KR102158000B1 - 유기 전계 발광 소자 - Google Patents
유기 전계 발광 소자 Download PDFInfo
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- KR102158000B1 KR102158000B1 KR1020130114260A KR20130114260A KR102158000B1 KR 102158000 B1 KR102158000 B1 KR 102158000B1 KR 1020130114260 A KR1020130114260 A KR 1020130114260A KR 20130114260 A KR20130114260 A KR 20130114260A KR 102158000 B1 KR102158000 B1 KR 102158000B1
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- compound
- formula
- organic electroluminescent
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- 239000002019 doping agent Substances 0.000 claims abstract description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 12
- 239000011368 organic material Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 58
- 239000010410 layer Substances 0.000 description 62
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 238000004440 column chromatography Methods 0.000 description 16
- -1 etc. Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 0 CC1C=CC(C(C)(C2)*(C3C=CC4N(C5(C)C=CC=CC5)c5ccc(c6ccccc6[s]6)c6c5C4(C)C3C)=C2C2=CC=CCC2C)=CC1 Chemical compound CC1C=CC(C(C)(C2)*(C3C=CC4N(C5(C)C=CC=CC5)c5ccc(c6ccccc6[s]6)c6c5C4(C)C3C)=C2C2=CC=CCC2C)=CC1 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 125000005104 aryl silyl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 2
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 2
- 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
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- BFMXBYPBWWMIPN-UHFFFAOYSA-N 5-phenyl-7h-indolo[2,3-b]carbazole Chemical compound C1=CC=CC=C1N1C2=CC(NC=3C4=CC=CC=3)=C4C=C2C2=CC=CC=C21 BFMXBYPBWWMIPN-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FSKRYLOXKLKTEJ-UHFFFAOYSA-N Cc1ccnc(-c2c(C)cc3[s]c(cccc4)c4c3c2)c1 Chemical compound Cc1ccnc(-c2c(C)cc3[s]c(cccc4)c4c3c2)c1 FSKRYLOXKLKTEJ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- MOSQXYPUMBJMRR-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cnc1-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)cnc1-c1ccccc1 MOSQXYPUMBJMRR-UHFFFAOYSA-N 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 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
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-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
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-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
- 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
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical compound CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-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
- QNGVEVOZKYHNGL-UHFFFAOYSA-N 2-chloro-4,6-diphenylpyrimidine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QNGVEVOZKYHNGL-UHFFFAOYSA-N 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
- KTERPBUFTWOSJB-UHFFFAOYSA-N 4-naphthalen-1-yl-1-N,1-N-diphenylcyclohexa-1,5-diene-1,4-diamine Chemical compound C1(=CC=CC2=CC=CC=C12)C1(CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)N KTERPBUFTWOSJB-UHFFFAOYSA-N 0.000 description 1
- CLXUVEFBRYOAER-UHFFFAOYSA-N C=Cc1c(C2NC=CC=C2)cc(c(cccc2-c3ccccc3)c2[o]2)c2c1 Chemical compound C=Cc1c(C2NC=CC=C2)cc(c(cccc2-c3ccccc3)c2[o]2)c2c1 CLXUVEFBRYOAER-UHFFFAOYSA-N 0.000 description 1
- SQPRSIKZFLPLFT-UHFFFAOYSA-N CC(C)(c(cccc1)c1C1=CC2c3c4cccc3)C1=CC2N4c(cc1)ccc1-c1nc(-c2ccccc2)nc(C2=CC=CCC2)n1 Chemical compound CC(C)(c(cccc1)c1C1=CC2c3c4cccc3)C1=CC2N4c(cc1)ccc1-c1nc(-c2ccccc2)nc(C2=CC=CCC2)n1 SQPRSIKZFLPLFT-UHFFFAOYSA-N 0.000 description 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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Classifications
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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
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- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- 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
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- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130114260A KR102158000B1 (ko) | 2013-09-26 | 2013-09-26 | 유기 전계 발광 소자 |
| PCT/KR2014/008963 WO2015046916A1 (en) | 2013-09-26 | 2014-09-25 | A combination of a host compound and a dopant compound |
| CN201480050614.9A CN105531349A (zh) | 2013-09-26 | 2014-09-25 | 主体化合物和掺杂剂化合物的组合 |
| TW103133466A TW201527298A (zh) | 2013-09-26 | 2014-09-26 | 主體化合物及摻雜劑化合物之組合 |
| TW104136465A TW201605841A (zh) | 2013-09-26 | 2014-09-26 | 主體化合物及摻雜劑化合物之組合 |
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| KR1020130114260A KR102158000B1 (ko) | 2013-09-26 | 2013-09-26 | 유기 전계 발광 소자 |
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| KR20150034333A KR20150034333A (ko) | 2015-04-03 |
| KR102158000B1 true KR102158000B1 (ko) | 2020-09-22 |
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| KR (1) | KR102158000B1 (zh) |
| CN (1) | CN105531349A (zh) |
| TW (2) | TW201605841A (zh) |
| WO (1) | WO2015046916A1 (zh) |
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| US10457699B2 (en) * | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| 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 |
| EP3026056B1 (en) * | 2014-11-28 | 2017-11-08 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
| WO2016186321A1 (en) * | 2015-05-19 | 2016-11-24 | Rohm And Haas Electronic Materials Korea Ltd. | Phosphorous host material and organic electroluminescent device comprising the same |
| KR20160136211A (ko) * | 2015-05-19 | 2016-11-29 | 롬엔드하스전자재료코리아유한회사 | 인광 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
| KR20170001552A (ko) * | 2015-06-26 | 2017-01-04 | 롬엔드하스전자재료코리아유한회사 | 복수종의 호스트 재료와 이를 포함하는 유기 전계 발광 소자 |
| CN106699753A (zh) * | 2015-07-14 | 2017-05-24 | 上海和辉光电有限公司 | 一种化合物及其应用 |
| JP6805235B2 (ja) * | 2015-08-11 | 2020-12-23 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
| KR102399570B1 (ko) | 2015-11-26 | 2022-05-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US11910707B2 (en) | 2015-12-23 | 2024-02-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
| KR102643060B1 (ko) * | 2016-03-28 | 2024-03-04 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| KR20170127101A (ko) | 2016-05-10 | 2017-11-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR20170129599A (ko) * | 2016-05-17 | 2017-11-27 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물, 유기 전계 발광 재료, 및 이를 포함하는 유기 전계 발광 소자 |
| KR102063664B1 (ko) * | 2016-05-17 | 2020-01-08 | 삼성에스디아이 주식회사 | 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 |
| WO2017200210A1 (en) * | 2016-05-17 | 2017-11-23 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same |
| CN107488182B (zh) * | 2016-06-09 | 2020-07-28 | 株式会社Lg化学 | 化合物及利用它的有机发光元件 |
| CN106117117B (zh) * | 2016-06-24 | 2018-05-18 | 中节能万润股份有限公司 | 一种含有卤素的芴基苯并吲哚衍生物的制备方法 |
| KR20180017682A (ko) | 2016-08-10 | 2018-02-21 | 삼성전자주식회사 | 실릴계 화합물 및 이를 포함하는 유기 발광 소자 |
| CN106397415A (zh) * | 2016-08-31 | 2017-02-15 | 江苏三月光电科技有限公司 | 一种基于氮杂苯的五元环取代化合物及其应用 |
| KR102529341B1 (ko) * | 2016-10-05 | 2023-05-09 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102498770B1 (ko) * | 2016-12-27 | 2023-02-10 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자 |
| KR20180098809A (ko) | 2017-02-27 | 2018-09-05 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
| KR102129508B1 (ko) * | 2017-07-14 | 2020-07-02 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
| CN109326741A (zh) * | 2017-08-01 | 2019-02-12 | 江苏三月光电科技有限公司 | 一种含有氮杂苯类化合物的有机发光器件 |
| CN107586299A (zh) * | 2017-09-29 | 2018-01-16 | 江苏三月光电科技有限公司 | 一种以氮杂苯为核心的有机化合物及其应用 |
| CN109970623B (zh) * | 2017-12-28 | 2021-01-12 | 武汉尚赛光电科技有限公司 | 三芳胺类衍生物及其制备方法、应用和器件 |
| CN108047235B (zh) * | 2017-12-29 | 2019-10-18 | 西安瑞联新材料股份有限公司 | 一种芳香族杂环化合物及其应用 |
| KR102125962B1 (ko) | 2018-01-17 | 2020-06-23 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
| US11217757B2 (en) | 2018-03-12 | 2022-01-04 | Universal Display Corporation | Host materials for electroluminescent devices |
| WO2019221483A1 (ko) * | 2018-05-14 | 2019-11-21 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR102184860B1 (ko) * | 2018-05-14 | 2020-12-01 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| CN109096291B (zh) * | 2018-08-22 | 2022-05-20 | 宇瑞(上海)化学有限公司 | 一种含二取代基吲哚并杂环化合物的有机光电器件及其应用 |
| CN109400590A (zh) * | 2018-11-21 | 2019-03-01 | 苏州大学 | 一种热活化延迟荧光材料及其在有机发光二极管中的应用 |
| CN110041376B (zh) * | 2019-06-06 | 2021-10-29 | 江西师范大学 | 一种环金属铱配合物及其制备方法和应用 |
| KR20210063747A (ko) | 2019-11-25 | 2021-06-02 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
| KR20210143652A (ko) * | 2020-05-20 | 2021-11-29 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
| CN113816996A (zh) * | 2020-06-20 | 2021-12-21 | 北京夏禾科技有限公司 | 一种磷光有机金属配合物及其应用 |
| CN113816997B (zh) | 2020-06-20 | 2024-05-28 | 北京夏禾科技有限公司 | 一种磷光有机金属配合物及其应用 |
| CN111808142A (zh) * | 2020-07-09 | 2020-10-23 | 奥来德(上海)光电材料科技有限公司 | 一种有机磷发光化合物及其制备方法和应用 |
| CN114516890A (zh) * | 2020-11-18 | 2022-05-20 | 北京夏禾科技有限公司 | 有机电致发光材料及其器件 |
| CN114907413A (zh) * | 2021-02-06 | 2022-08-16 | 北京夏禾科技有限公司 | 有机电致发光材料及其器件 |
| CN114075203B (zh) * | 2021-06-17 | 2023-06-13 | 陕西莱特迈思光电材料有限公司 | 一种有机化合物以及使用其的有机电致发光器件和电子装置 |
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| WO2008056746A1 (fr) * | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
| KR101511072B1 (ko) * | 2009-03-20 | 2015-04-10 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 |
| US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
| US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| US9193745B2 (en) * | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
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2013
- 2013-09-26 KR KR1020130114260A patent/KR102158000B1/ko active IP Right Grant
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- 2014-09-25 CN CN201480050614.9A patent/CN105531349A/zh active Pending
- 2014-09-25 WO PCT/KR2014/008963 patent/WO2015046916A1/en active Application Filing
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- 2014-09-26 TW TW103133466A patent/TW201527298A/zh unknown
Also Published As
| Publication number | Publication date |
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| CN105531349A (zh) | 2016-04-27 |
| WO2015046916A1 (en) | 2015-04-02 |
| KR20150034333A (ko) | 2015-04-03 |
| TW201527298A (zh) | 2015-07-16 |
| TW201605841A (zh) | 2016-02-16 |
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