by increasing the thermal stability of the material.
Generally, the glass transition temperature (Tg) should be increased to increase thermal stability. To increase the Tg, a number of substituents should be attached. However, the temperature of vapor deposition increases excessively when many substituents are combined and the material degrades and is damaged during vapor deposition. Therefore, a suitable Tg should be maintained by introducing a suitable number of substituents and the vapor deposition temperature should be kept low despite the high molecular weight. The present invention solves the above problems by introducing carbazolyl group to the 9-position of fluorene structure. Although the material of the present invention has a high molecular weight, it has a lower vapor deposition temperature than carbazole derivatives having a similar molecular weight. Furthermore, the materials of the present invention have a high Tg. This feature results from the carbazolyl group substituting the 9-position of the fluorene structure, thereby increasing the steric hindrance of the fluorene structure. The higher the steric hindrance, the less the interaction between the molecules and the lower the vapor deposition temperature.
Therefore, in order to exhibit excellent characteristics of the organic EL device, materials constituting the organic layers in the device, specifically, hosts or dopants should be appropriately selected. Meanwhile, korean patent nos. 10-0957288, 10-0948700, and 10-0955993 disclose a compound in which a nitrogen-containing heterocyclic group is bonded to a carbazolyl group, a compound in which a nitrogen-containing heterocyclic group is bonded to an aryl carbazole or a carbazolylalkylene group, and an indolocarbazole derivative of a specific structure as host materials in a light-emitting layer, respectively. However, the organic EL device including the compound described in the above publication still does not satisfy power efficiency, light emission efficiency, lifetime, and the like. Accordingly, the present inventors have attempted to find an organic electroluminescent compound that can provide an organic EL device having characteristics superior to those of the compounds described in the above publications, and have found a material having a high Tg and a low vapor deposition temperature via the introduction of a carbazolyl group at the 9-position of the fluorene structure, and thus can provide an organic EL device having high luminous efficiency and excellent characteristics.
Disclosure of Invention
Technical problem
It is an object of the present invention to provide an organic electroluminescent compound having high luminous efficiency and to provide an organic EL device comprising the organic electroluminescent compound and having a long driving life as well as improved power efficiency and current efficiency.
Solution to the problem
The present inventors found that the above object can be achieved by a compound represented by the following formula 1:
wherein
A1Represents a substituted or unsubstituted 5-to 30-membered heteroaryl;
L1represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted 5-to 30-membered heteroarylene;
R1represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted 5-to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group;
R2represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-to 30-membered heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted (C6-C30) arylamino, or substituted or unsubstituted(C1-C30) alkyl (C6-C30) arylamino or the following formula 2:
R2Forming a benzocarbazole by fusing to a carbazole ring;
R3represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-to 30-membered heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted (C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
x represents O, S, CR11R12、NR13Or SiR13R14；
R4、R5And R6Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-to 30-membered heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkylsilyl, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted (C6-C30) arylamino or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; or are linked to an adjacent substituent(s) to form a mono-or polycyclic (C3-C30) alicyclic or aromatic ring, a carbon atom of which may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
R11to R14Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted 5-to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono-or polycyclic (C3-C30) alicyclic or aromatic ring, a carbon atom of which may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
a. c, d and e each independently represent an integer of 1 to 4; wherein a, c, d or e is an integer of 2 or greater, each R2、R4、R5Or R6The same or different;
b represents an integer of 1 to 3; wherein b is an integer of 2 or greater, each R3The same or different;
n represents an integer of 0 or 1;
m represents an integer of 1 or 2; and
the heteroaryl (ene) group contains at least one heteroatom selected from B, N, O, S, P (═ O), Si, and P.
Advantageous effects of the invention
The organic electroluminescent compounds according to the present invention have high luminous efficiency compared to conventional materials, and thus organic EL devices comprising the compounds as light-emitting host materials have long driving lifetimes and improved power efficiency, thereby reducing consumed power.
Detailed Description
Modes for the invention
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.
The present invention relates to an organic electroluminescent compound represented by formula 1, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic EL device comprising the material.
In this context, "(C1-C30) (alkylene)" means a straight or branched chain (alkylene) group having 1 to 30 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. "(C2-C30) alkenyl" means a straight or branched alkenyl group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "(C2-C30) alkynyl" is a straight or branched chain alkynyl group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30) cycloalkyl" is a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "3-to 7-membered heterocycloalkyl" is a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, P (═ O), Si, and P, preferably O, S, and N, and 3 to 7, preferably 5 to 7, ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiacyclopentane, tetrahydropyran, and the like. "(C6-C30) (arylene) group" is a single or condensed ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, indenyl, triphenylenyl, pyrenyl, fused tetraphenyl, perylenyl, chrysenyl, tetracenyl, fluoranthenyl, and the like. A "3-to 30-membered (arylene) heteroaryl" is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, P (═ O), Si, and P, and having 3 to 30 ring backbone atoms; a monocyclic ring or a condensed ring condensed with at least one benzene ring; having preferably 3 to 20, more preferably 3 to 15 ring backbone atoms; may be partially saturated; may be a group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via a single bond; and include monocyclic heteroaryl groups including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused-ring heteroaryl groups including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenazinyl, phenanthridinyl, benzodioxolyl and the like. "halogen" includes F, Cl, Br and I.
In this context, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or group, i.e., a substituent. A of formula 11、h1、R1To R6And R11To R14The substituents of substituted (C1-C30) alkyl, substituted (C1-C30) alkoxy, substituted (C3-C30) cycloalkyl, substituted (C6-C30) (arylene), substituted 5-to 30-membered (arylene) heteroaryl, and substituted (C6-C30) aryl (C1-C30) alkyl of (a) are each independently at least one substituent selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; 3-to 7-membered heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; a 3-to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30) aryl group; (C6-C30) aryl unsubstituted or substituted with 3-to 30-membered heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di (C1-C30) alkylamino; mono-or di (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; a bis (C6-C30) arylboron group; a di (C1-C30) alkylboron group; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
The compound of formula 1 is represented by the following formula 3, 4 or 5:
wherein
A1、L1、R1To R5A, b, c, d, m and n are as defined in formula 1.
In the compound of formula 1, A1Preferably represents pyridine, pyrimidine, triazine, pyrazine, quinoline, quinazoline, quinoxaline or naphthyridine; l is1Represents a single bond or (C6-C20) arylene; r1Represents (C1-C20) alkyl, (C6-C20) aryl or 5-to 20-membered heteroaryl; r2Represents hydrogen, deuterium, (C6-C20) aryl, 5-to 20-membered heteroaryl, (C6-C20) arylamino, or formula 2, or a benzocarbazole formed by fusion to a carbazole ring; r3、R4、R5And R6Each independently represents hydrogen or (C1-C20) alkyl; and R is11To R14Each independently represents a (C1-C20) alkyl group, a (C6-C20) aryl group, or a 5-to 20-membered heteroaryl group.
The compound of formula 1 may be selected from the group consisting of:
the organic electroluminescent compounds according to the invention can be prepared by methods known to those skilled in the art and can be prepared, for example, according to the following reaction scheme 1:
reaction scheme 1
Wherein
A1、L1、R1To R5A, b, c, d, m and n are as defined in formula 1 and Hal represents halogen.
The present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising the same. The material may contain the organic electroluminescent compound of the present invention alone, or may further include conventional materials generally included in organic electroluminescent materials.
The organic electroluminescent device according to the present invention may include a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes at least one organic electroluminescent compound of formula 1.
One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic layer may include a light emitting layer, and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
The organic electroluminescent compound of formula 1 according to the present invention may be included as a light emitting layer. Preferably, the light emitting layer may further include at least one dopant, and may include other compounds as a second host material, if necessary, in addition to the organic electroluminescent compound of formula 1 of the present invention.
The present invention further provides a substance for producing an organic EL device. The substance comprises first and second host materials. The first host material includes the organic electroluminescent compound of the present invention. The weight ratio of the first host material to the second host material may be in the range of 1: 99 to 99: 1.
The second host material may be any one of known phosphorescent hosts, and is preferably selected from the group consisting of compounds of the following formulae 6 to 10 in view of luminous efficiency:
H-(Cz-L4)h-M (6)
H-(Cz)iL4-M (7)
wherein
Cz represents the following structure:
x represents O or S;
R21to R24Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-or 30-membered heteroaryl, or R25R26R27Si-; or are linked to adjacent substituents to form a mono-or polycyclic (C5-C30) alicyclic or aromatic ring, the carbon atoms of which may beSubstituted with at least one heteroatom selected from nitrogen, oxygen and sulfur;
R25to R27Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group;
L4represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted 5-or 30-membered heteroarylene;
m represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted 5-or 30-membered heteroaryl;
Y1and Y2Each independently represents-O-, -S-, -N (R)31) -or-C (R)32)(R33) -; and Y is1And Y2Not exist at the same time;
R31to R33Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted 5-or 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono-or polycyclic (C5-C30) alicyclic or aromatic ring, a carbon atom of which may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and R is32And R33May be the same or different;
h and i each independently represent an integer of 1 to 3;
j. k, l and m each independently represent an integer of 0 to 4;
wherein h, i, j, k, L or m is an integer of 2 or more, each (Cz-L)4) Each (Cz), each R21Each R22Each R23Or each R24The same or different.
Specifically, the second host material includes each of:
wherein TPS represents triphenylsilyl.
The dopant is preferably one or more phosphorescent dopants. The phosphorescent dopant material used for the organic electroluminescent device of the present invention is not particularly limited, but may be preferably selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably from ortho-metalated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably from ortho-metalated iridium complex compounds.
The dopant used in the organic electroluminescent device of the present invention may be selected from the group consisting of compounds represented by formulae 11 to 13 below:
wherein
L is selected from the following structures:
R100represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; r101To R109And R111To R123Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted(C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; r120To R123To adjacent substituents to form fused rings, such as quinoline; r124To R127Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; when R is124To R127When aryl, it is linked to an adjacent substituent to form a fused ring, e.g., fluorene; r201To R211Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; f and g each independently represent an integer of 1 to 3; wherein f or g is an integer of 2 or more, each R100May be the same or different; and n represents an integer of 1 to 3.
The dopant material includes each of:
the organic layer of the organic electroluminescent device of the present invention comprises the organic electroluminescent compound of formula 1 and may further include at least one compound selected from the group consisting of: arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device of the present invention, the organic layer may further include at least one metal selected from the group consisting of: organometallic of group 1 metals, group 2 metals, transition metals of period 4, transition metals of period 5, lanthanides and d-transition elements of the periodic table, or at least one complex compound comprising said metals.
In addition, the organic electroluminescent device of the present invention may emit white light by: the mode further comprises at least one light-emitting layer comprising a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound in addition to the organic electroluminescent compound of the present invention; and may further include a yellow or orange light emitting layer, if necessary.
Preferably, in the organic electroluminescent device of the present invention, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, referred to as "surface layer") may be disposed on the inner surface of one or both electrodes. Specifically, it is preferable that a chalcogenide (including oxide) layer having silicon or aluminum is disposed on the anode surface of the light emitting intermediate layer, and a metal halide layer or a metal oxide layer is disposed on the cathode surface of the electroluminescent intermediate layer. The surface layer provides operational stability of the organic electroluminescent device. Preferably, the chalcogenide compound comprises SiOX(1≤X≤2)、AlOX(X is more than or equal to 1 and less than or equal to 1.5), SiON, SiAlON and the like; the metal halide includes LiF, MgF2、CaF2Rare earth metal fluorides, etc.; and the metal oxide comprises Cs2O、Li2O, MgO, SrO, BaO, CaO, etc.
Preferably, in the organic electroluminescent device of the present invention, a mixed region of the electron transport compound and the reductive dopant or a mixed region of the hole transport compound and the oxidative dopant may be disposed on at least one surface of the pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region into the luminescent medium. In addition, the hole transport compound is oxidized into cations, and thus it becomes easier to inject and transport holes from the mixed region into the light emitting medium. Preferably, the oxidizing dopant includes various Lewis acids (Lewis acids) and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reductive dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device of the present invention, a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as spin coating, dip coating, flow coating method, or the like may be used.
When a wet film formation method is used, a thin film is formed by dissolving or dispersing a material constituting each layer in a suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, or the like). The solvent is not particularly limited as long as the material constituting each layer is soluble or dispersible in the solvent without causing any problem in forming the layer.
Hereinafter, the light emitting characteristics of the organic electroluminescent compounds, the preparation methods thereof, and the devices comprising the same according to the present invention will be described in detail with reference to the following examples:
example 1: preparation of Compound H-34
Preparation of Compounds 1-2
2-Bromobiphenyl (50.0g, 214.0mmol) and Tetrahydrofuran (THF) (1.0L) were cooled to-78 deg.C in a 3L Round Bottom Flask (RBF) and 2.5M n-butyllithium (103.0mL, 257.0mmol) was added thereto. After 2 hours, (4-bromophenyl) (phenyl) methanone (56.0g, 214.0mmol) was added to the flask. After 17 hours, with dichloromethane (MC) and H2O extract the mixture and pass the MC layer over MgSO4And (5) drying. The MC layer was concentrated to give Compound 1-1.
Stirring Compound 1 in 3L RBF under reflux-1, hydrochloric acid (100.0mL) and acetic acid (1.0L). After 14 hours, the resulting solid was filtered and the filtered solid was dissolved in chloroform (CHCl)3) And applied to column chromatography to obtain compound 1-2(35.0g, 42%).
Preparation of Compounds 1-3
Compounds 1-2(35.0g, 89.0mmol), bis (pinacolato) diborane (27.0g, 106.0mmol), bis (triphenylphosphine) palladium (II) dichloride (Pd (PPh) were stirred in 1L RBF at reflux3)2Cl2) (3.1g, 4.45mmol), potassium acetate (KOAc) (22.0g, 222.0mmol), and 1, 4-dioxane (445.0 mL). After 3 hours, with Dichloromethane (DCM) and H2The mixture was extracted with O and the DCM layer was passed over MgSO4Dried and filtered. Dissolving the obtained solid in CHCl3And applied to column chromatography to obtain compounds 1-3(22.0g, 56%).
Preparation of Compounds 1-4
Compounds 1-3(22.0g, 50.0mmol), 2-bromonitrobenzene (12.0g, 60.0mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh) were stirred under reflux in 500mL RBF3)4)(1.7g，1.5mmol)、K2CO3(13.7g, 99.4mmol), toluene (100.0mL), ethanol (EtOH) (25.0mL), and H2O (25.0L). After 5 hours, with DCM and H2The mixture was extracted with O and the DCM layer was passed over MgSO4Dried and filtered. Dissolving the obtained solid in CHCl3And applied to column chromatography to obtain compounds 1-4(15.0g, 70%).
Preparation of Compounds 1-5
Compounds 1-4(15.0g, 35.0mmol), triethyl phosphite (P (OEt) and stirred under reflux in 500mL RBF3) (100.0mL) and 1, 2-dichlorobenzene (1, 2-DCB) (50.0 mL). After 13 hours, the solvent was distilled off, and the residue was dissolved in CHCl3And applied to column chromatography to obtain compounds 1-5(8.42g, 59%).
Preparation of Compounds 1-6
Compound by stirring in 500mL RBF under refluxSubstances 1-5(8.4g, 21.0mmol), 1-bromo-3-iodobenzene (8.7g, 31.0mmol), Cul (2.0g, 10.3mmol), ethylenediamine (1.4mL, 21.0mmol), K3PO4(13.0g, 62.0mmol) and toluene (103.0mL) for 23 h. After completion of the reaction, let to cool to room temperature and use DCM and H2O extraction and DCM layer over MgSO4And (5) drying. The DCM layer was concentrated under reduced pressure and the resulting solution was applied to column chromatography to obtain compounds 1-6(9.5g, 94%).
Preparation of Compounds 1-7
Compounds 1-6(9.5g, 19.5mmol), bis (pinacolato) diborane (6.4g, 25.0mmol), Pd (PPh) were stirred in 500mL RBF at reflux3)2Cl2) (684.0mg, 0.97mmol), KOAc (4.8g, 49.0mmol), and 1, 4-dioxane (196.0 mL). After 6 hours, with DCM and H2The mixture was extracted with O and the DCM layer was passed over MgSO4Dried and filtered. Dissolving the obtained solid in CHCl3And applied to column chromatography to obtain compounds 1-7(8.0g, 69%).
Preparation of Compound H-34
Compounds 1-7(8.0g, 13.0mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.2g, 15.7mmol), Pd (PPh) in 250mL RBF were stirred at reflux3)4(454.0mg，0.39mmol)、K2CO3(3.6g, 26.0mmol), toluene (30.0mL), EtOH (7.0mL), and H2O (7.0 mL). After 3 hours, with DCM and H2The mixture was extracted with O and the DCM layer was passed over MgSO4Dried and filtered. Dissolving the obtained solid in CHCl3And applied to column chromatography to obtain compound H-34(3.95g, 42%).
mp 288 ℃, UV 290nm (in toluene), PL 430nm (in toluene), MS/EIMS 714.28
Example 2: preparation of Compound H-57
Preparation of Compound 2-1
Compounds 1-3(35.0g, 78.0mmol), 2, 5-dibromonitrobenzene (26.2g, 93.0mmol), Pd (PPh) were stirred in 2L RBF at 130 deg.C3)4(3.6g，3.1mmol)、Na2CO3(20.6g, 195.0mmol), toluene (400.0mL), EtOH (50.0mL), and H2O (100.0mL) overnight. With Ethyl Acetate (EA) and H2Treating the reaction mixture with MgSO4The water was removed, and the residue was distilled under reduced pressure. The crude product was applied to a sample having an MC: column chromatography of hexane (Hx) to obtain compound 2-1(30.0g, 75%) as a solid.
Preparation of Compound 2-2
Stirring Compound 2-1(30.0g, 57.8mmol), P (OEt) in 1L RBF at 150 deg.C3(200.0mL) and 1, 2-DCB (200.0mL) for 2 hours. The reaction mixture was distilled to obtain a solid. The crude product was applied to a sample having an MC: column chromatography of Hx afforded compound 2-2(19.0g, 68%) as a white solid.
Preparation of Compounds 2-3
Compounds 2-2(5.7g, 47.0mmol), Pd (PPh) were stirred at 120 ℃ in 500mL RBF3)4(1.8g，1.5mmol)、K2CO3(13.5g, 97.0mmol), toluene (200.0mL), EtOH (50.0mL), and H2O (50.0mL) for 2.5 h. With EA and H2Treating the reaction mixture with MgSO4The water was removed, and the residue was distilled under reduced pressure. The crude product was applied to a sample having an MC: column chromatography of Hx afforded compound 2-3(16.0g, 84%) as a white solid.
Preparation of Compound H-57
Compounds 2-3(10.0g, 20.6mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (9.6g, 24.8mmol), palladium (II) acetate (Pd (OAc))2) (232.0mg, 1.0mmol), 2-dicyclohexylphosphino-2 ', -6' -dimethoxydiphenyl (s-phos) (850.0mg, 2.0mmol), sodium tert-butoxide (NaOtBu) (5.0g, 51.6mmol) and o-xylene (200.0mL) for 2 h. With EA and H2Treating the reaction mixture with MgSO4The water was removed, and the residue was distilled under reduced pressure. The crude product was applied to a sample having an MC: column chromatography of Hx afforded Compound H-57(7.3g, 45%) as a white solid.
mp 312 ℃, UV 344nm (in toluene), PL 427nm (in toluene), MS/EIMS 791
Example 3: preparation of Compound H-90
Preparation of Compound 3-1
In a flask 9-fluorenone (20.0g, 111.0mmol) was dissolved in THF (554.0mL) and phenylmagnesium bromide (36.9mL) was added slowly thereto at 0 ℃. The mixture was stirred at room temperature for 24 hours. After completion of the reaction, the organic layer was extracted with EA and purified by MgSO4Removing residual water and drying. The layers were separated by column chromatography to obtain compound 3-1(20.0g, 70%).
Preparation of Compound 3-2
2-bromo-9H-carbazole (20.0g, 81.2mmol), phenylboronic acid (11.9g, 97.5mmol), Pd (PPh) were stirred in a flask under reflux3)4(4.7g，4.06mmol)、2M K2CO3(121.0mL), toluene (250.0mL), and EtOH (121.0mL) for 5 hours. After completion of the reaction, the organic layer was extracted with EA and purified by MgSO4Removing residual water and drying. The layers were separated by column chromatography to obtain compound 3-2(17.0g, 86%).
Preparation of Compounds 3-3
Compound 3-2(17.0g, 70.0mmol), 1-iodo-3-bromobenzene (17.7mL, 140.0mmol), Cul (6.6g, 35.0mmol), K3PO4(44.5g, 210.0mmol), Ethylenediamine (EDA) (4.7mL, 70.0mmol) and toluene (350.0mL) were dissolved in the flask and refluxed at 120 ℃ for 5 hours. After completion of the reaction, the organic layer was extracted with EA and purified by MgSO4Removing residual waterDrying is carried out. The layers were separated by column chromatography to obtain compound 3-3(27.0g, 97%).
Preparation of Compounds 3-4
In a flask, compound 3-3(27.0g, 67.7mmol) and compound 3-1(17.5g, 67.7mmol) were dissolved in (522.0 mL). P in addition to methanesulfonic acid (MSA)2O5(0.04mL, 1.35mmol) then the mixture was stirred for 10 minutes. After completion of the reaction, NaHCO was added3(solution) and the organic layer was extracted with DCM. By using MgSO4The remaining water was removed to dry the organic layer and separated by column chromatography to obtain compound 3-4(40.0g, 95%).
Preparation of Compounds 3-5
In a flask were placed compound 3-4(15.0g, 23.4mmol), 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (6.6g, 25.74mmol), palladium (II) chloride (PdCl)2(PPh3)4) (659.0mg, 0.94mmol) and KOAc (10.0g, 102.9mmol) were dissolved in 1, 4-dioxane (156.0 mL). The mixture was stirred at 120 ℃ for 4 hours. After completion of the reaction, the organic layer was extracted with EA and purified by MgSO4Removing residual water and drying. The organic layer was separated via column chromatography to obtain compound 3-5(10.6g, 66%).
Preparation of Compound H-90
Compounds 3-5(10.6g, 15.4mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.8g, 14.0mmol), Pd (PPh) were stirred in a flask at 120 deg.C3)4(820.0mg，0.77mmol)、2M K2CO3(60.0mL), EtOH (60.0mL), and toluene (180.0mL) for 5 hours. After completion of the reaction, the organic layer was extracted with EA and purified by MgSO4Removing residual water and drying. Compound H-90(4.0g, 32.7%) was obtained by recrystallization from EA and MeOH.
mp 256 ℃, UV 324nm (in toluene), PL 439nm (in toluene), MS/EIMS 790.95
Apparatus example 1: production of OLED devices Using organic electroluminescent Compounds according to the invention
An Organic Light Emitting Diode (OLED) device using the organic electroluminescent compound of the present invention was manufactured as follows: a transparent electrode Indium Tin Oxide (ITO) film (15. omega./sq) used on a glass substrate (Samsung Corning, Republic of Korea) of an OLED device was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water in this order, and then stored in isopropyl alcohol1，N1′- ([1, 1' -biphenyl)]-4, 4' -diyl) bis (N)1- (Naphthalen-1-yl) -N4，N4Introduction of diphenylbenzene-1, 4-diamine into the unit of the vacuum vapor deposition apparatus and subsequent control of the pressure in the apparatus chamber to 10-6And (4) supporting. Subsequently, a current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate. Next, N ' -bis (4-biphenyl) -N, N ' -bis (4-biphenyl) -4, 4 ' -diaminobiphenyl was introduced into another unit of the vacuum vapor deposition apparatus, and a current was applied to the unit to evaporate the introduced material, thereby forming a hole transport layer having a thickness of 20nm on the hole injection layer. The compound H-34 is introduced as a host into one unit of the vacuum vapor deposition apparatus, and the compound D-1 is introduced as a dopant into the other unit. The two materials were evaporated at different ratios, and the dopant was deposited in a doping amount of 15 wt% based on the total weight of the host and the dopant, so that a light emitting layer having a thickness of 30nm was formed on the hole transport layer. Followed by reacting 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole is incorporated into one unit and quinolyl lithium is incorporated into the other unit. Both materials were evaporated at the same ratio and deposited at doping amounts of 50 wt%, respectively, to form an electron transport layer having a thickness of 30nm on the light emitting layer. Next, after quinolyl lithium having a thickness of 2nm was deposited as an electron injection layer on the electron transport layer, an Al cathode having a thickness of 150nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thereby, an OLED device was manufactured. For manufacturing OLED devicesMaterials were purified by vacuum sublimation at 10-6 torr prior to use.
The fabricated OLED device showed a current density of 3.32mA/cm at 2.5V2And a luminance of 1310cd/m2Green light emission of (2).
Apparatus example 2: production of OLED devices Using organic electroluminescent Compounds according to the invention
An OLED device was fabricated in the same manner as device example 1, but with the compound H-57 instead being used as the host in the light emitting material.
The fabricated OLED device showed a current density of 7.26mA/cm at 2.6V2And a luminance of 2840cd/m2Green light emission of (2).
Example apparatus 3: production of OLED devices Using organic electroluminescent Compounds according to the invention
An OLED device was fabricated in the same manner as device example 1, but with the compound H-90 instead being used as the host in the light emitting material.
The fabricated OLED device showed a current density of 9.40mA/cm at 2.7V2And has a luminance of 3910cd/m2Green light emission of (2).
Apparatus example 4: production of OLED devices Using organic electroluminescent Compounds according to the invention
An OLED device was fabricated in the same manner as device example 1, but with the compound H-15 instead being used as the host in the light emitting material.
The fabricated OLED device showed a current density of 2.45mA/cm at 2.6V2And a luminance of 890cd/m2Green light emission of (2).
Comparative example 1: fabrication of OLED devices using conventional light emitting materials
An OLED device was fabricated in the same manner as in device example 1, except that compound 1 was used as a host and compound D-86 was used as a dopant in the light emitting material instead.
The fabricated OLED device showed a current density of 5.20mA/cm at 4.3V2And has a brightness of1020cd/m2Green light emission of (2).
Compound 1
The organic electroluminescent compounds according to the present invention provide superior light emitting characteristics compared to conventional light emitting substances. In addition, the organic electroluminescent device using the organic electroluminescent compound of the present invention as a light emitting host material provides good light emitting characteristics and reduces driving voltage, thereby enhancing power efficiency and improving power consumption.
Claims (5)
1. An organic electroluminescent compound represented by the following formula 1:
wherein
A1Represents a substituted or unsubstituted triazinyl group;
wherein the substituents of the substituted triazinyl group are each independently a (C6-C30) aryl group;
L1represents a single bond or an unsubstituted phenylene group;
R1represents an unsubstituted (C6-C30) aryl group;
R2represents hydrogen, deuterium, or an unsubstituted (C6-C30) aryl group;
R3represents hydrogen or deuterium;
R4and R5Each independently represents hydrogen or deuterium;
a. c and d each independently represent an integer of 1 to 4; wherein a, c or d is an integer of 2 or more, each R2、R4Or R5The same or different;
b represents an integer of 1 to 3; wherein b is an integer of 2 or greater, each R3The same or different;
n represents an integer of 0 or 1;
m represents an integer of 1.
2. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is represented by the following formula 3, 4 or 5:
wherein
A1、L1、R1To R5A, b, c, d, m and n are as defined in claim 1.
3. The organic electroluminescent compound according to claim 1, wherein R is1Represents a (C6-C20) aryl group; r2Represents hydrogen, deuterium, or (C6-C20) aryl.
4. An organic electroluminescent compound selected from the group consisting of:
5. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2013-0149733 | 2013-12-04 | ||
| KR1020130149733A KR102184893B1 (en) | 2013-12-04 | 2013-12-04 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| PCT/KR2014/011698 WO2015084021A1 (en) | 2013-12-04 | 2014-12-02 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105745200A CN105745200A (en) | 2016-07-06 |
| CN105745200B true CN105745200B (en) | 2021-08-17 |
Family
ID=53273713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480063398.1A Active CN105745200B (en) | 2013-12-04 | 2014-12-02 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6599860B2 (en) |
| KR (1) | KR102184893B1 (en) |
| CN (1) | CN105745200B (en) |
| TW (1) | TW201533036A (en) |
| WO (1) | WO2015084021A1 (en) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102411748B1 (en) * | 2014-03-17 | 2022-06-23 | 롬엔드하스전자재료코리아유한회사 | Electron Buffering Material and Organic Electroluminescent Device |
| WO2015142040A1 (en) | 2014-03-17 | 2015-09-24 | Rohm And Haas Electronic Materials Korea Ltd. | Electron buffering material and organic electroluminescent device |
| JP6588688B2 (en) * | 2014-03-27 | 2019-10-09 | 旭有機材株式会社 | Compound, composition and cured product |
| KR102427918B1 (en) * | 2014-04-29 | 2022-08-03 | 롬엔드하스전자재료코리아유한회사 | Electron transport material and an organic electroluminescence device comprising the same |
| WO2015167199A1 (en) * | 2014-04-29 | 2015-11-05 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
| WO2015190789A1 (en) * | 2014-06-09 | 2015-12-17 | Rohm And Haas Electronic Materials Korea Ltd. | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
| WO2017014546A1 (en) * | 2015-07-20 | 2017-01-26 | Rohm And Haas Electronic Materials Korea Ltd. | Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same |
| KR20170010715A (en) | 2015-07-20 | 2017-02-01 | 롬엔드하스전자재료코리아유한회사 | Luminescent Material for Delayed Fluorescence and Organic Electroluminescent Device Comprising the Same |
| US10580999B2 (en) | 2016-01-05 | 2020-03-03 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| KR102602194B1 (en) * | 2016-01-05 | 2023-11-15 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light-emitting device comprising the same |
| CN106496097B (en) * | 2016-08-31 | 2019-02-01 | 河南省科学院化学研究所有限公司 | A kind of bromo- 9-(9- phenyl fluorenes -9- base of 3-) carbazole synthetic method |
| CN106397303B (en) * | 2016-08-31 | 2019-04-12 | 河南省科学院化学研究所有限公司 | A kind of synthetic method of 9- (3- bromophenyl) -3- (9- phenyl -9H- fluorenyl) -9H- carbazole |
| CN107880028B (en) * | 2016-09-30 | 2021-03-02 | 中节能万润股份有限公司 | Compound with aza-benzene as core and organic electroluminescent device |
| CN107880031B (en) * | 2016-09-30 | 2021-03-02 | 中节能万润股份有限公司 | Compound with aza-benzene as core and application thereof in organic electroluminescent device |
| WO2018095389A1 (en) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Nitrogen-containing fused heterocyclic ring compound and application thereof |
| CN108148048B (en) * | 2016-12-06 | 2021-03-30 | 中节能万润股份有限公司 | Compound with aza-benzene as core and application thereof in organic electroluminescent device |
| CN108203428A (en) * | 2016-12-19 | 2018-06-26 | 江苏三月光电科技有限公司 | A kind of compound and its application using carbazole as core |
| CN108239070B (en) * | 2016-12-27 | 2021-06-15 | 中节能万润股份有限公司 | Compound with terparbazole as core and application of compound in organic electroluminescent device |
| CN108239072A (en) * | 2016-12-27 | 2018-07-03 | 江苏三月光电科技有限公司 | A kind of pyrrolotriazine derivatives and its application on organic electroluminescence device |
| KR20180097806A (en) | 2017-02-23 | 2018-09-03 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN107337680B (en) * | 2017-07-17 | 2019-02-22 | 江苏三月光电科技有限公司 | It is a kind of using fluorenes as the organic compound of core and its application in OLED device |
| KR102162402B1 (en) | 2017-07-21 | 2020-10-06 | 삼성에스디아이 주식회사 | Organic optoelectronic device and display device |
| CN108424420B (en) * | 2017-09-30 | 2021-01-12 | 北京绿人科技有限责任公司 | Triazine compound containing silicon atom, application thereof and organic electroluminescent device |
| EP3483153A1 (en) * | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and aryl group and their use in organic electronic devices |
| EP3483157A1 (en) * | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and hetero-fluorene group |
| KR102098920B1 (en) * | 2018-03-08 | 2020-04-10 | 대주전자재료 주식회사 | Organic compound comprising boron and organic electroluminescent device comprising the same |
| CN110272427B (en) * | 2018-03-14 | 2022-03-29 | 江苏三月科技股份有限公司 | Compound with fluorene as core, preparation method thereof and application thereof in organic electroluminescent device |
| KR102044943B1 (en) | 2018-05-28 | 2019-11-14 | 삼성에스디아이 주식회사 | Compound, composition and organic optoelectronic device and display device |
| CN112105619B (en) * | 2018-09-04 | 2023-09-29 | 株式会社Lg化学 | Polycyclic compound and organic light emitting device including the same |
| KR102471152B1 (en) * | 2019-01-10 | 2022-11-24 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| CN110437211A (en) * | 2019-07-15 | 2019-11-12 | 南京邮电大学 | A kind of thermal activation delayed fluorescence material and its preparation method and application |
| CN117777108B (en) * | 2024-02-27 | 2024-05-10 | 德州学院 | Carbazolofluorene-containing compound, organic light-emitting device using compound and preparation method of compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8377572B2 (en) * | 2007-09-21 | 2013-02-19 | Cheil Industries, Inc. | Polymer and organic photoelectric device including the same |
| CN102977006A (en) * | 2012-12-21 | 2013-03-20 | 南京邮电大学 | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof |
| US8586200B2 (en) * | 2007-09-14 | 2013-11-19 | Cheil Industries, Inc. | Organic compound, and organic photoelectric device including the same |
| CN104471021A (en) * | 2012-06-04 | 2015-03-25 | 株式会社P&Htech | Novel organic electroluminescent element compound and organic electroluminescent element comprising same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100957288B1 (en) | 2002-03-15 | 2010-05-12 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent devices and organic electroluminescent devices made by using the same |
| EP1489155A4 (en) | 2002-03-22 | 2006-02-01 | Idemitsu Kosan Co | Material for organic electroluminescent devices and organic electroluminescent devices made by using the same |
| CN101511834B (en) | 2006-11-09 | 2013-03-27 | 新日铁化学株式会社 | Compound for organic electroluminescent device and organic electroluminescent device |
| CN102421868B (en) * | 2009-05-15 | 2015-05-20 | 第一毛织株式会社 | Compound for organic photoelectric device and organic photoelectric device comprising same |
| WO2013183851A1 (en) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | Novel organic electroluminescent element compound and organic electroluminescent element comprising same |
| KR101550429B1 (en) * | 2013-04-30 | 2015-09-08 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
-
2013
- 2013-12-04 KR KR1020130149733A patent/KR102184893B1/en active IP Right Grant
-
2014
- 2014-12-02 CN CN201480063398.1A patent/CN105745200B/en active Active
- 2014-12-02 WO PCT/KR2014/011698 patent/WO2015084021A1/en active Application Filing
- 2014-12-02 JP JP2016532083A patent/JP6599860B2/en active Active
- 2014-12-03 TW TW103141931A patent/TW201533036A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586200B2 (en) * | 2007-09-14 | 2013-11-19 | Cheil Industries, Inc. | Organic compound, and organic photoelectric device including the same |
| US8377572B2 (en) * | 2007-09-21 | 2013-02-19 | Cheil Industries, Inc. | Polymer and organic photoelectric device including the same |
| CN104471021A (en) * | 2012-06-04 | 2015-03-25 | 株式会社P&Htech | Novel organic electroluminescent element compound and organic electroluminescent element comprising same |
| CN102977006A (en) * | 2012-12-21 | 2013-03-20 | 南京邮电大学 | Pyridine-fluorene organic electrophosphorescence main body luminescent material and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Jianfeng Zhao et al..One-pot synthesis of 2-bromo-4,5-diaza fluoren-9-one via a tandem oxidationebromination-rearrangement of phenanthroline and its hammer-shaped donoreacceptor organic semiconductors.《Tetrahedron》.2011,第67卷1977-1982. * |
| Xianghua Zhao et al..A bulky pyridinyl fluorene-fuctionalizing approach to synthesize diaryl fluorene-based bipolar host materials for efficient red, green, blue and white electrophosphorescent devices.《Journal of Materials Chemistry C》.2013,第1卷3482-3490. * |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201533036A (en) | 2015-09-01 |
| JP6599860B2 (en) | 2019-10-30 |
| JP2017501127A (en) | 2017-01-12 |
| KR102184893B1 (en) | 2020-12-01 |
| WO2015084021A1 (en) | 2015-06-11 |
| CN105745200A (en) | 2016-07-06 |
| KR20150064878A (en) | 2015-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105745200B (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| EP3145924B1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| JP6525381B2 (en) | Novel organic electroluminescent compound and organic electroluminescent device comprising the same | |
| CN106232591B (en) | Electron transport material and organic electroluminescent device comprising the same | |
| KR102411746B1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| JP6525382B2 (en) | Novel organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3137467B1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| KR102251474B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR101431645B1 (en) | Light-Emitting Layer and Organic Electroluminescence Device comprising the same | |
| KR102430648B1 (en) | A Hole Transport Material and an Organic Electroluminescent Device Comprising the Same | |
| CN105392789B (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR102659376B1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| CN106536526B (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR102397506B1 (en) | An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same | |
| KR20140024734A (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| KR20140035737A (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| TW201404861A (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| EP3440155B1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| KR101468402B1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| KR20140082486A (en) | Novel organic electroluminescent compounds and organic electroluminescent device containing the same | |
| KR102420202B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| JP7057787B2 (en) | Organic electroluminescent compounds and organic electroluminescent devices containing them | |
| KR20150073233A (en) | An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same | |
| JP6788581B2 (en) | New organic electroluminescent compounds and organic electroluminescent devices containing them | |
| KR102370068B1 (en) | Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |