WO2015084114A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- WO2015084114A1 WO2015084114A1 PCT/KR2014/011968 KR2014011968W WO2015084114A1 WO 2015084114 A1 WO2015084114 A1 WO 2015084114A1 KR 2014011968 W KR2014011968 W KR 2014011968W WO 2015084114 A1 WO2015084114 A1 WO 2015084114A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- aryl
- membered
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 128
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 19
- 125000005549 heteroarylene group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 65
- 239000000463 material Substances 0.000 description 58
- 239000000203 mixture Substances 0.000 description 44
- -1 2-methylbut-2-enyl Chemical group 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 239000002019 doping agent Substances 0.000 description 15
- 239000004305 biphenyl Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 235000010290 biphenyl Nutrition 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 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
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-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
- 238000000034 method Methods 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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
- JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 2
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 2
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 2
- SEQHEDQNODAFIU-UHFFFAOYSA-N 6-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2CCC(=O)C2=C1 SEQHEDQNODAFIU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- HAPOJKSPCGLOOD-UHFFFAOYSA-N Benzo[b]fluorene Chemical compound C1=CC=C2C=C3CC4=CC=CC=C4C3=CC2=C1 HAPOJKSPCGLOOD-UHFFFAOYSA-N 0.000 description 2
- FRIJWEQBTIZQMD-UHFFFAOYSA-N Benzo[c]fluorene Chemical compound C1=CC2=CC=CC=C2C2=C1CC1=CC=CC=C12 FRIJWEQBTIZQMD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- MLMNDNOSVOKYMT-UHFFFAOYSA-N benzo[b]fluoren-11-one Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C3=CC2=C1 MLMNDNOSVOKYMT-UHFFFAOYSA-N 0.000 description 2
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-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
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 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
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 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
- 230000008646 thermal stress Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 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
- 239000008096 xylene Substances 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- 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
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 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
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 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
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- KSONICAHAPRCMV-UHFFFAOYSA-N 5-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2C(=O)CCC2=C1 KSONICAHAPRCMV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NXTRQJAJPCXJPY-UHFFFAOYSA-N 910058-11-6 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 NXTRQJAJPCXJPY-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- DZAPZFBNZVILMS-UHFFFAOYSA-N C(C1)C=CC=C1[Si](c1ccccc1)(c1ccccc1)c1cccc(C2=CCNC([n]3c(cc(cc4)-c5ccccc5)c4c4c3cccc4)=N2)c1 Chemical compound C(C1)C=CC=C1[Si](c1ccccc1)(c1ccccc1)c1cccc(C2=CCNC([n]3c(cc(cc4)-c5ccccc5)c4c4c3cccc4)=N2)c1 DZAPZFBNZVILMS-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-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
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-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
- 125000000217 alkyl 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 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
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 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
- 239000011248 coating agent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=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
- 229960004132 diethyl ether Drugs 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
- 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
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 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
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000002910 rare earth metals Chemical class 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010189 synthetic method 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
- 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Definitions
- the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
- fluorescent materials have been widely used as light-emitting material.
- phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, phosphorescent light-emitting materials have been widely being researched.
- Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- BCP bathocuproine
- BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
- the organic EL device may be manufactured with a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised.
- a compound for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
- CuPc copper phthalocyanine
- NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
- TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
- MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
- Korean Patent Application Laying-open No. 10-2012-0029446, WO 2013-065589, and WO 2007-119800 disclose an amine derivative having a benzofluorene-based substituent, as a compound for an organic EL device.
- benzofluorene-based substituents of the references are benzo[ a ]fluorene- or benzo[ c ]fluorene-based substituents.
- An amine derivative having a benzo[ b ]fluorene-based substituent is not specifically disclosed in the references.
- the objective of the present disclosure is to provide an organic electroluminescent compound showing luminous efficiency such as current efficiency, and an organic electroluminescent device comprising the same.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and Ar 1 and Ar 2 may be fused with each other to form a ring;
- Ar 5 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
- L 2 represents a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano, a nitro, or a hydroxyl; or may be linked to an adjacent substituent(s) to form
- R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- n and m each independently, represent 0 or 1, provided that both n and m cannot be simultaneously 0;
- a represents an integer of 1 to 3; where a is an integer of 2 or more, each of R 1 may be the same or different;
- b represents an integer of 1 to 6; where b is an integer of 2 or more, each of R 2 may be the same or different;
- the heterocycloalkyl contains at least one hetero atom selected from O, S, and N.
- the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device showing excellence in luminous efficiency such as current efficiency.
- the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound.
- alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- Alkenyl includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- Alkynyl includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- substituted in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
- the substituents for the substituted alkyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, and the substituted arylalkyl of Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , and R 11 to R 17 of formula 1, each independently, are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl unsubstituted or substituted with a halogen; a (C1-C30)alkoxy; a (C6-C30)aryl; a (3- to 30-membered)heteroaryl unsubstitute
- the compound of formula 1 is represented by any one of the following formulae 2 to 4, and preferably the following formula 2 or 3:
- Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , a and b are as defined in formula 1 above.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl, and Ar 1 and Ar 2 may be fused with each other to form a ring; and more preferably, represent a substituted or unsubstituted (C6-C21)aryl, the substituent of the (C6-C21)aryl may be at least one selected from the group consisting of a (C1-C30)alkyl, a (C6-C21)aryl unsubstituted or substituted with a (C1-C10)alkyl, and a (5- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
- Ar 1 to Ar 4 each independently, may represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, and Ar 1 and Ar 2 may be fused with each other to form a ring.
- the substituent of Ar 1 to Ar 4 may be at least one selected from the group consisting of a (C1-C4)alkyl, phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, 9-phenylcarbazolyl, dibenzothiophenyl, and dibenzofuranyl.
- a (C1-C4)alkyl phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, 9-phenylcarbazolyl, dibenzothiophenyl, and dibenzofuranyl.
- the ring formed by Ar 1 and Ar 2 may be represented by the following formula 5:
- R 3 and R 4 each independently, represent hydrogen, a (C1-C30)alkyl, a (C6-C30)aryl, or a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; and * represents a site for connecting to L 1 .
- one of R 3 and R 4 represents hydrogen, and the other may be selected from the group consisting of a (C1-C4)alkyl; phenyl; biphenyl; naphthyl; carbazolyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl; dibenzothiophenyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl; and dibenzofuranyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl.
- a (C1-C4)alkyl phenyl; biphenyl; naphthyl
- carbazolyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl dibenzothiophenyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl
- dibenzofuranyl unsub
- Ar 5 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
- Ar 5 represents a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl.
- Ar 5 represents an unsubstituted (C1-C10)alkyl; a (C6-C18)aryl, unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C21)aryl, a (6- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C13)aryl, or a di(C6-C18)arylamino; or a (6- to 21-membered)heteroaryl unsubstituted or substituted with a (C1-C10)alkyl or a (C6-C18)aryl and containing a hetero atom(s) selected from N, O, and S.
- Ar 5 represents a (C1-C4)alkyl; phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, anthracenyl, or fluorenyl, unsubstituted or substituted with a (C1-C4)alkyl, phenyl, carbazolyl, diphenylpyrimidyl, diphenyltriazinyl, phenylbenzimidazolyl, diphenylamino, (phenyl)(biphenyl)amino, di(biphenyl)amino, or (phenyl)(naphthyl)amino; or carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, dibenzofuranyl, or benzonaphthofuranyl, unsubstituted or substituted with phenyl.
- L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
- L 1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene.
- L 1 represents a single bond; a (C6-C18)arylene unsubstituted or substituted with a (C1-C10)alkyl; or a (5- to 18-membered)heteroarylene unsubstituted or substituted with a (C1-C10)alkyl and containing nitrogen as a hetero atom.
- L 1 represents a single bond, phenyl, or pyrimidyl.
- L 2 represents a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
- L 2 represents a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene.
- L 2 represents an unsubstituted (C1-C10)alkylene; a (C6-C18)arylene unsubstituted or substituted with a (C1-C10)alkyl; or a (6- to 21-membered)heteroarylene unsubstituted or substituted with a (C1-C10)alkyl and containing oxygen as a hetero atom.
- L 2 represents a (C1-C4)alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, or dibenzofuranyl.
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 ), -Si(R 13 )(R 14 )(R 15 ), -S(R 16 ), -O(R 17 ), a cyano, a nitro, or a hydroxyl, or may be linked to an adjacent substituent(s) to form
- R 11 to R 17 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
- R 1 and R 2 each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, a substituted or unsubstituted (5- to 21-membered)heteroaryl, or -N(R 11 )(R 12 ).
- R 11 and R 12 each independently, represent a substituted or unsubstituted (C6-C21)aryl.
- R 1 and R 2 each independently, represent hydrogen; an unsubstituted (C6-C18)aryl; an unsubstituted (6- to 18-membered)heteroaryl containing nitrogen as a hetero atom; or -N(R 11 )(R 12 ). More preferably, R 11 and R 12 , each independently, represent an unsubstituted (C6-C18)aryl.
- R 1 and R 2 each independently, represent hydrogen, phenyl, pyridyl, pyrimidyl, carbazolyl, diphenylamino, (phenyl)(biphenyl)amino, di(biphenyl)amino, or (phenyl)(naphthyl)amino.
- n and m each independently, represent 0 or 1, provided that both n and m cannot be simultaneously 0.
- a represents an integer of 1 to 3; where a is an integer of 2 or more, each of R 1 may be the same or different. Preferably, a represents 1.
- b represents an integer of 1 to 6; where b is an integer of 2 or more, each of R 2 may be the same or different. Preferably, b represents 1.
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl; and Ar 1 and Ar 2 may be fused with each other to form a ring;
- Ar 5 represents a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5- to 21-membered)heteroaryl;
- L 1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5- to 21-membered)heteroarylene;
- L 2 represents a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsub
- Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C21)aryl
- the substituent of the (C6-C21)aryl may be at least one selected from the group consisting of a (C1-C30)alkyl, a (C6-C21)aryl unsubstituted or substituted with a (C1-C10)alkyl, and a (5- to 21-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl
- Ar 1 and Ar 2 may be fused with each other to form a ring
- Ar 5 represents an unsubstituted (C1-C10)alkyl, a (C6-C18)aryl, unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C21)aryl, a (6- to 21-membered)
- organic electroluminescent compound of formula 1 includes the following, but is not limited thereto:
- the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to one skilled in the art. For example, it can be prepared according to the following reaction scheme 1 or 2.
- the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
- the material may consist of the organic electroluminescent compound of the present disclosure. Otherwise, the material may further comprise a conventional compound(s) which has been comprised for an organic electroluminescent material, in addition to the compound of the present disclosure.
- the organic electroluminescent material may be a host material or a hole transport material.
- the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- the organic layer may comprise at least one compound of formula 1.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron buffer layer, and an electron blocking layer.
- the organic electroluminescent compound of the present disclosure may be comprised in at least one of the light-emitting layer and the hole transport layer.
- the organic electroluminescent compound of the present disclosure may be comprised as a hole transport material.
- the organic electroluminescent compound of the present disclosure may be comprised as a host material.
- the light-emitting layer may comprise a light-emitting material known in the art, or the organic electroluminescent compound of the present disclosure other than the one used as a hole transport material.
- the light-emitting material known in the art may be a host material known in the art, and may further comprise at least one dopant.
- the host material known in the art may be a fluorescent or phosphorescent host material known in the art.
- the organic electroluminescent compound of the present disclosure is comprised as a host material (a first host material) in a light-emitting layer
- at least one dopant may be further comprised, and if necessary, another compound may be comprised as a second host material.
- the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
- the compound selected from the group consisting of the compounds of formulae 6 to 8 below is preferable as the known host material or the second host material in view of luminous efficiency.
- R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl or R 25 R 26 R 27 Si-;
- R 25 to R 27 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
- L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
- M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered
- the host materials represented by formulae 6 to 8 include the following:
- TPS triphenylsilyl
- the dopant is preferably at least one phosphorescent dopant.
- the phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
- the phosphorescent dopant may be preferably selected from the group consisting of compounds represented by the following formulae 9 to 11.
- L is selected from the following structures:
- R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
- R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a cyano, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C1-C30)alkoxy; or R 106 to R 109 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a substituted or unsubstituted fluorene, a substituted or unsubstituted di
- the phosphorescent dopant material includes the following:
- a mixture or composition for preparing an organic electroluminescent device comprises the compound of the present disclosure.
- the mixture or composition may be a mixture or composition for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device.
- the compound of the present disclosure may be comprised as a host material.
- the mixture or composition may further comprise a second host material, for example, those selected from the compounds represented by formulae 6 to 8.
- the compound of the present disclosure may be comprised as a hole transport material.
- the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, wherein the organic layer may comprise a light-emitting layer or both a light-emitting layer and a hole transport layer, which may comprise the mixture or composition for preparing an organic electroluminescent device of the present disclosure.
- the organic electroluminescent device of the present disclosure may further comprise, in addition to the compound of formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic layer may further comprise a light-emitting layer and a charge generating layer.
- the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the art, besides the compound of the present disclosure.
- a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
- a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds
- the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
- a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
- organic electroluminescent compound of the present disclosure the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
- Compound 2-1 was prepared in the same manner as in Example 1 for the preparations of compounds 1-1 to 1-3, except for using 5-bromoindanone instead of 6-bromoindanone.
- OLED was produced using the material of the present disclosure as follows.
- a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone and isopropanol, sequentially, and was then stored in isopropanol.
- the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
- N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10E -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- Compound C-1 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- compound H-1 as shown in Table 2 below was introduced into one cell of the vacuum vapor depositing apparatus as a host material, and compound D-1 was introduced into another cell as a dopant.
- the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- an OLED was produced. All the materials used for producing the OLED were those purified by vacuum sublimation at 10E -6 torr.
- the produced OLED showed green emission having a luminance of 1,500 cd/m 2 and a current density of 3.5 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-71 was used to form a hole transport layer, and compounds H-2 and H-3 as shown in Table 2 below were used as a host.
- the produced OLED showed blue emission having a luminance of 700 cd/m 2 and a current density of 14.0 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-89 was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 900 cd/m 2 and a current density of 1.9 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound C-125 was used to form a hole transport layer, and compounds H-2 and H-3 were used as a host.
- the produced OLED showed blue emission having a luminance of 1,200 cd/m 2 and a current density of 25.0 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound T-1 as shown in Table 2 below was used to form a hole transport layer having a thickness of 20 nm.
- the produced OLED showed green emission having a luminance of 9,800 cd/m 2 and a current density of 26.1 mA/cm 2 .
- OLED was produced in the same manner as in Device Example 1, except that compound T-1 was used to form a hole transport layer, and compounds H-2 and H-3 were used as a host.
- the produced OLED showed blue emission having a luminance of 2,800 cd/m 2 and a current density of 141.2 mA/cm 2 .
- the compound for organic electronic material of the present disclosure has better luminous characteristics than the conventional compounds.
- the organic electroluminescent device comprising the compound for organic electronic material of the present disclosure shows excellences in luminous characteristics and lifespan.
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)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201480063491.2A CN105764876A (zh) | 2013-12-06 | 2014-12-05 | 有机电致发光化合物和包含所述化合物的有机电致发光装置 |
JP2016532095A JP6680675B2 (ja) | 2013-12-06 | 2014-12-05 | 有機電界発光化合物及びそれを含む有機電界発光デバイス |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2013-0151461 | 2013-12-06 | ||
KR1020130151461A KR101939552B1 (ko) | 2013-12-06 | 2013-12-06 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015084114A1 true WO2015084114A1 (en) | 2015-06-11 |
Family
ID=53273785
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2014/011968 WO2015084114A1 (en) | 2013-12-06 | 2014-12-05 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP6680675B2 (zh) |
KR (1) | KR101939552B1 (zh) |
CN (2) | CN105764876A (zh) |
TW (1) | TW201529539A (zh) |
WO (1) | WO2015084114A1 (zh) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017048184A (ja) * | 2015-09-03 | 2017-03-09 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
CN107043399A (zh) * | 2016-02-09 | 2017-08-15 | 环球展览公司 | 有机电致发光材料和装置 |
CN107108498A (zh) * | 2015-10-26 | 2017-08-29 | 株式会社Lg化学 | 胺化合物和包含其的有机发光元件 |
US20170294597A1 (en) * | 2016-04-11 | 2017-10-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2018070773A1 (en) * | 2016-10-11 | 2018-04-19 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device |
US20180186764A1 (en) * | 2015-09-09 | 2018-07-05 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
CN109071413A (zh) * | 2016-05-03 | 2018-12-21 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
WO2019004587A1 (en) * | 2017-06-30 | 2019-01-03 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING SAME |
JP2019515877A (ja) * | 2016-03-28 | 2019-06-13 | エルジー・ケム・リミテッド | 化合物およびこれを含む有機電子素子 |
US10505121B2 (en) * | 2018-02-02 | 2019-12-10 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element using the same, and electronic device thereof |
US10600968B2 (en) | 2017-04-03 | 2020-03-24 | Samsung Display Co., Ltd. | Amine compound and organic electroluminescence device including the same |
US10745362B2 (en) | 2015-05-14 | 2020-08-18 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising same |
US10875825B2 (en) | 2017-08-18 | 2020-12-29 | Samsung Display Co., Lid. | Amine-based compound and organic light-emitting device including the same |
US10976660B2 (en) * | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
EP3649102A4 (en) * | 2017-06-30 | 2021-04-14 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT JOINT AND ORGANIC ELECTROLUMINESCENT DEVICE WITH IT |
JP2021091726A (ja) * | 2015-12-17 | 2021-06-17 | 株式会社半導体エネルギー研究所 | 有機化合物 |
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
US11056652B2 (en) | 2013-12-06 | 2021-07-06 | Merck Patent Gmbh | Compounds and organic electronic devices |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
US20220336751A1 (en) * | 2019-12-19 | 2022-10-20 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic element, and electronic device |
US11653562B2 (en) | 2018-08-10 | 2023-05-16 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
US11696499B2 (en) * | 2016-05-10 | 2023-07-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
US11744146B2 (en) | 2017-02-03 | 2023-08-29 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting device including the same |
US11856842B2 (en) | 2015-11-26 | 2023-12-26 | Samsung Display Co., Ltd. | Organic light-emitting device |
US11910707B2 (en) | 2015-12-23 | 2024-02-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
US12048239B2 (en) | 2020-04-20 | 2024-07-23 | Samsung Sdi Co., Ltd. | Composition for organic optoelectronic device, organic optoelectronic device and display device |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6535671B2 (ja) * | 2013-12-26 | 2019-06-26 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電界発光化合物及びそれを含む有機電界発光デバイス |
KR102595922B1 (ko) | 2015-12-22 | 2023-10-31 | 삼성디스플레이 주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
KR102528297B1 (ko) * | 2015-12-28 | 2023-05-04 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102611417B1 (ko) * | 2016-01-25 | 2023-12-07 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR101840162B1 (ko) * | 2016-03-28 | 2018-04-27 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
CN107438596B (zh) * | 2016-04-12 | 2020-05-22 | 株式会社Lg化学 | 化合物及包含其的有机电子元件 |
KR102455660B1 (ko) | 2016-10-11 | 2022-10-19 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
KR102690159B1 (ko) | 2017-02-28 | 2024-08-01 | 듀폰스페셜티머터리얼스코리아 유한회사 | 유기 전계 발광 소자 |
KR102668890B1 (ko) * | 2017-04-03 | 2024-05-27 | 듀폰스페셜티머터리얼스코리아 유한회사 | 유기 전계 발광 소자 |
KR102022691B1 (ko) * | 2017-04-13 | 2019-09-18 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
CN107652224B (zh) * | 2017-10-27 | 2020-07-28 | 烟台九目化学股份有限公司 | 一种萘并芴类联咔唑类化合物及应用 |
WO2019185061A1 (zh) * | 2018-03-29 | 2019-10-03 | 江苏三月光电科技有限公司 | 一种基于双二甲基芴的化合物、制备方法及其应用 |
CN110317184A (zh) * | 2018-03-29 | 2019-10-11 | 江苏三月光电科技有限公司 | 一种基于双二甲基芴的化合物、制备方法及其应用 |
WO2020009554A1 (ko) * | 2018-07-06 | 2020-01-09 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
KR102233421B1 (ko) * | 2018-07-06 | 2021-03-29 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
KR20200007644A (ko) | 2018-07-13 | 2020-01-22 | 롬엔드하스전자재료코리아유한회사 | 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
CN109400487A (zh) * | 2018-11-12 | 2019-03-01 | 长春海谱润斯科技有限公司 | 一种芴类衍生物及其有机电致发光器件 |
CN111153902A (zh) * | 2020-01-15 | 2020-05-15 | 吉林奥来德光电材料股份有限公司 | 一种有机电致发光化合物及其制法和有机电致发光器件 |
CN113402462A (zh) * | 2020-03-16 | 2021-09-17 | 中国石油化工股份有限公司 | 稠环化合物及制备方法和应用及共主体材料、发光组合物、发光器件、照明设备和显示设备 |
KR102645708B1 (ko) * | 2020-05-27 | 2024-03-11 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR102531630B1 (ko) * | 2020-11-19 | 2023-05-15 | 엘티소재주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN113717093B (zh) * | 2021-07-12 | 2024-04-05 | 阜阳欣奕华材料科技有限公司 | 化合物与有机电致发光器件、显示装置 |
CN113549003B (zh) * | 2021-07-15 | 2023-08-01 | 阜阳欣奕华材料科技有限公司 | 一种化合物与有机电致发光器件、显示装置 |
CN114163301A (zh) * | 2021-10-28 | 2022-03-11 | 陕西维世诺新材料有限公司 | 一种苯并[b]芴衍生物的制备方法及其衍生物 |
CN116332773B (zh) * | 2023-05-30 | 2023-09-19 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法和应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102702075A (zh) * | 2012-06-13 | 2012-10-03 | 吉林奥来德光电材料股份有限公司 | 含有三芳胺结构的有机电致发光材料及制备方法和应用 |
US20120286247A1 (en) * | 2011-05-11 | 2012-11-15 | Samsung Mobile Display Co., Ltd. | Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus |
WO2013081410A1 (ko) * | 2011-11-30 | 2013-06-06 | 주식회사 두산 | 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
CN103187531A (zh) * | 2011-12-30 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 有机电致发光器件及双极性有机化合物的用途 |
CN103204798A (zh) * | 2012-11-12 | 2013-07-17 | 吉林奥来德光电材料股份有限公司 | 一种芳香胺衍生物、其制备方法以及由其制成的有机电致发光器件 |
KR20140027030A (ko) * | 2012-08-23 | 2014-03-06 | (주)씨에스엘쏠라 | 유기 발광 화합물 및 이를 이용한 유기 발광 소자 |
KR20140078096A (ko) * | 2012-12-17 | 2014-06-25 | 에스에프씨 주식회사 | 플루오렌구조를 포함하는 방향족 아민 유도체 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007119800A1 (ja) | 2006-04-13 | 2007-10-25 | Tosoh Corporation | ベンゾフルオレン化合物及びその用途 |
KR100984341B1 (ko) * | 2008-05-09 | 2010-09-30 | (주)씨에스엘쏠라 | 유기 발광 소자 및 이에 사용되는 유기 발광 화합물 |
KR101003851B1 (ko) * | 2008-06-18 | 2010-12-23 | (주)씨에스엘쏠라 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
EP2194110A1 (en) * | 2008-11-26 | 2010-06-09 | Gracel Display Inc. | Electroluminescent device using electroluminescent compounds |
KR101473019B1 (ko) * | 2009-04-10 | 2014-12-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
JP2011012047A (ja) | 2009-06-05 | 2011-01-20 | Tosoh Corp | アミン誘導体及び有機エレクトロルミネッセンス素子 |
KR20120081539A (ko) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
KR101430589B1 (ko) * | 2011-02-21 | 2014-08-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
TWI570095B (zh) | 2011-11-04 | 2017-02-11 | 捷恩智股份有限公司 | 苯并茀化合物、使用了該化合物的發光層用材料以及有機電場發光元件 |
-
2013
- 2013-12-06 KR KR1020130151461A patent/KR101939552B1/ko active Application Filing
-
2014
- 2014-12-05 CN CN201480063491.2A patent/CN105764876A/zh active Pending
- 2014-12-05 JP JP2016532095A patent/JP6680675B2/ja active Active
- 2014-12-05 WO PCT/KR2014/011968 patent/WO2015084114A1/en active Application Filing
- 2014-12-05 TW TW103142315A patent/TW201529539A/zh unknown
- 2014-12-05 CN CN202110960033.0A patent/CN113582856A/zh active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120286247A1 (en) * | 2011-05-11 | 2012-11-15 | Samsung Mobile Display Co., Ltd. | Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus |
WO2013081410A1 (ko) * | 2011-11-30 | 2013-06-06 | 주식회사 두산 | 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
CN103187531A (zh) * | 2011-12-30 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 有机电致发光器件及双极性有机化合物的用途 |
CN102702075A (zh) * | 2012-06-13 | 2012-10-03 | 吉林奥来德光电材料股份有限公司 | 含有三芳胺结构的有机电致发光材料及制备方法和应用 |
KR20140027030A (ko) * | 2012-08-23 | 2014-03-06 | (주)씨에스엘쏠라 | 유기 발광 화합물 및 이를 이용한 유기 발광 소자 |
CN103204798A (zh) * | 2012-11-12 | 2013-07-17 | 吉林奥来德光电材料股份有限公司 | 一种芳香胺衍生物、其制备方法以及由其制成的有机电致发光器件 |
KR20140078096A (ko) * | 2012-12-17 | 2014-06-25 | 에스에프씨 주식회사 | 플루오렌구조를 포함하는 방향족 아민 유도체 및 이를 포함하는 유기 발광 소자 |
Cited By (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11056652B2 (en) | 2013-12-06 | 2021-07-06 | Merck Patent Gmbh | Compounds and organic electronic devices |
US10745362B2 (en) | 2015-05-14 | 2020-08-18 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising same |
JP2022068208A (ja) * | 2015-09-03 | 2022-05-09 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US11605789B2 (en) | 2015-09-03 | 2023-03-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP7370400B2 (ja) | 2015-09-03 | 2023-10-27 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
JP7042871B2 (ja) | 2015-09-03 | 2022-03-28 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US11626563B2 (en) | 2015-09-03 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3159350A1 (en) * | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2017048184A (ja) * | 2015-09-03 | 2017-03-09 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
CN106946940A (zh) * | 2015-09-03 | 2017-07-14 | 环球展览公司 | 有机电致发光材料和装置 |
EP3760635A1 (en) * | 2015-09-03 | 2021-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2020172499A (ja) * | 2015-09-03 | 2020-10-22 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
JP2017048390A (ja) * | 2015-09-03 | 2017-03-09 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US10672996B2 (en) | 2015-09-03 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106946940B (zh) * | 2015-09-03 | 2023-07-18 | 环球展览公司 | 有机电致发光材料和装置 |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180186764A1 (en) * | 2015-09-09 | 2018-07-05 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
US11673875B2 (en) * | 2015-09-09 | 2023-06-13 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
CN107108498B (zh) * | 2015-10-26 | 2020-08-21 | 株式会社Lg化学 | 胺化合物和包含其的有机发光元件 |
CN107108498A (zh) * | 2015-10-26 | 2017-08-29 | 株式会社Lg化学 | 胺化合物和包含其的有机发光元件 |
US11856842B2 (en) | 2015-11-26 | 2023-12-26 | Samsung Display Co., Ltd. | Organic light-emitting device |
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
JP2021091726A (ja) * | 2015-12-17 | 2021-06-17 | 株式会社半導体エネルギー研究所 | 有機化合物 |
US11910707B2 (en) | 2015-12-23 | 2024-02-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
CN107043399A (zh) * | 2016-02-09 | 2017-08-15 | 环球展览公司 | 有机电致发光材料和装置 |
CN107043399B (zh) * | 2016-02-09 | 2021-08-17 | 环球展览公司 | 有机电致发光材料和装置 |
JP2019515877A (ja) * | 2016-03-28 | 2019-06-13 | エルジー・ケム・リミテッド | 化合物およびこれを含む有機電子素子 |
JP2017193536A (ja) * | 2016-04-11 | 2017-10-26 | ユニバーサル ディスプレイ コーポレイション | 有機発光材料及びデバイス |
US20170294597A1 (en) * | 2016-04-11 | 2017-10-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2022003041A (ja) * | 2016-04-11 | 2022-01-11 | ユニバーサル ディスプレイ コーポレイション | 有機発光材料及びデバイス |
US10236456B2 (en) * | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109071413A (zh) * | 2016-05-03 | 2018-12-21 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
JP2019515905A (ja) * | 2016-05-03 | 2019-06-13 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電界発光化合物及びそれを含む有機電界発光デバイス |
US10797243B2 (en) | 2016-05-03 | 2020-10-06 | Rohm And Haas Electronic Materials Korea Ltd | Organic electroluminescent compound and organic electroluminescent device comprising the same |
CN109071413B (zh) * | 2016-05-03 | 2023-04-04 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含其的有机电致发光装置 |
US11696499B2 (en) * | 2016-05-10 | 2023-07-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
US10976660B2 (en) * | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
WO2018070773A1 (en) * | 2016-10-11 | 2018-04-19 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device |
US11744146B2 (en) | 2017-02-03 | 2023-08-29 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting device including the same |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
US10600968B2 (en) | 2017-04-03 | 2020-03-24 | Samsung Display Co., Ltd. | Amine compound and organic electroluminescence device including the same |
US11844269B2 (en) | 2017-06-30 | 2023-12-12 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
EP3649102A4 (en) * | 2017-06-30 | 2021-04-14 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT JOINT AND ORGANIC ELECTROLUMINESCENT DEVICE WITH IT |
WO2019004587A1 (en) * | 2017-06-30 | 2019-01-03 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING SAME |
US10875825B2 (en) | 2017-08-18 | 2020-12-29 | Samsung Display Co., Lid. | Amine-based compound and organic light-emitting device including the same |
US10505121B2 (en) * | 2018-02-02 | 2019-12-10 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element using the same, and electronic device thereof |
US11653562B2 (en) | 2018-08-10 | 2023-05-16 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
US11605784B2 (en) * | 2019-12-19 | 2023-03-14 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic element, and electronic device |
US20220336751A1 (en) * | 2019-12-19 | 2022-10-20 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic element, and electronic device |
US12048239B2 (en) | 2020-04-20 | 2024-07-23 | Samsung Sdi Co., Ltd. | Composition for organic optoelectronic device, organic optoelectronic device and display device |
Also Published As
Publication number | Publication date |
---|---|
KR101939552B1 (ko) | 2019-01-17 |
CN105764876A (zh) | 2016-07-13 |
KR20150066202A (ko) | 2015-06-16 |
JP6680675B2 (ja) | 2020-04-15 |
TW201529539A (zh) | 2015-08-01 |
JP2017501566A (ja) | 2017-01-12 |
CN113582856A (zh) | 2021-11-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2015084114A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
WO2015099485A1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
WO2015012618A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
WO2015099486A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2013165189A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
EP2831197A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
WO2014030921A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
WO2015037965A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2015084021A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2014042420A1 (en) | A novel organic electroluminescence compound and an organic electroluminescence device containing the same | |
WO2013109045A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
WO2015009076A1 (en) | A combination of a dopant compound and a host compound and an organic electroluminescent device comprising the same | |
WO2013165192A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
EP2817387A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2014196805A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
WO2014129846A1 (en) | Organic electroluminescent compounds and an organic electroluminescent device comprising the same | |
EP2828254A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2015046955A1 (en) | Novel organic electroluminescent compound and organic electroluminescent device comprising the same | |
WO2014171779A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
EP3201200A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
WO2014061991A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device containing the same | |
WO2016036207A1 (en) | A hole transport material and an organic electroluminescent device comprising the same | |
WO2014200244A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2014088290A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
WO2015093814A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14867893 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2016532095 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 14867893 Country of ref document: EP Kind code of ref document: A1 |