WO2015046986A1 - 헤테로환 화합물 및 이를 이용한 유기 발광 소자 - Google Patents
헤테로환 화합물 및 이를 이용한 유기 발광 소자 Download PDFInfo
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- WO2015046986A1 WO2015046986A1 PCT/KR2014/009100 KR2014009100W WO2015046986A1 WO 2015046986 A1 WO2015046986 A1 WO 2015046986A1 KR 2014009100 W KR2014009100 W KR 2014009100W WO 2015046986 A1 WO2015046986 A1 WO 2015046986A1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims description 206
- 125000003118 aryl group Chemical group 0.000 claims description 96
- -1 sulfoxy group Chemical group 0.000 claims description 82
- 238000002347 injection Methods 0.000 claims description 60
- 239000007924 injection Substances 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 59
- 239000011368 organic material Substances 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002019 doping agent Substances 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005577 anthracene group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005264 aryl amine group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 9
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000003974 aralkylamines Chemical group 0.000 claims description 8
- 125000005462 imide group Chemical group 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002560 nitrile group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 195
- 238000003786 synthesis reaction Methods 0.000 description 193
- 239000010410 layer Substances 0.000 description 161
- 239000000463 material Substances 0.000 description 44
- 230000032258 transport Effects 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000758 substrate Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000151 deposition Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- RYKPDLZQIABTMY-UHFFFAOYSA-N 2-bromo-4-methoxy-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(Br)=C1 RYKPDLZQIABTMY-UHFFFAOYSA-N 0.000 description 5
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 5
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QIOZCMIWAVEQPN-UHFFFAOYSA-N [10-(4-phenylphenyl)anthracen-9-yl]boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C(C=C1)=CC=C1C1=CC=CC=C1 QIOZCMIWAVEQPN-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 4
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 4
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- JCLRVULNARKPMD-UHFFFAOYSA-N 1-[oxido(phenyl)phosphaniumyl]naphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1P(=O)C1=CC=CC=C1 JCLRVULNARKPMD-UHFFFAOYSA-N 0.000 description 2
- OIGFDBNUDSWYJE-UHFFFAOYSA-N 2-(9,10-diphenylanthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C(C=2C=CC=CC=2)=C2C(C=CC=C2)=C2C=3C=CC=CC=3)C2=C1 OIGFDBNUDSWYJE-UHFFFAOYSA-N 0.000 description 2
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 2
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 2
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UQEANKGXXSENNF-UHFFFAOYSA-N 4-bromo-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1F UQEANKGXXSENNF-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KDKBLCSXLKYXJQ-UHFFFAOYSA-N C1(=CC=C(C=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)B(O)O)C1=CC=CC=C1.C1(=CC=C(C=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)B(O)O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)B(O)O)C1=CC=CC=C1.C1(=CC=C(C=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)B(O)O)C1=CC=CC=C1 KDKBLCSXLKYXJQ-UHFFFAOYSA-N 0.000 description 2
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- 238000007650 screen-printing Methods 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
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- 239000005051 trimethylchlorosilane Substances 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Definitions
- the present specification relates to a heterocyclic compound and an organic light emitting device using the same.
- the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
- the principle of the organic light emitting phenomenon is as follows.
- An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
- the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
- the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
- organic materials having n-type properties that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used.
- the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states is preferable. desirable.
- An object of the present specification is to provide a heterocyclic compound and an organic light emitting device using the same.
- R 1 is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubsti
- R, R 'and R2 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substitute
- first electrode A first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. to provide.
- the heterocyclic compound according to one embodiment of the present specification has an appropriate energy level, and is excellent in electrochemical stability and thermal stability. Therefore, the organic light emitting device including the compound provides high efficiency and / or high driving stability.
- 1 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.
- an organic light emitting device including a heterocyclic compound represented by Chemical Formula 1 is provided.
- X is CRR '.
- X is a direct bond
- the heterocyclic compound represented by Chemical Formula 1 is represented by the following Chemical Formula 1A or the following Chemical Formula 2A.
- R1 to R8 are the same as defined in Formula 1,
- R9 and R10 are the same as or different from each other, and each independently the same as the definition of R and R '.
- substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Thiol group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Silyl groups; Aryl alkenyl group; Aryl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkylamine group; Aralkyl amine groups; Arylamine group; Heteroaryl group; Carbazole groups; Aryl group; Fluorenyl group; Arylalkyl group; Aryl alkenyl group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, S atoms, or substituted or un
- a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent to which two phenyl groups are linked.
- substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the amide group may be substituted with one or two of the nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
- Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
- the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
- the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
- the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
- the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted.
- the aryl group in the present specification may mean an aromatic ring.
- the aryl group is a monocyclic aryl group
- carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
- the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
- the polycyclic aryl group may be naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
- the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
- the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
- the present invention is not limited thereto.
- the amine group is not particularly limited, but is preferably 1 to 30.
- Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
- examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
- the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
- the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
- aryl amine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
- examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
- the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
- the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
- the heterocyclic group is a heterocyclic group containing one or more of O, N and S as heteroatoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
- the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzo
- heteroaryl group in the heteroarylamine group may be the same as the exemplified heterocyclic group.
- the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group and aralkylamine group is the same as the aryl group described above.
- the aryloxy group phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyl Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, and the like.
- arylthioxy group examples include a phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenyl.
- Thioxy groups and the like, and aryl sulfoxy groups include, but are not limited to, benzene sulfoxy groups and p-toluene sulfoxy groups.
- the alkyl group in the alkyl thioxy group and the alkyl sulfoxy group is the same as the example of the alkyl group mentioned above.
- the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
- the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups. Etc., but is not limited thereto.
- adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
- two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
- R, R 'and R2 to R8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted phosphine oxide group.
- R and R ' are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
- R is a substituted or unsubstituted alkyl group.
- R is a methyl group
- R ' is a substituted or unsubstituted alkyl group.
- R ' is a methyl group.
- R2 to R8 are the same as or different from each other, and each independently hydrogen; Substituted or substituted or unsubstituted aryl group; Or a substituted or unsubstituted phosphine oxide group.
- R2 to R8 are hydrogen.
- R2 to R8 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.
- R2 to R8 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.
- R2 to R8 are the same as or different from each other, and are each independently a substituted or unsubstituted phosphine oxide group.
- R2 to R8 are the same as or different from each other, and are each independently a substituted or unsubstituted fluorenyl group.
- the R2 to R8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted fluorene group; It is a substituted or unsubstituted phosphine oxide group.
- R2 to R8 are the same as or different from each other, and each independently hydrogen; Anthracenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a biphenyl group and a phenyl group; A phenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of naphthyl groups and anthracenyl groups substituted with phenyl groups; Phosphine oxide groups unsubstituted or substituted with one or two or more substituents selected from the group consisting of a phenyl group and a naphthyl group; Or a spirobifluorene group.
- R7 is hydrogen
- R7 is a substituted or unsubstituted aryl group.
- R7 is a substituted or unsubstituted anthracenyl group.
- R7 is an anthracenyl group substituted with a biphenyl group.
- R7 is an anthracenyl group substituted with a phenyl group.
- R7 is a substituted or unsubstituted phenyl group.
- R7 is a phenyl group substituted with a naphthyl group.
- R7 is a substituted or unsubstituted phosphine oxide group.
- R7 is a phosphine oxide group substituted with an aryl group.
- R7 is a phosphine oxide group substituted with a phenyl group.
- R7 is a phosphine oxide group substituted with a naphthyl group.
- R7 is a phosphine oxide group substituted with a phenyl group and a naphthyl group.
- R6 is a substituted or unsubstituted aryl group.
- R6 is an aryl group which is unsubstituted or substituted with an aryl group.
- R6 is an anthracene group substituted with an aryl group.
- R6 is an anthracene group substituted with a phenyl group.
- R5 is a substituted or unsubstituted aryl group.
- R5 is an aryl group which is unsubstituted or substituted with an aryl group.
- R5 is an anthracene group substituted with an aryl group.
- R5 is an anthracene group substituted with a phenyl group.
- R8 is a substituted or unsubstituted aryl group.
- R8 is an aryl group which is unsubstituted or substituted with an aryl group.
- R8 is an anthracene group substituted with an aryl group.
- R8 is an anthracene group substituted with a phenyl group.
- R3 is a substituted or unsubstituted aryl group.
- R3 is an aryl group which is unsubstituted or substituted with an aryl group.
- R3 is an anthracene group substituted with an aryl group.
- R3 is an anthracene group substituted with a phenyl group.
- R2 is a substituted or unsubstituted aryl group.
- R2 is an aryl group which is unsubstituted or substituted with an aryl group.
- R2 is a phenyl group unsubstituted or substituted with an aryl group.
- R2 is a phenyl group substituted with an anthracene group substituted with an aryl group.
- R2 is a phenyl group substituted with an anthracene group substituted with a phenyl group.
- R2 to R8 are the same as or different from each other, and each independently hydrogen; Or any one of the following structures.
- the structure is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubsti
- R1 is deuterium; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted alkyl group.
- R1 is a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.
- R1 is a substituted or unsubstituted alkyl group.
- R1 is a substituted or unsubstituted methyl group.
- R1 is a methyl group.
- R1 is a substituted or unsubstituted ethyl group.
- R1 is an ethyl group.
- R1 is a substituted or unsubstituted aryl group.
- R1 is a substituted or unsubstituted phenyl group.
- R1 is a phenyl group.
- R1 is a phenyl group substituted with a substituted or unsubstituted anthracenyl group.
- R1 is a phenyl group substituted with an anthracenyl group substituted with a biphenyl group.
- R1 is a phenyl group substituted with an anthracenyl group substituted with a phenyl group.
- the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-25.
- the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-25.
- the present specification may be prepared based on the preparation examples described below.
- a heterocyclic compound of Chemical Formula 1 may be prepared through a ring closure reaction, and R1 to R9 substituted with boronic acid or dioxoborolan group may be reacted to be represented by Chemical Formula 1 Heterocyclic compounds may be prepared, but are not limited thereto.
- the present specification also provides an organic light emitting device comprising the heterocyclic compound described above.
- first electrode A first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. to provide.
- the organic material layer includes an electron transport layer, an electron injection layer, or a layer for simultaneously transporting and transporting electrons, and the electron transport layer, an electron injection layer, or a layer for simultaneously transporting and transporting electrons. It includes the heterocyclic compound.
- the electron transport layer, the electron injection layer or the layer at the same time the electron transport and the electron injection is made of the heterocyclic compound only.
- the first electrode A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode.
- An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
- two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously performing electron transport and electron injection, and a hole blocking layer.
- the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound.
- the heterocyclic compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
- heterocyclic compound when included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
- the electron transport layer, the electron injection layer or the layer for simultaneously transporting and transporting electrons includes the heterocyclic compound as a p-type host, and includes an n-type dopant as a dopant.
- the n-type dopant includes an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound or a combination thereof.
- the n-type dopant is Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li 2 O , CsF or at least one selected from the group consisting of the following compounds.
- the light emitting layer includes the heterocyclic compound.
- the light emitting layer includes the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant.
- the phosphorescent dopant compound is represented by the following Chemical Formula 2.
- M1 is Ir or Os
- L10, L11, and L12 are the same as or different from each other, and each independently one of the following structures,
- p, q, q ', r, s, t, u', v ', w', x ', a, b', c ', d, d', f, g, h ', j, j' and k is an integer of 0 to 4, respectively,
- r ', s', t', u, v, w, x, y, y 'and e' are each an integer from 0 to 6,
- b, e, h, i, k 'and l are integers from 0 to 3
- c and g ' are each an integer of 0 to 2
- f ' is an integer from 0 to 5
- z is an integer from 0 to 8
- R10 to R65 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl group, a substituted or unsubstituted C 2 ⁇ 10; Aryl silyl group of the substituted or unsubstituted C 6 ⁇ 30 ring; A substituted or unsubstituted alkyl group of C 1-10; Substituted or unsubstituted C 2 Through C 10 Alkenyl group; Alkoxy group, a substituted or unsubstituted C 1 ⁇ 10 ring; Substituted or unsubstituted C 6 ⁇ C 20 An aryl group; And a substituted or unsubstituted C 5 to C 20 heterocyclic group, or groups adjacent to each other form a condensed ring of a monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic group.
- the phosphorescent dopant compound represented by Chemical Formula 2 is any one of the following compounds.
- the organic material layer further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.
- the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
- the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIGS. 1-10 For example, the structure of the organic light emitting device according to the present invention is illustrated in FIGS.
- FIG. 1 illustrates an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the structure is illustrated.
- the compound represented by Chemical Formula 1 may be included in the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.
- FIG. 2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the hole injection layer 3, the hole transport layer 4, or the electron transport layer 6.
- FIG 3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5 or the electron transport layer (6).
- FIG. 4 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the emission layer 5 or the electron transport layer 6.
- FIG. 5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1.
- the compound represented by Chemical Formula 1 may be included in the emission layer 5.
- the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the heterocyclic compound.
- the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- the first electrode is a cathode
- the second electrode is an anode
- the first electrode is an anode
- the second electrode is a cathode
- the substrate may be selected in consideration of optical and physical properties as needed.
- the substrate is preferably transparent.
- the substrate may be a hard material, but may be made of a flexible material such as plastic.
- the substrate may be made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (POM), and AS resin ( acrylonitrile styrene copolymer), ABS resin (acrylonitrile butadiene styrene copolymer), TAC (Triacetyl cellulose) and PAR (polyarylate) and the like, but are not limited thereto.
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- PP polypropylene
- PI polyimide
- PC polycarbonate
- PS polystyrene
- POM polyoxymethylene
- AS resin acrylonitrile styrene copolymer
- ABS resin acrylonitrile butadiene styrene copolymer
- TAC Triacetyl cellulose
- PAR polyarylate
- the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
- the positive electrode material that can be used herein include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
- the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
- the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
- the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
- the hole injection material preferably has a higher occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic material layer.
- the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organics, phthalocyanine derivatives, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, Perylene-based organic material, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- the light emitting layer may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
- At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
- the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
- the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
- the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
- the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
- the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
- the heterocyclic compound may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
- a glass substrate coated with a thin film of ITO (indium tin oxide) of 500 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. was used as a detergent
- distilled water was filtered secondly as a filter of Milpoir Co., Ltd. as distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 100 kPa on the prepared I TO transparent electrode to form a hole injection layer.
- the light emitting layer was formed by vacuum depositing the following GH and GD at a weight ratio of 10: 1 with a film thickness of 230 kPa on the hole transport layer.
- lithium fluoride (LiF) and aluminum were deposited to have a thickness of 15 kPa in sequence to form a cathode.
- the heterocyclic compound according to an exemplary embodiment of the present specification can be used as a material of the organic material layer of the organic light emitting device, in particular, when used in the electron injection and transport layer of the organic material layer, the organic light emitting device has efficiency, It can be seen that it shows excellent characteristics in driving voltage, stability and the like.
- the compound was excellent in thermal stability, it was confirmed that the deep HOMO level and hole stability exhibited excellent properties.
- the compound has the advantage of improving the efficiency, it is possible to improve the stability of the device by the thermal stability of the compound.
- BH and BD as described below were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to form a light emitting layer.
- the compound of Formula 1-6 and the following formula LiQ were vacuum-deposited on the emission layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa.
- lithium fluoride (LiF) and aluminum were deposited to have a thickness of 15 kPa in sequence to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
- the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
- aluminum is 2 ⁇ / sec
- the vacuum degree during deposition is 2 ⁇ 10
- the organic light-emitting device was manufactured by maintaining -7 to 5 x 10 -8 torr.
- Experimental Example 2-1 an organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that the compound of Formula ET-A was used instead of the compound of Formula 1-6.
- Table 2 shows the results when the current (10 mA / cm 2 ) is applied to the organic light emitting diodes manufactured by Experimental Examples 2-1 to 2-11 and Comparative Example 3.
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Abstract
Description
화합물 | 전압(V) | 효율(dc/A) | 색좌표 (x,y) | |
실험예 1-1 | 1-10 | 3.80 | 41.01 | (0.375, 0.619) |
실험예 1-2 | 1-11 | 3.62 | 41.35 | (0.374, 0.621) |
실험예 1-3 | 1-9 | 3.78 | 40.60 | (0.375, 0.619) |
실험예 1-4 | 1-5 | 3.77 | 40.23 | (0.374, 0.621) |
실험예 1-5 | 1-6 | 3.50 | 42.03 | (0.373, 0.620) |
실험예 1-6 | 1-8 | 3.84 | 40.22 | (0.374, 0.622) |
실험예 1-7 | 1-4 | 3.81 | 40.19 | (0.372, 0.621) |
실험예 1-8 | 1-7 | 3.77 | 41.08 | (0.376, 0.621) |
실험예 1-9 | 1-18 | 3.78 | 42.23 | (0.372, 0.622) |
실험예 1-10 | 1-15 | 4.00 | 40.27 | (0.374, 0.618) |
실험예 1-11 | 2-5 | 3.58 | 41.15 | (0.373, 0.619) |
실험예 1-12 | 2-6 | 3.67 | 41.23 | (0.374, 0.621) |
실험예 1-13 | 2-4 | 3.98 | 41.37 | (0.375, 0.622) |
실험예 1-14 | 2-8 | 3.57 | 42.21 | (0.371, 0.623) |
실험예 1-15 | 2-15 | 3.69 | 41.99 | (0.371, 0.620) |
실험예 1-16 | 2-19 | 3.49 | 43.11 | (0.372, 0.619) |
실험예 1-17 | 2-20 | 3.78 | 41.89 | (0.370, 0.620) |
실험예 1-18 | 2-21 | 3.59 | 40.53 | (0.372, 0.621) |
실험예 1-19 | 2-22 | 3.78 | 41.25 | (0.371, 0.620) |
비교예 1 | ET-A | 4.01 | 39.67 | (0.374, 0.622) |
비교예 2 | ET-B | 3.98 | 39.99 | (0.373, 0.621) |
화합물 | 전압(V) | 효율(dc/A) | 색좌표 (x,y) | |
실험예 2-1 | 1-6 | 3.86 | 5.07 | (0.141, 0.129) |
실험예 2-2 | 1-8 | 3.81 | 5.11 | (0.140, 0.130) |
실험예 2-3 | 1-15 | 3.78 | 5.20 | (0.141, 0.129) |
실험예 2-4 | 1-18 | 3.81 | 5.17 | (0.135, 0.131) |
실험예 2-5 | 2-6 | 3.95 | 4.99 | (0.142, 0.130) |
실험예 2-6 | 2-8 | 3.92 | 4.96 | (0.142, 0.131) |
실험예 2-7 | 2-15 | 3.81 | 5.19 | (0.135, 0.131) |
실험예 2-8 | 2-19 | 3.75 | 5.35 | (0.142, 0.130) |
실험예 2-9 | 2-20 | 3.91 | 4.94 | (0.140, 0.131) |
실험예 2-10 | 1-24 | 3.95 | 4.98 | (0.142, 0.130) |
실험예 2-11 | 1-25 | 3.82 | 5.01 | (0.141, 0.131) |
비교예 3 | ET-A | 4.05 | 4.75 | (0.141, 0.129) |
Claims (15)
- 하기 화학식 1로 표시되는 헤테로환 화합물:[화학식 1]화학식 1에 있어서,X는 직접결합; 또는 CRR'이고,R1은 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아마이드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이며,R, R' 및 R2 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아마이드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 N, O, S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이거나, R, R' 및 R2 내지 R8 중 인접하는 기는 서로 결합하여 지방족고리, 방향족고리, 지방족 헤테로고리 또는 방향족 헤테로고리를 형성하거나 스피로 결합을 형성한다.
- 청구항 1에 있어서,R1은 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 알킬기인 것인 헤테로환 화합물.
- 청구항 1에 있어서,R, R' 및 R2 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 포스핀옥사이드기인 것인 헤테로환 화합물.
- 청구항 1에 있어서,R2 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 포스핀옥사이드기인 것인 헤테로환 화합물.
- 청구항 1에 있어서,R2 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 하기 구조 중 어느 하나인 것인 헤테로환 화합물:상기 구조는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아마이드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 추가로 치환 또는 비치환될 수 있다.
- 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 발광층을 포함한 1층 이상의 유기물층을 포함하는 유기 발광 소자로서,상기 유기물층 중 1층 이상이 청구항 1 내지 7 중 어느 한 항에 따른 헤테로환 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 8에 있어서,상기 유기물층은 전자수송층, 전자주입층 또는 전자수송 및 전자주입을 동시에 하는 층을 포함하고,상기 전자수송층, 전자주입층 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 헤테로환 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 9에 있어서,상기 전자수송층, 전자주입층 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 헤테로환 화합물만으로 이루어진 것인 유기 발광 소자.
- 청구항 9에 있어서,상기 전자수송층, 전자주입층 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 헤테로환 화합물을 p-형 호스트로서 포함하고, n-형 도펀트를 도펀트로서 포함하는 것인 유기 발광 소자.
- 청구항 11에 있어서,상기 n-형 도펀트는 알칼리금속, 알칼리 금속 화합물, 알칼리 토금속, 또는 알칼리 토금속 화합물 또는 이들의 조합물을 포함하는 것인 유기 발광 소자.
- 청구항 8에 있어서,상기 발광층은 상기 헤테로환 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 13에 있어서,상기 발광층은 상기 헤테로환 화합물을 호스트로서 포함하고, 인광 도펀트 화합물을 도펀트로서 포함하는 것인 유기 발광 소자.
- 청구항 8에 있어서,상기 유기물층은 정공주입층, 정공수송층. 전자수송층, 전자주입층, 전자저지층 및 정공저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.
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US15/025,046 US10103336B2 (en) | 2013-09-30 | 2014-09-29 | Heterocyclic compound and organic light-emitting element using same |
EP14848459.5A EP3053984B1 (en) | 2013-09-30 | 2014-09-29 | Heterocyclic compound and organic light-emitting element using same |
JP2016545692A JP6178518B2 (ja) | 2013-09-30 | 2014-09-29 | 複素環化合物及びこれを用いた有機発光素子 |
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