KR20130053846A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents
Novel organic electroluminescence compounds and organic electroluminescence device using the same Download PDFInfo
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- KR20130053846A KR20130053846A KR1020110119529A KR20110119529A KR20130053846A KR 20130053846 A KR20130053846 A KR 20130053846A KR 1020110119529 A KR1020110119529 A KR 1020110119529A KR 20110119529 A KR20110119529 A KR 20110119529A KR 20130053846 A KR20130053846 A KR 20130053846A
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- South Korea
- Prior art keywords
- substituted
- alkyl
- unsubstituted
- compound
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 238000005401 electroluminescence Methods 0.000 title abstract description 8
- 239000002019 doping agent Substances 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 239000011368 organic material Substances 0.000 claims abstract description 9
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 3
- 150000003624 transition metals Chemical class 0.000 claims abstract description 3
- -1 cyano, N-carbazolyl Chemical group 0.000 claims description 36
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 2
- 239000010410 layer Substances 0.000 abstract description 45
- 239000000463 material Substances 0.000 abstract description 31
- 239000012044 organic layer Substances 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910052746 lanthanum Inorganic materials 0.000 abstract 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 3
- 0 CC1(*)*(cccc2C)c2-c2ccccc2C1(*)I(*1C2)c3ccccc3C1=CC=C2c(c(O)c(c(O)c1O)O)c1O Chemical compound CC1(*)*(cccc2C)c2-c2ccccc2C1(*)I(*1C2)c3ccccc3C1=CC=C2c(c(O)c(c(O)c1O)O)c1O 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000005580 triphenylene group Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052741 iridium 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 125000005493 quinolyl group Chemical group 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
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SHZGCJCMOBCMKK-GASJEMHNSA-N (3r,4s,5s,6r)-6-methyloxane-2,3,4,5-tetrol Chemical compound C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-GASJEMHNSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 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
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 1
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- 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
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- UUESRJFGZMCELZ-UHFFFAOYSA-K aluminum;2-methylquinoline-8-carboxylate;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21 UUESRJFGZMCELZ-UHFFFAOYSA-K 0.000 description 1
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
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- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
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- RZBXNUXJOWMNMF-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2cc(-c(cc3)ccc3-c(cc3)cc4c3c3ccccc3c3ccccc43)ccc2c2c1ccc1c2[o]c2cc(-[n]3c4ccccc4c4c3cccc4)ccc12 Chemical compound c(cc1)ccc1-[n]1c2cc(-c(cc3)ccc3-c(cc3)cc4c3c3ccccc3c3ccccc43)ccc2c2c1ccc1c2[o]c2cc(-[n]3c4ccccc4c4c3cccc4)ccc12 RZBXNUXJOWMNMF-UHFFFAOYSA-N 0.000 description 1
- RSVHSWWFABMRSS-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(-[n](c2ccc(c3ccccc3[s]3)c3c22)c3c2c(-c(cc2)ccc2-c(cc2)cc4c2c2ccccc2c2ccccc42)ccc3)c1 Chemical compound c(cc1)ccc1-c1cccc(-[n](c2ccc(c3ccccc3[s]3)c3c22)c3c2c(-c(cc2)ccc2-c(cc2)cc4c2c2ccccc2c2ccccc42)ccc3)c1 RSVHSWWFABMRSS-UHFFFAOYSA-N 0.000 description 1
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- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- JURBTQKVGNFPRJ-UHFFFAOYSA-N ditert-butyl(methyl)phosphane Chemical compound CC(C)(C)P(C)C(C)(C)C JURBTQKVGNFPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 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 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 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 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000005559 triazolylene 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
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Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2(bis(2-(2'-benzothienyl)-pyridinato-N,C-3')iridium(acetylacetonate)), Ir(ppy)3(tris(2-phenylpyridine)iridium) 및 Firpic (Bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium) 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다. The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, (acac) Ir (btp) 2 (bis (2- (2'-benzothienyl) -pyridinato-N, C-3 ') iridium (acetylacetonate)), Ir (ppy) 3 (tris (2-phenylpyridine) iridium) and Firpic (Bis (4,6-difluorophenylpyridinato-N, C2) picolinatoiridium) are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.
인광 발광체의 호스트 재료로는 현재까지 CBP(4,4'-N,N'-dicarbazole-biphenyl)가 가장 널리 알려져 있고, BCP(Bathocuproine) 및 BAlq(aluminum(III)bis(2-methyl-8-quinolinato)(4-phenylphenolate)) 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용해 고성능의 OLED을 개발한 바 있다. CBP (4,4'-N, N'-dicarbazole-biphenyl) is the most widely known host material for phosphorescent emitters, and BCP (Bathocuproine) and BAlq (aluminum (III) bis (2-methyl-8-) High-efficiency OLEDs using a hole blocking layer such as quinolinato) (4-phenylphenolate)) are known. In Japan, Pioneer and others have developed high-performance OLEDs using BAlq derivatives as hosts.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 단점을 갖고 있다. OLED에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력효율은 전압에 반비례하고, 따라서 OLED의 소비 전력을 낮으려면 전력 효율을 높여야 한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 사용되던 BAlq 또는 CBP와 같은 종래재료의 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. 또한, OLED 소자에 사용할 경우 수명 측면에서도 결코 만족스럽지 못하였다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the OLED, power efficiency = [(π / voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). In addition, when used for an OLED device, the lifetime was never satisfactory.
한편 한국특허공개공보 제KR2010-0056490호에는 트리페닐렌에 카바졸, 다이벤조퓨란, 다이벤조싸이오펜 등이 치환된 유기 전기 발광 소재용 화합물을 언급하고 있다. 상기 문헌에는 카바졸에 벤조싸이오펜, 인돌, 인덴, 벤조퓨란, 실롤 등의 고리가 융합된 헤테로아릴기가 트리페닐렌과 결합된 화합물을 개시하고 있지 않다. Meanwhile, Korean Patent Publication No. KR2010-0056490 discloses a compound for an organic electroluminescent material in which carbazole, dibenzofuran, dibenzothiophene and the like are substituted with triphenylene. This document does not disclose a compound in which a heteroaryl group in which a ring such as benzothiophene, indole, indene, benzofuran, silol and the like is fused to carbazole is bonded to triphenylene.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better light emission efficiency and excellent life characteristics of the material than the existing material, the driving life of the device This is not only very good, but also has an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.
[화학식 1][Formula 1]
[상기 화학식 1에서, L1은 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 또는 치환 또는 비치환된 (C6-C30)아릴렌이고; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR11R12-, -SiR13R14- 또는 -NR15-이며, 단, Y1 와 Y2가 동시에 존재하는 경우는 없고; Ar1은 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 또는 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬이며; R1 내지 R6 및 R11 내지 R15은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, -NR21R22, -SiR23R24R25, -SR26, -OR27 , 시아노, 나이트로 또는 하이드록시이고; R21 내지 R27는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (C2-C30)헤테로아릴이고; a, b 및 c는 각각 독립적으로 1 내지 4의 정수이며, a, b 및 c가 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고; d 및 e는 1 내지 3의 정수이며, d 및 e가 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고; f는 1 내지 2의 정수이며, f가 2의 정수인 경우 각각 동일하거나 상이할 수 있고; 상기 헤테로시클로알킬, 헤테로아릴렌 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.][In Formula 1, L 1 is a single bond, a substituted or unsubstituted (C2-C30) heteroarylene, or a substituted or unsubstituted (C6-C30) arylene; Y 1 and Y 2 are each independently -O-, -S-, -CR 11 R 12- , -SiR 13 R 14 -or -NR 15 -provided that Y 1 and Y 2 do not exist at the same time; Ar 1 is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted 5- to 7-membered heterocycloalkyl; R 1 to R 6 and R 11 to R 15 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, -NR 21 R 22 , -SiR 23 R 24 R 25 , -SR 26 , -OR 27 , cyano, nitro or hydroxy; R 21 to R 27 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) Heteroaryl; a, b and c are each independently integers of 1 to 4, and when a, b and c are integers of 2 or more, each may be the same or different; d and e are integers of 1 to 3, and may be the same or different when d and e are integers of 2 or more, respectively; f is an integer of 1 to 2, and may be the same or different when f is an integer of 2; Wherein said heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 바람직하게는 (C1-C20)알킬이고, 더 바람직하게는 (C1-C10)알킬이며, ‘(C6-C30)아릴’기는 바람직하게는 (C6-C20)아릴이다. ‘(C2-C30)헤테로아릴’기는 바람직하게는 (C2-C20)헤테로아릴이다. ‘(C3-C30)시클로알킬’기는 바람직하게는 (C3-C20)시클로알킬이고, 더 바람직하게는 (C3-C7)시클로알킬이다. ‘(C2-C30)알케닐 또는 알키닐’기는 바람직하게는 (C2-C20)알케닐 또는 알키닐이고, 더 바람직하게는 (C2-C10)알케닐 또는 알키닐이다.Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl. The '(C2-C30) heteroaryl' group is preferably (C2-C20) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 L1, Ar1, R1 내지 R6, R11 내지 R15 및 R21 내지 R27에 더 치환되는 치환기는 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, "substituted" means a case where is further substituted with an unsubstituted substituent, the L 1 , Ar 1 , Substituents further substituted by R 1 to R 6 , R 11 to R 15, and R 21 to R 27 are each deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30 ) Aryl, (C2-C30) heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) Cycloalkyl, 5- to 7-membered heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30 ) Alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) Arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) It means one or more selected from the group consisting of arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy.
구체적으로, 상기 L1은 단일결합, (C2-C30)헤테로아릴렌 또는 (C6-C30)아릴렌이고; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR11R12-, -SiR13R14- 또는 -NR15-이며, 단, Y1 와 Y2가 동시에 존재하는 경우는 없고; Ar1은 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이며; R1 내지 R6 및 R11 내지 R15은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴, -NR21R22 또는 -SiR23R24R25이고; R21 내지 R25는 각각 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이고; 상기 L1의 아릴렌 및 헤테로아릴렌, Ar1, R1 내지 R6 및 R11 내지 R15의 알킬, 아릴 및 헤테로아릴, R21 내지 R25의 알킬 및 아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 및 (C1-C30)알킬디(C6-C30)아릴실릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Specifically, L 1 is a single bond, (C2-C30) heteroarylene or (C6-C30) arylene; Y 1 and Y 2 are each independently -O-, -S-, -CR 11 R 12- , -SiR 13 R 14 -or -NR 15 -provided that Y 1 and Y 2 do not exist at the same time; Ar 1 is (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; R 1 to R 6 and R 11 to R 15 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl, -NR 21 R 22 or- SiR 23 R 24 R 25 ; R 21 to R 25 are each independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl; The arylene and heteroarylene of L 1 , Ar 1 , R 1 to R 6 and R 11 to R 15 , alkyl, aryl and heteroaryl, R 21 to R 25 , alkyl and aryl are each deuterium, halogen, (C1 -C30) alkyl, halogen substituted (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di It may be further substituted with one or more substituents selected from the group consisting of (C1-C30) alkyl (C6-C30) arylsilyl and (C1-C30) alkyldi (C6-C30) arylsilyl.
보다 구체적으로 상기 L1은 단일결합, 페닐렌, 비페닐렌, 터페닐렌, 인데닐렌, 플루오레닐렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 플루오란텐일렌, 2,3-다이하이드로-1H-인데닐렌, 티오페닐렌, 피롤릴렌, 피라졸릴렌, 티아졸릴렌, 옥사졸릴렌, 옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 퓨라잔일렌, 피리딜렌, 피리미딜렌, 벤조퓨란일렌, 벤조티오펜일렌, 인돌릴렌, 벤조이미다졸릴렌, 벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 벤조티아디아졸릴렌, 다이벤조퓨란닐렌 또는 다이벤조싸이오페닐렌이고; Ar1은 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 플루오레닐, 플루오란텐일, 터페닐일, 피렌일, 페릴렌, 피리딜, 피리미디닐, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 퀴놀릴, 이소퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 인데닐, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 퀴나졸릴, 퀴녹살리닐 또는 N-카바졸릴이고; R1 내지 R6 및 R11 내지 R15는 각각 독립적으로 수소, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 플루오레닐, 플루오란텐일, 터페닐일, 피렌일, 페릴렌, 피리딜, 피리미디닐, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 인데닐, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 퀴녹살리닐, N-카바졸릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴, 메틸다이페닐실릴 또는 트리페닐실릴이고; 상기 L1, Ar1, R1 내지 R6 및 R11 내지 R15의 치환기는 각각 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 9,9-다이메틸플루오레닐, 9,9-다이페닐플루오레닐, 플루오란텐일, 트리페닐렌일, 피리딜, 피리미디닐, 벤조티오펜일, 이미다졸릴, 벤조티아졸릴, 벤조이미다졸릴, 피렌일, 페릴렌일, 퀴놀릴, 이소퀴놀릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴 및 트리페닐실릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.More specifically, L 1 is a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, peryleneylene, fluoranthhenylene, 2,3-di Hydro-1H-indenylene, thiophenylene, pyrroylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, furazylene, pyridylene, Pyrimidylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, benzothiadiazolylene, di Benzofuranylene or dibenzothiophenylene; Ar 1 is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethyl Hexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, terphenylyl , Pyrenyl, perylene, pyridyl, pyrimidinyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, isoquinolyl, triazinyl, benzofuranyl, dibenzofuran 1, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, indenyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl, quinazolyl, quinoxalinyl or N-carbazolyl; R 1 to R 6 and R 11 to R 15 are each independently hydrogen, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl , n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, Phenyl, biphenyl, fluorenyl, fluoranthenyl, terphenylyl, pyrenyl, perylene, pyridyl, pyrimidinyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, qui Noyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, indenyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl , Phenanthrolinyl, quinoxalinyl, N-carbazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethyl Carbonyl silyl, methyl diphenyl silyl or triphenyl silyl gt; The substituents of L 1 , Ar 1 , R 1 to R 6 and R 11 to R 15 are each deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t- Butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl , Perfluoropropyl, perfluorobutyl, phenyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluoranthenyl, triphenylenyl, pyridyl, pyrimidinyl, benzo Thiophenyl, imidazolyl, benzothiazolyl, benzoimidazolyl, pyrenyl, peryleneyl, quinolyl, isoquinolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t -Butyldimethylsilyl, dimethylphenylsilyl and triphenylsilyl may be further substituted with one or more substituents selected from the group consisting of.
더욱 구체적으로 상기 
[상기 Ar1, R5, R6, R11 내지 R15, e 및 f는 상기 화학식 1에서의 정의와 동일하다.][Ar 1 , R 5 , R 6 , R 11 to R 15 , e and f are the same as defined in Formula 1 above.]
본 발명에 따른 유기 발광 화합물로는 대표적으로 하기의 화합물을 들 수 있다. Examples of the organic light emitting compound according to the present invention include the following compounds.
본 발명에 따른 유기 발광 화합물은 하기 반응식에 나타난 바와 같이 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in the following scheme.
[반응식 1][Reaction Scheme 1]
[반응식 2][Reaction Scheme 2]
[상기 반응식 1 및 2에서, L1, Ar1, Y1, Y2, R1 내지 R6, a, b, c, d, e 및 f는 상기 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.][In Reaction Schemes 1 and 2, L 1 , Ar 1 , Y 1 , Y 2 , R 1 to R 6 , a, b, c, d, e and f are the same as defined in Formula 1, Hal is Halogen.]
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖는 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다. 또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 화합물을 호스트 물질로 사용할 수 있으며 상기 화학식 1의 화합물에 다른 호스트 물질을 추가하여 사용할 수 있다.In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound represented by Chemical Formula 1. In addition, the organic material layer may include a light emitting layer, in which the compound of Formula 1 may be used as a host material, and another host material may be added to the compound of Formula 1.
상기 발광층에서 상기 화학식 1의 유기 전자재료용 화합물이 호스트로 사용되어질 때 하나 이상의 인광 도판트를 포함한다. 본 발명의 유기 전계 발광 소자에 적용되는 인광 도판트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 인광 도판트에 포함되는 금속으로서는 Ir, Pt 및 Cu에서 선택되는 것이 바람직하다. 구체적으로 상기 인광 도판트 화합물로서 다음과 같은 화합물을 사용하는 것이 바람직하다. When the compound for the organic electronic material of Formula 1 is used as a host in the light emitting layer includes at least one phosphorescent dopant. The phosphorescent dopant applied to the organic electroluminescent element of the present invention is not particularly limited, but is preferably selected from Ir, Pt and Cu as the metal included in the phosphorescent dopant applied to the organic electroluminescent element of the present invention. Specifically, it is preferable to use the following compounds as the phosphorescent dopant compound.
본 발명의 유기 전계 발광 소자는 화학식 1의 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention includes the compound of Formula 1, and at the same time, may include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in addition to the compound of Formula 1, an organic compound selected from the group consisting of Group 1, Group 2, Group 4, Group 5 transition metal, Lanthanide series metal and d- And the organic layer may further include a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. In addition, the organic material layer may simultaneously include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound to form an organic light emitting device that emits white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO X (1? X ? 2), AlO x (1? X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. 또한, 본 발명에 따른 유기 발광 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device. In addition, the organic light emitting compound according to the present invention has high electron transfer efficiency, which prevents crystallization during device fabrication and improves current characteristics of the device due to good layer formation, thereby lowering the driving voltage of the device and at the same time improving the power efficiency. There is an advantage to manufacture.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 방광 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, an organic bladder compound according to the present invention, a method for preparing the same, and a light emission characteristic of a device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.
[제조예 1] 화합물 28의 제조Preparation Example 1 Preparation of Compound 28
화합물 1-1 의 제조: 1,4-디브로모-2-니트로벤젠 (30g, 131mmol), 디벤조[b,d]티오펜-4-일보론산 (44g, 156.6mmol), Pd(PPh3)4(7.6g,6.58mmol) 및 Na2CO3(41.8g,394mmol)을 톨루엔(500mL)/EtOH(100mL)/정제수(100mL)에 투입 후 120℃에서 3시간동안 교반하였다. 반응 종결 후 정치하여 수층 제거 후 유층은 농축하였다. 실리카 컬럼 정제하여 화합물 1-1 (40g, 80%)을 얻었다. Preparation of Compound 1-1 : 1,4-dibromo-2-nitrobenzene (30 g, 131 mmol), dibenzo [ b , d ] thiophen-4-ylboronic acid (44 g, 156.6 mmol), Pd (PPh 3 ) 4 (7.6 g, 6.58 mmol) and Na 2 CO 3 (41.8 g, 394 mmol) were added to toluene (500 mL) / EtOH (100 mL) / purified water (100 mL) and stirred at 120 ° C. for 3 hours. After completion of the reaction, the mixture was allowed to stand to remove water, and the oil layer was concentrated. Silica column purification gave Compound 1-1 (40 g, 80%).
화합물 1-2 의 제조: 화합물 1-1 (40g, 104mmol)을 1,2-디클로로벤젠 (150mL)에 녹인 후 트리에톡시포스핀 (150mL)를 첨가하였다. 이 반응 혼합물을 150℃에서 20 간동안 교반하였다. 반응 혼합물을 상온으로 냉각시키고 용매인 1,2-디클로로벤젠과 트리에톡시포스핀은 감압 증류를 통해서 제거하였다. 남겨진 유기물은 에틸아세테이트 (500mL)로 추출한 후, 얻어진 유기층을 증류수 (50mL)로 씻어주었다. 유기층을 무수MgSO4으로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체는 실리카겔 컬럼크로마토그래피로 분리하여 화합물 1-2 (15.4g, 42%)을 얻었다. Preparation of Compound 1-2 : Compound 1-1 (40 g, 104 mmol) was dissolved in 1,2-dichlorobenzene (150 mL) and then triethoxyphosphine (150 mL) was added. The reaction mixture was stirred at 150 ° C. for 20 minutes. The reaction mixture was cooled to room temperature and solvents 1,2-dichlorobenzene and triethoxyphosphine were removed by distillation under reduced pressure. The remaining organics were extracted with ethyl acetate (500 mL), and the obtained organic layer was washed with distilled water (50 mL). The organic layer was dried over anhydrous MgSO 4 , and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography to obtain compound 1-2 (15.4 g, 42%).
화합물 1-3 의 제조: 화합물 1-2 (15.4g, 43.8mmol), 요오드벤젠 (13mL, 90mmol), 요오드화구리 (4.2g, 22.1mmol) 및 Cs2CO3 (42.8g, 131.4mmol)을 톨루엔 (250mL)에 녹인 후 80℃에서 10분간 교반하였다. 그리고 1,2-디아미노에탄 (1.5mL, 22.4mmol)을 넣은 후 140℃에서 12시간동안 교반하였다. 반응 종결 후 에틸아세테이트 (250mL)로 추출한 후, 얻어진 유기층을 증류수 (50mL)로 씻어주었다. 유기층을 무수MgSO4으로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체는 실리카겔 컬럼크로마토그래피로 분리하여 화합물 1-3 (13.3g, 71%)을 얻었다. Preparation of Compound 1-3 : Compound 1-2 (15.4 g, 43.8 mmol), Iodine Benzene (13 mL, 90 mmol), Copper Iodide (4.2 g, 22.1 mmol) and Cs 2 CO 3 (42.8 g, 131.4 mmol) was dissolved in toluene (250 mL) and stirred at 80 ° C. for 10 minutes. Then, 1,2-diaminoethane (1.5mL, 22.4mmol) was added thereto, followed by stirring at 140 ° C for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate (250 mL), and the obtained organic layer was washed with distilled water (50 mL). The organic layer was dried over anhydrous MgSO 4 , and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography to obtain compound 1-3 (13.3 g, 71%).
화합물 1-4 의 제조: 화합물 1-3 (13.3g, 31mol)를 THF (150mL)에 녹인 후 교반하면서 -78℃로 온도를 냉각시켰다. 그 후 n-부틸리튬 (15mL, 37.5mmol, 2.5M in hexane)을 천천히 적가하였다. 적가가 종결된 후 -78℃에서 1시간동안 교반하고, 트리메톡시보란 (5.2mL, 46.6mmol)을 천천히 넣은 후 1시간동안 교반하였다. 반응 종결 후 반응액의 온도를 상온으로 올리고 포화염화암모늄 수용액으로 반응을 종결시켰다. 상기 혼합물을 에틸아세테이트 (200mL)로 추출한 뒤 유기층을 무수MgSO4로 건조하고, 거른 후 감압 하에서 용매를 제거한 후, 재결정을 통하여 화합물 1-4 (8.5g, 70%)을 얻었다. Preparation of Compound 1-4 : Compound 1-3 (13.3 g, 31 mol) was dissolved in THF (150 mL) and then cooled to −78 ° C. while stirring. Then n-butyllithium (15 mL, 37.5 mmol, 2.5 M in hexane) was slowly added dropwise. After the addition was completed, the mixture was stirred for 1 hour at -78 ° C, trimethoxyborane (5.2 mL, 46.6 mmol) was added slowly, and the mixture was stirred for 1 hour. After completion of the reaction, the temperature of the reaction solution was raised to room temperature, and the reaction was terminated with a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (200 mL), the organic layer was dried over anhydrous MgSO 4 , filtered, and the solvent was removed under reduced pressure, and then compound 1-4 (8.5 g, 70%) was obtained by recrystallization.
화합물 1-5 의 제조: 화합물 1-4 (8g, 20.3mmol), 1,3-디브로모벤젠 (14.4g, 61mmol), Pd(PPh3)4 (1.8g, 1.56mmol) 및 Na2CO3 (6.45g, 60.9mmol)을 톨루엔 (100mL)/EtOH (25mL)/정제수 (25mL)에 투입 후 120℃에서 5시간동안 교반하였다. 반응 종결 후 정치하여 수층을 제거한 후 유기층은 농축하였다. 실리카겔 컬럼크로마토그래피로 분리하여 화합물 1-5 (7g, 69%)를 얻었다. Preparation of Compound 1-5 : Compound 1-4 (8 g, 20.3 mmol), 1,3-dibromobenzene (14.4 g, 61 mmol), Pd (PPh 3 ) 4 (1.8 g, 1.56 mmol) and Na 2 CO 3 (6.45 g, 60.9 mmol) was added to toluene (100 mL) / EtOH (25 mL) / purified water (25 mL) and stirred at 120 ° C. for 5 hours. After completion of the reaction, the mixture was left to stand, the aqueous layer was removed, and the organic layer was concentrated. Compound 1-5 (7 g, 69%) was obtained by silica gel column chromatography.
화합물 1-6 의 제조: 트리페닐렌 (10g, 43.8mol)를 디클로로메탄 (100mL)에 녹인 후 교반하면서 디클로로메탄 (100mL)로 묽힌 브롬 (2.3mL, 44.9mmol)을 천천히 적가하였다. 적가가 종결된 후 30분간 교반하였다. 반응 종결 후 포화티오황산나트륨 수용액으로 반응을 종결시켰다. 상기 혼합물을 디클로로메탄 (200mL)로 추출한 뒤 유기층을 무수MgSO4로 건조하고, 거른 후 감압 하에서 용매를 제거한 후, 실리카겔 컬럼크로마토그래피로 분리하여 화합물 1-6 (8g, 59%)을 얻었다. Preparation of Compound 1-6 : Triphenylene (10 g, 43.8 mol) was dissolved in dichloromethane (100 mL), and then bromine (2.3 mL, 44.9 mmol) diluted with dichloromethane (100 mL) was slowly added dropwise with stirring. After the addition was terminated, the mixture was stirred for 30 minutes. After completion of the reaction, the reaction was terminated with saturated aqueous sodium thiosulfate solution. The mixture was extracted with dichloromethane (200 mL), the organic layer was dried over anhydrous MgSO 4 , filtered, and the solvent was removed under reduced pressure, and then separated by silica gel column chromatography to obtain compound 1-6 (8 g, 59%).
화합물 1-7 의 제조: 화합물 1-6 (8g, 26mol)를 THF (100mL)에 녹인 후 교반하면서 -78℃로 냉각시켰다. 그 후 n-부틸리튬 (12.5mL, 31.3mmol, 2.5M in hexane)을 천천히 적가하였다. 적가가 종결된 후 -78℃에서 1시간동안 교반하고, 트리메톡시보란 (4.3mL, 39mmol)을 천천히 넣은 후 1시간동안 교반하였다. 반응 종결 후 반응액의 온도를 상온으로 올리고 포화염화암모늄 수용액으로 반응을 종결시켰다. 상기 혼합물을 에틸아세테이트 (100mL)로 추출한 뒤 유기층을 무수MgSO4로 건조하고, 거른 후 감압 하에서 용매를 제거한 후, 재결정을 통하여 화합물 1-7 (5.2g, 74%)을 얻었다. Preparation of Compound 1-7 : Compound 1-6 (8 g, 26 mol) was dissolved in THF (100 mL) and then cooled to -78 ° C while stirring. Then n-butyllithium (12.5 mL, 31.3 mmol, 2.5 M in hexane) was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred at -78 ° C for 1 hour, trimethoxyborane (4.3mL, 39mmol) was added slowly, followed by stirring for 1 hour. After completion of the reaction, the temperature of the reaction solution was raised to room temperature, and the reaction was terminated with a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (100 mL), the organic layer was dried over anhydrous MgSO 4 , filtered, and the solvent was removed under reduced pressure, and then compound 1-7 (5.2 g, 74%) was obtained by recrystallization.
화합물 28 의 제조: 화합물 1-5 (5g, 9.91mmol), 화합물 1-7 (4.1g, 15.1mmol), Pd(PPh3)4 (573mg, 0.5mmol) 및 K2CO3 (4.1g, 29.7mmol)을 톨루엔 (100mL)/EtOH (25mL)/정제수 (25mL)에 투입 후 120℃에서 20시간동안 교반하였다. 반응 종결 후 정치하여 수층을 제거한 후 유기층은 농축하였다. 실리카겔 컬럼크로마토그래피로 분리하여 화합물 28 (5.5g, 85%)를 얻었다. MS/FAB found 651.8, calculated 651.20 compound 28 Manufacture of: compound1-5 (5 g, 9.91 mmol), compound1-7 (4.1 g, 15.1 mmol), Pd (PPh3)4(573 mg, 0.5 mmol) and K2CO3 (4.1 g, 29.7 mmol) was added to toluene (100 mL) / EtOH (25 mL) / purified water (25 mL) and stirred at 120 ° C. for 20 hours. After completion of the reaction, the mixture was left to stand, the aqueous layer was removed, and the organic layer was concentrated. Compound separated by silica gel column chromatography28 (5.5g, 85%) was obtained. MS / FAB found 651.8, calculated 651.20
[제조예 2] 화합물 47의 제조Preparation Example 2 Preparation of Compound 47
화합물 2-1 의 제조: 2-브로모-9,9-디메틸-9H-플루오렌 (50.0g, 183mmol), 2-클로로벤젠아민 (28.4ml, 274.5mmol), Pd(OAc)2 (1.64g, 7.32mmol), P(t-Bu)3 (50%) (7.2ml, 14.64mmol) 및 NaOtBu (43.97g, 457.5mmol)을 톨루엔 (450mL)에 투입 후 하룻동안 환류 교반하였다. 반응 종결 후 실온으로 냉각한 뒤 증류수와 에틸아세테이트로 추출하였다. 유기층을 감압증류한 후 MC/Hex으로 컬럼분리하여 화합물 2-1 (46.7g, 80%)를 얻었다. Preparation of Compound 2-1 : 2-bromo-9,9-dimethyl-9H-fluorene (50.0 g, 183 mmol), 2-chlorobenzeneamine (28.4 ml, 274.5 mmol), Pd (OAc) 2 (1.64 g , 7.32 mmol), P (t-Bu) 3 (50%) (7.2 ml, 14.64 mmol) and NaO t Bu (43.97 g, 457.5 mmol) were added to toluene (450 mL) and stirred under reflux for one day. After completion of the reaction was cooled to room temperature and extracted with distilled water and ethyl acetate. After distilling the organic layer under reduced pressure, Compound 2-1 (46.7 g, 80%) was obtained by column separation with MC / Hex.
화합물 2-2 의 제조: 화합물 2-1 (46.7g, 14.6mmol), Pd(OAc)2 (1.64g, 7.3mmol), 디-터트-부틸메틸포스핀ㆍHBF4 (3.62g, 14.6mol), K2CO3 (60.5g, 438mmol) 및 DMA (500ml)을 혼합한 후 200℃에서 12시간동안 교반하였다. 반응 종결 후 에틸아세테이트를 사용하여 추출한 뒤 유기층을 무수MgSO4로 건조하고, 거른 후 감압 하에서 용매를 제거한 후, 컬럼분리하여 흰색 고체의 화합물 2-2 (35.17g, 85%)을 얻었다. Preparation of Compound 2-2 : Compound 2-1 (46.7 g, 14.6 mmol), Pd (OAc) 2 (1.64 g, 7.3 mmol), di-tert-butylmethylphosphine.HBF 4 (3.62 g, 14.6 mol) , K 2 CO 3 (60.5 g, 438 mmol) and DMA (500 ml) were mixed and stirred at 200 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and then the organic layer was dried over anhydrous MgSO 4 , filtered, and the solvent was removed under reduced pressure, followed by column separation to obtain a white solid compound 2-2 (35.17 g, 85%).
화합물 2-3 의 제조: 화합물 2-2 (30.17g, 106.47mmol), 아이오도벤젠 (23.74ml, 212.94mmol), CuI (10.14g, 53.24mmol), EDA (7.13ml, 106.47mmol) 및 K3PO4 (67.8g, 319.41mmol)을 톨루엔 (250ml)에 투입 후 하룻동안 환류교반하였다. MC로 추출한 후 감압증류한 후 MC/Hex으로 컬럼분리하여 화합물 2-3 (29.1g, 76%)를 얻었다. Preparation of Compound 2-3 : Compound 2-2 (30.17 g, 106.47 mmol), iodobenzene (23.74 ml, 212.94 mmol), CuI (10.14 g, 53.24 mmol), EDA (7.13 ml, 106.47 mmol) and K 3 PO 4 (67.8g, 319.41mmol) was added to toluene (250ml) and stirred under reflux for one day. Extraction with MC followed by distillation under reduced pressure and column separation with MC / Hex gave compound 2-3 (29.1 g, 76%).
화합물 2-4 의 제조: DMF (100mL)에 녹아있는 화합물 2-3 (29.1g, 80.95mmol)에 NBS (15.85g, 89.05mmol)를 0℃에서 투입한 후 하룻동안 교반하였다. 정제수를 투입하고 감압여과하여 얻어진 고체를 CHCl3로 녹여 컬럼분리하여 화합물 2-4 (30g, 85%)를 얻었다. Preparation of Compound 2-4 : NBS (15.85g, 89.05mmol) was added to Compound 2-3 (29.1g, 80.95mmol) dissolved in DMF (100mL) at 0 ° C, and stirred for 1 day. Purified water was added, and the solid obtained by filtration under reduced pressure was dissolved in CHCl 3 , and the resulting mixture was separated by column to obtain compound 2-4 (30 g, 85%).
화합물 2-5 의 제조: 화합물 2-4 (35g, 81mmol)을 THF(500mL)에 녹이고 -78℃에서 n-부틸리튬 (38.8mL,97.14mmol, 2.5M in hexane)을 천천히 첨가한 후 1시간동안 교반하였다. B(Oi-Pr)3 (27.9mL, 121.43mmol)을 첨가한 후 하룻동안 교반하였다. 1M HCl을 첨가하여 quenching한 후 증류수와 에틸아세테이트로 추출하였다. MC와 Hex으로 재결정하여 화합물 2-5 (28.5g, 87%)를 얻었다. Preparation of Compound 2-5 : Compound 2-4 (35 g, 81 mmol) was dissolved in THF (500 mL), and n -butyllithium (38.8 mL, 97.14 mmol, 2.5 M in hexane) was slowly added at -78 ° C for 1 hour. Was stirred. B (O i -Pr) 3 (27.9 mL, 121.43 mmol) was added and stirred for one day. After quenching by adding 1M HCl, the mixture was extracted with distilled water and ethyl acetate. Recrystallization with MC and Hex gave compound 2-5 (28.5 g, 87%).
화합물 2-6 의 제조: 화합물 2-5 (20.0g, 49.61mmol), 1,3-디브로모벤젠 (9mL, 74.42mmol), Pd(PPh3)4 (1.72g, 1.49mmol) 및 Na2CO3 (13.15g, 124.03mmol)을 톨루엔 (240mL)/EtOH (30mL)/정제수 (60mL)에 투입 후 하룻동안 환류 교반하였다. 반응 종결 후 실온으로 냉각한 뒤 증류수와 에틸아세테이트로 추출하였다. 유기층을 감압증류한 후 MC/Hex으로 컬럼분리하여 화합물 2-6 (19.5g, 76%)를 얻었다. Preparation of Compound 2-6 : Compound 2-5 (20.0 g, 49.61 mmol), 1,3-dibromobenzene (9 mL, 74.42 mmol), Pd (PPh 3 ) 4 (1.72 g, 1.49 mmol) and Na 2 CO 3 (13.15 g, 124.03 mmol) was added to toluene (240 mL) / EtOH (30 mL) / purified water (60 mL) and stirred under reflux for one day. After completion of the reaction was cooled to room temperature and extracted with distilled water and ethyl acetate. After distilling the organic layer under reduced pressure, Compound 2-6 (19.5 g, 76%) was obtained by column separation with MC / Hex.
화합물 2-7 의 제조: 화합물 2-6 (19.5g, 37.9mmol)을 THF(250mL)에 녹이고 -78℃에서 n-부틸리튬 (18.2mL, 45.49mmol, 2.5M in hexane)을 천천히 첨가한 후 1시간동안 교반하였다. B(Oi-Pr)3 (13.1mL, 56.85mmol)을 첨가한 후 하룻동안 교반하였다. 1M HCl을 첨가하여 quenching한 후 증류수와 에틸아세테이트로 추출하였다. MC와 Hex으로 재결정하여 화합물 2-7 (13.76g, 76%)를 얻었다. Preparation of Compound 2-7 : Compound 2-6 (19.5 g, 37.9 mmol) was dissolved in THF (250 mL) and n -butyllithium (18.2 mL, 45.49 mmol, 2.5 M in hexane) was slowly added at -78 ° C. Stirred for 1 hour. B (O i -Pr) 3 (13.1 mL, 56.85 mmol) was added and stirred for one day. After quenching by adding 1M HCl, the mixture was extracted with distilled water and ethyl acetate. Recrystallization with MC and Hex gave compound 2-7 (13.76 g, 76%).
화합물 47 의 제조: 화합물 2-7 (6.0g, 12.52mmol), 화합물 1-6 (3.5g, 11.38mmol), Pd(OAc)2 (0.128g, 0.569mmol), P(t-Bu)3 (50%) (0.55mL, 1.138mmol) 및 K3PO4 (7.25g, 34.14mmol)을 톨루엔 (70mL)/EtOH (17mL)/정제수 (17mL)에 투입 후 하룻동안 환류 교반하였다. 반응 종결 후 실온으로 냉각한 뒤 증류수와 에틸아세테이트로 추출하였다. 유기층을 감압증류한 후 MC/Hex으로 컬럼분리하여 화합물 47 (2.47g, 33%)를 얻었다. MS/FAB found 648.8, calculated 648.27 Preparation of Compound 47 : Compound 2-7 (6.0 g, 12.52 mmol), Compound 1-6 (3.5 g, 11.38 mmol), Pd (OAc) 2 (0.128 g, 0.569 mmol), P ( t- Bu) 3 ( 50%) (0.55 mL, 1.138 mmol) and K 3 PO 4 (7.25 g, 34.14 mmol) was added to toluene (70 mL) / EtOH (17 mL) / purified water (17 mL) and stirred under reflux for one day. After completion of the reaction was cooled to room temperature and extracted with distilled water and ethyl acetate. After distilling the organic layer under reduced pressure, Compound 47 (2.47 g, 33%) was obtained by column separation with MC / Hex. MS / FAB found 648.8, calculated 648.27
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작[Example 1] Fabrication of an OLED device using an organic light emitting compound according to the present invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-다이일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐벤젠-1,4-다이아민) (N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) 을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐 (N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl)을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 화합물 28를 넣고, 또 다른 셀에도 호스트로서 11-(4,6-다이페닐-1,3,5-트리아진-2-일)-12-페닐-11,12-다이하이드로인돌로[2,3-a]카바졸 (11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a]carbazole)을 넣은 후, 도판트로서 화합물 D-25을 넣어, 두 호스트 물질은 같은 속도로 증발시켜 50중량%으로, 도판트는 다른 속도로 증발시켜 15중량%으로 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸 (2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)을 넣고, 또 다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 각각 넣은 후, 두 물질을 같은속도로 증발시켜 50중량%으로 도핑함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 리튬 퀴놀레이트(Lithium quinolate)를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ′ -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) (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 added and evacuated until the vacuum in the chamber reached 10 -6 torr. A current was applied and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate, followed by N, N'-die (4-biphenyl) -N, N'-die (4) in another cell in the vacuum deposition equipment. -Biphenyl) -4,4'-diaminobiphenyl (N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl) is added thereto, and the cell A current was applied and evaporated to deposit a 20 nm-thick hole transport layer on the hole injection layer After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Into the compound 28 as a host in one cell in the deposition apparatus, and as a host to the other cell 11 (4,6-diphenyl-1,3,5-triazin-2-yl) -12- phenyl -11,12 -Dihydroindolo [2,3-a] carbazole (11- (4,6-diphenyl-1,3,5-triazin-2-yl) -12-phenyl-11,12-dihydroindolo [2,3 after loading the -a] carbazole), into the compound D-25 as a dopant, the two host materials are evaporated at the same speed as a 50% by weight, the dopant by doping with 15% by weight by evaporation at different rates to the hole transport layer A light emitting layer having a thickness of 30 nm was deposited thereon, and then 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl in one cell as an electron transporting layer on the light emitting layer. -1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole) Lithium quinolate was added to another cell, and both materials were evaporated at the same rate to 50% by weight. A 30 nm electron transport layer was deposited by doping. Subsequently, Lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device. Each compound was purified by vacuum sublimation under 10 -6 torr.
그 결과, 4.2 V의 전압에서 1.22 mA/cm2의 전류가 흘렀으며, 610 cd/m2의 녹색발광이 확인되었다. As a result, a current of 1.22 mA / cm 2 flowed at a voltage of 4.2 V, and green light emission of 610 cd / m 2 was confirmed.
[실시예 2] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작[Example 2] Fabrication of an OLED device using an organic light emitting compound according to the present invention
발광재료로서 화합물 28 대신 화합물 47을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 4.96 V의 전압에서 3.71 mA/cm2의 전류가 흘렀으며, 1830 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound 47 was used instead of Compound 28 as the light emitting material. As a result, a current of 3.71 mA / cm 2 flowed at a voltage of 4.96 V, and green light emission of 1830 cd / m 2 was confirmed.
[비교예 1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Fabrication of OLED device using light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-다이카바졸-바이페닐 (4,4‘-N,N'-dicarbazole-biphenyl), 도판트로는 화합물 D-2을 사용하여 발광층을 증착하고, 발광층과 전자 전달층 사이에 정공 저지층으로 알루미늄(III)비스(2-메틸-8-퀴놀리네이토)4-페닐페놀레이트 (aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate)을 10nm 두께로 증착한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 4.9 V의 전압에서 2.86 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다. 4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl) is deposited on the host as a light emitting material, and a light emitting layer is deposited using compound D-2 as a dopant. And aluminum (III) bis (2-methyl-8-quinolinate) 4-phenylphenolate (aluminum (III) bis (2-methyl-8-quinolinato) as a hole blocking layer between the light emitting layer and the electron transporting layer. An OLED device was manufactured in the same manner as in Example 1, except that 4-phenylphenolate) was deposited to a thickness of 10 nm. As a result, a current of 2.86 mA / cm 2 flowed at a voltage of 4.9 V, and green light emission of 1000 cd / m 2 was confirmed.
본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.
Claims (9)
[화학식 1]
[상기 화학식 1에서, L1은 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 또는 치환 또는 비치환된 (C6-C30)아릴렌이고; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR11R12-, -SiR13R14- 또는 -NR15-이며, 단, Y1 와 Y2가 동시에 존재하는 경우는 없고; Ar1은 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 또는 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬이며; R1 내지 R6 및 R11 내지 R15은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, -NR21R22, -SiR23R24R25, -SR26, -OR27 , 시아노, 나이트로 또는 하이드록시이고; R21 내지 R27는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (C2-C30)헤테로아릴이고; a, b 및 c는 각각 독립적으로 1 내지 4의 정수이며, a, b 및 c가 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고; d 및 e는 1 내지 3의 정수이며, d 및 e가 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고; f는 1 내지 2의 정수이며, f가 2의 정수인 경우 각각 동일하거나 상이할 수 있고; 상기 헤테로시클로알킬, 헤테로아릴렌 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]An organic light emitting compound represented by Formula 1 below:
[Formula 1]
[In Formula 1, L 1 is a single bond, a substituted or unsubstituted (C2-C30) heteroarylene, or a substituted or unsubstituted (C6-C30) arylene; Y 1 and Y 2 are each independently -O-, -S-, -CR 11 R 12- , -SiR 13 R 14 -or -NR 15 -provided that Y 1 and Y 2 do not exist at the same time; Ar 1 is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted 5- to 7-membered heterocycloalkyl; R 1 to R 6 and R 11 to R 15 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, -NR 21 R 22 , -SiR 23 R 24 R 25 , -SR 26 , -OR 27 , cyano, nitro or hydroxy; R 21 to R 27 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C2-C30) Heteroaryl; a, b and c are each independently integers of 1 to 4, and when a, b and c are integers of 2 or more, each may be the same or different; d and e are integers of 1 to 3, and may be the same or different when d and e are integers of 2 or more, respectively; f is an integer of 1 to 2, and may be the same or different when f is an integer of 2; Wherein said heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
상기 L1, Ar1, R1 내지 R6, R11 내지 R15 및 R21 내지 R27에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것인 유기 발광 화합물.The method of claim 1,
L 1 , Ar 1 , R 1 to R 6 , R 11 to R 15 And substituents further substituted for R 21 to R 27 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) heteroaryl, ( C1-C30) alkyl substituted (C2-C30) heteroaryl, (C6-C30) aryl substituted (C2-C30) heteroaryl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl , Tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, ( C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6- C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) At least one selected from the group consisting of C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy.
상기
[상기 Ar1, R5, R6, R11 내지 R15, e 및 f는 청구항 제1항에서의 정의와 동일하다.]The method of claim 1,
remind
[Ar 1 , R 5 , R 6 , R 11 to R 15 , e and f are the same as defined in claim 1.
상기 L1은 단일결합, (C2-C30)헤테로아릴렌 또는 (C6-C30)아릴렌이고; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR11R12-, -SiR13R14- 또는 -NR15-이며, 단, Y1 와 Y2가 동시에 존재하는 경우는 없고; Ar1은 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이며; R1 내지 R6 및 R11 내지 R15은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴, -NR21R22 또는 -SiR23R24R25이고; R21 내지 R25는 각각 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이고; 상기 L1의 아릴렌 및 헤테로아릴렌, Ar1, R1 내지 R6 및 R11 내지 R15의 알킬, 아릴 및 헤테로아릴, R21 내지 R25의 알킬 및 아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 및 (C1-C30)알킬디(C6-C30)아릴실릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것을 특징으로 하는 유기 발광 화합물.The method of claim 1,
L 1 is a single bond, (C2-C30) heteroarylene or (C6-C30) arylene; Y 1 and Y 2 are each independently -O-, -S-, -CR 11 R 12- , -SiR 13 R 14 -or -NR 15 -provided that Y 1 and Y 2 do not exist at the same time; Ar 1 is (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl; R 1 to R 6 and R 11 to R 15 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl or (C2-C30) heteroaryl, -NR 21 R 22 or- SiR 23 R 24 R 25 ; R 21 to R 25 are each independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl; The arylene and heteroarylene of L 1 , Ar 1 , R 1 to R 6 and R 11 to R 15 , alkyl, aryl and heteroaryl, R 21 to R 25 , alkyl and aryl are each deuterium, halogen, (C1 -C30) alkyl, halogen substituted (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di An organic light emitting compound, which may be further substituted with one or more substituents selected from the group consisting of (C1-C30) alkyl (C6-C30) arylsilyl and (C1-C30) alkyldi (C6-C30) arylsilyl .
하기 화합물로부터 선택되는 유기 발광 화합물.
An organic light-emitting compound selected from the following compounds.
상기 유기 전계 발광 소자가 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 이 유기물층이 상기 유기 발광 화합물 중 하나 이상과 인광 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method according to claim 6,
The organic electroluminescent device comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one of the organic light emitting compounds and at least one phosphorescent dopant.
상기 유기물층이 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물(A); 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 금속을 포함하는 착체화합물(B); 또는 이들의 혼합물을 포함하는 것인 유기 전계 발광 소자.8. The method of claim 7,
(A) at least one amine compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
상기 유기물층이 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것인 유기 전계 발광 소자.8. The method of claim 7,
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009023155A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| KR20110043270A (en) * | 2009-10-21 | 2011-04-27 | (주)씨에스엘쏠라 | Organic light emitting compound and organic light emitting device comprising the same |
| DE102009053836A1 (en) * | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| KR20110129766A (en) * | 2010-05-26 | 2011-12-02 | 덕산하이메탈(주) | Compound containing five membered heterocyclic compound, and organic electronic element using the same, terminal thereof |
| CN103889952A (en) * | 2011-10-20 | 2014-06-25 | 默克专利有限公司 | Materials for organic electroluminescent devices |
-
2011
- 2011-11-16 KR KR1020110119529A patent/KR20130053846A/en not_active Application Discontinuation
-
2012
- 2012-11-16 TW TW101142776A patent/TW201329200A/en unknown
- 2012-11-16 WO PCT/KR2012/009751 patent/WO2013073896A1/en active Application Filing
- 2012-11-16 CN CN201280067085.4A patent/CN104039921A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20150096018A (en) * | 2014-02-13 | 2015-08-24 | 삼성디스플레이 주식회사 | Condensed compound and organic light emitting diode comprising the same |
| WO2017043797A1 (en) * | 2015-09-09 | 2017-03-16 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| US10968208B2 (en) | 2015-09-09 | 2021-04-06 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof |
| CN107641116A (en) * | 2016-07-20 | 2018-01-30 | 株式会社Lg化学 | Polycyclic compound and the organic illuminating element for including it |
| KR20180010132A (en) * | 2016-07-20 | 2018-01-30 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting device comprising the same |
| KR20180138269A (en) * | 2017-06-20 | 2018-12-31 | 희성소재 (주) | Heterocyclic compound and organic light emitting device comprising the same |
| US12133459B2 (en) | 2019-01-15 | 2024-10-29 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising same |
| KR20230110912A (en) | 2022-01-17 | 2023-07-25 | 주식회사 에스켐 | Method for manufacturing naphthothiophene-based compound for organic light emitting material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104039921A (en) | 2014-09-10 |
| WO2013073896A1 (en) | 2013-05-23 |
| TW201329200A (en) | 2013-07-16 |
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